dataset_id large_stringclasses 414
values | reaction_id large_stringlengths 36 36 | reaction_smiles large_stringlengths 4 873 | rxn_insight_reaction large_stringlengths 19 1.07k | mapped_reaction_smiles large_stringlengths 14 3.37k | reactant_smiles large_stringlengths 1 581 | product_smiles large_stringlengths 1 433 | reagent_smiles large_stringclasses 634
values | catalyst_smiles large_stringlengths 1 683 ⌀ | solvent_smiles large_stringlengths 1 245 ⌀ | rxn_insight_class large_stringclasses 11
values | rxn_insight_name large_stringclasses 346
values | rxn_insight_tag large_stringlengths 64 64 | rxn_insight_tag2 large_stringlengths 64 64 | rxn_insight_scaffold large_stringlengths 5 288 ⌀ | rxn_insight_template large_stringlengths 24 2.64k ⌀ | yield_percent float64 -0.8 90,205,160,000B ⌀ | yield_measurements large_stringlengths 2 864 | temperature_value float64 -230 30.1k ⌀ | temperature_units large_stringclasses 3
values | reaction_time_value float64 0 4k ⌀ | time_units large_stringclasses 4
values | procedure_details large_stringlengths 1 23.6k ⌀ | reference large_stringclasses 96
values | doi large_stringclasses 19
values | functional_groups_reactants large_stringlengths 3 716 ⌀ | functional_groups_products large_stringlengths 3 539 ⌀ | participating_rings_reactants large_stringlengths 5 293 ⌀ | participating_rings_products large_stringlengths 5 271 ⌀ | all_rings_products large_stringlengths 5 271 ⌀ | byproduct_smiles large_stringclasses 176
values | agent_smiles large_stringlengths 1 712 ⌀ | temperature_c float64 -230 30.1k ⌀ | reaction_time_hours float64 0 2.16k ⌀ | reaction_smiles_with_agents large_stringlengths 4 882 |
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-907218e6526b4b39bc1c602a8542be49 | O=C(O)[C@@H](O)[C@H](O)C(=O)O>>O=C([O-])[C@@H](O)[C@H](O)C(=O)[O-] | C([C@@H](O)[C@H](O)C(=O)O)(=O)O.C1[C@@H]([C@H]([C@@H](CN1)O)O)CO>>C1[C@@H]([C@H]([C@@H](CN1)O)O)CO.C(=O)([O-])[C@@H](O)[C@H](O)C(=O)[O-] | [O:1]=[C:2]([OH:3])[C@@H:4]([OH:5])[C@H:6]([OH:7])[C:8](=[O:9])[OH:10]>>[O:1]=[C:2]([O-:3])[C@@H:4]([OH:5])[C@H:6]([OH:7])[C:8](=[O:9])[O-:10] | O=C(O)[C@@H](O)[C@H](O)C(=O)O | O=C([O-])[C@@H](O)[C@H](O)C(=O)[O-] | null | null | O | Oxidation | OtherReaction | 4af04878ecd22d61c6d7d46db52e672904d5e72408231940a5cea872324a16a2 | 4e878a1fdc9370141a3ed00507bdfaa037f36d163bb15c5076375a9835c80b8f | null | [O;D1;H0:1]=[C:2](-[OH;D1;+0:3])-[C:4]-[C:5]-[C:6](=[O;D1;H0:7])-[OH;D1;+0:8]>>[O-;H0;D1:8]-[C:6](=[O;D1;H0:7])-[C:5]-[C:4]-[C:2](-[O-;H0;D1:3])=[O;D1;H0:1] | 98.9 | [{"value": 98.0, "product": "C1[C@@H]([C@H]([C@@H](CN1)O)O)CO.C(=O)([O-])[C@@H](O)[C@H](O)C(=O)[O-]", "details": "PERCENTYIELD", "is_desired": false}, {"value": 98.9, "product": "C1[C@@H]([C@H]([C@@H](CN1)O)O)CO.C(=O)([O-])[C@@H](O)[C@H](O)C(=O)[O-]", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 10 | MINUTE | A solution of D-(−)-tartaric acid (204 mg, 1.359 mmol) in deionized water (2.0 mL) was added into the solution of isofagomine (200 mg, 2.0 equivalents) dissolved in deionized water (2.0 mL) at room temperature. The solution was stirred for 10 min and lyophilized overnight. The residue was further dried under vacuum at ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Carboxylic acid | null | null | null | null | null | O | null | 0.166667 | O=C(O)[C@@H](O)[C@H](O)C(=O)O>O>O=C([O-])[C@@H](O)[C@H](O)C(=O)[O-] |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-bbb351fe6fd04e98bd244d8546e5d60e | C=C1C[C@@H](C(=O)OCC)[C@H](C(=O)OCC)C1>>C=C1C[C@@H](C(=O)O)[C@H](C(=O)OCC)C1 | C(C)OC(=O)[C@H]1[C@@H](CC(C1)=C)C(=O)OCC.C([O-])([O-])=O.[K+].[K+].Cl>>C(C)OC(=O)[C@H]1[C@@H](CC(C1)=C)C(=O)O | CC[O:7][C:5]([C@@H:4]1[CH2:3][C:2](=[CH2:1])[CH2:14][C@H:8]1[C:9](=[O:10])[O:11][CH2:12][CH3:13])=[O:6]>>[CH2:1]=[C:2]1[CH2:3][C@@H:4]([C:5](=[O:6])[OH:7])[C@H:8]([C:9](=[O:10])[O:11][CH2:12][CH3:13])[CH2:14]1 | C=C1C[C@@H](C(=O)OCC)[C@H](C(=O)OCC)C1 | C=C1C[C@@H](C(=O)O)[C@H](C(=O)OCC)C1 | null | null | O.CO | Deprotection | Ester saponification (alkyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | C=C1CCCC1 | C-C-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4]>>[C:3]-[C:2](=[O;D1;H0:4])-[OH;D1;+0:1] | 49.1 | [{"value": 49.1, "product": "C(C)OC(=O)[C@H]1[C@@H](CC(C1)=C)C(=O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A suspension of 20.0 g of trans-(1SR,2SR)-4-methylene-cyclopentane-1,2-dicarboxylic acid diethyl ester and 36.6 g of potassium carbonate in 200 ml of MeOH was heated at reflux temperature for 2 h. The mixture was cooled to 22°, diluted with 200 ml of water, the pH was adjusted to 2 using 80 ml of 25% HCl and the mixtur... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | C1CCCC1 | Other | O.CO | null | null | C=C1C[C@@H](C(=O)OCC)[C@H](C(=O)OCC)C1>O.CO>C=C1C[C@@H](C(=O)O)[C@H](C(=O)OCC)C1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-874f0f7e20284885950217314592bb1d | C=C1C[C@@H](C(=O)O)[C@H](C(=O)OCC)C1.Nc1ccc(Cl)cc1>>C=C1C[C@@H](C(=O)Nc2ccc(Cl)cc2)[C@H](C(=O)OC)C1 | OC1=CC=CC=2NN=NC21.Cl.CN(CCCN=C=NCC)C.C(C)OC(=O)[C@H]1[C@@H](CC(C1)=C)C(=O)O.ClC1=CC=C(N)C=C1>>COC(=O)[C@H]1[C@@H](CC(C1)=C)C(NC1=CC=C(C=C1)Cl)=O | C[CH2:19][O:18][C:16]([C@H:15]1[C@H:4]([C:5](O)=[O:6])[CH2:3][C:2](=[CH2:1])[CH2:20]1)=[O:17].[NH2:7][c:8]1[cH:9][cH:10][c:11]([Cl:12])[cH:13][cH:14]1>>[CH2:1]=[C:2]1[CH2:3][C@@H:4]([C:5](=[O:6])[NH:7][c:8]2[cH:9][cH:10][c:11]([Cl:12])[cH:13][cH:14]2)[C@H:15]([C:16](=[O:17])[O:18][CH3:19])[CH2:20]1 | C=C1C[C@@H](C(=O)O)[C@H](C(=O)OCC)C1.Nc1ccc(Cl)cc1 | C=C1C[C@@H](C(=O)Nc2ccc(Cl)cc2)[C@H](C(=O)OC)C1 | null | null | CCN(CC)CC.CC#N | Acylation | OtherReaction | 3bf28875ce940bec3ebc23b5f3bab0901f018435242045ff199b1dd7ca0bb2b3 | bd93f76b28c347d49e1724c56040974bf1d3dcbde28ba19b6aa7c944fc5dd484 | C=C1CC[C@H](C(=O)Nc2ccccc2)C1 | C-[CH2;D2;+0:1]-[#8:2]-[C:3](=[O;D1;H0:4])-[C:5]-[C:6](-[C;H0;D3;+0:7](-O)=[O;D1;H0:8])-[C:9]-[C:10]=[C;D1;H2:11].[NH2;D1;+0:12]-[c:13](:[c:14]):[c:15]>>[C;D1;H2:11]=[C:10]-[C:9]-[C:6](-[C;H0;D3;+0:7](=[O;D1;H0:8])-[NH;D2;+0:12]-[c:13](:[c:14]):[c:15])-[C:5]-[C:3](=[O;D1;H0:4])-[#8:2]-[CH3;D1;+0:1] | 55.4 | [{"value": 55.4, "product": "COC(=O)[C@H]1[C@@H](CC(C1)=C)C(NC1=CC=C(C=C1)Cl)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | The crude mixture containing 1a (16.7 g) was dissolved in 500 ml of CH3CN and treated subsequently with 51 ml of NEt3, 25.0 g hydroxybenzotriazole and 31.3 g of N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride and stirring was continued at 22° C. for 30 min. The mixture was treated with 23.1 g of 4-chloroan... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Ester.Primary amine | Ester.Secondary amide | null | null | C1CCCC1.c1ccccc1 | HO- | CCN(CC)CC.CC#N | null | 0.5 | C=C1C[C@@H](C(=O)O)[C@H](C(=O)OCC)C1.Nc1ccc(Cl)cc1>CCN(CC)CC.CC#N>C=C1C[C@@H](C(=O)Nc2ccc(Cl)cc2)[C@H](C(=O)OC)C1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a779344bc4d8422e9828f1a68c0addd9 | C=C1C[C@@H](C(=O)Nc2ccc(Cl)cc2)[C@H](C(=O)OC)C1>>C=C1C[C@@H](C(=O)O)[C@H](C(=O)Nc2ccc(Cl)cc2)C1 | COC(=O)[C@H]1[C@@H](CC(C1)=C)C(NC1=CC=C(C=C1)Cl)=O>>ClC1=CC=C(C=C1)NC(=O)[C@H]1[C@@H](CC(C1)=C)C(=O)O | C[O:7][C:5](=[O:6])[C@H:8]1[C@H:4]([C:9](=[O:10])[NH:11][c:12]2[cH:13][cH:14][c:15]([Cl:16])[cH:17][cH:18]2)[CH2:3][C:2](=[CH2:1])[CH2:19]1>>[CH2:1]=[C:2]1[CH2:3][C@@H:4]([C:5](=[O:6])[OH:7])[C@H:8]([C:9](=[O:10])[NH:11][c:12]2[cH:13][cH:14][c:15]([Cl:16])[cH:17][cH:18]2)[CH2:19]1 | C=C1C[C@@H](C(=O)Nc2ccc(Cl)cc2)[C@H](C(=O)OC)C1 | C=C1C[C@@H](C(=O)O)[C@H](C(=O)Nc2ccc(Cl)cc2)C1 | null | null | CO.[OH-].[Na+] | Miscellaneous | Ester saponification (methyl deprotection) | 72bfc188ff30c9f80694ad619286ad6015a27c0992692c95fc6f33843ff64595 | efff1c8096c49f5ffa3170381757d0670eba1ebba95c4daf05c233e5c1bbdf96 | C=C1CC[C@H](C(=O)Nc2ccccc2)C1 | C-[O;H0;D2;+0:1]-[C;H0;D3;+0:2](=[O;D1;H0:3])-[C@@H;D3;+0:4]1-[C:5]-[C:6](=[C;D1;H2:7])-[C:8]-[C@H;D3;+0:9]-1-[C;H0;D3;+0:10](=[O;D1;H0:11])-[#7:12]-[c:13]>>[C;D1;H2:7]=[C:6]1-[C:5]-[C@@H;D3;+0:4](-[C;H0;D3;+0:10](=[O;D1;H0:11])-[#7:12]-[c:13])-[C@H;D3;+0:9](-[C;H0;D3;+0:2](=[O;D1;H0:3])-[OH;D1;+0:1])-[C:8]-1 | null | [] | null | null | null | null | The crude material 1b (13.7 g) was dissolved in 200 ml of MeOH and 20 ml of 7 N NaOH, the solution was stirred at 22° C. for 2 h and evaporated. The residue was partitioned between 0.1 N NaOH and CH2Cl2, the aqueous layer was washed with CH2Cl2 and the aqueous layer was acidified with 25% HCl, the suspension was filter... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Secondary amide | Carboxylic acid.Secondary amide | C1CCCC1 | C1CCCC1 | C1CCCC1.c1ccccc1 | Other | CO.[OH-].[Na+] | null | null | C=C1C[C@@H](C(=O)Nc2ccc(Cl)cc2)[C@H](C(=O)OC)C1>CO.[OH-].[Na+]>C=C1C[C@@H](C(=O)O)[C@H](C(=O)Nc2ccc(Cl)cc2)C1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-948f02989d8747778707dea01672f602 | C=C1C[C@@H](C(=O)O)[C@H](C(=O)OCC)C1.CC(C)(C)O.[N-]=[N+]=NP(=O)(c1ccccc1)c1ccccc1>>C=C1CC(NC(=O)OC(C)(C)C)C(C(=O)OC)C1 | CC(C)(C)O.C(C)OC(=O)[C@H]1[C@@H](CC(C1)=C)C(=O)O.CCN(CC)CC.C1(=CC=CC=C1)P(=O)(C1=CC=CC=C1)N=[N+]=[N-]>>COC(=O)C1C(CC(C1)=C)NC(=O)OC(C)(C)C | C[CH2:17][O:16][C:14]([C@H:13]1[C@H:4]([C:6](O)=[O:7])[CH2:3][C:2](=[CH2:1])[CH2:18]1)=[O:15].[OH:8][C:9]([CH3:10])([CH3:11])[CH3:12].[N-]=[N+]=[N:5]P(=O)(c1ccccc1)c1ccccc1>>[CH2:1]=[C:2]1[CH2:3][CH:4]([NH:5][C:6](=[O:7])[O:8][C:9]([CH3:10])([CH3:11])[CH3:12])[CH:13]([C:14](=[O:15])[O:16][CH3:17])[CH2:18]1 | C=C1C[C@@H](C(=O)O)[C@H](C(=O)OCC)C1.CC(C)(C)O.[N-]=[N+]=NP(=O)(c1ccccc1)c1ccccc1 | C=C1CC(NC(=O)OC(C)(C)C)C(C(=O)OC)C1 | null | null | C1(=CC=CC=C1)C | Protection | OtherReaction | 136944a1a3303309ac55275fa1a14b60cc0f29f5b963bb97b5c11e96d1e8c5b9 | f2e92b5e20ec18885db87a01f7679b5ebb1cd68f65a21ea18ef3566f94514ce6 | C=C1CCCC1 | C-[CH2;D2;+0:1]-[#8:2]-[C:3](=[O;D1;H0:4])-[C@@H;D3;+0:5]1-[C:6]-[C:7](=[C;D1;H2:8])-[C:9]-[C@H;D3;+0:10]-1-[C;H0;D3;+0:11](-O)=[O;D1;H0:12].O=P(-[N;H0;D2;+0:13]=[N+]=[N-])(-c1:c:c:c:c:c:1)-c1:c:c:c:c:c:1.[C;D1;H3:14]-[C:15](-[C;D1;H3:16])(-[C;D1;H3:17])-[OH;D1;+0:18]>>[C;D1;H2:8]=[C:7]1-[C:6]-[CH;D3;+0:5](-[C:3](=[O;D... | 59.3 | [{"value": 55.0, "product": "COC(=O)C1C(CC(C1)=C)NC(=O)OC(C)(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 59.3, "product": "COC(=O)C1C(CC(C1)=C)NC(=O)OC(C)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 16 | HOUR | To a solution of 2.03 g trans-(1SR,2SR)-4-methylene-cyclopentane-1,2-dicarboxylic acid ethyl ester (prepared and purified according to example 1 and 2, step 1) and 1.13 g of NEt3 in 25 ml of toluene was added drop wise at 22° C. 3.03 g of diphenylphosphoryl azide and the mixture was heated at 80° C. for 30 min. The mix... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Ester.Azide.Tertiary alcohol | Carbamic ester.Ester.Ether.Boc | C1CCCC1.c1ccccc1.c1ccccc1 | C1CCCC1 | C1CCCC1 | HO- | C1(=CC=CC=C1)C | null | 16 | C=C1C[C@@H](C(=O)O)[C@H](C(=O)OCC)C1.CC(C)(C)O.[N-]=[N+]=NP(=O)(c1ccccc1)c1ccccc1>C1(=CC=CC=C1)C>C=C1CC(NC(=O)OC(C)(C)C)C(C(=O)OC)C1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-dd47680ab9c74cf5a2274334146045a8 | C=C1CC(NC(=O)OC(C)(C)C)C(C(=O)OC)C1>>C=C1CC(NC(=O)OC(C)(C)C)C(C(=O)O)C1 | COC(=O)C1C(CC(C1)=C)NC(=O)OC(C)(C)C.O[Li].O>>C(C)(C)(C)OC(=O)NC1C(CC(C1)=C)C(=O)O | C[O:16][C:14]([CH:13]1[CH:4]([NH:5][C:6](=[O:7])[O:8][C:9]([CH3:10])([CH3:11])[CH3:12])[CH2:3][C:2](=[CH2:1])[CH2:17]1)=[O:15]>>[CH2:1]=[C:2]1[CH2:3][CH:4]([NH:5][C:6](=[O:7])[O:8][C:9]([CH3:10])([CH3:11])[CH3:12])[CH:13]([C:14](=[O:15])[OH:16])[CH2:17]1 | C=C1CC(NC(=O)OC(C)(C)C)C(C(=O)OC)C1 | C=C1CC(NC(=O)OC(C)(C)C)C(C(=O)O)C1 | null | null | O.CO | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | C=C1CCCC1 | C-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4]>>[C:3]-[C:2](=[O;D1;H0:4])-[OH;D1;+0:1] | 93.4 | [{"value": 93.0, "product": "C(C)(C)(C)OC(=O)NC1C(CC(C1)=C)C(=O)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 93.4, "product": "C(C)(C)(C)OC(=O)NC1C(CC(C1)=C)C(=O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | To a solution of 1.28 g of 35a in 30 ml of MeOH was added a solution of 0.42 g of LiOH.H2O in 10 ml of H2O and stirring was continued at 50° C. for 1 h. The solution was evaporated to approximately half of the volume, the aqueous layer was washed with Et2O, acidified with HCl, the suspension was filtered and the residu... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | C1CCCC1 | Other | O.CO | null | 1 | C=C1CC(NC(=O)OC(C)(C)C)C(C(=O)OC)C1>O.CO>C=C1CC(NC(=O)OC(C)(C)C)C(C(=O)O)C1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-42fa57afbabc4cbc93c9f7ca931f91b1 | C=C1CC(NC(=O)OC(C)(C)C)C(C(=O)O)C1.Nc1ccc(Cl)cc1>>C=C1CC(NC(=O)OC(C)(C)C)C(C(=O)Nc2ccc(Cl)cc2)C1 | C(C)(C)(C)OC(=O)NC1C(CC(C1)=C)C(=O)O.OC1=CC=CC=2NN=NC21.Cl.CN(CCCN=C=NCC)C.ClC1=CC=C(N)C=C1>>C(C)(C)(C)OC(NC1C(CC(C1)=C)C(NC1=CC=C(C=C1)Cl)=O)=O | O[C:14]([CH:13]1[CH:4]([NH:5][C:6](=[O:7])[O:8][C:9]([CH3:10])([CH3:11])[CH3:12])[CH2:3][C:2](=[CH2:1])[CH2:24]1)=[O:15].[NH2:16][c:17]1[cH:18][cH:19][c:20]([Cl:21])[cH:22][cH:23]1>>[CH2:1]=[C:2]1[CH2:3][CH:4]([NH:5][C:6](=[O:7])[O:8][C:9]([CH3:10])([CH3:11])[CH3:12])[CH:13]([C:14](=[O:15])[NH:16][c:17]2[cH:18][cH:19][... | C=C1CC(NC(=O)OC(C)(C)C)C(C(=O)O)C1.Nc1ccc(Cl)cc1 | C=C1CC(NC(=O)OC(C)(C)C)C(C(=O)Nc2ccc(Cl)cc2)C1 | null | null | CCN(CC)CC.C1CCOC1 | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | C=C1CCC(C(=O)Nc2ccccc2)C1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[C:5]-[C:6]=[C;D1;H2:7].[NH2;D1;+0:8]-[c:9](:[c:10]):[c:11]>>[C:4]-[C:3](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:8]-[c:9](:[c:10]):[c:11])-[C:5]-[C:6]=[C;D1;H2:7] | 64 | [{"value": 64.0, "product": "C(C)(C)(C)OC(NC1C(CC(C1)=C)C(NC1=CC=C(C=C1)Cl)=O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 64.0, "product": "C(C)(C)(C)OC(NC1C(CC(C1)=C)C(NC1=CC=C(C=C1)Cl)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 16 | HOUR | A stirred solution of 1.085 g of 35b in 10 ml of THF was treated subsequently with 1.25 ml of NEt3, 0.69 g hydroxybenzotriazole, 1.21 g of N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride and 0.63 g of 4-chloroaniline and stirring was continued at 22° C. for 16 h. The mixture was evaporated and the residue ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | C1CCCC1.c1ccccc1 | HO- | CCN(CC)CC.C1CCOC1 | null | 16 | C=C1CC(NC(=O)OC(C)(C)C)C(C(=O)O)C1.Nc1ccc(Cl)cc1>CCN(CC)CC.C1CCOC1>C=C1CC(NC(=O)OC(C)(C)C)C(C(=O)Nc2ccc(Cl)cc2)C1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-16ea1b0ba91649e1816daa82899cc1c5 | C=C1CC(NC(=O)OC(C)(C)C)C(C(=O)Nc2ccc(Cl)cc2)C1>>C=C1CC(N)C(C(=O)Nc2ccc(Cl)cc2)C1 | C(C)(C)(C)OC(NC1C(CC(C1)=C)C(NC1=CC=C(C=C1)Cl)=O)=O>>ClC1=CC=C(C=C1)NC(=O)C1C(CC(C1)=C)N | CC(C)(C)OC(=O)[NH:5][CH:4]1[CH2:3][C:2](=[CH2:1])[CH2:17][CH:6]1[C:7](=[O:8])[NH:9][c:10]1[cH:11][cH:12][c:13]([Cl:14])[cH:15][cH:16]1>>[CH2:1]=[C:2]1[CH2:3][CH:4]([NH2:5])[CH:6]([C:7](=[O:8])[NH:9][c:10]2[cH:11][cH:12][c:13]([Cl:14])[cH:15][cH:16]2)[CH2:17]1 | C=C1CC(NC(=O)OC(C)(C)C)C(C(=O)Nc2ccc(Cl)cc2)C1 | C=C1CC(N)C(C(=O)Nc2ccc(Cl)cc2)C1 | null | null | FC(C(=O)O)(F)F.C(Cl)Cl | Reduction | Hydrogenolysis of amides/imides/carbamates | 3c33dd2a2d355ee5ba0287367e209aa147a39aa00607f0c95fb2bf1ade45d014 | c5b5dffe7dd8beebdc1baa8b5b05300a9f7079e65dcfd42ade6f8a77ff09537d | C=C1CCC(C(=O)Nc2ccccc2)C1 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[C:2](-[C:3]-[C:4]=[C;D1;H2:5])-[C:6]-[C:7](-[#7:8])=[O;D1;H0:9]>>[#7:8]-[C:7](=[O;D1;H0:9])-[C:6]-[C:2](-[NH2;D1;+0:1])-[C:3]-[C:4]=[C;D1;H2:5] | 69 | [{"value": 69.0, "product": "ClC1=CC=C(C=C1)NC(=O)C1C(CC(C1)=C)N", "details": "PERCENTYIELD", "is_desired": false}, {"value": 68.5, "product": "ClC1=CC=C(C=C1)NC(=O)C1C(CC(C1)=C)N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 0.98 g of 35c in 10 ml of CH2Cl2 and 1.07 ml of trifluoroacetic acid was stirred at 22° C. for 2 h. The solution was evaporated and the residue partitioned between H2O and CH2Cl2. The aqueous layer was treated slowly with NaHCO3 until pH═8, the suspension was filtered, the residue washed with H2O and drie... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Primary amine | null | null | C1CCCC1.c1ccccc1 | HO- | FC(C(=O)O)(F)F.C(Cl)Cl | null | null | C=C1CC(NC(=O)OC(C)(C)C)C(C(=O)Nc2ccc(Cl)cc2)C1>FC(C(=O)O)(F)F.C(Cl)Cl>C=C1CC(N)C(C(=O)Nc2ccc(Cl)cc2)C1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-3687e99f63a84a9f816ec4bb068d0c28 | O=C(O)c1ccc(Br)cc1F.Oc1ccccn1>>O=C(O)c1ccc(-n2ccccc2=O)cc1F | BrC1=CC(=C(C(=O)O)C=C1)F.OC1=NC=CC=C1.OC=1C=CC=C2C=CC=NC12.C(=O)([O-])[O-].[K+].[K+]>>FC1=C(C(=O)O)C=CC(=C1)N1C(C=CC=C1)=O | Br[c:7]1[cH:6][cH:5][c:4]([C:2](=[O:1])[OH:3])[c:16]([F:17])[cH:15]1.