dataset_id large_stringclasses 414
values | reaction_id large_stringlengths 36 36 | reaction_smiles large_stringlengths 4 873 | rxn_insight_reaction large_stringlengths 19 1.07k | mapped_reaction_smiles large_stringlengths 14 3.37k | reactant_smiles large_stringlengths 1 581 | product_smiles large_stringlengths 1 433 | reagent_smiles large_stringclasses 634
values | catalyst_smiles large_stringlengths 1 683 ⌀ | solvent_smiles large_stringlengths 1 245 ⌀ | rxn_insight_class large_stringclasses 11
values | rxn_insight_name large_stringclasses 346
values | rxn_insight_tag large_stringlengths 64 64 | rxn_insight_tag2 large_stringlengths 64 64 | rxn_insight_scaffold large_stringlengths 5 288 ⌀ | rxn_insight_template large_stringlengths 24 2.64k ⌀ | yield_percent float64 -0.8 90,205,160,000B ⌀ | yield_measurements large_stringlengths 2 864 | temperature_value float64 -230 30.1k ⌀ | temperature_units large_stringclasses 3
values | reaction_time_value float64 0 4k ⌀ | time_units large_stringclasses 4
values | procedure_details large_stringlengths 1 23.6k ⌀ | reference large_stringclasses 96
values | doi large_stringclasses 19
values | functional_groups_reactants large_stringlengths 3 716 ⌀ | functional_groups_products large_stringlengths 3 539 ⌀ | participating_rings_reactants large_stringlengths 5 293 ⌀ | participating_rings_products large_stringlengths 5 271 ⌀ | all_rings_products large_stringlengths 5 271 ⌀ | byproduct_smiles large_stringclasses 176
values | agent_smiles large_stringlengths 1 712 ⌀ | temperature_c float64 -230 30.1k ⌀ | reaction_time_hours float64 0 2.16k ⌀ | reaction_smiles_with_agents large_stringlengths 4 882 |
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-0be49fb58b2f4f039baba09b76a48389 | CC(=O)c1ccncc1.O=C(C[P+](c1ccccc1)(c1ccccc1)c1ccccc1)OCc1ccccc1>>CC(=CC(=O)OCc1ccccc1)c1ccncc1 | C([O-])([O-])=O.[K+].[K+].CN(C=O)C.C(C)(=O)C1=CC=NC=C1.[Br-].C(C1=CC=CC=C1)OC(=O)C[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1>>N1=CC=C(C=C1)C(=CC(=O)OCC1=CC=CC=C1)C | O=[C:2]([CH3:1])[c:14]1[cH:15][cH:16][n:17][cH:18][cH:19]1.c1ccc([P+](c2ccccc2)(c2ccccc2)[CH2:3][C:4](=[O:5])[O:6][CH2:7][c:8]2[cH:9][cH:10][cH:11][cH:12][cH:13]2)cc1>>[CH3:1][C:2](=[CH:3][C:4](=[O:5])[O:6][CH2:7][c:8]1[cH:9][cH:10][cH:11][cH:12][cH:13]1)[c:14]1[cH:15][cH:16][n:17][cH:18][cH:19]1 | CC(=O)c1ccncc1.O=C(C[P+](c1ccccc1)(c1ccccc1)c1ccccc1)OCc1ccccc1 | CC(=CC(=O)OCc1ccccc1)c1ccncc1 | null | null | C(C)OCC | C-C Coupling | Wittig with Phosphonium | 7978659339fd553ad8927697c9e4fa421bb43020b82cb3c460189ff95e97c22d | 79a946b42eb7e7aee42e09efe41630192c1745e07085cd7f7f88cc7b599f9082 | O=C(C=Cc1ccncc1)OCc1ccccc1 | O=[C;H0;D3;+0:1](-[C;D1;H3:2])-[c:3]1:[c:4]:[c:5]:[#7;a:6]:[c:7]:[c:8]:1.[C:9]-[#8:10]-[C:11](=[O;D1;H0:12])-[CH2;D2;+0:13]-[P+](-c1:c:c:c:c:c:1)(-c1:c:c:c:c:c:1)-c1:c:c:c:c:c:1>>[C:9]-[#8:10]-[C:11](=[O;D1;H0:12])-[CH;D2;+0:13]=[C;H0;D3;+0:1](-[C;D1;H3:2])-[c:3]1:[c:4]:[c:5]:[#7;a:6]:[c:7]:[c:8]:1 | 42.4 | [{"value": 42.0, "product": "N1=CC=C(C=C1)C(=CC(=O)OCC1=CC=CC=C1)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 42.4, "product": "N1=CC=C(C=C1)C(=CC(=O)OCC1=CC=CC=C1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 70 | CELSIUS | null | null | N,N-Dimethylformamide (33 ml) was added to a mixture of 4-acetylpyridine (2.00 g, 16.5 mmol) and (benzyloxycarbonyl)methyltriphenylphosphonium bromide (8.94 g, 18.2 mmol), and the whole was stirred under ice-cooling. Potassium carbonate (9.12 g, 66.0 mmol) was added thereto, the external temperature was raised to 70° C... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ester | Ester | c1ccccc1.c1ccccc1.c1ccccc1 | null | c1ccccc1.c1ccncc1 | HO- | C(C)OCC | 70 | null | CC(=O)c1ccncc1.O=C(C[P+](c1ccccc1)(c1ccccc1)c1ccccc1)OCc1ccccc1>C(C)OCC>CC(=CC(=O)OCc1ccccc1)c1ccncc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-327817e6450444259c376fea7bea94c6 | CC(=CC(=O)OCc1ccccc1)c1ccncc1>>CC(CC(=O)O)c1ccncc1 | C(C)(=O)O.N1=CC=C(C=C1)C(=CC(=O)OCC1=CC=CC=C1)C>>N1=CC=C(C=C1)C(CC(=O)O)C | c1ccc(C[O:6][C:4]([CH:3]=[C:2]([CH3:1])[c:7]2[cH:8][cH:9][n:10][cH:11][cH:12]2)=[O:5])cc1>>[CH3:1][CH:2]([CH2:3][C:4](=[O:5])[OH:6])[c:7]1[cH:8][cH:9][n:10][cH:11][cH:12]1 | CC(=CC(=O)OCc1ccccc1)c1ccncc1 | CC(CC(=O)O)c1ccncc1 | null | null | CO | Deprotection | OtherReaction | 86a971d3e4f88009ab4c98512e9f1deb51b2f0ce5cbd068cc61ae878c1e58e2a | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccncc1 | [C;D1;H3:1]-[C;H0;D3;+0:2](=[CH;D2;+0:3]-[C:4](=[O;D1;H0:5])-[O;H0;D2;+0:6]-C-c1:c:c:c:c:c:1)-[c:7]1:[c:8]:[c:9]:[#7;a:10]:[c:11]:[c:12]:1>>[C;D1;H3:1]-[CH;D3;+0:2](-[CH2;D2;+0:3]-[C:4](=[O;D1;H0:5])-[OH;D1;+0:6])-[c:7]1:[c:8]:[c:9]:[#7;a:10]:[c:11]:[c:12]:1 | 60 | [{"value": 60.0, "product": "N1=CC=C(C=C1)C(CC(=O)O)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 59.6, "product": "N1=CC=C(C=C1)C(CC(=O)O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | Next, methanol (31 ml) and acetic acid (0.71 ml, 12.4 mmol) were added to benzyl 3-(4-pyridyl)-2-butenoate (1.75 g, 6.20 mmol), and a nitrogen gas was bubbled through the mixture at room temperature for 10 minutes. A catalytic amount of 10% palladium on carbon was added to the mixture, and the whole was stirred under a... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | c1ccccc1 | null | c1ccncc1 | Other | CO | null | 8 | CC(=CC(=O)OCc1ccccc1)c1ccncc1>CO>CC(CC(=O)O)c1ccncc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b671dbbc36d8445e87e60b8188c4510b | CC(CC(N)=O)c1ccncc1>>CC(CCN)c1ccncc1 | N1=CC=C(C=C1)C(CC(=O)N)C.CCOCC.[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+]>>N1=CC=C(C=C1)C(CCN)C | O=[C:4]([CH2:3][CH:2]([CH3:1])[c:6]1[cH:7][cH:8][n:9][cH:10][cH:11]1)[NH2:5]>>[CH3:1][CH:2]([CH2:3][CH2:4][NH2:5])[c:6]1[cH:7][cH:8][n:9][cH:10][cH:11]1 | CC(CC(N)=O)c1ccncc1 | CC(CCN)c1ccncc1 | null | null | C(C)(=O)OCC.C(Cl)Cl | Reduction | Reduction of primary amides to amines | 71f4ab6e4ff9fd6ad8fb6a6879cdc6c258d35bb85b9b40ad2783b874bf909ba4 | 8776a0c3e2f32dafe87200a597cd55df0b01414bf133bdc9f8f7e1171014bfad | c1ccncc1 | O=[C;H0;D3;+0:1](-[N;D1;H2:2])-[C:3]-[C:4]>>[C:4]-[C:3]-[CH2;D2;+0:1]-[N;D1;H2:2] | 75 | [{"value": 75.0, "product": "N1=CC=C(C=C1)C(CCN)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 71.3, "product": "N1=CC=C(C=C1)C(CCN)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Next, anhydrous ether (8 ml) was added to lithium aluminum hydride (0.16 g, 4.2 mmol) under a nitrogen atmosphere, and the mixture was stirred under ice-cooling. A solution of 3-(4-pyridyl)butyramide (0.22 g, 1.4 mmol) in anhydrous methylene chloride (8 ml) was added dropwise to the mixture over two minutes, the temper... | 10.6084/m9.figshare.5104873.v1 | null | Primary amide | null | null | null | c1ccncc1 | Other | C(C)(=O)OCC.C(Cl)Cl | null | null | CC(CC(N)=O)c1ccncc1>C(C)(=O)OCC.C(Cl)Cl>CC(CCN)c1ccncc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-058da2b8cb024016b60ad8909917c9ed | Brc1ccncc1.NCCN>>NCCNc1ccncc1 | C(CN)N.Cl.BrC1=CC=NC=C1.C([O-])([O-])=O.[K+].[K+]>>N1=CC=C(C=C1)NCCN | Br[c:5]1[cH:6][cH:7][n:8][cH:9][cH:10]1.[NH2:1][CH2:2][CH2:3][NH2:4]>>[NH2:1][CH2:2][CH2:3][NH:4][c:5]1[cH:6][cH:7][n:8][cH:9][cH:10]1 | Brc1ccncc1.NCCN | NCCNc1ccncc1 | null | null | null | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | c026a7bf7aba66b20cf21a13c528689aaaa1c05901524d62b36ca0c3b0572cef | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccncc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[#7;a:4]:[c:5]:[c:6]:1.[C:7]-[C:8]-[NH2;D1;+0:9]>>[C:7]-[C:8]-[NH;D2;+0:9]-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[#7;a:4]:[c:5]:[c:6]:1 | 77 | [{"value": 77.0, "product": "N1=CC=C(C=C1)NCCN", "details": "PERCENTYIELD", "is_desired": false}, {"value": 76.7, "product": "N1=CC=C(C=C1)NCCN", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 10 | MINUTE | Ethylenediamine (10.4 ml, 155 mmol) was added to 4-bromopyridine hydrochloride (3.00 g, 15.5 mmol) under a nitrogen atmosphere, and the mixture was refluxed for 1.5 hours. The temperature was cooled to room temperature, potassium carbonate (8.57 g, 62.0 mmol) was added to the reaction mixture, and the whole was stirred... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccncc1 | c1ccncc1 | c1ccncc1 | HBr | null | null | 0.166667 | Brc1ccncc1.NCCN>>NCCNc1ccncc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-df3482e526fd41a5bb74b930ff3f7cda | CC(=O)CC(=O)OC(C)(C)C.ClCc1ccncc1>>CCOC(=O)C(Cc1ccncc1)C(C)=O | C(O)([O-])=O.[Na+].C(CC(=O)C)(=O)OC(C)(C)C.[H-].[Na+].Cl.ClCC1=CC=NC=C1>>C(C)(=O)C(C(=O)OCC)CC1=CC=NC=C1 | C[C:2](C)([CH3:1])[O:3][C:4](=[O:5])[CH2:6][C:14]([CH3:15])=[O:16].Cl[CH2:7][c:8]1[cH:9][cH:10][n:11][cH:12][cH:13]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([CH2:7][c:8]1[cH:9][cH:10][n:11][cH:12][cH:13]1)[C:14]([CH3:15])=[O:16] | CC(=O)CC(=O)OC(C)(C)C.ClCc1ccncc1 | CCOC(=O)C(Cc1ccncc1)C(C)=O | null | null | CN(C=O)C | C-C Coupling | OtherReaction | 51ff748c0cf2861f2ad6789d4151623f0c0967827ce316885260ae190d8b78b6 | 514a7f57dd72c6e5d52bef5e17a9c2ec9f53c1a543e660ee98581ad5fd4bcf8c | c1ccncc1 | C-[C;H0;D4;+0:1](-C)(-[C;D1;H3:2])-[#8:3]-[C:4](=[O;D1;H0:5])-[CH2;D2;+0:6]-[C:7](-[C;D1;H3:8])=[O;D1;H0:9].Cl-[CH2;D2;+0:10]-[c:11]1:[c:12]:[c:13]:[#7;a:14]:[c:15]:[c:16]:1>>[C;D1;H3:8]-[C:7](=[O;D1;H0:9])-[CH;D3;+0:6](-[CH2;D2;+0:10]-[c:11]1:[c:12]:[c:13]:[#7;a:14]:[c:15]:[c:16]:1)-[C:4](=[O;D1;H0:5])-[#8:3]-[CH2;D2;... | 19.9 | [{"value": 18.0, "product": "C(C)(=O)C(C(=O)OCC)CC1=CC=NC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 19.9, "product": "C(C)(=O)C(C(=O)OCC)CC1=CC=NC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | MINUTE | Anhydrous N,N-dimethylformamide (41 ml) was added to sodium hydride (2.81 g, 70.3 mmol) under a nitrogen atmosphere, and the mixture was stirred under ice-cold water-cooling. A solution of t-butyl acetoacetate (6.33 g, 40.0 mmol) in N,N-dimethylformamide (20 ml) was added dropwise to the mixture over 10 minutes, after ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ketone.Ester.Boc | Ketone.Ester | null | null | c1ccncc1 | HCl | CN(C=O)C | null | 0.05 | CC(=O)CC(=O)OC(C)(C)C.ClCc1ccncc1>CN(C=O)C>CCOC(=O)C(Cc1ccncc1)C(C)=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-7af31c35343f4fb8a4bb6252b88ad271 | CCOC(=O)C(Cc1ccncc1)C(C)=O>>CC(=O)CCc1ccncc1 | Cl.C(C)(=O)C(C(=O)OCC)CC1=CC=NC=C1>>N1=CC=C(C=C1)CCC(C)=O | CCOC(=O)[CH:4]([C:2]([CH3:1])=[O:3])[CH2:5][c:6]1[cH:7][cH:8][n:9][cH:10][cH:11]1>>[CH3:1][C:2](=[O:3])[CH2:4][CH2:5][c:6]1[cH:7][cH:8][n:9][cH:10][cH:11]1 | CCOC(=O)C(Cc1ccncc1)C(C)=O | CC(=O)CCc1ccncc1 | null | null | null | Reduction | Decarboxylation | fdc964bea6eaeadfb2309e01318abba99b151c57fdaf3760a2830a6479750a9b | f277909394d9f4e61cc2cdb65fef123102672ca91cfff7f8513cb0baf66138ac | c1ccncc1 | C-C-O-C(=O)-[CH;D3;+0:1](-[C:2]-[c:3])-[C:4](-[C;D1;H3:5])=[O;D1;H0:6]>>[C;D1;H3:5]-[C:4](=[O;D1;H0:6])-[CH2;D2;+0:1]-[C:2]-[c:3] | 110.1 | [{"value": 89.0, "product": "N1=CC=C(C=C1)CCC(C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 110.1, "product": "N1=CC=C(C=C1)CCC(C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Next, 6 N hydrochloric acid (8 ml) was added to ethyl 2-acetyl-3-(4-pyridyl)propionate (1.20 g, 4.81 mmol), and the mixture was refluxed for 1.5 hours. The reaction mixture was concentrated under reduced pressure, 2-propanol (10 ml) was added to the concentrate, and the whole was concentrated under reduced pressure aga... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ester | Ketone | null | null | c1ccncc1 | HO- | null | null | null | CCOC(=O)C(Cc1ccncc1)C(C)=O>>CC(=O)CCc1ccncc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-0bf8c05fbae940ba8dcec8a3c39101cf | CC(=O)CCc1ccncc1.NO>>CC(CCc1ccncc1)=NO | C(O)([O-])=O.[Na+].N1=CC=C(C=C1)CCC(C)=O.C([O-])([O-])=O.[Na+].[Na+].Cl.NO>>N1=CC=C(C=C1)CCC(C)=NO | O=[C:2]([CH3:1])[CH2:3][CH2:4][c:5]1[cH:6][cH:7][n:8][cH:9][cH:10]1.[NH2:11][OH:12]>>[CH3:1][C:2]([CH2:3][CH2:4][c:5]1[cH:6][cH:7][n:8][cH:9][cH:10]1)=[N:11][OH:12] | CC(=O)CCc1ccncc1.NO | CC(CCc1ccncc1)=NO | null | null | C(C)(=O)OCC.O.O1CCCC1 | Heteroatom Alkylation and Arylation | OtherReaction | b5fd91d879f097d0ef2e8e2d3ef7d2ef0195968870a9602a47b8324c601790b9 | 1a0ef15294bdb221fb8888b5d4c7fcf00473b11e53da288791d32747daa48d23 | c1ccncc1 | O=[C;H0;D3;+0:1](-[C;D1;H3:2])-[C:3]-[C:4].[NH2;D1;+0:5]-[O;D1;H1:6]>>[C:4]-[C:3]-[C;H0;D3;+0:1](-[C;D1;H3:2])=[N;H0;D2;+0:5]-[O;D1;H1:6] | 90 | [{"value": 90.0, "product": "N1=CC=C(C=C1)CCC(C)=NO", "details": "PERCENTYIELD", "is_desired": false}, {"value": 89.8, "product": "N1=CC=C(C=C1)CCC(C)=NO", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Next, water (12 ml) and tetrahydrofuran (1.2 ml) were added to 4-(4-pyridyl)-2-butanone (736 mg, 3.96 mmol), and the mixture was stirred at room temperature. Sodium carbonate (483 mg, 4.56 mmol) and hydroxylamine hydrochloride (358 mg, 5.15 mmol) were added to the mixture, and the whole was stirred for 1.5 hours and th... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Primary amine | Oxime | null | null | c1ccncc1 | HO- | C(C)(=O)OCC.O.O1CCCC1 | null | null | CC(=O)CCc1ccncc1.NO>C(C)(=O)OCC.O.O1CCCC1>CC(CCc1ccncc1)=NO |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-55f973db0678448db852f6c144d998a1 | CC(CCc1ccncc1)=NO>>CC(N)CCc1ccncc1 | C(OC(C)(C)C)(OC(C)(C)C)=O.N1=CC=C(C=C1)CCC(C)=NO.[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+]>>NC(CCC1=CC=NC=C1)C | O[N:3]=[C:2]([CH3:1])[CH2:4][CH2:5][c:6]1[cH:7][cH:8][n:9][cH:10][cH:11]1>>[CH3:1][CH:2]([NH2:3])[CH2:4][CH2:5][c:6]1[cH:7][cH:8][n:9][cH:10][cH:11]1 | CC(CCc1ccncc1)=NO | CC(N)CCc1ccncc1 | null | null | C(Cl)(Cl)Cl.C(C)(=O)OCC.CCOCC | Reduction | OtherReaction | 2911de7676f9c054838849cab652dcb324de4944866edb887235c5bf7854a715 | 4a7bf747f64425b21ceaa04fbc4c046ccf522c774aa5649ec92eba03e46bfee5 | c1ccncc1 | O-[N;H0;D2;+0:1]=[C;H0;D3;+0:2](-[C;D1;H3:3])-[C:4]-[C:5]>>[C:5]-[C:4]-[CH;D3;+0:2](-[C;D1;H3:3])-[NH2;D1;+0:1] | 32 | [{"value": 32.0, "product": "NC(CCC1=CC=NC=C1)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 31.7, "product": "NC(CCC1=CC=NC=C1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | Next, anhydrous ether (19 ml) was added to lithium aluminum hydride (257 mg, 6.77 mmol) under a nitrogen atmosphere, and the mixture was stirred under ice-cooling. A solution of 4-(4-pyridyl)-2-butanoneoxime (556 mg, 3.38 mmol) in ether (15 ml) was added dropwise to the mixture over seven minutes, then the temperature ... | 10.6084/m9.figshare.5104873.v1 | null | Oxime | Primary amine | null | null | c1ccncc1 | Other | C(Cl)(Cl)Cl.C(C)(=O)OCC.CCOCC | null | 3 | CC(CCc1ccncc1)=NO>C(Cl)(Cl)Cl.C(C)(=O)OCC.CCOCC>CC(N)CCc1ccncc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-d0983ff7c02048699ba7f9023a7fbbfa | C1CCOC1.CC(C)C#N.CC(C)NC(C)C.O>>CC(C)(C#N)C(O)c1ccncc1 | C(C(C)C)#N.C(CCC)[Li].C(C)(C)NC(C)C.O1CCCC1.O>>OC(C(C#N)(C)C)C1=CC=NC=C1 | O1[CH2:6][CH2:8][CH2:9][CH2:10]1.[CH3:1][CH:2]([CH3:3])[C:4]#[N:5].CC(C)[NH:11][CH:12](C)[CH3:13].[OH2:7]>>[CH3:1][C:2]([CH3:3])([C:4]#[N:5])[CH:6]([OH:7])[c:8]1[cH:9][cH:10][n:11][cH:12][cH:13]1 | C1CCOC1.CC(C)C#N.CC(C)NC(C)C.O | CC(C)(C#N)C(O)c1ccncc1 | null | null | CCCCCC | Aromatic Heterocycle Formation | OtherReaction | 8bbcff325277e1bf5637770ce1565a241f0acca9eea4cc23cfdee7a4a596979a | 05c31d03bbbf30e1db62fd00b311545776a4e9e91bd125452eb623fe38168fe1 | c1ccncc1 | C-C(-C)-[NH;D2;+0:1]-[CH;D3;+0:2](-C)-[CH3;D1;+0:3].O1-[CH2;D2;+0:4]-[CH2;D2;+0:5]-[CH2;D2;+0:6]-[CH2;D2;+0:7]-1.[C;D1;H3:8]-[CH;D3;+0:9](-[C;D1;H3:10])-[C:11]#[N;D1;H0:12].[OH2;D0;+0:13]>>[C;D1;H3:8]-[C;H0;D4;+0:9](-[C;D1;H3:10])(-[C:11]#[N;D1;H0:12])-[CH;D3;+0:7](-[OH;D1;+0:13])-[c;H0;D3;+0:6]1:[cH;D2;+0:3]:[cH;D2;+0... | 71.6 | [{"value": 71.6, "product": "OC(C(C#N)(C)C)C1=CC=NC=C1", "details": "PERCENTYIELD", "is_desired": false}] | -78 | CELSIUS | 10 | MINUTE | A solution of diisopropylamine (10.0 ml, 71.5 mmol) in tetrahydrofuran (150 ml) was cooled to −78° C. under a nitrogen atmosphere, and a 1.6 N solution of butyllithium in hexane was added dropwise thereto over 10 minutes. The mixture was cooled with ice-cold water for 20 minutes and then cooled to −78° C. again, and is... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Secondary amine | Secondary alcohol | C1CCOC1 | c1ccncc1 | c1ccncc1 | HO- | CCCCCC | -78 | 0.166667 | C1CCOC1.CC(C)C#N.CC(C)NC(C)C.O>CCCCCC>CC(C)(C#N)C(O)c1ccncc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-e162f5a92b724cdcb52d12a66305c960 | CC(C)(C#N)C(O)c1ccncc1.Cc1ccc(S(=O)(=O)Cl)cc1>>Cc1ccc(S(=O)(=O)OC(c2ccncc2)C(C)(C)C#N)cc1 | C(C)N(CC)CC.OC(C(C#N)(C)C)C1=CC=NC=C1.C1(=CC=C(C=C1)S(=O)(=O)Cl)C>>CC(C#N)(C(OS(=O)(=O)C1=CC=C(C=C1)C)C1=CC=NC=C1)C | [OH:9][CH:10]([c:11]1[cH:12][cH:13][n:14][cH:15][cH:16]1)[C:17]([CH3:18])([CH3:19])[C:20]#[N:21].Cl[S:6]([c:5]1[cH:4][cH:3][c:2]([CH3:1])[cH:23][cH:22]1)(=[O:7])=[O:8]>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([S:6](=[O:7])(=[O:8])[O:9][CH:10]([c:11]2[cH:12][cH:13][n:14][cH:15][cH:16]2)[C:17]([CH3:18])([CH3:19])[C:20]#[N:21])[cH... | CC(C)(C#N)C(O)c1ccncc1.Cc1ccc(S(=O)(=O)Cl)cc1 | Cc1ccc(S(=O)(=O)OC(c2ccncc2)C(C)(C)C#N)cc1 | null | null | ClCCl | Acylation | Formation of Sulfonic Esters | ad3deb6f5d4dc7823aa3ad2bfe24985be1f3e6860ff8cc0ba215d7624074ef69 | ec645297cfd3107bffb1a4753ac125e48856598e58005e939bb2f0e91bf5e57c | O=S(=O)(OCc1ccncc1)c1ccccc1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6].[C:7]-[C:8](-[OH;D1;+0:9])-[c:10]>>[C:7]-[C:8](-[c:10])-[O;H0;D2;+0:9]-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6] | 37.4 | [{"value": 37.4, "product": "CC(C#N)(C(OS(=O)(=O)C1=CC=C(C=C1)C)C1=CC=NC=C1)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 37.3, "product": "CC(C#N)(C(OS(=O)(=O)C1=CC=C(C=C1)C)C1=CC=NC=C1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 50 | CELSIUS | 3 | DAY | Triethylamine (1.57 ml, 11.3 mmol) was added to a solution of 3-hydroxy-2,2-dimethyl-3-(4-pyridyl)propionitrile (1.00 g, 5.67 mmol) in dichloromethane (20 ml) at room temperature. Further, p-toluenesulfonyl chloride (1.30 g, 6.80 mmol) was added to the mixture, and the whole was warmed at 50° C. with stirring for three... | 10.6084/m9.figshare.5104873.v1 | null | Tosylate.Secondary alcohol.Sulfonyl halide | Tosylate | null | null | c1ccccc1.c1ccncc1 | HCl | ClCCl | 50 | 72 | CC(C)(C#N)C(O)c1ccncc1.Cc1ccc(S(=O)(=O)Cl)cc1>ClCCl>Cc1ccc(S(=O)(=O)OC(c2ccncc2)C(C)(C)C#N)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-46d8f288066544dda525fefef5f195a2 | Cc1ccc(S(=O)(=O)OC(c2ccncc2)C(C)(C)C#N)cc1>>CC(C)(CN)Cc1ccncc1 | CC(C#N)(C(OS(=O)(=O)C1=CC=C(C=C1)C)C1=CC=NC=C1)C.C(C)OCC.[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+]>>CC(CN)(CC1=CC=NC=C1)C | Cc1ccc(S(=O)(=O)O[CH:6]([C:2]([CH3:1])([CH3:3])[C:4]#[N:5])[c:7]2[cH:8][cH:9][n:10][cH:11][cH:12]2)cc1>>[CH3:1][C:2]([CH3:3])([CH2:4][NH2:5])[CH2:6][c:7]1[cH:8][cH:9][n:10][cH:11][cH:12]1 | Cc1ccc(S(=O)(=O)OC(c2ccncc2)C(C)(C)C#N)cc1 | CC(C)(CN)Cc1ccncc1 | null | null | O.O1CCCC1 | Functional Group Interconversion | OtherReaction | 4064755bff94ea8cc2ee22102ffc3bc7666c68061159025d0f9318895e4e1e37 | 2faa9cdf486379b7c62b40fa96e26ac98e80af3134bd0f0c49a7f1ebf160d1b3 | c1ccncc1 | C-c1:c:c:c(-S(=O)(=O)-O-[CH;D3;+0:1](-[c:2]2:[c:3]:[c:4]:[#7;a:5]:[c:6]:[c:7]:2)-[C:8](-[C;D1;H3:9])(-[C;D1;H3:10])-[C;H0;D2;+0:11]#[N;H0;D1;+0:12]):c:c:1>>[C;D1;H3:9]-[C:8](-[C;D1;H3:10])(-[CH2;D2;+0:11]-[NH2;D1;+0:12])-[CH2;D2;+0:1]-[c:2]1:[c:3]:[c:4]:[#7;a:5]:[c:6]:[c:7]:1 | 28 | [{"value": 28.0, "product": "CC(CN)(CC1=CC=NC=C1)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 27.7, "product": "CC(CN)(CC1=CC=NC=C1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | Anhydrous diethyl ether (10 ml) was dropwise to lithium aluminum hydride (345 mg, 9.10 mmol) under a nitrogen atmosphere and ice-cold water-cooling. Then, a solution of 2,2-dimethyl-3-(4-pyridyl)-3-(p-tolylsulfonyloxy)propionitrile (600 mg, 1.82 mmol) in tetrahydrofuran (10 ml) was added dropwise to the mixture. The wh... | 10.6084/m9.figshare.5104873.v1 | null | Tosylate.Nitrile | Primary amine | c1ccccc1 | null | c1ccncc1 | TsOH.HO- | O.O1CCCC1 | null | 8 | Cc1ccc(S(=O)(=O)OC(c2ccncc2)C(C)(C)C#N)cc1>O.O1CCCC1>CC(C)(CN)Cc1ccncc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-080b71591e8b426b8ee1dba74ac981e3 | C1CCOC1.CC#N.[Li][CH2]CCC.[NH4+]>>N#CCC(O)c1ccncc1 | [Cl-].[NH4+].C(C)(C)NC(C)C.C(CCC)[Li].CCCCCC.O1CCCC1.C(C)#N>>OC(CC#N)C1=CC=NC=C1 | [CH2:4]1[O:5][CH2:8][CH2:7][CH2:6]1.[N:1]#[C:2][CH3:3].[Li][CH2]C[CH2:11][CH3:10].[NH4+:9]>>[N:1]#[C:2][CH2:3][CH:4]([OH:5])[c:6]1[cH:7][cH:8][n:9][cH:10][cH:11]1 | C1CCOC1.CC#N.[Li][CH2]CCC.[NH4+] | N#CCC(O)c1ccncc1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | c02a0de28d87028a164d5d52eb4996f44531d4e097350d40a5e4cb3faa668db3 | 99a92e279df4f2839d84059a66b33597d2002f8facc6205196ca2d4c27e616f2 | c1ccncc1 | [CH2;D2;+0:1]1-[CH2;D2;+0:2]-[CH2;D2;+0:3]-[CH2;D2;+0:4]-[O;H0;D2;+0:5]-1.[CH3;D1;+0:6]-[CH2;D2;+0:7]-C-[CH2]-[Li].[CH3;D1;+0:8]-[C:9]#[N;D1;H0:10].[NH4+;D0:11]>>[N;D1;H0:10]#[C:9]-[CH2;D2;+0:8]-[CH;D3;+0:1](-[OH;D1;+0:5])-[c;H0;D3;+0:2]1:[cH;D2;+0:7]:[cH;D2;+0:6]:[n;H0;D2;+0:11]:[cH;D2;+0:4]:[cH;D2;+0:3]:1 | 63.5 | [{"value": 63.5, "product": "OC(CC#N)C1=CC=NC=C1", "details": "PERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 30 | MINUTE | Diisopropylamine (1.98 g, 19.6 mmol) was added dropwise to a solution of a butyllithium/hexane solution (10.5 ml, 16.8 mmol) in anhydrous tetrahydrofuran (20 ml) at −80° C. over five minutes, the temperature was raised to 0° C., and the mixture was stirred for 30 minutes. The mixture was cooled to −80° C. again, then a... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Alkyl lithium | Secondary alcohol | C1CCOC1 | c1ccncc1 | c1ccncc1 | Li | null | 0 | 0.5 | C1CCOC1.CC#N.[Li][CH2]CCC.[NH4+]>>N#CCC(O)c1ccncc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-5796659c7f674d9aaacb6e64badd6d98 | CC(C)(C)[Si](Cl)(c1ccccc1)c1ccccc1.N#CCC(O)c1ccncc1>>CC(C)(C)[Si](OC(CC#N)c1ccncc1)(c1ccccc1)c1ccccc1 | C(C)(C)(C)[Si](Cl)(C1=CC=CC=C1)C1=CC=CC=C1.N1C=NC=C1.CN(C=O)C.OC(CC#N)C1=CC=NC=C1>>O([Si](C1=CC=CC=C1)(C1=CC=CC=C1)C(C)(C)C)C(CC#N)C1=CC=NC=C1 | Cl[Si:5]([C:2]([CH3:1])([CH3:3])[CH3:4])([c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1)[c:23]1[cH:24][cH:25][cH:26][cH:27][cH:28]1.[OH:6][CH:7]([CH2:8][C:9]#[N:10])[c:11]1[cH:12][cH:13][n:14][cH:15][cH:16]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[Si:5]([O:6][CH:7]([CH2:8][C:9]#[N:10])[c:11]1[cH:12][cH:13][n:14][cH:15][cH:16]1)([... | CC(C)(C)[Si](Cl)(c1ccccc1)c1ccccc1.N#CCC(O)c1ccncc1 | CC(C)(C)[Si](OC(CC#N)c1ccncc1)(c1ccccc1)c1ccccc1 | null | null | C(C)(=O)OCC.CCOCC | Protection | Alcohol protection with silyl ethers | ea139b3cb6171a748fbc881d815cc598a14c6b8245b87168b4a15a10e325f24c | 1e2a25dd539d267852f3b05b92dd4080ece1d4c7abb9db1b6fd2b64d2b33a864 | c1ccc([SiH](OCc2ccncc2)c2ccccc2)cc1 | Cl-[Si;H0;D4;+0:1](-[c:2](:[c:3]):[c:4])(-[c:5](:[c:6]):[c:7])-[C:8](-[C;D1;H3:9])(-[C;D1;H3:10])-[C;D1;H3:11].[C:12]-[C:13](-[OH;D1;+0:14])-[c:15]>>[C:12]-[C:13](-[c:15])-[O;H0;D2;+0:14]-[Si;H0;D4;+0:1](-[c:2](:[c:3]):[c:4])(-[c:5](:[c:6]):[c:7])-[C:8](-[C;D1;H3:9])(-[C;D1;H3:10])-[C;D1;H3:11] | 98.9 | [{"value": 98.9, "product": "O([Si](C1=CC=CC=C1)(C1=CC=CC=C1)C(C)(C)C)C(CC#N)C1=CC=NC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 98.9, "product": "O([Si](C1=CC=CC=C1)(C1=CC=CC=C1)C(C)(C)C)C(CC#N)C1=CC=NC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Next, imidazole (4.60 g, 67.5 mmol) and N,N-dimethylformamide (30 ml) were added to the obtained 3-hydroxy-3-(4-pyridyl)propionitrile (1.00 g, 6.75 mmol), and the mixture was stirred at room temperature. t-Butyldiphenylchlorosilane (2.23 g, 8.10 mmol) was added to the mixture, and the whole was stirred for one day and ... