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witw78
Apr 18th, 2025
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  1. /home/xie.zhongwei/workspace/data/SMolInstruct/raw/test/forward_synthesis.jsonl
  2.  
  3. {"input": "CCN.CN1C=CC=C1C=O", "output": "CCNCC1=CC=CN1C", "task": "forward_synthesis", "split": "test", "original_reaction_smiles_with_atom_mapping": ["[CH2:1]([NH2:3])[CH3:2].[CH3:4][N:5]1[CH:9]=[CH:8][CH:7]=[C:6]1[CH:10]=O>>[CH2:1]([NH:3][CH2:10][C:6]1[N:5]([CH3:4])[CH:9]=[CH:8][CH:7]=1)[CH3:2]"]}
  4. {"input": "CN(C)C=CC(=O)C1=CC=CO1.CS(C)=O.Cl.N#CCC(N)=O.O.O=C([O-])[O-].[K+]", "output": "N#CC1=CC=C(C2=CC=CO2)NC1=O", "task": "forward_synthesis", "split": "test", "original_reaction_smiles_with_atom_mapping": ["CN(C)[CH:3]=[CH:4][C:5]([C:7]1[O:8][CH:9]=[CH:10][CH:11]=1)=O.[C:13]([CH2:15][C:16]([NH2:18])=[O:17])#[N:14].C(=O)([O-])[O-].[K+].[K+].Cl>CS(C)=O.O>[O:8]1[CH:9]=[CH:10][CH:11]=[C:7]1[C:5]1[NH:18][C:16](=[O:17])[C:15]([C:13]#[N:14])=[CH:3][CH:4]=1"]}
  5. {"input": "CCN(CC)CC.CS(=O)(=O)Cl.ClCCl.OCC1=COC(Cl)=N1.[Cl-].[NH4+]", "output": "CS(=O)(=O)OCC1=COC(Cl)=N1", "task": "forward_synthesis", "split": "test", "original_reaction_smiles_with_atom_mapping": ["[Cl:1][C:2]1[O:3][CH:4]=[C:5]([CH2:7][OH:8])[N:6]=1.[CH3:9][S:10](Cl)(=[O:12])=[O:11].C(N(CC)CC)C.[Cl-].[NH4+]>ClCCl>[CH3:9][S:10]([O:8][CH2:7][C:5]1[N:6]=[C:2]([Cl:1])[O:3][CH:4]=1)(=[O:12])=[O:11]"]}
  6. {"input": "C1=CC=NC=C1.CN(C)C1=CC=CC(C(=O)Cl)=C1.NC1=NNC2=CC=C([N+](=O)[O-])C=C12", "output": "CN(C)C1=CC=CC(C(=O)NC2=NNC3=CC=C([N+](=O)[O-])C=C23)=C1", "task": "forward_synthesis", "split": "test", "original_reaction_smiles_with_atom_mapping": ["[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][N:8]=[C:7]2[NH2:13])([O-:3])=[O:2].N1C=CC=CC=1.[CH3:20][N:21]([CH3:31])[C:22]1[CH:23]=[C:24]([CH:28]=[CH:29][CH:30]=1)[C:25](Cl)=[O:26]>>[CH3:20][N:21]([CH3:31])[C:22]1[CH:23]=[C:24]([CH:28]=[CH:29][CH:30]=1)[C:25]([NH:13][C:7]1[C:6]2[C:10](=[CH:11][CH:12]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=2)[NH:9][N:8]=1)=[O:26]"]}
  7. {"input": "CC1COC2=C3C(=CC(F)=C2C2=CSC(CN)=N2)C(=O)C(C(=O)O)=CN31.CCNCC1=NC(C2=C(F)C=C3C(=O)C(C(=O)O)=CN(CCF)C3=C2F)=CS1", "output": "CNCC1=NC(C2=C(F)C=C3C(=O)C(C(=O)O)=CN(CCF)C3=C2F)=CS1", "task": "forward_synthesis", "split": "test", "original_reaction_smiles_with_atom_mapping": ["[CH2:1]([NH:3][CH2:4][C:5]1[S:6][CH:7]=[C:8]([C:10]2[C:19]([F:20])=[C:18]3[C:13]([C:14](=[O:27])[C:15]([C:24]([OH:26])=[O:25])=[CH:16][N:17]3[CH2:21][CH2:22][F:23])=[CH:12][C:11]=2[F:28])[N:9]=1)C.NCC1SC=C(C2C(F)=CC3C(=O)C(C(O)=O)=CN4C(C)COC=2C=34)N=1>>[F:28][C:11]1[CH:12]=[C:13]2[C:18](=[C:19]([F:20])[C:10]=1[C:8]1[N:9]=[C:5]([CH2:4][NH:3][CH3:1])[S:6][CH:7]=1)[N:17]([CH2:21][CH2:22][F:23])[CH:16]=[C:15]([C:24]([OH:26])=[O:25])[C:14]2=[O:27]"]}
  8. {"input": "C1=CC=C([PH](C2=CC=CC=C2)(C2=CC=CC=C2)[Pd]([PH](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)([PH](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)[PH](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC(C)(C)OC(=O)N[C@H]1COCC[C@H]1NC1=NC(Cl)=C2C(=O)N(C(=O)OC(C)(C)C)CC2=C1F.CC1=CC=CC=C1.CCCC[Sn](CCCC)(CCCC)C1=CC2=CN=CC=C2S1", "output": "CC(C)(C)OC(=O)N[C@H]1CCCC[C@H]1NC1=NC(C2=CC3=CN=CC=C3S2)=C2C(=O)N(C(=O)OC(C)(C)C)CC2=C1F", "task": "forward_synthesis", "split": "test", "original_reaction_smiles_with_atom_mapping": ["[C:1]([O:5][C:6]([NH:8][C@@H:9]1[C@H:14]([NH:15][C:16]2[N:21]=[C:20](Cl)[C:19]3[C:23](=[O:33])[N:24]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:25][C:18]=3[C:17]=2[F:34])[CH2:13][CH2:12]O[CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C([Sn](CCCC)(CCCC)[C:40]1[S:48][C:47]2[CH:46]=[CH:45][N:44]=[CH:43][C:42]=2[CH:41]=1)CCC.[C:57]1(C)C=CC=CC=1>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:1]([O:5][C:6]([NH:8][C@H:9]1[CH2:10][CH2:57][CH2:12][CH2:13][C@H:14]1[NH:15][C:16]1[N:21]=[C:20]([C:40]2[S:48][C:47]3[CH:46]=[CH:45][N:44]=[CH:43][C:42]=3[CH:41]=2)[C:19]2[C:23](=[O:33])[N:24]([C:26]([O:28][C:29]([CH3:30])([CH3:32])[CH3:31])=[O:27])[CH2:25][C:18]=2[C:17]=1[F:34])=[O:7])([CH3:2])([CH3:3])[CH3:4]"]}
  9. {"input": "NC1=CC=C2C(=C1)C[C@@H]1NCCC[C@H]21.O=C(O)C1=CC=C2NC=NC2=C1", "output": "NC1=CC=C2C(=C1)C[C@H]1[C@@H]2CCCN1C(=O)C1=CC=C2NC=NC2=C1", "task": "forward_synthesis", "split": "test", "original_reaction_smiles_with_atom_mapping": ["[NH:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]([OH:12])=O)=[CH:9][C:4]=2[N:3]=[CH:2]1.[NH:13]1[CH2:18][CH2:17][CH2:16][C@@H:15]2[C:19]3[CH:20]=[CH:21][C:22]([NH2:26])=[CH:23][C:24]=3[CH2:25][C@H:14]12>>[NH2:26][C:22]1[CH:21]=[CH:20][C:19]2[C@@H:15]3[C@@H:14]([N:13]([C:10]([C:8]4[CH:7]=[CH:6][C:5]5[NH:1][CH:2]=[N:3][C:4]=5[CH:9]=4)=[O:12])[CH2:18][CH2:17][CH2:16]3)[CH2:25][C:24]=2[CH:23]=1"]}
  10. {"input": "COC1=CC(C(=O)O)=CC=C1C1=CC=CC=N1.C[Si](C)(C)OP(=O)=O.NC1=CN=CC=C1O", "output": "COC1=CC(C2=NC3=CN=CC=C3O2)=CC=C1C1=CC=CC=N1", "task": "forward_synthesis", "split": "test", "original_reaction_smiles_with_atom_mapping": ["C[Si](OP(=O)=O)(C)C.[NH2:9][C:10]1[CH:11]=[N:12][CH:13]=[CH:14][C:15]=1[OH:16].[CH3:17][O:18][C:19]1[CH:20]=[C:21]([CH:25]=[CH:26][C:27]=1[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][N:29]=1)[C:22](O)=O>>[CH3:17][O:18][C:19]1[CH:20]=[C:21]([C:22]2[O:16][C:15]3[CH:14]=[CH:13][N:12]=[CH:11][C:10]=3[N:9]=2)[CH:25]=[CH:26][C:27]=1[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][N:29]=1"]}
  11. {"input": "C1COCCO1.C[C@H](O)CN.O=S(=O)(NC1=CC=CC(C2=C(C3=CC=NC(Cl)=N3)SC(C3CCOCC3)=N2)=C1F)C1=COC=C1", "output": "C[C@H](O)CNC1=NC=CC(C2=C(C3=CC=CC(NS(=O)(=O)C4=COC=C4)=C3F)N=C(C3CCOCC3)S2)=N1", "task": "forward_synthesis", "split": "test", "original_reaction_smiles_with_atom_mapping": ["Cl[C:2]1[N:7]=[C:6]([C:8]2[S:12][C:11]([CH:13]3[CH2:18][CH2:17][O:16][CH2:15][CH2:14]3)=[N:10][C:9]=2[C:19]2[C:20]([F:34])=[C:21]([NH:25][S:26]([C:29]3[CH:33]=[CH:32][O:31][CH:30]=3)(=[O:28])=[O:27])[CH:22]=[CH:23][CH:24]=2)[CH:5]=[CH:4][N:3]=1.[NH2:35][CH2:36][C@@H:37]([OH:39])[CH3:38]>O1CCOCC1>[F:34][C:20]1[C:19]([C:9]2[N:10]=[C:11]([CH:13]3[CH2:18][CH2:17][O:16][CH2:15][CH2:14]3)[S:12][C:8]=2[C:6]2[CH:5]=[CH:4][N:3]=[C:2]([NH:35][CH2:36][C@@H:37]([OH:39])[CH3:38])[N:7]=2)=[CH:24][CH:23]=[CH:22][C:21]=1[NH:25][S:26]([C:29]1[CH:33]=[CH:32][O:31][CH:30]=1)(=[O:28])=[O:27]"]}
  12. {"input": "CCN(C(C)C)C(C)C.CCN=C=NCCCN(C)C.CN(C)C=O.CNC(=O)C1=CC=C(N)C=C1.COC1=CC=C(NC2=CC(C3=CC=CC(C(=O)O)=C3)=NN3C=CN=C23)N=C1OC.ON1N=NC2=CC=CC=C21", "output": "CNC(=O)C1=CC=C(NC(=O)C2=CC=CC(C3=NN4C=CN=C4C(NC4=CC=C(OC)C(OC)=N4)=C3)=C2)C=C1", "task": "forward_synthesis", "split": "test", "original_reaction_smiles_with_atom_mapping": ["[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([NH:11][C:12]2[C:13]3[N:14]([CH:27]=[CH:28][N:29]=3)[N:15]=[C:16]([C:18]3[CH:19]=[C:20]([CH:24]=[CH:25][CH:26]=3)[C:21](O)=[O:22])[CH:17]=2)=[N:7][C:8]=1[O:9][CH3:10].C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.CCN(C(C)C)C(C)C.[NH2:60][C:61]1[CH:70]=[CH:69][C:64]([C:65]([NH:67][CH3:68])=[O:66])=[CH:63][CH:62]=1>CN(C=O)C>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([NH:11][C:12]2[C:13]3[N:14]([CH:27]=[CH:28][N:29]=3)[N:15]=[C:16]([C:18]3[CH:19]=[C:20]([CH:24]=[CH:25][CH:26]=3)[C:21]([NH:60][C:61]3[CH:62]=[CH:63][C:64]([C:65](=[O:66])[NH:67][CH3:68])=[CH:69][CH:70]=3)=[O:22])[CH:17]=2)=[N:7][C:8]=1[O:9][CH3:10]"]}
  13. {"input": "CC(=O)[O-].CC1=CC(C2=CC=CC=C2)=CC(C)=C1[Pb+3].CC1=CC=CC=C1.CN(C)C1=CC=NC=C1.Cl.ClC(Cl)Cl.O=C1CC(=O)CC2(CCOCC2)C1", "output": "CC1=CC(C2=CC=CC=C2)=CC(C)=C1C1C(=O)CC2(CCOCC2)CC1=O", "task": "forward_synthesis", "split": "test", "original_reaction_smiles_with_atom_mapping": ["[CH2:1]1[C:6]2([CH2:11][C:10](=[O:12])[CH2:9][C:8](=[O:13])[CH2:7]2)[CH2:5][CH2:4][O:3][CH2:2]1.C1(C)C=CC=CC=1.C([O-])(=O)C.C([O-])(=O)C.C([O-])(=O)C.[CH3:33][C:34]1[C:39]([Pb+3])=[C:38]([CH3:41])[CH:37]=[C:36]([C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)[CH:35]=1.Cl>CN(C)C1C=CN=CC=1.C(Cl)(Cl)Cl>[CH3:33][C:34]1[CH:35]=[C:36]([C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)[CH:37]=[C:38]([CH3:41])[C:39]=1[CH:9]1[C:10](=[O:12])[CH2:11][C:6]2([CH2:5][CH2:4][O:3][CH2:2][CH2:1]2)[CH2:7][C:8]1=[O:13]"]}
  14. {"input": "CC(=O)O.CO.Cl.O=C1NC2=CC(C3=CC=CO3)=CC=C2C2=C1CCC2.[MgH2]", "output": "O=C1NC2=CC(C3=CC=CO3)=CC=C2C2CCCC12", "task": "forward_synthesis", "split": "test", "original_reaction_smiles_with_atom_mapping": ["[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[CH:7]=[CH:8][C:9]2[C:10]3[CH2:19][CH2:18][CH2:17][C:11]=3[C:12](=[O:16])[NH:13][C:14]=2[CH:15]=1.[Mg].C(O)(=O)C.Cl>CO>[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[CH:7]=[CH:8][C:9]2[CH:10]3[CH2:19][CH2:18][CH2:17][CH:11]3[C:12](=[O:16])[NH:13][C:14]=2[CH:15]=1"]}
  15. {"input": "N#CSCCl.OC(=S)C1=CC=CC=C1Cl", "output": "N#CSCOC(=S)C1=CC=CC=C1Cl", "task": "forward_synthesis", "split": "test", "original_reaction_smiles_with_atom_mapping": ["[Cl:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[S:5].Cl[CH2:12][S:13][C:14]#[N:15]>>[S:13]([CH2:12][O:6][C:4](=[S:5])[C:3]1[CH:7]=[CH:8][CH:9]=[CH:10][C:2]=1[Cl:1])[C:14]#[N:15]"]}
