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-c31cb9b44c404c10ba3aa533aa079e2b | ord-425b0d7fa4994b22b3823527f754cbae | COc1ccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccc(Cl)cc3F)C[C@@H]2C)cc1>>COc1ccc(C(=O)N2c3ccccc3[C@H](N)C[C@@H]2C)cc1 | ClC1=CC(=C(C=C1)N(C(C)=O)[C@@H]1C[C@@H](N(C2=CC=CC=C12)C(C1=CC=C(C=C1)OC)=O)C)F.FC1=CC=C(C(=O)Cl)C=C1>>COC1=CC=C(C(=O)N2[C@H](C[C@H](C3=CC=CC=C23)N)C)C=C1 | CC(=O)[N:17](c1ccc(Cl)cc1F)[C@H:16]1[c:15]2[c:10]([cH:11][cH:12][cH:13][cH:14]2)[N:9]([C:7]([c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:22][cH:21]2)=[O:8])[C@@H:19]([CH3:20])[CH2:18]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([C:7](=[O:8])[N:9]2[c:10]3[cH:11][cH:12][cH:13][cH:14][c:15]3[C@H:16]([NH2:17])[CH2:18][C@@H:19]2[CH3:... | COc1ccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccc(Cl)cc3F)C[C@@H]2C)cc1 | COc1ccc(C(=O)N2c3ccccc3[C@H](N)C[C@@H]2C)cc1 | null | null | null | Reduction | OtherReaction | d92dd7f766bc2fbe16dcf7a94e94f65a1bbe8d8b267946fd3311ac86741697b5 | 49e06ba3dca9c668787a59c7ab748b40e0239953b828b5dd26793ffc8ba0855c | O=C(c1ccccc1)N1CCCc2ccccc21 | C-C(=O)-[N;H0;D3;+0:1](-[C:2](-[C:3])-[c:4])-c1:c:c:c(-Cl):c:c:1-F>>[C:3]-[C:2](-[NH2;D1;+0:1])-[c:4] | null | [] | null | null | null | null | N-(4-chloro-2-fluorophenyl)-N-[(2S,4R)-1-(4-methoxybenzoyl)-2-methyl-1,2,3,4-tetrahydroquinolin-4-yl]acetamide was made following general procedure G, substituting 4-methoxybenzoyl chloride for 4-fluorobenzoyl chloride. The amine-aryl coupling was performed differently to what is described in procedure G. Therefore (2S... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Tertiary amide | Primary amine | c1ccccc1 | null | c1ccccc1.c1ccc2c(c1)CCC[NH]2 | HF | null | null | null | COc1ccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccc(Cl)cc3F)C[C@@H]2C)cc1>>COc1ccc(C(=O)N2c3ccccc3[C@H](N)C[C@@H]2C)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-78633439ddf642a3a95eb0b43b1b09d7 | CC(=O)Cl.COc1ccc(C(=O)N2c3ccccc3[C@H](Nc3ccc(Cl)cc3F)C[C@@H]2C)cc1>>COc1ccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccc(Cl)cc3F)C[C@@H]2C)cc1 | ClC1=CC(=C(C=C1)N[C@@H]1C[C@@H](N(C2=CC=CC=C12)C(C1=CC=C(C=C1)OC)=O)C)F.C(C)(C)N(CC)C(C)C.C(C)(=O)Cl>>ClC1=CC(=C(C=C1)N(C(C)=O)[C@@H]1C[C@@H](N(C2=CC=CC=C12)C(C1=CC=C(C=C1)OC)=O)C)F | Cl[C:18]([CH3:19])=[O:20].[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([C:7](=[O:8])[N:9]2[c:10]3[cH:11][cH:12][cH:13][cH:14][c:15]3[C@H:16]([NH:17][c:21]3[cH:22][cH:23][c:24]([Cl:25])[cH:26][c:27]3[F:28])[CH2:29][C@@H:30]2[CH3:31])[cH:32][cH:33]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([C:7](=[O:8])[N:9]2[c:10]3[cH:11][cH:12][cH:... | CC(=O)Cl.COc1ccc(C(=O)N2c3ccccc3[C@H](Nc3ccc(Cl)cc3F)C[C@@H]2C)cc1 | COc1ccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccc(Cl)cc3F)C[C@@H]2C)cc1 | null | null | null | Acylation | N-alkylation of secondary amines with alkyl halides | b92e0bfd3d683c1f2a209adfe70a67ad7cb0d87749eb59e8fe0cf1689bc291e0 | 96cb0a2fed10552c5770a45a2d6523b47ac3e38928b4a9c698d8577451182dcd | O=C(c1ccccc1)N1CC[C@@H](Nc2ccccc2)c2ccccc21 | Cl-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[C:4]-[C:5](-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9])-[c:10]>>[C:4]-[C:5](-[N;H0;D3;+0:6](-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3])-[c:7](:[c:8]):[c:9])-[c:10] | 92 | [{"value": 92.0, "product": "ClC1=CC(=C(C=C1)N(C(C)=O)[C@@H]1C[C@@H](N(C2=CC=CC=C12)C(C1=CC=C(C=C1)OC)=O)C)F", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 16 | HOUR | To a solution of (2S,4R)-N-(4-chloro-2-fluorophenyl)-1-(4-methoxybenzoyl)-2-methyl-1,2,3,4-tetrahydroquinolin-4-amine (60 mg, 0.14 mmol, 1 equ.) in acetyl chloride (0.5 mL) was added diisopropylethylamine (25 uL, 0.14 mmol, 1 equ.). The mixture was stirred at room temperature for 16 h. The mixture was concentrated unde... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Secondary amine | Tertiary amide | null | null | c1ccccc1.c1ccccc1.c1ccc2c(c1)CCC[NH]2 | HCl | null | null | 16 | CC(=O)Cl.COc1ccc(C(=O)N2c3ccccc3[C@H](Nc3ccc(Cl)cc3F)C[C@@H]2C)cc1>>COc1ccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccc(Cl)cc3F)C[C@@H]2C)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-185328c463a14c34a7f8240566847696 | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(C#N)cc2)c2ccccc21.[OH-]>>CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(C(N)=O)cc2)c2ccccc21 | Cl.ClC1=CC=C(C=C1)N(C(C)=O)[C@@H]1C[C@@H](N(C2=CC=CC=C12)C(C1=CC=C(C=C1)C#N)=O)C.[OH-].[K+].C(C)O>>C(C)(=O)N([C@@H]1C[C@@H](N(C2=CC=CC=C12)C(=O)C1=CC=C(C(=O)N)C=C1)C)C1=CC=C(C=C1)Cl | [CH3:1][C:2](=[O:3])[N:4]([c:5]1[cH:6][cH:7][c:8]([Cl:9])[cH:10][cH:11]1)[C@@H:12]1[CH2:13][C@H:14]([CH3:15])[N:16]([C:17](=[O:18])[c:19]2[cH:20][cH:21][c:22]([C:23]#[N:24])[cH:26][cH:27]2)[c:28]2[cH:29][cH:30][cH:31][cH:32][c:33]21.[OH-:25]>>[CH3:1][C:2](=[O:3])[N:4]([c:5]1[cH:6][cH:7][c:8]([Cl:9])[cH:10][cH:11]1)[C@@... | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(C#N)cc2)c2ccccc21.[OH-] | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(C(N)=O)cc2)c2ccccc21 | null | null | O.C(Cl)Cl | Heteroatom Alkylation and Arylation | OtherReaction | 1d1793919e847ed86dcb16487e62464531560dbf4782f9a5875bfe7e0477a3ec | d6f9d146e8ef95e62f1a3ab55a7e3b4ceec8856a5f71b6dccd4ad850f945b658 | O=C(c1ccccc1)N1CC[C@@H](Nc2ccccc2)c2ccccc21 | [N;H0;D1;+0:1]#[C;H0;D2;+0:2]-[c:3](:[c:4]):[c:5].[OH-;D0:6]>>[NH2;D1;+0:1]-[C;H0;D3;+0:2](=[O;H0;D1;+0:6])-[c:3](:[c:4]):[c:5] | null | [] | null | null | null | null | N-(4-chlorophenyl)-N-[(2S,4R)-1-(4-cyanobenzoyl)-2-methyl-1,2,3,4-tetrahydroquinolin-4-yl]acetamide (143 mg, 0.33 mmol) and potassium hydroxide (55 mg, 1.00 mmol)) were dissolved in water (150 mL), ethanol (3 mL) and heated to 70° C. for 4 h. The slurry was portioned between 1N HCl (until acidic) and methylene chloride... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile | Primary amide | null | null | c1ccccc1.c1ccccc1.c1ccc2c(c1)CCC[NH]2 | null | O.C(Cl)Cl | null | null | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(C#N)cc2)c2ccccc21.[OH-]>O.C(Cl)Cl>CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(C(N)=O)cc2)c2ccccc21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-fe3797a7dbed47b6b5a5670b3a947a45 | CCOC(=O)N1CCOc2ccc(C(=O)N3c4ccccc4C(N(C(C)=O)c4ccc(Cl)cc4)CC3C)cc21>>CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc3c(c2)NCCO3)c2ccccc21 | C(C)OC(=O)N1CCOC2=C1C=C(C=C2)C(=O)N2C(CC(C1=CC=CC=C21)N(C2=CC=C(C=C2)Cl)C(C)=O)C>>ClC1=CC=C(C=C1)N(C(C)=O)[C@@H]1C[C@@H](N(C2=CC=CC=C12)C(=O)C=1C=CC2=C(NCCO2)C1)C | CCOC(=O)[N:25]1[c:23]2[c:22]([cH:21][cH:20][c:19]([C:17]([N:16]3[CH:14]([CH3:15])[CH2:13][CH:12]([N:4]([C:2]([CH3:1])=[O:3])[c:5]4[cH:6][cH:7][c:8]([Cl:9])[cH:10][cH:11]4)[c:34]4[c:29]3[cH:30][cH:31][cH:32][cH:33]4)=[O:18])[cH:24]2)[O:28][CH2:27][CH2:26]1>>[CH3:1][C:2](=[O:3])[N:4]([c:5]1[cH:6][cH:7][c:8]([Cl:9])[cH:10... | CCOC(=O)N1CCOc2ccc(C(=O)N3c4ccccc4C(N(C(C)=O)c4ccc(Cl)cc4)CC3C)cc21 | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc3c(c2)NCCO3)c2ccccc21 | null | null | I[Si](C)(C)C.C(Cl)Cl | Reduction | Hydrogenolysis of tertiary amines | b9394cfd10271f5aae2de98b8422519c52d48ec7ce542c4d6938d462b9eccb91 | 20c36f41eeb07c3ba4437b51ba72e8ff3c22d0b27e7197b0e9af3127f331149f | O=C(c1ccc2c(c1)NCCO2)N1CC[C@@H](Nc2ccccc2)c2ccccc21 | C-C-O-C(=O)-[N;H0;D3;+0:1]1-[C:2]-[C:3]-[#8:4]-[c:5]:[c:6]-1:[c:7]>>[c:7]:[c:6]1:[c:5]-[#8:4]-[C:3]-[C:2]-[NH;D2;+0:1]-1 | null | [] | null | null | 4 | DAY | 6-{4-[Acetyl-(4-chloro-phenyl)-amino]-2-methyl-3,4-dihydro-2H-quinoline-1-carbonyl}-2,3-dihydro-benzo[1,4]oxazine-4-carboxylic acid ethyl ester was dissolved in methylene chloride (3 mL) and iodotrimethylsilane (1 mL). After 4 days, the reaction was quenched with sat. aq. NaHCO3. The residue was partitioned between met... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether | Secondary amine | c1ccc2c(c1)[NH]CCO2 | c1ccc2c(c1)NCCO2 | c1ccccc1.c1ccc2c(c1)NCCO2.c1ccc2c(c1)CCC[NH]2 | HO- | I[Si](C)(C)C.C(Cl)Cl | null | 96 | CCOC(=O)N1CCOc2ccc(C(=O)N3c4ccccc4C(N(C(C)=O)c4ccc(Cl)cc4)CC3C)cc21>I[Si](C)(C)C.C(Cl)Cl>CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc3c(c2)NCCO3)c2ccccc21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-516f5754b7e74eee9937bef93f434c35 | ClCCl.O=C(Cl)C(=O)Cl.O=C(Cl)c1ccc(-n2ccc(C(F)(F)F)n2)cc1.O=C(Cl)c1ccc(F)cc1.O=C(O)c1ccc(-n2ccc(C(F)(F)F)n2)cc1.O=C(O)c1ccc(-n2ccc(C(F)(F)F)n2)cc1>>CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(-n3ccc(C(F)(F)F)n3)cc2)c2ccccc21 | FC(C1=NN(C=C1)C1=CC=C(C(=O)Cl)C=C1)(F)F.FC(C1=NN(C=C1)C1=CC=C(C(=O)O)C=C1)(F)F.FC(C1=NN(C=C1)C1=CC=C(C(=O)O)C=C1)(F)F.C(C(=O)Cl)(=O)Cl.C(Cl)Cl.FC1=CC=C(C(=O)Cl)C=C1>>ClC1=CC=C(C=C1)N(C(C)=O)[C@@H]1C[C@@H](N(C2=CC=CC=C12)C(C1=CC=C(C=C1)N1N=C(C=C1)C(F)(F)F)=O)C | Cl[CH2:15][Cl:9].O=[C:1](Cl)[C:2](Cl)=[O:3].O=C(Cl)c1ccc(-n2ccc(C(F)(F)F)n2)[cH:38]c1.O=C(Cl)[c:5]1[cH:6][cH:7][c:8](F)[cH:10][cH:11]1.O=C(O)[c:35]1[cH:34][cH:39][c:12](-[n:4]2c[cH:13][c:14](C(F)(F)F)[n:16]2)[cH:37][cH:36]1.O[C:17](=[O:18])[c:19]1[cH:20][cH:21][c:22](-[n:23]2[cH:24][cH:25][c:26]([C:27]([F:28])([F:29])[... | ClCCl.O=C(Cl)C(=O)Cl.O=C(Cl)c1ccc(-n2ccc(C(F)(F)F)n2)cc1.O=C(Cl)c1ccc(F)cc1.O=C(O)c1ccc(-n2ccc(C(F)(F)F)n2)cc1.O=C(O)c1ccc(-n2ccc(C(F)(F)F)n2)cc1 | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(-n3ccc(C(F)(F)F)n3)cc2)c2ccccc21 | null | null | CN(C)C=O | Acylation | OtherReaction | 7efd7aba43b99b4481b45a40f37b36546ded286afd60fc497e71c42fec6ea510 | 19511973ea5991daa9d61b03fb9ad8183e84f37a8d2ae444e2d675ead47ce978 | O=C(c1ccc(-n2cccn2)cc1)N1CC[C@@H](Nc2ccccc2)c2ccccc21 | Cl-C(=O)-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c;H0;D3;+0:4](-F):[c:5]:[c:6]:1.Cl-C(=O)-c1:c:[cH;D2;+0:7]:c(-n2:c:c:c(-C(-F)(-F)-F):n:2):c:c:1.Cl-[C;H0;D3;+0:8](=O)-[C;H0;D3;+0:9](-Cl)=[O;D1;H0:10].Cl-[CH2;D2;+0:11]-[Cl;H0;D1;+0:12].F-C(-F)(-F)-[c;H0;D3;+0:13]1:[cH;D2;+0:14]:c:[n;H0;D3;+0:15](-[c;H0;D3;+0:16]2:[cH;D2;+0:17]:[c:... | null | [] | null | null | null | null | N-(4-chlorophenyl)-N-((2S,4R)-2-methyl-1-{4-[3-(trifluoromethyl)-1H-pyrazol-1-yl]benzoyl}-1,2,3,4-tetrahydroquinolin-4-yl)acetamide was prepared following general procedure A, substituting 4-[3-(trifluoromethyl)-1H-pyrazol-1-yl]benzoyl chloride for 4-fluorobenzoyl chloride. (4-[3-(trifluoromethyl)-1H-pyrazol-1-yl]benzo... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Acyl halide.Acyl halide.Acyl halide.Trifluoro group.Trifluoro group.Aromatic halide.Primary halide.Primary halide.Carboxylic acid.Carboxylic acid | Aromatic halide.Tertiary amide.Tertiary amide | c1ccccc1.c1cn[nH]c1.c1ccccc1.c1ccccc1.c1cc[nH]n1 | c1ccccc1.c1ccc2c(c1)CCC[NH]2 | c1ccccc1.c1ccccc1.c1cc[nH]n1.c1ccc2c(c1)CCC[NH]2 | HF | CN(C)C=O | null | null | ClCCl.O=C(Cl)C(=O)Cl.O=C(Cl)c1ccc(-n2ccc(C(F)(F)F)n2)cc1.O=C(Cl)c1ccc(F)cc1.O=C(O)c1ccc(-n2ccc(C(F)(F)F)n2)cc1.O=C(O)c1ccc(-n2ccc(C(F)(F)F)n2)cc1>CN(C)C=O>CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(-n3ccc(C(F)(F)F)n3)cc2)c2ccccc21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-534357b57cbd4470806b4d20a9c32b33 | CCOC(C)=O.C[C@H]1C[C@@H](N)c2ccccc2N1C(=O)c1ccc2c(c1)OCCN2C.OB(O)c1ccc(Cl)cc1>>CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc3c(c2)OCCN3C)c2ccccc21 | C(C)(=O)OCC.N[C@@H]1C[C@@H](N(C2=CC=CC=C12)C(=O)C1=CC2=C(N(CCO2)C)C=C1)C.ClC1=CC=C(C=C1)B(O)O.C(C)N(CC)CC>>ClC1=CC=C(C=C1)N(C(C)=O)[C@@H]1C[C@@H](N(C2=CC=CC=C12)C(=O)C1=CC2=C(N(CCO2)C)C=C1)C | CCO[C:2]([CH3:1])=[O:3].[NH2:4][C@@H:12]1[CH2:13][C@H:14]([CH3:15])[N:16]([C:17](=[O:18])[c:19]2[cH:20][cH:21][c:22]3[c:23]([cH:24]2)[O:25][CH2:26][CH2:27][N:28]3[CH3:29])[c:30]2[cH:31][cH:32][cH:33][cH:34][c:35]21.OB(O)[c:5]1[cH:6][cH:7][c:8]([Cl:9])[cH:10][cH:11]1>>[CH3:1][C:2](=[O:3])[N:4]([c:5]1[cH:6][cH:7][c:8]([C... | CCOC(C)=O.C[C@H]1C[C@@H](N)c2ccccc2N1C(=O)c1ccc2c(c1)OCCN2C.OB(O)c1ccc(Cl)cc1 | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc3c(c2)OCCN3C)c2ccccc21 | null | C(C)(=O)[O-].[Cu+2].C(C)(=O)[O-] | C(Cl)Cl | Acylation | OtherReaction | d5b79df0bcad37b68666465f98bdbf09561dfcc3b18a2acc5b3be323501cddff | d21a41b88b3a6857658a80208e904dc455b890b23aaf7d742d8a593a93afbd98 | O=C(c1ccc2c(c1)OCCN2)N1CC[C@@H](Nc2ccccc2)c2ccccc21 | C-C-O-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].O-B(-O)-[c;H0;D3;+0:4](:[c:5]:[c:6]):[c:7]:[c:8].[C:9]-[C:10](-[NH2;D1;+0:11])-[c:12]>>[C:9]-[C:10](-[N;H0;D3;+0:11](-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3])-[c;H0;D3;+0:4](:[c:5]:[c:6]):[c:7]:[c:8])-[c:12] | null | [] | 60 | CELSIUS | 1 | HOUR | To a solution of (2S,4R)-(4-amino-2-methyl-3,4-dihydro-2H-quinolin-1-yl)-(4-methyl-3,4-dihydro-2H-benzo[1,4]oxazin-7-yl)-methanone (662 mg, 1.87 mmol) in methylene chloride (8 mL) was added 4-chlorophenylboronic acid (583 mg, 3.74 mmol), triethylamine (1.81 ml, 13.09 mmol) and copper(II)acetate (681 mg, 3.74 mmol). The... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Primary amine.Boronic acid | Tertiary amide | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccc2c(c1)[NH]CCO2.c1ccc2c(c1)CCC[NH]2 | HO-.B | C(C)(=O)[O-].[Cu+2].C(C)(=O)[O-].C(Cl)Cl | 60 | 1 | CCOC(C)=O.C[C@H]1C[C@@H](N)c2ccccc2N1C(=O)c1ccc2c(c1)OCCN2C.OB(O)c1ccc(Cl)cc1>C(C)(=O)[O-].[Cu+2].C(C)(=O)[O-].C(Cl)Cl>CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc3c(c2)OCCN3C)c2ccccc21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-1a88f1be5bad4005a59d44751fa43e7f | CC(=O)Cl.C[C@H]1C[C@@H](Nc2ccc(Cl)cc2)c2ccccc2N1C(=O)c1ccc2c(c1)OCCN2C>>CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc3c(c2)OCCN3C)c2ccccc21 | C(C)(=O)Cl.ClC1=CC=C(C=C1)N[C@@H]1C[C@@H](N(C2=CC=CC=C12)C(=O)C1=CC2=C(N(CCO2)C)C=C1)C.C(C)(C)N(CC)C(C)C>>ClC1=CC=C(C=C1)N(C(C)=O)[C@@H]1C[C@@H](N(C2=CC=CC=C12)C(=O)C1=CC2=C(N(CCO2)C)C=C1)C | Cl[C:2]([CH3:1])=[O:3].[NH:4]([c:5]1[cH:6][cH:7][c:8]([Cl:9])[cH:10][cH:11]1)[C@@H:12]1[CH2:13][C@H:14]([CH3:15])[N:16]([C:17](=[O:18])[c:19]2[cH:20][cH:21][c:22]3[c:23]([cH:24]2)[O:25][CH2:26][CH2:27][N:28]3[CH3:29])[c:30]2[cH:31][cH:32][cH:33][cH:34][c:35]21>>[CH3:1][C:2](=[O:3])[N:4]([c:5]1[cH:6][cH:7][c:8]([Cl:9])[... | CC(=O)Cl.C[C@H]1C[C@@H](Nc2ccc(Cl)cc2)c2ccccc2N1C(=O)c1ccc2c(c1)OCCN2C | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc3c(c2)OCCN3C)c2ccccc21 | null | null | C(Cl)Cl | Acylation | N-alkylation of secondary amines with alkyl halides | b92e0bfd3d683c1f2a209adfe70a67ad7cb0d87749eb59e8fe0cf1689bc291e0 | 96cb0a2fed10552c5770a45a2d6523b47ac3e38928b4a9c698d8577451182dcd | O=C(c1ccc2c(c1)OCCN2)N1CC[C@@H](Nc2ccccc2)c2ccccc21 | Cl-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[C:4]-[C:5](-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9])-[c:10]>>[C:4]-[C:5](-[N;H0;D3;+0:6](-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3])-[c:7](:[c:8]):[c:9])-[c:10] | null | [] | null | null | 4 | HOUR | To a solution of (2S,4R)-[4-(4-Chloro-phenylamino)-2-methyl-3,4-dihydro-2H-quinolin-1-yl]-(4-methyl-3,4-dihydro-2H-benzo[1,4]oxazin-7-yl)-methanone (540 mg, 1.25 mmol) in methylene chloride (5 mL) was added diisopropylethylamine (0.240 mL, 1.37 mmol) followed by acetyl chloride (2 mL). The mixture was stirred at room t... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Secondary amine | Tertiary amide | null | null | c1ccccc1.c1ccc2c(c1)[NH]CCO2.c1ccc2c(c1)CCC[NH]2 | HCl | C(Cl)Cl | null | 4 | CC(=O)Cl.C[C@H]1C[C@@H](Nc2ccc(Cl)cc2)c2ccccc2N1C(=O)c1ccc2c(c1)OCCN2C>C(Cl)Cl>CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc3c(c2)OCCN3C)c2ccccc21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-427b9a5f1e954eb8a5c3958395bcb62c | C=CCCC(=O)OCC.C[C@H]1C[C@@H](NC(=O)OCc2ccccc2)c2ccccc2N1C(=O)c1ccc(I)cc1>>CCOC(=O)CC/C=C/c1ccc(C(=O)N2c3ccccc3[C@H](NC(=O)OCc3ccccc3)C[C@@H]2C)cc1 | IC1=CC=C(C(=O)N2[C@H](C[C@H](C3=CC=CC=C23)NC(OCC2=CC=CC=C2)=O)C)C=C1.C(C)OC(CCC=C)=O.C(C)(=O)[O-].[K+].C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1>>C(C1=CC=CC=C1)OC(=O)N[C@@H]1C[C@@H](N(C2=CC=CC=C12)C(=O)C1=CC=C(C=C1)/C=C/CCC(=O)OCC)C | [CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][CH2:7][CH:8]=[CH2:9].I[c:10]1[cH:11][cH:12][c:13]([C:14](=[O:15])[N:16]2[c:17]3[cH:18][cH:19][cH:20][cH:21][c:22]3[C@H:23]([NH:24][C:25](=[O:26])[O:27][CH2:28][c:29]3[cH:30][cH:31][cH:32][cH:33][cH:34]3)[CH2:35][C@@H:36]2[CH3:37])[cH:38][cH:39]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[... | C=CCCC(=O)OCC.C[C@H]1C[C@@H](NC(=O)OCc2ccccc2)c2ccccc2N1C(=O)c1ccc(I)cc1 | CCOC(=O)CC/C=C/c1ccc(C(=O)N2c3ccccc3[C@H](NC(=O)OCc3ccccc3)C[C@@H]2C)cc1 | null | [Cl-].C(CCC)[N+](CCCC)(CCCC)CCCC.C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-] | CN(C)C=O | C-C Coupling | OtherReaction | 2d4a44695e29e4a9ab430c3b66736ad86dd99247e7216f16f3ca137abca78747 | df8442c9f2045421fb18548edb9c6acaeb9710f63e741d9f72e0000ca35c948a | O=C(N[C@@H]1CCN(C(=O)c2ccccc2)c2ccccc21)OCc1ccccc1 | I-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[C:6]-[C:7]=[CH2;D1;+0:8]>>[C:6]/[C:7]=[CH;D2;+0:8]/[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5] | 83.3 | [{"value": 83.0, "product": "C(C1=CC=CC=C1)OC(=O)N[C@@H]1C[C@@H](N(C2=CC=CC=C12)C(=O)C1=CC=C(C=C1)/C=C/CCC(=O)OCC)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 83.3, "product": "C(C1=CC=CC=C1)OC(=O)N[C@@H]1C[C@@H](N(C2=CC=CC=C12)C(=O)C1=CC=C(C=C1)/C=C/CCC(=O)OCC)C", "details": "CALCULATEDPERCENTYIELD",... | null | null | 1 | HOUR | To a solution of benzyl [(2S,4R)-1-(4-iodobenzoyl)-2-methyl-1,2,3,4-tetrahydroquinolin-4-yl]carbamate (0.6 g, 1.14 mmol) in DMF (15 mL) at room temperature was added pent-4-enoic acid ethyl ester (0.292 g, 2.28 mmol), potassium acetate (0.67 g, 6.84 mmol), palladium acetate (0.05 g, 0.228 mmol), tetrabutylammonium chlo... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Allyl | null | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1.c1ccc2c(c1)CCC[NH]2 | HI | [Cl-].C(CCC)[N+](CCCC)(CCCC)CCCC.C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-].CN(C)C=O | null | 1 | C=CCCC(=O)OCC.C[C@H]1C[C@@H](NC(=O)OCc2ccccc2)c2ccccc2N1C(=O)c1ccc(I)cc1>[Cl-].C(CCC)[N+](CCCC)(CCCC)CCCC.C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-].CN(C)C=O>CCOC(=O)CC/C=C/c1ccc(C(=O)N2c3ccccc3[C@H](NC(=O)OCc3ccccc3)C[C@@H]2C)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-3128afadddc3442999db123be835d0e1 | CCOC(=O)CCCCc1ccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccc(Cl)cc3)C[C@@H]2C)cc1.[NH4+]>>CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(CCCCC(N)=O)cc2)c2ccccc21 | CN(C)C(=[N+](C)C)ON1C2=C(C=CC=N2)N=N1.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.C=1C=CC2=C(C1)N=NN2O.[Cl-].[NH4+].C(C)(=O)N([C@@H]1C[C@@H](N(C2=CC=CC=C12)C(=O)C1=CC=C(C=C1)CCCCC(=O)OCC)C)C1=CC=C(C=C1)Cl.C([O-])([O-])=O.[K+].[K+]>>C(C)(=O)N([C@@H]1C[C@@H](N(C2=CC=CC=C12)C(=O)C1=CC=C(C=C1)CCCCC(=O)N)C)C1=CC=C(C=C1)Cl | CCO[C:27]([CH2:26][CH2:25][CH2:24][CH2:23][c:22]1[cH:21][cH:20][c:19]([C:17]([N:16]2[C@@H:14]([CH3:15])[CH2:13][C@@H:12]([N:4]([C:2]([CH3:1])=[O:3])[c:5]3[cH:6][cH:7][c:8]([Cl:9])[cH:10][cH:11]3)[c:37]3[c:32]2[cH:33][cH:34][cH:35][cH:36]3)=[O:18])[cH:31][cH:30]1)=[O:29].[NH4+:28]>>[CH3:1][C:2](=[O:3])[N:4]([c:5]1[cH:6]... | CCOC(=O)CCCCc1ccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccc(Cl)cc3)C[C@@H]2C)cc1.[NH4+] | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(CCCCC(N)=O)cc2)c2ccccc21 | null | null | CN(C)C=O.CO | Acylation | OtherReaction | d5b10d4f469e7a196a3b04a6a9e159a7d90514b6df5b50c1197d4b1b774c04e1 | adc0ef6f6c1340dd2dbab737c85bf17fc842769181c5db1a2b4f82b391b28f9f | O=C(c1ccccc1)N1CC[C@@H](Nc2ccccc2)c2ccccc21 | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[NH4+;D0:5]>>[C:4]-[C:3]-[C;H0;D3;+0:1](-[NH2;D1;+0:5])=[O;D1;H0:2] | null | [] | 40 | CELSIUS | 18 | HOUR | Ethyl 5-(4-{[(2S,4R)-4-[acetyl(4-chlorophenyl)amino]-2-methyl-3,4-dihydroquinolin-1(2H)-yl]carbonyl}phenyl)pentanoate (0.135 g, 0.25 mmol) was hydrolyzed to the acid by dissolving in 6 ml methanol and potassium carbonate (0.2 g in 4 ml water) was added. The mixture was heated to 40° C. for 24 hours and methanol was rem... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary amide | null | null | c1ccccc1.c1ccccc1.c1ccc2c(c1)CCC[NH]2 | HO- | CN(C)C=O.CO | 40 | 18 | CCOC(=O)CCCCc1ccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccc(Cl)cc3)C[C@@H]2C)cc1.[NH4+]>CN(C)C=O.CO>CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(CCCCC(N)=O)cc2)c2ccccc21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-8009694dad56484686c2523b35f24ee9 | COc1ccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccc(Cl)cc3)C[C@@H]2C)cc1>>COc1ccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccccc3)C[C@@H]2C)cc1 | ClC1=CC=C(C=C1)N(C(C)=O)[C@@H]1C[C@@H](N(C2=CC=CC=C12)C(C1=CC=C(C=C1)OC)=O)C>>COC1=CC=C(C(=O)N2[C@H](C[C@H](C3=CC=CC=C23)N(C(C)=O)C2=CC=CC=C2)C)C=C1 | Cl[c:24]1[cH:23][cH:22][c:21]([N:17]([C@H:16]2[c:15]3[c:10]([cH:11][cH:12][cH:13][cH:14]3)[N:9]([C:7]([c:6]3[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:31][cH:30]3)=[O:8])[C@@H:28]([CH3:29])[CH2:27]2)[C:18]([CH3:19])=[O:20])[cH:26][cH:25]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([C:7](=[O:8])[N:9]2[c:10]3[cH:11][cH:12][cH:13][cH:1... | COc1ccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccc(Cl)cc3)C[C@@H]2C)cc1 | COc1ccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccccc3)C[C@@H]2C)cc1 | null | [Pd] | CO | Functional Group Interconversion | Aromatic dehalogenation | b66818d3926a4463fb8e1c3d4a89e94e47b4d46960d4bdb7bcfbeeec427cfd4e | 56de34d4a44cb25d9380269ee5e138b0f24b40a3a0db22c5508049dc775a861f | O=C(c1ccccc1)N1CC[C@@H](Nc2ccccc2)c2ccccc21 | 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] | 95.2 | [{"value": 95.0, "product": "COC1=CC=C(C(=O)N2[C@H](C[C@H](C3=CC=CC=C23)N(C(C)=O)C2=CC=CC=C2)C)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 95.2, "product": "COC1=CC=C(C(=O)N2[C@H](C[C@H](C3=CC=CC=C23)N(C(C)=O)C2=CC=CC=C2)C)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | (2S,4R)-N-(4-Chloro-phenyl)-N-[1-(4-methoxy-benzoyl)-2-methyl-1,2,3,4-tetrahydro-quinolin-4-yl]-acetamide (200 mg, 0.36 mmol) was dissolved in MeOH and a catalytic amount of Palladium on Carbon (10%) was added. The round bottom flask in which resided the resulting solution was evacuated and backfilled with hydrogen. Th... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | null | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1.c1ccc2c(c1)CCC[NH]2 | Other | [Pd].CO | null | 8 | COc1ccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccc(Cl)cc3)C[C@@H]2C)cc1>[Pd].CO>COc1ccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccccc3)C[C@@H]2C)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-00607726e7474170b55eb44769e4da10 | COC(=O)C(C)(C)CCOc1ccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccc(Cl)cc3)C[C@@H]2C)cc1F>>CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(OCCC(C)(C)C(=O)O)c(F)c2)c2ccccc21 | COC(C(CCOC1=C(C=C(C=C1)C(=O)N1[C@H](C[C@H](C2=CC=CC=C12)N(C1=CC=C(C=C1)Cl)C(C)=O)C)F)(C)C)=O.[OH-].[Li+].Cl>>C(C)(=O)N([C@@H]1C[C@@H](N(C2=CC=CC=C12)C(=O)C1=CC(=C(OCCC(C(=O)O)(C)C)C=C1)F)C)C1=CC=C(C=C1)Cl | C[O:31][C:29]([C:26]([CH2:25][CH2:24][O:23][c:22]1[cH:21][cH:20][c:19]([C:17]([N:16]2[C@@H:14]([CH3:15])[CH2:13][C@@H:12]([N:4]([C:2]([CH3:1])=[O:3])[c:5]3[cH:6][cH:7][c:8]([Cl:9])[cH:10][cH:11]3)[c:40]3[c:35]2[cH:36][cH:37][cH:38][cH:39]3)=[O:18])[cH:34][c:32]1[F:33])([CH3:27])[CH3:28])=[O:30]>>[CH3:1][C:2](=[O:3])[N:... | COC(=O)C(C)(C)CCOc1ccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccc(Cl)cc3)C[C@@H]2C)cc1F | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(OCCC(C)(C)C(=O)O)c(F)c2)c2ccccc21 | null | null | CO.C1CCOC1 | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | O=C(c1ccccc1)N1CC[C@@H](Nc2ccccc2)c2ccccc21 | 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] | null | [] | null | null | 1 | HOUR | (2S,4R)-4-(4-{4-[Acetyl-(4-chloro-phenyl)-amino]-2-methyl-3,4-dihydro-2H-quinoline-1-carbonyl}-2-fluoro-phenoxy)-2,2-dimethyl-butyric acid methyl ester (100 mg) was dissolved in methanol/THF (1:1, 5 mL), and lithium hydroxide (1.0N, 1 mL) was added. After 1 hour, the reaction was acidified (HCl) and extracted from with... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1.c1ccccc1.c1ccc2c(c1)CCC[NH]2 | Other | CO.C1CCOC1 | null | 1 | COC(=O)C(C)(C)CCOc1ccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccc(Cl)cc3)C[C@@H]2C)cc1F>CO.C1CCOC1>CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(OCCC(C)(C)C(=O)O)c(F)c2)c2ccccc21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-94f6cd23ee694e4c95608c31b58a9530 | CC(=O)O.CC(C)n1ncc2cc(C(=O)N3c4ccccc4[C@H](N)C[C@@H]3C)ccc21.OB(O)c1ccc(Cl)cc1>>CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc3c(cnn3C(C)C)c2)c2ccccc21 | Br.CC(=O)O.ClC1=CC=C(C=C1)B(O)O.C(C)N(CC)CC.N[C@@H]1C[C@@H](N(C2=CC=CC=C12)C(=O)C=1C=C2C=NN(C2=CC1)C(C)C)C>>ClC1=CC=C(C=C1)N(C(C)=O)[C@@H]1C[C@@H](N(C2=CC=CC=C12)C(=O)C=1C=C2C=NN(C2=CC1)C(C)C)C | O[C:2]([CH3:1])=[O:3].[NH2:4][C@@H:12]1[CH2:13][C@H:14]([CH3:15])[N:16]([C:17](=[O:18])[c:19]2[cH:20][cH:21][c:22]3[c:23]([cH:24][n:25][n:26]3[CH:27]([CH3:28])[CH3:29])[cH:30]2)[c:31]2[cH:32][cH:33][cH:34][cH:35][c:36]21.OB(O)[c:5]1[cH:6][cH:7][c:8]([Cl:9])[cH:10][cH:11]1>>[CH3:1][C:2](=[O:3])[N:4]([c:5]1[cH:6][cH:7][c... | CC(=O)O.CC(C)n1ncc2cc(C(=O)N3c4ccccc4[C@H](N)C[C@@H]3C)ccc21.OB(O)c1ccc(Cl)cc1 | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc3c(cnn3C(C)C)c2)c2ccccc21 | null | [Pd].C(C)(=O)[O-].[Cu+2].C(C)(=O)[O-] | ClCCl.N1=CC=CC=C1 | Acylation | OtherReaction | b210d0749be0070914f49434c7ba750557c7c260e12a30bdff5816327ee8e242 | 49621307eb2c1cae0ffe16756553688e1e2d3ddd29578a63d6bc32ba3a602763 | O=C(c1ccc2[nH]ncc2c1)N1CC[C@@H](Nc2ccccc2)c2ccccc21 | O-B(-O)-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].O-[C;H0;D3;+0:6](-[C;D1;H3:7])=[O;D1;H0:8].[C:9]-[C:10](-[NH2;D1;+0:11])-[c:12]>>[C:9]-[C:10](-[N;H0;D3;+0:11](-[C;H0;D3;+0:6](-[C;D1;H3:7])=[O;D1;H0:8])-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5])-[c:12] | null | [] | null | null | null | null | (2S,4R)-N-(4-Chloro-phenyl)-N-[1-(1-isopropyl-1H-indazole-5-carbonyl)-2-methyl-1,2,3,4-tetrahydro-quinolin-4-yl]-acetamide was prepared following general procedure G, substituting 1-Isopropyl-1H-indazole-5-carbonyl chloride for 4-fluorobenzoyl chloride. (1-Isopropyl-1H-indazole-5-carbonyl chloride was prepared in three... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine.Boronic acid | Tertiary amide | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccc2n[nH]cc2c1.c1ccc2c(c1)CCC[NH]2 | HO-.B | [Pd].C(C)(=O)[O-].[Cu+2].C(C)(=O)[O-].ClCCl.N1=CC=CC=C1 | null | null | CC(=O)O.CC(C)n1ncc2cc(C(=O)N3c4ccccc4[C@H](N)C[C@@H]3C)ccc21.OB(O)c1ccc(Cl)cc1>[Pd].C(C)(=O)[O-].