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol.Silyl protective group | Silyl protective group | null | null | c1ccncc1.c1ccccc1.c1ccccc1 | HCl | C(C)(=O)OCC.CCOCC | null | null | CC(C)(C)[Si](Cl)(c1ccccc1)c1ccccc1.N#CCC(O)c1ccncc1>C(C)(=O)OCC.CCOCC>CC(C)(C)[Si](OC(CC#N)c1ccncc1)(c1ccccc1)c1ccccc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-f849e22082904606b4e01986dc77a519 | CC(C)(C)[Si](OC(CC#N)c1ccncc1)(c1ccccc1)c1ccccc1>>CC(C)(C)[Si](OC(CCN)c1ccncc1)(c1ccccc1)c1ccccc1 | [H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+].O([Si](C1=CC=CC=C1)(C1=CC=CC=C1)C(C)(C)C)C(CC#N)C1=CC=NC=C1.C(C)(=O)OCC>>[Si](C1=CC=CC=C1)(C1=CC=CC=C1)(C(C)(C)C)OC(CCN)C1=CC=NC=C1 | [CH3:1][C:2]([CH3:3])([CH3:4])[Si:5]([O:6][CH:7]([CH2:8][C:9]#[N:10])[c:11]1[cH:12][cH:13][n:14][cH:15][cH:16]1)([c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1)[c:23]1[cH:24][cH:25][cH:26][cH:27][cH:28]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[Si:5]([O:6][CH:7]([CH2:8][CH2:9][NH2:10])[c:11]1[cH:12][cH:13][n:14][cH:15][cH:16]1)([c... | CC(C)(C)[Si](OC(CC#N)c1ccncc1)(c1ccccc1)c1ccccc1 | CC(C)(C)[Si](OC(CCN)c1ccncc1)(c1ccccc1)c1ccccc1 | null | null | O.C(C)OCC | Reduction | Reduction of nitrile to amine | 65bec2d9f430701d30dc9fcbe1c5418f3dfa174d67be035c50edfc71895dc9c7 | e8d1bc928b94bd4f5bf4b23363ce8f88b1ce7d146ba93829e7b8ad8dbe0007a7 | c1ccc([SiH](OCc2ccncc2)c2ccccc2)cc1 | [C:1]-[C:2]-[C;H0;D2;+0:3]#[N;H0;D1;+0:4]>>[C:1]-[C:2]-[CH2;D2;+0:3]-[NH2;D1;+0:4] | 17.8 | [{"value": 17.8, "product": "[Si](C1=CC=CC=C1)(C1=CC=CC=C1)(C(C)(C)C)OC(CCN)C1=CC=NC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 17.8, "product": "[Si](C1=CC=CC=C1)(C1=CC=CC=C1)(C(C)(C)C)OC(CCN)C1=CC=NC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | MINUTE | Lithium aluminum hydride (299 mg, 7.87 mmol) was suspended in anhydrous diethyl ether (10 ml) under a nitrogen atmosphere, and a solution of the obtained 3-(t-butyldiphenylsiloxy)-3-(4-pyridyl)propionitrile (1.00 g, 2.59 mmol) in anhydrous diethyl ether (15 ml) was added dropwise to the suspension under ice-cooling wit... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile | Primary amine | null | null | c1ccncc1.c1ccccc1.c1ccccc1 | null | O.C(C)OCC | null | 0.133333 | CC(C)(C)[Si](OC(CC#N)c1ccncc1)(c1ccccc1)c1ccccc1>O.C(C)OCC>CC(C)(C)[Si](OC(CCN)c1ccncc1)(c1ccccc1)c1ccccc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-0eb80d802e664db3981256e4c180b24f | CCCCCNCCC12CC3CC(CC(C3)C1)C2.NCCCc1ccncc1.O=C(n1ccnc1)n1ccnc1>>CCCCCN(CCC12CC3CC(CC(C3)C1)C2)C(=O)NCCCc1ccncc1 | C(=O)(N1C=NC=C1)N1C=NC=C1.NCCCC1=CC=NC=C1.Cl.C12(CC3CC(CC(C1)C3)C2)CCNCCCCC>>C12(CC3CC(CC(C1)C3)C2)CCN(C(=O)NCCCC2=CC=NC=C2)CCCCC | [CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][NH:6][CH2:7][CH2:8][C:9]12[CH2:10][CH:11]3[CH2:12][CH:13]([CH2:14][CH:15]([CH2:16]3)[CH2:17]1)[CH2:18]2.[NH2:21][CH2:22][CH2:23][CH2:24][c:25]1[cH:26][cH:27][n:28][cH:29][cH:30]1.c1cn([C:19](n2ccnc2)=[O:20])cn1>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][N:6]([CH2:7][CH2:8][C:9]12[CH2:10][C... | CCCCCNCCC12CC3CC(CC(C3)C1)C2.NCCCc1ccncc1.O=C(n1ccnc1)n1ccnc1 | CCCCCN(CCC12CC3CC(CC(C3)C1)C2)C(=O)NCCCc1ccncc1 | null | null | C(C)(=O)OCC.O1CCCC1 | Acylation | OtherReaction | f4dd0282cbfc717a6a9609eb36d2e65f9c0aac6e585fd933723172d3d62534b8 | 092fb1988ce3c31a0210cc9ec123f317c79841c29a05a3f2098134944f12c379 | O=C(NCCCc1ccncc1)NCCC12CC3CC(CC(C3)C1)C2 | [C:1]-[C:2]-[NH2;D1;+0:3].[C:4]-[C:5]-[NH;D2;+0:6]-[C:7]-[C:8].[O;D1;H0:9]=[C;H0;D3;+0:10](-n1:c:c:n:c:1)-n1:c:c:n:c:1>>[C:1]-[C:2]-[NH;D2;+0:3]-[C;H0;D3;+0:10](=[O;D1;H0:9])-[N;H0;D3;+0:6](-[C:5]-[C:4])-[C:7]-[C:8] | 73.6 | [{"value": 73.0, "product": "C12(CC3CC(CC(C1)C3)C2)CCN(C(=O)NCCCC2=CC=NC=C2)CCCCC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 73.6, "product": "C12(CC3CC(CC(C1)C3)C2)CCN(C(=O)NCCCC2=CC=NC=C2)CCCCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 20 | MINUTE | 1,1′-Carbonyldiimidazole (427 mg, 2.63 mmol) was added to a solution of 4-(3-aminopropyl)pyridine (Intermediate No. 2-1) (285 mg, 2.09 mmol) in tetrahydrofuran (10 ml), and the mixture was stirred at room temperature for 20 minutes. 2-(1-Adamantyl)-N-pentylethylamine hydrochloride (Intermediate No. 1-1) (571 mg, 2.00 m... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Secondary amine | Urea | c1c[nH]cn1.c1c[nH]cn1 | null | c1ccncc1.C1C2CC3CC1CC(C2)C3 | Other | C(C)(=O)OCC.O1CCCC1 | null | 0.333333 | CCCCCNCCC12CC3CC(CC(C3)C1)C2.NCCCc1ccncc1.O=C(n1ccnc1)n1ccnc1>C(C)(=O)OCC.O1CCCC1>CCCCCN(CCC12CC3CC(CC(C3)C1)C2)C(=O)NCCCc1ccncc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-4351c24f160f458fa676dd6b51a8dce8 | CCCNCCC12CC3CC(CC(C3)C1)C2.O=C(O)CCCCc1ccncc1>>CCCN(CCC12CC3CC(CC(C3)C1)C2)C(=O)CCCCc1ccncc1 | C12(CC3CC(CC(C1)C3)C2)CCNCCC.N1=CC=C(C=C1)CCCCC(=O)O.CN1CCOCC1.Cl.C(C)N=C=NCCCN(C)C>>C12(CC3CC(CC(C1)C3)C2)CCN(C(CCCCC2=CC=NC=C2)=O)CCC | [CH3:1][CH2:2][CH2:3][NH:4][CH2:5][CH2:6][C:7]12[CH2:8][CH:9]3[CH2:10][CH:11]([CH2:12][CH:13]([CH2:14]3)[CH2:15]1)[CH2:16]2.O[C:17](=[O:18])[CH2:19][CH2:20][CH2:21][CH2:22][c:23]1[cH:24][cH:25][n:26][cH:27][cH:28]1>>[CH3:1][CH2:2][CH2:3][N:4]([CH2:5][CH2:6][C:7]12[CH2:8][CH:9]3[CH2:10][CH:11]([CH2:12][CH:13]([CH2:14]3)... | CCCNCCC12CC3CC(CC(C3)C1)C2.O=C(O)CCCCc1ccncc1 | CCCN(CCC12CC3CC(CC(C3)C1)C2)C(=O)CCCCc1ccncc1 | null | null | CN(C=O)C | Acylation | Acylation of Nitrogen Nucleophiles by Carboxylic Acids | ac72df6259d5d7baee7abdbd4706ef4b4627f86ead9dc94f0cefcfcb37c21def | c5e4172490b2731ba9322b68af56376edadc31ce0bb9a3dfdea23a1817a852fd | O=C(CCCCc1ccncc1)NCCC12CC3CC(CC(C3)C1)C2 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[C:5]-[C:6]-[NH;D2;+0:7]-[C:8]-[C:9]>>[C:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[N;H0;D3;+0:7](-[C:6]-[C:5])-[C:8]-[C:9] | 33 | [{"value": 33.0, "product": "C12(CC3CC(CC(C1)C3)C2)CCN(C(CCCCC2=CC=NC=C2)=O)CCC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 32.3, "product": "C12(CC3CC(CC(C1)C3)C2)CCN(C(CCCCC2=CC=NC=C2)=O)CCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | N,N-Dimethylformamide (8.4 ml) was added to a mixture of 2-(1-adamantyl)-N-propylethylamine (Intermediate No. 1-6) (0.37 g, 1.7 mmol) and 5-(4-pyridyl)valeric acid (Intermediate No. 5-1) (0.30 g, 1.7 mmol), and the whole was stirred at room temperature. N-Methylmorpholine (0.27 ml, 2.5 mmol) and then 1-ethyl-3-(3-dimet... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | Tertiary amide | null | null | c1ccncc1.C1C2CC3CC1CC(C2)C3 | HO- | CN(C=O)C | null | null | CCCNCCC12CC3CC(CC(C3)C1)C2.O=C(O)CCCCc1ccncc1>CN(C=O)C>CCCN(CCC12CC3CC(CC(C3)C1)C2)C(=O)CCCCc1ccncc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-0a0971544254491fb73c8a18d6027388 | CN(CCN(CCC12CC3CC(CC(C3)C1)C2)C(=O)NCCCc1ccncc1)C(=O)OC(C)(C)C>>CNCCN(CCC12CC3CC(CC(C3)C1)C2)C(=O)NCCCc1ccncc1.Cl | C12(CC3CC(CC(C1)C3)C2)CCN(C(=O)NCCCC2=CC=NC=C2)CCN(C)C(=O)OC(C)(C)C.Cl>>Cl.Cl.C12(CC3CC(CC(C1)C3)C2)CCN(C(=O)NCCCC2=CC=NC=C2)CCNC | CC(C)(C)OC(=O)[N:2]([CH3:1])[CH2:3][CH2:4][N:5]([CH2:6][CH2:7][C:8]12[CH2:9][CH:10]3[CH2:11][CH:12]([CH2:13][CH:14]([CH2:15]3)[CH2:16]1)[CH2:17]2)[C:18](=[O:19])[NH:20][CH2:21][CH2:22][CH2:23][c:24]1[cH:25][cH:26][n:27][cH:28][cH:29]1>>[CH3:1][NH:2][CH2:3][CH2:4][N:5]([CH2:6][CH2:7][C:8]12[CH2:9][CH:10]3[CH2:11][CH:12]... | CN(CCN(CCC12CC3CC(CC(C3)C1)C2)C(=O)NCCCc1ccncc1)C(=O)OC(C)(C)C | CNCCN(CCC12CC3CC(CC(C3)C1)C2)C(=O)NCCCc1ccncc1.Cl | null | null | CO | Miscellaneous | Boc amine deprotection | 43bd7dbe082e19ce552084e8c807e7cb13b754bbd3730fa221829c57747abf05 | c95e79e18f8ea11cf22745e0eab38cab98566b1b63e7d80ee200f4cb4f94f00c | O=C(NCCCc1ccncc1)NCCC12CC3CC(CC(C3)C1)C2 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1](-[C;D1;H3:2])-[C:3]-[C:4]>>[C:4]-[C:3]-[NH;D2;+0:1]-[C;D1;H3:2] | null | [] | null | null | null | null | Methanol (4.4 ml) was added to 1-[2-(1-adamantyl)ethyl]-1-[2-[N-(t-butoxycarbonyl)-N-methylamino]ethyl]-3-[3-(4-pyridyl)propyl]urea (Compound No. 1-26) (0.30 g, 0.6 mmol), a calcium chloride tube was attached to the vessel, and the mixture was stirred at room temperature. A 10% solution of hydrogen chloride in methanol... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Secondary amine | null | null | c1ccncc1.C1C2CC3CC1CC(C2)C3 | HO- | CO | null | null | CN(CCN(CCC12CC3CC(CC(C3)C1)C2)C(=O)NCCCc1ccncc1)C(=O)OC(C)(C)C>CO>CNCCN(CCC12CC3CC(CC(C3)C1)C2)C(=O)NCCCc1ccncc1.Cl |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b337c3f6b67740aa913be31c3193b3a0 | CCCCCN(CCC12CC3CC(CC(C3)C1)C2)C(=O)NCCCc1ccncc1.CI>>CCCCCN(CCC12CC3CC(CC(C3)C1)C2)C(=O)NCCCc1cc[n+](C)cc1.[I-] | CI.C12(CC3CC(CC(C1)C3)C2)CCN(C(=O)NCCCC2=CC=NC=C2)CCCCC>>[I-].C12(CC3CC(CC(C1)C3)C2)CCN(C(NCCCC2=CC=[N+](C=C2)C)=O)CCCCC | [CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][N:6]([CH2:7][CH2:8][C:9]12[CH2:10][CH:11]3[CH2:12][CH:13]([CH2:14][CH:15]([CH2:16]3)[CH2:17]1)[CH2:18]2)[C:19](=[O:20])[NH:21][CH2:22][CH2:23][CH2:24][c:25]1[cH:26][cH:27][n:28][cH:30][cH:31]1.[CH3:29][I:32]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][N:6]([CH2:7][CH2:8][C:9]12[CH2:10][CH:1... | CCCCCN(CCC12CC3CC(CC(C3)C1)C2)C(=O)NCCCc1ccncc1.CI | CCCCCN(CCC12CC3CC(CC(C3)C1)C2)C(=O)NCCCc1cc[n+](C)cc1.[I-] | null | null | CC(=O)C | Functional Group Interconversion | OtherReaction | 54415aed4bb61f76efee9ed140374352608210a9fed7c372975c12eb7023cea2 | f1bbf9aa3c82f5e49be9f6d53533b6bb152f359232b6d32090c168949766aa71 | O=C(NCCCc1cc[nH+]cc1)NCCC12CC3CC(CC(C3)C1)C2 | [CH3;D1;+0:1]-[I;H0;D1;+0:2].[c:3]:[c:4]:[n;H0;D2;+0:5]:[c:6]:[c:7]>>[CH3;D1;+0:1]-[n+;H0;D3:5](:[c:4]:[c:3]):[c:6]:[c:7].[I-;H0;D0:2] | 96 | [{"value": 96.0, "product": "[I-].C12(CC3CC(CC(C1)C3)C2)CCN(C(NCCCC2=CC=[N+](C=C2)C)=O)CCCCC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Methyl iodide (90 μl, 1.5 mmol) was added to a solution of 1-[2-(1-adamantyl)ethyl]-1-pentyl-3-[3-(4-pyridyl)propyl]urea (Compound No. 1-1) (0.30 g, 0.73 mmol) in acetone (1.5 ml) at room temperature, and the mixture was stirred overnight. The solvent was evaporated under reduced pressure from the reaction mixture, and... | 10.6084/m9.figshare.5104873.v1 | null | null | null | c1ccncc1 | C1=CC=[NH+]C=C1 | C1=CC=[NH+]C=C1.C1C2CC3CC1CC(C2)C3 | null | CC(=O)C | null | null | CCCCCN(CCC12CC3CC(CC(C3)C1)C2)C(=O)NCCCc1ccncc1.CI>CC(=O)C>CCCCCN(CCC12CC3CC(CC(C3)C1)C2)C(=O)NCCCc1cc[n+](C)cc1.[I-] |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-14e89434f0004fa7ac104f39d66973e3 | CCCCCNCCC12CC3CC(CC(C3)C1)C2.O=C(ON1C(=O)CCC1=O)ON1C(=O)CCC1=O.OCCCc1ccncc1>>CCCCCN(CCC12CC3CC(CC(C3)C1)C2)C(=O)OCCCc1ccncc1 | Cl.C12(CC3CC(CC(C1)C3)C2)CCNCCCCC.C(C)N(CC)CC.N1=CC=C(C=C1)CCCO.C(C)N(CC)CC.C1CC(=O)N(C1=O)OC(=O)ON2C(=O)CCC2=O>>C12(CC3CC(CC(C1)C3)C2)CCN(C(OCCCC2=CC=NC=C2)=O)CCCCC | [CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][NH:6][CH2:7][CH2:8][C:9]12[CH2:10][CH:11]3[CH2:12][CH:13]([CH2:14][CH:15]([CH2:16]3)[CH2:17]1)[CH2:18]2.O=C1CCC(=O)N1O[C:19](ON1C(=O)CCC1=O)=[O:20].[OH:21][CH2:22][CH2:23][CH2:24][c:25]1[cH:26][cH:27][n:28][cH:29][cH:30]1>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][N:6]([CH2:7][CH2:8][C:9]1... | CCCCCNCCC12CC3CC(CC(C3)C1)C2.O=C(ON1C(=O)CCC1=O)ON1C(=O)CCC1=O.OCCCc1ccncc1 | CCCCCN(CCC12CC3CC(CC(C3)C1)C2)C(=O)OCCCc1ccncc1 | null | null | C(C)#N.C(Cl)Cl | Protection | OtherReaction | 8b9e879d3dc0019cebe28d642c4460a77293072162063883ee331602d768feec | bfeab205a966a93184efe1934af54cc9384e050b3ad5d01c68b0b0ced1840279 | O=C(NCCC12CC3CC(CC(C3)C1)C2)OCCCc1ccncc1 | O=C1-C-C-C(=O)-N-1-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-O-N1-C(=O)-C-C-C-1=O.[C:3]-[C:4]-[NH;D2;+0:5]-[C:6]-[C:7].[C:8]-[C:9]-[OH;D1;+0:10]>>[C:8]-[C:9]-[O;H0;D2;+0:10]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[N;H0;D3;+0:5](-[C:4]-[C:3])-[C:6]-[C:7] | 97 | [{"value": 97.0, "product": "C12(CC3CC(CC(C1)C3)C2)CCN(C(OCCCC2=CC=NC=C2)=O)CCCCC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 96.9, "product": "C12(CC3CC(CC(C1)C3)C2)CCN(C(OCCCC2=CC=NC=C2)=O)CCCCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2.5 | HOUR | 4-Pyridinepropanol (528 mg, 3.85 mmol) was dissolved in acetonitrile (20 ml) at room temperature, and then triethylamine (1.61 ml, 11.6 mmol) was added to the solution. Further, N,N-disuccinimidyl carbonate (1.48 g, 5.87 mmol) was added to the mixture, and the whole was stirred for 2.5 hours. The reaction mixture was c... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Tertiary amide.Tertiary amide.Tertiary amide.Primary alcohol.Secondary amine | Carbamic ester | C1CCNC1.C1CCNC1 | null | c1ccncc1.C1C2CC3CC1CC(C2)C3 | HO- | C(C)#N.C(Cl)Cl | null | 2.5 | CCCCCNCCC12CC3CC(CC(C3)C1)C2.O=C(ON1C(=O)CCC1=O)ON1C(=O)CCC1=O.OCCCc1ccncc1>C(C)#N.C(Cl)Cl>CCCCCN(CCC12CC3CC(CC(C3)C1)C2)C(=O)OCCCc1ccncc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-24fedf265b884140ae23bb719462767c | CC(C)(C)OC(=O)CCN(CCC12CC3CC(CC(C3)C1)C2)C(=O)NCCCc1ccncc1>>O=C1CCN(CCC23CC4CC(CC(C4)C2)C3)C(=O)N1CCCc1ccncc1 | Cl.C12(CC3CC(CC(C1)C3)C2)CCN(C(=O)NCCCC2=CC=NC=C2)CCC(=O)OC(C)(C)C.Cl.C(C)(=O)OCC>>Cl.C12(CC3CC(CC(C1)C3)C2)CCN2C(N(C(CC2)=O)CCCC2=CC=NC=C2)=O | CC(C)(C)O[C:3](=[O:2])[CH2:4][CH2:5][N:6]([CH2:7][CH2:8][C:9]12[CH2:10][CH:11]3[CH2:12][CH:13]([CH2:14][CH:15]([CH2:16]3)[CH2:17]1)[CH2:18]2)[C:19](=[O:20])[NH:21][CH2:22][CH2:23][CH2:24][c:25]1[cH:26][cH:27][n:28][cH:29][cH:30]1>>[O:2]=[C:3]1[CH2:4][CH2:5][N:6]([CH2:7][CH2:8][C:9]23[CH2:10][CH:11]4[CH2:12][CH:13]([CH2... | CC(C)(C)OC(=O)CCN(CCC12CC3CC(CC(C3)C1)C2)C(=O)NCCCc1ccncc1 | O=C1CCN(CCC23CC4CC(CC(C4)C2)C3)C(=O)N1CCCc1ccncc1 | null | null | O1CCOCC1 | Miscellaneous | OtherReaction | 922da0d12b97a4a213cd0e40f480336b5a71b2f3cfb74ba1dafae5a6adc74a55 | 441b236630c929976d8c67b614d7c4aa2f33fb79eaf787fc39eda13a24c9181f | O=C1CCN(CCC23CC4CC(CC(C4)C2)C3)C(=O)N1CCCc1ccncc1 | C-C(-C)(-C)-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4]-[#7:5](-[C:6])-[C:7](=[O;D1;H0:8])-[NH;D2;+0:9]-[C:10]-[C:11]>>[C:11]-[C:10]-[N;H0;D3;+0:9]1-[C:7](=[O;D1;H0:8])-[#7:5](-[C:6])-[C:4]-[C:3]-[C;H0;D3;+0:1]-1=[O;D1;H0:2] | 79 | [{"value": 79.0, "product": "Cl.C12(CC3CC(CC(C1)C3)C2)CCN2C(N(C(CC2)=O)CCCC2=CC=NC=C2)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | A 4 N solution of hydrogen chloride in 1,4-dioxane (2.5 ml) was added to 1-[2-(1-adamantyl)ethyl]-1-[2-(t-butoxycarbonyl)ethyl]-3-[3-(4-pyridyl)propyl]urea (Compound No. 1-69) (0.23 g, 0.49 mmol), and the mixture was stirred at room temperature overnight. The reaction mixture was concentrated under reduced pressure, a ... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Urea.Boc | Urea.Substituted dicarboximide | null | C1C[NH]C[NH]C1 | C1C[NH]C[NH]C1.c1ccncc1.C1C2CC3CC1CC(C2)C3 | HO- | O1CCOCC1 | null | 8 | CC(C)(C)OC(=O)CCN(CCC12CC3CC(CC(C3)C1)C2)C(=O)NCCCc1ccncc1>O1CCOCC1>O=C1CCN(CCC23CC4CC(CC(C4)C2)C3)C(=O)N1CCCc1ccncc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-1a9c8bf2a0c94a929282d4054ef2be97 | CCCCCNCCC12CC3CC(CC(C3)C1)C2.NCCCc1ccncc1.S=C(n1ccnc1)n1ccnc1>>CCCCCN(CCC12CC3CC(CC(C3)C1)C2)C(=S)NCCCc1ccncc1 | C(O)([O-])=O.[Na+].Cl.C12(CC3CC(CC(C1)C3)C2)CCNCCCCC.NCCCC1=CC=NC=C1.C(=S)(N1C=NC=C1)N1C=NC=C1>>C12(CC3CC(CC(C1)C3)C2)CCN(C(=S)NCCCC2=CC=NC=C2)CCCCC | [CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][NH:6][CH2:7][CH2:8][C:9]12[CH2:10][CH:11]3[CH2:12][CH:13]([CH2:14][CH:15]([CH2:16]3)[CH2:17]1)[CH2:18]2.[NH2:21][CH2:22][CH2:23][CH2:24][c:25]1[cH:26][cH:27][n:28][cH:29][cH:30]1.c1cn([C:19](n2ccnc2)=[S:20])cn1>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][N:6]([CH2:7][CH2:8][C:9]12[CH2:10][C... | CCCCCNCCC12CC3CC(CC(C3)C1)C2.NCCCc1ccncc1.S=C(n1ccnc1)n1ccnc1 | CCCCCN(CCC12CC3CC(CC(C3)C1)C2)C(=S)NCCCc1ccncc1 | null | null | C(C)(=O)OCC.O1CCCC1 | Heteroatom Alkylation and Arylation | OtherReaction | 8f6639d4c1d8e74fe1edd589fbd0e52f490ad6c8933b6e3ee8c7c59b99e2905a | ac8bed454cbd32bb2d251ac3f635c69390732f28930050cdce90686f9b13ad73 | S=C(NCCCc1ccncc1)NCCC12CC3CC(CC(C3)C1)C2 | [C:1]-[C:2]-[NH2;D1;+0:3].[C:4]-[C:5]-[NH;D2;+0:6]-[C:7]-[C:8].[S;D1;H0:9]=[C;H0;D3;+0:10](-n1:c:c:n:c:1)-n1:c:c:n:c:1>>[C:1]-[C:2]-[NH;D2;+0:3]-[C;H0;D3;+0:10](=[S;D1;H0:9])-[N;H0;D3;+0:6](-[C:5]-[C:4])-[C:7]-[C:8] | 24 | [{"value": 24.0, "product": "C12(CC3CC(CC(C1)C3)C2)CCN(C(=S)NCCCC2=CC=NC=C2)CCCCC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 23.4, "product": "C12(CC3CC(CC(C1)C3)C2)CCN(C(=S)NCCCC2=CC=NC=C2)CCCCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | A solution of 4-(3-aminopropyl)pyridine (Intermediate No. 2-1) (0.24 g, 1.8 mmol) in anhydrous tetrahydrofuran (10 ml) was added to 1,1′-thiocarbonyldiimidazole (0.31 g, 1.8 mmol) under a nitrogen atmosphere, and the mixture was stirred at room temperature. After one hour, a solution of 2-(1-adamantyl)-N-pentylethylami... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Secondary amine.Thiocarbonyl | Thiourea | c1c[nH]cn1.c1c[nH]cn1 | null | c1ccncc1.C1C2CC3CC1CC(C2)C3 | Other | C(C)(=O)OCC.O1CCCC1 | null | 1 | CCCCCNCCC12CC3CC(CC(C3)C1)C2.NCCCc1ccncc1.S=C(n1ccnc1)n1ccnc1>C(C)(=O)OCC.O1CCCC1>CCCCCN(CCC12CC3CC(CC(C3)C1)C2)C(=S)NCCCc1ccncc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-af7cd9850f9147579b0f06543321c27a | OCCN(CCc1ccccc1)C(=S)NCCCc1ccncc1>>S=C1N(CCCc2ccncc2)CCN1CCc1ccccc1 | C(C)(=O)OCC.N(=NC(=O)OC(C)C)C(=O)OC(C)C.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.OCCN(C(=S)NCCCC1=CC=NC=C1)CCC1=CC=CC=C1>>C(CC1=CC=CC=C1)N1C(N(CC1)CCCC1=CC=NC=C1)=S | O[CH2:13][CH2:14][N:15]([C:2](=[S:1])[NH:3][CH2:4][CH2:5][CH2:6][c:7]1[cH:8][cH:9][n:10][cH:11][cH:12]1)[CH2:16][CH2:17][c:18]1[cH:19][cH:20][cH:21][cH:22][cH:23]1>>[S:1]=[C:2]1[N:3]([CH2:4][CH2:5][CH2:6][c:7]2[cH:8][cH:9][n:10][cH:11][cH:12]2)[CH2:13][CH2:14][N:15]1[CH2:16][CH2:17][c:18]1[cH:19][cH:20][cH:21][cH:22][c... | OCCN(CCc1ccccc1)C(=S)NCCCc1ccncc1 | S=C1N(CCCc2ccncc2)CCN1CCc1ccccc1 | null | null | O1CCCC1 | Heteroatom Alkylation and Arylation | OtherReaction | 873208d89b8649ef87f12c88bf450ca1521ae8a0ed9b336d1a48072bb3c6fa6c | 0ae1dc149d1f03e918acabb377dcac7c4867689ea86352b2da5b4db692ace18e | S=C1N(CCCc2ccncc2)CCN1CCc1ccccc1 | O-[CH2;D2;+0:1]-[C:2]-[#7:3](-[C:4])-[C:5](=[S;D1;H0:6])-[NH;D2;+0:7]-[C:8]-[C:9]>>[C:4]-[#7:3]1-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:7](-[C:8]-[C:9])-[C:5]-1=[S;D1;H0:6] | 19 | [{"value": 19.0, "product": "C(CC1=CC=CC=C1)N1C(N(CC1)CCCC1=CC=NC=C1)=S", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 10 | MINUTE | Anhydrous tetrahydrofuran (2.5 ml) was added to a mixture of 1-(2-hydroxyethyl)-1-phenethyl-3-[3-(4-pyridyl)propyl]thiourea (Compound No. 7-2) (601 mg, 1.75 mmol) and triphenylphosphine (913 mg, 3.49 mmol), and the whole was stirred under ice/methanol-cooling. A solution of diisopropyl azodicarboxylate (710 mg, 3.49 mm... | 10.6084/m9.figshare.5104873.v1 | null | Thiourea.Primary alcohol | Thiourea | null | C1C[NH]C[NH]1 | C1C[NH]C[NH]1.c1ccncc1.c1ccccc1 | HO- | O1CCCC1 | null | 0.166667 | OCCN(CCc1ccccc1)C(=S)NCCCc1ccncc1>O1CCCC1>S=C1N(CCCc2ccncc2)CCN1CCc1ccccc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-ee27711b203844f8bf8d8399484f6c10 | O=C(n1ccnc1)n1ccnc1.c1cc(CCCNCCCNCCC23CC4CC(CC(C4)C2)C3)ccn1>>O=C1N(CCCc2ccncc2)CCCN1CCC12CC3CC(CC(C3)C1)C2 | C(=O)(N1C=NC=C1)N1C=NC=C1.C12(CC3CC(CC(C1)C3)C2)CCNCCCNCCCC2=CC=NC=C2>>C12(CC3CC(CC(C1)C3)C2)CCN2C(N(CCC2)CCCC2=CC=NC=C2)=O | c1cn([C:2](n2ccnc2)=[O:1])cn1.[NH:3]([CH2:4][CH2:5][CH2:6][c:7]1[cH:8][cH:9][n:10][cH:11][cH:12]1)[CH2:13][CH2:14][CH2:15][NH:16][CH2:17][CH2:18][C:19]12[CH2:20][CH:21]3[CH2:22][CH:23]([CH2:24][CH:25]([CH2:26]3)[CH2:27]1)[CH2:28]2>>[O:1]=[C:2]1[N:3]([CH2:4][CH2:5][CH2:6][c:7]2[cH:8][cH:9][n:10][cH:11][cH:12]2)[CH2:13][... | O=C(n1ccnc1)n1ccnc1.c1cc(CCCNCCCNCCC23CC4CC(CC(C4)C2)C3)ccn1 | O=C1N(CCCc2ccncc2)CCCN1CCC12CC3CC(CC(C3)C1)C2 | null | null | C(Cl)Cl | Acylation | OtherReaction | e4a2d3741b9929811cf43cf188d9249709cfe1ff5dc8caa574b4982cca8be41e | bf5bab008aedc534107e4f090e82dcd18197098a48ec0ce73cbefdfec414069e | O=C1N(CCCc2ccncc2)CCCN1CCC12CC3CC(CC(C3)C1)C2 | [C:1]-[C:2]-[NH;D2;+0:3]-[C:4]-[C:5]-[C:6]-[NH;D2;+0:7]-[C:8]-[C:9].[O;D1;H0:10]=[C;H0;D3;+0:11](-n1:c:c:n:c:1)-n1:c:c:n:c:1>>[C:1]-[C:2]-[N;H0;D3;+0:3]1-[C:4]-[C:5]-[C:6]-[N;H0;D3;+0:7](-[C:8]-[C:9])-[C;H0;D3;+0:11]-1=[O;D1;H0:10] | 9.4 | [{"value": 9.4, "product": "C12(CC3CC(CC(C1)C3)C2)CCN2C(N(CCC2)CCCC2=CC=NC=C2)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 9.1, "product": "C12(CC3CC(CC(C1)C3)C2)CCN2C(N(CCC2)CCCC2=CC=NC=C2)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | To anhydrous methylene chloride (50 ml) were added a solution of the obtained N-[2-(1-adamantyl)ethyl]-N′-[3-(4-pyridyl)propyl]-1,3-propanediamine (80 mg, 0.23 mmol) in anhydrous methylene chloride (10 ml) and a solution of 1,1′-carbonyldiimidazole (40 mg, 0.26 mmol) in anhydrous methylene chloride (10 ml) dropwise sim... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amine.Secondary amine | Urea | c1c[nH]cn1.c1c[nH]cn1 | C1C[NH]C[NH]C1 | C1C[NH]C[NH]C1.c1ccncc1.C1C2CC3CC1CC(C2)C3 | Other | C(Cl)Cl | null | 8 | O=C(n1ccnc1)n1ccnc1.c1cc(CCCNCCCNCCC23CC4CC(CC(C4)C2)C3)ccn1>C(Cl)Cl>O=C1N(CCCc2ccncc2)CCCN1CCC12CC3CC(CC(C3)C1)C2 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-bfd2588067c1403f8aeac3ae8a3fc03f | CC(=O)OC(C)=O.NN(CCC12CC3CC(CC(C3)C1)C2)C(=O)NCCCc1ccncc1>>CC(=O)NN(CCC12CC3CC(CC(C3)C1)C2)C(=O)NCCCc1ccncc1 | C(C)(=O)OC(C)=O.Cl.Cl.C12(CC3CC(CC(C1)C3)C2)CCN(C(=O)NCCCC2=CC=NC=C2)N>>C(C)(=O)NN(C(=O)NCCCC1=CC=NC=C1)CCC12CC3CC(CC(C1)C3)C2 | CC(=O)O[C:2]([CH3:1])=[O:3].[NH2:4][N:5]([CH2:6][CH2:7][C:8]12[CH2:9][CH:10]3[CH2:11][CH:12]([CH2:13][CH:14]([CH2:15]3)[CH2:16]1)[CH2:17]2)[C:18](=[O:19])[NH:20][CH2:21][CH2:22][CH2:23][c:24]1[cH:25][cH:26][n:27][cH:28][cH:29]1>>[CH3:1][C:2](=[O:3])[NH:4][N:5]([CH2:6][CH2:7][C:8]12[CH2:9][CH:10]3[CH2:11][CH:12]([CH2:13... | CC(=O)OC(C)=O.NN(CCC12CC3CC(CC(C3)C1)C2)C(=O)NCCCc1ccncc1 | CC(=O)NN(CCC12CC3CC(CC(C3)C1)C2)C(=O)NCCCc1ccncc1 | null | null | N1=CC=CC=C1 | Acylation | Aminolysis of esters | bc769be1025ffe6200aac8295da69588bd30740f1c88f9445fb357fd377f5b02 | f8bc0260496753222448b68ebd5c28910488e39633c2b1e5ea8ce82d40221d9d | O=C(NCCCc1ccncc1)NCCC12CC3CC(CC(C3)C1)C2 | C-C(=O)-O-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[#7:4]-[C:5](=[O;D1;H0:6])-[#7:7](-[C:8])-[NH2;D1;+0:9]>>[#7:4]-[C:5](=[O;D1;H0:6])-[#7:7](-[C:8])-[NH;D2;+0:9]-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3] | 58 | [{"value": 58.0, "product": "C(C)(=O)NN(C(=O)NCCCC1=CC=NC=C1)CCC12CC3CC(CC(C1)C3)C2", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 15 | MINUTE | Pyridine (2.0 ml) and acetic anhydride (1.0 ml) were added to 1-[2-(1-adamantyl)ethyl]-1-amino-3-[3-(4-pyridyl)propyl]urea dihydrochloride (Compound No. 3-3) (0.20 g, 0.47 mmol) at room temperature, and the mixture was stirred for 15 minutes. The solvent was evaporated under reduced pressure from the reaction mixture, ... | 10.6084/m9.figshare.5104873.v1 | null | Acylhydrazine.Anhydride | Acylhydrazine.Acylhydrazine | null | null | c1ccncc1.C1C2CC3CC1CC(C2)C3 | HO- | N1=CC=CC=C1 | null | 0.25 | CC(=O)OC(C)=O.NN(CCC12CC3CC(CC(C3)C1)C2)C(=O)NCCCc1ccncc1>N1=CC=CC=C1>CC(=O)NN(CCC12CC3CC(CC(C3)C1)C2)C(=O)NCCCc1ccncc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-d06aa87c346848db80212dbda11ac4e4 | CNCCC12CC3CC(CC(C3)C1)C2.CNCCCc1ccncc1.O=C(OC(Cl)(Cl)Cl)OC(Cl)(Cl)Cl>>CN(CCCc1ccncc1)C(=O)N(C)CCC12CC3CC(CC(C3)C1)C2 | CNCCCC1=CC=NC=C1.C(C)(C)N(CC)C(C)C.C12(CC3CC(CC(C1)C3)C2)CCNC.C(C)(C)N(CC)C(C)C.ClC(Cl)(OC(OC(Cl)(Cl)Cl)=O)Cl>>C12(CC3CC(CC(C1)C3)C2)CCN(C(=O)N(CCCC2=CC=NC=C2)C)C | [NH:14]([CH3:15])[CH2:16][CH2:17][C:18]12[CH2:19][CH:20]3[CH2:21][CH:22]([CH2:23][CH:24]([CH2:25]3)[CH2:26]1)[CH2:27]2.[CH3:1][NH:2][CH2:3][CH2:4][CH2:5][c:6]1[cH:7][cH:8][n:9][cH:10][cH:11]1.ClC(Cl)(Cl)O[C:12](OC(Cl)(Cl)Cl)=[O:13]>>[CH3:1][N:2]([CH2:3][CH2:4][CH2:5][c:6]1[cH:7][cH:8][n:9][cH:10][cH:11]1)[C:12](=[O:13]... | CNCCC12CC3CC(CC(C3)C1)C2.CNCCCc1ccncc1.O=C(OC(Cl)(Cl)Cl)OC(Cl)(Cl)Cl | CN(CCCc1ccncc1)C(=O)N(C)CCC12CC3CC(CC(C3)C1)C2 | null | null | ClCCl.C(C)OCC | Acylation | OtherReaction | 2d76b2fa33e1eb2b12d56b8ddc0c88ee82cb7b0608963818f0ec3d465f66c2f0 | c77dcb628c46f34db12abe282042119a29544ea9236aafae076c5fc9c8355903 | O=C(NCCCc1ccncc1)NCCC12CC3CC(CC(C3)C1)C2 | Cl-C(-Cl)(-Cl)-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-O-C(-Cl)(-Cl)-Cl.