dataset_id large_stringclasses 414
values | reaction_id large_stringlengths 36 36 | reaction_smiles large_stringlengths 4 873 | rxn_insight_reaction large_stringlengths 19 1.07k | mapped_reaction_smiles large_stringlengths 14 3.37k | reactant_smiles large_stringlengths 1 581 | product_smiles large_stringlengths 1 433 | reagent_smiles large_stringclasses 634
values | catalyst_smiles large_stringlengths 1 683 ⌀ | solvent_smiles large_stringlengths 1 245 ⌀ | rxn_insight_class large_stringclasses 11
values | rxn_insight_name large_stringclasses 346
values | rxn_insight_tag large_stringlengths 64 64 | rxn_insight_tag2 large_stringlengths 64 64 | rxn_insight_scaffold large_stringlengths 5 288 ⌀ | rxn_insight_template large_stringlengths 24 2.64k ⌀ | yield_percent float64 -0.8 90,205,160,000B ⌀ | yield_measurements large_stringlengths 2 864 | temperature_value float64 -230 30.1k ⌀ | temperature_units large_stringclasses 3
values | reaction_time_value float64 0 4k ⌀ | time_units large_stringclasses 4
values | procedure_details large_stringlengths 1 23.6k ⌀ | reference large_stringclasses 96
values | doi large_stringclasses 19
values | functional_groups_reactants large_stringlengths 3 716 ⌀ | functional_groups_products large_stringlengths 3 539 ⌀ | participating_rings_reactants large_stringlengths 5 293 ⌀ | participating_rings_products large_stringlengths 5 271 ⌀ | all_rings_products large_stringlengths 5 271 ⌀ | byproduct_smiles large_stringclasses 176
values | agent_smiles large_stringlengths 1 712 ⌀ | temperature_c float64 -230 30.1k ⌀ | reaction_time_hours float64 0 2.16k ⌀ | reaction_smiles_with_agents large_stringlengths 4 882 |
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-a20466eb704b4286a24630c1e60bd7a4 | NCCCC[C@@H](C(=O)O)N(C(=O)OCC1c2ccccc2-c2ccccc21)C(=O)OCC1c2ccccc2-c2ccccc21>>NCCCC[C@@H](C(=O)F)N(C(=O)OCC1c2ccccc2-c2ccccc21)C(=O)OCC1c2ccccc2-c2ccccc21 | N1=CC=CC=C1.N1=C(F)N=C(F)N=C1F.C(=O)(OCC1C2=CC=CC=C2C2=CC=CC=C12)N([C@@H](CCCCN)C(=O)O)C(=O)OCC1C2=CC=CC=C2C2=CC=CC=C12>>C(=O)(OCC1C2=CC=CC=C2C2=CC=CC=C12)N([C@@H](CCCCN)C(=O)F)C(=O)OCC1C2=CC=CC=C2C2=CC=CC=C12 | O[C:7]([C@H:6]([CH2:5][CH2:4][CH2:3][CH2:2][NH2:1])[N:10]([C:11](=[O:12])[O:13][CH2:14][CH:15]1[c:16]2[cH:17][cH:18][cH:19][cH:20][c:21]2-[c:22]2[cH:23][cH:24][cH:25][cH:26][c:27]21)[C:28](=[O:29])[O:30][CH2:31][CH:32]1[c:33]2[cH:34][cH:35][cH:36][cH:37][c:38]2-[c:39]2[cH:40][cH:41][cH:42][cH:43][c:44]21)=[O:8]>>[NH2:1... | NCCCC[C@@H](C(=O)O)N(C(=O)OCC1c2ccccc2-c2ccccc21)C(=O)OCC1c2ccccc2-c2ccccc21 | NCCCC[C@@H](C(=O)F)N(C(=O)OCC1c2ccccc2-c2ccccc21)C(=O)OCC1c2ccccc2-c2ccccc21 | null | null | ClCCl | Functional Group Interconversion | OtherReaction | c301c14a9dcd0670d52e8b77396cbe7fd8edeedd757bc43f4162ade1fc52fc93 | 787f545db5dc0b29dde55b5fbed7db8625b8055f49327f97ed4d83cc47c3af1d | O=C(NC(=O)OCC1c2ccccc2-c2ccccc21)OCC1c2ccccc2-c2ccccc21 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[#7:5](-[C:6]=[O;D1;H0:7])-[C:8]=[O;D1;H0:9]>>[C:4]-[C:3](-[#7:5](-[C:6]=[O;D1;H0:7])-[C:8]=[O;D1;H0:9])-[C;H0;D3;+0:1](-[F;D1;H0:10])=[O;D1;H0:2] | null | [] | null | null | 8 | HOUR | Bis-FMOC-L-Lysine (5 g, 8.46 mmol) (Bachem) was dissolved in dichloromethane (50 mL). Pyridine (0.69 mL, 8.46 mmol) (Aldrich) and cyanuric fluoride (1.14 g, 8.46 mmol) (Aldrich) were successively added at room temperature and the mixture was stirred overnight. Ice cold water (100 mL) was added and the resulting slurry ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Acyl halide | null | null | c1ccc2c(c1)Cc1ccccc12.c1ccc2c(c1)Cc1ccccc12 | null | ClCCl | null | 8 | NCCCC[C@@H](C(=O)O)N(C(=O)OCC1c2ccccc2-c2ccccc21)C(=O)OCC1c2ccccc2-c2ccccc21>ClCCl>NCCCC[C@@H](C(=O)F)N(C(=O)OCC1c2ccccc2-c2ccccc21)C(=O)OCC1c2ccccc2-c2ccccc21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-0c4289f38f9b4359b0462549c3b30f31 | O=C(N[C@@H](Cc1c[nH]c2ccccc12)C(=O)O)OCC1c2ccccc2-c2ccccc21>>O=C(N[C@@H](Cc1c[nH]c2ccccc12)C(=O)F)OCC1c2ccccc2-c2ccccc21 | N1=CC=CC=C1.N1=C(F)N=C(F)N=C1F.C(=O)(OCC1C2=CC=CC=C2C2=CC=CC=C12)N[C@@H](CC1=CNC2=CC=CC=C12)C(=O)O>>C(=O)(OCC1C2=CC=CC=C2C2=CC=CC=C12)N[C@@H](CC1=CNC2=CC=CC=C12)C(=O)F | O[C:15]([C@@H:4]([NH:3][C:2](=[O:1])[O:18][CH2:19][CH:20]1[c:21]2[cH:22][cH:23][cH:24][cH:25][c:26]2-[c:27]2[cH:28][cH:29][cH:30][cH:31][c:32]21)[CH2:5][c:6]1[cH:7][nH:8][c:9]2[cH:10][cH:11][cH:12][cH:13][c:14]12)=[O:16]>>[O:1]=[C:2]([NH:3][C@@H:4]([CH2:5][c:6]1[cH:7][nH:8][c:9]2[cH:10][cH:11][cH:12][cH:13][c:14]12)[C:... | O=C(N[C@@H](Cc1c[nH]c2ccccc12)C(=O)O)OCC1c2ccccc2-c2ccccc21 | O=C(N[C@@H](Cc1c[nH]c2ccccc12)C(=O)F)OCC1c2ccccc2-c2ccccc21 | null | null | ClCCl | Functional Group Interconversion | OtherReaction | c301c14a9dcd0670d52e8b77396cbe7fd8edeedd757bc43f4162ade1fc52fc93 | 787f545db5dc0b29dde55b5fbed7db8625b8055f49327f97ed4d83cc47c3af1d | O=C(NCCc1c[nH]c2ccccc12)OCC1c2ccccc2-c2ccccc21 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[#7:5]-[C:6]=[O;D1;H0:7]>>[C:4]-[C:3](-[#7:5]-[C:6]=[O;D1;H0:7])-[C;H0;D3;+0:1](-[F;D1;H0:8])=[O;D1;H0:2] | null | [] | null | null | 6.5 | HOUR | FMOC-L-Tryptophan (5 g, 11.72 mmol) (Bachem) was dissolved in dichloromethane (60 mL). Pyridine (0.95 mL, 11.72 mmol) (Aldrich) and cyanuric fluoride (1.58 g, 11.72 mmol) (Aldrich) were successively added at room temperature and the mixture was stirred for 6.5 hours. Ice cold water (100 mL) was added and the resulting ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Acyl halide | null | null | c1ccc2[nH]ccc2c1.c1ccc2c(c1)Cc1ccccc12 | null | ClCCl | null | 6.5 | O=C(N[C@@H](Cc1c[nH]c2ccccc12)C(=O)O)OCC1c2ccccc2-c2ccccc21>ClCCl>O=C(N[C@@H](Cc1c[nH]c2ccccc12)C(=O)F)OCC1c2ccccc2-c2ccccc21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-7e467cb3ee834f5c8c6a348a4e446e43 | CC(C)(C)OC[C@H](NC(=O)OCC1c2ccccc2-c2ccccc21)C(=O)O>>CC(C)(C)OC[C@H](NC(=O)OCC1c2ccccc2-c2ccccc21)C(=O)F | N1=CC=CC=C1.N1=C(F)N=C(F)N=C1F.C(=O)(OCC1C2=CC=CC=C2C2=CC=CC=C12)N[C@@H](COC(C)(C)C)C(=O)O>>C(=O)(OCC1C2=CC=CC=C2C2=CC=CC=C12)N[C@@H](COC(C)(C)C)C(=O)F | O[C:26]([C@H:7]([CH2:6][O:5][C:2]([CH3:1])([CH3:3])[CH3:4])[NH:8][C:9](=[O:10])[O:11][CH2:12][CH:13]1[c:14]2[cH:15][cH:16][cH:17][cH:18][c:19]2-[c:20]2[cH:21][cH:22][cH:23][cH:24][c:25]21)=[O:27]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][CH2:6][C@H:7]([NH:8][C:9](=[O:10])[O:11][CH2:12][CH:13]1[c:14]2[cH:15][cH:16][cH:17][cH... | CC(C)(C)OC[C@H](NC(=O)OCC1c2ccccc2-c2ccccc21)C(=O)O | CC(C)(C)OC[C@H](NC(=O)OCC1c2ccccc2-c2ccccc21)C(=O)F | null | null | ClCCl | Functional Group Interconversion | OtherReaction | c301c14a9dcd0670d52e8b77396cbe7fd8edeedd757bc43f4162ade1fc52fc93 | 787f545db5dc0b29dde55b5fbed7db8625b8055f49327f97ed4d83cc47c3af1d | c1ccc2c(c1)Cc1ccccc1-2 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[#7:5]-[C:6]=[O;D1;H0:7]>>[C:4]-[C:3](-[#7:5]-[C:6]=[O;D1;H0:7])-[C;H0;D3;+0:1](-[F;D1;H0:8])=[O;D1;H0:2] | null | [] | null | null | 8 | HOUR | N-FMOC-O-t-Butyl-L-serine (10 g, 26.07 mmol) (Bachem) was dissolved in dichloromethane (135 mL). Pyridine (2.11 mL, 26.07 mmol) (Aldrich) and cyanuric fluoride (3.52 g, 26.07 mmol) (Aldrich) were successively added at room temperature and the mixture was stirred overnight. Ice cold water (100 mL) was added and the resu... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Acyl halide | null | null | c1ccc2c(c1)Cc1ccccc12 | null | ClCCl | null | 8 | CC(C)(C)OC[C@H](NC(=O)OCC1c2ccccc2-c2ccccc21)C(=O)O>ClCCl>CC(C)(C)OC[C@H](NC(=O)OCC1c2ccccc2-c2ccccc21)C(=O)F |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-ff701405dbdb4c8d96cc24948af218ae | CSCC[C@@H](NC(=O)OCC1c2ccccc2-c2ccccc21)C(=O)O>>CSCC[C@@H](NC(=O)OCC1c2ccccc2-c2ccccc21)C(=O)F | N1=CC=CC=C1.N1=C(F)N=C(F)N=C1F.C(=O)(OCC1C2=CC=CC=C2C2=CC=CC=C12)N[C@H](CCSC)C(=O)O>>C(=O)(OCC1C2=CC=CC=C2C2=CC=CC=C12)N[C@H](CCSC)C(=O)F | O[C:24]([C@@H:5]([CH2:4][CH2:3][S:2][CH3:1])[NH:6][C:7](=[O:8])[O:9][CH2:10][CH:11]1[c:12]2[cH:13][cH:14][cH:15][cH:16][c:17]2-[c:18]2[cH:19][cH:20][cH:21][cH:22][c:23]21)=[O:25]>>[CH3:1][S:2][CH2:3][CH2:4][C@@H:5]([NH:6][C:7](=[O:8])[O:9][CH2:10][CH:11]1[c:12]2[cH:13][cH:14][cH:15][cH:16][c:17]2-[c:18]2[cH:19][cH:20][... | CSCC[C@@H](NC(=O)OCC1c2ccccc2-c2ccccc21)C(=O)O | CSCC[C@@H](NC(=O)OCC1c2ccccc2-c2ccccc21)C(=O)F | null | null | ClCCl | Functional Group Interconversion | OtherReaction | c301c14a9dcd0670d52e8b77396cbe7fd8edeedd757bc43f4162ade1fc52fc93 | 787f545db5dc0b29dde55b5fbed7db8625b8055f49327f97ed4d83cc47c3af1d | c1ccc2c(c1)Cc1ccccc1-2 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[#7:5]-[C:6]=[O;D1;H0:7]>>[C:4]-[C:3](-[#7:5]-[C:6]=[O;D1;H0:7])-[C;H0;D3;+0:1](-[F;D1;H0:8])=[O;D1;H0:2] | null | [] | null | null | 4 | HOUR | FMOC-D-Methionine (5.00 g, 13.46 mmol) (Bachem) was dissolved in dichloromethane (70 mL). Pyridine (1.09 mL, 13.46 mmol) (Aldrich) and cyanuric fluoride (1.82 g, 13.46 mmol) (Aldrich) were successively added at room temperature and the mixture was stirred for 4 hours. Ice cold water (100 mL) was added and the resulting... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Acyl halide | null | null | c1ccc2c(c1)Cc1ccccc12 | null | ClCCl | null | 4 | CSCC[C@@H](NC(=O)OCC1c2ccccc2-c2ccccc21)C(=O)O>ClCCl>CSCC[C@@H](NC(=O)OCC1c2ccccc2-c2ccccc21)C(=O)F |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-fdb8a9152bfd4faca050f70d5c0c0d5b | CC(C)(C)[Si](C)(C)Cl.O=[N+]([O-])c1ccc(O)cc1>>CC(C)(C)[Si](C)(C)Oc1ccc([N+](=O)[O-])cc1 | [Si](C)(C)(C(C)(C)C)Cl.[N+](=O)([O-])C1=CC=C(C=C1)O.N1C=NC=C1.[Si](C)(C)(C(C)(C)C)Cl>>[N+](=O)([O-])C1=CC=C(C=C1)O[Si](C(C)(C)C)(C)C | Cl[Si:5]([C:2]([CH3:1])([CH3:3])[CH3:4])([CH3:6])[CH3:7].[OH:8][c:9]1[cH:10][cH:11][c:12]([N+:13](=[O:14])[O-:15])[cH:16][cH:17]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[Si:5]([CH3:6])([CH3:7])[O:8][c:9]1[cH:10][cH:11][c:12]([N+:13](=[O:14])[O-:15])[cH:16][cH:17]1 | CC(C)(C)[Si](C)(C)Cl.O=[N+]([O-])c1ccc(O)cc1 | CC(C)(C)[Si](C)(C)Oc1ccc([N+](=O)[O-])cc1 | null | null | CN(C=O)C | Protection | Alcohol protection with silyl ethers | 91043baed1393f1ecd2302d7d0b31c01cf171d3977dd7c70afa1da52fa298c73 | 4a917c959d011f885a1269fa3c1f022ee5e09144996246d24e42e65634a451ac | c1ccccc1 | Cl-[Si;H0;D4;+0:1](-[C;D1;H3:2])(-[C;D1;H3:3])-[C:4](-[C;D1;H3:5])(-[C;D1;H3:6])-[C;D1;H3:7].[OH;D1;+0:8]-[c:9](:[c:10]):[c:11]>>[C;D1;H3:5]-[C:4](-[C;D1;H3:6])(-[C;D1;H3:7])-[Si;H0;D4;+0:1](-[C;D1;H3:2])(-[C;D1;H3:3])-[O;H0;D2;+0:8]-[c:9](:[c:10]):[c:11] | null | [] | null | null | 1 | DAY | To a solution of 4-nitrophenol (5.0 g, 35.9 mmol) (Aldrich) in dimethylformamide (50 mL) was added imidazole (3.18 g, 46.7 mmol) (Aldrich) and t-butyldimethylsilyl chloride (6.49 g, 43.1 mmol) (Avocado Research Chemicals Ltd.). The reaction mixture was stirred at room temperature for 1 day. TLC analysis showed starting... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic alcohol.Silyl protective group | TMS ether protective group | null | null | c1ccccc1 | HCl | CN(C=O)C | null | 24 | CC(C)(C)[Si](C)(C)Cl.O=[N+]([O-])c1ccc(O)cc1>CN(C=O)C>CC(C)(C)[Si](C)(C)Oc1ccc([N+](=O)[O-])cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-a803ccb62a404612ad797f6d240d47bb | CC(C)(C)[Si](C)(C)Oc1ccc([N+](=O)[O-])cc1>>CC(C)(C)[Si](C)(C)Oc1ccc(N)cc1 | [N+](=O)([O-])C1=CC=C(C=C1)O[Si](C(C)(C)C)(C)C>>C[Si](C(C)(C)C)(OC1=CC=C(C=C1)N)C | O=[N+:13]([O-])[c:12]1[cH:11][cH:10][c:9]([O:8][Si:5]([C:2]([CH3:1])([CH3:3])[CH3:4])([CH3:6])[CH3:7])[cH:15][cH:14]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[Si:5]([CH3:6])([CH3:7])[O:8][c:9]1[cH:10][cH:11][c:12]([NH2:13])[cH:14][cH:15]1 | CC(C)(C)[Si](C)(C)Oc1ccc([N+](=O)[O-])cc1 | CC(C)(C)[Si](C)(C)Oc1ccc(N)cc1 | null | [Pd] | C(C)(=O)OCC | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccccc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | null | null | A solution of 1-nitro4-(1,1,2,2-tetramethyl-1-silapropoxy)benzene (7.8 g, 30.8 mmol) (from Example 19a supra) and 10% Pd/C (0.70 g) (Aldrich) in ethyl acetate (100 mL) was hydrogenated for 1 day. The reaction mixture was filtered though Celite® and concentrated. The residue was purified by flash chromatography eluting ... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1 | Other | [Pd].C(C)(=O)OCC | null | null | CC(C)(C)[Si](C)(C)Oc1ccc([N+](=O)[O-])cc1>[Pd].C(C)(=O)OCC>CC(C)(C)[Si](C)(C)Oc1ccc(N)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-08b42f333f054ad0a9ab1a2e5240f66b | COC(=O)OC.COc1c(F)cc(C(C)=O)cc1F>>COC(=O)CC(=O)c1cc(F)c(OC)c(F)c1 | CC(=O)C1=CC(=C(C(=C1)F)OC)F.C(OC)(OC)=O>>FC=1C=C(C(=O)CC(=O)OC)C=C(C1OC)F | CO[C:3]([O:2][CH3:1])=[O:4].[CH3:5][C:6](=[O:7])[c:8]1[cH:9][c:10]([F:11])[c:12]([O:13][CH3:14])[c:15]([F:16])[cH:17]1>>[CH3:1][O:2][C:3](=[O:4])[CH2:5][C:6](=[O:7])[c:8]1[cH:9][c:10]([F:11])[c:12]([O:13][CH3:14])[c:15]([F:16])[cH:17]1 | COC(=O)OC.COc1c(F)cc(C(C)=O)cc1F | COC(=O)CC(=O)c1cc(F)c(OC)c(F)c1 | null | null | null | C-C Coupling | OtherReaction | 984c35cff4b3f334715b1696c3f8f2fb17ccd67fc374fcef5afdd55b5aabecf9 | d76b6fc9d01d8258e5777a3b2326a8d78a9d9a55717b27736ba55600205f4ed0 | c1ccccc1 | C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C;D1;H3:4].[CH3;D1;+0:5]-[C:6](=[O;D1;H0:7])-[c:8]>>[C;D1;H3:4]-[#8:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[CH2;D2;+0:5]-[C:6](=[O;D1;H0:7])-[c:8] | 97 | [{"value": 97.0, "product": "FC=1C=C(C(=O)CC(=O)OC)C=C(C1OC)F", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | This compound was prepared from 3,5-difluoro-4-methoxyacetophenone and dimethyl carbonate according to method A. Yellow solid; Yield: 97%; mp 64–67° C.; 1H-NMR (300 MHz, CDCl3) δ 3.77 (s, 3H), 3.93 (s, 2H), 4.13 (t, J=1.7 Hz, 3H), 7.52 (m, 2H). Minor tautomer: 3.81 (s, 3H), 4.06 (m, 3H), 5.58 (s, 1H), 7.34 (m, 2H), 12.... | 10.6084/m9.figshare.5104873.v1 | null | Carbonic Ester.Ketone | Ketone.Ester | null | null | c1ccccc1 | HO- | null | null | null | COC(=O)OC.COc1c(F)cc(C(C)=O)cc1F>>COC(=O)CC(=O)c1cc(F)c(OC)c(F)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-bebeddd30f25409fb8a19ebf0a18be6c | COc1ccc(-c2cc(C#N)c3cc(OC)ccc3n2)cc1>>N#Cc1cc(-c2ccc(O)cc2)nc2ccc(O)cc12 | C(#N)C1=CC(=NC2=CC=C(C=C12)OC)C1=CC=C(C=C1)OC.N1[C@@H](CCC1=O)C(=O)O.Br>>C(#N)C1=CC(=NC2=CC=C(C=C12)O)C1=CC=C(C=C1)O | C[O:10][c:9]1[cH:8][cH:7][c:6](-[c:5]2[cH:4][c:3]([C:2]#[N:1])[c:20]3[c:14]([n:13]2)[cH:15][cH:16][c:17]([O:18]C)[cH:19]3)[cH:12][cH:11]1>>[N:1]#[C:2][c:3]1[cH:4][c:5](-[c:6]2[cH:7][cH:8][c:9]([OH:10])[cH:11][cH:12]2)[n:13][c:14]2[cH:15][cH:16][c:17]([OH:18])[cH:19][c:20]12 | COc1ccc(-c2cc(C#N)c3cc(OC)ccc3n2)cc1 | N#Cc1cc(-c2ccc(O)cc2)nc2ccc(O)cc12 | null | null | null | Deprotection | OtherReaction | a0f05885bbc65ae2846cad0ac34029941211b2ef3a426958b0c8aa83bb16fe86 | 9df751cd682ad9d54ed75d7313aaead6a019c5d37ede15c4672866d319b900ff | c1ccc(-c2ccc3ccccc3n2)cc1 | C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4].C-[O;H0;D2;+0:5]-[c:6](:[c:7]):[c:8]>>[OH;D1;+0:1]-[c:2](:[c:3]):[c:4].[OH;D1;+0:5]-[c:6](:[c:7]):[c:8] | 89 | [{"value": 89.0, "product": "C(#N)C1=CC(=NC2=CC=C(C=C12)O)C1=CC=C(C=C1)O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | This compound was prepared from 9a using Pyr./HBr according to method I. Yellow solid; Yield: 89%; mp>240° C. (dec.); 1H-NMR (300 MHz, DMSO-d6) δ 6.92 (d, J=8.7 Hz, 2H), 7.30 (d, J=2.6 Hz, 1H), 7.45 (dd, J=9.1, 2.6 Hz, 1H), 8.02 (d, J=9.1 Hz, 1H), 8.13 (d, J=8.7 Hz, 2H), 8.58 (s, 1H), 9.93 (s, 1H), 10.64 (s, 1H); MS (E... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether | Aromatic alcohol.Aromatic alcohol | null | null | c1ccccc1.c1ccc2ncccc2c1 | Other | null | null | null | COc1ccc(-c2cc(C#N)c3cc(OC)ccc3n2)cc1>>N#Cc1cc(-c2ccc(O)cc2)nc2ccc(O)cc12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-61a03d10d06c4d8fafd1f62dfc401067 | C=[CH][Sn]([CH2]CCC)([CH2]CCC)[CH2]CCC.Oc1ccc(-c2cc(Br)c3cc(O)ccc3n2)cc1>>C=Cc1cc(-c2ccc(O)cc2)nc2ccc(O)cc12 | BrC1=CC(=NC2=CC=C(C=C12)O)C1=CC=C(C=C1)O.C(CCC)[Sn](C=C)(CCCC)CCCC>>OC1=CC=C(C=C1)C1=NC2=CC=C(C=C2C(=C1)C=C)O | CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[CH:2]=[CH2:1].Br[c:3]1[cH:4][c:5](-[c:6]2[cH:7][cH:8][c:9]([OH:10])[cH:11][cH:12]2)[n:13][c:14]2[cH:15][cH:16][c:17]([OH:18])[cH:19][c:20]12>>[CH2:1]=[CH:2][c:3]1[cH:4][c:5](-[c:6]2[cH:7][cH:8][c:9]([OH:10])[cH:11][cH:12]2)[n:13][c:14]2[cH:15][cH:16][c:17]([OH:18])[cH:19][c:20]12 | C=[CH][Sn]([CH2]CCC)([CH2]CCC)[CH2]CCC.Oc1ccc(-c2cc(Br)c3cc(O)ccc3n2)cc1 | C=Cc1cc(-c2ccc(O)cc2)nc2ccc(O)cc12 | null | null | null | C-C Coupling | Stille reaction_vinyl | b76d02284eab1606d02e43e8d6b217f827d8bc76b0b2203ccf942abed5fcc5b2 | ec03c739f58696d2a3659a73884744e1a490a20a587da6f115be382b663cf23d | c1ccc(-c2ccc3ccccc3n2)cc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3](-[c:4]):[#7;a:5]:[c:6](:[c:7]):[c:8]:1:[c:9].C-C-C-[CH2]-[Sn](-[CH2]-C-C-C)(-[CH2]-C-C-C)-[CH;D2;+0:10]=[C;D1;H2:11]>>[C;D1;H2:11]=[CH;D2;+0:10]-[c;H0;D3;+0:1]1:[c:2]:[c:3](-[c:4]):[#7;a:5]:[c:6](:[c:7]):[c:8]:1:[c:9] | 69 | [{"value": 69.0, "product": "OC1=CC=C(C=C1)C1=NC2=CC=C(C=C2C(=C1)C=C)O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | This compound was prepared from 6a and tributyl(vinyl)tin according to method J. Yellow solid; Yield: 69%; mp>200° C. (dec.); 1H-NMR (400 MHz, DMSO-d6) δ 5.69 (d, J=11.7 Hz, 1H), 6.23 (dd, J=18.3, 1.0 Hz, 1H), 6.90 (d, J=8.5 Hz, 2H), 7.31 (dd, J=9.0, 2.7 Hz, 1H), 7.35 (d, J=2.2 Hz, 1H), 7.40 (dd, J=17.3, 11.0 Hz, 1H), ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Vinyl.Tin | Vinyl | c1ccc2ncccc2c1 | c1ccc2ncccc2c1 | c1ccccc1.c1ccc2ncccc2c1 | HBr.Sn | null | null | null | C=[CH][Sn]([CH2]CCC)([CH2]CCC)[CH2]CCC.Oc1ccc(-c2cc(Br)c3cc(O)ccc3n2)cc1>>C=Cc1cc(-c2ccc(O)cc2)nc2ccc(O)cc12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-4c803b350ae34937859e5cb419f1475d | CCC[CH2][Sn]([C]#C[Si](C)(C)C)([CH2]CCC)[CH2]CCC.Oc1ccc(-c2cc(Br)c3cc(O)ccc3n2)cc1>>C[Si](C)(C)C#Cc1cc(-c2ccc(O)cc2)nc2ccc(O)cc12 | BrC1=CC(=NC2=CC=C(C=C12)O)C1=CC=C(C=C1)O.C[Si](C)(C)C#C[Sn](CCCC)(CCCC)CCCC>>OC1=CC=C(C=C1)C1=NC2=CC=C(C=C2C(=C1)C#C[Si](C)(C)C)O | CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[C:6]#[C:5][Si:2]([CH3:1])([CH3:3])[CH3:4].Br[c:7]1[cH:8][c:9](-[c:10]2[cH:11][cH:12][c:13]([OH:14])[cH:15][cH:16]2)[n:17][c:18]2[cH:19][cH:20][c:21]([OH:22])[cH:23][c:24]12>>[CH3:1][Si:2]([CH3:3])([CH3:4])[C:5]#[C:6][c:7]1[cH:8][c:9](-[c:10]2[cH:11][cH:12][c:13]([OH:14])[cH:15][cH:16]2)... | CCC[CH2][Sn]([C]#C[Si](C)(C)C)([CH2]CCC)[CH2]CCC.Oc1ccc(-c2cc(Br)c3cc(O)ccc3n2)cc1 | C[Si](C)(C)C#Cc1cc(-c2ccc(O)cc2)nc2ccc(O)cc12 | null | null | null | C-C Coupling | Stille reaction_other | 5b7d122d5cbf3feee31209339c4cd554facd746c4b7c95e3041c641d09f4e525 | 84197a108c0019520f13001872ce55981c95862f930591903269e152b52aac86 | c1ccc(-c2ccc3ccccc3n2)cc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3](-[c:4]):[#7;a:5]:[c:6](:[c:7]):[c:8]:1:[c:9].C-C-C-[CH2]-[Sn](-[C;H0;D2;+0:10]#[C:11]-[#14:12](-[C;D1;H3:13])(-[C;D1;H3:14])-[C;D1;H3:15])(-[CH2]-C-C-C)-[CH2]-C-C-C>>[C;D1;H3:13]-[#14:12](-[C;D1;H3:14])(-[C;D1;H3:15])-[C:11]#[C;H0;D2;+0:10]-[c;H0;D3;+0:1]1:[c:2]:[c:3](-[c:4]):[#7;a:5]:[c:... | 83 | [{"value": 83.0, "product": "OC1=CC=C(C=C1)C1=NC2=CC=C(C=C2C(=C1)C#C[Si](C)(C)C)O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | This compound was prepared from 6a and (trimethylsilylethynyl)tributyltin according to method J. Yellow powder; Yield: 83%; mp 210° C. (dec.); 1H-NMR (300 MHz, acetone-d6) δ 0.38 (s, 9H), 7.02 (d, J=8.7 Hz, 2H), 7.44 (dd, J=9.1, 2.7 Hz, 1H), 7.63 (d, J=2.7 Hz, 1H), 7.99 (d, J=9.1 Hz, 1H), 8.05 (s, 1H), 8.18 (d, J=8.7 H... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Alkyne.Tin | Alkyne | c1ccc2ncccc2c1 | c1ccc2ncccc2c1 | c1ccccc1.c1ccc2ncccc2c1 | HBr.Sn | null | null | null | CCC[CH2][Sn]([C]#C[Si](C)(C)C)([CH2]CCC)[CH2]CCC.Oc1ccc(-c2cc(Br)c3cc(O)ccc3n2)cc1>>C[Si](C)(C)C#Cc1cc(-c2ccc(O)cc2)nc2ccc(O)cc12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-9fbcc659dc29475ebabf18f9a67dbd15 | CCC[CH2][Sn]([C]#C[Si](C)(C)C)([CH2]CCC)[CH2]CCC.Oc1ccc2nc(-c3ccc(O)c(F)c3)cc(Br)c2c1>>C[Si](C)(C)C#Cc1cc(-c2ccc(O)c(F)c2)nc2ccc(O)cc12 | BrC1=CC(=NC2=CC=C(C=C12)O)C1=CC(=C(C=C1)O)F.C[Si](C)(C)C#C[Sn](CCCC)(CCCC)CCCC>>FC=1C=C(C=CC1O)C1=NC2=CC=C(C=C2C(=C1)C#C[Si](C)(C)C)O | CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[C:6]#[C:5][Si:2]([CH3:1])([CH3:3])[CH3:4].Br[c:7]1[cH:8][c:9](-[c:10]2[cH:11][cH:12][c:13]([OH:14])[c:15]([F:16])[cH:17]2)[n:18][c:19]2[cH:20][cH:21][c:22]([OH:23])[cH:24][c:25]12>>[CH3:1][Si:2]([CH3:3])([CH3:4])[C:5]#[C:6][c:7]1[cH:8][c:9](-[c:10]2[cH:11][cH:12][c:13]([OH:14])[c:15]([F... | CCC[CH2][Sn]([C]#C[Si](C)(C)C)([CH2]CCC)[CH2]CCC.Oc1ccc2nc(-c3ccc(O)c(F)c3)cc(Br)c2c1 | C[Si](C)(C)C#Cc1cc(-c2ccc(O)c(F)c2)nc2ccc(O)cc12 | null | null | null | C-C Coupling | Stille reaction_other | 5b7d122d5cbf3feee31209339c4cd554facd746c4b7c95e3041c641d09f4e525 | 84197a108c0019520f13001872ce55981c95862f930591903269e152b52aac86 | c1ccc(-c2ccc3ccccc3n2)cc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3](-[c:4]):[#7;a:5]:[c:6](:[c:7]):[c:8]:1:[c:9].C-C-C-[CH2]-[Sn](-[C;H0;D2;+0:10]#[C:11]-[#14:12](-[C;D1;H3:13])(-[C;D1;H3:14])-[C;D1;H3:15])(-[CH2]-C-C-C)-[CH2]-C-C-C>>[C;D1;H3:13]-[#14:12](-[C;D1;H3:14])(-[C;D1;H3:15])-[C:11]#[C;H0;D2;+0:10]-[c;H0;D3;+0:1]1:[c:2]:[c:3](-[c:4]):[#7;a:5]:[c:... | 94 | [{"value": 94.0, "product": "FC=1C=C(C=CC1O)C1=NC2=CC=C(C=C2C(=C1)C#C[Si](C)(C)C)O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | This compound was prepared from 6b and (trimethylsilylethynyl)tributyltin according to method J. Red powder; Yield: 94%; 1H-NMR (300 MHz, acetone-d6) δ 0.43 (s, 9H), 7.21 (dd, J=8.8, 8.8 Hz, 1H), 7.51 (dd, J=9.1, 2.7 Hz, 1H), 7.68 (d, J=2.7 Hz, 1H), 8.05 (m, 1H), 8.07 (d, J=9.0 Hz, 1H), 8.13 (s, 1H), 8.18 (dd, J=12.8, ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Alkyne.Tin | Alkyne | c1ccc2ncccc2c1 | c1ccc2ncccc2c1 | c1ccccc1.c1ccc2ncccc2c1 | HBr.Sn | null | null | null | CCC[CH2][Sn]([C]#C[Si](C)(C)C)([CH2]CCC)[CH2]CCC.Oc1ccc2nc(-c3ccc(O)c(F)c3)cc(Br)c2c1>>C[Si](C)(C)C#Cc1cc(-c2ccc(O)c(F)c2)nc2ccc(O)cc12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-03fd43b53d484816aceded56c9677dc8 | CCC[CH2][Sn]([C]#C[Si](C)(C)C)([CH2]CCC)[CH2]CCC.Oc1ccc2nc(-c3cc(F)c(O)c(F)c3)cc(Br)c2c1>>C#Cc1cc(-c2cc(F)c(O)c(F)c2)nc2ccc(O)cc12 | BrC1=CC(=NC2=CC=C(C=C12)O)C1=CC(=C(C(=C1)F)O)F.C[Si](C)(C)C#C[Sn](CCCC)(CCCC)CCCC>>FC=1C=C(C=C(C1O)F)C1=NC2=CC=C(C=C2C(=C1)C#C)O | CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[C:2]#[C:1][Si](C)(C)C.Br[c:3]1[cH:4][c:5](-[c:6]2[cH:7][c:8]([F:9])[c:10]([OH:11])[c:12]([F:13])[cH:14]2)[n:15][c:16]2[cH:17][cH:18][c:19]([OH:20])[cH:21][c:22]12>>[CH:1]#[C:2][c:3]1[cH:4][c:5](-[c:6]2[cH:7][c:8]([F:9])[c:10]([OH:11])[c:12]([F:13])[cH:14]2)[n:15][c:16]2[cH:17][cH:18][c:... | CCC[CH2][Sn]([C]#C[Si](C)(C)C)([CH2]CCC)[CH2]CCC.Oc1ccc2nc(-c3cc(F)c(O)c(F)c3)cc(Br)c2c1 | C#Cc1cc(-c2cc(F)c(O)c(F)c2)nc2ccc(O)cc12 | null | null | null | C-C Coupling | OtherReaction | 519663089044573005838583055d682ebb55d07ad1272ec0cac80bd42ad98882 | 42261e6f5c424e854c8a54f17242936ae7e106b9527e439abf449ecc45648867 | c1ccc(-c2ccc3ccccc3n2)cc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3](-[c:4]):[#7;a:5]:[c:6](:[c:7]):[c:8]:1:[c:9].C-C-C-[CH2]-[Sn](-[C;H0;D2;+0:10]#[C;H0;D2;+0:11]-[Si](-C)(-C)-C)(-[CH2]-C-C-C)-[CH2]-C-C-C>>[CH;D1;+0:11]#[C;H0;D2;+0:10]-[c;H0;D3;+0:1]1:[c:2]:[c:3](-[c:4]):[#7;a:5]:[c:6](:[c:7]):[c:8]:1:[c:9] | 87 | [{"value": 87.0, "product": "FC=1C=C(C=C(C1O)F)C1=NC2=CC=C(C=C2C(=C1)C#C)O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | This compound was prepared from 6c following a combination of method J using (trimethylsilylethynyl)tributyltin and method L. Yellow solid; Yield: 87%; mp 220° C. (dec.); 1H-NMR (300 MHz, acetone-d6) δ 4.39 (s, 1H), 7.45 (dd, J=9.1, 2.7 Hz, 1H), 7.60 (d, J=2.7 Hz, 1H), 7.95 (d, J=10.1 Hz, 1H), 7.96 (d, J=7.1 Hz, 1H), 8... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Alkyne.Silyl protective group.Tin | Alkyne | c1ccc2ncccc2c1 | c1ccc2ncccc2c1 | c1ccccc1.c1ccc2ncccc2c1 | HBr.Sn | null | null | null | CCC[CH2][Sn]([C]#C[Si](C)(C)C)([CH2]CCC)[CH2]CCC.Oc1ccc2nc(-c3cc(F)c(O)c(F)c3)cc(Br)c2c1>>C#Cc1cc(-c2cc(F)c(O)c(F)c2)nc2ccc(O)cc12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-61877ec17af6430e864c5fb131b6cb2a | CCC[CH2][Sn]([C]#Cc1ccccc1)([CH2]CCC)[CH2]CCC.Oc1ccc2nc(-c3ccc(O)c(F)c3)cc(Br)c2c1>>Oc1ccc2nc(-c3ccc(O)c(F)c3)cc(C#Cc3ccccc3)c2c1 | BrC1=CC(=NC2=CC=C(C=C12)O)C1=CC(=C(C=C1)O)F.C(CCC)[Sn](C#CC1=CC=CC=C1)(CCCC)CCCC>>FC=1C=C(C=CC1O)C1=NC2=CC=C(C=C2C(=C1)C#CC1=CC=CC=C1)O | CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[C:18]#[C:19][c:20]1[cH:21][cH:22][cH:23][cH:24][cH:25]1.Br[c:17]1[cH:16][c:7](-[c:8]2[cH:9][cH:10][c:11]([OH:12])[c:13]([F:14])[cH:15]2)[n:6][c:5]2[cH:4][cH:3][c:2]([OH:1])[cH:27][c:26]21>>[OH:1][c:2]1[cH:3][cH:4][c:5]2[n:6][c:7](-[c:8]3[cH:9][cH:10][c:11]([OH:12])[c:13]([F:14])[cH:15]3... | CCC[CH2][Sn]([C]#Cc1ccccc1)([CH2]CCC)[CH2]CCC.Oc1ccc2nc(-c3ccc(O)c(F)c3)cc(Br)c2c1 | Oc1ccc2nc(-c3ccc(O)c(F)c3)cc(C#Cc3ccccc3)c2c1 | null | null | null | C-C Coupling | Stille reaction_other | 5b7d122d5cbf3feee31209339c4cd554facd746c4b7c95e3041c641d09f4e525 | 84197a108c0019520f13001872ce55981c95862f930591903269e152b52aac86 | C(#Cc1cc(-c2ccccc2)nc2ccccc12)c1ccccc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3](-[c:4]):[#7;a:5]:[c:6](:[c:7]):[c:8]:1:[c:9].C-C-C-[CH2]-[Sn](-[C;H0;D2;+0:10]#[C:11]-[c:12])(-[CH2]-C-C-C)-[CH2]-C-C-C>>[c:12]-[C:11]#[C;H0;D2;+0:10]-[c;H0;D3;+0:1]1:[c:2]:[c:3](-[c:4]):[#7;a:5]:[c:6](:[c:7]):[c:8]:1:[c:9] | 92 | [{"value": 92.0, "product": "FC=1C=C(C=CC1O)C1=NC2=CC=C(C=C2C(=C1)C#CC1=CC=CC=C1)O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | This compound was prepared from 6b and tributyl(phenylethynyl)tin according to method J. Orange powder; Yield: 92%; mp 125–129° C; 1H-NMR (300 MHz, DMSO-d6) δ 7.08 (dd, J=8.8, 8.8 Hz, 1H), 7.36 (dd, J=9.0, 2.6 Hz, 1H), 7.53 (m, 3H), 7.59 (d, J=2.6 Hz, 1H), 7.74 (m, 2H), 7.94 (d, J=9.1 Hz, 2H), 8.05 (dd, J=13.0, 1.8 Hz,... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Alkyne.Tin | Alkyne | c1ccc2ncccc2c1 | c1ccc2ncccc2c1 | c1ccc2ncccc2c1.c1ccccc1.c1ccccc1 | HBr.Sn | null | null | null | CCC[CH2][Sn]([C]#Cc1ccccc1)([CH2]CCC)[CH2]CCC.Oc1ccc2nc(-c3ccc(O)c(F)c3)cc(Br)c2c1>>Oc1ccc2nc(-c3ccc(O)c(F)c3)cc(C#Cc3ccccc3)c2c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-51161c16317b4c838a8ed98ea6f53449 | CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[c]1nccs1.Oc1ccc2nc(-c3ccc(O)c(F)c3)cc(Br)c2c1>>Oc1ccc2nc(-c3ccc(O)c(F)c3)cc(-c3nccs3)c2c1 | BrC1=CC(=NC2=CC=C(C=C12)O)C1=CC(=C(C=C1)O)F.C(CCC)[Sn](C=1SC=CN1)(CCCC)CCCC>>FC=1C=C(C=CC1O)C1=NC2=CC=C(C=C2C(=C1)C=1SC=CN1)O | CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[c:18]1[n:19][cH:20][cH:21][s:22]1.Br[c:17]1[cH:16][c:7](-[c:8]2[cH:9][cH:10][c:11]([OH:12])[c:13]([F:14])[cH:15]2)[n:6][c:5]2[cH:4][cH:3][c:2]([OH:1])[cH:24][c:23]21>>[OH:1][c:2]1[cH:3][cH:4][c:5]2[n:6][c:7](-[c:8]3[cH:9][cH:10][c:11]([OH:12])[c:13]([F:14])[cH:15]3)[cH:16][c:17](-[c:18]... | CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[c]1nccs1.Oc1ccc2nc(-c3ccc(O)c(F)c3)cc(Br)c2c1 | Oc1ccc2nc(-c3ccc(O)c(F)c3)cc(-c3nccs3)c2c1 | null | null | null | C-C Coupling | Stille reaction_aryl | fc253538fac18be712decdf7e55d082e5584b30a027de13d08589650e0a5abd9 | db27eeefac0475c6d74fa10b3167e95a61caaae74e8bbafd45892452c0c3d4d6 | c1ccc(-c2cc(-c3nccs3)c3ccccc3n2)cc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3](-[c:4]):[#7;a:5]:[c:6](:[c:7]):[c:8]:1:[c:9].C-C-C-[CH2]-[Sn](-[CH2]-C-C-C)(-[CH2]-C-C-C)-[c;H0;D3;+0:10]1:[#16;a:11]:[c:12]:[c:13]:[#7;a:14]:1>>[c:9]:[c:8]1:[c:6](:[c:7]):[#7;a:5]:[c:3](-[c:4]):[c:2]:[c;H0;D3;+0:1]:1-[c;H0;D3;+0:10]1:[#16;a:11]:[c:12]:[c:13]:[#7;a:14]:1 | 56 | [{"value": 56.0, "product": "FC=1C=C(C=CC1O)C1=NC2=CC=C(C=C2C(=C1)C=1SC=CN1)O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | This compound was prepared from 6b and 2-tributylstannylthiazole according to method J. Yellow powder; Yield: 56%; mp>280° C. (dec.); 1H-NMR (400 MHz, DMSO-d6) δ 7.10 (t, J=8.8 Hz, 1H), 7.38 (dd, J=9.1, 2.7 Hz, 1H), 7.95–8.00 (m, 2H), 8.07–8.12 (m, 3H), 8.21 (m, 2H), 10.18 (s, 1H), 10.26 (s, 1H); MS (ESI) m/z 337 ([M−H... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Tin | null | c1cscn1.c1ccc2ncccc2c1 | c1ccc2ncccc2c1.c1cscn1 | c1ccc2ncccc2c1.c1ccccc1.c1cscn1 | HBr.Sn | null | null | null | CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[c]1nccs1.Oc1ccc2nc(-c3ccc(O)c(F)c3)cc(Br)c2c1>>Oc1ccc2nc(-c3ccc(O)c(F)c3)cc(-c3nccs3)c2c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-04c274e7ad19452d83077b67cba5d514 | Cc1ccc(B(O)O)cc1.Oc1ccc2nc(-c3ccc(O)c(F)c3)cc(Br)c2c1>>Cc1ccc(-c2cc(-c3ccc(O)c(F)c3)nc3ccc(O)cc23)cc1 | BrC1=CC(=NC2=CC=C(C=C12)O)C1=CC(=C(C=C1)O)F.B(C=1C=CC(=CC1)C)(O)O>>FC=1C=C(C=CC1O)C1=NC2=CC=C(C=C2C(=C1)C1=CC=C(C=C1)C)O | OB(O)[c:5]1[cH:4][cH:3][c:2]([CH3:1])[cH:26][cH:25]1.Br[c:6]1[cH:7][c:8](-[c:9]2[cH:10][cH:11][c:12]([OH:13])[c:14]([F:15])[cH:16]2)[n:17][c:18]2[cH:19][cH:20][c:21]([OH:22])[cH:23][c:24]12>>[CH3:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[cH:7][c:8](-[c:9]3[cH:10][cH:11][c:12]([OH:13])[c:14]([F:15])[cH:16]3)[n:17][c:18]3[cH:19]... | Cc1ccc(B(O)O)cc1.Oc1ccc2nc(-c3ccc(O)c(F)c3)cc(Br)c2c1 | Cc1ccc(-c2cc(-c3ccc(O)c(F)c3)nc3ccc(O)cc23)cc1 | null | null | null | C-C Coupling | Suzuki coupling with boronic acids | 73d3d45d842e591351c81053feb1b3096820b80e5a86db47217e78e2a9707cc8 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(-c2cc(-c3ccccc3)c3ccccc3n2)cc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3](-[c:4]):[#7;a:5]:[c:6](:[c:7]):[c:8]:1:[c:9].O-B(-O)-[c;H0;D3;+0:10](:[c:11]:[c:12]):[c:13]:[c:14]>>[c:7]:[c:6]1:[#7;a:5]:[c:3](-[c:4]):[c:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:10](:[c:11]:[c:12]):[c:13]:[c:14]):[c:8]:1:[c:9] | 85 | [{"value": 85.0, "product": "FC=1C=C(C=CC1O)C1=NC2=CC=C(C=C2C(=C1)C1=CC=C(C=C1)C)O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | This compound was prepared from 6b using p-tolylboronic acid according to method P. Orange powder; Yield: 85%; mp 184–188° C.; 1H-NMR (300 MHz, DMSO-d6) δ 2.44 (s, 3H), 7.07 (dd, J=8.8, 8.8 Hz, 1H), 7.12 (d, J=2.6 Hz, 1H), 7.31 (dd, J=9.1, 2.6 Hz, 1H), 7.40 (d, J=8.0 Hz, 2H), 7.49 (d, J=8.0 Hz, 2H), 7.82 (s, 1H), 7.94 ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccccc1.c1ccc2ncccc2c1 | c1ccccc1.c1ccc2ncccc2c1 | c1ccccc1.c1ccccc1.c1ccc2ncccc2c1 | HBr.B | null | null | null | Cc1ccc(B(O)O)cc1.Oc1ccc2nc(-c3ccc(O)c(F)c3)cc(Br)c2c1>>Cc1ccc(-c2cc(-c3ccc(O)c(F)c3)nc3ccc(O)cc23)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-2fa5700fd5364c35af981aebf453db3e | OB(O)c1ccc(F)cc1.Oc1ccc2nc(-c3ccc(O)c(F)c3)cc(Br)c2c1>>Oc1ccc2nc(-c3ccc(O)c(F)c3)cc(-c3ccc(F)cc3)c2c1 | BrC1=CC(=NC2=CC=C(C=C12)O)C1=CC(=C(C=C1)O)F.FC1=CC=C(C=C1)B(O)O>>FC=1C=C(C=CC1O)C1=NC2=CC=C(C=C2C(=C1)C1=CC=C(C=C1)F)O | OB(O)[c:18]1[cH:19][cH:20][c:21]([F:22])[cH:23][cH:24]1.Br[c:17]1[cH:16][c:7](-[c:8]2[cH:9][cH:10][c:11]([OH:12])[c:13]([F:14])[cH:15]2)[n:6][c:5]2[cH:4][cH:3][c:2]([OH:1])[cH:26][c:25]21>>[OH:1][c:2]1[cH:3][cH:4][c:5]2[n:6][c:7](-[c:8]3[cH:9][cH:10][c:11]([OH:12])[c:13]([F:14])[cH:15]3)[cH:16][c:17](-[c:18]3[cH:19][cH... | OB(O)c1ccc(F)cc1.Oc1ccc2nc(-c3ccc(O)c(F)c3)cc(Br)c2c1 | Oc1ccc2nc(-c3ccc(O)c(F)c3)cc(-c3ccc(F)cc3)c2c1 | null | null | null | C-C Coupling | Suzuki coupling with boronic acids | 73d3d45d842e591351c81053feb1b3096820b80e5a86db47217e78e2a9707cc8 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(-c2cc(-c3ccccc3)c3ccccc3n2)cc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3](-[c:4]):[#7;a:5]:[c:6](:[c:7]):[c:8]:1:[c:9].O-B(-O)-[c;H0;D3;+0:10](:[c:11]:[c:12]):[c:13]:[c:14]>>[c:12]:[c:11]:[c;H0;D3;+0:10](-[c;H0;D3;+0:1]1:[c:2]:[c:3](-[c:4]):[#7;a:5]:[c:6](:[c:7]):[c:8]:1:[c:9]):[c:13]:[c:14] | 90 | [{"value": 90.0, "product": "FC=1C=C(C=CC1O)C1=NC2=CC=C(C=C2C(=C1)C1=CC=C(C=C1)F)O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | This compound was prepared from 6b using 4-fluorophenylboronic acid according to method P. Orange powder; Yield: 90%; mp 240–243° C.; 1H-NMR (300 MHz, DMSO-d6) δ 7.05 (d, J=2.6 Hz, 1H), 7.07 (dd, J=8.9, 8.7 Hz, 1H), 7.32 (dd, J=9.0, 2.6 Hz, 1H), 7.44 (dd, J=8.9, 8.9 Hz, 2H), 7.63 (m, 2H), 7.86 (s, 1H), 7.95 (dd, J=8.4,... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccccc1.c1ccc2ncccc2c1 | c1ccc2ncccc2c1.c1ccccc1 | c1ccc2ncccc2c1.c1ccccc1.c1ccccc1 | HBr.B | null | null | null | OB(O)c1ccc(F)cc1.Oc1ccc2nc(-c3ccc(O)c(F)c3)cc(Br)c2c1>>Oc1ccc2nc(-c3ccc(O)c(F)c3)cc(-c3ccc(F)cc3)c2c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-2e87ef03d13944988967e1bb4dcac910 | OB(O)c1ccc(Cl)cc1.Oc1ccc2nc(-c3ccc(O)c(F)c3)cc(Br)c2c1>>Oc1ccc2nc(-c3ccc(O)c(F)c3)cc(-c3ccc(Cl)cc3)c2c1 | BrC1=CC(=NC2=CC=C(C=C12)O)C1=CC(=C(C=C1)O)F.ClC1=CC=C(C=C1)B(O)O>>ClC1=CC=C(C=C1)C1=CC(=NC2=CC=C(C=C12)O)C1=CC(=C(C=C1)O)F | OB(O)[c:18]1[cH:19][cH:20][c:21]([Cl:22])[cH:23][cH:24]1.Br[c:17]1[cH:16][c:7](-[c:8]2[cH:9][cH:10][c:11]([OH:12])[c:13]([F:14])[cH:15]2)[n:6][c:5]2[cH:4][cH:3][c:2]([OH:1])[cH:26][c:25]21>>[OH:1][c:2]1[cH:3][cH:4][c:5]2[n:6][c:7](-[c:8]3[cH:9][cH:10][c:11]([OH:12])[c:13]([F:14])[cH:15]3)[cH:16][c:17](-[c:18]3[cH:19][c... | OB(O)c1ccc(Cl)cc1.Oc1ccc2nc(-c3ccc(O)c(F)c3)cc(Br)c2c1 | Oc1ccc2nc(-c3ccc(O)c(F)c3)cc(-c3ccc(Cl)cc3)c2c1 | null | null | null | C-C Coupling | Suzuki coupling with boronic acids | 73d3d45d842e591351c81053feb1b3096820b80e5a86db47217e78e2a9707cc8 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(-c2cc(-c3ccccc3)c3ccccc3n2)cc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3](-[c:4]):[#7;a:5]:[c:6](:[c:7]):[c:8]:1:[c:9].O-B(-O)-[c;H0;D3;+0:10](:[c:11]:[c:12]):[c:13]:[c:14]>>[c:12]:[c:11]:[c;H0;D3;+0:10](-[c;H0;D3;+0:1]1:[c:2]:[c:3](-[c:4]):[#7;a:5]:[c:6](:[c:7]):[c:8]:1:[c:9]):[c:13]:[c:14] | 87 | [{"value": 87.0, "product": "ClC1=CC=C(C=C1)C1=CC(=NC2=CC=C(C=C12)O)C1=CC(=C(C=C1)O)F", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | This compound was prepared from 6b using 4-chlorophenylboronic acid according to method P. Orange powder; Yield: 87%; mp 140–147° C.; 1H-NMR (400 MHz, DMSO-d6) δ 7.03 (d, J=2.7 Hz, 1H), 7.06 (t, J=8.8 Hz, 1H), 7.32 (dd, J=9.1, 2.7 Hz, 1H), 7.63 (d, J=8.8 Hz, 2H), 7.67 (d, J=8.7 Hz, 2H), 7.87 (s, 1H), 7.93–7.98 (m, 2H),... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccccc1.c1ccc2ncccc2c1 | c1ccc2ncccc2c1.c1ccccc1 | c1ccc2ncccc2c1.c1ccccc1.c1ccccc1 | HBr.B | null | null | null | OB(O)c1ccc(Cl)cc1.Oc1ccc2nc(-c3ccc(O)c(F)c3)cc(Br)c2c1>>Oc1ccc2nc(-c3ccc(O)c(F)c3)cc(-c3ccc(Cl)cc3)c2c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-abdf39d15bf8495fba05b5d7db69b61a | N#Cc1ccc(B(O)O)cc1.Oc1ccc2nc(-c3ccc(O)c(F)c3)cc(Br)c2c1>>N#Cc1ccc(-c2cc(-c3ccc(O)c(F)c3)nc3ccc(O)cc23)cc1 | BrC1=CC(=NC2=CC=C(C=C12)O)C1=CC(=C(C=C1)O)F.C(#N)C1=CC=C(C=C1)B(O)O>>C(#N)C1=CC=C(C=C1)C1=CC(=NC2=CC=C(C=C12)O)C1=CC(=C(C=C1)O)F | OB(O)[c:6]1[cH:5][cH:4][c:3]([C:2]#[N:1])[cH:27][cH:26]1.Br[c:7]1[cH:8][c:9](-[c:10]2[cH:11][cH:12][c:13]([OH:14])[c:15]([F:16])[cH:17]2)[n:18][c:19]2[cH:20][cH:21][c:22]([OH:23])[cH:24][c:25]12>>[N:1]#[C:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][c:9](-[c:10]3[cH:11][cH:12][c:13]([OH:14])[c:15]([F:16])[cH:17]3)[n:18][c:1... | N#Cc1ccc(B(O)O)cc1.Oc1ccc2nc(-c3ccc(O)c(F)c3)cc(Br)c2c1 | N#Cc1ccc(-c2cc(-c3ccc(O)c(F)c3)nc3ccc(O)cc23)cc1 | null | null | null | C-C Coupling | Suzuki coupling with boronic acids | 73d3d45d842e591351c81053feb1b3096820b80e5a86db47217e78e2a9707cc8 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(-c2cc(-c3ccccc3)c3ccccc3n2)cc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3](-[c:4]):[#7;a:5]:[c:6](:[c:7]):[c:8]:1:[c:9].O-B(-O)-[c;H0;D3;+0:10](:[c:11]:[c:12]):[c:13]:[c:14]>>[c:4]-[c:3]1:[#7;a:5]:[c:6](:[c:7]):[c:8](:[c:9]):[c;H0;D3;+0:1](-[c;H0;D3;+0:10](:[c:11]:[c:12]):[c:13]:[c:14]):[c:2]:1 | 52 | [{"value": 52.0, "product": "C(#N)C1=CC=C(C=C1)C1=CC(=NC2=CC=C(C=C12)O)C1=CC(=C(C=C1)O)F", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | This compound was prepared from 6b using 4-cyanophenylboronic acid according to method P. Yellow powder; Yield: 52%; mp 266–267° C.; 1H-NMR (400 MHz, DMSO-d6) δ 6.97 (d, J=2.7 Hz, 1H), 7.07 (t, J=8.8 Hz, 1H), 7.34 (dd, J=9.0, 2.6 Hz, 1H), 7.82 (d, J=8.5 Hz, 2H), 7.92 (s, 1H), 7.95–8.00 (m, 2H), 8.07–8.10 (m, 3H), 10.00... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccccc1.c1ccc2ncccc2c1 | c1ccccc1.c1ccc2ncccc2c1 | c1ccccc1.c1ccccc1.c1ccc2ncccc2c1 | HBr.B | null | null | null | N#Cc1ccc(B(O)O)cc1.Oc1ccc2nc(-c3ccc(O)c(F)c3)cc(Br)c2c1>>N#Cc1ccc(-c2cc(-c3ccc(O)c(F)c3)nc3ccc(O)cc23)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-3b1a5620622c48788ea58af1537cfdc0 | OB(O)c1ccc(C(F)(F)F)cc1.Oc1ccc2nc(-c3ccc(O)c(F)c3)cc(Br)c2c1>>Oc1ccc2nc(-c3ccc(O)c(F)c3)cc(-c3ccc(C(F)(F)F)cc3)c2c1 | BrC1=CC(=NC2=CC=C(C=C12)O)C1=CC(=C(C=C1)O)F.FC(C1=CC=C(C=C1)B(O)O)(F)F>>FC=1C=C(C=CC1O)C1=NC2=CC=C(C=C2C(=C1)C1=CC=C(C=C1)C(F)(F)F)O | OB(O)[c:18]1[cH:19][cH:20][c:21]([C:22]([F:23])([F:24])[F:25])[cH:26][cH:27]1.Br[c:17]1[cH:16][c:7](-[c:8]2[cH:9][cH:10][c:11]([OH:12])[c:13]([F:14])[cH:15]2)[n:6][c:5]2[cH:4][cH:3][c:2]([OH:1])[cH:29][c:28]21>>[OH:1][c:2]1[cH:3][cH:4][c:5]2[n:6][c:7](-[c:8]3[cH:9][cH:10][c:11]([OH:12])[c:13]([F:14])[cH:15]3)[cH:16][c:... | OB(O)c1ccc(C(F)(F)F)cc1.Oc1ccc2nc(-c3ccc(O)c(F)c3)cc(Br)c2c1 | Oc1ccc2nc(-c3ccc(O)c(F)c3)cc(-c3ccc(C(F)(F)F)cc3)c2c1 | null | null | null | C-C Coupling | Suzuki coupling with boronic acids | 73d3d45d842e591351c81053feb1b3096820b80e5a86db47217e78e2a9707cc8 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(-c2cc(-c3ccccc3)c3ccccc3n2)cc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3](-[c:4]):[#7;a:5]:[c:6](:[c:7]):[c:8]:1:[c:9].O-B(-O)-[c;H0;D3;+0:10](:[c:11]:[c:12]):[c:13]:[c:14]>>[c:12]:[c:11]:[c;H0;D3;+0:10](-[c;H0;D3;+0:1]1:[c:2]:[c:3](-[c:4]):[#7;a:5]:[c:6](:[c:7]):[c:8]:1:[c:9]):[c:13]:[c:14] | 76 | [{"value": 76.0, "product": "FC=1C=C(C=CC1O)C1=NC2=CC=C(C=C2C(=C1)C1=CC=C(C=C1)C(F)(F)F)O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | This compound was prepared from 6b using 4-trifluoromethylphenylboronic acid according to method P. Yellow crystals; Yield: 76%; mp 299–300° C.; 1H-NMR (400 MHz, DMSO-d6) δ 7.07 (dd, J=8.8, 8.8 Hz, 1H), 7.12 (d, J=2.6 Hz, 1H), 7.31 (dd, J=9.1, 2.6 Hz, 1H), 7.40 (d, J=8.0 Hz, 2H), 7.49 (d, J=8.0 Hz, 2H), 7.82 (s, 1H), 7... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccccc1.c1ccc2ncccc2c1 | c1ccc2ncccc2c1.c1ccccc1 | c1ccc2ncccc2c1.c1ccccc1.c1ccccc1 | HBr.B | null | null | null | OB(O)c1ccc(C(F)(F)F)cc1.Oc1ccc2nc(-c3ccc(O)c(F)c3)cc(Br)c2c1>>Oc1ccc2nc(-c3ccc(O)c(F)c3)cc(-c3ccc(C(F)(F)F)cc3)c2c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-0e818c8419c54a7fac724398d987ee72 | OB(O)c1ccsc1.Oc1ccc2nc(-c3ccc(O)c(F)c3)cc(Br)c2c1>>Oc1ccc2nc(-c3ccc(O)c(F)c3)cc(-c3ccsc3)c2c1 | BrC1=CC(=NC2=CC=C(C=C12)O)C1=CC(=C(C=C1)O)F.S1C=C(C=C1)B(O)O>>FC=1C=C(C=CC1O)C1=NC2=CC=C(C=C2C(=C1)C1=CSC=C1)O | OB(O)[c:18]1[cH:19][cH:20][s:21][cH:22]1.Br[c:17]1[cH:16][c:7](-[c:8]2[cH:9][cH:10][c:11]([OH:12])[c:13]([F:14])[cH:15]2)[n:6][c:5]2[cH:4][cH:3][c:2]([OH:1])[cH:24][c:23]21>>[OH:1][c:2]1[cH:3][cH:4][c:5]2[n:6][c:7](-[c:8]3[cH:9][cH:10][c:11]([OH:12])[c:13]([F:14])[cH:15]3)[cH:16][c:17](-[c:18]3[cH:19][cH:20][s:21][cH:2... | OB(O)c1ccsc1.Oc1ccc2nc(-c3ccc(O)c(F)c3)cc(Br)c2c1 | Oc1ccc2nc(-c3ccc(O)c(F)c3)cc(-c3ccsc3)c2c1 | null | null | null | C-C Coupling | Suzuki coupling with boronic acids | 7ec2bb10523ea4edebf661f837af8541c569fb5ea40337ce1dd151fc4300fa1e | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(-c2cc(-c3ccsc3)c3ccccc3n2)cc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3](-[c:4]):[#7;a:5]:[c:6](:[c:7]):[c:8]:1:[c:9].O-B(-O)-[c;H0;D3;+0:10]1:[c:11]:[c:12]:[#16;a:13]:[c:14]:1>>[c:9]:[c:8]1:[c:6](:[c:7]):[#7;a:5]:[c:3](-[c:4]):[c:2]:[c;H0;D3;+0:1]:1-[c;H0;D3;+0:10]1:[c:11]:[c:12]:[#16;a:13]:[c:14]:1 | 95 | [{"value": 95.0, "product": "FC=1C=C(C=CC1O)C1=NC2=CC=C(C=C2C(=C1)C1=CSC=C1)O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | This compound was prepared from 6b using 3-thiopheneboronic acid according to method P. Orange powder; Yield: 95%; mp>160° C. (dec.); 1H-NMR (400 MHz, DMSO-d6) δ 7.06 (t, J=8.8 Hz, 1H), 7.30–7.33 (m, 2H), 7.50 (dd, J=4.9, 1.2 Hz, 1H), 7.82 (dd, J=4.9, 3.0 Hz, 1H), 7.90–7.95 (m, 4H), 8.06 (dd, J=13.0, 2.1 Hz, 1H), 9.97 ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccsc1.c1ccc2ncccc2c1 | c1ccc2ncccc2c1.c1ccsc1 | c1ccc2ncccc2c1.c1ccccc1.c1ccsc1 | HBr.B | null | null | null | OB(O)c1ccsc1.Oc1ccc2nc(-c3ccc(O)c(F)c3)cc(Br)c2c1>>Oc1ccc2nc(-c3ccc(O)c(F)c3)cc(-c3ccsc3)c2c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-2462d807654541a2a1bf0f369b69e9aa | OB(O)c1ccncc1.Oc1ccc2nc(-c3ccc(O)c(F)c3)cc(Br)c2c1>>Oc1ccc2nc(-c3ccc(O)c(F)c3)cc(-c3ccncc3)c2c1 | BrC1=CC(=NC2=CC=C(C=C12)O)C1=CC(=C(C=C1)O)F.N1=CC=C(C=C1)B(O)O>>FC=1C=C(C=CC1O)C1=NC2=CC=C(C=C2C(=C1)C1=CC=NC=C1)O | OB(O)[c:18]1[cH:19][cH:20][n:21][cH:22][cH:23]1.Br[c:17]1[cH:16][c:7](-[c:8]2[cH:9][cH:10][c:11]([OH:12])[c:13]([F:14])[cH:15]2)[n:6][c:5]2[cH:4][cH:3][c:2]([OH:1])[cH:25][c:24]21>>[OH:1][c:2]1[cH:3][cH:4][c:5]2[n:6][c:7](-[c:8]3[cH:9][cH:10][c:11]([OH:12])[c:13]([F:14])[cH:15]3)[cH:16][c:17](-[c:18]3[cH:19][cH:20][n:2... | OB(O)c1ccncc1.Oc1ccc2nc(-c3ccc(O)c(F)c3)cc(Br)c2c1 | Oc1ccc2nc(-c3ccc(O)c(F)c3)cc(-c3ccncc3)c2c1 | null | null | null | C-C Coupling | Suzuki coupling with boronic acids | 65c50f146f4e013debcd45594af7db1f345f787e9158328ac1b943e3b140f8c7 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(-c2cc(-c3ccncc3)c3ccccc3n2)cc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3](-[c:4]):[#7;a:5]:[c:6](:[c:7]):[c:8]:1:[c:9].O-B(-O)-[c;H0;D3;+0:10]1:[c:11]:[c:12]:[#7;a:13]:[c:14]:[c:15]:1>>[c:9]:[c:8]1:[c:6](:[c:7]):[#7;a:5]:[c:3](-[c:4]):[c:2]:[c;H0;D3;+0:1]:1-[c;H0;D3;+0:10]1:[c:11]:[c:12]:[#7;a:13]:[c:14]:[c:15]:1 | 20 | [{"value": 20.0, "product": "FC=1C=C(C=CC1O)C1=NC2=CC=C(C=C2C(=C1)C1=CC=NC=C1)O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | This compound was prepared from 6b using 4-pyridinylboronic acid according to method P. Yellow powder; Yield: 20%; mp>350° C. (dec.); 1H-NMR (400 MHz, DMSO-d6) δ 7.02 (d, J=2.6 Hz, 1H), 7.07 (t, J=8.8 Hz, 1H), 7.34 (dd, J=9.0, 2.6 Hz, 1H), 7.64 (d, J=5.9 Hz, 2H), 7.93 (s, 1H), 7.95–8.00 (m, 2H), 8.08 (dd, J=13.0, 2.1 H... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccncc1.c1ccc2ncccc2c1 | c1ccc2ncccc2c1.c1ccncc1 | c1ccc2ncccc2c1.c1ccccc1.c1ccncc1 | HBr.B | null | null | null | OB(O)c1ccncc1.Oc1ccc2nc(-c3ccc(O)c(F)c3)cc(Br)c2c1>>Oc1ccc2nc(-c3ccc(O)c(F)c3)cc(-c3ccncc3)c2c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-bf76c2d6b3c04c949b881161cb4b3370 | OB(O)c1cncnc1.Oc1ccc2nc(-c3ccc(O)c(F)c3)cc(Br)c2c1>>Oc1ccc2nc(-c3ccc(O)c(F)c3)cc(-c3cncnc3)c2c1 | BrC1=CC(=NC2=CC=C(C=C12)O)C1=CC(=C(C=C1)O)F.N1=CN=CC(=C1)B(O)O>>FC=1C=C(C=CC1O)C1=NC2=CC=C(C=C2C(=C1)C=1C=NC=NC1)O | OB(O)[c:18]1[cH:19][n:20][cH:21][n:22][cH:23]1.Br[c:17]1[cH:16][c:7](-[c:8]2[cH:9][cH:10][c:11]([OH:12])[c:13]([F:14])[cH:15]2)[n:6][c:5]2[cH:4][cH:3][c:2]([OH:1])[cH:25][c:24]21>>[OH:1][c:2]1[cH:3][cH:4][c:5]2[n:6][c:7](-[c:8]3[cH:9][cH:10][c:11]([OH:12])[c:13]([F:14])[cH:15]3)[cH:16][c:17](-[c:18]3[cH:19][n:20][cH:21... | OB(O)c1cncnc1.Oc1ccc2nc(-c3ccc(O)c(F)c3)cc(Br)c2c1 | Oc1ccc2nc(-c3ccc(O)c(F)c3)cc(-c3cncnc3)c2c1 | null | null | null | C-C Coupling | Suzuki coupling with boronic acids | 0d1faee6975c7818135cd293769cc69788382bc29eaa2ec7b2053932304d61e3 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(-c2cc(-c3cncnc3)c3ccccc3n2)cc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3](-[c:4]):[#7;a:5]:[c:6](:[c:7]):[c:8]:1:[c:9].O-B(-O)-[c;H0;D3;+0:10]1:[c:11]:[#7;a:12]:[c:13]:[#7;a:14]:[c:15]:1>>[c:9]:[c:8]1:[c:6](:[c:7]):[#7;a:5]:[c:3](-[c:4]):[c:2]:[c;H0;D3;+0:1]:1-[c;H0;D3;+0:10]1:[c:11]:[#7;a:12]:[c:13]:[#7;a:14]:[c:15]:1 | 34 | [{"value": 34.0, "product": "FC=1C=C(C=CC1O)C1=NC2=CC=C(C=C2C(=C1)C=1C=NC=NC1)O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | This compound was prepared from 6b using 5-pyrimidinylboronic acid according to method P. Yellow powder; Yield: 34%; mp>340° C. (dec.); 1H-NMR (400 MHz, DMSO-d6) δ 7.00 (d, J=2.6 Hz, 1H), 7.08 (t, J=8.8 Hz, 1H), 7.36 (dd, J=9.0, 2.6 Hz, 1 H), 7.98–8.02 (m, 2H), 8.08 (s, 1H), 8.11 (dd, J=13.1, 2.2 Hz, 1H), 9.11 (s, 2H),... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1cncnc1.c1ccc2ncccc2c1 | c1ccc2ncccc2c1.c1cncnc1 | c1ccc2ncccc2c1.c1ccccc1.c1cncnc1 | HBr.B | null | null | null | OB(O)c1cncnc1.Oc1ccc2nc(-c3ccc(O)c(F)c3)cc(Br)c2c1>>Oc1ccc2nc(-c3ccc(O)c(F)c3)cc(-c3cncnc3)c2c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-24f6748ad3254b64b7ff404d539083cd | OB(O)c1ccc(F)cc1.Oc1ccc(-c2nc3ccc(O)cc3c(Br)c2Cl)cc1>>Oc1ccc(-c2nc3ccc(O)cc3c(-c3ccc(F)cc3)c2Cl)cc1 | BrC1=C(C(=NC2=CC=C(C=C12)O)C1=CC=C(C=C1)O)Cl.FC1=CC=C(C=C1)B(O)O>>ClC=1C(=NC2=CC=C(C=C2C1C1=CC=C(C=C1)F)O)C1=CC=C(C=C1)O | OB(O)[c:16]1[cH:17][cH:18][c:19]([F:20])[cH:21][cH:22]1.Br[c:15]1[c:14]2[c:8]([n:7][c:6](-[c:5]3[cH:4][cH:3][c:2]([OH:1])[cH:26][cH:25]3)[c:23]1[Cl:24])[cH:9][cH:10][c:11]([OH:12])[cH:13]2>>[OH:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[n:7][c:8]3[cH:9][cH:10][c:11]([OH:12])[cH:13][c:14]3[c:15](-[c:16]3[cH:17][cH:18][c:19]([F:2... | OB(O)c1ccc(F)cc1.Oc1ccc(-c2nc3ccc(O)cc3c(Br)c2Cl)cc1 | Oc1ccc(-c2nc3ccc(O)cc3c(-c3ccc(F)cc3)c2Cl)cc1 | null | null | null | C-C Coupling | Suzuki coupling with boronic acids | 73d3d45d842e591351c81053feb1b3096820b80e5a86db47217e78e2a9707cc8 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(-c2cc(-c3ccccc3)c3ccccc3n2)cc1 | Br-[c;H0;D3;+0:1]1:[c:2](:[c:3]):[c:4](:[c:5]):[#7;a:6]:[c:7](-[c:8]):[c:9]:1-[Cl;D1;H0:10].O-B(-O)-[c;H0;D3;+0:11](:[c:12]:[c:13]):[c:14]:[c:15]>>[Cl;D1;H0:10]-[c:9]1:[c:7](-[c:8]):[#7;a:6]:[c:4](:[c:5]):[c:2](:[c:3]):[c;H0;D3;+0:1]:1-[c;H0;D3;+0:11](:[c:12]:[c:13]):[c:14]:[c:15] | 95 | [{"value": 95.0, "product": "ClC=1C(=NC2=CC=C(C=C2C1C1=CC=C(C=C1)F)O)C1=CC=C(C=C1)O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | This compound was prepared from 35a and 4-fluorophenylboronic acid according to method P. White solid; Yield: 95%; mp 295–296° C.; 1H-NMR (300 MHz, DMSO-d6) δ 6.55 (d, J=2.6 Hz, 1H), 6.87 (d, J=8.6 Hz, 2H), 7.31 (dd, J=9.1, 2.6 Hz, 1H), 7.45 (m, 4H), 7.57 (d, J=8.6 Hz, 2H), 7.92 (d, J=9.1 Hz, 1H), 9.73 (s, 1H), 10.07 (... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccccc1.c1ccc2ncccc2c1 | c1ccc2ncccc2c1.c1ccccc1 | c1ccccc1.c1ccc2ncccc2c1.c1ccccc1 | HBr.B | null | null | null | OB(O)c1ccc(F)cc1.Oc1ccc(-c2nc3ccc(O)cc3c(Br)c2Cl)cc1>>Oc1ccc(-c2nc3ccc(O)cc3c(-c3ccc(F)cc3)c2Cl)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-2b0d9ce6dac1428494fdac9548bda8fb | COc1ccc2nc(-c3ccc(OC)c(F)c3)c(Cl)c(Br)c2c1.O=C1CC[C@@H](C(=O)O)N1>>N#Cc1c(Cl)c(-c2ccc(O)c(F)c2)nc2ccc(O)cc12 | BrC1=C(C(=NC2=CC=C(C=C12)OC)C1=CC(=C(C=C1)OC)F)Cl.N1[C@@H](CCC1=O)C(=O)O.Cl>>ClC=1C(=NC2=CC=C(C=C2C1C#N)O)C1=CC(=C(C=C1)O)F | C[O:11][c:10]1[cH:9][cH:8][c:7](-[c:6]2[c:4]([Cl:5])[c:3](Br)[c:22]3[c:16]([n:15]2)[cH:17][cH:18][c:19]([O:20]C)[cH:21]3)[cH:14][c:12]1[F:13].O=C(O)[C@@H]1CC[C:2](=O)[NH:1]1>>[N:1]#[C:2][c:3]1[c:4]([Cl:5])[c:6](-[c:7]2[cH:8][cH:9][c:10]([OH:11])[c:12]([F:13])[cH:14]2)[n:15][c:16]2[cH:17][cH:18][c:19]([OH:20])[cH:21][c:... | COc1ccc2nc(-c3ccc(OC)c(F)c3)c(Cl)c(Br)c2c1.O=C1CC[C@@H](C(=O)O)N1 | N#Cc1c(Cl)c(-c2ccc(O)c(F)c2)nc2ccc(O)cc12 | null | null | null | C-C Coupling | OtherReaction | e0141a8a25f67f65ff4a531b5b01a33f09546dbc4f21eaf313e861d84a1da590 | 84342470fb695059ed8ce211dd27ea5e5a1d7559cdd73a98a0caf487589adb38 | c1ccc(-c2ccc3ccccc3n2)cc1 | Br-[c;H0;D3;+0:1]1:[c:2]2:[c:3]:[c:4](-[O;H0;D2;+0:5]-C):[c:6]:[c:7]:[c:8]:2:[#7;a:9]:[c:10](-[c:11]):[c:12]:1-[Cl;D1;H0:13].C-[O;H0;D2;+0:14]-[c:15](:[c:16]):[c:17].O-C(=O)-[C@H]1-C-C-[C;H0;D3;+0:18](=O)-[NH;D2;+0:19]-1>>[Cl;D1;H0:13]-[c:12]1:[c:10](-[c:11]):[#7;a:9]:[c:8]2:[c:7]:[c:6]:[c:4](-[OH;D1;+0:5]):[c:3]:[c:2]... | 41 | [{"value": 41.0, "product": "ClC=1C(=NC2=CC=C(C=C2C1C#N)O)C1=CC(=C(C=C1)O)F", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | This compound was prepared from 34b according to method F and method G (using Pyr./HCl). Yellow solid; Yield: 41% (for two steps); mp 325–328° C. (dec.); 1H-NMR (300 MHz, DMSO-d6) δ 7.10 (dd, J=8.8, 8.7 Hz, 1H), 7.27 (d, J=2.5 Hz, 1H), 7.43 (dd, J=8.4, 1.4 Hz, 1H), 7.49 (dd, J=9.2, 2.5 Hz, 1H), 7.55 (dd, J=12.2, 2.0 Hz... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Carboxylic acid.Ether.Ether.Secondary amide | Nitrile.Aromatic alcohol.Aromatic alcohol | c1ccc2ncccc2c1.C1CCNC1 | c1ccc2ncccc2c1 | c1ccccc1.c1ccc2ncccc2c1 | HBr | null | null | null | COc1ccc2nc(-c3ccc(OC)c(F)c3)c(Cl)c(Br)c2c1.O=C1CC[C@@H](C(=O)O)N1>>N#Cc1c(Cl)c(-c2ccc(O)c(F)c2)nc2ccc(O)cc12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-33d7c3429b6b44bb87a813f255e9b2cc | CCC[CH2][Sn]([C]#C[Si](C)(C)C)([CH2]CCC)[CH2]CCC.Oc1cc(Cl)c2nc(-c3ccc(O)c(F)c3)cc(Br)c2c1>>C#Cc1cc(-c2ccc(O)c(F)c2)nc2c(Cl)cc(O)cc12 | BrC1=CC(=NC2=C(C=C(C=C12)O)Cl)C1=CC(=C(C=C1)O)F.C[Si](C)(C)C#C[Sn](CCCC)(CCCC)CCCC>>ClC=1C=C(C=C2C(=CC(=NC12)C1=CC(=C(C=C1)O)F)C#C)O | CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[C:2]#[C:1][Si](C)(C)C.Br[c:3]1[cH:4][c:5](-[c:6]2[cH:7][cH:8][c:9]([OH:10])[c:11]([F:12])[cH:13]2)[n:14][c:15]2[c:16]([Cl:17])[cH:18][c:19]([OH:20])[cH:21][c:22]12>>[CH:1]#[C:2][c:3]1[cH:4][c:5](-[c:6]2[cH:7][cH:8][c:9]([OH:10])[c:11]([F:12])[cH:13]2)[n:14][c:15]2[c:16]([Cl:17])[cH:18][... | CCC[CH2][Sn]([C]#C[Si](C)(C)C)([CH2]CCC)[CH2]CCC.Oc1cc(Cl)c2nc(-c3ccc(O)c(F)c3)cc(Br)c2c1 | C#Cc1cc(-c2ccc(O)c(F)c2)nc2c(Cl)cc(O)cc12 | null | null | null | C-C Coupling | OtherReaction | 519663089044573005838583055d682ebb55d07ad1272ec0cac80bd42ad98882 | 42261e6f5c424e854c8a54f17242936ae7e106b9527e439abf449ecc45648867 | c1ccc(-c2ccc3ccccc3n2)cc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3](-[c:4]):[#7;a:5]:[c:6](:[c:7]):[c:8]:1:[c:9].C-C-C-[CH2]-[Sn](-[C;H0;D2;+0:10]#[C;H0;D2;+0:11]-[Si](-C)(-C)-C)(-[CH2]-C-C-C)-[CH2]-C-C-C>>[CH;D1;+0:11]#[C;H0;D2;+0:10]-[c;H0;D3;+0:1]1:[c:2]:[c:3](-[c:4]):[#7;a:5]:[c:6](:[c:7]):[c:8]:1:[c:9] | 73 | [{"value": 73.0, "product": "ClC=1C=C(C=C2C(=CC(=NC12)C1=CC(=C(C=C1)O)F)C#C)O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | This compound was prepared from 45a following a combination of method J using (trimethylsilylethynyl)tributyltin and method L. Yellow solid; Yield: 73%; mp 210° C. (dec.); 1H-NMR (400 MHz, DMSO-d6) δ 5.06 (s, 1H), 7.09 (dd, J=8.9, 8.8 Hz, 1H), 7.45 (d, J=2.6 Hz, 1H), 7.56 (d, J=2.6 Hz, 1H), 8.00 (dd, J=8.5, 1.7 Hz, 1H)... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Alkyne.Silyl protective group.Tin | Alkyne | c1ccc2ncccc2c1 | c1ccc2ncccc2c1 | c1ccccc1.c1ccc2ncccc2c1 | HBr.Sn | null | null | null | CCC[CH2][Sn]([C]#C[Si](C)(C)C)([CH2]CCC)[CH2]CCC.Oc1cc(Cl)c2nc(-c3ccc(O)c(F)c3)cc(Br)c2c1>>C#Cc1cc(-c2ccc(O)c(F)c2)nc2c(Cl)cc(O)cc12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-d2ccbacffcae40e28a57686d20464e40 | C=[CH][Sn]([CH2]CCC)([CH2]CCC)[CH2]CCC.Oc1cc(Cl)c2nc(-c3ccc(O)c(F)c3)cc(Br)c2c1>>C=Cc1cc(-c2ccc(O)c(F)c2)nc2c(Cl)cc(O)cc12 | BrC1=CC(=NC2=C(C=C(C=C12)O)Cl)C1=CC(=C(C=C1)O)F.C(CCC)[Sn](C=C)(CCCC)CCCC>>ClC=1C=C(C=C2C(=CC(=NC12)C1=CC(=C(C=C1)O)F)C=C)O | CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[CH:2]=[CH2:1].Br[c:3]1[cH:4][c:5](-[c:6]2[cH:7][cH:8][c:9]([OH:10])[c:11]([F:12])[cH:13]2)[n:14][c:15]2[c:16]([Cl:17])[cH:18][c:19]([OH:20])[cH:21][c:22]12>>[CH2:1]=[CH:2][c:3]1[cH:4][c:5](-[c:6]2[cH:7][cH:8][c:9]([OH:10])[c:11]([F:12])[cH:13]2)[n:14][c:15]2[c:16]([Cl:17])[cH:18][c:19](... | C=[CH][Sn]([CH2]CCC)([CH2]CCC)[CH2]CCC.Oc1cc(Cl)c2nc(-c3ccc(O)c(F)c3)cc(Br)c2c1 | C=Cc1cc(-c2ccc(O)c(F)c2)nc2c(Cl)cc(O)cc12 | null | null | null | C-C Coupling | Stille reaction_vinyl | b76d02284eab1606d02e43e8d6b217f827d8bc76b0b2203ccf942abed5fcc5b2 | ec03c739f58696d2a3659a73884744e1a490a20a587da6f115be382b663cf23d | c1ccc(-c2ccc3ccccc3n2)cc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3](-[c:4]):[#7;a:5]:[c:6](:[c:7]):[c:8]:1:[c:9].C-C-C-[CH2]-[Sn](-[CH2]-C-C-C)(-[CH2]-C-C-C)-[CH;D2;+0:10]=[C;D1;H2:11]>>[C;D1;H2:11]=[CH;D2;+0:10]-[c;H0;D3;+0:1]1:[c:2]:[c:3](-[c:4]):[#7;a:5]:[c:6](:[c:7]):[c:8]:1:[c:9] | 84 | [{"value": 84.0, "product": "ClC=1C=C(C=C2C(=CC(=NC12)C1=CC(=C(C=C1)O)F)C=C)O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | This compound was prepared from 45a based on method J using 1.1 equiv. of tributyl(vinyl)tin at 90° C. Red solid; Yield: 84%; mp 225° C. (dec.); 1H-NMR (400 MHz, DMSO-d6) δ 5.74 (dd, J=11.1, 1.0 Hz, 1H), 6.30 (dd, J=17.3, 1.1 Hz, 1H), 7.10 (dd, J=8.8, 8.8 Hz, 1H), 7.35 (d, J=2.6 Hz, 1H), 7.38 (dd, J=17.3, 11.1 Hz, 1H),... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Vinyl.Tin | Vinyl | c1ccc2ncccc2c1 | c1ccc2ncccc2c1 | c1ccccc1.c1ccc2ncccc2c1 | HBr.Sn | null | null | null | C=[CH][Sn]([CH2]CCC)([CH2]CCC)[CH2]CCC.Oc1cc(Cl)c2nc(-c3ccc(O)c(F)c3)cc(Br)c2c1>>C=Cc1cc(-c2ccc(O)c(F)c2)nc2c(Cl)cc(O)cc12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-22992e010418414795f879d0f01603fc | N#Cc1ccc(B(O)O)cc1.Oc1cc(Cl)c2nc(-c3ccc(O)c(F)c3)cc(Br)c2c1>>N#Cc1ccc(-c2cc(-c3ccc(O)c(F)c3)nc3c(Cl)cc(O)cc23)cc1 | BrC1=CC(=NC2=C(C=C(C=C12)O)Cl)C1=CC(=C(C=C1)O)F.C(#N)C1=CC=C(C=C1)B(O)O>>ClC=1C=C(C=C2C(=CC(=NC12)C1=CC(=C(C=C1)O)F)C1=CC=C(C=C1)C#N)O | OB(O)[c:6]1[cH:5][cH:4][c:3]([C:2]#[N:1])[cH:28][cH:27]1.Br[c:7]1[cH:8][c:9](-[c:10]2[cH:11][cH:12][c:13]([OH:14])[c:15]([F:16])[cH:17]2)[n:18][c:19]2[c:20]([Cl:21])[cH:22][c:23]([OH:24])[cH:25][c:26]12>>[N:1]#[C:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][c:9](-[c:10]3[cH:11][cH:12][c:13]([OH:14])[c:15]([F:16])[cH:17]3)[n... | N#Cc1ccc(B(O)O)cc1.Oc1cc(Cl)c2nc(-c3ccc(O)c(F)c3)cc(Br)c2c1 | N#Cc1ccc(-c2cc(-c3ccc(O)c(F)c3)nc3c(Cl)cc(O)cc23)cc1 | null | null | null | C-C Coupling | Suzuki coupling with boronic acids | 73d3d45d842e591351c81053feb1b3096820b80e5a86db47217e78e2a9707cc8 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(-c2cc(-c3ccccc3)c3ccccc3n2)cc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3](-[c:4]):[#7;a:5]:[c:6](:[c:7]):[c:8]:1:[c:9].O-B(-O)-[c;H0;D3;+0:10](:[c:11]:[c:12]):[c:13]:[c:14]>>[c:4]-[c:3]1:[#7;a:5]:[c:6](:[c:7]):[c:8](:[c:9]):[c;H0;D3;+0:1](-[c;H0;D3;+0:10](:[c:11]:[c:12]):[c:13]:[c:14]):[c:2]:1 | 94 | [{"value": 94.0, "product": "ClC=1C=C(C=C2C(=CC(=NC12)C1=CC(=C(C=C1)O)F)C1=CC=C(C=C1)C#N)O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | This compound was prepared from 45a using 4-cyanophenylboronic acid according to method P. Yellow solid; Yield: 94%; mp 324° C. (dec.); 1H-NMR (400 MHz, DMSO-d6) δ 6.93 (d, J=2.5 Hz, 1H), 7.09 (dd, J=8.8, 8.8 Hz, 1H), 7.54 (d, J=2.6 Hz, 1H), 7.81 (d, J=8.4 Hz, 2H), 8.03 (s, 1H), 8.04 (dd, J=8.5, 1.6 Hz, 1H), 8.09 (d, J... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccccc1.c1ccc2ncccc2c1 | c1ccccc1.c1ccc2ncccc2c1 | c1ccccc1.c1ccccc1.c1ccc2ncccc2c1 | HBr.B | null | null | null | N#Cc1ccc(B(O)O)cc1.Oc1cc(Cl)c2nc(-c3ccc(O)c(F)c3)cc(Br)c2c1>>N#Cc1ccc(-c2cc(-c3ccc(O)c(F)c3)nc3c(Cl)cc(O)cc23)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-81279442efa746b7a617ec2073a76c32 | COc1ccc(B(O)O)cc1.Oc1cc(Cl)c2nc(-c3ccc(O)c(F)c3)cc(Br)c2c1>>COc1ccc(-c2cc(-c3ccc(O)c(F)c3)nc3c(Cl)cc(O)cc23)cc1 | BrC1=CC(=NC2=C(C=C(C=C12)O)Cl)C1=CC(=C(C=C1)O)F.COC1=CC=C(C=C1)B(O)O>>ClC=1C=C(C=C2C(=CC(=NC12)C1=CC(=C(C=C1)O)F)C1=CC=C(C=C1)OC)O | OB(O)[c:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:28][cH:27]1.Br[c:7]1[cH:8][c:9](-[c:10]2[cH:11][cH:12][c:13]([OH:14])[c:15]([F:16])[cH:17]2)[n:18][c:19]2[c:20]([Cl:21])[cH:22][c:23]([OH:24])[cH:25][c:26]12>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][c:9](-[c:10]3[cH:11][cH:12][c:13]([OH:14])[c:15]([F:16])[cH:17]3)... | COc1ccc(B(O)O)cc1.Oc1cc(Cl)c2nc(-c3ccc(O)c(F)c3)cc(Br)c2c1 | COc1ccc(-c2cc(-c3ccc(O)c(F)c3)nc3c(Cl)cc(O)cc23)cc1 | null | null | null | C-C Coupling | Suzuki coupling with boronic acids | 73d3d45d842e591351c81053feb1b3096820b80e5a86db47217e78e2a9707cc8 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(-c2cc(-c3ccccc3)c3ccccc3n2)cc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3](-[c:4]):[#7;a:5]:[c:6](:[c:7]):[c:8]:1:[c:9].O-B(-O)-[c;H0;D3;+0:10](:[c:11]:[c:12]):[c:13]:[c:14]>>[c:4]-[c:3]1:[#7;a:5]:[c:6](:[c:7]):[c:8](:[c:9]):[c;H0;D3;+0:1](-[c;H0;D3;+0:10](:[c:11]:[c:12]):[c:13]:[c:14]):[c:2]:1 | 97 | [{"value": 97.0, "product": "ClC=1C=C(C=C2C(=CC(=NC12)C1=CC(=C(C=C1)O)F)C1=CC=C(C=C1)OC)O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | This compound was prepared from 45a using 4-methoxyphenylboronic acid according to method P. Orange solid; Yield: 97%; mp 140–142° C.; 1H-NMR (400 MHz, DMSO-d6) δ 3.87 (s, 3H), 7.09 (dd, J=8.8, 8.8 Hz, 1H), 7.11 (d, J=2.7 Hz, 1H), 7.16 (d, J=8.8 Hz, 2H), 7.51 (d, J=2.6 Hz, 1H), 7.53 (d, J=8.8 Hz, 2H), 7.93(s, 1H), 8.02... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccccc1.c1ccc2ncccc2c1 | c1ccccc1.c1ccc2ncccc2c1 | c1ccccc1.c1ccccc1.c1ccc2ncccc2c1 | HBr.B | null | null | null | COc1ccc(B(O)O)cc1.Oc1cc(Cl)c2nc(-c3ccc(O)c(F)c3)cc(Br)c2c1>>COc1ccc(-c2cc(-c3ccc(O)c(F)c3)nc3c(Cl)cc(O)cc23)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-5ba227c56f3a4e9babf17bf816fa60e1 | COc1cc(Br)c2nc(-c3ccc(OC)c(F)c3)cc(O)c2c1.N#Cc1ccc(B(O)O)cc1>>COc1cc(-c2ccc(C#N)cc2)c2nc(-c3ccc(OC)c(F)c3)cc(O)c2c1 | BrC=1C=C(C=C2C(=CC(=NC12)C1=CC(=C(C=C1)OC)F)O)OC.C(#N)C1=CC=C(C=C1)B(O)O>>C(#N)C1=CC=C(C=C1)C=1C=C(C=C2C(=CC(=NC12)C1=CC(=C(C=C1)OC)F)O)OC | Br[c:5]1[cH:4][c:3]([O:2][CH3:1])[cH:30][c:29]2[c:14]1[n:15][c:16](-[c:17]1[cH:18][cH:19][c:20]([O:21][CH3:22])[c:23]([F:24])[cH:25]1)[cH:26][c:27]2[OH:28].OB(O)[c:6]1[cH:7][cH:8][c:9]([C:10]#[N:11])[cH:12][cH:13]1>>[CH3:1][O:2][c:3]1[cH:4][c:5](-[c:6]2[cH:7][cH:8][c:9]([C:10]#[N:11])[cH:12][cH:13]2)[c:14]2[n:15][c:16]... | COc1cc(Br)c2nc(-c3ccc(OC)c(F)c3)cc(O)c2c1.N#Cc1ccc(B(O)O)cc1 | COc1cc(-c2ccc(C#N)cc2)c2nc(-c3ccc(OC)c(F)c3)cc(O)c2c1 | null | null | null | C-C Coupling | Suzuki coupling with boronic acids | 73d3d45d842e591351c81053feb1b3096820b80e5a86db47217e78e2a9707cc8 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(-c2ccc3cccc(-c4ccccc4)c3n2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](:[c:5]):[#7;a:6]:[c:7].O-B(-O)-[c;H0;D3;+0:8](:[c:9]:[c:10]):[c:11]:[c:12]>>[c:10]:[c:9]:[c;H0;D3;+0:8](-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](:[c:5]):[#7;a:6]:[c:7]):[c:11]:[c:12] | 56 | [{"value": 56.0, "product": "C(#N)C1=CC=C(C=C1)C=1C=C(C=C2C(=CC(=NC12)C1=CC(=C(C=C1)OC)F)O)OC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | This compound was prepared from 41b using 4-cyanophenylboronic acid according to method P. Orange solid; Yield: 56%; mp 248–250° C.; 1H NMR (300 MHz, DMSO-d6) δ 3.89 (s, 3H), 3.94 (s, 3H), 7.28 (t, J=8.8 Hz, 1H), 7.36 (s, 1H), 7.44 (d, J=2.9 Hz, 1H), 7.53 (d, J=2.9 Hz, 1H), 7.75–7.79 (m, 2H), 7.97 (br s, 4H), 11.50 (s,... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccc2ncccc2c1.c1ccccc1 | c1ccccc1.c1ccc2ncccc2c1 | c1ccccc1.c1ccc2ncccc2c1.c1ccccc1 | HBr.B | null | null | null | COc1cc(Br)c2nc(-c3ccc(OC)c(F)c3)cc(O)c2c1.N#Cc1ccc(B(O)O)cc1>>COc1cc(-c2ccc(C#N)cc2)c2nc(-c3ccc(OC)c(F)c3)cc(O)c2c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-3b6de8a0b0db409880422faff950189b | Nc1ccccc1.O=[N+]([O-])c1ccc(Cl)cc1>>O=[N+]([O-])c1ccc(Nc2ccccc2)cc1 | NC1=CC=CC=C1.[N+](=O)([O-])C1=CC=C(C=C1)Cl.NC1=CC=CC=C1>>C1=CC=C(C=C1)NC2=CC=C(C=C2)[N+](=O)[O-] | [NH2:8][c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1.Cl[c:7]1[cH:6][cH:5][c:4]([N+:2](=[O:1])[O-:3])[cH:16][cH:15]1>>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][cH:6][c:7]([NH:8][c:9]2[cH:10][cH:11][cH:12][cH:13][cH:14]2)[cH:15][cH:16]1 | Nc1ccccc1.O=[N+]([O-])c1ccc(Cl)cc1 | O=[N+]([O-])c1ccc(Nc2ccccc2)cc1 | null | null | null | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | da9dae6a655c4bd18887b692f91621e77027436294d6e1fc7be7295afb364796 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2ccccc2)cc1 | Cl-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[c:8]:[c:7](-[NH;D2;+0:6]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5]):[c:9] | null | [] | null | null | null | null | aniline method, where p-nitro-chlorobenzene and aniline as raw materials react in the presence of a catalyst to produce 4-nitrodiphenylamine, then, 4-nitrodiphenylamine is reduced by sodium sulfide to form 4-aminodiphenylamine;
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1 | HCl | null | null | null | Nc1ccccc1.O=[N+]([O-])c1ccc(Cl)cc1>>O=[N+]([O-])c1ccc(Nc2ccccc2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-34bb9f2f23f345d6881cdbdf4c474d23 | O=[N+]([O-])c1ccc(Nc2ccccc2)cc1>>Nc1ccc(Nc2ccccc2)cc1 | C1=CC=C(C=C1)NC2=CC=C(C=C2)[N+](=O)[O-].[S-2].[Na+].[Na+]>>C1=CC=C(C=C1)NC2=CC=C(C=C2)N | O=[N+:1]([O-])[c:2]1[cH:3][cH:4][c:5]([NH:6][c:7]2[cH:8][cH:9][cH:10][cH:11][cH:12]2)[cH:13][cH:14]1>>[NH2:1][c:2]1[cH:3][cH:4][c:5]([NH:6][c:7]2[cH:8][cH:9][cH:10][cH:11][cH:12]2)[cH:13][cH:14]1 | O=[N+]([O-])c1ccc(Nc2ccccc2)cc1 | Nc1ccc(Nc2ccccc2)cc1 | null | null | null | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccc(Nc2ccccc2)cc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | null | null | aniline method, where p-nitro-chlorobenzene and aniline as raw materials react in the presence of a catalyst to produce 4-nitrodiphenylamine, then, 4-nitrodiphenylamine is reduced by sodium sulfide to form 4-aminodiphenylamine;
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1.c1ccccc1 | Other | null | null | null | O=[N+]([O-])c1ccc(Nc2ccccc2)cc1>>Nc1ccc(Nc2ccccc2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-7a9eeef338d34ed09b7439bf73611b0e | Nc1ccccc1.O=[N+]([O-])c1ccc(Cl)cc1>>O=[N+]([O-])c1ccc(Nc2ccccc2)cc1 | C(=O)NC1=CC=CC=C1.NC1=CC=CC=C1.[N+](=O)([O-])C1=CC=C(C=C1)Cl.C([O-])([O-])=O.[K+].[K+].C(=O)NC1=CC=CC=C1>>C1=CC=C(C=C1)NC2=CC=C(C=C2)[N+](=O)[O-] | [NH2:8][c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1.Cl[c:7]1[cH:6][cH:5][c:4]([N+:2](=[O:1])[O-:3])[cH:16][cH:15]1>>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][cH:6][c:7]([NH:8][c:9]2[cH:10][cH:11][cH:12][cH:13][cH:14]2)[cH:15][cH:16]1 | Nc1ccccc1.O=[N+]([O-])c1ccc(Cl)cc1 | O=[N+]([O-])c1ccc(Nc2ccccc2)cc1 | null | null | C(=O)O | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | da9dae6a655c4bd18887b692f91621e77027436294d6e1fc7be7295afb364796 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2ccccc2)cc1 | Cl-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[c:8]:[c:7](-[NH;D2;+0:6]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5]):[c:9] | null | [] | null | null | null | null | formanilide method, where formic acid and aniline are used as starting materials to prepare formanilide, which in turn reacts with p-nitro-chlorobenzene in the presence of an acid-binding agent such as potassium carbonate, to produce 4-nitrodiphenylamine, and then, 4-nitrodiphenylamine is reduced by sodium sulfide to f... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1 | HCl | C(=O)O | null | null | Nc1ccccc1.O=[N+]([O-])c1ccc(Cl)cc1>C(=O)O>O=[N+]([O-])c1ccc(Nc2ccccc2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-fb202ce28fce4b4aa4357668711c12d9 | O=[N+]([O-])c1ccc(Nc2ccccc2)cc1>>Nc1ccc(Nc2ccccc2)cc1 | C1=CC=C(C=C1)NC2=CC=C(C=C2)[N+](=O)[O-].[S-2].[Na+].[Na+]>>C1=CC=C(C=C1)NC2=CC=C(C=C2)N | O=[N+:1]([O-])[c:2]1[cH:3][cH:4][c:5]([NH:6][c:7]2[cH:8][cH:9][cH:10][cH:11][cH:12]2)[cH:13][cH:14]1>>[NH2:1][c:2]1[cH:3][cH:4][c:5]([NH:6][c:7]2[cH:8][cH:9][cH:10][cH:11][cH:12]2)[cH:13][cH:14]1 | O=[N+]([O-])c1ccc(Nc2ccccc2)cc1 | Nc1ccc(Nc2ccccc2)cc1 | null | null | null | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccc(Nc2ccccc2)cc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | null | null | formanilide method, where formic acid and aniline are used as starting materials to prepare formanilide, which in turn reacts with p-nitro-chlorobenzene in the presence of an acid-binding agent such as potassium carbonate, to produce 4-nitrodiphenylamine, and then, 4-nitrodiphenylamine is reduced by sodium sulfide to f... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1.c1ccccc1 | Other | null | null | null | O=[N+]([O-])c1ccc(Nc2ccccc2)cc1>>Nc1ccc(Nc2ccccc2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-e70b01ed6e6a4bcc904277bc74d3110e | c1ccc(Nc2ccccc2)cc1>>O=NN(c1ccccc1)c1ccccc1 | C1(=CC=CC=C1)NC1=CC=CC=C1.C1(=CC=CC=C1)NC1=CC=CC=C1.N(=O)[O-]>>N(=O)N(C1=CC=CC=C1)C1=CC=CC=C1 | [NH:3]([c:4]1[cH:5][cH:6][cH:7][cH:8][cH:9]1)[c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1>>[O:1]=[N:2][N:3]([c:4]1[cH:5][cH:6][cH:7][cH:8][cH:9]1)[c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1 | c1ccc(Nc2ccccc2)cc1 | O=NN(c1ccccc1)c1ccccc1 | null | null | null | Miscellaneous | OtherReaction | 97abfb757cd7a417aa05bf509390cc1dd42c2b1a0c96b91f95f5f6968df59ae4 | 797765290ff12ff8fc5d8a85352c4763898223fe8d7887a890f0208d031bd39f | c1ccc(Nc2ccccc2)cc1 | [c:1]:[c:2](-[NH;D2;+0:3]-[c:4](:[c:5]):[c:6]):[c:7]>>[O;D1;H0:8]=[#7:9]-[N;H0;D3;+0:3](-[c:2](:[c:1]):[c:7])-[c:4](:[c:5]):[c:6] | null | [] | null | null | null | null | diphenylamine method, where diphenylamine as raw material is nitrosated using a nitrite in an organic solvent to produce N-nitrosodiphenylamine, which is rearranged to 4-nitrosodiphenylamine hydrochloride under the action of anhydrous hydrogen chloride, and then, 4-nitrosodiphenylamine hydrochloride is neutralized with... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amine | Hydrazone | null | null | c1ccccc1.c1ccccc1 | Other | null | null | null | c1ccc(Nc2ccccc2)cc1>>O=NN(c1ccccc1)c1ccccc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-0cb97dc9f2f146dc81187fbd22e6bbc9 | CN(C)C.CO.COC(=O)OC>>COC(=O)[O-].C[N+](C)(C)C | C(OC)(OC)=O.CN(C)C.CO>>COC([O-])=O.C[N+](C)(C)C | [CH3:6][N:7]([CH3:8])[CH3:10].O[CH3:9].C[O:5][C:3]([O:2][CH3:1])=[O:4]>>[CH3:1][O:2][C:3](=[O:4])[O-:5].[CH3:6][N+:7]([CH3:8])([CH3:9])[CH3:10] | CN(C)C.CO.COC(=O)OC | COC(=O)[O-].C[N+](C)(C)C | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 3efa28bb7da20a8af742e588325974a8592b70db1c0bb0a9fae065dded35e252 | 607e925a6fd3c9c7471bcd5f5d75e257a9747db166c67a5d6c2c89cac4bbbe92 | null | C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#8:4]-[C;D1;H3:5].O-[CH3;D1;+0:6].[C;D1;H3:7]-[N;H0;D3;+0:8](-[C;D1;H3:9])-[C;D1;H3:10]>>[C;D1;H3:5]-[#8:4]-[C:2](-[O-;H0;D1:1])=[O;D1;H0:3].[C;D1;H3:7]-[N+;H0;D4:8](-[C;D1;H3:9])(-[C;D1;H3:10])-[CH3;D1;+0:6] | 80.2 | [{"value": 80.2, "product": "COC([O-])=O.C[N+](C)(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 80.1, "product": "COC([O-])=O.C[N+](C)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 140 | CELSIUS | 4 | HOUR | To a 1.5 L autoclave equipped with a stirrer and a heating means were added 90 g (11.0 mol) of dimethyl carbonate, 59 g (1.0 mol) of trimethyl amine and 510 g (15 mol) of methanol. Stirring was initiated after the autoclave was sealed. The autoclave was heat to 140° C., and pressure was 1.5 MPa. The reaction was kept a... | 10.6084/m9.figshare.5104873.v1 | null | Carbonic Ester.Tertiary amine.Methanol | Carbonic Acid | null | null | null | HO- | null | 140 | 4 | CN(C)C.CO.COC(=O)OC>>COC(=O)[O-].C[N+](C)(C)C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-e695220a42e7464caba10ab706dbb1bd | CCN(CC)CC.CCOS(=O)(=O)OCC>>CC[N+](CC)(CC)CC | [OH-].[Na+].S(=O)(=O)(OCC)OCC.C(C)N(CC)CC.C(C)O>>[OH-].C(C)[N+](CC)(CC)CC | [CH3:1][CH2:2][N:3]([CH2:4][CH3:5])[CH2:8][CH3:9].CCOS(=O)(=O)O[CH2:6][CH3:7]>>[CH3:1][CH2:2][N+:3]([CH2:4][CH3:5])([CH2:6][CH3:7])[CH2:8][CH3:9] | CCN(CC)CC.CCOS(=O)(=O)OCC | CC[N+](CC)(CC)CC | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 4fb461fd1d845eeffcd721907fb84dda2a83d6f16d6187a0c591ac1d342a1cfa | 7c33147a6170e63e1fbe1110c4ce069481be57a96b70c4a5a6d7e8253f321bd2 | null | C-C-O-S(=O)(=O)-O-[CH2;D2;+0:1]-[C;D1;H3:2].[C;D1;H3:3]-[C:4]-[N;H0;D3;+0:5](-[C:6]-[C;D1;H3:7])-[C:8]-[C;D1;H3:9]>>[C;D1;H3:3]-[C:4]-[N+;H0;D4:5](-[C:6]-[C;D1;H3:7])(-[C:8]-[C;D1;H3:9])-[CH2;D2;+0:1]-[C;D1;H3:2] | 410.2 | [{"value": 95.7, "product": "[OH-].C(C)[N+](CC)(CC)CC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 410.2, "product": "[OH-].C(C)[N+](CC)(CC)CC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 140 | CELSIUS | 4 | HOUR | To a 1.5 L autoclave equipped with a stirrer and a heating means were added 154 g (1.0 mol) of diethyl sulfate, 101 g (1.0 mol) of triethyl amine and 690 g (15 mol) of ethanol. Stirring was initiated after the autoclave was sealed. The autoclave was heat to 140° C., and pressure was 1.0 MPa. The reaction was kept at 14... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amine | null | null | null | null | HO- | null | 140 | 4 | CCN(CC)CC.CCOS(=O)(=O)OCC>>CC[N+](CC)(CC)CC |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-d031c2a1d4404c0f8c49a7f6d73e8050 | CC(C)(C)C(=O)CC(=O)C(C)(C)C.O.[OH-].[Zr+4]>>CC(C)(C)C(=O)/C=C(\O)C(C)(C)C.CC(C)(C)C(=O)/C=C(\O)C(C)(C)C.CC(C)(C)C(=O)/C=C(\O)C(C)(C)C.CC(C)(C)C(=O)/C=C(\O)C(C)(C)C.[Zr] | [OH-].[Na+].[Cl-].[Cl-].[Cl-].[Cl-].[Zr+4].CC(C)(C(CC(C(C)(C)C)=O)=O)C.O>>CC(/C(=C/C(=O)C(C)(C)C)/O)(C)C.CC(/C(=C/C(=O)C(C)(C)C)/O)(C)C.CC(/C(=C/C(=O)C(C)(C)C)/O)(C)C.CC(/C(=C/C(=O)C(C)(C)C)/O)(C)C.[Zr] | [CH3:1][C:2]([CH3:3])([CH3:21])[C:31](=[O:32])[CH2:33][C:34](=[O:35])[C:36]([CH3:37])([CH3:38])[CH3:39].[OH2:19].[OH-:6].[Zr+4:53]>>[CH3:1][C:2]([CH3:3])([CH3:4])[C:5](=[O:6])/[CH:7]=[C:8](\[OH:9])[C:10]([CH3:11])([CH3:12])[CH3:13].[CH3:14][C:15]([CH3:16])([CH3:17])[C:18](=[O:19])/[CH:20]=[C:21](\[OH:22])[C:23]([CH3:24... | CC(C)(C)C(=O)CC(=O)C(C)(C)C.O.[OH-].[Zr+4] | CC(C)(C)C(=O)/C=C(\O)C(C)(C)C.CC(C)(C)C(=O)/C=C(\O)C(C)(C)C.CC(C)(C)C(=O)/C=C(\O)C(C)(C)C.CC(C)(C)C(=O)/C=C(\O)C(C)(C)C.[Zr] | null | null | CO | Acylation | OtherReaction | c22a721143f01f2466799be601772121394a32f25a80d253214aff053096e802 | 8d45196a57eebe875f9534d6f941f1cdc4cbacb7d09ae2588ed02920a79b77f0 | null | [C;D1;H3:1]-[C;H0;D4;+0:2](-[C;D1;H3:3])(-[CH3;D1;+0:4])-[C;H0;D3;+0:5](=[O;D1;H0:6])-[CH2;D2;+0:7]-[C;H0;D3;+0:8](=[O;H0;D1;+0:9])-[C:10](-[C;D1;H3:11])(-[C;D1;H3:12])-[C;D1;H3:13].[OH-;D0:14].[OH2;D0;+0:15].[Zr+4;H0;D0:16]>>[C;D1;H3:17]-[C:18](-[C;D1;H3:19])(-[C;D1;H3:20])-[C;H0;D3;+0:5](=[O;D1;H0:6])/[CH;D2;+0:7]=[C... | 98.2 | [{"value": 98.2, "product": "CC(/C(=C/C(=O)C(C)(C)C)/O)(C)C.CC(/C(=C/C(=O)C(C)(C)C)/O)(C)C.CC(/C(=C/C(=O)C(C)(C)C)/O)(C)C.CC(/C(=C/C(=O)C(C)(C)C)/O)(C)C.[Zr]", "details": "PERCENTYIELD", "is_desired": false}, {"value": 98.1, "product": "CC(/C(=C/C(=O)C(C)(C)C)/O)(C)C.CC(/C(=C/C(=O)C(C)(C)C)/O)(C)C.CC(/C(=C/C(=O)C(C)(C)... | null | null | 1 | HOUR | To 177 g of methanol, 43.7 g (0.216 mol) of 2,2,6,6-tetramethyl-3,5-heptanedione of 91% purity was dropwise added with stirring. To the resulting solution, a solution, which had been obtained by dissolving 12.7 g (0.054 mol) of ZrCl4 of 99% purity in 218 g of methanol and cooled to room temperature, was added over a pe... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ketone | Ketone.Ketone.Ketone.Ketone.Enol.Enol.Enol.Enol | null | null | null | null | CO | null | 1 | CC(C)(C)C(=O)CC(=O)C(C)(C)C.O.[OH-].[Zr+4]>CO>CC(C)(C)C(=O)/C=C(\O)C(C)(C)C.CC(C)(C)C(=O)/C=C(\O)C(C)(C)C.CC(C)(C)C(=O)/C=C(\O)C(C)(C)C.CC(C)(C)C(=O)/C=C(\O)C(C)(C)C.[Zr] |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-dc825329a9534658b229511a87c5a84d | C1=CC2CCC1C2.C1=CC2CCC1C2>>C1=C2C3CCC(C3)C2CCC1 | C1CC2CC1C=C2.C1CC2CC1C=C2.C=CC=C>>C12CCC(C3CCCC=C13)C2 | [CH:2]1=[CH:8][CH:6]2[CH2:5][CH2:4][CH:3]1[CH2:7]2.C1=[CH:1][CH:11]2CC1[CH2:9][CH2:10]2>>[CH:1]1=[C:2]2[CH:3]3[CH2:4][CH2:5][CH:6]([CH2:7]3)[CH:8]2[CH2:9][CH2:10][CH2:11]1 | C1=CC2CCC1C2.C1=CC2CCC1C2 | C1=C2C3CCC(C3)C2CCC1 | null | CC1=CC=C(C=C1)O | null | Functional Group Interconversion | OtherReaction | 4ea1134b1431d680e613361a257dab0dc489a867ad8d3f93cf902a03efa8b1be | f1bbf9aa3c82f5e49be9f6d53533b6bb152f359232b6d32090c168949766aa71 | C1=C2C3CCC(C3)C2CCC1 | C1-C2-C=[CH;D2;+0:1]-[CH;D3;+0:2]-1-[C:3]-[CH2;D2;+0:4]-2.[C:5]1-[C:6]-[C:7]2-[C:8]-[C:9]-1-[CH;D2;+0:10]=[CH;D2;+0:11]-2>>[C:3]1-[CH2;D2;+0:2]-[CH;D2;+0:1]=[C;H0;D3;+0:10]2-[C:9]3-[C:5]-[C:6]-[C:7](-[C:8]-3)-[CH;D3;+0:11]-2-[CH2;D2;+0:4]-1 | 145.8 | [{"value": 73.0, "product": "C12CCC(C3CCCC=C13)C2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 145.8, "product": "C12CCC(C3CCCC=C13)C2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 200 | CELSIUS | null | null | A 400 ml autoclave was charged with bicyclo[2,2,1]-2-heptene (152 g, Aldrich), 4-methylphenol (1 g, Aldrich), and butadiene (110 g). The mixture was heated at 200° C. for 10 hours. The reaction mixtures from four identical reactions were combined and distilled at atmosphere to give starting bicyclo[2,2,1]-2-heptene (30... | 10.6084/m9.figshare.5104873.v1 | null | null | null | C1=CC2CCC1C2.C1=CC2CCC1C2 | C1=C2C3CCC(C3)C2CCC1 | C1=C2C3CCC(C3)C2CCC1 | Other | CC1=CC=C(C=C1)O | 200 | null | C1=CC2CCC1C2.C1=CC2CCC1C2>CC1=CC=C(C=C1)O>C1=C2C3CCC(C3)C2CCC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-76944fac672d4c29a68933501960dba5 | C1=C2C3CCC(C3)C2CCC1>>C1CCC2C3CCC(C3)C2C1 | [H][H].C12CCC(C3CCCC=C13)C2.[H][H]>>C12CCC(C3CCCCC13)C2 | [CH2:1]1[CH2:2][CH:3]=[C:4]2[CH:5]3[CH2:6][CH2:7][CH:8]([CH2:9]3)[CH:10]2[CH2:11]1>>[CH2:1]1[CH2:2][CH2:3][CH:4]2[CH:5]3[CH2:6][CH2:7][CH:8]([CH2:9]3)[CH:10]2[CH2:11]1 | C1=C2C3CCC(C3)C2CCC1 | C1CCC2C3CCC(C3)C2C1 | null | [Pd] | CO | Reduction | Hydrogenation (double to single) | 417c0c693fb009b1a7c8e162fdb847862fb77f86e94f4c844a69fd0bd6589a7c | 312e9350dcad67590617294c0eb017edf0b9fbfe6133c06a3f393b871a889092 | C1CCC2C3CCC(C3)C2C1 | [C:1]-[C:2]1-[C:3]-[C:4]-[C:5]2-[C:6]-[C:7]-[C:8]-[CH;D2;+0:9]=[C;H0;D3;+0:10]-2-1>>[C:1]-[C:2]1-[C:3]-[C:4]-[C:5]2-[C:6]-[C:7]-[C:8]-[CH2;D2;+0:9]-[CH;D3;+0:10]-2-1 | 257.6 | [{"value": 86.0, "product": "C12CCC(C3CCCCC13)C2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 257.6, "product": "C12CCC(C3CCCCC13)C2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 45 | MINUTE | A 400 ml autoclave was charged with octahydro-1,4-methanonaphthalene (122 g, prepared as described above), methanol (100 ml, Burdick & Jackson, HPLC grade), and palladium on activated carbon (1.5 g containing 10% Pd, Alfa products, powder). The autoclave was closed and sealed, then shaken under 50 psig hydrogen pressur... | 10.6084/m9.figshare.5104873.v1 | null | null | null | C1=C2C3CCC(C3)C2CCC1 | C1CCC2C3CCC(C3)C2C1 | C1CCC2C3CCC(C3)C2C1 | null | [Pd].CO | null | 0.75 | C1=C2C3CCC(C3)C2CCC1>[Pd].CO>C1CCC2C3CCC(C3)C2C1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-3bf2e6545296467986cc10fd18ef8ea4 | FC(F)(F)C1CC2CC1C1=CCCCC12>>FC(F)(F)C1CC2CC1C1CCCCC21 | [H][H].FC(C1C2C3=CCCCC3C(C1)C2)(F)F.