[Cu+2].C(C)(=O)[O-].ClCCl.N1=CC=CC=C1>CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc3c(cnn3C(C)C)c2)c2ccccc21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a92fb496713c4fc5871cfb210e11746e | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2cnn(C(C)C)c2)c2ccccc21.CC(C)n1cc(C(=O)Cl)cn1.Cc1nn(C)c2sc(C(=O)O)cc12>>CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2cc3c(C)nn(C)c3s2)c2ccccc21.Cc1nn(C)c2sc(C(=O)Cl)cc12 | CN1N=C(C2=C1SC(=C2)C(=O)O)C.C(C(=O)Cl)(=O)Cl.ClC1=CC=C(C=C1)N(C(C)=O)[C@@H]1C[C@@H](N(C2=CC=CC=C12)C(=O)C=1C=NN(C1)C(C)C)C.C(C)(C)N1N=CC(=C1)C(=O)Cl>>ClC1=CC=C(C=C1)N(C(C)=O)[C@@H]1C[C@@H](N(C2=CC=CC=C12)C(=O)C1=CC2=C(N(N=C2C)C)S1)C.CN1N=C(C2=C1SC(=C2)C(=O)Cl)C | CC(C)n1nc[c:19]([C:17]([N:16]2[C@@H:14]([CH3:15])[CH2:13][C@@H:12]([N:4]([C:2]([CH3:1])=[O:3])[c:5]3[cH:6][cH:7][c:8]([Cl:9])[cH:10][cH:11]3)[c:34]3[c:29]2[cH:30][cH:31][cH:32][cH:33]3)=[O:18])[cH:20]1.C[CH:26]([CH3:23])[n:25]1[n:24][cH:22][c:21](C(=O)[Cl:45])[cH:27]1.O[C:43]([c:42]1[s:28][c:40]2[n:38]([CH3:39])[n:37][... | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2cnn(C(C)C)c2)c2ccccc21.CC(C)n1cc(C(=O)Cl)cn1.Cc1nn(C)c2sc(C(=O)O)cc12 | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2cc3c(C)nn(C)c3s2)c2ccccc21.Cc1nn(C)c2sc(C(=O)Cl)cc12 | null | null | ClCCl.CN(C)C=O | C-C Coupling | OtherReaction | 15c91b93e844b7d740f458a2fea8a78b27c46351434cff9c909523c1228b4cfc | edd0926fab5e8066ac1a42785cd03484ec38f412dfee015a3bcc3bcaf826acdc | O=C(c1cc2cn[nH]c2s1)N1CC[C@@H](Nc2ccccc2)c2ccccc21.c1cc2cn[nH]c2s1 | C-C(-C)-n1:[cH;D2;+0:1]:[c;H0;D3;+0:2](-[C:3](=[O;D1;H0:4])-[#7:5](-[C:6])-[c:7]):c:n:1.C-[CH;D3;+0:8](-[CH3;D1;+0:9])-[#7;a:10]1:[#7;a:11]:[cH;D2;+0:12]:[c;H0;D3;+0:13](-C(=O)-[Cl;H0;D1;+0:14]):[cH;D2;+0:15]:1.O-[C;H0;D3;+0:16](=[O;D1;H0:17])-[c;H0;D3;+0:18]1:[c:19]:[c:20]2:[c:21](-[C;D1;H3:22]):[#7;a:23]:[#7;a:24](-[... | null | [] | null | null | null | null | N-(4-Chlorophenyl)-N-{(2S,4R)-1-[(1,3-dimethyl-1H-thieno[2,3-c]pyrazol-5-yl)carbonyl]-2-methyl-1,2,3,4-tetrahydroquinolin-4-yl}acetamide was prepared following the procedure for N-(4-chlorophenyl)-N-{(2S,4R)-1-[(1-isopropyl-1H-pyrazol-4-yl)carbonyl]-2-methyl-1,2,3,4-tetrahydroquinolin-4-yl}acetamide substituting 1,3-di... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Carboxylic acid | Acyl halide | c1cn[nH]c1.c1cn[nH]c1.c1cc2cn[nH]c2s1 | c1cc2c[nH]nc2s1.c1cc2c[nH]nc2s1 | c1ccccc1.c1cc2c[nH]nc2s1.c1ccc2c(c1)CCC[NH]2.c1cc2c[nH]nc2s1 | HO- | ClCCl.CN(C)C=O | null | null | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2cnn(C(C)C)c2)c2ccccc21.CC(C)n1cc(C(=O)Cl)cn1.Cc1nn(C)c2sc(C(=O)O)cc12>ClCCl.CN(C)C=O>CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2cc3c(C)nn(C)c3s2)c2ccccc21.Cc1nn(C)c2sc(C(=O)Cl)cc12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-b278750930c742c0af53f041ab8367ae | COc1ccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3cccc4c3ccn4C(=O)OC(C)(C)C)C[C@@H]2C)cc1>>COc1ccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3cccc4[nH]ccc34)C[C@@H]2C)cc1 | C(C)(=O)N(C1=C2C=CN(C2=CC=C1)C(=O)OC(C)(C)C)[C@@H]1C[C@@H](N(C2=CC=CC=C12)C(C1=CC=C(C=C1)OC)=O)C>>N1C=CC2=C(C=CC=C12)N(C(C)=O)[C@@H]1C[C@@H](N(C2=CC=CC=C12)C(C1=CC=C(C=C1)OC)=O)C | CC(C)(C)OC(=O)[n:26]1[c:25]2[cH:24][cH:23][cH:22][c:21]([N:17]([C@H:16]3[c:15]4[c:10]([cH:11][cH:12][cH:13][cH:14]4)[N:9]([C:7]([c:6]4[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:34][cH:33]4)=[O:8])[C@@H:31]([CH3:32])[CH2:30]3)[C:18]([CH3:19])=[O:20])[c:29]2[cH:28][cH:27]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([C:7](=[O:8])[N:9]2... | COc1ccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3cccc4c3ccn4C(=O)OC(C)(C)C)C[C@@H]2C)cc1 | COc1ccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3cccc4[nH]ccc34)C[C@@H]2C)cc1 | null | null | Cl.O1CCOCC1 | Reduction | Boc amine deprotection | 42add5cbb5098100ca964321579ee6eb449e9641492081de05db5169b8facbfb | e1bf5a54b1f87284564f107662531aec2aff7de801e4606340967b38924afb28 | O=C(c1ccccc1)N1CC[C@@H](Nc2cccc3[nH]ccc23)c2ccccc21 | C-C(-C)(-C)-O-C(=O)-[n;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[c:5]:1:[c:6]>>[c:6]:[c:5]1:[c:4]:[c:3]:[c:2]:[nH;D2;+0:1]:1 | 28 | [{"value": 28.0, "product": "N1C=CC2=C(C=CC=C12)N(C(C)=O)[C@@H]1C[C@@H](N(C2=CC=CC=C12)C(C1=CC=C(C=C1)OC)=O)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 25.9, "product": "N1C=CC2=C(C=CC=C12)N(C(C)=O)[C@@H]1C[C@@H](N(C2=CC=CC=C12)C(C1=CC=C(C=C1)OC)=O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired... | null | null | null | null | tert-Butyl 4-{acetyl[(2S,4R)-1-(4-methoxybenzoyl)-2-methyl-1,2,3,4-tetrahydroquinolin-4-yl]amino}-1H-indole-1-carboxylate (0.035 g, 0.068 mmol) was stirred in 4 N HCl in dioxane (1 mL) for 24 h and then evaporated to dryness. The residue was dissolved in ethyl acetate, washed with 1N NaOH, water, brine, dried over sodi... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Boc | null | c1cccc2[nH]ccc12 | c1ccc2[nH]ccc2c1 | c1ccccc1.c1ccc2[nH]ccc2c1.c1ccc2c(c1)CCC[NH]2 | HO- | Cl.O1CCOCC1 | null | null | COc1ccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3cccc4c3ccn4C(=O)OC(C)(C)C)C[C@@H]2C)cc1>Cl.O1CCOCC1>COc1ccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3cccc4[nH]ccc34)C[C@@H]2C)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-9539a104c8c94838b2af679d2bb9327b | COC(=O)C(C)(C)CCN(C)c1ccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccc(Cl)cc3)C[C@@H]2C)cc1>>CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(N(C)CCC(C)(C)C(=O)O)cc2)c2ccccc21 | C(C)(=O)N([C@@H]1C[C@@H](N(C2=CC=CC=C12)C(=O)C1=CC=C(C=C1)N(CCC(C(=O)OC)(C)C)C)C)C1=CC=C(C=C1)Cl.[OH-].[Na+]>>C(C)(=O)N([C@@H]1C[C@@H](N(C2=CC=CC=C12)C(=O)C1=CC=C(C=C1)N(CCC(C(=O)O)(C)C)C)C)C1=CC=C(C=C1)Cl | C[O:32][C:30]([C:27]([CH2:26][CH2:25][N:23]([c:22]1[cH:21][cH:20][c:19]([C:17]([N:16]2[C@@H:14]([CH3:15])[CH2:13][C@@H:12]([N:4]([C:2]([CH3:1])=[O:3])[c:5]3[cH:6][cH:7][c:8]([Cl:9])[cH:10][cH:11]3)[c:40]3[c:35]2[cH:36][cH:37][cH:38][cH:39]3)=[O:18])[cH:34][cH:33]1)[CH3:24])([CH3:28])[CH3:29])=[O:31]>>[CH3:1][C:2](=[O:3... | COC(=O)C(C)(C)CCN(C)c1ccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccc(Cl)cc3)C[C@@H]2C)cc1 | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(N(C)CCC(C)(C)C(=O)O)cc2)c2ccccc21 | null | null | CO.O1CCCC1.O | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | O=C(c1ccccc1)N1CC[C@@H](Nc2ccccc2)c2ccccc21 | 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] | null | [] | 40 | CELSIUS | null | null | Methyl 4-[(4-{[(2S,4R)-4-[acetyl(4-chlorophenyl)amino]-2-methyl-3,4-dihydroquinolin-1(2H)-yl]carbonyl}phenyl)(methyl)amino]-2,2-dimethylbutanoate was dissolved in methanol/tetrahydrofuran/water (2/1/1) then sodium hydroxide (3 equivalents) was added and reaction mixture heated to 40° C. for 2 h. The mixture was concent... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1.c1ccccc1.c1ccc2c(c1)CCC[NH]2 | Other | CO.O1CCCC1.O | 40 | null | COC(=O)C(C)(C)CCN(C)c1ccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccc(Cl)cc3)C[C@@H]2C)cc1>CO.O1CCCC1.O>CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(N(C)CCC(C)(C)C(=O)O)cc2)c2ccccc21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-77f9ed3a9e87443c81d3f56ab132efd9 | CC(=O)Cl.COc1ccc(C(=O)N2c3ccccc3[C@H](N(C(=O)CO)c3ccc(Cl)cc3)C[C@@H]2C)cc1>>COc1ccc(C(=O)N2c3ccccc3[C@H](N(C(=O)COC(C)=O)c3ccc(Cl)cc3)C[C@@H]2C)cc1 | ClC1=CC=C(C=C1)N(C(CO)=O)[C@@H]1C[C@@H](N(C2=CC=CC=C12)C(C1=CC=C(C=C1)OC)=O)C.FC1=CC=C(C(=O)Cl)C=C1.C(C)(=O)Cl>>C(C)(=O)OCC(=O)N([C@@H]1C[C@@H](N(C2=CC=CC=C12)C(C1=CC=C(C=C1)OC)=O)C)C1=CC=C(C=C1)Cl | Cl[C:22]([CH3:23])=[O:24].[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([C:7](=[O:8])[N:9]2[c:10]3[cH:11][cH:12][cH:13][cH:14][c:15]3[C@H:16]([N:17]([C:18](=[O:19])[CH2:20][OH:21])[c:25]3[cH:26][cH:27][c:28]([Cl:29])[cH:30][cH:31]3)[CH2:32][C@@H:33]2[CH3:34])[cH:35][cH:36]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([C:7](=[O:8])[N:9]... | CC(=O)Cl.COc1ccc(C(=O)N2c3ccccc3[C@H](N(C(=O)CO)c3ccc(Cl)cc3)C[C@@H]2C)cc1 | COc1ccc(C(=O)N2c3ccccc3[C@H](N(C(=O)COC(C)=O)c3ccc(Cl)cc3)C[C@@H]2C)cc1 | null | null | null | Acylation | Schotten-Baumann to ester | 6cefe709828c5bd4655f254e75d5dff9e8876e192e7dd47256c1bc0067bc5291 | d8a7643b81ed07a6f633aa99465180dfa0565e61ae25aef36338ebb9837c9cef | O=C(c1ccccc1)N1CC[C@@H](Nc2ccccc2)c2ccccc21 | Cl-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[C:4]-[#7:5](-[c:6])-[C:7](=[O;D1;H0:8])-[C:9]-[OH;D1;+0:10]>>[C:4]-[#7:5](-[c:6])-[C:7](=[O;D1;H0:8])-[C:9]-[O;H0;D2;+0:10]-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3] | null | [] | null | null | null | null | N-(4-chlorophenyl)-2-hydroxy-N-[(2S,4R)-1-(4-methoxybenzoyl)-2-methyl-1,2,3,4-tetrahydroquinolin-4-yl]acetamide was made following general procedure G, substituting 4-methoxybenzoyl chloride for 4-fluorobenzoyl chloride. Procedure A was followed further substituting acetoxyacetylchloride for acetyl chloride in the last... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary alcohol | Ester | null | null | c1ccccc1.c1ccccc1.c1ccc2c(c1)CCC[NH]2 | HCl | null | null | null | CC(=O)Cl.COc1ccc(C(=O)N2c3ccccc3[C@H](N(C(=O)CO)c3ccc(Cl)cc3)C[C@@H]2C)cc1>>COc1ccc(C(=O)N2c3ccccc3[C@H](N(C(=O)COC(C)=O)c3ccc(Cl)cc3)C[C@@H]2C)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-b4fb5c09234746ec83b42e3c0c9e2e37 | COc1ccc(C(=O)N2c3ccccc3[C@H](N(C(=O)COC(C)=O)c3ccc(Cl)cc3)C[C@@H]2C)cc1>>COc1ccc(C(=O)N2c3ccccc3[C@H](N(C(=O)CO)c3ccc(Cl)cc3)C[C@@H]2C)cc1 | C(C)(=O)OCC(=O)N([C@@H]1C[C@@H](N(C2=CC=CC=C12)C(C1=CC=C(C=C1)OC)=O)C)C1=CC=C(C=C1)Cl.C([O-])([O-])=O.[K+].[K+]>>ClC1=CC=C(C=C1)N(C(CO)=O)[C@@H]1C[C@@H](N(C2=CC=CC=C12)C(C1=CC=C(C=C1)OC)=O)C | CC(=O)[O:21][CH2:20][C:18]([N:17]([C@H:16]1[c:15]2[c:10]([cH:11][cH:12][cH:13][cH:14]2)[N:9]([C:7]([c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:33][cH:32]2)=[O:8])[C@@H:30]([CH3:31])[CH2:29]1)[c:22]1[cH:23][cH:24][c:25]([Cl:26])[cH:27][cH:28]1)=[O:19]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([C:7](=[O:8])[N:9]2[c:10]3[cH:11][c... | COc1ccc(C(=O)N2c3ccccc3[C@H](N(C(=O)COC(C)=O)c3ccc(Cl)cc3)C[C@@H]2C)cc1 | COc1ccc(C(=O)N2c3ccccc3[C@H](N(C(=O)CO)c3ccc(Cl)cc3)C[C@@H]2C)cc1 | null | null | O.CO | Reduction | Hydrolysis or Hydrogenolysis of Carboxylic Esters or Thioesters | 21d61543c6ec8a8cebe1b3ef55ef3dd20acbf79a4f1c12a7fb51e32be7a3248a | 1fbcd628a0426673c5d10aa49a977cd2d1ae02a8cdf57bbb10d94aa03a94e937 | O=C(c1ccccc1)N1CC[C@@H](Nc2ccccc2)c2ccccc21 | C-C(=O)-[O;H0;D2;+0:1]-[C:2]-[C:3](=[O;D1;H0:4])-[#7:5](-[C:6])-[c:7]>>[C:6]-[#7:5](-[c:7])-[C:3](=[O;D1;H0:4])-[C:2]-[OH;D1;+0:1] | 84 | [{"value": 84.0, "product": "ClC1=CC=C(C=C1)N(C(CO)=O)[C@@H]1C[C@@H](N(C2=CC=CC=C12)C(C1=CC=C(C=C1)OC)=O)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 83.4, "product": "ClC1=CC=C(C=C1)N(C(CO)=O)[C@@H]1C[C@@H](N(C2=CC=CC=C12)C(C1=CC=C(C=C1)OC)=O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": fal... | null | null | 4 | HOUR | 2-{(4-Chlorophenyl)[(2S,4R)-1-(4-methoxybenzoyl)-2-methyl-1,2,3,4-tetrahydroquinolin-4-yl]amino}-2-oxoethyl acetate (496 mg, 0.98 mmol, 1 eq.) was dissolved in methanol (12 ml). A solution of potassium carbonate (1.08 g, 7.84 mmol, 8 eq.) in water (5 ml) was added and reaction mixture was stirred at room temperature fo... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary alcohol | null | null | c1ccccc1.c1ccccc1.c1ccc2c(c1)CCC[NH]2 | HO- | O.CO | null | 4 | COc1ccc(C(=O)N2c3ccccc3[C@H](N(C(=O)COC(C)=O)c3ccc(Cl)cc3)C[C@@H]2C)cc1>O.CO>COc1ccc(C(=O)N2c3ccccc3[C@H](N(C(=O)CO)c3ccc(Cl)cc3)C[C@@H]2C)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-47125615988f44448d32b8b079878f43 | CCOC(=O)N1CCOc2ccc(C(=O)N3c4ccccc4[C@H](N)C[C@@H]3C)cc21.CCOC(C)=O.OB(O)c1ccc(Cl)cc1>>CCOC(=O)N1CCOc2ccc(C(=O)N3c4ccccc4[C@H](N(C(C)=O)c4ccc(Cl)cc4)C[C@@H]3C)cc21 | C(C)(=O)OCC.C(C)OC(=O)N1CCOC2=C1C=C(C=C2)C(=O)N2[C@H](C[C@H](C1=CC=CC=C21)N)C.ClC1=CC=C(C=C1)B(O)O.C(C)N(CC)CC>>C(C)OC(=O)N1CCOC2=C1C=C(C=C2)C(=O)N2[C@H](C[C@H](C1=CC=CC=C21)N(C2=CC=C(C=C2)Cl)C(C)=O)C | [CH3:1][CH2:2][O:3][C:4](=[O:5])[N:6]1[CH2:7][CH2:8][O:9][c:10]2[cH:11][cH:12][c:13]([C:14](=[O:15])[N:16]3[c:17]4[cH:18][cH:19][cH:20][cH:21][c:22]4[C@H:23]([NH2:24])[CH2:35][C@@H:36]3[CH3:37])[cH:38][c:39]21.CCO[C:25]([CH3:26])=[O:27].OB(O)[c:28]1[cH:29][cH:30][c:31]([Cl:32])[cH:33][cH:34]1>>[CH3:1][CH2:2][O:3][C:4](... | CCOC(=O)N1CCOc2ccc(C(=O)N3c4ccccc4[C@H](N)C[C@@H]3C)cc21.CCOC(C)=O.OB(O)c1ccc(Cl)cc1 | CCOC(=O)N1CCOc2ccc(C(=O)N3c4ccccc4[C@H](N(C(C)=O)c4ccc(Cl)cc4)C[C@@H]3C)cc21 | null | C(C)(=O)[O-].[Cu+2].C(C)(=O)[O-] | C(Cl)Cl | Acylation | OtherReaction | d5b79df0bcad37b68666465f98bdbf09561dfcc3b18a2acc5b3be323501cddff | d21a41b88b3a6857658a80208e904dc455b890b23aaf7d742d8a593a93afbd98 | O=C(c1ccc2c(c1)NCCO2)N1CC[C@@H](Nc2ccccc2)c2ccccc21 | C-C-O-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].O-B(-O)-[c;H0;D3;+0:4](:[c:5]:[c:6]):[c:7]:[c:8].[C:9]-[C:10](-[NH2;D1;+0:11])-[c:12]>>[C:9]-[C:10](-[N;H0;D3;+0:11](-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3])-[c;H0;D3;+0:4](:[c:5]:[c:6]):[c:7]:[c:8])-[c:12] | null | [] | 60 | CELSIUS | 1 | HOUR | To a solution of (2S,4R)-6-(4-Amino-2-methyl-3,4-dihydro-2H-quinoline-1-carbonyl)-2,3-dihydro-benzo[1,4]oxazine-4-carboxylic acid ethyl ester (470 mg, 1.18 mmol) in methylene chloride was added 4-chlorophenylboronic acid (368 mg, 2.36 mmol), triethylamine (1.31 mL, 9.42 mmol) and copper(II)acetate (429 mg, 2.36 mmol). ... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Primary amine.Boronic acid | Tertiary amide | c1ccccc1 | c1ccccc1 | c1ccc2c(c1)[NH]CCO2.c1ccccc1.c1ccc2c(c1)CCC[NH]2 | HO-.B | C(C)(=O)[O-].[Cu+2].C(C)(=O)[O-].C(Cl)Cl | 60 | 1 | CCOC(=O)N1CCOc2ccc(C(=O)N3c4ccccc4[C@H](N)C[C@@H]3C)cc21.CCOC(C)=O.OB(O)c1ccc(Cl)cc1>C(C)(=O)[O-].[Cu+2].C(C)(=O)[O-].C(Cl)Cl>CCOC(=O)N1CCOc2ccc(C(=O)N3c4ccccc4[C@H](N(C(C)=O)c4ccc(Cl)cc4)C[C@@H]3C)cc21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-2b7043dea18c49ecaa89891f8f1cfd79 | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2cnn(C(C)C)c2)c2ccccc21.CC(C)n1cc(C(=O)Cl)cn1.CCOC(=O)CBr.CN(C)C=O.O=C([O-])[O-]>>CCOC(=O)COc1cc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccc(Cl)cc3)C[C@@H]2C)on1.CCOC(=O)COc1cc(C(=O)OC)on1 | CN(C)C=O.ClC1=CC=C(C=C1)N(C(C)=O)[C@@H]1C[C@@H](N(C2=CC=CC=C12)C(=O)C=1C=NN(C1)C(C)C)C.C(C)(C)N1N=CC(=C1)C(=O)Cl.BrCC(=O)OCC.[I-].[K+].C([O-])([O-])=O.[K+].[K+]>>C(C)(=O)N([C@@H]1C[C@@H](N(C2=CC=CC=C12)C(=O)C1=CC(=NO1)OCC(=O)OCC)C)C1=CC=C(C=C1)Cl.C(C)OC(COC1=NOC(=C1)C(=O)OC)=O | C[CH:8](C)[n:36]1[cH:9][c:10]([C:11](=[O:12])[N:13]2[c:14]3[cH:15][cH:16][cH:17][cH:18][c:19]3[C@H:20]([N:21]([C:22]([CH3:23])=[O:24])[c:25]3[cH:26][cH:27][c:28]([Cl:29])[cH:30][cH:31]3)[CH2:32][C@@H:33]2[CH3:34])[cH:44][n:52]1.C[CH:2](n1nc[c:46]([C:47](Cl)=[O:48])[cH:45]1)[CH3:1].Br[CH2:42][C:40]([O:39][CH2:38][CH3:37... | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2cnn(C(C)C)c2)c2ccccc21.CC(C)n1cc(C(=O)Cl)cn1.CCOC(=O)CBr.CN(C)C=O.O=C([O-])[O-] | CCOC(=O)COc1cc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccc(Cl)cc3)C[C@@H]2C)on1.CCOC(=O)COc1cc(C(=O)OC)on1 | null | null | O | C-C Coupling | OtherReaction | 08810427c4c0e31dafc8f7ebd66e20edb12d5450aa08e906222990d5b22b78ec | daf6492869802736994e63bf3927f2ca6eb2dd2bc3c50c4a1f461dbd67fd8762 | O=C(c1ccno1)N1CC[C@@H](Nc2ccccc2)c2ccccc21.c1cnoc1 | Br-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#8:4]-[C:5].C-N(-[CH3;D1;+0:6])-[CH;D2;+0:7]=[O;H0;D1;+0:8].C-[CH;D3;+0:9](-C)-[n;H0;D3;+0:10]1:[cH;D2;+0:11]:[c;H0;D3;+0:12](-[C:13](=[O;D1;H0:14])-[#7:15](-[C:16])-[c:17]):[cH;D2;+0:18]:[n;H0;D2;+0:19]:1.C-[CH;D3;+0:20](-[C;D1;H3:21])-n1:[cH;D2;+0:22]:[c;H0;D3;+0:23](-[C;H0;D3;+0... | 60 | [{"value": 60.0, "product": "C(C)OC(COC1=NOC(=C1)C(=O)OC)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Ethyl [(5-{[(2S,4R)-4-[acetyl(4-chlorophenyl)amino]-2-methyl-3,4-dihydroquinolin-1(2H)-yl]carbonyl}isoxazol-3-yl)oxy]acetate was prepared following the procedure for N-(4-chlorophenyl)-N-{(2S,4R)-1-[(1-isopropyl-1H-pyrazol-4-yl)carbonyl]-2-methyl-1,2,3,4-tetrahydroquinolin-4-yl}acetamide substituting ethyl {[5-(chloroc... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary halide.Ester.Tertiary amide | Ester.Ester.Ester.Ether.Ether | c1cn[nH]c1.c1cn[nH]c1 | c1cnoc1.c1cnoc1 | c1cnoc1.c1ccccc1.c1ccc2c(c1)CCC[NH]2.c1cnoc1 | HCl.Br- | O | null | null | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2cnn(C(C)C)c2)c2ccccc21.CC(C)n1cc(C(=O)Cl)cn1.CCOC(=O)CBr.CN(C)C=O.O=C([O-])[O-]>O>CCOC(=O)COc1cc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccc(Cl)cc3)C[C@@H]2C)on1.CCOC(=O)COc1cc(C(=O)OC)on1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ef2e8696b1f84443b63d5a49f32f0a8e | CCOC(=O)COc1cc(C(=O)OC)on1>>O=C(O)COc1cc(C(=O)O)on1 | C(C)OC(COC1=NOC(=C1)C(=O)OC)=O.[OH-].[Na+]>>C(=O)(O)COC1=NOC(=C1)C(=O)O | CC[O:3][C:2](=[O:1])[CH2:4][O:5][c:6]1[cH:7][c:8]([C:9](=[O:10])[O:11]C)[o:12][n:13]1>>[O:1]=[C:2]([OH:3])[CH2:4][O:5][c:6]1[cH:7][c:8]([C:9](=[O:10])[OH:11])[o:12][n:13]1 | CCOC(=O)COc1cc(C(=O)OC)on1 | O=C(O)COc1cc(C(=O)O)on1 | null | null | CO | Deprotection | OtherReaction | 6e62db7aac546f574bcfb83067ba8906c30fcbfedfc37aa16b5eaad33833f45a | ed5fed81ba501ef41c88831ec6b9463b899bfdd0815c4145ae51c79addb226d0 | c1cnoc1 | C-C-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4].C-[O;H0;D2;+0:5]-[C:6](=[O;D1;H0:7])-[c:8]:[#8;a:9]:[#7;a:10]>>[#7;a:10]:[#8;a:9]:[c:8]-[C:6](=[O;D1;H0:7])-[OH;D1;+0:5].[C:3]-[C:2](=[O;D1;H0:4])-[OH;D1;+0:1] | 86 | [{"value": 86.0, "product": "C(=O)(O)COC1=NOC(=C1)C(=O)O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Ethyl [(5-{[(2S,4R)-4-[acetyl(4-chlorophenyl)amino]-2-methyl-3,4-dihydroquinolin-1(2H)-yl]carbonyl}isoxazol-3-yl)oxy]acetate was prepared following the procedure for N-(4-chlorophenyl)-N-{(2S,4R)-1-[(1-isopropyl-1H-pyrazol-4-yl)carbonyl]-2-methyl-1,2,3,4-tetrahydroquinolin-4-yl}acetamide substituting ethyl {[5-(chloroc... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester | Carboxylic acid.Carboxylic acid | null | null | c1cnoc1 | Other | CO | null | null | CCOC(=O)COc1cc(C(=O)OC)on1>CO>O=C(O)COc1cc(C(=O)O)on1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d33ca123addf4bd2bf9b5f3beef49be2 | CCOC(=O)COc1cc(C(=O)O)on1.O=C(Cl)C(=O)Cl>>CCOC(=O)COc1cc(C(=O)Cl)on1 | C(C)OC(COC1=NOC(=C1)C(=O)O)=O.C(C(=O)Cl)(=O)Cl.CN(C)C=O>>ClC(=O)C1=CC(=NO1)OCC(=O)OCC | O[C:11]([c:10]1[cH:9][c:8]([O:7][CH2:6][C:4]([O:3][CH2:2][CH3:1])=[O:5])[n:15][o:14]1)=[O:12].O=C(Cl)C(=O)[Cl:13]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][O:7][c:8]1[cH:9][c:10]([C:11](=[O:12])[Cl:13])[o:14][n:15]1 | CCOC(=O)COc1cc(C(=O)O)on1.O=C(Cl)C(=O)Cl | CCOC(=O)COc1cc(C(=O)Cl)on1 | null | null | ClCCl | Functional Group Interconversion | Alcohol to chloride_Other | 013cec2edeb273a7a148f349d36a52d99ff4e7bcf8eed78085df830088e387ac | aedb1f68dc5b7eb0583043e1125b741382b17974140a2f46554f0110e2ddc884 | c1cnoc1 | Cl-C(=O)-C(=O)-[Cl;H0;D1;+0:1].O-[C;H0;D3;+0:2](=[O;D1;H0:3])-[c:4]1:[#8;a:5]:[#7;a:6]:[c:7]:[c:8]:1>>[Cl;H0;D1;+0:1]-[C;H0;D3;+0:2](=[O;D1;H0:3])-[c:4]1:[#8;a:5]:[#7;a:6]:[c:7]:[c:8]:1 | null | [] | null | null | null | null | Ethyl [(5-{[(2S,4R)-4-[acetyl(4-chlorophenyl)amino]-2-methyl-3,4-dihydroquinolin-1(2H)-yl]carbonyl}isoxazol-3-yl)oxy]acetate was prepared following the procedure for N-(4-chlorophenyl)-N-{(2S,4R)-1-[(1-isopropyl-1H-pyrazol-4-yl)carbonyl]-2-methyl-1,2,3,4-tetrahydroquinolin-4-yl}acetamide substituting ethyl {[5-(chloroc... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Acyl halide.Carboxylic acid | Acyl halide | null | null | c1cnoc1 | HCl | ClCCl | null | null | CCOC(=O)COc1cc(C(=O)O)on1.O=C(Cl)C(=O)Cl>ClCCl>CCOC(=O)COc1cc(C(=O)Cl)on1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-20e6ab1c70c14c8a9169fd6d3e4de842 | CCOC(=O)COc1cc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccc(Cl)cc3)C[C@@H]2C)on1>>CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2cc(OCC(=O)O)no2)c2ccccc21 | C(C)(=O)N([C@@H]1C[C@@H](N(C2=CC=CC=C12)C(=O)C1=CC(=NO1)OCC(=O)OCC)C)C1=CC=C(C=C1)Cl.O.[OH-].[Li+]>>C(C)(=O)N([C@@H]1C[C@@H](N(C2=CC=CC=C12)C(=O)C1=CC(=NO1)OCC(=O)O)C)C1=CC=C(C=C1)Cl | CC[O:26][C:24]([CH2:23][O:22][c:21]1[cH:20][c:19]([C:17]([N:16]2[C@@H:14]([CH3:15])[CH2:13][C@@H:12]([N:4]([C:2]([CH3:1])=[O:3])[c:5]3[cH:6][cH:7][c:8]([Cl:9])[cH:10][cH:11]3)[c:34]3[c:29]2[cH:30][cH:31][cH:32][cH:33]3)=[O:18])[o:28][n:27]1)=[O:25]>>[CH3:1][C:2](=[O:3])[N:4]([c:5]1[cH:6][cH:7][c:8]([Cl:9])[cH:10][cH:11... | CCOC(=O)COc1cc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccc(Cl)cc3)C[C@@H]2C)on1 | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2cc(OCC(=O)O)no2)c2ccccc21 | null | null | CO | Deprotection | Ester saponification (alkyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | O=C(c1ccno1)N1CC[C@@H](Nc2ccccc2)c2ccccc21 | 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] | 60 | [{"value": 60.0, "product": "C(C)(=O)N([C@@H]1C[C@@H](N(C2=CC=CC=C12)C(=O)C1=CC(=NO1)OCC(=O)O)C)C1=CC=C(C=C1)Cl", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Ethyl [(5-{[(2S,4R)-4-[acetyl(4-chlorophenyl)amino]-2-methyl-3,4-dihydroquinolin-1(2H)-yl]carbonyl}isoxazol-3-yl)oxy]acetate was prepared following the procedure for N-(4-chlorophenyl)-N-{(2S,4R)-1-[(1-isopropyl-1H-pyrazol-4-yl)carbonyl]-2-methyl-1,2,3,4-tetrahydroquinolin-4-yl}acetamide substituting ethyl {[5-(chloroc... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1.c1cnoc1.c1ccc2c(c1)CCC[NH]2 | Other | CO | null | null | CCOC(=O)COc1cc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccc(Cl)cc3)C[C@@H]2C)on1>CO>CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2cc(OCC(=O)O)no2)c2ccccc21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a9da0719d6ca484cbe4fa7c148a5d084 | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2cnn(C(C)C)c2)c2ccccc21.CC(C)n1cc(C(=O)Cl)cn1.CCOC(=O)C(C)(C)CCBr.CN(C)C=O.O=C([O-])[O-]>>CCOC(=O)C(C)(C)CCOc1cc(C(=O)Cl)on1.CCOC(=O)C(C)(C)CCOc1cc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccc(Cl)cc3)C[C@@H]2C)on1.CCOC(=O)C(C)(C)CCOc1cc(C(=O)OC)on1 | CN(C)C=O.ClC1=CC=C(C=C1)N(C(C)=O)[C@@H]1C[C@@H](N(C2=CC=CC=C12)C(=O)C=1C=NN(C1)C(C)C)C.C(C)(C)N1N=CC(=C1)C(=O)Cl.BrCCC(C(=O)OCC)(C)C.[I-].[K+].C([O-])([O-])=O.[K+].[K+]>>C(C)(=O)N([C@@H]1C[C@@H](N(C2=CC=CC=C12)C(=O)C1=CC(=NO1)OCCC(C(=O)OCC)(C)C)C)C1=CC=C(C=C1)Cl.ClC(=O)C1=CC(=NO1)OCCC(C(=O)OCC)(C)C.C(C)OC(C(CCOC1=NOC(=... | [CH3:12][CH:21]([n:19]1[cH:32][c:33]([C:34](=[O:35])[N:36]2[c:37]3[cH:38][cH:39][cH:40][cH:41][c:42]3[C@H:43]([N:44]([C:45]([CH3:46])=[O:47])[c:48]3[cH:49][cH:50][c:51]([Cl:52])[cH:53][cH:54]3)[CH2:55][C@@H:56]2[CH3:57])[cH:71][n:79]1)[CH3:28].n1([CH:61]([CH3:60])[CH3:68])[cH:13][c:14]([C:15](=[O:16])[Cl:17])[cH:74][n:... | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2cnn(C(C)C)c2)c2ccccc21.CC(C)n1cc(C(=O)Cl)cn1.CCOC(=O)C(C)(C)CCBr.CN(C)C=O.O=C([O-])[O-] | CCOC(=O)C(C)(C)CCOc1cc(C(=O)Cl)on1.CCOC(=O)C(C)(C)CCOc1cc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccc(Cl)cc3)C[C@@H]2C)on1.CCOC(=O)C(C)(C)CCOc1cc(C(=O)OC)on1 | null | null | O | Aromatic Heterocycle Formation | OtherReaction | 3a2cd6134da7826e7429281d49e797b26a247553ce02cb083c2ac3164bccfd3b | d9387545c091c51eabac81afe0f00c5d3f07ac9c7c9540c1c44a5bab97382420 | O=C(c1ccno1)N1CC[C@@H](Nc2ccccc2)c2ccccc21.c1cnoc1.c1cnoc1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3]-[C:4](-[#8:5])=[O;D1;H0:6].[C;D1;H3:7]-[CH;D3;+0:8](-[CH3;D1;+0:9])-n1:[cH;D2;+0:10]:[c;H0;D3;+0:11](-[C:12](-[Cl;D1;H0:13])=[O;D1;H0:14]):[cH;D2;+0:15]:[n;H0;D2;+0:16]:1.[CH3;D1;+0:17]-N(-[CH3;D1;+0:18])-[CH;D2;+0:19]=[O;H0;D1;+0:20].[C:21]-[#7:22](-[C:23](=[O;D1;H0:24])-[c;H0;D3;+0:25]1:[... | null | [] | null | null | null | null | Ethyl 4-[(5-{[(2S,4R)-4-[acetyl(4-chlorophenyl)amino]-2-methyl-3,4-dihydroquinolin-1(2H)-yl]carbonyl}isoxazol-3-yl)oxy]-2,2-dimethylbutanoate was prepared following the procedure for N-(4-chlorophenyl)-N-{(2S,4R)-1-[(1-isopropyl-1H-pyrazol-4-yl)carbonyl]-2-methyl-1,2,3,4-tetrahydroquinolin-4-yl}acetamide, substituting ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Tertiary amide | Ester.Ester.Ester.Ether.Ether.Ether | c1cn[nH]c1.c1cn[nH]c1 | c1cnoc1.c1cnoc1.c1cnoc1 | c1cnoc1.c1cnoc1.c1ccccc1.c1ccc2c(c1)CCC[NH]2.c1cnoc1 | Br- | O | null | null | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2cnn(C(C)C)c2)c2ccccc21.CC(C)n1cc(C(=O)Cl)cn1.CCOC(=O)C(C)(C)CCBr.CN(C)C=O.O=C([O-])[O-]>O>CCOC(=O)C(C)(C)CCOc1cc(C(=O)Cl)on1.CCOC(=O)C(C)(C)CCOc1cc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccc(Cl)cc3)C[C@@H]2C)on1.CCOC(=O)C(C)(C)CCOc1cc(C(=O)OC)on1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-5804354907264415ad42fcd73a5917ca | COc1ccc(C(=O)N2c3ccccc3[C@H](NC(=O)OCc3ccccc3)C[C@@H]2C)cc1>>COc1ccc(C(=O)N2c3ccccc3[C@H](N)C[C@@H]2C)cc1 | C(C1=CC=CC=C1)OC(N[C@@H]1C[C@@H](N(C2=CC=CC=C12)C(C1=CC=C(C=C1)OC)=O)C)=O>>N[C@@H]1C[C@@H](N(C2=CC=CC=C12)C(=O)C1=CC=C(C=C1)OC)C | O=C(OCc1ccccc1)[NH:17][C@H:16]1[c:15]2[c:10]([cH:11][cH:12][cH:13][cH:14]2)[N:9]([C:7]([c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:22][cH:21]2)=[O:8])[C@@H:19]([CH3:20])[CH2:18]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([C:7](=[O:8])[N:9]2[c:10]3[cH:11][cH:12][cH:13][cH:14][c:15]3[C@H:16]([NH2:17])[CH2:18][C@@H:19]2[CH3:20])[... | COc1ccc(C(=O)N2c3ccccc3[C@H](NC(=O)OCc3ccccc3)C[C@@H]2C)cc1 | COc1ccc(C(=O)N2c3ccccc3[C@H](N)C[C@@H]2C)cc1 | null | [Pd] | C(C)O | Reduction | Hydrogenolysis of amides/imides/carbamates | 087b6600ba91d3df931fe6979f2445c192cbfd59e04fd2d8a10f7c7573ac669f | 4e549866ec1acadec4c84aaf8495992a28ec78d8ea5ef1b9f44dd843b0dcb7d4 | O=C(c1ccccc1)N1CCCc2ccccc21 | O=C(-O-C-c1:c:c:c:c:c:1)-[NH;D2;+0:1]-[C:2](-[C:3])-[c:4]>>[C:3]-[C:2](-[NH2;D1;+0:1])-[c:4] | null | [] | null | null | 4 | HOUR | (2S,4R)-[1-(4-methoxybenzoyl)-2-methyl-1,2,3,4-tetrahydro-quinolin-4-yl]-carbamic acid benzyl ester (1.00 equiv.) was dissolved in ethanol (30 mL). The vessel in which resided the resulting solution was evacuated and backfilled with argon. A catalytic amount of Palladium on Carbon (10%, 0.10 equiv. by wt.) was added. T... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether | Primary amine | c1ccccc1 | null | c1ccccc1.c1ccc2c(c1)CCC[NH]2 | HO- | [Pd].C(C)O | null | 4 | COc1ccc(C(=O)N2c3ccccc3[C@H](NC(=O)OCc3ccccc3)C[C@@H]2C)cc1>[Pd].C(C)O>COc1ccc(C(=O)N2c3ccccc3[C@H](N)C[C@@H]2C)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ff4d180ba80a482b9e5386c5819c5170 | COc1ccc(C(=O)N2c3ccccc3[C@H](N)C[C@@H]2C)cc1.O=[N+]([O-])c1ccc(B(O)O)cc1>>COc1ccc(C(=O)N2c3ccccc3[C@H](Nc3ccc([N+](=O)[O-])cc3)C[C@@H]2C)cc1 | C(C)(=O)OCC.N[C@@H]1C[C@@H](N(C2=CC=CC=C12)C(=O)C1=CC=C(C=C1)OC)C.[N+](=O)([O-])C1=CC=C(C=C1)B(O)O.N1=CC=CC=C1>>COC1=CC=C(C=C1)C(=O)N1[C@H](C[C@H](C2=CC=CC=C12)NC1=CC=C(C=C1)[N+](=O)[O-])C | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([C:7](=[O:8])[N:9]2[c:10]3[cH:11][cH:12][cH:13][cH:14][c:15]3[C@H:16]([NH2:17])[CH2:27][C@@H:28]2[CH3:29])[cH:30][cH:31]1.OB(O)[c:18]1[cH:19][cH:20][c:21]([N+:22](=[O:23])[O-:24])[cH:25][cH:26]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([C:7](=[O:8])[N:9]2[c:10]3[cH:11][cH:12][cH:13][cH:1... | COc1ccc(C(=O)N2c3ccccc3[C@H](N)C[C@@H]2C)cc1.O=[N+]([O-])c1ccc(B(O)O)cc1 | COc1ccc(C(=O)N2c3ccccc3[C@H](Nc3ccc([N+](=O)[O-])cc3)C[C@@H]2C)cc1 | null | C(C)(=O)[O-].[Cu+2].C(C)(=O)[O-] | CN(C)C=O | Functional Group Addition | Petasis reaction with amines and boronic acids | f3a3deec78a4c59ad4805bc1bc7e2afd5094c4db08eb97c040b7aa35f49e0111 | 9ffbcc2fa72eea0571f83107c67a8772758cc82f1a93d93731e05645a35157fb | O=C(c1ccccc1)N1CC[C@@H](Nc2ccccc2)c2ccccc21 | O-B(-O)-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[C:6]-[C:7](-[NH2;D1;+0:8])-[c:9]>>[C:6]-[C:7](-[NH;D2;+0:8]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5])-[c:9] | null | [] | 60 | CELSIUS | 1 | HOUR | To a solution of (2S,4R)-(4-amino-2-methyl-3,4-dihydro-2H-quinolin-1-yl)-(4-methoxy-phenyl)-methanone (1.00 equiv.) in DMF was added 4-nitrophenylboronic acid (2.00 equiv.), pyridine (2.50 equiv.) and copper(II)acetate (2.00 equiv.). The heterogeneous green mixture was stirred open to air for 1 h and then warmed to 60°... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Boronic acid | Secondary amine | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1.c1ccc2c(c1)CCC[NH]2 | HO-.B | C(C)(=O)[O-].[Cu+2].C(C)(=O)[O-].CN(C)C=O | 60 | 1 | COc1ccc(C(=O)N2c3ccccc3[C@H](N)C[C@@H]2C)cc1.O=[N+]([O-])c1ccc(B(O)O)cc1>C(C)(=O)[O-].[Cu+2].C(C)(=O)[O-].CN(C)C=O>COc1ccc(C(=O)N2c3ccccc3[C@H](Nc3ccc([N+](=O)[O-])cc3)C[C@@H]2C)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-4f823a42c0e84cbf9a59d53103631673 | CC(=O)Cl.COc1ccc(C(=O)N2c3ccccc3[C@H](Nc3ccc([N+](=O)[O-])cc3)C[C@@H]2C)cc1>>COc1ccc(C(=O)N2c3ccccc3C(N(C(C)=O)c3ccc([N+](=O)[O-])cc3)CC2C)cc1 | C(C)(=O)Cl.