[C:3]-[C:4]-[NH;D2;+0:5]-[C;D1;H3:6].[C:7]-[C:8]-[NH;D2;+0:9]-[C;D1;H3:10]>>[C:3]-[C:4]-[N;H0;D3;+0:5](-[C;D1;H3:6])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[N;H0;D3;+0:9](-[C;D1;H3:10])-[C:8]-[C:7] | 141.6 | [{"value": 54.0, "product": "C12(CC3CC(CC(C1)C3)C2)CCN(C(=O)N(CCCC2=CC=NC=C2)C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 141.6, "product": "C12(CC3CC(CC(C1)C3)C2)CCN(C(=O)N(CCCC2=CC=NC=C2)C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 17 | MINUTE | A solution of triphosgene (190 mg, 0.640 mmol) in dichloromethane (6.0 ml) was stirred at room temperature under a nitrogen atmosphere. A solution of 2-(1-adamantyl)-N-methylethylamine (Intermediate No. 3-1) (330 mg, 1.71 mmol) and diisopropylethylamine (0.357 ml, 2.05 mmol) in dichloromethane (6.0 ml) was added dropwi... | 10.6084/m9.figshare.5104873.v1 | null | Trichloro group.Trichloro group.Carbonic Ester.Secondary amine.Secondary amine | Urea | null | null | c1ccncc1.C1C2CC3CC1CC(C2)C3 | HCl | ClCCl.C(C)OCC | null | 0.283333 | CNCCC12CC3CC(CC(C3)C1)C2.CNCCCc1ccncc1.O=C(OC(Cl)(Cl)Cl)OC(Cl)(Cl)Cl>ClCCl.C(C)OCC>CN(CCCc1ccncc1)C(=O)N(C)CCC12CC3CC(CC(C3)C1)C2 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-fb48d7daa0574f5e892827858802681b | O=C(NCCCc1ccncc1)N(CCC12CC3CC(CC(C3)C1)C2)OCc1ccccc1>>O=C(NCCCc1ccncc1)N(O)CCC12CC3CC(CC(C3)C1)C2 | Cl.C12(CC3CC(CC(C1)C3)C2)CCN(C(=O)NCCCC2=CC=NC=C2)OCC2=CC=CC=C2>>C12(CC3CC(CC(C1)C3)C2)CCN(C(=O)NCCCC2=CC=NC=C2)O | c1ccc(C[O:14][N:13]([C:2](=[O:1])[NH:3][CH2:4][CH2:5][CH2:6][c:7]2[cH:8][cH:9][n:10][cH:11][cH:12]2)[CH2:15][CH2:16][C:17]23[CH2:18][CH:19]4[CH2:20][CH:21]([CH2:22][CH:23]([CH2:24]4)[CH2:25]2)[CH2:26]3)cc1>>[O:1]=[C:2]([NH:3][CH2:4][CH2:5][CH2:6][c:7]1[cH:8][cH:9][n:10][cH:11][cH:12]1)[N:13]([OH:14])[CH2:15][CH2:16][C:... | O=C(NCCCc1ccncc1)N(CCC12CC3CC(CC(C3)C1)C2)OCc1ccccc1 | O=C(NCCCc1ccncc1)N(O)CCC12CC3CC(CC(C3)C1)C2 | null | null | null | Deprotection | OtherReaction | 94fa5e5ed4a5b32c4aba0dd3c8151bfdd08491d1bc6453e9fd01d7dc3e51cd0f | 30a26bc929988d0041b9998cdccd1d65eb125114a78065ed35d40f50c965c0a7 | O=C(NCCCc1ccncc1)NCCC12CC3CC(CC(C3)C1)C2 | [#7:1]-[C:2](=[O;D1;H0:3])-[#7:4](-[C:5])-[O;H0;D2;+0:6]-C-c1:c:c:c:c:c:1>>[#7:1]-[C:2](=[O;D1;H0:3])-[#7:4](-[C:5])-[OH;D1;+0:6] | 34 | [{"value": 34.0, "product": "C12(CC3CC(CC(C1)C3)C2)CCN(C(=O)NCCCC2=CC=NC=C2)O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 3 | DAY | 2 N Hydrochloric acid (4.0 ml) was added to a solution of 1-[2-(1-adamantyl)ethyl]-1-benzyloxy-3-[3-(4-pyridyl)propyl]urea (Compound No. 1-28) (438 mg, 0.978 mmol) in methanol (9.78 ml), and a nitrogen gas was bubbled through the mixture. To the mixture was added 10% palladium on carbon (43 mg), and the whole was stirr... | 10.6084/m9.figshare.5104873.v1 | null | null | null | c1ccccc1 | null | c1ccncc1.C1C2CC3CC1CC(C2)C3 | Other | null | null | 72 | O=C(NCCCc1ccncc1)N(CCC12CC3CC(CC(C3)C1)C2)OCc1ccccc1>>O=C(NCCCc1ccncc1)N(O)CCC12CC3CC(CC(C3)C1)C2 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-7c9faa00da474823a42f76ed03b4aa2b | Cl>>Cl | Cl.C(C)(=O)OCC.C12(CC3CC(CC(C1)C3)C2)CCN(C(=O)NCCCC2=CC=NC=C2)CCCCC>>Cl.C12(CC3CC(CC(C1)C3)C2)CCN(C(=O)NCCCC2=CC=NC=C2)CCCCC | [ClH:31]>>[ClH:31] | Cl | Cl | null | null | C(Cl)(Cl)Cl | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | null | null | 43 | [{"value": 43.0, "product": "Cl.C12(CC3CC(CC(C1)C3)C2)CCN(C(=O)NCCCC2=CC=NC=C2)CCCCC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A 4 N solution of hydrogen chloride in ethyl acetate (0.400 ml, 1.60 mmol) was added to a solution of 1-[2-(1-adamantyl)ethyl]-1-pentyl-3-[3-(4-pyridyl)propyl]urea (Compound No. 1-1) (200 mg, 0.486 mmol) in chloroform (0.3 ml). The solvent was evaporated under reduced pressure, and the precipitated solid was washed wit... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | null | null | C(Cl)(Cl)Cl | null | null | Cl>C(Cl)(Cl)Cl>Cl |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-37e5e7e01b6d4992bf0891f740c4cd15 | CCCCCN(CCC12CC3CC(CC(C3)C1)C2)C(=O)NCCC(O[Si](C)(C)C(C)(C)C)c1ccncc1>>CCCCCN(CCC12CC3CC(CC(C3)C1)C2)C(=O)NCCC(O)c1ccncc1 | C12(CC3CC(CC(C1)C3)C2)CCN(C(=O)NCCC(C2=CC=NC=C2)O[Si](C)(C)C(C)(C)C)CCCCC>>C12(CC3CC(CC(C1)C3)C2)CCN(C(=O)NCCC(C2=CC=NC=C2)O)CCCCC | CC(C)(C)[Si](C)(C)[O:25][CH:24]([CH2:23][CH2:22][NH:21][C:19]([N:6]([CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])[CH2:7][CH2:8][C:9]12[CH2:10][CH:11]3[CH2:12][CH:13]([CH2:14][CH:15]([CH2:16]3)[CH2:17]1)[CH2:18]2)=[O:20])[c:26]1[cH:27][cH:28][n:29][cH:30][cH:31]1>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][N:6]([CH2:7][CH2:8][C:9]12[CH... | CCCCCN(CCC12CC3CC(CC(C3)C1)C2)C(=O)NCCC(O[Si](C)(C)C(C)(C)C)c1ccncc1 | CCCCCN(CCC12CC3CC(CC(C3)C1)C2)C(=O)NCCC(O)c1ccncc1 | null | null | Cl.CO | Deprotection | Alcohol deprotection from silyl ethers | 050b4fb4e1e9936189860d27dded10ae70a294a642c52f800eb9d5aaef7955cc | 88623e19d23cdfe8e1a4c167fd6cfc51d774a1c784b87a7bb2df8153ee93e67a | O=C(NCCCc1ccncc1)NCCC12CC3CC(CC(C3)C1)C2 | C-C(-C)(-C)-[Si](-C)(-C)-[O;H0;D2;+0:1]-[C:2](-[C:3])-[c:4]>>[C:3]-[C:2](-[OH;D1;+0:1])-[c:4] | 55.3 | [{"value": 55.3, "product": "C12(CC3CC(CC(C1)C3)C2)CCN(C(=O)NCCC(C2=CC=NC=C2)O)CCCCC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 1-[2-(1-adamantyl)ethyl]-3-[3-(t-butyldimethylsilyloxy)-3-(4-pyridyl)propyl]-1-pentylurea (Compound No. 1-138) (136 mg, 0.250 mmol) in 10% hydrogen chloride-methanol (2.3 ml) was stirred at room temperature for three days. The solvent was evaporated under reduced pressure, the residue was distributed with... | 10.6084/m9.figshare.5104873.v1 | null | TMS ether protective group | Secondary alcohol | null | null | c1ccncc1.C1C2CC3CC1CC(C2)C3 | Other | Cl.CO | null | null | CCCCCN(CCC12CC3CC(CC(C3)C1)C2)C(=O)NCCC(O[Si](C)(C)C(C)(C)C)c1ccncc1>Cl.CO>CCCCCN(CCC12CC3CC(CC(C3)C1)C2)C(=O)NCCC(O)c1ccncc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b777ff91edf849818303f364dcaebf2f | CCCCCN(CCC12CC3CC(CC(C3)C1)C2)C(=O)NC/C=C\c1ccncc1>>CCCCCN(CCC12CC3CC(CC(C3)C1)C2)C(=O)NC[C@@H]1C[C@@H]1c1ccncc1 | C(C)[Zn]CC.CCCCCC.ClCI.C12(CC3CC(CC(C1)C3)C2)CCN(C(=O)NC\C=C/C2=CC=NC=C2)CCCCC.[Cl-].[NH4+].[Cl-].[NH4+]>>C12(CC3CC(CC(C1)C3)C2)CCN(C(=O)NC[C@H]2[C@H](C2)C2=CC=NC=C2)CCCCC | [CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][N:6]([CH2:7][CH2:8][C:9]12[CH2:10][CH:11]3[CH2:12][CH:13]([CH2:14][CH:15]([CH2:16]3)[CH2:17]1)[CH2:18]2)[C:19](=[O:20])[NH:21][CH2:22]/[CH:23]=[CH:25]\[c:26]1[cH:27][cH:28][n:29][cH:30][cH:31]1>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][N:6]([CH2:7][CH2:8][C:9]12[CH2:10][CH:11]3[CH2:12][CH... | CCCCCN(CCC12CC3CC(CC(C3)C1)C2)C(=O)NC/C=C\c1ccncc1 | CCCCCN(CCC12CC3CC(CC(C3)C1)C2)C(=O)NC[C@@H]1C[C@@H]1c1ccncc1 | null | null | C(C)(=O)OCC.ClCCCl | C-C Coupling | OtherReaction | ac91075a06a8cce8890c40dac805065f8c8b8f1e346a2fcf9830e69753a8b680 | 410ec9b1cc243569e4ff568c248f0b402403802e002b4018f576af3f6960507b | O=C(NCCC12CC3CC(CC(C3)C1)C2)NC[C@@H]1C[C@@H]1c1ccncc1 | [#7:1]-[C:2](=[O;D1;H0:3])-[#7:4]-[C:5]/[CH;D2;+0:6]=[CH;D2;+0:7]\[c:8]1:[c:9]:[c:10]:[#7;a:11]:[c:12]:[c:13]:1>>[#7:1]-[C:2](=[O;D1;H0:3])-[#7:4]-[C:5]-[C@@H;D3;+0:6]1-[C:14]-[C@@H;D3;+0:7]-1-[c:8]1:[c:9]:[c:10]:[#7;a:11]:[c:12]:[c:13]:1 | 3.5 | [{"value": 3.5, "product": "C12(CC3CC(CC(C1)C3)C2)CCN(C(=O)NC[C@H]2[C@H](C2)C2=CC=NC=C2)CCCCC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | A 1.0 M solution of diethylzinc in hexane (3.1 ml, 3.1 mmol) and chloroiodomethane (0.44 ml, 6.1 mol) were added to a solution of (Z)-1-[2-(1-adamantyl)ethyl]-1-pentyl-3-[3-(4-pyridyl)-2-propenyl]urea (Compound No. 1-111) in anhydrous 1,2-dichloroethane (3 ml) under a nitrogen atmosphere and ice-cooling, and the mixtur... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | C1CC1 | C1CC1.c1ccncc1.C1C2CC3CC1CC(C2)C3 | Other | C(C)(=O)OCC.ClCCCl | null | 1 | CCCCCN(CCC12CC3CC(CC(C3)C1)C2)C(=O)NC/C=C\c1ccncc1>C(C)(=O)OCC.ClCCCl>CCCCCN(CCC12CC3CC(CC(C3)C1)C2)C(=O)NC[C@@H]1C[C@@H]1c1ccncc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-7ea1582158b34c4ca63e8152da8e7658 | CCCCCN(CCC12CC3CC(CC(C3)C1)C2)C(=O)NCCCc1ccncc1.O=C(OO)c1cccc(Cl)c1>>CCCCCN(CCC12CC3CC(CC(C3)C1)C2)C(=O)NCCCc1cc[n+]([O-])cc1 | ClC1=CC(=CC=C1)C(=O)OO.C12(CC3CC(CC(C1)C3)C2)CCN(C(=O)NCCCC2=CC=NC=C2)CCCCC.[OH-].[Na+]>>C12(CC3CC(CC(C1)C3)C2)CCN(C(NCCCC2=CC=[N+](C=C2)[O-])=O)CCCCC | [CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][N:6]([CH2:7][CH2:8][C:9]12[CH2:10][CH:11]3[CH2:12][CH:13]([CH2:14][CH:15]([CH2:16]3)[CH2:17]1)[CH2:18]2)[C:19](=[O:20])[NH:21][CH2:22][CH2:23][CH2:24][c:25]1[cH:26][cH:27][n:28][cH:30][cH:31]1.O=C(O[OH:29])c1cccc(Cl)c1>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][N:6]([CH2:7][CH2:8][C:9]12[C... | CCCCCN(CCC12CC3CC(CC(C3)C1)C2)C(=O)NCCCc1ccncc1.O=C(OO)c1cccc(Cl)c1 | CCCCCN(CCC12CC3CC(CC(C3)C1)C2)C(=O)NCCCc1cc[n+]([O-])cc1 | null | null | C(Cl)(Cl)Cl | Miscellaneous | OtherReaction | 5b2b5a1eb88c9671c4a604b6f76054cc01cd86a1985fc147f7e56f19c4844d35 | 98b338a9d01476c0929fd5672e7509121bfe69600fd72e4d1cc6f1782e2d05d9 | O=C(NCCCc1cc[nH+]cc1)NCCC12CC3CC(CC(C3)C1)C2 | Cl-c1:c:c:c:c(-C(=O)-O-[OH;D1;+0:1]):c:1.[c:2]:[c:3]:[n;H0;D2;+0:4]:[c:5]:[c:6]>>[O-;H0;D1:1]-[n+;H0;D3:4](:[c:3]:[c:2]):[c:5]:[c:6] | 94.2 | [{"value": 94.2, "product": "C12(CC3CC(CC(C1)C3)C2)CCN(C(NCCCC2=CC=[N+](C=C2)[O-])=O)CCCCC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | m-Chloroperbenzoic acid (2.5 g, 15 mmol) was added to a solution of 1-[2-(1-adamantyl)ethyl]-1-pentyl-3-[3-(4-pyridyl)propyl]urea (Compound No. 1-1) (3.0 g, 7.3 mmol) at room temperature under a nitrogen atmosphere, and the mixture was stirred overnight. The reaction mixture was distributed with chloroform (20 ml) and ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Peroxide | null | c1ccncc1.c1ccccc1 | C1=CC=[NH+]C=C1 | C1=CC=[NH+]C=C1.C1C2CC3CC1CC(C2)C3 | HCl | C(Cl)(Cl)Cl | null | 8 | CCCCCN(CCC12CC3CC(CC(C3)C1)C2)C(=O)NCCCc1ccncc1.O=C(OO)c1cccc(Cl)c1>C(Cl)(Cl)Cl>CCCCCN(CCC12CC3CC(CC(C3)C1)C2)C(=O)NCCCc1cc[n+]([O-])cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-beb3fd4514fb43ec9f20a3ae1ab5419e | CNCCN(CCC12CC3CC(CC(C3)C1)C2)C(=O)NCCCc1ccncc1.COCCCl>>COCCN(C)CCN(CCC12CC3CC(CC(C3)C1)C2)C(=O)NCCCc1ccncc1 | C12(CC3CC(CC(C1)C3)C2)CCN(C(=O)NCCCC2=CC=NC=C2)CCNC.C([O-])([O-])=O.[K+].[K+].[I-].[Na+].COCCCl>>C12(CC3CC(CC(C1)C3)C2)CCN(C(=O)NCCCC2=CC=NC=C2)CCN(C)CCOC | [NH:5]([CH3:6])[CH2:7][CH2:8][N:9]([CH2:10][CH2:11][C:12]12[CH2:13][CH:14]3[CH2:15][CH:16]([CH2:17][CH:18]([CH2:19]3)[CH2:20]1)[CH2:21]2)[C:22](=[O:23])[NH:24][CH2:25][CH2:26][CH2:27][c:28]1[cH:29][cH:30][n:31][cH:32][cH:33]1.Cl[CH2:4][CH2:3][O:2][CH3:1]>>[CH3:1][O:2][CH2:3][CH2:4][N:5]([CH3:6])[CH2:7][CH2:8][N:9]([CH2... | CNCCN(CCC12CC3CC(CC(C3)C1)C2)C(=O)NCCCc1ccncc1.COCCCl | COCCN(C)CCN(CCC12CC3CC(CC(C3)C1)C2)C(=O)NCCCc1ccncc1 | null | null | O.CN(C=O)C.C(C)OCC | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 6d58cac08ccced0a33ed16fbca180bc12aa011288d6476106d98a7b2cbc3d709 | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | O=C(NCCCc1ccncc1)NCCC12CC3CC(CC(C3)C1)C2 | Cl-[CH2;D2;+0:1]-[C:2]-[#8:3].[C:4]-[C:5]-[NH;D2;+0:6]-[C;D1;H3:7]>>[#8:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:6](-[C;D1;H3:7])-[C:5]-[C:4] | 32.1 | [{"value": 32.1, "product": "C12(CC3CC(CC(C1)C3)C2)CCN(C(=O)NCCCC2=CC=NC=C2)CCN(C)CCOC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 32.1, "product": "C12(CC3CC(CC(C1)C3)C2)CCN(C(=O)NCCCC2=CC=NC=C2)CCN(C)CCOC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | 8 | HOUR | To N,N-dimethylformamide (20 ml) were added 1-[2-(1-adamantyl)ethyl]-1-(2-methylaminoethyl)-3-[3-(4-pyridyl)propyl]urea (1.50 g, 3.76 mmol), which was a free base of Compound No. 3-1, potassium carbonate (1.56 g, 11.3 mmol) and sodium iodide (1.69 g, 11.3 mmol) at room temperature, then 2-chloroethyl methyl ether (412 ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | null | null | c1ccncc1.C1C2CC3CC1CC(C2)C3 | HCl | O.CN(C=O)C.C(C)OCC | 80 | 8 | CNCCN(CCC12CC3CC(CC(C3)C1)C2)C(=O)NCCCc1ccncc1.COCCCl>O.CN(C=O)C.C(C)OCC>COCCN(C)CCN(CCC12CC3CC(CC(C3)C1)C2)C(=O)NCCCc1ccncc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-7be440cf55a742dbbf2f5f861b28233a | CCCCCNCCC12CC3CC(CC(C3)C1)C2.O=C(O)CBr>>CCCCCN(CCC12CC3CC(CC(C3)C1)C2)C(=O)CBr | C(O)([O-])=O.[Na+].CN1CCOCC1.C(OCC(C)C)(=O)Cl.BrCC(=O)O.Cl.C12(CC3CC(CC(C1)C3)C2)CCNCCCCC>>C12(CC3CC(CC(C1)C3)C2)CCN(C(CBr)=O)CCCCC | [CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][NH:6][CH2:7][CH2:8][C:9]12[CH2:10][CH:11]3[CH2:12][CH:13]([CH2:14][CH:15]([CH2:16]3)[CH2:17]1)[CH2:18]2.O[C:19](=[O:20])[CH2:21][Br:22]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][N:6]([CH2:7][CH2:8][C:9]12[CH2:10][CH:11]3[CH2:12][CH:13]([CH2:14][CH:15]([CH2:16]3)[CH2:17]1)[CH2:18]2)[C:19](... | CCCCCNCCC12CC3CC(CC(C3)C1)C2.O=C(O)CBr | CCCCCN(CCC12CC3CC(CC(C3)C1)C2)C(=O)CBr | null | null | C(C)(=O)OCC.O1CCCC1 | Acylation | Acylation of Nitrogen Nucleophiles by Carboxylic Acids | ac72df6259d5d7baee7abdbd4706ef4b4627f86ead9dc94f0cefcfcb37c21def | c5e4172490b2731ba9322b68af56376edadc31ce0bb9a3dfdea23a1817a852fd | C1C2CC3CC1CC(C2)C3 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[Br;D1;H0:4].[C:5]-[C:6]-[NH;D2;+0:7]-[C:8]-[C:9]>>[Br;D1;H0:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[N;H0;D3;+0:7](-[C:6]-[C:5])-[C:8]-[C:9] | null | [] | -15 | CELSIUS | null | null | Bromoacetic acid (0.50 g, 3.6 mmol) was dissolved in anhydrous tetrahydrofuran (20 ml), and the solution was stirred at −15° C. under a nitrogen atmosphere. N-Methylmorpholine (0.40 ml, 3.6 mmol) and isobutyl chlorocarbonate (0.45 ml, 3.5 mmol) were added to the solution. Then, a solution of a free base of 2-(1-adamant... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | Tertiary amide | null | null | C1C2CC3CC1CC(C2)C3 | HO- | C(C)(=O)OCC.O1CCCC1 | -15 | null | CCCCCNCCC12CC3CC(CC(C3)C1)C2.O=C(O)CBr>C(C)(=O)OCC.O1CCCC1>CCCCCN(CCC12CC3CC(CC(C3)C1)C2)C(=O)CBr |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-9c3e5bf933da48958d386228a5bce4fa | CCCCCN(CCC12CC3CC(CC(C3)C1)C2)C(=O)CBr.NCCc1ccncc1>>CCCCCN(CCC12CC3CC(CC(C3)C1)C2)C(=O)CNCCc1ccncc1 | C12(CC3CC(CC(C1)C3)C2)CCN(C(CBr)=O)CCCCC.C([O-])([O-])=O.[K+].[K+].CI.NCCC1=CC=NC=C1>>C12(CC3CC(CC(C1)C3)C2)CCN(C(CNCCC2=CC=NC=C2)=O)CCCCC | Br[CH2:21][C:19]([N:6]([CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])[CH2:7][CH2:8][C:9]12[CH2:10][CH:11]3[CH2:12][CH:13]([CH2:14][CH:15]([CH2:16]3)[CH2:17]1)[CH2:18]2)=[O:20].[NH2:22][CH2:23][CH2:24][c:25]1[cH:26][cH:27][n:28][cH:29][cH:30]1>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][N:6]([CH2:7][CH2:8][C:9]12[CH2:10][CH:11]3[CH2:12]... | CCCCCN(CCC12CC3CC(CC(C3)C1)C2)C(=O)CBr.NCCc1ccncc1 | CCCCCN(CCC12CC3CC(CC(C3)C1)C2)C(=O)CNCCc1ccncc1 | null | null | O.CN(C=O)C.C(C)OCC | Heteroatom Alkylation and Arylation | N-alkylation of primary amines with alkyl halides | fc19a1445ff204e66e51735d0191465bda3c6691fd233624a54742c9d4828411 | 0b1d32f56ad00f1e5bdae9390f9227bbea012fa2f8203aac34726b8a6761cc7c | O=C(CNCCc1ccncc1)NCCC12CC3CC(CC(C3)C1)C2 | Br-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#7:4](-[C:5])-[C:6].[C:7]-[C:8]-[NH2;D1;+0:9]>>[C:7]-[C:8]-[NH;D2;+0:9]-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#7:4](-[C:5])-[C:6] | 41.6 | [{"value": 40.0, "product": "C12(CC3CC(CC(C1)C3)C2)CCN(C(CNCCC2=CC=NC=C2)=O)CCCCC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 41.6, "product": "C12(CC3CC(CC(C1)C3)C2)CCN(C(CNCCC2=CC=NC=C2)=O)CCCCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 75 | CELSIUS | 8 | HOUR | Next, 2-bromoacetic acid N-[2-(1-adamantyl)ethyl]-N-pentylamide (1.3 g, 3.5 mmol) was dissolved in anhydrous N,N-dimethylformamide (30 ml), potassium carbonate (1.5 g, 11 mmol), methyl iodide (1.6 g, 11 mmol) and 4-(2-aminoethyl)pyridine (0.43 g, 3.5 mmol) were added to the solution, and the mixture was stirred at an e... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary amine | Secondary amine | null | null | c1ccncc1.C1C2CC3CC1CC(C2)C3 | HBr | O.CN(C=O)C.C(C)OCC | 75 | 8 | CCCCCN(CCC12CC3CC(CC(C3)C1)C2)C(=O)CBr.NCCc1ccncc1>O.CN(C=O)C.C(C)OCC>CCCCCN(CCC12CC3CC(CC(C3)C1)C2)C(=O)CNCCc1ccncc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-327e302bf75244758d1922dd20b55bbb | CCCCCN(CCC12CC3CC(CC(C3)C1)C2)C(=O)[C@H]1CCCN1C(=O)OC(C)(C)C>>CCCCCN(CCC12CC3CC(CC(C3)C1)C2)C(=O)[C@H]1CCCN1 | Cl.O1CCOCC1.C12(CC3CC(CC(C1)C3)C2)CCN(C(=O)[C@@H]2N(CCC2)C(=O)OC(C)(C)C)CCCCC>>Cl.C12(CC3CC(CC(C1)C3)C2)CCN(C(=O)[C@@H]2NCCC2)CCCCC | CC(C)(C)OC(=O)[N:25]1[C@@H:21]([C:19]([N:6]([CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])[CH2:7][CH2:8][C:9]23[CH2:10][CH:11]4[CH2:12][CH:13]([CH2:14][CH:15]([CH2:16]4)[CH2:17]2)[CH2:18]3)=[O:20])[CH2:22][CH2:23][CH2:24]1>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][N:6]([CH2:7][CH2:8][C:9]12[CH2:10][CH:11]3[CH2:12][CH:13]([CH2:14][CH:... | CCCCCN(CCC12CC3CC(CC(C3)C1)C2)C(=O)[C@H]1CCCN1C(=O)OC(C)(C)C | CCCCCN(CCC12CC3CC(CC(C3)C1)C2)C(=O)[C@H]1CCCN1 | null | null | null | Reduction | Boc amine deprotection | 7b506000be0005f6be41b2386b5bd6a8c45f704baa22d692d2f2ec984758e4ad | a94b29c7264c852156fc1cdd4a0951a4fc26c06d0edc9e50c743825dbf79e3fd | O=C(NCCC12CC3CC(CC(C3)C1)C2)[C@H]1CCCN1 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1]1-[C:2]-[C:3]-[C:4]-[C:5]-1-[C:6](=[O;D1;H0:7])-[#7:8](-[C:9])-[C:10]>>[C:9]-[#7:8](-[C:10])-[C:6](=[O;D1;H0:7])-[C:5]1-[C:4]-[C:3]-[C:2]-[NH;D2;+0:1]-1 | null | [] | null | null | 1.5 | HOUR | Next, 4 N hydrogen chloride/dioxane (20 ml, 81 mmol) was added to (R)-1-(t-butoxycarbonyl)-2-pyrrolidinecarboxylic acid N-[2-(1-adamantyl)ethyl]-N-pentylamide (1.8 g, 4.0 mmol) under ice-cooling, then the temperature was raised to room temperature, and the mixture was stirred for 1.5 hours. The reaction mixture was con... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Secondary amine | C1CC[NH]C1 | C1CCNC1 | C1CCNC1.C1C2CC3CC1CC(C2)C3 | HO- | null | null | 1.5 | CCCCCN(CCC12CC3CC(CC(C3)C1)C2)C(=O)[C@H]1CCCN1C(=O)OC(C)(C)C>>CCCCCN(CCC12CC3CC(CC(C3)C1)C2)C(=O)[C@H]1CCCN1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-69caa58474a641298e579f0a71042a19 | CCCCCN(CCC12CC3CC(CC(C3)C1)C2)C(=O)[C@H]1CCCN1.ClCCc1ccncc1>>CCCCCN(CCC12CC3CC(CC(C3)C1)C2)C(=O)[C@H]1CCCN1CCc1ccncc1 | Cl.C12(CC3CC(CC(C1)C3)C2)CCN(C(=O)[C@@H]2NCCC2)CCCCC.[OH-].[Na+].C([O-])([O-])=O.[K+].[K+].CI.Cl.ClCCC1=CC=NC=C1>>Cl.C12(CC3CC(CC(C1)C3)C2)CCN(C(=O)[C@@H]2N(CCC2)CCC2=CC=NC=C2)CCCCC | [CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][N:6]([CH2:7][CH2:8][C:9]12[CH2:10][CH:11]3[CH2:12][CH:13]([CH2:14][CH:15]([CH2:16]3)[CH2:17]1)[CH2:18]2)[C:19](=[O:20])[C@H:21]1[CH2:22][CH2:23][CH2:24][NH:25]1.Cl[CH2:26][CH2:27][c:28]1[cH:29][cH:30][n:31][cH:32][cH:33]1>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][N:6]([CH2:7][CH2:8][C:9]1... | CCCCCN(CCC12CC3CC(CC(C3)C1)C2)C(=O)[C@H]1CCCN1.ClCCc1ccncc1 | CCCCCN(CCC12CC3CC(CC(C3)C1)C2)C(=O)[C@H]1CCCN1CCc1ccncc1 | null | null | CN(C=O)C.C(C)OCC | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 19b442dc26882f89f7423416f5e0a16bdb8e48776df57991434a0634e21f0505 | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | O=C(NCCC12CC3CC(CC(C3)C1)C2)[C@H]1CCCN1CCc1ccncc1 | Cl-[CH2;D2;+0:1]-[C:2]-[c:3].[C:4]-[#7:5](-[C:6])-[C:7](=[O;D1;H0:8])-[C:9]1-[C:10]-[C:11]-[C:12]-[NH;D2;+0:13]-1>>[C:4]-[#7:5](-[C:6])-[C:7](=[O;D1;H0:8])-[C:9]1-[C:10]-[C:11]-[C:12]-[N;H0;D3;+0:13]-1-[CH2;D2;+0:1]-[C:2]-[c:3] | 47 | [{"value": 47.0, "product": "Cl.C12(CC3CC(CC(C1)C3)C2)CCN(C(=O)[C@@H]2N(CCC2)CCC2=CC=NC=C2)CCCCC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 44.3, "product": "Cl.C12(CC3CC(CC(C1)C3)C2)CCN(C(=O)[C@@H]2N(CCC2)CCC2=CC=NC=C2)CCCCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | 8 | HOUR | Next, (R)-2-pyrrolidinecarboxylic acid N-[2-(1-adamantyl)ethyl]-N-pentylamide hydrochloride (1.4 g, 3.7 mmol) was dissolved in anhydrous N,N-dimethylformamide (40 ml), potassium carbonate (2.6 g, 19 mmol), methyl iodide (1.7 g, 11 mmol) and 4-(2-chloroethyl)pyridine hydrochloride (0.70 g, 3.7 mmol) were added to the so... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1CCNC1 | C1CC[NH]C1 | C1CC[NH]C1.c1ccncc1.C1C2CC3CC1CC(C2)C3 | HCl | CN(C=O)C.C(C)OCC | 80 | 8 | CCCCCN(CCC12CC3CC(CC(C3)C1)C2)C(=O)[C@H]1CCCN1.ClCCc1ccncc1>CN(C=O)C.C(C)OCC>CCCCCN(CCC12CC3CC(CC(C3)C1)C2)C(=O)[C@H]1CCCN1CCc1ccncc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-3a43e2cffc69433ca1bd156c67c925a2 | CC(C)(C)OC(=O)NCCC(=O)O.CCCCCNCCC12CC3CC(CC(C3)C1)C2>>CCCCCN(CCC12CC3CC(CC(C3)C1)C2)C(=O)CCNC(=O)OC(C)(C)C | C(O)([O-])=O.[Na+].Cl.C12(CC3CC(CC(C1)C3)C2)CCNCCCCC.C(C)(C)(C)OC(=O)NCCC(=O)O.CN1CCOCC1.C(OCC(C)C)(=O)Cl>>C12(CC3CC(CC(C1)C3)C2)CCN(C(CCNC(=O)OC(C)(C)C)=O)CCCCC | O[C:19](=[O:20])[CH2:21][CH2:22][NH:23][C:24](=[O:25])[O:26][C:27]([CH3:28])([CH3:29])[CH3:30].[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][NH:6][CH2:7][CH2:8][C:9]12[CH2:10][CH:11]3[CH2:12][CH:13]([CH2:14][CH:15]([CH2:16]3)[CH2:17]1)[CH2:18]2>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][N:6]([CH2:7][CH2:8][C:9]12[CH2:10][CH:11]3[CH2:1... | CC(C)(C)OC(=O)NCCC(=O)O.CCCCCNCCC12CC3CC(CC(C3)C1)C2 | CCCCCN(CCC12CC3CC(CC(C3)C1)C2)C(=O)CCNC(=O)OC(C)(C)C | null | null | C(C)(=O)OCC.O1CCCC1 | Acylation | Acylation of Nitrogen Nucleophiles by Carboxylic Acids | ac72df6259d5d7baee7abdbd4706ef4b4627f86ead9dc94f0cefcfcb37c21def | c5e4172490b2731ba9322b68af56376edadc31ce0bb9a3dfdea23a1817a852fd | C1C2CC3CC1CC(C2)C3 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[C:5]-[C:6]-[NH;D2;+0:7]-[C:8]-[C:9]>>[C:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[N;H0;D3;+0:7](-[C:6]-[C:5])-[C:8]-[C:9] | 85.2 | [{"value": 85.0, "product": "C12(CC3CC(CC(C1)C3)C2)CCN(C(CCNC(=O)OC(C)(C)C)=O)CCCCC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 85.2, "product": "C12(CC3CC(CC(C1)C3)C2)CCN(C(CCNC(=O)OC(C)(C)C)=O)CCCCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -15 | CELSIUS | null | null | 3-(t-Butoxycarbonylamino)propionic acid (1.0 g, 5.3 mmol) was dissolved in anhydrous tetrahydrofuran (15 ml), and N-methylmorpholine (0.6 ml, 5.5 mmol) was added to the solution. The mixture was stirred at −15° C., and isobutyl chlorocarbonate (0.7 ml, 5.4 mmol) was added thereto. Then, a solution of a free base of 2-(... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | Tertiary amide | null | null | C1C2CC3CC1CC(C2)C3 | HO- | C(C)(=O)OCC.O1CCCC1 | -15 | null | CC(C)(C)OC(=O)NCCC(=O)O.CCCCCNCCC12CC3CC(CC(C3)C1)C2>C(C)(=O)OCC.O1CCCC1>CCCCCN(CCC12CC3CC(CC(C3)C1)C2)C(=O)CCNC(=O)OC(C)(C)C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-5e6ea597a9fd4f3e9d2e415a9a3753ea | CCCCCN(CCC12CC3CC(CC(C3)C1)C2)C(=O)CCN=Cc1ccncc1>>CCCCCN(CCC12CC3CC(CC(C3)C1)C2)C(=O)CCNCc1ccncc1 | C12(CC3CC(CC(C1)C3)C2)CCN(C(CCN=CC2=CC=NC=C2)=O)CCCCC>>C12(CC3CC(CC(C1)C3)C2)CCN(C(CCNCC2=CC=NC=C2)=O)CCCCC | [CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][N:6]([CH2:7][CH2:8][C:9]12[CH2:10][CH:11]3[CH2:12][CH:13]([CH2:14][CH:15]([CH2:16]3)[CH2:17]1)[CH2:18]2)[C:19](=[O:20])[CH2:21][CH2:22][N:23]=[CH:24][c:25]1[cH:26][cH:27][n:28][cH:29][cH:30]1>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][N:6]([CH2:7][CH2:8][C:9]12[CH2:10][CH:11]3[CH2:12][CH:1... | CCCCCN(CCC12CC3CC(CC(C3)C1)C2)C(=O)CCN=Cc1ccncc1 | CCCCCN(CCC12CC3CC(CC(C3)C1)C2)C(=O)CCNCc1ccncc1 | null | [Pd] | CO | Reduction | OtherReaction | d4a3c3af6b6e3a46274c741e9feddcd7af52a8fba8716af75123ec94a3d0151d | 469efbca661320a0d72c32f19625ec46edbc3ad7686cf46fdd0591eb136a8d7e | O=C(CCNCc1ccncc1)NCCC12CC3CC(CC(C3)C1)C2 | [#7:1]-[C:2](=[O;D1;H0:3])-[C:4]-[C:5]-[N;H0;D2;+0:6]=[CH;D2;+0:7]-[c:8]1:[c:9]:[c:10]:[#7;a:11]:[c:12]:[c:13]:1>>[#7:1]-[C:2](=[O;D1;H0:3])-[C:4]-[C:5]-[NH;D2;+0:6]-[CH2;D2;+0:7]-[c:8]1:[c:9]:[c:10]:[#7;a:11]:[c:12]:[c:13]:1 | 36.1 | [{"value": 36.0, "product": "C12(CC3CC(CC(C1)C3)C2)CCN(C(CCNCC2=CC=NC=C2)=O)CCCCC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 36.1, "product": "C12(CC3CC(CC(C1)C3)C2)CCN(C(CCNCC2=CC=NC=C2)=O)CCCCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 7 | HOUR | 3-(4-Pyridylmethylideneamino)propionic acid N-[2-(1-adamantyl)ethyl]-N-pentylamide (Compound No. 21-1) (1.6 g, 3.9 mmol) was dissolved in methanol, 10% palladium on carbon (catalytic amount) was added to the solution, and the mixture was stirred under hydrogen at 1 atm and room temperature for seven hours. The 10% pall... | 10.6084/m9.figshare.5104873.v1 | null | Substituted imine | Secondary amine | null | null | c1ccncc1.C1C2CC3CC1CC(C2)C3 | null | [Pd].CO | null | 7 | CCCCCN(CCC12CC3CC(CC(C3)C1)C2)C(=O)CCN=Cc1ccncc1>[Pd].CO>CCCCCN(CCC12CC3CC(CC(C3)C1)C2)C(=O)CCNCc1ccncc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-658d17ce5a994ee6a0847b17239b3d4c | CC(=O)NCCN(CCC12CC3CC(CC(C3)C1)C2)C(=O)NCCCc1ccncc1>>NCCN(CCC12CC3CC(CC(C3)C1)C2)C(=O)NCCCc1ccncc1 | C(Cl)(Cl)Cl.Cl.C(C)(=O)NCCN(C(=O)NCCCC1=CC=NC=C1)CCC12CC3CC(CC(C1)C3)C2.