  16. {"input": "CC(=O)[O-].CC(C)NCC(=O)N1CC(C)(C)C2=CC=C(N3C(=O)N(CC4=CC=NC(Cl)=C4)C(C)(C)C3=O)C=C21.CC1(C)C2=CC=C(P(C3=CC=CC=C3)C3=CC=CC=C3)C=C2OC2=CC(P(C3=CC=CC=C3)C3=CC=CC=C3)=CC=C21.CN1CCCC1=O.ClCCl.NC1=CC=CN=C1.O=C([O-])[O-].[Cs+].[Pd+2]", "output": "CC(C)NCC(=O)N1CC(C)(C)C2=CC=C(N3C(=O)N(CC4=CC=NC(NC5=CC=CN=C5)=C4)C(C)(C)C3=O)C=C21", "task": "forward_synthesis", "split": "test", "original_reaction_smiles_with_atom_mapping": ["Cl[C:2]1[CH:7]=[C:6]([CH2:8][N:9]2[C:13]([CH3:15])([CH3:14])[C:12](=[O:16])[N:11]([C:17]3[CH:25]=[C:24]4[C:20]([C:21]([CH3:34])([CH3:33])[CH2:22][N:23]4[C:26](=[O:32])[CH2:27][NH:28][CH:29]([CH3:31])[CH3:30])=[CH:19][CH:18]=3)[C:10]2=[O:35])[CH:5]=[CH:4][N:3]=1.[NH2:36][C:37]1[CH:38]=[N:39][CH:40]=[CH:41][CH:42]=1.CC1(C)C2C=CC(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=2OC2C1=CC=C(P(C1C=CC=CC=1)C1C=CC=CC=1)C=2.C(=O)([O-])[O-].[Cs+].[Cs+]>CN1CCCC1=O.ClCCl.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH:29]([NH:28][CH2:27][C:26]([N:23]1[C:24]2[C:20](=[CH:19][CH:18]=[C:17]([N:11]3[C:12](=[O:16])[C:13]([CH3:15])([CH3:14])[N:9]([CH2:8][C:6]4[CH:5]=[CH:4][N:3]=[C:2]([NH:36][C:37]5[CH:38]=[N:39][CH:40]=[CH:41][CH:42]=5)[CH:7]=4)[C:10]3=[O:35])[CH:25]=2)[C:21]([CH3:34])([CH3:33])[CH2:22]1)=[O:32])([CH3:31])[CH3:30]"]}
  17. {"input": "C1CCOC1.CC(C)(C)C1=CC(N)=NO1.NC1=NNC=C1.O=C1NC2=CC=CC=C2/C1=C/O", "output": "CC(C)(C)C1=CC(NC=C2C(=O)NC3=CC=CC=C23)=NO1", "task": "forward_synthesis", "split": "test", "original_reaction_smiles_with_atom_mapping": ["NC1C=CNN=1.O/[CH:8]=[C:9]1\\[C:10](=[O:18])[NH:11][C:12]2[C:17]\\1=[CH:16][CH:15]=[CH:14][CH:13]=2.[C:19]([C:23]1[O:27][N:26]=[C:25]([NH2:28])[CH:24]=1)([CH3:22])([CH3:21])[CH3:20]>O1CCCC1>[C:19]([C:23]1[O:27][N:26]=[C:25]([NH:28][CH:8]=[C:9]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[NH:11][C:10]2=[O:18])[CH:24]=1)([CH3:22])([CH3:21])[CH3:20]"]}
  18. {"input": "Br.CCOC(=O)C1=C(C2=CC(OC)=C(OC)C([N+](=O)[O-])=C2)OC=N1", "output": "NCC(=O)C1=CC(O)=C(O)C([N+](=O)[O-])=C1", "task": "forward_synthesis", "split": "test", "original_reaction_smiles_with_atom_mapping": ["C[O:2][C:3]1[CH:4]=[C:5]([C:14]2[O:18]C=[N:16][C:15]=2C(OCC)=O)[CH:6]=[C:7]([N+:11]([O-:13])=[O:12])[C:8]=1[O:9]C.[BrH:24]>>[BrH:24].[NH2:16][CH2:15][C:14]([C:5]1[CH:6]=[C:7]([N+:11]([O-:13])=[O:12])[C:8]([OH:9])=[C:3]([OH:2])[CH:4]=1)=[O:18]"]}
  19. {"input": "C1CCOC1.CCOC(=O)C1=C(C2=CC=CC=C2)C2=CC=C(OC)C=C2C1=O.Cl[Mg]C1CCCCC1", "output": "CCOC(=O)C1=C(C2=CC=CC=C2)C2=CC=C(OC)C=C2C1(O)C1CCCCC1", "task": "forward_synthesis", "split": "test", "original_reaction_smiles_with_atom_mapping": ["[CH2:1]([O:3][C:4]([C:6]1[C:7](=[O:23])[C:8]2[C:13]([C:14]=1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[CH:12][CH:11]=[C:10]([O:21][CH3:22])[CH:9]=2)=[O:5])[CH3:2].[CH:24]1([Mg]Cl)[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1>C1COCC1>[CH2:1]([O:3][C:4]([C:6]1[C:7]([CH:24]2[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]2)([OH:23])[C:8]2[C:13]([C:14]=1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[CH:12][CH:11]=[C:10]([O:21][CH3:22])[CH:9]=2)=[O:5])[CH3:2]"]}
  20. {"input": "CCCCC1=CC=C(CNCC2=CC=CC(CC(=O)OC)=C2)C=C1.CN1C=NC(S(=O)(=O)Cl)=C1", "output": "CCCCC1=CC=C(CN(CC2=CC=CC(CC(=O)OC)=C2)S(=O)(=O)C2=CN(C)C=N2)C=C1", "task": "forward_synthesis", "split": "test", "original_reaction_smiles_with_atom_mapping": ["[CH3:1][O:2][C:3](=[O:24])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([CH2:11][NH:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([CH2:20][CH2:21][CH2:22][CH3:23])=[CH:16][CH:15]=2)[CH:6]=1.[CH3:25][N:26]1[CH:30]=[C:29]([S:31](Cl)(=[O:33])=[O:32])[N:28]=[CH:27]1>>[CH3:1][O:2][C:3](=[O:24])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([CH2:11][N:12]([CH2:13][C:14]2[CH:19]=[CH:18][C:17]([CH2:20][CH2:21][CH2:22][CH3:23])=[CH:16][CH:15]=2)[S:31]([C:29]2[N:28]=[CH:27][N:26]([CH3:25])[CH:30]=2)(=[O:33])=[O:32])[CH:6]=1"]}
  21. {"input": "C1=CC=C(CN2C(NC3CCNC3)=NC3=CC=CC=C32)N=C1.CN(C)C=O.Cl.N#CCCl.O=C([O-])[O-].[Na+]", "output": "N#CCN1CCC(NC2=NC3=CC=CC=C3N2CC2=CC=CC=N2)C1", "task": "forward_synthesis", "split": "test", "original_reaction_smiles_with_atom_mapping": ["Cl.Cl.[N:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:9][N:10]1[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[N:12]=[C:11]1[NH:19][CH:20]1[CH2:24][CH2:23][NH:22][CH2:21]1.C(=O)([O-])[O-].[Na+].[Na+].Cl[CH2:32][C:33]#[N:34]>CN(C)C=O>[N:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:9][N:10]1[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[N:12]=[C:11]1[NH:19][CH:20]1[CH2:24][CH2:23][N:22]([CH2:32][C:33]#[N:34])[CH2:21]1"]}
  22. {"input": "CC1=CC=CC=C1.CCO.CCOC(=O)N1CCN(CCC2=CC=CC(Cl)=C2)CC1.CCOC(=O)N1CCNCC1.ClC1=CC=CC(CCBr)=C1.O.[K+].[OH-]", "output": "ClC1=CC=CC(CCN2CCNCC2)=C1", "task": "forward_synthesis", "split": "test", "original_reaction_smiles_with_atom_mapping": ["[OH-].[K+].C(OC([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([Cl:22])[CH:17]=2)[CH2:10][CH2:9]1)=O)C.C(OC(N1CCNCC1)=O)C.ClC1C=C(CCBr)C=CC=1>O.C1(C)C=CC=CC=1.C(O)C>[Cl:22][C:18]1[CH:17]=[C:16]([CH2:15][CH2:14][N:11]2[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]2)[CH:21]=[CH:20][CH:19]=1"]}
  23. {"input": "CC[Si](CC)(CC)O[C@@H]1C[C@H](O)[C@H](C/C=C\\CCCC23OCC(C)(CO2)CO3)[C@H]1CS(=O)(=O)C1=CC=CC=C1.O=P(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1", "output": "CC12COC(CCC/C=C\\C[C@@H]3[C@@H](CS(=O)(=O)C4=CC=CC=C4)[C@H](O)C[C@@H]3O)(OC1)OC2", "task": "forward_synthesis", "split": "test", "original_reaction_smiles_with_atom_mapping": ["[CH3:1][C:2]12[CH2:9][O:8][C:5]([CH2:10][CH2:11][CH2:12]/[CH:13]=[CH:14]\\[CH2:15][C@@H:16]3[C@@H:20]([CH2:21][S:22]([C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)(=[O:24])=[O:23])[C@H:19]([O:31][Si](CC)(CC)CC)[CH2:18][C@@H:17]3[OH:39])([O:6][CH2:7]1)[O:4][CH2:3]2.C1(P(=O)(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>>[CH3:1][C:2]12[CH2:7][O:6][C:5]([CH2:10][CH2:11][CH2:12]/[CH:13]=[CH:14]\\[CH2:15][C@@H:16]3[C@@H:20]([CH2:21][S:22]([C:25]4[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=4)(=[O:24])=[O:23])[C@H:19]([OH:31])[CH2:18][C@@H:17]3[OH:39])([O:4][CH2:3]1)[O:8][CH2:9]2"]}
  24. {"input": "C1COCCO1.CC1(C)C2=CC=CC(P(C3=CC=CC=C3)C3=CC=CC=C3)=C2OC2=C(P(C3=CC=CC=C3)C3=CC=CC=C3)C=CC=C21.CC1=C(Br)C=CC2=C(Cl)C=CN=C12.CCN(C(C)C)C(C)C.O=C(/C=C/C1=CC=CC=C1)/C=C/C1=CC=CC=C1.SCC1=CC=CC=C1.[Pd]", "output": "CC1=C(SCC2=CC=CC=C2)C=CC2=C(Cl)C=CN=C12", "task": "forward_synthesis", "split": "test", "original_reaction_smiles_with_atom_mapping": ["Br[C:2]1[C:11]([CH3:12])=[C:10]2[C:5]([C:6]([Cl:13])=[CH:7][CH:8]=[N:9]2)=[CH:4][CH:3]=1.CCN(C(C)C)C(C)C.CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.[CH2:65]([SH:72])[C:66]1[CH:71]=[CH:70][CH:69]=[CH:68][CH:67]=1>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O1CCOCC1>[CH2:65]([S:72][C:2]1[C:11]([CH3:12])=[C:10]2[C:5]([C:6]([Cl:13])=[CH:7][CH:8]=[N:9]2)=[CH:4][CH:3]=1)[C:66]1[CH:71]=[CH:70][CH:69]=[CH:68][CH:67]=1"]}
  25. {"input": "CC1=C(Br)C(=O)N(C2CCCC2)C2=NC(S(C)=O)=NC=C12.CC1=CC=CC=C1.CN1CCN(C2=CC=C(N)N=C2)CC1", "output": "CC1=C(Br)C(=O)N(C2CCCC2)C2=NC(NC3=CC=C(N4CCN(C)CC4)C=N3)=NC=C12", "task": "forward_synthesis", "split": "test", "original_reaction_smiles_with_atom_mapping": ["[Br:1][C:2]1[C:14](=[O:15])[N:13]([CH:16]2[CH2:20][CH2:19][CH2:18][CH2:17]2)[C:5]2[N:6]=[C:7](S(C)=O)[N:8]=[CH:9][C:4]=2[C:3]=1[CH3:21].[CH3:22][N:23]1[CH2:28][CH2:27][N:26]([C:29]2[CH:30]=[CH:31][C:32]([NH2:35])=[N:33][CH:34]=2)[CH2:25][CH2:24]1>C1(C)C=CC=CC=1>[Br:1][C:2]1[C:14](=[O:15])[N:13]([CH:16]2[CH2:20][CH2:19][CH2:18][CH2:17]2)[C:5]2[N:6]=[C:7]([NH:35][C:32]3[CH:31]=[CH:30][C:29]([N:26]4[CH2:27][CH2:28][N:23]([CH3:22])[CH2:24][CH2:25]4)=[CH:34][N:33]=3)[N:8]=[CH:9][C:4]=2[C:3]=1[CH3:21]"]}
  26. {"input": "CN(C)C=O.ClCCCBr.N#CC1=CC=C(C2=CC=CC=C2)C(O)=C1.O=C([O-])[O-].[K+]", "output": "N#CC1=CC=C(C2=CC=CC=C2)C(OCCCCl)=C1", "task": "forward_synthesis", "split": "test", "original_reaction_smiles_with_atom_mapping": ["[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:5]#[N:6].C(=O)([O-])[O-].[K+].[K+].Br[CH2:23][CH2:24][CH2:25][Cl:26]>CN(C)C=O>[Cl:26][CH2:25][CH2:24][CH2:23][O:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)[C:5]#[N:6]"]}
  27. {"input": "C1CCOC1.CCOC(=O)CCCCC(=O)C1=C(C)C=C(C)C(C)=C1O.[Al+3].[H-].[Li+]", "output": "CC1=CC(C)=C(C(O)CCCCCO)C(O)=C1C", "task": "forward_synthesis", "split": "test", "original_reaction_smiles_with_atom_mapping": ["[OH:1][C:2]1[C:18]([CH3:19])=[C:17]([CH3:20])[CH:16]=[C:15]([CH3:21])[C:3]=1[C:4]([CH2:6][CH2:7][CH2:8][CH2:9][C:10](OCC)=[O:11])=[O:5].[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[OH:1][C:2]1[C:18]([CH3:19])=[C:17]([CH3:20])[CH:16]=[C:15]([CH3:21])[C:3]=1[CH:4]([OH:5])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][OH:11]"]}
  28. {"input": "C1=CN=C(N2CCNCC2)N=C1.COC1=CC=C(CN(CC2=CC=C(OC)C=C2)C2=NC=C(C3=NC(N4CCOCC4)=NC4=C3CCN4C3=CC=C(C(=O)O)C=C3)C=N2)C=C1.Cl", "output": "COC1=CC=C(CN(CC2=CC=C(OC)C=C2)C2=NC=C(C3=NC(N4CCOCC4)=NC4=C3CCN4C3=CC=C(C(=O)N4CCN(C5=NC=CC=N5)CC4)C=C3)C=N2)C=C1", "task": "forward_synthesis", "split": "test", "original_reaction_smiles_with_atom_mapping": ["[CH3:1][O:2][C:3]1[CH:49]=[CH:48][C:6]([CH2:7][N:8]([CH2:39][C:40]2[CH:45]=[CH:44][C:43]([O:46][CH3:47])=[CH:42][CH:41]=2)[C:9]2[N:14]=[CH:13][C:12]([C:15]3[C:16]4[CH2:29][CH2:28][N:27]([C:30]5[CH:38]=[CH:37][C:33]([C:34](O)=[O:35])=[CH:32][CH:31]=5)[C:17]=4[N:18]=[C:19]([N:21]4[CH2:26][CH2:25][O:24][CH2:23][CH2:22]4)[N:20]=3)=[CH:11][N:10]=2)=[CH:5][CH:4]=1.Cl.Cl.[N:52]1[CH:57]=[CH:56][CH:55]=[N:54][C:53]=1[N:58]1[CH2:63][CH2:62][NH:61][CH2:60][CH2:59]1>>[CH3:1][O:2][C:3]1[CH:49]=[CH:48][C:6]([CH2:7][N:8]([CH2:39][C:40]2[CH:45]=[CH:44][C:43]([O:46][CH3:47])=[CH:42][CH:41]=2)[C:9]2[N:14]=[CH:13][C:12]([C:15]3[C:16]4[CH2:29][CH2:28][N:27]([C:30]5[CH:31]=[CH:32][C:33]([C:34]([N:61]6[CH2:62][CH2:63][N:58]([C:53]7[N:52]=[CH:57][CH:56]=[CH:55][N:54]=7)[CH2:59][CH2:60]6)=[O:35])=[CH:37][CH:38]=5)[C:17]=4[N:18]=[C:19]([N:21]4[CH2:22][CH2:23][O:24][CH2:25][CH2:26]4)[N:20]=3)=[CH:11][N:10]=2)=[CH:5][CH:4]=1"]}