[n:8]1[cH:9][cH:10][cH:11][cH:12][c:13]1[OH:14]>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][cH:6][c:7](-[n:8]2[cH:9][cH:10][cH:11][cH:12][c:13]2=[O:14])[cH:15][c:16]1[F:17] | O=C(O)c1ccc(Br)cc1F.Oc1ccccn1 | O=C(O)c1ccc(-n2ccccc2=O)cc1F | null | null | O.CS(=O)C | Acylation | OtherReaction | 4308b383a3710ca54de2d883c53ac81bae07d58b1e4603761dc4ccecde83005c | 9fb0a4734c628f8028aa0d8a5f3520861ccd6e9f72791fbc28874467838ebc37 | O=c1ccccn1-c1ccccc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[OH;D1;+0:6]-[c;H0;D3;+0:7]1:[c:8]:[c:9]:[c:10]:[c:11]:[n;H0;D2;+0:12]:1>>[O;H0;D1;+0:6]=[c;H0;D3;+0:7]1:[c:8]:[c:9]:[c:10]:[c:11]:[n;H0;D3;+0:12]:1-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5] | 49.4 | [{"value": 49.4, "product": "FC1=C(C(=O)O)C=CC(=C1)N1C(C=CC=C1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 150 | CELSIUS | null | null | To a solution of 10.96 g of 4-bromo-2-fluoro-benzoic acid in 40 ml of DMSO was added subsequently 6.67 g of 2-hydroxypyridine, 1.10 g of 8-hydroxyquinoline, 1.43 g of Cu(I)I and 7.61 g of K2CO3 and the mixture was heated to 150° C. for 18 h. The suspension was diluted with water, filtered, the residue was washed with A... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic alcohol | null | c1ccccc1.c1ccncc1 | c1ccccc1.c1ccncc1 | c1ccccc1.c1ccncc1 | HBr | O.CS(=O)C | 150 | null | O=C(O)c1ccc(Br)cc1F.Oc1ccccn1>O.CS(=O)C>O=C(O)c1ccc(-n2ccccc2=O)cc1F |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a1cc029d64cf4cc0906cc80cbeb6081b | C=C1CC(N)C(C(=O)Nc2ccc(Cl)cc2)C1.O=C(O)c1ccc(-n2ccccc2=O)cc1F>>C=C1CC(NC(=O)c2ccc(-n3ccccc3=O)cc2F)C(C(=O)Nc2ccc(Cl)cc2)C1 | ClC1=CC=C(C=C1)NC(=O)C1C(CC(C1)=C)N.FC1=C(C(=O)O)C=CC(=C1)N1C(C=CC=C1)=O>>ClC1=CC=C(C=C1)NC(=O)C1C(CC(C1)=C)NC(C1=C(C=C(C=C1)N1C(C=CC=C1)=O)F)=O | [CH2:1]=[C:2]1[CH2:3][CH:4]([NH2:5])[CH:22]([C:23](=[O:24])[NH:25][c:26]2[cH:27][cH:28][c:29]([Cl:30])[cH:31][cH:32]2)[CH2:33]1.O[C:6](=[O:7])[c:8]1[cH:9][cH:10][c:11](-[n:12]2[cH:13][cH:14][cH:15][cH:16][c:17]2=[O:18])[cH:19][c:20]1[F:21]>>[CH2:1]=[C:2]1[CH2:3][CH:4]([NH:5][C:6](=[O:7])[c:8]2[cH:9][cH:10][c:11](-[n:12... | C=C1CC(N)C(C(=O)Nc2ccc(Cl)cc2)C1.O=C(O)c1ccc(-n2ccccc2=O)cc1F | C=C1CC(NC(=O)c2ccc(-n3ccccc3=O)cc2F)C(C(=O)Nc2ccc(Cl)cc2)C1 | null | null | null | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | C=C1CC(NC(=O)c2ccc(-n3ccccc3=O)cc2)C(C(=O)Nc2ccccc2)C1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[#7:6]-[C:7](=[O;D1;H0:8])-[C:9]-[C:10](-[NH2;D1;+0:11])-[C:12]-[C:13]=[C;D1;H2:14]>>[#7:6]-[C:7](=[O;D1;H0:8])-[C:9]-[C:10](-[NH;D2;+0:11]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5])-[C:12]-[C:13]=[C;D1;H2:14] | 69 | [{"value": 69.0, "product": "ClC1=CC=C(C=C1)NC(=O)C1C(CC(C1)=C)NC(C1=C(C=C(C=C1)N1C(C=CC=C1)=O)F)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Starting from 35d and 35e, the title compound was prepared in 69% yield according to the procedure for example 1 and 2, step 2. MS: 466.3 (M+H)+.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | C1CCCC1.c1ccccc1.c1ccncc1.c1ccccc1 | HO- | null | null | null | C=C1CC(N)C(C(=O)Nc2ccc(Cl)cc2)C1.O=C(O)c1ccc(-n2ccccc2=O)cc1F>>C=C1CC(NC(=O)c2ccc(-n3ccccc3=O)cc2F)C(C(=O)Nc2ccc(Cl)cc2)C1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-9171da76c4674278a26445b9f01b58ab | C=C1C[C@@H](C(=O)OCC)[C@H](C(=O)OCC)C1>>C=C1C[C@H](C(=O)OCC)[C@@H](C(=O)OCC)C1 | [OH-].[Na+].C(C)OC(=O)[C@H]1[C@@H](CC(C1)=C)C(=O)OCC.P(=O)([O-])([O-])[O-].[K+].[K+].[K+].[Na+].[Cl-]>>C(C)OC(=O)[C@@H]1[C@H](CC(C1)=C)C(=O)OCC | [CH2:1]=[C:2]1[CH2:3][C@@H:4]([C:5](=[O:6])[O:7][CH2:8][CH3:9])[C@H:10]([C:11](=[O:12])[O:13][CH2:14][CH3:15])[CH2:16]1>>[CH2:1]=[C:2]1[CH2:3][C@H:4]([C:5](=[O:6])[O:7][CH2:8][CH3:9])[C@@H:10]([C:11](=[O:12])[O:13][CH2:14][CH3:15])[CH2:16]1 | C=C1C[C@@H](C(=O)OCC)[C@H](C(=O)OCC)C1 | C=C1C[C@H](C(=O)OCC)[C@@H](C(=O)OCC)C1 | null | null | null | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | C=C1CCCC1 | null | 44.5 | [{"value": 44.5, "product": "C(C)OC(=O)[C@@H]1[C@H](CC(C1)=C)C(=O)OCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 7 | CELSIUS | null | null | An emulsion of 1.1 g racemic trans-4-Methylene-cyclopentane-1,2-dicarboxylic acid diethyl ester (Merck 8.14188.0010) in an aqueous buffer (potassium phosphate 5 mM, NaCl 0.1 M) was adjusted to pH 7.0. Under stirring at 7° C. the hydrolysis was performed with 14 mg lipase PN from Phycomyces nitens [Wako Chemicals GmbH N... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | C1CCCC1 | null | null | 7 | null | C=C1C[C@@H](C(=O)OCC)[C@H](C(=O)OCC)C1>>C=C1C[C@H](C(=O)OCC)[C@@H](C(=O)OCC)C1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-34aaaf9b7bff4c39818c9297ecafd186 | C=C1C[C@H](C(=O)OCC)[C@@H](C(=O)OCC)C1>>C=C1C[C@H](C(=O)O)[C@@H](C(=O)OCC)C1 | [OH-].[Na+].C(C)OC(=O)[C@@H]1[C@H](CC(C1)=C)C(=O)OCC.P(=O)([O-])([O-])[O-].[K+].[K+].[K+].[Na+].[Cl-]>>C(C)OC(=O)[C@@H]1[C@H](CC(C1)=C)C(=O)O | CC[O:7][C:5]([C@H:4]1[CH2:3][C:2](=[CH2:1])[CH2:14][C@@H:8]1[C:9](=[O:10])[O:11][CH2:12][CH3:13])=[O:6]>>[CH2:1]=[C:2]1[CH2:3][C@H:4]([C:5](=[O:6])[OH:7])[C@@H:8]([C:9](=[O:10])[O:11][CH2:12][CH3:13])[CH2:14]1 | C=C1C[C@H](C(=O)OCC)[C@@H](C(=O)OCC)C1 | C=C1C[C@H](C(=O)O)[C@@H](C(=O)OCC)C1 | null | null | null | Deprotection | Ester saponification (alkyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | C=C1CCCC1 | C-C-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4]>>[C:3]-[C:2](=[O;D1;H0:4])-[OH;D1;+0:1] | 86 | [{"value": 86.0, "product": "C(C)OC(=O)[C@@H]1[C@H](CC(C1)=C)C(=O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | An emulsion of 1.7 g 41a in an aqueous buffer (potassium phosphate 3 mM, NaCl 0.1 M) was adjusted to pH 7.5. Under stirring at room temperature the hydrolysis was performed with 15 mg lipase OF from Candida rugosa under pH control (pH-static, 1M NaOH). After consumption of 6.5 ml 1M NaOH solution and 7 h the reaction m... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | C1CCCC1 | Other | null | null | null | C=C1C[C@H](C(=O)OCC)[C@@H](C(=O)OCC)C1>>C=C1C[C@H](C(=O)O)[C@@H](C(=O)OCC)C1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-f785e51d06b84c14b68035a34ef9de19 | C=C1C[C@H](C(=O)O)[C@@H](C(=O)OCC)C1.Nc1ccc(-n2ccccc2=O)cc1F>>C=C1C[C@H](C(=O)Nc2ccc(-n3ccccc3=O)cc2F)[C@@H](C(=O)OCC)C1 | C(C)OC(=O)[C@@H]1[C@H](CC(C1)=C)C(=O)O.ClC(=O)OCC(C)C.NC1=C(C=C(C=C1)N1C(C=CC=C1)=O)F>>C(C)OC(=O)[C@@H]1[C@H](CC(C1)=C)C(NC1=C(C=C(C=C1)N1C(C=CC=C1)=O)F)=O | O[C:5]([C@H:4]1[CH2:3][C:2](=[CH2:1])[CH2:28][C@@H:22]1[C:23](=[O:24])[O:25][CH2:26][CH3:27])=[O:6].[NH2:7][c:8]1[cH:9][cH:10][c:11](-[n:12]2[cH:13][cH:14][cH:15][cH:16][c:17]2=[O:18])[cH:19][c:20]1[F:21]>>[CH2:1]=[C:2]1[CH2:3][C@H:4]([C:5](=[O:6])[NH:7][c:8]2[cH:9][cH:10][c:11](-[n:12]3[cH:13][cH:14][cH:15][cH:16][c:1... | C=C1C[C@H](C(=O)O)[C@@H](C(=O)OCC)C1.Nc1ccc(-n2ccccc2=O)cc1F | C=C1C[C@H](C(=O)Nc2ccc(-n3ccccc3=O)cc2F)[C@@H](C(=O)OCC)C1 | null | null | CN(C)C=O.CN1CCOCC1.C1CCOC1 | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | C=C1CC[C@@H](C(=O)Nc2ccc(-n3ccccc3=O)cc2)C1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4]-[C:5](-[#8:6])=[O;D1;H0:7])-[C:8]-[C:9]=[C;D1;H2:10].[NH2;D1;+0:11]-[c:12](:[c:13]):[c:14]>>[#8:6]-[C:5](=[O;D1;H0:7])-[C:4]-[C:3](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:11]-[c:12](:[c:13]):[c:14])-[C:8]-[C:9]=[C;D1;H2:10] | 66 | [{"value": 66.0, "product": "C(C)OC(=O)[C@@H]1[C@H](CC(C1)=C)C(NC1=C(C=C(C=C1)N1C(C=CC=C1)=O)F)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | To a solution of 1.0 g of 41b in 10 ml of THF and 0.61 ml of N-methylmorpholine was added at −12° C. 0.72 ml of isobutyl chloroformate and stirring was continued at −15° C. for 30 min and at 20° C. for 1 h. The suspension obtained was added to a hot (60° C.) solution of 1.13 g of 1-(4-amino-3-fluoro-phenyl)-1H-pyridin-... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | C1CCCC1.c1ccccc1.c1ccncc1 | HO- | CN(C)C=O.CN1CCOCC1.C1CCOC1 | null | 1 | C=C1C[C@H](C(=O)O)[C@@H](C(=O)OCC)C1.Nc1ccc(-n2ccccc2=O)cc1F>CN(C)C=O.CN1CCOCC1.C1CCOC1>C=C1C[C@H](C(=O)Nc2ccc(-n3ccccc3=O)cc2F)[C@@H](C(=O)OCC)C1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ebd3d6c044f84cc9a66afcd766b68400 | Nc1ccc(Cl)cc1.O=C1C=CC(=O)O1>>O=C(O)/C=C\C(=O)Nc1ccc(Cl)cc1 | C1(\C=C/C(=O)O1)=O.ClC1=CC=C(N)C=C1>>ClC1=CC=C(C=C1)NC(=O)\C=C/C(=O)O | [NH2:8][c:9]1[cH:10][cH:11][c:12]([Cl:13])[cH:14][cH:15]1.[O:1]=[C:2]1[O:3][C:6](=[O:7])[CH:5]=[CH:4]1>>[O:1]=[C:2]([OH:3])/[CH:4]=[CH:5]\[C:6](=[O:7])[NH:8][c:9]1[cH:10][cH:11][c:12]([Cl:13])[cH:14][cH:15]1 | Nc1ccc(Cl)cc1.O=C1C=CC(=O)O1 | O=C(O)/C=C\C(=O)Nc1ccc(Cl)cc1 | null | null | C(C)#N | Acylation | OtherReaction | 167c64d23e09803118fc6a0c2e419ae61f1d34b060caa5549f619df29edcd65f | babc03c287bd8cfa2865fae168af372e93ed67f910f700d8b87af94362c61841 | c1ccccc1 | [NH2;D1;+0:1]-[c:2](:[c:3]):[c:4].[O;D1;H0:5]=[C:6]1-[C:7]=[C:8]-[C;H0;D3;+0:9](=[O;D1;H0:10])-[O;H0;D2;+0:11]-1>>[O;D1;H0:5]=[C:6](-[OH;D1;+0:11])/[C:7]=[C:8]\[C;H0;D3;+0:9](=[O;D1;H0:10])-[NH;D2;+0:1]-[c:2](:[c:3]):[c:4] | 97.1 | [{"value": 97.0, "product": "ClC1=CC=C(C=C1)NC(=O)\\C=C/C(=O)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 97.1, "product": "ClC1=CC=C(C=C1)NC(=O)\\C=C/C(=O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 24 | HOUR | A solution of 29.3 g (300 mmol) of maleic anhydride in 500 ml of acetonitrile was treated portionwise with 40 g (310 mmol) of 4-chloroaniline and stirred at room temperature during 24 hrs. The thick precipitate that had formed was filtered off, washed with cold acetonitrile and dried i.v. to yield 65.7 g (97%)of the ti... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Primary amine | Carboxylic acid.Secondary amide | C1=CCOC1 | null | c1ccccc1 | null | C(C)#N | null | 24 | Nc1ccc(Cl)cc1.O=C1C=CC(=O)O1>C(C)#N>O=C(O)/C=C\C(=O)Nc1ccc(Cl)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-befc109c4e5b4818a83415c21aacd7d1 | O=C(O)/C=C\C(=O)Nc1ccc(Cl)cc1>>O=C1C=CC(=O)N1c1ccc(Cl)cc1 | ClC1=CC=C(C=C1)NC(=O)\C=C/C(=O)O.C[Si](C)(C)N[Si](C)(C)C.Cl>>ClC1=CC=C(C=C1)N1C(C=CC1=O)=O | O[C:2](=[O:1])/[CH:3]=[CH:4]\[C:5](=[O:6])[NH:7][c:8]1[cH:9][cH:10][c:11]([Cl:12])[cH:13][cH:14]1>>[O:1]=[C:2]1[CH:3]=[CH:4][C:5](=[O:6])[N:7]1[c:8]1[cH:9][cH:10][c:11]([Cl:12])[cH:13][cH:14]1 | O=C(O)/C=C\C(=O)Nc1ccc(Cl)cc1 | O=C1C=CC(=O)N1c1ccc(Cl)cc1 | null | [Cl-].[Cl-].[Zn+2] | C1=CC=CC=C1 | Miscellaneous | OtherReaction | fecf48c59be3cbdc0ce087b20e9fa269ee3fcac32445ce272bbdc89102043fe7 | 48e6b2b999f3f15ec39998545386900040317bcbdbb4347c7e2886995a8c9772 | O=C1C=CC(=O)N1c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])/[C:3]=[C:4]\[C:5](=[O;D1;H0:6])-[NH;D2;+0:7]-[c:8](:[c:9]):[c:10]>>[O;D1;H0:2]=[C;H0;D3;+0:1]1-[C:3]=[C:4]-[C:5](=[O;D1;H0:6])-[N;H0;D3;+0:7]-1-[c:8](:[c:9]):[c:10] | 97 | [{"value": 97.0, "product": "ClC1=CC=C(C=C1)N1C(C=CC1=O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 97.0, "product": "ClC1=CC=C(C=C1)N1C(C=CC1=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | In Analogy to the procedure given in Mhaske et al., Synthesis, 2003, p863-870: A solution of 65 g (288 mmol) of (Z)-3-(4-chloro-phenylcarbamoyl)-acrylic acid in 300 ml of benzene was treated with 41.2 g (302 mmol) of zinc dichloride, dropwise with 90.1 ml (432 mmol) of bis(trimethylsilyl)amine and refluxed during 5 hrs... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amide | Substituted dicarboximide | null | C1=CC[NH]C1 | C1=CC[NH]C1.c1ccccc1 | HO- | [Cl-].[Cl-].[Zn+2].C1=CC=CC=C1 | null | null | O=C(O)/C=C\C(=O)Nc1ccc(Cl)cc1>[Cl-].[Cl-].[Zn+2].C1=CC=CC=C1>O=C1C=CC(=O)N1c1ccc(Cl)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-01f24a38bb21480da8e3ab11a692e97a | CCOC(=O)C=[N+]=[N-].O=C1C=CC(=O)N1c1ccc(Cl)cc1>>CCOC(=O)C1C2C(=O)N(c3ccc(Cl)cc3)C(=O)C12 | ClC1=CC=C(C=C1)N1C(C=CC1=O)=O.C(C)OC(C=[N+]=[N-])=O>>C(C)OC(=O)C1C2C(N(C(C12)=O)C1=CC=C(C=C1)Cl)=O | [N-]=[N+]=[CH:6][C:4]([O:3][CH2:2][CH3:1])=[O:5].[CH:7]1=[CH:20][C:18](=[O:19])[N:10]([c:11]2[cH:12][cH:13][c:14]([Cl:15])[cH:16][cH:17]2)[C:8]1=[O:9]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]1[CH:7]2[C:8](=[O:9])[N:10]([c:11]3[cH:12][cH:13][c:14]([Cl:15])[cH:16][cH:17]3)[C:18](=[O:19])[CH:20]12 | CCOC(=O)C=[N+]=[N-].O=C1C=CC(=O)N1c1ccc(Cl)cc1 | CCOC(=O)C1C2C(=O)N(c3ccc(Cl)cc3)C(=O)C12 | null | null | C=1(C(=CC=CC1)C)C | C-C Coupling | OtherReaction | b3907611f56aaaea5fdd12ab720953c488457938f885c7a1795c4bfd7a1a2e67 | 2bf044f9aa3102f7e58ada063c1d8beb18b3b23505b944ca768ff7e6f4f49661 | O=C1C2CC2C(=O)N1c1ccccc1 | [C:1]-[#8:2]-[C:3](=[O;D1;H0:4])-[CH;D2;+0:5]=[N+]=[N-].[O;D1;H0:6]=[C:7]1-[CH;D2;+0:8]=[CH;D2;+0:9]-[C:10](=[O;D1;H0:11])-[#7:12]-1-[c:13]>>[C:1]-[#8:2]-[C:3](=[O;D1;H0:4])-[CH;D3;+0:5]1-[CH;D3;+0:8]2-[C:7](=[O;D1;H0:6])-[#7:12](-[c:13])-[C:10](=[O;D1;H0:11])-[CH;D3;+0:9]-2-1 | 35 | [{"value": 35.0, "product": "C(C)OC(=O)C1C2C(N(C(C12)=O)C1=CC=C(C=C1)Cl)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 34.8, "product": "C(C)OC(=O)C1C2C(N(C(C12)=O)C1=CC=C(C=C1)Cl)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 19.4 g (93 mmol) of 1-(4-chloro-phenyl)-pyrrole-2,5-dione in 120 ml of xylene was treated with 19.4 ml (187 mmol) of ethyldiazoacetate and refluxed during 12 hrs. Evaporation of the solvent and chromatography on silica gel with toluene and then a gradient of toluene/AcOEt from 95:5 to 90:10 gave 9.5 g(35%... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Diazo | Ester | C1=CC[NH]C1 | C1[NH]CC2CC12 | C1[NH]CC2CC12.c1ccccc1 | Other | C=1(C(=CC=CC1)C)C | null | null | CCOC(=O)C=[N+]=[N-].O=C1C=CC(=O)N1c1ccc(Cl)cc1>C=1(C(=CC=CC1)C)C>CCOC(=O)C1C2C(=O)N(c3ccc(Cl)cc3)C(=O)C12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-f0500249342f437da4972a50b3c26b60 | CCOC(=O)C1C2C(=O)N(c3ccc(Cl)cc3)C(=O)C12.Nc1ccc(-n2ccccc2=O)cc1F>>CCOC(=O)C1C(C(=O)Nc2ccc(Cl)cc2)C1C(=O)Nc1ccc(-n2ccccc2=O)cc1F | Cl.C(C)OC(=O)C1C2C(N(C(C12)=O)C1=CC=C(C=C1)Cl)=O.C[Si](C)(C)[N-][Si](C)(C)C.[Li+].NC1=C(C=C(C=C1)N1C(C=CC=C1)=O)F>>C(C)OC(=O)C1C(C1C(NC1=C(C=C(C=C1)N1C(C=CC=C1)=O)F)=O)C(NC1=CC=C(C=C1)Cl)=O | [CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]1[CH:7]2[C:8](=[O:9])[N:10]([c:11]3[cH:12][cH:13][c:14]([Cl:15])[cH:16][cH:17]3)[C:19](=[O:20])[CH:18]12.[NH2:21][c:22]1[cH:23][cH:24][c:25](-[n:26]2[cH:27][cH:28][cH:29][cH:30][c:31]2=[O:32])[cH:33][c:34]1[F:35]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]1[CH:7]([C:8](=[O:9])[NH:10][c... | CCOC(=O)C1C2C(=O)N(c3ccc(Cl)cc3)C(=O)C12.Nc1ccc(-n2ccccc2=O)cc1F | CCOC(=O)C1C(C(=O)Nc2ccc(Cl)cc2)C1C(=O)Nc1ccc(-n2ccccc2=O)cc1F | null | null | C1CCOC1 | Acylation | OtherReaction | 54a0d6b7a6245a7cbbf3baeb2a511e2b626ea0970d3987a3f1bccd4c1e2a148f | c5dbbff33268430c8bfa22331d710773ca50cd979a5fb6dcb4356e0495eb059b | O=C(Nc1ccccc1)C1CC1C(=O)Nc1ccc(-n2ccccc2=O)cc1 | [#8:1]-[C:2](=[O;D1;H0:3])-[C:4]1-[C:5]2-[C:6]-1-[C:7](=[O;D1;H0:8])-[N;H0;D3;+0:9](-[c:10](:[c:11]):[c:12])-[C;H0;D3;+0:13]-2=[O;D1;H0:14].[NH2;D1;+0:15]-[c:16](:[c:17]):[c:18]>>[#8:1]-[C:2](=[O;D1;H0:3])-[C:4]1-[C:5](-[C;H0;D3;+0:13](=[O;D1;H0:14])-[NH;D2;+0:15]-[c:16](:[c:17]):[c:18])-[C:6]-1-[C:7](=[O;D1;H0:8])-[NH... | 24 | [{"value": 24.0, "product": "C(C)OC(=O)C1C(C1C(NC1=C(C=C(C=C1)N1C(C=CC=C1)=O)F)=O)C(NC1=CC=C(C=C1)Cl)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | A solution of 7 g (34 mmol) of 1-(4-amino-3-fluoro-phenyl)-1H-pyridin-2-one (prepared according to C. F. Bigge et al., patent application WO 2003045912) in 25 ml of THF was cooled to −78° C. and treated dropwise with 41 ml of a 1M lithium bis(trimethylsilyl)amide-solution in THF and stirred for 30 min. To this solution... | 10.6084/m9.figshare.5104873.v1 | null | Substituted dicarboximide.Primary amine | Secondary amide.Secondary amide | C1[NH]CC2CC12 | null | C1CC1.c1ccccc1.c1ccccc1.c1ccncc1 | null | C1CCOC1 | null | 0.5 | CCOC(=O)C1C2C(=O)N(c3ccc(Cl)cc3)C(=O)C12.Nc1ccc(-n2ccccc2=O)cc1F>C1CCOC1>CCOC(=O)C1C(C(=O)Nc2ccc(Cl)cc2)C1C(=O)Nc1ccc(-n2ccccc2=O)cc1F |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-576a1ea47e45462dad2e5c13b42a3598 | CCOC(=O)C1C(C(=O)Nc2ccc(Cl)cc2)C1C(=O)Nc1ccc(-n2ccccc2=O)cc1F>>O=C(O)C1C(C(=O)Nc2ccc(Cl)cc2)C1C(=O)Nc1ccc(-n2ccccc2=O)cc1F | Cl.C(C)OC(=O)C1C(C1C(NC1=C(C=C(C=C1)N1C(C=CC=C1)=O)F)=O)C(NC1=CC=C(C=C1)Cl)=O.[Li+].[OH-]>>ClC1=CC=C(C=C1)NC(=O)C1C(C1C(NC1=C(C=C(C=C1)N1C(C=CC=C1)=O)F)=O)C(=O)O | CC[O:3][C:2](=[O:1])[CH:4]1[CH:5]([C:6](=[O:7])[NH:8][c:9]2[cH:10][cH:11][c:12]([Cl:13])[cH:14][cH:15]2)[CH:16]1[C:17](=[O:18])[NH:19][c:20]1[cH:21][cH:22][c:23](-[n:24]2[cH:25][cH:26][cH:27][cH:28][c:29]2=[O:30])[cH:31][c:32]1[F:33]>>[O:1]=[C:2]([OH:3])[CH:4]1[CH:5]([C:6](=[O:7])[NH:8][c:9]2[cH:10][cH:11][c:12]([Cl:13... | CCOC(=O)C1C(C(=O)Nc2ccc(Cl)cc2)C1C(=O)Nc1ccc(-n2ccccc2=O)cc1F | O=C(O)C1C(C(=O)Nc2ccc(Cl)cc2)C1C(=O)Nc1ccc(-n2ccccc2=O)cc1F | null | null | C1CCOC1 | Deprotection | Ester saponification (alkyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | O=C(Nc1ccccc1)C1CC1C(=O)Nc1ccc(-n2ccccc2=O)cc1 | C-C-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4]>>[C:3]-[C:2](=[O;D1;H0:4])-[OH;D1;+0:1] | 86.5 | [{"value": 86.0, "product": "ClC1=CC=C(C=C1)NC(=O)C1C(C1C(NC1=C(C=C(C=C1)N1C(C=CC=C1)=O)F)=O)C(=O)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 86.5, "product": "ClC1=CC=C(C=C1)NC(=O)C1C(C1C(NC1=C(C=C(C=C1)N1C(C=CC=C1)=O)F)=O)C(=O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | A solution of 80 mg (0.16 mmol) of (1RS,2RS,3SR)-2-(4-chloro-phenylcarbamoyl)-3-[2-fluoro-4-(2-oxo-2H-pyridin-1-yl)-phenylcarbamoyl]-cyclopropanecarboxylic acid ethyl ester (example 68) in a mixture of 10 ml of THF and 10 ml of a 1M aqueous LiOH-solution was stirred during 2 hrs at room temperature. The mixture was pou... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | C1CC1.c1ccccc1.c1ccccc1.c1ccncc1 | Other | C1CCOC1 | null | 2 | CCOC(=O)C1C(C(=O)Nc2ccc(Cl)cc2)C1C(=O)Nc1ccc(-n2ccccc2=O)cc1F>C1CCOC1>O=C(O)C1C(C(=O)Nc2ccc(Cl)cc2)C1C(=O)Nc1ccc(-n2ccccc2=O)cc1F |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-443283d1e67e46c58576fc7b5ca5ccaa | C=C1C[C@H](C(=O)O)[C@@H](C(=O)OCC)C1.Nc1ccc(Cl)cn1>>C=C1C[C@H](C(=O)Nc2ccc(Cl)cn2)[C@@H](C(=O)OCC)C1 | C(C)OC(=O)[C@@H]1[C@H](CC(C1)=C)C(=O)O.NC1=NC=C(C=C1)Cl>>C(C)OC(=O)[C@@H]1[C@H](CC(C1)=C)C(NC1=NC=C(C=C1)Cl)=O | O[C:5]([C@H:4]1[CH2:3][C:2](=[CH2:1])[CH2:21][C@@H:15]1[C:16](=[O:17])[O:18][CH2:19][CH3:20])=[O:6].[NH2:7][c:8]1[cH:9][cH:10][c:11]([Cl:12])[cH:13][n:14]1>>[CH2:1]=[C:2]1[CH2:3][C@H:4]([C:5](=[O:6])[NH:7][c:8]2[cH:9][cH:10][c:11]([Cl:12])[cH:13][n:14]2)[C@@H:15]([C:16](=[O:17])[O:18][CH2:19][CH3:20])[CH2:21]1 | C=C1C[C@H](C(=O)O)[C@@H](C(=O)OCC)C1.Nc1ccc(Cl)cn1 | C=C1C[C@H](C(=O)Nc2ccc(Cl)cn2)[C@@H](C(=O)OCC)C1 | null | null | null | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | C=C1CC[C@@H](C(=O)Nc2ccccn2)C1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4]-[C:5](-[#8:6])=[O;D1;H0:7])-[C:8]-[C:9]=[C;D1;H2:10].[NH2;D1;+0:11]-[c:12](:[c:13]):[#7;a:14]:[c:15]>>[#8:6]-[C:5](=[O;D1;H0:7])-[C:4]-[C:3](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:11]-[c:12](:[c:13]):[#7;a:14]:[c:15])-[C:8]-[C:9]=[C;D1;H2:10] | 48 | [{"value": 48.0, "product": "C(C)OC(=O)[C@@H]1[C@H](CC(C1)=C)C(NC1=NC=C(C=C1)Cl)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Starting from 41b, the title compound was prepared in 48% yield according to the procedure for example 1 and 2, step 2 using 2-amino-5-chloropyridine. MS: 309.1 (M+H)+.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | C1CCCC1.c1ccncc1 | HO- | null | null | null | C=C1C[C@H](C(=O)O)[C@@H](C(=O)OCC)C1.Nc1ccc(Cl)cn1>>C=C1C[C@H](C(=O)Nc2ccc(Cl)cn2)[C@@H](C(=O)OCC)C1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d81b8457cb9e443291174a14e7f153ee | CO.O=C(O)C1C(C(=O)Nc2ccc(-n3ccccc3=O)cc2F)C1c1ccccc1>>COC(=O)C1C(C(=O)Nc2ccc(-n3ccccc3=O)cc2F)C1c1ccccc1 | FC1=C(C=CC(=C1)N1C(C=CC=C1)=O)NC(=O)C1C(C1C1=CC=CC=C1)C(=O)O.S(=O)(Cl)Cl.CO>>COC(=O)C1C(C1C1=CC=CC=C1)C(NC1=C(C=C(C=C1)N1C(C=CC=C1)=O)F)=O | [CH3:1][OH:2].O[C:3](=[O:4])[CH:5]1[CH:6]([C:7](=[O:8])[NH:9][c:10]2[cH:11][cH:12][c:13](-[n:14]3[cH:15][cH:16][cH:17][cH:18][c:19]3=[O:20])[cH:21][c:22]2[F:23])[CH:24]1[c:25]1[cH:26][cH:27][cH:28][cH:29][cH:30]1>>[CH3:1][O:2][C:3](=[O:4])[CH:5]1[CH:6]([C:7](=[O:8])[NH:9][c:10]2[cH:11][cH:12][c:13](-[n:14]3[cH:15][cH:1... | CO.O=C(O)C1C(C(=O)Nc2ccc(-n3ccccc3=O)cc2F)C1c1ccccc1 | COC(=O)C1C(C(=O)Nc2ccc(-n3ccccc3=O)cc2F)C1c1ccccc1 | null | null | null | Protection | Esterification of Carboxylic Acids | 9cecdbd189c6f9c3648521d17154d013842a5498de4e76e65efb1d842973340b | af0b8064f2e82ebe66c4c29d2391785ac1b993104265ccdc4d67ca79e36fa3c8 | O=C(Nc1ccc(-n2ccccc2=O)cc1)C1CC1c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]1-[C:4]-[C:5]-1-[C:6](-[#7:7])=[O;D1;H0:8].[C;D1;H3:9]-[OH;D1;+0:10]>>[#7:7]-[C:6](=[O;D1;H0:8])-[C:5]1-[C:4]-[C:3]-1-[C;H0;D3;+0:1](=[O;D1;H0:2])-[O;H0;D2;+0:10]-[C;D1;H3:9] | null | [] | null | null | 8 | HOUR | A solution of 140 mg (0.36 mmol) of (1RS,2SR,3SR)-2-[2-fluoro-4-(2-oxo-2H-pyridin-1-yl)-phenylcarbamoyl]-3-phenyl-cyclopropanecarboxylic acid in 5 ml of methanol was treated at 0° C. with ca. 0.1 ml of thionylchloride and left to stirr overnight at RT. Evaporation of the solvent gave 160 mg of (1RS,2SR,3SR)-2-[2-fluoro... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Methanol | Ester | null | null | C1CC1.c1ccccc1.c1ccncc1.c1ccccc1 | HO- | null | null | 8 | CO.O=C(O)C1C(C(=O)Nc2ccc(-n3ccccc3=O)cc2F)C1c1ccccc1>>COC(=O)C1C(C(=O)Nc2ccc(-n3ccccc3=O)cc2F)C1c1ccccc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-94141face69b4a28a8869761c8e6b73a | CCOC(=O)C1C2COC(=O)C21.Nc1ccc(-n2ccccc2=O)cc1F>>CCOC(=O)C1C(CO)C1C(=O)Nc1ccc(-n2ccccc2=O)cc1F | Cl.C(C)OC(=O)C1C2COC(C12)=O.NC1=C(C=C(C=C1)N1C(C=CC=C1)=O)F.C[Si](C)(C)[N-][Si](C)(C)C.[Li+]>>C(C)OC(=O)C1C(C1CO)C(NC1=C(C=C(C=C1)N1C(C=CC=C1)=O)F)=O | [CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]1[CH:7]2[CH2:8][O:9][C:11](=[O:12])[CH:10]12.[NH2:13][c:14]1[cH:15][cH:16][c:17](-[n:18]2[cH:19][cH:20][cH:21][cH:22][c:23]2=[O:24])[cH:25][c:26]1[F:27]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]1[CH:7]([CH2:8][OH:9])[CH:10]1[C:11](=[O:12])[NH:13][c:14]1[cH:15][cH:16][c:17](-[n:18]2[c... | CCOC(=O)C1C2COC(=O)C21.Nc1ccc(-n2ccccc2=O)cc1F | CCOC(=O)C1C(CO)C1C(=O)Nc1ccc(-n2ccccc2=O)cc1F | null | null | C1CCOC1 | Acylation | OtherReaction | 69a7881b740d2f5f830cdb942d0f936308bff4c2ddda3b485ae5d1afa3371fb1 | 93d3d2d91fa5d15fd0f361e38c72a0c2e4bde37efa822e4566162d5af70167b6 | O=C(Nc1ccc(-n2ccccc2=O)cc1)C1CC1 | [#8:1]-[C:2](=[O;D1;H0:3])-[C:4]1-[C:5]2-[C:6]-1-[C:7]-[O;H0;D2;+0:8]-[C;H0;D3;+0:9]-2=[O;D1;H0:10].[NH2;D1;+0:11]-[c:12](:[c:13]):[c:14]>>[#8:1]-[C:2](=[O;D1;H0:3])-[C:4]1-[C:5](-[C;H0;D3;+0:9](=[O;D1;H0:10])-[NH;D2;+0:11]-[c:12](:[c:13]):[c:14])-[C:6]-1-[C:7]-[OH;D1;+0:8] | 58 | [{"value": 57.0, "product": "C(C)OC(=O)C1C(C1CO)C(NC1=C(C=C(C=C1)N1C(C=CC=C1)=O)F)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 58.0, "product": "C(C)OC(=O)C1C(C1CO)C(NC1=C(C=C(C=C1)N1C(C=CC=C1)=O)F)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | A solution of 600 mg (2.9 mmol) of 1-(4-amino-3-fluoro-phenyl)-1H-pyridin-2-one (prepared according to C. F. Bigge et al., patent application WO 2003045912) in 10 ml of THF was cooled to −78° C. and treated dropwise with 3.2 ml of a 1M lithium bis(trimethylsilyl)amide-solution in THF and stirred for 30 min. To this sol... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Primary amine | Secondary amide.Primary alcohol | C1OCC2CC12 | null | C1CC1.c1ccccc1.c1ccncc1 | null | C1CCOC1 | null | 0.5 | CCOC(=O)C1C2COC(=O)C21.Nc1ccc(-n2ccccc2=O)cc1F>C1CCOC1>CCOC(=O)C1C(CO)C1C(=O)Nc1ccc(-n2ccccc2=O)cc1F |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-7dc9203d9e5b41e8b98b1e3760198f6b | COC(=O)C1C(C(=O)Nc2ccc(Cl)cn2)C1C(=O)Nc1ccc(-n2ccccc2=O)cc1F>>O=C(O)C1C(C(=O)Nc2ccc(Cl)cn2)C1C(=O)Nc1ccc(-n2ccccc2=O)cc1F | Cl.COC(=O)C1C(C1C(NC1=C(C=C(C=C1)N1C(C=CC=C1)=O)F)=O)C(NC1=NC=C(C=C1)Cl)=O.[Li+].[OH-]>>ClC=1C=CC(=NC1)NC(=O)C1C(C1C(NC1=C(C=C(C=C1)N1C(C=CC=C1)=O)F)=O)C(=O)O | C[O:3][C:2](=[O:1])[CH:4]1[CH:5]([C:6](=[O:7])[NH:8][c:9]2[cH:10][cH:11][c:12]([Cl:13])[cH:14][n:15]2)[CH:16]1[C:17](=[O:18])[NH:19][c:20]1[cH:21][cH:22][c:23](-[n:24]2[cH:25][cH:26][cH:27][cH:28][c:29]2=[O:30])[cH:31][c:32]1[F:33]>>[O:1]=[C:2]([OH:3])[CH:4]1[CH:5]([C:6](=[O:7])[NH:8][c:9]2[cH:10][cH:11][c:12]([Cl:13])... | COC(=O)C1C(C(=O)Nc2ccc(Cl)cn2)C1C(=O)Nc1ccc(-n2ccccc2=O)cc1F | O=C(O)C1C(C(=O)Nc2ccc(Cl)cn2)C1C(=O)Nc1ccc(-n2ccccc2=O)cc1F | null | null | C1CCOC1 | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | O=C(Nc1ccc(-n2ccccc2=O)cc1)C1CC1C(=O)Nc1ccccn1 | C-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4]>>[C:3]-[C:2](=[O;D1;H0:4])-[OH;D1;+0:1] | 68.3 | [{"value": 68.0, "product": "ClC=1C=CC(=NC1)NC(=O)C1C(C1C(NC1=C(C=C(C=C1)N1C(C=CC=C1)=O)F)=O)C(=O)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 68.3, "product": "ClC=1C=CC(=NC1)NC(=O)C1C(C1C(NC1=C(C=C(C=C1)N1C(C=CC=C1)=O)F)=O)C(=O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | A solution of 68 mg (0.14 mmol) of (1RS,2SR,3RS)-2-(5-chloro-pyridin-2-ylcarbamoyl)-3-[2-fluoro-4-(2-oxo-2H-pyridin-1-yl)-phenylcarbamoyl]-cyclopropanecarboxylic acid methyl ester (example 114, step 5) in 1.5 ml of THF was treated with 0.2 ml of a 1M aqueous LiOH solution, stirred at RT during 2 hrs and acidified to pH... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | C1CC1.c1ccncc1.c1ccccc1.c1ccncc1 | Other | C1CCOC1 | null | 2 | COC(=O)C1C(C(=O)Nc2ccc(Cl)cn2)C1C(=O)Nc1ccc(-n2ccccc2=O)cc1F>C1CCOC1>O=C(O)C1C(C(=O)Nc2ccc(Cl)cn2)C1C(=O)Nc1ccc(-n2ccccc2=O)cc1F |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-581c221020e9422f95f707d475439026 | Nc1ccc(-n2ccc(OCc3ccccc3)cc2=O)cc1F>>Nc1ccc(-n2ccc(O)cc2=O)cc1F | NC1=C(C=C(C=C1)N1C(C=C(C=C1)OCC1=CC=CC=C1)=O)F>>NC1=C(C=C(C=C1)N1C(C=C(C=C1)O)=O)F | c1ccc(C[O:10][c:9]2[cH:8][cH:7][n:6](-[c:5]3[cH:4][cH:3][c:2]([NH2:1])[c:15]([F:16])[cH:14]3)[c:12](=[O:13])[cH:11]2)cc1>>[NH2:1][c:2]1[cH:3][cH:4][c:5](-[n:6]2[cH:7][cH:8][c:9]([OH:10])[cH:11][c:12]2=[O:13])[cH:14][c:15]1[F:16] | Nc1ccc(-n2ccc(OCc3ccccc3)cc2=O)cc1F | Nc1ccc(-n2ccc(O)cc2=O)cc1F | null | [Pd] | CO | Deprotection | Hydroxyl benzyl deprotection | 36869d1fe85185a14d9eb30bf05178c600a9b6eca277ffaf3803578c30e0bf5d | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | O=c1ccccn1-c1ccccc1 | C(-[O;H0;D2;+0:1]-[c:2]1:[c:3]:[c:4]:[#7;a:5]:[c:6]:[c:7]:1)-c1:c:c:c:c:c:1>>[OH;D1;+0:1]-[c:2]1:[c:3]:[c:4]:[#7;a:5]:[c:6]:[c:7]:1 | 97 | [{"value": 97.0, "product": "NC1=C(C=C(C=C1)N1C(C=C(C=C1)O)=O)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 96.7, "product": "NC1=C(C=C(C=C1)N1C(C=C(C=C1)O)=O)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | A solution of 580 mg (1.87 mmol) 1-(4-amino-3-fluoro-phenyl)-4-benzyloxy-1H-pyridin-2-one (example 144, step 1) in 20 ml of MeOH was treated with 140 mg of Pd/C (10%) and hydrogenated at atmospheric pressure under vigorous stirring for 3 hrs. Filtration and evaporation of the solvent gave 398 mg (97%) of 1-(4-Amino-3-f... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | c1ccccc1 | null | c1ccccc1.c1ccncc1 | Other | [Pd].CO | null | 3 | Nc1ccc(-n2ccc(OCc3ccccc3)cc2=O)cc1F>[Pd].CO>Nc1ccc(-n2ccc(O)cc2=O)cc1F |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-71f674dad4e143ab951272dcf324cfbc | CCOC(=O)C1C(C(=O)Nc2ccc(Cl)cc2)C1C(=O)Nc1ccc(-n2ccc(O)cc2=O)cc1F.COS(=O)(=O)OC>>CCOC(=O)C1C(C(=O)Nc2ccc(Cl)cc2)C1C(=O)Nc1ccc(-n2ccc(OC)cc2=O)cc1F | C(C)OC(=O)C1C(C1C(NC1=C(C=C(C=C1)N1C(C=C(C=C1)O)=O)F)=O)C(NC1=CC=C(C=C1)Cl)=O.C([O-])([O-])=O.[K+].[K+].COS(=O)(=O)OC>>C(C)OC(=O)C1C(C1C(NC1=C(C=C(C=C1)N1C(C=C(C=C1)OC)=O)F)=O)C(NC1=CC=C(C=C1)Cl)=O | [CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]1[CH:7]([C:8](=[O:9])[NH:10][c:11]2[cH:12][cH:13][c:14]([Cl:15])[cH:16][cH:17]2)[CH:18]1[C:19](=[O:20])[NH:21][c:22]1[cH:23][cH:24][c:25](-[n:26]2[cH:27][cH:28][c:29]([OH:30])[cH:32][c:33]2=[O:34])[cH:35][c:36]1[F:37].COS(=O)(=O)O[CH3:31]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]1[CH... | CCOC(=O)C1C(C(=O)Nc2ccc(Cl)cc2)C1C(=O)Nc1ccc(-n2ccc(O)cc2=O)cc1F.COS(=O)(=O)OC | CCOC(=O)C1C(C(=O)Nc2ccc(Cl)cc2)C1C(=O)Nc1ccc(-n2ccc(OC)cc2=O)cc1F | null | null | CC(=O)C | Heteroatom Alkylation and Arylation | Methylation of OH with DMS | b8b041187bac58376aae824630608e7deb49a01db3d652291f8b379c10d4e434 | 0f0966e3597a58033417ecee71659f4d0c082f95d46b1e52c95541e6e4a59086 | O=C(Nc1ccccc1)C1CC1C(=O)Nc1ccc(-n2ccccc2=O)cc1 | C-O-S(=O)(=O)-O-[CH3;D1;+0:1].[OH;D1;+0:2]-[c:3]1:[c:4]:[c:5]:[#7;a:6]:[c:7]:[c:8]:1>>[CH3;D1;+0:1]-[O;H0;D2;+0:2]-[c:3]1:[c:4]:[c:5]:[#7;a:6]:[c:7]:[c:8]:1 | 13.5 | [{"value": 13.0, "product": "C(C)OC(=O)C1C(C1C(NC1=C(C=C(C=C1)N1C(C=C(C=C1)OC)=O)F)=O)C(NC1=CC=C(C=C1)Cl)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 13.5, "product": "C(C)OC(=O)C1C(C1C(NC1=C(C=C(C=C1)N1C(C=C(C=C1)OC)=O)F)=O)C(NC1=CC=C(C=C1)Cl)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": f... | null | null | 2 | HOUR | A solution of 35 mg (0.07 mmol) of (1SR,2RS,3SR)-2-(4-chloro-phenylcarbamoyl)-3-[2-fluoro-4-(4-hydroxy-2-oxo-2H-pyridin-1-yl)-phenylcarbamoyl]-cyclopropanecarboxylic acid ethyl ester (example 142, step 2) in 5 ml of acetone was treated with 94 mg (0.6 mmol) of potassium carbonate and 8 ul (0.08 mmol) of dimethylsulfate... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic alcohol | Ether | null | null | C1CC1.c1ccccc1.c1ccccc1.c1ccncc1 | HO- | CC(=O)C | null | 2 | CCOC(=O)C1C(C(=O)Nc2ccc(Cl)cc2)C1C(=O)Nc1ccc(-n2ccc(O)cc2=O)cc1F.COS(=O)(=O)OC>CC(=O)C>CCOC(=O)C1C(C(=O)Nc2ccc(Cl)cc2)C1C(=O)Nc1ccc(-n2ccc(OC)cc2=O)cc1F |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-34c53b7818264de3813ba31788b88df6 | Nc1ccc(Br)cc1F.O=c1cc(OCc2ccccc2)cc[nH]1>>Nc1ccc(-n2ccc(OCc3ccccc3)cc2=O)cc1F | C(C1=CC=CC=C1)OC1=CC(NC=C1)=O.BrC1=CC(=C(N)C=C1)F.NC1=C(C=C(C=C1)N1C(C=CC=C1)=O)F>>NC1=C(C=C(C=C1)N1C(C=C(C=C1)OCC1=CC=CC=C1)=O)F | Br[c:5]1[cH:4][cH:3][c:2]([NH2:1])[c:22]([F:23])[cH:21]1.[nH:6]1[cH:7][cH:8][c:9]([O:10][CH2:11][c:12]2[cH:13][cH:14][cH:15][cH:16][cH:17]2)[cH:18][c:19]1=[O:20]>>[NH2:1][c:2]1[cH:3][cH:4][c:5](-[n:6]2[cH:7][cH:8][c:9]([O:10][CH2:11][c:12]3[cH:13][cH:14][cH:15][cH:16][cH:17]3)[cH:18][c:19]2=[O:20])[cH:21][c:22]1[F:23] | Nc1ccc(Br)cc1F.O=c1cc(OCc2ccccc2)cc[nH]1 | Nc1ccc(-n2ccc(OCc3ccccc3)cc2=O)cc1F | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | c4bca3c6c7e7a85c1215b056751d6c9e665b6c9ad3e374f5595f04141f3d67ff | e3660767655c50df0f92afc78c794dd2af7cf646bf1430960eafd30c23bf3fa7 | O=c1cc(OCc2ccccc2)ccn1-c1ccccc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[O;D1;H0:6]=[c:7](:[c:8]):[nH;D2;+0:9]:[c:10]:[c:11]>>[O;D1;H0:6]=[c:7](:[c:8]):[n;H0;D3;+0:9](-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5]):[c:10]:[c:11] | null | [] | null | null | null | null | 1-(4-Amino-3-fluoro-phenyl)-4-benzyloxy-1H-pyridin-2-one was prepared from 4-benzyloxy-1H-pyridin-2-one and 4-bromo-2-fluoroaniline in analogy to the procedure described for the preparation of 1-(4-amino-3-fluoro-phenyl)-1H-pyridin-2-one described in C. F. Bigge et al., patent application WO 2003045912. MS: 311 (M+H)+.... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | null | c1ccccc1.c1ccncc1 | c1ccccc1.c1ccncc1 | c1ccccc1.c1ccncc1.c1ccccc1 | HBr | null | null | null | Nc1ccc(Br)cc1F.O=c1cc(OCc2ccccc2)cc[nH]1>>Nc1ccc(-n2ccc(OCc3ccccc3)cc2=O)cc1F |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-4b6f7ef19e5547d19076744adbf0728d | CCOC(=O)C1C(C(=O)Nc2ccc(Cl)cc2)C1C(=O)Nc1ccc(-n2ccc(OCC(=O)O)cc2=O)cc1F.CNC>>CCOC(=O)C1C(C(=O)Nc2ccc(Cl)cc2)C1C(=O)Nc1ccc(-n2ccc(OCC(=O)N(C)C)cc2=O)cc1F | Cl.C(C)OC(=O)C1C(C1C(NC1=CC=C(C=C1)Cl)=O)C(NC1=C(C=C(C=C1)N1C(C=C(C=C1)OCC(=O)O)=O)F)=O.Cl.CNC.ON1N=NC2=C1C=CC=C2.CN1CCOCC1.Cl.CN(CCCN=C=NCC)C>>C(C)OC(=O)C1C(C1C(NC1=C(C=C(C=C1)N1C(C=C(C=C1)OCC(N(C)C)=O)=O)F)=O)C(NC1=CC=C(C=C1)Cl)=O | O[C:32]([CH2:31][O:30][c:29]1[cH:28][cH:27][n:26](-[c:25]2[cH:24][cH:23][c:22]([NH:21][C:19]([CH:18]3[CH:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[CH:7]3[C:8](=[O:9])[NH:10][c:11]3[cH:12][cH:13][c:14]([Cl:15])[cH:16][cH:17]3)=[O:20])[c:41]([F:42])[cH:40]2)[c:38](=[O:39])[cH:37]1)=[O:33].[NH:34]([CH3:35])[CH3:36]>>[CH3:1][CH... | CCOC(=O)C1C(C(=O)Nc2ccc(Cl)cc2)C1C(=O)Nc1ccc(-n2ccc(OCC(=O)O)cc2=O)cc1F.CNC | CCOC(=O)C1C(C(=O)Nc2ccc(Cl)cc2)C1C(=O)Nc1ccc(-n2ccc(OCC(=O)N(C)C)cc2=O)cc1F | null | null | CN(C)C=O | Acylation | Acylation of Nitrogen Nucleophiles by Carboxylic Acids | ac72df6259d5d7baee7abdbd4706ef4b4627f86ead9dc94f0cefcfcb37c21def | c5e4172490b2731ba9322b68af56376edadc31ce0bb9a3dfdea23a1817a852fd | O=C(Nc1ccccc1)C1CC1C(=O)Nc1ccc(-n2ccccc2=O)cc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[#8:4].[C;D1;H3:5]-[NH;D2;+0:6]-[C;D1;H3:7]>>[#8:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[N;H0;D3;+0:6](-[C;D1;H3:5])-[C;D1;H3:7] | 95 | [{"value": 95.0, "product": "C(C)OC(=O)C1C(C1C(NC1=C(C=C(C=C1)N1C(C=C(C=C1)OCC(N(C)C)=O)=O)F)=O)C(NC1=CC=C(C=C1)Cl)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 91.8, "product": "C(C)OC(=O)C1C(C1C(NC1=C(C=C(C=C1)N1C(C=C(C=C1)OCC(N(C)C)=O)=O)F)=O)C(NC1=CC=C(C=C1)Cl)=O", "details": "CALCULATEDPERCENTYIE... | null | null | 10 | HOUR | A mixture of 23 mg (0.04 mmol) of (1SR,2RS,3SR) 2-[4-(4-carboxymethoxy-2-oxo-2H-pyridin-1-yl)-2-fluoro-phenylcarbamoyl]-3-(4-chloro-phenylcarbamoyl) cyclopropanecarboxylic acid ethyl ester (example 155), 5 mg (0.06 mmol) of dimethylamine hydrochloride, 1 mg of 1-hydroxybenzotriazole, and 25 ul (0.23 mmol) of N-methylmo... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | Tertiary amide | null | null | C1CC1.c1ccccc1.c1ccccc1.c1ccncc1 | HO- | CN(C)C=O | null | 10 | CCOC(=O)C1C(C(=O)Nc2ccc(Cl)cc2)C1C(=O)Nc1ccc(-n2ccc(OCC(=O)O)cc2=O)cc1F.CNC>CN(C)C=O>CCOC(=O)C1C(C(=O)Nc2ccc(Cl)cc2)C1C(=O)Nc1ccc(-n2ccc(OCC(=O)N(C)C)cc2=O)cc1F |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-f88b300ee6cc4b8eab49e12e227ee7d7 | CCOC(=O)C1C(C(=O)Nc2ccc(Cl)cc2)C1C(=O)Nc1ccc(-n2ccc(OCC(=O)OC(C)(C)C)cc2=O)cc1F>>CCOC(=O)C1C(C(=O)Nc2ccc(Cl)cc2)C1C(=O)Nc1ccc(-n2ccc(OCC(=O)O)cc2=O)cc1F | C(C)OC(=O)C1C(C1C(NC1=CC=C(C=C1)Cl)=O)C(NC1=C(C=C(C=C1)N1C(C=C(C=C1)OCC(=O)OC(C)(C)C)=O)F)=O.FC(C(=O)O)(F)F>>C(C)OC(=O)C1C(C1C(NC1=CC=C(C=C1)Cl)=O)C(NC1=C(C=C(C=C1)N1C(C=C(C=C1)OCC(=O)O)=O)F)=O | CC(C)(C)[O:34][C:32]([CH2:31][O:30][c:29]1[cH:28][cH:27][n:26](-[c:25]2[cH:24][cH:23][c:22]([NH:21][C:19]([CH:18]3[CH:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[CH:7]3[C:8](=[O:9])[NH:10][c:11]3[cH:12][cH:13][c:14]([Cl:15])[cH:16][cH:17]3)=[O:20])[c:39]([F:40])[cH:38]2)[c:36](=[O:37])[cH:35]1)=[O:33]>>[CH3:1][CH2:2][O:3][C:4... | CCOC(=O)C1C(C(=O)Nc2ccc(Cl)cc2)C1C(=O)Nc1ccc(-n2ccc(OCC(=O)OC(C)(C)C)cc2=O)cc1F | CCOC(=O)C1C(C(=O)Nc2ccc(Cl)cc2)C1C(=O)Nc1ccc(-n2ccc(OCC(=O)O)cc2=O)cc1F | null | null | null | Deprotection | Deprotection of carboxylic acid | 152e5537e48c95b4a3e767536b0f9f68d1308e5f484070828ab5ed951805157a | 7f019d4cfe9b3036d0a2d3a3209aa0e1fcb05418ebee15a4be5e125d315d5f01 | O=C(Nc1ccccc1)C1CC1C(=O)Nc1ccc(-n2ccccc2=O)cc1 | C-C(-C)(-C)-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4]>>[C:3]-[C:2](=[O;D1;H0:4])-[OH;D1;+0:1] | 69 | [{"value": 69.0, "product": "C(C)OC(=O)C1C(C1C(NC1=CC=C(C=C1)Cl)=O)C(NC1=C(C=C(C=C1)N1C(C=C(C=C1)OCC(=O)O)=O)F)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 67.8, "product": "C(C)OC(=O)C1C(C1C(NC1=CC=C(C=C1)Cl)=O)C(NC1=C(C=C(C=C1)N1C(C=C(C=C1)OCC(=O)O)=O)F)=O", "details": "CALCULATEDPERCENTYIELD", "is... | 75 | CELSIUS | 40 | MINUTE | A solution of 49 mg (0.08 mmol) of (1SR,2SR,3RS)-2-[4-(4-tert-butoxycarbonylmethoxy-2-oxo-2H-pyridin-1-yl)-2-fluoro-phenylcarbamoyl]-3-(4-chloro-phenylcarbamoyl)-cyclopropanecarboxylic acid ethyl ester in 3 ml of 1,2-dichloromethane was treated with 28 ul of trifluoroacetic acid and stirred at 75° C. during 40 min. Eva... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Boc | Carboxylic acid | null | null | C1CC1.c1ccccc1.c1ccccc1.c1ccncc1 | Other | null | 75 | 0.666667 | CCOC(=O)C1C(C(=O)Nc2ccc(Cl)cc2)C1C(=O)Nc1ccc(-n2ccc(OCC(=O)OC(C)(C)C)cc2=O)cc1F>>CCOC(=O)C1C(C(=O)Nc2ccc(Cl)cc2)C1C(=O)Nc1ccc(-n2ccc(OCC(=O)O)cc2=O)cc1F |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-228c5fc2707a43a489978db56dbc3af7 | COc1ccc(CCl)cc1.OC/C=C/CO>>COc1ccc(COC/C=C/CO)cc1 | [Na+].[Cl-].COC1=CC=C(CCl)C=C1.C(\C=C\CO)O.[H-].[Na+]>>COC1=CC=C(COC/C=C/CO)C=C1 | Cl[CH2:7][c:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:15][cH:14]1.[OH:8][CH2:9]/[CH:10]=[CH:11]/[CH2:12][OH:13]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][O:8][CH2:9]/[CH:10]=[CH:11]/[CH2:12][OH:13])[cH:14][cH:15]1 | COc1ccc(CCl)cc1.OC/C=C/CO | COc1ccc(COC/C=C/CO)cc1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | dd3f9c60e1f90d961a7c01d970ae213561355ee1451f276a3b04696e4b6fae5c | 46a6e883cf919b4006e69abfdfd883f458f55c08b3200960c6a5b57c4139fbca | c1ccccc1 | Cl-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[C:5]/[C:6]=[C:7]/[C:8]-[OH;D1;+0:9]>>[C:5]/[C:6]=[C:7]/[C:8]-[O;H0;D2;+0:9]-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4] | 21 | [{"value": 21.0, "product": "COC1=CC=C(COC/C=C/CO)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 20.5, "product": "COC1=CC=C(COC/C=C/CO)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 45 | MINUTE | A solution of 11.8 g (133.4 mmol) of trans 2-butene-1,4-diol in 100 ml of DMF was treated with 6.4 g (147 mmol) of sodium hydride dispersion on oil (55%), stirred at 0° C. for 45 min., and treated dropwise with 25.1 g (160 mmol) of 4-methoxybenzylchloride. The mixture was stirred during 5 hrs at RT and then poured into... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary alcohol | Ether | null | null | c1ccccc1 | HCl | CN(C)C=O | 0 | 0.75 | COc1ccc(CCl)cc1.OC/C=C/CO>CN(C)C=O>COc1ccc(COC/C=C/CO)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-15f35c06e96d498e9afbd4d1d1db75ea | COc1ccc(COCC=CCOC(=O)C=[N+]=[N-])cc1>>COc1ccc(COC[C@H]2[C@@H]3COC(=O)[C@H]23)cc1 | COC1=CC=C(COCC=CCOC(C=[N+]=[N-])=O)C=C1>>COC1=CC=C(COC[C@H]2[C@@H]3COC([C@H]23)=O)C=C1 | [N-]=[N+]=[CH:16][C:14]([O:13][CH2:12][CH:11]=[CH:10][CH2:9][O:8][CH2:7][c:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:18][cH:17]1)=[O:15]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][O:8][CH2:9][C@H:10]2[C@@H:11]3[CH2:12][O:13][C:14](=[O:15])[C@H:16]23)[cH:17][cH:18]1 | COc1ccc(COCC=CCOC(=O)C=[N+]=[N-])cc1 | COc1ccc(COC[C@H]2[C@@H]3COC(=O)[C@H]23)cc1 | null | null | ClCCl | C-C Coupling | OtherReaction | 48aae0167faec840c55360f4c42a9634a99b490782f71ffc3d251e8d2acde28f | 2bf044f9aa3102f7e58ada063c1d8beb18b3b23505b944ca768ff7e6f4f49661 | O=C1OC[C@H]2[C@H](COCc3ccccc3)[C@@H]12 | [#8:1]-[C:2]-[CH;D2;+0:3]=[CH;D2;+0:4]-[C:5]-[#8:6]-[C:7](=[O;D1;H0:8])-[CH;D2;+0:9]=[N+]=[N-]>>[#8:1]-[C:2]-[C@H;D3;+0:3]1-[C@@H;D3;+0:4]2-[C:5]-[#8:6]-[C:7](=[O;D1;H0:8])-[C@@H;D3;+0:9]-2-1 | 96 | [{"value": 96.0, "product": "COC1=CC=C(COC[C@H]2[C@@H]3COC([C@H]23)=O)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 95.1, "product": "COC1=CC=C(COC[C@H]2[C@@H]3COC([C@H]23)=O)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 1 g (3.6 mmol) of diazo-acetic acid 4-(4-methoxy-benzyloxy)-but-2-enyl ester in 50 ml dichloromethane under reflux were added within 8 hrs of 25 mg (0.03 mmol) of Rh2 (5S-MEPY)4 (Doyle dirhodium catalyst from Acros, CAS: 132435-65-5) dissolved in 100 ml of dichloromethane. Refluxing for another 20 hrs,... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Diazo | Ester | null | C1OC[C@H]2C[C@@H]12 | c1ccccc1.C1OC[C@H]2C[C@@H]12 | Other | ClCCl | null | null | COc1ccc(COCC=CCOC(=O)C=[N+]=[N-])cc1>ClCCl>COc1ccc(COC[C@H]2[C@@H]3COC(=O)[C@H]23)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-82455f92875a431cb285d19e454c5c5e | COc1ccc(COC[C@H]2[C@@H]3COC(=O)[C@H]23)cc1.Nc1ccc(-n2ccccc2=O)cc1F>>COc1ccc(COC[C@H]2[C@H](CO)[C@@H]2C(=O)Nc2ccc(-n3ccccc3=O)cc2F)cc1 | C[Si](C)(C)[N-][Si](C)(C)C.[Li+].Cl.NC1=C(C=C(C=C1)N1C(C=CC=C1)=O)F.COC1=CC=C(COC[C@H]2[C@@H]3COC([C@H]23)=O)C=C1>>FC1=C(C=CC(=C1)N1C(C=CC=C1)=O)NC(=O)[C@H]1[C@H]([C@@H]1COCC1=CC=C(C=C1)OC)CO | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][O:8][CH2:9][C@H:10]2[C@@H:11]3[CH2:12][O:13][C:15](=[O:16])[C@H:14]23)[cH:32][cH:33]1.[NH2:17][c:18]1[cH:19][cH:20][c:21](-[n:22]2[cH:23][cH:24][cH:25][cH:26][c:27]2=[O:28])[cH:29][c:30]1[F:31]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][O:8][CH2:9][C@H:10]2[C@H:11]([CH2:12]... | COc1ccc(COC[C@H]2[C@@H]3COC(=O)[C@H]23)cc1.Nc1ccc(-n2ccccc2=O)cc1F | COc1ccc(COC[C@H]2[C@H](CO)[C@@H]2C(=O)Nc2ccc(-n3ccccc3=O)cc2F)cc1 | null | null | CCOC(=O)C.C1CCOC1 | Acylation | OtherReaction | d131db01cc7882f6b2dc1d75ead3a8190f440b4eb2c2ab2d5243808c1dcc3dd5 | 93d3d2d91fa5d15fd0f361e38c72a0c2e4bde37efa822e4566162d5af70167b6 | O=C(Nc1ccc(-n2ccccc2=O)cc1)[C@H]1C[C@@H]1COCc1ccccc1 | [NH2;D1;+0:1]-[c:2](:[c:3]):[c:4].[O;D1;H0:5]=[C;H0;D3;+0:6]1-[O;H0;D2;+0:7]-[C:8]-[C:9]2-[C:10]-[C:11]-2-1>>[O;D1;H0:5]=[C;H0;D3;+0:6](-[NH;D2;+0:1]-[c:2](:[c:3]):[c:4])-[C:11]1-[C:10]-[C:9]-1-[C:8]-[OH;D1;+0:7] | 78 | [{"value": 77.0, "product": "FC1=C(C=CC(=C1)N1C(C=CC=C1)=O)NC(=O)[C@H]1[C@H]([C@@H]1COCC1=CC=C(C=C1)OC)CO", "details": "PERCENTYIELD", "is_desired": false}, {"value": 78.0, "product": "FC1=C(C=CC(=C1)N1C(C=CC=C1)=O)NC(=O)[C@H]1[C@H]([C@@H]1COCC1=CC=C(C=C1)OC)CO", "details": "CALCULATEDPERCENTYIELD", "is_desired": false... | 78 | CELSIUS | 30 | MINUTE | A solution of 850 mg (3.4 mmol) of 1-(4-amino-3-fluoro-phenyl)-1H-pyridin-2-one (prepared according to C. F. Bigge et al., patent application WO 2003045912) in 80 ml of THF was cooled to −78° C., treated dropwise with 4.8 ml of a 1M lithium bis(trimethylsilyl)amide-solution in THF and stirred for 30 min at 78° C. To th... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Primary amine | Secondary amide.Primary alcohol | C1OC[C@H]2C[C@@H]12 | null | c1ccccc1.C1CC1.c1ccccc1.c1ccncc1 | null | CCOC(=O)C.C1CCOC1 | 78 | 0.5 | COc1ccc(COC[C@H]2[C@@H]3COC(=O)[C@H]23)cc1.Nc1ccc(-n2ccccc2=O)cc1F>CCOC(=O)C.C1CCOC1>COc1ccc(COC[C@H]2[C@H](CO)[C@@H]2C(=O)Nc2ccc(-n3ccccc3=O)cc2F)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-b684634275db4f42b800778664501e6f | CI.COc1ccc(OC[C@@H]2[C@@H](C(=O)Nc3ccc(-n4ccccc4=O)cc3F)[C@H]2C(=O)O)cc1>>COC(=O)[C@H]1[C@H](COc2ccc(OC)cc2)[C@H]1C(=O)Nc1ccc(-n2ccccc2=O)cc1F | [OH-].[Na+].FC1=C(C=CC(=C1)N1C(C=CC=C1)=O)NC(=O)[C@H]1[C@H]([C@@H]1COC1=CC=C(C=C1)OC)C(=O)O.C(=O)([O-])[O-].[K+].[K+].IC>>COC(=O)[C@@H]1[C@@H]([C@H]1COC1=CC=C(C=C1)OC)C(NC1=C(C=C(C=C1)N1C(C=CC=C1)=O)F)=O | I[CH3:1].[OH:2][C:3](=[O:4])[C@H:5]1[C@H:6]([CH2:7][O:8][c:9]2[cH:10][cH:11][c:12]([O:13][CH3:14])[cH:15][cH:16]2)[C@H:17]1[C:18](=[O:19])[NH:20][c:21]1[cH:22][cH:23][c:24](-[n:25]2[cH:26][cH:27][cH:28][cH:29][c:30]2=[O:31])[cH:32][c:33]1[F:34]>>[CH3:1][O:2][C:3](=[O:4])[C@H:5]1[C@H:6]([CH2:7][O:8][c:9]2[cH:10][cH:11][... | CI.COc1ccc(OC[C@@H]2[C@@H](C(=O)Nc3ccc(-n4ccccc4=O)cc3F)[C@H]2C(=O)O)cc1 | COC(=O)[C@H]1[C@H](COc2ccc(OC)cc2)[C@H]1C(=O)Nc1ccc(-n2ccccc2=O)cc1F | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 9474aa79a2adc7353c0c02444ca598a6f486ecdd7ed5edb9ae0645721ee50389 | badd4f82161bb0ee7acffd023ea4caae5d036bce7065c10ab0a06e83a6a6f119 | O=C(Nc1ccc(-n2ccccc2=O)cc1)[C@H]1C[C@@H]1COc1ccccc1 | I-[CH3;D1;+0:1].[C:2]-[C:3](=[O;D1;H0:4])-[OH;D1;+0:5]>>[C:2]-[C:3](=[O;D1;H0:4])-[O;H0;D2;+0:5]-[CH3;D1;+0:1] | 101.5 | [{"value": 97.0, "product": "COC(=O)[C@@H]1[C@@H]([C@H]1COC1=CC=C(C=C1)OC)C(NC1=C(C=C(C=C1)N1C(C=CC=C1)=O)F)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 101.5, "product": "COC(=O)[C@@H]1[C@@H]([C@H]1COC1=CC=C(C=C1)OC)C(NC1=C(C=C(C=C1)N1C(C=CC=C1)=O)F)=O", "details": "CALCULATEDPERCENTYIELD", "is_desi... | null | null | 3 | HOUR | A solution of 90 mg (0.19 mmol) of (1S,2R,3R) 2-[2-fluoro-4-(2-oxo-2H-pyridin-1-yl)-phenylcarbamoyl]-3-(4-methoxy-phenoxymethyl)-cyclopropanecarboxylic acid in 3 ml of DMF was treated with 100 mg of K2CO3 and 0.5 ml ml of iodomethane. The mixture was stirred for 3 hrs and poured into a diluted aqueous solution of NaOH.... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Ester | null | null | C1CC1.c1ccccc1.c1ccccc1.c1ccncc1 | HI | CN(C)C=O | null | 3 | CI.COc1ccc(OC[C@@H]2[C@@H](C(=O)Nc3ccc(-n4ccccc4=O)cc3F)[C@H]2C(=O)O)cc1>CN(C)C=O>COC(=O)[C@H]1[C@H](COc2ccc(OC)cc2)[C@H]1C(=O)Nc1ccc(-n2ccccc2=O)cc1F |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-23b3204104d74d3296d53d262f0c8187 | CC1(C(=O)O)CC1C(=O)Nc1ccc(Cl)cn1.CO>>COC(=O)C1(C)CC1C(=O)Nc1ccc(Cl)cn1 | ClC=1C=CC(=NC1)NC(=O)C1C(C1)(C(=O)O)C.CO>>COC(=O)C1(C(C1)C(NC1=NC=C(C=C1)Cl)=O)C | O[C:3](=[O:4])[C:5]1([CH3:6])[CH2:7][CH:8]1[C:9](=[O:10])[NH:11][c:12]1[cH:13][cH:14][c:15]([Cl:16])[cH:17][n:18]1.[CH3:1][OH:2]>>[CH3:1][O:2][C:3](=[O:4])[C:5]1([CH3:6])[CH2:7][CH:8]1[C:9](=[O:10])[NH:11][c:12]1[cH:13][cH:14][c:15]([Cl:16])[cH:17][n:18]1 | CC1(C(=O)O)CC1C(=O)Nc1ccc(Cl)cn1.CO | COC(=O)C1(C)CC1C(=O)Nc1ccc(Cl)cn1 | null | S(=O)(Cl)Cl.S(=O)(Cl)Cl | null | Protection | Esterification of Carboxylic Acids | 9cecdbd189c6f9c3648521d17154d013842a5498de4e76e65efb1d842973340b | af0b8064f2e82ebe66c4c29d2391785ac1b993104265ccdc4d67ca79e36fa3c8 | O=C(Nc1ccccn1)C1CC1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]1(-[C;D1;H3:4])-[C:5]-[C:6]-1-[C:7](-[#7:8])=[O;D1;H0:9].[C;D1;H3:10]-[OH;D1;+0:11]>>[#7:8]-[C:7](=[O;D1;H0:9])-[C:6]1-[C:5]-[C:3]-1(-[C;D1;H3:4])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[O;H0;D2;+0:11]-[C;D1;H3:10] | null | [] | 0 | CELSIUS | null | null | A suspension of (1SR,2RS)-2-(5-chloro-pyridin-2-ylcarbamoyl)-1-methyl-cyclopropane-carboxylic acid (176 mg) in MeOH (5 ml) was cooled to 0° C. and treated with thionyl chloride (15 drops). After stirring for 2 hrs at 0° C. additional thionyl chloride (10 drops) was added. The clear solution was concentrated. The crude ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Methanol | Ester | null | null | C1CC1.c1ccncc1 | HO- | S(=O)(Cl)Cl.S(=O)(Cl)Cl | 0 | null | CC1(C(=O)O)CC1C(=O)Nc1ccc(Cl)cn1.CO>S(=O)(Cl)Cl.S(=O)(Cl)Cl>COC(=O)C1(C)CC1C(=O)Nc1ccc(Cl)cn1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-4503bf05abfa4d1e8d80f322c67cb6b6 | Nc1ccc(-n2ccccc2=O)cc1F.O=C1OC(=O)C2CC12>>O=C(O)C1CC1C(=O)Nc1ccc(-n2ccccc2=O)cc1F | C12C(OC(C2C1)=O)=O.NC1=C(C=C(C=C1)N1C(C=CC=C1)=O)F>>FC1=C(C=CC(=C1)N1C(C=CC=C1)=O)NC(=O)C1C(C1)C(=O)O | [NH2:9][c:10]1[cH:11][cH:12][c:13](-[n:14]2[cH:15][cH:16][cH:17][cH:18][c:19]2=[O:20])[cH:21][c:22]1[F:23].[O:1]=[C:2]1[O:3][C:7](=[O:8])[CH:6]2[CH:4]1[CH2:5]2>>[O:1]=[C:2]([OH:3])[CH:4]1[CH2:5][CH:6]1[C:7](=[O:8])[NH:9][c:10]1[cH:11][cH:12][c:13](-[n:14]2[cH:15][cH:16][cH:17][cH:18][c:19]2=[O:20])[cH:21][c:22]1[F:23] | Nc1ccc(-n2ccccc2=O)cc1F.O=C1OC(=O)C2CC12 | O=C(O)C1CC1C(=O)Nc1ccc(-n2ccccc2=O)cc1F | null | null | C1CCOC1 | Acylation | OtherReaction | e703520c7562ce45f4229de31c7594eb37a30a19130a8d74d6df634b89de6365 | babc03c287bd8cfa2865fae168af372e93ed67f910f700d8b87af94362c61841 | O=C(Nc1ccc(-n2ccccc2=O)cc1)C1CC1 | [NH2;D1;+0:1]-[c:2](:[c:3]):[c:4].[O;D1;H0:5]=[C:6]1-[O;H0;D2;+0:7]-[C;H0;D3;+0:8](=[O;D1;H0:9])-[C:10]2-[C:11]-[C:12]-1-2>>[O;D1;H0:5]=[C:6](-[OH;D1;+0:7])-[C:12]1-[C:11]-[C:10]-1-[C;H0;D3;+0:8](=[O;D1;H0:9])-[NH;D2;+0:1]-[c:2](:[c:3]):[c:4] | 31.9 | [{"value": 31.9, "product": "FC1=C(C=CC(=C1)N1C(C=CC=C1)=O)NC(=O)C1C(C1)C(=O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 3-oxabicyclo[3.1.0]hexane-2,4-dione (160 mg) in THF (5 ml) was treated with 1-(4-amino-3-fluoro-phenyl)-1H-pyridin-2-one (321 mg; CAS 536747-52-1, prepared according to C. F. Bigge et al., patent application WO 2003045912). The suspension was stirred over night at r.t. The solid was collected by filtratio... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Primary amine | Carboxylic acid.Secondary amide | C1OCC2CC12 | null | C1CC1.c1ccccc1.c1ccncc1 | null | C1CCOC1 | null | null | Nc1ccc(-n2ccccc2=O)cc1F.O=C1OC(=O)C2CC12>C1CCOC1>O=C(O)C1CC1C(=O)Nc1ccc(-n2ccccc2=O)cc1F |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d491ba9104c64357b1bf083aa7de18f9 | CO.O=C(O)C1CC1C(=O)Nc1ccc(-n2ccccc2=O)cc1F>>COC(=O)C1CC1C(=O)Nc1ccc(-n2ccccc2=O)cc1F | FC1=C(C=CC(=C1)N1C(C=CC=C1)=O)NC(=O)C1C(C1)C(=O)O.CO>>COC(=O)C1C(C1)C(NC1=C(C=C(C=C1)N1C(C=CC=C1)=O)F)=O | [CH3:1][OH:2].O[C:3](=[O:4])[CH:5]1[CH2:6][CH:7]1[C:8](=[O:9])[NH:10][c:11]1[cH:12][cH:13][c:14](-[n:15]2[cH:16][cH:17][cH:18][cH:19][c:20]2=[O:21])[cH:22][c:23]1[F:24]>>[CH3:1][O:2][C:3](=[O:4])[CH:5]1[CH2:6][CH:7]1[C:8](=[O:9])[NH:10][c:11]1[cH:12][cH:13][c:14](-[n:15]2[cH:16][cH:17][cH:18][cH:19][c:20]2=[O:21])[cH:2... | CO.O=C(O)C1CC1C(=O)Nc1ccc(-n2ccccc2=O)cc1F | COC(=O)C1CC1C(=O)Nc1ccc(-n2ccccc2=O)cc1F | null | S(=O)(Cl)Cl | null | Protection | Esterification of Carboxylic Acids | 9cecdbd189c6f9c3648521d17154d013842a5498de4e76e65efb1d842973340b | af0b8064f2e82ebe66c4c29d2391785ac1b993104265ccdc4d67ca79e36fa3c8 | O=C(Nc1ccc(-n2ccccc2=O)cc1)C1CC1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]1-[C:4]-[C:5]-1-[C:6](-[#7:7])=[O;D1;H0:8].[C;D1;H3:9]-[OH;D1;+0:10]>>[#7:7]-[C:6](=[O;D1;H0:8])-[C:5]1-[C:4]-[C:3]-1-[C;H0;D3;+0:1](=[O;D1;H0:2])-[O;H0;D2;+0:10]-[C;D1;H3:9] | null | [] | 0 | CELSIUS | 3 | HOUR | A stirred suspension of (1RS,2SR)-2-[2-fluoro-4-(2-oxo-2H-pyridin-1-yl)-phenylcarbamoyl]-cyclopropanecarboxylic acid (140 mg) in MeOH (5 ml) was cooled to 0° C. and treated with thionyl chloride (10 drops). The mixture turned immediately into a clear solution. Stirring was continued for 3 hrs at 0° C. Then the reaction... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Methanol | Ester | null | null | C1CC1.c1ccccc1.c1ccncc1 | HO- | S(=O)(Cl)Cl | 0 | 3 | CO.O=C(O)C1CC1C(=O)Nc1ccc(-n2ccccc2=O)cc1F>S(=O)(Cl)Cl>COC(=O)C1CC1C(=O)Nc1ccc(-n2ccccc2=O)cc1F |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-9d805015ed7f431bbc8d0c72fbb7b28f | COc1cccc(CCN)c1.N#C[O-]>>COc1cccc(CCNC(N)=O)c1 | COC=1C=C(C=CC1)CCN.Cl.[O-]C#N.[K+]>>COC=1C=C(C=CC1)CCNC(=O)N | [CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]([CH2:8][CH2:9][NH2:10])[cH:14]1.[C:11](#[N:12])[O-:13]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]([CH2:8][CH2:9][NH:10][C:11]([NH2:12])=[O:13])[cH:14]1 | COc1cccc(CCN)c1.N#C[O-] | COc1cccc(CCNC(N)=O)c1 | null | null | O | Acylation | OtherReaction | f8798d1193af6f9b314ac8855e814716b90ff3758bcfa29778cc632fcaa83b7a | 5efe06db19c806d9e9798893351dc14c0cc48f1e8f8c857f54c6171e86c96a1b | c1ccccc1 | [C:1]-[C:2]-[NH2;D1;+0:3].[N;H0;D1;+0:4]#[C;H0;D2;+0:5]-[O-;H0;D1:6]>>[C:1]-[C:2]-[NH;D2;+0:3]-[C;H0;D3;+0:5](-[NH2;D1;+0:4])=[O;H0;D1;+0:6] | 83.1 | [{"value": 83.0, "product": "COC=1C=C(C=CC1)CCNC(=O)N", "details": "PERCENTYIELD", "is_desired": false}, {"value": 83.1, "product": "COC=1C=C(C=CC1)CCNC(=O)N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 50 | CELSIUS | 2 | HOUR | To a solution of 2-(3-methoxy-phenyl)-ethylamine (1) (50.0 g, 331 mmol) and concentrated HCl (27.6 mL) in water (350 mL), potassium cyanate (28.2 g, 348 mmol) was added and stirred at 50° C. for 2 hours, then at room temperature for 2 days. Formed precipitate was collected by filtration. The solid was washed with water... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile.Primary amine | Urea | null | null | c1ccccc1 | null | O | 50 | 2 | COc1cccc(CCN)c1.N#C[O-]>O>COc1cccc(CCNC(N)=O)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-9f43836919cc44168d960ef77667b36f | CCO.COc1cccc(CCNC(N)=O)c1.COc1cccc(CCNC(N)=O)c1>>COc1cccc(CCN2C(=O)CC(=O)NC2=O)c1 | O.COC=1C=C(C=CC1)CCNC(=O)N.CCO.CC[O-].