[OH-].[Na+]>>C12(CC3CC(CC(C1)C3)C2)CCN(C(=O)NCCCC2=CC=NC=C2)CCN | CC(=O)[NH:1][CH2:2][CH2:3][N:4]([CH2:5][CH2:6][C:7]12[CH2:8][CH:9]3[CH2:10][CH:11]([CH2:12][CH:13]([CH2:14]3)[CH2:15]1)[CH2:16]2)[C:17](=[O:18])[NH:19][CH2:20][CH2:21][CH2:22][c:23]1[cH:24][cH:25][n:26][cH:27][cH:28]1>>[NH2:1][CH2:2][CH2:3][N:4]([CH2:5][CH2:6][C:7]12[CH2:8][CH:9]3[CH2:10][CH:11]([CH2:12][CH:13]([CH2:14... | CC(=O)NCCN(CCC12CC3CC(CC(C3)C1)C2)C(=O)NCCCc1ccncc1 | NCCN(CCC12CC3CC(CC(C3)C1)C2)C(=O)NCCCc1ccncc1 | null | null | CO.O | Reduction | Hydrogenolysis of amides/imides/carbamates | 755df58c254dea764fdda078ffd678ec540bba057c83683be04c253f1270ac7b | 025f7cefe51e71668ad5d09fca32df168e9b538347403e4d5c1748073e538adc | O=C(NCCCc1ccncc1)NCCC12CC3CC(CC(C3)C1)C2 | C-C(=O)-[NH;D2;+0:1]-[C:2]-[C:3]>>[C:3]-[C:2]-[NH2;D1;+0:1] | 21.7 | [{"value": 21.7, "product": "C12(CC3CC(CC(C1)C3)C2)CCN(C(=O)NCCCC2=CC=NC=C2)CCN", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 3 | DAY | Under ice-cooling, 6 N hydrochloric acid (15 ml) was added to a solution of 1-[2-(acetylamino)ethyl]-1-[2-(1-adamantyl)ethyl]-3-[3-(4-pyridyl)propyl]urea (Compound No. 1-103) (1.02 g, 2.39 mmol) in methanol (10 ml), and the mixture was heated at 90° C. with stirring for three days. The reaction mixture was neutralized ... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide | Primary amine | null | null | c1ccncc1.C1C2CC3CC1CC(C2)C3 | HO- | CO.O | null | 72 | CC(=O)NCCN(CCC12CC3CC(CC(C3)C1)C2)C(=O)NCCCc1ccncc1>CO.O>NCCN(CCC12CC3CC(CC(C3)C1)C2)C(=O)NCCCc1ccncc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-255a07025eca44d1b3ec05d62aa736eb | CCCCCNCCC12CC3CC(CC(C3)C1)C2.CO.O=C(Cl)COCC(=O)Cl>>CCCCCN(CCC12CC3CC(CC(C3)C1)C2)C(=O)COCC(=O)OC | CO.Cl.C12(CC3CC(CC(C1)C3)C2)CCNCCCCC.C(COCC(=O)Cl)(=O)Cl.C(C)N(CC)CC>>C12(CC3CC(CC(C1)C3)C2)CCN(C(COCC(=O)OC)=O)CCCCC | [CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][NH:6][CH2:7][CH2:8][C:9]12[CH2:10][CH:11]3[CH2:12][CH:13]([CH2:14][CH:15]([CH2:16]3)[CH2:17]1)[CH2:18]2.[OH:26][CH3:27].Cl[C:19](=[O:20])[CH2:21][O:22][CH2:23][C:24](Cl)=[O:25]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][N:6]([CH2:7][CH2:8][C:9]12[CH2:10][CH:11]3[CH2:12][CH:13]([CH2:14][CH:... | CCCCCNCCC12CC3CC(CC(C3)C1)C2.CO.O=C(Cl)COCC(=O)Cl | CCCCCN(CCC12CC3CC(CC(C3)C1)C2)C(=O)COCC(=O)OC | null | null | ClCCl | Acylation | OtherReaction | 829fb7a313546f30059b2e7849f95004f1dd42df6bc3620dd41f407ef6d225aa | 438ba3ba739a75ff3d60fdcfabd35952de218c3a312d7734daafa8a2a64a92e2 | C1C2CC3CC1CC(C2)C3 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[#8:4]-[C:5]-[C;H0;D3;+0:6](-Cl)=[O;D1;H0:7].[C;D1;H3:8]-[OH;D1;+0:9].[C:10]-[C:11]-[NH;D2;+0:12]-[C:13]-[C:14]>>[C:10]-[C:11]-[N;H0;D3;+0:12](-[C:13]-[C:14])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[#8:4]-[C:5]-[C;H0;D3;+0:6](=[O;D1;H0:7])-[O;H0;D2;+0:9]-[C;D1;H3:8] | 60 | [{"value": 60.0, "product": "C12(CC3CC(CC(C1)C3)C2)CCN(C(COCC(=O)OC)=O)CCCCC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | 2-(1-Adamantyl)-N-pentylethylamine hydrochloride (Intermediate No. 1-1) (0.50 g, 1.7 mmol) was added to a solution of diglycolyl chloride (0.31 ml, 2.6 mmol) and triethylamine (0.70 ml, 5.1 mmol) in anhydrous dichloromethane (6 ml) under ice-cooling, and the mixture was stirred at room temperature overnight. Methanol (... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Acyl halide.Secondary amine.Methanol | Ester.Tertiary amide | null | null | C1C2CC3CC1CC(C2)C3 | HCl | ClCCl | null | 8 | CCCCCNCCC12CC3CC(CC(C3)C1)C2.CO.O=C(Cl)COCC(=O)Cl>ClCCl>CCCCCN(CCC12CC3CC(CC(C3)C1)C2)C(=O)COCC(=O)OC |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-2c635ed316974a799655bfc4decc52db | CCCCCN(CCC12CC3CC(CC(C3)C1)C2)C(=O)COCC(=O)OC>>CCCCCN(CCC12CC3CC(CC(C3)C1)C2)C(=O)COCCO | [BH4-].[Na+].C12(CC3CC(CC(C1)C3)C2)CCN(C(COCC(=O)OC)=O)CCCCC.O.C(C)(=O)OCC.O>>C12(CC3CC(CC(C1)C3)C2)CCN(C(COCCO)=O)CCCCC | CO[C:24]([CH2:23][O:22][CH2:21][C:19]([N:6]([CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])[CH2:7][CH2:8][C:9]12[CH2:10][CH:11]3[CH2:12][CH:13]([CH2:14][CH:15]([CH2:16]3)[CH2:17]1)[CH2:18]2)=[O:20])=[O:25]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][N:6]([CH2:7][CH2:8][C:9]12[CH2:10][CH:11]3[CH2:12][CH:13]([CH2:14][CH:15]([CH2:16]3)[CH2... | CCCCCN(CCC12CC3CC(CC(C3)C1)C2)C(=O)COCC(=O)OC | CCCCCN(CCC12CC3CC(CC(C3)C1)C2)C(=O)COCCO | null | null | CO | Reduction | Reduction of ester to primary alcohol | 21d61543c6ec8a8cebe1b3ef55ef3dd20acbf79a4f1c12a7fb51e32be7a3248a | 1fbcd628a0426673c5d10aa49a977cd2d1ae02a8cdf57bbb10d94aa03a94e937 | C1C2CC3CC1CC(C2)C3 | C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[C:3]-[#8:4]>>[#8:4]-[C:3]-[CH2;D2;+0:1]-[OH;D1;+0:2] | 22 | [{"value": 22.0, "product": "C12(CC3CC(CC(C1)C3)C2)CCN(C(COCCO)=O)CCCCC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 21.9, "product": "C12(CC3CC(CC(C1)C3)C2)CCN(C(COCCO)=O)CCCCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | Next, sodium borohydride (0.18 g, 4.8 mmol) was added to a solution of 2-methoxycarbonylmethoxyacetic acid N-[2-(1-adamantyl)ethyl]-N-pentylamide (0.37 g, 0.96 mmol) in methanol (3 ml) under ice-cooling, and the mixture was stirred at room temperature overnight. Water (10 ml) was added to the reaction mixture, and the ... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary alcohol | null | null | C1C2CC3CC1CC(C2)C3 | Other | CO | null | 8 | CCCCCN(CCC12CC3CC(CC(C3)C1)C2)C(=O)COCC(=O)OC>CO>CCCCCN(CCC12CC3CC(CC(C3)C1)C2)C(=O)COCCO |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-e566d59fdc5441c397562ebe5a903995 | CCCCCN(CCC12CC3CC(CC(C3)C1)C2)C(=O)NCCC(O)c1ccncc1>>CCCCCN(CCC12CC3CC(CC(C3)C1)C2)C(=O)NCCC(=O)c1ccncc1 | CC(=O)OI1(C2=CC=CC=C2C(=O)O1)(OC(=O)C)OC(=O)C.C12(CC3CC(CC(C1)C3)C2)CCN(C(=O)NCCC(C2=CC=NC=C2)O)CCCCC.S(=O)([O-])[O-].[Na+].[Na+].C(O)([O-])=O.[Na+]>>C12(CC3CC(CC(C1)C3)C2)CCN(C(=O)NCCC(C2=CC=NC=C2)=O)CCCCC | [CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][N:6]([CH2:7][CH2:8][C:9]12[CH2:10][CH:11]3[CH2:12][CH:13]([CH2:14][CH:15]([CH2:16]3)[CH2:17]1)[CH2:18]2)[C:19](=[O:20])[NH:21][CH2:22][CH2:23][CH:24]([OH:25])[c:26]1[cH:27][cH:28][n:29][cH:30][cH:31]1>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][N:6]([CH2:7][CH2:8][C:9]12[CH2:10][CH:11]3[CH2... | CCCCCN(CCC12CC3CC(CC(C3)C1)C2)C(=O)NCCC(O)c1ccncc1 | CCCCCN(CCC12CC3CC(CC(C3)C1)C2)C(=O)NCCC(=O)c1ccncc1 | null | null | ClCCl.O.C(C)(=O)OCC | Oxidation | Oxidation or Dehydrogenation of Alcohols to Aldehydes and Ketones | c7c20d2959ac48847b03cc1265962cf99a8ec8a85900c087dabb30077298c66c | 767cfd93f5821ebb9e1e72addd9cb404b20b0c821d246ae6b87a5776b74a455b | O=C(NCCC(=O)c1ccncc1)NCCC12CC3CC(CC(C3)C1)C2 | [C:1]-[C:2]-[CH;D3;+0:3](-[OH;D1;+0:4])-[c:5]1:[c:6]:[c:7]:[#7;a:8]:[c:9]:[c:10]:1>>[C:1]-[C:2]-[C;H0;D3;+0:3](=[O;H0;D1;+0:4])-[c:5]1:[c:6]:[c:7]:[#7;a:8]:[c:9]:[c:10]:1 | 87.8 | [{"value": 87.8, "product": "C12(CC3CC(CC(C1)C3)C2)CCN(C(=O)NCCC(C2=CC=NC=C2)=O)CCCCC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 87.7, "product": "C12(CC3CC(CC(C1)C3)C2)CCN(C(=O)NCCC(C2=CC=NC=C2)=O)CCCCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | 1,1,1-Triacetoxy-1,1-dihydro-1,2-benziodoxol-3(1H)-one (221 mg, 0.526 mmol) was added to a solution of 1-[2-(1-adamantyl)ethyl]-3-[3-hydroxy-3-(4-pyridyl)propyl]-1-pentylurea (100 mg, 0.234 mmol) in anhydrous dichloromethane (2 ml) under ice-cooling, the temperature was raised to room temperature, and the mixture was s... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol | Ketone | null | null | c1ccncc1.C1C2CC3CC1CC(C2)C3 | null | ClCCl.O.C(C)(=O)OCC | null | 1 | CCCCCN(CCC12CC3CC(CC(C3)C1)C2)C(=O)NCCC(O)c1ccncc1>ClCCl.O.C(C)(=O)OCC>CCCCCN(CCC12CC3CC(CC(C3)C1)C2)C(=O)NCCC(=O)c1ccncc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-18311b9ff0854255a339b2693026a150 | Nc1ccccc1.O=C1Nc2ccccc2C1=CO>>O=C1Nc2ccccc2C1=CNc1ccccc1 | OC=C1C(NC2=CC=CC=C12)=O.NC1=CC=CC=C1>>C1(=CC=CC=C1)NC=C1C(NC2=CC=CC=C12)=O | [NH2:12][c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1.O[CH:11]=[C:10]1[C:2](=[O:1])[NH:3][c:4]2[cH:5][cH:6][cH:7][cH:8][c:9]21>>[O:1]=[C:2]1[NH:3][c:4]2[cH:5][cH:6][cH:7][cH:8][c:9]2[C:10]1=[CH:11][NH:12][c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1 | Nc1ccccc1.O=C1Nc2ccccc2C1=CO | O=C1Nc2ccccc2C1=CNc1ccccc1 | null | null | O1CCCC1 | Heteroatom Alkylation and Arylation | Reductive amination with alcohol | ac661a5987df49e763a2386679221354b73376953f4071e32e52e2d7e8877593 | dc27e5e3871ba014ddcdbe66aa8244518b94cc851f1ff4159b6674656bc3b780 | O=C1Nc2ccccc2C1=CNc1ccccc1 | O-[CH;D2;+0:1]=[C:2]1-[c:3]:[c:4]-[#7:5]-[C:6]-1=[O;D1;H0:7].[NH2;D1;+0:8]-[c:9](:[c:10]):[c:11]>>[O;D1;H0:7]=[C:6]1-[#7:5]-[c:4]:[c:3]-[C:2]-1=[CH;D2;+0:1]-[NH;D2;+0:8]-[c:9](:[c:10]):[c:11] | null | [] | null | null | null | null | E & Z 3-[(hydroxy)-methylene]-1,3-dihydro-indol-2-one is reacted with 0.022 gms. of aniline by refluxing in tetrahydrofuran (1.2 mL) for 12 hours to yield a quantitative amount (39 mg) of the named compound as a solid following concentration in vacuo, dilution with isopropanol and filtration.
Conditions: See reaction.n... | 10.6084/m9.figshare.5104873.v1 | null | Enol.Primary amine | Enamine | null | null | c1ccc2c(c1)CCN2.c1ccccc1 | HO- | O1CCCC1 | null | null | Nc1ccccc1.O=C1Nc2ccccc2C1=CO>O1CCCC1>O=C1Nc2ccccc2C1=CNc1ccccc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-1f33a1e8fa42410bae228af1555c306e | C1CCNC1.O=C1Nc2ccccc2C1=CNc1ccc(OCCCCI)cc1>>O=C1Nc2ccccc2C1=CNc1ccc(OCCCCN2CCCC2)cc1 | ICCCCOC1=CC=C(C=C1)NC=C1C(NC2=CC=CC=C12)=O.N1CCCC1>>N1(CCCC1)CCCCOC1=CC=C(C=C1)NC=C1C(NC2=CC=CC=C12)=O | [NH:22]1[CH2:23][CH2:24][CH2:25][CH2:26]1.I[CH2:21][CH2:20][CH2:19][CH2:18][O:17][c:16]1[cH:15][cH:14][c:13]([NH:12][CH:11]=[C:10]2[C:2](=[O:1])[NH:3][c:4]3[cH:5][cH:6][cH:7][cH:8][c:9]32)[cH:28][cH:27]1>>[O:1]=[C:2]1[NH:3][c:4]2[cH:5][cH:6][cH:7][cH:8][c:9]2[C:10]1=[CH:11][NH:12][c:13]1[cH:14][cH:15][c:16]([O:17][CH2:... | C1CCNC1.O=C1Nc2ccccc2C1=CNc1ccc(OCCCCI)cc1 | O=C1Nc2ccccc2C1=CNc1ccc(OCCCCN2CCCC2)cc1 | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 19b442dc26882f89f7423416f5e0a16bdb8e48776df57991434a0634e21f0505 | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | O=C1Nc2ccccc2C1=CNc1ccc(OCCCCN2CCCC2)cc1 | I-[CH2;D2;+0:1]-[C:2]-[C:3].[C:4]1-[C:5]-[C:6]-[C:7]-[NH;D2;+0:8]-1>>[C:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:8]1-[C:4]-[C:5]-[C:6]-[C:7]-1 | null | [] | null | null | null | null | In a manner similar to that described in Example 207, 3-{[4-(4-Iodo-butoxy)-phenylamino]-methylene}-1,3-dihydro-indol-2-one and pyrrolidine are converted to the named compound
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1CCNC1 | C1CC[NH]C1 | c1ccc2c(c1)CCN2.c1ccccc1.C1CC[NH]C1 | HI | null | null | null | C1CCNC1.O=C1Nc2ccccc2C1=CNc1ccc(OCCCCI)cc1>>O=C1Nc2ccccc2C1=CNc1ccc(OCCCCN2CCCC2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-ba0f07da5b164eb392ee45a4e001eba6 | ClCCCBr.O=C1Nc2ccccc2C1=CNc1ccc(O)cc1>>O=C1Nc2ccccc2C1=CNc1ccc(OCCCCl)cc1 | OC1=CC=C(C=C1)NC=C1C(NC2=CC=CC=C12)=O.C([O-])([O-])=O.[K+].[K+].BrCCCCl>>ClCCCOC1=CC=C(C=C1)NC=C1C(NC2=CC=CC=C12)=O | Br[CH2:18][CH2:19][CH2:20][Cl:21].[O:1]=[C:2]1[NH:3][c:4]2[cH:5][cH:6][cH:7][cH:8][c:9]2[C:10]1=[CH:11][NH:12][c:13]1[cH:14][cH:15][c:16]([OH:17])[cH:22][cH:23]1>>[O:1]=[C:2]1[NH:3][c:4]2[cH:5][cH:6][cH:7][cH:8][c:9]2[C:10]1=[CH:11][NH:12][c:13]1[cH:14][cH:15][c:16]([O:17][CH2:18][CH2:19][CH2:20][Cl:21])[cH:22][cH:23]1 | ClCCCBr.O=C1Nc2ccccc2C1=CNc1ccc(O)cc1 | O=C1Nc2ccccc2C1=CNc1ccc(OCCCCl)cc1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | O=C1Nc2ccccc2C1=CNc1ccccc1 | 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] | 58 | [{"value": 58.0, "product": "ClCCCOC1=CC=C(C=C1)NC=C1C(NC2=CC=CC=C12)=O", "details": "PERCENTYIELD", "is_desired": false}] | 40 | CELSIUS | null | null | A solution of 3-[(4-hydroxy-phenylamino)-methylene]-1,3-dihydro-indol-2-one (0.945 g, 3.75 mmol) in 20 mL DMF is treated with potassium carbonate (777 mg, 1.5 equiv.) and 1-bromo-3-chloropropane (1.1 equiv.). The reaction mixture is heated to 40° C. for 3 h. The reaction mixture is partitioned between EtOAc and water. ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccc2c(c1)CCN2.c1ccccc1 | HBr | CN(C)C=O | 40 | null | ClCCCBr.O=C1Nc2ccccc2C1=CNc1ccc(O)cc1>CN(C)C=O>O=C1Nc2ccccc2C1=CNc1ccc(OCCCCl)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-e59928bf063b45659a6ee618c58ae04a | ClCCCCBr.O=C1Nc2ccccc2C1=CNc1ccc(O)cc1>>O=C1Nc2ccccc2C1=CNc1ccc(OCCCCCl)cc1 | OC1=CC=C(C=C1)NC=C1C(NC2=CC=CC=C12)=O.C([O-])([O-])=O.[K+].[K+].BrCCCCCl>>ClCCCCOC1=CC=C(C=C1)NC=C1C(NC2=CC=CC=C12)=O | Br[CH2:18][CH2:19][CH2:20][CH2:21][Cl:22].[O:1]=[C:2]1[NH:3][c:4]2[cH:5][cH:6][cH:7][cH:8][c:9]2[C:10]1=[CH:11][NH:12][c:13]1[cH:14][cH:15][c:16]([OH:17])[cH:23][cH:24]1>>[O:1]=[C:2]1[NH:3][c:4]2[cH:5][cH:6][cH:7][cH:8][c:9]2[C:10]1=[CH:11][NH:12][c:13]1[cH:14][cH:15][c:16]([O:17][CH2:18][CH2:19][CH2:20][CH2:21][Cl:22]... | ClCCCCBr.O=C1Nc2ccccc2C1=CNc1ccc(O)cc1 | O=C1Nc2ccccc2C1=CNc1ccc(OCCCCCl)cc1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | O=C1Nc2ccccc2C1=CNc1ccccc1 | 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] | 47 | [{"value": 47.0, "product": "ClCCCCOC1=CC=C(C=C1)NC=C1C(NC2=CC=CC=C12)=O", "details": "PERCENTYIELD", "is_desired": false}] | 40 | CELSIUS | null | null | A solution of 3-[(4-hydroxy-phenylamino)-methylene]-1,3-dihydro-indol-2-one (0.945 g, 3.75 mmol) in 20 mL DMF is treated with potassium carbonate (777 mg, 1.5 equiv.) and 1-bromo-4-chlorobutane (1.1 equiv.). The reaction mixture is heated to 40° C. for 3 h. The reaction mixture is partitioned between EtOAc and water. T... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccc2c(c1)CCN2.c1ccccc1 | HBr | CN(C)C=O | 40 | null | ClCCCCBr.O=C1Nc2ccccc2C1=CNc1ccc(O)cc1>CN(C)C=O>O=C1Nc2ccccc2C1=CNc1ccc(OCCCCCl)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-376a8b6d4bac47d5b8381fcf27c41b3d | O=C1Nc2ccccc2C1=CNc1ccc(OCCCCl)cc1.[I-]>>O=C1Nc2ccccc2C1=CNc1ccc(OCCCI)cc1 | ClCCCOC1=CC=C(C=C1)NC=C1C(NC2=CC=CC=C12)=O.[Na+].[I-]>>ICCCOC1=CC=C(C=C1)NC=C1C(NC2=CC=CC=C12)=O | Cl[CH2:20][CH2:19][CH2:18][O:17][c:16]1[cH:15][cH:14][c:13]([NH:12][CH:11]=[C:10]2[C:2](=[O:1])[NH:3][c:4]3[cH:5][cH:6][cH:7][cH:8][c:9]32)[cH:23][cH:22]1.[I-:21]>>[O:1]=[C:2]1[NH:3][c:4]2[cH:5][cH:6][cH:7][cH:8][c:9]2[C:10]1=[CH:11][NH:12][c:13]1[cH:14][cH:15][c:16]([O:17][CH2:18][CH2:19][CH2:20][I:21])[cH:22][cH:23]1 | O=C1Nc2ccccc2C1=CNc1ccc(OCCCCl)cc1.[I-] | O=C1Nc2ccccc2C1=CNc1ccc(OCCCI)cc1 | null | null | CC(=O)C | Functional Group Interconversion | OtherReaction | e944a2acb95a43a23818321f2ac2f96ba2f2b8d34f52c1cfd1e3802d2403177f | e2ca6f9fe1078a3836d617896a4e5cc310fb155ca459b021e2b549b3e61f1df7 | O=C1Nc2ccccc2C1=CNc1ccccc1 | Cl-[CH2;D2;+0:1]-[C:2]-[C:3].[I-;H0;D0:4]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[I;H0;D1;+0:4] | 100 | [{"value": 100.0, "product": "ICCCOC1=CC=C(C=C1)NC=C1C(NC2=CC=CC=C12)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 3-{[4-(3-Chloro-propoxy)-phenylamino]-methylene}-1,3-dihydro-indol-2-one (45 mg, 0.137 mmol) and NaI (103 mg, 5 equiv.) in 1 mL acetone is heated at 80° C. overnight. The reaction mixture is cooled to room temperature and evaporated to dryness. The residue is dissolved in EtOAc and H2O. The organic layer ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | Primary halide | null | null | c1ccc2c(c1)CCN2.c1ccccc1 | Other | CC(=O)C | null | null | O=C1Nc2ccccc2C1=CNc1ccc(OCCCCl)cc1.[I-]>CC(=O)C>O=C1Nc2ccccc2C1=CNc1ccc(OCCCI)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-4ce9bc2afe0f407fa3bed3b3ce2b156e | C1COCCN1.O=C1Nc2ccccc2C1=CNc1ccc(OCCCCI)cc1>>O=C1Nc2ccccc2C1=CNc1ccc(OCCCCN2CCOCC2)cc1 | ICCCCOC1=CC=C(C=C1)NC=C1C(NC2=CC=CC=C12)=O.N1CCOCC1>>N1(CCOCC1)CCCCOC1=CC=C(C=C1)NC=C1C(NC2=CC=CC=C12)=O | [NH:22]1[CH2:23][CH2:24][O:25][CH2:26][CH2:27]1.I[CH2:21][CH2:20][CH2:19][CH2:18][O:17][c:16]1[cH:15][cH:14][c:13]([NH:12][CH:11]=[C:10]2[C:2](=[O:1])[NH:3][c:4]3[cH:5][cH:6][cH:7][cH:8][c:9]32)[cH:29][cH:28]1>>[O:1]=[C:2]1[NH:3][c:4]2[cH:5][cH:6][cH:7][cH:8][c:9]2[C:10]1=[CH:11][NH:12][c:13]1[cH:14][cH:15][c:16]([O:17... | C1COCCN1.O=C1Nc2ccccc2C1=CNc1ccc(OCCCCI)cc1 | O=C1Nc2ccccc2C1=CNc1ccc(OCCCCN2CCOCC2)cc1 | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 2bad30dcdb0a20edb8ce877f072b133eedfd870621da393ec393128bfee00977 | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | O=C1Nc2ccccc2C1=CNc1ccc(OCCCCN2CCOCC2)cc1 | I-[CH2;D2;+0:1]-[C:2]-[C:3].[#8:4]1-[C:5]-[C:6]-[NH;D2;+0:7]-[C:8]-[C:9]-1>>[C:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:7]1-[C:6]-[C:5]-[#8:4]-[C:9]-[C:8]-1 | null | [] | null | null | null | null | In a manner similar to that described in Example 207, 3-{[4-(4-Iodo-butoxy)-phenylamino]-methylene}-1,3-dihydro-indol-2-one and morpholine are converted to the named compound.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1COCCN1 | C1COCC[NH]1 | c1ccc2c(c1)CCN2.c1ccccc1.C1COCC[NH]1 | HI | null | null | null | C1COCCN1.O=C1Nc2ccccc2C1=CNc1ccc(OCCCCI)cc1>>O=C1Nc2ccccc2C1=CNc1ccc(OCCCCN2CCOCC2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-e21fe4f1ea89493f96de461328f548a8 | CCNCC.O=C1Nc2ccccc2C1=CNc1ccc(OCCCCI)cc1>>CCN(CC)CCCCOc1ccc(NC=C2C(=O)Nc3ccccc32)cc1 | ICCCCOC1=CC=C(C=C1)NC=C1C(NC2=CC=CC=C12)=O.C(C)NCC>>C(C)N(CCCCOC1=CC=C(C=C1)NC=C1C(NC2=CC=CC=C12)=O)CC | [CH3:1][CH2:2][NH:3][CH2:4][CH3:5].I[CH2:6][CH2:7][CH2:8][CH2:9][O:10][c:11]1[cH:12][cH:13][c:14]([NH:15][CH:16]=[C:17]2[C:18](=[O:19])[NH:20][c:21]3[cH:22][cH:23][cH:24][cH:25][c:26]32)[cH:27][cH:28]1>>[CH3:1][CH2:2][N:3]([CH2:4][CH3:5])[CH2:6][CH2:7][CH2:8][CH2:9][O:10][c:11]1[cH:12][cH:13][c:14]([NH:15][CH:16]=[C:17... | CCNCC.O=C1Nc2ccccc2C1=CNc1ccc(OCCCCI)cc1 | CCN(CC)CCCCOc1ccc(NC=C2C(=O)Nc3ccccc32)cc1 | null | null | CO | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 6d58cac08ccced0a33ed16fbca180bc12aa011288d6476106d98a7b2cbc3d709 | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | O=C1Nc2ccccc2C1=CNc1ccccc1 | I-[CH2;D2;+0:1]-[C:2]-[C:3].[C;D1;H3:4]-[C:5]-[NH;D2;+0:6]-[C:7]-[C;D1;H3:8]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:6](-[C:5]-[C;D1;H3:4])-[C:7]-[C;D1;H3:8] | null | [] | 50 | CELSIUS | null | null | A 25 mL pressure tube is charged with 3-{[4-(4-Iodo-butoxy)-phenylamino]-methylene}-1,3-dihydro-indol-2-one (75 mg, 0.173 mmol), diethylamine (2 mL) and the reaction mixture is heated at 50° C. for 3 h. The reaction mixture is cooled to room temperature and partitioned between EtOAc and H2O. The organic layer is washed... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | null | null | c1ccccc1.c1ccc2c(c1)CCN2 | HI | CO | 50 | null | CCNCC.O=C1Nc2ccccc2C1=CNc1ccc(OCCCCI)cc1>CO>CCN(CC)CCCCOc1ccc(NC=C2C(=O)Nc3ccccc32)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-c525420225184c11a976f1ed67d370d3 | CN1CCNCC1.O=C1Nc2ccccc2C1=CNc1ccc(OCCCCI)cc1>>CN1CCN(CCCCOc2ccc(NC=C3C(=O)Nc4ccccc43)cc2)CC1 | ICCCCOC1=CC=C(C=C1)NC=C1C(NC2=CC=CC=C12)=O.CN1CCNCC1>>CN1CCN(CC1)CCCCOC1=CC=C(C=C1)NC=C1C(NC2=CC=CC=C12)=O | [CH3:1][N:2]1[CH2:3][CH2:4][NH:5][CH2:29][CH2:30]1.I[CH2:6][CH2:7][CH2:8][CH2:9][O:10][c:11]1[cH:12][cH:13][c:14]([NH:15][CH:16]=[C:17]2[C:18](=[O:19])[NH:20][c:21]3[cH:22][cH:23][cH:24][cH:25][c:26]32)[cH:27][cH:28]1>>[CH3:1][N:2]1[CH2:3][CH2:4][N:5]([CH2:6][CH2:7][CH2:8][CH2:9][O:10][c:11]2[cH:12][cH:13][c:14]([NH:15... | CN1CCNCC1.O=C1Nc2ccccc2C1=CNc1ccc(OCCCCI)cc1 | CN1CCN(CCCCOc2ccc(NC=C3C(=O)Nc4ccccc43)cc2)CC1 | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | b703623ddc3b029d4716c15f5414f41773434bcc7e3f3853faf62273596bed77 | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | O=C1Nc2ccccc2C1=CNc1ccc(OCCCCN2CCNCC2)cc1 | I-[CH2;D2;+0:1]-[C:2]-[C:3].[#7:4]1-[C:5]-[C:6]-[NH;D2;+0:7]-[C:8]-[C:9]-1>>[C:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:7]1-[C:6]-[C:5]-[#7:4]-[C:9]-[C:8]-1 | null | [] | null | null | null | null | In a manner similar to that described in Example 207, 3-{[4-(4-Iodo-butoxy)-phenylamino]-methylene}-1,3-dihydro-indol-2-one and N-methylpiperazine are converted to the named compound.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1C[NH]CCN1 | C1C[NH]CC[NH]1 | C1C[NH]CC[NH]1.c1ccccc1.c1ccc2c(c1)CCN2 | HI | null | null | null | CN1CCNCC1.O=C1Nc2ccccc2C1=CNc1ccc(OCCCCI)cc1>>CN1CCN(CCCCOc2ccc(NC=C3C(=O)Nc4ccccc43)cc2)CC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-02bd20cc43fe4eafb90c3db1d4787cd4 | C1CCNCC1.O=C1Nc2ccccc2C1=CNc1ccc(OCCCCI)cc1>>O=C1Nc2ccccc2C1=CNc1ccc(OCCCCN2CCCCC2)cc1 | ICCCCOC1=CC=C(C=C1)NC=C1C(NC2=CC=CC=C12)=O.N1CCCCC1>>N1(CCCCC1)CCCCOC1=CC=C(C=C1)NC=C1C(NC2=CC=CC=C12)=O | [NH:22]1[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27]1.I[CH2:21][CH2:20][CH2:19][CH2:18][O:17][c:16]1[cH:15][cH:14][c:13]([NH:12][CH:11]=[C:10]2[C:2](=[O:1])[NH:3][c:4]3[cH:5][cH:6][cH:7][cH:8][c:9]32)[cH:29][cH:28]1>>[O:1]=[C:2]1[NH:3][c:4]2[cH:5][cH:6][cH:7][cH:8][c:9]2[C:10]1=[CH:11][NH:12][c:13]1[cH:14][cH:15][c:16]([O:... | C1CCNCC1.O=C1Nc2ccccc2C1=CNc1ccc(OCCCCI)cc1 | O=C1Nc2ccccc2C1=CNc1ccc(OCCCCN2CCCCC2)cc1 | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 0240b8450ff2c489d02f5f0d90bc953079d7a3ab239d35a03f26392fc248b4ef | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | O=C1Nc2ccccc2C1=CNc1ccc(OCCCCN2CCCCC2)cc1 | I-[CH2;D2;+0:1]-[C:2]-[C:3].[C:4]-[C:5]-[NH;D2;+0:6]-[C:7]-[C:8]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:6](-[C:5]-[C:4])-[C:7]-[C:8] | null | [] | null | null | null | null | In a manner similar to that described in Example 207, 3-{[4-(4-Iodo-butoxy)-phenylamino]-methylene}-1,3-dihydro-indol-2-one and piperidine are converted to the named compound