  29. {"input": "CC(=O)O.COC1=CC=C(CNC2=NC=NC3=C2C=CN3[C@@H]2O[C@H](CN(CCCCC(=O)NC3=CC=C(C(C)(C)C)C=C3N)C(C)C)[C@H]3OC(C)(C)O[C@H]32)C(OC)=C1", "output": "COC1=CC=C(CNC2=NC=NC3=C2C=CN3[C@@H]2O[C@H](CN(CCCCC3=NC4=CC(C(C)(C)C)=CC=C4N3)C(C)C)[C@H]3OC(C)(C)O[C@H]32)C(OC)=C1", "task": "forward_synthesis", "split": "test", "original_reaction_smiles_with_atom_mapping": ["[NH2:1][C:2]1[CH:7]=[C:6]([C:8]([CH3:11])([CH3:10])[CH3:9])[CH:5]=[CH:4][C:3]=1[NH:12][C:13](=O)[CH2:14][CH2:15][CH2:16][CH2:17][N:18]([CH2:22][C@@H:23]1[C@@H:30]2[C@@H:26]([O:27][C:28]([CH3:32])([CH3:31])[O:29]2)[C@H:25]([N:33]2[C:37]3[N:38]=[CH:39][N:40]=[C:41]([NH:42][CH2:43][C:44]4[CH:49]=[CH:48][C:47]([O:50][CH3:51])=[CH:46][C:45]=4[O:52][CH3:53])[C:36]=3[CH:35]=[CH:34]2)[O:24]1)[CH:19]([CH3:21])[CH3:20]>C(O)(=O)C>[C:8]([C:6]1[CH:5]=[CH:4][C:3]2[NH:12][C:13]([CH2:14][CH2:15][CH2:16][CH2:17][N:18]([CH2:22][C@@H:23]3[C@H:30]4[O:29][C:28]([CH3:31])([CH3:32])[O:27][C@H:26]4[C@H:25]([N:33]4[C:37]5[N:38]=[CH:39][N:40]=[C:41]([NH:42][CH2:43][C:44]6[CH:49]=[CH:48][C:47]([O:50][CH3:51])=[CH:46][C:45]=6[O:52][CH3:53])[C:36]=5[CH:35]=[CH:34]4)[O:24]3)[CH:19]([CH3:21])[CH3:20])=[N:1][C:2]=2[CH:7]=1)([CH3:9])([CH3:11])[CH3:10]"]}
  30. {"input": "C1CCOC1.CCN(CC)S(F)(F)F.CCOC(=O)C1=CN2C3=C(CCN2CO)C(F)=C(F)C=C3C1=O.CO", "output": "CCOC(=O)C1=CN2C3=C(CCN2COC)C(F)=C(F)C=C3C1=O", "task": "forward_synthesis", "split": "test", "original_reaction_smiles_with_atom_mapping": ["[F:1][C:2]1[C:11]([F:12])=[CH:10][C:9]2[C:13](=[O:21])[C:14]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:15][N:7]3[C:8]=2[C:3]=1[CH2:4][CH2:5][N:6]3[CH2:22][OH:23].[CH2:24](N(S(F)(F)F)CC)C.CO>O1CCCC1>[F:1][C:2]1[C:11]([F:12])=[CH:10][C:9]2[C:13](=[O:21])[C:14]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:15][N:7]3[C:8]=2[C:3]=1[CH2:4][CH2:5][N:6]3[CH2:22][O:23][CH3:24]"]}
  31. {"input": "C1=CC=C(P(C2=CC=CC=C2)[C-]2C=CC=C2)C=C1.C=C(OC)O[Si](C)(C)C(C)(C)C.CC(=O)[O-].CC1=NC2=CC(Cl)=CC(OS(=O)(=O)C(F)(F)F)=C2C(C)=C1CC1=CC=C(Cl)C=C1.CC1=NC2=CC(OS(=O)(=O)C(F)(F)F)=CC(Cl)=C2C(C)=C1CC1=CC=C(Cl)C=C1.CCOC(C)=O.CN(C)C=O.O=C(C=CC1=CC=CC=C1)C=CC1=CC=CC=C1.[Fe+2].[Na+].[Pd]", "output": "COC(=O)CC1=CC(Cl)=CC2=NC(C)=C(CC3=CC=C(Cl)C=C3)C(C)=C12", "task": "forward_synthesis", "split": "test", "original_reaction_smiles_with_atom_mapping": ["[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([CH3:21])=[C:7]([CH2:13][C:14]3[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=3)[C:8]([CH3:12])=[N:9]2)=[C:4](OS(C(F)(F)F)(=O)=O)[CH:3]=1.ClC1C=C(OS(C(F)(F)F)(=O)=O)C=C2C=1C(C)=C(CC1C=CC(Cl)=CC=1)C(C)=N2.C([Si]([O:66][C:67]([O:69][CH3:70])=[CH2:68])(C)C)(C)(C)C.C([O-])(=O)C.[Na+]>CN(C)C=O.C(OCC)(=O)C.[Pd].C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[CH3:70][O:69][C:67](=[O:66])[CH2:68][C:4]1[CH:3]=[C:2]([Cl:1])[CH:11]=[C:10]2[C:5]=1[C:6]([CH3:21])=[C:7]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=1)[C:8]([CH3:12])=[N:9]2"]}
  32. {"input": "CC(=O)[O-].CC1=CC=C(Cl)C=C1C1CC(=O)CC(=O)C1.CCO.[NH4+]", "output": "CC1=CC=C(Cl)C=C1C1CC(=O)C=C(N)C1", "task": "forward_synthesis", "split": "test", "original_reaction_smiles_with_atom_mapping": ["[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:16])=[C:6]([CH:8]2[CH2:13][C:12](=O)[CH2:11][C:10](=[O:15])[CH2:9]2)[CH:7]=1.C([O-])(=O)C.[NH4+:21]>C(O)C>[NH2:21][C:12]1[CH2:13][CH:8]([C:6]2[CH:7]=[C:2]([Cl:1])[CH:3]=[CH:4][C:5]=2[CH3:16])[CH2:9][C:10](=[O:15])[CH:11]=1"]}
  33. {"input": "CCC(=O)[O-].CCO.FC(F)(F)C1=CN=C2C(=C1)C=CN2CC1=CC=NC=C1.O.[K+].[OH-]", "output": "O=C(O)C1=CC2=CC(C(F)(F)F)=CN=C2N1CC1=CC=NC=C1", "task": "forward_synthesis", "split": "test", "original_reaction_smiles_with_atom_mapping": ["[OH-].[K+].[F:3][C:4]([F:22])([F:21])[C:5]1[CH:6]=[C:7]2[CH:13]=[CH:12][N:11]([CH2:14][C:15]3[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=3)[C:8]2=[N:9][CH:10]=1.CC[C:25]([O-:27])=[O:26]>O.C(O)C>[F:22][C:4]([F:21])([F:3])[C:5]1[CH:6]=[C:7]2[CH:13]=[C:12]([C:25]([OH:27])=[O:26])[N:11]([CH2:14][C:15]3[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=3)[C:8]2=[N:9][CH:10]=1"]}
  34. {"input": "CC(C)[N-]C(C)C.CI.CN(C)C=O.N#CC1=CC=C(C2NC(=O)N(C3=CC=CC(C(F)(F)F)=C3)C3=C2C(=O)CCC3)C=C1.O.[Li+]", "output": "CN1C(=O)N(C2=CC=CC(C(F)(F)F)=C2)C2=C(C(=O)CCC2)C1C1=CC=C(C#N)C=C1", "task": "forward_synthesis", "split": "test", "original_reaction_smiles_with_atom_mapping": ["[CH:1]([N-]C(C)C)(C)C.[Li+].[O:9]=[C:10]1[NH:19][CH:18]([C:20]2[CH:27]=[CH:26][C:23]([C:24]#[N:25])=[CH:22][CH:21]=2)[C:17]2[C:16](=[O:28])[CH2:15][CH2:14][CH2:13][C:12]=2[N:11]1[C:29]1[CH:34]=[CH:33][CH:32]=[C:31]([C:35]([F:38])([F:37])[F:36])[CH:30]=1.CI.O>CN(C)C=O>[F:37][C:35]([F:38])([F:36])[C:31]1[CH:30]=[C:29]([N:11]2[C:12]3[CH2:13][CH2:14][CH2:15][C:16](=[O:28])[C:17]=3[CH:18]([C:20]3[CH:21]=[CH:22][C:23]([C:24]#[N:25])=[CH:26][CH:27]=3)[N:19]([CH3:1])[C:10]2=[O:9])[CH:34]=[CH:33][CH:32]=1"]}
  35. {"input": "BrBr.CC(=O)O.O=CC1=CC(=O)C(OCC2=CC=CC=C2)=CN1", "output": "O=CC1=C(Br)C(=O)C(OCC2=CC=CC=C2)=CN1", "task": "forward_synthesis", "split": "test", "original_reaction_smiles_with_atom_mapping": ["[O:1]=[C:2]1[C:7]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:6][NH:5][C:4]([CH:16]=[O:17])=[CH:3]1.[Br:18]Br>CC(O)=O>[Br:18][C:3]1[C:2](=[O:1])[C:7]([O:8][CH2:9][C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)=[CH:6][NH:5][C:4]=1[CH:16]=[O:17]"]}
  36. {"input": "CC(C)(C)C1=CC(F)=C2C(=O)N(C3=CC=CC(N4C=C(C#N)C=N4)=C3)N=CC2=C1.CCO.O", "output": "CC(C)(C)C1=CC(F)=C2C(=O)N(C3=CC=CC(N4C=C(C(N)=O)C=N4)=C3)N=CC2=C1", "task": "forward_synthesis", "split": "test", "original_reaction_smiles_with_atom_mapping": ["[C:1]([C:5]1[CH:6]=[C:7]2[C:12](=[C:13]([F:15])[CH:14]=1)[C:11](=[O:16])[N:10]([C:17]1[CH:18]=[C:19]([N:23]3[CH:27]=[C:26]([C:28]#[N:29])[CH:25]=[N:24]3)[CH:20]=[CH:21][CH:22]=1)[N:9]=[CH:8]2)([CH3:4])([CH3:3])[CH3:2].C([OH:32])C>O>[C:1]([C:5]1[CH:6]=[C:7]2[C:12](=[C:13]([F:15])[CH:14]=1)[C:11](=[O:16])[N:10]([C:17]1[CH:18]=[C:19]([N:23]3[CH:27]=[C:26]([C:28]([NH2:29])=[O:32])[CH:25]=[N:24]3)[CH:20]=[CH:21][CH:22]=1)[N:9]=[CH:8]2)([CH3:4])([CH3:2])[CH3:3]"]}
  37. {"input": "C1=CC=NC=C1.C1CCOC1.CC1=CC(N)=CC(N2CCC3=CC=CC=C3C2)=N1.CCOC(=O)C(=O)Cl", "output": "CCOC(=O)C(=O)NC1=CC(C)=NC(N2CCC3=CC=CC=C3C2)=C1", "task": "forward_synthesis", "split": "test", "original_reaction_smiles_with_atom_mapping": ["Cl[C:2](=[O:8])[C:3]([O:5][CH2:6][CH3:7])=[O:4].[CH2:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH2:12][CH2:11][N:10]1[C:19]1[CH:24]=[C:23]([NH2:25])[CH:22]=[C:21]([CH3:26])[N:20]=1>C1COCC1.N1C=CC=CC=1>[CH2:6]([O:5][C:3](=[O:4])[C:2]([NH:25][C:23]1[CH:22]=[C:21]([CH3:26])[N:20]=[C:19]([N:10]2[CH2:11][CH2:12][C:13]3[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH2:9]2)[CH:24]=1)=[O:8])[CH3:7]"]}
  38. {"input": "CC(C)(C)OC(=O)N1CCC(C2=CC=C(OCCCOCC3=CC=CC=C3)C=C2)C(OCC2=CC=C3C=CC(CBr)=CC3=C2)C1.CN(C)CC1=CC=C2C=CC(COC3CN(C(=O)OC(C)(C)C)CCC3C3=CC=C(OCCCOCC4=CC=CC=C4)C=C3)=CC2=C1.OCCOC1CCCCO1", "output": "OCCOCC1=CC=C2C=CC(COC3CNCCC3C3=CC=C(OCCCOCC4=CC=CC=C4)C=C3)=CC2=C1", "task": "forward_synthesis", "split": "test", "original_reaction_smiles_with_atom_mapping": ["[CH2:1]([O:8][CH2:9][CH2:10][CH2:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([CH:19]2[CH2:24][CH2:23][N:22](C(OC(C)(C)C)=O)[CH2:21][CH:20]2[O:32][CH2:33][C:34]2[CH:43]=[CH:42]C3[C:36](=[CH:37]C(CBr)=CC=3)[CH:35]=2)=[CH:15][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O1[CH2:51][CH2:50][CH2:49][CH2:48][CH:47]1[O:52][CH2:53][CH2:54][OH:55].C(OCCCOC1C=CC(C2CCN(C(OC(C)(C)C)=O)CC2OCC2C=CC3C(=CC(CN(C)C)=CC=3)C=2)=CC=1)C1C=CC=CC=1>>[CH2:1]([O:8][CH2:9][CH2:10][CH2:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([CH:19]2[CH2:24][CH2:23][NH:22][CH2:21][CH:20]2[O:32][CH2:33][C:34]2[CH:35]=[C:36]3[C:51]([CH:50]=[CH:49][C:48]([CH2:47][O:52][CH2:53][CH2:54][OH:55])=[CH:37]3)=[CH:42][CH:43]=2)=[CH:15][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1"]}
  39. {"input": "CCOC(=O)N1CCC(Br)C(O[Si](C)(C)C(C)(C)C)C1.CCOC(=O)N1CCC(N=[N+]=[N-])C(O)C1", "output": "CCOC(=O)N1CCC(N=[N+]=[N-])C(O[Si](C)(C)C(C)(C)C)C1", "task": "forward_synthesis", "split": "test", "original_reaction_smiles_with_atom_mapping": ["[N:1]([CH:4]1[CH2:9][CH2:8][N:7]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH2:6][CH:5]1[OH:15])=[N+:2]=[N-:3].BrC1CCN(C(OCC)=O)CC1O[Si:29]([C:32]([CH3:35])([CH3:34])[CH3:33])([CH3:31])[CH3:30]>>[N:1]([CH:4]1[CH2:9][CH2:8][N:7]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH2:6][CH:5]1[O:15][Si:29]([C:32]([CH3:35])([CH3:34])[CH3:33])([CH3:31])[CH3:30])=[N+:2]=[N-:3]"]}