[N+](=O)([O-])C1=CC=C(C=C1)N[C@@H]1C[C@@H](N(C2=CC=CC=C12)C(=O)C1=CC=C(C=C1)OC)C.C(C)(C)N(CC)C(C)C>>[N+](=O)([O-])C1=CC=C(C=C1)N(C(C)=O)C1CC(N(C2=CC=CC=C12)C(C1=CC=C(C=C1)OC)=O)C | Cl[C:18]([CH3:19])=[O:20].[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([C:7](=[O:8])[N:9]2[c:10]3[cH:11][cH:12][cH:13][cH:14][c:15]3[C@H:16]([NH:17][c:21]3[cH:22][cH:23][c:24]([N+:25](=[O:26])[O-:27])[cH:28][cH:29]3)[CH2:30][C@@H:31]2[CH3:32])[cH:33][cH:34]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([C:7](=[O:8])[N:9]2[c:10]3[cH:11]... | CC(=O)Cl.COc1ccc(C(=O)N2c3ccccc3[C@H](Nc3ccc([N+](=O)[O-])cc3)C[C@@H]2C)cc1 | COc1ccc(C(=O)N2c3ccccc3C(N(C(C)=O)c3ccc([N+](=O)[O-])cc3)CC2C)cc1 | null | null | C(Cl)Cl | Acylation | N-alkylation of secondary amines with alkyl halides | b92e0bfd3d683c1f2a209adfe70a67ad7cb0d87749eb59e8fe0cf1689bc291e0 | 96cb0a2fed10552c5770a45a2d6523b47ac3e38928b4a9c698d8577451182dcd | O=C(c1ccccc1)N1CCC(Nc2ccccc2)c2ccccc21 | Cl-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[c:4]:[c:5]1:[c:6]-[#7:7]-[C:8]-[C:9]-[C@H;D3;+0:10]-1-[NH;D2;+0:11]-[c:12](:[c:13]):[c:14]>>[C;D1;H3:2]-[C;H0;D3;+0:1](=[O;D1;H0:3])-[N;H0;D3;+0:11](-[CH;D3;+0:10]1-[C:9]-[C:8]-[#7:7]-[c:6]:[c:5]-1:[c:4])-[c:12](:[c:13]):[c:14] | null | [] | null | null | 48 | HOUR | To a solution of (2S,4R)-[4-(4-nitro-phenylamino)-2-methyl-3,4-dihydro-2H-quinolin-1-yl]-(4-methoxy-phenyl)-methanone (1.00 equiv.) in methylene chloride was added diisopropylethylamine (1.05 equiv) followed by acetyl chloride (1.00 equiv). The mixture was stirred at rt 48 h. The mixture was concentrated under reduced ... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Secondary amine | Tertiary amide | null | null | c1ccccc1.c1ccccc1.c1ccc2c(c1)CCC[NH]2 | HCl | C(Cl)Cl | null | 48 | CC(=O)Cl.COc1ccc(C(=O)N2c3ccccc3[C@H](Nc3ccc([N+](=O)[O-])cc3)C[C@@H]2C)cc1>C(Cl)Cl>COc1ccc(C(=O)N2c3ccccc3C(N(C(C)=O)c3ccc([N+](=O)[O-])cc3)CC2C)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-488ed7ba3be84fecb01dc4ac52382e51 | COC1CCC(OC)O1.COc1ccc(C(=O)N2c3ccccc3C(N(C(C)=O)c3ccc(N)cc3)CC2C)cc1>>COc1ccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccc(-n4cccc4)cc3)C[C@@H]2C)cc1 | COC1OC(CC1)OC.NC1=CC=C(C=C1)N(C(C)=O)C1CC(N(C2=CC=CC=C12)C(C1=CC=C(C=C1)OC)=O)C.OS(=O)(=O)O.NC1=CC=CC=C1.C(=O)(O)[O-].[Na+]>>COC1=CC=C(C(=O)N2[C@H](C[C@H](C3=CC=CC=C23)N(C(C)=O)C2=CC=C(C=C2)N2C=CC=C2)C)C=C1 | CO[CH:26]1O[CH:29](OC)[CH2:28][CH2:27]1.[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([C:7](=[O:8])[N:9]2[c:10]3[cH:11][cH:12][cH:13][cH:14][c:15]3[CH:16]([N:17]([C:18]([CH3:19])=[O:20])[c:21]3[cH:22][cH:23][c:24]([NH2:25])[cH:30][cH:31]3)[CH2:32][CH:33]2[CH3:34])[cH:35][cH:36]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([C:7](=[O:8])... | COC1CCC(OC)O1.COc1ccc(C(=O)N2c3ccccc3C(N(C(C)=O)c3ccc(N)cc3)CC2C)cc1 | COc1ccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccc(-n4cccc4)cc3)C[C@@H]2C)cc1 | null | null | CO.C1CCOC1 | Aromatic Heterocycle Formation | OtherReaction | 0e9d22b0723ec2930c6f0b28cb06c2d86835df697b962917265b2a52889a76e9 | 37da407ba22aeb87f9320448e7710117027e549cd7c89e722598c54789c5481f | O=C(c1ccccc1)N1CC[C@@H](Nc2ccc(-n3cccc3)cc2)c2ccccc21 | C-O-[CH;D3;+0:1]1-O-[CH;D3;+0:2](-O-C)-[CH2;D2;+0:3]-[CH2;D2;+0:4]-1.[NH2;D1;+0:5]-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]>>[c:8]:[c:7]:[c;H0;D3;+0:6](-[n;H0;D3;+0:5]1:[cH;D2;+0:1]:[cH;D2;+0:4]:[cH;D2;+0:3]:[cH;D2;+0:2]:1):[c:9]:[c:10] | null | [] | null | null | null | null | N-(4-amino-phenyl)-N-[1-(4-methoxy-benzoyl)-2-methyl-1,2,3,4-tetrahydro-quinolin-4-yl]-acetamide (22 mg, 0.05 mmol) was dissolved in MeOH:THF (1 mL each) and cooled to 10° C. 2,5-dimethoxy-tetrahydrofuran (1.25 equiv.) was dissolved in THF and catalytic H2SO4, and added drop wise to the aniline mixture. The mixture was... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether.Ether.Primary amine | null | C1CCOC1 | c1cc[nH]c1 | c1ccccc1.c1ccccc1.c1cc[nH]c1.c1ccc2c(c1)CCC[NH]2 | HO- | CO.C1CCOC1 | null | null | COC1CCC(OC)O1.COc1ccc(C(=O)N2c3ccccc3C(N(C(C)=O)c3ccc(N)cc3)CC2C)cc1>CO.C1CCOC1>COc1ccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccc(-n4cccc4)cc3)C[C@@H]2C)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ec0d7d1729e94e1391dec2cf72e75ddf | COc1ccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccncc3)C[C@@H]2C)cc1>>COc1ccc(C(=O)N2c3ccccc3[C@H](N)C[C@@H]2C)cc1 | COC1=CC=C(C(=O)N2[C@H](C[C@H](C3=CC=CC=C23)N(C(C)=O)C2=CC=NC=C2)C)C=C1.FC1=CC=C(C(=O)Cl)C=C1>>COC1=CC=C(C(=O)N2[C@H](C[C@H](C3=CC=CC=C23)N)C)C=C1 | CC(=O)[N:17](c1ccncc1)[C@H:16]1[c:15]2[c:10]([cH:11][cH:12][cH:13][cH:14]2)[N:9]([C:7]([c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:22][cH:21]2)=[O:8])[C@@H:19]([CH3:20])[CH2:18]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([C:7](=[O:8])[N:9]2[c:10]3[cH:11][cH:12][cH:13][cH:14][c:15]3[C@H:16]([NH2:17])[CH2:18][C@@H:19]2[CH3:20])[... | COc1ccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccncc3)C[C@@H]2C)cc1 | COc1ccc(C(=O)N2c3ccccc3[C@H](N)C[C@@H]2C)cc1 | null | null | null | Reduction | OtherReaction | 76fc567d17af101afc4274920efc47186f371dc83cc33bd4c146b365ec4fe29d | b6ecdf8828e00ae514386eea0ddddd5ef4b4a45a73b1f3e69d39008dedb0e977 | O=C(c1ccccc1)N1CCCc2ccccc21 | C-C(=O)-[N;H0;D3;+0:1](-[C:2](-[C:3])-[c:4])-c1:c:c:n:c:c:1>>[C:3]-[C:2](-[NH2;D1;+0:1])-[c:4] | null | [] | null | null | null | null | N-[(2S,4R)-1-(4-methoxybenzoyl)-2-methyl-1,2,3,4-tetrahydroquinolin-4-yl]-N-pyridin-4-ylacetamide was made following general procedure G, substituting 4-methoxybenzoyl chloride for 4-fluorobenzoyl chloride. The amine-aryl coupling was performed differently to what is described in procedure G. Therefore (2S,4R)-1-(4-met... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide | Primary amine | c1ccncc1 | null | c1ccccc1.c1ccc2c(c1)CCC[NH]2 | HO- | null | null | null | COc1ccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccncc3)C[C@@H]2C)cc1>>COc1ccc(C(=O)N2c3ccccc3[C@H](N)C[C@@H]2C)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-1d093cc2a53448c3806da023214b521f | CC(=O)Cl.COc1ccc(C(=O)N2c3ccccc3[C@H](Nc3ccncc3)C[C@@H]2C)cc1>>COc1ccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccncc3)C[C@@H]2C)cc1 | C(C)(=O)Cl.COC1=CC=C(C(=O)N2[C@H](C[C@H](C3=CC=CC=C23)NC2=CC=NC=C2)C)C=C1.C(C)(C)N(CC)C(C)C>>COC1=CC=C(C(=O)N2[C@H](C[C@H](C3=CC=CC=C23)N(C(C)=O)C2=CC=NC=C2)C)C=C1 | Cl[C:18]([CH3:19])=[O:20].[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([C:7](=[O:8])[N:9]2[c:10]3[cH:11][cH:12][cH:13][cH:14][c:15]3[C@H:16]([NH:17][c:21]3[cH:22][cH:23][n:24][cH:25][cH:26]3)[CH2:27][C@@H:28]2[CH3:29])[cH:30][cH:31]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([C:7](=[O:8])[N:9]2[c:10]3[cH:11][cH:12][cH:13][cH:14][c:1... | CC(=O)Cl.COc1ccc(C(=O)N2c3ccccc3[C@H](Nc3ccncc3)C[C@@H]2C)cc1 | COc1ccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccncc3)C[C@@H]2C)cc1 | null | null | C(Cl)Cl | Acylation | N-alkylation of secondary amines with alkyl halides | b92e0bfd3d683c1f2a209adfe70a67ad7cb0d87749eb59e8fe0cf1689bc291e0 | 96cb0a2fed10552c5770a45a2d6523b47ac3e38928b4a9c698d8577451182dcd | O=C(c1ccccc1)N1CC[C@@H](Nc2ccncc2)c2ccccc21 | Cl-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[C:4]-[C:5](-[NH;D2;+0:6]-[c:7]1:[c:8]:[c:9]:[#7;a:10]:[c:11]:[c:12]:1)-[c:13]>>[C:4]-[C:5](-[N;H0;D3;+0:6](-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3])-[c:7]1:[c:8]:[c:9]:[#7;a:10]:[c:11]:[c:12]:1)-[c:13] | 61 | [{"value": 61.0, "product": "COC1=CC=C(C(=O)N2[C@H](C[C@H](C3=CC=CC=C23)N(C(C)=O)C2=CC=NC=C2)C)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 60.2, "product": "COC1=CC=C(C(=O)N2[C@H](C[C@H](C3=CC=CC=C23)N(C(C)=O)C2=CC=NC=C2)C)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | To a solution of (2S,4R)-1-(4-methoxybenzoyl)-2-methyl-N-pyridin-4-yl-1,2,3,4-tetrahydroquinolin-4-amine (90 mg, 0.24 mmol, 1 equ.) in methylene chloride (0.8 mL) was added diisopropylethylamine (84 uL, 0.48 mmol, 2 equ.) followed by acetyl chloride (340 uL, 4.80 mmol, 20 equ.). The mixture was stirred at room temperat... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Secondary amine | Tertiary amide | null | null | c1ccccc1.c1ccncc1.c1ccc2c(c1)CCC[NH]2 | HCl | C(Cl)Cl | null | 2 | CC(=O)Cl.COc1ccc(C(=O)N2c3ccccc3[C@H](Nc3ccncc3)C[C@@H]2C)cc1>C(Cl)Cl>COc1ccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccncc3)C[C@@H]2C)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-8a36c0fdeba94a5583f46b1c5c60c01f | COc1ccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccc(Cl)cc3C)C[C@@H]2C)cc1>>COc1ccc(C(=O)N2c3ccccc3[C@H](N)C[C@@H]2C)cc1 | ClC1=CC(=C(C=C1)N(C(C)=O)[C@@H]1C[C@@H](N(C2=CC=CC=C12)C(C1=CC=C(C=C1)OC)=O)C)C.FC1=CC=C(C(=O)Cl)C=C1>>COC1=CC=C(C(=O)N2[C@H](C[C@H](C3=CC=CC=C23)N)C)C=C1 | CC(=O)[N:17](c1ccc(Cl)cc1C)[C@H:16]1[c:15]2[c:10]([cH:11][cH:12][cH:13][cH:14]2)[N:9]([C:7]([c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:22][cH:21]2)=[O:8])[C@@H:19]([CH3:20])[CH2:18]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([C:7](=[O:8])[N:9]2[c:10]3[cH:11][cH:12][cH:13][cH:14][c:15]3[C@H:16]([NH2:17])[CH2:18][C@@H:19]2[CH3:... | COc1ccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccc(Cl)cc3C)C[C@@H]2C)cc1 | COc1ccc(C(=O)N2c3ccccc3[C@H](N)C[C@@H]2C)cc1 | null | null | null | Reduction | OtherReaction | 69ade7084af88ddffae90deb44c09e0c476b222fcdeb2da3e52886d1c22e74d7 | 2e45e9423fbaf161029375476baedc687fb5d07b407064b643e17c8e77249ca5 | O=C(c1ccccc1)N1CCCc2ccccc21 | C-C(=O)-[N;H0;D3;+0:1](-[C:2](-[C:3])-[c:4])-c1:c:c:c(-Cl):c:c:1-C>>[C:3]-[C:2](-[NH2;D1;+0:1])-[c:4] | null | [] | null | null | null | null | N-(4-chloro-2-methylphenyl)-N-[(2S,4R)-1-(4-methoxybenzoyl)-2-methyl-1,2,3,4-tetrahydroquinolin-4-yl]acetamide was made following general procedure G, substituting 4-methoxybenzoyl chloride for 4-fluorobenzoyl chloride. The amine-aryl coupling was performed differently to what is described in procedure G. Therefore (2S... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Tertiary amide | Primary amine | c1ccccc1 | null | c1ccccc1.c1ccc2c(c1)CCC[NH]2 | HCl | null | null | null | COc1ccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccc(Cl)cc3C)C[C@@H]2C)cc1>>COc1ccc(C(=O)N2c3ccccc3[C@H](N)C[C@@H]2C)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-03d9916989184068b80e32df42f4744c | CC(=O)Cl.COc1ccc(C(=O)N2c3ccccc3[C@H](Nc3ccc(Cl)cc3C)C[C@@H]2C)cc1>>COc1ccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccc(Cl)cc3C)C[C@@H]2C)cc1 | ClC1=CC(=C(C=C1)N[C@@H]1C[C@@H](N(C2=CC=CC=C12)C(C1=CC=C(C=C1)OC)=O)C)C.C(C)(C)N(CC)C(C)C.C(C)(=O)Cl>>ClC1=CC(=C(C=C1)N(C(C)=O)[C@@H]1C[C@@H](N(C2=CC=CC=C12)C(C1=CC=C(C=C1)OC)=O)C)C | Cl[C:18]([CH3:19])=[O:20].[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([C:7](=[O:8])[N:9]2[c:10]3[cH:11][cH:12][cH:13][cH:14][c:15]3[C@H:16]([NH:17][c:21]3[cH:22][cH:23][c:24]([Cl:25])[cH:26][c:27]3[CH3:28])[CH2:29][C@@H:30]2[CH3:31])[cH:32][cH:33]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([C:7](=[O:8])[N:9]2[c:10]3[cH:11][cH:12][c... | CC(=O)Cl.COc1ccc(C(=O)N2c3ccccc3[C@H](Nc3ccc(Cl)cc3C)C[C@@H]2C)cc1 | COc1ccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccc(Cl)cc3C)C[C@@H]2C)cc1 | null | null | null | Acylation | N-alkylation of secondary amines with alkyl halides | b92e0bfd3d683c1f2a209adfe70a67ad7cb0d87749eb59e8fe0cf1689bc291e0 | 96cb0a2fed10552c5770a45a2d6523b47ac3e38928b4a9c698d8577451182dcd | O=C(c1ccccc1)N1CC[C@@H](Nc2ccccc2)c2ccccc21 | Cl-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[C:4]-[C:5](-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9])-[c:10]>>[C:4]-[C:5](-[N;H0;D3;+0:6](-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3])-[c:7](:[c:8]):[c:9])-[c:10] | 92 | [{"value": 92.0, "product": "ClC1=CC(=C(C=C1)N(C(C)=O)[C@@H]1C[C@@H](N(C2=CC=CC=C12)C(C1=CC=C(C=C1)OC)=O)C)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 5 | HOUR | To a solution of (2S,4R)-N-(4-chloro-2-methylphenyl)-1-(4-methoxybenzoyl)-2-methyl-1,2,3,4-tetrahydroquinolin-4-amine (140 mg, 0.33 mmol, 1 equ.) in acetyl chloride (1.0 mL) was added diisopropylethylamine (58 uL, 0.33 mmol, 1 equ.). The mixture was stirred at room temperature for 5 h. The mixture was concentrated unde... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Secondary amine | Tertiary amide | null | null | c1ccccc1.c1ccccc1.c1ccc2c(c1)CCC[NH]2 | HCl | null | null | 5 | CC(=O)Cl.COc1ccc(C(=O)N2c3ccccc3[C@H](Nc3ccc(Cl)cc3C)C[C@@H]2C)cc1>>COc1ccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccc(Cl)cc3C)C[C@@H]2C)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-5398365646f94010a1d6ec6a5b5c7211 | CC(=O)Cl.C[C@H]1C[C@@H](Nc2ccc(Cl)cc2)c2ccccc2N1C(=O)c1cc(C(F)(F)F)cc(C(F)(F)F)c1>>CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2cc(C(F)(F)F)cc(C(F)(F)F)c2)c2ccccc21 | FC(C=1C=C(C=C(C1)C(F)(F)F)C(=O)N1[C@H](C[C@H](C2=CC=CC=C12)NC1=CC=C(C=C1)Cl)C)(F)F.C(C)(=O)Cl.C(C)N(CC)CC.C(Cl)Cl>>FC(C=1C=C(C(=O)N2[C@H](C[C@H](C3=CC=CC=C23)N(C(C)=O)C2=CC=C(C=C2)Cl)C)C=C(C1)C(F)(F)F)(F)F | Cl[C:2]([CH3:1])=[O:3].[NH:4]([c:5]1[cH:6][cH:7][c:8]([Cl:9])[cH:10][cH:11]1)[C@@H:12]1[CH2:13][C@H:14]([CH3:15])[N:16]([C:17](=[O:18])[c:19]2[cH:20][c:21]([C:22]([F:23])([F:24])[F:25])[cH:26][c:27]([C:28]([F:29])([F:30])[F:31])[cH:32]2)[c:33]2[cH:34][cH:35][cH:36][cH:37][c:38]21>>[CH3:1][C:2](=[O:3])[N:4]([c:5]1[cH:6]... | CC(=O)Cl.C[C@H]1C[C@@H](Nc2ccc(Cl)cc2)c2ccccc2N1C(=O)c1cc(C(F)(F)F)cc(C(F)(F)F)c1 | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2cc(C(F)(F)F)cc(C(F)(F)F)c2)c2ccccc21 | null | null | null | Acylation | N-alkylation of secondary amines with alkyl halides | b92e0bfd3d683c1f2a209adfe70a67ad7cb0d87749eb59e8fe0cf1689bc291e0 | 96cb0a2fed10552c5770a45a2d6523b47ac3e38928b4a9c698d8577451182dcd | O=C(c1ccccc1)N1CC[C@@H](Nc2ccccc2)c2ccccc21 | Cl-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[C:4]-[C:5](-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9])-[c:10]>>[C:4]-[C:5](-[N;H0;D3;+0:6](-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3])-[c:7](:[c:8]):[c:9])-[c:10] | 86 | [{"value": 86.0, "product": "FC(C=1C=C(C(=O)N2[C@H](C[C@H](C3=CC=CC=C23)N(C(C)=O)C2=CC=C(C=C2)Cl)C)C=C(C1)C(F)(F)F)(F)F", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | A solution of (3,5-bis(trifluoromethyl)phenyl)((2S,4R)-4-(4-chlorophenylamino)-2-methyl-3,4-dihydroquinolin-1(2H)-yl)methanone (19.44 g, 0.037 mol) in acetyl chloride (5 mL) was cooled to 0° C. and triethylamine (6.59 mL, 0.037 mol) was added dropwise over 30 min, a precipitate forms during this time. An additional 250... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Secondary amine | Tertiary amide | null | null | c1ccccc1.c1ccccc1.c1ccc2c(c1)CCC[NH]2 | HCl | null | null | 8 | CC(=O)Cl.C[C@H]1C[C@@H](Nc2ccc(Cl)cc2)c2ccccc2N1C(=O)c1cc(C(F)(F)F)cc(C(F)(F)F)c1>>CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2cc(C(F)(F)F)cc(C(F)(F)F)c2)c2ccccc21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-7429fc6ca7b44e1ba04bd99200e259bc | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(NCCC(=O)O)cc2)c2ccccc21.[NH4+]>>CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(NCCC(N)=O)cc2)c2ccccc21 | [Cl-].[NH4+].C=1C=CC2=C(C1)N=NN2O.CN(C)C(=[N+](C)C)ON1C2=C(C=CC=N2)N=N1.F[P-](F)(F)(F)(F)F.C(C)(C)N(CC)C(C)C.C(C)(=O)N([C@@H]1C[C@@H](N(C2=CC=CC=C12)C(=O)C1=CC=C(C=C1)NCCC(=O)O)C)C1=CC=C(C=C1)Cl>>C(C)(=O)N([C@@H]1C[C@@H](N(C2=CC=CC=C12)C(=O)C1=CC=C(C=C1)NCCC(=O)N)C)C1=CC=C(C=C1)Cl | O[C:26]([CH2:25][CH2:24][NH:23][c:22]1[cH:21][cH:20][c:19]([C:17]([N:16]2[C@@H:14]([CH3:15])[CH2:13][C@@H:12]([N:4]([C:2]([CH3:1])=[O:3])[c:5]3[cH:6][cH:7][c:8]([Cl:9])[cH:10][cH:11]3)[c:36]3[c:31]2[cH:32][cH:33][cH:34][cH:35]3)=[O:18])[cH:30][cH:29]1)=[O:28].[NH4+:27]>>[CH3:1][C:2](=[O:3])[N:4]([c:5]1[cH:6][cH:7][c:8]... | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(NCCC(=O)O)cc2)c2ccccc21.[NH4+] | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(NCCC(N)=O)cc2)c2ccccc21 | null | null | CN(C)C=O.C(C)(=O)OCC | Acylation | Carboxylic acid to amide conversion | 1283aef55d7ee699f097a8e5267689198c76ba671644401547f902657820236d | cb0a71c3fb37a76e96fbd81aae6f95a28398a03d1ad2c8e877085e735efb98f1 | O=C(c1ccccc1)N1CC[C@@H](Nc2ccccc2)c2ccccc21 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[NH4+;D0:5]>>[C:4]-[C:3]-[C;H0;D3;+0:1](-[NH2;D1;+0:5])=[O;D1;H0:2] | null | [] | null | null | 18 | HOUR | (2S,4R)-3-(4-{4-[Acetyl-(4-chloro-phenyl)-amino]-2-methyl-3,4-dihydro-2H-quinoline-1-carbonyl}-phenylamino)-propionamide was prepared from (2S,4R)-3-(4-{4-[acetyl(4-chloro-phenyl)-amino]-2-methyl-3,4-dihydro-2H-quinoline-1-carbonyl}-phenylamino)-propionic acid. The acid (0.060 g, 0.118 mmol) was dissolved in DMF (1.5 m... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Primary amide | null | null | c1ccccc1.c1ccccc1.c1ccc2c(c1)CCC[NH]2 | HO- | CN(C)C=O.C(C)(=O)OCC | null | 18 | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(NCCC(=O)O)cc2)c2ccccc21.[NH4+]>CN(C)C=O.C(C)(=O)OCC>CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(NCCC(N)=O)cc2)c2ccccc21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-cb467bc9a786406ab8d272b646b1c508 | COC(=O)C(C)(C)CCOc1ccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccc(Cl)cc3)C[C@@H]2C)cc1F>>CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(OCCC(C)(C)C(=O)O)c(F)c2)c2ccccc21 | C(C)(=O)N([C@@H]1C[C@@H](N(C2=CC=CC=C12)C(=O)C1=CC(=C(OCCC(C(=O)OC)(C)C)C=C1)F)C)C1=CC=C(C=C1)Cl.[Li+].[OH-]>>C(C)(=O)N([C@@H]1C[C@@H](N(C2=CC=CC=C12)C(=O)C1=CC(=C(OCCC(C(=O)O)(C)C)C=C1)F)C)C1=CC=C(C=C1)Cl | C[O:31][C:29]([C:26]([CH2:25][CH2:24][O:23][c:22]1[cH:21][cH:20][c:19]([C:17]([N:16]2[C@@H:14]([CH3:15])[CH2:13][C@@H:12]([N:4]([C:2]([CH3:1])=[O:3])[c:5]3[cH:6][cH:7][c:8]([Cl:9])[cH:10][cH:11]3)[c:40]3[c:35]2[cH:36][cH:37][cH:38][cH:39]3)=[O:18])[cH:34][c:32]1[F:33])([CH3:27])[CH3:28])=[O:30]>>[CH3:1][C:2](=[O:3])[N:... | COC(=O)C(C)(C)CCOc1ccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccc(Cl)cc3)C[C@@H]2C)cc1F | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(OCCC(C)(C)C(=O)O)c(F)c2)c2ccccc21 | null | null | CO.C1CCOC1 | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | O=C(c1ccccc1)N1CC[C@@H](Nc2ccccc2)c2ccccc21 | 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": 70.0, "product": "C(C)(=O)N([C@@H]1C[C@@H](N(C2=CC=CC=C12)C(=O)C1=CC(=C(OCCC(C(=O)O)(C)C)C=C1)F)C)C1=CC=C(C=C1)Cl", "details": "PERCENTYIELD", "is_desired": false}, {"value": 70.5, "product": "C(C)(=O)N([C@@H]1C[C@@H](N(C2=CC=CC=C12)C(=O)C1=CC(=C(OCCC(C(=O)O)(C)C)C=C1)F)C)C1=CC=C(C=C1)Cl", "details": "CALCUL... | null | null | 8 | HOUR | To the solution of methyl 4-(4-{[(2S,4R)-4-[acetyl(4-chlorophenyl)amino]-2-methyl-3,4-dihydroquinolin-1(2H)-yl]carbonyl}-2-fluorophenoxy)-2,2-dimethylbutanoate (176 mg, 0.30 mmol) in MeOH/THF (1 mL/1 mL) was added excessive LiOH (1N aqueous solution). The reaction mixture was stirred at r.t. overnight. The reaction was... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1.c1ccccc1.c1ccc2c(c1)CCC[NH]2 | Other | CO.C1CCOC1 | null | 8 | COC(=O)C(C)(C)CCOc1ccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccc(Cl)cc3)C[C@@H]2C)cc1F>CO.C1CCOC1>CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(OCCC(C)(C)C(=O)O)c(F)c2)c2ccccc21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-9dd67dbf49b0479e84dc553da0a6f407 | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(O)cc2)c2ccccc21.CCOC(=O)C(F)Br>>CCOC(=O)[C@H](F)Oc1ccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccc(Cl)cc3)CC2C)cc1 | ClC1=CC=C(C=C1)N(C(C)=O)[C@@H]1C[C@@H](N(C2=CC=CC=C12)C(C1=CC=C(C=C1)O)=O)C.C(=O)([O-])[O-].[Cs+].[Cs+].C(C)OC(C(F)Br)=O>>C(C)OC([C@H](F)OC1=CC=C(C=C1)C(=O)N1C(C[C@H](C2=CC=CC=C12)N(C1=CC=C(C=C1)Cl)C(C)=O)C)=O | [OH:8][c:9]1[cH:10][cH:11][c:12]([C:13](=[O:14])[N:15]2[c:16]3[cH:17][cH:18][cH:19][cH:20][c:21]3[C@H:22]([N:23]([C:24]([CH3:25])=[O:26])[c:27]3[cH:28][cH:29][c:30]([Cl:31])[cH:32][cH:33]3)[CH2:34][C@@H:35]2[CH3:36])[cH:37][cH:38]1.Br[CH:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[F:7]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[C@H:6]... | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(O)cc2)c2ccccc21.CCOC(=O)C(F)Br | CCOC(=O)[C@H](F)Oc1ccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccc(Cl)cc3)CC2C)cc1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | b4a5d39314a5c443cda9b2e0e236243ac442dfde1252cc812738ea1c57498207 | 6a03f897cefed753ca7beb47f7ee547f94bbaa026873cf266e2d9e7227c9679e | O=C(c1ccccc1)N1CC[C@@H](Nc2ccccc2)c2ccccc21 | Br-[CH;D3;+0:1](-[F;D1;H0:2])-[C:3](=[O;D1;H0:4])-[#8:5]-[C:6].[OH;D1;+0:7]-[c:8](:[c:9]):[c:10]>>[C:6]-[#8:5]-[C:3](=[O;D1;H0:4])-[C@H;D3;+0:1](-[F;D1;H0:2])-[O;H0;D2;+0:7]-[c:8](:[c:9]):[c:10] | null | [] | null | null | 8 | HOUR | (2S,4R)-N-(4-Chloro-phenyl)-N-[1-(4-hydroxy-benzoyl)-2-methyl-1,2,3,4-tetrahydro-quinolin-4-yl]-acetamide (202 mg, 0.46 mmol) was dissolved in DMF (2 mL) at room temperature. Cs2CO3 (760 mg, 2.33 mmol) was added followed by bromo-fluoro-acetic acid ethyl ester (0.070 mL, 0.583 mmol) and the reaction was allowed to stir... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Secondary halide.Ester.Aromatic alcohol | Secondary halide.Ester.Ether | null | null | c1ccccc1.c1ccccc1.c1ccc2c(c1)CCC[NH]2 | HBr | CN(C)C=O | null | 8 | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(O)cc2)c2ccccc21.CCOC(=O)C(F)Br>CN(C)C=O>CCOC(=O)[C@H](F)Oc1ccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccc(Cl)cc3)CC2C)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-7763ed6ac07849ec84896e5dafb72433 | COC(=O)C(C)(C)CCOc1ccc(C(=O)N2c3ccccc3[C@H](N(C(=O)C(C)C)c3ccc(Cl)cc3)C[C@@H]2C)cc1>>CC(C)C(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(OCCC(C)(C)C(=O)O)cc2)c2ccccc21 | ClC1=CC=C(C=C1)N([C@@H]1C[C@@H](N(C2=CC=CC=C12)C(=O)C1=CC=C(OCCC(C(=O)OC)(C)C)C=C1)C)C(C(C)C)=O.[OH-].[Na+]>>ClC1=CC=C(C=C1)N([C@@H]1C[C@@H](N(C2=CC=CC=C12)C(=O)C1=CC=C(OCCC(C(=O)O)(C)C)C=C1)C)C(C(C)C)=O | C[O:33][C:31]([C:28]([CH2:27][CH2:26][O:25][c:24]1[cH:23][cH:22][c:21]([C:19]([N:18]2[C@@H:16]([CH3:17])[CH2:15][C@@H:14]([N:6]([C:4]([CH:2]([CH3:1])[CH3:3])=[O:5])[c:7]3[cH:8][cH:9][c:10]([Cl:11])[cH:12][cH:13]3)[c:41]3[c:36]2[cH:37][cH:38][cH:39][cH:40]3)=[O:20])[cH:35][cH:34]1)([CH3:29])[CH3:30])=[O:32]>>[CH3:1][CH:... | COC(=O)C(C)(C)CCOc1ccc(C(=O)N2c3ccccc3[C@H](N(C(=O)C(C)C)c3ccc(Cl)cc3)C[C@@H]2C)cc1 | CC(C)C(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(OCCC(C)(C)C(=O)O)cc2)c2ccccc21 | null | null | CO.O1CCCC1.O | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | O=C(c1ccccc1)N1CC[C@@H](Nc2ccccc2)c2ccccc21 | 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] | null | [] | 40 | CELSIUS | 8 | HOUR | Methyl 4-(4-{[(2S,4R)-4-[(4-chlorophenyl)(isobutyryl)amino]-2-methyl-3,4-dihydroquinolin-1(2H)-yl]carbonyl}phenoxy)-2,2-dimethylbutanoate was dissolved in methanol/tetrahydrofuran/water (2/1/1) then sodium hydroxide (3 equivalents) was added and reaction mixture stirred at 40° C. overnight. The mixture was concentrated... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1.c1ccccc1.c1ccc2c(c1)CCC[NH]2 | Other | CO.O1CCCC1.O | 40 | 8 | COC(=O)C(C)(C)CCOc1ccc(C(=O)N2c3ccccc3[C@H](N(C(=O)C(C)C)c3ccc(Cl)cc3)C[C@@H]2C)cc1>CO.O1CCCC1.O>CC(C)C(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(OCCC(C)(C)C(=O)O)cc2)c2ccccc21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-114dec0569914f41baf939b57f2aa16f | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(OCCCN)cc2)c2ccccc21.CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(OCCCN)cc2)c2ccccc21.CCOC(=O)C(C)(C)Br.O=C([O-])[O-]>>CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(OCCCNCC(=O)O)cc2)c2ccccc21.CCOC(=O)CNCCCOc1ccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccc(Cl)cc3)C[C@@H]... | NCCCOC1=CC=C(C(=O)N2[C@H](C[C@H](C3=CC=CC=C23)N(C(C)=O)C2=CC=C(C=C2)Cl)C)C=C1.NCCCOC1=CC=C(C(=O)N2[C@H](C[C@H](C3=CC=CC=C23)N(C(C)=O)C2=CC=C(C=C2)Cl)C)C=C1.BrC(C(=O)OCC)(C)C.C([O-])([O-])=O.[K+].[K+]>>C(C)(=O)N([C@@H]1C[C@@H](N(C2=CC=CC=C12)C(=O)C1=CC=C(OCCCNCC(=O)O)C=C1)C)C1=CC=C(C=C1)Cl.C(C)OC(CNCCCOC1=CC=C(C=C1)C(=O... | [NH2:46][CH2:47][CH2:48][CH2:49][O:50][c:51]1[cH:52][cH:53][c:54]([C:55](=[O:56])[N:57]2[c:58]3[cH:59][cH:60][cH:61][cH:62][c:63]3[C@H:64]([N:65]([C:66]([CH3:67])=[O:68])[c:69]3[cH:70][cH:71][c:72]([Cl:73])[cH:74][cH:75]3)[CH2:76][C@@H:77]2[CH3:78])[cH:79][cH:80]1.[CH3:1][C:2](=[O:3])[N:4]([c:5]1[cH:6][cH:7][c:8]([Cl:9... | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(OCCCN)cc2)c2ccccc21.CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(OCCCN)cc2)c2ccccc21.CCOC(=O)C(C)(C)Br.O=C([O-])[O-] | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(OCCCNCC(=O)O)cc2)c2ccccc21.CCOC(=O)CNCCCOc1ccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccc(Cl)cc3)C[C@@H]2C)cc1 | null | null | CN(C=O)C | C-C Coupling | OtherReaction | 85ce140ed7df019d78749a483fc7030af41431c1c32010e1ce1fdf480af5ee36 | baad18433170eb92a62d67bae9e800b7ec6b2c9b09d470edf2e3a10a60cf5177 | O=C(c1ccccc1)N1CC[C@@H](Nc2ccccc2)c2ccccc21.O=C(c1ccccc1)N1CC[C@@H](Nc2ccccc2)c2ccccc21 | Br-[C;H0;D4;+0:1](-C)(-[CH3;D1;+0:2])-[C:3](=[O;D1;H0:4])-[#8:5]-[C:6].[C:7]-[C:8]-[NH2;D1;+0:9].[C:10]-[C:11]-[NH2;D1;+0:12].[O-;H0;D1:13]-[C;H0;D3;+0:14](-[O-])=[O;D1;H0:15]>>[C:6]-[#8:5]-[C:3](=[O;D1;H0:4])-[CH2;D2;+0:1]-[NH;D2;+0:9]-[C:8]-[C:7].[C:10]-[C:11]-[NH;D2;+0:12]-[CH2;D2;+0:2]-[C;H0;D3;+0:14](=[O;D1;H0:15]... | 12 | [{"value": 12.0, "product": "C(C)OC(CNCCCOC1=CC=C(C=C1)C(=O)N1[C@H](C[C@H](C2=CC=CC=C12)N(C1=CC=C(C=C1)Cl)C(C)=O)C)=O", "details": "PERCENTYIELD", "is_desired": false}] | 50 | CELSIUS | null | null | {[3-(4-{[(2S,4R)-4-[acetyl(4-chlorophenyl)amino]-2-methyl-3,4-dihydroquinolin-1(2H)-yl]carbonyl}phenoxy)propyl]amino}acetic acid was prepared from (2S,4R)-N-{1-[4-(3-amino-propoxy)-benzoyl]-2-methyl-1,2,3,4-tetrahydro-quinolin-4-yl}-N-(4-chloro-phenyl)-acetamide. (2S,4R)-N-{1-[4-(3-amino-propoxy)-benzoyl]-2-methyl-1,2,... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary halide.Ester.Primary amine.Primary amine | Carboxylic acid.Ester.Secondary amine.Secondary amine | null | null | c1ccccc1.c1ccccc1.c1ccc2c(c1)CCC[NH]2.c1ccccc1.c1ccccc1.c1ccc2c(c1)CCC[NH]2 | HBr | CN(C=O)C | 50 | null | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(OCCCN)cc2)c2ccccc21.CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(OCCCN)cc2)c2ccccc21.CCOC(=O)C(C)(C)Br.O=C([O-])[O-]>CN(C=O)C>CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(OCCCNCC(=O)O)cc2)c2ccccc21.CCOC(=O)CNCCCOc1ccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccc(Cl)cc3... |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-0862fb5a6db144608d6618f49de238b1 | CCOC(=O)CNCCCOc1ccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccc(Cl)cc3)C[C@@H]2C)cc1>>CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(OCCCNCC(=O)O)cc2)c2ccccc21 | C(C)OC(CNCCCOC1=CC=C(C=C1)C(=O)N1[C@H](C[C@H](C2=CC=CC=C12)N(C1=CC=C(C=C1)Cl)C(C)=O)C)=O.C(C)O.[OH-].