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1CCNCC1 | C1CC[NH]CC1 | c1ccc2c(c1)CCN2.c1ccccc1.C1CC[NH]CC1 | HI | null | null | null | C1CCNCC1.O=C1Nc2ccccc2C1=CNc1ccc(OCCCCI)cc1>>O=C1Nc2ccccc2C1=CNc1ccc(OCCCCN2CCCCC2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-46c12e1cbaa24d7e81d4058a71332211 | CCNCC.O=C1Nc2ccccc2C1=CNc1ccc(OCCCI)cc1>>CCN(CC)CCCOc1ccc(NC=C2C(=O)Nc3ccccc32)cc1 | ICCCOC1=CC=C(C=C1)NC=C1C(NC2=CC=CC=C12)=O.C(C)NCC>>C(C)N(CCCOC1=CC=C(C=C1)NC=C1C(NC2=CC=CC=C12)=O)CC | [CH3:1][CH2:2][NH:3][CH2:4][CH3:5].I[CH2:6][CH2:7][CH2:8][O:9][c:10]1[cH:11][cH:12][c:13]([NH:14][CH:15]=[C:16]2[C:17](=[O:18])[NH:19][c:20]3[cH:21][cH:22][cH:23][cH:24][c:25]32)[cH:26][cH:27]1>>[CH3:1][CH2:2][N:3]([CH2:4][CH3:5])[CH2:6][CH2:7][CH2:8][O:9][c:10]1[cH:11][cH:12][c:13]([NH:14][CH:15]=[C:16]2[C:17](=[O:18]... | CCNCC.O=C1Nc2ccccc2C1=CNc1ccc(OCCCI)cc1 | CCN(CC)CCCOc1ccc(NC=C2C(=O)Nc3ccccc32)cc1 | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 6d58cac08ccced0a33ed16fbca180bc12aa011288d6476106d98a7b2cbc3d709 | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | O=C1Nc2ccccc2C1=CNc1ccccc1 | I-[CH2;D2;+0:1]-[C:2]-[C:3].[C;D1;H3:4]-[C:5]-[NH;D2;+0:6]-[C:7]-[C;D1;H3:8]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:6](-[C:5]-[C;D1;H3:4])-[C:7]-[C;D1;H3:8] | null | [] | null | null | null | null | In a manner similar to that described in Example 217, 3-{[4-(3-Iodo-propoxy)-phenylamino]-methylene}-1,3-dihydro-indol-2-one and diethylamine are converted to the named compound.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | null | null | c1ccccc1.c1ccc2c(c1)CCN2 | HI | null | null | null | CCNCC.O=C1Nc2ccccc2C1=CNc1ccc(OCCCI)cc1>>CCN(CC)CCCOc1ccc(NC=C2C(=O)Nc3ccccc32)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-85975efea6174381b8be906b725ccd58 | C1COCCN1.O=C1Nc2ccccc2C1=CNc1ccc(OCCCI)cc1>>O=C1Nc2ccccc2C1=CNc1ccc(OCCCN2CCOCC2)cc1 | ICCCOC1=CC=C(C=C1)NC=C1C(NC2=CC=CC=C12)=O.N1CCOCC1>>N1(CCOCC1)CCCOC1=CC=C(C=C1)NC=C1C(NC2=CC=CC=C12)=O | [NH:21]1[CH2:22][CH2:23][O:24][CH2:25][CH2:26]1.I[CH2:20][CH2:19][CH2:18][O:17][c:16]1[cH:15][cH:14][c:13]([NH:12][CH:11]=[C:10]2[C:2](=[O:1])[NH:3][c:4]3[cH:5][cH:6][cH:7][cH:8][c:9]32)[cH:28][cH:27]1>>[O:1]=[C:2]1[NH:3][c:4]2[cH:5][cH:6][cH:7][cH:8][c:9]2[C:10]1=[CH:11][NH:12][c:13]1[cH:14][cH:15][c:16]([O:17][CH2:18... | C1COCCN1.O=C1Nc2ccccc2C1=CNc1ccc(OCCCI)cc1 | O=C1Nc2ccccc2C1=CNc1ccc(OCCCN2CCOCC2)cc1 | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 2bad30dcdb0a20edb8ce877f072b133eedfd870621da393ec393128bfee00977 | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | O=C1Nc2ccccc2C1=CNc1ccc(OCCCN2CCOCC2)cc1 | I-[CH2;D2;+0:1]-[C:2]-[C:3].[#8:4]1-[C:5]-[C:6]-[NH;D2;+0:7]-[C:8]-[C:9]-1>>[C:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:7]1-[C:6]-[C:5]-[#8:4]-[C:9]-[C:8]-1 | null | [] | null | null | null | null | In a manner similar to that described in Example 217, 3-{[4-(3-Iodo-propoxy)-phenylamino]-methylene}-1,3-dihydro-indol-2-one and morpholine are converted to the named compound.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1COCCN1 | C1COCC[NH]1 | c1ccc2c(c1)CCN2.c1ccccc1.C1COCC[NH]1 | HI | null | null | null | C1COCCN1.O=C1Nc2ccccc2C1=CNc1ccc(OCCCI)cc1>>O=C1Nc2ccccc2C1=CNc1ccc(OCCCN2CCOCC2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-7625ffc6f36c4761b43c3ef79262e1bb | C1CCNC1.O=C1Nc2ccccc2C1=CNc1ccc(OCCCI)cc1>>O=C1Nc2ccccc2C1=CNc1ccc(OCCCN2CCCC2)cc1 | ICCCOC1=CC=C(C=C1)NC=C1C(NC2=CC=CC=C12)=O.N1CCCC1>>N1(CCCC1)CCCOC1=CC=C(C=C1)NC=C1C(NC2=CC=CC=C12)=O | [NH:21]1[CH2:22][CH2:23][CH2:24][CH2:25]1.I[CH2:20][CH2:19][CH2:18][O:17][c:16]1[cH:15][cH:14][c:13]([NH:12][CH:11]=[C:10]2[C:2](=[O:1])[NH:3][c:4]3[cH:5][cH:6][cH:7][cH:8][c:9]32)[cH:27][cH:26]1>>[O:1]=[C:2]1[NH:3][c:4]2[cH:5][cH:6][cH:7][cH:8][c:9]2[C:10]1=[CH:11][NH:12][c:13]1[cH:14][cH:15][c:16]([O:17][CH2:18][CH2:... | C1CCNC1.O=C1Nc2ccccc2C1=CNc1ccc(OCCCI)cc1 | O=C1Nc2ccccc2C1=CNc1ccc(OCCCN2CCCC2)cc1 | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 19b442dc26882f89f7423416f5e0a16bdb8e48776df57991434a0634e21f0505 | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | O=C1Nc2ccccc2C1=CNc1ccc(OCCCN2CCCC2)cc1 | I-[CH2;D2;+0:1]-[C:2]-[C:3].[C:4]1-[C:5]-[C:6]-[C:7]-[NH;D2;+0:8]-1>>[C:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:8]1-[C:4]-[C:5]-[C:6]-[C:7]-1 | null | [] | null | null | null | null | In a manner similar to that described in Example 217, 3-{[4-(3-Iodo-propoxy)-phenylamino]-methylene}-1,3-dihydro-indol-2-one and pyrrolidine are converted to the named compound.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1CCNC1 | C1CC[NH]C1 | c1ccc2c(c1)CCN2.c1ccccc1.C1CC[NH]C1 | HI | null | null | null | C1CCNC1.O=C1Nc2ccccc2C1=CNc1ccc(OCCCI)cc1>>O=C1Nc2ccccc2C1=CNc1ccc(OCCCN2CCCC2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-31d312c2e45f4f3c8790dd87c1ce3c70 | CN1CCNCC1.O=C1Nc2ccccc2C1=CNc1ccc(OCCCI)cc1>>CN1CCN(CCCOc2ccc(NC=C3C(=O)Nc4ccccc43)cc2)CC1 | CCOC(=O)C.ICCCOC1=CC=C(C=C1)NC=C1C(NC2=CC=CC=C12)=O.CN1CCNCC1>>CN1CCN(CC1)CCCOC1=CC=C(C=C1)NC=C1C(NC2=CC=CC=C12)=O | [CH3:1][N:2]1[CH2:3][CH2:4][NH:5][CH2:28][CH2:29]1.I[CH2:6][CH2:7][CH2:8][O:9][c:10]1[cH:11][cH:12][c:13]([NH:14][CH:15]=[C:16]2[C:17](=[O:18])[NH:19][c:20]3[cH:21][cH:22][cH:23][cH:24][c:25]32)[cH:26][cH:27]1>>[CH3:1][N:2]1[CH2:3][CH2:4][N:5]([CH2:6][CH2:7][CH2:8][O:9][c:10]2[cH:11][cH:12][c:13]([NH:14][CH:15]=[C:16]3... | CN1CCNCC1.O=C1Nc2ccccc2C1=CNc1ccc(OCCCI)cc1 | CN1CCN(CCCOc2ccc(NC=C3C(=O)Nc4ccccc43)cc2)CC1 | null | null | C1CCOC1 | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | b703623ddc3b029d4716c15f5414f41773434bcc7e3f3853faf62273596bed77 | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | O=C1Nc2ccccc2C1=CNc1ccc(OCCCN2CCNCC2)cc1 | I-[CH2;D2;+0:1]-[C:2]-[C:3].[#7:4]1-[C:5]-[C:6]-[NH;D2;+0:7]-[C:8]-[C:9]-1>>[C:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:7]1-[C:6]-[C:5]-[#7:4]-[C:9]-[C:8]-1 | null | [] | 50 | CELSIUS | null | null | A solution of 3-{[4-(3-Iodo-propoxy)-phenylamino]-methylene}-1,3-dihydro-indol-2-one (66 mg, 0.157 mmol) in 1 mL THF is treated with 1-methylpiperazine (37.2 μL, 2.2 equiv.) and the resulting reaction mixture is heated at 50° C. for 4 h. The reaction mixture is cooled to room temperature and concentrated under reduced ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1C[NH]CCN1 | C1C[NH]CC[NH]1 | C1C[NH]CC[NH]1.c1ccccc1.c1ccc2c(c1)CCN2 | HI | C1CCOC1 | 50 | null | CN1CCNCC1.O=C1Nc2ccccc2C1=CNc1ccc(OCCCI)cc1>C1CCOC1>CN1CCN(CCCOc2ccc(NC=C3C(=O)Nc4ccccc43)cc2)CC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-54e4df941dd84a3ab372f0f3792b8388 | C1CCNCC1.O=C1Nc2ccccc2C1=CNc1ccc(OCCCI)cc1>>O=C1Nc2ccccc2C1=CNc1ccc(OCCCN2CCCCC2)cc1 | ICCCOC1=CC=C(C=C1)NC=C1C(NC2=CC=CC=C12)=O.N1CCCCC1>>N1(CCCCC1)CCCOC1=CC=C(C=C1)NC=C1C(NC2=CC=CC=C12)=O | [NH:21]1[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26]1.I[CH2:20][CH2:19][CH2:18][O:17][c:16]1[cH:15][cH:14][c:13]([NH:12][CH:11]=[C:10]2[C:2](=[O:1])[NH:3][c:4]3[cH:5][cH:6][cH:7][cH:8][c:9]32)[cH:28][cH:27]1>>[O:1]=[C:2]1[NH:3][c:4]2[cH:5][cH:6][cH:7][cH:8][c:9]2[C:10]1=[CH:11][NH:12][c:13]1[cH:14][cH:15][c:16]([O:17][CH2:... | C1CCNCC1.O=C1Nc2ccccc2C1=CNc1ccc(OCCCI)cc1 | O=C1Nc2ccccc2C1=CNc1ccc(OCCCN2CCCCC2)cc1 | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 0240b8450ff2c489d02f5f0d90bc953079d7a3ab239d35a03f26392fc248b4ef | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | O=C1Nc2ccccc2C1=CNc1ccc(OCCCN2CCCCC2)cc1 | I-[CH2;D2;+0:1]-[C:2]-[C:3].[C:4]-[C:5]-[NH;D2;+0:6]-[C:7]-[C:8]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:6](-[C:5]-[C:4])-[C:7]-[C:8] | null | [] | null | null | null | null | In a manner similar to that described in Example 217, 3-{[4-(3-Iodo-propoxy)-phenylamino]-methylene}-1,3-dihydro-indol-2-one and piperidine are converted to the named compound.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1CCNCC1 | C1CC[NH]CC1 | c1ccc2c(c1)CCN2.c1ccccc1.C1CC[NH]CC1 | HI | null | null | null | C1CCNCC1.O=C1Nc2ccccc2C1=CNc1ccc(OCCCI)cc1>>O=C1Nc2ccccc2C1=CNc1ccc(OCCCN2CCCCC2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-51c4e561f3e04a4db6bb822285a3df3d | C1CSCCN1.O=C1Nc2ccccc2C1=CNc1ccc(OCCCI)cc1>>O=C1Nc2ccccc2C1=CNc1ccc(OCCCN2CCSCC2)cc1 | ICCCOC1=CC=C(C=C1)NC=C1C(NC2=CC=CC=C12)=O.N1CCSCC1>>N1(CCSCC1)CCCOC1=CC=C(C=C1)NC=C1C(NC2=CC=CC=C12)=O | [NH:21]1[CH2:22][CH2:23][S:24][CH2:25][CH2:26]1.I[CH2:20][CH2:19][CH2:18][O:17][c:16]1[cH:15][cH:14][c:13]([NH:12][CH:11]=[C:10]2[C:2](=[O:1])[NH:3][c:4]3[cH:5][cH:6][cH:7][cH:8][c:9]32)[cH:28][cH:27]1>>[O:1]=[C:2]1[NH:3][c:4]2[cH:5][cH:6][cH:7][cH:8][c:9]2[C:10]1=[CH:11][NH:12][c:13]1[cH:14][cH:15][c:16]([O:17][CH2:18... | C1CSCCN1.O=C1Nc2ccccc2C1=CNc1ccc(OCCCI)cc1 | O=C1Nc2ccccc2C1=CNc1ccc(OCCCN2CCSCC2)cc1 | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 31b0b9e0d8fa3b7db3a979cae26f03e95f940fcd41af95ddcbf849f2eb58ca68 | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | O=C1Nc2ccccc2C1=CNc1ccc(OCCCN2CCSCC2)cc1 | I-[CH2;D2;+0:1]-[C:2]-[C:3].[#16:4]1-[C:5]-[C:6]-[NH;D2;+0:7]-[C:8]-[C:9]-1>>[C:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:7]1-[C:6]-[C:5]-[#16:4]-[C:9]-[C:8]-1 | null | [] | null | null | null | null | In a manner similar to that described in Example 217, 3-{[4-(3-Iodo-propoxy)-phenylamino]-methylene}-1,3-dihydro-indol-2-one and thiomorpholine are converted to the named compound.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1CSCCN1 | C1CSCC[NH]1 | c1ccc2c(c1)CCN2.c1ccccc1.C1CSCC[NH]1 | HI | null | null | null | C1CSCCN1.O=C1Nc2ccccc2C1=CNc1ccc(OCCCI)cc1>>O=C1Nc2ccccc2C1=CNc1ccc(OCCCN2CCSCC2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-c281f04e7e534b75997dda3f8bd42dee | C1CSCCN1.O=C1Nc2ccccc2C1=CNc1ccc(OCCCCI)cc1>>O=C1Nc2ccccc2C1=CNc1ccc(OCCCCN2CCSCC2)cc1 | ICCCCOC1=CC=C(C=C1)NC=C1C(NC2=CC=CC=C12)=O.N1CCSCC1>>N1(CCSCC1)CCCCOC1=CC=C(C=C1)NC=C1C(NC2=CC=CC=C12)=O | [NH:22]1[CH2:23][CH2:24][S:25][CH2:26][CH2:27]1.I[CH2:21][CH2:20][CH2:19][CH2:18][O:17][c:16]1[cH:15][cH:14][c:13]([NH:12][CH:11]=[C:10]2[C:2](=[O:1])[NH:3][c:4]3[cH:5][cH:6][cH:7][cH:8][c:9]32)[cH:29][cH:28]1>>[O:1]=[C:2]1[NH:3][c:4]2[cH:5][cH:6][cH:7][cH:8][c:9]2[C:10]1=[CH:11][NH:12][c:13]1[cH:14][cH:15][c:16]([O:17... | C1CSCCN1.O=C1Nc2ccccc2C1=CNc1ccc(OCCCCI)cc1 | O=C1Nc2ccccc2C1=CNc1ccc(OCCCCN2CCSCC2)cc1 | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 31b0b9e0d8fa3b7db3a979cae26f03e95f940fcd41af95ddcbf849f2eb58ca68 | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | O=C1Nc2ccccc2C1=CNc1ccc(OCCCCN2CCSCC2)cc1 | I-[CH2;D2;+0:1]-[C:2]-[C:3].[#16:4]1-[C:5]-[C:6]-[NH;D2;+0:7]-[C:8]-[C:9]-1>>[C:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:7]1-[C:6]-[C:5]-[#16:4]-[C:9]-[C:8]-1 | null | [] | null | null | null | null | In a manner similar to that described in Example 207, 3-{[4-(4-Iodo-butoxy)-phenylamino]-methylene}-1,3-dihydro-indol-2-one and thiomorpholine are converted to the named compound.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1CSCCN1 | C1CSCC[NH]1 | c1ccc2c(c1)CCN2.c1ccccc1.C1CSCC[NH]1 | HI | null | null | null | C1CSCCN1.O=C1Nc2ccccc2C1=CNc1ccc(OCCCCI)cc1>>O=C1Nc2ccccc2C1=CNc1ccc(OCCCCN2CCSCC2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-5ca2a8c3e9374019bae1ccdcfb592cf8 | CCN(CC)CCCOc1ccc(N)cc1.Cc1cccc2c1C(=CO)C(=O)N2>>CCN(CC)CCCOc1ccc(NC=C2C(=O)Nc3cccc(C)c32)cc1 | C(C)N(CCCOC1=CC=C(C=C1)N)CC.CC1=C2C(C(NC2=CC=C1)=O)=CO>>C(C)N(CCCOC1=CC=C(C=C1)NC=C1C(NC2=CC=CC(=C12)C)=O)CC | [CH3:1][CH2:2][N:3]([CH2:4][CH3:5])[CH2:6][CH2:7][CH2:8][O:9][c:10]1[cH:11][cH:12][c:13]([NH2:14])[cH:27][cH:28]1.O[CH:15]=[C:16]1[C:17](=[O:18])[NH:19][c:20]2[cH:21][cH:22][cH:23][c:24]([CH3:25])[c:26]21>>[CH3:1][CH2:2][N:3]([CH2:4][CH3:5])[CH2:6][CH2:7][CH2:8][O:9][c:10]1[cH:11][cH:12][c:13]([NH:14][CH:15]=[C:16]2[C:... | CCN(CC)CCCOc1ccc(N)cc1.Cc1cccc2c1C(=CO)C(=O)N2 | CCN(CC)CCCOc1ccc(NC=C2C(=O)Nc3cccc(C)c32)cc1 | null | null | C1CCOC1 | Heteroatom Alkylation and Arylation | Reductive amination with alcohol | ac661a5987df49e763a2386679221354b73376953f4071e32e52e2d7e8877593 | dc27e5e3871ba014ddcdbe66aa8244518b94cc851f1ff4159b6674656bc3b780 | O=C1Nc2ccccc2C1=CNc1ccccc1 | O-[CH;D2;+0:1]=[C:2]1-[c:3]:[c:4]-[#7:5]-[C:6]-1=[O;D1;H0:7].[NH2;D1;+0:8]-[c:9](:[c:10]):[c:11]>>[O;D1;H0:7]=[C:6]1-[#7:5]-[c:4]:[c:3]-[C:2]-1=[CH;D2;+0:1]-[NH;D2;+0:8]-[c:9](:[c:10]):[c:11] | 52 | [{"value": 52.0, "product": "C(C)N(CCCOC1=CC=C(C=C1)NC=C1C(NC2=CC=CC(=C12)C)=O)CC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 52.0, "product": "C(C)N(CCCOC1=CC=C(C=C1)NC=C1C(NC2=CC=CC(=C12)C)=O)CC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 72 | CELSIUS | null | null | To a solution of 4-(3-diethylamino-propoxy)-phenylamine (913 mg, 1.3 equiv.) in THF (14 mL) is added 4-methyl-3-hydroxymethylene-1,3-dihydro-indol-2-one (554 mg, 3.17 mmol) in one portion. The resulting reaction mixture is stirred and heated at 72° C. overnight. The reaction solution is cooled to room temperature and p... | 10.6084/m9.figshare.5104873.v1 | null | Enol.Primary amine | Enamine | null | null | c1ccccc1.c1ccc2c(c1)CCN2 | HO- | C1CCOC1 | 72 | null | CCN(CC)CCCOc1ccc(N)cc1.Cc1cccc2c1C(=CO)C(=O)N2>C1CCOC1>CCN(CC)CCCOc1ccc(NC=C2C(=O)Nc3cccc(C)c32)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b8a7013060c64ea0a72ae1347253d224 | CCN(CC)CCCO.O=[N+]([O-])c1ccc(F)cc1>>CCN(CC)CCCOc1ccc([N+](=O)[O-])cc1 | FC1=CC=C(C=C1)[N+](=O)[O-].C(C)N(CCCO)CC.CC(C)([O-])C.[K+]>>C(C)N(CCCOC1=CC=C(C=C1)[N+](=O)[O-])CC | [CH3:1][CH2:2][N:3]([CH2:4][CH3:5])[CH2:6][CH2:7][CH2:8][OH:9].F[c:10]1[cH:11][cH:12][c:13]([N+:14](=[O:15])[O-:16])[cH:17][cH:18]1>>[CH3:1][CH2:2][N:3]([CH2:4][CH3:5])[CH2:6][CH2:7][CH2:8][O:9][c:10]1[cH:11][cH:12][c:13]([N+:14](=[O:15])[O-:16])[cH:17][cH:18]1 | CCN(CC)CCCO.O=[N+]([O-])c1ccc(F)cc1 | CCN(CC)CCCOc1ccc([N+](=O)[O-])cc1 | null | null | C1CCOC1 | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 4821d6d7238522ee9ef4538c00647e855becf4de3d9c939c0cec2b01c1e5e915 | a4cafa7bcd156e21cca6eaac1b32e28ec8540642a31181122e6957f3d7559631 | c1ccccc1 | F-[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] | 71.2 | [{"value": 71.0, "product": "C(C)N(CCCOC1=CC=C(C=C1)[N+](=O)[O-])CC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 71.2, "product": "C(C)N(CCCOC1=CC=C(C=C1)[N+](=O)[O-])CC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 5 | MINUTE | A solution of 3-diethylamino-1-propanol (2.97 mL, 20 mmol) in THF (40 mL) at 0° C. is treated potassium tert-butoxide (2.36 g, 1.05 equiv.) in one portion. The reaction mixture is stirred at 0° C. for 5 min during which time it becomes reddish brown. Neat 1-fluoro-4-nitrobenzene (2.82 g, 1 equiv.) is added dropwise and... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary alcohol | Ether | c1ccccc1 | c1ccccc1 | c1ccccc1 | HF | C1CCOC1 | 0 | 0.083333 | CCN(CC)CCCO.O=[N+]([O-])c1ccc(F)cc1>C1CCOC1>CCN(CC)CCCOc1ccc([N+](=O)[O-])cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-4617c2c237a047b3afb73ffa4846eb05 | CCN(CC)CCCOc1ccc([N+](=O)[O-])cc1>>CCN(CC)CCCOc1ccc(N)cc1 | C(C)N(CCCOC1=CC=C(C=C1)[N+](=O)[O-])CC.O.NN>>C(C)N(CCCOC1=CC=C(C=C1)N)CC | O=[N+:14]([O-])[c:13]1[cH:12][cH:11][c:10]([O:9][CH2:8][CH2:7][CH2:6][N:3]([CH2:2][CH3:1])[CH2:4][CH3:5])[cH:16][cH:15]1>>[CH3:1][CH2:2][N:3]([CH2:4][CH3:5])[CH2:6][CH2:7][CH2:8][O:9][c:10]1[cH:11][cH:12][c:13]([NH2:14])[cH:15][cH:16]1 | CCN(CC)CCCOc1ccc([N+](=O)[O-])cc1 | CCN(CC)CCCOc1ccc(N)cc1 | null | [Ni] | C(C)O | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccccc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | 50 | CELSIUS | 3 | HOUR | A solution of diethyl-[3-(4-nitro-phenoxy)-propyl]-amine (15.2 g, 60.4 mmol) is dissolved in absolute ethanol (350 mL) and to this solution is added hydrazine monohydrate (18 mL, 6 equiv.) followed by the addition of a small portion of Raney nickel. The reaction mixture is heated to 50° C. with stirring for 3 h until a... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1 | Other | [Ni].C(C)O | 50 | 3 | CCN(CC)CCCOc1ccc([N+](=O)[O-])cc1>[Ni].C(C)O>CCN(CC)CCCOc1ccc(N)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-7168e53720db4e3aa8848f17266be001 | CCN(CC)CCCOc1ccc(N)cc1.O=C1Nc2ccc(Cl)cc2C1=CO>>CCN(CC)CCCOc1ccc(NC=C2C(=O)Nc3ccc(Cl)cc32)cc1 | C(C)N(CCCOC1=CC=C(C=C1)N)CC.ClC=1C=C2C(C(NC2=CC1)=O)=CO>>ClC=1C=C2C(C(NC2=CC1)=O)=CNC1=CC=C(C=C1)OCCCN(CC)CC | [CH3:1][CH2:2][N:3]([CH2:4][CH3:5])[CH2:6][CH2:7][CH2:8][O:9][c:10]1[cH:11][cH:12][c:13]([NH2:14])[cH:27][cH:28]1.O[CH:15]=[C:16]1[C:17](=[O:18])[NH:19][c:20]2[cH:21][cH:22][c:23]([Cl:24])[cH:25][c:26]21>>[CH3:1][CH2:2][N:3]([CH2:4][CH3:5])[CH2:6][CH2:7][CH2:8][O:9][c:10]1[cH:11][cH:12][c:13]([NH:14][CH:15]=[C:16]2[C:1... | CCN(CC)CCCOc1ccc(N)cc1.O=C1Nc2ccc(Cl)cc2C1=CO | CCN(CC)CCCOc1ccc(NC=C2C(=O)Nc3ccc(Cl)cc32)cc1 | null | null | null | Heteroatom Alkylation and Arylation | Reductive amination with alcohol | ac661a5987df49e763a2386679221354b73376953f4071e32e52e2d7e8877593 | dc27e5e3871ba014ddcdbe66aa8244518b94cc851f1ff4159b6674656bc3b780 | O=C1Nc2ccccc2C1=CNc1ccccc1 | O-[CH;D2;+0:1]=[C:2]1-[c:3]:[c:4]-[#7:5]-[C:6]-1=[O;D1;H0:7].[NH2;D1;+0:8]-[c:9](:[c:10]):[c:11]>>[O;D1;H0:7]=[C:6]1-[#7:5]-[c:4]:[c:3]-[C:2]-1=[CH;D2;+0:1]-[NH;D2;+0:8]-[c:9](:[c:10]):[c:11] | 46 | [{"value": 46.0, "product": "ClC=1C=C2C(C(NC2=CC1)=O)=CNC1=CC=C(C=C1)OCCCN(CC)CC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 45.7, "product": "ClC=1C=C2C(C(NC2=CC1)=O)=CNC1=CC=C(C=C1)OCCCN(CC)CC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | In a manner similar to that described in Example 231, 4-(3-diethylamino-propoxy)-phenylamine (911 mg, 1.3 equiv.) and 5-chloro-3-hydroxymethylene-1,3-dihydro-indol-2-one (617 mg, 3.16 mmol, 1 equiv.) are reacted to give the named compound as a yellow solid (577 mg, 46%).
Conditions: See reaction.notes.procedure_details... | 10.6084/m9.figshare.5104873.v1 | null | Enol.Primary amine | Enamine | null | null | c1ccccc1.c1ccc2c(c1)CCN2 | HO- | null | null | null | CCN(CC)CCCOc1ccc(N)cc1.O=C1Nc2ccc(Cl)cc2C1=CO>>CCN(CC)CCCOc1ccc(NC=C2C(=O)Nc3ccc(Cl)cc32)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-8efe51c5709445b7b864f1173e787e4c | CCN(CC)CCCOc1ccc(N)cc1.O=C1Nc2ccc(F)cc2C1=CO>>CCN(CC)CCCOc1ccc(NC=C2C(=O)Nc3ccc(F)cc32)cc1 | C(C)N(CCCOC1=CC=C(C=C1)N)CC.FC=1C=C2C(C(NC2=CC1)=O)=CO>>C(C)N(CCCOC1=CC=C(C=C1)NC=C1C(NC2=CC=C(C=C12)F)=O)CC | [CH3:1][CH2:2][N:3]([CH2:4][CH3:5])[CH2:6][CH2:7][CH2:8][O:9][c:10]1[cH:11][cH:12][c:13]([NH2:14])[cH:27][cH:28]1.O[CH:15]=[C:16]1[C:17](=[O:18])[NH:19][c:20]2[cH:21][cH:22][c:23]([F:24])[cH:25][c:26]21>>[CH3:1][CH2:2][N:3]([CH2:4][CH3:5])[CH2:6][CH2:7][CH2:8][O:9][c:10]1[cH:11][cH:12][c:13]([NH:14][CH:15]=[C:16]2[C:17... | CCN(CC)CCCOc1ccc(N)cc1.O=C1Nc2ccc(F)cc2C1=CO | CCN(CC)CCCOc1ccc(NC=C2C(=O)Nc3ccc(F)cc32)cc1 | null | null | null | Heteroatom Alkylation and Arylation | Reductive amination with alcohol | ac661a5987df49e763a2386679221354b73376953f4071e32e52e2d7e8877593 | dc27e5e3871ba014ddcdbe66aa8244518b94cc851f1ff4159b6674656bc3b780 | O=C1Nc2ccccc2C1=CNc1ccccc1 | O-[CH;D2;+0:1]=[C:2]1-[c:3]:[c:4]-[#7:5]-[C:6]-1=[O;D1;H0:7].[NH2;D1;+0:8]-[c:9](:[c:10]):[c:11]>>[O;D1;H0:7]=[C:6]1-[#7:5]-[c:4]:[c:3]-[C:2]-1=[CH;D2;+0:1]-[NH;D2;+0:8]-[c:9](:[c:10]):[c:11] | 41 | [{"value": 41.0, "product": "C(C)N(CCCOC1=CC=C(C=C1)NC=C1C(NC2=CC=C(C=C12)F)=O)CC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 41.0, "product": "C(C)N(CCCOC1=CC=C(C=C1)NC=C1C(NC2=CC=C(C=C12)F)=O)CC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | In a manner similar to that described in Example 231, 4-(3-diethylamino-propoxy)-phenylamine (161 mg, 1.3 equiv.) and 5-fluoro-3-hydroxymethylene-1,3-dihydro-indol-2-one (100 mg, 0.56 mmol, 1 equiv.) are reacted to give the named compound as a yellow solid (88 mg, 41%).
Conditions: See reaction.notes.procedure_details.... | 10.6084/m9.figshare.5104873.v1 | null | Enol.Primary amine | Enamine | null | null | c1ccccc1.c1ccc2c(c1)CCN2 | HO- | null | null | null | CCN(CC)CCCOc1ccc(N)cc1.O=C1Nc2ccc(F)cc2C1=CO>>CCN(CC)CCCOc1ccc(NC=C2C(=O)Nc3ccc(F)cc32)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-0b04e4dbf963449c9950d42ba3e15343 | CCN(CC)CCCOc1ccc(N)cc1.O=C1Nc2cc(F)ccc2C1=CO>>CCN(CC)CCCOc1ccc(NC=C2C(=O)Nc3cc(F)ccc32)cc1 | C(C)N(CCCOC1=CC=C(C=C1)N)CC.FC1=CC=C2C(C(NC2=C1)=O)=CO>>C(C)N(CCCOC1=CC=C(C=C1)NC=C1C(NC2=CC(=CC=C12)F)=O)CC | [CH3:1][CH2:2][N:3]([CH2:4][CH3:5])[CH2:6][CH2:7][CH2:8][O:9][c:10]1[cH:11][cH:12][c:13]([NH2:14])[cH:27][cH:28]1.O[CH:15]=[C:16]1[C:17](=[O:18])[NH:19][c:20]2[cH:21][c:22]([F:23])[cH:24][cH:25][c:26]21>>[CH3:1][CH2:2][N:3]([CH2:4][CH3:5])[CH2:6][CH2:7][CH2:8][O:9][c:10]1[cH:11][cH:12][c:13]([NH:14][CH:15]=[C:16]2[C:17... | CCN(CC)CCCOc1ccc(N)cc1.O=C1Nc2cc(F)ccc2C1=CO | CCN(CC)CCCOc1ccc(NC=C2C(=O)Nc3cc(F)ccc32)cc1 | null | null | null | Heteroatom Alkylation and Arylation | Reductive amination with alcohol | ac661a5987df49e763a2386679221354b73376953f4071e32e52e2d7e8877593 | dc27e5e3871ba014ddcdbe66aa8244518b94cc851f1ff4159b6674656bc3b780 | O=C1Nc2ccccc2C1=CNc1ccccc1 | O-[CH;D2;+0:1]=[C:2]1-[c:3]:[c:4]-[#7:5]-[C:6]-1=[O;D1;H0:7].[NH2;D1;+0:8]-[c:9](:[c:10]):[c:11]>>[O;D1;H0:7]=[C:6]1-[#7:5]-[c:4]:[c:3]-[C:2]-1=[CH;D2;+0:1]-[NH;D2;+0:8]-[c:9](:[c:10]):[c:11] | 61.4 | [{"value": 61.0, "product": "C(C)N(CCCOC1=CC=C(C=C1)NC=C1C(NC2=CC(=CC=C12)F)=O)CC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 61.4, "product": "C(C)N(CCCOC1=CC=C(C=C1)NC=C1C(NC2=CC(=CC=C12)F)=O)CC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | In a manner similar to that described in Example 231, 4-(3-diethylamino-propoxy)-phenylamine (5 g, 1.3 equiv.) and 6-fluoro-3-hydroxymethylene-1,3-dihydro-indol-2-one (3.12 g, 17.4 mmol, 1 equiv.) are reacted to give the named compound as a yellow solid (4.1 g, 61%).
Conditions: See reaction.notes.procedure_details.
Wo... | 10.6084/m9.figshare.5104873.v1 | null | Enol.Primary amine | Enamine | null | null | c1ccccc1.c1ccc2c(c1)CCN2 | HO- | null | null | null | CCN(CC)CCCOc1ccc(N)cc1.O=C1Nc2cc(F)ccc2C1=CO>>CCN(CC)CCCOc1ccc(NC=C2C(=O)Nc3cc(F)ccc32)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-e48903f80f9f421c91edcec7605af2eb | NCCN1CCOCC1.O=[N+]([O-])c1ccc(F)cc1>>O=[N+]([O-])c1ccc(NCCN2CCOCC2)cc1 | FC1=CC=C(C=C1)[N+](=O)[O-].N1(CCOCC1)CCN.C(C)(C)NC(C)C>>N1(CCOCC1)CCNC1=CC=C(C=C1)[N+](=O)[O-] | [NH2:8][CH2:9][CH2:10][N:11]1[CH2:12][CH2:13][O:14][CH2:15][CH2:16]1.F[c:7]1[cH:6][cH:5][c:4]([N+:2](=[O:1])[O-:3])[cH:18][cH:17]1>>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][cH:6][c:7]([NH:8][CH2:9][CH2:10][N:11]2[CH2:12][CH2:13][O:14][CH2:15][CH2:16]2)[cH:17][cH:18]1 | NCCN1CCOCC1.O=[N+]([O-])c1ccc(F)cc1 | O=[N+]([O-])c1ccc(NCCN2CCOCC2)cc1 | null | null | ClCCl.O1CCOCC1 | Heteroatom Alkylation and Arylation | Buchwald-Hartwig/Ullmann-Goldberg/N-arylation primary amine | da9dae6a655c4bd18887b692f91621e77027436294d6e1fc7be7295afb364796 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(NCCN2CCOCC2)cc1 | F-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[C:6]-[C:7]-[NH2;D1;+0:8]>>[C:6]-[C:7]-[NH;D2;+0:8]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5] | null | [] | 105 | CELSIUS | null | null | A mixture of 7.5 mL of p-fluoronitrobenzene, 10.25 mL 2-morpholin-4-yl-ethylamine and 15 mL N,N-diisopropylamine in 36 mL dioxane is heated at 105° C. for 2 days. The reaction mixture is cooled to room temperature, diluted with dichloromethane (360 mL) and washed with water (3×290 mL). Upon evaporation to dryness, the ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccccc1 | c1ccccc1 | c1ccccc1.C1COCC[NH]1 | HF | ClCCl.O1CCOCC1 | 105 | null | NCCN1CCOCC1.O=[N+]([O-])c1ccc(F)cc1>ClCCl.O1CCOCC1>O=[N+]([O-])c1ccc(NCCN2CCOCC2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-1b27c4984f864dd2b9902d284580b1e4 | Cc1cccc2c1C(=CO)C(=O)N2.Nc1ccc(OCCCN2CCCCC2)cc1>>Cc1cccc2c1C(=CNc1ccc(OCCCN3CCCCC3)cc1)C(=O)N2 | N1(CCCCC1)CCCOC1=CC=C(C=C1)N.CC1=C2C(C(NC2=CC=C1)=O)=CO>>CC1=C2C(C(NC2=CC=C1)=O)=CNC1=CC=C(C=C1)OCCCN1CCCCC1 | O[CH:9]=[C:8]1[c:7]2[c:2]([CH3:1])[cH:3][cH:4][cH:5][c:6]2[NH:29][C:27]1=[O:28].[NH2:10][c:11]1[cH:12][cH:13][c:14]([O:15][CH2:16][CH2:17][CH2:18][N:19]2[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24]2)[cH:25][cH:26]1>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][c:6]2[c:7]1[C:8](=[CH:9][NH:10][c:11]1[cH:12][cH:13][c:14]([O:15][CH2:16][CH... | Cc1cccc2c1C(=CO)C(=O)N2.Nc1ccc(OCCCN2CCCCC2)cc1 | Cc1cccc2c1C(=CNc1ccc(OCCCN3CCCCC3)cc1)C(=O)N2 | null | null | null | Heteroatom Alkylation and Arylation | Reductive amination with alcohol | ac661a5987df49e763a2386679221354b73376953f4071e32e52e2d7e8877593 | dc27e5e3871ba014ddcdbe66aa8244518b94cc851f1ff4159b6674656bc3b780 | O=C1Nc2ccccc2C1=CNc1ccc(OCCCN2CCCCC2)cc1 | O-[CH;D2;+0:1]=[C:2]1-[c:3]:[c:4]-[#7:5]-[C:6]-1=[O;D1;H0:7].[NH2;D1;+0:8]-[c:9](:[c:10]):[c:11]>>[O;D1;H0:7]=[C:6]1-[#7:5]-[c:4]:[c:3]-[C:2]-1=[CH;D2;+0:1]-[NH;D2;+0:8]-[c:9](:[c:10]):[c:11] | 49.6 | [{"value": 49.0, "product": "CC1=C2C(C(NC2=CC=C1)=O)=CNC1=CC=C(C=C1)OCCCN1CCCCC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 49.6, "product": "CC1=C2C(C(NC2=CC=C1)=O)=CNC1=CC=C(C=C1)OCCCN1CCCCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | In a manner similar to that described in Example 231, 4-(3-Piperidin-1-yl-propoxy)-phenylamine (0.61 g, 1.3 equiv.) and 4-methyl-3-hydroxymethylene-1,3-dihydro-indol-2-one (0.35 g, 2 mmol, 1 equiv.) are reacted to give the named compound as a yellow solid (388 mg, 49%).