[Na+].CCO.COC=1C=C(C=CC1)CCNC(=O)N.CCO.Cl>>COC=1C=C(C=CC1)CCN1C(NC(CC1=O)=O)=O | [CH3:13][CH2:14][OH:15].COc1cccc(CCN[C:17]([NH2:16])=[O:18])c1.N[C:11]([NH:10][CH2:9][CH2:8][c:7]1[cH:6][cH:5][cH:4][c:3]([O:2][CH3:1])[cH:19]1)=[O:12]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]([CH2:8][CH2:9][N:10]2[C:11](=[O:12])[CH2:13][C:14](=[O:15])[NH:16][C:17]2=[O:18])[cH:19]1 | CCO.COc1cccc(CCNC(N)=O)c1.COc1cccc(CCNC(N)=O)c1 | COc1cccc(CCN2C(=O)CC(=O)NC2=O)c1 | null | null | null | C-C Coupling | OtherReaction | b7ca0daf00e44af477d8b8b8c083fc5050fa3b397a12547a6331f3ff762b2a22 | e7ff2d155be7a3b7decc6e2151672c81c36269e075e29092e633dcf1e6958c07 | O=C1CC(=O)N(CCc2ccccc2)C(=O)N1 | C-O-c1:c:c:c:c(-C-C-N-[C;H0;D3;+0:1](-[NH2;D1;+0:2])=[O;D1;H0:3]):c:1.N-[C;H0;D3;+0:4](=[O;D1;H0:5])-[NH;D2;+0:6]-[C:7]-[C:8].[CH3;D1;+0:9]-[CH2;D2;+0:10]-[OH;D1;+0:11]>>[C:8]-[C:7]-[N;H0;D3;+0:6]1-[C;H0;D3;+0:4](=[O;D1;H0:5])-[CH2;D2;+0:9]-[C;H0;D3;+0:10](=[O;H0;D1;+0:11])-[NH;D2;+0:2]-[C;H0;D3;+0:1]-1=[O;D1;H0:3] | 74 | [{"value": 74.0, "product": "COC=1C=C(C=CC1)CCN1C(NC(CC1=O)=O)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of NaOEt (144 mmol, fleshly prepared from 3.3 g of Na) in EtOH (80 mL), a solution of ethyl malonate (2) (22 mL, 144 mmol) in EtOH (250 mL) was added. The mixture was refluxed then added a solution of [2-(3-methoxy-phenyl)-ethyl]-urea (2) (23.3 g, 120 mmol) in EtOH (300 mL). The reaction mixture was reflu... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Urea.Urea.Primary alcohol | Urea.Unsubstituted dicarboximide.Substituted dicarboximide | c1ccccc1 | C1C[NH]CNC1 | c1ccccc1.C1C[NH]CNC1 | HO- | null | null | null | CCO.COc1cccc(CCNC(N)=O)c1.COc1cccc(CCNC(N)=O)c1>>COc1cccc(CCN2C(=O)CC(=O)NC2=O)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-28670c17abff4d0d958f5c309490c30d | COc1ccc2c(c1)CCn1c-2cc(Cl)nc1=O.Nc1ccc2[nH]ncc2c1>>COc1ccc2c(c1)CCn1c-2cc(Nc2ccc3[nH]ncc3c2)nc1=O | ClC1=NC(N2C(C3=CC=C(C=C3CC2)OC)=C1)=O.N1N=CC2=CC(=CC=C12)N>>N1N=CC2=CC(=CC=C12)NC1=NC(N2C(C3=CC=C(C=C3CC2)OC)=C1)=O | Cl[c:14]1[cH:13][c:12]2[n:11]([c:26](=[O:27])[n:25]1)[CH2:10][CH2:9][c:7]1[c:6]-2[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:8]1.[NH2:15][c:16]1[cH:17][cH:18][c:19]2[nH:20][n:21][cH:22][c:23]2[cH:24]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([cH:8]1)[CH2:9][CH2:10][n:11]1[c:12]-2[cH:13][c:14]([NH:15][c:16]2[cH:17][cH:18][c:19... | COc1ccc2c(c1)CCn1c-2cc(Cl)nc1=O.Nc1ccc2[nH]ncc2c1 | COc1ccc2c(c1)CCn1c-2cc(Nc2ccc3[nH]ncc3c2)nc1=O | null | null | null | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c8475104970a63fce3d52b085fd15febf776cee9f570c7a80516c8bef4cb52de | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | O=c1nc(Nc2ccc3[nH]ncc3c2)cc2n1CCc1ccccc1-2 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3](=[O;D1;H0:4]):[#7;a:5](:[c:6](:[c:7]:1)-[c:8])-[C:9].[NH2;D1;+0:10]-[c:11](:[c:12]):[c:13]>>[C:9]-[#7;a:5]1:[c:6](:[c:7]:[c;H0;D3;+0:1](-[NH;D2;+0:10]-[c:11](:[c:12]):[c:13]):[#7;a:2]:[c:3]:1=[O;D1;H0:4])-[c:8] | null | [] | null | null | null | null | The title compound was prepared from 2-chloro-9-methoxy-6,7-dihydro-pyrimido[6,1-a]isoquinolin-4-one (4) and 1H-indazol-5-ylamine as in Example 1 d. 1H-NMR (400 MHz, d6-DMSO) δ 13.00 (br, 1H), 9.60 (s, 1H), 8.36 (br, 1H), 8.06 (s, 1H), 7.69 (d, 1H), 7.51 (m, 2H), 7.10-6.95 (2H), 6.35 (s, 1H), 3.99 (t, 2H), 3.84 (s, 3H)... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccc2c(c1)CCn1cnccc21 | c1ccc2c(c1)CCn1cnccc21 | c1ccc2c(c1)CCn1cnccc21.c1ccc2[nH]ncc2c1 | HCl | null | null | null | COc1ccc2c(c1)CCn1c-2cc(Cl)nc1=O.Nc1ccc2[nH]ncc2c1>>COc1ccc2c(c1)CCn1c-2cc(Nc2ccc3[nH]ncc3c2)nc1=O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-f48d66c02cb24b2da3b05215ca1ea5b0 | COc1ccc2c(c1)CCn1c-2cc(Cl)nc1=O.COc1cccc(C)c1N>>COc1ccc2c(c1)CCn1c-2cc(Nc2c(C)cccc2OC)nc1=O | ClC1=NC(N2C(C3=CC=C(C=C3CC2)OC)=C1)=O.COC1=C(N)C(=CC=C1)C>>COC=1C=C2CCN3C(C2=CC1)=CC(=NC3=O)NC3=C(C=CC=C3C)OC | Cl[c:14]1[cH:13][c:12]2[n:11]([c:26](=[O:27])[n:25]1)[CH2:10][CH2:9][c:7]1[c:6]-2[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:8]1.[NH2:15][c:16]1[c:17]([CH3:18])[cH:19][cH:20][cH:21][c:22]1[O:23][CH3:24]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([cH:8]1)[CH2:9][CH2:10][n:11]1[c:12]-2[cH:13][c:14]([NH:15][c:16]2[c:17]([CH3:18])[... | COc1ccc2c(c1)CCn1c-2cc(Cl)nc1=O.COc1cccc(C)c1N | COc1ccc2c(c1)CCn1c-2cc(Nc2c(C)cccc2OC)nc1=O | null | null | null | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c8475104970a63fce3d52b085fd15febf776cee9f570c7a80516c8bef4cb52de | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | O=c1nc(Nc2ccccc2)cc2n1CCc1ccccc1-2 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3](=[O;D1;H0:4]):[#7;a:5](:[c:6](:[c:7]:1)-[c:8])-[C:9].[NH2;D1;+0:10]-[c:11](:[c:12]):[c:13]>>[C:9]-[#7;a:5]1:[c:6](:[c:7]:[c;H0;D3;+0:1](-[NH;D2;+0:10]-[c:11](:[c:12]):[c:13]):[#7;a:2]:[c:3]:1=[O;D1;H0:4])-[c:8] | null | [] | null | null | null | null | The title compound was prepared from 2-chloro-9-methoxy-6,7-dihydro-pyrimido[6,1-a]isoquinolin-4-one (4) and 2-methoxy-6-methyl-aniline as in Example 1 d. 1H-NMR (400 MHz, d6-DMSO) δ 8.71 (br, 1H), 7.71 (br, 1H), 7.35-6.80 (5H), 6.39 (br, 1H), 3.92 (br, 2H), 3.83 (br, 3H), 3.74 (br, 3H), 2.94 (t, 2H) and 2.14 (br, 3H);... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccc2c(c1)CCn1cnccc21 | c1ccc2c(c1)CCn1cnccc21 | c1ccc2c(c1)CCn1cnccc21.c1ccccc1 | HCl | null | null | null | COc1ccc2c(c1)CCn1c-2cc(Cl)nc1=O.COc1cccc(C)c1N>>COc1ccc2c(c1)CCn1c-2cc(Nc2c(C)cccc2OC)nc1=O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-2634d225563c4a6a92ea2b62881e43a7 | COc1ccc2c(c1)CCn1c-2cc(Cl)nc1=O.Nc1ccc2cn[nH]c2c1>>COc1ccc2c(c1)CCn1c-2cc(Nc2ccc3cn[nH]c3c2)nc1=O | ClC1=NC(N2C(C3=CC=C(C=C3CC2)OC)=C1)=O.N1N=CC2=CC=C(C=C12)N>>N1N=CC2=CC=C(C=C12)NC1=NC(N2C(C3=CC=C(C=C3CC2)OC)=C1)=O | Cl[c:14]1[cH:13][c:12]2[n:11]([c:26](=[O:27])[n:25]1)[CH2:10][CH2:9][c:7]1[c:6]-2[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:8]1.[NH2:15][c:16]1[cH:17][cH:18][c:19]2[cH:20][n:21][nH:22][c:23]2[cH:24]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([cH:8]1)[CH2:9][CH2:10][n:11]1[c:12]-2[cH:13][c:14]([NH:15][c:16]2[cH:17][cH:18][c:19... | COc1ccc2c(c1)CCn1c-2cc(Cl)nc1=O.Nc1ccc2cn[nH]c2c1 | COc1ccc2c(c1)CCn1c-2cc(Nc2ccc3cn[nH]c3c2)nc1=O | null | null | null | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c8475104970a63fce3d52b085fd15febf776cee9f570c7a80516c8bef4cb52de | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | O=c1nc(Nc2ccc3cn[nH]c3c2)cc2n1CCc1ccccc1-2 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3](=[O;D1;H0:4]):[#7;a:5](:[c:6](:[c:7]:1)-[c:8])-[C:9].[#7;a:10]:[c:11]:[c:12]:[c:13](-[NH2;D1;+0:14]):[c:15]>>[#7;a:10]:[c:11]:[c:12]:[c:13](-[NH;D2;+0:14]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3](=[O;D1;H0:4]):[#7;a:5](:[c:6](:[c:7]:1)-[c:8])-[C:9]):[c:15] | null | [] | null | null | null | null | The title compound was prepared from 2-chloro-9-methoxy-6,7-dihydro-pyrimido[6,1-a]isoquinolin-4-one (4) and 1H-indazol-6-ylamine as in Example 1 d. 1H-NMR (400 MHz, d6-DMSO) δ 12.95 (br, 1H), 9.76 (s, 1H), 8.60 (s, 1H), 7.96 (s, 1H), 7.72-7.60 (2H), 7.15-6.95 (3H), 6.42 (s, 1H), 4.01 (t, 2H), 3.85 (s, 3H) and 2.98 (t,... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccc2c(c1)CCn1cnccc21 | c1ccc2c(c1)CCn1cnccc21 | c1ccc2c(c1)CCn1cnccc21.c1ccc2n[nH]cc2c1 | HCl | null | null | null | COc1ccc2c(c1)CCn1c-2cc(Cl)nc1=O.Nc1ccc2cn[nH]c2c1>>COc1ccc2c(c1)CCn1c-2cc(Nc2ccc3cn[nH]c3c2)nc1=O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-692a05dc5eb14e8ca643b1e2a0b9b9dc | COc1ccc2c(c1)CCn1c-2cc(Cl)nc1=O.Nc1ccccc1Br>>COc1ccc2c(c1)CCn1c-2cc(Nc2ccccc2Br)nc1=O | ClC1=NC(N2C(C3=CC=C(C=C3CC2)OC)=C1)=O.BrC1=C(N)C=CC=C1>>BrC1=C(C=CC=C1)NC1=NC(N2C(C3=CC=C(C=C3CC2)OC)=C1)=O | Cl[c:14]1[cH:13][c:12]2[n:11]([c:24](=[O:25])[n:23]1)[CH2:10][CH2:9][c:7]1[c:6]-2[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:8]1.[NH2:15][c:16]1[cH:17][cH:18][cH:19][cH:20][c:21]1[Br:22]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([cH:8]1)[CH2:9][CH2:10][n:11]1[c:12]-2[cH:13][c:14]([NH:15][c:16]2[cH:17][cH:18][cH:19][cH:20][c:21... | COc1ccc2c(c1)CCn1c-2cc(Cl)nc1=O.Nc1ccccc1Br | COc1ccc2c(c1)CCn1c-2cc(Nc2ccccc2Br)nc1=O | null | null | null | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c8475104970a63fce3d52b085fd15febf776cee9f570c7a80516c8bef4cb52de | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | O=c1nc(Nc2ccccc2)cc2n1CCc1ccccc1-2 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3](=[O;D1;H0:4]):[#7;a:5](:[c:6](:[c:7]:1)-[c:8])-[C:9].[NH2;D1;+0:10]-[c:11](:[c:12]):[c:13]>>[C:9]-[#7;a:5]1:[c:6](:[c:7]:[c;H0;D3;+0:1](-[NH;D2;+0:10]-[c:11](:[c:12]):[c:13]):[#7;a:2]:[c:3]:1=[O;D1;H0:4])-[c:8] | null | [] | null | null | null | null | The title compound was prepared from 2-chloro-9-methoxy-6,7-dihydro-pyrimido[6,1-a]isoquinolin-4-one (4) and 2-bromo-aniline as in Example 1 d. 1H-NMR (400 MHz, d6-DMSO) δ 9.06 (br, 1H), 7.76 (br, 1H), 7.69 (2H), 7.41 (t, 1H), 7.16 (t, 1H), 7.05-6.95 (2H), 6.47 (br, 1H), 3.96 (t, 2H), 3.84 (s, 3H) and 2.96 (t, 2H); MS ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccc2c(c1)CCn1cnccc21 | c1ccc2c(c1)CCn1cnccc21 | c1ccc2c(c1)CCn1cnccc21.c1ccccc1 | HCl | null | null | null | COc1ccc2c(c1)CCn1c-2cc(Cl)nc1=O.Nc1ccccc1Br>>COc1ccc2c(c1)CCn1c-2cc(Nc2ccccc2Br)nc1=O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-3476ab91ea64458395b40ed72ba1626d | COc1ccc2c(c1)CCn1c-2cc(Cl)nc1=O.Nc1cccc(S(N)(=O)=O)c1>>COc1ccc2c(c1)CCn1c-2cc(Nc2cccc(S(N)(=O)=O)c2)nc1=O | ClC1=NC(N2C(C3=CC=C(C=C3CC2)OC)=C1)=O.NC=1C=C(C=CC1)S(=O)(=O)N>>COC=1C=C2CCN3C(C2=CC1)=CC(=NC3=O)NC=3C=C(C=CC3)S(=O)(=O)N | Cl[c:14]1[cH:13][c:12]2[n:11]([c:27](=[O:28])[n:26]1)[CH2:10][CH2:9][c:7]1[c:6]-2[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:8]1.[NH2:15][c:16]1[cH:17][cH:18][cH:19][c:20]([S:21]([NH2:22])(=[O:23])=[O:24])[cH:25]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([cH:8]1)[CH2:9][CH2:10][n:11]1[c:12]-2[cH:13][c:14]([NH:15][c:16]2[cH:17... | COc1ccc2c(c1)CCn1c-2cc(Cl)nc1=O.Nc1cccc(S(N)(=O)=O)c1 | COc1ccc2c(c1)CCn1c-2cc(Nc2cccc(S(N)(=O)=O)c2)nc1=O | null | null | null | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c8475104970a63fce3d52b085fd15febf776cee9f570c7a80516c8bef4cb52de | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | O=c1nc(Nc2ccccc2)cc2n1CCc1ccccc1-2 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3](=[O;D1;H0:4]):[#7;a:5](:[c:6](:[c:7]:1)-[c:8])-[C:9].[NH2;D1;+0:10]-[c:11](:[c:12]):[c:13]>>[C:9]-[#7;a:5]1:[c:6](:[c:7]:[c;H0;D3;+0:1](-[NH;D2;+0:10]-[c:11](:[c:12]):[c:13]):[#7;a:2]:[c:3]:1=[O;D1;H0:4])-[c:8] | null | [] | null | null | null | null | The title compound was prepared from 2-chloro-9-methoxy-6,7-dihydro-pyrimido[6,1-a]isoquinolin-4-one (4) and 3-amino-benzenesulfonamide as in Example 1 d. 1H-NMR (400 MHz, d6-DMSO) δ 9.91 (s, 1H), 8.17 (d, 1H), 8.11 (s, 1H), 7.70 (d, 1H), 7.54 (t, 1H), 7.48 (d, 1H), 7.39 (br, 2H), 7.05-6.98 (2H), 6.37 (s, 1H), 4.00 (t,... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccc2c(c1)CCn1cnccc21 | c1ccc2c(c1)CCn1cnccc21 | c1ccc2c(c1)CCn1cnccc21.c1ccccc1 | HCl | null | null | null | COc1ccc2c(c1)CCn1c-2cc(Cl)nc1=O.Nc1cccc(S(N)(=O)=O)c1>>COc1ccc2c(c1)CCn1c-2cc(Nc2cccc(S(N)(=O)=O)c2)nc1=O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ae42f06ab2d6487b929a0031b4ccdb27 | COc1ccc2c(c1)CCn1c-2cc(Cl)nc1=O.Nc1ccccc1Cl>>COc1ccc2c(c1)CCn1c-2cc(Nc2ccccc2Cl)nc1=O | ClC1=NC(N2C(C3=CC=C(C=C3CC2)OC)=C1)=O.ClC1=C(N)C=CC=C1>>ClC1=C(C=CC=C1)NC1=NC(N2C(C3=CC=C(C=C3CC2)OC)=C1)=O | Cl[c:14]1[cH:13][c:12]2[n:11]([c:24](=[O:25])[n:23]1)[CH2:10][CH2:9][c:7]1[c:6]-2[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:8]1.[NH2:15][c:16]1[cH:17][cH:18][cH:19][cH:20][c:21]1[Cl:22]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([cH:8]1)[CH2:9][CH2:10][n:11]1[c:12]-2[cH:13][c:14]([NH:15][c:16]2[cH:17][cH:18][cH:19][cH:20][c:21... | COc1ccc2c(c1)CCn1c-2cc(Cl)nc1=O.Nc1ccccc1Cl | COc1ccc2c(c1)CCn1c-2cc(Nc2ccccc2Cl)nc1=O | null | null | null | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c8475104970a63fce3d52b085fd15febf776cee9f570c7a80516c8bef4cb52de | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | O=c1nc(Nc2ccccc2)cc2n1CCc1ccccc1-2 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3](=[O;D1;H0:4]):[#7;a:5](:[c:6](:[c:7]:1)-[c:8])-[C:9].[NH2;D1;+0:10]-[c:11](:[c:12]):[c:13]>>[C:9]-[#7;a:5]1:[c:6](:[c:7]:[c;H0;D3;+0:1](-[NH;D2;+0:10]-[c:11](:[c:12]):[c:13]):[#7;a:2]:[c:3]:1=[O;D1;H0:4])-[c:8] | null | [] | null | null | null | null | The title compound was prepared from 2-chloro-9-methoxy-6,7-dihydro-pyrimido[6,1-a]isoquinolin-4-one (4) and 2-chloro-aniline as in Example 1 d. 1H-NMR (400 MHz, d6-DMSO) δ 9.10 (br, 1H), 7.91 (brd, 1H), 7.70 (brd, 1H), 7.53 (dd, 1H), 7.37 (t, 1H), 7.21 (t, 1H), 7.05-6.95 (2H), 6.55 (br, 1H), 3.97 (t, 2H), 3.84 (s, 3H)... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccc2c(c1)CCn1cnccc21 | c1ccc2c(c1)CCn1cnccc21 | c1ccc2c(c1)CCn1cnccc21.c1ccccc1 | HCl | null | null | null | COc1ccc2c(c1)CCn1c-2cc(Cl)nc1=O.Nc1ccccc1Cl>>COc1ccc2c(c1)CCn1c-2cc(Nc2ccccc2Cl)nc1=O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-da40987323084fe2ad68f524ed25d5a7 | COc1ccc2c(c1)CCn1c-2cc(Cl)nc1=O.Cc1cccc(C)c1N>>COc1ccc2c(c1)CCn1c-2cc(Nc2c(C)cccc2C)nc1=O | ClC1=NC(N2C(C3=CC=C(C=C3CC2)OC)=C1)=O.CC1=C(N)C(=CC=C1)C>>CC1=C(C(=CC=C1)C)NC1=NC(N2C(C3=CC=C(C=C3CC2)OC)=C1)=O | Cl[c:14]1[cH:13][c:12]2[n:11]([c:25](=[O:26])[n:24]1)[CH2:10][CH2:9][c:7]1[c:6]-2[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:8]1.[NH2:15][c:16]1[c:17]([CH3:18])[cH:19][cH:20][cH:21][c:22]1[CH3:23]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([cH:8]1)[CH2:9][CH2:10][n:11]1[c:12]-2[cH:13][c:14]([NH:15][c:16]2[c:17]([CH3:18])[cH:19]... | COc1ccc2c(c1)CCn1c-2cc(Cl)nc1=O.Cc1cccc(C)c1N | COc1ccc2c(c1)CCn1c-2cc(Nc2c(C)cccc2C)nc1=O | null | null | null | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c8475104970a63fce3d52b085fd15febf776cee9f570c7a80516c8bef4cb52de | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | O=c1nc(Nc2ccccc2)cc2n1CCc1ccccc1-2 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3](=[O;D1;H0:4]):[#7;a:5](:[c:6](:[c:7]:1)-[c:8])-[C:9].[NH2;D1;+0:10]-[c:11](:[c:12]):[c:13]>>[C:9]-[#7;a:5]1:[c:6](:[c:7]:[c;H0;D3;+0:1](-[NH;D2;+0:10]-[c:11](:[c:12]):[c:13]):[#7;a:2]:[c:3]:1=[O;D1;H0:4])-[c:8] | null | [] | null | null | null | null | The title compound was prepared from 2-chloro-9-methoxy-6,7-dihydro-pyrimido[6,1-a]isoquinolin-4-one (4) and 2,6-dimethyl-aniline as in Example 1 d. 1H-NMR as two isomeric mixture (400 MHz, d6-DMSO) δ 8.96 and 8.87 (br, 1H), 7.75 and 7.29 (d, 1H), 7.23-6.80 (5H), 6.37 and 5.33 (br, 1H), 3.96 and 3.92 (t, 2H), 3.84 and ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccc2c(c1)CCn1cnccc21 | c1ccc2c(c1)CCn1cnccc21 | c1ccc2c(c1)CCn1cnccc21.c1ccccc1 | HCl | null | null | null | COc1ccc2c(c1)CCn1c-2cc(Cl)nc1=O.Cc1cccc(C)c1N>>COc1ccc2c(c1)CCn1c-2cc(Nc2c(C)cccc2C)nc1=O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-b3272511036a47d788066056645698f7 | COc1ccc2c(c1)CCn1c-2cc(Cl)nc1=O.Nc1c(F)cccc1Br>>COc1ccc2c(c1)CCn1c-2cc(Nc2c(F)cccc2Br)nc1=O | ClC1=NC(N2C(C3=CC=C(C=C3CC2)OC)=C1)=O.BrC1=C(N)C(=CC=C1)F>>BrC1=C(C(=CC=C1)F)NC1=NC(N2C(C3=CC=C(C=C3CC2)OC)=C1)=O | Cl[c:14]1[cH:13][c:12]2[n:11]([c:25](=[O:26])[n:24]1)[CH2:10][CH2:9][c:7]1[c:6]-2[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:8]1.[NH2:15][c:16]1[c:17]([F:18])[cH:19][cH:20][cH:21][c:22]1[Br:23]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([cH:8]1)[CH2:9][CH2:10][n:11]1[c:12]-2[cH:13][c:14]([NH:15][c:16]2[c:17]([F:18])[cH:19][cH:2... | COc1ccc2c(c1)CCn1c-2cc(Cl)nc1=O.Nc1c(F)cccc1Br | COc1ccc2c(c1)CCn1c-2cc(Nc2c(F)cccc2Br)nc1=O | null | null | null | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c8475104970a63fce3d52b085fd15febf776cee9f570c7a80516c8bef4cb52de | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | O=c1nc(Nc2ccccc2)cc2n1CCc1ccccc1-2 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3](=[O;D1;H0:4]):[#7;a:5](:[c:6](:[c:7]:1)-[c:8])-[C:9].[NH2;D1;+0:10]-[c:11](:[c:12]):[c:13]>>[C:9]-[#7;a:5]1:[c:6](:[c:7]:[c;H0;D3;+0:1](-[NH;D2;+0:10]-[c:11](:[c:12]):[c:13]):[#7;a:2]:[c:3]:1=[O;D1;H0:4])-[c:8] | null | [] | null | null | null | null | The title compound was prepared from 2-chloro-9-methoxy-6,7-dihydro-pyrimido[6,1-a]isoquinolin-4-one (4) and 2-bromo-6-fluoro-aniline as in Example 1 d. 1H-NMR (400 MHz, d6-DMSO) δ 9.26 (br, 1H), 7.72 (br, 1H), 7.57 (brd, 1H), 7.34 (br, 2H), 7.05-6.95 (2H), 6.37 (br, 1H), 3.94 (t, 2H), 3.84 (s, 3H) and 2.96 (t, 2H); MS... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccc2c(c1)CCn1cnccc21 | c1ccc2c(c1)CCn1cnccc21 | c1ccc2c(c1)CCn1cnccc21.c1ccccc1 | HCl | null | null | null | COc1ccc2c(c1)CCn1c-2cc(Cl)nc1=O.Nc1c(F)cccc1Br>>COc1ccc2c(c1)CCn1c-2cc(Nc2c(F)cccc2Br)nc1=O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-fc0adbbcac84454fbc08c21418c2b918 | COc1ccc2c(c1)CCn1c-2cc(Cl)nc1=O.COc1cccc(N)c1>>COc1cccc(Nc2cc3n(c(=O)n2)CCc2cc(OC)ccc2-3)c1 | ClC1=NC(N2C(C3=CC=C(C=C3CC2)OC)=C1)=O.COC=1C=C(N)C=CC1>>COC=1C=C(C=CC1)NC1=NC(N2C(C3=CC=C(C=C3CC2)OC)=C1)=O | Cl[c:9]1[cH:10][c:11]2[n:12]([c:13](=[O:14])[n:15]1)[CH2:16][CH2:17][c:18]1[cH:19][c:20]([O:21][CH3:22])[cH:23][cH:24][c:25]1-2.