[Na+]>>C(C)(=O)N([C@@H]1C[C@@H](N(C2=CC=CC=C12)C(=O)C1=CC=C(OCCCNCC(=O)O)C=C1)C)C1=CC=C(C=C1)Cl | CC[O:31][C:29]([CH2:28][NH:27][CH2:26][CH2:25][CH2:24][O:23][c:22]1[cH:21][cH:20][c:19]([C:17]([N:16]2[C@@H:14]([CH3:15])[CH2:13][C@@H:12]([N:4]([C:2]([CH3:1])=[O:3])[c:5]3[cH:6][cH:7][c:8]([Cl:9])[cH:10][cH:11]3)[c:39]3[c:34]2[cH:35][cH:36][cH:37][cH:38]3)=[O:18])[cH:33][cH:32]1)=[O:30]>>[CH3:1][C:2](=[O:3])[N:4]([c:5... | CCOC(=O)CNCCCOc1ccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccc(Cl)cc3)C[C@@H]2C)cc1 | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(OCCCNCC(=O)O)cc2)c2ccccc21 | null | null | O1CCCC1 | Deprotection | Ester saponification (alkyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | O=C(c1ccccc1)N1CC[C@@H](Nc2ccccc2)c2ccccc21 | 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] | 75 | [{"value": 75.0, "product": "C(C)(=O)N([C@@H]1C[C@@H](N(C2=CC=CC=C12)C(=O)C1=CC=C(OCCCNCC(=O)O)C=C1)C)C1=CC=C(C=C1)Cl", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | {[3-(4-{[(2S,4R)-4-[acetyl(4-chlorophenyl)amino]-2-methyl-3,4-dihydroquinolin-1(2H)-yl]carbonyl}phenoxy)propyl]amino}acetic ethyl ester was hydrolyzed to the acid by dissolving in tetrahydrofuran and ethanol and sodium hydroxide (1N) was added. The mixture was stirred at room temperature overnight. The mixture was cool... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1.c1ccccc1.c1ccc2c(c1)CCC[NH]2 | Other | O1CCCC1 | null | 8 | CCOC(=O)CNCCCOc1ccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccc(Cl)cc3)C[C@@H]2C)cc1>O1CCCC1>CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(OCCCNCC(=O)O)cc2)c2ccccc21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-3573696cebef47f8b539e4cb7f4aa5bc | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(OC3CCC(C(=O)O)CC3)cc2)c2ccccc21.[NH4+]>>CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(OC3CCC(C(N)=O)CC3)cc2)c2ccccc21 | C1CCOC1.C(C)(=O)N([C@@H]1C[C@@H](N(C2=CC=CC=C12)C(=O)C1=CC=C(OC2CCC(CC2)C(=O)O)C=C1)C)C1=CC=C(C=C1)Cl.C=1C=CC2=C(C1)N=NN2O.CCN=C=NCCCN(C)C.[Cl-].[NH4+]>>C(C)(=O)N([C@@H]1C[C@@H](N(C2=CC=CC=C12)C(=O)C1=CC=C(OC2CCC(CC2)C(=O)N)C=C1)C)C1=CC=C(C=C1)Cl | O[C:28]([CH:27]1[CH2:26][CH2:25][CH:24]([O:23][c:22]2[cH:21][cH:20][c:19]([C:17]([N:16]3[C@@H:14]([CH3:15])[CH2:13][C@@H:12]([N:4]([C:2]([CH3:1])=[O:3])[c:5]4[cH:6][cH:7][c:8]([Cl:9])[cH:10][cH:11]4)[c:40]4[c:35]3[cH:36][cH:37][cH:38][cH:39]4)=[O:18])[cH:34][cH:33]2)[CH2:32][CH2:31]1)=[O:30].[NH4+:29]>>[CH3:1][C:2](=[O... | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(OC3CCC(C(=O)O)CC3)cc2)c2ccccc21.[NH4+] | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(OC3CCC(C(N)=O)CC3)cc2)c2ccccc21 | null | CN(C)C=O | C(C)(=O)OCC | Acylation | Carboxylic acid to amide conversion | 1283aef55d7ee699f097a8e5267689198c76ba671644401547f902657820236d | cb0a71c3fb37a76e96fbd81aae6f95a28398a03d1ad2c8e877085e735efb98f1 | O=C(c1ccc(OC2CCCCC2)cc1)N1CC[C@@H](Nc2ccccc2)c2ccccc21 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[C:5].[NH4+;D0:6]>>[C:4]-[C:3](-[C;H0;D3;+0:1](-[NH2;D1;+0:6])=[O;D1;H0:2])-[C:5] | 71 | [{"value": 71.0, "product": "C(C)(=O)N([C@@H]1C[C@@H](N(C2=CC=CC=C12)C(=O)C1=CC=C(OC2CCC(CC2)C(=O)N)C=C1)C)C1=CC=C(C=C1)Cl", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 11 | HOUR | (2S,4R)-4-(4-{4-[Acetyl-(4-chloro-phenyl)-amino]-2-methyl-3,4-dihydro-2H-quinoline-1-carbonyl}-phenoxy)-cyclohexanecarboxylic acid (0.070 g, 0.125 mmol) was converted to the amide by dissolving in THF (1 mL) at room temperature. HOBt (0.025 g), EDCI (0.035 g), and ammonium chloride (0.014 g, 0.25 mmol) was added along ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Primary amide | null | null | c1ccccc1.c1ccccc1.C1CCCCC1.c1ccc2c(c1)CCC[NH]2 | HO- | CN(C)C=O.C(C)(=O)OCC | null | 11 | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(OC3CCC(C(=O)O)CC3)cc2)c2ccccc21.[NH4+]>CN(C)C=O.C(C)(=O)OCC>CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(OC3CCC(C(N)=O)CC3)cc2)c2ccccc21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a3e433dfc78b40fab5037762e0988ff9 | COc1ccc(C(=O)N2c3ccccc3[C@H](N(C(=O)C3CC3)c3ccc(Cl)cc3)C[C@@H]2C)cc1>>C[C@H]1C[C@@H](N(C(=O)C2CC2)c2ccc(Cl)cc2)c2ccccc2N1C(=O)c1ccc(O)cc1 | ClC1=CC=C(C=C1)N(C(=O)C1CC1)[C@@H]1C[C@@H](N(C2=CC=CC=C12)C(C1=CC=C(C=C1)OC)=O)C.B(Br)(Br)Br>>ClC1=CC=C(C=C1)N(C(=O)C1CC1)[C@@H]1C[C@@H](N(C2=CC=CC=C12)C(C1=CC=C(C=C1)O)=O)C | C[O:31][c:30]1[cH:29][cH:28][c:27]([C:25]([N:24]2[C@@H:2]([CH3:1])[CH2:3][C@@H:4]([N:5]([C:6](=[O:7])[CH:8]3[CH2:9][CH2:10]3)[c:11]3[cH:12][cH:13][c:14]([Cl:15])[cH:16][cH:17]3)[c:18]3[cH:19][cH:20][cH:21][cH:22][c:23]32)=[O:26])[cH:33][cH:32]1>>[CH3:1][C@H:2]1[CH2:3][C@@H:4]([N:5]([C:6](=[O:7])[CH:8]2[CH2:9][CH2:10]2)... | COc1ccc(C(=O)N2c3ccccc3[C@H](N(C(=O)C3CC3)c3ccc(Cl)cc3)C[C@@H]2C)cc1 | C[C@H]1C[C@@H](N(C(=O)C2CC2)c2ccc(Cl)cc2)c2ccccc2N1C(=O)c1ccc(O)cc1 | null | null | C(Cl)Cl | Deprotection | Cleavage of methoxy ethers to alcohols | c5320c7dfa4f544d4900efcae9b3262bf0d5286bcf39c86109232351f35b23d5 | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | O=C(c1ccccc1)N1CC[C@@H](N(C(=O)C2CC2)c2ccccc2)c2ccccc21 | C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[OH;D1;+0:1]-[c:2](:[c:3]):[c:4] | 98.1 | [{"value": 98.0, "product": "ClC1=CC=C(C=C1)N(C(=O)C1CC1)[C@@H]1C[C@@H](N(C2=CC=CC=C12)C(C1=CC=C(C=C1)O)=O)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 98.1, "product": "ClC1=CC=C(C=C1)N(C(=O)C1CC1)[C@@H]1C[C@@H](N(C2=CC=CC=C12)C(C1=CC=C(C=C1)O)=O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired":... | null | null | 4 | HOUR | To a solution of N-(4-chlorophenyl)-N-[(2S,4R)-1-(4-methoxybenzoyl)-2-methyl-1,2,3,4-tetrahydroquinolin-4-yl]cyclopropanecarboxamide (200 mg, 0.42 mmol, 1 equ.) in methylene chloride (0.3 mL) was added a 1 M solution of boron tribromide in methylene chloride (1.2 mL, 1.26 mmol, 3 equ.). The reaction mixture was stirred... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | null | null | C1CC1.c1ccccc1.c1ccc2c(c1)CCC[NH]2.c1ccccc1 | Other | C(Cl)Cl | null | 4 | COc1ccc(C(=O)N2c3ccccc3[C@H](N(C(=O)C3CC3)c3ccc(Cl)cc3)C[C@@H]2C)cc1>C(Cl)Cl>C[C@H]1C[C@@H](N(C(=O)C2CC2)c2ccc(Cl)cc2)c2ccccc2N1C(=O)c1ccc(O)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-3ec990318aa842b0a8aa7d128b64c51a | C=CCC(C)(C)C(=O)OC.COC(=O)C1=CC=CC(F)(Br)C1>>COC(=O)c1ccc(/C=C/CC(C)(C)C(=O)OC)c(F)c1 | COC(C=1CC(C=CC1)(F)Br)=O.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C(C)(=O)[O-].[K+].CC(C(=O)OC)(CC=C)C>>FC=1C=C(C(=O)OC)C=CC1\C=C\CC(C(=O)OC)(C)C | [CH2:9]=[CH:10][CH2:11][C:12]([CH3:13])([CH3:14])[C:15](=[O:16])[O:17][CH3:18].Br[C:19]1([F:20])[CH:8]=[CH:7][CH:6]=[C:5]([C:3]([O:2][CH3:1])=[O:4])[CH2:21]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8](/[CH:9]=[CH:10]/[CH2:11][C:12]([CH3:13])([CH3:14])[C:15](=[O:16])[O:17][CH3:18])[c:19]([F:20])[cH:21]1 | C=CCC(C)(C)C(=O)OC.COC(=O)C1=CC=CC(F)(Br)C1 | COC(=O)c1ccc(/C=C/CC(C)(C)C(=O)OC)c(F)c1 | null | [Cl-].C(CCC)[N+](CCCC)(CCCC)CCCC.C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-] | CN(C=O)C | C-C Coupling | OtherReaction | cec44053563f2a43dba0cc3feeb46f2573d35c2009d333d4b42036f44d99070a | 590a858358bdd7960af36d29559dbd36f713a74d9933580f6c1a28b7888836e0 | c1ccccc1 | Br-[C;H0;D4;+0:1]1(-[F;D1;H0:2])-[CH2;D2;+0:3]-[C;H0;D3;+0:4](-[C:5](=[O;D1;H0:6])-[#8:7]-[C;D1;H3:8])=[CH;D2;+0:9]-[CH;D2;+0:10]=[CH;D2;+0:11]-1.[C:12]-[C:13]=[CH2;D1;+0:14]>>[C:12]/[C:13]=[CH;D2;+0:14]/[c;H0;D3;+0:11]1:[cH;D2;+0:10]:[cH;D2;+0:9]:[c;H0;D3;+0:4](-[C:5](=[O;D1;H0:6])-[#8:7]-[C;D1;H3:8]):[cH;D2;+0:3]:[c;... | null | [] | 130 | CELSIUS | null | null | Methyl 5-(4-{[(2S,4R)-4-[acetyl(4-chlorophenyl)amino]-2-methyl-3,4-dihydro1quinolin-1(2H)-yl]carbonyl}-2-fluorophenyl)-2,2-dimethylpentanoate was prepared following general procedure B, substituting methyl 5-[4-(chlorocarbonyl)-2-fluorophenyl]-2,2-dimethylpentanoate for 6-trifluoromethyl nicotinyl chloride. (Methyl 5-[... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary halide.Tertiary halide.Ester.Allyl.Conjugated diene | Aromatic halide.Ester | C1=CCCC=C1 | c1ccccc1 | c1ccccc1 | HBr | [Cl-].C(CCC)[N+](CCCC)(CCCC)CCCC.C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-].CN(C=O)C | 130 | null | C=CCC(C)(C)C(=O)OC.COC(=O)C1=CC=CC(F)(Br)C1>[Cl-].C(CCC)[N+](CCCC)(CCCC)CCCC.C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-].CN(C=O)C>COC(=O)c1ccc(/C=C/CC(C)(C)C(=O)OC)c(F)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d0f906a6f13d4c0ea7a866b804f4667e | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(O)cc2)c2ccccc21.CCOC(=O)C(C)(C)CCl>>CCOC(=O)C(C)(C)COc1ccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccc(Cl)cc3)C[C@@H]2C)cc1 | ClC1=CC=C(C=C1)N(C(C)=O)[C@@H]1C[C@@H](N(C2=CC=CC=C12)C(C1=CC=C(C=C1)O)=O)C.C(=O)([O-])[O-].[K+].[K+].C(C)OC(C(CCl)(C)C)=O>>C(C)OC(C(COC1=CC=C(C=C1)C(=O)N1[C@H](C[C@H](C2=CC=CC=C12)N(C1=CC=C(C=C1)Cl)C(C)=O)C)(C)C)=O | [OH:10][c:11]1[cH:12][cH:13][c:14]([C:15](=[O:16])[N:17]2[c:18]3[cH:19][cH:20][cH:21][cH:22][c:23]3[C@H:24]([N:25]([C:26]([CH3:27])=[O:28])[c:29]3[cH:30][cH:31][c:32]([Cl:33])[cH:34][cH:35]3)[CH2:36][C@@H:37]2[CH3:38])[cH:39][cH:40]1.Cl[CH2:9][C:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])([CH3:7])[CH3:8]>>[CH3:1][CH2:2][O:3][... | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(O)cc2)c2ccccc21.CCOC(=O)C(C)(C)CCl | CCOC(=O)C(C)(C)COc1ccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccc(Cl)cc3)C[C@@H]2C)cc1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | O=C(c1ccccc1)N1CC[C@@H](Nc2ccccc2)c2ccccc21 | Cl-[CH2;D2;+0:1]-[C:2](-[C;D1;H3:3])(-[C;D1;H3:4])-[C:5](=[O;D1;H0:6])-[#8:7]-[C:8].[OH;D1;+0:9]-[c:10](:[c:11]):[c:12]>>[C:8]-[#8:7]-[C:5](=[O;D1;H0:6])-[C:2](-[C;D1;H3:3])(-[C;D1;H3:4])-[CH2;D2;+0:1]-[O;H0;D2;+0:9]-[c:10](:[c:11]):[c:12] | 32 | [{"value": 32.0, "product": "C(C)OC(C(COC1=CC=C(C=C1)C(=O)N1[C@H](C[C@H](C2=CC=CC=C12)N(C1=CC=C(C=C1)Cl)C(C)=O)C)(C)C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 31.2, "product": "C(C)OC(C(COC1=CC=C(C=C1)C(=O)N1[C@H](C[C@H](C2=CC=CC=C12)N(C1=CC=C(C=C1)Cl)C(C)=O)C)(C)C)=O", "details": "CALCULATEDPERC... | 90 | CELSIUS | null | null | (2S,4R)-N-(4-Chloro-phenyl)-N-[1-(4-hydroxy-benzoyl)-2-methyl-1,2,3,4-tetrahydro-quinolin-4-yl]-acetamide (0.32 g, 0.74 mmol) was dissolved in 10 ml DMF at room temperature and K2CO3 (0.51 g, 3.7 mmol) was added. 3-Chloro-2,2-dimethyl-propionic acid ethyl ester (0.25 g, 1.52 mmol) was added and the reaction was allowed... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccccc1.c1ccccc1.c1ccc2c(c1)CCC[NH]2 | HCl | CN(C)C=O | 90 | null | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(O)cc2)c2ccccc21.CCOC(=O)C(C)(C)CCl>CN(C)C=O>CCOC(=O)C(C)(C)COc1ccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccc(Cl)cc3)C[C@@H]2C)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-3f3cbef47fbf4db59ebe0ebb6442b3ed | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(O)cc2)c2ccccc21.O=S(=O)(O)CCCCl>>CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(OCCCS(=O)(=O)O)cc2)c2ccccc21 | ClC1=CC=C(C=C1)N(C(C)=O)[C@@H]1C[C@@H](N(C2=CC=CC=C12)C(C1=CC=C(C=C1)O)=O)C.[H-].[Na+].ClCCCS(=O)(=O)O>>C(C)(=O)N([C@@H]1C[C@@H](N(C2=CC=CC=C12)C(=O)C1=CC=C(OCCCS(=O)(=O)O)C=C1)C)C1=CC=C(C=C1)Cl | [CH3:1][C:2](=[O:3])[N:4]([c:5]1[cH:6][cH:7][c:8]([Cl:9])[cH:10][cH:11]1)[C@@H:12]1[CH2:13][C@H:14]([CH3:15])[N:16]([C:17](=[O:18])[c:19]2[cH:20][cH:21][c:22]([OH:23])[cH:31][cH:32]2)[c:33]2[cH:34][cH:35][cH:36][cH:37][c:38]21.Cl[CH2:24][CH2:25][CH2:26][S:27](=[O:28])(=[O:29])[OH:30]>>[CH3:1][C:2](=[O:3])[N:4]([c:5]1[c... | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(O)cc2)c2ccccc21.O=S(=O)(O)CCCCl | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(OCCCS(=O)(=O)O)cc2)c2ccccc21 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | O=C(c1ccccc1)N1CC[C@@H](Nc2ccccc2)c2ccccc21 | Cl-[CH2;D2;+0:1]-[C:2]-[C:3].[OH;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:4]-[c:5](:[c:6]):[c:7] | null | [] | null | null | null | null | (2S,4R)-N-(4-Chloro-phenyl)-N-[1-(4-hydroxy-benzoyl)-2-methyl-1,2,3,4-tetrahydro-quinolin-4-yl]-acetamide (207 mg, 0.481 mmol) was dissolved in DMF (5 mL) at room temperature. NaH (58 mg, 2.40 mmol) was added followed by 3-chloro-propane-1-sulfonic acid (sodium salt, 135 mg, 0.60 mmol) and the reaction was allowed to s... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccccc1.c1ccccc1.c1ccc2c(c1)CCC[NH]2 | HCl | CN(C)C=O | null | null | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(O)cc2)c2ccccc21.O=S(=O)(O)CCCCl>CN(C)C=O>CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(OCCCS(=O)(=O)O)cc2)c2ccccc21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-fc90f4123de642d0ab9537c5d7803333 | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(F)c(O)c2)c2ccccc21.COC(=O)C(C)(C)CCBr>>COC(=O)C(C)(C)CCOc1cc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccc(Cl)cc3)C[C@@H]2C)ccc1F | ClC1=CC=C(C=C1)N(C(C)=O)[C@@H]1C[C@@H](N(C2=CC=CC=C12)C(C1=CC(=C(C=C1)F)O)=O)C.C(=O)([O-])[O-].[Cs+].[Cs+].BrCCC(C(=O)OC)(C)C>>C(C)(=O)N([C@@H]1C[C@@H](N(C2=CC=CC=C12)C(=O)C=1C=CC(=C(OCCC(C(=O)OC)(C)C)C1)F)C)C1=CC=C(C=C1)Cl | [OH:10][c:11]1[cH:12][c:13]([C:14](=[O:15])[N:16]2[c:17]3[cH:18][cH:19][cH:20][cH:21][c:22]3[C@H:23]([N:24]([C:25]([CH3:26])=[O:27])[c:28]3[cH:29][cH:30][c:31]([Cl:32])[cH:33][cH:34]3)[CH2:35][C@@H:36]2[CH3:37])[cH:38][cH:39][c:40]1[F:41].Br[CH2:9][CH2:8][C:5]([C:3]([O:2][CH3:1])=[O:4])([CH3:6])[CH3:7]>>[CH3:1][O:2][C:... | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(F)c(O)c2)c2ccccc21.COC(=O)C(C)(C)CCBr | COC(=O)C(C)(C)CCOc1cc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccc(Cl)cc3)C[C@@H]2C)ccc1F | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | O=C(c1ccccc1)N1CC[C@@H](Nc2ccccc2)c2ccccc21 | Br-[CH2;D2;+0:1]-[C:2]-[C:3]-[C:4](-[#8:5])=[O;D1;H0:6].[OH;D1;+0:7]-[c:8](:[c:9]):[c:10]>>[#8:5]-[C:4](=[O;D1;H0:6])-[C:3]-[C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:7]-[c:8](:[c:9]):[c:10] | 52 | [{"value": 52.0, "product": "C(C)(=O)N([C@@H]1C[C@@H](N(C2=CC=CC=C12)C(=O)C=1C=CC(=C(OCCC(C(=O)OC)(C)C)C1)F)C)C1=CC=C(C=C1)Cl", "details": "PERCENTYIELD", "is_desired": false}, {"value": 46.9, "product": "C(C)(=O)N([C@@H]1C[C@@H](N(C2=CC=CC=C12)C(=O)C=1C=CC(=C(OCCC(C(=O)OC)(C)C)C1)F)C)C1=CC=C(C=C1)Cl", "details": "CALC... | null | null | 8 | HOUR | N-(4-chlorophenyl)-N-[(2S,4R)-1-(4-fluoro-3-hydroxybenzoyl)-2-methyl-1,2,3,4-tetrahydroquinolin-4-yl]acetamide (476 mg, 1.05 mmol) was dissolved in DMF at room temperature and Cs2CO3 (854 mg, 2.63 mmol) was added. Methyl 4-bromo-2,2-dimethylbutanoate (702 mg, 1.58 mmol) was added and the reaction was stirred at r.t. ov... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccccc1.c1ccccc1.c1ccc2c(c1)CCC[NH]2 | HBr | CN(C)C=O | null | 8 | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(F)c(O)c2)c2ccccc21.COC(=O)C(C)(C)CCBr>CN(C)C=O>COC(=O)C(C)(C)CCOc1cc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccc(Cl)cc3)C[C@@H]2C)ccc1F |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-5c62ccf86eb749f88ae578bd3cd8560d | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(F)c(O[Si](C)(C)C(C)(C)C)c2)c2ccccc21>>CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(F)c(O)c2)c2ccccc21 | C(C)(C)(C)[Si](OC=1C=C(C(=O)N2[C@H](C[C@H](C3=CC=CC=C23)N(C(C)=O)C2=CC=C(C=C2)Cl)C)C=CC1F)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>>ClC1=CC=C(C=C1)N(C(C)=O)[C@@H]1C[C@@H](N(C2=CC=CC=C12)C(C1=CC(=C(C=C1)F)O)=O)C | CC(C)(C)[Si](C)(C)[O:25][c:24]1[c:22]([F:23])[cH:21][cH:20][c:19]([C:17]([N:16]2[C@@H:14]([CH3:15])[CH2:13][C@@H:12]([N:4]([C:2]([CH3:1])=[O:3])[c:5]3[cH:6][cH:7][c:8]([Cl:9])[cH:10][cH:11]3)[c:32]3[c:27]2[cH:28][cH:29][cH:30][cH:31]3)=[O:18])[cH:26]1>>[CH3:1][C:2](=[O:3])[N:4]([c:5]1[cH:6][cH:7][c:8]([Cl:9])[cH:10][cH... | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(F)c(O[Si](C)(C)C(C)(C)C)c2)c2ccccc21 | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(F)c(O)c2)c2ccccc21 | null | null | ClCCl | Deprotection | Alcohol deprotection from silyl ethers | e70131badc7d7d580ed75b2dfb3ce6df2a5f496b2119611cf5354e1267babe73 | b09ece7bccc3ff762f4ff5407ad846fffba6d6a63735853c86a86d29904f54ed | O=C(c1ccccc1)N1CC[C@@H](Nc2ccccc2)c2ccccc21 | C-C(-C)(-C)-[Si](-C)(-C)-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[OH;D1;+0:1]-[c:2](:[c:3]):[c:4] | 110.9 | [{"value": 100.0, "product": "ClC1=CC=C(C=C1)N(C(C)=O)[C@@H]1C[C@@H](N(C2=CC=CC=C12)C(C1=CC(=C(C=C1)F)O)=O)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 110.9, "product": "ClC1=CC=C(C=C1)N(C(C)=O)[C@@H]1C[C@@H](N(C2=CC=CC=C12)C(C1=CC(=C(C=C1)F)O)=O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired":... | null | null | null | null | N-[(2S,4R)-1-(3-{[tert-butyl-(dimethyl)silyl]oxy}-4-fluorobenzoyl)-2-methyl-1,2,3,4-tetrahydroquinolin-4-yl]-N-(4-chlorophenyl)acetamide (543 mg, 0.95 mmol) was dissolved in dichloromethane and a solution of TBAF (1.0 M in THF, 5.0 mL) was added; the reaction mixture was stirred at room temperature for until no startin... | 10.6084/m9.figshare.5104873.v1 | null | TMS ether protective group | Aromatic alcohol | null | null | c1ccccc1.c1ccccc1.c1ccc2c(c1)CCC[NH]2 | Other | ClCCl | null | null | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(F)c(O[Si](C)(C)C(C)(C)C)c2)c2ccccc21>ClCCl>CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(F)c(O)c2)c2ccccc21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-4a9379993f7c4b638179dca48983574c | CCOC(=O)C1CCC(Oc2ccc(C(=O)N3c4ccccc4[C@H](N(C(C)=O)c4ccc(Cl)cc4)C[C@@H]3C)cc2)CC1>>CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(OC3CCC(C(=O)O)CC3)cc2)c2ccccc21 | C(C)OC(=O)C1CCC(CC1)OC1=CC=C(C=C1)C(=O)N1[C@H](C[C@H](C2=CC=CC=C12)N(C1=CC=C(C=C1)Cl)C(C)=O)C.C(C)O.[OH-].[Na+]>>C(C)(=O)N([C@@H]1C[C@@H](N(C2=CC=CC=C12)C(=O)C1=CC=C(OC2CCC(CC2)C(=O)O)C=C1)C)C1=CC=C(C=C1)Cl | CC[O:30][C:28]([CH:27]1[CH2:26][CH2:25][CH:24]([O:23][c:22]2[cH:21][cH:20][c:19]([C:17]([N:16]3[C@@H:14]([CH3:15])[CH2:13][C@@H:12]([N:4]([C:2]([CH3:1])=[O:3])[c:5]4[cH:6][cH:7][c:8]([Cl:9])[cH:10][cH:11]4)[c:40]4[c:35]3[cH:36][cH:37][cH:38][cH:39]4)=[O:18])[cH:34][cH:33]2)[CH2:32][CH2:31]1)=[O:29]>>[CH3:1][C:2](=[O:3]... | CCOC(=O)C1CCC(Oc2ccc(C(=O)N3c4ccccc4[C@H](N(C(C)=O)c4ccc(Cl)cc4)C[C@@H]3C)cc2)CC1 | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(OC3CCC(C(=O)O)CC3)cc2)c2ccccc21 | null | null | O1CCCC1 | Deprotection | Ester saponification (alkyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | O=C(c1ccc(OC2CCCCC2)cc1)N1CC[C@@H](Nc2ccccc2)c2ccccc21 | 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] | 62 | [{"value": 62.0, "product": "C(C)(=O)N([C@@H]1C[C@@H](N(C2=CC=CC=C12)C(=O)C1=CC=C(OC2CCC(CC2)C(=O)O)C=C1)C)C1=CC=C(C=C1)Cl", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 10 | HOUR | (2S,4R)-4-(4-{4-[Acetyl-(4-chloro-phenyl)-amino]-2-methyl-3,4-dihydro-2H-quinoline-1-carbonyl}-phenoxy)-cyclohexanecarboxylic acid ethyl ester (0.060, 0.10 mmol) was hydrolyzed to the acid by dissolving in tetrahydrofuran and ethanol and sodium hydroxide (1N) was added. The mixture was stirred at room temperature 10 ho... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1.c1ccccc1.C1CCCCC1.c1ccc2c(c1)CCC[NH]2 | Other | O1CCCC1 | null | 10 | CCOC(=O)C1CCC(Oc2ccc(C(=O)N3c4ccccc4[C@H](N(C(C)=O)c4ccc(Cl)cc4)C[C@@H]3C)cc2)CC1>O1CCCC1>CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(OC3CCC(C(=O)O)CC3)cc2)c2ccccc21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-bb6a2808ad384237b06f54398dc5aa61 | CC(=O)OCC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2cc(C(F)(F)F)cc(C(F)(F)F)c2)c2ccccc21>>C[C@H]1C[C@@H](N(C(=O)CO)c2ccc(Cl)cc2)c2ccccc2N1 | C(C)(=O)OCC(=O)N(C1=CC=C(C=C1)Cl)[C@@H]1C[C@@H](N(C2=CC=CC=C12)C(C1=CC(=CC(=C1)C(F)(F)F)C(F)(F)F)=O)C.[OH-].[K+].Cl>>ClC1=CC=C(C=C1)N(C(CO)=O)[C@@H]1C[C@@H](NC2=CC=CC=C12)C | CC(=O)[O:9][CH2:8][C:6]([N:5]([C@@H:4]1[CH2:3][C@H:2]([CH3:1])[N:23](C(=O)c2cc(C(F)(F)F)cc(C(F)(F)F)c2)[c:22]2[c:17]1[cH:18][cH:19][cH:20][cH:21]2)[c:10]1[cH:11][cH:12][c:13]([Cl:14])[cH:15][cH:16]1)=[O:7]>>[CH3:1][C@H:2]1[CH2:3][C@@H:4]([N:5]([C:6](=[O:7])[CH2:8][OH:9])[c:10]2[cH:11][cH:12][c:13]([Cl:14])[cH:15][cH:16... | CC(=O)OCC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2cc(C(F)(F)F)cc(C(F)(F)F)c2)c2ccccc21 | C[C@H]1C[C@@H](N(C(=O)CO)c2ccc(Cl)cc2)c2ccccc2N1 | null | null | O.C(C)O | Reduction | OtherReaction | cc3c05781d5bf0cc8d4d3d203997ba1665241eb99d100470add2c87f4a66cc78 | 83355dffd4f3f1a79824143fd500545d59e799dd65acc9de934ece20d30d5e94 | c1ccc(N[C@@H]2CCNc3ccccc32)cc1 | C-C(=O)-[O;H0;D2;+0:1]-[C:2]-[C:3](=[O;D1;H0:4])-[#7:5](-[c:6])-[C:7]1-[C:8]-[C:9](-[C;D1;H3:10])-[N;H0;D3;+0:11](-C(=O)-c2:c:c(-C(-F)(-F)-F):c:c(-C(-F)(-F)-F):c:2)-[c:12](:[c:13]):[c:14]-1>>[C;D1;H3:10]-[C:9]1-[C:8]-[C:7](-[#7:5](-[c:6])-[C:3](=[O;D1;H0:4])-[C:2]-[OH;D1;+0:1])-[c:14]:[c:12](:[c:13])-[NH;D2;+0:11]-1 | null | [] | 70 | CELSIUS | null | null | To a solution of 2-[{(2S,4R)-1-[3,5-bis(trifluoromethyl)benzoyl]-2-methyl-1,2,3,4-tetrahydroquinolin-4-yl}(4-chlorophenyl)amino]-2-oxoethyl acetate (500 mg, 0.82 mmol, 1 equ.) in ethanol (6 mL) and water (1 mL) was added potassium hydroxide (229 mg, 4.1 mmol, 5 equ.). The mixture was heated to 70° C. for 4 h. The mixtu... | 10.6084/m9.figshare.5104873.v1 | null | Trifluoro group.Trifluoro group.Ester.Tertiary amide | Primary alcohol.Secondary amine | c1ccccc1.c1ccc2c(c1)CCC[NH]2 | c1ccc2c(c1)CCCN2 | c1ccccc1.c1ccc2c(c1)CCCN2 | HF | O.C(C)O | 70 | null | CC(=O)OCC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2cc(C(F)(F)F)cc(C(F)(F)F)c2)c2ccccc21>O.C(C)O>C[C@H]1C[C@@H](N(C(=O)CO)c2ccc(Cl)cc2)c2ccccc2N1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-942d515f57e3447b811ce3444195e7b7 | CC(=O)O.C[C@H]1C[C@@H](N(C(=O)CO)c2ccc(Cl)cc2)c2ccccc2N1>>CC(=O)OCC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)Nc2ccccc21 | ClC1=CC=C(C=C1)N(C(CO)=O)[C@@H]1C[C@@H](NC2=CC=CC=C12)C.C(CCl)Cl.C(C)(=O)O>>C(C)(=O)OCC(=O)N([C@@H]1C[C@@H](NC2=CC=CC=C12)C)C1=CC=C(C=C1)Cl | O[C:2]([CH3:1])=[O:3].[OH:4][CH2:5][C:6](=[O:7])[N:8]([c:9]1[cH:10][cH:11][c:12]([Cl:13])[cH:14][cH:15]1)[C@@H:16]1[CH2:17][C@H:18]([CH3:19])[NH:20][c:21]2[cH:22][cH:23][cH:24][cH:25][c:26]21>>[CH3:1][C:2](=[O:3])[O:4][CH2:5][C:6](=[O:7])[N:8]([c:9]1[cH:10][cH:11][c:12]([Cl:13])[cH:14][cH:15]1)[C@@H:16]1[CH2:17][C@H:18... | CC(=O)O.C[C@H]1C[C@@H](N(C(=O)CO)c2ccc(Cl)cc2)c2ccccc2N1 | CC(=O)OCC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)Nc2ccccc21 | null | null | C(Cl)Cl | Acylation | Esterification of Carboxylic Acids | d9bd78214ee7dbc907e499722ae01849a72d188753963443e5df9fe42c31c43b | 3652e761944e8ef7ee40675a156c8ae39909c72166786934d88652debf2ec1ac | c1ccc(N[C@@H]2CCNc3ccccc32)cc1 | O-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[C:4]-[#7:5](-[c:6])-[C:7](=[O;D1;H0:8])-[C:9]-[OH;D1;+0:10]>>[C:4]-[#7:5](-[c:6])-[C:7](=[O;D1;H0:8])-[C:9]-[O;H0;D2;+0:10]-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3] | 84 | [{"value": 84.0, "product": "C(C)(=O)OCC(=O)N([C@@H]1C[C@@H](NC2=CC=CC=C12)C)C1=CC=C(C=C1)Cl", "details": "PERCENTYIELD", "is_desired": false}, {"value": 70.7, "product": "C(C)(=O)OCC(=O)N([C@@H]1C[C@@H](NC2=CC=CC=C12)C)C1=CC=C(C=C1)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 20 | HOUR | N-(4-Chlorophenyl)-2-hydroxy-N-[(2S,4R)-2-methyl-1,2,3,4-tetrahydroquinolin-4-yl]acetamide (300 mg, 0.91 mmol, 1 equ.) was dissolved in methylene chloride (3 mL). To this solution was added EDC (464 mg, 2.7 mmol, 3 equ.) and acetic acid (164 mg, 2.7 mmol, 3 equ.) and the reaction mixture was stirred at room temperature... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary alcohol | Ester | null | null | c1ccccc1.c1ccc2c(c1)CCCN2 | HO- | C(Cl)Cl | null | 20 | CC(=O)O.C[C@H]1C[C@@H](N(C(=O)CO)c2ccc(Cl)cc2)c2ccccc2N1>C(Cl)Cl>CC(=O)OCC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)Nc2ccccc21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d66277e98d1f4a59a5cad9023b6c3b9e | CC(=O)OCC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)Nc2ccccc21.COC(=O)C(C)(C)CCCc1ccc(C(=O)Cl)cc1>>COC(=O)C(C)(C)CCCc1ccc(C(=O)N2c3ccccc3[C@H](N(C(=O)COC(C)=O)c3ccc(Cl)cc3)C[C@@H]2C)cc1 | ClC(=O)C1=CC=C(C=C1)CCCC(C(=O)OC)(C)C.C(C)(=O)OCC(=O)N([C@@H]1C[C@@H](NC2=CC=CC=C12)C)C1=CC=C(C=C1)Cl.C(C)(C)N(CC)C(C)C>>C(C)(=O)OCC(=O)N([C@@H]1C[C@@H](N(C2=CC=CC=C12)C(=O)C1=CC=C(C=C1)CCCC(C(=O)OC)(C)C)C)C1=CC=C(C=C1)Cl | [NH:17]1[c:18]2[cH:19][cH:20][cH:21][cH:22][c:23]2[C@H:24]([N:25]([C:26](=[O:27])[CH2:28][O:29][C:30]([CH3:31])=[O:32])[c:33]2[cH:34][cH:35][c:36]([Cl:37])[cH:38][cH:39]2)[CH2:40][C@@H:41]1[CH3:42].Cl[C:15]([c:14]1[cH:13][cH:12][c:11]([CH2:10][CH2:9][CH2:8][C:5]([C:3]([O:2][CH3:1])=[O:4])([CH3:6])[CH3:7])[cH:44][cH:43]... | CC(=O)OCC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)Nc2ccccc21.COC(=O)C(C)(C)CCCc1ccc(C(=O)Cl)cc1 | COC(=O)C(C)(C)CCCc1ccc(C(=O)N2c3ccccc3[C@H](N(C(=O)COC(C)=O)c3ccc(Cl)cc3)C[C@@H]2C)cc1 | null | null | C(Cl)Cl | Acylation | N-alkylation of secondary amines with alkyl halides | 20af49e2ebd8e13ce8273786fd70e980d9c80eb9362be37fe2fe9cf2d75c9b8d | 96cb0a2fed10552c5770a45a2d6523b47ac3e38928b4a9c698d8577451182dcd | O=C(c1ccccc1)N1CC[C@@H](Nc2ccccc2)c2ccccc21 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[C:6]-[C:7](-[C;D1;H3:8])-[NH;D2;+0:9]-[c:10](:[c:11]):[c:12]>>[C:6]-[C:7](-[C;D1;H3:8])-[N;H0;D3;+0:9](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5])-[c:10](:[c:11]):[c:12] | 40 | [{"value": 40.0, "product": "C(C)(=O)OCC(=O)N([C@@H]1C[C@@H](N(C2=CC=CC=C12)C(=O)C1=CC=C(C=C1)CCCC(C(=O)OC)(C)C)C)C1=CC=C(C=C1)Cl", "details": "PERCENTYIELD", "is_desired": false}, {"value": 39.5, "product": "C(C)(=O)OCC(=O)N([C@@H]1C[C@@H](N(C2=CC=CC=C12)C(=O)C1=CC=C(C=C1)CCCC(C(=O)OC)(C)C)C)C1=CC=C(C=C1)Cl", "details... | null | null | null | null | To a solution of 2-{(4-chlorophenyl)[(2S,4R)-2-methyl-1,2,3,4-tetrahydroquinolin-4-yl]amino}-2-oxoethyl acetate (170 mg, 0.45 mmol, 1 equ.) in methylene chloride (2.0 mL) at room temperature was added diisopropylethylamine (127 uL, 0.73 mmol, 1.60 equ.) followed by methyl 5-[4-(chlorocarbonyl)phenyl]-2,2-dimethylpentan... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Secondary amine | Tertiary amide | c1ccc2c(c1)CCCN2 | c1ccc2c(c1)CCC[NH]2 | c1ccccc1.c1ccccc1.c1ccc2c(c1)CCC[NH]2 | HCl | C(Cl)Cl | null | null | CC(=O)OCC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)Nc2ccccc21.COC(=O)C(C)(C)CCCc1ccc(C(=O)Cl)cc1>C(Cl)Cl>COC(=O)C(C)(C)CCCc1ccc(C(=O)N2c3ccccc3[C@H](N(C(=O)COC(C)=O)c3ccc(Cl)cc3)C[C@@H]2C)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-6194b864aa8a4b1e9ac5f444369a9624 | CN1CC(O)CC1C(=O)O.C[Si](C)(C)C=[N+]=[N-]>>COC(=O)C1CC(O)CN1C | OC1CC(N(C1)C)C(=O)O.C[Si](C)(C)C=[N+]=[N-]>>COC(=O)C1N(CC(C1)O)C | [OH:2][C:3](=[O:4])[CH:5]1[CH2:6][CH:7]([OH:8])[CH2:9][N:10]1[CH3:11].C[Si](C)(C)[CH:1]=[N+]=[N-]>>[CH3:1][O:2][C:3](=[O:4])[CH:5]1[CH2:6][CH:7]([OH:8])[CH2:9][N:10]1[CH3:11] | CN1CC(O)CC1C(=O)O.C[Si](C)(C)C=[N+]=[N-] | COC(=O)C1CC(O)CN1C | null | null | CO | Heteroatom Alkylation and Arylation | O-alkylation of carboxylic acids with diazo compounds | 39589be0e9a30df66714fe618d22a8ac0fb24901dbf2ead1ab33e31556c7ac64 | 8b539baf7aeb5ab868833e33306bad77200a853d562904197e13de2e27e229d7 | C1CCNC1 | C-[Si](-C)(-C)-[CH;D2;+0:1]=[N+]=[N-].[#7:2]-[C:3]-[C:4](=[O;D1;H0:5])-[OH;D1;+0:6]>>[#7:2]-[C:3]-[C:4](=[O;D1;H0:5])-[O;H0;D2;+0:6]-[CH3;D1;+0:1] | null | [] | null | null | null | null | 4-Hydroxy-1-methyl-pyrrolidine-2-carboxylic acid (0.27 g, 1.85 mmol) was dissolved in 5 ml methanol at room temperature and (trimethylsilyl)diazomethane (2M solution in hexane) was added until solution become yellow. The mixture was concentrated down to afford crude 4-hydroxy-1-methyl-pyrrolidine-2-carboxylic acid meth... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Diazo.Silyl protective group | Ester | null | null | C1CC[NH]C1 | Other | CO | null | null | CN1CC(O)CC1C(=O)O.C[Si](C)(C)C=[N+]=[N-]>CO>COC(=O)C1CC(O)CN1C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-57d4663b805f49958326765e43d5b9ad | BrCCCc1cccnc1.CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(O)cc2)c2ccccc21>>CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(OCCCc3cccnc3)cc2)c2ccccc21 | ClC1=CC=C(C=C1)N(C(C)=O)[C@@H]1C[C@@H](N(C2=CC=CC=C12)C(C1=CC=C(C=C1)O)=O)C.C(=O)([O-])[O-].[K+].