  40. {"input": "C1CC2=C(C1)O2.C1CCOC1.CC(=O)[O-].CC(C)O.CC(C)OP(OC(C)C)OC(C)C.CCCCCC.CN1CCCC1=NC1=NC=NC2=C1NC=N2.CN1CCCC1=O.CS(C)=O.NC1=NC=NC2=C1NC=N2.[Li]CCCC.[Pd+2]", "output": "CN1CCCC1=NC1=NC=NC2=C1N=CN2C1C=CC(O)C1", "task": "forward_synthesis", "split": "test", "original_reaction_smiles_with_atom_mapping": ["P(OC(C)C)(OC(C)C)OC(C)C.C([Li])CCC.CCCCCC.[CH3:25][N:26]1[CH2:30][CH2:29][CH2:28][C:27]1=[N:31][C:32]1[N:40]=[CH:39][N:38]=[C:37]2[C:33]=1[NH:34][CH:35]=[N:36]2.N1C(N)=C2C(N=CN2)=NC=1.[O:51]1[C:53]2[CH2:54][CH2:55][CH2:56][C:52]1=2>O1CCCC1.CC(O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.CN1CCCC1=O.CS(C)=O>[CH3:25][N:26]1[CH2:30][CH2:29][CH2:28][C:27]1=[N:31][C:32]1[N:40]=[CH:39][N:38]=[C:37]2[C:33]=1[N:34]=[CH:35][N:36]2[CH:55]1[CH2:56][CH:52]([OH:51])[CH:53]=[CH:54]1"]}
  41. {"input": "BrB(Br)Br.CCOC(=O)NC1COC2=CC=C(OC)C=C2C1CC1=CC=CC=C1.ClCCl.O=C([O-])O.[Na+]", "output": "CCOC(=O)NC1COC2=CC=C(O)C=C2C1CC1=CC=CC=C1", "task": "forward_synthesis", "split": "test", "original_reaction_smiles_with_atom_mapping": ["[CH2:1]([CH:8]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([O:18]C)[CH:16]=2)[O:11][CH2:10][CH:9]1[NH:20][C:21](=[O:25])[O:22][CH2:23][CH3:24])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.B(Br)(Br)Br.C(=O)([O-])O.[Na+]>C(Cl)Cl>[CH2:1]([CH:8]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([OH:18])[CH:16]=2)[O:11][CH2:10][CH:9]1[NH:20][C:21](=[O:25])[O:22][CH2:23][CH3:24])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1"]}
  42. {"input": "C1=CC=C([PH](C2=CC=CC=C2)(C2=CC=CC=C2)[Pd]([PH](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)([PH](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)[PH](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1COCCO1.CC1(C)OB(C2=CC=C3C(=O)OCC3=C2)OC1(C)C.COC1=CC=C(Br)C(OC)=C1OCC1CC1.O=C([O-])[O-].[Cs+]", "output": "COC1=CC=C(C2=CC=C3C(=O)OCC3=C2)C(OC)=C1OCC1CC1", "task": "forward_synthesis", "split": "test", "original_reaction_smiles_with_atom_mapping": ["CC1(C)C(C)(C)OB([C:9]2[CH:10]=[C:11]3[C:15](=[CH:16][CH:17]=2)[C:14](=[O:18])[O:13][CH2:12]3)O1.C(=O)([O-])[O-].[Cs+].[Cs+].Br[C:27]1[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[C:29]([O:35][CH2:36][CH:37]2[CH2:39][CH2:38]2)[C:28]=1[O:40][CH3:41]>O1CCOCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH:37]1([CH2:36][O:35][C:29]2[C:28]([O:40][CH3:41])=[C:27]([C:9]3[CH:10]=[C:11]4[C:15](=[CH:16][CH:17]=3)[C:14](=[O:18])[O:13][CH2:12]4)[CH:32]=[CH:31][C:30]=2[O:33][CH3:34])[CH2:38][CH2:39]1"]}
  43. {"input": "C1CCOC1.CCN(C(C)C)C(C)C.CN(C)C(ON1C(=O)CCC1=O)=[N+](C)C.F[B-](F)(F)F.O=C(O)CCCOC1=CC=C2NC(=O)OC(C#CC3CC3)(C(F)(F)F)C2=C1", "output": "O=C(CCCOC1=CC=C2NC(=O)OC(C#CC3CC3)(C(F)(F)F)C2=C1)ON1C(=O)CCC1=O", "task": "forward_synthesis", "split": "test", "original_reaction_smiles_with_atom_mapping": ["[CH:1]1([C:4]#[C:5][C:6]2([C:24]([F:27])([F:26])[F:25])[O:11][C:10](=[O:12])[NH:9][C:8]3[CH:13]=[CH:14][C:15]([O:17][CH2:18][CH2:19][CH2:20][C:21]([OH:23])=[O:22])=[CH:16][C:7]2=3)[CH2:3][CH2:2]1.C(N(CC)C(C)C)(C)C.[B-](F)(F)(F)F.CN(C(O[N:50]1[C:55](=[O:56])[CH2:54][CH2:53][C:51]1=[O:52])=[N+](C)C)C>C1COCC1>[O:52]=[C:51]1[CH2:53][CH2:54][C:55](=[O:56])[N:50]1[O:22][C:21](=[O:23])[CH2:20][CH2:19][CH2:18][O:17][C:15]1[CH:14]=[CH:13][C:8]2[NH:9][C:10](=[O:12])[O:11][C:6]([C:5]#[C:4][CH:1]3[CH2:3][CH2:2]3)([C:24]([F:27])([F:26])[F:25])[C:7]=2[CH:16]=1"]}
  44. {"input": "CO.ClCCl.O=C(CC1(C2=CC=CC=C2)CCC1)C1=CC=CC=N1.[BH4-].[Na+]", "output": "OC(CC1(C2=CC=CC=C2)CCC1)C1=CC=CC=N1", "task": "forward_synthesis", "split": "test", "original_reaction_smiles_with_atom_mapping": ["[C:1]1([C:7]2([CH2:11][C:12]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=3)=[O:13])[CH2:10][CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[BH4-].[Na+].ClCCl>ClCCl.CO>[C:1]1([C:7]2([CH2:11][CH:12]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=3)[OH:13])[CH2:10][CH2:9][CH2:8]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1"]}
  45. {"input": "CCOC(=O)C1=C(C)N=C(N2C=NNC2=O)S1.FC1(F)CC1CBr.FC1=CC=C(CBr)C=C1", "output": "CCOC(=O)C1=C(C)N=C(N2C=NN(CC3=CC=C(F)C=C3)C2=O)S1", "task": "forward_synthesis", "split": "test", "original_reaction_smiles_with_atom_mapping": ["BrCC1CC1(F)F.Br[CH2:9][C:10]1[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=1.[CH3:17][C:18]1[N:19]=[C:20]([N:28]2[C:32](=[O:33])[NH:31][N:30]=[CH:29]2)[S:21][C:22]=1[C:23]([O:25][CH2:26][CH3:27])=[O:24]>>[F:16][C:13]1[CH:14]=[CH:15][C:10]([CH2:9][N:31]2[C:32](=[O:33])[N:28]([C:20]3[S:21][C:22]([C:23]([O:25][CH2:26][CH3:27])=[O:24])=[C:18]([CH3:17])[N:19]=3)[CH:29]=[N:30]2)=[CH:11][CH:12]=1"]}
  46. {"input": "C=CC1=CC=NC=C1.CC(=O)[O-].CC1=CC=CC=C1P(C1=CC=CC=C1C)C1=CC=CC=C1C.CCN(CC)CC.CN(C)C=O.COC1=CC=CC=C1CNC1=CC=C2C=C(Br)C=CC2=N1.O.[Pd+2]", "output": "COC1=CC=CC=C1CNC1=CC=C2C=C(/C=C/C3=CC=NC=C3)C=CC2=N1", "task": "forward_synthesis", "split": "test", "original_reaction_smiles_with_atom_mapping": ["Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([NH:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[O:20][CH3:21])[CH:6]=[CH:5]2.[CH:22]([C:24]1[CH:29]=[CH:28][N:27]=[CH:26][CH:25]=1)=[CH2:23].C(N(CC)CC)C.C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C>CN(C)C=O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O>[CH3:21][O:20][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=1[CH2:13][NH:12][C:7]1[CH:6]=[CH:5][C:4]2[C:9](=[CH:10][CH:11]=[C:2](/[CH:23]=[CH:22]/[C:24]3[CH:29]=[CH:28][N:27]=[CH:26][CH:25]=3)[CH:3]=2)[N:8]=1"]}
  47. {"input": "C1CCOC1.CO.ClCCl.O=C(C1=CC=C(C2=CC=NC=C2)C=C1)N1CCN(S(=O)(=O)C2=CC3=CC=C(Cl)C=C3N2S(=O)(=O)C2=CC=CC=C2)CC1.O=C([O-])O.[Cl-].[K+].[NH4+].[Na+].[OH-]", "output": "O=C(C1=CC=C(C2=CC=NC=C2)C=C1)N1CCN(S(=O)(=O)C2=CC3=CC=C(Cl)C=C3N2)CC1", "task": "forward_synthesis", "split": "test", "original_reaction_smiles_with_atom_mapping": ["C1(S([N:10]2[C:18]3[C:13](=[CH:14][CH:15]=[C:16]([Cl:19])[CH:17]=3)[CH:12]=[C:11]2[S:20]([N:23]2[CH2:28][CH2:27][N:26]([C:29](=[O:42])[C:30]3[CH:35]=[CH:34][C:33]([C:36]4[CH:41]=[CH:40][N:39]=[CH:38][CH:37]=4)=[CH:32][CH:31]=3)[CH2:25][CH2:24]2)(=[O:22])=[O:21])(=O)=O)C=CC=CC=1.[OH-].[K+].[Cl-].[NH4+].C(=O)(O)[O-].[Na+]>O1CCCC1.ClCCl.CO>[Cl:19][C:16]1[CH:17]=[C:18]2[C:13]([CH:12]=[C:11]([S:20]([N:23]3[CH2:28][CH2:27][N:26]([C:29](=[O:42])[C:30]4[CH:31]=[CH:32][C:33]([C:36]5[CH:41]=[CH:40][N:39]=[CH:38][CH:37]=5)=[CH:34][CH:35]=4)[CH2:25][CH2:24]3)(=[O:22])=[O:21])[NH:10]2)=[CH:14][CH:15]=1"]}
  48. {"input": "BrBr.CC(=O)O.CC(=O)[O-].COC1=CC=C(N)C=N1.[Na+].[OH-]", "output": "COC1=CC=C(N)C(Br)=N1", "task": "forward_synthesis", "split": "test", "original_reaction_smiles_with_atom_mapping": ["[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH2:9])=[CH:5][N:4]=1.C([O-])(=O)C.[Na+].[Br:15]Br.[OH-].[Na+]>C(O)(=O)C>[NH2:9][C:6]1[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[N:4][C:5]=1[Br:15]"]}
  49. {"input": "CN1CCC2=C(N)C=CC=C2C1.COC1=CC=C(C(=O)Cl)C(OC)=C1", "output": "COC1=CC=C(C(=O)NC2=CC=CC3=C2CCN(C)C3)C(OC)=C1.Cl", "task": "forward_synthesis", "split": "test", "original_reaction_smiles_with_atom_mapping": ["[NH2:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][N:6]([CH3:12])[CH2:7]2.[CH3:13][O:14][C:15]1[CH:23]=[C:22]([O:24][CH3:25])[CH:21]=[CH:20][C:16]=1[C:17]([Cl:19])=[O:18]>>[ClH:19].[CH3:12][N:6]1[CH2:5][CH2:4][C:3]2[C:8](=[CH:9][CH:10]=[CH:11][C:2]=2[NH:1][C:17](=[O:18])[C:16]2[CH:20]=[CH:21][C:22]([O:24][CH3:25])=[CH:23][C:15]=2[O:14][CH3:13])[CH2:7]1"]}
  50. {"input": "CCC1=CC=CC(N)=C1.CCOCC.N#CBr", "output": "CCC1=CC=CC(NC#N)=C1", "task": "forward_synthesis", "split": "test", "original_reaction_smiles_with_atom_mapping": ["[N:1]#[C:2]Br.[CH2:4]([C:6]1[CH:7]=[C:8]([CH:10]=[CH:11][CH:12]=1)[NH2:9])[CH3:5]>CCOCC>[CH2:4]([C:6]1[CH:7]=[C:8]([NH:9][C:2]#[N:1])[CH:10]=[CH:11][CH:12]=1)[CH3:5]", "[N:1]#[C:2]Br.[CH2:4]([C:6]1[CH:7]=[C:8]([CH:10]=[CH:11][CH:12]=1)[NH2:9])[CH3:5]>C(OCC)C>[CH2:4]([C:6]1[CH:7]=[C:8]([NH:9][C:2]#[N:1])[CH:10]=[CH:11][CH:12]=1)[CH3:5]"]}
  51. {"input": "CC(C)=O.CCCCCCCCCCCCNC(=N)NC(=N)NCC1=CC=C(S(N)(=O)=O)C=C1.CO.Cl", "output": "CCCCCCCCCCCCNC1=NC(C)(C)N=C(NCC2=CC=C(S(N)(=O)=O)C=C2)N1", "task": "forward_synthesis", "split": "test", "original_reaction_smiles_with_atom_mapping": ["CO.Cl.Cl.Cl.[S:6]([C:10]1[CH:35]=[CH:34][C:13]([CH2:14][NH:15][C:16]([NH:18][C:19]([NH:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])=[NH:20])=[NH:17])=[CH:12][CH:11]=1)(=[O:9])(=[O:8])[NH2:7].[CH3:36][C:37]([CH3:39])=O>>[CH3:36][C:37]1([CH3:39])[N:17]=[C:16]([NH:15][CH2:14][C:13]2[CH:12]=[CH:11][C:10]([S:6](=[O:8])(=[O:9])[NH2:7])=[CH:35][CH:34]=2)[NH:18][C:19]([NH:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])=[N:20]1"]}
  52. {"input": "BrB(Br)Br.COC1=CC=CC2=C1C(CC(N)=O)=CN2CC1=CC=CC=C1", "output": "NC(=O)CC1=CN(CC2=CC=CC=C2)C2=CC=CC(O)=C12", "task": "forward_synthesis", "split": "test", "original_reaction_smiles_with_atom_mapping": ["C[O:2][C:3]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:4]=1[C:5]([CH2:19][C:20]([NH2:22])=[O:21])=[CH:6][N:7]2[CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.B(Br)(Br)Br>>[OH:2][C:3]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:4]=1[C:5]([CH2:19][C:20]([NH2:22])=[O:21])=[CH:6][N:7]2[CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1"]}
  53.  
  54.  
  55. /home/xie.zhongwei/workspace/data/SMolInstruct/raw/test/retrosynthesis.jsonl
  56.  