Conditions: See reaction.notes.procedure_details.... | 10.6084/m9.figshare.5104873.v1 | null | Enol.Primary amine | Enamine | null | null | c1ccccc1.C1CC[NH]CC1.c1ccc2c(c1)CCN2 | HO- | null | null | null | Cc1cccc2c1C(=CO)C(=O)N2.Nc1ccc(OCCCN2CCCCC2)cc1>>Cc1cccc2c1C(=CNc1ccc(OCCCN3CCCCC3)cc1)C(=O)N2 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-39972d6427cf4e2ea1dd90c91ff689a3 | Nc1ccc(OCCCN2CCCCC2)cc1.O=C1Nc2cc(F)ccc2C1=CO>>O=C1Nc2cc(F)ccc2C1=CNc1ccc(OCCCN2CCCCC2)cc1 | N1(CCCCC1)CCCOC1=CC=C(C=C1)N.FC1=CC=C2C(C(NC2=C1)=O)=CO>>FC1=CC=C2C(C(NC2=C1)=O)=CNC1=CC=C(C=C1)OCCCN1CCCCC1 | [NH2:13][c:14]1[cH:15][cH:16][c:17]([O:18][CH2:19][CH2:20][CH2:21][N:22]2[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27]2)[cH:28][cH:29]1.O[CH:12]=[C:11]1[C:2](=[O:1])[NH:3][c:4]2[cH:5][c:6]([F:7])[cH:8][cH:9][c:10]21>>[O:1]=[C:2]1[NH:3][c:4]2[cH:5][c:6]([F:7])[cH:8][cH:9][c:10]2[C:11]1=[CH:12][NH:13][c:14]1[cH:15][cH:16][c:1... | Nc1ccc(OCCCN2CCCCC2)cc1.O=C1Nc2cc(F)ccc2C1=CO | O=C1Nc2cc(F)ccc2C1=CNc1ccc(OCCCN2CCCCC2)cc1 | null | null | null | Heteroatom Alkylation and Arylation | Reductive amination with alcohol | ac661a5987df49e763a2386679221354b73376953f4071e32e52e2d7e8877593 | dc27e5e3871ba014ddcdbe66aa8244518b94cc851f1ff4159b6674656bc3b780 | O=C1Nc2ccccc2C1=CNc1ccc(OCCCN2CCCCC2)cc1 | O-[CH;D2;+0:1]=[C:2]1-[c:3]:[c:4]-[#7:5]-[C:6]-1=[O;D1;H0:7].[NH2;D1;+0:8]-[c:9](:[c:10]):[c:11]>>[O;D1;H0:7]=[C:6]1-[#7:5]-[c:4]:[c:3]-[C:2]-1=[CH;D2;+0:1]-[NH;D2;+0:8]-[c:9](:[c:10]):[c:11] | 59 | [{"value": 59.0, "product": "FC1=CC=C2C(C(NC2=C1)=O)=CNC1=CC=C(C=C1)OCCCN1CCCCC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 58.8, "product": "FC1=CC=C2C(C(NC2=C1)=O)=CNC1=CC=C(C=C1)OCCCN1CCCCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | In a manner similar to that described in Example 231, 4-(3-Piperidin-1-yl-propoxy)-phenylamine (0.61 g, 1.3 equiv.) and 6-fluoro-3-hydroxymethylene-1,3-dihydro-indol-2-one (0.358 g, 2.00 mmol, 1 equiv.) are reacted to give the named compound as a yellow solid (465 mg, 59%).
Conditions: See reaction.notes.procedure_deta... | 10.6084/m9.figshare.5104873.v1 | null | Enol.Primary amine | Enamine | null | null | c1ccc2c(c1)CCN2.c1ccccc1.C1CC[NH]CC1 | HO- | null | null | null | Nc1ccc(OCCCN2CCCCC2)cc1.O=C1Nc2cc(F)ccc2C1=CO>>O=C1Nc2cc(F)ccc2C1=CNc1ccc(OCCCN2CCCCC2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-36e23053addd4a0a9e9dd0af87d2f080 | Nc1ccc(OCCCN2CCCCC2)cc1.O=C1Nc2ccc(F)cc2C1=CO>>O=C1Nc2ccc(F)cc2C1=CN(c1ccccc1)c1ccc(OCCCN2CCCCC2)cc1 | N1(CCCCC1)CCCOC1=CC=C(C=C1)N.FC=1C=C2C(C(NC2=CC1)=O)=CO>>FC=1C=C2C(C(NC2=CC1)=O)=CN(C1=CC=CC=C1)C1=CC=C(C=C1)OCCCN1CCCCC1 | [NH2:13][c:20]1[cH:21][cH:14][c:23]([O:24][CH2:25][CH2:26][CH2:27][N:28]2[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33]2)[cH:34][cH:35]1.O[CH:12]=[C:11]1[C:2](=[O:1])[NH:3][c:4]2[cH:5][cH:6][c:7]([F:8])[cH:9][c:10]21>>[O:1]=[C:2]1[NH:3][c:4]2[cH:5][cH:6][c:7]([F:8])[cH:9][c:10]2[C:11]1=[CH:12][N:13]([c:14]1[cH:15][cH:16][cH:... | Nc1ccc(OCCCN2CCCCC2)cc1.O=C1Nc2ccc(F)cc2C1=CO | O=C1Nc2ccc(F)cc2C1=CN(c1ccccc1)c1ccc(OCCCN2CCCCC2)cc1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | ee380e69425494e2ad8ce6db49a000daf422649e515e371bb2a3428b8284ddc6 | 75008dcb95ebdefb9ebaaf9dbfbe866fb9b9227bfa04c0e82a556361bbe652e3 | O=C1Nc2ccccc2C1=CN(c1ccccc1)c1ccc(OCCCN2CCCCC2)cc1 | O-[CH;D2;+0:1]=[C:2]1-[c:3]:[c:4]-[#7:5]-[C:6]-1=[O;D1;H0:7].[C:8]-[#8:9]-[c;H0;D3;+0:10]1:[c:11]:[c:12]:[c:13](-[NH2;D1;+0:14]):[cH;D2;+0:15]:[cH;D2;+0:16]:1>>[C:8]-[#8:9]-[c;H0;D3;+0:10]1:[c:17]:[cH;D2;+0:15]:[c:13](-[N;H0;D3;+0:14](-[CH;D2;+0:1]=[C:2]2-[c:3]:[c:4]-[#7:5]-[C:6]-2=[O;D1;H0:7])-[c;H0;D3;+0:16](:[c:18]:... | 66.1 | [{"value": 47.0, "product": "FC=1C=C2C(C(NC2=CC1)=O)=CN(C1=CC=CC=C1)C1=CC=C(C=C1)OCCCN1CCCCC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 66.1, "product": "FC=1C=C2C(C(NC2=CC1)=O)=CN(C1=CC=CC=C1)C1=CC=C(C=C1)OCCCN1CCCCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | In a manner similar to that described in Example 231, 4-(3-piperidin-1-yl-propoxy)-phenylamine (0.57 g, 1.3 equiv.) and 5-fluoro-3-hydroxymethylene-1,3-dihydro-indol-2-one (0.363 g, 2 mmol, 1 equiv.) are reacted to give the named compound as a yellow solid (379 mg, 47%).
Conditions: See reaction.notes.procedure_details... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Enol.Primary amine | Enamine.Ether | c1ccccc1 | c1ccccc1.c1ccccc1 | c1ccc2c(c1)CCN2.c1ccccc1.c1ccccc1.C1CC[NH]CC1 | null | null | null | null | Nc1ccc(OCCCN2CCCCC2)cc1.O=C1Nc2ccc(F)cc2C1=CO>>O=C1Nc2ccc(F)cc2C1=CN(c1ccccc1)c1ccc(OCCCN2CCCCC2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-59c1782dce1341d2b9b6b447e36aac0d | Nc1ccc(OCCCN2CCCCC2)cc1.O=C1Nc2ccc(Cl)cc2C1=CO>>O=C1Nc2ccc(Cl)cc2C1=CNc1ccc(OCCCN2CCCCC2)cc1 | N1(CCCCC1)CCCOC1=CC=C(C=C1)N.ClC=1C=C2C(C(NC2=CC1)=O)=CO>>ClC=1C=C2C(C(NC2=CC1)=O)=CNC1=CC=C(C=C1)OCCCN1CCCCC1 | [NH2:13][c:14]1[cH:15][cH:16][c:17]([O:18][CH2:19][CH2:20][CH2:21][N:22]2[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27]2)[cH:28][cH:29]1.O[CH:12]=[C:11]1[C:2](=[O:1])[NH:3][c:4]2[cH:5][cH:6][c:7]([Cl:8])[cH:9][c:10]21>>[O:1]=[C:2]1[NH:3][c:4]2[cH:5][cH:6][c:7]([Cl:8])[cH:9][c:10]2[C:11]1=[CH:12][NH:13][c:14]1[cH:15][cH:16][c... | Nc1ccc(OCCCN2CCCCC2)cc1.O=C1Nc2ccc(Cl)cc2C1=CO | O=C1Nc2ccc(Cl)cc2C1=CNc1ccc(OCCCN2CCCCC2)cc1 | null | null | null | Heteroatom Alkylation and Arylation | Reductive amination with alcohol | ac661a5987df49e763a2386679221354b73376953f4071e32e52e2d7e8877593 | dc27e5e3871ba014ddcdbe66aa8244518b94cc851f1ff4159b6674656bc3b780 | O=C1Nc2ccccc2C1=CNc1ccc(OCCCN2CCCCC2)cc1 | O-[CH;D2;+0:1]=[C:2]1-[c:3]:[c:4]-[#7:5]-[C:6]-1=[O;D1;H0:7].[NH2;D1;+0:8]-[c:9](:[c:10]):[c:11]>>[O;D1;H0:7]=[C:6]1-[#7:5]-[c:4]:[c:3]-[C:2]-1=[CH;D2;+0:1]-[NH;D2;+0:8]-[c:9](:[c:10]):[c:11] | 58 | [{"value": 58.0, "product": "ClC=1C=C2C(C(NC2=CC1)=O)=CNC1=CC=C(C=C1)OCCCN1CCCCC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 56.3, "product": "ClC=1C=C2C(C(NC2=CC1)=O)=CNC1=CC=C(C=C1)OCCCN1CCCCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | In a manner similar to that described in Example 231, 4-(3-piperidin-1-yl-propoxy)-phenylamine (550 mg, 1.3 equiv.) and 5-chloro-3-hydroxymethylene-1,3-dihydro-indol-2-one (380 mg, 2.00 mmol, 1 equiv.) are reacted to give the named compound as a yellow solid (464 mg, 58%).
Conditions: See reaction.notes.procedure_detai... | 10.6084/m9.figshare.5104873.v1 | null | Enol.Primary amine | Enamine | null | null | c1ccc2c(c1)CCN2.c1ccccc1.C1CC[NH]CC1 | HO- | null | null | null | Nc1ccc(OCCCN2CCCCC2)cc1.O=C1Nc2ccc(Cl)cc2C1=CO>>O=C1Nc2ccc(Cl)cc2C1=CNc1ccc(OCCCN2CCCCC2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-85af3b0df0924a6f8cf6ee4342847a42 | Cc1cccc2c1C(=CO)C(=O)N2.Nc1ccc(OCCCCN2CCCCC2)cc1>>Cc1cccc2c1C(=CNc1ccc(OCCCCN3CCCCC3)cc1)C(=O)N2 | N1(CCCCC1)CCCCOC1=CC=C(C=C1)N.CC1=C2C(C(NC2=CC=C1)=O)=CO>>CC1=C2C(C(NC2=CC=C1)=O)=CNC1=CC=C(C=C1)OCCCCN1CCCCC1 | O[CH:9]=[C:8]1[c:7]2[c:2]([CH3:1])[cH:3][cH:4][cH:5][c:6]2[NH:30][C:28]1=[O:29].[NH2:10][c:11]1[cH:12][cH:13][c:14]([O:15][CH2:16][CH2:17][CH2:18][CH2:19][N:20]2[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25]2)[cH:26][cH:27]1>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][c:6]2[c:7]1[C:8](=[CH:9][NH:10][c:11]1[cH:12][cH:13][c:14]([O:15][CH... | Cc1cccc2c1C(=CO)C(=O)N2.Nc1ccc(OCCCCN2CCCCC2)cc1 | Cc1cccc2c1C(=CNc1ccc(OCCCCN3CCCCC3)cc1)C(=O)N2 | null | null | null | Heteroatom Alkylation and Arylation | Reductive amination with alcohol | ac661a5987df49e763a2386679221354b73376953f4071e32e52e2d7e8877593 | dc27e5e3871ba014ddcdbe66aa8244518b94cc851f1ff4159b6674656bc3b780 | O=C1Nc2ccccc2C1=CNc1ccc(OCCCCN2CCCCC2)cc1 | O-[CH;D2;+0:1]=[C:2]1-[c:3]:[c:4]-[#7:5]-[C:6]-1=[O;D1;H0:7].[NH2;D1;+0:8]-[c:9](:[c:10]):[c:11]>>[O;D1;H0:7]=[C:6]1-[#7:5]-[c:4]:[c:3]-[C:2]-1=[CH;D2;+0:1]-[NH;D2;+0:8]-[c:9](:[c:10]):[c:11] | 53.2 | [{"value": 53.0, "product": "CC1=C2C(C(NC2=CC=C1)=O)=CNC1=CC=C(C=C1)OCCCCN1CCCCC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 53.2, "product": "CC1=C2C(C(NC2=CC=C1)=O)=CNC1=CC=C(C=C1)OCCCCN1CCCCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | In a manner similar to that described in Example 231, 4-(4-Piperidin-1-yl-butoxy)-phenylamine (1.19 g, 1.1 equiv.) and 4-methyl-3-hydroxymethylene-1,3-dihydro-indol-2-one (0.79 g, 4.5 mmol, 1 equiv.) are reacted to give the named compound as a yellow solid (0.97 g, 53%).
Conditions: See reaction.notes.procedure_details... | 10.6084/m9.figshare.5104873.v1 | null | Enol.Primary amine | Enamine | null | null | c1ccccc1.C1CC[NH]CC1.c1ccc2c(c1)CCN2 | HO- | null | null | null | Cc1cccc2c1C(=CO)C(=O)N2.Nc1ccc(OCCCCN2CCCCC2)cc1>>Cc1cccc2c1C(=CNc1ccc(OCCCCN3CCCCC3)cc1)C(=O)N2 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-bd36ddb1ba5c4fc28ef4bc92558c279d | Nc1ccc(OCCCCN2CCCCC2)cc1.O=C1Nc2cc(F)ccc2C1=CO>>O=C1Nc2cc(F)ccc2C1=CNc1ccc(OCCCCN2CCCCC2)cc1 | N1(CCCCC1)CCCCOC1=CC=C(C=C1)N.FC1=CC=C2C(C(NC2=C1)=O)=CO>>FC1=CC=C2C(C(NC2=C1)=O)=CNC1=CC=C(C=C1)OCCCCN1CCCCC1 | [NH2:13][c:14]1[cH:15][cH:16][c:17]([O:18][CH2:19][CH2:20][CH2:21][CH2:22][N:23]2[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28]2)[cH:29][cH:30]1.O[CH:12]=[C:11]1[C:2](=[O:1])[NH:3][c:4]2[cH:5][c:6]([F:7])[cH:8][cH:9][c:10]21>>[O:1]=[C:2]1[NH:3][c:4]2[cH:5][c:6]([F:7])[cH:8][cH:9][c:10]2[C:11]1=[CH:12][NH:13][c:14]1[cH:15][cH... | Nc1ccc(OCCCCN2CCCCC2)cc1.O=C1Nc2cc(F)ccc2C1=CO | O=C1Nc2cc(F)ccc2C1=CNc1ccc(OCCCCN2CCCCC2)cc1 | null | null | null | Heteroatom Alkylation and Arylation | Reductive amination with alcohol | ac661a5987df49e763a2386679221354b73376953f4071e32e52e2d7e8877593 | dc27e5e3871ba014ddcdbe66aa8244518b94cc851f1ff4159b6674656bc3b780 | O=C1Nc2ccccc2C1=CNc1ccc(OCCCCN2CCCCC2)cc1 | O-[CH;D2;+0:1]=[C:2]1-[c:3]:[c:4]-[#7:5]-[C:6]-1=[O;D1;H0:7].[NH2;D1;+0:8]-[c:9](:[c:10]):[c:11]>>[O;D1;H0:7]=[C:6]1-[#7:5]-[c:4]:[c:3]-[C:2]-1=[CH;D2;+0:1]-[NH;D2;+0:8]-[c:9](:[c:10]):[c:11] | 73 | [{"value": 73.0, "product": "FC1=CC=C2C(C(NC2=C1)=O)=CNC1=CC=C(C=C1)OCCCCN1CCCCC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 72.3, "product": "FC1=CC=C2C(C(NC2=C1)=O)=CNC1=CC=C(C=C1)OCCCCN1CCCCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | In a manner similar to that described in Example 231, 4-(4-piperidin-1-yl-butoxy)-phenylamine (400 mg, 1.1 equiv.) and 6-fluoro-3-hydroxymethylene-1,3-dihydro-indol-2-one (263 mg, 1.47 mmol, 1 equiv.) are reacted to give the named compound as a yellow solid (435 mg, 73%).
Conditions: See reaction.notes.procedure_detail... | 10.6084/m9.figshare.5104873.v1 | null | Enol.Primary amine | Enamine | null | null | c1ccc2c(c1)CCN2.c1ccccc1.C1CC[NH]CC1 | HO- | null | null | null | Nc1ccc(OCCCCN2CCCCC2)cc1.O=C1Nc2cc(F)ccc2C1=CO>>O=C1Nc2cc(F)ccc2C1=CNc1ccc(OCCCCN2CCCCC2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-917046f5e1ea4624a55632873b38e4e0 | CCN(CC)CCCOc1ccc(N)cc1F.O=C1Nc2ccccc2C1=CO>>CCN(CC)CCCOc1ccc(NC=C2C(=O)Nc3ccccc32)cc1F | C(C)N(CCCOC1=C(C=C(C=C1)N)F)CC.OC=C1C(NC2=CC=CC=C12)=O>>C(C)N(CCCOC1=C(C=C(C=C1)NC=C1C(NC2=CC=CC=C12)=O)F)CC | [CH3:1][CH2:2][N:3]([CH2:4][CH3:5])[CH2:6][CH2:7][CH2:8][O:9][c:10]1[cH:11][cH:12][c:13]([NH2:14])[cH:26][c:27]1[F:28].O[CH:15]=[C:16]1[C:17](=[O:18])[NH:19][c:20]2[cH:21][cH:22][cH:23][cH:24][c:25]21>>[CH3:1][CH2:2][N:3]([CH2:4][CH3:5])[CH2:6][CH2:7][CH2:8][O:9][c:10]1[cH:11][cH:12][c:13]([NH:14][CH:15]=[C:16]2[C:17](... | CCN(CC)CCCOc1ccc(N)cc1F.O=C1Nc2ccccc2C1=CO | CCN(CC)CCCOc1ccc(NC=C2C(=O)Nc3ccccc32)cc1F | null | null | null | Heteroatom Alkylation and Arylation | Reductive amination with alcohol | ac661a5987df49e763a2386679221354b73376953f4071e32e52e2d7e8877593 | dc27e5e3871ba014ddcdbe66aa8244518b94cc851f1ff4159b6674656bc3b780 | O=C1Nc2ccccc2C1=CNc1ccccc1 | O-[CH;D2;+0:1]=[C:2]1-[c:3]:[c:4]-[#7:5]-[C:6]-1=[O;D1;H0:7].[NH2;D1;+0:8]-[c:9](:[c:10]):[c:11]>>[O;D1;H0:7]=[C:6]1-[#7:5]-[c:4]:[c:3]-[C:2]-1=[CH;D2;+0:1]-[NH;D2;+0:8]-[c:9](:[c:10]):[c:11] | 24 | [{"value": 24.0, "product": "C(C)N(CCCOC1=C(C=C(C=C1)NC=C1C(NC2=CC=CC=C12)=O)F)CC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 23.5, "product": "C(C)N(CCCOC1=C(C=C(C=C1)NC=C1C(NC2=CC=CC=C12)=O)F)CC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | In a manner similar to that described in Example 231, 4-(3-Diethylamino-propoxy)-3-fluoro-phenylamine (400 mg, 1.1 equiv.) and 3-hydroxymethylene-1,3-dihydro-indol-2-one (242 mg, 1.5 mmol, 1 equiv.) are reacted to give the named compound as a yellow solid (135 mg, 24%).
Conditions: See reaction.notes.procedure_details.... | 10.6084/m9.figshare.5104873.v1 | null | Enol.Primary amine | Enamine | null | null | c1ccccc1.c1ccc2c(c1)CCN2 | HO- | null | null | null | CCN(CC)CCCOc1ccc(N)cc1F.O=C1Nc2ccccc2C1=CO>>CCN(CC)CCCOc1ccc(NC=C2C(=O)Nc3ccccc32)cc1F |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-56b3fcc70da64331a887512e770547de | CCN(CC)CCCO.O=[N+]([O-])c1ccc(F)c(F)c1>>CCN(CC)CCCOc1ccc([N+](=O)[O-])cc1F | FC=1C=C(C=CC1F)[N+](=O)[O-].C(C)N(CCCO)CC>>C(C)N(CCCOC1=C(C=C(C=C1)[N+](=O)[O-])F)CC | [CH3:1][CH2:2][N:3]([CH2:4][CH3:5])[CH2:6][CH2:7][CH2:8][OH:9].F[c:10]1[cH:11][cH:12][c:13]([N+:14](=[O:15])[O-:16])[cH:17][c:18]1[F:19]>>[CH3:1][CH2:2][N:3]([CH2:4][CH3:5])[CH2:6][CH2:7][CH2:8][O:9][c:10]1[cH:11][cH:12][c:13]([N+:14](=[O:15])[O-:16])[cH:17][c:18]1[F:19] | CCN(CC)CCCO.O=[N+]([O-])c1ccc(F)c(F)c1 | CCN(CC)CCCOc1ccc([N+](=O)[O-])cc1F | null | null | null | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 4821d6d7238522ee9ef4538c00647e855becf4de3d9c939c0cec2b01c1e5e915 | a4cafa7bcd156e21cca6eaac1b32e28ec8540642a31181122e6957f3d7559631 | c1ccccc1 | F-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[F;D1;H0:5]):[c:6].[C:7]-[C:8]-[OH;D1;+0:9]>>[C:7]-[C:8]-[O;H0;D2;+0:9]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[F;D1;H0:5]):[c:6] | null | [] | null | null | null | null | In a manner similar to that described in Example 231a, 3,4-difluoronitrobenzene (6.7 mL, 60.6 mmol, 1 equiv.) and 3-diethylamino-1-propanol (9 mL, 1 equiv.) are converted to the named compound as a brown oil (16.3 g).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary alcohol | Ether | c1ccccc1 | c1ccccc1 | c1ccccc1 | HF | null | null | null | CCN(CC)CCCO.O=[N+]([O-])c1ccc(F)c(F)c1>>CCN(CC)CCCOc1ccc([N+](=O)[O-])cc1F |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-978f02367a434d51be57306a9935f100 | CCN(CC)CCCOc1ccc(N)cc1F.Cc1cccc2c1C(=CO)C(=O)N2>>CCN(CC)CCCOc1ccc(NC=C2C(=O)Nc3cccc(C)c32)cc1F | C(C)N(CCCOC1=C(C=C(C=C1)N)F)CC.CC1=C2C(C(NC2=CC=C1)=O)=CO>>C(C)N(CCCOC1=C(C=C(C=C1)NC=C1C(NC2=CC=CC(=C12)C)=O)F)CC | [CH3:1][CH2:2][N:3]([CH2:4][CH3:5])[CH2:6][CH2:7][CH2:8][O:9][c:10]1[cH:11][cH:12][c:13]([NH2:14])[cH:27][c:28]1[F:29].O[CH:15]=[C:16]1[C:17](=[O:18])[NH:19][c:20]2[cH:21][cH:22][cH:23][c:24]([CH3:25])[c:26]21>>[CH3:1][CH2:2][N:3]([CH2:4][CH3:5])[CH2:6][CH2:7][CH2:8][O:9][c:10]1[cH:11][cH:12][c:13]([NH:14][CH:15]=[C:16... | CCN(CC)CCCOc1ccc(N)cc1F.Cc1cccc2c1C(=CO)C(=O)N2 | CCN(CC)CCCOc1ccc(NC=C2C(=O)Nc3cccc(C)c32)cc1F | null | null | null | Heteroatom Alkylation and Arylation | Reductive amination with alcohol | ac661a5987df49e763a2386679221354b73376953f4071e32e52e2d7e8877593 | dc27e5e3871ba014ddcdbe66aa8244518b94cc851f1ff4159b6674656bc3b780 | O=C1Nc2ccccc2C1=CNc1ccccc1 | O-[CH;D2;+0:1]=[C:2]1-[c:3]:[c:4]-[#7:5]-[C:6]-1=[O;D1;H0:7].[NH2;D1;+0:8]-[c:9](:[c:10]):[c:11]>>[O;D1;H0:7]=[C:6]1-[#7:5]-[c:4]:[c:3]-[C:2]-1=[CH;D2;+0:1]-[NH;D2;+0:8]-[c:9](:[c:10]):[c:11] | 49.3 | [{"value": 49.0, "product": "C(C)N(CCCOC1=C(C=C(C=C1)NC=C1C(NC2=CC=CC(=C12)C)=O)F)CC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 49.3, "product": "C(C)N(CCCOC1=C(C=C(C=C1)NC=C1C(NC2=CC=CC(=C12)C)=O)F)CC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | In a manner similar to that described in Example 231, 4-(3-diethylamino-propoxy)-3-fluoro-phenylamine (400 mg, 1.1 equiv.) and 4-methyl-3-hydroxymethylene-1,3-dihydro-indol-2-one (263 mg, 1.5 mmol, 1 equiv.) are reacted to give the named compound as a yellow solid (294 mg, 49%).
Conditions: See reaction.notes.procedure... | 10.6084/m9.figshare.5104873.v1 | null | Enol.Primary amine | Enamine | null | null | c1ccccc1.c1ccc2c(c1)CCN2 | HO- | null | null | null | CCN(CC)CCCOc1ccc(N)cc1F.Cc1cccc2c1C(=CO)C(=O)N2>>CCN(CC)CCCOc1ccc(NC=C2C(=O)Nc3cccc(C)c32)cc1F |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-13194c9eb6f14dfab646843313ca3dbe | CCN(CC)CCCOc1ccc(N)cc1F.O=C1Nc2cc(F)ccc2C1=CO>>CCN(CC)CCCOc1ccc(NC=C2C(=O)Nc3cc(F)ccc32)cc1F | C(C)N(CCCOC1=C(C=C(C=C1)N)F)CC.FC1=CC=C2C(C(NC2=C1)=O)=CO>>C(C)N(CCCOC1=C(C=C(C=C1)NC=C1C(NC2=CC(=CC=C12)F)=O)F)CC | [CH3:1][CH2:2][N:3]([CH2:4][CH3:5])[CH2:6][CH2:7][CH2:8][O:9][c:10]1[cH:11][cH:12][c:13]([NH2:14])[cH:27][c:28]1[F:29].O[CH:15]=[C:16]1[C:17](=[O:18])[NH:19][c:20]2[cH:21][c:22]([F:23])[cH:24][cH:25][c:26]21>>[CH3:1][CH2:2][N:3]([CH2:4][CH3:5])[CH2:6][CH2:7][CH2:8][O:9][c:10]1[cH:11][cH:12][c:13]([NH:14][CH:15]=[C:16]2... | CCN(CC)CCCOc1ccc(N)cc1F.O=C1Nc2cc(F)ccc2C1=CO | CCN(CC)CCCOc1ccc(NC=C2C(=O)Nc3cc(F)ccc32)cc1F | null | null | null | Heteroatom Alkylation and Arylation | Reductive amination with alcohol | ac661a5987df49e763a2386679221354b73376953f4071e32e52e2d7e8877593 | dc27e5e3871ba014ddcdbe66aa8244518b94cc851f1ff4159b6674656bc3b780 | O=C1Nc2ccccc2C1=CNc1ccccc1 | O-[CH;D2;+0:1]=[C:2]1-[c:3]:[c:4]-[#7:5]-[C:6]-1=[O;D1;H0:7].[NH2;D1;+0:8]-[c:9](:[c:10]):[c:11]>>[O;D1;H0:7]=[C:6]1-[#7:5]-[c:4]:[c:3]-[C:2]-1=[CH;D2;+0:1]-[NH;D2;+0:8]-[c:9](:[c:10]):[c:11] | 32.4 | [{"value": 32.0, "product": "C(C)N(CCCOC1=C(C=C(C=C1)NC=C1C(NC2=CC(=CC=C12)F)=O)F)CC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 32.4, "product": "C(C)N(CCCOC1=C(C=C(C=C1)NC=C1C(NC2=CC(=CC=C12)F)=O)F)CC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | In a manner similar to that described in Example 231, 4-(3-diethylamino-propoxy)-3-fluoro-phenylamine (400 mg, 1.1 equiv.) and 6-fluoro-3-hydroxymethylene-1,3-dihydro-indol-2-one (269 mg, 1.5 mmol, 1 equiv.) are reacted to give the named compound as a yellow solid (195 mg, 32%).
Conditions: See reaction.notes.procedure... | 10.6084/m9.figshare.5104873.v1 | null | Enol.Primary amine | Enamine | null | null | c1ccccc1.c1ccc2c(c1)CCN2 | HO- | null | null | null | CCN(CC)CCCOc1ccc(N)cc1F.O=C1Nc2cc(F)ccc2C1=CO>>CCN(CC)CCCOc1ccc(NC=C2C(=O)Nc3cc(F)ccc32)cc1F |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-9eb33a487b964fc5a945498871875f25 | C1CCNCC1.O=C(O)c1ccc([N+](=O)[O-])cc1>>O=C(c1ccc([N+](=O)[O-])cc1)N1CCCCC1 | C([O-])(O)=O.[Na+].[N+](=O)([O-])C1=CC=C(C(=O)O)C=C1.N1CCCCC1>>[N+](=O)([O-])C1=CC=C(C(=O)N2CCCCC2)C=C1 | [NH:12]1[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]1.O[C:2](=[O:1])[c:3]1[cH:4][cH:5][c:6]([N+:7](=[O:8])[O-:9])[cH:10][cH:11]1>>[O:1]=[C:2]([c:3]1[cH:4][cH:5][c:6]([N+:7](=[O:8])[O-:9])[cH:10][cH:11]1)[N:12]1[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]1 | C1CCNCC1.O=C(O)c1ccc([N+](=O)[O-])cc1 | O=C(c1ccc([N+](=O)[O-])cc1)N1CCCCC1 | null | null | O1CCCC1 | Acylation | Acylation of Nitrogen Nucleophiles by Carboxylic Acids | fbfce93ec1ece674255bb96c5cec09ad611382b41cf117dfe580015e21744a71 | c5e4172490b2731ba9322b68af56376edadc31ce0bb9a3dfdea23a1817a852fd | O=C(c1ccccc1)N1CCCCC1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[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](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5])-[C:9]-[C:10] | null | [] | null | null | null | null | A room temperature solution of 5.04 gms. 4-nitro-benzoic acid in tetrahydrofuran (10 mL) is treated with 5.14 gms. 1′,1′-carbonyl-diimidizole and immediately immersed in an ice bath. The reaction mixture is stirred in the ice bath for 30 minutes, then it is allowed to warm to room temperature. Once at room temperature ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | Tertiary amide | C1CCNCC1 | C1CC[NH]CC1 | c1ccccc1.C1CC[NH]CC1 | HO- | O1CCCC1 | null | null | C1CCNCC1.O=C(O)c1ccc([N+](=O)[O-])cc1>O1CCCC1>O=C(c1ccc([N+](=O)[O-])cc1)N1CCCCC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-84c0540ea44042d38bfeda88949d5104 | O=C(c1ccc([N+](=O)[O-])cc1)N1CCCCC1>>O=[N+]([O-])c1ccc(CN2CCCCC2)cc1 | B.O1CCCC1.[N+](=O)([O-])C1=CC=C(C(=O)N2CCCCC2)C=C1.B>>[N+](=O)([O-])C1=CC=C(CN2CCCCC2)C=C1 | O=[C:8]([c:7]1[cH:6][cH:5][c:4]([N+:2](=[O:1])[O-:3])[cH:16][cH:15]1)[N:9]1[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14]1>>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][cH:6][c:7]([CH2:8][N:9]2[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14]2)[cH:15][cH:16]1 | O=C(c1ccc([N+](=O)[O-])cc1)N1CCCCC1 | O=[N+]([O-])c1ccc(CN2CCCCC2)cc1 | null | null | O1CCCC1 | Reduction | Reduction of tertiary amides to amines | f74c5a050b269ec4da3871c266f01344b7447381f47cda744f8b1e9c225ae62d | c8f3c617792f7a4fae96b8a97dc0ce23461ab85d8a738fe6caacff776ef51ffa | c1ccc(CN2CCCCC2)cc1 | O=[C;H0;D3;+0:1](-[#7:2](-[C:3])-[C:4])-[c:5](:[c:6]):[c:7]>>[C:3]-[#7:2](-[CH2;D2;+0:1]-[c:5](:[c:6]):[c:7])-[C:4] | 87 | [{"value": 87.0, "product": "[N+](=O)([O-])C1=CC=C(CN2CCCCC2)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | null | null | 1-(4-Nitrobenzoyl)piperidine (0.1125 gms.) is then dissolved in tetrahydrofuran (1 mL) and slowly added dropwise to a 0° C., 1.0 M solution (4 mL) of Borane in tetrahydrofuran. The reaction mixture is maintained at 0° C. for 20 minutes following the completion of the addition to the Borane/tetrahydrofuran solution. The... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide | null | null | null | c1ccccc1.C1CC[NH]CC1 | Other | O1CCCC1 | 0 | null | O=C(c1ccc([N+](=O)[O-])cc1)N1CCCCC1>O1CCCC1>O=[N+]([O-])c1ccc(CN2CCCCC2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-1439421f0cf641689aef96f1a9448bf3 | CC(=O)O.O=[N+]([O-])c1ccc(CN2CCCCC2)cc1.c1ccc(NCN2CCCCC2)cc1>>O=C1Nc2ccccc2C1=CNc1ccc(CN2CCCCC2)cc1 | [N+](=O)([O-])C1=CC=C(CN2CCCCC2)C=C1.Cl.[OH-].[Na+].N1(CCCCC1)CNC1=CC=CC=C1.C(C)(=O)O>>N1(CCCCC1)CC1=CC=C(C=C1)NC=C1C(NC2=CC=CC=C12)=O | O[C:2](=[O:1])[CH3:10].O=[N+:3]([O-])[c:13]1[cH:14][cH:15][c:16]([CH2:17][N:18]2[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23]2)[cH:24][cH:25]1.C1CCN([CH2:11][NH:12][c:4]2[cH:5][cH:6][cH:7][cH:8][cH:9]2)CC1>>[O:1]=[C:2]1[NH:3][c:4]2[cH:5][cH:6][cH:7][cH:8][c:9]2[C:10]1=[CH:11][NH:12][c:13]1[cH:14][cH:15][c:16]([CH2:17][N:18]... | CC(=O)O.O=[N+]([O-])c1ccc(CN2CCCCC2)cc1.c1ccc(NCN2CCCCC2)cc1 | O=C1Nc2ccccc2C1=CNc1ccc(CN2CCCCC2)cc1 | null | null | O | Acylation | OtherReaction | 81911f8886c3f4fed197597da722c901ab7efcd5b3d7eea80b238777fcb17a61 | 2a4ee568c5349d39f928818528236a391eed962a025d9cf847245c085e3a88ee | O=C1Nc2ccccc2C1=CNc1ccc(CN2CCCCC2)cc1 | C1-C-C-N(-[CH2;D2;+0:1]-[NH;D2;+0:2]-[c;H0;D3;+0:3]2:[c:4]:[c:5]:[c:6]:[c:7]:[cH;D2;+0:8]:2)-C-C-1.O-[C;H0;D3;+0:9](-[CH3;D1;+0:10])=[O;D1;H0:11].O=[N+;H0;D3:12](-[O-])-[c;H0;D3;+0:13](:[c:14]:[c:15]):[c:16]:[c:17]>>[O;D1;H0:11]=[C;H0;D3;+0:9]1-[NH;D2;+0:12]-[c;H0;D3;+0:3]2:[c:4]:[c:5]:[c:6]:[c:7]:[c;H0;D3;+0:8]:2-[C;H... | null | [] | null | null | null | null | 1-(4-Nitro-benzyl)-piperidine (0.5052 gms.) is suspended in 25 mL of a 1:1 (v:v) solution of acetic acid and water. The suspension is then treated with 45 mL of an ˜10 wt. % solution of TiCl3 in 20–30 wt. % HCl, dropwise. Over the course of the addition a color change from colorless to purple to black ensues. The react... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Nitro group.Secondary amine.Tertiary amine | Enamine.Secondary amide | c1ccccc1.C1CCNCC1.c1ccccc1 | c1ccc2c(c1)CCN2.c1ccccc1 | c1ccc2c(c1)CCN2.c1ccccc1.C1CC[NH]CC1 | HO- | O | null | null | CC(=O)O.O=[N+]([O-])c1ccc(CN2CCCCC2)cc1.c1ccc(NCN2CCCCC2)cc1>O>O=C1Nc2ccccc2C1=CNc1ccc(CN2CCCCC2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-8874118d27aa44d7b91f1495e05dff77 | Cc1cccc2c1C(=CO)C(=O)N2.Nc1ccc(OCCN2CCCCC2)cc1>>Cc1cccc2c1C(=CNc1ccc(OCCN3CCCCC3)cc1)C(=O)N2 | N1(CCCCC1)CCOC1=CC=C(C=C1)N.CC1=C2C(C(NC2=CC=C1)=O)=CO>>CC1=C2C(C(NC2=CC=C1)=O)=CNC1=CC=C(C=C1)OCCN1CCCCC1 | O[CH:9]=[C:8]1[c:7]2[c:2]([CH3:1])[cH:3][cH:4][cH:5][c:6]2[NH:28][C:26]1=[O:27].[NH2:10][c:11]1[cH:12][cH:13][c:14]([O:15][CH2:16][CH2:17][N:18]2[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23]2)[cH:24][cH:25]1>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][c:6]2[c:7]1[C:8](=[CH:9][NH:10][c:11]1[cH:12][cH:13][c:14]([O:15][CH2:16][CH2:17][N:... | Cc1cccc2c1C(=CO)C(=O)N2.Nc1ccc(OCCN2CCCCC2)cc1 | Cc1cccc2c1C(=CNc1ccc(OCCN3CCCCC3)cc1)C(=O)N2 | null | null | null | Heteroatom Alkylation and Arylation | Reductive amination with alcohol | ac661a5987df49e763a2386679221354b73376953f4071e32e52e2d7e8877593 | dc27e5e3871ba014ddcdbe66aa8244518b94cc851f1ff4159b6674656bc3b780 | O=C1Nc2ccccc2C1=CNc1ccc(OCCN2CCCCC2)cc1 | O-[CH;D2;+0:1]=[C:2]1-[c:3]:[c:4]-[#7:5]-[C:6]-1=[O;D1;H0:7].[NH2;D1;+0:8]-[c:9](:[c:10]):[c:11]>>[O;D1;H0:7]=[C:6]1-[#7:5]-[c:4]:[c:3]-[C:2]-1=[CH;D2;+0:1]-[NH;D2;+0:8]-[c:9](:[c:10]):[c:11] | 49.1 | [{"value": 49.0, "product": "CC1=C2C(C(NC2=CC=C1)=O)=CNC1=CC=C(C=C1)OCCN1CCCCC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 49.1, "product": "CC1=C2C(C(NC2=CC=C1)=O)=CNC1=CC=C(C=C1)OCCN1CCCCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | In a manner similar to that described in Example 231, 4-(2-piperidin-1-yl-ethoxy)-phenylamine (754 mg, 1.2 equiv.) and 4-methyl-3-hydroxymethylene-1,3-dihydro-indol-2-one (500 mg, 2.86 mmol, 1 equiv.) are reacted to give the named compound as a yellow solid (530 mg, 49%).