[K+].BrCCCC=1C=NC=CC1>>ClC1=CC=C(C=C1)N(C(C)=O)[C@@H]1C[C@@H](N(C2=CC=CC=C12)C(C1=CC=C(C=C1)OCCCC=1C=NC=CC1)=O)C | Br[CH2:24][CH2:25][CH2:26][c:27]1[cH:28][cH:29][cH:30][n:31][cH:32]1.[CH3:1][C:2](=[O:3])[N:4]([c:5]1[cH:6][cH:7][c:8]([Cl:9])[cH:10][cH:11]1)[C@@H:12]1[CH2:13][C@H:14]([CH3:15])[N:16]([C:17](=[O:18])[c:19]2[cH:20][cH:21][c:22]([OH:23])[cH:33][cH:34]2)[c:35]2[cH:36][cH:37][cH:38][cH:39][c:40]21>>[CH3:1][C:2](=[O:3])[N:... | BrCCCc1cccnc1.CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(O)cc2)c2ccccc21 | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(OCCCc3cccnc3)cc2)c2ccccc21 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | O=C(c1ccc(OCCCc2cccnc2)cc1)N1CC[C@@H](Nc2ccccc2)c2ccccc21 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[OH;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:4]-[c:5](:[c:6]):[c:7] | null | [] | 90 | CELSIUS | null | null | (2S,4R)-N-(4-Chloro-phenyl)-N-[1-(4-hydroxy-benzoyl)-2-methyl-1,2,3,4-tetrahydro-quinolin-4-yl]-acetamide was dissolved in DMF (5 mL) at room temperature. K2CO3 was added followed by 3-(3-bromo-propyl)-pyridine and the reaction was allowed to stir at 90° C. over night. The reaction mixture was concentrated in vacuo. Th... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccccc1.c1ccccc1.c1ccncc1.c1ccc2c(c1)CCC[NH]2 | HBr | CN(C)C=O | 90 | null | BrCCCc1cccnc1.CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(O)cc2)c2ccccc21>CN(C)C=O>CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(OCCCc3cccnc3)cc2)c2ccccc21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-0975063f50214ea4ad66ecdb8ca58fe1 | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(OCc3ccc(C(=O)O)o3)cc2)c2ccccc21.[NH4+]>>CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(OCc3ccc(C(N)=O)o3)cc2)c2ccccc21 | C(C)(=O)N([C@@H]1C[C@@H](N(C2=CC=CC=C12)C(=O)C1=CC=C(OCC2=CC=C(O2)C(=O)O)C=C1)C)C1=CC=C(C=C1)Cl.C=1C=CC2=C(C1)N=NN2O.CCN=C=NCCCN(C)C.[Cl-].[NH4+]>>C(C)(=O)N([C@@H]1C[C@@H](N(C2=CC=CC=C12)C(=O)C1=CC=C(OCC2=CC=C(O2)C(=O)N)C=C1)C)C1=CC=C(C=C1)Cl | O[C:29]([c:28]1[cH:27][cH:26][c:25]([CH2:24][O:23][c:22]2[cH:21][cH:20][c:19]([C:17]([N:16]3[C@@H:14]([CH3:15])[CH2:13][C@@H:12]([N:4]([C:2]([CH3:1])=[O:3])[c:5]4[cH:6][cH:7][c:8]([Cl:9])[cH:10][cH:11]4)[c:40]4[c:35]3[cH:36][cH:37][cH:38][cH:39]4)=[O:18])[cH:34][cH:33]2)[o:32]1)=[O:31].[NH4+:30]>>[CH3:1][C:2](=[O:3])[N... | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(OCc3ccc(C(=O)O)o3)cc2)c2ccccc21.[NH4+] | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(OCc3ccc(C(N)=O)o3)cc2)c2ccccc21 | null | CN(C)C=O | C(C)(=O)OCC.C1CCOC1 | Acylation | Carboxylic acid to amide conversion | 1283aef55d7ee699f097a8e5267689198c76ba671644401547f902657820236d | cb0a71c3fb37a76e96fbd81aae6f95a28398a03d1ad2c8e877085e735efb98f1 | O=C(c1ccc(OCc2ccco2)cc1)N1CC[C@@H](Nc2ccccc2)c2ccccc21 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[#8;a:5]:[c:6].[NH4+;D0:7]>>[NH2;D1;+0:7]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[#8;a:5]:[c:6] | 61 | [{"value": 61.0, "product": "C(C)(=O)N([C@@H]1C[C@@H](N(C2=CC=CC=C12)C(=O)C1=CC=C(OCC2=CC=C(O2)C(=O)N)C=C1)C)C1=CC=C(C=C1)Cl", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 11 | HOUR | (2S,4R)-5-(4-{4-[Acetyl-(4-chloro-phenyl)-amino]-2-methyl-3,4-dihydro-2H-quinoline-1-carbonyl}-phenoxymethyl)-furan-2-carboxylic acid (0.065 g, 0.12 mmol) was converted to the amide by dissolving in THF (1 mL) at room temperature. HOBt (0.024 g), EDCI (0.033 g), and ammonium chloride (0.013 g, 0.232 mmol) was added alo... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Primary amide | null | null | c1ccccc1.c1ccccc1.c1ccoc1.c1ccc2c(c1)CCC[NH]2 | HO- | CN(C)C=O.C(C)(=O)OCC.C1CCOC1 | null | 11 | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(OCc3ccc(C(=O)O)o3)cc2)c2ccccc21.[NH4+]>CN(C)C=O.C(C)(=O)OCC.C1CCOC1>CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(OCc3ccc(C(N)=O)o3)cc2)c2ccccc21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-f453b0676496406c9cd3738e011c6da1 | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(O)cc2)c2ccccc21.CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(OCCCN3CCN(C(=O)OC(C)(C)C)CC3)cc2)c2ccccc21.CC(C)(C)OC(=O)N1CCN(CCCCl)CC1>>CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(OCCCN3CCNCC3)cc2)c2ccccc21 | C(=O)([O-])[O-].[K+].[K+].C(C)(C)(C)OC(=O)N1CCN(CC1)CCCOC1=CC=C(C=C1)C(=O)N1[C@H](C[C@H](C2=CC=CC=C12)N(C1=CC=C(C=C1)Cl)C(C)=O)C.ClC1=CC=C(C=C1)N(C(C)=O)[C@@H]1C[C@@H](N(C2=CC=CC=C12)C(C1=CC=C(C=C1)O)=O)C.C(C)(C)(C)OC(=O)N1CCN(CC1)CCCCl>>ClC1=CC=C(C=C1)N(C(C)=O)[C@@H]1C[C@@H](N(C2=CC=CC=C12)C(C1=CC=C(C=C1)OCCCN1CCNCC1)... | [CH3:1][C:2](=[O:3])[N:4]([c:5]1[cH:6][cH:7][c:8]([Cl:9])[cH:10][cH:11]1)[C@@H:12]1[CH2:13][C@H:14]([CH3:15])[N:16]([C:17](=[O:18])[c:19]2[cH:20][cH:21][c:22]([OH:23])[cH:33][cH:34]2)[c:35]2[cH:36][cH:37][cH:38][cH:39][c:40]21.CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(O[CH2:24][CH2:25][CH2:26]N3CCN(C(=O)OC(C)(C... | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(O)cc2)c2ccccc21.CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(OCCCN3CCN(C(=O)OC(C)(C)C)CC3)cc2)c2ccccc21.CC(C)(C)OC(=O)N1CCN(CCCCl)CC1 | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(OCCCN3CCNCC3)cc2)c2ccccc21 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | OtherReaction | 2e90dc5a2a34d7606cb364a22871edc1bf43aab8a1b98625588a8e5ad1b9e0c6 | bfa789cac20a4cd0c25eaf6f43e2b2ee089209e3d34aa8afab8b6fd61ef4b300 | O=C(c1ccc(OCCCN2CCNCC2)cc1)N1CC[C@@H](Nc2ccccc2)c2ccccc21 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1]1-[C:2]-[C:3]-[N;H0;D3;+0:4](-C-C-C-Cl)-[C:5]-[C:6]-1.C-C(=O)-N(-[C@H]1-C-[C@H](-C)-N(-C(=O)-c2:c:c:c(-O-[CH2;D2;+0:7]-[C:8]-[CH2;D2;+0:9]-N3-C-C-N(-C(=O)-O-C(-C)(-C)-C)-C-C-3):c:c:2)-c2:c:c:c:c:c:2-1)-c1:c:c:c(-Cl):c:c:1.[OH;D1;+0:10]-[c:11](:[c:12]):[c:13]>>[c:12]:[c:11](-[O;H0;D2;+0... | 50 | [{"value": 50.0, "product": "ClC1=CC=C(C=C1)N(C(C)=O)[C@@H]1C[C@@H](N(C2=CC=CC=C12)C(C1=CC=C(C=C1)OCCCN1CCNCC1)=O)C", "details": "PERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | null | null | (2S,4R)-N-(4-Chloro-phenyl)-N-{2-methyl-1-[4-(3-piperazin-1-yl-propoxy)-benzoyl]-1,2,3,4-tetrahydro-quinolin-4-yl}-acetamide was prepared from (2S,4R)-4-[3-(4-{4-[acetyl(4-chloro-phenyl)-amino]-2-methyl-3,4-dihydro-2H-quinoline-1-carbonyl}-phenoxy)-propyl]-piperazine-1-carboxylic acid tert-butyl ester. (2S,4R)-N-(4-Chl... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary halide.Carbamic ester.Carbamic ester.Ether.Ether.Ether.Tertiary amide.Tertiary amide.Aromatic alcohol.Tertiary amine.Tertiary amine.Boc.Boc | Ether.Secondary amine.Tertiary amine | c1ccccc1.c1ccccc1.C1CNCCN1.c1ccc2c(c1)CCCN2.C1C[NH]CC[NH]1 | C1C[NH]CCN1 | c1ccccc1.c1ccccc1.C1C[NH]CCN1.c1ccc2c(c1)CCC[NH]2 | HCl | CN(C)C=O | 80 | null | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(O)cc2)c2ccccc21.CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(OCCCN3CCN(C(=O)OC(C)(C)C)CC3)cc2)c2ccccc21.CC(C)(C)OC(=O)N1CCN(CCCCl)CC1>CN(C)C=O>CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(OCCCN3CCNCC3)cc2)c2ccccc21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-7700194ea30e4e7da9ed7288a7c2fb68 | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(OCCCN3CCN(C(=O)OC(C)(C)C)CC3)cc2)c2ccccc21>>CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(OCCCN3CCNCC3)cc2)c2ccccc21 | C(C)(C)(C)OC(=O)N1CCN(CC1)CCCOC1=CC=C(C=C1)C(=O)N1[C@H](C[C@H](C2=CC=CC=C12)N(C1=CC=C(C=C1)Cl)C(C)=O)C>>ClC1=CC=C(C=C1)N(C(C)=O)[C@@H]1C[C@@H](N(C2=CC=CC=C12)C(C1=CC=C(C=C1)OCCCN1CCNCC1)=O)C | CC(C)(C)OC(=O)[N:30]1[CH2:29][CH2:28][N:27]([CH2:26][CH2:25][CH2:24][O:23][c:22]2[cH:21][cH:20][c:19]([C:17]([N:16]3[C@@H:14]([CH3:15])[CH2:13][C@@H:12]([N:4]([C:2]([CH3:1])=[O:3])[c:5]4[cH:6][cH:7][c:8]([Cl:9])[cH:10][cH:11]4)[c:40]4[c:35]3[cH:36][cH:37][cH:38][cH:39]4)=[O:18])[cH:34][cH:33]2)[CH2:32][CH2:31]1>>[CH3:1... | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(OCCCN3CCN(C(=O)OC(C)(C)C)CC3)cc2)c2ccccc21 | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(OCCCN3CCNCC3)cc2)c2ccccc21 | null | null | Cl.O1CCOCC1 | Reduction | Boc amine deprotection | 2c25e19aee181a3c5131cfdfda27035fd54d4379a11d745dfb75d386bacfd500 | a94b29c7264c852156fc1cdd4a0951a4fc26c06d0edc9e50c743825dbf79e3fd | O=C(c1ccc(OCCCN2CCNCC2)cc1)N1CC[C@@H](Nc2ccccc2)c2ccccc21 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1]1-[C:2]-[C:3]-[#7:4]-[C:5]-[C:6]-1>>[#7:4]1-[C:3]-[C:2]-[NH;D2;+0:1]-[C:6]-[C:5]-1 | 100 | [{"value": 100.0, "product": "ClC1=CC=C(C=C1)N(C(C)=O)[C@@H]1C[C@@H](N(C2=CC=CC=C12)C(C1=CC=C(C=C1)OCCCN1CCNCC1)=O)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | (2S,4R)-N-(4-Chloro-phenyl)-N-{2-methyl-1-[4-(3-piperazin-1-yl-propoxy)-benzoyl]-1,2,3,4-tetrahydro-quinolin-4-yl}-acetamide was prepared from (2S,4R)-4-[3-(4-{4-[acetyl(4-chloro-phenyl)-amino]-2-methyl-3,4-dihydro-2H-quinoline-1-carbonyl}-phenoxy)-propyl]-piperazine-1-carboxylic acid tert-butyl ester. (2S,4R)-N-(4-Chl... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Secondary amine | C1C[NH]CC[NH]1 | C1C[NH]CCN1 | c1ccccc1.c1ccccc1.C1C[NH]CCN1.c1ccc2c(c1)CCC[NH]2 | HO- | Cl.O1CCOCC1 | null | 2 | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(OCCCN3CCN(C(=O)OC(C)(C)C)CC3)cc2)c2ccccc21>Cl.O1CCOCC1>CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(OCCCN3CCNCC3)cc2)c2ccccc21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-3061ed6efacc4b96a7b16685ded4c08a | COc1c(F)cc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccc(Cl)cc3)C[C@@H]2C)cc1F>>CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2cc(F)c(O)c(F)c2)c2ccccc21 | ClC1=CC=C(C=C1)N(C(C)=O)[C@@H]1C[C@@H](N(C2=CC=CC=C12)C(C1=CC(=C(C(=C1)F)OC)F)=O)C.B(Br)(Br)Br>>ClC1=CC=C(C=C1)N(C(C)=O)[C@@H]1C[C@@H](N(C2=CC=CC=C12)C(C1=CC(=C(C(=C1)F)O)F)=O)C | C[O:24][c:23]1[c:21]([F:22])[cH:20][c:19]([C:17]([N:16]2[C@@H:14]([CH3:15])[CH2:13][C@@H:12]([N:4]([C:2]([CH3:1])=[O:3])[c:5]3[cH:6][cH:7][c:8]([Cl:9])[cH:10][cH:11]3)[c:33]3[c:28]2[cH:29][cH:30][cH:31][cH:32]3)=[O:18])[cH:27][c:25]1[F:26]>>[CH3:1][C:2](=[O:3])[N:4]([c:5]1[cH:6][cH:7][c:8]([Cl:9])[cH:10][cH:11]1)[C@@H:... | COc1c(F)cc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccc(Cl)cc3)C[C@@H]2C)cc1F | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2cc(F)c(O)c(F)c2)c2ccccc21 | null | null | ClCCl | Deprotection | Cleavage of methoxy ethers to alcohols | c5320c7dfa4f544d4900efcae9b3262bf0d5286bcf39c86109232351f35b23d5 | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | O=C(c1ccccc1)N1CC[C@@H](Nc2ccccc2)c2ccccc21 | C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[OH;D1;+0:1]-[c:2](:[c:3]):[c:4] | 78.7 | [{"value": 78.0, "product": "ClC1=CC=C(C=C1)N(C(C)=O)[C@@H]1C[C@@H](N(C2=CC=CC=C12)C(C1=CC(=C(C(=C1)F)O)F)=O)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 78.7, "product": "ClC1=CC=C(C=C1)N(C(C)=O)[C@@H]1C[C@@H](N(C2=CC=CC=C12)C(C1=CC(=C(C(=C1)F)O)F)=O)C", "details": "CALCULATEDPERCENTYIELD", "is_desir... | null | null | null | null | N-(4-chlorophenyl)-N-[(2S,4R)-1-(3,5-difluoro-4-methoxybenzoyl)-2-methyl-1,2,3,4-tetrahydroquinolin-4-yl]acetamide (200 mg, 0.41 mmol) was dissolved in dichloromethane and a solution of BBr3 (1.0 M in dichloromethane, 10 mL) was added; the reaction was allowed to stir at room temperature for until no starting material ... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | null | null | c1ccccc1.c1ccccc1.c1ccc2c(c1)CCC[NH]2 | Other | ClCCl | null | null | COc1c(F)cc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccc(Cl)cc3)C[C@@H]2C)cc1F>ClCCl>CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2cc(F)c(O)c(F)c2)c2ccccc21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-89a3a2907acd4c60942e8903b4fca9a9 | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2cc(F)c(O)c(F)c2)c2ccccc21.COC(=O)C(C)(C)CCBr>>COC(=O)C(C)(C)CCOc1c(F)cc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccc(Cl)cc3)C[C@@H]2C)cc1F | ClC1=CC=C(C=C1)N(C(C)=O)[C@@H]1C[C@@H](N(C2=CC=CC=C12)C(C1=CC(=C(C(=C1)F)O)F)=O)C.C(=O)([O-])[O-].[Cs+].[Cs+].BrCCC(C(=O)OC)(C)C>>C(C)(=O)N([C@@H]1C[C@@H](N(C2=CC=CC=C12)C(=O)C1=CC(=C(OCCC(C(=O)OC)(C)C)C(=C1)F)F)C)C1=CC=C(C=C1)Cl | [OH:10][c:11]1[c:12]([F:13])[cH:14][c:15]([C:16](=[O:17])[N:18]2[c:19]3[cH:20][cH:21][cH:22][cH:23][c:24]3[C@H:25]([N:26]([C:27]([CH3:28])=[O:29])[c:30]3[cH:31][cH:32][c:33]([Cl:34])[cH:35][cH:36]3)[CH2:37][C@@H:38]2[CH3:39])[cH:40][c:41]1[F:42].Br[CH2:9][CH2:8][C:5]([C:3]([O:2][CH3:1])=[O:4])([CH3:6])[CH3:7]>>[CH3:1][... | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2cc(F)c(O)c(F)c2)c2ccccc21.COC(=O)C(C)(C)CCBr | COC(=O)C(C)(C)CCOc1c(F)cc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccc(Cl)cc3)C[C@@H]2C)cc1F | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | O=C(c1ccccc1)N1CC[C@@H](Nc2ccccc2)c2ccccc21 | Br-[CH2;D2;+0:1]-[C:2]-[C:3]-[C:4](-[#8:5])=[O;D1;H0:6].[OH;D1;+0:7]-[c:8](:[c:9]):[c:10]>>[#8:5]-[C:4](=[O;D1;H0:6])-[C:3]-[C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:7]-[c:8](:[c:9]):[c:10] | 61.6 | [{"value": 61.0, "product": "C(C)(=O)N([C@@H]1C[C@@H](N(C2=CC=CC=C12)C(=O)C1=CC(=C(OCCC(C(=O)OC)(C)C)C(=C1)F)F)C)C1=CC=C(C=C1)Cl", "details": "PERCENTYIELD", "is_desired": false}, {"value": 61.6, "product": "C(C)(=O)N([C@@H]1C[C@@H](N(C2=CC=CC=C12)C(=O)C1=CC(=C(OCCC(C(=O)OC)(C)C)C(=C1)F)F)C)C1=CC=C(C=C1)Cl", "details":... | null | null | 8 | HOUR | N-(4-chlorophenyl)-N-[(2S,4R)-1-(3,5-difluoro-4-hydroxybenzoyl)-2-methyl-1,2,3,4-tetrahydroquinolin-4-yl]acetamide (150 mg, 0.32 mmol) was dissolved in DMF at room temperature and Cs2CO3 (259 mg, 0.80 mmol) was added. Methyl 4-bromo-2,2-dimethylbutanoate (157 mg, 0.48 mmol) was added and the reaction was stirred at roo... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccccc1.c1ccccc1.c1ccc2c(c1)CCC[NH]2 | HBr | CN(C)C=O | null | 8 | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2cc(F)c(O)c(F)c2)c2ccccc21.COC(=O)C(C)(C)CCBr>CN(C)C=O>COC(=O)C(C)(C)CCOc1c(F)cc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccc(Cl)cc3)C[C@@H]2C)cc1F |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-febfa0afe65845b4a5376e0a5e2deaa6 | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(N3CCC(C(=O)O)CC3)cc2)c2ccccc21.[NH4+]>>CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(N3CCC(C(N)=O)CC3)cc2)c2ccccc21 | [Cl-].[NH4+].C=1C=CC2=C(C1)N=NN2O.CN(C)C(=[N+](C)C)ON1C2=C(C=CC=N2)N=N1.F[P-](F)(F)(F)(F)F.C(C)(C)N(CC)C(C)C.C(C)(=O)N([C@@H]1C[C@@H](N(C2=CC=CC=C12)C(=O)C1=CC=C(C=C1)N1CCC(CC1)C(=O)O)C)C1=CC=C(C=C1)Cl>>C(C)(=O)N([C@@H]1C[C@@H](N(C2=CC=CC=C12)C(=O)C1=CC=C(C=C1)N1CCC(CC1)C(=O)N)C)C1=CC=C(C=C1)Cl | O[C:27]([CH:26]1[CH2:25][CH2:24][N:23]([c:22]2[cH:21][cH:20][c:19]([C:17]([N:16]3[C@@H:14]([CH3:15])[CH2:13][C@@H:12]([N:4]([C:2]([CH3:1])=[O:3])[c:5]4[cH:6][cH:7][c:8]([Cl:9])[cH:10][cH:11]4)[c:39]4[c:34]3[cH:35][cH:36][cH:37][cH:38]4)=[O:18])[cH:33][cH:32]2)[CH2:31][CH2:30]1)=[O:29].[NH4+:28]>>[CH3:1][C:2](=[O:3])[N:... | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(N3CCC(C(=O)O)CC3)cc2)c2ccccc21.[NH4+] | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(N3CCC(C(N)=O)CC3)cc2)c2ccccc21 | null | null | CN(C)C=O.C(C)(=O)OCC | Acylation | Carboxylic acid to amide conversion | 1283aef55d7ee699f097a8e5267689198c76ba671644401547f902657820236d | cb0a71c3fb37a76e96fbd81aae6f95a28398a03d1ad2c8e877085e735efb98f1 | O=C(c1ccc(N2CCCCC2)cc1)N1CC[C@@H](Nc2ccccc2)c2ccccc21 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[C:5].[NH4+;D0:6]>>[C:4]-[C:3](-[C;H0;D3;+0:1](-[NH2;D1;+0:6])=[O;D1;H0:2])-[C:5] | null | [] | null | null | 16 | HOUR | (2S,4R)-1-(4-{4-[Acetyl-(4-chloro-phenyl)-amino]-2-methyl-3,4-dihydro-2H-quinoline-1-carbonyl}-phenyl)-piperidine-4-carboxylic acid amide was prepared from (2S,4R)-1-(4-{4-[acetyl(4-chloro-phenyl)-amino]-2-methyl-3,4-dihydro-2H-quinoline-1-carbonyl}-phenyl)-piperidine-4-carboxylic acid. The acid (0.120 g, 0.22 mmol) wa... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Primary amide | null | null | c1ccccc1.c1ccccc1.C1CC[NH]CC1.c1ccc2c(c1)CCC[NH]2 | HO- | CN(C)C=O.C(C)(=O)OCC | null | 16 | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(N3CCC(C(=O)O)CC3)cc2)c2ccccc21.[NH4+]>CN(C)C=O.C(C)(=O)OCC>CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(N3CCC(C(N)=O)CC3)cc2)c2ccccc21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-8ebfd296bffc4168bc484359eb1ddf50 | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(O)nc2)c2ccccc21.COC(=O)C(C)(C)CCBr.COC(=O)C(C)(C)CCBr.COc1ccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccc(Cl)cc3)C[C@@H]2C)cn1>>COC(=O)C(C)(C)CCOc1ccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccc(Cl)cc3)C[C@@H]2C)cn1.COC(=O)C(C)(C)CCn1cc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccc(Cl)cc3)C[C@@H... | ClC1=CC=C(C=C1)N(C(C)=O)[C@@H]1C[C@@H](N(C2=CC=CC=C12)C(=O)C=1C=NC(=CC1)OC)C.ClC1=CC=C(C=C1)N(C(C)=O)[C@@H]1C[C@@H](N(C2=CC=CC=C12)C(=O)C=1C=NC(=CC1)OC)C.[Si](C)(C)(C)I.BrCCC(C(=O)OC)(C)C.[Al].ClC1=CC=C(C=C1)N(C(C)=O)[C@@H]1C[C@@H](N(C2=CC=CC=C12)C(=O)C=1C=NC(=CC1)O)C.BrCCC(C(=O)OC)(C)C>>C(C)(=O)N([C@@H]1C[C@@H](N(C2=C... | [OH:10][c:11]1[cH:12][cH:13][c:14]([C:15](=[O:16])[N:17]2[c:18]3[cH:19][cH:20][cH:21][cH:22][c:23]3[C@H:24]([N:25]([C:26]([CH3:27])=[O:28])[c:29]3[cH:30][cH:31][c:32]([Cl:33])[cH:34][cH:35]3)[CH2:36][C@@H:37]2[CH3:38])[cH:39][n:40]1.Br[CH2:49][CH2:48][C:45]([C:43]([O:42][CH3:41])=[O:44])([CH3:46])[CH3:47].Br[CH2:9][CH2... | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(O)nc2)c2ccccc21.COC(=O)C(C)(C)CCBr.COC(=O)C(C)(C)CCBr.COc1ccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccc(Cl)cc3)C[C@@H]2C)cn1 | COC(=O)C(C)(C)CCOc1ccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccc(Cl)cc3)C[C@@H]2C)cn1.COC(=O)C(C)(C)CCn1cc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccc(Cl)cc3)C[C@@H]2C)ccc1=O | null | C([O-])([O-])=O.[Ag+2] | CN(C=O)C.C(Cl)Cl | Acylation | OtherReaction | cb3eea33e8070e9f3f5e11706ed3969c0f32e648b1ff89d9d81d8c48963d0925 | eed310011e237c9d1634b8d2011b7ae3f1598bae2c40f6e7c8627702087e358a | O=C(c1ccc(=O)[nH]c1)N1CC[C@@H](Nc2ccccc2)c2ccccc21.O=C(c1cccnc1)N1CC[C@@H](Nc2ccccc2)c2ccccc21 | Br-[CH2;D2;+0:1]-[C:2]-[C:3]-[C:4](-[#8:5])=[O;D1;H0:6].Br-[CH2;D2;+0:7]-[C:8]-[C:9]-[C:10](-[#8:11])=[O;D1;H0:12].C-[O;H0;D2;+0:13]-[c;H0;D3;+0:14]1:[c:15]:[c:16]:[c:17](-[C:18](-[#7:19])=[O;D1;H0:20]):[c:21]:[n;H0;D2;+0:22]:1.[OH;D1;+0:23]-[c:24](:[c:25]):[#7;a:26]:[c:27]>>[#7:19]-[C:18](=[O;D1;H0:20])-[c:17]1:[c:21]... | 32 | [{"value": 32.0, "product": "C(C)(=O)N([C@@H]1C[C@@H](N(C2=CC=CC=C12)C(=O)C=1C=CC(=NC1)OCCC(C(=O)OC)(C)C)C)C1=CC=C(C=C1)Cl", "details": "PERCENTYIELD", "is_desired": false}, {"value": 32.0, "product": "C(C)(=O)N([C@@H]1C[C@@H](N(C2=CC=CC=C12)C(=O)C=1C=CC(N(C1)CCC(C(=O)OC)(C)C)=O)C)C1=CC=C(C=C1)Cl", "details": "PERCENTY... | null | null | 14 | HOUR | Methyl 4-[(5-{[(2S,4R)-4-[acetyl(4-chlorophenyl)amino]-2-methyl-3,4-dihydroquinolin-1(2H)-yl]carbonyl}pyridin-2-yl)oxy]-2,2-dimethylbutanoate was prepared from (2S,4R)-N-(4-chloro-phenyl)-N-[1-(6-methoxy-pyridine-3-carbonyl)-2-methyl-1,2,3,4-tetrahydro-quinolin-4-yl]-acetamide by deprotection of the methoxy and elabora... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary halide.Ether.Aromatic alcohol | Ether | c1ccncc1 | c1ccncc1 | c1ccncc1.c1ccccc1.c1ccc2c(c1)CCC[NH]2.c1ccncc1.c1ccccc1.c1ccc2c(c1)CCC[NH]2 | HBr | C([O-])([O-])=O.[Ag+2].CN(C=O)C.C(Cl)Cl | null | 14 | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(O)nc2)c2ccccc21.COC(=O)C(C)(C)CCBr.COC(=O)C(C)(C)CCBr.COc1ccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccc(Cl)cc3)C[C@@H]2C)cn1>C([O-])([O-])=O.[Ag+2].CN(C=O)C.C(Cl)Cl>COC(=O)C(C)(C)CCOc1ccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccc(Cl)cc3)C[C@@H]2C)cn1.COC(=O)C(C)(C)CCn1cc(C(=O)N2c3c... |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-4427dbe6f55d4b5a9b94c15c61ee6b54 | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(CN)cc2)c2ccccc21>>CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(C#N)cc2)c2ccccc21 | NCC1=CC=C(C(=O)N2[C@H](C[C@H](C3=CC=CC=C23)N(C(C)=O)C2=CC=C(C=C2)Cl)C)C=C1.FC(C1=NC=C(CCl)C=C1)(F)F>>ClC1=CC=C(C=C1)N(C(C)=O)[C@@H]1C[C@@H](N(C2=CC=CC=C12)C(C1=CC=C(C=C1)C#N)=O)C | [CH3:1][C:2](=[O:3])[N:4]([c:5]1[cH:6][cH:7][c:8]([Cl:9])[cH:10][cH:11]1)[C@@H:12]1[CH2:13][C@H:14]([CH3:15])[N:16]([C:17](=[O:18])[c:19]2[cH:20][cH:21][c:22]([CH2:23][NH2:24])[cH:25][cH:26]2)[c:27]2[cH:28][cH:29][cH:30][cH:31][c:32]21>>[CH3:1][C:2](=[O:3])[N:4]([c:5]1[cH:6][cH:7][c:8]([Cl:9])[cH:10][cH:11]1)[C@@H:12]1... | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(CN)cc2)c2ccccc21 | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(C#N)cc2)c2ccccc21 | null | null | null | Oxidation | OtherReaction | ac5c3ce1830d1d2f361a1aa656654ba2cf9d12f5ae14f5bbc507e5ce2e782a9d | 6be52931fddcbf34eb2e47e72b291d97a0f52d81412705e5a3068ffcb8150fea | O=C(c1ccccc1)N1CC[C@@H](Nc2ccccc2)c2ccccc21 | [NH2;D1;+0:1]-[CH2;D2;+0:2]-[c:3](:[c:4]):[c:5]>>[N;H0;D1;+0:1]#[C;H0;D2;+0:2]-[c:3](:[c:4]):[c:5] | null | [] | null | null | null | null | N-{(2S,4R)-1-[4-(aminomethyl)benzoyl]-2-methyl-1,2,3,4-tetrahydroquinolin-4-yl}-N-(4-chlorophenyl)acetamide was made following general procedure H, substituting 4-cyanobenzoyl chloride for 6-trifluoromethyl nicotinyl chloride. The rest of the procedure is followed as indicated in general procedure H to yield the corres... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | Nitrile | null | null | c1ccccc1.c1ccccc1.c1ccc2c(c1)CCC[NH]2 | null | null | null | null | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(CN)cc2)c2ccccc21>>CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(C#N)cc2)c2ccccc21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-93c98320a7f3439db997db72a95d930e | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(C#N)cc2)c2ccccc21>>CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(CN)cc2)c2ccccc21 | [BH4-].[Na+].ClC1=CC=C(C=C1)N(C(C)=O)[C@@H]1C[C@@H](N(C2=CC=CC=C12)C(C1=CC=C(C=C1)C#N)=O)C>>NCC1=CC=C(C(=O)N2[C@H](C[C@H](C3=CC=CC=C23)N(C(C)=O)C2=CC=C(C=C2)Cl)C)C=C1 | [CH3:1][C:2](=[O:3])[N:4]([c:5]1[cH:6][cH:7][c:8]([Cl:9])[cH:10][cH:11]1)[C@@H:12]1[CH2:13][C@H:14]([CH3:15])[N:16]([C:17](=[O:18])[c:19]2[cH:20][cH:21][c:22]([C:23]#[N:24])[cH:25][cH:26]2)[c:27]2[cH:28][cH:29][cH:30][cH:31][c:32]21>>[CH3:1][C:2](=[O:3])[N:4]([c:5]1[cH:6][cH:7][c:8]([Cl:9])[cH:10][cH:11]1)[C@@H:12]1[CH... | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(C#N)cc2)c2ccccc21 | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(CN)cc2)c2ccccc21 | null | [Co](Cl)Cl | C(C)O | Reduction | Reduction of nitrile to amine | 65bec2d9f430701d30dc9fcbe1c5418f3dfa174d67be035c50edfc71895dc9c7 | e8d1bc928b94bd4f5bf4b23363ce8f88b1ce7d146ba93829e7b8ad8dbe0007a7 | O=C(c1ccccc1)N1CC[C@@H](Nc2ccccc2)c2ccccc21 | [N;H0;D1;+0:1]#[C;H0;D2;+0:2]-[c:3](:[c:4]):[c:5]>>[NH2;D1;+0:1]-[CH2;D2;+0:2]-[c:3](:[c:4]):[c:5] | 83 | [{"value": 83.0, "product": "NCC1=CC=C(C(=O)N2[C@H](C[C@H](C3=CC=CC=C23)N(C(C)=O)C2=CC=C(C=C2)Cl)C)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 82.3, "product": "NCC1=CC=C(C(=O)N2[C@H](C[C@H](C3=CC=CC=C23)N(C(C)=O)C2=CC=C(C=C2)Cl)C)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | N-{(2S,4R)-1-[4-(aminomethyl)benzoyl]-2-methyl-1,2,3,4-tetrahydroquinolin-4-yl}-N-(4-chlorophenyl)acetamide was made following general procedure H, substituting 4-cyanobenzoyl chloride for 6-trifluoromethyl nicotinyl chloride. The rest of the procedure is followed as indicated in general procedure H to yield the corres... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile | Primary amine | null | null | c1ccccc1.c1ccccc1.c1ccc2c(c1)CCC[NH]2 | null | [Co](Cl)Cl.C(C)O | null | 2 | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(C#N)cc2)c2ccccc21>[Co](Cl)Cl.C(C)O>CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(CN)cc2)c2ccccc21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-b720726e9c70432e8a451e15e34acb90 | COc1ccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccc(Cl)cc3)C[C@@H]2C)cc1F>>CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(O)c(F)c2)c2ccccc21 | ClC1=CC=C(C=C1)N(C(C)=O)[C@@H]1C[C@@H](N(C2=CC=CC=C12)C(C1=CC(=C(C=C1)OC)F)=O)C.B(Br)(Br)Br>>ClC1=CC=C(C=C1)N(C(C)=O)[C@@H]1C[C@@H](N(C2=CC=CC=C12)C(C1=CC(=C(C=C1)O)F)=O)C | C[O:23][c:22]1[cH:21][cH:20][c:19]([C:17]([N:16]2[C@@H:14]([CH3:15])[CH2:13][C@@H:12]([N:4]([C:2]([CH3:1])=[O:3])[c:5]3[cH:6][cH:7][c:8]([Cl:9])[cH:10][cH:11]3)[c:32]3[c:27]2[cH:28][cH:29][cH:30][cH:31]3)=[O:18])[cH:26][c:24]1[F:25]>>[CH3:1][C:2](=[O:3])[N:4]([c:5]1[cH:6][cH:7][c:8]([Cl:9])[cH:10][cH:11]1)[C@@H:12]1[CH... | COc1ccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccc(Cl)cc3)C[C@@H]2C)cc1F | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(O)c(F)c2)c2ccccc21 | null | null | ClCCl | Deprotection | Cleavage of methoxy ethers to alcohols | c5320c7dfa4f544d4900efcae9b3262bf0d5286bcf39c86109232351f35b23d5 | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | O=C(c1ccccc1)N1CC[C@@H](Nc2ccccc2)c2ccccc21 | C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[OH;D1;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | null | null | N-(4-chlorophenyl)-N-[(2S,4R)-1-(3-fluoro-4-methoxybenzoyl)-2-methyl-1,2,3,4-tetrahydro-quinolin-4-yl]acetamide was dissolved in dichloromethane and a solution of BBr3 (1.0 M in dichloromethane, 10 mL) was added; the reaction was allowed to stir at room temperature for until no starting material remained. The reaction ... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | null | null | c1ccccc1.c1ccccc1.c1ccc2c(c1)CCC[NH]2 | Other | ClCCl | null | null | COc1ccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccc(Cl)cc3)C[C@@H]2C)cc1F>ClCCl>CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(O)c(F)c2)c2ccccc21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-67ed045c76d94923a3d9d06a441c196a | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(O)c(F)c2)c2ccccc21.COC(=O)C(C)(C)CCBr>>COC(=O)C(C)(C)CCOc1ccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccc(Cl)cc3)C[C@@H]2C)cc1F | ClC1=CC=C(C=C1)N(C(C)=O)[C@@H]1C[C@@H](N(C2=CC=CC=C12)C(C1=CC(=C(C=C1)O)F)=O)C.C(=O)([O-])[O-].[Cs+].[Cs+].BrCCC(C(=O)OC)(C)C>>C(C)(=O)N([C@@H]1C[C@@H](N(C2=CC=CC=C12)C(=O)C1=CC(=C(OCCC(C(=O)OC)(C)C)C=C1)F)C)C1=CC=C(C=C1)Cl | [OH:10][c:11]1[cH:12][cH:13][c:14]([C:15](=[O:16])[N:17]2[c:18]3[cH:19][cH:20][cH:21][cH:22][c:23]3[C@H:24]([N:25]([C:26]([CH3:27])=[O:28])[c:29]3[cH:30][cH:31][c:32]([Cl:33])[cH:34][cH:35]3)[CH2:36][C@@H:37]2[CH3:38])[cH:39][c:40]1[F:41].Br[CH2:9][CH2:8][C:5]([C:3]([O:2][CH3:1])=[O:4])([CH3:6])[CH3:7]>>[CH3:1][O:2][C:... | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(O)c(F)c2)c2ccccc21.COC(=O)C(C)(C)CCBr | COC(=O)C(C)(C)CCOc1ccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccc(Cl)cc3)C[C@@H]2C)cc1F | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | O=C(c1ccccc1)N1CC[C@@H](Nc2ccccc2)c2ccccc21 | Br-[CH2;D2;+0:1]-[C:2]-[C:3]-[C:4](-[#8:5])=[O;D1;H0:6].[OH;D1;+0:7]-[c:8](:[c:9]):[c:10]>>[#8:5]-[C:4](=[O;D1;H0:6])-[C:3]-[C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:7]-[c:8](:[c:9]):[c:10] | 43.3 | [{"value": 43.0, "product": "C(C)(=O)N([C@@H]1C[C@@H](N(C2=CC=CC=C12)C(=O)C1=CC(=C(OCCC(C(=O)OC)(C)C)C=C1)F)C)C1=CC=C(C=C1)Cl", "details": "PERCENTYIELD", "is_desired": false}, {"value": 43.3, "product": "C(C)(=O)N([C@@H]1C[C@@H](N(C2=CC=CC=C12)C(=O)C1=CC(=C(OCCC(C(=O)OC)(C)C)C=C1)F)C)C1=CC=C(C=C1)Cl", "details": "CALC... | null | null | 8 | HOUR | N-(4-chlorophenyl)-N-[(2S,4R)-1-(3-fluoro-4-hydroxybenzoyl)-2-methyl-1,2,3,4-tetrahydroquinolin-4-yl]acetamide (317 mg, 0.70 mmol) was dissolved in DMF at room temperature and Cs2CO3 (567 mg, 1.75 mmol) was added. Methyl 4-bromo-2,2-dimethylbutanoate (465 mg, 1.05 mmol) was added and the reaction was stirred at room te... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccccc1.c1ccccc1.c1ccc2c(c1)CCC[NH]2 | HBr | CN(C)C=O | null | 8 | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(O)c(F)c2)c2ccccc21.COC(=O)C(C)(C)CCBr>CN(C)C=O>COC(=O)C(C)(C)CCOc1ccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccc(Cl)cc3)C[C@@H]2C)cc1F |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-c5298b408298432e9b34470546c398e6 | CC(=O)N(c1ccc(Cl)cc1)C1CC(C)N(C(=O)c2ccc(N)cc2)c2ccccc21.O=C=NCCCl>>CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(N3CCNC3=O)cc2)c2ccccc21 | NC1=CC=C(C(=O)N2C(CC(C3=CC=CC=C23)N(C(C)=O)C2=CC=C(C=C2)Cl)C)C=C1.C(C)N(CC)CC.ClCCN=C=O>>ClC1=CC=C(C=C1)N(C(C)=O)[C@@H]1C[C@@H](N(C2=CC=CC=C12)C(C1=CC=C(C=C1)N1C(NCC1)=O)=O)C | [CH3:1][C:2](=[O:3])[N:4]([c:5]1[cH:6][cH:7][c:8]([Cl:9])[cH:10][cH:11]1)[CH:12]1[CH2:13][CH:14]([CH3:15])[N:16]([C:17](=[O:18])[c:19]2[cH:20][cH:21][c:22]([NH2:23])[cH:29][cH:30]2)[c:31]2[cH:32][cH:33][cH:34][cH:35][c:36]21.Cl[CH2:24][CH2:25][N:26]=[C:27]=[O:28]>>[CH3:1][C:2](=[O:3])[N:4]([c:5]1[cH:6][cH:7][c:8]([Cl:9... | CC(=O)N(c1ccc(Cl)cc1)C1CC(C)N(C(=O)c2ccc(N)cc2)c2ccccc21.O=C=NCCCl | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(N3CCNC3=O)cc2)c2ccccc21 | null | null | C(Cl)Cl | Acylation | OtherReaction | f37cf7a9ad0f5f76d1e1865cfd1e56f59ddf36de00b20b3db75c778c41365215 | 4027078f43f05c269e15aab569503cb296a7859c76790295b091602f9a2be99b | O=C1NCCN1c1ccc(C(=O)N2CC[C@@H](Nc3ccccc3)c3ccccc32)cc1 | Cl-[CH2;D2;+0:1]-[C:2]-[N;H0;D2;+0:3]=[C;H0;D2;+0:4]=[O;D1;H0:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[O;D1;H0:5]=[C;H0;D3;+0:4]1-[NH;D2;+0:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:6]-1-[c:7](:[c:8]):[c:9] | null | [] | null | null | null | null | N-[1-(4-Amino-benzoyl)-2-methyl-1,2,3,4-tetrahydro-quinolin-4-yl]-N-(4-chloro-phenyl)-acetamide (156 mg, 0.373 mmol) was dissolved in methylene chloride (3 mL) and was added triethylamine (0.078 mL, 0.559 mmol) and 1-chloro-2-isocyanato-ethane 0.038 mL, 0.448 mmol). The reaction was stirred at room temperature over nig... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Isocyanate.Primary amine | Urea | null | C1CNC[NH]1 | c1ccccc1.c1ccccc1.C1CNC[NH]1.c1ccc2c(c1)CCC[NH]2 | HCl | C(Cl)Cl | null | null | CC(=O)N(c1ccc(Cl)cc1)C1CC(C)N(C(=O)c2ccc(N)cc2)c2ccccc21.O=C=NCCCl>C(Cl)Cl>CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(N3CCNC3=O)cc2)c2ccccc21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-016c0a28ebad401fb22e451500a15c10 | COC(=O)CCCN(C)c1ccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccc(Cl)cc3)C[C@@H]2C)cc1>>CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(N(C)CCCC(=O)O)cc2)c2ccccc21 | C(C)O.[OH-].[Li+].COC(CCCN(C)C1=CC=C(C=C1)C(=O)N1[C@H](C[C@H](C2=CC=CC=C12)N(C1=CC=C(C=C1)Cl)C(C)=O)C)=O>>C(C)(=O)N([C@@H]1C[C@@H](N(C2=CC=CC=C12)C(=O)C1=CC=C(C=C1)N(CCCC(=O)O)C)C)C1=CC=C(C=C1)Cl | C[O:30][C:28]([CH2:27][CH2:26][CH2:25][N:23]([c:22]1[cH:21][cH:20][c:19]([C:17]([N:16]2[C@@H:14]([CH3:15])[CH2:13][C@@H:12]([N:4]([C:2]([CH3:1])=[O:3])[c:5]3[cH:6][cH:7][c:8]([Cl:9])[cH:10][cH:11]3)[c:38]3[c:33]2[cH:34][cH:35][cH:36][cH:37]3)=[O:18])[cH:32][cH:31]1)[CH3:24])=[O:29]>>[CH3:1][C:2](=[O:3])[N:4]([c:5]1[cH:... | COC(=O)CCCN(C)c1ccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccc(Cl)cc3)C[C@@H]2C)cc1 | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(N(C)CCCC(=O)O)cc2)c2ccccc21 | null | null | O1CCCC1 | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | O=C(c1ccccc1)N1CC[C@@H](Nc2ccccc2)c2ccccc21 | 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] | null | [] | 50 | CELSIUS | null | null | (2S,4R)-4-[(4-{4-[Acetyl-(4-chloro-phenyl)-amino]-2-methyl-3,4-dihydro-2H-quinoline-1-carbonyl}-phenyl)-methyl-amino]-butyric acid was prepared from (2S,4R)-4-[(4-{4-[acetyl(4-chloro-phenyl)-amino]-2-methyl-3,4-dihydro-2H-quinoline-1-carbonyl}-phenyl)-methyl-amino]-butyric acid methyl ester was hydrolyzed to the acid b... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1.c1ccccc1.c1ccc2c(c1)CCC[NH]2 | Other | O1CCCC1 | 50 | null | COC(=O)CCCN(C)c1ccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccc(Cl)cc3)C[C@@H]2C)cc1>O1CCCC1>CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(N(C)CCCC(=O)O)cc2)c2ccccc21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-8f7997eefabb47a8868bf467e90a5a97 | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(O)cc2)c2ccccc21.CC(C)(O)CCCBr>>CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(OCCCC(C)(C)O)cc2)c2ccccc21 | ClC1=CC=C(C=C1)N(C(C)=O)[C@@H]1C[C@@H](N(C2=CC=CC=C12)C(C1=CC=C(C=C1)O)=O)C.C(=O)([O-])[O-].[K+].[K+].BrCCCC(C)(O)C>>ClC1=CC=C(C=C1)N(C(C)=O)[C@@H]1C[C@@H](N(C2=CC=CC=C12)C(C1=CC=C(C=C1)OCCCC(C)(C)O)=O)C | [CH3:1][C:2](=[O:3])[N:4]([c:5]1[cH:6][cH:7][c:8]([Cl:9])[cH:10][cH:11]1)[C@@H:12]1[CH2:13][C@H:14]([CH3:15])[N:16]([C:17](=[O:18])[c:19]2[cH:20][cH:21][c:22]([OH:23])[cH:31][cH:32]2)[c:33]2[cH:34][cH:35][cH:36][cH:37][c:38]21.Br[CH2:24][CH2:25][CH2:26][C:27]([CH3:28])([CH3:29])[OH:30]>>[CH3:1][C:2](=[O:3])[N:4]([c:5]1... | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(O)cc2)c2ccccc21.CC(C)(O)CCCBr | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(OCCCC(C)(C)O)cc2)c2ccccc21 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | O=C(c1ccccc1)N1CC[C@@H](Nc2ccccc2)c2ccccc21 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[OH;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:4]-[c:5](:[c:6]):[c:7] | 79 | [{"value": 79.0, "product": "ClC1=CC=C(C=C1)N(C(C)=O)[C@@H]1C[C@@H](N(C2=CC=CC=C12)C(C1=CC=C(C=C1)OCCCC(C)(C)O)=O)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 78.8, "product": "ClC1=CC=C(C=C1)N(C(C)=O)[C@@H]1C[C@@H](N(C2=CC=CC=C12)C(C1=CC=C(C=C1)OCCCC(C)(C)O)=O)C", "details": "CALCULATEDPERCENTYIELD",... | 80 | CELSIUS | null | null | (2S,4R)-N-(4-Chloro-phenyl)-N-[1-(4-hydroxy-benzoyl)-2-methyl-1,2,3,4-tetrahydro-quinolin-4-yl]-acetamide (0.1 g, 0.23 mmol) was dissolved in DMF (5 mL) at room temperature. K2CO3 (0.317 g, 2.3 mmol) was added. 5-Bromo-2-methyl-pentan-2-ol (0.092 g, 0.51 mmol) was added and the reaction was allowed to heat to 80° C. ov... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccccc1.c1ccccc1.c1ccc2c(c1)CCC[NH]2 | HBr | CN(C)C=O | 80 | null | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(O)cc2)c2ccccc21.CC(C)(O)CCCBr>CN(C)C=O>CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(OCCCC(C)(C)O)cc2)c2ccccc21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-cefe76de20e24eb88d668fffd35a3609 | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(O)cc2)c2ccccc21.ClCC1CO1>>CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(OCC3CO3)cc2)c2ccccc21 | ClC1=CC=C(C=C1)N(C(C)=O)[C@@H]1C[C@@H](N(C2=CC=CC=C12)C(C1=CC=C(C=C1)O)=O)C.C(=O)([O-])[O-].[K+].[K+].ClCC1OC1>>ClC1=CC=C(C=C1)N(C(C)=O)[C@@H]1C[C@@H](N(C2=CC=CC=C12)C(C1=CC=C(C=C1)OCC1OC1)=O)C | [CH3:1][C:2](=[O:3])[N:4]([c:5]1[cH:6][cH:7][c:8]([Cl:9])[cH:10][cH:11]1)[C@@H:12]1[CH2:13][C@H:14]([CH3:15])[N:16]([C:17](=[O:18])[c:19]2[cH:20][cH:21][c:22]([OH:23])[cH:28][cH:29]2)[c:30]2[cH:31][cH:32][cH:33][cH:34][c:35]21.Cl[CH2:24][CH:25]1[CH2:26][O:27]1>>[CH3:1][C:2](=[O:3])[N:4]([c:5]1[cH:6][cH:7][c:8]([Cl:9])[... | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(O)cc2)c2ccccc21.ClCC1CO1 | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(OCC3CO3)cc2)c2ccccc21 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | O=C(c1ccc(OCC2CO2)cc1)N1CC[C@@H](Nc2ccccc2)c2ccccc21 | Cl-[CH2;D2;+0:1]-[C:2]1-[#8:3]-[C:4]-1.[OH;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[c:7]:[c:6](-[O;H0;D2;+0:5]-[CH2;D2;+0:1]-[C:2]1-[#8:3]-[C:4]-1):[c:8] | 98.3 | [{"value": 77.0, "product": "ClC1=CC=C(C=C1)N(C(C)=O)[C@@H]1C[C@@H](N(C2=CC=CC=C12)C(C1=CC=C(C=C1)OCC1OC1)=O)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 98.3, "product": "ClC1=CC=C(C=C1)N(C(C)=O)[C@@H]1C[C@@H](N(C2=CC=CC=C12)C(C1=CC=C(C=C1)OCC1OC1)=O)C", "details": "CALCULATEDPERCENTYIELD", "is_desir... | 80 | CELSIUS | null | null | (2S,4R)-N-(4-Chloro-phenyl)-N-[1-(4-hydroxy-benzoyl)-2-methyl-1,2,3,4-tetrahydro-quinolin-4-yl]-acetamide (0.5 g, 1.14 mmol) was dissolved in DMF at room temperature and K2CO3 (1.26 g, 9.13 mmol) was added. 2-Chloromethyl-oxirane (0.42 g, 4.57 mmol) was added and the reaction was allowed to heat to 80° C. overnight. Th... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccccc1.c1ccccc1.C1CO1.c1ccc2c(c1)CCC[NH]2 | HCl | CN(C)C=O | 80 | null | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(O)cc2)c2ccccc21.ClCC1CO1>CN(C)C=O>CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(OCC3CO3)cc2)c2ccccc21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-c6c0cf70711c47f89026ad950f4e6147 | COC(=O)C(C)(C)CCCc1ccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccc(Cl)cc3)C[C@@H]2C)cc1>>CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(CCCC(C)(C)C(=O)O)cc2)c2ccccc21 | COC(C(CCCC1=CC=C(C=C1)C(=O)N1[C@H](C[C@H](C2=CC=CC=C12)N(C1=CC=C(C=C1)Cl)C(C)=O)C)(C)C)=O.[OH-].[Na+]>>C(C)(=O)N([C@@H]1C[C@@H](N(C2=CC=CC=C12)C(=O)C1=CC=C(C=C1)CCCC(C(=O)O)(C)C)C)C1=CC=C(C=C1)Cl | C[O:31][C:29]([C:26]([CH2:25][CH2:24][CH2:23][c:22]1[cH:21][cH:20][c:19]([C:17]([N:16]2[C@@H:14]([CH3:15])[CH2:13][C@@H:12]([N:4]([C:2]([CH3:1])=[O:3])[c:5]3[cH:6][cH:7][c:8]([Cl:9])[cH:10][cH:11]3)[c:39]3[c:34]2[cH:35][cH:36][cH:37][cH:38]3)=[O:18])[cH:33][cH:32]1)([CH3:27])[CH3:28])=[O:30]>>[CH3:1][C:2](=[O:3])[N:4](... | COC(=O)C(C)(C)CCCc1ccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccc(Cl)cc3)C[C@@H]2C)cc1 | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(CCCC(C)(C)C(=O)O)cc2)c2ccccc21 | null | null | O.CO.O1CCCC1 | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | O=C(c1ccccc1)N1CC[C@@H](Nc2ccccc2)c2ccccc21 | 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] | 60 | [{"value": 60.0, "product": "C(C)(=O)N([C@@H]1C[C@@H](N(C2=CC=CC=C12)C(=O)C1=CC=C(C=C1)CCCC(C(=O)O)(C)C)C)C1=CC=C(C=C1)Cl", "details": "PERCENTYIELD", "is_desired": false}, {"value": 60.0, "product": "C(C)(=O)N([C@@H]1C[C@@H](N(C2=CC=CC=C12)C(=O)C1=CC=C(C=C1)CCCC(C(=O)O)(C)C)C)C1=CC=C(C=C1)Cl", "details": "CALCULATEDPE... | 60 | CELSIUS | null | null | 5-(4-{(2S,4R)-4-[acetyl(4-chloro-phenyl)-amino]-2-methyl-3,4-dihydro-2H-quinoline-1-carbonyl}-phenyl)-2,2-dimethyl-pentanoic acid methyl ester (500 mg, 0.89 mmol, 1 eq.) was dissolved in methanol/tetrahydrofuran (2/1) (4 ml). A solution of sodium hydroxide (71 mg, 1.8 mmol, 2 eq.) in water (1 ml) was added and reaction... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1.c1ccccc1.c1ccc2c(c1)CCC[NH]2 | Other | O.CO.O1CCCC1 | 60 | null | COC(=O)C(C)(C)CCCc1ccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccc(Cl)cc3)C[C@@H]2C)cc1>O.CO.O1CCCC1>CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(CCCC(C)(C)C(=O)O)cc2)c2ccccc21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-40a6ccf4648e4083a27814efb89a04c0 | COc1ccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccc(NC(=O)OCc4ccccc4)cc3)C[C@@H]2C)cc1>>COc1ccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccc(N)cc3)C[C@@H]2C)cc1 | C(C)(=O)N(C1=CC=C(C=C1)NC(OCC1=CC=CC=C1)=O)[C@@H]1C[C@@H](N(C2=CC=CC=C12)C(C1=CC=C(C=C1)OC)=O)C>>NC1=CC=C(C=C1)N(C(C)=O)[C@@H]1C[C@@H](N(C2=CC=CC=C12)C(C1=CC=C(C=C1)OC)=O)C | O=C(OCc1ccccc1)[NH:25][c:24]1[cH:23][cH:22][c:21]([N:17]([C@H:16]2[c:15]3[c:10]([cH:11][cH:12][cH:13][cH:14]3)[N:9]([C:7]([c:6]3[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:32][cH:31]3)=[O:8])[C@@H:29]([CH3:30])[CH2:28]2)[C:18]([CH3:19])=[O:20])[cH:27][cH:26]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([C:7](=[O:8])[N:9]2[c:10]3[cH:11... | COc1ccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccc(NC(=O)OCc4ccccc4)cc3)C[C@@H]2C)cc1 | COc1ccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccc(N)cc3)C[C@@H]2C)cc1 | null | [Pd] | CO | Reduction | Hydrogenolysis of amides/imides/carbamates | 087b6600ba91d3df931fe6979f2445c192cbfd59e04fd2d8a10f7c7573ac669f | 4e549866ec1acadec4c84aaf8495992a28ec78d8ea5ef1b9f44dd843b0dcb7d4 | O=C(c1ccccc1)N1CC[C@@H](Nc2ccccc2)c2ccccc21 | O=C(-O-C-c1:c:c:c:c:c:1)-[NH;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | 2 | HOUR | Benzyl (4-{acetyl[(2S,4R)-1-(4-methoxybenzoyl)-2-methyl-1,2,3,4-tetrahydroquinolin-4-yl]amino}phenyl)carbamate was dissolved in MeOH and was added a catalytic amount of Palladium on Carbon (10%). The system was purged by Hydrogen gas, the subjected to 1 atm of H2 for 2 h. The reaction was quenched with air and filtered... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether | Primary amine | c1ccccc1 | null | c1ccccc1.c1ccccc1.c1ccc2c(c1)CCC[NH]2 | HO- | [Pd].CO | null | 2 | COc1ccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccc(NC(=O)OCc4ccccc4)cc3)C[C@@H]2C)cc1>[Pd].CO>COc1ccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccc(N)cc3)C[C@@H]2C)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-40840153529243fdbf17ca5637a03392 | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(OCCC(C)(C)C(=O)O)cc2)c2ccccc21.CS(N)(=O)=O>>CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(OCCC(C)(C)C(=O)NS(C)(=O)=O)cc2)c2ccccc21 | C(C)(=O)N([C@@H]1C[C@@H](N(C2=CC=CC=C12)C(=O)C1=CC=C(OCCC(C(=O)O)(C)C)C=C1)C)C1=CC=C(C=C1)Cl.CN(C)C=O.CS(=O)(=O)N>>ClC1=CC=C(C=C1)N(C(C)=O)[C@@H]1C[C@@H](N(C2=CC=CC=C12)C(C1=CC=C(C=C1)OCCC(C(=O)NS(=O)(=O)C)(C)C)=O)C | O[C:29]([C:26]([CH2:25][CH2:24][O:23][c:22]1[cH:21][cH:20][c:19]([C:17]([N:16]2[C@@H:14]([CH3:15])[CH2:13][C@@H:12]([N:4]([C:2]([CH3:1])=[O:3])[c:5]3[cH:6][cH:7][c:8]([Cl:9])[cH:10][cH:11]3)[c:43]3[c:38]2[cH:39][cH:40][cH:41][cH:42]3)=[O:18])[cH:37][cH:36]1)([CH3:27])[CH3:28])=[O:30].[NH2:31][S:32]([CH3:33])(=[O:34])=[... | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(OCCC(C)(C)C(=O)O)cc2)c2ccccc21.CS(N)(=O)=O | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(OCCC(C)(C)C(=O)NS(C)(=O)=O)cc2)c2ccccc21 | null | null | C(Cl)Cl.C(C(=O)Cl)(=O)Cl | Acylation | Carboxylic acid with primary amine to amide | 195a412a8235704efe2985cdc18467ba661e632bab7b61944399ecc813e32a09 | 5e4665bad9c6f58dddd98c5f95e436c640b4c0118b04efea5cd58c7d1755401d | O=C(c1ccccc1)N1CC[C@@H](Nc2ccccc2)c2ccccc21 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])(-[C;D1;H3:5])-[C;D1;H3:6].[C;D1;H3:7]-[#16:8](-[NH2;D1;+0:9])(=[O;D1;H0:10])=[O;D1;H0:11]>>[C:4]-[C:3](-[C;D1;H3:5])(-[C;D1;H3:6])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:9]-[#16:8](-[C;D1;H3:7])(=[O;D1;H0:10])=[O;D1;H0:11] | null | [] | null | null | null | null | (2S,4R)-4-(4-{4-[Acetyl-(4-chloro-phenyl)-amino]-2-methyl-3,4-dihydro-2H-quinoline-1-carbonyl}-phenoxy)-2,2-dimethyl-butyric acid (200 mg, 0.37 mmol) was dissolved in methylene chloride (5 mL) and oxalyl chloride (2 mL). A single drop of DMF was added, and the mixture was stirred at room temperature until gas evolution... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonamide.Carboxylic acid | Sulfonamide.Secondary amide | null | null | c1ccccc1.c1ccccc1.c1ccc2c(c1)CCC[NH]2 | HO- | C(Cl)Cl.C(C(=O)Cl)(=O)Cl | null | null | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(OCCC(C)(C)C(=O)O)cc2)c2ccccc21.CS(N)(=O)=O>C(Cl)Cl.C(C(=O)Cl)(=O)Cl>CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(OCCC(C)(C)C(=O)NS(C)(=O)=O)cc2)c2ccccc21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-433aac779362428ca7ba64aa1edae43c | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2cc(C(F)(F)F)cc(C(F)(F)F)c2)c2ccc(Cl)cc21.CCc1ccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccc(Cl)cc3)C[C@@H]2C)cn1.COC(=O)c1ccc(Cl)nc1.O=C(Cl)c1cc(C(F)(F)F)cc(C(F)(F)F)c1>>CCc1ccc(C(=O)N2c3ccc(Cl)cc3[C@H](N(C(C)=O)c3ccc(Cl)cc3)C[C@@H]2C)cn1.CCc1ccc(CCl)cn1 | ClC1=NC=C(C(=O)OC)C=C1.FC(C=1C=C(C(=O)N2[C@H](C[C@H](C3=CC(=CC=C23)Cl)N(C(C)=O)C2=CC=C(C=C2)Cl)C)C=C(C1)C(F)(F)F)(F)F.ClC1=CC=C(C=C1)N(C(C)=O)[C@@H]1C[C@@H](N(C2=CC=CC=C12)C(=O)C=1C=NC(=CC1)CC)C.FC(C=1C=C(C(=O)Cl)C=C(C1)C(F)(F)F)(F)F>>ClC=1C=C2[C@@H](C[C@@H](N(C2=CC1)C(=O)C=1C=NC(=CC1)CC)C)N(C(C)=O)C1=CC=C(C=C1)Cl.C(C)... | FC(F)(F)c1cc(C(F)(F)F)c[c:6]([C:7](=[O:8])[N:9]2[c:10]3[cH:11][cH:12][c:13]([Cl:14])[cH:15][c:16]3[C@H:17]([N:18]([C:19]([CH3:20])=[O:21])[c:22]3[cH:23][cH:24][c:25]([Cl:26])[cH:27][cH:28]3)[CH2:29][C@@H:30]2[CH3:31])c1.CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)[c:39]2[cH:38][cH:37][c:36]([CH2:35][CH3:34])[n:43][cH:4... | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2cc(C(F)(F)F)cc(C(F)(F)F)c2)c2ccc(Cl)cc21.CCc1ccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccc(Cl)cc3)C[C@@H]2C)cn1.COC(=O)c1ccc(Cl)nc1.O=C(Cl)c1cc(C(F)(F)F)cc(C(F)(F)F)c1 | CCc1ccc(C(=O)N2c3ccc(Cl)cc3[C@H](N(C(C)=O)c3ccc(Cl)cc3)C[C@@H]2C)cn1.CCc1ccc(CCl)cn1 | null | null | null | C-C Coupling | OtherReaction | 94936b50ede0589ceddb51bfd0526e44744ef6bd0a8f1b7daf946455f196bafa | 54d9f26861cc63ff190e6c74176f91c87344340754274c573a4ba194b02c5cd4 | O=C(c1cccnc1)N1CC[C@@H](Nc2ccccc2)c2ccccc21.c1ccncc1 | C-C(=O)-N(-[C@H]1-C-[C@H](-C)-N(-C(=O)-[c;H0;D3;+0:1]2:[c:2]:[c:3]:[c:4]:[#7;a:5]:[c:6]:2)-c2:c:c:c:c:c:2-1)-c1:c:c:c(-Cl):c:c:1.Cl-[c;H0;D3;+0:7]1:[#7;a:8]:[cH;D2;+0:9]:c(-[C;H0;D3;+0:10](=O)-O-[CH3;D1;+0:11]):[cH;D2;+0:12]:[c:13]:1.F-C(-F)(-F)-c1:c:[c;H0;D3;+0:14](-[C:15](=[O;D1;H0:16])-[#7:17](-[C:18])-[c:19]):c:c(-... | null | [] | null | null | null | null | N-{(2S,4R)-6-Chloro-1-[(6-ethylpyridin-3-yl)carbonyl]-2-methyl-1,2,3,4-tetrahydroquinolin-4-yl}-N-(4-chlorophenyl)acetamide was prepared following the procedure described for N-{(2S,4R)-1-[3,5-bis(trifluoromethyl)benzoyl]-6-chloro-2-methyl-1,2,3,4-tetrahydroquinolin-4-yl}-N-(4-chlorophenyl)acetamide substituting 6-ethy... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Trifluoro group.Trifluoro group.Trifluoro group.Trifluoro group.Aromatic halide.Aromatic halide.Ester.Tertiary amide.Tertiary amide | Primary halide | c1ccccc1.c1ccccc1.c1ccncc1.c1ccc2c(c1)CCCN2.c1ccncc1.c1ccccc1 | c1ccncc1.c1ccncc1 | c1ccncc1.c1ccccc1.c1ccc2c(c1)CCC[NH]2.c1ccncc1 | HF | null | null | null | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2cc(C(F)(F)F)cc(C(F)(F)F)c2)c2ccc(Cl)cc21.CCc1ccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccc(Cl)cc3)C[C@@H]2C)cn1.COC(=O)c1ccc(Cl)nc1.O=C(Cl)c1cc(C(F)(F)F)cc(C(F)(F)F)c1>>CCc1ccc(C(=O)N2c3ccc(Cl)cc3[C@H](N(C(C)=O)c3ccc(Cl)cc3)C[C@@H]2C)cn1.CCc1ccc(CCl)cn1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-853ea3c5ceb945febb40bb8f607ef5c3 | COC(=O)C(C)(C)CCOc1ccc(C(=O)N2c3ccccc3[C@H](N(C(=O)C3CC3)c3ccc(Cl)cc3)C[C@@H]2C)cc1>>C[C@H]1C[C@@H](N(C(=O)C2CC2)c2ccc(Cl)cc2)c2ccccc2N1C(=O)c1ccc(OCCC(C)(C)C(=O)O)cc1 | ClC1=CC=C(C=C1)N([C@@H]1C[C@@H](N(C2=CC=CC=C12)C(=O)C1=CC=C(OCCC(C(=O)OC)(C)C)C=C1)C)C(=O)C1CC1.[OH-].[Na+]>>ClC1=CC=C(C=C1)N([C@@H]1C[C@@H](N(C2=CC=CC=C12)C(=O)C1=CC=C(OCCC(C(=O)O)(C)C)C=C1)C)C(=O)C1CC1 | C[O:39][C:37]([C:34]([CH2:33][CH2:32][O:31][c:30]1[cH:29][cH:28][c:27]([C:25]([N:24]2[C@@H:2]([CH3:1])[CH2:3][C@@H:4]([N:5]([C:6](=[O:7])[CH:8]3[CH2:9][CH2:10]3)[c:11]3[cH:12][cH:13][c:14]([Cl:15])[cH:16][cH:17]3)[c:18]3[cH:19][cH:20][cH:21][cH:22][c:23]32)=[O:26])[cH:41][cH:40]1)([CH3:35])[CH3:36])=[O:38]>>[CH3:1][C@H... | COC(=O)C(C)(C)CCOc1ccc(C(=O)N2c3ccccc3[C@H](N(C(=O)C3CC3)c3ccc(Cl)cc3)C[C@@H]2C)cc1 | C[C@H]1C[C@@H](N(C(=O)C2CC2)c2ccc(Cl)cc2)c2ccccc2N1C(=O)c1ccc(OCCC(C)(C)C(=O)O)cc1 | null | null | O.CO.O1CCCC1 | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | O=C(c1ccccc1)N1CC[C@@H](N(C(=O)C2CC2)c2ccccc2)c2ccccc21 | 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] | 87 | [{"value": 87.0, "product": "ClC1=CC=C(C=C1)N([C@@H]1C[C@@H](N(C2=CC=CC=C12)C(=O)C1=CC=C(OCCC(C(=O)O)(C)C)C=C1)C)C(=O)C1CC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 86.9, "product": "ClC1=CC=C(C=C1)N([C@@H]1C[C@@H](N(C2=CC=CC=C12)C(=O)C1=CC=C(OCCC(C(=O)O)(C)C)C=C1)C)C(=O)C1CC1", "details": "CALCULAT... | 40 | CELSIUS | null | null | Methyl 4-(4-{[(2S,4R)-4-[(4-chlorophenyl)(cyclopropylcarbonyl)amino]-2-methyl-3,4-dihydroquinolin-1(2H)-yl]carbonyl}phenoxy)-2,2-dimethylbutanoate (100 mg, 0.17 mmol, 1 equ.) was dissolved in methanol/tetrahydrofuran (2/1) (1 ml). A solution of sodium hydroxide (21 mg, 0.51 mmol, 3 eq.) in water (0.5 ml) was added and ... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | C1CC1.c1ccccc1.c1ccc2c(c1)CCC[NH]2.c1ccccc1 | Other | O.CO.O1CCCC1 | 40 | null | COC(=O)C(C)(C)CCOc1ccc(C(=O)N2c3ccccc3[C@H](N(C(=O)C3CC3)c3ccc(Cl)cc3)C[C@@H]2C)cc1>O.CO.O1CCCC1>C[C@H]1C[C@@H](N(C(=O)C2CC2)c2ccc(Cl)cc2)c2ccccc2N1C(=O)c1ccc(OCCC(C)(C)C(=O)O)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-90e2427c2c1f47b09894c70bbe445f5b | CCc1cc(C(=O)OC)ccc1F>>CCc1cc(C(=O)O)ccc1F | C(C)C=1C=C(C(=O)OC)C=CC1F.[OH-].[Li+]>>FC1=C(C=C(C(=O)O)C=C1)CC | C[O:8][C:6]([c:5]1[cH:4][c:3]([CH2:2][CH3:1])[c:11]([F:12])[cH:10][cH:9]1)=[O:7]>>[CH3:1][CH2:2][c:3]1[cH:4][c:5]([C:6](=[O:7])[OH:8])[cH:9][cH:10][c:11]1[F:12] | CCc1cc(C(=O)OC)ccc1F | CCc1cc(C(=O)O)ccc1F | null | [Pd] | CO.O1CCCC1.O.CO | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccccc1 | C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]>>[O;D1;H0:3]=[C:2](-[OH;D1;+0:1])-[c:4] | null | [] | null | null | 2 | HOUR | (4-fluoro-3-ethylbenzoyl chloride was prepared in 5 steps from 3-bromo-4-fluorobenzoic acid. 3-bromo-4-fluorobenzoic acid was converted to methyl 3-bromo-4-fluorobenzoate by treatment with trimethylsilyl diazomethane (1.5 equivalents) in benzene/methanol (4/1) at room temperature. Subsequent reaction with tributyl(viny... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1 | Other | [Pd].CO.O1CCCC1.O.CO | null | 2 | CCc1cc(C(=O)OC)ccc1F>[Pd].CO.O1CCCC1.O.CO>CCc1cc(C(=O)O)ccc1F |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-53b6a1d374464c7dadaa4a3f7b6367b9 | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(O)cc2)c2ccccc21.CC(C)(CCO)n1ccnc1>>CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(OCCC(C)(C)n3ccnc3)cc2)c2ccccc21 | CCOC(=O)/N=N/C(=O)OCC.ClC1=CC=C(C=C1)N(C(C)=O)[C@@H]1C[C@@H](N(C2=CC=CC=C12)C(C1=CC=C(C=C1)O)=O)C.N1(C=NC=C1)C(CCO)(C)C.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3>>ClC1=CC=C(C=C1)N(C(C)=O)[C@@H]1C[C@@H](N(C2=CC=CC=C12)C(C1=CC=C(C=C1)OCCC(C)(C)N1C=NC=C1)=O)C | [CH3:1][C:2](=[O:3])[N:4]([c:5]1[cH:6][cH:7][c:8]([Cl:9])[cH:10][cH:11]1)[C@@H:12]1[CH2:13][C@H:14]([CH3:15])[N:16]([C:17](=[O:18])[c:19]2[cH:20][cH:21][c:22]([OH:23])[cH:34][cH:35]2)[c:36]2[cH:37][cH:38][cH:39][cH:40][c:41]21.O[CH2:24][CH2:25][C:26]([CH3:27])([CH3:28])[n:29]1[cH:30][cH:31][n:32][cH:33]1>>[CH3:1][C:2](... | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(O)cc2)c2ccccc21.CC(C)(CCO)n1ccnc1 | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(OCCC(C)(C)n3ccnc3)cc2)c2ccccc21 | null | null | C1=CC=CC=C1 | Heteroatom Alkylation and Arylation | Mitsunobu aryl ether | 86bfb73617450d22f9456ed5ce4d96a73f1f8fc0c016bebae57fda68e2da86a2 | 2258bd14c3b5449b92dc09cf9fa522f88d5071b4af20f7e968b60aa1ae6db0cf | O=C(c1ccc(OCCCn2ccnc2)cc1)N1CC[C@@H](Nc2ccccc2)c2ccccc21 | O-[CH2;D2;+0:1]-[C:2]-[C:3].[OH;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:4]-[c:5](:[c:6]):[c:7] | 46 | [{"value": 46.0, "product": "ClC1=CC=C(C=C1)N(C(C)=O)[C@@H]1C[C@@H](N(C2=CC=CC=C12)C(C1=CC=C(C=C1)OCCC(C)(C)N1C=NC=C1)=O)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 5 | MINUTE | 3-Imidazol-1-yl-3-methyl-butan-1-ol was dissolved in benzene at room temperature with PPh3 (0.088 g, 0.33 mmol) added (2S,4R)-N-(4-chloro-phenyl)-N-[1-(4-hydroxy-benzoyl)-2-methyl-1,2,3,4-tetrahydro-quinolin-4-yl]-acetamide (0.133 g, 0.30 mmol) and stirred for 5 min. DEAD (0.058 g, 0.33 mmol) was added and the reaction... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Aromatic alcohol | Ether | null | null | c1ccccc1.c1ccccc1.c1c[nH]cn1.c1ccc2c(c1)CCC[NH]2 | HO- | C1=CC=CC=C1 | null | 0.083333 | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(O)cc2)c2ccccc21.CC(C)(CCO)n1ccnc1>C1=CC=CC=C1>CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(OCCC(C)(C)n3ccnc3)cc2)c2ccccc21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-217d6172dd4a4309820f436cdcba0e57 | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(OCC3CCNCC3)cc2)c2ccccc21.CC=O>>CCN1CCC(COc2ccc(C(=O)N3c4ccccc4[C@H](N(C(C)=O)c4ccc(Cl)cc4)C[C@@H]3C)cc2)CC1 | ClC1=CC=C(C=C1)N(C(C)=O)[C@@H]1C[C@@H](N(C2=CC=CC=C12)C(C1=CC=C(C=C1)OCC1CCNCC1)=O)C.C(C)=O.[BH-](OC(=O)C)(OC(=O)C)OC(=O)C.[Na+]>>ClC1=CC=C(C=C1)N(C(C)=O)[C@@H]1C[C@@H](N(C2=CC=CC=C12)C(C1=CC=C(C=C1)OCC1CCN(CC1)CC)=O)C | [NH:3]1[CH2:4][CH2:5][CH:6]([CH2:7][O:8][c:9]2[cH:10][cH:11][c:12]([C:13](=[O:14])[N:15]3[c:16]4[cH:17][cH:18][cH:19][cH:20][c:21]4[C@H:22]([N:23]([C:24]([CH3:25])=[O:26])[c:27]4[cH:28][cH:29][c:30]([Cl:31])[cH:32][cH:33]4)[CH2:34][C@@H:35]3[CH3:36])[cH:37][cH:38]2)[CH2:39][CH2:40]1.O=[CH:2][CH3:1]>>[CH3:1][CH2:2][N:3]... | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(OCC3CCNCC3)cc2)c2ccccc21.CC=O | CCN1CCC(COc2ccc(C(=O)N3c4ccccc4[C@H](N(C(C)=O)c4ccc(Cl)cc4)C[C@@H]3C)cc2)CC1 | null | null | ClCCl | Heteroatom Alkylation and Arylation | reductive amination | d0e659bc8d1e29e09a61320b4c537e66ad57335a51368c8bd48de9bdffa59372 | 2d03f38884b1fbb0c0d6e6f2de31afb25102fec87f347c3a123e064c1bfef0ad | O=C(c1ccc(OCC2CCNCC2)cc1)N1CC[C@@H](Nc2ccccc2)c2ccccc21 | O=[CH;D2;+0:1]-[C;D1;H3:2].[C:3]-[C:4]-[NH;D2;+0:5]-[C:6]-[C:7]>>[C:3]-[C:4]-[N;H0;D3;+0:5](-[CH2;D2;+0:1]-[C;D1;H3:2])-[C:6]-[C:7] | 55 | [{"value": 55.0, "product": "ClC1=CC=C(C=C1)N(C(C)=O)[C@@H]1C[C@@H](N(C2=CC=CC=C12)C(C1=CC=C(C=C1)OCC1CCN(CC1)CC)=O)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The piperdine was reacted with acetaldehyde, Na(OAc)3BH in dichloromethane at room temperature overnight. Then washed with 1N NaOH, dried over MgSO4, filtered and concentrated down. The crude residue was purified by silica gel chromatography (10% methanol/90% dichloromethane) to afford the product (55%).