  57. {"input": "CN1CC2CN(C3=CC=C4C(=C3)[C@@H]3C[C@H]4OCC=CCCCC(=O)N[C@@H](CC4=CC(F)=CC(F)=C4)[C@H](O)CN3)CC2C1", "output": "CN1CC2CNCC2C1.O=C1CCCC=CCO[C@@H]2C[C@H](NC[C@@H](O)[C@H](CC3=CC(F)=CC(F)=C3)N1)C1=CC(Br)=CC=C12", "task": "retrosynthesis", "split": "test", "original_reaction_smiles_with_atom_mapping": ["Br[c:31]1[cH:32][cH:33][c:34]2[c:50]([cH:51]1)[C@H:49]1[NH:48][CH2:47][C@@H:46]([OH:53])[C@H:45]([CH2:54][c:55]3[cH:56][c:57]([F:62])[cH:58][c:59]([F:61])[cH:60]3)[NH:44][C:43](=[O:63])[CH2:42][CH2:41][CH2:40][CH:39]=[CH:38][CH2:37][O:36][C@@H:35]2[CH2:52]1.[CH3:64][N:65]1[CH2:66][CH:67]2[CH2:68][NH:69][CH2:70][CH:71]2[CH2:72]1>C=CCO[C@@H]1C[C@H](NC[C@@H](O)[C@@H](N)Cc2cc(F)cc(F)c2)c2cc(Br)ccc21>[c:31]1([N:69]2[CH2:68][CH:67]3[CH2:66][N:65]([CH3:64])[CH2:72][CH:71]3[CH2:70]2)[cH:32][cH:33][c:34]2[c:50]([cH:51]1)[C@H:49]1[NH:48][CH2:47][C@@H:46]([OH:53])[C@H:45]([CH2:54][c:55]3[cH:56][c:57]([F:62])[cH:58][c:59]([F:61])[cH:60]3)[NH:44][C:43](=[O:63])[CH2:42][CH2:41][CH2:40][CH:39]=[CH:38][CH2:37][O:36][C@@H:35]2[CH2:52]1"]}
  58. {"input": "CCOC(=O)C1=C(C(C)C)N(C2=CC=CC=C2F)N=N1", "output": "CCOC(=O)CC(=O)C(C)C.[N-]=[N+]=NC1=CC=CC=C1F", "task": "retrosynthesis", "split": "test", "original_reaction_smiles_with_atom_mapping": ["O=[C:12]([CH:13]([CH3:14])[CH3:15])[CH2:17][C:18](=[O:19])[O:20][CH2:21][CH3:22].[N:23](=[N+:24]=[N-:25])[c:26]1[c:27]([F:32])[cH:28][cH:29][cH:30][cH:31]1>CN(C=O)C.C1CCC2=NCCCN2CC1.O>[c:12]1([CH:13]([CH3:14])[CH3:15])[c:17]([C:18](=[O:19])[O:20][CH2:21][CH3:22])[n:25][n:24][n:23]1-[c:26]1[c:27]([F:32])[cH:28][cH:29][cH:30][cH:31]1"]}
  59. {"input": "CC[C@H]1[C@@H](O)C(F)(F)C(=O)N1C1=CC=C(C#N)C(Cl)=C1", "output": "CC[C@@H]1NC(=O)C(F)(F)[C@@H]1O.N#CC1=CC=C(Br)C=C1Cl", "task": "retrosynthesis", "split": "test", "original_reaction_smiles_with_atom_mapping": ["Br[c:2]1[cH:3][c:4]([Cl:10])[c:5]([C:6]#[N:7])[cH:8][cH:9]1.[CH2:11]([CH3:12])[C@H:13]1[C@@H:14]([OH:21])[C:15]([F:19])([F:20])[C:16](=[O:18])[NH:17]1>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].CC1(C)c2cccc(P(c3ccccc3)c3ccccc3)c2Oc2c(P(c3ccccc3)c3ccccc3)cccc21.O=C([O-])[O-].[Cs+].[Cs+]>[c:2]1([N:17]2[C@@H:13]([CH2:11][CH3:12])[C@@H:14]([OH:21])[C:15]([F:19])([F:20])[C:16]2=[O:18])[cH:3][c:4]([Cl:10])[c:5]([C:6]#[N:7])[cH:8][cH:9]1"]}
  60. {"input": "CC[Si](CC)(CC)OC(C)(C)C1=NC2=NC=C(Br)N2C=C1", "output": "CC(C)(O)C1=NC2=NC=C(Br)N2C=C1.CC[Si](CC)(CC)OS(=O)(=O)C(F)(F)F", "task": "retrosynthesis", "split": "test", "original_reaction_smiles_with_atom_mapping": ["O=S(=O)(C(F)(F)F)[O:6][Si:7]([CH2:8][CH3:9])([CH2:10][CH3:11])[CH2:12][CH3:13].O[C:26]([c:24]1[cH:23][cH:22][n:21]2[c:17]([Br:16])[cH:18][n:19][c:20]2[n:25]1)([CH3:27])[CH3:28]>ClCCl.CCN(C(C)C)C(C)C>[O:6]([Si:7]([CH2:8][CH3:9])([CH2:10][CH3:11])[CH2:12][CH3:13])[C:26]([c:24]1[cH:23][cH:22][n:21]2[c:17]([Br:16])[cH:18][n:19][c:20]2[n:25]1)([CH3:27])[CH3:28]"]}
  61. {"input": "COC1=CC=CC=C1C(OCCN(C)C)C1=CC=C(NC(=O)C2(C3=CC=C4OCOC4=C3)CC2)N=C1", "output": "CN(C)CCO.COC1=CC=CC=C1C(O)C1=CC=C(NC(=O)C2(C3=CC=C4OCOC4=C3)CC2)N=C1", "task": "retrosynthesis", "split": "test", "original_reaction_smiles_with_atom_mapping": ["[O:1]1[CH2:2][O:3][c:4]2[c:5]1[cH:6][cH:7][c:8]([C:10]1([C:13](=[O:14])[NH:15][c:16]3[n:17][cH:18][c:19]([CH:22]([c:23]4[c:24]([O:29][CH3:30])[cH:25][cH:26][cH:27][cH:28]4)[OH:31])[cH:20][cH:21]3)[CH2:11][CH2:12]1)[cH:9]2.O[CH2:35][CH2:34][N:33]([CH3:32])[CH3:37]>COc1ccccc1C(OCCCO)c1ccc(NC(=O)C2(c3ccc4c(c3)OCO4)CC2)nc1>[O:1]1[CH2:2][O:3][c:4]2[c:5]1[cH:6][cH:7][c:8]([C:10]1([C:13](=[O:14])[NH:15][c:16]3[n:17][cH:18][c:19]([CH:22]([c:23]4[c:24]([O:29][CH3:30])[cH:25][cH:26][cH:27][cH:28]4)[O:31][CH2:35][CH2:34][N:33]([CH3:32])[CH3:37])[cH:20][cH:21]3)[CH2:11][CH2:12]1)[cH:9]2", "[O:1]1[CH2:2][O:3][c:4]2[c:5]1[cH:6][cH:7][c:8]([C:10]1([C:13](=[O:14])[NH:15][c:16]3[n:17][cH:18][c:19]([CH:22]([c:23]4[c:24]([O:29][CH3:30])[cH:25][cH:26][cH:27][cH:28]4)[OH:31])[cH:20][cH:21]3)[CH2:11][CH2:12]1)[cH:9]2.O[CH2:35][CH2:34][N:33]([CH3:32])[CH3:37]>COc1ccccc1C(OCC(C)O)c1ccc(NC(=O)C2(c3ccc4c(c3)OCO4)CC2)nc1>[O:1]1[CH2:2][O:3][c:4]2[c:5]1[cH:6][cH:7][c:8]([C:10]1([C:13](=[O:14])[NH:15][c:16]3[n:17][cH:18][c:19]([CH:22]([c:23]4[c:24]([O:29][CH3:30])[cH:25][cH:26][cH:27][cH:28]4)[O:31][CH2:35][CH2:34][N:33]([CH3:32])[CH3:37])[cH:20][cH:21]3)[CH2:11][CH2:12]1)[cH:9]2"]}
  62. {"input": "CC1=CC(CCl)=CC(C)=N1", "output": "CC1=CC(CO)=CC(C)=N1.O=S(Cl)Cl", "task": "retrosynthesis", "split": "test", "original_reaction_smiles_with_atom_mapping": ["O[CH2:8][c:6]1[cH:5][c:4]([CH3:10])[n:3][c:2]([CH3:1])[cH:7]1.O=S(Cl)[Cl:17]>CN(C=O)C.ClCCCl>[CH3:1][c:2]1[n:3][c:4]([CH3:10])[cH:5][c:6]([CH2:8][Cl:17])[cH:7]1", "[CH3:1][C:2]1[CH:7]=[C:6]([CH2:8]O)[CH:5]=[C:4]([CH3:10])[N:3]=1.S(Cl)([Cl:13])=O>C(Cl)(Cl)Cl>[CH3:1][c:2]1[n:3][c:4]([CH3:10])[cH:5][c:6]([CH2:8][Cl:13])[cH:7]1"]}
  63. {"input": "CC1=CC=NC=C1C1=CN=C2C(=C1)C(C1=NC3=CC=NC=C3N1)=NN2C1CCCCO1", "output": "CC1=CC=NC=C1C1=CN=C2C(=C1)C(C=O)=NN2C1CCCCO1.NC1=CC=NC=C1N", "task": "retrosynthesis", "split": "test", "original_reaction_smiles_with_atom_mapping": ["O=[CH:17][c:16]1[c:10]2[cH:9][c:8](-[c:3]3[c:2]([CH3:1])[cH:7][cH:6][n:5][cH:4]3)[cH:13][n:12][c:11]2[n:14]([CH:19]2[O:20][CH2:21][CH2:22][CH2:23][CH2:24]2)[n:15]1.[NH2:25][c:26]1[cH:27][n:28][cH:29][cH:30][c:31]1[NH2:32]>CN(C=O)C.[S]>[CH3:1][c:2]1[c:3](-[c:8]2[cH:9][c:10]3[c:11]([n:12][cH:13]2)[n:14]([CH:19]2[O:20][CH2:21][CH2:22][CH2:23][CH2:24]2)[n:15][c:16]3-[c:17]2[nH:25][c:26]3[cH:27][n:28][cH:29][cH:30][c:31]3[n:32]2)[cH:4][n:5][cH:6][cH:7]1"]}
  64. {"input": "COC1=CC=C(N2C(CO)=CC3=C(SC=C3)S2(=O)=O)C=C1", "output": "COC(=O)C1=CC2=C(SC=C2)S(=O)(=O)N1C1=CC=C(OC)C=C1", "task": "retrosynthesis", "split": "test", "original_reaction_smiles_with_atom_mapping": ["CO[C:24]([C:23]1=[CH:22][c:21]2[c:20]([s:30][cH:29][cH:28]2)[S:19](=[O:31])(=[O:32])[N:18]1[c:15]1[cH:14][cH:13][c:12]([O:11][CH3:10])[cH:17][cH:16]1)=[O:25]>C1COCC1.CC(C)C[AlH]CC(C)C>[CH3:10][O:11][c:12]1[cH:13][cH:14][c:15]([N:18]2[S:19](=[O:31])(=[O:32])[c:20]3[c:21]([cH:28][cH:29][s:30]3)[CH:22]=[C:23]2[CH2:24][OH:25])[cH:16][cH:17]1"]}
  65. {"input": "O=C1CC(C2=CC=CC(Cl)=C2)C2(C(=O)NC3=CC(Cl)=CC=C32)C(C2=CC=CC=C2Cl)N1", "output": "CCOC(=O)N1C(=O)C2(C3=CC=C(Cl)C=C31)C(C1=CC=CC(Cl)=C1)CC(=O)NC2C1=CC=CC=C1Cl", "task": "retrosynthesis", "split": "test", "original_reaction_smiles_with_atom_mapping": ["CCOC(=O)[N:6]1[C:7](=[O:36])[C:8]2([CH:9]([c:22]3[c:23]([Cl:28])[cH:24][cH:25][cH:26][cH:27]3)[NH:10][C:11](=[O:21])[CH2:12][CH:13]2[c:14]2[cH:15][c:16]([Cl:20])[cH:17][cH:18][cH:19]2)[c:29]2[cH:30][cH:31][c:32]([Cl:35])[cH:33][c:34]21>CO.[OH-].[Na+]>[NH:6]1[C:7](=[O:36])[C:8]2([CH:9]([c:22]3[c:23]([Cl:28])[cH:24][cH:25][cH:26][cH:27]3)[NH:10][C:11](=[O:21])[CH2:12][CH:13]2[c:14]2[cH:15][c:16]([Cl:20])[cH:17][cH:18][cH:19]2)[c:29]2[cH:30][cH:31][c:32]([Cl:35])[cH:33][c:34]21"]}
  66. {"input": "CC(C)[C@@H](C(=O)N[C@@H](C)C(=O)N1CCC[C@@H](C(=O)OCC(Cl)(Cl)Cl)N1)N(C)C(=O)OC(C)(C)C", "output": "CC(C)[C@@H](C(=O)O)N(C)C(=O)OC(C)(C)C.C[C@H](N)C(=O)N1CCC[C@@H](C(=O)OCC(Cl)(Cl)Cl)N1", "task": "retrosynthesis", "split": "test", "original_reaction_smiles_with_atom_mapping": ["[Cl:1][C:2]([CH2:3][O:4][C:5](=[O:6])[C@H:7]1[NH:8][N:9]([C:13]([C@H:14]([CH3:15])[NH2:16])=[O:17])[CH2:10][CH2:11][CH2:12]1)([Cl:18])[Cl:19].O[C:29]([C@@H:28]([N:27]([C:25]([O:24][C:20]([CH3:21])([CH3:22])[CH3:23])=[O:26])[CH3:35])[CH:32]([CH3:33])[CH3:34])=[O:30]>C(#N)C.CCN(C(C)C)C(C)C.C[NH3+].F[P-](F)(F)(F)(F)F.CN(C)C(On1nnc2cccnc21)=[N+](C)C.F[P-](F)(F)(F)(F)F>[Cl:1][C:2]([CH2:3][O:4][C:5](=[O:6])[C@H:7]1[NH:8][N:9]([C:13]([C@H:14]([CH3:15])[NH:16][C:29]([C@@H:28]([N:27]([C:25]([O:24][C:20]([CH3:21])([CH3:22])[CH3:23])=[O:26])[CH3:35])[CH:32]([CH3:33])[CH3:34])=[O:30])=[O:17])[CH2:10][CH2:11][CH2:12]1)([Cl:18])[Cl:19]"]}
  67. {"input": "COCOC1=C(C)C=C(/C=C/C2=CC=CC(C(=O)SC3=CC=CC=C3)=C2)C=C1C", "output": "COCOC1=C(C)C=C(/C=C/C2=CC=CC(C(=O)O)=C2)C=C1C.SC1=CC=CC=C1", "task": "retrosynthesis", "split": "test", "original_reaction_smiles_with_atom_mapping": ["O=[C:14]([c:13]1[cH:12][c:11](/[CH:10]=[CH:9]/[c:8]2[cH:7][c:6]([CH3:23])[c:5]([O:4][CH2:3][O:2][CH3:1])[c:21]([CH3:22])[cH:20]2)[cH:19][cH:18][cH:17]1)[OH:16].[c:39]1([SH:45])[cH:40][cH:41][cH:42][cH:43][cH:44]1>C(Cl)Cl.CN(C1C=CN=CC=1)C.C(=NC1CCCCC1)=NC1CCCCC1>[CH3:1][O:2][CH2:3][O:4][c:5]1[c:6]([CH3:23])[cH:7][c:8](/[CH:9]=[CH:10]/[c:11]2[cH:12][c:13]([C:14](=[O:16])[S:45][c:39]3[cH:40][cH:41][cH:42][cH:43][cH:44]3)[cH:17][cH:18][cH:19]2)[cH:20][c:21]1[CH3:22]"]}
  68. {"input": "CC1(C)S[C@@H]2C(N)C(=O)N2C1C1=NN=NN1", "output": "CC1(C)S[C@@H]2C(NC(C3=CC=CC=C3)(C3=CC=CC=C3)C3=CC=CC=C3)C(=O)N2C1C1=NN=NN1", "task": "retrosynthesis", "split": "test", "original_reaction_smiles_with_atom_mapping": ["c1ccc(C(c2ccccc2)(c2ccccc2)[NH:24][CH:25]2[C@@H:26]3[N:27]([CH:28]([c:33]4[n:34][n:35][n:36][nH:37]4)[C:29]([CH3:31])([CH3:32])[S:30]3)[C:38]2=[O:39])cc1>CCOCC.CC(C)=O.O.Cc1ccc(S(=O)(=O)O)cc1>[NH2:24][CH:25]1[C@@H:26]2[N:27]([CH:28]([c:33]3[nH:34][n:35][n:36][n:37]3)[C:29]([CH3:31])([CH3:32])[S:30]2)[C:38]1=[O:39]"]}