Conditions: See reaction.notes.procedure_detail... | 10.6084/m9.figshare.5104873.v1 | null | Enol.Primary amine | Enamine | null | null | c1ccccc1.C1CC[NH]CC1.c1ccc2c(c1)CCN2 | HO- | null | null | null | Cc1cccc2c1C(=CO)C(=O)N2.Nc1ccc(OCCN2CCCCC2)cc1>>Cc1cccc2c1C(=CNc1ccc(OCCN3CCCCC3)cc1)C(=O)N2 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-2c1dfd4b31064722a1df6681b995593f | Nc1ccc(OCCN2CCCCC2)cc1.O=C1Nc2cc(F)ccc2C1=CO>>O=C1Nc2cc(F)ccc2C1=CNc1ccc(OCCN2CCCCC2)cc1 | N1(CCCCC1)CCOC1=CC=C(C=C1)N.FC1=CC=C2C(C(NC2=C1)=O)=CO>>FC1=CC=C2C(C(NC2=C1)=O)=CNC1=CC=C(C=C1)OCCN1CCCCC1 | [NH2:13][c:14]1[cH:15][cH:16][c:17]([O:18][CH2:19][CH2:20][N:21]2[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26]2)[cH:27][cH:28]1.O[CH:12]=[C:11]1[C:2](=[O:1])[NH:3][c:4]2[cH:5][c:6]([F:7])[cH:8][cH:9][c:10]21>>[O:1]=[C:2]1[NH:3][c:4]2[cH:5][c:6]([F:7])[cH:8][cH:9][c:10]2[C:11]1=[CH:12][NH:13][c:14]1[cH:15][cH:16][c:17]([O:18... | Nc1ccc(OCCN2CCCCC2)cc1.O=C1Nc2cc(F)ccc2C1=CO | O=C1Nc2cc(F)ccc2C1=CNc1ccc(OCCN2CCCCC2)cc1 | null | null | null | Heteroatom Alkylation and Arylation | Reductive amination with alcohol | ac661a5987df49e763a2386679221354b73376953f4071e32e52e2d7e8877593 | dc27e5e3871ba014ddcdbe66aa8244518b94cc851f1ff4159b6674656bc3b780 | O=C1Nc2ccccc2C1=CNc1ccc(OCCN2CCCCC2)cc1 | O-[CH;D2;+0:1]=[C:2]1-[c:3]:[c:4]-[#7:5]-[C:6]-1=[O;D1;H0:7].[NH2;D1;+0:8]-[c:9](:[c:10]):[c:11]>>[O;D1;H0:7]=[C:6]1-[#7:5]-[c:4]:[c:3]-[C:2]-1=[CH;D2;+0:1]-[NH;D2;+0:8]-[c:9](:[c:10]):[c:11] | 70 | [{"value": 70.0, "product": "FC1=CC=C2C(C(NC2=C1)=O)=CNC1=CC=C(C=C1)OCCN1CCCCC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 70.0, "product": "FC1=CC=C2C(C(NC2=C1)=O)=CNC1=CC=C(C=C1)OCCN1CCCCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | In a manner similar to that described in Example 231, 4-(2-piperidin-1-yl-ethoxy)-phenylamine (737 mg, 1.2 equiv.) and 6-fluoro-3-hydroxymethylene-1,3-dihydro-indol-2-one (500 mg, 2.79 mmol, 1 equiv.) are reacted to give the named compound as a yellow solid (745 mg, 70%).
Conditions: See reaction.notes.procedure_detail... | 10.6084/m9.figshare.5104873.v1 | null | Enol.Primary amine | Enamine | null | null | c1ccc2c(c1)CCN2.c1ccccc1.C1CC[NH]CC1 | HO- | null | null | null | Nc1ccc(OCCN2CCCCC2)cc1.O=C1Nc2cc(F)ccc2C1=CO>>O=C1Nc2cc(F)ccc2C1=CNc1ccc(OCCN2CCCCC2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-09bf3815c8364dcdaaccc405ae35d62c | Nc1ccc(OCCN2CCCCC2)cc1.O=C1Nc2ccccc2C1=CO>>O=C1Nc2ccccc2C1=CNc1ccc(OCCN2CCCCC2)cc1 | N1(CCCCC1)CCOC1=CC=C(C=C1)N.OC=C1C(NC2=CC=CC=C12)=O>>N1(CCCCC1)CCOC1=CC=C(C=C1)NC=C1C(NC2=CC=CC=C12)=O | [NH2:12][c:13]1[cH:14][cH:15][c:16]([O:17][CH2:18][CH2:19][N:20]2[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25]2)[cH:26][cH:27]1.O[CH:11]=[C:10]1[C:2](=[O:1])[NH:3][c:4]2[cH:5][cH:6][cH:7][cH:8][c:9]21>>[O:1]=[C:2]1[NH:3][c:4]2[cH:5][cH:6][cH:7][cH:8][c:9]2[C:10]1=[CH:11][NH:12][c:13]1[cH:14][cH:15][c:16]([O:17][CH2:18][CH2:... | Nc1ccc(OCCN2CCCCC2)cc1.O=C1Nc2ccccc2C1=CO | O=C1Nc2ccccc2C1=CNc1ccc(OCCN2CCCCC2)cc1 | null | null | null | Heteroatom Alkylation and Arylation | Reductive amination with alcohol | ac661a5987df49e763a2386679221354b73376953f4071e32e52e2d7e8877593 | dc27e5e3871ba014ddcdbe66aa8244518b94cc851f1ff4159b6674656bc3b780 | O=C1Nc2ccccc2C1=CNc1ccc(OCCN2CCCCC2)cc1 | O-[CH;D2;+0:1]=[C:2]1-[c:3]:[c:4]-[#7:5]-[C:6]-1=[O;D1;H0:7].[NH2;D1;+0:8]-[c:9](:[c:10]):[c:11]>>[O;D1;H0:7]=[C:6]1-[#7:5]-[c:4]:[c:3]-[C:2]-1=[CH;D2;+0:1]-[NH;D2;+0:8]-[c:9](:[c:10]):[c:11] | 80 | [{"value": 80.0, "product": "N1(CCCCC1)CCOC1=CC=C(C=C1)NC=C1C(NC2=CC=CC=C12)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 79.5, "product": "N1(CCCCC1)CCOC1=CC=C(C=C1)NC=C1C(NC2=CC=CC=C12)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | In a manner similar to that described in Example 231, 4-(2-piperidin-1-yl-ethoxy)-phenylamine (820 mg, 1.2 equiv.) and 3-hydroxymethylene-1,3-dihydro-indol-2-one (500 mg, 3.11 mmol, 1 equiv.) are reacted to give the named compound as a yellow solid (899 mg, 80%).
Conditions: See reaction.notes.procedure_details.
Workup... | 10.6084/m9.figshare.5104873.v1 | null | Enol.Primary amine | Enamine | null | null | c1ccc2c(c1)CCN2.c1ccccc1.C1CC[NH]CC1 | HO- | null | null | null | Nc1ccc(OCCN2CCCCC2)cc1.O=C1Nc2ccccc2C1=CO>>O=C1Nc2ccccc2C1=CNc1ccc(OCCN2CCCCC2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-4ae606b410724582ab5bb8053290d27b | Nc1ccc(OCCCN2CCCCC2)cc1.O=C1Nc2cccc(F)c2C1=CO>>O=C1Nc2cccc(F)c2C1=CNc1ccc(OCCCN2CCCCC2)cc1 | N1(CCCCC1)CCCOC1=CC=C(C=C1)N.FC1=C2C(C(NC2=CC=C1)=O)=CO>>FC1=C2C(C(NC2=CC=C1)=O)=CNC1=CC=C(C=C1)OCCCN1CCCCC1 | [NH2:13][c:14]1[cH:15][cH:16][c:17]([O:18][CH2:19][CH2:20][CH2:21][N:22]2[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27]2)[cH:28][cH:29]1.O[CH:12]=[C:11]1[C:2](=[O:1])[NH:3][c:4]2[cH:5][cH:6][cH:7][c:8]([F:9])[c:10]21>>[O:1]=[C:2]1[NH:3][c:4]2[cH:5][cH:6][cH:7][c:8]([F:9])[c:10]2[C:11]1=[CH:12][NH:13][c:14]1[cH:15][cH:16][c:1... | Nc1ccc(OCCCN2CCCCC2)cc1.O=C1Nc2cccc(F)c2C1=CO | O=C1Nc2cccc(F)c2C1=CNc1ccc(OCCCN2CCCCC2)cc1 | null | null | null | Heteroatom Alkylation and Arylation | Reductive amination with alcohol | ac661a5987df49e763a2386679221354b73376953f4071e32e52e2d7e8877593 | dc27e5e3871ba014ddcdbe66aa8244518b94cc851f1ff4159b6674656bc3b780 | O=C1Nc2ccccc2C1=CNc1ccc(OCCCN2CCCCC2)cc1 | O-[CH;D2;+0:1]=[C:2]1-[c:3]:[c:4]-[#7:5]-[C:6]-1=[O;D1;H0:7].[NH2;D1;+0:8]-[c:9](:[c:10]):[c:11]>>[O;D1;H0:7]=[C:6]1-[#7:5]-[c:4]:[c:3]-[C:2]-1=[CH;D2;+0:1]-[NH;D2;+0:8]-[c:9](:[c:10]):[c:11] | null | [] | null | null | null | null | In a manner similar to that described in Example 231, 4-(3-piperidin-1-yl-propoxy)-phenylamine (610 mg, 1.3 equiv.) and 4-fluoro-3-hydroxymethylene-1,3-dihydro-indol-2-one (360 mg, 2 mmol, 1 equiv.) are converted to the named compound as a yellow solid (625 mg, 79%).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Enol.Primary amine | Enamine | null | null | c1ccc2c(c1)CCN2.c1ccccc1.C1CC[NH]CC1 | HO- | null | null | null | Nc1ccc(OCCCN2CCCCC2)cc1.O=C1Nc2cccc(F)c2C1=CO>>O=C1Nc2cccc(F)c2C1=CNc1ccc(OCCCN2CCCCC2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-e18d183b19cc496388abf111c69b9c47 | Nc1ccc(OCCN2CCCCC2)cc1.O=C1Nc2cccc(F)c2C1=CO>>O=C1Nc2cccc(F)c2C1=CNc1ccc(OCCN2CCCCC2)cc1 | N1(CCCCC1)CCOC1=CC=C(C=C1)N.FC1=C2C(C(NC2=CC=C1)=O)=CO>>FC1=C2C(C(NC2=CC=C1)=O)=CNC1=CC=C(C=C1)OCCN1CCCCC1 | [NH2:13][c:14]1[cH:15][cH:16][c:17]([O:18][CH2:19][CH2:20][N:21]2[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26]2)[cH:27][cH:28]1.O[CH:12]=[C:11]1[C:2](=[O:1])[NH:3][c:4]2[cH:5][cH:6][cH:7][c:8]([F:9])[c:10]21>>[O:1]=[C:2]1[NH:3][c:4]2[cH:5][cH:6][cH:7][c:8]([F:9])[c:10]2[C:11]1=[CH:12][NH:13][c:14]1[cH:15][cH:16][c:17]([O:18... | Nc1ccc(OCCN2CCCCC2)cc1.O=C1Nc2cccc(F)c2C1=CO | O=C1Nc2cccc(F)c2C1=CNc1ccc(OCCN2CCCCC2)cc1 | null | null | null | Heteroatom Alkylation and Arylation | Reductive amination with alcohol | ac661a5987df49e763a2386679221354b73376953f4071e32e52e2d7e8877593 | dc27e5e3871ba014ddcdbe66aa8244518b94cc851f1ff4159b6674656bc3b780 | O=C1Nc2ccccc2C1=CNc1ccc(OCCN2CCCCC2)cc1 | O-[CH;D2;+0:1]=[C:2]1-[c:3]:[c:4]-[#7:5]-[C:6]-1=[O;D1;H0:7].[NH2;D1;+0:8]-[c:9](:[c:10]):[c:11]>>[O;D1;H0:7]=[C:6]1-[#7:5]-[c:4]:[c:3]-[C:2]-1=[CH;D2;+0:1]-[NH;D2;+0:8]-[c:9](:[c:10]):[c:11] | 63 | [{"value": 63.0, "product": "FC1=C2C(C(NC2=CC=C1)=O)=CNC1=CC=C(C=C1)OCCN1CCCCC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 62.6, "product": "FC1=C2C(C(NC2=CC=C1)=O)=CNC1=CC=C(C=C1)OCCN1CCCCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | In a manner similar to that described in Example 231, 4-(2-piperidin-1-yl-ethoxy)-phenylamine (600 mg, 1.2 equiv.) and 4-fluoro-3-hydroxymethylene-1,3-dihydro-indol-2-one (407 mg, 2.27 mmol, 1 equiv.) (4-Fluorooxindole may be prepared as described in Synthesis 1991, 10, 871) are reacted to give the named compound as a ... | 10.6084/m9.figshare.5104873.v1 | null | Enol.Primary amine | Enamine | null | null | c1ccc2c(c1)CCN2.c1ccccc1.C1CC[NH]CC1 | HO- | null | null | null | Nc1ccc(OCCN2CCCCC2)cc1.O=C1Nc2cccc(F)c2C1=CO>>O=C1Nc2cccc(F)c2C1=CNc1ccc(OCCN2CCCCC2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-28c01fcc627b48ac80d444d4648e9962 | Nc1ccc(OCCN2CCCCC2)cc1.O=C1Nc2ccc(Cl)cc2C1=CO>>O=C1Nc2ccc(Cl)cc2C1=CNc1ccc(OCCN2CCCCC2)cc1 | N1(CCCCC1)CCOC1=CC=C(C=C1)N.ClC=1C=C2C(C(NC2=CC1)=O)=CO>>ClC=1C=C2C(C(NC2=CC1)=O)=CNC1=CC=C(C=C1)OCCN1CCCCC1 | [NH2:13][c:14]1[cH:15][cH:16][c:17]([O:18][CH2:19][CH2:20][N:21]2[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26]2)[cH:27][cH:28]1.O[CH:12]=[C:11]1[C:2](=[O:1])[NH:3][c:4]2[cH:5][cH:6][c:7]([Cl:8])[cH:9][c:10]21>>[O:1]=[C:2]1[NH:3][c:4]2[cH:5][cH:6][c:7]([Cl:8])[cH:9][c:10]2[C:11]1=[CH:12][NH:13][c:14]1[cH:15][cH:16][c:17]([O:... | Nc1ccc(OCCN2CCCCC2)cc1.O=C1Nc2ccc(Cl)cc2C1=CO | O=C1Nc2ccc(Cl)cc2C1=CNc1ccc(OCCN2CCCCC2)cc1 | null | null | null | Heteroatom Alkylation and Arylation | Reductive amination with alcohol | ac661a5987df49e763a2386679221354b73376953f4071e32e52e2d7e8877593 | dc27e5e3871ba014ddcdbe66aa8244518b94cc851f1ff4159b6674656bc3b780 | O=C1Nc2ccccc2C1=CNc1ccc(OCCN2CCCCC2)cc1 | O-[CH;D2;+0:1]=[C:2]1-[c:3]:[c:4]-[#7:5]-[C:6]-1=[O;D1;H0:7].[NH2;D1;+0:8]-[c:9](:[c:10]):[c:11]>>[O;D1;H0:7]=[C:6]1-[#7:5]-[c:4]:[c:3]-[C:2]-1=[CH;D2;+0:1]-[NH;D2;+0:8]-[c:9](:[c:10]):[c:11] | 57 | [{"value": 57.0, "product": "ClC=1C=C2C(C(NC2=CC1)=O)=CNC1=CC=C(C=C1)OCCN1CCCCC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 56.8, "product": "ClC=1C=C2C(C(NC2=CC1)=O)=CNC1=CC=C(C=C1)OCCN1CCCCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | In a manner similar to that described in Example 231, 4-(2-piperidin-1-yl-ethoxy)-phenylamine (600 mg, 1.2 equiv.) and 5-chloro-3-hydroxymethylene-1,3-dihydro-indol-2-one (444 mg, 2.27 mmol, 1 equiv.) are reacted to give the named compound as a yellow solid (513 mg, 57%).
Conditions: See reaction.notes.procedure_detail... | 10.6084/m9.figshare.5104873.v1 | null | Enol.Primary amine | Enamine | null | null | c1ccc2c(c1)CCN2.c1ccccc1.C1CC[NH]CC1 | HO- | null | null | null | Nc1ccc(OCCN2CCCCC2)cc1.O=C1Nc2ccc(Cl)cc2C1=CO>>O=C1Nc2ccc(Cl)cc2C1=CNc1ccc(OCCN2CCCCC2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-0ad458f5ff7a449ca578753d7b398b45 | Nc1ccc(OCCN2CCCCC2)cc1.O=C1Nc2ccc(F)cc2C1=CO>>O=C1Nc2ccc(F)cc2C1=CNc1ccc(OCCN2CCCCC2)cc1 | N1(CCCCC1)CCOC1=CC=C(C=C1)N.FC=1C=C2C(C(NC2=CC1)=O)=CO>>FC=1C=C2C(C(NC2=CC1)=O)=CNC1=CC=C(C=C1)OCCN1CCCCC1 | [NH2:13][c:14]1[cH:15][cH:16][c:17]([O:18][CH2:19][CH2:20][N:21]2[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26]2)[cH:27][cH:28]1.O[CH:12]=[C:11]1[C:2](=[O:1])[NH:3][c:4]2[cH:5][cH:6][c:7]([F:8])[cH:9][c:10]21>>[O:1]=[C:2]1[NH:3][c:4]2[cH:5][cH:6][c:7]([F:8])[cH:9][c:10]2[C:11]1=[CH:12][NH:13][c:14]1[cH:15][cH:16][c:17]([O:18... | Nc1ccc(OCCN2CCCCC2)cc1.O=C1Nc2ccc(F)cc2C1=CO | O=C1Nc2ccc(F)cc2C1=CNc1ccc(OCCN2CCCCC2)cc1 | null | null | null | Heteroatom Alkylation and Arylation | Reductive amination with alcohol | ac661a5987df49e763a2386679221354b73376953f4071e32e52e2d7e8877593 | dc27e5e3871ba014ddcdbe66aa8244518b94cc851f1ff4159b6674656bc3b780 | O=C1Nc2ccccc2C1=CNc1ccc(OCCN2CCCCC2)cc1 | O-[CH;D2;+0:1]=[C:2]1-[c:3]:[c:4]-[#7:5]-[C:6]-1=[O;D1;H0:7].[NH2;D1;+0:8]-[c:9](:[c:10]):[c:11]>>[O;D1;H0:7]=[C:6]1-[#7:5]-[c:4]:[c:3]-[C:2]-1=[CH;D2;+0:1]-[NH;D2;+0:8]-[c:9](:[c:10]):[c:11] | 74.4 | [{"value": 74.0, "product": "FC=1C=C2C(C(NC2=CC1)=O)=CNC1=CC=C(C=C1)OCCN1CCCCC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 74.4, "product": "FC=1C=C2C(C(NC2=CC1)=O)=CNC1=CC=C(C=C1)OCCN1CCCCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | In a manner similar to that described in Example 231, 4-(2-piperidin-1-yl-ethoxy)-phenylamine (600 mg, 1.2 equiv.) and 5-fluoro-3-hydroxymethylene-1,3-dihydro-indol-2-one (407 mg, 2.27 mmol, 1 equiv.) are reacted to give the named compound as a yellow solid (644 mg, 74%).
Conditions: See reaction.notes.procedure_detail... | 10.6084/m9.figshare.5104873.v1 | null | Enol.Primary amine | Enamine | null | null | c1ccc2c(c1)CCN2.c1ccccc1.C1CC[NH]CC1 | HO- | null | null | null | Nc1ccc(OCCN2CCCCC2)cc1.O=C1Nc2ccc(F)cc2C1=CO>>O=C1Nc2ccc(F)cc2C1=CNc1ccc(OCCN2CCCCC2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-e20d14176b5048e8a6ea5c9122514271 | CCN(CC)CCOc1ccc(N)cc1.Cc1cccc2c1C(=CO)C(=O)N2>>CCN(CC)CCOc1ccc(NC=C2C(=O)Nc3cccc(C)c32)cc1 | C(C)N(CCOC1=CC=C(C=C1)N)CC.CC1=C2C(C(NC2=CC=C1)=O)=CO>>C(C)N(CCOC1=CC=C(C=C1)NC=C1C(NC2=CC=CC(=C12)C)=O)CC | [CH3:1][CH2:2][N:3]([CH2:4][CH3:5])[CH2:6][CH2:7][O:8][c:9]1[cH:10][cH:11][c:12]([NH2:13])[cH:26][cH:27]1.O[CH:14]=[C:15]1[C:16](=[O:17])[NH:18][c:19]2[cH:20][cH:21][cH:22][c:23]([CH3:24])[c:25]21>>[CH3:1][CH2:2][N:3]([CH2:4][CH3:5])[CH2:6][CH2:7][O:8][c:9]1[cH:10][cH:11][c:12]([NH:13][CH:14]=[C:15]2[C:16](=[O:17])[NH:... | CCN(CC)CCOc1ccc(N)cc1.Cc1cccc2c1C(=CO)C(=O)N2 | CCN(CC)CCOc1ccc(NC=C2C(=O)Nc3cccc(C)c32)cc1 | null | null | null | Heteroatom Alkylation and Arylation | Reductive amination with alcohol | ac661a5987df49e763a2386679221354b73376953f4071e32e52e2d7e8877593 | dc27e5e3871ba014ddcdbe66aa8244518b94cc851f1ff4159b6674656bc3b780 | O=C1Nc2ccccc2C1=CNc1ccccc1 | O-[CH;D2;+0:1]=[C:2]1-[c:3]:[c:4]-[#7:5]-[C:6]-1=[O;D1;H0:7].[NH2;D1;+0:8]-[c:9](:[c:10]):[c:11]>>[O;D1;H0:7]=[C:6]1-[#7:5]-[c:4]:[c:3]-[C:2]-1=[CH;D2;+0:1]-[NH;D2;+0:8]-[c:9](:[c:10]):[c:11] | 23 | [{"value": 23.0, "product": "C(C)N(CCOC1=CC=C(C=C1)NC=C1C(NC2=CC=CC(=C12)C)=O)CC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 22.7, "product": "C(C)N(CCOC1=CC=C(C=C1)NC=C1C(NC2=CC=CC(=C12)C)=O)CC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | In a manner similar to that describe in Example 231, 4-(2-diethylamino-ethoxy)-phenylamine (713 mg, 1.2 equiv.) and 4-methyl-3-hydroxymethylene-1,3-dihydro-indol-2-one (500 mg, 2.86 mmol, 1 equiv.) are reacted to give the named compound as a yellow solid (237 mg, 23%).
Conditions: See reaction.notes.procedure_details.
... | 10.6084/m9.figshare.5104873.v1 | null | Enol.Primary amine | Enamine | null | null | c1ccccc1.c1ccc2c(c1)CCN2 | HO- | null | null | null | CCN(CC)CCOc1ccc(N)cc1.Cc1cccc2c1C(=CO)C(=O)N2>>CCN(CC)CCOc1ccc(NC=C2C(=O)Nc3cccc(C)c32)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-4193ad0a81c14c51bbee8ad564058001 | CCN(CC)CCOc1ccc(N)cc1.O=C1Nc2ccccc2C1=CO>>CCN(CC)CCOc1ccc(NC=C2C(=O)Nc3ccccc32)cc1 | C(C)N(CCOC1=CC=C(C=C1)N)CC.OC=C1C(NC2=CC=CC=C12)=O>>C(C)N(CCOC1=CC=C(C=C1)NC=C1C(NC2=CC=CC=C12)=O)CC | [CH3:1][CH2:2][N:3]([CH2:4][CH3:5])[CH2:6][CH2:7][O:8][c:9]1[cH:10][cH:11][c:12]([NH2:13])[cH:25][cH:26]1.O[CH:14]=[C:15]1[C:16](=[O:17])[NH:18][c:19]2[cH:20][cH:21][cH:22][cH:23][c:24]21>>[CH3:1][CH2:2][N:3]([CH2:4][CH3:5])[CH2:6][CH2:7][O:8][c:9]1[cH:10][cH:11][c:12]([NH:13][CH:14]=[C:15]2[C:16](=[O:17])[NH:18][c:19]... | CCN(CC)CCOc1ccc(N)cc1.O=C1Nc2ccccc2C1=CO | CCN(CC)CCOc1ccc(NC=C2C(=O)Nc3ccccc32)cc1 | null | null | null | Heteroatom Alkylation and Arylation | Reductive amination with alcohol | ac661a5987df49e763a2386679221354b73376953f4071e32e52e2d7e8877593 | dc27e5e3871ba014ddcdbe66aa8244518b94cc851f1ff4159b6674656bc3b780 | O=C1Nc2ccccc2C1=CNc1ccccc1 | O-[CH;D2;+0:1]=[C:2]1-[c:3]:[c:4]-[#7:5]-[C:6]-1=[O;D1;H0:7].[NH2;D1;+0:8]-[c:9](:[c:10]):[c:11]>>[O;D1;H0:7]=[C:6]1-[#7:5]-[c:4]:[c:3]-[C:2]-1=[CH;D2;+0:1]-[NH;D2;+0:8]-[c:9](:[c:10]):[c:11] | 51 | [{"value": 51.0, "product": "C(C)N(CCOC1=CC=C(C=C1)NC=C1C(NC2=CC=CC=C12)=O)CC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 51.0, "product": "C(C)N(CCOC1=CC=C(C=C1)NC=C1C(NC2=CC=CC=C12)=O)CC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | In a manner similar to that described in Example 231, 4-(2-diethylaminoethoxy)-phenylamine (775 mg, 1.2 equiv.) and 3-hydroxymethylene-1,3-dihydro-indol-2-one (500 mg, 3.11 mmol, 1 equiv.) are reacted to give the named compound as a yellow solid (557 mg, 51%).
Conditions: See reaction.notes.procedure_details.
Workup: a... | 10.6084/m9.figshare.5104873.v1 | null | Enol.Primary amine | Enamine | null | null | c1ccccc1.c1ccc2c(c1)CCN2 | HO- | null | null | null | CCN(CC)CCOc1ccc(N)cc1.O=C1Nc2ccccc2C1=CO>>CCN(CC)CCOc1ccc(NC=C2C(=O)Nc3ccccc32)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-fbe1967216c44cbb8fff20d89bdee88c | CCN(CC)CCOc1ccc(N)cc1.O=C1Nc2cc(F)ccc2C1=CO>>CCN(CC)CCOc1ccc(NC=C2C(=O)Nc3cc(F)ccc32)cc1 | C(C)N(CCOC1=CC=C(C=C1)N)CC.FC1=CC=C2C(C(NC2=C1)=O)=CO>>C(C)N(CCOC1=CC=C(C=C1)NC=C1C(NC2=CC(=CC=C12)F)=O)CC | [CH3:1][CH2:2][N:3]([CH2:4][CH3:5])[CH2:6][CH2:7][O:8][c:9]1[cH:10][cH:11][c:12]([NH2:13])[cH:26][cH:27]1.O[CH:14]=[C:15]1[C:16](=[O:17])[NH:18][c:19]2[cH:20][c:21]([F:22])[cH:23][cH:24][c:25]21>>[CH3:1][CH2:2][N:3]([CH2:4][CH3:5])[CH2:6][CH2:7][O:8][c:9]1[cH:10][cH:11][c:12]([NH:13][CH:14]=[C:15]2[C:16](=[O:17])[NH:18... | CCN(CC)CCOc1ccc(N)cc1.O=C1Nc2cc(F)ccc2C1=CO | CCN(CC)CCOc1ccc(NC=C2C(=O)Nc3cc(F)ccc32)cc1 | null | null | null | Heteroatom Alkylation and Arylation | Reductive amination with alcohol | ac661a5987df49e763a2386679221354b73376953f4071e32e52e2d7e8877593 | dc27e5e3871ba014ddcdbe66aa8244518b94cc851f1ff4159b6674656bc3b780 | O=C1Nc2ccccc2C1=CNc1ccccc1 | O-[CH;D2;+0:1]=[C:2]1-[c:3]:[c:4]-[#7:5]-[C:6]-1=[O;D1;H0:7].[NH2;D1;+0:8]-[c:9](:[c:10]):[c:11]>>[O;D1;H0:7]=[C:6]1-[#7:5]-[c:4]:[c:3]-[C:2]-1=[CH;D2;+0:1]-[NH;D2;+0:8]-[c:9](:[c:10]):[c:11] | 39 | [{"value": 39.0, "product": "C(C)N(CCOC1=CC=C(C=C1)NC=C1C(NC2=CC(=CC=C12)F)=O)CC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 38.7, "product": "C(C)N(CCOC1=CC=C(C=C1)NC=C1C(NC2=CC(=CC=C12)F)=O)CC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | In a manner similar to that described in Example 231, 4-(2-Diethylamino-ethoxy)-phenylamine (697 mg, 1.2 equiv.) and 6-fluoro-3-hydroxymethylene-1,3-dihydro-indol-2-one (500 mg, 2.79 mmol, 1 equiv.) are reacted to give the named compound as a yellow solid (399 mg, 39%).
Conditions: See reaction.notes.procedure_details.... | 10.6084/m9.figshare.5104873.v1 | null | Enol.Primary amine | Enamine | null | null | c1ccccc1.c1ccc2c(c1)CCN2 | HO- | null | null | null | CCN(CC)CCOc1ccc(N)cc1.O=C1Nc2cc(F)ccc2C1=CO>>CCN(CC)CCOc1ccc(NC=C2C(=O)Nc3cc(F)ccc32)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-1b58fd880a684035bb71cfdf1ee7c3ae | CCN(CC)CCCOc1ccc(N)cc1F.O=C1Nc2cccc(F)c2C1=CO>>CCN(CC)CCCOc1ccc(NC=C2C(=O)Nc3cccc(F)c32)cc1F | C(C)N(CCCOC1=C(C=C(C=C1)N)F)CC.FC1=C2C(C(NC2=CC=C1)=O)=CO>>C(C)N(CCCOC1=C(C=C(C=C1)NC=C1C(NC2=CC=CC(=C12)F)=O)F)CC | [CH3:1][CH2:2][N:3]([CH2:4][CH3:5])[CH2:6][CH2:7][CH2:8][O:9][c:10]1[cH:11][cH:12][c:13]([NH2:14])[cH:27][c:28]1[F:29].O[CH:15]=[C:16]1[C:17](=[O:18])[NH:19][c:20]2[cH:21][cH:22][cH:23][c:24]([F:25])[c:26]21>>[CH3:1][CH2:2][N:3]([CH2:4][CH3:5])[CH2:6][CH2:7][CH2:8][O:9][c:10]1[cH:11][cH:12][c:13]([NH:14][CH:15]=[C:16]2... | CCN(CC)CCCOc1ccc(N)cc1F.O=C1Nc2cccc(F)c2C1=CO | CCN(CC)CCCOc1ccc(NC=C2C(=O)Nc3cccc(F)c32)cc1F | null | null | null | Heteroatom Alkylation and Arylation | Reductive amination with alcohol | ac661a5987df49e763a2386679221354b73376953f4071e32e52e2d7e8877593 | dc27e5e3871ba014ddcdbe66aa8244518b94cc851f1ff4159b6674656bc3b780 | O=C1Nc2ccccc2C1=CNc1ccccc1 | O-[CH;D2;+0:1]=[C:2]1-[c:3]:[c:4]-[#7:5]-[C:6]-1=[O;D1;H0:7].[NH2;D1;+0:8]-[c:9](:[c:10]):[c:11]>>[O;D1;H0:7]=[C:6]1-[#7:5]-[c:4]:[c:3]-[C:2]-1=[CH;D2;+0:1]-[NH;D2;+0:8]-[c:9](:[c:10]):[c:11] | 67.4 | [{"value": 67.0, "product": "C(C)N(CCCOC1=C(C=C(C=C1)NC=C1C(NC2=CC=CC(=C12)F)=O)F)CC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 67.4, "product": "C(C)N(CCCOC1=C(C=C(C=C1)NC=C1C(NC2=CC=CC(=C12)F)=O)F)CC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | In a manner similar to that described in Example 231, 4-(3-Diethylamino-propoxy)-3-fluoro-phenylamine (720 mg, 1.5 equiv.) and 4-fluoro-3-hydroxymethylene-1,3-dihydro-indol-2-one (358 mg, 2.00 mmol) are reacted to give the named compound as a yellow solid (541 mg, 67%).