Conditions: Se... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Secondary amine | Tertiary amine | C1CCNCC1 | C1CC[NH]CC1 | C1CC[NH]CC1.c1ccccc1.c1ccccc1.c1ccc2c(c1)CCC[NH]2 | Other | ClCCl | null | null | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(OCC3CCNCC3)cc2)c2ccccc21.CC=O>ClCCl>CCN1CCC(COc2ccc(C(=O)N3c4ccccc4[C@H](N(C(C)=O)c4ccc(Cl)cc4)C[C@@H]3C)cc2)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-fa1545499cc04897b27dabdb60c8c706 | COC(=O)C(C)(C)CCOc1cc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccc(Cl)cc3)C[C@@H]2C)ccc1F>>CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(F)c(OCCC(C)(C)C(=O)O)c2)c2ccccc21 | C(C)(=O)N([C@@H]1C[C@@H](N(C2=CC=CC=C12)C(=O)C=1C=CC(=C(OCCC(C(=O)OC)(C)C)C1)F)C)C1=CC=C(C=C1)Cl.[Li+].[OH-]>>C(C)(=O)N([C@@H]1C[C@@H](N(C2=CC=CC=C12)C(=O)C=1C=CC(=C(OCCC(C(=O)O)(C)C)C1)F)C)C1=CC=C(C=C1)Cl | C[O:33][C:31]([C:28]([CH2:27][CH2:26][O:25][c:24]1[c:22]([F:23])[cH:21][cH:20][c:19]([C:17]([N:16]2[C@@H:14]([CH3:15])[CH2:13][C@@H:12]([N:4]([C:2]([CH3:1])=[O:3])[c:5]3[cH:6][cH:7][c:8]([Cl:9])[cH:10][cH:11]3)[c:40]3[c:35]2[cH:36][cH:37][cH:38][cH:39]3)=[O:18])[cH:34]1)([CH3:29])[CH3:30])=[O:32]>>[CH3:1][C:2](=[O:3])[... | COC(=O)C(C)(C)CCOc1cc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccc(Cl)cc3)C[C@@H]2C)ccc1F | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(F)c(OCCC(C)(C)C(=O)O)c2)c2ccccc21 | null | null | CO.C1CCOC1 | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | O=C(c1ccccc1)N1CC[C@@H](Nc2ccccc2)c2ccccc21 | 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] | null | [] | null | null | 8 | HOUR | To the solution of Methyl 4-(5-{[(2S,4R)-4-[acetyl(4-chlorophenyl)amino]-2-methyl-3,4-dihydroquinolin-1(2H)-yl]carbonyl}-2-fluorophenoxy)-2,2-dimethylbutanoate in MeOH/THF (1 mL/1 mL) was added excessive LiOH (1N aqueous solution). The reaction mixture was stirred at r.t. for overnight. The reaction was quenched by add... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1.c1ccccc1.c1ccc2c(c1)CCC[NH]2 | Other | CO.C1CCOC1 | null | 8 | COC(=O)C(C)(C)CCOc1cc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccc(Cl)cc3)C[C@@H]2C)ccc1F>CO.C1CCOC1>CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(F)c(OCCC(C)(C)C(=O)O)c2)c2ccccc21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-61d2f884d424442d8dd39ecaf517e5d6 | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(N(S(C)(=O)=O)S(C)(=O)=O)cc2)c2ccccc21>>CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(NS(C)(=O)=O)cc2)c2ccccc21 | O.C([O-])(O)=O.[Na+].CS(=O)(=O)N(C1=CC=C(C(=O)N2[C@H](C[C@H](C3=CC=CC=C23)N(C(C)=O)C2=CC=C(C=C2)Cl)C)C=C1)S(=O)(=O)C.[OH-].[Na+]>>ClC1=CC=C(C=C1)N(C(C)=O)[C@@H]1C[C@@H](N(C2=CC=CC=C12)C(C1=CC=C(C=C1)NS(=O)(=O)C)=O)C | CS(=O)(=O)[N:23]([c:22]1[cH:21][cH:20][c:19]([C:17]([N:16]2[C@@H:14]([CH3:15])[CH2:13][C@@H:12]([N:4]([C:2]([CH3:1])=[O:3])[c:5]3[cH:6][cH:7][c:8]([Cl:9])[cH:10][cH:11]3)[c:35]3[c:30]2[cH:31][cH:32][cH:33][cH:34]3)=[O:18])[cH:29][cH:28]1)[S:24]([CH3:25])(=[O:26])=[O:27]>>[CH3:1][C:2](=[O:3])[N:4]([c:5]1[cH:6][cH:7][c:8... | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(N(S(C)(=O)=O)S(C)(=O)=O)cc2)c2ccccc21 | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(NS(C)(=O)=O)cc2)c2ccccc21 | null | null | O1CCCC1 | Reduction | Hydrogenolysis of tertiary amines | de0c360cde7152c6dc8d2dc7689a99d4783d487dca4b5e872fbf9bc8168f99f7 | 40552f2058ccfb8ff7e827f21cb476a78a40df984798f4706d5812adf64d0001 | O=C(c1ccccc1)N1CC[C@@H](Nc2ccccc2)c2ccccc21 | C-S(=O)(=O)-[N;H0;D3;+0:1](-[c:2](:[c:3]):[c:4])-[#16:5](-[C;D1;H3:6])(=[O;D1;H0:7])=[O;D1;H0:8]>>[C;D1;H3:6]-[#16:5](=[O;D1;H0:7])(=[O;D1;H0:8])-[NH;D2;+0:1]-[c:2](:[c:3]):[c:4] | 84.3 | [{"value": 76.0, "product": "ClC1=CC=C(C=C1)N(C(C)=O)[C@@H]1C[C@@H](N(C2=CC=CC=C12)C(C1=CC=C(C=C1)NS(=O)(=O)C)=O)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 84.3, "product": "ClC1=CC=C(C=C1)N(C(C)=O)[C@@H]1C[C@@H](N(C2=CC=CC=C12)C(C1=CC=C(C=C1)NS(=O)(=O)C)=O)C", "details": "CALCULATEDPERCENTYIELD", "... | null | null | 2 | DAY | To a solution of N-((2S,4R)-1-{4-[bis(methylsulfonyl)amino]benzoyl}-2-methyl-1,2,3,4-tetrahydroquinolin-4-yl)-N-(4-chlorophenyl)acetamide (259 mg, 0.44 mmol) in tetrahydrofuran (5.0 mL) at room temperature was added 1.0 M sodium hydroxide (0.880 mL, 0.88 mmol). The reaction was stirred at room temperature for 2 days. T... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amine | Sulfonamide | null | null | c1ccccc1.c1ccccc1.c1ccc2c(c1)CCC[NH]2 | HO- | O1CCCC1 | null | 48 | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(N(S(C)(=O)=O)S(C)(=O)=O)cc2)c2ccccc21>O1CCCC1>CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(NS(C)(=O)=O)cc2)c2ccccc21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-8e80d6b8a1c748f68ed40bad6c5176e6 | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(OCCCN)cc2)c2ccccc21.CN1CCC[C@H]1C(=O)O>>CC(=O)N(c1ccc(Cl)cc1)[C@@H]1CC(C)N(C(=O)c2ccc(OCCCNC(=O)[C@@H]3CCCN3C)cc2)c2ccccc21 | NCCCOC1=CC=C(C(=O)N2[C@H](C[C@H](C3=CC=CC=C23)N(C(C)=O)C2=CC=C(C=C2)Cl)C)C=C1.CN1[C@H](C(=O)O)CCC1.C(CCl)Cl>>C(C)(=O)N([C@@H]1CC(N(C2=CC=CC=C12)C(=O)C1=CC=C(OCCCNC(=O)[C@H]2N(CCC2)C)C=C1)C)C1=CC=C(C=C1)Cl | [CH3:1][C:2](=[O:3])[N:4]([c:5]1[cH:6][cH:7][c:8]([Cl:9])[cH:10][cH:11]1)[C@@H:12]1[CH2:13][C@H:14]([CH3:15])[N:16]([C:17](=[O:18])[c:19]2[cH:20][cH:21][c:22]([O:23][CH2:24][CH2:25][CH2:26][NH2:27])[cH:36][cH:37]2)[c:38]2[cH:39][cH:40][cH:41][cH:42][c:43]21.O[C:28](=[O:29])[C@@H:30]1[CH2:31][CH2:32][CH2:33][N:34]1[CH3:... | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(OCCCN)cc2)c2ccccc21.CN1CCC[C@H]1C(=O)O | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1CC(C)N(C(=O)c2ccc(OCCCNC(=O)[C@@H]3CCCN3C)cc2)c2ccccc21 | null | null | N1=CC=CC=C1.C(Cl)Cl | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(NCCCOc1ccc(C(=O)N2CC[C@@H](Nc3ccccc3)c3ccccc32)cc1)[C@@H]1CCCN1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[#7:5](-[C;D1;H3:6])-[C:7].[C:8]-[C:9]-[NH2;D1;+0:10]>>[C:8]-[C:9]-[NH;D2;+0:10]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[#7:5](-[C;D1;H3:6])-[C:7] | null | [] | null | null | 1 | HOUR | (2S,4R)-N-{1-[4-(3-Amino-propoxy)-benzoyl]-2-methyl-1,2,3,4-tetrahydro-quinolin-4-yl}-N-(4-chloro-phenyl)-acetamide (100 mg, 0.204 mmol) was dissolved in methylene chloride (2 mL) and pyridine (2 mL). N-methyl proline (33 mg, 0.255 mmol) and EDC (63 mg, 0.255 mmol) were added and the reaction was stirred for 1 hour. Th... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccccc1.C1CC[NH]C1.c1ccc2c(c1)CCC[NH]2 | HO- | N1=CC=CC=C1.C(Cl)Cl | null | 1 | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(OCCCN)cc2)c2ccccc21.CN1CCC[C@H]1C(=O)O>N1=CC=CC=C1.C(Cl)Cl>CC(=O)N(c1ccc(Cl)cc1)[C@@H]1CC(C)N(C(=O)c2ccc(OCCCNC(=O)[C@@H]3CCCN3C)cc2)c2ccccc21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-98f502800b7d437cb016572d856ab44a | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(OCCC(C)(C)C(=O)O)cc2)c2ccccc21>>CC(=O)N(c1ccc(Cl)cc1)[C@H]1C[C@@H](C)N(C(=O)c2ccc(OCCC(C)(C)C(=O)O)cc2)c2ccccc21 | C(C)(=O)N([C@@H]1C[C@@H](N(C2=CC=CC=C12)C(=O)C1=CC=C(OCCC(C(=O)O)(C)C)C=C1)C)C1=CC=C(C=C1)Cl.ClC1=CC=C(C=C1)N(C(C)=O)[C@@H]1C[C@@H](N(C2=CC=CC=C12)C(C1=CC=C(C=C1)OC)=O)C>>C(C)(=O)N([C@H]1C[C@H](N(C2=CC=CC=C12)C(=O)C1=CC=C(OCCC(C(=O)O)(C)C)C=C1)C)C1=CC=C(C=C1)Cl | [CH3:1][C:2](=[O:3])[N:4]([c:5]1[cH:6][cH:7][c:8]([Cl:9])[cH:10][cH:11]1)[C@@H:12]1[CH2:13][C@H:14]([CH3:15])[N:16]([C:17](=[O:18])[c:19]2[cH:20][cH:21][c:22]([O:23][CH2:24][CH2:25][C:26]([CH3:27])([CH3:28])[C:29](=[O:30])[OH:31])[cH:32][cH:33]2)[c:34]2[cH:35][cH:36][cH:37][cH:38][c:39]21>>[CH3:1][C:2](=[O:3])[N:4]([c:... | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(OCCC(C)(C)C(=O)O)cc2)c2ccccc21 | CC(=O)N(c1ccc(Cl)cc1)[C@H]1C[C@@H](C)N(C(=O)c2ccc(OCCC(C)(C)C(=O)O)cc2)c2ccccc21 | null | null | null | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | O=C(c1ccccc1)N1CC[C@H](Nc2ccccc2)c2ccccc21 | null | null | [] | null | null | null | null | 4-(4-{[(2R,4S)-4-[acetyl(4-chlorophenyl)amino]-2-methyl-3,4-dihydroquinolin-1(2H)-yl]carbonyl}phenoxy)-2,2-dimethylbutanoic acid was prepared following the procedure to prepare 4-(4-{[(2S,4R)-4-[acetyl(4-chlorophenyl)amino]-2-methyl-3,4-dihydro-quinolin-1(2H)-yl]carbonyl}phenoxy)-2,2-dimethylbutanoic acid, substituting... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | c1ccccc1.c1ccccc1.c1ccc2c(c1)CCC[NH]2 | null | null | null | null | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(OCCC(C)(C)C(=O)O)cc2)c2ccccc21>>CC(=O)N(c1ccc(Cl)cc1)[C@H]1C[C@@H](C)N(C(=O)c2ccc(OCCC(C)(C)C(=O)O)cc2)c2ccccc21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-12ca8a4bd50c4230a6f0da0d9d204f48 | CC(=O)CCCc1ccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccc(Cl)cc3)C[C@@H]2C)cc1>>CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(CCCC(C)(C)O)cc2)c2ccccc21 | ClC1=CC=C(C=C1)N(C(C)=O)[C@@H]1C[C@@H](N(C2=CC=CC=C12)C(C1=CC=C(C=C1)CCCC(C)=O)=O)C.C[Mg+].[Br-]>>ClC1=CC=C(C=C1)N(C(C)=O)[C@@H]1C[C@@H](N(C2=CC=CC=C12)C(C1=CC=C(C=C1)CCCC(C)(C)O)=O)C | [CH3:1][C:2](=[O:3])[N:4]([c:5]1[cH:6][cH:7][c:8]([Cl:9])[cH:10][cH:11]1)[C@@H:12]1[CH2:13][C@H:14]([CH3:15])[N:16]([C:17](=[O:18])[c:19]2[cH:20][cH:21][c:22]([CH2:23][CH2:24][CH2:25][C:26]([CH3:27])=[O:29])[cH:30][cH:31]2)[c:32]2[cH:33][cH:34][cH:35][cH:36][c:37]21>>[CH3:1][C:2](=[O:3])[N:4]([c:5]1[cH:6][cH:7][c:8]([C... | CC(=O)CCCc1ccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccc(Cl)cc3)C[C@@H]2C)cc1 | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(CCCC(C)(C)O)cc2)c2ccccc21 | null | null | C1CCOC1 | Miscellaneous | OtherReaction | 7e61014f084ef66fe8691c8f1abaf493e11079effe9d87ae329e041d937b8b3a | 8811b4d793f7cfa9f0f1f47a008648edabb54f371f76dfa680dd5b2e1564c6c5 | O=C(c1ccccc1)N1CC[C@@H](Nc2ccccc2)c2ccccc21 | [C:1]-[C:2]-[C;H0;D3;+0:3](-[C;D1;H3:4])=[O;H0;D1;+0:5]>>[C:1]-[C:2]-[C;H0;D4;+0:3](-[C;D1;H3:4])(-[C;D1;H3:6])-[OH;D1;+0:5] | 40 | [{"value": 40.0, "product": "ClC1=CC=C(C=C1)N(C(C)=O)[C@@H]1C[C@@H](N(C2=CC=CC=C12)C(C1=CC=C(C=C1)CCCC(C)(C)O)=O)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 39.0, "product": "ClC1=CC=C(C=C1)N(C(C)=O)[C@@H]1C[C@@H](N(C2=CC=CC=C12)C(C1=CC=C(C=C1)CCCC(C)(C)O)=O)C", "details": "CALCULATEDPERCENTYIELD", "... | 0 | CELSIUS | 2 | HOUR | To a solution of N-(4-chlorophenyl)-N-((2S,4R)-2-methyl-1-(4-(4-oxopentyl)benzoyl)-1,2,3,4-tetrahydroquinolin-4-yl)acetamide (40 mg, 0.079 mmol) in THF (2 mL), was added MeMgBr (68 uL, 0.095 mmol, 1.4 M solution in THF) at 0° C. The mixture was stirred at 0° C. for 2 h. After quenching with sat. NH4Cl solution, the mix... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Tertiary alcohol | null | null | c1ccccc1.c1ccccc1.c1ccc2c(c1)CCC[NH]2 | Other | C1CCOC1 | 0 | 2 | CC(=O)CCCc1ccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccc(Cl)cc3)C[C@@H]2C)cc1>C1CCOC1>CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(CCCC(C)(C)O)cc2)c2ccccc21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-b2b9ea51be7b485ea06c0c3cbdacbeab | COc1c(F)cc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccc(Cl)cc3)C[C@@H]2C)cc1F>>CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2cc(F)c(O)c(F)c2)c2ccccc21 | ClC1=CC=C(C=C1)N(C(C)=O)[C@@H]1C[C@@H](N(C2=CC=CC=C12)C(C1=CC(=C(C(=C1)F)OC)F)=O)C.B(Br)(Br)Br>>ClC1=CC=C(C=C1)N(C(C)=O)[C@@H]1C[C@@H](N(C2=CC=CC=C12)C(C1=CC(=C(C(=C1)F)O)F)=O)C | C[O:24][c:23]1[c:21]([F:22])[cH:20][c:19]([C:17]([N:16]2[C@@H:14]([CH3:15])[CH2:13][C@@H:12]([N:4]([C:2]([CH3:1])=[O:3])[c:5]3[cH:6][cH:7][c:8]([Cl:9])[cH:10][cH:11]3)[c:33]3[c:28]2[cH:29][cH:30][cH:31][cH:32]3)=[O:18])[cH:27][c:25]1[F:26]>>[CH3:1][C:2](=[O:3])[N:4]([c:5]1[cH:6][cH:7][c:8]([Cl:9])[cH:10][cH:11]1)[C@@H:... | COc1c(F)cc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccc(Cl)cc3)C[C@@H]2C)cc1F | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2cc(F)c(O)c(F)c2)c2ccccc21 | null | null | ClCCl | Deprotection | Cleavage of methoxy ethers to alcohols | c5320c7dfa4f544d4900efcae9b3262bf0d5286bcf39c86109232351f35b23d5 | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | O=C(c1ccccc1)N1CC[C@@H](Nc2ccccc2)c2ccccc21 | C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[OH;D1;+0:1]-[c:2](:[c:3]):[c:4] | 78.7 | [{"value": 78.0, "product": "ClC1=CC=C(C=C1)N(C(C)=O)[C@@H]1C[C@@H](N(C2=CC=CC=C12)C(C1=CC(=C(C(=C1)F)O)F)=O)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 78.7, "product": "ClC1=CC=C(C=C1)N(C(C)=O)[C@@H]1C[C@@H](N(C2=CC=CC=C12)C(C1=CC(=C(C(=C1)F)O)F)=O)C", "details": "CALCULATEDPERCENTYIELD", "is_desir... | null | null | null | null | N-(4-chlorophenyl)-N-[(2S,4R)-1-(3,5-difluoro-4-methoxybenzoyl)-2-methyl-1,2,3,4-tetrahydroquinolin-4-yl]acetamide (200 mg, 0.41 mmol) was dissolved in dichloromethane and a solution of BBr3 (1.0 M in dichloromethane, 3.0 mL) was added; the reaction mixture was stirred at room temperature for until no starting material... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | null | null | c1ccccc1.c1ccccc1.c1ccc2c(c1)CCC[NH]2 | Other | ClCCl | null | null | COc1c(F)cc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccc(Cl)cc3)C[C@@H]2C)cc1F>ClCCl>CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2cc(F)c(O)c(F)c2)c2ccccc21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-dc52b191e34d4cd99f8b626c4f71e0c6 | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(OCCCN)cc2)c2ccccc21.COC(=O)Cl>>COC(=O)NCCCOc1ccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccc(Cl)cc3)C[C@@H]2C)cc1 | NCCCOC1=CC=C(C(=O)N2[C@H](C[C@H](C3=CC=CC=C23)N(C(C)=O)C2=CC=C(C=C2)Cl)C)C=C1.ClC(=O)OC>>COC(NCCCOC1=CC=C(C=C1)C(=O)N1[C@H](C[C@H](C2=CC=CC=C12)N(C1=CC=C(C=C1)Cl)C(C)=O)C)=O | [NH2:5][CH2:6][CH2:7][CH2:8][O:9][c:10]1[cH:11][cH:12][c:13]([C:14](=[O:15])[N:16]2[c:17]3[cH:18][cH:19][cH:20][cH:21][c:22]3[C@H:23]([N:24]([C:25]([CH3:26])=[O:27])[c:28]3[cH:29][cH:30][c:31]([Cl:32])[cH:33][cH:34]3)[CH2:35][C@@H:36]2[CH3:37])[cH:38][cH:39]1.Cl[C:3]([O:2][CH3:1])=[O:4]>>[CH3:1][O:2][C:3](=[O:4])[NH:5]... | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(OCCCN)cc2)c2ccccc21.COC(=O)Cl | COC(=O)NCCCOc1ccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccc(Cl)cc3)C[C@@H]2C)cc1 | null | null | C(Cl)Cl | Protection | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 038720aa61a7efa0f2a9ee6f2e0adf63a9ffdc2be4697c11a6215baef34f97b2 | 205f353513ce9506ab61831799da8fb73ec2ef5cfa927664496d3ce72c438860 | O=C(c1ccccc1)N1CC[C@@H](Nc2ccccc2)c2ccccc21 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C;D1;H3:4].[C:5]-[C:6]-[NH2;D1;+0:7]>>[C:5]-[C:6]-[NH;D2;+0:7]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C;D1;H3:4] | 52 | [{"value": 52.0, "product": "COC(NCCCOC1=CC=C(C=C1)C(=O)N1[C@H](C[C@H](C2=CC=CC=C12)N(C1=CC=C(C=C1)Cl)C(C)=O)C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 43.0, "product": "COC(NCCCOC1=CC=C(C=C1)C(=O)N1[C@H](C[C@H](C2=CC=CC=C12)N(C1=CC=C(C=C1)Cl)C(C)=O)C)=O", "details": "CALCULATEDPERCENTYIELD", "is... | null | null | 18 | HOUR | (2S,4R)-N-{1-[4-(3-Amino-propoxy)-benzoyl]-2-methyl-1,2,3,4-tetrahydro-quinolin-4-yl}-N-(4-chloro-phenyl)-acetamide (150 mg, 0.30 mmol) was dissolved in DCM (1 mL). To this solution was added TEA (36.4 mg, 0.36 mmol) followed by methyl chloroformate (34 mg, 0.36 mmol). The reaction mixture was stirred at room temperatu... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Ether.Primary amine | Carbamic ester | null | null | c1ccccc1.c1ccccc1.c1ccc2c(c1)CCC[NH]2 | HCl | C(Cl)Cl | null | 18 | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(OCCCN)cc2)c2ccccc21.COC(=O)Cl>C(Cl)Cl>COC(=O)NCCCOc1ccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccc(Cl)cc3)C[C@@H]2C)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-02d179395a7c42c29f7a5b41e2967e41 | COC(=O)c1ccc(COc2ccc(C(=O)N3c4ccccc4[C@H](N(C(C)=O)c4ccc(Cl)cc4)C[C@@H]3C)cc2)o1>>CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(OCc3ccc(C(=O)O)o3)cc2)c2ccccc21 | COC(=O)C=1OC(=CC1)COC1=CC=C(C=C1)C(=O)N1[C@H](C[C@H](C2=CC=CC=C12)N(C1=CC=C(C=C1)Cl)C(C)=O)C.C(C)O.[OH-].[Na+]>>C(C)(=O)N([C@@H]1C[C@@H](N(C2=CC=CC=C12)C(=O)C1=CC=C(OCC2=CC=C(O2)C(=O)O)C=C1)C)C1=CC=C(C=C1)Cl | C[O:31][C:29]([c:28]1[cH:27][cH:26][c:25]([CH2:24][O:23][c:22]2[cH:21][cH:20][c:19]([C:17]([N:16]3[C@@H:14]([CH3:15])[CH2:13][C@@H:12]([N:4]([C:2]([CH3:1])=[O:3])[c:5]4[cH:6][cH:7][c:8]([Cl:9])[cH:10][cH:11]4)[c:40]4[c:35]3[cH:36][cH:37][cH:38][cH:39]4)=[O:18])[cH:34][cH:33]2)[o:32]1)=[O:30]>>[CH3:1][C:2](=[O:3])[N:4](... | COC(=O)c1ccc(COc2ccc(C(=O)N3c4ccccc4[C@H](N(C(C)=O)c4ccc(Cl)cc4)C[C@@H]3C)cc2)o1 | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(OCc3ccc(C(=O)O)o3)cc2)c2ccccc21 | null | null | O1CCCC1 | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | O=C(c1ccc(OCc2ccco2)cc1)N1CC[C@@H](Nc2ccccc2)c2ccccc21 | C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]:[#8;a:5]>>[#8;a:5]:[c:4]-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1] | null | [] | null | null | 4 | HOUR | (2S,4R)-5-(4-{4-[Acetyl-(4-chloro-phenyl)-amino]-2-methyl-3,4-dihydro-2H-quinoline-1-carbonyl}-phenoxymethyl)-furan-2-carboxylic acid methyl ester (0.145 g, 0.25 mmol) was hydrolyzed to the acid by dissolving in tetrahydrofuran and ethanol and sodium hydroxide (1N) was added. The mixture was stirred at room temperature... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1.c1ccccc1.c1ccoc1.c1ccc2c(c1)CCC[NH]2 | Other | O1CCCC1 | null | 4 | COC(=O)c1ccc(COc2ccc(C(=O)N3c4ccccc4[C@H](N(C(C)=O)c4ccc(Cl)cc4)C[C@@H]3C)cc2)o1>O1CCCC1>CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(OCc3ccc(C(=O)O)o3)cc2)c2ccccc21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-48311e6822004b5fb134fa57b17d727d | CC(N)=O.COC(=O)C(=C[O-])C(OC)OC>>COC(=O)c1cnc(C)nc1 | Cl.C(C)(=O)N.COC(C(=C[O-])C(=O)OC)OC.[Na+].CN(C=O)C>>CC1=NC=C(C=N1)C(=O)OC | O=[C:8]([CH3:9])[NH2:10].CO[CH:6](OC)[C:5]([C:3]([O:2][CH3:1])=[O:4])=[CH:11][O-]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][n:7][c:8]([CH3:9])[n:10][cH:11]1 | CC(N)=O.COC(=O)C(=C[O-])C(OC)OC | COC(=O)c1cnc(C)nc1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | c99c005b9407326da56e76b50f4dd84c25b6e915d5663e90eda36909527618cf | 508036d318a8048f2d7ac8fdf8bbcc4daff877d5b758b7becdb5bd510dcca62d | c1cncnc1 | C-O-[CH;D3;+0:1](-O-C)-[C;H0;D3;+0:2](=[CH;D2;+0:3]-[O-])-[C:4](=[O;D1;H0:5])-[#8:6]-[C;D1;H3:7].O=[C;H0;D3;+0:8](-[C;D1;H3:9])-[NH2;D1;+0:10]>>[C;D1;H3:7]-[#8:6]-[C:4](=[O;D1;H0:5])-[c;H0;D3;+0:2]1:[cH;D2;+0:3]:[n;H0;D2;+0:10]:[c;H0;D3;+0:8](-[C;D1;H3:9]):[#7;a:11]:[cH;D2;+0:1]:1 | null | [] | 100 | CELSIUS | null | null | N-(4-chlorophenyl)-N-{(2S,4R)-2-methyl-1-[(2-methylpyrimidin-5-yl)carbonyl]-1,2,3,4-tetrahydroquinolin-4-yl}acetamide was prepared following general procedure H, substituting 2-methylpyrimidine-5-carbonyl chloride for 6-trifluoromethyl nicotinyl chloride. (2-methylpyrimidine-5-carbonyl chloride was prepared in four ste... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ether.Ether.Primary amide | Ester | null | c1cncnc1 | c1cncnc1 | HO- | null | 100 | null | CC(N)=O.COC(=O)C(=C[O-])C(OC)OC>>COC(=O)c1cnc(C)nc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-3975f0ddc3c24bc78b568678041c3aa4 | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(O)cc2)c2ccccc21.CCOC(=O)CCCBr>>CCOC(=O)CCCOc1ccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccc(Cl)cc3)C[C@@H]2C)cc1 | ClC1=CC=C(C=C1)N(C(C)=O)[C@@H]1C[C@@H](N(C2=CC=CC=C12)C(C1=CC=C(C=C1)O)=O)C.C(=O)([O-])[O-].[K+].[K+].C(C)OC(CCCBr)=O>>C(C)OC(CCCOC1=CC=C(C=C1)C(=O)N1[C@H](C[C@H](C2=CC=CC=C12)N(C1=CC=C(C=C1)Cl)C(C)=O)C)=O | [OH:9][c:10]1[cH:11][cH:12][c:13]([C:14](=[O:15])[N:16]2[c:17]3[cH:18][cH:19][cH:20][cH:21][c:22]3[C@H:23]([N:24]([C:25]([CH3:26])=[O:27])[c:28]3[cH:29][cH:30][c:31]([Cl:32])[cH:33][cH:34]3)[CH2:35][C@@H:36]2[CH3:37])[cH:38][cH:39]1.Br[CH2:8][CH2:7][CH2:6][C:4]([O:3][CH2:2][CH3:1])=[O:5]>>[CH3:1][CH2:2][O:3][C:4](=[O:5... | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(O)cc2)c2ccccc21.CCOC(=O)CCCBr | CCOC(=O)CCCOc1ccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccc(Cl)cc3)C[C@@H]2C)cc1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | O=C(c1ccccc1)N1CC[C@@H](Nc2ccccc2)c2ccccc21 | Br-[CH2;D2;+0:1]-[C:2]-[C:3]-[C:4](-[#8:5])=[O;D1;H0:6].[OH;D1;+0:7]-[c:8](:[c:9]):[c:10]>>[#8:5]-[C:4](=[O;D1;H0:6])-[C:3]-[C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:7]-[c:8](:[c:9]):[c:10] | null | [] | 80 | CELSIUS | null | null | (2S,4R)-N-(4-Chloro-phenyl)-N-[1-(4-hydroxy-benzoyl)-2-methyl-1,2,3,4-tetrahydro-quinolin-4-yl]-acetamide was dissolved in DMF at room temperature and K2CO3 was added. Ethyl-4-bromobutyrate was added and the reaction was allowed to heat to 80° C. overnight. The reaction mixture was concentrated in vacuo. The residue wa... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccccc1.c1ccccc1.c1ccc2c(c1)CCC[NH]2 | HBr | CN(C)C=O | 80 | null | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(O)cc2)c2ccccc21.CCOC(=O)CCCBr>CN(C)C=O>CCOC(=O)CCCOc1ccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccc(Cl)cc3)C[C@@H]2C)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-3fa66ee1848241f38ef8c6c545005537 | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(O)cc2)c2ccccc21.COC(=O)c1cccc(CBr)c1>>COC(=O)c1cccc(COc2ccc(C(=O)N3c4ccccc4[C@H](N(C(C)=O)c4ccc(Cl)cc4)C[C@@H]3C)cc2)c1 | ClC1=CC=C(C=C1)N(C(C)=O)[C@@H]1C[C@@H](N(C2=CC=CC=C12)C(C1=CC=C(C=C1)O)=O)C.C(=O)([O-])[O-].[Cs+].[Cs+].BrCC=1C=C(C(=O)OC)C=CC1>>COC(C1=CC(=CC=C1)COC1=CC=C(C=C1)C(=O)N1[C@H](C[C@H](C2=CC=CC=C12)N(C1=CC=C(C=C1)Cl)C(C)=O)C)=O | [OH:11][c:12]1[cH:13][cH:14][c:15]([C:16](=[O:17])[N:18]2[c:19]3[cH:20][cH:21][cH:22][cH:23][c:24]3[C@H:25]([N:26]([C:27]([CH3:28])=[O:29])[c:30]3[cH:31][cH:32][c:33]([Cl:34])[cH:35][cH:36]3)[CH2:37][C@@H:38]2[CH3:39])[cH:40][cH:41]1.Br[CH2:10][c:9]1[cH:8][cH:7][cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[cH:42]1>>[CH3:1][O:... | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(O)cc2)c2ccccc21.COC(=O)c1cccc(CBr)c1 | COC(=O)c1cccc(COc2ccc(C(=O)N3c4ccccc4[C@H](N(C(C)=O)c4ccc(Cl)cc4)C[C@@H]3C)cc2)c1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | O=C(c1ccc(OCc2ccccc2)cc1)N1CC[C@@H](Nc2ccccc2)c2ccccc21 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[OH;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[c:7]:[c:6](-[O;H0;D2;+0:5]-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4]):[c:8] | 54.4 | [{"value": 54.0, "product": "COC(C1=CC(=CC=C1)COC1=CC=C(C=C1)C(=O)N1[C@H](C[C@H](C2=CC=CC=C12)N(C1=CC=C(C=C1)Cl)C(C)=O)C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 54.4, "product": "COC(C1=CC(=CC=C1)COC1=CC=C(C=C1)C(=O)N1[C@H](C[C@H](C2=CC=CC=C12)N(C1=CC=C(C=C1)Cl)C(C)=O)C)=O", "details": "CALCULAT... | null | null | 18 | HOUR | (2S,4R)-N-(4-Chloro-phenyl)-N-[1-(4-hydroxy-benzoyl)-2-methyl-1,2,3,4-tetrahydro-quinolin-4-yl]-acetamide (150 mg, 0.35 mmol) was dissolved in DMF (5 mL) at room temperature. Cs2CO3 (283 mg, 0.87 mmol) was added followed by methyl 3-(bromomethyl)benzoate (119 mg, 0.52 mmol) and the reaction was stirred at room temperat... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccccc1.c1ccccc1.c1ccccc1.c1ccc2c(c1)CCC[NH]2 | HBr | CN(C)C=O | null | 18 | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(O)cc2)c2ccccc21.COC(=O)c1cccc(CBr)c1>CN(C)C=O>COC(=O)c1cccc(COc2ccc(C(=O)N3c4ccccc4[C@H](N(C(C)=O)c4ccc(Cl)cc4)C[C@@H]3C)cc2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-4b58686b737a43c9820eb1d963663eba | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(OS(=O)(=O)C(F)(F)F)cc2)c2ccccc21.CCOC(=O)C1CCNCC1>>CCOC(=O)C1CCN(c2ccc(C(=O)N3c4ccccc4[C@H](N(C(C)=O)c4ccc(Cl)cc4)C[C@@H]3C)cc2)CC1 | C(C)OC(=O)C1CCNCC1.C(=O)([O-])[O-].[Cs+].[Cs+].C=1C=CC(=CC1)P(C=2C=CC=CC2)C3=CC=C4C=CC=CC4=C3C5=C6C=CC=CC6=CC=C5P(C=7C=CC=CC7)C=8C=CC=CC8.C1COCCOCCOCCOCCOCCO1.C(C)(=O)N([C@@H]1C[C@@H](N(C2=CC=CC=C12)C(=O)C1=CC=C(C=C1)OS(=O)(=O)C(F)(F)F)C)C1=CC=C(C=C1)Cl>>C(C)OC(=O)C1CCN(CC1)C1=CC=C(C=C1)C(=O)N1[C@H](C[C@H](C2=CC=CC=C12... | O=S(=O)(O[c:10]1[cH:11][cH:12][c:13]([C:14](=[O:15])[N:16]2[c:17]3[cH:18][cH:19][cH:20][cH:21][c:22]3[C@H:23]([N:24]([C:25]([CH3:26])=[O:27])[c:28]3[cH:29][cH:30][c:31]([Cl:32])[cH:33][cH:34]3)[CH2:35][C@@H:36]2[CH3:37])[cH:38][cH:39]1)C(F)(F)F.[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]1[CH2:7][CH2:8][NH:9][CH2:40][CH2:41]... | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(OS(=O)(=O)C(F)(F)F)cc2)c2ccccc21.CCOC(=O)C1CCNCC1 | CCOC(=O)C1CCN(c2ccc(C(=O)N3c4ccccc4[C@H](N(C(C)=O)c4ccc(Cl)cc4)C[C@@H]3C)cc2)CC1 | null | C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd] | C1(=CC=CC=C1)C | Heteroatom Alkylation and Arylation | Alkylation of amines | f949f1d3fd566ba42e2236794c8fa62f2dccce09ff5ca665dca94a2a29579577 | 9a1a0c2e1b87bdf69534c723b7058cd90b31cce176c7a3bc658b2756600b117c | O=C(c1ccc(N2CCCCC2)cc1)N1CC[C@@H](Nc2ccccc2)c2ccccc21 | F-C(-F)(-F)-S(=O)(=O)-O-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[C:6]-[C:7]-[NH;D2;+0:8]-[C:9]-[C:10]>>[C:6]-[C:7]-[N;H0;D3;+0:8](-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5])-[C:9]-[C:10] | null | [] | null | null | null | null | (2S,4R)-1-(4-{4-[Acetyl-(4-chloro-phenyl)-amino]-2-methyl-3,4-dihydro-2H-quinoline-1-carbonyl}-phenyl)-piperidine-4-carboxylic acid ethyl ester was prepared from (2S,4R)-trifluoro-methanesulfonic acid 4-{4-[acetyl(4-chloro-phenyl)-amino]-2-methyl-3,4-dihydro-2H-quinoline-1-carbonyl}-phenyl ester by adding piperidine-4-... | 10.6084/m9.figshare.5104873.v1 | null | Triflate.Secondary amine | Tertiary amine | c1ccccc1.C1CCNCC1 | C1CC[NH]CC1.c1ccccc1 | C1CC[NH]CC1.c1ccccc1.c1ccccc1.c1ccc2c(c1)CCC[NH]2 | TfOH.HO- | C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].C1(=CC=CC=C1)C | null | null | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(OS(=O)(=O)C(F)(F)F)cc2)c2ccccc21.CCOC(=O)C1CCNCC1>C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].C1(=CC=CC=C1)C>CCOC(=O)C1CCN(c2ccc(C(=O)N3c4ccccc4[C@H](N(C(C)=O)c4ccc(Cl)cc4)C[C@@H]3C)cc... |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-46d7c213297442b69d3385686280f83d | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(OCCCN)cc2)c2ccccc21.O=C(Cl)OCCBr>>CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(OCCCN3CCOC3=O)cc2)c2ccccc21 | C(=O)([O-])[O-].[Cs+].[Cs+].C(C)N(CC)CC.NCCCOC1=CC=C(C(=O)N2[C@H](C[C@H](C3=CC=CC=C23)N(C(C)=O)C2=CC=C(C=C2)Cl)C)C=C1.BrCCOC(=O)Cl>>ClC1=CC=C(C=C1)N(C(C)=O)[C@@H]1C[C@@H](N(C2=CC=CC=C12)C(C1=CC=C(C=C1)OCCCN1C(OCC1)=O)=O)C | [CH3:1][C:2](=[O:3])[N:4]([c:5]1[cH:6][cH:7][c:8]([Cl:9])[cH:10][cH:11]1)[C@@H:12]1[CH2:13][C@H:14]([CH3:15])[N:16]([C:17](=[O:18])[c:19]2[cH:20][cH:21][c:22]([O:23][CH2:24][CH2:25][CH2:26][NH2:27])[cH:33][cH:34]2)[c:35]2[cH:36][cH:37][cH:38][cH:39][c:40]21.Cl[C:31]([O:30][CH2:29][CH2:28]Br)=[O:32]>>[CH3:1][C:2](=[O:3]... | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(OCCCN)cc2)c2ccccc21.O=C(Cl)OCCBr | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(OCCCN3CCOC3=O)cc2)c2ccccc21 | null | null | C(Cl)Cl.CN(C)C=O | Protection | OtherReaction | 15613fb2a10be402bb909c91fd72914a5bd3a21a9fe5a928a138d607049bdc15 | 2c78a61345fd52f9bd102038239c266d368f2005df51acc4baccc29a58dd2e3c | O=C1OCCN1CCCOc1ccc(C(=O)N2CC[C@@H](Nc3ccccc3)c3ccccc32)cc1 | Br-[CH2;D2;+0:1]-[C:2]-[#8:3]-[C;H0;D3;+0:4](-Cl)=[O;D1;H0:5].[C:6]-[C:7]-[NH2;D1;+0:8]>>[C:6]-[C:7]-[N;H0;D3;+0:8]1-[CH2;D2;+0:1]-[C:2]-[#8:3]-[C;H0;D3;+0:4]-1=[O;D1;H0:5] | null | [] | null | null | 1 | HOUR | (2S,4R)-N-{1-[4-(3-Amino-propoxy)-benzoyl]-2-methyl-1,2,3,4-tetrahydro-quinolin-4-yl}-N-(4-chloro-phenyl)-acetamide (50 mg, 0.102 mmol) was dissolved in methylene chloride (3 mL) and triethylamine (0.150 mL, 1.08 mmol) and cooled to −40° C. 2-Bromoethylchloroformate (0.016 mL, 0.153 mmol) was added and the reaction was... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary halide.Ether.Primary amine | Carbamic ester.Ether | null | C1COC[NH]1 | c1ccccc1.c1ccccc1.C1COC[NH]1.c1ccc2c(c1)CCC[NH]2 | HCl.Br- | C(Cl)Cl.CN(C)C=O | null | 1 | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(OCCCN)cc2)c2ccccc21.O=C(Cl)OCCBr>C(Cl)Cl.CN(C)C=O>CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(OCCCN3CCOC3=O)cc2)c2ccccc21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-20fa5cb7d0a742e587ae4f600aa59609 | CC(=O)N(c1ccc(Cl)cc1)C1CC(C)N(C(=O)c2ccc(OCCC(C)(C)C(=O)O)cc2)c2ccccc21>>CC(=O)N(c1ccccc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(OCCC(C)(C)C(=O)O)cc2)c2ccccc21 | C(C)(=O)N(C1CC(N(C2=CC=CC=C12)C(=O)C1=CC=C(OCCC(C(=O)O)(C)C)C=C1)C)C1=CC=C(C=C1)Cl>>C(C)(=O)N([C@@H]1C[C@@H](N(C2=CC=CC=C12)C(=O)C1=CC=C(OCCC(C(=O)O)(C)C)C=C1)C)C1=CC=CC=C1 | Cl[c:8]1[cH:7][cH:6][c:5]([N:4]([C:2]([CH3:1])=[O:3])[CH:11]2[CH2:12][CH:13]([CH3:14])[N:15]([C:16](=[O:17])[c:18]3[cH:19][cH:20][c:21]([O:22][CH2:23][CH2:24][C:25]([CH3:26])([CH3:27])[C:28](=[O:29])[OH:30])[cH:31][cH:32]3)[c:33]3[cH:34][cH:35][cH:36][cH:37][c:38]32)[cH:10][cH:9]1>>[CH3:1][C:2](=[O:3])[N:4]([c:5]1[cH:6... | CC(=O)N(c1ccc(Cl)cc1)C1CC(C)N(C(=O)c2ccc(OCCC(C)(C)C(=O)O)cc2)c2ccccc21 | CC(=O)N(c1ccccc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(OCCC(C)(C)C(=O)O)cc2)c2ccccc21 | null | [Pd] | C(C)O | Functional Group Interconversion | Aromatic dehalogenation | b66818d3926a4463fb8e1c3d4a89e94e47b4d46960d4bdb7bcfbeeec427cfd4e | 56de34d4a44cb25d9380269ee5e138b0f24b40a3a0db22c5508049dc775a861f | O=C(c1ccccc1)N1CC[C@@H](Nc2ccccc2)c2ccccc21 | Cl-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5]>>[c:5]:[c:4]:[cH;D2;+0:1]:[c:2]:[c:3] | null | [] | null | null | 3 | HOUR | 4-(4-{4-[Acetyl-(4-chloro-phenyl)-amino]-2-methyl-3,4-dihydro-2H-quinoline-1-carbonyl}-phenoxy)-2,2-dimethyl-butyric acid (300 mg, 0.545 mmol) was dissolved in ethanol. Pd/C (10% Palladium) was added, followed by H2 gas (1 atm-balloon). After 3 hours, the reaction mixture was filtered and concentrated. The crude residu... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | null | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1.c1ccc2c(c1)CCC[NH]2 | Other | [Pd].C(C)O | null | 3 | CC(=O)N(c1ccc(Cl)cc1)C1CC(C)N(C(=O)c2ccc(OCCC(C)(C)C(=O)O)cc2)c2ccccc21>[Pd].C(C)O>CC(=O)N(c1ccccc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(OCCC(C)(C)C(=O)O)cc2)c2ccccc21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-41a8cfe9bf9b4d32a4294e6f1769bfda | CCOC(=O)[C@H](F)Oc1ccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccc(Cl)cc3)CC2C)cc1>>CC(=O)N(c1ccc(Cl)cc1)[C@@H]1CC(C)N(C(=O)c2ccc(O[C@@H](F)C(=O)O)cc2)c2ccccc21 | C(C)OC([C@H](F)OC1=CC=C(C=C1)C(=O)N1C(C[C@H](C2=CC=CC=C12)N(C1=CC=C(C=C1)Cl)C(C)=O)C)=O.[OH-].[K+]>>C(C)(=O)N([C@@H]1CC(N(C2=CC=CC=C12)C(=O)C1=CC=C(O[C@H](C(=O)O)F)C=C1)C)C1=CC=C(C=C1)Cl | CC[O:28][C:26]([C@@H:24]([O:23][c:22]1[cH:21][cH:20][c:19]([C:17]([N:16]2[CH:14]([CH3:15])[CH2:13][C@@H:12]([N:4]([C:2]([CH3:1])=[O:3])[c:5]3[cH:6][cH:7][c:8]([Cl:9])[cH:10][cH:11]3)[c:36]3[c:31]2[cH:32][cH:33][cH:34][cH:35]3)=[O:18])[cH:30][cH:29]1)[F:25])=[O:27]>>[CH3:1][C:2](=[O:3])[N:4]([c:5]1[cH:6][cH:7][c:8]([Cl:... | CCOC(=O)[C@H](F)Oc1ccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccc(Cl)cc3)CC2C)cc1 | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1CC(C)N(C(=O)c2ccc(O[C@@H](F)C(=O)O)cc2)c2ccccc21 | null | null | CO.C1CCOC1 | Deprotection | Ester saponification (alkyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | O=C(c1ccccc1)N1CC[C@@H](Nc2ccccc2)c2ccccc21 | 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] | null | [] | null | null | 1 | HOUR | (2S,4R)-(4-{4-[Acetyl-(4-chloro-phenyl)-amino]-2-methyl-3,4-dihydro-2H-quinoline-1-carbonyl}-phenoxy)-fluoro-acetic acid ethyl ester (100 mg) was dissolved in methanol/THF (1:1, 5 mL), and potassium hydroxide (1.0N, 1 mL) was added. After 1 hour, the reaction was acidified and extracted with methylene chloride. The org... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1.c1ccccc1.c1ccc2c(c1)CCC[NH]2 | Other | CO.C1CCOC1 | null | 1 | CCOC(=O)[C@H](F)Oc1ccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccc(Cl)cc3)CC2C)cc1>CO.C1CCOC1>CC(=O)N(c1ccc(Cl)cc1)[C@@H]1CC(C)N(C(=O)c2ccc(O[C@@H](F)C(=O)O)cc2)c2ccccc21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-706040e5038f4dac820eb79bab8c39b3 | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(O)cc2)c2ccccc21.CCOC(=O)C1CCC(O)CC1>>CCOC(=O)C1CCC(Oc2ccc(C(=O)N3c4ccccc4[C@H](N(C(C)=O)c4ccc(Cl)cc4)C[C@@H]3C)cc2)CC1 | C(C)OC(=O)C1CCC(CC1)O.ClC1=CC=C(C=C1)N(C(C)=O)[C@@H]1C[C@@H](N(C2=CC=CC=C12)C(C1=CC=C(C=C1)O)=O)C.N(=NC(=O)OCC)C(=O)OCC.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3>>C(C)OC(=O)C1CCC(CC1)OC1=CC=C(C=C1)C(=O)N1[C@H](C[C@H](C2=CC=CC=C12)N(C1=CC=C(C=C1)Cl)C(C)=O)C | O[c:11]1[cH:12][cH:13][c:14]([C:15](=[O:16])[N:17]2[c:18]3[cH:19][cH:20][cH:21][cH:22][c:23]3[C@H:24]([N:25]([C:26]([CH3:27])=[O:28])[c:29]3[cH:30][cH:31][c:32]([Cl:33])[cH:34][cH:35]3)[CH2:36][C@@H:37]2[CH3:38])[cH:39][cH:40]1.[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]1[CH2:7][CH2:8][CH:9]([OH:10])[CH2:41][CH2:42]1>>[CH3:... | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(O)cc2)c2ccccc21.CCOC(=O)C1CCC(O)CC1 | CCOC(=O)C1CCC(Oc2ccc(C(=O)N3c4ccccc4[C@H](N(C(C)=O)c4ccc(Cl)cc4)C[C@@H]3C)cc2)CC1 | null | null | C1CCOC1 | Heteroatom Alkylation and Arylation | Mitsunobu aryl ether | de817abd28aa0a6201a692784d613d548e53f67c49ed49b6eff382c8e9e7a9e4 | 776ba735002e33225fbc578943016110c2c43efefd97bfeea4ec3cc2e2e1532f | O=C(c1ccc(OC2CCCCC2)cc1)N1CC[C@@H](Nc2ccccc2)c2ccccc21 | O-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[C:6]-[C:7](-[OH;D1;+0:8])-[C:9]>>[C:6]-[C:7](-[O;H0;D2;+0:8]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5])-[C:9] | 37 | [{"value": 37.0, "product": "C(C)OC(=O)C1CCC(CC1)OC1=CC=C(C=C1)C(=O)N1[C@H](C[C@H](C2=CC=CC=C12)N(C1=CC=C(C=C1)Cl)C(C)=O)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 36.9, "product": "C(C)OC(=O)C1CCC(CC1)OC1=CC=C(C=C1)C(=O)N1[C@H](C[C@H](C2=CC=CC=C12)N(C1=CC=C(C=C1)Cl)C(C)=O)C", "details": "CALCULATED... | 0 | CELSIUS | 10 | MINUTE | To a solution of diethyl azodicarboxylate (120 mg) in 5 ml THF at 0° C., was added PPh3 (181 mg). The mixture was stirred for 10 min at 0° C. Then (2S,4R)-N-(4-Chloro-phenyl)-N-[1-(4-hydroxy-benzoyl)-2-methyl-1,2,3,4-tetrahydro-quinolin-4-yl]-acetamide (200 mg) was added. The mixture was stirred for 20 min at 0° C. 4-H... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol.Aromatic alcohol | Ether | c1ccccc1 | c1ccccc1 | C1CCCCC1.c1ccccc1.c1ccccc1.c1ccc2c(c1)CCC[NH]2 | HO- | C1CCOC1 | 0 | 0.166667 | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(O)cc2)c2ccccc21.CCOC(=O)C1CCC(O)CC1>C1CCOC1>CCOC(=O)C1CCC(Oc2ccc(C(=O)N3c4ccccc4[C@H](N(C(C)=O)c4ccc(Cl)cc4)C[C@@H]3C)cc2)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-18b6d17178be4e53895593555fe05479 | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(O)cc2)c2ccccc21.COC(=O)[C@@H]1CCC[C@H]1CO>>COC(=O)C1CCCC1COc1ccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccc(Cl)cc3)C[C@@H]2C)cc1 | CCOC(=O)/N=N/C(=O)OCC.ClC1=CC=C(C=C1)N(C(C)=O)[C@@H]1C[C@@H](N(C2=CC=CC=C12)C(C1=CC=C(C=C1)O)=O)C.COC(=O)[C@H]1[C@@H](CCC1)CO.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3>>C(C)(=O)N([C@@H]1C[C@@H](N(C2=CC=CC=C12)C(=O)C1=CC=C(OCC2C(CCC2)C(=O)OC)C=C1)C)C1=CC=C(C=C1)Cl | O[c:12]1[cH:13][cH:14][c:15]([C:16](=[O:17])[N:18]2[c:19]3[cH:20][cH:21][cH:22][cH:23][c:24]3[C@H:25]([N:26]([C:27]([CH3:28])=[O:29])[c:30]3[cH:31][cH:32][c:33]([Cl:34])[cH:35][cH:36]3)[CH2:37][C@@H:38]2[CH3:39])[cH:40][cH:41]1.[CH3:1][O:2][C:3](=[O:4])[C@@H:5]1[CH2:6][CH2:7][CH2:8][C@H:9]1[CH2:10][OH:11]>>[CH3:1][O:2]... | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(O)cc2)c2ccccc21.COC(=O)[C@@H]1CCC[C@H]1CO | COC(=O)C1CCCC1COc1ccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccc(Cl)cc3)C[C@@H]2C)cc1 | null | null | C1(=CC=CC=C1)C | Heteroatom Alkylation and Arylation | Mitsunobu aryl ether | 8915084acbaaf997bf0f89ff5187cb2f89c25dc683fffc57b3391298c8430dd9 | 2258bd14c3b5449b92dc09cf9fa522f88d5071b4af20f7e968b60aa1ae6db0cf | O=C(c1ccc(OCC2CCCC2)cc1)N1CC[C@@H](Nc2ccccc2)c2ccccc21 | 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] | 90.7 | [{"value": 90.0, "product": "C(C)(=O)N([C@@H]1C[C@@H](N(C2=CC=CC=C12)C(=O)C1=CC=C(OCC2C(CCC2)C(=O)OC)C=C1)C)C1=CC=C(C=C1)Cl", "details": "PERCENTYIELD", "is_desired": false}, {"value": 90.7, "product": "C(C)(=O)N([C@@H]1C[C@@H](N(C2=CC=CC=C12)C(=O)C1=CC=C(OCC2C(CCC2)C(=O)OC)C=C1)C)C1=CC=C(C=C1)Cl", "details": "CALCULAT... | null | null | 18 | HOUR | Trans-2-Hydroxymethyl-cyclopentanecarboxylic acid methyl ester (0.127 g, 0.81 mmol) was dissolved in 10 ml toluene at room temperature with PPh3 (0.211 g, 0.81 mmol), then added N-(4-chlorophenyl)-N-[(2S,4R)-1-(4-hydroxybenzoyl)-2-methyl-1,2,3,4-tetrahydro-quinolin-4-yl]acetamide (0.1 g, 0.23 mmol) and stirred for 5 mi... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Aromatic alcohol | Ether | c1ccccc1 | c1ccccc1 | C1CCCC1.c1ccccc1.c1ccccc1.c1ccc2c(c1)CCC[NH]2 | HO- | C1(=CC=CC=C1)C | null | 18 | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(O)cc2)c2ccccc21.COC(=O)[C@@H]1CCC[C@H]1CO>C1(=CC=CC=C1)C>COC(=O)C1CCCC1COc1ccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccc(Cl)cc3)C[C@@H]2C)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-9353f8dd2c2e46cfadafb8bff33b9e85 | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(OCC3CCCC3C(=O)[O-])cc2)c2ccccc21>>CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(OC[C@@H]3CCC[C@H]3C(=O)O)cc2)c2ccccc21 | C(C)(=O)N([C@@H]1C[C@@H](N(C2=CC=CC=C12)C(=O)C1=CC=C(OCC2C(CCC2)C(=O)[O-])C=C1)C)C1=CC=C(C=C1)Cl.C([O-])([O-])=O.[K+].[K+]>>C(C)(=O)N([C@@H]1C[C@@H](N(C2=CC=CC=C12)C(=O)C1=CC=C(OC[C@H]2[C@@H](CCC2)C(=O)O)C=C1)C)C1=CC=C(C=C1)Cl | [CH3:1][C:2](=[O:3])[N:4]([c:5]1[cH:6][cH:7][c:8]([Cl:9])[cH:10][cH:11]1)[C@@H:12]1[CH2:13][C@H:14]([CH3:15])[N:16]([C:17](=[O:18])[c:19]2[cH:20][cH:21][c:22]([O:23][CH2:24][CH:25]3[CH2:26][CH2:27][CH2:28][CH:29]3[C:30](=[O:31])[O-:32])[cH:33][cH:34]2)[c:35]2[cH:36][cH:37][cH:38][cH:39][c:40]21>>[CH3:1][C:2](=[O:3])[N:... | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(OCC3CCCC3C(=O)[O-])cc2)c2ccccc21 | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(OC[C@@H]3CCC[C@H]3C(=O)O)cc2)c2ccccc21 | null | null | CO | Reduction | Carboxylate to carboxylic acid | 65edb34f59b888c9ecb87d6c8e9fd76d082de6afc49403d96c457f834c73148e | 222e2311064b3cb906d6bdeba44711f5dada050c096bbbcc7b35038975f228e8 | O=C(c1ccc(OCC2CCCC2)cc1)N1CC[C@@H](Nc2ccccc2)c2ccccc21 | [C:1]-[C:2](-[O-;H0;D1:3])=[O;D1;H0:4]>>[C:1]-[C:2](=[O;D1;H0:4])-[OH;D1;+0:3] | 10 | [{"value": 10.0, "product": "C(C)(=O)N([C@@H]1C[C@@H](N(C2=CC=CC=C12)C(=O)C1=CC=C(OC[C@H]2[C@@H](CCC2)C(=O)O)C=C1)C)C1=CC=C(C=C1)Cl", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 2 | DAY | 2-[(4-{[(2S,4R)-4-[acetyl(4-chlorophenyl)amino]-2-methyl-3,4-dihydroquinolin-1(2H)-yl]carbonyl}phenoxy)methyl]cyclopentanecarboxylate was hydrolyzed to the acid by dissolving in 5 ml methanol and potassium carbonate (0.100 g in 4 ml water) was added. The mixture was stirred for 2 days. The mixture was cooled to room te... | 10.6084/m9.figshare.5104873.v1 | null | null | Carboxylic acid | null | null | c1ccccc1.c1ccccc1.C1CCCC1.c1ccc2c(c1)CCC[NH]2 | null | CO | null | 48 | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(OCC3CCCC3C(=O)[O-])cc2)c2ccccc21>CO>CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(OC[C@@H]3CCC[C@H]3C(=O)O)cc2)c2ccccc21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ff72a5a95c5149c4a3fe7f172e5afa93 | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(OCCCN)cc2)c2ccccc21.C[Si](C)(C)N=C=O>>CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(OCCCNC(N)=O)cc2)c2ccccc21 | NCCCOC1=CC=C(C(=O)N2[C@H](C[C@H](C3=CC=CC=C23)N(C(C)=O)C2=CC=C(C=C2)Cl)C)C=C1.C[Si](C)(C)N=C=O>>ClC1=CC=C(C=C1)N(C(C)=O)[C@@H]1C[C@@H](N(C2=CC=CC=C12)C(C1=CC=C(C=C1)OCCCNC(=O)N)=O)C | [CH3:1][C:2](=[O:3])[N:4]([c:5]1[cH:6][cH:7][c:8]([Cl:9])[cH:10][cH:11]1)[C@@H:12]1[CH2:13][C@H:14]([CH3:15])[N:16]([C:17](=[O:18])[c:19]2[cH:20][cH:21][c:22]([O:23][CH2:24][CH2:25][CH2:26][NH2:27])[cH:31][cH:32]2)[c:33]2[cH:34][cH:35][cH:36][cH:37][c:38]21.C[Si](C)(C)[N:29]=[C:28]=[O:30]>>[CH3:1][C:2](=[O:3])[N:4]([c:... | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(OCCCN)cc2)c2ccccc21.C[Si](C)(C)N=C=O | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(OCCCNC(N)=O)cc2)c2ccccc21 | null | null | C(Cl)Cl | Acylation | OtherReaction | 6a5835c8b8db4f5aab8dd346fe49f2c81431cc20bacbaaab23b789ee31cca635 | 6bd8ab6a1c9de6e6b254509d33e097f855d6773ea4cd727c3f1a12189fe3db41 | O=C(c1ccccc1)N1CC[C@@H](Nc2ccccc2)c2ccccc21 | C-[Si](-C)(-C)-[N;H0;D2;+0:1]=[C;H0;D2;+0:2]=[O;D1;H0:3].[C:4]-[C:5]-[NH2;D1;+0:6]>>[C:4]-[C:5]-[NH;D2;+0:6]-[C;H0;D3;+0:2](-[NH2;D1;+0:1])=[O;D1;H0:3] | 17 | [{"value": 17.0, "product": "ClC1=CC=C(C=C1)N(C(C)=O)[C@@H]1C[C@@H](N(C2=CC=CC=C12)C(C1=CC=C(C=C1)OCCCNC(=O)N)=O)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 16.8, "product": "ClC1=CC=C(C=C1)N(C(C)=O)[C@@H]1C[C@@H](N(C2=CC=CC=C12)C(C1=CC=C(C=C1)OCCCNC(=O)N)=O)C", "details": "CALCULATEDPERCENTYIELD", "... | null | null | 18 | HOUR | To a solution of (2S,4R)-N-{1-[4-(3-Amino-propoxy)-benzoyl]-2-methyl-1,2,3,4-tetrahydro-quinolin-4-yl}-N-(4-chloro-phenyl)-acetamide (50 mg, 0.10 mmol) in DCM (1 mL) was added trimethylsilyl isocyanate (23 mg, 0.20 mmol). The reaction mixture was stirred at room temperature for 18 hours. The reaction was quenched by ad... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Silyl protective group | Urea | null | null | c1ccccc1.c1ccccc1.c1ccc2c(c1)CCC[NH]2 | Other | C(Cl)Cl | null | 18 | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(OCCCN)cc2)c2ccccc21.C[Si](C)(C)N=C=O>C(Cl)Cl>CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(OCCCNC(N)=O)cc2)c2ccccc21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-c6a1481f2eb64ff7bb5c602b6786876e | BrCCn1ccnc1.CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(O)cc2)c2ccccc21>>CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(OCCn3ccnc3)cc2)c2ccccc21 | ClC1=CC=C(C=C1)N(C(C)=O)[C@@H]1C[C@@H](N(C2=CC=CC=C12)C(C1=CC=C(C=C1)O)=O)C.C(=O)([O-])[O-].[K+].[K+].BrCCN1C=NC=C1>>ClC1=CC=C(C=C1)N(C(C)=O)[C@@H]1C[C@@H](N(C2=CC=CC=C12)C(C1=CC=C(C=C1)OCCN1C=NC=C1)=O)C | Br[CH2:24][CH2:25][n:26]1[cH:27][cH:28][n:29][cH:30]1.[CH3:1][C:2](=[O:3])[N:4]([c:5]1[cH:6][cH:7][c:8]([Cl:9])[cH:10][cH:11]1)[C@@H:12]1[CH2:13][C@H:14]([CH3:15])[N:16]([C:17](=[O:18])[c:19]2[cH:20][cH:21][c:22]([OH:23])[cH:31][cH:32]2)[c:33]2[cH:34][cH:35][cH:36][cH:37][c:38]21>>[CH3:1][C:2](=[O:3])[N:4]([c:5]1[cH:6]... | BrCCn1ccnc1.CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(O)cc2)c2ccccc21 | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(OCCn3ccnc3)cc2)c2ccccc21 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | O=C(c1ccc(OCCn2ccnc2)cc1)N1CC[C@@H](Nc2ccccc2)c2ccccc21 | Br-[CH2;D2;+0:1]-[C:2]-[#7;a:3].[OH;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[#7;a:3]-[C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:4]-[c:5](:[c:6]):[c:7] | 76 | [{"value": 76.0, "product": "ClC1=CC=C(C=C1)N(C(C)=O)[C@@H]1C[C@@H](N(C2=CC=CC=C12)C(C1=CC=C(C=C1)OCCN1C=NC=C1)=O)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 75.6, "product": "ClC1=CC=C(C=C1)N(C(C)=O)[C@@H]1C[C@@H](N(C2=CC=CC=C12)C(C1=CC=C(C=C1)OCCN1C=NC=C1)=O)C", "details": "CALCULATEDPERCENTYIELD",... | 80 | CELSIUS | null | null | (2S,4R)-N-(4-Chloro-phenyl)-N-[1-(4-hydroxy-benzoyl)-2-methyl-1,2,3,4-tetrahydro-quinolin-4-yl]-acetamide (0.065 g, 0.15 mmol) was dissolved in DMF at room temperature and K2CO3 (0.12 g, 0.87 mmol) was added. 1-(2-Bromo-ethyl)-1H-imidazole (0.08 g, 0.45 mmol) was added and the reaction was allowed to heat to 80° C. ove... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccccc1.c1ccccc1.c1c[nH]cn1.c1ccc2c(c1)CCC[NH]2 | HBr | CN(C)C=O | 80 | null | BrCCn1ccnc1.CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(O)cc2)c2ccccc21>CN(C)C=O>CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(OCCn3ccnc3)cc2)c2ccccc21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a42dd5c064554bc2866a792dbe662f81 | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(O)cc2)c2ccccc21.COC(=O)C(C)(C)CCBr>>COC(=O)C(C)(C)CCOc1ccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccc(Cl)cc3)C[C@@H]2C)cc1 | ClC1=CC=C(C=C1)N(C(C)=O)[C@@H]1C[C@@H](N(C2=CC=CC=C12)C(C1=CC=C(C=C1)O)=O)C.C(=O)([O-])[O-].[K+].[K+].COC(C(CCBr)(C)C)=O>>COC(C(CCOC1=CC=C(C=C1)C(=O)N1[C@H](C[C@H](C2=CC=CC=C12)N(C1=CC=C(C=C1)Cl)C(C)=O)C)(C)C)=O | [OH:10][c:11]1[cH:12][cH:13][c:14]([C:15](=[O:16])[N:17]2[c:18]3[cH:19][cH:20][cH:21][cH:22][c:23]3[C@H:24]([N:25]([C:26]([CH3:27])=[O:28])[c:29]3[cH:30][cH:31][c:32]([Cl:33])[cH:34][cH:35]3)[CH2:36][C@@H:37]2[CH3:38])[cH:39][cH:40]1.Br[CH2:9][CH2:8][C:5]([C:3]([O:2][CH3:1])=[O:4])([CH3:6])[CH3:7]>>[CH3:1][O:2][C:3](=[... | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(O)cc2)c2ccccc21.COC(=O)C(C)(C)CCBr | COC(=O)C(C)(C)CCOc1ccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccc(Cl)cc3)C[C@@H]2C)cc1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | O=C(c1ccccc1)N1CC[C@@H](Nc2ccccc2)c2ccccc21 | Br-[CH2;D2;+0:1]-[C:2]-[C:3]-[C:4](-[#8:5])=[O;D1;H0:6].[OH;D1;+0:7]-[c:8](:[c:9]):[c:10]>>[#8:5]-[C:4](=[O;D1;H0:6])-[C:3]-[C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:7]-[c:8](:[c:9]):[c:10] | 77 | [{"value": 77.0, "product": "COC(C(CCOC1=CC=C(C=C1)C(=O)N1[C@H](C[C@H](C2=CC=CC=C12)N(C1=CC=C(C=C1)Cl)C(C)=O)C)(C)C)=O", "details": "PERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | null | null | (2S,4R)-N-(4-Chloro-phenyl)-N-[1-(4-hydroxy-benzoyl)-2-methyl-1,2,3,4-tetrahydro-quinolin-4-yl]-acetamide (0.126 g, 0.242 mmol) was dissolved in 3 ml DMF at room temperature and K2CO3 (0.267 g, 1.94 mmol) was added. 4-Bromo-2,2-dimethyl-butyric acid methyl ester (0.202 g, 0.969 mmol, prepared according to the procedure... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccccc1.c1ccccc1.c1ccc2c(c1)CCC[NH]2 | HBr | CN(C)C=O | 80 | null | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(O)cc2)c2ccccc21.COC(=O)C(C)(C)CCBr>CN(C)C=O>COC(=O)C(C)(C)CCOc1ccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccc(Cl)cc3)C[C@@H]2C)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-bb0a0e7b03734479b72b3075e9fd152a | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(N3CCCC(C(=O)O)C3)cc2)c2ccccc21.[NH4+]>>CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(N3CCCC(C(N)=O)C3)cc2)c2ccccc21 | [Cl-].[NH4+].C=1C=CC2=C(C1)N=NN2O.CN(C)C(=[N+](C)C)ON1C2=C(C=CC=N2)N=N1.F[P-](F)(F)(F)(F)F.C(C)(C)N(CC)C(C)C.C(C)(=O)N([C@@H]1C[C@@H](N(C2=CC=CC=C12)C(=O)C1=CC=C(C=C1)N1CC(CCC1)C(=O)O)C)C1=CC=C(C=C1)Cl>>C(C)(=O)N([C@@H]1C[C@@H](N(C2=CC=CC=C12)C(=O)C1=CC=C(C=C1)N1CC(CCC1)C(=O)N)C)C1=CC=C(C=C1)Cl | O[C:28]([CH:27]1[CH2:26][CH2:25][CH2:24][N:23]([c:22]2[cH:21][cH:20][c:19]([C:17]([N:16]3[C@@H:14]([CH3:15])[CH2:13][C@@H:12]([N:4]([C:2]([CH3:1])=[O:3])[c:5]4[cH:6][cH:7][c:8]([Cl:9])[cH:10][cH:11]4)[c:39]4[c:34]3[cH:35][cH:36][cH:37][cH:38]4)=[O:18])[cH:33][cH:32]2)[CH2:31]1)=[O:30].[NH4+:29]>>[CH3:1][C:2](=[O:3])[N:... | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(N3CCCC(C(=O)O)C3)cc2)c2ccccc21.[NH4+] | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(N3CCCC(C(N)=O)C3)cc2)c2ccccc21 | null | null | CN(C)C=O.C(C)(=O)OCC | Acylation | Carboxylic acid to amide conversion | 1283aef55d7ee699f097a8e5267689198c76ba671644401547f902657820236d | cb0a71c3fb37a76e96fbd81aae6f95a28398a03d1ad2c8e877085e735efb98f1 | O=C(c1ccc(N2CCCCC2)cc1)N1CC[C@@H](Nc2ccccc2)c2ccccc21 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[C:5]-[#7:6].[NH4+;D0:7]>>[#7:6]-[C:5]-[C:3](-[C;H0;D3;+0:1](-[NH2;D1;+0:7])=[O;D1;H0:2])-[C:4] | null | [] | null | null | 16 | HOUR | (2S,4R)-1-(4-{4-[Acetyl-(4-chloro-phenyl)-amino]-2-methyl-3,4-dihydro-2H-quinoline-1-carbonyl}-phenyl)-piperidine-3-carboxylic acid amide was prepared from (2S,4R)-1-(4-{4-[Acetyl-(4-chloro-phenyl)-amino]-2-methyl-3,4-dihydro-2H-quinoline-1-carbonyl}-phenyl)-piperidine-3-carboxylic acid. The acid (0.2 g, 0.366 mmol) wa... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Primary amide | null | null | c1ccccc1.c1ccccc1.C1CC[NH]CC1.c1ccc2c(c1)CCC[NH]2 | HO- | CN(C)C=O.C(C)(=O)OCC | null | 16 | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(N3CCCC(C(=O)O)C3)cc2)c2ccccc21.[NH4+]>CN(C)C=O.C(C)(=O)OCC>CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(N3CCCC(C(N)=O)C3)cc2)c2ccccc21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-fa551e689318482c890d0cab8c473395 | CC(=O)Cl.CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(OCC3CCNCC3)cc2)c2ccccc21>>CC(=O)N1CCC(COc2ccc(C(=O)N3c4ccccc4[C@H](N(C(C)=O)c4ccc(Cl)cc4)C[C@@H]3C)cc2)CC1 | ClC1=CC=C(C=C1)N(C(C)=O)[C@@H]1C[C@@H](N(C2=CC=CC=C12)C(C1=CC=C(C=C1)OCC1CCNCC1)=O)C.CCN(C(C)C)C(C)C.C(C)(=O)Cl>>C(C)(=O)N1CCC(CC1)COC1=CC=C(C(=O)N2[C@H](C[C@H](C3=CC=CC=C23)N(C(C)=O)C2=CC=C(C=C2)Cl)C)C=C1 | Cl[C:2]([CH3:1])=[O:3].[NH:4]1[CH2:5][CH2:6][CH:7]([CH2:8][O:9][c:10]2[cH:11][cH:12][c:13]([C:14](=[O:15])[N:16]3[c:17]4[cH:18][cH:19][cH:20][cH:21][c:22]4[C@H:23]([N:24]([C:25]([CH3:26])=[O:27])[c:28]4[cH:29][cH:30][c:31]([Cl:32])[cH:33][cH:34]4)[CH2:35][C@@H:36]3[CH3:37])[cH:38][cH:39]2)[CH2:40][CH2:41]1>>[CH3:1][C:2... | CC(=O)Cl.CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(OCC3CCNCC3)cc2)c2ccccc21 | CC(=O)N1CCC(COc2ccc(C(=O)N3c4ccccc4[C@H](N(C(C)=O)c4ccc(Cl)cc4)C[C@@H]3C)cc2)CC1 | null | null | ClCCl | Acylation | N-alkylation of secondary amines with alkyl halides | aaa7c80569e6aa145ac8d7318e06893ee71aff0c965e85eca836522c948938d5 | 96cb0a2fed10552c5770a45a2d6523b47ac3e38928b4a9c698d8577451182dcd | O=C(c1ccc(OCC2CCNCC2)cc1)N1CC[C@@H](Nc2ccccc2)c2ccccc21 | Cl-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[C:4]-[C:5]-[NH;D2;+0:6]-[C:7]-[C:8]>>[C:4]-[C:5]-[N;H0;D3;+0:6](-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3])-[C:7]-[C:8] | 61 | [{"value": 49.0, "product": "C(C)(=O)N1CCC(CC1)COC1=CC=C(C(=O)N2[C@H](C[C@H](C3=CC=CC=C23)N(C(C)=O)C2=CC=C(C=C2)Cl)C)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 61.0, "product": "C(C)(=O)N1CCC(CC1)COC1=CC=C(C(=O)N2[C@H](C[C@H](C3=CC=CC=C23)N(C(C)=O)C2=CC=C(C=C2)Cl)C)C=C1", "details": "CALCULATEDPE... | null | null | 8 | HOUR | (2S,4R)-N-(4-Chloro-phenyl)-N-{2-methyl-1-[4-(piperidin-4-ylmethoxy)-benzoyl]-1,2,3,4-tetrahydro-quinolin-4-yl}-acetamide (0.075 g, 0.14 mmol) was dissolved in dichloromethane at room temperature. DIEA (0.1 mL, 0.56 mmol) and acetyl chloride (0.2 mL, 2.8 mmol) was added. The reaction was stirred at room temperature ove... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Secondary amine | Tertiary amide | C1CCNCC1 | C1CC[NH]CC1 | C1CC[NH]CC1.c1ccccc1.c1ccccc1.c1ccc2c(c1)CCC[NH]2 | HCl | ClCCl | null | 8 | CC(=O)Cl.CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(OCC3CCNCC3)cc2)c2ccccc21>ClCCl>CC(=O)N1CCC(COc2ccc(C(=O)N3c4ccccc4[C@H](N(C(C)=O)c4ccc(Cl)cc4)C[C@@H]3C)cc2)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-f01ab17bfb7c4adebc2abb8cb0da1863 | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(OCCCN)cc2)c2ccccc21.CCOC(=O)CBr>>CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(OCCCNCC(=O)O)cc2)c2ccccc21 | NCCCOC1=CC=C(C(=O)N2[C@H](C[C@H](C3=CC=CC=C23)N(C(C)=O)C2=CC=C(C=C2)Cl)C)C=C1.NCCCOC1=CC=C(C(=O)N2[C@H](C[C@H](C3=CC=CC=C23)N(C(C)=O)C2=CC=C(C=C2)Cl)C)C=C1.BrCC(=O)OCC.C([O-])([O-])=O.[K+].[K+]>>C(C)(=O)N([C@@H]1C[C@@H](N(C2=CC=CC=C12)C(=O)C1=CC=C(OCCCNCC(=O)O)C=C1)C)C1=CC=C(C=C1)Cl | [CH3:1][C:2](=[O:3])[N:4]([c:5]1[cH:6][cH:7][c:8]([Cl:9])[cH:10][cH:11]1)[C@@H:12]1[CH2:13][C@H:14]([CH3:15])[N:16]([C:17](=[O:18])[c:19]2[cH:20][cH:21][c:22]([O:23][CH2:24][CH2:25][CH2:26][NH2:27])[cH:32][cH:33]2)[c:34]2[cH:35][cH:36][cH:37][cH:38][c:39]21.CC[O:31][C:29]([CH2:28]Br)=[O:30]>>[CH3:1][C:2](=[O:3])[N:4]([... | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(OCCCN)cc2)c2ccccc21.CCOC(=O)CBr | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(OCCCNCC(=O)O)cc2)c2ccccc21 | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | OtherReaction | 92415cd0d503587dbc9232020ecee975743c4b5ccf369938adbe25f985d01623 | 3a5c5926d99d81cbe840ec25b6cb76f2e082bfbc6b5b9f02c592b9a82d36478b | O=C(c1ccccc1)N1CC[C@@H](Nc2ccccc2)c2ccccc21 | Br-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[O;H0;D2;+0:4]-C-C.[C:5]-[C:6]-[NH2;D1;+0:7]>>[C:5]-[C:6]-[NH;D2;+0:7]-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[OH;D1;+0:4] | null | [] | 50 | CELSIUS | null | null | {[3-(4-{[(2S,4R)-4-[acetyl(4-chlorophenyl)amino]-2-methyl-3,4-dihydroquinolin-1(2H)-yl]carbonyl}phenoxy)propyl]amino}acetic acid was prepared from (2S,4R)-N-{1-[4-(3-amino-propoxy)-benzoyl]-2-methyl-1,2,3,4-tetrahydro-quinolin-4-yl}-N-(4-chloro-phenyl)-acetamide. (2S,4R)-N-{1-[4-(3-amino-propoxy)-benzoyl]-2-methyl-1,2,... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester.Primary amine | Carboxylic acid.Secondary amine | null | null | c1ccccc1.c1ccccc1.c1ccc2c(c1)CCC[NH]2 | HBr | CN(C=O)C | 50 | null | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(OCCCN)cc2)c2ccccc21.CCOC(=O)CBr>CN(C=O)C>CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(OCCCNCC(=O)O)cc2)c2ccccc21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-7dc1f59994ee47179349fa16d76ae94a | CCOC(=O)CNCCCOc1ccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccc(Cl)cc3)C[C@@H]2C)cc1>>CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(OCCCNCC(=O)O)cc2)c2ccccc21 | C(C)OC(CNCCCOC1=CC=C(C=C1)C(=O)N1[C@H](C[C@H](C2=CC=CC=C12)N(C1=CC=C(C=C1)Cl)C(C)=O)C)=O.C(C)O.[OH-].[Na+]>>C(C)(=O)N([C@@H]1C[C@@H](N(C2=CC=CC=C12)C(=O)C1=CC=C(OCCCNCC(=O)O)C=C1)C)C1=CC=C(C=C1)Cl | CC[O:31][C:29]([CH2:28][NH:27][CH2:26][CH2:25][CH2:24][O:23][c:22]1[cH:21][cH:20][c:19]([C:17]([N:16]2[C@@H:14]([CH3:15])[CH2:13][C@@H:12]([N:4]([C:2]([CH3:1])=[O:3])[c:5]3[cH:6][cH:7][c:8]([Cl:9])[cH:10][cH:11]3)[c:39]3[c:34]2[cH:35][cH:36][cH:37][cH:38]3)=[O:18])[cH:33][cH:32]1)=[O:30]>>[CH3:1][C:2](=[O:3])[N:4]([c:5... | CCOC(=O)CNCCCOc1ccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccc(Cl)cc3)C[C@@H]2C)cc1 | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(OCCCNCC(=O)O)cc2)c2ccccc21 | null | null | O1CCCC1 | Deprotection | Ester saponification (alkyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | O=C(c1ccccc1)N1CC[C@@H](Nc2ccccc2)c2ccccc21 | 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] | 60 | [{"value": 60.0, "product": "C(C)(=O)N([C@@H]1C[C@@H](N(C2=CC=CC=C12)C(=O)C1=CC=C(OCCCNCC(=O)O)C=C1)C)C1=CC=C(C=C1)Cl", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | {[3-(4-{[(2S,4R)-4-[acetyl(4-chlorophenyl)amino]-2-methyl-3,4-dihydroquinolin-1(2H)-yl]carbonyl}phenoxy)propyl]amino}acetic ethyl ester was hydrolyzed to the acid by dissolving in tetrahydrofuran and ethanol and sodium hydroxide (1N) was added. The mixture was stirred at room temperature overnight. The mixture was cool... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1.c1ccccc1.c1ccc2c(c1)CCC[NH]2 | Other | O1CCCC1 | null | 8 | CCOC(=O)CNCCCOc1ccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccc(Cl)cc3)C[C@@H]2C)cc1>O1CCCC1>CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(OCCCNCC(=O)O)cc2)c2ccccc21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-3456898986f84a9da8fecfc1c8aecc03 | BrCCCn1cccn1.CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(O)cc2)c2ccccc21>>CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(OCCCn3cccn3)cc2)c2ccccc21 | BrCCCN1N=CC=C1.BrCCCBr.N1N=CC=C1.[H-].[Na+].C(=O)([O-])[O-].[K+].[K+].ClC1=CC=C(C=C1)N(C(C)=O)[C@@H]1C[C@@H](N(C2=CC=CC=C12)C(C1=CC=C(C=C1)O)=O)C>>ClC1=CC=C(C=C1)N(C(C)=O)[C@@H]1C[C@@H](N(C2=CC=CC=C12)C(C1=CC=C(C=C1)OCCCN1N=CC=C1)=O)C | Br[CH2:24][CH2:25][CH2:26][n:27]1[cH:28][cH:29][cH:30][n:31]1.[CH3:1][C:2](=[O:3])[N:4]([c:5]1[cH:6][cH:7][c:8]([Cl:9])[cH:10][cH:11]1)[C@@H:12]1[CH2:13][C@H:14]([CH3:15])[N:16]([C:17](=[O:18])[c:19]2[cH:20][cH:21][c:22]([OH:23])[cH:32][cH:33]2)[c:34]2[cH:35][cH:36][cH:37][cH:38][c:39]21>>[CH3:1][C:2](=[O:3])[N:4]([c:5... | BrCCCn1cccn1.CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(O)cc2)c2ccccc21 | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(OCCCn3cccn3)cc2)c2ccccc21 | null | null | O1CCCC1.CN(C)C=O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | O=C(c1ccc(OCCCn2cccn2)cc1)N1CC[C@@H](Nc2ccccc2)c2ccccc21 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[OH;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:4]-[c:5](:[c:6]):[c:7] | null | [] | 70 | CELSIUS | 3 | HOUR | (2S,4R)-N-(4-Chloro-phenyl)-N-[1-(4-hydroxy-benzoyl)-2-methyl-1,2,3,4-tetrahydro-quinolin-4-yl]-acetamide (75 mg, 0.17 mmol) was dissolved in DMF (1 mL) at room temperature. K2CO3 (47 mg, 0.34 mmol) was added followed by 1-(3-bromopropyl)-pyrazole (64 mg, 0.34 mmol) (prepared from the reaction of 1,3-dibromopropane and... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccccc1.c1ccccc1.c1cn[nH]c1.c1ccc2c(c1)CCC[NH]2 | HBr | O1CCCC1.CN(C)C=O | 70 | 3 | BrCCCn1cccn1.CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(O)cc2)c2ccccc21>O1CCCC1.CN(C)C=O>CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(OCCCn3cccn3)cc2)c2ccccc21 |
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