  69. {"input": "CCOC(=O)CC1=CC=C(C2=C(C)C=C(C(CC)(CC)C3=CC=C(/C=C/C(O)(CC)CC)C(C)=C3)C=C2C)N=C1", "output": "CCC(O)(/C=C/C1=CC=C(C(CC)(CC)C2=CC(C)=C(B3OC(C)(C)C(C)(C)O3)C(C)=C2)C=C1C)CC.CCOC(=O)CC1=CC=C(Cl)N=C1", "task": "retrosynthesis", "split": "test", "original_reaction_smiles_with_atom_mapping": ["Cl[c:9]1[n:8][cH:7][c:6]([CH2:5][C:4]([O:3][CH2:1][CH3:2])=[O:13])[cH:11][cH:10]1.CC1(C)OB([c:28]2[c:23]([CH3:22])[cH:24][c:25]([C:39]([CH2:40][CH3:41])([CH2:42][CH3:43])[c:44]3[cH:45][c:46]([CH3:58])[c:47](/[CH:50]=[CH:51]/[C:52]([CH2:53][CH3:54])([OH:55])[CH2:56][CH3:57])[cH:48][cH:49]3)[cH:26][c:27]2[CH3:38])OC1(C)C>CN(C)C=O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O=P([O-])([O-])[O-].[K+].[K+].[K+].CCOC(C)=O>[CH2:1]([CH3:2])[O:3][C:4]([CH2:5][c:6]1[cH:7][n:8][c:9](-[c:28]2[c:23]([CH3:22])[cH:24][c:25]([C:39]([CH2:40][CH3:41])([CH2:42][CH3:43])[c:44]3[cH:45][c:46]([CH3:58])[c:47](/[CH:50]=[CH:51]/[C:52]([CH2:53][CH3:54])([OH:55])[CH2:56][CH3:57])[cH:48][cH:49]3)[cH:26][c:27]2[CH3:38])[cH:10][cH:11]1)=[O:13]"]}
  70. {"input": "O=C(O)COCCCCCCC(F)(F)C(F)(F)F", "output": "CCOC(=O)CBr.OCCCCCCC(F)(F)C(F)(F)F", "task": "retrosynthesis", "split": "test", "original_reaction_smiles_with_atom_mapping": ["[F:1][C:2]([C:3]([F:4])([F:5])[F:6])([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][OH:13])[F:14].CC[O:21][C:19]([CH2:18]Br)=[O:20]>O1CCCC1.[Na+]>[F:1][C:2]([C:3]([F:4])([F:5])[F:6])([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][O:13][CH2:18][C:19](=[O:20])[OH:21])[F:14]"]}
  71. {"input": "COC(=O)C(C)(C)[C@H]1CCCN(C)C1", "output": "COC(=O)C(C)(C)C1CCCNC1.O=CO", "task": "retrosynthesis", "split": "test", "original_reaction_smiles_with_atom_mapping": ["[CH3:2][O:3][C:4]([C:5]([CH3:6])([CH:7]1[CH2:8][NH:9][CH2:10][CH2:11][CH2:12]1)[CH3:13])=[O:14].O=[CH:15]O>[OH-].[Na+].Cl.C=O>[CH3:2][O:3][C:4]([C:5]([CH3:6])([C@@H:7]1[CH2:8][N:9]([CH3:15])[CH2:10][CH2:11][CH2:12]1)[CH3:13])=[O:14]"]}
  72. {"input": "COC(=O)C(C)(C)C1CCCN(C)C1", "output": "COC(=O)C(C)(C)C1CCCNC1.O=CO", "task": "retrosynthesis", "split": "test", "original_reaction_smiles_with_atom_mapping": ["[CH3:2][O:3][C:4]([C:5]([CH3:6])([CH:7]1[CH2:8][NH:9][CH2:10][CH2:11][CH2:12]1)[CH3:13])=[O:14].O=[CH:15]O>[OH-].[Na+].Cl.C=O>[CH3:2][O:3][C:4]([C:5]([CH3:6])([CH:7]1[CH2:8][N:9]([CH3:15])[CH2:10][CH2:11][CH2:12]1)[CH3:13])=[O:14]"]}
  73. {"input": "CN(C)OC(=O)C1=C(O)C=CC=C1Cl", "output": "CN(C)O.O=C(O)C1=C(O)C=CC=C1Cl", "task": "retrosynthesis", "split": "test", "original_reaction_smiles_with_atom_mapping": ["[Cl:1][c:2]1[cH:3][cH:4][cH:5][c:6]([OH:11])[c:7]1[C:8](=[O:9])[OH:10].O[N:14]([CH3:13])[CH3:16]>O1CCCC1.Cl.CCN(CC)CC.O>[Cl:1][c:2]1[cH:3][cH:4][cH:5][c:6]([OH:11])[c:7]1[C:8](=[O:9])[O:10][N:14]([CH3:13])[CH3:16]"]}
  74. {"input": "CC1=NN2C=C(C#CC3=CC=CC=C3F)C=NC2=C1", "output": "C#CC1=CC=CC=C1F.CC1=NN2C=C(Br)C=NC2=C1", "task": "retrosynthesis", "split": "test", "original_reaction_smiles_with_atom_mapping": ["Br[C:2]1[CH:3]=[N:4][C:5]2[N:6]([N:8]=[C:9]([CH3:11])[CH:10]=2)[CH:7]=1.[C:12]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[F:20])#[CH:13]>>[c:2]1([C:13]#[C:12][c:14]2[c:15]([F:20])[cH:16][cH:17][cH:18][cH:19]2)[cH:3][n:4][c:5]2[n:6]([cH:7]1)[n:8][c:9]([CH3:11])[cH:10]2"]}
  75. {"input": "FC1(C2=CC=C3CNCC3=C2)COC1", "output": "CCN(CC)S(F)(F)F.OC1(C2=CC=C3CNCC3=C2)COC1", "task": "retrosynthesis", "split": "test", "original_reaction_smiles_with_atom_mapping": ["[CH2:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10]3(O)[CH2:13][O:12][CH2:11]3)=[CH:7][CH:8]=2)[CH2:3][NH:2]1.C(N(S(F)(F)[F:21])CC)C>C(#N)C.[N+](C)([O-])=O>[CH2:1]1[NH:2][CH2:3][c:4]2[cH:5][c:6]([C:10]3([F:21])[CH2:11][O:12][CH2:13]3)[cH:7][cH:8][c:9]21"]}
  76. {"input": "O=C(O)C1=CC=C2C(=C1)N=C(C1=CC=C3N=C(CCN4C=CC=N4)C=CC3=C1)N2C1CCCCC1", "output": "CC(=O)CCN1C=CC=N1.O=C(O)C1=CC=C2C(=C1)N=C(C1=CC=C3N=C(C4=CC(Br)=CC=C4O)C=CC3=C1)N2C1CCCCC1", "task": "retrosynthesis", "split": "test", "original_reaction_smiles_with_atom_mapping": ["Oc1ccc(Br)[cH:7][c:6]1-[c:8]1[n:9][c:10]2[cH:11][cH:12][c:13](-[c:18]3[n:19][c:20]4[c:21]([n:22]3[CH:23]3[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28]3)[cH:29][cH:30][c:31]([C:33](=[O:34])[OH:35])[cH:32]4)[cH:14][c:15]2[cH:16][cH:17]1.CC(=O)CC[n:37]1[n:38][cH:39][cH:40][cH:41]1>C(O)C.[OH-].[K+]>[cH:6]1[cH:7][c:11]2[c:10]([n:9][c:8]1[CH2:17][CH2:16][n:37]1[n:38][cH:39][cH:40][cH:41]1)[cH:15][cH:14][c:13](-[c:18]1[n:19][c:20]3[c:21]([n:22]1[CH:23]1[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28]1)[cH:29][cH:30][c:31]([C:33](=[O:34])[OH:35])[cH:32]3)[cH:12]2"]}
  77. {"input": "O=C(N[C@H](CC1=CC=C(C2=CC=CC=C2)C=C1)C[C@@H](CO)C(=O)O)C1=NC(Cl)=NN1", "output": "CCOC(=O)[C@H](CO)C[C@@H](CC1=CC=C(C2=CC=CC=C2)C=C1)NC(=O)OC(C)(C)C.O=C(O)C1=NC(Cl)=NN1", "task": "retrosynthesis", "split": "test", "original_reaction_smiles_with_atom_mapping": ["O=[C:7]([c:4]1[n:3][c:2]([Cl:1])[n:6][nH:5]1)[OH:9].CC[O:36][C:37]([C@@H:38]([CH2:39][C@@H:40]([CH2:41][c:42]1[cH:43][cH:44][c:45](-[c:48]2[cH:49][cH:50][cH:51][cH:52][cH:53]2)[cH:46][cH:47]1)[NH:54]C(=O)OC(C)(C)C)[CH2:62][OH:63])=[O:64]>CN(C=O)C.CC#N.CN(C)C(On1nnc2cccnc21)=[N+](C)C.F[P-](F)(F)(F)(F)F.Cl.C1COCCO1>[Cl:1][c:2]1[n:3][c:4]([C:7](=[O:9])[NH:54][C@@H:40]([CH2:39][C@H:38]([C:37](=[O:36])[OH:64])[CH2:62][OH:63])[CH2:41][c:42]2[cH:43][cH:44][c:45](-[c:48]3[cH:49][cH:50][cH:51][cH:52][cH:53]3)[cH:46][cH:47]2)[nH:5][n:6]1"]}
  78. {"input": "O=[N+]([O-])C1=CC=CC(CC2=COC=C2)=C1", "output": "O=[N+]([O-])C1=CC=CC(CBr)=C1.OB(O)C1=COC=C1", "task": "retrosynthesis", "split": "test", "original_reaction_smiles_with_atom_mapping": ["[O:1]1[CH:5]=[CH:4][C:3](B(O)O)=[CH:2]1.[N+:9]([C:12]1[CH:13]=[C:14]([CH:17]=[CH:18][CH:19]=1)[CH2:15]Br)([O-:11])=[O:10]>>[o:1]1[cH:2][c:3]([CH2:15][c:14]2[cH:13][c:12]([N+:9](=[O:10])[O-:11])[cH:19][cH:18][cH:17]2)[cH:4][cH:5]1"]}
  79. {"input": "O=C(O)CNC1=CC=C(Br)C=C1C(=O)O", "output": "NC1=CC=C(Br)C=C1C(=O)O.O=C(O)CCl", "task": "retrosynthesis", "split": "test", "original_reaction_smiles_with_atom_mapping": ["[NH2:1][c:2]1[c:3]([C:4](=[O:5])[OH:6])[cH:7][c:8]([Br:11])[cH:9][cH:10]1.Cl[CH2:13][C:14](=[O:15])[OH:16]>C([O-])([O-])=O.[Na+].[Na+].CCOCC.Cl>[NH:1]([c:2]1[c:3]([C:4](=[O:5])[OH:6])[cH:7][c:8]([Br:11])[cH:9][cH:10]1)[CH2:13][C:14](=[O:15])[OH:16]"]}
  80. {"input": "CCOC(=O)C1=CC(C2CC2)=NC2=C1C(C)=NN2C1CCCC1", "output": "CC1=NN(C2CCCC2)C(N)=C1.CCOC(=O)C(=O)CC(=O)C1CC1", "task": "retrosynthesis", "split": "test", "original_reaction_smiles_with_atom_mapping": ["[CH:1]1([N:6]2[C:10]([NH2:11])=[CH:9][C:8]([CH3:12])=[N:7]2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH:13]1([C:16](=O)[CH2:17][C:18](=O)[C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH2:15][CH2:14]1>C1C=CC=CC=1>[CH:1]1([n:6]2[n:7][c:8]([CH3:12])[c:9]3[c:10]2[n:11][c:16]([CH:13]2[CH2:14][CH2:15]2)[cH:17][c:18]3[C:19](=[O:20])[O:21][CH2:22][CH3:23])[CH2:2][CH2:3][CH2:4][CH2:5]1"]}
  81. {"input": "NC1=C(F)C(NCCNC2=CC=CC=N2)=C(F)C2=C1C(=O)C(C(=O)O)=CN2C1CC1", "output": "NC1=C(F)C(F)=C(F)C2=C1C(=O)C(C(=O)O)=CN2C1CC1.NCCNC1=CC=CC=N1", "task": "retrosynthesis", "split": "test", "original_reaction_smiles_with_atom_mapping": ["[NH2:1][C:2]1[C:11]([F:12])=[C:10](F)[C:9]([F:14])=[C:8]2[C:3]=1[C:4](=[O:21])[C:5]([C:18]([OH:20])=[O:19])=[CH:6][N:7]2[CH:15]1[CH2:17][CH2:16]1.[N:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[NH:28][CH2:29][CH2:30][NH2:31]>CS(C)=O>[NH2:1][c:2]1[c:3]2[c:4](=[O:21])[c:5]([C:18](=[O:19])[OH:20])[cH:6][n:7]([CH:15]3[CH2:16][CH2:17]3)[c:8]2[c:9]([F:14])[c:10]([NH:31][CH2:30][CH2:29][NH:28][c:23]2[n:22][cH:27][cH:26][cH:25][cH:24]2)[c:11]1[F:12]"]}
  82. {"input": "O=C(O)CCSC1=CC=CC=C1", "output": "C=CC(=O)O.SC1=CC=CC=C1", "task": "retrosynthesis", "split": "test", "original_reaction_smiles_with_atom_mapping": ["[c:1]1([SH:7])[cH:2][cH:3][cH:4][cH:5][cH:6]1.[C:15]([CH:16]=[CH2:17])(=[O:18])[OH:19]>C1COCC1.CCN(CC)CC.Cl>[c:1]1([S:7][CH2:17][CH2:16][C:15](=[O:18])[OH:19])[cH:2][cH:3][cH:4][cH:5][cH:6]1"]}
  83. {"input": "CC1=CSC(C)=C1C1=C(C#N)C(C)=NN1C1=CC=C(O)C=C1F", "output": "CC1=NN(C2=CC=C(O)C=C2F)C(I)=C1C#N.CCCC[Sn](CCCC)(CCCC)C1=C(C)SC=C1C", "task": "retrosynthesis", "split": "test", "original_reaction_smiles_with_atom_mapping": ["[F:1][C:2]1[CH:7]=[C:6]([OH:8])[CH:5]=[CH:4][C:3]=1[N:9]1[C:13](I)=[C:12]([C:15]#[N:16])[C:11]([CH3:17])=[N:10]1.C([Sn](CCCC)(CCCC)[C:23]1[C:27]([CH3:28])=[CH:26][S:25][C:24]=1[CH3:29])CCC>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[F:1][c:2]1[c:3](-[n:9]2[n:10][c:11]([CH3:17])[c:12]([C:15]#[N:16])[c:13]2-[c:23]2[c:24]([CH3:29])[s:25][cH:26][c:27]2[CH3:28])[cH:4][cH:5][c:6]([OH:8])[cH:7]1"]}