[H][H]>>FC(C1C2C3CCCCC3C(C1)C2)(F)F | [F:1][C:2]([F:3])([F:4])[CH:5]1[CH2:6][CH:7]2[CH2:8][CH:9]1[C:10]1=[CH:11][CH2:12][CH2:13][CH2:14][CH:15]21>>[F:1][C:2]([F:3])([F:4])[CH:5]1[CH2:6][CH:7]2[CH2:8][CH:9]1[CH:10]1[CH2:11][CH2:12][CH2:13][CH2:14][CH:15]21 | FC(F)(F)C1CC2CC1C1=CCCCC12 | FC(F)(F)C1CC2CC1C1CCCCC21 | null | [Pd] | CO | Reduction | Hydrogenation (double to single) | 417c0c693fb009b1a7c8e162fdb847862fb77f86e94f4c844a69fd0bd6589a7c | 312e9350dcad67590617294c0eb017edf0b9fbfe6133c06a3f393b871a889092 | C1CCC2C3CCC(C3)C2C1 | [C:1]-[C:2]1-[C:3]-[C:4]-[C:5]2-[C:6]-[C:7]-[C:8]-[CH;D2;+0:9]=[C;H0;D3;+0:10]-2-1>>[C:1]-[C:2]1-[C:3]-[C:4]-[C:5]2-[C:6]-[C:7]-[C:8]-[CH2;D2;+0:9]-[CH;D3;+0:10]-2-1 | null | [] | null | null | 45 | MINUTE | A 400 ml autoclave is charged with 177 g of the thus purified octahydro-2-trifluormethyl-1,4-methanonaphthalene, methanol (100 ml, Burdick & Jackson, HPLC grade), and palladium on activated carbon (1.5 g containing 10% Pd, Alfa products, powder). The autoclave is closed and sealed, then it is shaken under 50 psig hydro... | 10.6084/m9.figshare.5104873.v1 | null | null | null | C1=C2C3CCC(C3)C2CCC1 | C1CCC2C3CCC(C3)C2C1 | C1CCC2C3CCC(C3)C2C1 | null | [Pd].CO | null | 0.75 | FC(F)(F)C1CC2CC1C1=CCCCC12>[Pd].CO>FC(F)(F)C1CC2CC1C1CCCCC21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-acb43fa5eb1b42d09e33b5d59c24f091 | CCN=C=NCCCN(C)C.CSCC[C@H](N)C(=O)O.C[C@H](N)C(=O)OC(C)(C)C.On1nnc2ccccc21>>CSCC[C@H](NC(=O)OCc1ccccc1)C(=O)N[C@@H](C)C(=O)OC(C)(C)C | C(C)(C)(C)OC([C@@H](N)C)=O.Cl.CN(CCCN=C=NCC)C.N[C@@H](CCSC)C(=O)O.C=1C=CC2=C(C1)N=NN2O>>C(C1=CC=CC=C1)OC(=O)N[C@@H](CCSC)C(=O)N[C@@H](C)C(=O)OC(C)(C)C | CN(C)CCCN=[C:7]=N[CH2:10][CH3:15].[CH3:1][S:2][CH2:3][CH2:4][C@H:5]([NH2:6])[C:17]([OH:8])=[O:18].[NH2:19][C@@H:20]([CH3:21])[C:22](=[O:23])[O:24][C:25]([CH3:26])([CH3:27])[CH3:28].n1nn([OH:9])[c:11]2c1[cH:12][cH:13][cH:14][cH:16]2>>[CH3:1][S:2][CH2:3][CH2:4][C@H:5]([NH:6][C:7](=[O:8])[O:9][CH2:10][c:11]1[cH:12][cH:13]... | CCN=C=NCCCN(C)C.CSCC[C@H](N)C(=O)O.C[C@H](N)C(=O)OC(C)(C)C.On1nnc2ccccc21 | CSCC[C@H](NC(=O)OCc1ccccc1)C(=O)N[C@@H](C)C(=O)OC(C)(C)C | null | null | CN(C)C=O.C(C)N(CC)CC | C-C Coupling | OtherReaction | 6d620ff54c8c76eb4d36b8abf9fffc2c5f76c8423bbc100610eca837575e5129 | 8df2b912fdba47beb0926dfbece6afe0e78922d84c3228bfea7a541631ccb925 | c1ccccc1 | C-N(-C)-C-C-C-N=[C;H0;D2;+0:1]=N-[CH2;D2;+0:2]-[CH3;D1;+0:3].[C;D1;H3:4]-[C:5](-[NH2;D1;+0:6])-[C:7](=[O;D1;H0:8])-[#8:9]-[C:10](-[C;D1;H3:11])(-[C;D1;H3:12])-[C;D1;H3:13].[C:14]-[C:15](-[NH2;D1;+0:16])-[C;H0;D3;+0:17](=[O;D1;H0:18])-[OH;D1;+0:19].[OH;D1;+0:20]-n1:n:n:c2:[cH;D2;+0:21]:[c:22]:[cH;D2;+0:23]:[cH;D2;+0:24]... | 109.3 | [{"value": 109.3, "product": "C(C1=CC=CC=C1)OC(=O)N[C@@H](CCSC)C(=O)N[C@@H](C)C(=O)OC(C)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | Z-Protected L-methionine (10 g) was dissolved in DMF (200 ml) and 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (8.13 g) was added followed by HOBT (5.72 g) and triethylamine (19.7 ml). The mixture was stirred for 1 h then L-alanine tert-butyl ester (7.7 g) was added and stirring continued for 18 h. The... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine.Primary amine.Tertiary amine | Carbamic ester.Ether.Secondary amide | c1ccc2[nH]nnc2c1 | c1ccccc1 | c1ccccc1 | Other | CN(C)C=O.C(C)N(CC)CC | null | 1 | CCN=C=NCCCN(C)C.CSCC[C@H](N)C(=O)O.C[C@H](N)C(=O)OC(C)(C)C.On1nnc2ccccc21>CN(C)C=O.C(C)N(CC)CC>CSCC[C@H](NC(=O)OCc1ccccc1)C(=O)N[C@@H](C)C(=O)OC(C)(C)C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-4bd47d9e549343d0b97d459c637f4d5c | C[C@@H](C(=O)OC(C)(C)C)N1CC[C@H](NC(=O)OCc2ccccc2)C1=O>>C[C@@H](C(=O)O)N1CC[C@H](NC(=O)OCc2ccccc2)C1=O | C(C1=CC=CC=C1)OC(=O)N[C@@H]1C(N(CC1)[C@H](C(=O)OC(C)(C)C)C)=O.FC(C(=O)O)(F)F>>C(C1=CC=CC=C1)OC(=O)N[C@@H]1C(N(CC1)[C@H](C(=O)O)C)=O | CC(C)(C)[O:5][C:3]([C@H:2]([CH3:1])[N:6]1[CH2:7][CH2:8][C@H:9]([NH:10][C:11](=[O:12])[O:13][CH2:14][c:15]2[cH:16][cH:17][cH:18][cH:19][cH:20]2)[C:21]1=[O:22])=[O:4]>>[CH3:1][C@@H:2]([C:3](=[O:4])[OH:5])[N:6]1[CH2:7][CH2:8][C@H:9]([NH:10][C:11](=[O:12])[O:13][CH2:14][c:15]2[cH:16][cH:17][cH:18][cH:19][cH:20]2)[C:21]1=[O... | C[C@@H](C(=O)OC(C)(C)C)N1CC[C@H](NC(=O)OCc2ccccc2)C1=O | C[C@@H](C(=O)O)N1CC[C@H](NC(=O)OCc2ccccc2)C1=O | null | null | C(Cl)Cl | Deprotection | Deprotection of carboxylic acid | 152e5537e48c95b4a3e767536b0f9f68d1308e5f484070828ab5ed951805157a | 7f019d4cfe9b3036d0a2d3a3209aa0e1fcb05418ebee15a4be5e125d315d5f01 | O=C(N[C@H]1CCNC1=O)OCc1ccccc1 | C-C(-C)(-C)-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4]>>[C:3]-[C:2](=[O;D1;H0:4])-[OH;D1;+0:1] | 100.1 | [{"value": 100.1, "product": "C(C1=CC=CC=C1)OC(=O)N[C@@H]1C(N(CC1)[C@H](C(=O)O)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1.5 | HOUR | tert-Butyl (2S)-2-((3S)-3-{[(benzyloxy)carbonyl]amino}-2-oxopyrrolidin-1-yl)propanoate (0.5 g) was dissolved in DCM (7 ml), and trifluoroacetic acid (4.7 ml) was added. The mixture was stirred at room temperature for 1.5 h and then concentrated under reduced pressure to give the title compound (0.423 g) as a colourless... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Boc | Carboxylic acid | null | null | C1CC[NH]C1.c1ccccc1 | Other | C(Cl)Cl | null | 1.5 | C[C@@H](C(=O)OC(C)(C)C)N1CC[C@H](NC(=O)OCc2ccccc2)C1=O>C(Cl)Cl>C[C@@H](C(=O)O)N1CC[C@H](NC(=O)OCc2ccccc2)C1=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-f3a66bbcb3f94cea9e8f39b795a686a8 | C1CCNCC1.C[C@@H](C(=O)O)N1CC[C@H](NC(=O)OCc2ccccc2)C1=O>>C[C@@H](C(=O)N1CCCCC1)N1CC[C@H](NC(=O)OCc2ccccc2)C1=O | N1CCCCC1.C(C1=CC=CC=C1)OC(=O)N[C@@H]1C(N(CC1)[C@H](C(=O)O)C)=O.Cl.CN(CCCN=C=NCC)C.C=1C=CC2=C(C1)N=NN2O>>C[C@@H](C(N1CCCCC1)=O)N1C([C@H](CC1)NC(OCC1=CC=CC=C1)=O)=O | [NH:5]1[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10]1.O[C:3]([C@H:2]([CH3:1])[N:11]1[CH2:12][CH2:13][C@H:14]([NH:15][C:16](=[O:17])[O:18][CH2:19][c:20]2[cH:21][cH:22][cH:23][cH:24][cH:25]2)[C:26]1=[O:27])=[O:4]>>[CH3:1][C@@H:2]([C:3](=[O:4])[N:5]1[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10]1)[N:11]1[CH2:12][CH2:13][C@H:14]([NH:15][C:16... | C1CCNCC1.C[C@@H](C(=O)O)N1CC[C@H](NC(=O)OCc2ccccc2)C1=O | C[C@@H](C(=O)N1CCCCC1)N1CC[C@H](NC(=O)OCc2ccccc2)C1=O | null | null | C(Cl)Cl.C(C)N(CC)CC | Acylation | Acylation of Nitrogen Nucleophiles by Carboxylic Acids | fbfce93ec1ece674255bb96c5cec09ad611382b41cf117dfe580015e21744a71 | c5e4172490b2731ba9322b68af56376edadc31ce0bb9a3dfdea23a1817a852fd | O=C(N[C@H]1CCN(CC(=O)N2CCCCC2)C1=O)OCc1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C;D1;H3:4])-[#7:5]-[C:6]=[O;D1;H0:7].[C:8]-[C:9]-[NH;D2;+0:10]-[C:11]-[C:12]>>[C:8]-[C:9]-[N;H0;D3;+0:10](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C;D1;H3:4])-[#7:5]-[C:6]=[O;D1;H0:7])-[C:11]-[C:12] | 68.8 | [{"value": 68.8, "product": "C[C@@H](C(N1CCCCC1)=O)N1C([C@H](CC1)NC(OCC1=CC=CC=C1)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 5 | MINUTE | To a solution of (2S)-2-((3S)-3-{[(benzyloxy)carbonyl]amino}-2-oxopyrrolidin-1-yl)propanoic acid (3.1 g) in DCM (30 ml) were added 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (4.6 g), HOBT (3.2 g) and triethylamine (2.5 ml) and the mixture was stirred at room temperature for 5 min. Piperidine (2.9 ml)... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | Tertiary amide | C1CCNCC1 | C1CC[NH]CC1 | C1CC[NH]CC1.C1CC[NH]C1.c1ccccc1 | HO- | C(Cl)Cl.C(C)N(CC)CC | null | 0.083333 | C1CCNCC1.C[C@@H](C(=O)O)N1CC[C@H](NC(=O)OCc2ccccc2)C1=O>C(Cl)Cl.C(C)N(CC)CC>C[C@@H](C(=O)N1CCCCC1)N1CC[C@H](NC(=O)OCc2ccccc2)C1=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-0e293147cef644178865951b6e7d89d5 | C[C@@H](C(=O)OC(C)(C)C)N1CC[C@H](NS(=O)(=O)c2ccc3cc(Cl)ccc3c2)C1=O>>C[C@@H](C(=O)O)N1CC[C@H](NS(=O)(=O)c2ccc3cc(Cl)ccc3c2)C1=O | ClC=1C=C2C=CC(=CC2=CC1)S(=O)(=O)N[C@@H]1C(N(CC1)[C@H](C(=O)OC(C)(C)C)C)=O.FC(C(=O)O)(F)F>>ClC=1C=C2C=CC(=CC2=CC1)S(=O)(=O)N[C@@H]1C(N(CC1)[C@H](C(=O)O)C)=O | CC(C)(C)[O:5][C:3]([C@H:2]([CH3:1])[N:6]1[CH2:7][CH2:8][C@H:9]([NH:10][S:11](=[O:12])(=[O:13])[c:14]2[cH:15][cH:16][c:17]3[cH:18][c:19]([Cl:20])[cH:21][cH:22][c:23]3[cH:24]2)[C:25]1=[O:26])=[O:4]>>[CH3:1][C@@H:2]([C:3](=[O:4])[OH:5])[N:6]1[CH2:7][CH2:8][C@H:9]([NH:10][S:11](=[O:12])(=[O:13])[c:14]2[cH:15][cH:16][c:17]3... | C[C@@H](C(=O)OC(C)(C)C)N1CC[C@H](NS(=O)(=O)c2ccc3cc(Cl)ccc3c2)C1=O | C[C@@H](C(=O)O)N1CC[C@H](NS(=O)(=O)c2ccc3cc(Cl)ccc3c2)C1=O | null | null | C(Cl)Cl | Deprotection | Deprotection of carboxylic acid | 152e5537e48c95b4a3e767536b0f9f68d1308e5f484070828ab5ed951805157a | 7f019d4cfe9b3036d0a2d3a3209aa0e1fcb05418ebee15a4be5e125d315d5f01 | O=C1NCC[C@@H]1NS(=O)(=O)c1ccc2ccccc2c1 | C-C(-C)(-C)-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4]>>[C:3]-[C:2](=[O;D1;H0:4])-[OH;D1;+0:1] | 99.4 | [{"value": 99.4, "product": "ClC=1C=C2C=CC(=CC2=CC1)S(=O)(=O)N[C@@H]1C(N(CC1)[C@H](C(=O)O)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2.5 | HOUR | tert-Butyl (2S)-2-((3S)-3-{[(6-chloro-2-naphthyl)sulfonyl]amino}-2-oxopyrrolidin-1-yl)propanoate (0.643 g) was dissolved in DCM (19 ml), and trifluoroacetic acid (19 ml) was added. The mixture was stirred at room temperature for 2.5 h and then concentrated under reduced pressure. Anhydrous DCM (4 ml) was added and the ... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Boc | Carboxylic acid | null | null | C1CC[NH]C1.c1ccc2ccccc2c1 | Other | C(Cl)Cl | null | 2.5 | C[C@@H](C(=O)OC(C)(C)C)N1CC[C@H](NS(=O)(=O)c2ccc3cc(Cl)ccc3c2)C1=O>C(Cl)Cl>C[C@@H](C(=O)O)N1CC[C@H](NS(=O)(=O)c2ccc3cc(Cl)ccc3c2)C1=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-ccc78d613f444ad6b89c8dad33303608 | CCOC(=O)C(CCBr)N=[N+]=[N-].C[C@@H](N)C(=O)OC(C)(C)C>>C[C@H](C(=O)OC(C)(C)C)N1CCC(N=[N+]=[N-])C1=O | C(C)(C)(C)OC([C@H](N)C)=O.C(C)(C)N(C(C)C)CC.N(=[N+]=[N-])C(C(=O)OCC)CCBr.[I-].[Na+]>>N(=[N+]=[N-])C1C(N(CC1)[C@@H](C(=O)OC(C)(C)C)C)=O | CCO[C:17]([CH:13]([CH2:12][CH2:11]Br)[N:14]=[N+:15]=[N-:16])=[O:18].[CH3:1][C@H:2]([C:3](=[O:4])[O:5][C:6]([CH3:7])([CH3:8])[CH3:9])[NH2:10]>>[CH3:1][C@H:2]([C:3](=[O:4])[O:5][C:6]([CH3:7])([CH3:8])[CH3:9])[N:10]1[CH2:11][CH2:12][CH:13]([N:14]=[N+:15]=[N-:16])[C:17]1=[O:18] | CCOC(=O)C(CCBr)N=[N+]=[N-].C[C@@H](N)C(=O)OC(C)(C)C | C[C@H](C(=O)OC(C)(C)C)N1CCC(N=[N+]=[N-])C1=O | null | null | C(C)#N | Acylation | OtherReaction | 819e3f2b7868adc1c1b9de9bb195abc43156b28c3cf194597f96cec7ac859f91 | 0eb062b0407fca631aebf8550994dc507c145d19ea7e1f961f104337865aa8f4 | O=C1CCCN1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3](-[#7:4]=[#7;+:5]=[N;-;D1;H0:6])-[C;H0;D3;+0:7](=[O;D1;H0:8])-O-C-C.[C;D1;H3:9]-[C:10](-[NH2;D1;+0:11])-[C:12](=[O;D1;H0:13])-[#8:14]-[C:15](-[C;D1;H3:16])(-[C;D1;H3:17])-[C;D1;H3:18]>>[C;D1;H3:9]-[C:10](-[C:12](=[O;D1;H0:13])-[#8:14]-[C:15](-[C;D1;H3:16])(-[C;D1;H3:17])-[C;D1;H3:18])-[N;H0;... | 18.9 | [{"value": 18.9, "product": "N(=[N+]=[N-])C1C(N(CC1)[C@@H](C(=O)OC(C)(C)C)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | null | null | To a solution of D-alanine tert-butylester (1.28 g) and N,N-diisopropylethyamine (1.22 ml) in acetonitrile (15 ml), was added a solution of ethyl 2-azido-4-bromobutanoate (1 g) and sodium iodide (0.02 g) in acetonitrile (5 ml). The mixture was heated at 60° C. for 60 h and then concentrated under pressure to give a bro... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester.Primary amine | Tertiary amide | null | C1CC[NH]C1 | C1CC[NH]C1 | HBr | C(C)#N | 60 | null | CCOC(=O)C(CCBr)N=[N+]=[N-].C[C@@H](N)C(=O)OC(C)(C)C>C(C)#N>C[C@H](C(=O)OC(C)(C)C)N1CCC(N=[N+]=[N-])C1=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-e844e5c076c84bcdb7aca1ff5d4592b9 | CCOC(=O)C(CCI)N=[N+]=[N-].C[C@H](N)C(=O)OC(C)(C)C>>C[C@@H](C(=O)OC(C)(C)C)N1CCC(N=[N+]=[N-])C1=O | N(=[N+]=[N-])C(C(=O)OCC)CCI.C(C)(C)(C)OC([C@@H](N)C)=O>>N(=[N+]=[N-])C1C(N(CC1)[C@H](C(=O)OC(C)(C)C)C)=O | CCO[C:17]([CH:13]([CH2:12][CH2:11]I)[N:14]=[N+:15]=[N-:16])=[O:18].[CH3:1][C@@H:2]([C:3](=[O:4])[O:5][C:6]([CH3:7])([CH3:8])[CH3:9])[NH2:10]>>[CH3:1][C@@H:2]([C:3](=[O:4])[O:5][C:6]([CH3:7])([CH3:8])[CH3:9])[N:10]1[CH2:11][CH2:12][CH:13]([N:14]=[N+:15]=[N-:16])[C:17]1=[O:18] | CCOC(=O)C(CCI)N=[N+]=[N-].C[C@H](N)C(=O)OC(C)(C)C | C[C@@H](C(=O)OC(C)(C)C)N1CCC(N=[N+]=[N-])C1=O | null | null | null | Acylation | OtherReaction | 819e3f2b7868adc1c1b9de9bb195abc43156b28c3cf194597f96cec7ac859f91 | 0eb062b0407fca631aebf8550994dc507c145d19ea7e1f961f104337865aa8f4 | O=C1CCCN1 | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[#7:4]=[#7;+:5]=[N;-;D1;H0:6])-[C:7]-[CH2;D2;+0:8]-I.[C;D1;H3:9]-[C:10](-[NH2;D1;+0:11])-[C:12](=[O;D1;H0:13])-[#8:14]-[C:15](-[C;D1;H3:16])(-[C;D1;H3:17])-[C;D1;H3:18]>>[C;D1;H3:9]-[C:10](-[C:12](=[O;D1;H0:13])-[#8:14]-[C:15](-[C;D1;H3:16])(-[C;D1;H3:17])-[C;D1;H3:18])-[N;H0;D... | null | [] | null | null | null | null | Using ethyl 2-azido-4-iodobutanoate and L-alanine tert-butyl ester, and the procedure described for Intermediate 33, the title compound was prepared as a mixture of two diastereoisomers.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester.Primary amine | Tertiary amide | null | C1CC[NH]C1 | C1CC[NH]C1 | HI | null | null | null | CCOC(=O)C(CCI)N=[N+]=[N-].C[C@H](N)C(=O)OC(C)(C)C>>C[C@@H](C(=O)OC(C)(C)C)N1CCC(N=[N+]=[N-])C1=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-2e791d8ad3284a08bf77aa27bde8bef4 | CCC(=O)CBr.C[C@@H](C(=O)OC(C)(C)C)N1CC[C@H](NS(=O)(=O)c2ccc3cc(Cl)ccc3c2)C1=O>>CCC(=O)CN([C@H]1CCN([C@@H](C)C(=O)OC(C)(C)C)C1=O)S(=O)(=O)c1ccc2cc(Cl)ccc2c1 | ClC=1C=C2C=CC(=CC2=CC1)S(=O)(=O)N[C@@H]1C(N(CC1)[C@H](C(=O)OC(C)(C)C)C)=O.C[Si](C)(C)[N-][Si](C)(C)C.[Li+].CO.BrCC(CC)=O>>ClC=1C=C2C=CC(=CC2=CC1)S(=O)(=O)N([C@@H]1C(N(CC1)[C@H](C(=O)OC(C)(C)C)C)=O)CC(CC)=O | Br[CH2:5][C:3]([CH2:2][CH3:1])=[O:4].[NH:6]([C@H:7]1[CH2:8][CH2:9][N:10]([C@@H:11]([CH3:12])[C:13](=[O:14])[O:15][C:16]([CH3:17])([CH3:18])[CH3:19])[C:20]1=[O:21])[S:22](=[O:23])(=[O:24])[c:25]1[cH:26][cH:27][c:28]2[cH:29][c:30]([Cl:31])[cH:32][cH:33][c:34]2[cH:35]1>>[CH3:1][CH2:2][C:3](=[O:4])[CH2:5][N:6]([C@H:7]1[CH2... | CCC(=O)CBr.C[C@@H](C(=O)OC(C)(C)C)N1CC[C@H](NS(=O)(=O)c2ccc3cc(Cl)ccc3c2)C1=O | CCC(=O)CN([C@H]1CCN([C@@H](C)C(=O)OC(C)(C)C)C1=O)S(=O)(=O)c1ccc2cc(Cl)ccc2c1 | null | null | C1CCOC1 | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 3e42d5bcca7444f83191a46ba1444dcefee0e07920df674140f242a2d256ea8d | 73633c824b1cf45c7f3d2af586c5778a55c8407a45442da8b8f942e0aebaa600 | O=C1NCC[C@@H]1NS(=O)(=O)c1ccc2ccccc2c1 | Br-[CH2;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4].[#8:5]-[C:6](=[O;D1;H0:7])-[C:8]-[#7:9]1-[C:10]-[C:11]-[C:12](-[NH;D2;+0:13]-[#16:14](=[O;D1;H0:15])(=[O;D1;H0:16])-[c:17])-[C:18]-1=[O;D1;H0:19]>>[#8:5]-[C:6](=[O;D1;H0:7])-[C:8]-[#7:9]1-[C:10]-[C:11]-[C:12](-[N;H0;D3;+0:13](-[CH2;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4])-[#16:14](... | null | [] | null | null | 72 | HOUR | A solution of tert-butyl (2S)-2-((3S)-3-{[(6-chloro-2-naphthyl)sulfonyl]amino}-2-oxopyrrolidin-1-yl)propanoate (0.07 g) in THF (2 ml) was cooled to −78° C. under nitrogen, and treated with lithium bis(trimethylsilyl) amide (1.0M solution in THF; 0.186 ml), followed by 1-bromo-2-butanone (0.08 ml). The resultant solutio... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonamide.Primary halide | Ketone.Tertiary amine | null | null | C1CC[NH]C1.c1ccc2ccccc2c1 | HBr | C1CCOC1 | null | 72 | CCC(=O)CBr.C[C@@H](C(=O)OC(C)(C)C)N1CC[C@H](NS(=O)(=O)c2ccc3cc(Cl)ccc3c2)C1=O>C1CCOC1>CCC(=O)CN([C@H]1CCN([C@@H](C)C(=O)OC(C)(C)C)C1=O)S(=O)(=O)c1ccc2cc(Cl)ccc2c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-43b9e540a68748f4a883cdf2e800a1a2 | CCC(=O)CN([C@H]1CCN([C@@H](C)C(=O)OC(C)(C)C)C1=O)S(=O)(=O)c1ccc2cc(Cl)ccc2c1>>CCC(=O)CN([C@H]1CCN([C@@H](C)C(=O)O)C1=O)S(=O)(=O)c1ccc2cc(Cl)ccc2c1 | ClC=1C=C2C=CC(=CC2=CC1)S(=O)(=O)N([C@@H]1C(N(CC1)[C@H](C(=O)OC(C)(C)C)C)=O)CC(CC)=O.FC(C(=O)O)(F)F>>ClC=1C=C2C=CC(=CC2=CC1)S(=O)(=O)N([C@@H]1C(N(CC1)[C@H](C(=O)O)C)=O)CC(CC)=O | CC(C)(C)[O:15][C:13]([C@@H:11]([N:10]1[CH2:9][CH2:8][C@H:7]([N:6]([CH2:5][C:3]([CH2:2][CH3:1])=[O:4])[S:18](=[O:19])(=[O:20])[c:21]2[cH:22][cH:23][c:24]3[cH:25][c:26]([Cl:27])[cH:28][cH:29][c:30]3[cH:31]2)[C:16]1=[O:17])[CH3:12])=[O:14]>>[CH3:1][CH2:2][C:3](=[O:4])[CH2:5][N:6]([C@H:7]1[CH2:8][CH2:9][N:10]([C@@H:11]([CH... | CCC(=O)CN([C@H]1CCN([C@@H](C)C(=O)OC(C)(C)C)C1=O)S(=O)(=O)c1ccc2cc(Cl)ccc2c1 | CCC(=O)CN([C@H]1CCN([C@@H](C)C(=O)O)C1=O)S(=O)(=O)c1ccc2cc(Cl)ccc2c1 | null | null | C(Cl)Cl | Deprotection | Deprotection of carboxylic acid | 152e5537e48c95b4a3e767536b0f9f68d1308e5f484070828ab5ed951805157a | 7f019d4cfe9b3036d0a2d3a3209aa0e1fcb05418ebee15a4be5e125d315d5f01 | O=C1NCC[C@@H]1NS(=O)(=O)c1ccc2ccccc2c1 | C-C(-C)(-C)-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4]>>[C:3]-[C:2](=[O;D1;H0:4])-[OH;D1;+0:1] | 100.8 | [{"value": 100.8, "product": "ClC=1C=C2C=CC(=CC2=CC1)S(=O)(=O)N([C@@H]1C(N(CC1)[C@H](C(=O)O)C)=O)CC(CC)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1.5 | HOUR | tert-Butyl (2S)-2-{(3S)-3-[[(6-chloro-2-naphthyl)sulfonyl](2-oxobutyl)amino]-2-oxopyrrolidin-1-yl}propanoate (0.07 g) was dissolved in DCM (2 ml), and trifluoroacetic acid (2 ml) was added. The mixture was stirred at room temperature for 1.5 h and then partitioned between water and DCM. The organic layer was separated,... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Boc | Carboxylic acid | null | null | C1CC[NH]C1.c1ccc2ccccc2c1 | Other | C(Cl)Cl | null | 1.5 | CCC(=O)CN([C@H]1CCN([C@@H](C)C(=O)OC(C)(C)C)C1=O)S(=O)(=O)c1ccc2cc(Cl)ccc2c1>C(Cl)Cl>CCC(=O)CN([C@H]1CCN([C@@H](C)C(=O)O)C1=O)S(=O)(=O)c1ccc2cc(Cl)ccc2c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-45ff7524fc5340a38581577b0a458e5b | COS(=O)(=O)c1ccc(C)cc1.C[C@@H](C(=O)OC(C)(C)C)N1CC[C@H](NS(=O)(=O)c2ccc3cc(Cl)ccc3c2)C1=O>>C[C@@H](C(=O)OC(C)(C)C)N1CC[C@H](N(C)S(=O)(=O)c2ccc3cc(Cl)ccc3c2)C1=O | C[Si](C)(C)[N-][Si](C)(C)C.[Li+].ClC=1C=C2C=CC(=CC2=CC1)S(=O)(=O)N[C@@H]1C(N(CC1)[C@H](C(=O)OC(C)(C)C)C)=O.S(=O)(=O)(OC)C1=CC=C(C)C=C1>>ClC=1C=C2C=CC(=CC2=CC1)S(=O)(=O)N([C@@H]1C(N(CC1)[C@H](C(=O)OC(C)(C)C)C)=O)C | Cc1ccc(S(=O)(=O)O[CH3:15])cc1.[CH3:1][C@@H:2]([C:3](=[O:4])[O:5][C:6]([CH3:7])([CH3:8])[CH3:9])[N:10]1[CH2:11][CH2:12][C@H:13]([NH:14][S:16](=[O:17])(=[O:18])[c:19]2[cH:20][cH:21][c:22]3[cH:23][c:24]([Cl:25])[cH:26][cH:27][c:28]3[cH:29]2)[C:30]1=[O:31]>>[CH3:1][C@@H:2]([C:3](=[O:4])[O:5][C:6]([CH3:7])([CH3:8])[CH3:9])[... | COS(=O)(=O)c1ccc(C)cc1.C[C@@H](C(=O)OC(C)(C)C)N1CC[C@H](NS(=O)(=O)c2ccc3cc(Cl)ccc3c2)C1=O | C[C@@H](C(=O)OC(C)(C)C)N1CC[C@H](N(C)S(=O)(=O)c2ccc3cc(Cl)ccc3c2)C1=O | null | null | C1CCOC1 | Heteroatom Alkylation and Arylation | N-methylation | 1e744aaec43d4cae0f62ffc033588ec8c1162aa614027d68ba7b84bcec4663fb | 67298390bbcc11d70c41987c4ac06c2607123196b8179aab003bf84a312a9881 | O=C1NCC[C@@H]1NS(=O)(=O)c1ccc2ccccc2c1 | C-c1:c:c:c(-S(=O)(=O)-O-[CH3;D1;+0:1]):c:c:1.[#8:2]-[C:3](=[O;D1;H0:4])-[C:5]-[#7:6]1-[C:7]-[C:8]-[C:9](-[NH;D2;+0:10]-[#16:11](=[O;D1;H0:12])(=[O;D1;H0:13])-[c:14])-[C:15]-1=[O;D1;H0:16]>>[#8:2]-[C:3](=[O;D1;H0:4])-[C:5]-[#7:6]1-[C:7]-[C:8]-[C:9](-[N;H0;D3;+0:10](-[CH3;D1;+0:1])-[#16:11](=[O;D1;H0:12])(=[O;D1;H0:13])-... | null | [] | null | null | 16 | HOUR | A solution of tert-butyl (2S)-2-((3S)-3-{[(6-chloro-2-naphthyl)sulfonyl]amino}-2-oxopyrrolidin-1-yl)propanoate (0.1 g) in THF (5 ml) was cooled to −78° C. under nitrogen, and treated with lithium bis(trimethylsilyl) amide (1.0M solution in THF; 0.23 ml), followed by methyl tosylate (0.206 g). The resultant solution was... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonamide.Tosylate | Tertiary amine | c1ccccc1 | null | C1CC[NH]C1.c1ccc2ccccc2c1 | TsOH.HO- | C1CCOC1 | null | 16 | COS(=O)(=O)c1ccc(C)cc1.C[C@@H](C(=O)OC(C)(C)C)N1CC[C@H](NS(=O)(=O)c2ccc3cc(Cl)ccc3c2)C1=O>C1CCOC1>C[C@@H](C(=O)OC(C)(C)C)N1CC[C@H](N(C)S(=O)(=O)c2ccc3cc(Cl)ccc3c2)C1=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-afe77ad6405b44e491a4a99117a535e9 | C[C@@H](C(=O)OC(C)(C)C)N1CC[C@H](N(C)S(=O)(=O)c2ccc3cc(Cl)ccc3c2)C1=O>>C[C@@H](C(=O)O)N1CC[C@H](N(C)S(=O)(=O)c2ccc3cc(Cl)ccc3c2)C1=O | ClC=1C=C2C=CC(=CC2=CC1)S(=O)(=O)N([C@@H]1C(N(CC1)[C@H](C(=O)OC(C)(C)C)C)=O)C.FC(C(=O)O)(F)F>>ClC=1C=C2C=CC(=CC2=CC1)S(=O)(=O)N([C@@H]1C(N(CC1)[C@H](C(=O)O)C)=O)C | CC(C)(C)[O:5][C:3]([C@H:2]([CH3:1])[N:6]1[CH2:7][CH2:8][C@H:9]([N:10]([CH3:11])[S:12](=[O:13])(=[O:14])[c:15]2[cH:16][cH:17][c:18]3[cH:19][c:20]([Cl:21])[cH:22][cH:23][c:24]3[cH:25]2)[C:26]1=[O:27])=[O:4]>>[CH3:1][C@@H:2]([C:3](=[O:4])[OH:5])[N:6]1[CH2:7][CH2:8][C@H:9]([N:10]([CH3:11])[S:12](=[O:13])(=[O:14])[c:15]2[cH... | C[C@@H](C(=O)OC(C)(C)C)N1CC[C@H](N(C)S(=O)(=O)c2ccc3cc(Cl)ccc3c2)C1=O | C[C@@H](C(=O)O)N1CC[C@H](N(C)S(=O)(=O)c2ccc3cc(Cl)ccc3c2)C1=O | null | null | C(Cl)Cl | Deprotection | Deprotection of carboxylic acid | 152e5537e48c95b4a3e767536b0f9f68d1308e5f484070828ab5ed951805157a | 7f019d4cfe9b3036d0a2d3a3209aa0e1fcb05418ebee15a4be5e125d315d5f01 | O=C1NCC[C@@H]1NS(=O)(=O)c1ccc2ccccc2c1 | C-C(-C)(-C)-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4]>>[C:3]-[C:2](=[O;D1;H0:4])-[OH;D1;+0:1] | 102.3 | [{"value": 102.3, "product": "ClC=1C=C2C=CC(=CC2=CC1)S(=O)(=O)N([C@@H]1C(N(CC1)[C@H](C(=O)O)C)=O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1.5 | HOUR | tert-Butyl (2S)-2-{(3S)-3-[[(6-chloro-2-naphthyl)sulfonyl](methyl)amino]-2-oxopyrrolidin-1-yl}propanoate (0.1 g) was dissolved in DCM (2 ml), and trifluoroacetic acid (2 ml) was added. The mixture was stirred at room temperature for 1.5 h and then partitioned between water and DCM. The organic layer was separated, drie... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Boc | Carboxylic acid | null | null | C1CC[NH]C1.c1ccc2ccccc2c1 | Other | C(Cl)Cl | null | 1.5 | C[C@@H](C(=O)OC(C)(C)C)N1CC[C@H](N(C)S(=O)(=O)c2ccc3cc(Cl)ccc3c2)C1=O>C(Cl)Cl>C[C@@H](C(=O)O)N1CC[C@H](N(C)S(=O)(=O)c2ccc3cc(Cl)ccc3c2)C1=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-e1e715609e01411ba597fa73de2bd029 | CC(C)(C)OC(=O)N1CCCC(N)C1.CN(C)C=O.On1nnc2ccccc21>>CC(C)(C)OC(=O)N1CCCC(NC(=O)c2ccccc2)C1 | Cl.CN(CCCN=C=NCC)C.C=1C=CC2=C(C1)N=NN2O.C(C)N(CC)CC.NC1CN(CCC1)C(=O)OC(C)(C)C.CN(C)C=O.CN(C)C=O>>C(C1=CC=CC=C1)(=O)NC1CN(CCC1)C(=O)OC(C)(C)C | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][CH2:11][CH:12]([NH2:13])[CH2:22]1.CN(C)[CH:14]=[O:15].On1nn[c:16]2[cH:17][cH:18][cH:19][cH:20][c:21]12>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][CH2:11][CH:12]([NH:13][C:14](=[O:15])[c:16]2[cH:17][cH:18][cH:19][cH:20][cH:... | CC(C)(C)OC(=O)N1CCCC(N)C1.CN(C)C=O.On1nnc2ccccc21 | CC(C)(C)OC(=O)N1CCCC(NC(=O)c2ccccc2)C1 | null | null | null | Acylation | OtherReaction | eb7fb864e129846ce9d20c39f662befcabafa5211a5b135db173c20539cde95a | d0f759e36e4db8bedafa647876c8fc5b29c30b781d9a211c65bebd3576e0d0b4 | O=C(NC1CCCNC1)c1ccccc1 | C-N(-C)-[CH;D2;+0:1]=[O;D1;H0:2].O-n1:n:n:[c;H0;D3;+0:3]2:[c:4]:[c:5]:[c:6]:[c:7]:[c;H0;D3;+0:8]:2:1.[#7:9]-[C:10]-[C:11](-[NH2;D1;+0:12])-[C:13]>>[#7:9]-[C:10]-[C:11](-[NH;D2;+0:12]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c;H0;D3;+0:3]1:[c:4]:[c:5]:[c:6]:[c:7]:[cH;D2;+0:8]:1)-[C:13] | null | [] | null | null | 1 | HOUR | A solution of benzoic add (0.123 g) in DMF (5 ml) was treated with 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (0.231 g), HOBT (0.163 g) and triethylamine (0.56 ml) and stirred at room temperature for 1 h. A solution of 3-amino-1-N-Boc-piperidine (0.3 g) in DMF (1 ml) was then added and stirring conti... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Primary amine | Secondary amide | c1ccc2[nH]nnc2c1 | c1ccccc1 | C1CC[NH]CC1.c1ccccc1 | HO- | null | null | 1 | CC(C)(C)OC(=O)N1CCCC(N)C1.CN(C)C=O.On1nnc2ccccc21>>CC(C)(C)OC(=O)N1CCCC(NC(=O)c2ccccc2)C1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-c3bcead969a34b93b1d3e7c8a3b42396 | CC(C)(C)OC(=O)N1CCCC(NC(=O)c2ccccc2)C1>>O=C(NC1CCCNC1)c1ccccc1 | N.C(C1=CC=CC=C1)(=O)NC1CN(CCC1)C(=O)OC(C)(C)C.FC(C(=O)O)(F)F>>N1CC(CCC1)NC(C1=CC=CC=C1)=O | CC(C)(C)OC(=O)[N:8]1[CH2:7][CH2:6][CH2:5][CH:4]([NH:3][C:2](=[O:1])[c:10]2[cH:11][cH:12][cH:13][cH:14][cH:15]2)[CH2:9]1>>[O:1]=[C:2]([NH:3][CH:4]1[CH2:5][CH2:6][CH2:7][NH:8][CH2:9]1)[c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1 | CC(C)(C)OC(=O)N1CCCC(NC(=O)c2ccccc2)C1 | O=C(NC1CCCNC1)c1ccccc1 | null | null | C(Cl)Cl | Reduction | Boc amine deprotection | bf3cd5dc3e17e694d8665c89f5d7e08e8763b18436a633eb66e9bf530b8b0316 | a94b29c7264c852156fc1cdd4a0951a4fc26c06d0edc9e50c743825dbf79e3fd | O=C(NC1CCCNC1)c1ccccc1 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1](-[C:2]-[C:3])-[C:4]-[C:5]>>[C:5]-[C:4]-[NH;D2;+0:1]-[C:2]-[C:3] | 105.6 | [{"value": 105.6, "product": "N1CC(CCC1)NC(C1=CC=CC=C1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 6 | HOUR | A solution of tert-butyl 3-(benzoylamino)piperidine-1-carboxylate (0.120 g) in DCM (5 ml) was treated with trifluoroacetic acid (5 ml) and stirred at room temperature for 6 h. The mixture was concentrated under reduced pressure to give a yellow oil which following neutralisation with aqueous ammonia solution, was purif... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Secondary amine | C1CC[NH]CC1 | C1CCNCC1 | C1CCNCC1.c1ccccc1 | HO- | C(Cl)Cl | null | 6 | CC(C)(C)OC(=O)N1CCCC(NC(=O)c2ccccc2)C1>C(Cl)Cl>O=C(NC1CCCNC1)c1ccccc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-cef424cf0bb042ad81892277b4dd1e2e | C[C@@H](C(=O)OC(C)(C)C)N1CC[C@H](N(Cc2nccs2)S(=O)(=O)c2ccc3cc(Cl)ccc3c2)C1=O>>C[C@@H](C(=O)O)N1CC[C@H](N(Cc2nccs2)S(=O)(=O)c2ccc3cc(Cl)ccc3c2)C1=O | ClC=1C=C2C=CC(=CC2=CC1)S(=O)(=O)N([C@@H]1C(N(CC1)[C@H](C(=O)OC(C)(C)C)C)=O)CC=1SC=CN1.FC(C(=O)O)(F)F>>ClC=1C=C2C=CC(=CC2=CC1)S(=O)(=O)N([C@@H]1C(N(CC1)[C@H](C(=O)O)C)=O)CC=1SC=CN1 | CC(C)(C)[O:5][C:3]([C@H:2]([CH3:1])[N:6]1[CH2:7][CH2:8][C@H:9]([N:10]([CH2:11][c:12]2[n:13][cH:14][cH:15][s:16]2)[S:17](=[O:18])(=[O:19])[c:20]2[cH:21][cH:22][c:23]3[cH:24][c:25]([Cl:26])[cH:27][cH:28][c:29]3[cH:30]2)[C:31]1=[O:32])=[O:4]>>[CH3:1][C@@H:2]([C:3](=[O:4])[OH:5])[N:6]1[CH2:7][CH2:8][C@H:9]([N:10]([CH2:11][... | C[C@@H](C(=O)OC(C)(C)C)N1CC[C@H](N(Cc2nccs2)S(=O)(=O)c2ccc3cc(Cl)ccc3c2)C1=O | C[C@@H](C(=O)O)N1CC[C@H](N(Cc2nccs2)S(=O)(=O)c2ccc3cc(Cl)ccc3c2)C1=O | null | null | C(Cl)Cl | Deprotection | Deprotection of carboxylic acid | 152e5537e48c95b4a3e767536b0f9f68d1308e5f484070828ab5ed951805157a | 7f019d4cfe9b3036d0a2d3a3209aa0e1fcb05418ebee15a4be5e125d315d5f01 | O=C1NCC[C@@H]1N(Cc1nccs1)S(=O)(=O)c1ccc2ccccc2c1 | C-C(-C)(-C)-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4]>>[C:3]-[C:2](=[O;D1;H0:4])-[OH;D1;+0:1] | 70.5 | [{"value": 70.5, "product": "ClC=1C=C2C=CC(=CC2=CC1)S(=O)(=O)N([C@@H]1C(N(CC1)[C@H](C(=O)O)C)=O)CC=1SC=CN1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | A solution of tert-butyl (2S)-2-{(3S)-3-[[(6-chloro-2-naphthyl)sulfonyl](1,3-thiazol-2-ylmethyl)amino]-2-oxopyrrolidin-1-yl}propanoate (0.03 g) in DCM (1 ml) was treated with trifluoroacetic acid (1 ml) and stirred at room temperature for 1 h. The solution was then concentrated under reduced pressure to give the title ... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Boc | Carboxylic acid | null | null | C1CC[NH]C1.c1cscn1.c1ccc2ccccc2c1 | Other | C(Cl)Cl | null | 1 | C[C@@H](C(=O)OC(C)(C)C)N1CC[C@H](N(Cc2nccs2)S(=O)(=O)c2ccc3cc(Cl)ccc3c2)C1=O>C(Cl)Cl>C[C@@H](C(=O)O)N1CC[C@H](N(Cc2nccs2)S(=O)(=O)c2ccc3cc(Cl)ccc3c2)C1=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-0d66f2913bdf4cf684ad6583f5f27c4b | CCOC(C)=O.N[C@H](CCC(=O)O)C(=O)O.O=C(Cl)OCc1ccccc1>>COC(=O)CC[C@@H](NC(=O)OCc1ccccc1)C(=O)OC | S(=O)(Cl)Cl.N[C@H](CCC(=O)O)C(=O)O.C(O)([O-])=O.[K+].ClC(=O)OCC1=CC=CC=C1.C(C)(=O)OCC>>C(C1=CC=CC=C1)OC(=O)N[C@@H](C(=O)OC)CCC(=O)OC | CC(=O)O[CH2:1][CH3:22].[OH:2][C:3](=[O:4])[CH2:5][CH2:6][C@@H:7]([NH2:8])[C:19](=[O:20])[OH:21].Cl[C:9](=[O:10])[O:11][CH2:12][c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1>>[CH3:1][O:2][C:3](=[O:4])[CH2:5][CH2:6][C@@H:7]([NH:8][C:9](=[O:10])[O:11][CH2:12][c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1)[C:19](=[O:20])[O:21][C... | CCOC(C)=O.N[C@H](CCC(=O)O)C(=O)O.O=C(Cl)OCc1ccccc1 | COC(=O)CC[C@@H](NC(=O)OCc1ccccc1)C(=O)OC | null | null | CO.O | Protection | OtherReaction | 0f9327ec2e19bacfcf1a90db37669b7bebdc518f6ed740ed1723aab5a8fa05e0 | 388ff98aac8b3e1f916bc2d53b085f5ef557692d32ded4c7247c38bc8fd0411b | c1ccccc1 | C-C(=O)-O-[CH2;D2;+0:1]-[CH3;D1;+0:2].Cl-[C;H0;D3;+0:3](=[O;D1;H0:4])-[#8:5]-[C:6].[NH2;D1;+0:7]-[C:8](-[C:9]-[C:10]-[C:11](=[O;D1;H0:12])-[OH;D1;+0:13])-[C:14](=[O;D1;H0:15])-[OH;D1;+0:16]>>[C:6]-[#8:5]-[C;H0;D3;+0:3](=[O;D1;H0:4])-[NH;D2;+0:7]-[C:8](-[C:9]-[C:10]-[C:11](=[O;D1;H0:12])-[O;H0;D2;+0:13]-[CH3;D1;+0:1])-[... | null | [] | null | null | 5 | HOUR | Thionyl chloride (30 ml) was added to a cooled solution of D-glutamic acid (33.2 g) in methanol (250 ml) and the mixture subsequently heated under reflux for 16 h. On cooling, the mixture was concentrated under reduced pressure and the residue azeotroped with toluene to give a white solid. This was stirred with ethyl a... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Carboxylic acid.Carboxylic acid.Ester.Ether.Primary amine | Carbamic ester.Ester.Ester | null | null | c1ccccc1 | HCl | CO.O | null | 5 | CCOC(C)=O.N[C@H](CCC(=O)O)C(=O)O.O=C(Cl)OCc1ccccc1>CO.O>COC(=O)CC[C@@H](NC(=O)OCc1ccccc1)C(=O)OC |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-0716b8127315465ca5bb1dda1907bd78 | O=C([O-])CCC(NC(=O)OCc1ccccc1)C(=O)[O-]>>O=C(N[C@@H](CO)CCCO)OCc1ccccc1 | C(C1=CC=CC=C1)OC(=O)NC(C(=O)[O-])CCC(=O)[O-].[BH4-].[Li+]>>OCCC[C@H](CO)NC(OCC1=CC=CC=C1)=O | O=[C:9]([CH2:8][CH2:7][CH:4]([NH:3][C:2](=[O:1])[O:11][CH2:12][c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1)[C:5]([O-])=[O:6])[O-:10]>>[O:1]=[C:2]([NH:3][C@@H:4]([CH2:5][OH:6])[CH2:7][CH2:8][CH2:9][OH:10])[O:11][CH2:12][c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1 | O=C([O-])CCC(NC(=O)OCc1ccccc1)C(=O)[O-] | O=C(N[C@@H](CO)CCCO)OCc1ccccc1 | null | null | C1CCOC1.O.[Cl-].[Na+].O | Reduction | OtherReaction | c387793b491dae4262adcc791c73ba45fdff80869e7dcc0bd64fdd10818b0c85 | 44678ab29171bc4545e94bd412bac5255e3f987f15856a5641a6790aa4279e90 | c1ccccc1 | O=[C;H0;D3;+0:1](-[O-;H0;D1:2])-[C:3]-[C:4]-[CH;D3;+0:5](-[#7:6]-[C:7](-[#8:8])=[O;D1;H0:9])-[C;H0;D3;+0:10](-[O-])=[O;H0;D1;+0:11]>>[#8:8]-[C:7](=[O;D1;H0:9])-[#7:6]-[C@H;D3;+0:5](-[C:4]-[C:3]-[CH2;D2;+0:1]-[OH;D1;+0:2])-[CH2;D2;+0:10]-[OH;D1;+0:11] | 81.2 | [{"value": 81.2, "product": "OCCC[C@H](CO)NC(OCC1=CC=CC=C1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | DAY | A solution of dimethyl (2R)-2-{[((benzyloxy)carbonyl]amino}pentanedioate (22.4 g) in dry THF (74 ml) was added dropwise over 1 h to a stirred mixture of lithium borohydride (4.5 g) in THF (200 ml) at room temperature, under nitrogen. Stirring at room temperature was continued for 3 days. The reaction mixture was dilute... | 10.6084/m9.figshare.5104873.v1 | null | null | Primary alcohol.Primary alcohol | null | null | c1ccccc1 | Other | C1CCOC1.O.[Cl-].[Na+].O | null | 72 | O=C([O-])CCC(NC(=O)OCc1ccccc1)C(=O)[O-]>C1CCOC1.O.[Cl-].[Na+].O>O=C(N[C@@H](CO)CCCO)OCc1ccccc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-f0d992a9a8f14e6b9e4f8b4467f7e8d6 | CS(=O)(=O)Cl.O=C(N[C@@H](CO)CCCO)OCc1ccccc1.O=C([O-])O>>CS(=O)(=O)OCCC[C@H](COS(C)(=O)=O)NC(=O)OCc1ccccc1 | OCCC[C@H](CO)NC(OCC1=CC=CC=C1)=O.C(C)N(CC)CC.C([O-])(O)=O.[Na+].CS(=O)(=O)Cl>>CS(=O)(=O)OC[C@@H](CCCOS(=O)(=O)C)NC(=O)OCC1=CC=CC=C1 | Cl[S:2]([CH3:1])(=[O:3])=[O:4].[OH:5][CH2:6][CH2:7][CH2:8][C@H:9]([CH2:10][OH:11])[NH:16][C:17](=[O:18])[O:19][CH2:20][c:21]1[cH:22][cH:23][cH:24][cH:25][cH:26]1.[O-][C:13]([OH:14])=[O:15]>>[CH3:1][S:2](=[O:3])(=[O:4])[O:5][CH2:6][CH2:7][CH2:8][C@H:9]([CH2:10][O:11][S:12]([CH3:13])(=[O:14])=[O:15])[NH:16][C:17](=[O:18]... | CS(=O)(=O)Cl.O=C(N[C@@H](CO)CCCO)OCc1ccccc1.O=C([O-])O | CS(=O)(=O)OCCC[C@H](COS(C)(=O)=O)NC(=O)OCc1ccccc1 | null | null | C(Cl)Cl | Oxidation | OtherReaction | 9d4d934bcbeb2d0c12301956d4f6b3081ef6785a160067cffd9435031b1840c5 | 7b7a07a5549da95bb7017f46e245561bcc3563036e9e87ce717294d15e35b2cc | c1ccccc1 | Cl-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4].[C:5]-[C:6]-[OH;D1;+0:7].[C:8]-[C:9]-[OH;D1;+0:10].[O-]-[C;H0;D3;+0:11](=[O;H0;D1;+0:12])-[OH;D1;+0:13]>>[C:8]-[C:9]-[O;H0;D2;+0:10]-[#16:14](-[CH3;D1;+0:11])(=[O;H0;D1;+0:13])=[O;H0;D1;+0:12].[C:5]-[C:6]-[O;H0;D2;+0:7]-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])... | null | [] | null | null | 10 | MINUTE | A solution of benzyl (1R)-4-hydroxy-1-(hydroxymethyl)butylcarbamate (1.5 g) in DCM (60 ml) was treated with triethylamine (3.3 ml) and stirred at room temperature for 10 min. Methanesulphonyl chloride (1.34 ml) was then added dropwise and the resultant mixture stirred at 0° C. for 75 min. Sodium bicarbonate solution wa... | 10.6084/m9.figshare.5104873.v1 | null | Carbonic Acid.Primary alcohol.Primary alcohol.Sulfonyl halide | Mesylate.Mesylate | null | null | c1ccccc1 | Other | C(Cl)Cl | null | 0.166667 | CS(=O)(=O)Cl.O=C(N[C@@H](CO)CCCO)OCc1ccccc1.O=C([O-])O>C(Cl)Cl>CS(=O)(=O)OCCC[C@H](COS(C)(=O)=O)NC(=O)OCc1ccccc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-d7f656c0db30491b9bd260da1a6f071a | CS(=O)(=O)OCCC[C@H](COS(C)(=O)=O)NC(=O)OCc1ccccc1.N>>O=C(N[C@@H]1CCCNC1)OCc1ccccc1 | N.CS(=O)(=O)OC[C@@H](CCCOS(=O)(=O)C)NC(=O)OCC1=CC=CC=C1>>N1C[C@@H](CCC1)NC(OCC1=CC=CC=C1)=O | CS(=O)(=O)O[CH2:7][CH2:6][CH2:5][C@@H:4]([NH:3][C:2](=[O:1])[O:10][CH2:11][c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1)[CH2:9]OS(C)(=O)=O.[NH3:8]>>[O:1]=[C:2]([NH:3][C@@H:4]1[CH2:5][CH2:6][CH2:7][NH:8][CH2:9]1)[O:10][CH2:11][c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1 | CS(=O)(=O)OCCC[C@H](COS(C)(=O)=O)NC(=O)OCc1ccccc1.N | O=C(N[C@@H]1CCCNC1)OCc1ccccc1 | null | null | C1CCOC1 | Heteroatom Alkylation and Arylation | OtherReaction | 0e1938088af445a4e2d42a1889b47fa5020ec9c67bd21c065d2bda8123847234 | 02cf7cdaee4e88b5c5cc4f98c273950b8431482c5462982230888681be2f5507 | O=C(N[C@@H]1CCCNC1)OCc1ccccc1 | C-S(=O)(=O)-O-[CH2;D2;+0:1]-[C:2]-[C:3]-[C:4](-[#7:5]-[C:6]=[O;D1;H0:7])-[CH2;D2;+0:8]-O-S(-C)(=O)=O.[NH3;D0;+0:9]>>[O;D1;H0:7]=[C:6]-[#7:5]-[C:4]1-[C:3]-[C:2]-[CH2;D2;+0:1]-[NH;D2;+0:9]-[CH2;D2;+0:8]-1 | null | [] | null | null | 46 | HOUR | Liquid ammonia (ca. 30 ml) was added to a solution of (2R)-2-{[(benzyloxy)carbonyl]amino}-5-[(methylsulfonyl)oxy]pentyl methanesulfonate (1 g) in THF (15 ml) at −78° C. in a bomb reaction vessel and then the resultant mixture was allowed to reach room temperature. After 46 h, the solution was concentrated under reduced... | 10.6084/m9.figshare.5104873.v1 | null | Mesylate.Mesylate | Secondary amine | null | C1CCNCC1 | C1CCNCC1.c1ccccc1 | MsOH.HO- | C1CCOC1 | null | 46 | CS(=O)(=O)OCCC[C@H](COS(C)(=O)=O)NC(=O)OCc1ccccc1.N>C1CCOC1>O=C(N[C@@H]1CCCNC1)OCc1ccccc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-6537f41a60ef4c66bb92600fe8b85d0b | C[C@@H](C(=O)O)N1CC[C@H](NS(=O)(=O)c2ccc3cc(Cl)ccc3c2)C1=O.O=C(N[C@H]1CCCNC1)OCc1ccccc1>>C[C@@H](C(=O)N1CCC[C@H](NC(=O)OCc2ccccc2)C1)N1CC[C@H](NS(=O)(=O)c2ccc3cc(Cl)ccc3c2)C1=O | ClC=1C=C2C=CC(=CC2=CC1)S(=O)(=O)N[C@@H]1C(N(CC1)[C@H](C(=O)O)C)=O.Cl.CN(CCCN=C=NCC)C.C=1C=CC2=C(C1)N=NN2O.N1C[C@H](CCC1)NC(OCC1=CC=CC=C1)=O>>ClC=1C=C2C=CC(=CC2=CC1)S(=O)(=O)N[C@@H]1C(N(CC1)[C@H](C(=O)N1C[C@H](CCC1)NC(OCC1=CC=CC=C1)=O)C)=O | O[C:3]([C@H:2]([CH3:1])[N:22]1[CH2:23][CH2:24][C@H:25]([NH:26][S:27](=[O:28])(=[O:29])[c:30]2[cH:31][cH:32][c:33]3[cH:34][c:35]([Cl:36])[cH:37][cH:38][c:39]3[cH:40]2)[C:41]1=[O:42])=[O:4].[NH:5]1[CH2:6][CH2:7][CH2:8][C@H:9]([NH:10][C:11](=[O:12])[O:13][CH2:14][c:15]2[cH:16][cH:17][cH:18][cH:19][cH:20]2)[CH2:21]1>>[CH3:... | C[C@@H](C(=O)O)N1CC[C@H](NS(=O)(=O)c2ccc3cc(Cl)ccc3c2)C1=O.O=C(N[C@H]1CCCNC1)OCc1ccccc1 | C[C@@H](C(=O)N1CCC[C@H](NC(=O)OCc2ccccc2)C1)N1CC[C@H](NS(=O)(=O)c2ccc3cc(Cl)ccc3c2)C1=O | null | null | C(Cl)Cl.C(C)N(CC)CC | Acylation | Acylation of Nitrogen Nucleophiles by Carboxylic Acids | fbfce93ec1ece674255bb96c5cec09ad611382b41cf117dfe580015e21744a71 | c5e4172490b2731ba9322b68af56376edadc31ce0bb9a3dfdea23a1817a852fd | O=C(N[C@H]1CCCN(C(=O)CN2CC[C@H](NS(=O)(=O)c3ccc4ccccc4c3)C2=O)C1)OCc1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C;D1;H3:4])-[#7:5]-[C:6]=[O;D1;H0:7].[C:8]-[C:9]-[NH;D2;+0:10]-[C:11]-[C:12]>>[C:8]-[C:9]-[N;H0;D3;+0:10](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C;D1;H3:4])-[#7:5]-[C:6]=[O;D1;H0:7])-[C:11]-[C:12] | 42.5 | [{"value": 42.5, "product": "ClC=1C=C2C=CC(=CC2=CC1)S(=O)(=O)N[C@@H]1C(N(CC1)[C@H](C(=O)N1C[C@H](CCC1)NC(OCC1=CC=CC=C1)=O)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | A solution of (2S)-2-((3S)-3-{[(6-chloro-2-naphthyl)sulfonyl]amino}-2-oxopyrrolidin-1-yl)propanoic acid (0.408 g) in DCM (21 ml) was treated with 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (0.394 g), HOBT (0.278 g) and triethylamine (0.286 ml) and stirred at room temperature for 1 h. A solution of be... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | Tertiary amide | C1CCNCC1 | C1CC[NH]CC1 | C1CC[NH]CC1.c1ccccc1.C1CC[NH]C1.c1ccc2ccccc2c1 | HO- | C(Cl)Cl.C(C)N(CC)CC | null | 1 | C[C@@H](C(=O)O)N1CC[C@H](NS(=O)(=O)c2ccc3cc(Cl)ccc3c2)C1=O.O=C(N[C@H]1CCCNC1)OCc1ccccc1>C(Cl)Cl.C(C)N(CC)CC>C[C@@H](C(=O)N1CCC[C@H](NC(=O)OCc2ccccc2)C1)N1CC[C@H](NS(=O)(=O)c2ccc3cc(Cl)ccc3c2)C1=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-da9cd41501664b12815cadc2aacf7368 | C1COCCN1.C[C@@H](C(=O)O)N1CC[C@H](NC(=O)OCc2ccccc2)C1=O>>C[C@@H](C(=O)N1CCOCC1)N1CC[C@H](NC(=O)OCc2ccccc2)C1=O | N1CCOCC1.C(C1=CC=CC=C1)OC(=O)N[C@@H]1C(N(CC1)[C@H](C(=O)O)C)=O.F[B-](F)(F)F.N1(N=NC2=C1C=CC=C2)OC(=[N+](C)C)N(C)C.[Cl-].[NH4+].C(C)(C)N(C(C)C)CC>>C[C@@H](C(=O)N1CCOCC1)N1C([C@H](CC1)NC(OCC1=CC=CC=C1)=O)=O | [NH:5]1[CH2:6][CH2:7][O:8][CH2:9][CH2:10]1.O[C:3]([C@H:2]([CH3:1])[N:11]1[CH2:12][CH2:13][C@H:14]([NH:15][C:16](=[O:17])[O:18][CH2:19][c:20]2[cH:21][cH:22][cH:23][cH:24][cH:25]2)[C:26]1=[O:27])=[O:4]>>[CH3:1][C@@H:2]([C:3](=[O:4])[N:5]1[CH2:6][CH2:7][O:8][CH2:9][CH2:10]1)[N:11]1[CH2:12][CH2:13][C@H:14]([NH:15][C:16](=[... | C1COCCN1.C[C@@H](C(=O)O)N1CC[C@H](NC(=O)OCc2ccccc2)C1=O | C[C@@H](C(=O)N1CCOCC1)N1CC[C@H](NC(=O)OCc2ccccc2)C1=O | null | null | CN(C)C=O | Acylation | Acylation of Nitrogen Nucleophiles by Carboxylic Acids | 2ef483949e7ba3e5f888cf14cdce25fa611f75be09fdf1854a473be519821b59 | c5e4172490b2731ba9322b68af56376edadc31ce0bb9a3dfdea23a1817a852fd | O=C(N[C@H]1CCN(CC(=O)N2CCOCC2)C1=O)OCc1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C;D1;H3:4])-[#7:5]-[C:6]=[O;D1;H0:7].[#8:8]1-[C:9]-[C:10]-[NH;D2;+0:11]-[C:12]-[C:13]-1>>[C;D1;H3:4]-[C:3](-[#7:5]-[C:6]=[O;D1;H0:7])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[N;H0;D3;+0:11]1-[C:12]-[C:13]-[#8:8]-[C:9]-[C:10]-1 | null | [] | null | null | 2.5 | HOUR | (2S)-2-((3S)-3-{[(Benzyloxy)carbonyl]amino}-2-oxopyrrolidin-1-yl)propanoic acid (84.5 g) was dissolved in DMF (2I) and O-(benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium tetrafluoroborate (161 g) was added, followed by N,N-diisopropylethylamine (92 ml) and morpholine (46 ml). The mixture was stirred under nitrogen for ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | Tertiary amide | C1COCCN1 | C1COCC[NH]1 | C1COCC[NH]1.C1CC[NH]C1.c1ccccc1 | HO- | CN(C)C=O | null | 2.5 | C1COCCN1.C[C@@H](C(=O)O)N1CC[C@H](NC(=O)OCc2ccccc2)C1=O>CN(C)C=O>C[C@@H](C(=O)N1CCOCC1)N1CC[C@H](NC(=O)OCc2ccccc2)C1=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-c54c7d41fb7c4d1fb6d25147d00d8589 | C[C@@H](C(=O)N1CCOCC1)N1CC[C@H](NC(=O)OCc2ccccc2)C1=O>>C[C@@H](C(=O)N1CCOCC1)N1CC[C@H](N)C1=O | C[C@@H](C(=O)N1CCOCC1)N1C([C@H](CC1)NC(OCC1=CC=CC=C1)=O)=O>>N[C@@H]1C(N(CC1)[C@H](C(=O)N1CCOCC1)C)=O | O=C(OCc1ccccc1)[NH:15][C@H:14]1[CH2:13][CH2:12][N:11]([C@@H:2]([CH3:1])[C:3](=[O:4])[N:5]2[CH2:6][CH2:7][O:8][CH2:9][CH2:10]2)[C:16]1=[O:17]>>[CH3:1][C@@H:2]([C:3](=[O:4])[N:5]1[CH2:6][CH2:7][O:8][CH2:9][CH2:10]1)[N:11]1[CH2:12][CH2:13][C@H:14]([NH2:15])[C:16]1=[O:17] | C[C@@H](C(=O)N1CCOCC1)N1CC[C@H](NC(=O)OCc2ccccc2)C1=O | C[C@@H](C(=O)N1CCOCC1)N1CC[C@H](N)C1=O | null | [Pd] | C(C)O | Reduction | Hydrogenolysis of amides/imides/carbamates | 087b6600ba91d3df931fe6979f2445c192cbfd59e04fd2d8a10f7c7573ac669f | 4e549866ec1acadec4c84aaf8495992a28ec78d8ea5ef1b9f44dd843b0dcb7d4 | O=C(CN1CCCC1=O)N1CCOCC1 | O=C(-O-C-c1:c:c:c:c:c:1)-[NH;D2;+0:1]-[C:2]1-[C:3]-[C:4]-[#7:5](-[C:6]-[C:7](-[#7:8])=[O;D1;H0:9])-[C:10]-1=[O;D1;H0:11]>>[#7:8]-[C:7](=[O;D1;H0:9])-[C:6]-[#7:5]1-[C:4]-[C:3]-[C:2](-[NH2;D1;+0:1])-[C:10]-1=[O;D1;H0:11] | 95.7 | [{"value": 95.7, "product": "N[C@@H]1C(N(CC1)[C@H](C(=O)N1CCOCC1)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 16 | HOUR | A mixture of benzyl (3S)-1-[(1S)-1-methyl-2-morpholin-4-yl-2-oxoethyl]-2-oxopyrrolidin-3-ylcarbamate (20 g), 10% palladium on carbon (2 g) and ethanol (1.3 l) was stirred under an atmosphere of hydrogen for 16 h. The reaction mixture was filtered through Celite™ and the filtrate was concentrated under reduced pressure ... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether | Primary amine | c1ccccc1 | null | C1COCC[NH]1.C1CC[NH]C1 | HO- | [Pd].C(C)O | null | 16 | C[C@@H](C(=O)N1CCOCC1)N1CC[C@H](NC(=O)OCc2ccccc2)C1=O>[Pd].C(C)O>C[C@@H](C(=O)N1CCOCC1)N1CC[C@H](N)C1=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-41adcde0d5054088a64cf77e9b050dd6 | C[C@@H](C(=O)OC(C)(C)C)N1CC[C@H](NS(=O)(=O)c2ccc3cc(Cl)ccc3c2)C1=O.O=C(CBr)OCc1ccccc1>>C[C@@H](C(=O)OC(C)(C)C)N1CC[C@H](N(CC(=O)OCc2ccccc2)S(=O)(=O)c2ccc3cc(Cl)ccc3c2)C1=O | ClC=1C=C2C=CC(=CC2=CC1)S(=O)(=O)N[C@@H]1C(N(CC1)[C@H](C(=O)OC(C)(C)C)C)=O.C([O-])([O-])=O.[K+].[K+].C(C1=CC=CC=C1)OC(CBr)=O>>ClC=1C=C2C=CC(=CC2=CC1)S(=O)(=O)N([C@@H]1C(N(CC1)[C@H](C(=O)OC(C)(C)C)C)=O)CC(=O)OCC1=CC=CC=C1 | [CH3:1][C@@H:2]([C:3](=[O:4])[O:5][C:6]([CH3:7])([CH3:8])[CH3:9])[N:10]1[CH2:11][CH2:12][C@H:13]([NH:14][S:26](=[O:27])(=[O:28])[c:29]2[cH:30][cH:31][c:32]3[cH:33][c:34]([Cl:35])[cH:36][cH:37][c:38]3[cH:39]2)[C:40]1=[O:41].Br[CH2:15][C:16](=[O:17])[O:18][CH2:19][c:20]1[cH:21][cH:22][cH:23][cH:24][cH:25]1>>[CH3:1][C@@H:... | C[C@@H](C(=O)OC(C)(C)C)N1CC[C@H](NS(=O)(=O)c2ccc3cc(Cl)ccc3c2)C1=O.O=C(CBr)OCc1ccccc1 | C[C@@H](C(=O)OC(C)(C)C)N1CC[C@H](N(CC(=O)OCc2ccccc2)S(=O)(=O)c2ccc3cc(Cl)ccc3c2)C1=O | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 2f528facaf9aa1ab05620b510ae63e5e27715204b772ae8ea86d62f30b49e54b | dc829e3fdfa2d32260f0309a759a8629d6d95173de69dce05d7915b3a870e113 | O=C(CN([C@H]1CCNC1=O)S(=O)(=O)c1ccc2ccccc2c1)OCc1ccccc1 | Br-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#8:4]-[C:5].[#8:6]-[C:7](=[O;D1;H0:8])-[C:9]-[#7:10]1-[C:11]-[C:12]-[C:13](-[NH;D2;+0:14]-[#16:15](=[O;D1;H0:16])(=[O;D1;H0:17])-[c:18])-[C:19]-1=[O;D1;H0:20]>>[#8:6]-[C:7](=[O;D1;H0:8])-[C:9]-[#7:10]1-[C:11]-[C:12]-[C:13](-[N;H0;D3;+0:14](-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#8:4]-... | 115.5 | [{"value": 115.5, "product": "ClC=1C=C2C=CC(=CC2=CC1)S(=O)(=O)N([C@@H]1C(N(CC1)[C@H](C(=O)OC(C)(C)C)C)=O)CC(=O)OCC1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 72 | HOUR | To a solution of tert-butyl (2S)-2-((3S)-3-{[(6-chloro-2-naphthyl)sulfonyl]amino}-2-oxopyrrolidin-1-yl)propanoate (1 g) in DMF (20 ml) was added potassium carbonate (0.92 g) and benzyl-2-bromoacetate (0.33 g), and the mixture was stirred under nitrogen at room temperature for 72 h. The reaction mixture was filtered, co... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonamide.Primary halide | Ester.Tertiary amine | null | null | C1CC[NH]C1.c1ccccc1.c1ccc2ccccc2c1 | HBr | CN(C)C=O | null | 72 | C[C@@H](C(=O)OC(C)(C)C)N1CC[C@H](NS(=O)(=O)c2ccc3cc(Cl)ccc3c2)C1=O.O=C(CBr)OCc1ccccc1>CN(C)C=O>C[C@@H](C(=O)OC(C)(C)C)N1CC[C@H](N(CC(=O)OCc2ccccc2)S(=O)(=O)c2ccc3cc(Cl)ccc3c2)C1=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-a765f630bfcc4d368621ba25c966168e | O=C(O)c1cc2cc(Cl)ccc2o1>>Clc1ccc2occc2c1 | ClC=1C=CC2=C(C=C(O2)C(=O)O)C1>>ClC=1C=CC2=C(C=CO2)C1 | O=C(O)[c:7]1[o:6][c:5]2[cH:4][cH:3][c:2]([Cl:1])[cH:10][c:9]2[cH:8]1>>[Cl:1][c:2]1[cH:3][cH:4][c:5]2[o:6][cH:7][cH:8][c:9]2[cH:10]1 | O=C(O)c1cc2cc(Cl)ccc2o1 | Clc1ccc2occc2c1 | null | [Cu] | CN1C(CCC1)=O | Reduction | Decarboxylation | 1e06ee8694605f99df1524a985cad3553546b6740d6b4031e52d0cb2491b70c3 | 292164ffdf89eeb341ee9424f24084b252a703a26bb77721b558b0f8a8528c45 | c1ccc2occc2c1 | O-C(=O)-[c;H0;D3;+0:1]1:[#8;a:2]:[c:3]:[c:4]:[c:5]:1>>[#8;a:2]1:[c:3]:[c:4]:[c:5]:[cH;D2;+0:1]:1 | 418.7 | [{"value": 418.7, "product": "ClC=1C=CC2=C(C=CO2)C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 250 | CELSIUS | null | null | To a solution of 5-chloro-1-benzofuran-2-carboxylic acid (0.2 g) in 1-methyl-2-pyrrolidinone (2 ml) was added copper granules (0.2 g). The reaction mixture was heated at 250° C. for 3.5 min in a microwave. The reaction vessel was cooled to room temperature and the mixture combined with four other similar mixtures and t... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | null | c1ccc2occc2c1 | c1ccc2occc2c1 | c1ccc2occc2c1 | Other | [Cu].CN1C(CCC1)=O | 250 | null | O=C(O)c1cc2cc(Cl)ccc2o1>[Cu].CN1C(CCC1)=O>Clc1ccc2occc2c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-ae0f49a59f394151a37927a4235f4ff1 | CC(C)(C)[Si](C)(C)Oc1ccc(C=O)cc1Cl>>C=Cc1ccc(O)c(Cl)c1 | ClC=1C=C(C=O)C=CC1O[Si](C)(C)C(C)(C)C.C(CCC)[Li]>>ClC1=C(C=CC(=C1)C=C)O | CC(C)(C)[Si](C)(C)[O:7][c:6]1[cH:5][cH:4][c:3]([CH:2]=O)[cH:10][c:8]1[Cl:9]>>[CH2:1]=[CH:2][c:3]1[cH:4][cH:5][c:6]([OH:7])[c:8]([Cl:9])[cH:10]1 | CC(C)(C)[Si](C)(C)Oc1ccc(C=O)cc1Cl | C=Cc1ccc(O)c(Cl)c1 | null | [Br-].C[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1 | C1CCOC1 | Functional Group Interconversion | OtherReaction | 2e8f050b566a6b6ad6c7b65706622195f93eadf1eda7a7bb5d8cc2e9f4ca6ccf | 2005cf38c32b3fecba26a2825de56bb6eb2bc7995e575116f2f19492ff2fec94 | c1ccccc1 | C-C(-C)(-C)-[Si](-C)(-C)-[O;H0;D2;+0:1]-[c:2]1:[c:3]:[c:4]:[c:5](-[CH;D2;+0:6]=O):[c:7]:[c:8]:1>>[C;D1;H2:9]=[CH;D2;+0:6]-[c:5]1:[c:7]:[c:8]:[c:2](-[OH;D1;+0:1]):[c:3]:[c:4]:1 | null | [] | 0 | CELSIUS | 20 | MINUTE | To a slurry of methyltriphenylphosphonium bromide (0.23 g) in dry THF (5 ml) under nitrogen at −78° C., n-butyl lithium (1.6M in hexanes, 0.37 ml) was added dropwise over 2 min. The mixture was allowed to warm to 0° C., stirred for 20 min, cooled to −78° C. and a solution of 3-chloro-4-[[(1,1-dimethylethyl)dimethylsily... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.TMS ether protective group | Aromatic alcohol.Vinyl | null | null | c1ccccc1 | HO- | [Br-].C[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1.C1CCOC1 | 0 | 0.333333 | CC(C)(C)[Si](C)(C)Oc1ccc(C=O)cc1Cl>[Br-].C[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1.C1CCOC1>C=Cc1ccc(O)c(Cl)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-c90cb717958747869b5e662292221011 | CC(C)(C)[Si](C)(C)Cl.O=Cc1ccc(Cl)c(O)c1>>CC(C)(C)[Si](C)(C)Oc1cc(C=O)ccc1Cl | ClC1=C(C=C(C=O)C=C1)O.[Si](C)(C)(C(C)(C)C)Cl.C(C)N(CC)CC>>[Si](C)(C)(C(C)(C)C)OC=1C=C(C=O)C=CC1Cl | Cl[Si:5]([C:2]([CH3:1])([CH3:3])[CH3:4])([CH3:6])[CH3:7].[OH:8][c:9]1[cH:10][c:11]([CH:12]=[O:13])[cH:14][cH:15][c:16]1[Cl:17]>>[CH3:1][C:2]([CH3:3])([CH3:4])[Si:5]([CH3:6])([CH3:7])[O:8][c:9]1[cH:10][c:11]([CH:12]=[O:13])[cH:14][cH:15][c:16]1[Cl:17] | CC(C)(C)[Si](C)(C)Cl.O=Cc1ccc(Cl)c(O)c1 | CC(C)(C)[Si](C)(C)Oc1cc(C=O)ccc1Cl | null | null | C(Cl)Cl | Protection | Alcohol protection with silyl ethers | 91043baed1393f1ecd2302d7d0b31c01cf171d3977dd7c70afa1da52fa298c73 | 4a917c959d011f885a1269fa3c1f022ee5e09144996246d24e42e65634a451ac | c1ccccc1 | Cl-[Si;H0;D4;+0:1](-[C;D1;H3:2])(-[C;D1;H3:3])-[C:4](-[C;D1;H3:5])(-[C;D1;H3:6])-[C;D1;H3:7].[OH;D1;+0:8]-[c:9](:[c:10]):[c:11]>>[C;D1;H3:5]-[C:4](-[C;D1;H3:6])(-[C;D1;H3:7])-[Si;H0;D4;+0:1](-[C;D1;H3:2])(-[C;D1;H3:3])-[O;H0;D2;+0:8]-[c:9](:[c:10]):[c:11] | null | [] | null | null | 19 | HOUR | A mixture of 4-chloro-3-hydroxy-benzaldehyde* (0.354 g), 4-N,N-dimethylaminopyridine (0.028 g), tert-butyldimethylsilyl chloride (0.409 g) and triethylamine (0.473 ml) in DCM (15 ml) was stirred at room temperature under nitrogen for 19 h. The mixture was quenched with saturated aqueous sodium bicarbonate and extracted... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic alcohol.Silyl protective group | TMS ether protective group | null | null | c1ccccc1 | HCl | C(Cl)Cl | null | 19 | CC(C)(C)[Si](C)(C)Cl.O=Cc1ccc(Cl)c(O)c1>C(Cl)Cl>CC(C)(C)[Si](C)(C)Oc1cc(C=O)ccc1Cl |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-80dd5a41b73146389c0160db8e0b5bbb | CCC(N)C(=O)OC(C)(C)C.CCOC(=O)C(CCBr)N=[N+]=[N-]>>CCOC(=O)C(CCNC(CC)C(=O)OC(C)(C)C)N=[N+]=[N-] | NC(C(=O)OC(C)(C)C)CC.N(=[N+]=[N-])C(C(=O)OCC)CCBr.C(C)N(CC)CC>>N(=[N+]=[N-])C(C(=O)OCC)CCNC(CC)C(=O)OC(C)(C)C | [NH2:9][CH:10]([CH2:11][CH3:12])[C:13](=[O:14])[O:15][C:16]([CH3:17])([CH3:18])[CH3:19].Br[CH2:8][CH2:7][CH:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[N:20]=[N+:21]=[N-:22]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([CH2:7][CH2:8][NH:9][CH:10]([CH2:11][CH3:12])[C:13](=[O:14])[O:15][C:16]([CH3:17])([CH3:18])[CH3:19])[N:20]=[N+:2... | CCC(N)C(=O)OC(C)(C)C.CCOC(=O)C(CCBr)N=[N+]=[N-] | CCOC(=O)C(CCNC(CC)C(=O)OC(C)(C)C)N=[N+]=[N-] | null | null | C(C)#N | Heteroatom Alkylation and Arylation | N-alkylation of primary amines with alkyl halides | fc19a1445ff204e66e51735d0191465bda3c6691fd233624a54742c9d4828411 | 0b1d32f56ad00f1e5bdae9390f9227bbea012fa2f8203aac34726b8a6761cc7c | null | Br-[CH2;D2;+0:1]-[C:2]-[C:3]-[C:4](-[#8:5])=[O;D1;H0:6].[C:7]-[C:8](-[NH2;D1;+0:9])-[C:10](=[O;D1;H0:11])-[#8:12]-[C:13](-[C;D1;H3:14])(-[C;D1;H3:15])-[C;D1;H3:16]>>[#8:5]-[C:4](=[O;D1;H0:6])-[C:3]-[C:2]-[CH2;D2;+0:1]-[NH;D2;+0:9]-[C:8](-[C:7])-[C:10](=[O;D1;H0:11])-[#8:12]-[C:13](-[C;D1;H3:14])(-[C;D1;H3:15])-[C;D1;H3... | 52.5 | [{"value": 52.5, "product": "N(=[N+]=[N-])C(C(=O)OCC)CCNC(CC)C(=O)OC(C)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 50 | CELSIUS | null | null | To a solution of tert-butyl 2-amino-butanoate (0.397 g) and ethyl 2-azido-4-bromo-butanoate (0.286 g) in acetonitrile (5 ml) was added triethylamine (0.347 ml). The mixture was heated at 50° C. for 18 h, cooled and evaporated onto silica gel (Merck.7734). The pre-absorbed material was purified by flash column chromatog... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary amine | Secondary amine | null | null | null | HBr | C(C)#N | 50 | null | CCC(N)C(=O)OC(C)(C)C.CCOC(=O)C(CCBr)N=[N+]=[N-]>C(C)#N>CCOC(=O)C(CCNC(CC)C(=O)OC(C)(C)C)N=[N+]=[N-] |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-11adef3129b84f0b94db91599fbd1023 | CCO.C[C@H](C(=O)OC(C)(C)C)N1CC[C@@H](NS(=O)(=O)c2ccc3cc(Cl)ccc3c2)C1=O>>CCC(C(=O)OC(C)(C)C)N1CCC(NS(=O)(=O)c2ccc3cc(Cl)ccc3c2)C1=O | C(C)(C)NC(C)C.ClC=1C=C2C=CC(=CC2=CC1)S(=O)(=O)N[C@H]1C(N(CC1)[C@@H](C(=O)OC(C)(C)C)C)=O.C(C)O>>ClC=1C=C2C=CC(=CC2=CC1)S(=O)(=O)NC1C(N(CC1)C(C(=O)OC(C)(C)C)CC)=O | OC[CH3:1].[CH3:2][C@H:3]([C:4](=[O:5])[O:6][C:7]([CH3:8])([CH3:9])[CH3:10])[N:11]1[CH2:12][CH2:13][C@@H:14]([NH:15][S:16](=[O:17])(=[O:18])[c:19]2[cH:20][cH:21][c:22]3[cH:23][c:24]([Cl:25])[cH:26][cH:27][c:28]3[cH:29]2)[C:30]1=[O:31]>>[CH3:1][CH2:2][CH:3]([C:4](=[O:5])[O:6][C:7]([CH3:8])([CH3:9])[CH3:10])[N:11]1[CH2:12... | CCO.C[C@H](C(=O)OC(C)(C)C)N1CC[C@@H](NS(=O)(=O)c2ccc3cc(Cl)ccc3c2)C1=O | CCC(C(=O)OC(C)(C)C)N1CCC(NS(=O)(=O)c2ccc3cc(Cl)ccc3c2)C1=O | null | [Pd] | C(Cl)Cl | C-C Coupling | C-methylation | 861590323101b9187e0da132999bd5db6e6f128995dfe411cf8248c6aee7d060 | 5086858461038ad8c4c4a388cee61b6d9e9118227e969bc00fcc5a7517669191 | O=C1NCCC1NS(=O)(=O)c1ccc2ccccc2c1 | O-C-[CH3;D1;+0:1].[C:2]-[#7:3](-[C@H;D3;+0:4](-[CH3;D1;+0:5])-[C:6](=[O;D1;H0:7])-[#8:8]-[C:9](-[C;D1;H3:10])(-[C;D1;H3:11])-[C;D1;H3:12])-[C:13](=[O;D1;H0:14])-[C:15]>>[C:2]-[#7:3](-[CH;D3;+0:4](-[CH2;D2;+0:5]-[CH3;D1;+0:1])-[C:6](=[O;D1;H0:7])-[#8:8]-[C:9](-[C;D1;H3:10])(-[C;D1;H3:11])-[C;D1;H3:12])-[C:13](=[O;D1;H0:... | null | [] | null | null | 18 | HOUR | A mixture of Intermediate 112 [Mixture 1] (0.051 g), 10% palladium on carbon (0.01 g) and ethanol (5 ml) was stirred under an atmosphere of hydrogen for 18 h. The reaction mixture was filtered through Celite™ and the filtrate was concentrated under reduced pressure to give a yellow gum. The gum (0.034 g) in DCM (2 ml) ... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | null | null | null | C1CC[NH]C1.c1ccc2ccccc2c1 | HO- | [Pd].C(Cl)Cl | null | 18 | CCO.C[C@H](C(=O)OC(C)(C)C)N1CC[C@@H](NS(=O)(=O)c2ccc3cc(Cl)ccc3c2)C1=O>[Pd].C(Cl)Cl>CCC(C(=O)OC(C)(C)C)N1CCC(NS(=O)(=O)c2ccc3cc(Cl)ccc3c2)C1=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-18976329a6ca4e37a8fefcfba77a9493 | C1COCCN1.C[C@@H](C(=O)O)N1CC[C@H](NS(=O)(=O)c2ccc3cc(Cl)ccc3c2)C1=O>>C[C@@H](C(=O)N1CCOCC1)N1CC[C@H](NS(=O)(=O)c2ccc3cc(Cl)ccc3c2)C1=O | N1CCOCC1.ClC=1C=C2C=CC(=CC2=CC1)S(=O)(=O)N[C@@H]1C(N(CC1)[C@H](C(=O)O)C)=O.ClC=1C=C2C=CC(=CC2=CC1)S(=O)(=O)N[C@@H]1C(N(CC1)[C@H](C(=O)O)C)=O.Cl.CN(CCCN=C=NCC)C.C=1C=CC2=C(C1)N=NN2O>>ClC=1C=C2C=CC(=CC2=CC1)S(=O)(=O)N[C@@H]1C(N(CC1)[C@H](C(=O)N1CCOCC1)C)=O | [NH:5]1[CH2:6][CH2:7][O:8][CH2:9][CH2:10]1.O[C:3]([C@H:2]([CH3:1])[N:11]1[CH2:12][CH2:13][C@H:14]([NH:15][S:16](=[O:17])(=[O:18])[c:19]2[cH:20][cH:21][c:22]3[cH:23][c:24]([Cl:25])[cH:26][cH:27][c:28]3[cH:29]2)[C:30]1=[O:31])=[O:4]>>[CH3:1][C@@H:2]([C:3](=[O:4])[N:5]1[CH2:6][CH2:7][O:8][CH2:9][CH2:10]1)[N:11]1[CH2:12][C... | C1COCCN1.C[C@@H](C(=O)O)N1CC[C@H](NS(=O)(=O)c2ccc3cc(Cl)ccc3c2)C1=O | C[C@@H](C(=O)N1CCOCC1)N1CC[C@H](NS(=O)(=O)c2ccc3cc(Cl)ccc3c2)C1=O | null | null | C(Cl)Cl.C(C)N(CC)CC | Acylation | Acylation of Nitrogen Nucleophiles by Carboxylic Acids | 2ef483949e7ba3e5f888cf14cdce25fa611f75be09fdf1854a473be519821b59 | c5e4172490b2731ba9322b68af56376edadc31ce0bb9a3dfdea23a1817a852fd | O=C(CN1CC[C@H](NS(=O)(=O)c2ccc3ccccc3c2)C1=O)N1CCOCC1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C;D1;H3:4])-[#7:5]-[C:6]=[O;D1;H0:7].[#8:8]1-[C:9]-[C:10]-[NH;D2;+0:11]-[C:12]-[C:13]-1>>[C;D1;H3:4]-[C:3](-[#7:5]-[C:6]=[O;D1;H0:7])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[N;H0;D3;+0:11]1-[C:12]-[C:13]-[#8:8]-[C:9]-[C:10]-1 | null | [] | null | null | 30 | MINUTE | To a solution of (2S)-2-((3S)-3-{[(6-chloro-2-naphthyl)sulfonyl]amino}-2-oxopyrrolidin-1-yl)propanoic acid [Intermediate 29] (0.105 g) in DCM (10 ml) were added 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (0.152 g), HOBT (0.107 g) and triethylamine (0.222 ml) and the mixture was stirred at room temper... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | Tertiary amide | C1COCCN1 | C1COCC[NH]1 | C1COCC[NH]1.C1CC[NH]C1.c1ccc2ccccc2c1 | HO- | C(Cl)Cl.C(C)N(CC)CC | null | 0.5 | C1COCCN1.C[C@@H](C(=O)O)N1CC[C@H](NS(=O)(=O)c2ccc3cc(Cl)ccc3c2)C1=O>C(Cl)Cl.C(C)N(CC)CC>C[C@@H](C(=O)N1CCOCC1)N1CC[C@H](NS(=O)(=O)c2ccc3cc(Cl)ccc3c2)C1=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-7fc146245d2646ceb6e43fdc8a567d2e | C1CCNCC1.C[C@@H](C(=O)OC(C)(C)C)N1CC[C@H](NS(=O)(=O)/C=C/c2ccc(Cl)cc2)C1=O>>C[C@@H](C(=O)N1CCCCC1)N1CC[C@H](NS(=O)(=O)/C=C/c2ccc(Cl)cc2)C1=O | Cl.CN(CCCN=C=NCC)C.C=1C=CC2=C(C1)N=NN2O.FC(C(=O)O)(F)F.N1CCCCC1.ClC1=CC=C(C=C1)/C=C/S(=O)(=O)N[C@@H]1C(N(CC1)[C@H](C(=O)OC(C)(C)C)C)=O>>ClC1=CC=C(C=C1)/C=C/S(=O)(=O)N[C@@H]1C(N(CC1)[C@H](C(N1CCCCC1)=O)C)=O | [NH:5]1[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10]1.CC(C)(C)O[C:3]([C@H:2]([CH3:1])[N:11]1[CH2:12][CH2:13][C@H:14]([NH:15][S:16](=[O:17])(=[O:18])/[CH:19]=[CH:20]/[c:21]2[cH:22][cH:23][c:24]([Cl:25])[cH:26][cH:27]2)[C:28]1=[O:29])=[O:4]>>[CH3:1][C@@H:2]([C:3](=[O:4])[N:5]1[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10]1)[N:11]1[CH2:12][... | C1CCNCC1.C[C@@H](C(=O)OC(C)(C)C)N1CC[C@H](NS(=O)(=O)/C=C/c2ccc(Cl)cc2)C1=O | C[C@@H](C(=O)N1CCCCC1)N1CC[C@H](NS(=O)(=O)/C=C/c2ccc(Cl)cc2)C1=O | null | null | C(Cl)Cl.C(C)N(CC)CC | Acylation | Aminolysis of esters | a20b0e549c926e15da0ab6c9f432f3e8da8a2d0c59e3c6d1c2419879bcd6ef9b | a230d8ef639419dcbb4a41f52df2a77ab969b1b79d00c9710330f813c3417267 | O=C(CN1CC[C@H](NS(=O)(=O)/C=C/c2ccccc2)C1=O)N1CCCCC1 | C-C(-C)(-C)-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C;D1;H3:4])-[#7:5]-[C:6]=[O;D1;H0:7].[C:8]-[C:9]-[NH;D2;+0:10]-[C:11]-[C:12]>>[C:8]-[C:9]-[N;H0;D3;+0:10](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C;D1;H3:4])-[#7:5]-[C:6]=[O;D1;H0:7])-[C:11]-[C:12] | 21.3 | [{"value": 21.3, "product": "ClC1=CC=C(C=C1)/C=C/S(=O)(=O)N[C@@H]1C(N(CC1)[C@H](C(N1CCCCC1)=O)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | tert-Butyl (2S)-2-[(3S)-3-({[(E)-2-(4-chlorophenyl)ethenyl]sulfonyl}amino)-2-oxopyrrolidin-1-yl]propanoate (0.192 g) was dissolved in DCM (2 ml) and treated with trifluoroacetic acid (2 ml) and stirred at room temperature for 2 h. The mixture was then concentrated under reduced pressure to give an oil which was subsequ... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Secondary amine.Boc | Tertiary amide | C1CCNCC1 | C1CC[NH]CC1 | C1CC[NH]CC1.C1CC[NH]C1.c1ccccc1 | HO- | C(Cl)Cl.C(C)N(CC)CC | null | 2 | C1CCNCC1.C[C@@H](C(=O)OC(C)(C)C)N1CC[C@H](NS(=O)(=O)/C=C/c2ccc(Cl)cc2)C1=O>C(Cl)Cl.C(C)N(CC)CC>C[C@@H](C(=O)N1CCCCC1)N1CC[C@H](NS(=O)(=O)/C=C/c2ccc(Cl)cc2)C1=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-eb3527bffa1344d285bd826e249706ce | C[C@@H](C(=O)N1CCCC(NC(=O)OC(C)(C)C)C1)N1CC[C@H](NS(=O)(=O)c2ccc3cc(Cl)ccc3c2)C1=O>>C[C@@H](C(=O)N1CCCC(N)C1)N1CC[C@H](NS(=O)(=O)c2ccc3cc(Cl)ccc3c2)C1=O | ClC=1C=C2C=CC(=CC2=CC1)S(=O)(=O)N[C@@H]1C(N(CC1)[C@H](C(=O)N1CC(CCC1)NC(OC(C)(C)C)=O)C)=O.FC(C(=O)O)(F)F>>NC1CN(CCC1)C([C@H](C)N1C([C@H](CC1)NS(=O)(=O)C1=CC2=CC=C(C=C2C=C1)Cl)=O)=O | CC(C)(C)OC(=O)[NH:10][CH:9]1[CH2:8][CH2:7][CH2:6][N:5]([C:3]([C@H:2]([CH3:1])[N:12]2[CH2:13][CH2:14][C@H:15]([NH:16][S:17](=[O:18])(=[O:19])[c:20]3[cH:21][cH:22][c:23]4[cH:24][c:25]([Cl:26])[cH:27][cH:28][c:29]4[cH:30]3)[C:31]2=[O:32])=[O:4])[CH2:11]1>>[CH3:1][C@@H:2]([C:3](=[O:4])[N:5]1[CH2:6][CH2:7][CH2:8][CH:9]([NH2... | C[C@@H](C(=O)N1CCCC(NC(=O)OC(C)(C)C)C1)N1CC[C@H](NS(=O)(=O)c2ccc3cc(Cl)ccc3c2)C1=O | C[C@@H](C(=O)N1CCCC(N)C1)N1CC[C@H](NS(=O)(=O)c2ccc3cc(Cl)ccc3c2)C1=O | null | null | C(Cl)Cl | Reduction | Hydrogenolysis of amides/imides/carbamates | 3c33dd2a2d355ee5ba0287367e209aa147a39aa00607f0c95fb2bf1ade45d014 | c5b5dffe7dd8beebdc1baa8b5b05300a9f7079e65dcfd42ade6f8a77ff09537d | O=C(CN1CC[C@H](NS(=O)(=O)c2ccc3ccccc3c2)C1=O)N1CCCCC1 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[C:2](-[C:3])-[C:4]-[#7:5]>>[#7:5]-[C:4]-[C:2](-[NH2;D1;+0:1])-[C:3] | 76.6 | [{"value": 76.6, "product": "NC1CN(CCC1)C([C@H](C)N1C([C@H](CC1)NS(=O)(=O)C1=CC2=CC=C(C=C2C=C1)Cl)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | tert-Butyl 1-[(2S)-2-((3S)-3-{[(6-chloro-2-naphthyl)sulfonyl]amino}-2-oxopyrrolidin-1-yl)propanoyl]piperidin-3-ylcarbamate (0.6 g) was dissolved in DCM (11 ml) and trifluoroacetic acid (11 ml) was added. The mixture was stirred at room temperature for 2 h and then concentrated under reduced pressure. The residue was di... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Primary amine | null | null | C1CC[NH]CC1.C1CC[NH]C1.c1ccc2ccccc2c1 | HO- | C(Cl)Cl | null | 2 | C[C@@H](C(=O)N1CCCC(NC(=O)OC(C)(C)C)C1)N1CC[C@H](NS(=O)(=O)c2ccc3cc(Cl)ccc3c2)C1=O>C(Cl)Cl>C[C@@H](C(=O)N1CCCC(N)C1)N1CC[C@H](NS(=O)(=O)c2ccc3cc(Cl)ccc3c2)C1=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-3cee8656047a4293930211c443eeb1e4 | CC1CCCNC1.C[C@@H](C(=O)O)N1CC[C@H](NS(=O)(=O)c2ccc3cc(Cl)ccc3c2)C1=O>>CC1CCCN(C(=O)[C@H](C)N2CC[C@H](NS(=O)(=O)c3ccc4cc(Cl)ccc4c3)C2=O)C1 | ClC=1C=C2C=CC(=CC2=CC1)S(=O)(=O)N[C@@H]1C(N(CC1)[C@H](C(=O)O)C)=O.CC1CNCCC1>>ClC=1C=C2C=CC(=CC2=CC1)S(=O)(=O)N[C@@H]1C(N(CC1)[C@H](C(=O)N1CC(CCC1)C)C)=O | [CH3:1][CH:2]1[CH2:3][CH2:4][CH2:5][NH:6][CH2:32]1.O[C:7](=[O:8])[C@H:9]([CH3:10])[N:11]1[CH2:12][CH2:13][C@H:14]([NH:15][S:16](=[O:17])(=[O:18])[c:19]2[cH:20][cH:21][c:22]3[cH:23][c:24]([Cl:25])[cH:26][cH:27][c:28]3[cH:29]2)[C:30]1=[O:31]>>[CH3:1][CH:2]1[CH2:3][CH2:4][CH2:5][N:6]([C:7](=[O:8])[C@H:9]([CH3:10])[N:11]2[... | CC1CCCNC1.C[C@@H](C(=O)O)N1CC[C@H](NS(=O)(=O)c2ccc3cc(Cl)ccc3c2)C1=O | CC1CCCN(C(=O)[C@H](C)N2CC[C@H](NS(=O)(=O)c3ccc4cc(Cl)ccc4c3)C2=O)C1 | null | null | CN(C)C=O.C(Cl)Cl.C(C)(C)N(C(C)C)CC | Acylation | Acylation of Nitrogen Nucleophiles by Carboxylic Acids | fbfce93ec1ece674255bb96c5cec09ad611382b41cf117dfe580015e21744a71 | c5e4172490b2731ba9322b68af56376edadc31ce0bb9a3dfdea23a1817a852fd | O=C(CN1CC[C@H](NS(=O)(=O)c2ccc3ccccc3c2)C1=O)N1CCCCC1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C;D1;H3:4])-[#7:5]-[C:6]=[O;D1;H0:7].[C:8]-[C:9]-[NH;D2;+0:10]-[C:11]-[C:12]>>[C:8]-[C:9]-[N;H0;D3;+0:10](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C;D1;H3:4])-[#7:5]-[C:6]=[O;D1;H0:7])-[C:11]-[C:12] | 27.3 | [{"value": 27.3, "product": "ClC=1C=C2C=CC(=CC2=CC1)S(=O)(=O)N[C@@H]1C(N(CC1)[C@H](C(=O)N1CC(CCC1)C)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 4 | DAY | To polymer N-cyclohexylcarbodiimide-N′-propyloxymethyl polystyrene (0.038 g) in an Alltech™ tube was added a solution of (2S)-2-((3S)-3-{[(6-chloro-2-naphthyl)sulfonyl]amino}-2-oxopyrrolidin-1-yl)propanoic acid (0.007 g) in DCM (0.9 ml) followed by 3-methylpiperidine (0.0025 g) in DMF (0.1 ml) and N,N-diisopropylethyla... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | Tertiary amide | C1CCNCC1 | C1CC[NH]CC1 | C1CC[NH]CC1.C1CC[NH]C1.c1ccc2ccccc2c1 | HO- | CN(C)C=O.C(Cl)Cl.C(C)(C)N(C(C)C)CC | null | 96 | CC1CCCNC1.C[C@@H](C(=O)O)N1CC[C@H](NS(=O)(=O)c2ccc3cc(Cl)ccc3c2)C1=O>CN(C)C=O.C(Cl)Cl.C(C)(C)N(C(C)C)CC>CC1CCCN(C(=O)[C@H](C)N2CC[C@H](NS(=O)(=O)c3ccc4cc(Cl)ccc4c3)C2=O)C1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-f53b241f8dee44fe8e3b65a30b106c34 | CC(C)(C)OC(=O)NC1CCCNC1.C[C@@H](C(=O)O)N1CC[C@H](NS(=O)(=O)c2ccc3cc(Cl)ccc3c2)C1=O>>C[C@@H](C(=O)N1CCCC(NC(=O)OC(C)(C)C)C1)N1CC[C@H](NS(=O)(=O)c2ccc3cc(Cl)ccc3c2)C1=O | ClC=1C=C2C=CC(=CC2=CC1)S(=O)(=O)N[C@@H]1C(N(CC1)[C@H](C(=O)O)C)=O.N1CC(CCC1)NC(OC(C)(C)C)=O>>ClC=1C=C2C=CC(=CC2=CC1)S(=O)(=O)N[C@@H]1C(N(CC1)[C@H](C(=O)N1CC(CCC1)NC(OC(C)(C)C)=O)C)=O | [NH:5]1[CH2:6][CH2:7][CH2:8][CH:9]([NH:10][C:11](=[O:12])[O:13][C:14]([CH3:15])([CH3:16])[CH3:17])[CH2:18]1.O[C:3]([C@H:2]([CH3:1])[N:19]1[CH2:20][CH2:21][C@H:22]([NH:23][S:24](=[O:25])(=[O:26])[c:27]2[cH:28][cH:29][c:30]3[cH:31][c:32]([Cl:33])[cH:34][cH:35][c:36]3[cH:37]2)[C:38]1=[O:39])=[O:4]>>[CH3:1][C@@H:2]([C:3](=... | CC(C)(C)OC(=O)NC1CCCNC1.C[C@@H](C(=O)O)N1CC[C@H](NS(=O)(=O)c2ccc3cc(Cl)ccc3c2)C1=O | C[C@@H](C(=O)N1CCCC(NC(=O)OC(C)(C)C)C1)N1CC[C@H](NS(=O)(=O)c2ccc3cc(Cl)ccc3c2)C1=O | null | null | null | Acylation | Acylation of Nitrogen Nucleophiles by Carboxylic Acids | fbfce93ec1ece674255bb96c5cec09ad611382b41cf117dfe580015e21744a71 | c5e4172490b2731ba9322b68af56376edadc31ce0bb9a3dfdea23a1817a852fd | O=C(CN1CC[C@H](NS(=O)(=O)c2ccc3ccccc3c2)C1=O)N1CCCCC1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C;D1;H3:4])-[#7:5]-[C:6]=[O;D1;H0:7].[C:8]-[C:9]-[NH;D2;+0:10]-[C:11]-[C:12]>>[C:8]-[C:9]-[N;H0;D3;+0:10](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C;D1;H3:4])-[#7:5]-[C:6]=[O;D1;H0:7])-[C:11]-[C:12] | null | [] | null | null | null | null | The title compound was prepared using Intermediate 29 and tert-butyl piperidin-3-ylcarbamate, and the synthetic procedure described for Example 1.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | Tertiary amide | C1CCNCC1 | C1CC[NH]CC1 | C1CC[NH]CC1.C1CC[NH]C1.c1ccc2ccccc2c1 | HO- | null | null | null | CC(C)(C)OC(=O)NC1CCCNC1.C[C@@H](C(=O)O)N1CC[C@H](NS(=O)(=O)c2ccc3cc(Cl)ccc3c2)C1=O>>C[C@@H](C(=O)N1CCCC(NC(=O)OC(C)(C)C)C1)N1CC[C@H](NS(=O)(=O)c2ccc3cc(Cl)ccc3c2)C1=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-735af55b970e46e6a71764fc75e55f39 | C#CC(=O)O.C[C@@H](C(=O)N1CCCC(N)C1)N1CC[C@H](NS(=O)(=O)c2ccc3cc(Cl)ccc3c2)C1=O>>C#CC(=O)NC1CCCN(C(=O)[C@H](C)N2CC[C@H](NS(=O)(=O)c3ccc4cc(Cl)ccc4c3)C2=O)C1 | NC1CN(CCC1)C([C@H](C)N1C([C@H](CC1)NS(=O)(=O)C1=CC2=CC=C(C=C2C=C1)Cl)=O)=O.C(C#C)(=O)O.C(C)(C)N(C(C)C)CC.CN(C)C(=[N+](C)C)ON1C2=C(C=CC=N2)N=N1.F[P-](F)(F)(F)(F)F>>ClC=1C=C2C=CC(=CC2=CC1)S(=O)(=O)N[C@@H]1C(N(CC1)[C@H](C(=O)N1CC(CCC1)NC(C#C)=O)C)=O | O[C:3]([C:2]#[CH:1])=[O:4].[NH2:5][CH:6]1[CH2:7][CH2:8][CH2:9][N:10]([C:11](=[O:12])[C@H:13]([CH3:14])[N:15]2[CH2:16][CH2:17][C@H:18]([NH:19][S:20](=[O:21])(=[O:22])[c:23]3[cH:24][cH:25][c:26]4[cH:27][c:28]([Cl:29])[cH:30][cH:31][c:32]4[cH:33]3)[C:34]2=[O:35])[CH2:36]1>>[CH:1]#[C:2][C:3](=[O:4])[NH:5][CH:6]1[CH2:7][CH2... | C#CC(=O)O.C[C@@H](C(=O)N1CCCC(N)C1)N1CC[C@H](NS(=O)(=O)c2ccc3cc(Cl)ccc3c2)C1=O | C#CC(=O)NC1CCCN(C(=O)[C@H](C)N2CC[C@H](NS(=O)(=O)c3ccc4cc(Cl)ccc4c3)C2=O)C1 | null | null | CN(C)C=O | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(CN1CC[C@H](NS(=O)(=O)c2ccc3ccccc3c2)C1=O)N1CCCCC1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]#[C;D1;H1:4].[#7:5]-[C:6]-[C:7](-[NH2;D1;+0:8])-[C:9]>>[#7:5]-[C:6]-[C:7](-[NH;D2;+0:8]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]#[C;D1;H1:4])-[C:9] | 115.5 | [{"value": 115.5, "product": "ClC=1C=C2C=CC(=CC2=CC1)S(=O)(=O)N[C@@H]1C(N(CC1)[C@H](C(=O)N1CC(CCC1)NC(C#C)=O)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 18 | HOUR | To a solution of N-{(3S)-1-[(1S)-2-(3-aminopiperidin-1-yl)-1-methyl-2-oxoethyl]-2-oxopyrrolidin-3-yl}-6-chloronaphthalene-2-sulfonamide (0.005 g) in DMF (0.5 ml) were added propiolic acid (0.001 g), N,N-diisopropylethylamine (0.0044 ml) and o-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (0.... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | C1CC[NH]CC1.C1CC[NH]C1.c1ccc2ccccc2c1 | HO- | CN(C)C=O | null | 18 | C#CC(=O)O.C[C@@H](C(=O)N1CCCC(N)C1)N1CC[C@H](NS(=O)(=O)c2ccc3cc(Cl)ccc3c2)C1=O>CN(C)C=O>C#CC(=O)NC1CCCN(C(=O)[C@H](C)N2CC[C@H](NS(=O)(=O)c3ccc4cc(Cl)ccc4c3)C2=O)C1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-f76981696ab54f1ea4848af4078fc098 | C[C@@H](C(=O)N1CCOCC1)N1CC[C@H](NS(=O)(=O)c2ccc3cc(Cl)ccc3c2)C1=O.OCc1ccoc1>>C[C@@H](C(=O)N1CCOCC1)N1CC[C@H](N(Cc2ccoc2)S(=O)(=O)c2ccc3cc(Cl)ccc3c2)C1=O | ClC=1C=C2C=CC(=CC2=CC1)S(=O)(=O)N[C@@H]1C(N(CC1)[C@H](C(=O)N1CCOCC1)C)=O.N(=NC(=O)OC(C)C)C(=O)OC(C)C.O1C=C(C=C1)CO.C(CCC)P(CCCC)CCCC>>ClC=1C=C2C=CC(=CC2=CC1)S(=O)(=O)N([C@@H]1C(N(CC1)[C@H](C(=O)N1CCOCC1)C)=O)CC1=COC=C1 | [CH3:1][C@@H:2]([C:3](=[O:4])[N:5]1[CH2:6][CH2:7][O:8][CH2:9][CH2:10]1)[N:11]1[CH2:12][CH2:13][C@H:14]([NH:15][S:22](=[O:23])(=[O:24])[c:25]2[cH:26][cH:27][c:28]3[cH:29][c:30]([Cl:31])[cH:32][cH:33][c:34]3[cH:35]2)[C:36]1=[O:37].O[CH2:16][c:17]1[cH:18][cH:19][o:20][cH:21]1>>[CH3:1][C@@H:2]([C:3](=[O:4])[N:5]1[CH2:6][CH... | C[C@@H](C(=O)N1CCOCC1)N1CC[C@H](NS(=O)(=O)c2ccc3cc(Cl)ccc3c2)C1=O.OCc1ccoc1 | C[C@@H](C(=O)N1CCOCC1)N1CC[C@H](N(Cc2ccoc2)S(=O)(=O)c2ccc3cc(Cl)ccc3c2)C1=O | null | null | C1CCOC1 | Heteroatom Alkylation and Arylation | Mitsunobu_sulfonamide | 0bda68210bc1a4edc8064b140a39ccb3ef813b89c5267469bd545dded6906cd4 | 2497efd1dadfa61592e966deb414dc4463866875b7ffd693ba98c7592e2a7ec2 | O=C(CN1CC[C@H](N(Cc2ccoc2)S(=O)(=O)c2ccc3ccccc3c2)C1=O)N1CCOCC1 | O-[CH2;D2;+0:1]-[c:2]1:[c:3]:[c:4]:[#8;a:5]:[c:6]:1.[#7:7]-[C:8](=[O;D1;H0:9])-[C:10]-[#7:11]1-[C:12]-[C:13]-[C:14](-[NH;D2;+0:15]-[#16:16](=[O;D1;H0:17])(=[O;D1;H0:18])-[c:19])-[C:20]-1=[O;D1;H0:21]>>[#7:7]-[C:8](=[O;D1;H0:9])-[C:10]-[#7:11]1-[C:12]-[C:13]-[C:14](-[N;H0;D3;+0:15](-[CH2;D2;+0:1]-[c:2]2:[c:3]:[c:4]:[#8;... | null | [] | null | null | 60 | HOUR | A solution of 6-chloro-N-{(3S)-1-[(1S)-1-methyl-2-morpholin-4-yl-2-oxoethyl]-2-oxopyrrolidin-3-yl}naphthalene-2-sulfonamide (0.015 g) in THF (0.5 ml) was treated with diisopropyl azodicarboxylate (0.01 ml), 3-furanmethanol (0.004 ml) and tri-n-butylphosphine (0.008 ml) and shaken at room temperature for 60 h. The mixtu... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonamide.Primary alcohol | Tertiary amine | null | null | C1COCC[NH]1.C1CC[NH]C1.c1ccoc1.c1ccc2ccccc2c1 | HO- | C1CCOC1 | null | 60 | C[C@@H](C(=O)N1CCOCC1)N1CC[C@H](NS(=O)(=O)c2ccc3cc(Cl)ccc3c2)C1=O.OCc1ccoc1>C1CCOC1>C[C@@H](C(=O)N1CCOCC1)N1CC[C@H](N(Cc2ccoc2)S(=O)(=O)c2ccc3cc(Cl)ccc3c2)C1=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-7a26f7ca820749cf8efbed27692d508a | C[C@H](C(=O)OC(C)(C)C)N1CC[C@H](NS(=O)(=O)c2ccc3cc(Cl)ccc3c2)C1=O.O=C(NC1CCCNC1)c1ccccc1>>C[C@H](C(=O)N1CCCC(NC(=O)c2ccccc2)C1)N1CC[C@H](NS(=O)(=O)c2ccc3cc(Cl)ccc3c2)C1=O | ClC=1C=C2C=CC(=CC2=CC1)S(=O)(=O)N[C@@H]1C(N(CC1)[C@@H](C(=O)OC(C)(C)C)C)=O.FC(C(=O)O)(F)F.Cl.CN(CCCN=C=NCC)C.C=1C=CC2=C(C1)N=NN2O.N1CC(CCC1)NC(C1=CC=CC=C1)=O>>ClC=1C=C2C=CC(=CC2=CC1)S(=O)(=O)N[C@@H]1C(N(CC1)[C@@H](C(=O)N1CC(CCC1)NC(C1=CC=CC=C1)=O)C)=O | CC(C)(C)O[C:3]([C@@H:2]([CH3:1])[N:20]1[CH2:21][CH2:22][C@H:23]([NH:24][S:25](=[O:26])(=[O:27])[c:28]2[cH:29][cH:30][c:31]3[cH:32][c:33]([Cl:34])[cH:35][cH:36][c:37]3[cH:38]2)[C:39]1=[O:40])=[O:4].[NH:5]1[CH2:6][CH2:7][CH2:8][CH:9]([NH:10][C:11](=[O:12])[c:13]2[cH:14][cH:15][cH:16][cH:17][cH:18]2)[CH2:19]1>>[CH3:1][C@H... | C[C@H](C(=O)OC(C)(C)C)N1CC[C@H](NS(=O)(=O)c2ccc3cc(Cl)ccc3c2)C1=O.O=C(NC1CCCNC1)c1ccccc1 | C[C@H](C(=O)N1CCCC(NC(=O)c2ccccc2)C1)N1CC[C@H](NS(=O)(=O)c2ccc3cc(Cl)ccc3c2)C1=O | null | null | C(Cl)Cl.C(C)N(CC)CC | Acylation | Aminolysis of esters | a20b0e549c926e15da0ab6c9f432f3e8da8a2d0c59e3c6d1c2419879bcd6ef9b | a230d8ef639419dcbb4a41f52df2a77ab969b1b79d00c9710330f813c3417267 | O=C(NC1CCCN(C(=O)CN2CC[C@H](NS(=O)(=O)c3ccc4ccccc4c3)C2=O)C1)c1ccccc1 | C-C(-C)(-C)-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C;D1;H3:4])-[#7:5]-[C:6]=[O;D1;H0:7].[C:8]-[C:9]-[NH;D2;+0:10]-[C:11]-[C:12]>>[C:8]-[C:9]-[N;H0;D3;+0:10](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C;D1;H3:4])-[#7:5]-[C:6]=[O;D1;H0:7])-[C:11]-[C:12] | 37.3 | [{"value": 37.3, "product": "ClC=1C=C2C=CC(=CC2=CC1)S(=O)(=O)N[C@@H]1C(N(CC1)[C@@H](C(=O)N1CC(CCC1)NC(C1=CC=CC=C1)=O)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | A solution of tert-butyl (2R)-2-((3S)-3-{[(6-chloro-2-naphthyl)sulfonyl]amino)-2-oxopyrrolidin-1-yl)propanoate (0.025 g) in DCM (1 ml) was treated with trifluoroacetic acid (1 ml) and stirred at room temperature for 2 h. The mixture was then concentrated under reduced pressure to give an oil which was subsequently trea... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Secondary amine.Boc | Tertiary amide | C1CCNCC1 | C1CC[NH]CC1 | C1CC[NH]CC1.c1ccccc1.C1CC[NH]C1.c1ccc2ccccc2c1 | HO- | C(Cl)Cl.C(C)N(CC)CC | null | 2 | C[C@H](C(=O)OC(C)(C)C)N1CC[C@H](NS(=O)(=O)c2ccc3cc(Cl)ccc3c2)C1=O.O=C(NC1CCCNC1)c1ccccc1>C(Cl)Cl.C(C)N(CC)CC>C[C@H](C(=O)N1CCCC(NC(=O)c2ccccc2)C1)N1CC[C@H](NS(=O)(=O)c2ccc3cc(Cl)ccc3c2)C1=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-2a63c23aabf6477a95f607a9610fff33 | C1COCCN1.CCC(=O)CN([C@H]1CCN([C@@H](C)C(=O)O)C1=O)S(=O)(=O)c1ccc2cc(Cl)ccc2c1>>CCC(=O)CN([C@H]1CCN([C@@H](C)C(=O)N2CCOCC2)C1=O)S(=O)(=O)c1ccc2cc(Cl)ccc2c1 | N1CCOCC1.ClC=1C=C2C=CC(=CC2=CC1)S(=O)(=O)N([C@@H]1C(N(CC1)[C@H](C(=O)O)C)=O)CC(CC)=O.Cl.CN(CCCN=C=NCC)C.C=1C=CC2=C(C1)N=NN2O>>ClC=1C=C2C=CC(=CC2=CC1)S(=O)(=O)N(CC(CC)=O)[C@@H]1C(N(CC1)[C@H](C(=O)N1CCOCC1)C)=O | [NH:15]1[CH2:16][CH2:17][O:18][CH2:19][CH2:20]1.O[C:13]([C@@H:11]([N:10]1[CH2:9][CH2:8][C@H:7]([N:6]([CH2:5][C:3]([CH2:2][CH3:1])=[O:4])[S:23](=[O:24])(=[O:25])[c:26]2[cH:27][cH:28][c:29]3[cH:30][c:31]([Cl:32])[cH:33][cH:34][c:35]3[cH:36]2)[C:21]1=[O:22])[CH3:12])=[O:14]>>[CH3:1][CH2:2][C:3](=[O:4])[CH2:5][N:6]([C@H:7]... | C1COCCN1.CCC(=O)CN([C@H]1CCN([C@@H](C)C(=O)O)C1=O)S(=O)(=O)c1ccc2cc(Cl)ccc2c1 | CCC(=O)CN([C@H]1CCN([C@@H](C)C(=O)N2CCOCC2)C1=O)S(=O)(=O)c1ccc2cc(Cl)ccc2c1 | null | null | C(Cl)Cl.C(C)N(CC)CC | Acylation | Acylation of Nitrogen Nucleophiles by Carboxylic Acids | 2ef483949e7ba3e5f888cf14cdce25fa611f75be09fdf1854a473be519821b59 | c5e4172490b2731ba9322b68af56376edadc31ce0bb9a3dfdea23a1817a852fd | O=C(CN1CC[C@H](NS(=O)(=O)c2ccc3ccccc3c2)C1=O)N1CCOCC1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C;D1;H3:4])-[#7:5]-[C:6]=[O;D1;H0:7].[#8:8]1-[C:9]-[C:10]-[NH;D2;+0:11]-[C:12]-[C:13]-1>>[C;D1;H3:4]-[C:3](-[#7:5]-[C:6]=[O;D1;H0:7])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[N;H0;D3;+0:11]1-[C:10]-[C:9]-[#8:8]-[C:13]-[C:12]-1 | null | [] | null | null | 30 | MINUTE | To a solution of (2S)-2-{(3S)-3-[[(6-chloro-2-naphthyl)sulfonyl](2-oxobutyl)amino]-2-oxopyrrolidin-1-yl}propanoic acid (0.035 g) in DCM (2 ml) were added 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (0.044 g), HOBT (0.031 g) and triethylamine (0.064 ml) and the mixture was stirred at room temperature f... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | Tertiary amide | C1COCCN1 | C1COCC[NH]1 | C1CC[NH]C1.C1COCC[NH]1.c1ccc2ccccc2c1 | HO- | C(Cl)Cl.C(C)N(CC)CC | null | 0.5 | C1COCCN1.CCC(=O)CN([C@H]1CCN([C@@H](C)C(=O)O)C1=O)S(=O)(=O)c1ccc2cc(Cl)ccc2c1>C(Cl)Cl.C(C)N(CC)CC>CCC(=O)CN([C@H]1CCN([C@@H](C)C(=O)N2CCOCC2)C1=O)S(=O)(=O)c1ccc2cc(Cl)ccc2c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-0d303d5cecda4a898a2f1582f72973c0 | CC1CCCNC1.C[C@H](C(=O)O)N1CC[C@H](NS(=O)(=O)c2ccc3cc(Cl)ccc3c2)C1=O>>CC1CCCN(C(=O)[C@@H](C)N2CC[C@H](NS(=O)(=O)c3ccc4cc(Cl)ccc4c3)C2=O)C1 | CC1CNCCC1.ClC=1C=C2C=CC(=CC2=CC1)S(=O)(=O)N[C@@H]1C(N(CC1)[C@@H](C(=O)O)C)=O.Cl.CN(CCCN=C=NCC)C.C=1C=CC2=C(C1)N=NN2O>>ClC=1C=C2C=CC(=CC2=CC1)S(=O)(=O)N[C@@H]1C(N(CC1)[C@@H](C(=O)N1CC(CCC1)C)C)=O | [CH3:1][CH:2]1[CH2:3][CH2:4][CH2:5][NH:6][CH2:32]1.O[C:7](=[O:8])[C@@H:9]([CH3:10])[N:11]1[CH2:12][CH2:13][C@H:14]([NH:15][S:16](=[O:17])(=[O:18])[c:19]2[cH:20][cH:21][c:22]3[cH:23][c:24]([Cl:25])[cH:26][cH:27][c:28]3[cH:29]2)[C:30]1=[O:31]>>[CH3:1][CH:2]1[CH2:3][CH2:4][CH2:5][N:6]([C:7](=[O:8])[C@@H:9]([CH3:10])[N:11]... | CC1CCCNC1.C[C@H](C(=O)O)N1CC[C@H](NS(=O)(=O)c2ccc3cc(Cl)ccc3c2)C1=O | CC1CCCN(C(=O)[C@@H](C)N2CC[C@H](NS(=O)(=O)c3ccc4cc(Cl)ccc4c3)C2=O)C1 | null | null | C(Cl)Cl.C(C)N(CC)CC | Acylation | Acylation of Nitrogen Nucleophiles by Carboxylic Acids | fbfce93ec1ece674255bb96c5cec09ad611382b41cf117dfe580015e21744a71 | c5e4172490b2731ba9322b68af56376edadc31ce0bb9a3dfdea23a1817a852fd | O=C(CN1CC[C@H](NS(=O)(=O)c2ccc3ccccc3c2)C1=O)N1CCCCC1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C;D1;H3:4])-[#7:5]-[C:6]=[O;D1;H0:7].[C:8]-[C:9]-[NH;D2;+0:10]-[C:11]-[C:12]>>[C:8]-[C:9]-[N;H0;D3;+0:10](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C;D1;H3:4])-[#7:5]-[C:6]=[O;D1;H0:7])-[C:11]-[C:12] | null | [] | null | null | 75 | MINUTE | To a solution of (2R)-2-((3S)-3-{[(6-chloro-2-naphthyl)sulfonyl]amino}-2-oxopyrrolidin-1-yl)propanoic acid (0.018 g) in DCM (0.5 ml) were added 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (0.018 g), HOBT (0.013 g) and triethylamine (0.039 ml) and the mixture was stirred at room temperature for 75 min.... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | Tertiary amide | C1CCNCC1 | C1CC[NH]CC1 | C1CC[NH]CC1.C1CC[NH]C1.c1ccc2ccccc2c1 | HO- | C(Cl)Cl.C(C)N(CC)CC | null | 1.25 | CC1CCCNC1.C[C@H](C(=O)O)N1CC[C@H](NS(=O)(=O)c2ccc3cc(Cl)ccc3c2)C1=O>C(Cl)Cl.C(C)N(CC)CC>CC1CCCN(C(=O)[C@@H](C)N2CC[C@H](NS(=O)(=O)c3ccc4cc(Cl)ccc4c3)C2=O)C1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-6f90fee4c2b2423b968f48b74db08314 | C[C@@H](C(=O)N1CCOCC1)N1CC[C@H](NS(=O)(=O)c2ccc3cc(Cl)ccc3c2)C1=O.N#CCBr>>C[C@@H](C(=O)N1CCOCC1)N1CC[C@H](N(CC#N)S(=O)(=O)c2ccc3cc(Cl)ccc3c2)C1=O | ClC=1C=C2C=CC(=CC2=CC1)S(=O)(=O)N[C@@H]1C(N(CC1)[C@H](C(=O)N1CCOCC1)C)=O.C[Si](C)(C)[N-][Si](C)(C)C.[Li+].C[Si](C)(C)[N-][Si](C)(C)C.