Conditions: See reaction.notes.procedure_details.... | 10.6084/m9.figshare.5104873.v1 | null | Enol.Primary amine | Enamine | null | null | c1ccccc1.c1ccc2c(c1)CCN2 | HO- | null | null | null | CCN(CC)CCCOc1ccc(N)cc1F.O=C1Nc2cccc(F)c2C1=CO>>CCN(CC)CCCOc1ccc(NC=C2C(=O)Nc3cccc(F)c32)cc1F |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-842c8a1fc9d040ed9e1571297c6d1a76 | COc1cccc(B(O)O)c1.O=[N+]([O-])c1cc(Br)ccc1F>>COc1cccc(-c2ccc(F)c([N+](=O)[O-])c2)c1 | C([O-])([O-])=O.[Na+].[Na+].BrC1=CC(=C(C=C1)F)[N+](=O)[O-].COC=1C=C(C=CC1)B(O)O.C1(=CC=CC=C1)C>>FC1=C(C=C(C=C1)C1=CC(=CC=C1)OC)[N+](=O)[O-] | OB(O)[c:7]1[cH:6][cH:5][cH:4][c:3]([O:2][CH3:1])[cH:18]1.Br[c:8]1[cH:9][cH:10][c:11]([F:12])[c:13]([N+:14](=[O:15])[O-:16])[cH:17]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7](-[c:8]2[cH:9][cH:10][c:11]([F:12])[c:13]([N+:14](=[O:15])[O-:16])[cH:17]2)[cH:18]1 | COc1cccc(B(O)O)c1.O=[N+]([O-])c1cc(Br)ccc1F | COc1cccc(-c2ccc(F)c([N+](=O)[O-])c2)c1 | null | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1 | C(C)O | C-C Coupling | Suzuki coupling with boronic acids | d79a78c79f0c392f0911481acf5c300cc98205269acdb93c24fb610a61c4c868 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(-c2ccccc2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].O-B(-O)-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]>>[c:5]:[c:4]:[c;H0;D3;+0:1](-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]):[c:2]:[c:3] | null | [] | null | null | null | null | 4-Bromo-1-fluoro-2-nitro-benzene (5 gms.), 3.85 gms. 3-methoxyphenylboronic acid and 22 mL of a 2M aqueous solution of sodium carbonate are suspended in 100 mL of a 1:1 (v:v) mix of toluene and ethanol. The resulting suspension is then treated with 0.8 gms. tetrakis(triphenylphosphine)palladium(0) at room temperature. ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | HBr.B | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.C(C)O | null | null | COc1cccc(B(O)O)c1.O=[N+]([O-])c1cc(Br)ccc1F>C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.C(C)O>COc1cccc(-c2ccc(F)c([N+](=O)[O-])c2)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-3093fa988b704db1b269470ed64cbdd4 | COC(=O)C(C(=O)OC)c1ccc(-c2cccc(OC)c2)cc1[N+](=O)[O-]>>COc1cccc(-c2ccc(CC(=O)O)c([N+](=O)[O-])c2)c1 | COC(C(C(=O)OC)C1=C(C=C(C=C1)C1=CC(=CC=C1)OC)[N+](=O)[O-])=O>>COC=1C=C(C=CC1)C1=CC(=C(C=C1)CC(=O)O)[N+](=O)[O-] | COC(=O)[CH:12]([c:11]1[cH:10][cH:9][c:8](-[c:7]2[cH:6][cH:5][cH:4][c:3]([O:2][CH3:1])[cH:21]2)[cH:20][c:16]1[N+:17](=[O:18])[O-:19])[C:13](=[O:14])[O:15]C>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7](-[c:8]2[cH:9][cH:10][c:11]([CH2:12][C:13](=[O:14])[OH:15])[c:16]([N+:17](=[O:18])[O-:19])[cH:20]2)[cH:21]1 | COC(=O)C(C(=O)OC)c1ccc(-c2cccc(OC)c2)cc1[N+](=O)[O-] | COc1cccc(-c2ccc(CC(=O)O)c([N+](=O)[O-])c2)c1 | null | null | Cl | Reduction | OtherReaction | 5ba27bafcd96d74a94be636caed9361c02821d71f9ddac00396de4e018da642b | 6d9edf77f3bf4688cdf5f5c3ccf062016b04f2e19a67399a3ca7c7e8d575cc5a | c1ccc(-c2ccccc2)cc1 | C-O-C(=O)-[CH;D3;+0:1](-[C:2](=[O;D1;H0:3])-[O;H0;D2;+0:4]-C)-[c:5](:[c:6]):[c:7]>>[O;D1;H0:3]=[C:2](-[OH;D1;+0:4])-[CH2;D2;+0:1]-[c:5](:[c:6]):[c:7] | null | [] | 110 | CELSIUS | null | null | 2-(3′-Methoxy-3-nitro-biphenyl-4-yl)-malonic acid dimethyl ester (4.4023 gms.) is suspended in 45 mL of 6N HCl and heated at 110° C. for 4 days. The reaction mixture is cooled to room temperature and the precipitate is collected by filtration. As the solid material is in rather large chunks, the solid purification is s... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester | Carboxylic acid | null | null | c1ccccc1.c1ccccc1 | HO- | Cl | 110 | null | COC(=O)C(C(=O)OC)c1ccc(-c2cccc(OC)c2)cc1[N+](=O)[O-]>Cl>COc1cccc(-c2ccc(CC(=O)O)c([N+](=O)[O-])c2)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-e83cfed6237146ecaad1c4492e25a9ff | COc1cccc(-c2ccc3c(c2)NC(=O)C3=CO)c1.Nc1ccc(N2CCOCC2)cc1>>COc1cccc(-c2ccc3c(c2)NC(=O)C3=CNc2ccc(N3CCOCC3)cc2)c1 | OC=C1C(NC2=CC(=CC=C12)C1=CC(=CC=C1)OC)=O.N1(CCOCC1)C1=CC=C(C=C1)N>>COC=1C=C(C=CC1)C1=CC=C2C(C(NC2=C1)=O)=CNC1=CC=C(C=C1)N1CCOCC1 | O[CH:18]=[C:17]1[c:11]2[cH:10][cH:9][c:8](-[c:7]3[cH:6][cH:5][cH:4][c:3]([O:2][CH3:1])[cH:32]3)[cH:13][c:12]2[NH:14][C:15]1=[O:16].[NH2:19][c:20]1[cH:21][cH:22][c:23]([N:24]2[CH2:25][CH2:26][O:27][CH2:28][CH2:29]2)[cH:30][cH:31]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7](-[c:8]2[cH:9][cH:10][c:11]3[c:12]([cH:13]2)[NH:... | COc1cccc(-c2ccc3c(c2)NC(=O)C3=CO)c1.Nc1ccc(N2CCOCC2)cc1 | COc1cccc(-c2ccc3c(c2)NC(=O)C3=CNc2ccc(N3CCOCC3)cc2)c1 | null | null | O1CCCC1 | Heteroatom Alkylation and Arylation | Reductive amination with alcohol | ac661a5987df49e763a2386679221354b73376953f4071e32e52e2d7e8877593 | dc27e5e3871ba014ddcdbe66aa8244518b94cc851f1ff4159b6674656bc3b780 | O=C1Nc2cc(-c3ccccc3)ccc2C1=CNc1ccc(N2CCOCC2)cc1 | O-[CH;D2;+0:1]=[C:2]1-[c:3]:[c:4]-[#7:5]-[C:6]-1=[O;D1;H0:7].[NH2;D1;+0:8]-[c:9](:[c:10]):[c:11]>>[O;D1;H0:7]=[C:6]1-[#7:5]-[c:4]:[c:3]-[C:2]-1=[CH;D2;+0:1]-[NH;D2;+0:8]-[c:9](:[c:10]):[c:11] | null | [] | null | null | null | null | The named compound is prepared by refluxing 0.020 gms E & Z 3-hydroxymethylene-6-(3-methoxy-phenyl)-1,3-dihydro-indol-2-one with 0.020 gms. 4-morpholin-4-yl-phenylamine in tetrahydrofuran (0.33 mL) for 2 days. Following cooling to room temperature, solvent evaporation in vacuo, trituration with isopropanol and filtrati... | 10.6084/m9.figshare.5104873.v1 | null | Enol.Primary amine | Enamine | null | null | c1ccccc1.c1ccc2c(c1)CCN2.c1ccccc1.C1COCC[NH]1 | HO- | O1CCCC1 | null | null | COc1cccc(-c2ccc3c(c2)NC(=O)C3=CO)c1.Nc1ccc(N2CCOCC2)cc1>O1CCCC1>COc1cccc(-c2ccc3c(c2)NC(=O)C3=CNc2ccc(N3CCOCC3)cc2)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-a2382c20b073413a90f8631784926c2c | Nc1ccc(OCCN2CCCC2)cc1.O=C1Nc2cc(F)ccc2C1=CO>>O=C1Nc2cc(F)ccc2C1=CNc1ccc(OCCN2CCCC2)cc1 | N1(CCCC1)CCOC1=CC=C(C=C1)N.FC1=CC=C2C(C(NC2=C1)=O)=CO>>FC1=CC=C2C(C(NC2=C1)=O)=CNC1=CC=C(C=C1)OCCN1CCCC1 | [NH2:13][c:14]1[cH:15][cH:16][c:17]([O:18][CH2:19][CH2:20][N:21]2[CH2:22][CH2:23][CH2:24][CH2:25]2)[cH:26][cH:27]1.O[CH:12]=[C:11]1[C:2](=[O:1])[NH:3][c:4]2[cH:5][c:6]([F:7])[cH:8][cH:9][c:10]21>>[O:1]=[C:2]1[NH:3][c:4]2[cH:5][c:6]([F:7])[cH:8][cH:9][c:10]2[C:11]1=[CH:12][NH:13][c:14]1[cH:15][cH:16][c:17]([O:18][CH2:19... | Nc1ccc(OCCN2CCCC2)cc1.O=C1Nc2cc(F)ccc2C1=CO | O=C1Nc2cc(F)ccc2C1=CNc1ccc(OCCN2CCCC2)cc1 | null | null | null | Heteroatom Alkylation and Arylation | Reductive amination with alcohol | ac661a5987df49e763a2386679221354b73376953f4071e32e52e2d7e8877593 | dc27e5e3871ba014ddcdbe66aa8244518b94cc851f1ff4159b6674656bc3b780 | O=C1Nc2ccccc2C1=CNc1ccc(OCCN2CCCC2)cc1 | O-[CH;D2;+0:1]=[C:2]1-[c:3]:[c:4]-[#7:5]-[C:6]-1=[O;D1;H0:7].[NH2;D1;+0:8]-[c:9](:[c:10]):[c:11]>>[O;D1;H0:7]=[C:6]1-[#7:5]-[c:4]:[c:3]-[C:2]-1=[CH;D2;+0:1]-[NH;D2;+0:8]-[c:9](:[c:10]):[c:11] | 48.8 | [{"value": 48.0, "product": "FC1=CC=C2C(C(NC2=C1)=O)=CNC1=CC=C(C=C1)OCCN1CCCC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 48.8, "product": "FC1=CC=C2C(C(NC2=C1)=O)=CNC1=CC=C(C=C1)OCCN1CCCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | In a manner similar to that described in Example 231, 4-(2-pyrrolidin-1-yl-ethoxy)-phenylamine (690 mg, 1.2 equiv.) and 6-fluoro-3-hydroxymethylene-1,3-dihydro-indol-2-one (500 mg, 2.79 mmol, 1 equiv.) are reacted to give the named compound as a yellow solid (500 mg, 48%).
Conditions: See reaction.notes.procedure_detai... | 10.6084/m9.figshare.5104873.v1 | null | Enol.Primary amine | Enamine | null | null | c1ccc2c(c1)CCN2.c1ccccc1.C1CC[NH]C1 | HO- | null | null | null | Nc1ccc(OCCN2CCCC2)cc1.O=C1Nc2cc(F)ccc2C1=CO>>O=C1Nc2cc(F)ccc2C1=CNc1ccc(OCCN2CCCC2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-f19948af1f4d4cf1ab8fc0ae7d18da41 | Nc1ccc(OCCN2CCCC2)cc1.O=C1Nc2ccccc2C1=CO>>O=C1Nc2ccccc2C1=CNc1ccc(OCCN2CCCC2)cc1 | N1(CCCC1)CCOC1=CC=C(C=C1)N.OC=C1C(NC2=CC=CC=C12)=O>>N1(CCCC1)CCOC1=CC=C(C=C1)NC=C1C(NC2=CC=CC=C12)=O | [NH2:12][c:13]1[cH:14][cH:15][c:16]([O:17][CH2:18][CH2:19][N:20]2[CH2:21][CH2:22][CH2:23][CH2:24]2)[cH:25][cH:26]1.O[CH:11]=[C:10]1[C:2](=[O:1])[NH:3][c:4]2[cH:5][cH:6][cH:7][cH:8][c:9]21>>[O:1]=[C:2]1[NH:3][c:4]2[cH:5][cH:6][cH:7][cH:8][c:9]2[C:10]1=[CH:11][NH:12][c:13]1[cH:14][cH:15][c:16]([O:17][CH2:18][CH2:19][N:20... | Nc1ccc(OCCN2CCCC2)cc1.O=C1Nc2ccccc2C1=CO | O=C1Nc2ccccc2C1=CNc1ccc(OCCN2CCCC2)cc1 | null | null | null | Heteroatom Alkylation and Arylation | Reductive amination with alcohol | ac661a5987df49e763a2386679221354b73376953f4071e32e52e2d7e8877593 | dc27e5e3871ba014ddcdbe66aa8244518b94cc851f1ff4159b6674656bc3b780 | O=C1Nc2ccccc2C1=CNc1ccc(OCCN2CCCC2)cc1 | O-[CH;D2;+0:1]=[C:2]1-[c:3]:[c:4]-[#7:5]-[C:6]-1=[O;D1;H0:7].[NH2;D1;+0:8]-[c:9](:[c:10]):[c:11]>>[O;D1;H0:7]=[C:6]1-[#7:5]-[c:4]:[c:3]-[C:2]-1=[CH;D2;+0:1]-[NH;D2;+0:8]-[c:9](:[c:10]):[c:11] | 64 | [{"value": 64.0, "product": "N1(CCCC1)CCOC1=CC=C(C=C1)NC=C1C(NC2=CC=CC=C12)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 63.5, "product": "N1(CCCC1)CCOC1=CC=C(C=C1)NC=C1C(NC2=CC=CC=C12)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | In a manner similar to that described in Example 231, 4-(2-pyrrolidin-1-yl-ethoxy)-phenylamine (767 mg, 1.2 equiv.) and 3-hydroxymethylene-1,3-dihydro-indol-2-one (500 mg, 3.11 mmol, 1 equiv.) are reacted to give the named compound as a yellow solid (690 mg, 64%).
Conditions: See reaction.notes.procedure_details.
Worku... | 10.6084/m9.figshare.5104873.v1 | null | Enol.Primary amine | Enamine | null | null | c1ccc2c(c1)CCN2.c1ccccc1.C1CC[NH]C1 | HO- | null | null | null | Nc1ccc(OCCN2CCCC2)cc1.O=C1Nc2ccccc2C1=CO>>O=C1Nc2ccccc2C1=CNc1ccc(OCCN2CCCC2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-ce4b58c430e84771ac46e534aefbc03e | Nc1ccc(OCCN2CCCC2)cc1.O=C1Nc2cccc(F)c2C1=CO>>O=C1Nc2cccc(F)c2C1=CNc1ccc(OCCN2CCCC2)cc1 | N1(CCCC1)CCOC1=CC=C(C=C1)N.FC1=C2C(C(NC2=CC=C1)=O)=CO>>FC1=C2C(C(NC2=CC=C1)=O)=CNC1=CC=C(C=C1)OCCN1CCCC1 | [NH2:13][c:14]1[cH:15][cH:16][c:17]([O:18][CH2:19][CH2:20][N:21]2[CH2:22][CH2:23][CH2:24][CH2:25]2)[cH:26][cH:27]1.O[CH:12]=[C:11]1[C:2](=[O:1])[NH:3][c:4]2[cH:5][cH:6][cH:7][c:8]([F:9])[c:10]21>>[O:1]=[C:2]1[NH:3][c:4]2[cH:5][cH:6][cH:7][c:8]([F:9])[c:10]2[C:11]1=[CH:12][NH:13][c:14]1[cH:15][cH:16][c:17]([O:18][CH2:19... | Nc1ccc(OCCN2CCCC2)cc1.O=C1Nc2cccc(F)c2C1=CO | O=C1Nc2cccc(F)c2C1=CNc1ccc(OCCN2CCCC2)cc1 | null | null | null | Heteroatom Alkylation and Arylation | Reductive amination with alcohol | ac661a5987df49e763a2386679221354b73376953f4071e32e52e2d7e8877593 | dc27e5e3871ba014ddcdbe66aa8244518b94cc851f1ff4159b6674656bc3b780 | O=C1Nc2ccccc2C1=CNc1ccc(OCCN2CCCC2)cc1 | O-[CH;D2;+0:1]=[C:2]1-[c:3]:[c:4]-[#7:5]-[C:6]-1=[O;D1;H0:7].[NH2;D1;+0:8]-[c:9](:[c:10]):[c:11]>>[O;D1;H0:7]=[C:6]1-[#7:5]-[c:4]:[c:3]-[C:2]-1=[CH;D2;+0:1]-[NH;D2;+0:8]-[c:9](:[c:10]):[c:11] | 77.1 | [{"value": 77.0, "product": "FC1=C2C(C(NC2=CC=C1)=O)=CNC1=CC=C(C=C1)OCCN1CCCC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 77.1, "product": "FC1=C2C(C(NC2=CC=C1)=O)=CNC1=CC=C(C=C1)OCCN1CCCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | In a manner similar to that described in Example 231, 4-(2-pyrrolidin-1-yl-ethoxy)-phenylamine (690 mg, 1.2 equiv.) and 4-fluoro-3-hydroxymethylene-1,3-dihydro-indol-2-one (500 mg, 2.79 mmol, 1 equiv.) to give the named compound as a yellow solid (790 mg, 77.0%).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Enol.Primary amine | Enamine | null | null | c1ccc2c(c1)CCN2.c1ccccc1.C1CC[NH]C1 | HO- | null | null | null | Nc1ccc(OCCN2CCCC2)cc1.O=C1Nc2cccc(F)c2C1=CO>>O=C1Nc2cccc(F)c2C1=CNc1ccc(OCCN2CCCC2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-7c64fb7189b2415199b6b89369a8a6fb | Nc1ccc(OCCN2CCCC2)cc1.O=C1Nc2ccc(F)cc2C1=CO>>O=C1Nc2ccc(F)cc2C1=CNc1ccc(OCCN2CCCC2)cc1 | N1(CCCC1)CCOC1=CC=C(C=C1)N.FC=1C=C2C(C(NC2=CC1)=O)=CO>>FC=1C=C2C(C(NC2=CC1)=O)=CNC1=CC=C(C=C1)OCCN1CCCC1 | [NH2:13][c:14]1[cH:15][cH:16][c:17]([O:18][CH2:19][CH2:20][N:21]2[CH2:22][CH2:23][CH2:24][CH2:25]2)[cH:26][cH:27]1.O[CH:12]=[C:11]1[C:2](=[O:1])[NH:3][c:4]2[cH:5][cH:6][c:7]([F:8])[cH:9][c:10]21>>[O:1]=[C:2]1[NH:3][c:4]2[cH:5][cH:6][c:7]([F:8])[cH:9][c:10]2[C:11]1=[CH:12][NH:13][c:14]1[cH:15][cH:16][c:17]([O:18][CH2:19... | Nc1ccc(OCCN2CCCC2)cc1.O=C1Nc2ccc(F)cc2C1=CO | O=C1Nc2ccc(F)cc2C1=CNc1ccc(OCCN2CCCC2)cc1 | null | null | null | Heteroatom Alkylation and Arylation | Reductive amination with alcohol | ac661a5987df49e763a2386679221354b73376953f4071e32e52e2d7e8877593 | dc27e5e3871ba014ddcdbe66aa8244518b94cc851f1ff4159b6674656bc3b780 | O=C1Nc2ccccc2C1=CNc1ccc(OCCN2CCCC2)cc1 | O-[CH;D2;+0:1]=[C:2]1-[c:3]:[c:4]-[#7:5]-[C:6]-1=[O;D1;H0:7].[NH2;D1;+0:8]-[c:9](:[c:10]):[c:11]>>[O;D1;H0:7]=[C:6]1-[#7:5]-[c:4]:[c:3]-[C:2]-1=[CH;D2;+0:1]-[NH;D2;+0:8]-[c:9](:[c:10]):[c:11] | 69 | [{"value": 69.0, "product": "FC=1C=C2C(C(NC2=CC1)=O)=CNC1=CC=C(C=C1)OCCN1CCCC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 68.8, "product": "FC=1C=C2C(C(NC2=CC1)=O)=CNC1=CC=C(C=C1)OCCN1CCCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | In a manner similar to that described in Example 231, 4-(2-Pyrrolidin-1-yl-ethoxy)-phenylamine (690 mg, 1.2 equiv.) and 5-fluoro-3-hydroxymethylene-1,3-dihydro-indol-2-one (500 mg, 2.79 mmol, 1 equiv.) are reacted to give the named compound as a yellow solid (705 mg, 69%).
Conditions: See reaction.notes.procedure_detai... | 10.6084/m9.figshare.5104873.v1 | null | Enol.Primary amine | Enamine | null | null | c1ccc2c(c1)CCN2.c1ccccc1.C1CC[NH]C1 | HO- | null | null | null | Nc1ccc(OCCN2CCCC2)cc1.O=C1Nc2ccc(F)cc2C1=CO>>O=C1Nc2ccc(F)cc2C1=CNc1ccc(OCCN2CCCC2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-e4ed8fa2876743748633148fa540b5c2 | Nc1ccc(OCCN2CCCC2)cc1.O=C1Nc2ccc(Cl)cc2C1=CO>>O=C1Nc2ccc(Cl)cc2C1=CNc1ccc(OCCN2CCCC2)cc1 | N1(CCCC1)CCOC1=CC=C(C=C1)N.ClC=1C=C2C(C(NC2=CC1)=O)=CO>>ClC=1C=C2C(C(NC2=CC1)=O)=CNC1=CC=C(C=C1)OCCN1CCCC1 | [NH2:13][c:14]1[cH:15][cH:16][c:17]([O:18][CH2:19][CH2:20][N:21]2[CH2:22][CH2:23][CH2:24][CH2:25]2)[cH:26][cH:27]1.O[CH:12]=[C:11]1[C:2](=[O:1])[NH:3][c:4]2[cH:5][cH:6][c:7]([Cl:8])[cH:9][c:10]21>>[O:1]=[C:2]1[NH:3][c:4]2[cH:5][cH:6][c:7]([Cl:8])[cH:9][c:10]2[C:11]1=[CH:12][NH:13][c:14]1[cH:15][cH:16][c:17]([O:18][CH2:... | Nc1ccc(OCCN2CCCC2)cc1.O=C1Nc2ccc(Cl)cc2C1=CO | O=C1Nc2ccc(Cl)cc2C1=CNc1ccc(OCCN2CCCC2)cc1 | null | null | null | Heteroatom Alkylation and Arylation | Reductive amination with alcohol | ac661a5987df49e763a2386679221354b73376953f4071e32e52e2d7e8877593 | dc27e5e3871ba014ddcdbe66aa8244518b94cc851f1ff4159b6674656bc3b780 | O=C1Nc2ccccc2C1=CNc1ccc(OCCN2CCCC2)cc1 | O-[CH;D2;+0:1]=[C:2]1-[c:3]:[c:4]-[#7:5]-[C:6]-1=[O;D1;H0:7].[NH2;D1;+0:8]-[c:9](:[c:10]):[c:11]>>[O;D1;H0:7]=[C:6]1-[#7:5]-[c:4]:[c:3]-[C:2]-1=[CH;D2;+0:1]-[NH;D2;+0:8]-[c:9](:[c:10]):[c:11] | 79 | [{"value": 79.0, "product": "ClC=1C=C2C(C(NC2=CC1)=O)=CNC1=CC=C(C=C1)OCCN1CCCC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 78.9, "product": "ClC=1C=C2C(C(NC2=CC1)=O)=CNC1=CC=C(C=C1)OCCN1CCCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | In a manner similar to that described in Example 231, 4-(2-Pyrrolidin-1-yl-ethoxy)-phenylamine (632 mg, 1.2 equiv.) and 5-chloro-3-hydroxymethylene-1,3-dihydro-indol-2-one (500 mg, 2.56 mmol, 1 equiv.) are reacted to give the named compound as a yellow solid (775 mg, 79%).
Conditions: See reaction.notes.procedure_detai... | 10.6084/m9.figshare.5104873.v1 | null | Enol.Primary amine | Enamine | null | null | c1ccc2c(c1)CCN2.c1ccccc1.C1CC[NH]C1 | HO- | null | null | null | Nc1ccc(OCCN2CCCC2)cc1.O=C1Nc2ccc(Cl)cc2C1=CO>>O=C1Nc2ccc(Cl)cc2C1=CNc1ccc(OCCN2CCCC2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-76889c47bc604c94bffd53a4958f5462 | COc1cccc(-c2ccc3c(c2)NC(=O)C3=CO)c1.Nc1ccc(OCCCN2CCCCC2)cc1>>COc1cccc(-c2ccc3c(c2)NC(=O)C3=CNc2ccc(OCCCN3CCCCC3)cc2)c1 | OC=C1C(NC2=CC(=CC=C12)C1=CC(=CC=C1)OC)=O.N1(CCCCC1)CCCOC1=CC=C(C=C1)N>>COC=1C=C(C=CC1)C1=CC=C2C(C(NC2=C1)=O)=CNC1=CC=C(C=C1)OCCCN1CCCCC1 | O[CH:18]=[C:17]1[c:11]2[cH:10][cH:9][c:8](-[c:7]3[cH:6][cH:5][cH:4][c:3]([O:2][CH3:1])[cH:36]3)[cH:13][c:12]2[NH:14][C:15]1=[O:16].[NH2:19][c:20]1[cH:21][cH:22][c:23]([O:24][CH2:25][CH2:26][CH2:27][N:28]2[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33]2)[cH:34][cH:35]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7](-[c:8]2[cH:9][c... | COc1cccc(-c2ccc3c(c2)NC(=O)C3=CO)c1.Nc1ccc(OCCCN2CCCCC2)cc1 | COc1cccc(-c2ccc3c(c2)NC(=O)C3=CNc2ccc(OCCCN3CCCCC3)cc2)c1 | null | null | O1CCCC1 | Heteroatom Alkylation and Arylation | Reductive amination with alcohol | ac661a5987df49e763a2386679221354b73376953f4071e32e52e2d7e8877593 | dc27e5e3871ba014ddcdbe66aa8244518b94cc851f1ff4159b6674656bc3b780 | O=C1Nc2cc(-c3ccccc3)ccc2C1=CNc1ccc(OCCCN2CCCCC2)cc1 | O-[CH;D2;+0:1]=[C:2]1-[c:3]:[c:4]-[#7:5]-[C:6]-1=[O;D1;H0:7].[NH2;D1;+0:8]-[c:9](:[c:10]):[c:11]>>[O;D1;H0:7]=[C:6]1-[#7:5]-[c:4]:[c:3]-[C:2]-1=[CH;D2;+0:1]-[NH;D2;+0:8]-[c:9](:[c:10]):[c:11] | null | [] | null | null | null | null | The named compound is prepared by refluxing 0.020 gms E & Z 3-hydroxymethylene-6-(3-methoxy-phenyl)-1,3-dihydro-indol-2-one (see example 268) with 0.0375 gms 4-(3-piperidin-1-yl-propoxy)-phenylamine (used in the preparation of Example 218) in tetrahydrofuran (0.33 mL) for 36 h. Following cooling to room temperature, so... | 10.6084/m9.figshare.5104873.v1 | null | Enol.Primary amine | Enamine | null | null | c1ccccc1.c1ccc2c(c1)CCN2.c1ccccc1.C1CC[NH]CC1 | HO- | O1CCCC1 | null | null | COc1cccc(-c2ccc3c(c2)NC(=O)C3=CO)c1.Nc1ccc(OCCCN2CCCCC2)cc1>O1CCCC1>COc1cccc(-c2ccc3c(c2)NC(=O)C3=CNc2ccc(OCCCN3CCCCC3)cc2)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-2148a18e37e141fc89ef9749d3d20235 | CCN(CC)CCCOc1ccc(N)cc1.COc1cccc(-c2ccc3c(c2)NC(=O)C3=CO)c1>>CCN(CC)CCCOc1ccc(NC=C2C(=O)Nc3cc(-c4cccc(OC)c4)ccc32)cc1 | OC=C1C(NC2=CC(=CC=C12)C1=CC(=CC=C1)OC)=O.C(C)N(CCCOC1=CC=C(C=C1)N)CC>>C(C)N(CCCOC1=CC=C(C=C1)NC=C1C(NC2=CC(=CC=C12)C1=CC(=CC=C1)OC)=O)CC | [CH3:1][CH2:2][N:3]([CH2:4][CH3:5])[CH2:6][CH2:7][CH2:8][O:9][c:10]1[cH:11][cH:12][c:13]([NH2:14])[cH:34][cH:35]1.O[CH:15]=[C:16]1[C:17](=[O:18])[NH:19][c:20]2[cH:21][c:22](-[c:23]3[cH:24][cH:25][cH:26][c:27]([O:28][CH3:29])[cH:30]3)[cH:31][cH:32][c:33]21>>[CH3:1][CH2:2][N:3]([CH2:4][CH3:5])[CH2:6][CH2:7][CH2:8][O:9][c... | CCN(CC)CCCOc1ccc(N)cc1.COc1cccc(-c2ccc3c(c2)NC(=O)C3=CO)c1 | CCN(CC)CCCOc1ccc(NC=C2C(=O)Nc3cc(-c4cccc(OC)c4)ccc32)cc1 | null | null | O1CCCC1 | Heteroatom Alkylation and Arylation | Reductive amination with alcohol | ac661a5987df49e763a2386679221354b73376953f4071e32e52e2d7e8877593 | dc27e5e3871ba014ddcdbe66aa8244518b94cc851f1ff4159b6674656bc3b780 | O=C1Nc2cc(-c3ccccc3)ccc2C1=CNc1ccccc1 | O-[CH;D2;+0:1]=[C:2]1-[c:3]:[c:4]-[#7:5]-[C:6]-1=[O;D1;H0:7].[NH2;D1;+0:8]-[c:9](:[c:10]):[c:11]>>[O;D1;H0:7]=[C:6]1-[#7:5]-[c:4]:[c:3]-[C:2]-1=[CH;D2;+0:1]-[NH;D2;+0:8]-[c:9](:[c:10]):[c:11] | null | [] | null | null | null | null | The named compound is prepared by refluxing 0.020 gms E & Z 3-Hydroxymethylene-6-(3-methoxy-phenyl)-1,3-dihydro-indol-2-one (see example 268) with 0.0327 gms 4-(3-diethylamino-propoxy)-phenylamine (used in the preparation of Example 214) in tetrahydrofuran (0.33 mL) for 36 h. Following cooling to room temperature, solv... | 10.6084/m9.figshare.5104873.v1 | null | Enol.Primary amine | Enamine | null | null | c1ccccc1.c1ccc2c(c1)CCN2.c1ccccc1 | HO- | O1CCCC1 | null | null | CCN(CC)CCCOc1ccc(N)cc1.COc1cccc(-c2ccc3c(c2)NC(=O)C3=CO)c1>O1CCCC1>CCN(CC)CCCOc1ccc(NC=C2C(=O)Nc3cc(-c4cccc(OC)c4)ccc32)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-c9bf66c10baf433d9eede5e31b36809b | CN1CCCC(COc2ccc(N)cc2)C1.Cc1cccc2c1C(=CO)C(=O)N2>>Cc1cccc2c1C(=CNc1ccc(OCC3CCCN(C)C3)cc1)C(=O)N2 | CN1CC(CCC1)COC1=CC=C(C=C1)N.CC1=C2C(C(NC2=CC=C1)=O)=CO>>CC1=C2C(C(NC2=CC=C1)=O)=CNC1=CC=C(C=C1)OCC1CN(CCC1)C | [NH2:10][c:11]1[cH:12][cH:13][c:14]([O:15][CH2:16][CH:17]2[CH2:18][CH2:19][CH2:20][N:21]([CH3:22])[CH2:23]2)[cH:24][cH:25]1.O[CH:9]=[C:8]1[c:7]2[c:2]([CH3:1])[cH:3][cH:4][cH:5][c:6]2[NH:28][C:26]1=[O:27]>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][c:6]2[c:7]1[C:8](=[CH:9][NH:10][c:11]1[cH:12][cH:13][c:14]([O:15][CH2:16][CH:17]3[C... | CN1CCCC(COc2ccc(N)cc2)C1.Cc1cccc2c1C(=CO)C(=O)N2 | Cc1cccc2c1C(=CNc1ccc(OCC3CCCN(C)C3)cc1)C(=O)N2 | null | null | null | Heteroatom Alkylation and Arylation | Reductive amination with alcohol | ac661a5987df49e763a2386679221354b73376953f4071e32e52e2d7e8877593 | dc27e5e3871ba014ddcdbe66aa8244518b94cc851f1ff4159b6674656bc3b780 | O=C1Nc2ccccc2C1=CNc1ccc(OCC2CCCNC2)cc1 | O-[CH;D2;+0:1]=[C:2]1-[c:3]:[c:4]-[#7:5]-[C:6]-1=[O;D1;H0:7].[NH2;D1;+0:8]-[c:9](:[c:10]):[c:11]>>[O;D1;H0:7]=[C:6]1-[#7:5]-[c:4]:[c:3]-[C:2]-1=[CH;D2;+0:1]-[NH;D2;+0:8]-[c:9](:[c:10]):[c:11] | 51 | [{"value": 51.0, "product": "CC1=C2C(C(NC2=CC=C1)=O)=CNC1=CC=C(C=C1)OCC1CN(CCC1)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 51.0, "product": "CC1=C2C(C(NC2=CC=C1)=O)=CNC1=CC=C(C=C1)OCC1CN(CCC1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | In a manner similar to that described in Example 231, 4-(1-methyl-piperidin-3-ylmethoxy)-phenylamine (603 mg, 1.2 equiv.) and 4-methyl-3-hydroxymethylene-1,3-dihydro-indol-2-one (400 mg, 2.28 mmol, 1 equiv.) are reacted to give the named compound as a yellow solid (439 mg, 51%).
Conditions: See reaction.notes.procedure... | 10.6084/m9.figshare.5104873.v1 | null | Enol.Primary amine | Enamine | null | null | c1ccccc1.C1CC[NH]CC1.c1ccc2c(c1)CCN2 | HO- | null | null | null | CN1CCCC(COc2ccc(N)cc2)C1.Cc1cccc2c1C(=CO)C(=O)N2>>Cc1cccc2c1C(=CNc1ccc(OCC3CCCN(C)C3)cc1)C(=O)N2 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-d0bf15e3be6f45c0b9d561ea4cb75913 | CN1CCCC(COc2ccc(N)cc2)C1.O=C1Nc2cc(F)ccc2C1=CO>>CN1CCCC(COc2ccc(NC=C3C(=O)Nc4cc(F)ccc43)cc2)C1 | CN1CC(CCC1)COC1=CC=C(C=C1)N.FC1=CC=C2C(C(NC2=C1)=O)=CO>>FC1=CC=C2C(C(NC2=C1)=O)=CNC1=CC=C(C=C1)OCC1CN(CCC1)C | [CH3:1][N:2]1[CH2:3][CH2:4][CH2:5][CH:6]([CH2:7][O:8][c:9]2[cH:10][cH:11][c:12]([NH2:13])[cH:26][cH:27]2)[CH2:28]1.O[CH:14]=[C:15]1[C:16](=[O:17])[NH:18][c:19]2[cH:20][c:21]([F:22])[cH:23][cH:24][c:25]21>>[CH3:1][N:2]1[CH2:3][CH2:4][CH2:5][CH:6]([CH2:7][O:8][c:9]2[cH:10][cH:11][c:12]([NH:13][CH:14]=[C:15]3[C:16](=[O:17... | CN1CCCC(COc2ccc(N)cc2)C1.O=C1Nc2cc(F)ccc2C1=CO | CN1CCCC(COc2ccc(NC=C3C(=O)Nc4cc(F)ccc43)cc2)C1 | null | null | null | Heteroatom Alkylation and Arylation | Reductive amination with alcohol | ac661a5987df49e763a2386679221354b73376953f4071e32e52e2d7e8877593 | dc27e5e3871ba014ddcdbe66aa8244518b94cc851f1ff4159b6674656bc3b780 | O=C1Nc2ccccc2C1=CNc1ccc(OCC2CCCNC2)cc1 | O-[CH;D2;+0:1]=[C:2]1-[c:3]:[c:4]-[#7:5]-[C:6]-1=[O;D1;H0:7].[NH2;D1;+0:8]-[c:9](:[c:10]):[c:11]>>[O;D1;H0:7]=[C:6]1-[#7:5]-[c:4]:[c:3]-[C:2]-1=[CH;D2;+0:1]-[NH;D2;+0:8]-[c:9](:[c:10]):[c:11] | 55 | [{"value": 55.0, "product": "FC1=CC=C2C(C(NC2=C1)=O)=CNC1=CC=C(C=C1)OCC1CN(CCC1)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 54.8, "product": "FC1=CC=C2C(C(NC2=C1)=O)=CNC1=CC=C(C=C1)OCC1CN(CCC1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | In a manner similar to that described in Example 231, 4-(1-methylpiperidin-3-ylmethoxy)-phenylamine (590 mg, 1.2 equiv.) and 6-fluoro-3-hydroxymethylene-1,3-dihydro-indol-2-one (400 mg, 2.23 mmol, 1 equiv.) are reacted to give the named compound as a yellow solid (466 mg, 55%).
Conditions: See reaction.notes.procedure_... | 10.6084/m9.figshare.5104873.v1 | null | Enol.Primary amine | Enamine | null | null | C1CC[NH]CC1.c1ccccc1.c1ccc2c(c1)CCN2 | HO- | null | null | null | CN1CCCC(COc2ccc(N)cc2)C1.O=C1Nc2cc(F)ccc2C1=CO>>CN1CCCC(COc2ccc(NC=C3C(=O)Nc4cc(F)ccc43)cc2)C1 |
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