  84. {"input": "CC(C)(C)OC(=O)C=CC1=CC=C(O[Si](C2=CC=CC=C2)(C2=CC=CC=C2)C(C)(C)C)C=C1C=O", "output": "CC(C)(C)OC(=O)C=CC1=CC=C(O)C=C1C=O.CC(C)(C)[Si](Cl)(C1=CC=CC=C1)C1=CC=CC=C1", "task": "retrosynthesis", "split": "test", "original_reaction_smiles_with_atom_mapping": ["[C:1]([CH3:2])([CH3:3])([CH3:4])[O:5][C:6]([CH:7]=[CH:8][c:9]1[c:10]([CH:16]=[O:17])[cH:11][c:12]([OH:15])[cH:13][cH:14]1)=[O:18].Cl[Si:23]([C:19]([CH3:20])([CH3:21])[CH3:22])([c:24]1[cH:25][cH:26][cH:27][cH:28][cH:29]1)[c:30]1[cH:31][cH:32][cH:33][cH:34][cH:35]1>C(Cl)Cl.CCN(CC)CC>[C:1]([CH3:2])([CH3:3])([CH3:4])[O:5][C:6]([CH:7]=[CH:8][c:9]1[c:10]([CH:16]=[O:17])[cH:11][c:12]([O:15][Si:23]([C:19]([CH3:20])([CH3:21])[CH3:22])([c:24]2[cH:25][cH:26][cH:27][cH:28][cH:29]2)[c:30]2[cH:31][cH:32][cH:33][cH:34][cH:35]2)[cH:13][cH:14]1)=[O:18]"]}
  85. {"input": "CCOC(=O)CCC1=CC=C(N(C2CCC3=C(C4=C(C)C=C(O[Si](C)(C)C(C)(C)C)C=C4C)C=CC=C32)S(=O)(=O)C2=CC=CC=C2[N+](=O)[O-])C=C1F", "output": "CC1=CC(O[Si](C)(C)C(C)(C)C)=CC(C)=C1B(O)O.CCOC(=O)CCC1=CC=C(N(C2CCC3=C(OS(=O)(=O)C(F)(F)F)C=CC=C32)S(=O)(=O)C2=CC=CC=C2[N+](=O)[O-])C=C1F", "task": "retrosynthesis", "split": "test", "original_reaction_smiles_with_atom_mapping": ["O=S(=O)(O[c:13]1[c:12]2[c:17]([cH:16][cH:15][cH:14]1)[CH:9]([N:8]([c:6]1[cH:5][cH:4][c:3]([CH2:38][CH2:39][C:40](=[O:41])[O:42][CH2:43][CH3:44])[c:2]([F:1])[cH:7]1)[S:26](=[O:27])(=[O:28])[c:29]1[c:30]([N+:35](=[O:36])[O-:37])[cH:31][cH:32][cH:33][cH:34]1)[CH2:10][CH2:11]2)C(F)(F)F.OB(O)[c:56]1[c:55]([CH3:63])[cH:54][c:53]([O:52][Si:45]([CH3:46])([CH3:47])[C:48]([CH3:49])([CH3:50])[CH3:51])[cH:58][c:57]1[CH3:59]>O.C(O)C.C1(C)C=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O=C([O-])[O-].[Na+].[Na+]>[F:1][c:2]1[c:3]([CH2:38][CH2:39][C:40](=[O:41])[O:42][CH2:43][CH3:44])[cH:4][cH:5][c:6]([N:8]([CH:9]2[CH2:10][CH2:11][c:12]3[c:13](-[c:56]4[c:55]([CH3:63])[cH:54][c:53]([O:52][Si:45]([CH3:46])([CH3:47])[C:48]([CH3:49])([CH3:50])[CH3:51])[cH:58][c:57]4[CH3:59])[cH:14][cH:15][cH:16][c:17]32)[S:26](=[O:27])(=[O:28])[c:29]2[c:30]([N+:35](=[O:36])[O-:37])[cH:31][cH:32][cH:33][cH:34]2)[cH:7]1"]}
  86. {"input": "N#CC(C1=CC=C(Cl)C=C1)C1=C(Cl)C=C(NN=CC2=CC=CC=C2)C=C1Cl", "output": "N#CC(C1=CC=C(Cl)C=C1)C1=C(Cl)C=C(NN)C=C1Cl.O=CC1=CC=CC=C1", "task": "retrosynthesis", "split": "test", "original_reaction_smiles_with_atom_mapping": ["[Cl:1][c:2]1[cH:3][cH:4][c:5]([CH:6]([C:7]#[N:8])[c:9]2[c:10]([Cl:18])[cH:11][c:12]([NH:16][NH2:17])[cH:13][c:14]2[Cl:15])[cH:19][cH:20]1.O=[CH:21][c:22]1[cH:23][cH:24][cH:25][cH:26][cH:27]1>C(OC(=O)C)C.O=S(=O)([O-])[O-].[Mg+2]>[Cl:1][c:2]1[cH:3][cH:4][c:5]([CH:6]([C:7]#[N:8])[c:9]2[c:10]([Cl:18])[cH:11][c:12]([NH:16][N:17]=[CH:21][c:22]3[cH:23][cH:24][cH:25][cH:26][cH:27]3)[cH:13][c:14]2[Cl:15])[cH:19][cH:20]1"]}
  87. {"input": "CCOC(=O)C1CC2(CCN(C3=NC(N)=NC(NCC4=CC=C5C=CC=CC5=C4)=N3)CC2)CN1C(=O)OCC1=CC=CC=C1", "output": "CCOC(=O)C1CC2(CCN(C3=NC(N)=NC(Cl)=N3)CC2)CN1C(=O)OCC1=CC=CC=C1.NCC1=CC=C2C=CC=CC2=C1", "task": "retrosynthesis", "split": "test", "original_reaction_smiles_with_atom_mapping": ["Cl[c:6]1[n:5][c:4]([N:9]2[CH2:10][CH2:11][C:12]3([CH2:13][CH:14]([C:27](=[O:28])[O:29][CH2:30][CH3:31])[N:15]([C:17](=[O:18])[O:19][CH2:20][c:21]4[cH:22][cH:23][cH:24][cH:25][cH:26]4)[CH2:16]3)[CH2:32][CH2:33]2)[n:3][c:2]([NH2:1])[n:7]1.[cH:34]1[c:35]([CH2:44][NH2:45])[cH:36][cH:37][c:38]2[cH:39][cH:40][cH:41][cH:42][c:43]12>C(O)(C)C.CCN(CC)CC>[NH2:1][c:2]1[n:3][c:4]([N:9]2[CH2:10][CH2:11][C:12]3([CH2:13][CH:14]([C:27](=[O:28])[O:29][CH2:30][CH3:31])[N:15]([C:17](=[O:18])[O:19][CH2:20][c:21]4[cH:22][cH:23][cH:24][cH:25][cH:26]4)[CH2:16]3)[CH2:32][CH2:33]2)[n:5][c:6]([NH:45][CH2:44][c:35]2[cH:34][c:43]3[c:38]([cH:37][cH:36]2)[cH:39][cH:40][cH:41][cH:42]3)[n:7]1"]}
  88. {"input": "CC1=CC=C2N=C(N3CCS(=O)C4=CC=CC=C4C3)N=C(N3CCC(NC(=O)OC(C)(C)C)C3)C2=C1", "output": "CC(C)(C)OC(=O)NC1CCNC1.CC1=CC=C2N=C(N3CCS(=O)C4=CC=CC=C4C3)NC(=O)C2=C1", "task": "retrosynthesis", "split": "test", "original_reaction_smiles_with_atom_mapping": ["O=[c:45]1[c:44]2[cH:43][c:42]([CH3:41])[cH:51][cH:50][c:49]2[n:48][c:47]([N:52]2[CH2:53][CH2:54][S:55](=[O:63])[c:56]3[c:57]([cH:59][cH:60][cH:61][cH:62]3)[CH2:58]2)[nH:46]1.[NH:65]1[CH2:66][CH:67]([NH:70][C:71]([O:72][C:73]([CH3:74])([CH3:75])[CH3:76])=[O:77])[CH2:68][CH2:69]1>Cc1ccc2nc(N3CCS(=O)c4ccccc4C3)nc(N[C@H]3CN(C(=O)OCc4ccccc4)C[C@@H]3F)c2c1>[CH3:41][c:42]1[cH:43][c:44]2[c:45]([N:65]3[CH2:66][CH:67]([NH:70][C:71]([O:72][C:73]([CH3:74])([CH3:75])[CH3:76])=[O:77])[CH2:68][CH2:69]3)[n:46][c:47]([N:52]3[CH2:53][CH2:54][S:55](=[O:63])[c:56]4[c:57]([cH:59][cH:60][cH:61][cH:62]4)[CH2:58]3)[n:48][c:49]2[cH:50][cH:51]1"]}
  89. {"input": "CN1C=C(C(=O)CC(C2=CC=C(Br)C=C2)C2=CC=CC=C2Cl)C=CC1=O", "output": "O=C(CC(C1=CC=C(Br)C=C1)C1=CC=CC=C1Cl)C1=CNC(=O)C=C1.O=C([O-])[O-]", "task": "retrosynthesis", "split": "test", "original_reaction_smiles_with_atom_mapping": ["[Br:1][c:2]1[cH:3][cH:4][c:5]([CH:8]([CH2:9][C:10](=[O:11])[c:12]2[cH:13][cH:14][c:15](=[O:18])[nH:16][cH:17]2)[c:19]2[c:20]([Cl:25])[cH:21][cH:22][cH:23][cH:24]2)[cH:6][cH:7]1.O=[C:28]([O-])[O-]>CI.[K+].[K+]>[Br:1][c:2]1[cH:3][cH:4][c:5]([CH:8]([CH2:9][C:10](=[O:11])[c:12]2[cH:13][cH:14][c:15](=[O:18])[n:16]([CH3:28])[cH:17]2)[c:19]2[c:20]([Cl:25])[cH:21][cH:22][cH:23][cH:24]2)[cH:6][cH:7]1"]}
  90. {"input": "O=S(=O)(C1=CC=CC=C1)C1=CC=C(S[C@@H]2SC[C@@H](O)[C@H](O)[C@H]2O)C=C1", "output": "CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@H](SC2=CC=C(S(=O)(=O)C3=CC=CC=C3)C=C2)SC[C@H]1OC(C)=O", "task": "retrosynthesis", "split": "test", "original_reaction_smiles_with_atom_mapping": ["CC(=O)[O:7][C@H:8]1[C@H:9]([S:10][c:11]2[cH:12][cH:13][c:14]([S:17](=[O:18])(=[O:19])[c:20]3[cH:21][cH:22][cH:23][cH:24][cH:25]3)[cH:15][cH:16]2)[S:26][CH2:27][C@@H:28]([O:34]C(C)=O)[C@@H:29]1[O:30]C(C)=O>CO.C(O)C.O.C[O-].[Na+].C1CCOC1>[OH:7][C@H:8]1[C@H:9]([S:10][c:11]2[cH:12][cH:13][c:14]([S:17](=[O:18])(=[O:19])[c:20]3[cH:21][cH:22][cH:23][cH:24][cH:25]3)[cH:15][cH:16]2)[S:26][CH2:27][C@@H:28]([OH:34])[C@@H:29]1[OH:30]"]}
  91. {"input": "O=C(C1=CN=CN=C1)C1=CC(Br)=CC=C1F", "output": "OC(C1=CN=CN=C1)C1=CC(Br)=CC=C1F", "task": "retrosynthesis", "split": "test", "original_reaction_smiles_with_atom_mapping": ["[Br:1][c:2]1[cH:3][cH:4][c:5]([F:16])[c:6]([CH:8]([OH:9])[c:10]2[cH:11][n:12][cH:13][n:14][cH:15]2)[cH:7]1>C(Cl)Cl.CC(=O)OI1(OC(C)=O)(OC(C)=O)OC(=O)c2ccccc21>[Br:1][c:2]1[cH:3][cH:4][c:5]([F:16])[c:6]([C:8](=[O:9])[c:10]2[cH:11][n:12][cH:13][n:14][cH:15]2)[cH:7]1"]}
  92. {"input": "CCCCCCCCCCCCC1=CC=C(C(=O)CC)C=C1", "output": "CCC(=O)Cl.CCCCCCCCCCCCC1=CC=CC=C1", "task": "retrosynthesis", "split": "test", "original_reaction_smiles_with_atom_mapping": ["Cl[C:5]([CH2:6][CH3:7])=[O:8].[CH2:10]([CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[c:22]1[cH:23][cH:24][cH:25][cH:26][cH:27]1>C(Cl)(Cl)(Cl)Cl.[Cl-].[Al+3].[Cl-].[Cl-].Cl>[C:5]([CH2:6][CH3:7])(=[O:8])[c:25]1[cH:24][cH:23][c:22]([CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[cH:27][cH:26]1"]}
  93. {"input": "C[N+]1(C)CCCC2=C(N)C=CC(O)=C21", "output": "C[N+]1(C)CCCC2=C(N=NC3=CC=CC=C3)C=CC(O)=C21", "task": "retrosynthesis", "split": "test", "original_reaction_smiles_with_atom_mapping": ["c1ccc(N=[N:14][c:8]2[c:7]3[c:12]([c:11]([OH:13])[cH:10][cH:9]2)[N+:3]([CH3:2])([CH3:22])[CH2:4][CH2:5][CH2:6]3)cc1>[Pd].O.[Br-].CO.[H][H]>[CH3:2][N+:3]1([CH3:22])[CH2:4][CH2:5][CH2:6][c:7]2[c:8]([NH2:14])[cH:9][cH:10][c:11]([OH:13])[c:12]21"]}
  94. {"input": "NCC(=O)N1CCN(C2=NC3=C(N4CCOCC4)N=C(C4=CN=C(N)N=C4)N=C3N2CC2CC2)CC1", "output": "CC(C)(C)OC(=O)NCC(=O)O.NC1=NC=C(C2=NC(N3CCOCC3)=C3N=C(N4CCNCC4)N(CC4CC4)C3=N2)C=N1", "task": "retrosynthesis", "split": "test", "original_reaction_smiles_with_atom_mapping": ["[CH:31]1([CH2:34][n:35]2[c:36]3[n:37][c:38](-[c:56]4[cH:57][n:58][c:59]([NH2:62])[n:60][cH:61]4)[n:39][c:40]([N:50]4[CH2:51][CH2:52][O:53][CH2:54][CH2:55]4)[c:41]3[n:42][c:43]2[N:44]2[CH2:45][CH2:46][NH:47][CH2:48][CH2:49]2)[CH2:32][CH2:33]1.CC(C)(C)OC(=O)[NH:70][CH2:71][C:72](O)=[O:73]>ClCCl.CO.CN(C)C=O.O.On1nnc2ccccc21.Cl.CCN=C=NCCCN(C)C.CCN(CC)CC>[CH:31]1([CH2:34][n:35]2[c:36]3[n:37][c:38](-[c:56]4[cH:57][n:58][c:59]([NH2:62])[n:60][cH:61]4)[n:39][c:40]([N:50]4[CH2:51][CH2:52][O:53][CH2:54][CH2:55]4)[c:41]3[n:42][c:43]2[N:44]2[CH2:45][CH2:46][N:47]([C:72]([CH2:71][NH2:70])=[O:73])[CH2:48][CH2:49]2)[CH2:32][CH2:33]1"]}
  95. {"input": "CC(=O)SC[C@@H](C(=O)N1C(=O)OC[C@H]1CC1=CC=CC=C1)C(C)C", "output": "CC(C)C(CI)C(=O)N1C(=O)OC[C@H]1CC1=CC=CC=C1.CC([O-])=S", "task": "retrosynthesis", "split": "test", "original_reaction_smiles_with_atom_mapping": ["[C:1]([CH3:2])(=[S:3])[O-:4].I[CH2:24][CH:20]([C:19]([N:14]1[C@H:13]([CH2:6][c:7]2[cH:8][cH:9][cH:10][cH:11][cH:12]2)[CH2:17][O:16][C:15]1=[O:18])=[O:26])[CH:21]([CH3:22])[CH3:23]>CN(C)C=O.[K+].O>[C:1]([CH3:2])([S:3][CH2:24][C@@H:20]([C:19]([N:14]1[C@H:13]([CH2:6][c:7]2[cH:8][cH:9][cH:10][cH:11][cH:12]2)[CH2:17][O:16][C:15]1=[O:18])=[O:26])[CH:21]([CH3:22])[CH3:23])=[O:4]"]}