[Li+].BrCC#N>>ClC=1C=C2C=CC(=CC2=CC1)S(=O)(=O)N([C@@H]1C(N(CC1)[C@H](C(=O)N1CCOCC1)C)=O)CC#N | [CH3:1][C@@H:2]([C:3](=[O:4])[N:5]1[CH2:6][CH2:7][O:8][CH2:9][CH2:10]1)[N:11]1[CH2:12][CH2:13][C@H:14]([NH:15][S:19](=[O:20])(=[O:21])[c:22]2[cH:23][cH:24][c:25]3[cH:26][c:27]([Cl:28])[cH:29][cH:30][c:31]3[cH:32]2)[C:33]1=[O:34].Br[CH2:16][C:17]#[N:18]>>[CH3:1][C@@H:2]([C:3](=[O:4])[N:5]1[CH2:6][CH2:7][O:8][CH2:9][CH2:... | C[C@@H](C(=O)N1CCOCC1)N1CC[C@H](NS(=O)(=O)c2ccc3cc(Cl)ccc3c2)C1=O.N#CCBr | C[C@@H](C(=O)N1CCOCC1)N1CC[C@H](N(CC#N)S(=O)(=O)c2ccc3cc(Cl)ccc3c2)C1=O | null | null | C1CCOC1 | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 0fe6648877a29ae177a907a0d252f35d8beab440bf428116c5424a67bc0e72cd | 0b054affe7e4bb904ceae512aabc19d89c93551cb46dfbc6f220fc85e5eeff75 | O=C(CN1CC[C@H](NS(=O)(=O)c2ccc3ccccc3c2)C1=O)N1CCOCC1 | Br-[CH2;D2;+0:1]-[C:2]#[N;D1;H0:3].[#7:4]-[C:5](=[O;D1;H0:6])-[C:7]-[#7:8]1-[C:9]-[C:10]-[C:11](-[NH;D2;+0:12]-[#16:13](=[O;D1;H0:14])(=[O;D1;H0:15])-[c:16])-[C:17]-1=[O;D1;H0:18]>>[#7:4]-[C:5](=[O;D1;H0:6])-[C:7]-[#7:8]1-[C:9]-[C:10]-[C:11](-[N;H0;D3;+0:12](-[CH2;D2;+0:1]-[C:2]#[N;D1;H0:3])-[#16:13](=[O;D1;H0:14])(=[O... | 27.7 | [{"value": 27.7, "product": "ClC=1C=C2C=CC(=CC2=CC1)S(=O)(=O)N([C@@H]1C(N(CC1)[C@H](C(=O)N1CCOCC1)C)=O)CC#N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -78 | CELSIUS | 16 | HOUR | A solution of 6-chloro-N-{(3S)-1-[(1S)-1-methyl-2-morpholin-4-yl-2-oxoethyl]-2-oxopyrrolidin-3-yl}naphthalene-2-sulfonamide (0.01 g) in THF (2 ml) was cooled to −78° C. under nitrogen, and treated with lithium bis(trimethylsilyl) amide (1.0M solution in THF; 0.026 ml), followed by bromoacetonitrile (0.013 g). The resul... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonamide.Primary halide | Tertiary amine | null | null | C1COCC[NH]1.C1CC[NH]C1.c1ccc2ccccc2c1 | HBr | C1CCOC1 | -78 | 16 | C[C@@H](C(=O)N1CCOCC1)N1CC[C@H](NS(=O)(=O)c2ccc3cc(Cl)ccc3c2)C1=O.N#CCBr>C1CCOC1>C[C@@H](C(=O)N1CCOCC1)N1CC[C@H](N(CC#N)S(=O)(=O)c2ccc3cc(Cl)ccc3c2)C1=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-c3726134f7ce47758660d338cb2302ac | COC(=O)CN([C@H]1CCN([C@@H](C)C(=O)N2CCOCC2)C1=O)S(=O)(=O)c1ccc2cc(Cl)ccc2c1>>C[C@@H](C(=O)N1CCOCC1)N1CC[C@H](N(CC(=O)O)S(=O)(=O)c2ccc3cc(Cl)ccc3c2)C1=O | Cl.ClC=1C=C2C=CC(=CC2=CC1)S(=O)(=O)N(CC(=O)OC)[C@@H]1C(N(CC1)[C@H](C(=O)N1CCOCC1)C)=O.[OH-].[Li+]>>ClC=1C=C2C=CC(=CC2=CC1)S(=O)(=O)N(CC(=O)O)[C@@H]1C(N(CC1)[C@H](C(=O)N1CCOCC1)C)=O | C[O:19][C:17]([CH2:16][N:15]([C@H:14]1[CH2:13][CH2:12][N:11]([C@@H:2]([CH3:1])[C:3](=[O:4])[N:5]2[CH2:6][CH2:7][O:8][CH2:9][CH2:10]2)[C:34]1=[O:35])[S:20](=[O:21])(=[O:22])[c:23]1[cH:24][cH:25][c:26]2[cH:27][c:28]([Cl:29])[cH:30][cH:31][c:32]2[cH:33]1)=[O:18]>>[CH3:1][C@@H:2]([C:3](=[O:4])[N:5]1[CH2:6][CH2:7][O:8][CH2:... | COC(=O)CN([C@H]1CCN([C@@H](C)C(=O)N2CCOCC2)C1=O)S(=O)(=O)c1ccc2cc(Cl)ccc2c1 | C[C@@H](C(=O)N1CCOCC1)N1CC[C@H](N(CC(=O)O)S(=O)(=O)c2ccc3cc(Cl)ccc3c2)C1=O | null | null | C1CCOC1.O | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | O=C(CN1CC[C@H](NS(=O)(=O)c2ccc3ccccc3c2)C1=O)N1CCOCC1 | C-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4]>>[C:3]-[C:2](=[O;D1;H0:4])-[OH;D1;+0:1] | 61.6 | [{"value": 61.6, "product": "ClC=1C=C2C=CC(=CC2=CC1)S(=O)(=O)N(CC(=O)O)[C@@H]1C(N(CC1)[C@H](C(=O)N1CCOCC1)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of methyl N-[(6-chloro-2-naphthyl)sulfonyl]-N-{(3S)-1-[(1S)-1-methyl-2-morpholin-4-yl-2-oxoethyl]-2-oxopyrrolidin-3-yl}glycinate (0.010 g) in THF (2 ml) was added lithium hydroxide (0.003 g) in water (2 ml), and the resultant solution stirred for 16 h. The mixture was acidified to pH5 using hydrochloric a... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | C1COCC[NH]1.C1CC[NH]C1.c1ccc2ccccc2c1 | Other | C1CCOC1.O | null | null | COC(=O)CN([C@H]1CCN([C@@H](C)C(=O)N2CCOCC2)C1=O)S(=O)(=O)c1ccc2cc(Cl)ccc2c1>C1CCOC1.O>C[C@@H](C(=O)N1CCOCC1)N1CC[C@H](N(CC(=O)O)S(=O)(=O)c2ccc3cc(Cl)ccc3c2)C1=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-c61282f557ce4c26a0dea4a210034ac1 | CCOC(=O)C1CCCCN1.C[C@@H](C(=O)O)N1CC[C@H](NS(=O)(=O)c2ccc3cc(Cl)ccc3c2)C1=O>>C[C@@H](C(=O)N1CCCCC1C(=O)O)N1CC[C@H](NS(=O)(=O)c2ccc3cc(Cl)ccc3c2)C1=O | N1C(C(=O)OCC)CCCC1.ClC=1C=C2C=CC(=CC2=CC1)S(=O)(=O)N[C@@H]1C(N(CC1)[C@H](C(=O)O)C)=O.Cl.CN(CCCN=C=NCC)C.C=1C=CC2=C(C1)N=NN2O>>ClC=1C=C2C=CC(=CC2=CC1)S(=O)(=O)N[C@@H]1C(N(CC1)[C@H](C(=O)N1C(CCCC1)C(=O)O)C)=O | CC[O:13][C:11]([CH:10]1[NH:5][CH2:6][CH2:7][CH2:8][CH2:9]1)=[O:12].O[C:3]([C@H:2]([CH3:1])[N:14]1[CH2:15][CH2:16][C@H:17]([NH:18][S:19](=[O:20])(=[O:21])[c:22]2[cH:23][cH:24][c:25]3[cH:26][c:27]([Cl:28])[cH:29][cH:30][c:31]3[cH:32]2)[C:33]1=[O:34])=[O:4]>>[CH3:1][C@@H:2]([C:3](=[O:4])[N:5]1[CH2:6][CH2:7][CH2:8][CH2:9][... | CCOC(=O)C1CCCCN1.C[C@@H](C(=O)O)N1CC[C@H](NS(=O)(=O)c2ccc3cc(Cl)ccc3c2)C1=O | C[C@@H](C(=O)N1CCCCC1C(=O)O)N1CC[C@H](NS(=O)(=O)c2ccc3cc(Cl)ccc3c2)C1=O | null | null | C(Cl)Cl.C(C)N(CC)CC | Protection | OtherReaction | c14ebbb227134a7db53a92ba8c7e0f6e66e80fb137e8c94bc7392ee524bc2ca3 | a9275dd4bfdd260ffab0c2af4db0d4d1bb31d9d460b4e9fcded21863ffc3ef53 | O=C(CN1CC[C@H](NS(=O)(=O)c2ccc3ccccc3c2)C1=O)N1CCCCC1 | C-C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[C:4](-[C:5])-[NH;D2;+0:6]-[C:7]-[C:8].O-[C;H0;D3;+0:9](=[O;D1;H0:10])-[C:11](-[C;D1;H3:12])-[#7:13]-[C:14]=[O;D1;H0:15]>>[C:8]-[C:7]-[N;H0;D3;+0:6](-[C;H0;D3;+0:9](=[O;D1;H0:10])-[C:11](-[C;D1;H3:12])-[#7:13]-[C:14]=[O;D1;H0:15])-[C:4](-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1])-[C:5] | 21.9 | [{"value": 21.9, "product": "ClC=1C=C2C=CC(=CC2=CC1)S(=O)(=O)N[C@@H]1C(N(CC1)[C@H](C(=O)N1C(CCCC1)C(=O)O)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | To a solution of (2S)-2-((3S)-3-{[(6-chloro-2-naphthyl)sulfonyl]amino}-2-oxopyrrolidin-1-yl)propanoic acid (0.025 g) in DCM (10 ml) were added 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (0.036 g), HOBT (0.026 g) and triethylamine (0.026 ml) and the mixture was stirred at room temperature for 30 min. ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Ester.Secondary amine | Carboxylic acid.Tertiary amide | C1CCNCC1 | C1CC[NH]CC1 | C1CC[NH]CC1.C1CC[NH]C1.c1ccc2ccccc2c1 | HO- | C(Cl)Cl.C(C)N(CC)CC | null | 0.5 | CCOC(=O)C1CCCCN1.C[C@@H](C(=O)O)N1CC[C@H](NS(=O)(=O)c2ccc3cc(Cl)ccc3c2)C1=O>C(Cl)Cl.C(C)N(CC)CC>C[C@@H](C(=O)N1CCCCC1C(=O)O)N1CC[C@H](NS(=O)(=O)c2ccc3cc(Cl)ccc3c2)C1=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-ed4fcacec1d04b19971e56835f5b19ec | C1CCNCC1.C[C@H](C(=O)OC(C)(C)C)N1CC[C@H](NS(=O)(=O)c2ccc3cc(Cl)ccc3c2)C1=O>>C[C@H](C(=O)N1CCCCC1)N1CC[C@H](NS(=O)(=O)c2ccc3cc(Cl)ccc3c2)C1=O | ClC=1C=C2C=CC(=CC2=CC1)S(=O)(=O)N[C@@H]1C(N(CC1)[C@@H](C(=O)OC(C)(C)C)C)=O.FC(C(=O)O)(F)F.Cl.CN(CCCN=C=NCC)C.C=1C=CC2=C(C1)N=NN2O.N1CCCCC1>>ClC=1C=C2C=CC(=CC2=CC1)S(=O)(=O)N[C@@H]1C(N(CC1)[C@@H](C(N1CCCCC1)=O)C)=O | [NH:5]1[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10]1.CC(C)(C)O[C:3]([C@@H:2]([CH3:1])[N:11]1[CH2:12][CH2:13][C@H:14]([NH:15][S:16](=[O:17])(=[O:18])[c:19]2[cH:20][cH:21][c:22]3[cH:23][c:24]([Cl:25])[cH:26][cH:27][c:28]3[cH:29]2)[C:30]1=[O:31])=[O:4]>>[CH3:1][C@H:2]([C:3](=[O:4])[N:5]1[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10]1)[N:11... | C1CCNCC1.C[C@H](C(=O)OC(C)(C)C)N1CC[C@H](NS(=O)(=O)c2ccc3cc(Cl)ccc3c2)C1=O | C[C@H](C(=O)N1CCCCC1)N1CC[C@H](NS(=O)(=O)c2ccc3cc(Cl)ccc3c2)C1=O | null | null | C(Cl)Cl.C(C)N(CC)CC | Acylation | Aminolysis of esters | a20b0e549c926e15da0ab6c9f432f3e8da8a2d0c59e3c6d1c2419879bcd6ef9b | a230d8ef639419dcbb4a41f52df2a77ab969b1b79d00c9710330f813c3417267 | O=C(CN1CC[C@H](NS(=O)(=O)c2ccc3ccccc3c2)C1=O)N1CCCCC1 | C-C(-C)(-C)-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C;D1;H3:4])-[#7:5]-[C:6]=[O;D1;H0:7].[C:8]-[C:9]-[NH;D2;+0:10]-[C:11]-[C:12]>>[C:8]-[C:9]-[N;H0;D3;+0:10](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C;D1;H3:4])-[#7:5]-[C:6]=[O;D1;H0:7])-[C:11]-[C:12] | 82 | [{"value": 82.0, "product": "ClC=1C=C2C=CC(=CC2=CC1)S(=O)(=O)N[C@@H]1C(N(CC1)[C@@H](C(N1CCCCC1)=O)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | A solution of tert-butyl (2R)-2-((3S)-3-{[(6-chloro-2-naphthyl)sulfonyl]amino}-2-oxopyrrolidin-1-yl)propanoate (0.025 g) in DCM (3 ml) was treated with trifluoroacetic acid (3 ml) and stirred at room temperature for 2 h. The mixture was then concentrated under reduced pressure to give an oil which was subsequently trea... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Secondary amine.Boc | Tertiary amide | C1CCNCC1 | C1CC[NH]CC1 | C1CC[NH]CC1.C1CC[NH]C1.c1ccc2ccccc2c1 | HO- | C(Cl)Cl.C(C)N(CC)CC | null | 2 | C1CCNCC1.C[C@H](C(=O)OC(C)(C)C)N1CC[C@H](NS(=O)(=O)c2ccc3cc(Cl)ccc3c2)C1=O>C(Cl)Cl.C(C)N(CC)CC>C[C@H](C(=O)N1CCCCC1)N1CC[C@H](NS(=O)(=O)c2ccc3cc(Cl)ccc3c2)C1=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-58e4412befac46d3ad1ca83cda34a7c0 | C1CCNCC1.C[C@@H](C(=O)O)N1CC[C@H](N(C)S(=O)(=O)c2ccc3cc(Cl)ccc3c2)C1=O>>C[C@@H](C(=O)N1CCCCC1)N1CC[C@H](N(C)S(=O)(=O)c2ccc3cc(Cl)ccc3c2)C1=O | N1CCCCC1.ClC=1C=C2C=CC(=CC2=CC1)S(=O)(=O)N([C@@H]1C(N(CC1)[C@H](C(=O)O)C)=O)C.Cl.CN(CCCN=C=NCC)C.C=1C=CC2=C(C1)N=NN2O>>ClC=1C=C2C=CC(=CC2=CC1)S(=O)(=O)N([C@@H]1C(N(CC1)[C@H](C(N1CCCCC1)=O)C)=O)C | [NH:5]1[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10]1.O[C:3]([C@H:2]([CH3:1])[N:11]1[CH2:12][CH2:13][C@H:14]([N:15]([CH3:16])[S:17](=[O:18])(=[O:19])[c:20]2[cH:21][cH:22][c:23]3[cH:24][c:25]([Cl:26])[cH:27][cH:28][c:29]3[cH:30]2)[C:31]1=[O:32])=[O:4]>>[CH3:1][C@@H:2]([C:3](=[O:4])[N:5]1[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10]1)[N:1... | C1CCNCC1.C[C@@H](C(=O)O)N1CC[C@H](N(C)S(=O)(=O)c2ccc3cc(Cl)ccc3c2)C1=O | C[C@@H](C(=O)N1CCCCC1)N1CC[C@H](N(C)S(=O)(=O)c2ccc3cc(Cl)ccc3c2)C1=O | null | null | C(Cl)Cl.C(C)N(CC)CC | Acylation | Acylation of Nitrogen Nucleophiles by Carboxylic Acids | fbfce93ec1ece674255bb96c5cec09ad611382b41cf117dfe580015e21744a71 | c5e4172490b2731ba9322b68af56376edadc31ce0bb9a3dfdea23a1817a852fd | O=C(CN1CC[C@H](NS(=O)(=O)c2ccc3ccccc3c2)C1=O)N1CCCCC1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C;D1;H3:4])-[#7:5]-[C:6]=[O;D1;H0:7].[C:8]-[C:9]-[NH;D2;+0:10]-[C:11]-[C:12]>>[C:8]-[C:9]-[N;H0;D3;+0:10](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C;D1;H3:4])-[#7:5]-[C:6]=[O;D1;H0:7])-[C:11]-[C:12] | 8.6 | [{"value": 8.6, "product": "ClC=1C=C2C=CC(=CC2=CC1)S(=O)(=O)N([C@@H]1C(N(CC1)[C@H](C(N1CCCCC1)=O)C)=O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | To a solution of (2S)-2{(3S)-3-[[(6-chloro-2-naphthyl)sulfonyl](methyl)amino]-2-oxopyrrolidin-1-yl}propanoic acid (0.020 g) in DCM (2 ml) were added 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (0.011 g), HOBT (0.007 g) and triethylamine (0.020 ml) and the mixture was stirred at room temperature for 30... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | Tertiary amide | C1CCNCC1 | C1CC[NH]CC1 | C1CC[NH]CC1.C1CC[NH]C1.c1ccc2ccccc2c1 | HO- | C(Cl)Cl.C(C)N(CC)CC | null | 0.5 | C1CCNCC1.C[C@@H](C(=O)O)N1CC[C@H](N(C)S(=O)(=O)c2ccc3cc(Cl)ccc3c2)C1=O>C(Cl)Cl.C(C)N(CC)CC>C[C@@H](C(=O)N1CCCCC1)N1CC[C@H](N(C)S(=O)(=O)c2ccc3cc(Cl)ccc3c2)C1=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-bdf12c227e064ebabdacb44df1860c0a | C1CCNCC1.COC(=O)CN([C@H]1CCN([C@@H](C)C(=O)O)C1=O)S(=O)(=O)c1ccc2cc(Cl)ccc2c1>>COC(=O)CN([C@H]1CCN([C@@H](C)C(=O)N2CCCCC2)C1=O)S(=O)(=O)c1ccc2cc(Cl)ccc2c1 | N1CCCCC1.ClC=1C=C2C=CC(=CC2=CC1)S(=O)(=O)N([C@@H]1C(N(CC1)[C@H](C(=O)O)C)=O)CC(=O)OC.Cl.CN(CCCN=C=NCC)C.C=1C=CC2=C(C1)N=NN2O>>ClC=1C=C2C=CC(=CC2=CC1)S(=O)(=O)N(CC(=O)OC)[C@@H]1C(N(CC1)[C@H](C(N1CCCCC1)=O)C)=O | [NH:15]1[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20]1.O[C:13]([C@@H:11]([N:10]1[CH2:9][CH2:8][C@H:7]([N:6]([CH2:5][C:3]([O:2][CH3:1])=[O:4])[S:23](=[O:24])(=[O:25])[c:26]2[cH:27][cH:28][c:29]3[cH:30][c:31]([Cl:32])[cH:33][cH:34][c:35]3[cH:36]2)[C:21]1=[O:22])[CH3:12])=[O:14]>>[CH3:1][O:2][C:3](=[O:4])[CH2:5][N:6]([C@H:7]1[... | C1CCNCC1.COC(=O)CN([C@H]1CCN([C@@H](C)C(=O)O)C1=O)S(=O)(=O)c1ccc2cc(Cl)ccc2c1 | COC(=O)CN([C@H]1CCN([C@@H](C)C(=O)N2CCCCC2)C1=O)S(=O)(=O)c1ccc2cc(Cl)ccc2c1 | null | null | C(Cl)Cl.C(C)N(CC)CC | Acylation | Acylation of Nitrogen Nucleophiles by Carboxylic Acids | fbfce93ec1ece674255bb96c5cec09ad611382b41cf117dfe580015e21744a71 | c5e4172490b2731ba9322b68af56376edadc31ce0bb9a3dfdea23a1817a852fd | O=C(CN1CC[C@H](NS(=O)(=O)c2ccc3ccccc3c2)C1=O)N1CCCCC1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C;D1;H3:4])-[#7:5]-[C:6]=[O;D1;H0:7].[C:8]-[C:9]-[NH;D2;+0:10]-[C:11]-[C:12]>>[C:8]-[C:9]-[N;H0;D3;+0:10](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C;D1;H3:4])-[#7:5]-[C:6]=[O;D1;H0:7])-[C:11]-[C:12] | 46.5 | [{"value": 46.5, "product": "ClC=1C=C2C=CC(=CC2=CC1)S(=O)(=O)N(CC(=O)OC)[C@@H]1C(N(CC1)[C@H](C(N1CCCCC1)=O)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | To a solution of (2S)-2-{(3S)-3-[[(6-chloro-2-naphthyl)sulfonyl](2-methoxy-2-oxoethyl)amino]-2-oxopyrrolidin-1-yl}propanoic acid (0.032 g) in DCM (5 ml) were added 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (0.02 g), HOBT (0.014 g) and triethylamine (0.034 ml) and the mixture was stirred at room temp... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | Tertiary amide | C1CCNCC1 | C1CC[NH]CC1 | C1CC[NH]C1.C1CC[NH]CC1.c1ccc2ccccc2c1 | HO- | C(Cl)Cl.C(C)N(CC)CC | null | 1 | C1CCNCC1.COC(=O)CN([C@H]1CCN([C@@H](C)C(=O)O)C1=O)S(=O)(=O)c1ccc2cc(Cl)ccc2c1>C(Cl)Cl.C(C)N(CC)CC>COC(=O)CN([C@H]1CCN([C@@H](C)C(=O)N2CCCCC2)C1=O)S(=O)(=O)c1ccc2cc(Cl)ccc2c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-49ce8660a0d44e569b4a46c3a121a7e7 | COC(=O)CN([C@H]1CCN([C@@H](C)C(=O)N2CCCCC2)C1=O)S(=O)(=O)c1ccc2cc(Cl)ccc2c1.[OH-]>>CO.C[C@@H](C(=O)N1CCCCC1)N1CC[C@H](N(CC(=O)O)S(=O)(=O)c2ccc3cc(Cl)ccc3c2)C1=O | ClC=1C=C2C=CC(=CC2=CC1)S(=O)(=O)N(CC(=O)OC)[C@@H]1C(N(CC1)[C@H](C(N1CCCCC1)=O)C)=O.[OH-].[Li+].Cl>>Cl.CO.ClC=1C=C2C=CC(=CC2=CC1)S(=O)(=O)N(CC(=O)O)[C@@H]1C(N(CC1)[C@H](C(N1CCCCC1)=O)C)=O | [CH3:1][O:2][C:19]([CH2:18][N:17]([C@H:16]1[CH2:15][CH2:14][N:13]([C@@H:4]([CH3:3])[C:5](=[O:6])[N:7]2[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12]2)[C:36]1=[O:37])[S:22](=[O:23])(=[O:24])[c:25]1[cH:26][cH:27][c:28]2[cH:29][c:30]([Cl:31])[cH:32][cH:33][c:34]2[cH:35]1)=[O:20].[OH-:21]>>[CH3:1][OH:2].[CH3:3][C@@H:4]([C:5](=[O:6... | COC(=O)CN([C@H]1CCN([C@@H](C)C(=O)N2CCCCC2)C1=O)S(=O)(=O)c1ccc2cc(Cl)ccc2c1.[OH-] | CO.C[C@@H](C(=O)N1CCCCC1)N1CC[C@H](N(CC(=O)O)S(=O)(=O)c2ccc3cc(Cl)ccc3c2)C1=O | null | null | C1CCOC1.O | Acylation | OtherReaction | db9ee1d9bb846253c10c2f639d42c12d092d033c3651a71ea16dc0ecf4a55bdc | c5cee7247c9bd9461d9349ac8515839185f2e1daff3eef7b9c67c8b1310a1abe | O=C(CN1CC[C@H](NS(=O)(=O)c2ccc3ccccc3c2)C1=O)N1CCCCC1 | [#7:1]-[C:2]-[C;H0;D3;+0:3](=[O;D1;H0:4])-[O;H0;D2;+0:5]-[C;D1;H3:6].[OH-;D0:7]>>[#7:1]-[C:2]-[C;H0;D3;+0:3](=[O;D1;H0:4])-[OH;D1;+0:7].[C;D1;H3:6]-[OH;D1;+0:5] | 205.4 | [{"value": 10.0, "product": "Cl.CO", "details": "PERCENTYIELD", "is_desired": false}, {"value": 205.4, "product": "ClC=1C=C2C=CC(=CC2=CC1)S(=O)(=O)N(CC(=O)O)[C@@H]1C(N(CC1)[C@H](C(N1CCCCC1)=O)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of methyl N-[(6-chloro-2-naphthyl)sulfonyl]-N-{(3S)-1-[(1S)-1-methyl-2-oxo-2-piperidin-1-ylethyl]-2-oxopyrrolidin-3-yl}glycinate (0.010 g) in THF (1 ml) was added lithium hydroxide (0.005 g) in water (1 ml), and the resultant solution stirred for 16 h. The mixture was acidified to pH5 using hydrochloric a... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid.Methanol | null | null | C1CC[NH]CC1.C1CC[NH]C1.c1ccc2ccccc2c1 | null | C1CCOC1.O | null | null | COC(=O)CN([C@H]1CCN([C@@H](C)C(=O)N2CCCCC2)C1=O)S(=O)(=O)c1ccc2cc(Cl)ccc2c1.[OH-]>C1CCOC1.O>CO.C[C@@H](C(=O)N1CCCCC1)N1CC[C@H](N(CC(=O)O)S(=O)(=O)c2ccc3cc(Cl)ccc3c2)C1=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-df5abb0d36a745ff964e2f8fa27724ba | C[C@@H](C(=O)N1CCCCC1)N1CC[C@H](NS(=O)(=O)c2ccc3cc(Cl)ccc3c2)C1=O.N#CCBr>>C[C@@H](C(=O)N1CCCCC1)N1CC[C@H](N(CC#N)S(=O)(=O)c2ccc3cc(Cl)ccc3c2)C1=O | ClC=1C=C2C=CC(=CC2=CC1)S(=O)(=O)N[C@@H]1C(N(CC1)[C@H](C(N1CCCCC1)=O)C)=O.C[Si](C)(C)[N-][Si](C)(C)C.[Li+].C[Si](C)(C)[N-][Si](C)(C)C.[Li+].BrCC#N>>ClC=1C=C2C=CC(=CC2=CC1)S(=O)(=O)N([C@@H]1C(N(CC1)[C@H](C(N1CCCCC1)=O)C)=O)CC#N | [CH3:1][C@@H:2]([C:3](=[O:4])[N:5]1[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10]1)[N:11]1[CH2:12][CH2:13][C@H:14]([NH:15][S:19](=[O:20])(=[O:21])[c:22]2[cH:23][cH:24][c:25]3[cH:26][c:27]([Cl:28])[cH:29][cH:30][c:31]3[cH:32]2)[C:33]1=[O:34].Br[CH2:16][C:17]#[N:18]>>[CH3:1][C@@H:2]([C:3](=[O:4])[N:5]1[CH2:6][CH2:7][CH2:8][CH2:9][... | C[C@@H](C(=O)N1CCCCC1)N1CC[C@H](NS(=O)(=O)c2ccc3cc(Cl)ccc3c2)C1=O.N#CCBr | C[C@@H](C(=O)N1CCCCC1)N1CC[C@H](N(CC#N)S(=O)(=O)c2ccc3cc(Cl)ccc3c2)C1=O | null | null | C1CCOC1 | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 0fe6648877a29ae177a907a0d252f35d8beab440bf428116c5424a67bc0e72cd | 0b054affe7e4bb904ceae512aabc19d89c93551cb46dfbc6f220fc85e5eeff75 | O=C(CN1CC[C@H](NS(=O)(=O)c2ccc3ccccc3c2)C1=O)N1CCCCC1 | Br-[CH2;D2;+0:1]-[C:2]#[N;D1;H0:3].[#7:4]-[C:5](=[O;D1;H0:6])-[C:7]-[#7:8]1-[C:9]-[C:10]-[C:11](-[NH;D2;+0:12]-[#16:13](=[O;D1;H0:14])(=[O;D1;H0:15])-[c:16])-[C:17]-1=[O;D1;H0:18]>>[#7:4]-[C:5](=[O;D1;H0:6])-[C:7]-[#7:8]1-[C:9]-[C:10]-[C:11](-[N;H0;D3;+0:12](-[CH2;D2;+0:1]-[C:2]#[N;D1;H0:3])-[#16:13](=[O;D1;H0:14])(=[O... | 43 | [{"value": 43.0, "product": "ClC=1C=C2C=CC(=CC2=CC1)S(=O)(=O)N([C@@H]1C(N(CC1)[C@H](C(N1CCCCC1)=O)C)=O)CC#N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -78 | CELSIUS | 16 | HOUR | A solution of 6-chloro-N-{(3S)-1-[(1S)-1-methyl-2-oxo-2-piperidin-1-ylethyl]-2-oxopyrrolidin-3-yl}naphthalene-2-sulfonamide (0.015 g) in THF (2 ml) was cooled to −78° C. under nitrogen, and treated with lithium bis(trimethylsilyl) amide (1.0M solution in THF; 0.042 ml), followed by bromoacetonitrile (0.019 g). The resu... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonamide.Primary halide | Tertiary amine | null | null | C1CC[NH]CC1.C1CC[NH]C1.c1ccc2ccccc2c1 | HBr | C1CCOC1 | -78 | 16 | C[C@@H](C(=O)N1CCCCC1)N1CC[C@H](NS(=O)(=O)c2ccc3cc(Cl)ccc3c2)C1=O.N#CCBr>C1CCOC1>C[C@@H](C(=O)N1CCCCC1)N1CC[C@H](N(CC#N)S(=O)(=O)c2ccc3cc(Cl)ccc3c2)C1=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-a3dd945734854eb2b4129c81254e1bbf | C[C@H](C(=O)OC(C)(C)C)N1CC[C@H](N(C)S(=O)(=O)c2ccc3cc(Cl)ccc3c2)C1=O.O=C(NC1CCCNC1)c1ccccc1>>C[C@H](C(=O)N1CCCC(NC(=O)c2ccccc2)C1)N1CC[C@H](N(C)S(=O)(=O)c2ccc3cc(Cl)ccc3c2)C1=O | ClC=1C=C2C=CC(=CC2=CC1)S(=O)(=O)N([C@@H]1C(N(CC1)[C@@H](C(=O)OC(C)(C)C)C)=O)C.FC(C(=O)O)(F)F.Cl.CN(CCCN=C=NCC)C.C=1C=CC2=C(C1)N=NN2O.N1CC(CCC1)NC(C1=CC=CC=C1)=O>>ClC=1C=C2C=CC(=CC2=CC1)S(=O)(=O)N([C@@H]1C(N(CC1)[C@@H](C(=O)N1CC(CCC1)NC(C1=CC=CC=C1)=O)C)=O)C | CC(C)(C)O[C:3]([C@@H:2]([CH3:1])[N:20]1[CH2:21][CH2:22][C@H:23]([N:24]([CH3:25])[S:26](=[O:27])(=[O:28])[c:29]2[cH:30][cH:31][c:32]3[cH:33][c:34]([Cl:35])[cH:36][cH:37][c:38]3[cH:39]2)[C:40]1=[O:41])=[O:4].[NH:5]1[CH2:6][CH2:7][CH2:8][CH:9]([NH:10][C:11](=[O:12])[c:13]2[cH:14][cH:15][cH:16][cH:17][cH:18]2)[CH2:19]1>>[C... | C[C@H](C(=O)OC(C)(C)C)N1CC[C@H](N(C)S(=O)(=O)c2ccc3cc(Cl)ccc3c2)C1=O.O=C(NC1CCCNC1)c1ccccc1 | C[C@H](C(=O)N1CCCC(NC(=O)c2ccccc2)C1)N1CC[C@H](N(C)S(=O)(=O)c2ccc3cc(Cl)ccc3c2)C1=O | null | null | C(Cl)Cl.C(C)N(CC)CC | Acylation | Aminolysis of esters | a20b0e549c926e15da0ab6c9f432f3e8da8a2d0c59e3c6d1c2419879bcd6ef9b | a230d8ef639419dcbb4a41f52df2a77ab969b1b79d00c9710330f813c3417267 | O=C(NC1CCCN(C(=O)CN2CC[C@H](NS(=O)(=O)c3ccc4ccccc4c3)C2=O)C1)c1ccccc1 | C-C(-C)(-C)-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C;D1;H3:4])-[#7:5]-[C:6]=[O;D1;H0:7].[C:8]-[C:9]-[NH;D2;+0:10]-[C:11]-[C:12]>>[C:8]-[C:9]-[N;H0;D3;+0:10](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C;D1;H3:4])-[#7:5]-[C:6]=[O;D1;H0:7])-[C:11]-[C:12] | 55.2 | [{"value": 55.2, "product": "ClC=1C=C2C=CC(=CC2=CC1)S(=O)(=O)N([C@@H]1C(N(CC1)[C@@H](C(=O)N1CC(CCC1)NC(C1=CC=CC=C1)=O)C)=O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | A solution of tert-butyl (2R)-2-{(3S)-3-[[(6-chloro-2-naphthyl)sulfonyl](methyl)amino]-2-oxopyrrolidin-1-yl}propanoate (0.017 g) in DCM (0.5 ml) was treated with trifluoroacetic acid (0.5 ml) and stirred at room temperature for 2 h. The mixture was then concentrated under reduced pressure to give an oil which was subse... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Secondary amine.Boc | Tertiary amide | C1CCNCC1 | C1CC[NH]CC1 | C1CC[NH]CC1.c1ccccc1.C1CC[NH]C1.c1ccc2ccccc2c1 | HO- | C(Cl)Cl.C(C)N(CC)CC | null | 2 | C[C@H](C(=O)OC(C)(C)C)N1CC[C@H](N(C)S(=O)(=O)c2ccc3cc(Cl)ccc3c2)C1=O.O=C(NC1CCCNC1)c1ccccc1>C(Cl)Cl.C(C)N(CC)CC>C[C@H](C(=O)N1CCCC(NC(=O)c2ccccc2)C1)N1CC[C@H](N(C)S(=O)(=O)c2ccc3cc(Cl)ccc3c2)C1=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-993085dca3ef4537b2715ac868b3332c | CC=O.C[C@@H](C(=O)N1CCCC(N)C1)N1CC[C@H](NS(=O)(=O)c2ccc3cc(Cl)ccc3c2)C1=O>>CCNC1CCCN(C(=O)[C@H](C)N2CC[C@H](NS(=O)(=O)c3ccc4cc(Cl)ccc4c3)C2=O)C1 | C(C)=O.NC1CN(CCC1)C([C@H](C)N1C([C@H](CC1)NS(=O)(=O)C1=CC2=CC=C(C=C2C=C1)Cl)=O)=O.C(C)(=O)O.C(C)(=O)O.C(C)(=O)O[BH-](OC(C)=O)OC(C)=O.C(C)[N+](CC)(CC)CC.C(C)=O>>ClC=1C=C2C=CC(=CC2=CC1)S(=O)(=O)N[C@@H]1C(N(CC1)[C@H](C(=O)N1CC(CCC1)NCC)C)=O | O=[CH:2][CH3:1].[NH2:3][CH:4]1[CH2:5][CH2:6][CH2:7][N:8]([C:9](=[O:10])[C@H:11]([CH3:12])[N:13]2[CH2:14][CH2:15][C@H:16]([NH:17][S:18](=[O:19])(=[O:20])[c:21]3[cH:22][cH:23][c:24]4[cH:25][c:26]([Cl:27])[cH:28][cH:29][c:30]4[cH:31]3)[C:32]2=[O:33])[CH2:34]1>>[CH3:1][CH2:2][NH:3][CH:4]1[CH2:5][CH2:6][CH2:7][N:8]([C:9](=[... | CC=O.C[C@@H](C(=O)N1CCCC(N)C1)N1CC[C@H](NS(=O)(=O)c2ccc3cc(Cl)ccc3c2)C1=O | CCNC1CCCN(C(=O)[C@H](C)N2CC[C@H](NS(=O)(=O)c3ccc4cc(Cl)ccc4c3)C2=O)C1 | null | null | C(Cl)Cl | Heteroatom Alkylation and Arylation | Reductive amination with aldehyde | 422be648aea52bce28ccc8fb32ec3178aaa47bbd624f063874619362f075b5f2 | 7915721a3e395aed85e3c40dc4d725c571a931ac517c6a0da16f2a2b0bb5eac7 | O=C(CN1CC[C@H](NS(=O)(=O)c2ccc3ccccc3c2)C1=O)N1CCCCC1 | O=[CH;D2;+0:1]-[C;D1;H3:2].[#7:3]-[C:4]-[C:5](-[NH2;D1;+0:6])-[C:7]>>[#7:3]-[C:4]-[C:5](-[NH;D2;+0:6]-[CH2;D2;+0:1]-[C;D1;H3:2])-[C:7] | null | [] | null | null | 60 | HOUR | To a solution of acetaldehyde (0.041 ml from a stock solution made up from 0.0127 l acetaldehyde dissolved in 1 ml DCM)) in dry DCM (0.4 ml) treated with acetic acid (0.1 ml from a stock solution made up from 0.0054 ml acetic acid dissolved in 1 ml DCM) was added N-{(3S)-1-[(1S)-2-(3-aminopiperidin-1-yl)-1-methyl-2-oxo... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Primary amine | Secondary amine | null | null | C1CC[NH]CC1.C1CC[NH]C1.c1ccc2ccccc2c1 | Other | C(Cl)Cl | null | 60 | CC=O.C[C@@H](C(=O)N1CCCC(N)C1)N1CC[C@H](NS(=O)(=O)c2ccc3cc(Cl)ccc3c2)C1=O>C(Cl)Cl>CCNC1CCCN(C(=O)[C@H](C)N2CC[C@H](NS(=O)(=O)c3ccc4cc(Cl)ccc4c3)C2=O)C1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-2092c867fb284e948b6e81396fe38769 | C[C@@H](C(=O)O)N1CC[C@H](NS(=O)(=O)c2ccc3cc(Cl)ccc3c2)C1=O.O=C(N[C@H]1CCCNC1)OCc1ccccc1>>C[C@@H](C(=O)N1CCC[C@H](NC(=O)OCc2ccccc2)C1)N1CC[C@H](NS(=O)(=O)c2ccc3cc(Cl)ccc3c2)C1=O | ClC=1C=C2C=CC(=CC2=CC1)S(=O)(=O)N[C@@H]1C(N(CC1)[C@H](C(=O)O)C)=O.Cl.CN(CCCN=C=NCC)C.C=1C=CC2=C(C1)N=NN2O.N1C[C@H](CCC1)NC(OCC1=CC=CC=C1)=O>>ClC=1C=C2C=CC(=CC2=CC1)S(=O)(=O)N[C@@H]1C(N(CC1)[C@H](C(=O)N1C[C@H](CCC1)NC(OCC1=CC=CC=C1)=O)C)=O | O[C:3]([C@H:2]([CH3:1])[N:22]1[CH2:23][CH2:24][C@H:25]([NH:26][S:27](=[O:28])(=[O:29])[c:30]2[cH:31][cH:32][c:33]3[cH:34][c:35]([Cl:36])[cH:37][cH:38][c:39]3[cH:40]2)[C:41]1=[O:42])=[O:4].[NH:5]1[CH2:6][CH2:7][CH2:8][C@H:9]([NH:10][C:11](=[O:12])[O:13][CH2:14][c:15]2[cH:16][cH:17][cH:18][cH:19][cH:20]2)[CH2:21]1>>[CH3:... | C[C@@H](C(=O)O)N1CC[C@H](NS(=O)(=O)c2ccc3cc(Cl)ccc3c2)C1=O.O=C(N[C@H]1CCCNC1)OCc1ccccc1 | C[C@@H](C(=O)N1CCC[C@H](NC(=O)OCc2ccccc2)C1)N1CC[C@H](NS(=O)(=O)c2ccc3cc(Cl)ccc3c2)C1=O | null | null | C(Cl)Cl.C(C)N(CC)CC | Acylation | Acylation of Nitrogen Nucleophiles by Carboxylic Acids | fbfce93ec1ece674255bb96c5cec09ad611382b41cf117dfe580015e21744a71 | c5e4172490b2731ba9322b68af56376edadc31ce0bb9a3dfdea23a1817a852fd | O=C(N[C@H]1CCCN(C(=O)CN2CC[C@H](NS(=O)(=O)c3ccc4ccccc4c3)C2=O)C1)OCc1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C;D1;H3:4])-[#7:5]-[C:6]=[O;D1;H0:7].[C:8]-[C:9]-[NH;D2;+0:10]-[C:11]-[C:12]>>[C:8]-[C:9]-[N;H0;D3;+0:10](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C;D1;H3:4])-[#7:5]-[C:6]=[O;D1;H0:7])-[C:11]-[C:12] | 42.5 | [{"value": 42.5, "product": "ClC=1C=C2C=CC(=CC2=CC1)S(=O)(=O)N[C@@H]1C(N(CC1)[C@H](C(=O)N1C[C@H](CCC1)NC(OCC1=CC=CC=C1)=O)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | A solution of (2S)-2-((3S)-3-{[(6-chloro-2-naphthyl)sulfonyl]amino}-2-oxopyrrolidin-1-yl)propanoic acid (0.408 g) in DCM (21 ml) was treated with 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (0.394 g), HOBT (0.278 g) and triethylamine (0.286 ml) and stirred at room temperature for 1 h. A solution of be... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | Tertiary amide | C1CCNCC1 | C1CC[NH]CC1 | C1CC[NH]CC1.c1ccccc1.C1CC[NH]C1.c1ccc2ccccc2c1 | HO- | C(Cl)Cl.C(C)N(CC)CC | null | 1 | C[C@@H](C(=O)O)N1CC[C@H](NS(=O)(=O)c2ccc3cc(Cl)ccc3c2)C1=O.O=C(N[C@H]1CCCNC1)OCc1ccccc1>C(Cl)Cl.C(C)N(CC)CC>C[C@@H](C(=O)N1CCC[C@H](NC(=O)OCc2ccccc2)C1)N1CC[C@H](NS(=O)(=O)c2ccc3cc(Cl)ccc3c2)C1=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-81c46fc548a2432dba9495e6a550bdcd | C[C@@H](C(=O)N1CCC[C@H](NC(=O)OCc2ccccc2)C1)N1CC[C@H](NS(=O)(=O)c2ccc3cc(Cl)ccc3c2)C1=O>>C[C@@H](C(=O)N1CCC[C@H](N)C1)N1CC[C@H](NS(=O)(=O)c2ccc3cc(Cl)ccc3c2)C1=O | ClC=1C=C2C=CC(=CC2=CC1)S(=O)(=O)N[C@@H]1C(N(CC1)[C@H](C(=O)N1C[C@H](CCC1)NC(OCC1=CC=CC=C1)=O)C)=O.FC(C(=O)O)(F)F>>N[C@@H]1CN(CCC1)C([C@H](C)N1C([C@H](CC1)NS(=O)(=O)C1=CC2=CC=C(C=C2C=C1)Cl)=O)=O | O=C(OCc1ccccc1)[NH:10][C@H:9]1[CH2:8][CH2:7][CH2:6][N:5]([C:3]([C@H:2]([CH3:1])[N:12]2[CH2:13][CH2:14][C@H:15]([NH:16][S:17](=[O:18])(=[O:19])[c:20]3[cH:21][cH:22][c:23]4[cH:24][c:25]([Cl:26])[cH:27][cH:28][c:29]4[cH:30]3)[C:31]2=[O:32])=[O:4])[CH2:11]1>>[CH3:1][C@@H:2]([C:3](=[O:4])[N:5]1[CH2:6][CH2:7][CH2:8][C@H:9]([... | C[C@@H](C(=O)N1CCC[C@H](NC(=O)OCc2ccccc2)C1)N1CC[C@H](NS(=O)(=O)c2ccc3cc(Cl)ccc3c2)C1=O | C[C@@H](C(=O)N1CCC[C@H](N)C1)N1CC[C@H](NS(=O)(=O)c2ccc3cc(Cl)ccc3c2)C1=O | null | null | C(Cl)Cl | Reduction | Hydrogenolysis of amides/imides/carbamates | 087b6600ba91d3df931fe6979f2445c192cbfd59e04fd2d8a10f7c7573ac669f | 4e549866ec1acadec4c84aaf8495992a28ec78d8ea5ef1b9f44dd843b0dcb7d4 | O=C(CN1CC[C@H](NS(=O)(=O)c2ccc3ccccc3c2)C1=O)N1CCCCC1 | O=C(-O-C-c1:c:c:c:c:c:1)-[NH;D2;+0:1]-[C:2](-[C:3])-[C:4]-[#7:5]>>[#7:5]-[C:4]-[C:2](-[NH2;D1;+0:1])-[C:3] | 93 | [{"value": 93.0, "product": "N[C@@H]1CN(CCC1)C([C@H](C)N1C([C@H](CC1)NS(=O)(=O)C1=CC2=CC=C(C=C2C=C1)Cl)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 6 | HOUR | Benzyl (3S)-1-[(2S)-2-((3S)-3-{[(6-chloro-2-naphthyl)sulfonyl]amino}-2-oxopyrrolidin-1-yl)propanoyl]piperidin-3-ylcarbamate (0.128 g) was dissolved in DCM (3.5 ml) and treated with trifluoroacetic acid (10.5 ml) and stirred at room temperature for 6 h. The mixture was concentrated under reduced pressure and the residue... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether | Primary amine | c1ccccc1 | null | C1CC[NH]CC1.C1CC[NH]C1.c1ccc2ccccc2c1 | HO- | C(Cl)Cl | null | 6 | C[C@@H](C(=O)N1CCC[C@H](NC(=O)OCc2ccccc2)C1)N1CC[C@H](NS(=O)(=O)c2ccc3cc(Cl)ccc3c2)C1=O>C(Cl)Cl>C[C@@H](C(=O)N1CCC[C@H](N)C1)N1CC[C@H](NS(=O)(=O)c2ccc3cc(Cl)ccc3c2)C1=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-76208bbd205a40dfb12b242c62aea99a | C[C@@H](C(=O)N1CCOCC1)N1CC[C@H](N)C1=O.O=S(=O)(Cl)c1cc2cc(Cl)ccc2o1>>C[C@@H](C(=O)N1CCOCC1)N1CC[C@H](NS(=O)(=O)c2cc3cc(Cl)ccc3o2)C1=O | [Cl-].[NH4+].N[C@@H]1C(N(CC1)[C@H](C(=O)N1CCOCC1)C)=O.ClC=1C=CC2=C(C=C(O2)S(=O)(=O)Cl)C1>>ClC=1C=CC2=C(C=C(O2)S(=O)(=O)N[C@@H]2C(N(CC2)[C@H](C(=O)N2CCOCC2)C)=O)C1 | [CH3:1][C@@H:2]([C:3](=[O:4])[N:5]1[CH2:6][CH2:7][O:8][CH2:9][CH2:10]1)[N:11]1[CH2:12][CH2:13][C@H:14]([NH2:15])[C:29]1=[O:30].Cl[S:16](=[O:17])(=[O:18])[c:19]1[cH:20][c:21]2[cH:22][c:23]([Cl:24])[cH:25][cH:26][c:27]2[o:28]1>>[CH3:1][C@@H:2]([C:3](=[O:4])[N:5]1[CH2:6][CH2:7][O:8][CH2:9][CH2:10]1)[N:11]1[CH2:12][CH2:13]... | C[C@@H](C(=O)N1CCOCC1)N1CC[C@H](N)C1=O.O=S(=O)(Cl)c1cc2cc(Cl)ccc2o1 | C[C@@H](C(=O)N1CCOCC1)N1CC[C@H](NS(=O)(=O)c2cc3cc(Cl)ccc3o2)C1=O | null | null | C(C)#N.N1=CC=CC=C1 | Acylation | Sulfonamide synthesis (Schotten-Baumann) primary amine | 4c44ef6d7646f6ef25dd125d2c32c713d8dcae7c603407faa5f0fb810631670e | 8fce8115d8a725afa92eb3910ded29d4c852e5133eba78a425054f41f7142603 | O=C(CN1CC[C@H](NS(=O)(=O)c2cc3ccccc3o2)C1=O)N1CCOCC1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[#8;a:6]:[c:7].[#7:8]-[C:9](=[O;D1;H0:10])-[C:11]-[#7:12]1-[C:13]-[C:14]-[C:15](-[NH2;D1;+0:16])-[C:17]-1=[O;D1;H0:18]>>[#7:8]-[C:9](=[O;D1;H0:10])-[C:11]-[#7:12]1-[C:13]-[C:14]-[C:15](-[NH;D2;+0:16]-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[#8... | 55.1 | [{"value": 55.1, "product": "ClC=1C=CC2=C(C=C(O2)S(=O)(=O)N[C@@H]2C(N(CC2)[C@H](C(=O)N2CCOCC2)C)=O)C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 72 | HOUR | To a solution of (3S)-3-amino-1-[(1S)-1-methyl-2-morpholin-4-yl-2-oxoethyl]pyrrolidin-2-one (0.077 g) in anhydrous acetonitrile (2ml) were added 5-chloro-1-benzofuran-2-sulfonyl chloride (0.043 g) in acetonitrile (2 ml) and pyridine (0.057 ml), and the mixture was stirred at room temperature for 72 h. Saturated ammoniu... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Sulfonyl halide | Sulfonamide | null | null | C1COCC[NH]1.C1CC[NH]C1.c1ccc2occc2c1 | HCl | C(C)#N.N1=CC=CC=C1 | null | 72 | C[C@@H](C(=O)N1CCOCC1)N1CC[C@H](N)C1=O.O=S(=O)(Cl)c1cc2cc(Cl)ccc2o1>C(C)#N.N1=CC=CC=C1>C[C@@H](C(=O)N1CCOCC1)N1CC[C@H](NS(=O)(=O)c2cc3cc(Cl)ccc3o2)C1=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-89d649d4b7be4c728ab42cad047e2397 | C[C@@H](C(=O)N1CCC[C@@H](NC(=O)OCc2ccccc2)C1)N1CC[C@H](NS(=O)(=O)c2ccc3cc(Cl)ccc3c2)C1=O>>C[C@@H](C(=O)N1CCC[C@@H](NC(=O)OCc2ccccc2)C1)N1CC[C@H](NS(=O)(=O)c2ccc3ccccc3c2)C1=O | ClC=1C=C2C=CC(=CC2=CC1)S(=O)(=O)N[C@@H]1C(N(CC1)[C@H](C(=O)N1C[C@@H](CCC1)NC(OCC1=CC=CC=C1)=O)C)=O>>C1=C(C=CC2=CC=CC=C12)S(=O)(=O)N[C@@H]1C(N(CC1)[C@H](C(=O)N1C[C@@H](CCC1)NC(OCC1=CC=CC=C1)=O)C)=O | Cl[c:35]1[cH:34][c:33]2[cH:32][cH:31][c:30]([S:27]([NH:26][C@H:25]3[CH2:24][CH2:23][N:22]([C@@H:2]([CH3:1])[C:3](=[O:4])[N:5]4[CH2:6][CH2:7][CH2:8][C@@H:9]([NH:10][C:11](=[O:12])[O:13][CH2:14][c:15]5[cH:16][cH:17][cH:18][cH:19][cH:20]5)[CH2:21]4)[C:40]3=[O:41])(=[O:28])=[O:29])[cH:39][c:38]2[cH:37][cH:36]1>>[CH3:1][C@@... | C[C@@H](C(=O)N1CCC[C@@H](NC(=O)OCc2ccccc2)C1)N1CC[C@H](NS(=O)(=O)c2ccc3cc(Cl)ccc3c2)C1=O | C[C@@H](C(=O)N1CCC[C@@H](NC(=O)OCc2ccccc2)C1)N1CC[C@H](NS(=O)(=O)c2ccc3ccccc3c2)C1=O | null | [Pd] | C(C)O | Functional Group Interconversion | Aromatic dehalogenation | b59c5c205c966b4215325ef1ee4f08427e93cdf8277de7587f9668b39e907bde | 56de34d4a44cb25d9380269ee5e138b0f24b40a3a0db22c5508049dc775a861f | O=C(N[C@@H]1CCCN(C(=O)CN2CC[C@H](NS(=O)(=O)c3ccc4ccccc4c3)C2=O)C1)OCc1ccccc1 | Cl-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5]>>[c:3]:[c:2]:[cH;D2;+0:1]:[c:4]:[c:5] | 3 | [{"value": 3.0, "product": "C1=C(C=CC2=CC=CC=C12)S(=O)(=O)N[C@@H]1C(N(CC1)[C@H](C(=O)N1C[C@@H](CCC1)NC(OCC1=CC=CC=C1)=O)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 17 | HOUR | A mixture of benzyl (3R)-1-[(2S)-2-((3S)-3-{[(6-chloro-2-naphthyl)sulfonyl]amino}-2-oxopyrrolidin-1-yl)propanoyl]piperidin-3-ylcarbamate (0.350 g), 10% palladium on carbon (0.035 g) and ethanol (1000 ml) was stirred under an atmosphere of hydrogen for 17 h. The reaction mixture was filtered through Harbolite™ and the f... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | null | c1ccc2ccccc2c1 | c1ccc2ccccc2c1 | C1CC[NH]CC1.c1ccccc1.C1CC[NH]C1.c1ccc2ccccc2c1 | Other | [Pd].C(C)O | null | 17 | C[C@@H](C(=O)N1CCC[C@@H](NC(=O)OCc2ccccc2)C1)N1CC[C@H](NS(=O)(=O)c2ccc3cc(Cl)ccc3c2)C1=O>[Pd].C(C)O>C[C@@H](C(=O)N1CCC[C@@H](NC(=O)OCc2ccccc2)C1)N1CC[C@H](NS(=O)(=O)c2ccc3ccccc3c2)C1=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-42bdb3fb724a4485a85ae3d72f154c89 | CC(C)(C)OC(=O)N1CC2CNCC(C2)C1.C[C@@H](C(=O)O)N1CC[C@H](NS(=O)(=O)c2ccc3cc(Cl)ccc3c2)C1=O>>C[C@@H](C(=O)N1C[C@@H]2C[C@@H](CN(C(=O)OC(C)(C)C)C2)C1)N1CC[C@H](NS(=O)(=O)c2ccc3cc(Cl)ccc3c2)C1=O | ClC=1C=C2C=CC(=CC2=CC1)S(=O)(=O)N[C@@H]1C(N(CC1)[C@H](C(=O)O)C)=O.C12CN(CC(CNC1)C2)C(=O)OC(C)(C)C.C12CN(CC(CNC1)C2)C(=O)OC(C)(C)C>>ClC=1C=C2C=CC(=CC2=CC1)S(=O)(=O)N[C@@H]1C(N(CC1)[C@H](C(=O)N1C[C@H]2CN(C[C@@H](C1)C2)C(=O)OC(C)(C)C)C)=O | [NH:5]1[CH2:6][CH:7]2[CH2:8][CH:9]([CH2:10][N:11]([C:12](=[O:13])[O:14][C:15]([CH3:16])([CH3:17])[CH3:18])[CH2:19]2)[CH2:20]1.O[C:3]([C@H:2]([CH3:1])[N:21]1[CH2:22][CH2:23][C@H:24]([NH:25][S:26](=[O:27])(=[O:28])[c:29]2[cH:30][cH:31][c:32]3[cH:33][c:34]([Cl:35])[cH:36][cH:37][c:38]3[cH:39]2)[C:40]1=[O:41])=[O:4]>>[CH3:... | CC(C)(C)OC(=O)N1CC2CNCC(C2)C1.C[C@@H](C(=O)O)N1CC[C@H](NS(=O)(=O)c2ccc3cc(Cl)ccc3c2)C1=O | C[C@@H](C(=O)N1C[C@@H]2C[C@@H](CN(C(=O)OC(C)(C)C)C2)C1)N1CC[C@H](NS(=O)(=O)c2ccc3cc(Cl)ccc3c2)C1=O | null | null | null | Acylation | Acylation of Nitrogen Nucleophiles by Carboxylic Acids | 44fc7912ae653980c4958be1f5d66acd2f9ee13d2d0f8a1d50fa0b7e22c15fc8 | c5e4172490b2731ba9322b68af56376edadc31ce0bb9a3dfdea23a1817a852fd | O=C(CN1CC[C@H](NS(=O)(=O)c2ccc3ccccc3c2)C1=O)N1C[C@@H]2CNC[C@@H](C2)C1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C;D1;H3:4])-[#7:5]-[C:6]=[O;D1;H0:7].[C:8]-[C:9]-[NH;D2;+0:10]-[C:11]-[C:12]>>[C:8]-[C:9]-[N;H0;D3;+0:10](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C;D1;H3:4])-[#7:5]-[C:6]=[O;D1;H0:7])-[C:11]-[C:12] | null | [] | null | null | null | null | Using (2S)-2-((3S)-3-{[(6-chloro-2-naphthyl)sulfonyl]amino}-2-oxopyrrolidin-1-yl)propanoic acid and 3,7-diazabicyclo[3.3.1]nonane-3-carboxylic acid, 1,1-dimethylethyl ester* and the synthetic procedure described in Example 1, the title compound was prepared. * Reference for 3,7-Diazabicyclo[3.3.1]nonane-3-carboxylic ac... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | Tertiary amide | C1[NH]CC2CNCC1C2 | C1[NH]C[C@H]2C[NH]C[C@@H]1C2 | C1CC[NH]C1.C1[NH]C[C@H]2C[NH]C[C@@H]1C2.c1ccc2ccccc2c1 | HO- | null | null | null | CC(C)(C)OC(=O)N1CC2CNCC(C2)C1.C[C@@H](C(=O)O)N1CC[C@H](NS(=O)(=O)c2ccc3cc(Cl)ccc3c2)C1=O>>C[C@@H](C(=O)N1C[C@@H]2C[C@@H](CN(C(=O)OC(C)(C)C)C2)C1)N1CC[C@H](NS(=O)(=O)c2ccc3cc(Cl)ccc3c2)C1=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-bce6d1b0269345ada7d58941bda39329 | C[C@@H](C(=O)N1CCOCC1)N1CC[C@H](NS(=O)(=O)/C=C/c2ccc(Cl)c(O[Si](c3ccccc3)(c3ccccc3)C(C)(C)C)c2)C1=O>>C[C@@H](C(=O)N1CCOCC1)N1CC[C@H](NS(=O)(=O)/C=C/c2ccc(Cl)c(O)c2)C1=O | [Si](C1=CC=CC=C1)(C1=CC=CC=C1)(C(C)(C)C)OC=1C=C(C=CC1Cl)/C=C/S(=O)(=O)N[C@@H]1C(N(CC1)[C@H](C(=O)N1CCOCC1)C)=O.[F-].C(CCC)[N+](CCCC)(CCCC)CCCC>>ClC1=C(C=C(C=C1)/C=C/S(=O)(=O)N[C@@H]1C(N(CC1)[C@H](C(=O)N1CCOCC1)C)=O)O | CC(C)(C)[Si](c1ccccc1)(c1ccccc1)[O:27][c:26]1[c:24]([Cl:25])[cH:23][cH:22][c:21](/[CH:20]=[CH:19]/[S:16]([NH:15][C@H:14]2[CH2:13][CH2:12][N:11]([C@@H:2]([CH3:1])[C:3](=[O:4])[N:5]3[CH2:6][CH2:7][O:8][CH2:9][CH2:10]3)[C:29]2=[O:30])(=[O:17])=[O:18])[cH:28]1>>[CH3:1][C@@H:2]([C:3](=[O:4])[N:5]1[CH2:6][CH2:7][O:8][CH2:9][... | C[C@@H](C(=O)N1CCOCC1)N1CC[C@H](NS(=O)(=O)/C=C/c2ccc(Cl)c(O[Si](c3ccccc3)(c3ccccc3)C(C)(C)C)c2)C1=O | C[C@@H](C(=O)N1CCOCC1)N1CC[C@H](NS(=O)(=O)/C=C/c2ccc(Cl)c(O)c2)C1=O | null | null | C1CCOC1 | Deprotection | Alcohol deprotection from silyl ethers | cb7a55bba7beea8afc666e12e8162e54d37a49e453e1640ce533ca6190b41190 | bcb3a8510d04057b612b045a6ac632b147a7a112beeedd4cca92670e4d4c910b | O=C(CN1CC[C@H](NS(=O)(=O)/C=C/c2ccccc2)C1=O)N1CCOCC1 | C-C(-C)(-C)-[Si](-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4])(-c1:c:c:c:c:c:1)-c1:c:c:c:c:c:1>>[OH;D1;+0:1]-[c:2](:[c:3]):[c:4] | 83.8 | [{"value": 83.8, "product": "ClC1=C(C=C(C=C1)/C=C/S(=O)(=O)N[C@@H]1C(N(CC1)[C@H](C(=O)N1CCOCC1)C)=O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of (E)-2-(3-{[tert-butyl(diphenyl)silyl]oxy}-4-chlorophenyl)-N-{(3S)-1-[(1S)-1-methyl-2-morpholin-4-yl-2-oxoethyl]-2-oxopyrrolidin-3-yl}ethenesulfonamide (0.0078 g) in THF (0.3 ml) at −78° C. under nitrogen, tetra n-butylammonium fluoride (1M in THF, 0.014 ml) was added. The mixture was allowed to warm to... | 10.6084/m9.figshare.5104873.v1 | null | Silyl protective group | Aromatic alcohol | c1ccccc1.c1ccccc1 | null | C1COCC[NH]1.C1CC[NH]C1.c1ccccc1 | Other | C1CCOC1 | null | null | C[C@@H](C(=O)N1CCOCC1)N1CC[C@H](NS(=O)(=O)/C=C/c2ccc(Cl)c(O[Si](c3ccccc3)(c3ccccc3)C(C)(C)C)c2)C1=O>C1CCOC1>C[C@@H](C(=O)N1CCOCC1)N1CC[C@H](NS(=O)(=O)/C=C/c2ccc(Cl)c(O)c2)C1=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-68e91174ffe545608aa7ac5a653e7839 | CCOC(C)=O.CN(C)C=O.C[C@H](C(=O)OC(C)(C)C)N1CC[C@@H](NS(=O)(=O)c2ccc3cc(Cl)ccc3c2)C1=O.ClCCN1CCOCC1>>C[C@@H](C(=O)N1CCOCC1)N1CC[C@H](N(CCN2CCOCC2)S(=O)(=O)c2ccc3cc(Cl)ccc3c2)C1=O.O=CO | ClC=1C=C2C=CC(=CC2=CC1)S(=O)(=O)N[C@H]1C(N(CC1)[C@@H](C(=O)OC(C)(C)C)C)=O.Cl.ClCCN1CCOCC1.C([O-])([O-])=O.[K+].[K+].C(C)(=O)OCC.CN(C)C=O>>C(=O)O.ClC=1C=C2C=CC(=CC2=CC1)S(=O)(=O)N(CCN1CCOCC1)[C@@H]1C(N(CC1)[C@H](C(=O)N1CCOCC1)C)=O | CC(=O)OC[CH3:9].[N:5]([CH3:6])([CH3:10])[CH:41]=[O:40].CC(C)(C)[O:42][C:3]([C@@H:2]([CH3:1])[N:11]1[CH2:12][CH2:13][C@@H:14]([NH:15][S:24](=[O:25])(=[O:26])[c:27]2[cH:28][cH:29][c:30]3[cH:31][c:32]([Cl:33])[cH:34][cH:35][c:36]3[cH:37]2)[C:38]1=[O:39])=[O:4].Cl[CH2:16][CH2:17][N:18]1[CH2:19][CH2:20][O:21][CH2:22][CH2:23... | CCOC(C)=O.CN(C)C=O.C[C@H](C(=O)OC(C)(C)C)N1CC[C@@H](NS(=O)(=O)c2ccc3cc(Cl)ccc3c2)C1=O.ClCCN1CCOCC1 | C[C@@H](C(=O)N1CCOCC1)N1CC[C@H](N(CCN2CCOCC2)S(=O)(=O)c2ccc3cc(Cl)ccc3c2)C1=O.O=CO | null | null | O | Acylation | OtherReaction | 587a1834265d09e21c27d59c0e628af6623281afa9b3c943f1851b83330a735f | b845315bf5a7e52aca0797a39b510d29efd809527ec0cb2a85bae61afde03eff | O=C(CN1CC[C@H](N(CCN2CCOCC2)S(=O)(=O)c2ccc3ccccc3c2)C1=O)N1CCOCC1 | C-C(-C)(-C)-[O;H0;D2;+0:1]-[C;H0;D3;+0:2](=[O;D1;H0:3])-[C:4](-[C;D1;H3:5])-[#7:6]1-[C:7]-[C:8]-[C:9](-[NH;D2;+0:10]-[#16:11](=[O;D1;H0:12])(=[O;D1;H0:13])-[c:14])-[C:15]-1=[O;D1;H0:16].C-C(=O)-O-C-[CH3;D1;+0:17].Cl-[CH2;D2;+0:18]-[C:19]-[#7:20].[CH3;D1;+0:21]-[N;H0;D3;+0:22](-[CH3;D1;+0:23])-[CH;D2;+0:24]=[O;D1;H0:25]... | null | [] | 40 | CELSIUS | 2 | HOUR | Example 1 (0.05 g) was dissolved in DMF (1 ml) and treated with chloroethylmorpholine hydrochloride (0.062 g) and potassium carbonate (0.093 g), and stirred at 40° C. for 2 h. The mixture was then heated at 80° C. for 8 h, cooled and treated with ethyl acetate and water. The organic extraxt was dried (over magnesium su... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonamide.Primary halide.Ester.Ester.Tertiary amide.Boc | Carboxylic acid.Ether.Tertiary amide.Tertiary amine | null | C1COCC[NH]1 | C1COCC[NH]1.C1CC[NH]C1.C1COCC[NH]1.c1ccc2ccccc2c1 | HCl | O | 40 | 2 | CCOC(C)=O.CN(C)C=O.C[C@H](C(=O)OC(C)(C)C)N1CC[C@@H](NS(=O)(=O)c2ccc3cc(Cl)ccc3c2)C1=O.ClCCN1CCOCC1>O>C[C@@H](C(=O)N1CCOCC1)N1CC[C@H](N(CCN2CCOCC2)S(=O)(=O)c2ccc3cc(Cl)ccc3c2)C1=O.O=CO |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-1c85433b4ec64678bbc860768912d388 | O=C(O)c1cccnc1-c1cccnc1>>OCc1cccnc1-c1cccnc1 | CO.N1=C(C(=CC=C1)C(=O)O)C=1C=NC=CC1.C(C)N(CC)CC.Cl.[BH4-].[Na+]>>OCC=1C(=NC=CC1)C=1C=NC=CC1 | O=[C:2]([OH:1])[c:3]1[cH:4][cH:5][cH:6][n:7][c:8]1-[c:9]1[cH:10][cH:11][cH:12][n:13][cH:14]1>>[OH:1][CH2:2][c:3]1[cH:4][cH:5][cH:6][n:7][c:8]1-[c:9]1[cH:10][cH:11][cH:12][n:13][cH:14]1 | O=C(O)c1cccnc1-c1cccnc1 | OCc1cccnc1-c1cccnc1 | null | null | O1CCCC1 | Reduction | Reduction of carboxylic acid to primary alcohol | 0db83a5ebe1e318b78b55461cf7eb8f7c004eef0f9e3b6666d3df4c96b5f665e | 93b4621647b04d2ad2f2825215b1567f171ba61fe10d136b5db6ea0470aa4932 | c1ccc(-c2cccnc2)nc1 | O=[C;H0;D3;+0:1](-[O;D1;H1:2])-[c:3](:[c:4]):[c:5](-[c:6]:[c:7]:[#7;a:8]):[#7;a:9]:[c:10]>>[#7;a:8]:[c:7]:[c:6]-[c:5](:[#7;a:9]:[c:10]):[c:3](-[CH2;D2;+0:1]-[O;D1;H1:2]):[c:4] | 84.4 | [{"value": 84.0, "product": "OCC=1C(=NC=CC1)C=1C=NC=CC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 84.4, "product": "OCC=1C(=NC=CC1)C=1C=NC=CC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 20 | CELSIUS | null | null | To a continually stirred, ice-cold solution of 2,3′-bipyridine-3-carboxylic acid (0.28 g, 1.40 mmole) in dry tetrahydrofuran (10 ml) and triethylamine (0.20 ml, 1.43 mmole) ethyl chloroformate (0.14 ml, 1.46 mmole) was added drop-by-drop over a 30 minute period. The precipitated product was then filtered and washed sev... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Primary alcohol | null | null | c1ccncc1.c1ccncc1 | Other | O1CCCC1 | 20 | null | O=C(O)c1cccnc1-c1cccnc1>O1CCCC1>OCc1cccnc1-c1cccnc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-522eee91ca144361b417e0fe45341314 | OCc1cccnc1-c1cccnc1>>Cc1cccnc1-c1cccnc1 | OCC=1C(=NC=CC1)C=1C=NC=CC1.Cl.O1CCOCC1>>CC=1C(=NC=CC1)C=1C=NC=CC1 | O[CH2:1][c:2]1[cH:3][cH:4][cH:5][n:6][c:7]1-[c:8]1[cH:9][cH:10][cH:11][n:12][cH:13]1>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][n:6][c:7]1-[c:8]1[cH:9][cH:10][cH:11][n:12][cH:13]1 | OCc1cccnc1-c1cccnc1 | Cc1cccnc1-c1cccnc1 | null | [Pd] | CO | Reduction | OtherReaction | 1deafbccd34c1d747dea179c0b63e48cd7fc76936d377fecabe099ecef578991 | 0a2c8330040d049ae67653e1474aff520bf8a2d8c908ffd7076f536576936945 | c1ccc(-c2cccnc2)nc1 | O-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4](-[c:5]:[c:6]:[#7;a:7]):[#7;a:8]:[c:9]>>[#7;a:7]:[c:6]:[c:5]-[c:4](:[#7;a:8]:[c:9]):[c:2](-[CH3;D1;+0:1]):[c:3] | 76.1 | [{"value": 76.0, "product": "CC=1C(=NC=CC1)C=1C=NC=CC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 76.1, "product": "CC=1C(=NC=CC1)C=1C=NC=CC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | A 3-hydroxymethyl-2,3′-bipyridyl (42.3 mg, 0.227 mmole) solution containing methanol (5 ml) and 4N solution of hydrogen chloride in dry 1,4-dioxane (0.57 ml, 2.3 mmole) was hydrogenated in the presence of palladium on activated carbon catalyst (10%, 40 mg) at room temperature and ambient pressure for 3 hours. The catal... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | null | null | null | c1ccncc1.c1ccncc1 | Other | [Pd].CO | null | 3 | OCc1cccnc1-c1cccnc1>[Pd].CO>Cc1cccnc1-c1cccnc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b86fd53c2c1347ee8ef00fd260228086 | CCO>>CCO.O.OCC(O)CO | C(C)O.C(CCCCCCC\C=C/CCCCCCCC)(=O)OCC(O)CO>>C(C)O.O.OCC(O)CO.C(CCCCCCC\C=C/CCCCCCCC)(=O)OCC(O)CO | [CH3:26][CH2:27][OH:28]>>[CH3:26][CH2:27][OH:28].[OH2:29].[OH:30][CH2:31][CH:32]([OH:33])[CH2:34][OH:35] | CCO | CCO.O.OCC(O)CO | null | null | O.OCC(O)CO | Miscellaneous | OtherReaction | a244f833733718b07f52109095aa98cd5943ebccc6e7556166190ea2fb1e9527 | 3886f50ccf014aba7d974a7f782a7e63fb3f50b880ebcf5701bc7ab1c8a8ad31 | null | null | null | [] | null | null | null | null | 95% ethanol (USP) was diluted with water (USP), glycerin (USP), and glycerol monooleate (Eastman Chemical, Kingsport N.Y.) to provide a final solution at ethanol/water/glycerin/glycerol monooleate percent ratios of 35/59/5/1, respectively. Oxybutynin free base was then dissolved into the above solution to a concentrati... | 10.6084/m9.figshare.5104873.v1 | null | null | Primary alcohol.Primary alcohol.Secondary alcohol | null | null | null | Other | O.OCC(O)CO | null | null | CCO>O.OCC(O)CO>CCO.O.OCC(O)CO |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-fe246bcbccfc45eab97f443429b20fe3 | OCC1CC2C=CC1C2.Oc1ccc(I)cc1>>Ic1ccc(OCC2CC3C=CC2C3)cc1 | CCOC(=O)/N=N/C(=O)OCC.C12C(CC(C=C1)C2)CO.IC1=CC=C(C=C1)O.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1>>IC1=CC=C(C=C1)OCC1C2C=CC(C1)C2 | [OH:6][CH2:7][CH:8]1[CH2:9][CH:10]2[CH:11]=[CH:12][CH:13]1[CH2:14]2.O[c:5]1[cH:4][cH:3][c:2]([I:1])[cH:16][cH:15]1>>[I:1][c:2]1[cH:3][cH:4][c:5]([O:6][CH2:7][CH:8]2[CH2:9][CH:10]3[CH:11]=[CH:12][CH:13]2[CH2:14]3)[cH:15][cH:16]1 | OCC1CC2C=CC1C2.Oc1ccc(I)cc1 | Ic1ccc(OCC2CC3C=CC2C3)cc1 | null | null | O1CCCC1 | Heteroatom Alkylation and Arylation | Mitsunobu aryl ether | 8915084acbaaf997bf0f89ff5187cb2f89c25dc683fffc57b3391298c8430dd9 | 2258bd14c3b5449b92dc09cf9fa522f88d5071b4af20f7e968b60aa1ae6db0cf | C1=CC2CC1CC2COc1ccccc1 | O-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[C:6]-[C:7]-[OH;D1;+0:8]>>[C:6]-[C:7]-[O;H0;D2;+0:8]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5] | 97 | [{"value": 97.0, "product": "IC1=CC=C(C=C1)OCC1C2C=CC(C1)C2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 92.0, "product": "IC1=CC=C(C=C1)OCC1C2C=CC(C1)C2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 18 | HOUR | Diethylazodicarboxylate (8.7 g) was added dropwise to a solution of 5-norbornene-2-methanol (6.2 g, 0.05 mol), 4-iodophenol (11.0 g, 0.05 mol) and triphenylphosphine (13.1 g, 0.05 mol) in 100 mL of anhydrous tetrahydrofuran. After completion of the addition, the resulting solution was stirred for 18 h at room temperatu... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Aromatic alcohol | Ether | c1ccccc1 | c1ccccc1 | C1=CC2CCC1C2.c1ccccc1 | HO- | O1CCCC1 | null | 18 | OCC1CC2C=CC1C2.Oc1ccc(I)cc1>O1CCCC1>Ic1ccc(OCC2CC3C=CC2C3)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-9bdd41d1c9294f7b851c289c0070b4ce | BrCCCCBr.CCC1(CO)COC1>>CCC1(COCCCCBr)COC1 | OCC1(COC1)CC.BrCCCCBr.CCCCCC.[OH-].[Na+]>>BrCCCCOCC1(COC1)CC | Br[CH2:6][CH2:7][CH2:8][CH2:9][Br:10].[CH3:1][CH2:2][C:3]1([CH2:4][OH:5])[CH2:11][O:12][CH2:13]1>>[CH3:1][CH2:2][C:3]1([CH2:4][O:5][CH2:6][CH2:7][CH2:8][CH2:9][Br:10])[CH2:11][O:12][CH2:13]1 | BrCCCCBr.CCC1(CO)COC1 | CCC1(COCCCCBr)COC1 | null | [Br-].C(CCC)[N+](CCCC)(CCCC)CCCC | O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | dd3f9c60e1f90d961a7c01d970ae213561355ee1451f276a3b04696e4b6fae5c | 46a6e883cf919b4006e69abfdfd883f458f55c08b3200960c6a5b57c4139fbca | C1COC1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[C:4]-[C:5]-[OH;D1;+0:6]>>[C:4]-[C:5]-[O;H0;D2;+0:6]-[CH2;D2;+0:1]-[C:2]-[C:3] | 45 | [{"value": 44.0, "product": "BrCCCCOCC1(COC1)CC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 45.0, "product": "BrCCCCOCC1(COC1)CC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | 5 | HOUR | Into a 2 L egg plant type flask were charged 46.3 g (0.40 mol) of 3-hydroxymethyl-3-ethyloxetane (product name: OXT-101 manufactured by Toagosei Co., Ltd.), 250.3 g (1.16 mol) of 1,4-dibromobutane (reagent, manufactured by Tokyo Kasei Kogyo Co., Ltd.), and 275 ml of hexane. 500 ml of a 33% sodium hydroxide aqueous solu... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary alcohol | Ether | null | null | C1COC1 | HBr | [Br-].C(CCC)[N+](CCCC)(CCCC)CCCC.O | 80 | 5 | BrCCCCBr.CCC1(CO)COC1>[Br-].C(CCC)[N+](CCCC)(CCCC)CCCC.O>CCC1(COCCCCBr)COC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-e20a963324004b499bf87587735aa884 | CCC1(COCCCCBr)COC1.CCOC(=O)c1ccc(O)cc1>>CCC1(COCCCCOc2ccc(C(=O)O)cc2)COC1 | OC1=CC=C(C(=O)OCC)C=C1.BrCCCCOCC1(COC1)CC>>C(C)C1(COC1)COCCCCOC1=CC=C(C(=O)O)C=C1 | Br[CH2:9][CH2:8][CH2:7][CH2:6][O:5][CH2:4][C:3]1([CH2:2][CH3:1])[CH2:20][O:21][CH2:22]1.CC[O:17][C:15]([c:14]1[cH:13][cH:12][c:11]([OH:10])[cH:19][cH:18]1)=[O:16]>>[CH3:1][CH2:2][C:3]1([CH2:4][O:5][CH2:6][CH2:7][CH2:8][CH2:9][O:10][c:11]2[cH:12][cH:13][c:14]([C:15](=[O:16])[OH:17])[cH:18][cH:19]2)[CH2:20][O:21][CH2:22]... | CCC1(COCCCCBr)COC1.CCOC(=O)c1ccc(O)cc1 | CCC1(COCCCCOc2ccc(C(=O)O)cc2)COC1 | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | OtherReaction | c47049bacd28cc701f2e77df376a2fcefecd5392e081f9a62473cff265d23a8c | 017337a0828c32d10d28543003ae15a8b492b5e2f69019c65a4461eabc617d95 | c1ccc(OCCCCOCC2COC2)cc1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].C-C-[O;H0;D2;+0:4]-[C:5](=[O;D1;H0:6])-[c:7].[OH;D1;+0:8]-[c:9](:[c:10]):[c:11]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:8]-[c:9](:[c:10]):[c:11].[O;D1;H0:6]=[C:5](-[OH;D1;+0:4])-[c:7] | 90.3 | [{"value": 89.0, "product": "C(C)C1(COC1)COCCCCOC1=CC=C(C(=O)O)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 90.3, "product": "C(C)C1(COC1)COCCCCOC1=CC=C(C(=O)O)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | 4 | HOUR | In a 300 ml three neck flask, 5.2 g (31 mmol) of ethyl p-hydroxybenzoate, 4.7 g (34 mmol) of potassium carbonate anhydride, and 7.8 g (31 mmol) of the 3-[(4-bromobutoxy)methyl]-3-ethyloxetane were dissolved in 50 ml of dimethylformamide. After the solution remained turbid was heated to a temperature of 80° C. and stirr... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester.Aromatic alcohol | Carboxylic acid.Ether | null | null | c1ccccc1.C1COC1 | HBr | CN(C=O)C | 80 | 4 | CCC1(COCCCCBr)COC1.CCOC(=O)c1ccc(O)cc1>CN(C=O)C>CCC1(COCCCCOc2ccc(C(=O)O)cc2)COC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-1c09bba65c034d81b66bbb9495a49de8 | C1=COCCC1.O=C(O)c1ccc(O)cc1>>O=C(O)c1ccc(OC2CCCCO2)cc1 | O1CCCC=C1.OC1=CC=C(C(=O)O)C=C1.C(Cl)Cl>>O1C(CCCC1)OC1=CC=C(C(=O)O)C=C1 | [CH:9]1=[CH:10][CH2:11][CH2:12][CH2:13][O:14]1.[O:1]=[C:2]([OH:3])[c:4]1[cH:5][cH:6][c:7]([OH:8])[cH:15][cH:16]1>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][cH:6][c:7]([O:8][CH:9]2[CH2:10][CH2:11][CH2:12][CH2:13][O:14]2)[cH:15][cH:16]1 | C1=COCCC1.O=C(O)c1ccc(O)cc1 | O=C(O)c1ccc(OC2CCCCO2)cc1 | null | C1(=CC=C(C=C1)S(=O)(=O)[O-])C.[NH+]1=CC=CC=C1 | CCOCC | Heteroatom Alkylation and Arylation | oxa-Michael addition | 1c7c788bec8addec628516b12629525fab255984248a4af23c71106a7726e25d | da6d2e768f263ce18da31b53a21ee41abe25d00717257e942f83f912a04f86d8 | c1ccc(OC2CCCCO2)cc1 | [#8:1]1-[C:2]-[C:3]-[C:4]-[CH;D2;+0:5]=[CH;D2;+0:6]-1.[OH;D1;+0:7]-[c:8](:[c:9]):[c:10]>>[c:9]:[c:8](-[O;H0;D2;+0:7]-[CH;D3;+0:6]1-[#8:1]-[C:2]-[C:3]-[C:4]-[CH2;D2;+0:5]-1):[c:10] | 86.2 | [{"value": 86.2, "product": "O1C(CCCC1)OC1=CC=C(C(=O)O)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | Into a 300 ml three neck flask were charged 25.4 g of 2,3-dihydropyran (reagent, manufactured by Tokyo Kasei Kogyo Co., Ltd.), 41.4 g of p-hydroxybenzoic acid (reagent, manufactured by Tokyo Kasei Kogyo Co., Ltd.), and 3.7 g of pyridinium p-toluenesulfonate (reagent, manufactured by Tokyo Kasei Kogyo Co., Ltd.). The mi... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Aromatic alcohol | Ether.Ether | C1=COCCC1 | C1CCOCC1 | c1ccccc1.C1CCOCC1 | null | C1(=CC=C(C=C1)S(=O)(=O)[O-])C.[NH+]1=CC=CC=C1.CCOCC | null | 3 | C1=COCCC1.O=C(O)c1ccc(O)cc1>C1(=CC=C(C=C1)S(=O)(=O)[O-])C.[NH+]1=CC=CC=C1.CCOCC>O=C(O)c1ccc(OC2CCCCO2)cc1 |
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