  96. {"input": "CC(C)(C)OC(=O)C[C@@H](CCCC1=CC=CC=C1)C(=O)O", "output": "CC(C)(C)OC(=O)C/C(=C\\CCC1=CC=CC=C1)C(=O)O", "task": "retrosynthesis", "split": "test", "original_reaction_smiles_with_atom_mapping": ["[C:1]([CH3:2])([CH3:3])([CH3:4])[O:5][C:6]([CH2:7]/[C:8]([C:9](=[O:10])[OH:11])=[CH:12]\\[CH2:13][CH2:14][c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1)=[O:21]>CO.NC1CCCCC1>[C:1]([CH3:2])([CH3:3])([CH3:4])[O:5][C:6]([CH2:7][C@H:8]([C:9](=[O:10])[OH:11])[CH2:12][CH2:13][CH2:14][c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1)=[O:21]", "[C:1]([O:5][C:6](=[O:21])[CH2:7]/[C:8](=[CH:12]\\[CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)/[C:9]([OH:11])=[O:10])([CH3:4])([CH3:3])[CH3:2]>CO>[C:1]([CH3:2])([CH3:3])([CH3:4])[O:5][C:6]([CH2:7][C@H:8]([C:9](=[O:10])[OH:11])[CH2:12][CH2:13][CH2:14][c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1)=[O:21]", "[C:8]([CH3:9])([CH3:10])([CH3:11])[O:12][C:13]([CH2:14]/[C:15]([C:16](=[O:17])[OH:18])=[CH:19]\\[CH2:20][CH2:21][c:22]1[cH:23][cH:24][cH:25][cH:26][cH:27]1)=[O:28]>CO.NC1CCCCC1>[C:8]([CH3:9])([CH3:10])([CH3:11])[O:12][C:13]([CH2:14][C@H:15]([C:16](=[O:17])[OH:18])[CH2:19][CH2:20][CH2:21][c:22]1[cH:23][cH:24][cH:25][cH:26][cH:27]1)=[O:28]"]}
  97. {"input": "CCOC(=O)C1=CC(N2C(N)=NC(C(F)(F)F)=CC2=O)=CC=C1Cl", "output": "CCOC(=O)C1=CC(N2C(S(C)(=O)=O)=NC(C(F)(F)F)=CC2=O)=CC=C1Cl.N", "task": "retrosynthesis", "split": "test", "original_reaction_smiles_with_atom_mapping": ["[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:13](=[O:14])[CH:12]=[C:11]([C:15]([F:18])([F:17])[F:16])[N:10]=[C:9]2S(C)(=O)=O)=[CH:4][C:3]=1[C:23]([O:25][CH2:26][CH3:27])=[O:24].[NH3:28]>C1COCC1>[Cl:1][c:2]1[c:3]([C:23](=[O:24])[O:25][CH2:26][CH3:27])[cH:4][c:5](-[n:8]2[c:9]([NH2:28])[n:10][c:11]([C:15]([F:16])([F:17])[F:18])[cH:12][c:13]2=[O:14])[cH:6][cH:7]1"]}
  98. {"input": "COC(=O)C(=CC1=CC(OC)=C(OC)C(OC)=C1)N=[N+]=[N-]", "output": "COC(=O)CN=[N+]=[N-].COC1=CC(C=O)=CC(OC)=C1OC", "task": "retrosynthesis", "split": "test", "original_reaction_smiles_with_atom_mapping": ["O=[CH:6][c:5]1[cH:4][c:3]([O:2][CH3:1])[c:10]([O:11][CH3:12])[c:9]([O:13][CH3:14])[cH:8]1.[N:15](=[N+:16]=[N-:17])[CH2:18][C:19](=[O:20])[O:21][CH3:22]>CO.[Na]>[CH3:1][O:2][c:3]1[cH:4][c:5]([CH:6]=[C:18]([N:15]=[N+:16]=[N-:17])[C:19](=[O:20])[O:21][CH3:22])[cH:8][c:9]([O:13][CH3:14])[c:10]1[O:11][CH3:12]"]}
  99. {"input": "N#CC1=CC=C(C(=O)NC2=CC=C(F)C([C@]3(C(F)F)COCC(N)=N3)=C2)N=C1", "output": "CC(C)(C)OC(=O)NC1=N[C@@](C2=CC(NC(=O)C3=CC=C(C#N)C=N3)=CC=C2F)(C(F)F)COC1", "task": "retrosynthesis", "split": "test", "original_reaction_smiles_with_atom_mapping": ["CC(C)(C)OC(=O)[NH:7][C:8]1=[N:13][C@:12]([CH:14]([F:15])[F:16])([c:17]2[c:18]([F:34])[cH:19][cH:20][c:21]([NH:23][C:24](=[O:25])[c:26]3[n:27][cH:28][c:29]([C:32]#[N:33])[cH:30][cH:31]3)[cH:22]2)[CH2:11][O:10][CH2:9]1>C(Cl)Cl.O=C(O)C(F)(F)F>[NH2:7][C:8]1=[N:13][C@:12]([CH:14]([F:15])[F:16])([c:17]2[c:18]([F:34])[cH:19][cH:20][c:21]([NH:23][C:24](=[O:25])[c:26]3[n:27][cH:28][c:29]([C:32]#[N:33])[cH:30][cH:31]3)[cH:22]2)[CH2:11][O:10][CH2:9]1"]}
  100. {"input": "N#CC1=CC=C(N(CCSC2=CC=C(O)C=C2)N2C=NN=C2)C=C1", "output": "N#CC1=CC=C(N(CCBr)N2C=NN=C2)C=C1.OC1=CC=C(S)C=C1", "task": "retrosynthesis", "split": "test", "original_reaction_smiles_with_atom_mapping": ["Br[CH2:2][CH2:3][N:4]([c:5]1[cH:6][cH:7][c:8]([C:9]#[N:10])[cH:11][cH:12]1)[n:13]1[cH:14][n:15][n:16][cH:17]1.[OH:18][c:19]1[cH:20][cH:21][c:22]([SH:25])[cH:23][cH:24]1>CN(C=O)C.O.O=C([O-])[O-].[K+].[K+].CCOC(C)=O>[CH2:2]([CH2:3][N:4]([c:5]1[cH:6][cH:7][c:8]([C:9]#[N:10])[cH:11][cH:12]1)[n:13]1[cH:14][n:15][n:16][cH:17]1)[S:25][c:22]1[cH:21][cH:20][c:19]([OH:18])[cH:24][cH:23]1"]}
  101. {"input": "CN(C)C1(CC2=CC=CC=C2)CCC(O)(C2=CC3=CC=CC=C3S2)CC1", "output": "C1=CC=C2SC=CC2=C1.CN(C)C1(CC2=CC=CC=C2)CCC(=O)CC1", "task": "retrosynthesis", "split": "test", "original_reaction_smiles_with_atom_mapping": ["[s:1]1[c:2]2[c:3]([cH:4][cH:5]1)[cH:6][cH:7][cH:8][cH:9]2.[CH2:20]([c:21]1[cH:22][cH:23][cH:24][cH:25][cH:26]1)[C:27]1([N:34]([CH3:35])[CH3:36])[CH2:28][CH2:29][C:30](=[O:33])[CH2:31][CH2:32]1>C1COCC1.[Li]C(C)(C)C.CCCCC>[s:1]1[c:2]2[c:3]([cH:4][c:5]1[C:30]1([OH:33])[CH2:29][CH2:28][C:27]([CH2:20][c:21]3[cH:22][cH:23][cH:24][cH:25][cH:26]3)([N:34]([CH3:35])[CH3:36])[CH2:32][CH2:31]1)[cH:6][cH:7][cH:8][cH:9]2"]}
  102. {"input": "COC(=O)[C@H](CC(=O)CC1=CC=CC=C1)NC(=O)OCC1=CC=CC=C1", "output": "COC(=O)[C@H](CC(=O)Cl)NC(=O)OCC1=CC=CC=C1.Cl[Mg]CC1=CC=CC=C1", "task": "retrosynthesis", "split": "test", "original_reaction_smiles_with_atom_mapping": ["Cl[Mg][CH2:3][c:4]1[cH:5][cH:6][cH:7][cH:8][cH:9]1.Cl[C:29]([CH2:28][C@H:23]([NH:22][C:20]([O:19][CH2:12][c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1)=[O:21])[C:24](=[O:25])[O:26][CH3:27])=[O:30]>C1COCC1.[Br-].[Li+]>[CH2:3]([c:4]1[cH:5][cH:6][cH:7][cH:8][cH:9]1)[C:29]([CH2:28][C@H:23]([NH:22][C:20]([O:19][CH2:12][c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1)=[O:21])[C:24](=[O:25])[O:26][CH3:27])=[O:30]", "Cl[Mg][CH2:3][c:4]1[cH:5][cH:6][cH:7][cH:8][cH:9]1.Cl[C:29]([CH2:28][C@H:23]([NH:22][C:20]([O:19][CH2:12][c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1)=[O:21])[C:24](=[O:25])[O:26][CH3:27])=[O:30]>C1COCC1.ClCCl.[Br-].[Li+].[NH4+].[Cl-]>[CH2:3]([c:4]1[cH:5][cH:6][cH:7][cH:8][cH:9]1)[C:29]([CH2:28][C@H:23]([NH:22][C:20]([O:19][CH2:12][c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1)=[O:21])[C:24](=[O:25])[O:26][CH3:27])=[O:30]"]}
  103. {"input": "CC1=C(N2CCN(C(=O)C3=NC=CC=N3)CC2)N=C2C=C(F)C=C(F)C2=C1NC1=CN=CC(N2CCOCC2)=C1", "output": "CC1=C(N2CCNCC2)N=C2C=C(F)C=C(F)C2=C1NC1=CN=CC(N2CCOCC2)=C1.O=C(O)C1=NC=CC=N1", "task": "retrosynthesis", "split": "test", "original_reaction_smiles_with_atom_mapping": ["[F:1][C:2]1[CH:11]=[C:10]([F:12])[CH:9]=[C:8]2[C:3]=1[C:4]([NH:20][C:21]1[CH:22]=[N:23][CH:24]=[C:25]([N:27]3[CH2:32][CH2:31][O:30][CH2:29][CH2:28]3)[CH:26]=1)=[C:5]([CH3:19])[C:6]([N:13]1[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1)=[N:7]2.[N:33]1[CH:38]=[CH:37][CH:36]=[N:35][C:34]=1[C:39](O)=[O:40]>>[F:1][c:2]1[c:3]2[c:4]([NH:20][c:21]3[cH:22][n:23][cH:24][c:25]([N:27]4[CH2:28][CH2:29][O:30][CH2:31][CH2:32]4)[cH:26]3)[c:5]([CH3:19])[c:6]([N:13]3[CH2:14][CH2:15][N:16]([C:39]([c:34]4[n:33][cH:38][cH:37][cH:36][n:35]4)=[O:40])[CH2:17][CH2:18]3)[n:7][c:8]2[cH:9][c:10]([F:12])[cH:11]1"]}
  104. {"input": "CCCN1C(=O)C2=C(N=C(CC3=NN=NN3)N2)N(CCC2=CC=C([N+](=O)[O-])C=C2)C1=O", "output": "CCCN1C(=O)C(N)=C(N)N(CCC2=CC=C([N+](=O)[O-])C=C2)C1=O.O=C(O)CC1=NN=NN1", "task": "retrosynthesis", "split": "test", "original_reaction_smiles_with_atom_mapping": ["[NH:1]1[C:5]([CH2:6][C:7](O)=O)=[N:4][N:3]=[N:2]1.[NH2:10][C:11]1[C:12](=[O:33])[N:13]([CH2:30][CH2:31][CH3:32])[C:14](=[O:29])[N:15]([CH2:18][CH2:19][C:20]2[CH:25]=[CH:24][C:23]([N+:26]([O-:28])=[O:27])=[CH:22][CH:21]=2)[C:16]=1[NH2:17]>>[nH:1]1[n:2][n:3][n:4][c:5]1[CH2:6][c:7]1[nH:10][c:11]2[c:12](=[O:33])[n:13]([CH2:30][CH2:31][CH3:32])[c:14](=[O:29])[n:15]([CH2:18][CH2:19][c:20]3[cH:21][cH:22][c:23]([N+:26](=[O:27])[O-:28])[cH:24][cH:25]3)[c:16]2[n:17]1"]}
  105. {"input": "CCCN(CCC)C(=O)C1=CC(C(=O)N[C@@H](CC2=CC=CC=C2)[C@H](O)CNCC2=CC=CC(OC)=C2)=CC(C2=CSC=C2)=C1", "output": "CCCN(CCC)C(=O)C1=CC(C(=O)O)=CC(C2=CSC=C2)=C1.COC1=CC=CC(CNC[C@@H](O)[C@@H](N)CC2=CC(F)=CC(F)=C2)=C1", "task": "retrosynthesis", "split": "test", "original_reaction_smiles_with_atom_mapping": ["O=[C:10]([c:9]1[cH:8][c:7]([C:5]([N:4]([CH2:1][CH2:2][CH3:3])[CH2:21][CH2:22][CH3:23])=[O:6])[cH:15][c:14](-[c:16]2[cH:17][s:18][cH:19][cH:20]2)[cH:13]1)[OH:12].F[c:49]1[cH:48][c:47]([CH2:46][C@H:32]([NH2:31])[C@@H:33]([CH2:34][NH:35][CH2:36][c:37]2[cH:38][c:39]([O:43][CH3:44])[cH:40][cH:41][cH:42]2)[OH:45])[cH:52][c:51](F)[cH:50]1>CN(C=O)C.O.O=C(O)C(F)(F)F.On1nnc2ccccc21.CCN(CC)CC.ClCCCl>[CH2:1]([CH2:2][CH3:3])[N:4]([C:5](=[O:6])[c:7]1[cH:8][c:9]([C:10](=[O:12])[NH:31][C@H:32]([C@@H:33]([CH2:34][NH:35][CH2:36][c:37]2[cH:38][c:39]([O:43][CH3:44])[cH:40][cH:41][cH:42]2)[OH:45])[CH2:46][c:47]2[cH:48][cH:49][cH:50][cH:51][cH:52]2)[cH:13][c:14](-[c:16]2[cH:17][s:18][cH:19][cH:20]2)[cH:15]1)[CH2:21][CH2:22][CH3:23]"]}
  106. {"input": "COC(=O)CCON1C(C)(C)CC(OCC2=CC=CC=C2)CC1(C)C", "output": "C=CC(=O)OC.CC1(C)CC(OCC2=CC=CC=C2)CC(C)(C)N1O", "task": "retrosynthesis", "split": "test", "original_reaction_smiles_with_atom_mapping": ["[CH2:1]([c:2]1[cH:3][cH:4][cH:5][cH:6][cH:7]1)[O:8][CH:9]1[CH2:10][C:11]([CH3:18])([CH3:19])[N:12]([OH:17])[C:13]([CH3:15])([CH3:16])[CH2:14]1.[C:32]([CH:33]=[CH2:34])(=[O:35])[O:36][CH3:37]>[Pd].O1CCCC1.O=S(=O)([O-])[O-].[Mg+2].CC(C)(C)[O-].[K+]>[CH2:1]([c:2]1[cH:3][cH:4][cH:5][cH:6][cH:7]1)[O:8][CH:9]1[CH2:10][C:11]([CH3:18])([CH3:19])[N:12]([O:17][CH2:34][CH2:33][C:32](=[O:35])[O:36][CH3:37])[C:13]([CH3:15])([CH3:16])[CH2:14]1"]}
  107.  
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