[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]([NH2:8])[cH:26]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]([NH:8][c:9]2[cH:10][c:11]3[n:12]([c:13](=[O:14])[n:15]2)[CH2:16][CH2:17][c:18]2[cH:19][c:2... | COc1ccc2c(c1)CCn1c-2cc(Cl)nc1=O.COc1cccc(N)c1 | COc1cccc(Nc2cc3n(c(=O)n2)CCc2cc(OC)ccc2-3)c1 | null | null | null | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c8475104970a63fce3d52b085fd15febf776cee9f570c7a80516c8bef4cb52de | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | O=c1nc(Nc2ccccc2)cc2n1CCc1ccccc1-2 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3](=[O;D1;H0:4]):[#7;a:5](:[c:6](:[c:7]:1)-[c:8])-[C:9].[NH2;D1;+0:10]-[c:11](:[c:12]):[c:13]>>[C:9]-[#7;a:5]1:[c:6](:[c:7]:[c;H0;D3;+0:1](-[NH;D2;+0:10]-[c:11](:[c:12]):[c:13]):[#7;a:2]:[c:3]:1=[O;D1;H0:4])-[c:8] | null | [] | null | null | null | null | The title compound was prepared from 2-chloro-9-methoxy-6,7-dihydro-pyrimido[6,1-a]isoquinolin-4-one (4) and 3-methoxyaniline as in Example 1 d. 1H-NMR (400 MHz, d6-DMSO) δ 9.59 (s, 1H), 7.68 (d, 1H), 7.52 (br, 1H), 7.30 (d, 1H), 7.23 (t, 1H), 7.05-6.95 (2H), 6.63 (dd, 1H), 6.35 (s, 1H), 3.98 (t, 2H), 3.84 (s, 3H), 3.7... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccc2c(c1)CCn1cnccc21 | c1ccc2c(c1)CCn1cnccc21 | c1ccccc1.c1ccc2c(c1)CCn1cnccc21 | HCl | null | null | null | COc1ccc2c(c1)CCn1c-2cc(Cl)nc1=O.COc1cccc(N)c1>>COc1cccc(Nc2cc3n(c(=O)n2)CCc2cc(OC)ccc2-3)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-1213ad2a0e2b4298960163ed0da23b17 | COc1ccc2c(c1)CCn1c-2cc(Cl)nc1=O.Cc1cccc(O)c1N>>COc1ccc2c(c1)CCn1c-2cc(Nc2c(C)cccc2O)nc1=O | ClC1=NC(N2C(C3=CC=C(C=C3CC2)OC)=C1)=O.OC1=C(N)C(=CC=C1)C>>OC1=C(C(=CC=C1)C)NC1=NC(N2C(C3=CC=C(C=C3CC2)OC)=C1)=O | Cl[c:14]1[cH:13][c:12]2[n:11]([c:25](=[O:26])[n:24]1)[CH2:10][CH2:9][c:7]1[c:6]-2[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:8]1.[NH2:15][c:16]1[c:17]([CH3:18])[cH:19][cH:20][cH:21][c:22]1[OH:23]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([cH:8]1)[CH2:9][CH2:10][n:11]1[c:12]-2[cH:13][c:14]([NH:15][c:16]2[c:17]([CH3:18])[cH:19][... | COc1ccc2c(c1)CCn1c-2cc(Cl)nc1=O.Cc1cccc(O)c1N | COc1ccc2c(c1)CCn1c-2cc(Nc2c(C)cccc2O)nc1=O | null | null | null | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c8475104970a63fce3d52b085fd15febf776cee9f570c7a80516c8bef4cb52de | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | O=c1nc(Nc2ccccc2)cc2n1CCc1ccccc1-2 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3](=[O;D1;H0:4]):[#7;a:5](:[c:6](:[c:7]:1)-[c:8])-[C:9].[NH2;D1;+0:10]-[c:11](:[c:12]):[c:13]>>[C:9]-[#7;a:5]1:[c:6](:[c:7]:[c;H0;D3;+0:1](-[NH;D2;+0:10]-[c:11](:[c:12]):[c:13]):[#7;a:2]:[c:3]:1=[O;D1;H0:4])-[c:8] | null | [] | null | null | null | null | The title compound was prepared from 2-chloro-9-methoxy-6,7-dihydro-pyrimido[6,1-a]isoquinolin-4-one (4) and 2-hydroxy-6-methyl-aniline as in Example 1 d. 1H-NMR (400 MHz, d6-DMSO, at 60° C.) δ 9.39 (br, 1H), 8.60 (br, 1H), 7.61 (br, 1H), 7.05-6.95 (3H), 6.75 (d, 1H), 6.73 (d, 1H), 6.34 (br, 1H), 3.95 (t, 2H), 3.83 (s,... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccc2c(c1)CCn1cnccc21 | c1ccc2c(c1)CCn1cnccc21 | c1ccc2c(c1)CCn1cnccc21.c1ccccc1 | HCl | null | null | null | COc1ccc2c(c1)CCn1c-2cc(Cl)nc1=O.Cc1cccc(O)c1N>>COc1ccc2c(c1)CCn1c-2cc(Nc2c(C)cccc2O)nc1=O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-bf986b7aaf984030a8ed8da032def2d9 | COc1ccc(-c2ccccc2)cc1N.COc1ccc2c(c1)CCn1c-2cc(Cl)nc1=O>>COc1ccc2c(c1)CCn1c-2cc(Nc2cc(-c3ccccc3)ccc2OC)nc1=O | ClC1=NC(N2C(C3=CC=C(C=C3CC2)OC)=C1)=O.NC=1C=C(C=CC1OC)C1=CC=CC=C1>>COC=1C=C2CCN3C(C2=CC1)=CC(=NC3=O)NC=3C=C(C=CC3OC)C3=CC=CC=C3 | [NH2:15][c:16]1[cH:17][c:18](-[c:19]2[cH:20][cH:21][cH:22][cH:23][cH:24]2)[cH:25][cH:26][c:27]1[O:28][CH3:29].Cl[c:14]1[cH:13][c:12]2[n:11]([c:31](=[O:32])[n:30]1)[CH2:10][CH2:9][c:7]1[c:6]-2[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:8]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([cH:8]1)[CH2:9][CH2:10][n:11]1[c:12]-2[cH:13][c... | COc1ccc(-c2ccccc2)cc1N.COc1ccc2c(c1)CCn1c-2cc(Cl)nc1=O | COc1ccc2c(c1)CCn1c-2cc(Nc2cc(-c3ccccc3)ccc2OC)nc1=O | null | null | null | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c8475104970a63fce3d52b085fd15febf776cee9f570c7a80516c8bef4cb52de | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | O=c1nc(Nc2cccc(-c3ccccc3)c2)cc2n1CCc1ccccc1-2 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3](=[O;D1;H0:4]):[#7;a:5](:[c:6](:[c:7]:1)-[c:8])-[C:9].[NH2;D1;+0:10]-[c:11](:[c:12]):[c:13]>>[C:9]-[#7;a:5]1:[c:6](:[c:7]:[c;H0;D3;+0:1](-[NH;D2;+0:10]-[c:11](:[c:12]):[c:13]):[#7;a:2]:[c:3]:1=[O;D1;H0:4])-[c:8] | null | [] | null | null | null | null | The title compound was prepared from 2-chloro-9-methoxy-6,7-dihydro-pyrimido[6,1-a]isoquinolin-4-one (4) and 3-amino-4-methoxy-biphenyl as in Example 1 d. 1H-NMR (400 MHz, d8-DMSO) δ 8.85 (s, 1H), 8.55 (br, 1H), 7.70 (d, 1H), 7.60 (d, 2H), 7.46 (t, 2H), 7.38 (dd, 1H), 7.33 (t, 1H), 7.16 (d, 1H), 7.02 (dd, 1H), 6.98 (d,... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccc2c(c1)CCn1cnccc21 | c1ccc2c(c1)CCn1cnccc21 | c1ccc2c(c1)CCn1cnccc21.c1ccccc1.c1ccccc1 | HCl | null | null | null | COc1ccc(-c2ccccc2)cc1N.COc1ccc2c(c1)CCn1c-2cc(Cl)nc1=O>>COc1ccc2c(c1)CCn1c-2cc(Nc2cc(-c3ccccc3)ccc2OC)nc1=O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d9f835ed430e4e08ae863940294eabf6 | CCOC(=O)c1cccc(N)c1.COc1ccc2c(c1)CCn1c-2cc(Cl)nc1=O>>CCOC(=O)c1cccc(Nc2cc3n(c(=O)n2)CCc2cc(OC)ccc2-3)c1 | ClC1=NC(N2C(C3=CC=C(C=C3CC2)OC)=C1)=O.C(C)OC(C1=CC(=CC=C1)N)=O>>C(C)OC(C1=CC(=CC=C1)NC1=NC(N2C(C3=CC=C(C=C3CC2)OC)=C1)=O)=O | [CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][cH:9][c:10]([NH2:11])[cH:29]1.Cl[c:12]1[cH:13][c:14]2[n:15]([c:16](=[O:17])[n:18]1)[CH2:19][CH2:20][c:21]1[cH:22][c:23]([O:24][CH3:25])[cH:26][cH:27][c:28]1-2>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][cH:9][c:10]([NH:11][c:12]2[cH:13][c:14]3[n:15]([c:16](=[O:... | CCOC(=O)c1cccc(N)c1.COc1ccc2c(c1)CCn1c-2cc(Cl)nc1=O | CCOC(=O)c1cccc(Nc2cc3n(c(=O)n2)CCc2cc(OC)ccc2-3)c1 | null | null | null | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c8475104970a63fce3d52b085fd15febf776cee9f570c7a80516c8bef4cb52de | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | O=c1nc(Nc2ccccc2)cc2n1CCc1ccccc1-2 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3](=[O;D1;H0:4]):[#7;a:5](:[c:6](:[c:7]:1)-[c:8])-[C:9].[NH2;D1;+0:10]-[c:11](:[c:12]):[c:13]>>[C:9]-[#7;a:5]1:[c:6](:[c:7]:[c;H0;D3;+0:1](-[NH;D2;+0:10]-[c:11](:[c:12]):[c:13]):[#7;a:2]:[c:3]:1=[O;D1;H0:4])-[c:8] | null | [] | null | null | null | null | The title compound was prepared from 2-chloro-9-methoxy-6,7-dihydro-pyrimido[6,1-a]isoquinolin-4-one (4) and 3-amino-benzoic acid ethyl ester as in Example 1 d. 1H-NMR (400 MHz, d0-DMSO) δ 9.84 (s, 1H), 8.26 (s, 1H), 8.21 (d, 1H), 7.70 (d, 1H), 7.62 (d, 1H), 7.49 (t, 1H), 7.05-6.97 (2H), 6.36 (s, 1H), 4.33 (q, 2H), 3.9... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccc2c(c1)CCn1cnccc21 | c1ccc2c(c1)CCn1cnccc21 | c1ccccc1.c1ccc2c(c1)CCn1cnccc21 | HCl | null | null | null | CCOC(=O)c1cccc(N)c1.COc1ccc2c(c1)CCn1c-2cc(Cl)nc1=O>>CCOC(=O)c1cccc(Nc2cc3n(c(=O)n2)CCc2cc(OC)ccc2-3)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e9e6ae9ae5d84a0db20bb294f7ccb050 | COc1ccc2c(c1)CCn1c-2cc(Cl)nc1=O.COc1ccccc1N>>COc1ccc2c(c1)CCn1c-2cc(Nc2ccccc2OC)nc1=O | ClC1=NC(N2C(C3=CC=C(C=C3CC2)OC)=C1)=O.COC1=C(N)C=CC=C1>>COC=1C=C2CCN3C(C2=CC1)=CC(=NC3=O)NC3=C(C=CC=C3)OC | Cl[c:14]1[cH:13][c:12]2[n:11]([c:25](=[O:26])[n:24]1)[CH2:10][CH2:9][c:7]1[c:6]-2[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:8]1.[NH2:15][c:16]1[cH:17][cH:18][cH:19][cH:20][c:21]1[O:22][CH3:23]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([cH:8]1)[CH2:9][CH2:10][n:11]1[c:12]-2[cH:13][c:14]([NH:15][c:16]2[cH:17][cH:18][cH:19][cH:2... | COc1ccc2c(c1)CCn1c-2cc(Cl)nc1=O.COc1ccccc1N | COc1ccc2c(c1)CCn1c-2cc(Nc2ccccc2OC)nc1=O | null | null | null | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c8475104970a63fce3d52b085fd15febf776cee9f570c7a80516c8bef4cb52de | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | O=c1nc(Nc2ccccc2)cc2n1CCc1ccccc1-2 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3](=[O;D1;H0:4]):[#7;a:5](:[c:6](:[c:7]:1)-[c:8])-[C:9].[NH2;D1;+0:10]-[c:11](:[c:12]):[c:13]>>[C:9]-[#7;a:5]1:[c:6](:[c:7]:[c;H0;D3;+0:1](-[NH;D2;+0:10]-[c:11](:[c:12]):[c:13]):[#7;a:2]:[c:3]:1=[O;D1;H0:4])-[c:8] | null | [] | null | null | null | null | The title compound was prepared from 2-chloro-9-methoxy-6,7-dihydro-pyrimido[6,1-a]isoquinolin-4-one (4) and 2-methoxy-aniline as in Example 1 d. 1H-NMR (400 MHz, d6-DMSO) 88.74 (s, 1H), 8.24 (br, 1H), 7.69 (d, 1H), 7.12-6.92 (5H), 6.70 (br, 1H), 3.97 (t, 2H), 3.87 (s, 3H), 3.84 (s, 3H) and 2.96 (t, 2H); MS (ESI) (M+H)... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccc2c(c1)CCn1cnccc21 | c1ccc2c(c1)CCn1cnccc21 | c1ccc2c(c1)CCn1cnccc21.c1ccccc1 | HCl | null | null | null | COc1ccc2c(c1)CCn1c-2cc(Cl)nc1=O.COc1ccccc1N>>COc1ccc2c(c1)CCn1c-2cc(Nc2ccccc2OC)nc1=O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-5841729151dc4f0c9c7ee07f39357ea2 | COc1ccc2c(c1)CCn1c-2cc(Cl)nc1=O.Nc1ccccc1C(F)(F)F>>COc1ccc2c(c1)CCn1c-2cc(Nc2ccccc2C(F)(F)F)nc1=O | ClC1=NC(N2C(C3=CC=C(C=C3CC2)OC)=C1)=O.FC(C1=C(N)C=CC=C1)(F)F>>COC=1C=C2CCN3C(C2=CC1)=CC(=NC3=O)NC3=C(C=CC=C3)C(F)(F)F | Cl[c:14]1[cH:13][c:12]2[n:11]([c:27](=[O:28])[n:26]1)[CH2:10][CH2:9][c:7]1[c:6]-2[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:8]1.[NH2:15][c:16]1[cH:17][cH:18][cH:19][cH:20][c:21]1[C:22]([F:23])([F:24])[F:25]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([cH:8]1)[CH2:9][CH2:10][n:11]1[c:12]-2[cH:13][c:14]([NH:15][c:16]2[cH:17][cH:1... | COc1ccc2c(c1)CCn1c-2cc(Cl)nc1=O.Nc1ccccc1C(F)(F)F | COc1ccc2c(c1)CCn1c-2cc(Nc2ccccc2C(F)(F)F)nc1=O | null | null | null | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c8475104970a63fce3d52b085fd15febf776cee9f570c7a80516c8bef4cb52de | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | O=c1nc(Nc2ccccc2)cc2n1CCc1ccccc1-2 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3](=[O;D1;H0:4]):[#7;a:5](:[c:6](:[c:7]:1)-[c:8])-[C:9].[NH2;D1;+0:10]-[c:11](:[c:12]):[c:13]>>[C:9]-[#7;a:5]1:[c:6](:[c:7]:[c;H0;D3;+0:1](-[NH;D2;+0:10]-[c:11](:[c:12]):[c:13]):[#7;a:2]:[c:3]:1=[O;D1;H0:4])-[c:8] | null | [] | null | null | null | null | The title compound was prepared from 2-chloro-9-methoxy-6,7-dihydro-pyrimido[6,1-a]isoquinolin-4-one (4) and 2-trifluoromethyl-aniline as in Example 1 d. 1H-NMR (400 MHz, d6-DMSO) δ 9.10 (br, 1H), 7.90-7.35 (5H), 6.98 (2H), 6.42 (br, 1H), 3.94 (brt, 2H), 3.83 (s, 3H) and 2.95 (t, 2H); MS (ESI) (M+H)+ 388.
Conditions: S... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccc2c(c1)CCn1cnccc21 | c1ccc2c(c1)CCn1cnccc21 | c1ccc2c(c1)CCn1cnccc21.c1ccccc1 | HCl | null | null | null | COc1ccc2c(c1)CCn1c-2cc(Cl)nc1=O.Nc1ccccc1C(F)(F)F>>COc1ccc2c(c1)CCn1c-2cc(Nc2ccccc2C(F)(F)F)nc1=O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-eff3521913c2417e908e24d825848e7c | COc1ccc2c(c1)CCn1c-2cc(Cl)nc1=O.Cc1cc(Cl)cc(C)c1N>>COc1ccc2c(c1)CCn1c-2cc(Nc2c(C)cc(Cl)cc2C)nc1=O | ClC1=NC(N2C(C3=CC=C(C=C3CC2)OC)=C1)=O.ClC1=CC(=C(N)C(=C1)C)C>>ClC1=CC(=C(C(=C1)C)NC1=NC(N2C(C3=CC=C(C=C3CC2)OC)=C1)=O)C | Cl[c:14]1[cH:13][c:12]2[n:11]([c:26](=[O:27])[n:25]1)[CH2:10][CH2:9][c:7]1[c:6]-2[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:8]1.[NH2:15][c:16]1[c:17]([CH3:18])[cH:19][c:20]([Cl:21])[cH:22][c:23]1[CH3:24]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([cH:8]1)[CH2:9][CH2:10][n:11]1[c:12]-2[cH:13][c:14]([NH:15][c:16]2[c:17]([CH3:18]... | COc1ccc2c(c1)CCn1c-2cc(Cl)nc1=O.Cc1cc(Cl)cc(C)c1N | COc1ccc2c(c1)CCn1c-2cc(Nc2c(C)cc(Cl)cc2C)nc1=O | null | null | null | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c8475104970a63fce3d52b085fd15febf776cee9f570c7a80516c8bef4cb52de | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | O=c1nc(Nc2ccccc2)cc2n1CCc1ccccc1-2 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3](=[O;D1;H0:4]):[#7;a:5](:[c:6](:[c:7]:1)-[c:8])-[C:9].[NH2;D1;+0:10]-[c:11](:[c:12]):[c:13]>>[C:9]-[#7;a:5]1:[c:6](:[c:7]:[c;H0;D3;+0:1](-[NH;D2;+0:10]-[c:11](:[c:12]):[c:13]):[#7;a:2]:[c:3]:1=[O;D1;H0:4])-[c:8] | null | [] | null | null | null | null | The title compound was prepared from 2-chloro-9-methoxy-6,7-dihydro-pyrimido[6,1-a]isoquinolin-4-one (4) and 4-Chloro-2,6-dimethyl-aniline as in Example 1 d. 1H-NMR (400 MHz, d6-DMSO) δ 8.73 (br, 1H), 7.72 (br, 1H), 7.19 (s, 2H), 7.03-6.95 (2H), 6.36 (br, 1H), 3.95 (t, 2H), 3.85 (s, 3H), 2.96 (t, 2H) and 2.18 (s, 6H); ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccc2c(c1)CCn1cnccc21 | c1ccc2c(c1)CCn1cnccc21 | c1ccc2c(c1)CCn1cnccc21.c1ccccc1 | HCl | null | null | null | COc1ccc2c(c1)CCn1c-2cc(Cl)nc1=O.Cc1cc(Cl)cc(C)c1N>>COc1ccc2c(c1)CCn1c-2cc(Nc2c(C)cc(Cl)cc2C)nc1=O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ffc01c1b489b4d53a6148a0d3a600342 | COc1ccc2c(c1)CCn1c-2cc(Cl)nc1=O.Nc1cccc2ncccc12>>COc1ccc2c(c1)CCn1c-2cc(Nc2cccc3ncccc23)nc1=O | ClC1=NC(N2C(C3=CC=C(C=C3CC2)OC)=C1)=O.NC1=C2C=CC=NC2=CC=C1>>COC=1C=C2CCN3C(C2=CC1)=CC(=NC3=O)NC3=C1C=CC=NC1=CC=C3 | Cl[c:14]1[cH:13][c:12]2[n:11]([c:27](=[O:28])[n:26]1)[CH2:10][CH2:9][c:7]1[c:6]-2[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:8]1.[NH2:15][c:16]1[cH:17][cH:18][cH:19][c:20]2[n:21][cH:22][cH:23][cH:24][c:25]12>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([cH:8]1)[CH2:9][CH2:10][n:11]1[c:12]-2[cH:13][c:14]([NH:15][c:16]2[cH:17][cH:1... | COc1ccc2c(c1)CCn1c-2cc(Cl)nc1=O.Nc1cccc2ncccc12 | COc1ccc2c(c1)CCn1c-2cc(Nc2cccc3ncccc23)nc1=O | null | null | null | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c8475104970a63fce3d52b085fd15febf776cee9f570c7a80516c8bef4cb52de | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | O=c1nc(Nc2cccc3ncccc23)cc2n1CCc1ccccc1-2 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3](=[O;D1;H0:4]):[#7;a:5](:[c:6](:[c:7]:1)-[c:8])-[C:9].[#7;a:10]:[c:11]:[c:12]:[c:13](-[NH2;D1;+0:14]):[c:15]>>[#7;a:10]:[c:11]:[c:12]:[c:13](-[NH;D2;+0:14]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3](=[O;D1;H0:4]):[#7;a:5](:[c:6](:[c:7]:1)-[c:8])-[C:9]):[c:15] | null | [] | null | null | null | null | The title compound was prepared from 2-chloro-9-methoxy-6,7-dihydro-pyrimido[6,1-a]isoquinolin-4-one (4) and 5-amino-quinoline as in Example 1 d. 1H-NMR (400 MHz, d6-DMSO) δ 9.68 (br, 1H), 8.93 (dd, 1H), 8.47 (d, 1H), 7.89 (2H), 7.79 (t, 1H), 7.70 (d, 1H), 7.57 (dd, 1H), 7.03-6.97 (2H), 6.49 (br, 1H), 3.97 (t, 2H), 3.8... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccc2c(c1)CCn1cnccc21 | c1ccc2c(c1)CCn1cnccc21 | c1ccc2c(c1)CCn1cnccc21.c1ccc2ncccc2c1 | HCl | null | null | null | COc1ccc2c(c1)CCn1c-2cc(Cl)nc1=O.Nc1cccc2ncccc12>>COc1ccc2c(c1)CCn1c-2cc(Nc2cccc3ncccc23)nc1=O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-c16444c92ddc4fdfa9dee910b7189801 | COc1ccc2c(c1)CCn1c-2cc(Cl)nc1=O.NNc1ccccc1Br>>COc1ccc2c(c1)CCn1c-2cc(NNc2ccccc2Br)nc1=O | ClC1=NC(N2C(C3=CC=C(C=C3CC2)OC)=C1)=O.BrC1=C(C=CC=C1)NN>>BrC1=C(C=CC=C1)NNC1=NC(N2C(C3=CC=C(C=C3CC2)OC)=C1)=O | Cl[c:14]1[cH:13][c:12]2[n:11]([c:25](=[O:26])[n:24]1)[CH2:10][CH2:9][c:7]1[c:6]-2[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:8]1.[NH2:15][NH:16][c:17]1[cH:18][cH:19][cH:20][cH:21][c:22]1[Br:23]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([cH:8]1)[CH2:9][CH2:10][n:11]1[c:12]-2[cH:13][c:14]([NH:15][NH:16][c:17]2[cH:18][cH:19][cH:2... | COc1ccc2c(c1)CCn1c-2cc(Cl)nc1=O.NNc1ccccc1Br | COc1ccc2c(c1)CCn1c-2cc(NNc2ccccc2Br)nc1=O | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | ce26decf59eb6bfa42e6c1e2b26f98592223e1c8c92a1a68b7456a5e295b547b | 61806bbf8bb8981e140ee503663af0ef0e69dc4f34f6582f974a2e4218f7da88 | O=c1nc(NNc2ccccc2)cc2n1CCc1ccccc1-2 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3](=[O;D1;H0:4]):[#7;a:5](:[c:6](:[c:7]:1)-[c:8])-[C:9].[NH2;D1;+0:10]-[#7:11]-[c:12]>>[C:9]-[#7;a:5]1:[c:6](:[c:7]:[c;H0;D3;+0:1](-[NH;D2;+0:10]-[#7:11]-[c:12]):[#7;a:2]:[c:3]:1=[O;D1;H0:4])-[c:8] | null | [] | null | null | null | null | The title compound was prepared from 2-chloro-9-methoxy-6,7-dihydro-pyrimido[6,1-a]isoquinolin-4-one (4) and (2-bromo-phenyl)-hydrazine as in Example 1 d. 1H-NMR (400 MHz, d6-DMSO at 60° C.) δ 9.19 (br, 1H), 7.66 (brd, 1H), 7.46 (d, 1H), 7.44 (br, 1H), 7.20 (t, 1H), 6.98-6.75 (3H), 6.71 (t, 1H), 6.23 (s, 1H), 3.94 (t, ... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Aromatic halide | Hydrazine | c1ccc2c(c1)CCn1cnccc21 | c1ccc2c(c1)CCn1cnccc21 | c1ccc2c(c1)CCn1cnccc21.c1ccccc1 | HCl | null | null | null | COc1ccc2c(c1)CCn1c-2cc(Cl)nc1=O.NNc1ccccc1Br>>COc1ccc2c(c1)CCn1c-2cc(NNc2ccccc2Br)nc1=O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ba53c7a73ab848acbfbb41d961be87ed | CN(N)c1ccccc1.COc1ccc2c(c1)CCn1c-2cc(Cl)nc1=O>>COc1ccc2c(c1)CCn1c-2cc(NN(C)c2ccccc2)nc1=O | ClC1=NC(N2C(C3=CC=C(C=C3CC2)OC)=C1)=O.CN(N)C1=CC=CC=C1>>COC=1C=C2CCN3C(C2=CC1)=CC(=NC3=O)NN(C3=CC=CC=C3)C | [NH2:15][N:16]([CH3:17])[c:18]1[cH:19][cH:20][cH:21][cH:22][cH:23]1.Cl[c:14]1[cH:13][c:12]2[n:11]([c:25](=[O:26])[n:24]1)[CH2:10][CH2:9][c:7]1[c:6]-2[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:8]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([cH:8]1)[CH2:9][CH2:10][n:11]1[c:12]-2[cH:13][c:14]([NH:15][N:16]([CH3:17])[c:18]2[cH:19]... | CN(N)c1ccccc1.COc1ccc2c(c1)CCn1c-2cc(Cl)nc1=O | COc1ccc2c(c1)CCn1c-2cc(NN(C)c2ccccc2)nc1=O | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | ce26decf59eb6bfa42e6c1e2b26f98592223e1c8c92a1a68b7456a5e295b547b | 61806bbf8bb8981e140ee503663af0ef0e69dc4f34f6582f974a2e4218f7da88 | O=c1nc(NNc2ccccc2)cc2n1CCc1ccccc1-2 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3](=[O;D1;H0:4]):[#7;a:5](:[c:6](:[c:7]:1)-[c:8])-[C:9].[C;D1;H3:10]-[#7:11](-[NH2;D1;+0:12])-[c:13]>>[C:9]-[#7;a:5]1:[c:6](:[c:7]:[c;H0;D3;+0:1](-[NH;D2;+0:12]-[#7:11](-[C;D1;H3:10])-[c:13]):[#7;a:2]:[c:3]:1=[O;D1;H0:4])-[c:8] | null | [] | null | null | null | null | The title compound was prepared from 2-chloro-9-methoxy-6,7-dihydro-pyrimido[6,1-a]isoquinolin-4-one (4) and N-methyl-N-phenyl-hydrazine as in Example 1 d. 1H-NMR (400 MHz, d6-DMSO at 60° C.) δ 9.12 (br, 1H), 7.68 (d, 1H), 7.22 (t, 2H), 6.95-6.75 (5H), 6.24 (s, 1H), 3.96 (br, 2H), 3.82 (s, 3H), 3.16 (s, 3H) and 2.94 (t... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Aromatic halide | Hydrazine | c1ccc2c(c1)CCn1cnccc21 | c1ccc2c(c1)CCn1cnccc21 | c1ccc2c(c1)CCn1cnccc21.c1ccccc1 | HCl | null | null | null | CN(N)c1ccccc1.COc1ccc2c(c1)CCn1c-2cc(Cl)nc1=O>>COc1ccc2c(c1)CCn1c-2cc(NN(C)c2ccccc2)nc1=O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-6580181d4669429b928a3ea281be0832 | CC(C)(C)OC(=O)NCCN.COc1ccc2c(c1)CCn1c-2cc(Cl)nc1=O>>COc1ccc2c(c1)CCn1c-2cc(NCCN)nc1=O | ClC1=NC(N2C(C3=CC=C(C=C3CC2)OC)=C1)=O.C(=O)(OC(C)(C)C)NCCN.Cl>>NCCNC1=NC(N2C(C3=CC=C(C=C3CC2)OC)=C1)=O | CC(C)(C)OC(=O)[NH:18][CH2:17][CH2:16][NH2:15].Cl[c:14]1[cH:13][c:12]2[n:11]([c:20](=[O:21])[n:19]1)[CH2:10][CH2:9][c:7]1[c:6]-2[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:8]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([cH:8]1)[CH2:9][CH2:10][n:11]1[c:12]-2[cH:13][c:14]([NH:15][CH2:16][CH2:17][NH2:18])[n:19][c:20]1=[O:21] | CC(C)(C)OC(=O)NCCN.COc1ccc2c(c1)CCn1c-2cc(Cl)nc1=O | COc1ccc2c(c1)CCn1c-2cc(NCCN)nc1=O | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 382dfd19e134b9fc7475f308567af6de9b45919acfda7adb00989c5ee9ce7027 | b189e21881719932ff7e93d2cee73d5d9b679e27f974877dd5fa270130c3c7ff | O=c1nccc2n1CCc1ccccc1-2 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[C:2]-[C:3]-[NH2;D1;+0:4].Cl-[c;H0;D3;+0:5]1:[#7;a:6]:[c:7](=[O;D1;H0:8]):[#7;a:9](:[c:10](:[c:11]:1)-[c:12])-[C:13]>>[C:13]-[#7;a:9]1:[c:10](:[c:11]:[c;H0;D3;+0:5](-[NH;D2;+0:4]-[C:3]-[C:2]-[NH2;D1;+0:1]):[#7;a:6]:[c:7]:1=[O;D1;H0:8])-[c:12] | null | [] | null | null | null | null | The title compound was prepared from 2-chloro-9-methoxy-6,7-dihydro-pyrimido[6,1-a]isoquinolin-4-one (4) and N-Boc-ethylenediamine as in Example 1 d, followed by treatment with HCl. 1H-NMR as mixture of two isomers (400 MHz, d6-DMSO) δ 9.25-8.40 (1H), 8.32 and 7.70 (d, 1H), 8.12 and 8.02 (br, 3H), 7.07-7.00 (m, 2H), 6.... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Carbamic ester.Ether.Primary amine.Boc | Primary amine.Secondary amine | c1ccc2c(c1)CCn1cnccc21 | c1ccc2c(c1)CCn1cnccc21 | c1ccc2c(c1)CCn1cnccc21 | HCl | null | null | null | CC(C)(C)OC(=O)NCCN.COc1ccc2c(c1)CCn1c-2cc(Cl)nc1=O>>COc1ccc2c(c1)CCn1c-2cc(NCCN)nc1=O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-1e5338f5ebdd4ad69327ba6377e40e8b | COc1ccc2c(c1)CCn1c-2cc(Cl)nc1=O.NCCN1CCCC1>>COc1ccc2c(c1)CCn1c-2cc(NCCN2CCCC2)nc1=O | ClC1=NC(N2C(C3=CC=C(C=C3CC2)OC)=C1)=O.N1(CCCC1)CCN.Cl>>COC=1C=C2CCN3C(C2=CC1)=CC(=NC3=O)NCCN3CCCC3 | Cl[c:14]1[cH:13][c:12]2[n:11]([c:24](=[O:25])[n:23]1)[CH2:10][CH2:9][c:7]1[c:6]-2[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:8]1.[NH2:15][CH2:16][CH2:17][N:18]1[CH2:19][CH2:20][CH2:21][CH2:22]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([cH:8]1)[CH2:9][CH2:10][n:11]1[c:12]-2[cH:13][c:14]([NH:15][CH2:16][CH2:17][N:18]2[CH2:19][C... | COc1ccc2c(c1)CCn1c-2cc(Cl)nc1=O.NCCN1CCCC1 | COc1ccc2c(c1)CCn1c-2cc(NCCN2CCCC2)nc1=O | null | null | null | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | c8475104970a63fce3d52b085fd15febf776cee9f570c7a80516c8bef4cb52de | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | O=c1nc(NCCN2CCCC2)cc2n1CCc1ccccc1-2 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3](=[O;D1;H0:4]):[#7;a:5](:[c:6](:[c:7]:1)-[c:8])-[C:9].[C:10]-[C:11]-[NH2;D1;+0:12]>>[C:9]-[#7;a:5]1:[c:6](:[c:7]:[c;H0;D3;+0:1](-[NH;D2;+0:12]-[C:11]-[C:10]):[#7;a:2]:[c:3]:1=[O;D1;H0:4])-[c:8] | null | [] | null | null | null | null | The title compound was prepared from 2-chloro-9-methoxy-6,7-dihydro-pyrimido[6, 1-a]isoquinolin-4-one (4) and 2-pyrrolidin-1-yl-ethylamine as in Example 1 d, followed by treatment with HCl. 1H-NMR (400 MHz, dB-DMSO) δ 7.64 (d, 1H), 7.59 (br, 1H), 7.00-6.92 (2H), 6.18 (s, 1H), 3.92 (t, 2H), 3.82 (s, 3H), 3.46 (m, 2H), 2... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccc2c(c1)CCn1cnccc21 | c1ccc2c(c1)CCn1cnccc21 | c1ccc2c(c1)CCn1cnccc21.C1CC[NH]C1 | HCl | null | null | null | COc1ccc2c(c1)CCn1c-2cc(Cl)nc1=O.NCCN1CCCC1>>COc1ccc2c(c1)CCn1c-2cc(NCCN2CCCC2)nc1=O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-7111dc4b01da4ae5b296add8e13344e3 | CN(C)CCN.COc1ccc2c(c1)CCn1c-2cc(Cl)nc1=O>>COc1ccc2c(c1)CCn1c-2cc(NCCN(C)C)nc1=O | ClC1=NC(N2C(C3=CC=C(C=C3CC2)OC)=C1)=O.CN(CCN)C>>CN(CCNC1=NC(N2C(C3=CC=C(C=C3CC2)OC)=C1)=O)C | [NH2:15][CH2:16][CH2:17][N:18]([CH3:19])[CH3:20].Cl[c:14]1[cH:13][c:12]2[n:11]([c:22](=[O:23])[n:21]1)[CH2:10][CH2:9][c:7]1[c:6]-2[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:8]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([cH:8]1)[CH2:9][CH2:10][n:11]1[c:12]-2[cH:13][c:14]([NH:15][CH2:16][CH2:17][N:18]([CH3:19])[CH3:20])[n:21][c... | CN(C)CCN.COc1ccc2c(c1)CCn1c-2cc(Cl)nc1=O | COc1ccc2c(c1)CCn1c-2cc(NCCN(C)C)nc1=O | null | null | null | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | c8475104970a63fce3d52b085fd15febf776cee9f570c7a80516c8bef4cb52de | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | O=c1nccc2n1CCc1ccccc1-2 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3](=[O;D1;H0:4]):[#7;a:5](:[c:6](:[c:7]:1)-[c:8])-[C:9].[C:10]-[C:11]-[NH2;D1;+0:12]>>[C:9]-[#7;a:5]1:[c:6](:[c:7]:[c;H0;D3;+0:1](-[NH;D2;+0:12]-[C:11]-[C:10]):[#7;a:2]:[c:3]:1=[O;D1;H0:4])-[c:8] | null | [] | null | null | null | null | The title compound was prepared from 2-chloro-9-methoxy-6,7-dihydro-pyrimido[6,1-a]isoquinolin-4-one (4) and 2-dimethylamino-ethylamine as in Example 1 d. 1H-NMR (400 MHz, d6-DMSO) δ 7.81 (br, 1H), 7.78 (d, 1H), 7.01-6.95 (2H), 6.16 (s, 1H), 3.94 (t, 2H), 3.83 (s, 3H), 3.62 (br, 2H), 3.21 (br, 2H), 2.93 (t, 2H) and 2.8... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccc2c(c1)CCn1cnccc21 | c1ccc2c(c1)CCn1cnccc21 | c1ccc2c(c1)CCn1cnccc21 | HCl | null | null | null | CN(C)CCN.COc1ccc2c(c1)CCn1c-2cc(Cl)nc1=O>>COc1ccc2c(c1)CCn1c-2cc(NCCN(C)C)nc1=O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-39bcad5e35974ea09b9fa16f04031455 | COc1ccc2c(c1)CCn1c-2cc(Cl)nc1=O.NCCO>>COc1ccc2c(c1)CCn1c-2cc(NCCO)nc1=O | ClC1=NC(N2C(C3=CC=C(C=C3CC2)OC)=C1)=O.OCCN>>OCCNC1=NC(N2C(C3=CC=C(C=C3CC2)OC)=C1)=O | Cl[c:14]1[cH:13][c:12]2[n:11]([c:20](=[O:21])[n:19]1)[CH2:10][CH2:9][c:7]1[c:6]-2[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:8]1.[NH2:15][CH2:16][CH2:17][OH:18]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([cH:8]1)[CH2:9][CH2:10][n:11]1[c:12]-2[cH:13][c:14]([NH:15][CH2:16][CH2:17][OH:18])[n:19][c:20]1=[O:21] | COc1ccc2c(c1)CCn1c-2cc(Cl)nc1=O.NCCO | COc1ccc2c(c1)CCn1c-2cc(NCCO)nc1=O | null | null | O | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | c8475104970a63fce3d52b085fd15febf776cee9f570c7a80516c8bef4cb52de | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | O=c1nccc2n1CCc1ccccc1-2 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3](=[O;D1;H0:4]):[#7;a:5](:[c:6](:[c:7]:1)-[c:8])-[C:9].[C:10]-[C:11]-[NH2;D1;+0:12]>>[C:9]-[#7;a:5]1:[c:6](:[c:7]:[c;H0;D3;+0:1](-[NH;D2;+0:12]-[C:11]-[C:10]):[#7;a:2]:[c:3]:1=[O;D1;H0:4])-[c:8] | null | [] | null | null | null | null | The title compound was prepared from 2-chloro-9-methoxy-6,7-dihydro-pyrimido[6,1-a]isoquinolin-4-one (4) and 2-hydroxy-ethylamine as in Example 1 d. 1H-NMR (400 MHz, d6-DMSO) δ 7.62 (d 1H), 7.54 (t, 1H), 7.00-6.93 (2H), 6.17 (s, 1H), 4.85 (t, 1H), 3.91 (t, 2H), 3.82 (s, 3H) 3.50 (q, 2H), 2.91 (t, 2H) and 2H were overla... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccc2c(c1)CCn1cnccc21 | c1ccc2c(c1)CCn1cnccc21 | c1ccc2c(c1)CCn1cnccc21 | HCl | O | null | null | COc1ccc2c(c1)CCn1c-2cc(Cl)nc1=O.NCCO>O>COc1ccc2c(c1)CCn1c-2cc(NCCO)nc1=O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-4acff6614dbd4f5fb7a6d29c62be86a7 | COc1ccc(CN)cc1.COc1ccc2c(c1)CCn1c-2cc(Cl)nc1=O>>COc1ccc(CNc2cc3n(c(=O)n2)CCc2cc(OC)ccc2-3)cc1 | ClC1=NC(N2C(C3=CC=C(C=C3CC2)OC)=C1)=O.COC1=CC=C(CN)C=C1>>COC=1C=C2CCN3C(C2=CC1)=CC(=NC3=O)NCC3=CC=C(C=C3)OC | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][NH2:8])[cH:26][cH:27]1.Cl[c:9]1[cH:10][c:11]2[n:12]([c:13](=[O:14])[n:15]1)[CH2:16][CH2:17][c:18]1[cH:19][c:20]([O:21][CH3:22])[cH:23][cH:24][c:25]1-2>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][NH:8][c:9]2[cH:10][c:11]3[n:12]([c:13](=[O:14])[n:15]2)[CH2:16][CH2:17][c:18]2[c... | COc1ccc(CN)cc1.COc1ccc2c(c1)CCn1c-2cc(Cl)nc1=O | COc1ccc(CNc2cc3n(c(=O)n2)CCc2cc(OC)ccc2-3)cc1 | null | null | null | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | c8475104970a63fce3d52b085fd15febf776cee9f570c7a80516c8bef4cb52de | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | O=c1nc(NCc2ccccc2)cc2n1CCc1ccccc1-2 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3](=[O;D1;H0:4]):[#7;a:5](:[c:6](:[c:7]:1)-[c:8])-[C:9].[NH2;D1;+0:10]-[C:11]-[c:12]>>[C:9]-[#7;a:5]1:[c:6](:[c:7]:[c;H0;D3;+0:1](-[NH;D2;+0:10]-[C:11]-[c:12]):[#7;a:2]:[c:3]:1=[O;D1;H0:4])-[c:8] | null | [] | null | null | null | null | The title compound was prepared from 2-chloro-9-methoxy-6,7-dihydro-pyrimido[6,1-a]isoquinolin-4-one (4) and 4-methoxy-benzylamine as in Example 1 d. 1H-NMR (400 MHz, d6-DMSO) δ 7.89 (t, 1H), 7.63 (d, 1H), 7.25 (d, 2H), 7.0-6.93 (2H), 6.90 (d, 2H), 6.16 (s, 1H), 4.45 (d, 2H), 3.92 (t, 2H), 3.82 (s, 3H), 3.73 (s, 3H) an... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccc2c(c1)CCn1cnccc21 | c1ccc2c(c1)CCn1cnccc21 | c1ccccc1.c1ccc2c(c1)CCn1cnccc21 | HCl | null | null | null | COc1ccc(CN)cc1.COc1ccc2c(c1)CCn1c-2cc(Cl)nc1=O>>COc1ccc(CNc2cc3n(c(=O)n2)CCc2cc(OC)ccc2-3)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-f62b863b715e41fdbb0bd864707ef00d | COc1ccc2c(c1)CCn1c-2cc(Cl)nc1=O.COc1cccc(CN)c1>>COc1cccc(CNc2cc3n(c(=O)n2)CCc2cc(OC)ccc2-3)c1 | ClC1=NC(N2C(C3=CC=C(C=C3CC2)OC)=C1)=O.COC=1C=C(CN)C=CC1>>COC=1C=C2CCN3C(C2=CC1)=CC(=NC3=O)NCC3=CC(=CC=C3)OC | Cl[c:10]1[cH:11][c:12]2[n:13]([c:14](=[O:15])[n:16]1)[CH2:17][CH2:18][c:19]1[cH:20][c:21]([O:22][CH3:23])[cH:24][cH:25][c:26]1-2.[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]([CH2:8][NH2:9])[cH:27]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]([CH2:8][NH:9][c:10]2[cH:11][c:12]3[n:13]([c:14](=[O:15])[n:16]2)[CH2:17][CH2:18][c... | COc1ccc2c(c1)CCn1c-2cc(Cl)nc1=O.COc1cccc(CN)c1 | COc1cccc(CNc2cc3n(c(=O)n2)CCc2cc(OC)ccc2-3)c1 | null | null | null | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | c8475104970a63fce3d52b085fd15febf776cee9f570c7a80516c8bef4cb52de | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | O=c1nc(NCc2ccccc2)cc2n1CCc1ccccc1-2 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3](=[O;D1;H0:4]):[#7;a:5](:[c:6](:[c:7]:1)-[c:8])-[C:9].[NH2;D1;+0:10]-[C:11]-[c:12]>>[C:9]-[#7;a:5]1:[c:6](:[c:7]:[c;H0;D3;+0:1](-[NH;D2;+0:10]-[C:11]-[c:12]):[#7;a:2]:[c:3]:1=[O;D1;H0:4])-[c:8] | null | [] | null | null | null | null | The title compound was prepared from 2-chloro-9-methoxy-6,7-dihydro-pyrimido[6,1-a]isoquinolin-4-one (4) and 3-methoxy-benzylamine as in Example 1 d. 1H-NMR (400 MHz, d6-DMSO) δ 7.95 (t, 1H), 7.65 (d, 1H), 7.25 (t, 1H), 7.00-6.85 (4H), 6.82 (dd, 1H), 6.19 (s, 1H), 4.50 (d, 2H), 3.92 (t, 2H), 3.82 (s, 3H), 3.74 (s, 3H) ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccc2c(c1)CCn1cnccc21 | c1ccc2c(c1)CCn1cnccc21 | c1ccccc1.c1ccc2c(c1)CCn1cnccc21 | HCl | null | null | null | COc1ccc2c(c1)CCn1c-2cc(Cl)nc1=O.COc1cccc(CN)c1>>COc1cccc(CNc2cc3n(c(=O)n2)CCc2cc(OC)ccc2-3)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-cf67d6ff22444f638f10987d1139d1ca | COc1ccc2c(c1)CCn1c-2cc(Cl)nc1=O.Nc1cccc([N+](=O)[O-])c1>>COc1ccc2c(c1)CCn1c-2cc(Nc2cccc([N+](=O)[O-])c2)nc1=O | ClC1=NC(N2C(C3=CC=C(C=C3CC2)OC)=C1)=O.[N+](=O)([O-])C=1C=C(N)C=CC1>>[N+](=O)([O-])C=1C=C(C=CC1)NC1=NC(N2C(C3=CC=C(C=C3CC2)OC)=C1)=O | Cl[c:14]1[cH:13][c:12]2[n:11]([c:26](=[O:27])[n:25]1)[CH2:10][CH2:9][c:7]1[c:6]-2[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:8]1.[NH2:15][c:16]1[cH:17][cH:18][cH:19][c:20]([N+:21](=[O:22])[O-:23])[cH:24]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([cH:8]1)[CH2:9][CH2:10][n:11]1[c:12]-2[cH:13][c:14]([NH:15][c:16]2[cH:17][cH:18][... | COc1ccc2c(c1)CCn1c-2cc(Cl)nc1=O.Nc1cccc([N+](=O)[O-])c1 | COc1ccc2c(c1)CCn1c-2cc(Nc2cccc([N+](=O)[O-])c2)nc1=O | null | null | null | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c8475104970a63fce3d52b085fd15febf776cee9f570c7a80516c8bef4cb52de | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | O=c1nc(Nc2ccccc2)cc2n1CCc1ccccc1-2 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3](=[O;D1;H0:4]):[#7;a:5](:[c:6](:[c:7]:1)-[c:8])-[C:9].[NH2;D1;+0:10]-[c:11](:[c:12]):[c:13]>>[C:9]-[#7;a:5]1:[c:6](:[c:7]:[c;H0;D3;+0:1](-[NH;D2;+0:10]-[c:11](:[c:12]):[c:13]):[#7;a:2]:[c:3]:1=[O;D1;H0:4])-[c:8] | null | [] | null | null | null | null | The title compound was prepared from 2-chloro-9-methoxy-6,7-dihydro-pyrimido[6,1-a]isoquinolin-4-one (4) and 3-nitro-aniline as in Example 1 d. 1H-NMR (400 MHz, d6-DMSO) δ 10.10 (s, 1H), 8.87 (s, 1H), 8.13 (d, 1H), 7.88 (m, 1H), 7.73 (d, 1H), 7.63 (t, 1H), 7.02 (m, 2H), 6.38 (s, 1H), 4.01 (t, 2H), 3.85 (s, 3H) and 2.99... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccc2c(c1)CCn1cnccc21 | c1ccc2c(c1)CCn1cnccc21 | c1ccc2c(c1)CCn1cnccc21.c1ccccc1 | HCl | null | null | null | COc1ccc2c(c1)CCn1c-2cc(Cl)nc1=O.Nc1cccc([N+](=O)[O-])c1>>COc1ccc2c(c1)CCn1c-2cc(Nc2cccc([N+](=O)[O-])c2)nc1=O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-2b11ce1c1196459d9ab1fb7188eaac05 | COc1ccc2c(c1)CCn1c-2cc(Nc2cccc([N+](=O)[O-])c2)nc1=O>>COc1ccc2c(c1)CCn1c-2cc(Nc2cccc(N)c2)nc1=O | [N+](=O)([O-])C=1C=C(C=CC1)NC1=NC(N2C(C3=CC=C(C=C3CC2)OC)=C1)=O.CO>>NC=1C=C(C=CC1)NC1=NC(N2C(C3=CC=C(C=C3CC2)OC)=C1)=O | O=[N+:21]([O-])[c:20]1[cH:19][cH:18][cH:17][c:16]([NH:15][c:14]2[cH:13][c:12]3[n:11]([c:24](=[O:25])[n:23]2)[CH2:10][CH2:9][c:7]2[c:6]-3[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:8]2)[cH:22]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([cH:8]1)[CH2:9][CH2:10][n:11]1[c:12]-2[cH:13][c:14]([NH:15][c:16]2[cH:17][cH:18][cH:19][c:20]... | COc1ccc2c(c1)CCn1c-2cc(Nc2cccc([N+](=O)[O-])c2)nc1=O | COc1ccc2c(c1)CCn1c-2cc(Nc2cccc(N)c2)nc1=O | null | [Zn] | CC(=O)O | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | O=c1nc(Nc2ccccc2)cc2n1CCc1ccccc1-2 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | 46 | [{"value": 46.0, "product": "NC=1C=C(C=CC1)NC1=NC(N2C(C3=CC=C(C=C3CC2)OC)=C1)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 45.9, "product": "NC=1C=C(C=CC1)NC1=NC(N2C(C3=CC=C(C=C3CC2)OC)=C1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | To a solution of 2-(3-nitro-phenylamino)-9-methoxy-6,7-dihydro-pyrimido[6,1-a]isoquinolin-4-one (5) (525.4 mg, 1.4 mmol) in AcOH (40 mL), Zn powder (ca. 300 mg) was added and stirred at room temperature for 3 hrs, then at 40° C. overnight. After cooling, MeOH was added to the mixture and insoluble materials were remove... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccc2c(c1)CCn1cnccc21.c1ccccc1 | Other | [Zn].CC(=O)O | null | 3 | COc1ccc2c(c1)CCn1c-2cc(Nc2cccc([N+](=O)[O-])c2)nc1=O>[Zn].CC(=O)O>COc1ccc2c(c1)CCn1c-2cc(Nc2cccc(N)c2)nc1=O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ea46a3d1777743fbbf413506f854f8b9 | COc1ccc2c(c1)CCn1c-2cc(Nc2cccc(N)c2)nc1=O.O=C(Cl)c1cccc(Br)c1>>COc1ccc2c(c1)CCn1c-2cc(Nc2cccc(NC(=O)c3cccc(Br)c3)c2)nc1=O | NC=1C=C(C=CC1)NC1=NC(N2C(C3=CC=C(C=C3CC2)OC)=C1)=O.C(C)N(CC)CC.BrC=1C=C(C(=O)Cl)C=CC1>>BrC=1C=C(C(=O)NC2=CC(=CC=C2)NC2=NC(N3C(C4=CC=C(C=C4CC3)OC)=C2)=O)C=CC1 | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([cH:8]1)[CH2:9][CH2:10][n:11]1[c:12]-2[cH:13][c:14]([NH:15][c:16]2[cH:17][cH:18][cH:19][c:20]([NH2:21])[cH:31]2)[n:32][c:33]1=[O:34].Cl[C:22](=[O:23])[c:24]1[cH:25][cH:26][cH:27][c:28]([Br:29])[cH:30]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([cH:8]1)[CH2:9][CH2:10][n:11]1[c:... | COc1ccc2c(c1)CCn1c-2cc(Nc2cccc(N)c2)nc1=O.O=C(Cl)c1cccc(Br)c1 | COc1ccc2c(c1)CCn1c-2cc(Nc2cccc(NC(=O)c3cccc(Br)c3)c2)nc1=O | null | null | C1CCOC1 | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=C(Nc1cccc(Nc2cc3n(c(=O)n2)CCc2ccccc2-3)c1)c1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9])-[c:3](:[c:4]):[c:5] | 81.5 | [{"value": 81.0, "product": "BrC=1C=C(C(=O)NC2=CC(=CC=C2)NC2=NC(N3C(C4=CC=C(C=C4CC3)OC)=C2)=O)C=CC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 81.5, "product": "BrC=1C=C(C(=O)NC2=CC(=CC=C2)NC2=NC(N3C(C4=CC=C(C=C4CC3)OC)=C2)=O)C=CC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 50 | CELSIUS | 2 | HOUR | To a mixture of 2-(3-amino-phenylamino)-9-methoxy-6,7-dihydro-pyrimido[6,1-a]isoquinolin-4-one (§) (20.0 mg, 0.06 mmol) in THF (2 mL), triethylamine (13 μL, 0.09 mmol) and 3-bromobenzoylchloride (10 μL, 0.07 mmol) was added and stirred at 50° C. for 2 hrs. The mixture was quenched with concentrated HCl and purified on ... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccc2c(c1)CCn1cnccc21.c1ccccc1.c1ccccc1 | HCl | C1CCOC1 | 50 | 2 | COc1ccc2c(c1)CCn1c-2cc(Nc2cccc(N)c2)nc1=O.O=C(Cl)c1cccc(Br)c1>C1CCOC1>COc1ccc2c(c1)CCn1c-2cc(Nc2cccc(NC(=O)c3cccc(Br)c3)c2)nc1=O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-115897dd37cd4c5e810d7740212b0657 | COc1ccc2c(c1)CCn1c-2cc(Nc2cccc(N)c2)nc1=O.O=C(Cl)C1CCCC1>>COc1ccc2c(c1)CCn1c-2cc(Nc2cccc(NC(=O)C3CCCC3)c2)nc1=O | NC=1C=C(C=CC1)NC1=NC(N2C(C3=CC=C(C=C3CC2)OC)=C1)=O.C1(CCCC1)C(=O)Cl>>COC=1C=C2CCN3C(C2=CC1)=CC(=NC3=O)NC=3C=C(C=CC3)NC(=O)C3CCCC3 | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([cH:8]1)[CH2:9][CH2:10][n:11]1[c:12]-2[cH:13][c:14]([NH:15][c:16]2[cH:17][cH:18][cH:19][c:20]([NH2:21])[cH:29]2)[n:30][c:31]1=[O:32].Cl[C:22](=[O:23])[CH:24]1[CH2:25][CH2:26][CH2:27][CH2:28]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([cH:8]1)[CH2:9][CH2:10][n:11]1[c:12]-2[cH:1... | COc1ccc2c(c1)CCn1c-2cc(Nc2cccc(N)c2)nc1=O.O=C(Cl)C1CCCC1 | COc1ccc2c(c1)CCn1c-2cc(Nc2cccc(NC(=O)C3CCCC3)c2)nc1=O | null | null | null | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=C(Nc1cccc(Nc2cc3n(c(=O)n2)CCc2ccccc2-3)c1)C1CCCC1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[C:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[C:4]-[C:3](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9])-[C:5] | null | [] | null | null | null | null | The title compound was prepared from 2-(3-amino-phenylamino)-9-methoxy-6,7-dihydro-pyrimido[6,1-a]isoquinolin-4-one (6) and cyclopentanecarbonyl chloride according the method described in Example 28 c. 1H-NMR (400 MHz, d6-DMSO) δ 9.92 (s, 1H), 9.66 (br, 1H), 7.91 (s, 1H), 7.69 (d, 1H), 7.57 (br, 1H), 7.28-7.20 (2H), 7.... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccc2c(c1)CCn1cnccc21.c1ccccc1.C1CCCC1 | HCl | null | null | null | COc1ccc2c(c1)CCn1c-2cc(Nc2cccc(N)c2)nc1=O.O=C(Cl)C1CCCC1>>COc1ccc2c(c1)CCn1c-2cc(Nc2cccc(NC(=O)C3CCCC3)c2)nc1=O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-491a7ba3f81e432ebb1e348bdfdb572c | COc1ccc2c(c1)CCn1c-2cc(Nc2cccc(N)c2)nc1=O>>COc1ccc2c(c1)CCn1c-2cc(N)nc1=O | NC=1C=C(C=CC1)NC1=NC(N2C(C3=CC=C(C=C3CC2)OC)=C1)=O>>NC1=NC(N2C(C3=CC=C(C=C3CC2)OC)=C1)=O | Nc1cccc([NH:15][c:14]2[cH:13][c:12]3[n:11]([c:17](=[O:18])[n:16]2)[CH2:10][CH2:9][c:7]2[c:6]-3[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:8]2)c1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([cH:8]1)[CH2:9][CH2:10][n:11]1[c:12]-2[cH:13][c:14]([NH2:15])[n:16][c:17]1=[O:18] | COc1ccc2c(c1)CCn1c-2cc(Nc2cccc(N)c2)nc1=O | COc1ccc2c(c1)CCn1c-2cc(N)nc1=O | null | null | N.CCO | Deprotection | OtherReaction | 955efe56b73efe78896f5751de3370dad7e37edbc310c8e85e537e031af3ae72 | 71840037a637bcecd93dda6b5aa82c17bae11bfdbce0748faef9b27643e2c10a | O=c1nccc2n1CCc1ccccc1-2 | N-c1:c:c:c:c(-[NH;D2;+0:1]-[c:2]2:[#7;a:3]:[c:4]:[#7;a:5]:[c:6]:[c:7]:2):c:1>>[NH2;D1;+0:1]-[c:2]1:[#7;a:3]:[c:4]:[#7;a:5]:[c:6]:[c:7]:1 | 105.5 | [{"value": 105.5, "product": "NC1=NC(N2C(C3=CC=C(C=C3CC2)OC)=C1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 120 | CELSIUS | 8 | HOUR | To a suspension of 2-chloro-9-methoxy-6,7-dihydro-pyrimido[6,1-a]isoquinolin-4-one (6) (919 mg, 3.5 mmol) in NH3/EtOH (7 mL) was stirred in an autoclave at 120° C. overnight. After cooling, the precipitate was filtered and washed with MeOH to give the title compound (898.3 mg, quant.). 1H-NMR (400 MHz, d6-DMSO) δ 7.99 ... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Secondary amine | Primary amine | c1ccccc1 | null | c1ccc2c(c1)CCn1cnccc21 | Other | N.CCO | 120 | 8 | COc1ccc2c(c1)CCn1c-2cc(Nc2cccc(N)c2)nc1=O>N.CCO>COc1ccc2c(c1)CCn1c-2cc(N)nc1=O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-108e0b8006264da1af16c9338792a540 | COc1ccc2c(c1)CCn1c-2cc(N)nc1=O.O=C(Cl)c1c(Cl)cc(Cl)cc1Cl>>COc1ccc2c(c1)CCn1c-2cc(NC(=O)c2c(Cl)cc(Cl)cc2Cl)nc1=O | NC1=NC(N2C(C3=CC=C(C=C3CC2)OC)=C1)=O.ClC1=C(C(=O)Cl)C(=CC(=C1)Cl)Cl>>ClC1=C(C(=O)NC2=NC(N3C(C4=CC=C(C=C4CC3)OC)=C2)=O)C(=CC(=C1)Cl)Cl | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([cH:8]1)[CH2:9][CH2:10][n:11]1[c:12]-2[cH:13][c:14]([NH2:15])[n:27][c:28]1=[O:29].Cl[C:16](=[O:17])[c:18]1[c:19]([Cl:20])[cH:21][c:22]([Cl:23])[cH:24][c:25]1[Cl:26]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([cH:8]1)[CH2:9][CH2:10][n:11]1[c:12]-2[cH:13][c:14]([NH:15][C:16](=[O:... | COc1ccc2c(c1)CCn1c-2cc(N)nc1=O.O=C(Cl)c1c(Cl)cc(Cl)cc1Cl | COc1ccc2c(c1)CCn1c-2cc(NC(=O)c2c(Cl)cc(Cl)cc2Cl)nc1=O | null | CN(C)C=1C=CN=CC1 | C(Cl)(Cl)Cl | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=C(Nc1cc2n(c(=O)n1)CCc1ccccc1-2)c1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[NH2;D1;+0:6]-[c:7]1:[#7;a:8]:[c:9]:[#7;a:10]:[c:11]:[c:12]:1>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7]1:[#7;a:8]:[c:9]:[#7;a:10]:[c:11]:[c:12]:1)-[c:3](:[c:4]):[c:5] | 24 | [{"value": 24.0, "product": "ClC1=C(C(=O)NC2=NC(N3C(C4=CC=C(C=C4CC3)OC)=C2)=O)C(=CC(=C1)Cl)Cl", "details": "PERCENTYIELD", "is_desired": false}, {"value": 23.7, "product": "ClC1=C(C(=O)NC2=NC(N3C(C4=CC=C(C=C4CC3)OC)=C2)=O)C(=CC(=C1)Cl)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 25 | CELSIUS | 8 | HOUR | To a suspension of 2-amino-9-methoxy-6,7-dihydro-pyrimido[6,1-a]isoquinolin-4-one (7) (40 mg, 0.16 mmol) in CHCl3 (3 mL), DMAP (30.1 mg, 0.24 mmol) and 2,4,6-trichlorobenzoyl chloride (37.5 uL, 0.24 mmol) was added and stirred at 25° C. overnight. After cooling, the mixture was purified on BondElut® SCX (Varian Incorpo... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccc2c(c1)CCn1cnccc21.c1ccccc1 | HCl | CN(C)C=1C=CN=CC1.C(Cl)(Cl)Cl | 25 | 8 | COc1ccc2c(c1)CCn1c-2cc(N)nc1=O.O=C(Cl)c1c(Cl)cc(Cl)cc1Cl>CN(C)C=1C=CN=CC1.C(Cl)(Cl)Cl>COc1ccc2c(c1)CCn1c-2cc(NC(=O)c2c(Cl)cc(Cl)cc2Cl)nc1=O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-0acb0b6fd4e84fcfbd9ddc5057e095ed | COc1ccc(C(=O)OCC2CC2CBr)cc1.[C-]#N>>COc1ccc(C(=O)OCC2(CC#N)CC2)cc1 | COC1=CC=C(C(=O)OCC2C(C2)CBr)C=C1.[C-]#N.[K+].C([O-])(O)=O.[Na+]>>COC1=CC=C(C(=O)OCC2(CC2)CC#N)C=C1 | Br[CH2:15][CH:16]1[CH:11]([CH2:10][O:9][C:7]([c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:18][cH:17]2)=[O:8])[CH2:12]1.[C-:13]#[N:14]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([C:7](=[O:8])[O:9][CH2:10][C:11]2([CH2:12][C:13]#[N:14])[CH2:15][CH2:16]2)[cH:17][cH:18]1 | COc1ccc(C(=O)OCC2CC2CBr)cc1.[C-]#N | COc1ccc(C(=O)OCC2(CC#N)CC2)cc1 | null | null | O.C(C)O | C-C Coupling | OtherReaction | ab6bf26f9886a8d1b65eb4801b5d4f33196eb2fe0f1cd4ce637f89e29c0a4643 | 1dbefa1fc17e03074aa3f6619987f71dfa9a1cb0d61de142a880cd3f05e4f004 | O=C(OCC1CC1)c1ccccc1 | Br-[CH2;D2;+0:1]-[CH;D3;+0:2]1-[CH2;D2;+0:3]-[CH;D3;+0:4]-1-[C:5]-[#8:6]-[C:7]=[O;D1;H0:8].[C-;H0;D1:9]#[N;D1;H0:10]>>[N;D1;H0:10]#[C;H0;D2;+0:9]-[CH2;D2;+0:3]-[C;H0;D4;+0:4]1(-[C:5]-[#8:6]-[C:7]=[O;D1;H0:8])-[CH2;D2;+0:1]-[CH2;D2;+0:2]-1 | null | [] | 35 | CELSIUS | 2 | DAY | 261 mg of compound 10a was dissolved in 5 ml ethanol. A solution of 98 mg potassium cyanide in 5 ml water was added and the mixture was stirred at 35° C. for two days. 10 ml of a saturated aqueous sodium bicarbonate was added. The mixture was extracted twice with ethyl acetate. The combined extracts were dried with sod... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | Nitrile | C1CC1 | C1CC1 | c1ccccc1.C1CC1 | Br- | O.C(C)O | 35 | 48 | COc1ccc(C(=O)OCC2CC2CBr)cc1.[C-]#N>O.C(C)O>COc1ccc(C(=O)OCC2(CC#N)CC2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-f224ec6f8a7b411681d41b4cca8facae | COc1cc2c(Cl)c(C#N)cnc2cc1OCCCCl.Nc1c(Cl)ccc2c1OCO2>>COc1cc2c(Nc3c(Cl)ccc4c3OCO4)c(C#N)cnc2cc1OCCCCl | C[Si](N[Si](C)(C)C)(C)C.[Na].ClC1=CC=C2C(=C1N)OCO2.ClC1=C(C=NC2=CC(=C(C=C12)OC)OCCCCl)C#N>>ClC1=CC=C2C(=C1NC1=C(C=NC3=CC(=C(C=C13)OC)OCCCCl)C#N)OCO2 | Cl[c:6]1[c:5]2[cH:4][c:3]([O:2][CH3:1])[c:25]([O:26][CH2:27][CH2:28][CH2:29][Cl:30])[cH:24][c:23]2[n:22][cH:21][c:18]1[C:19]#[N:20].[NH2:7][c:8]1[c:9]([Cl:10])[cH:11][cH:12][c:13]2[c:14]1[O:15][CH2:16][O:17]2>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([NH:7][c:8]3[c:9]([Cl:10])[cH:11][cH:12][c:13]4[c:14]3[O:15][CH2:16][O:17]... | COc1cc2c(Cl)c(C#N)cnc2cc1OCCCCl.Nc1c(Cl)ccc2c1OCO2 | COc1cc2c(Nc3c(Cl)ccc4c3OCO4)c(C#N)cnc2cc1OCCCCl | null | null | O.CN(C)C=O | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | 45e8470a78418ade39424f40732aa5ecf6717a7e5d47830a67429c5970ebd551 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1cc(Nc2ccnc3ccccc23)c2c(c1)OCO2 | Cl-[c;H0;D3;+0:1]1:[c:2](-[C:3]#[N;D1;H0:4]):[c:5]:[#7;a:6]:[c:7](:[c:8]):[c:9]:1:[c:10].[#8:11]-[c:12]:[c:13](-[NH2;D1;+0:14]):[c:15]>>[#8:11]-[c:12]:[c:13](-[NH;D2;+0:14]-[c;H0;D3;+0:1]1:[c:2](-[C:3]#[N;D1;H0:4]):[c:5]:[#7;a:6]:[c:7](:[c:8]):[c:9]:1:[c:10]):[c:15] | 86.5 | [{"value": 86.5, "product": "ClC1=CC=C2C(=C1NC1=C(C=NC3=CC(=C(C=C13)OC)OCCCCl)C#N)OCO2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 5 | MINUTE | Sodium hexamethyldisilazane (1M solution in THF; 3.34 ml) was added to a solution of 6-chloro-2,3-methylenedioxyaniline (0.573 g) in DMF (12 ml) that was cooled to 0° C. and the mixture was stirred for 5 minutes. A solution of 4-chloro-7-(3-chloropropoxy)-3-cyano-6-methoxyquinoline (0.5 g) in DMF (3 ml) was added and t... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccc2ncccc2c1 | c1ccc2ncccc2c1 | c1ccc2c(c1)OCO2.c1ccc2ncccc2c1 | HCl | O.CN(C)C=O | 0 | 0.083333 | COc1cc2c(Cl)c(C#N)cnc2cc1OCCCCl.Nc1c(Cl)ccc2c1OCO2>O.CN(C)C=O>COc1cc2c(Nc3c(Cl)ccc4c3OCO4)c(C#N)cnc2cc1OCCCCl |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a45a50c6621a4e088906e4c8c0cd3295 | CO.O=C(O)c1cccc(O)c1O>>COC(=O)c1cccc(O)c1O | OC1=C(C(=O)O)C=CC=C1O.CO>>OC1=C(C(=O)OC)C=CC=C1O | [CH3:1][OH:2].O[C:3](=[O:4])[c:5]1[cH:6][cH:7][cH:8][c:9]([OH:10])[c:11]1[OH:12]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][cH:8][c:9]([OH:10])[c:11]1[OH:12] | CO.O=C(O)c1cccc(O)c1O | COC(=O)c1cccc(O)c1O | null | S(O)(O)(=O)=O | null | Protection | Esterification of Carboxylic Acids | 9cecdbd189c6f9c3648521d17154d013842a5498de4e76e65efb1d842973340b | af0b8064f2e82ebe66c4c29d2391785ac1b993104265ccdc4d67ca79e36fa3c8 | c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[C;D1;H3:6]-[OH;D1;+0:7]>>[C;D1;H3:6]-[O;H0;D2;+0:7]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5] | null | [] | 60 | CELSIUS | null | null | A mixture of 2,3-dihydroxybenzoic acid (5 g), methanol (50 ml) and concentrated sulphuric acid (10 drops) was stirred and heated to 60° C. for 24 hours. The mixture was evaporated and the residue was taken up in ethyl acetate. The organic solution was washed with a saturated solution of sodium bicarbonate, dried over m... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Methanol | Ester | null | null | c1ccccc1 | HO- | S(O)(O)(=O)=O | 60 | null | CO.O=C(O)c1cccc(O)c1O>S(O)(O)(=O)=O>COC(=O)c1cccc(O)c1O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a69c7a0cf7e74c18b0e09732f80e77bf | COc1cc2c(Cl)c(C#N)cnc2cc1O.Nc1cccc2c1OCO2>>COc1cc2c(Nc3cccc4c3OCO4)c(C#N)cnc2cc1O | ClC1=C(C=NC2=CC(=C(C=C12)OC)O)C#N.C1OC2=C(N)C=CC=C2O1>>C(#N)C=1C=NC2=CC(=C(C=C2C1NC1=C2C(=CC=C1)OCO2)OC)O | Cl[c:6]1[c:5]2[cH:4][c:3]([O:2][CH3:1])[c:24]([OH:25])[cH:23][c:22]2[n:21][cH:20][c:17]1[C:18]#[N:19].[NH2:7][c:8]1[cH:9][cH:10][cH:11][c:12]2[c:13]1[O:14][CH2:15][O:16]2>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([NH:7][c:8]3[cH:9][cH:10][cH:11][c:12]4[c:13]3[O:14][CH2:15][O:16]4)[c:17]([C:18]#[N:19])[cH:20][n:21][c:22]2[cH... | COc1cc2c(Cl)c(C#N)cnc2cc1O.Nc1cccc2c1OCO2 | COc1cc2c(Nc3cccc4c3OCO4)c(C#N)cnc2cc1O | null | null | C(CC)O | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | 45e8470a78418ade39424f40732aa5ecf6717a7e5d47830a67429c5970ebd551 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1cc(Nc2ccnc3ccccc23)c2c(c1)OCO2 | Cl-[c;H0;D3;+0:1]1:[c:2](-[C:3]#[N;D1;H0:4]):[c:5]:[#7;a:6]:[c:7](:[c:8]):[c:9]:1:[c:10].[#8:11]-[c:12]:[c:13](-[NH2;D1;+0:14]):[c:15]>>[#8:11]-[c:12]:[c:13](-[NH;D2;+0:14]-[c;H0;D3;+0:1]1:[c:2](-[C:3]#[N;D1;H0:4]):[c:5]:[#7;a:6]:[c:7](:[c:8]):[c:9]:1:[c:10]):[c:15] | null | [] | 115 | CELSIUS | null | null | A mixture of 4-chloro-3-cyano-7-hydroxy-6-methoxyquinoline (5 g), 2,3-methylenedioxyaniline (3.07 g) and propanol (100 ml) was stirred and heated to 115° C. for 18 hours. The resultant precipitate was isolated, washed in turn with propanol and diethyl ether and dried under vacuum. There was thus obtained the title comp... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccc2ncccc2c1 | c1ccc2ncccc2c1 | c1ccc2c(c1)OCO2.c1ccc2ncccc2c1 | HCl | C(CC)O | 115 | null | COc1cc2c(Cl)c(C#N)cnc2cc1O.Nc1cccc2c1OCO2>C(CC)O>COc1cc2c(Nc3cccc4c3OCO4)c(C#N)cnc2cc1O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-cd01101c1137484d92df54c3e56ba1c6 | COc1cc2c(Nc3cccc4c3OCO4)c(C#N)cnc2cc1O.OCCBr>>COc1cc2c(Nc3cccc4c3OCO4)c(C#N)cnc2cc1OCCBr | C(#N)C=1C=NC2=CC(=C(C=C2C1NC1=C2C(=CC=C1)OCO2)OC)O.BrCCO>>BrCCOC1=C(C=C2C(=C(C=NC2=C1)C#N)NC1=C2C(=CC=C1)OCO2)OC | [CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([NH:7][c:8]3[cH:9][cH:10][cH:11][c:12]4[c:13]3[O:14][CH2:15][O:16]4)[c:17]([C:18]#[N:19])[cH:20][n:21][c:22]2[cH:23][c:24]1[OH:25].O[CH2:26][CH2:27][Br:28]>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([NH:7][c:8]3[cH:9][cH:10][cH:11][c:12]4[c:13]3[O:14][CH2:15][O:16]4)[c:17]([C:18]#[N:19])[c... | COc1cc2c(Nc3cccc4c3OCO4)c(C#N)cnc2cc1O.OCCBr | COc1cc2c(Nc3cccc4c3OCO4)c(C#N)cnc2cc1OCCBr | null | null | null | Heteroatom Alkylation and Arylation | Mitsunobu aryl ether | 86bfb73617450d22f9456ed5ce4d96a73f1f8fc0c016bebae57fda68e2da86a2 | 2258bd14c3b5449b92dc09cf9fa522f88d5071b4af20f7e968b60aa1ae6db0cf | c1cc(Nc2ccnc3ccccc23)c2c(c1)OCO2 | O-[CH2;D2;+0:1]-[C:2]-[Br;D1;H0:3].[#7;a:4]:[c:5]:[c:6]:[c:7](-[OH;D1;+0:8]):[c:9]>>[#7;a:4]:[c:5]:[c:6]:[c:7](-[O;H0;D2;+0:8]-[CH2;D2;+0:1]-[C:2]-[Br;D1;H0:3]):[c:9] | 82 | [{"value": 82.0, "product": "BrCCOC1=C(C=C2C(=C(C=NC2=C1)C#N)NC1=C2C(=CC=C1)OCO2)OC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Using an analogous procedure to that described in Example 8, 3-cyano-7-hydroxy-6-methoxy-4-(2,3-methylenedioxyanilino)quinoline was reacted with 2-bromoethanol to give the title compound in 82% yield; NMR Spectrum: (DMSOd6) 3.88 (t, 2H), 3.94 (s, 3H), 4.51 (t, 2H), 5.96 (s, 2H), 6.8-6.93 (m, 3H), 7.34 (s, 1H), 7.8 (s, ... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Aromatic alcohol | Ether | null | null | c1ccc2c(c1)OCO2.c1ccc2ncccc2c1 | HO- | null | null | null | COc1cc2c(Nc3cccc4c3OCO4)c(C#N)cnc2cc1O.OCCBr>>COc1cc2c(Nc3cccc4c3OCO4)c(C#N)cnc2cc1OCCBr |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-02299f06a64e41adb6ac5ef29d0c9252 | C1COCCN1.COc1cc2c(Nc3cccc4c3OCO4)c(C#N)cnc2cc1OC[C@H]1CO1>>COc1cc2c(Nc3cccc4c3OCO4)c(C#N)cnc2cc1OC[C@H](O)CN1CCOCC1 | C(#N)C=1C=NC2=CC(=C(C=C2C1NC1=C2C(=CC=C1)OCO2)OC)OC[C@H]2CO2.N1CCOCC1>>C(#N)C=1C=NC2=CC(=C(C=C2C1NC1=C2C(=CC=C1)OCO2)OC)OC[C@@H](CN2CCOCC2)O | [NH:30]1[CH2:31][CH2:32][O:33][CH2:34][CH2:35]1.[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([NH:7][c:8]3[cH:9][cH:10][cH:11][c:12]4[c:13]3[O:14][CH2:15][O:16]4)[c:17]([C:18]#[N:19])[cH:20][n:21][c:22]2[cH:23][c:24]1[O:25][CH2:26][C@@H:27]1[O:28][CH2:29]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([NH:7][c:8]3[cH:9][cH:10][cH:11][c:1... | C1COCCN1.COc1cc2c(Nc3cccc4c3OCO4)c(C#N)cnc2cc1OC[C@H]1CO1 | COc1cc2c(Nc3cccc4c3OCO4)c(C#N)cnc2cc1OC[C@H](O)CN1CCOCC1 | null | null | C(CC)O | Heteroatom Alkylation and Arylation | Ring opening of epoxide with amine | 851dfc16280bb8f11cdb75741b500ca1a156bb53c804ef98fc4ef4b1d0f67de0 | 97e758d6c4c8255d25541eb6c6a6f62e7dc30829ea162ca3392731efabc98a65 | c1cc(Nc2ccnc3cc(OCCCN4CCOCC4)ccc23)c2c(c1)OCO2 | [#8:1]-[C:2]-[C@H;D3;+0:3]1-[CH2;D2;+0:4]-[O;H0;D2;+0:5]-1.[#8:6]1-[C:7]-[C:8]-[NH;D2;+0:9]-[C:10]-[C:11]-1>>[#8:1]-[C:2]-[C@H;D3;+0:3](-[OH;D1;+0:5])-[CH2;D2;+0:4]-[N;H0;D3;+0:9]1-[C:8]-[C:7]-[#8:6]-[C:11]-[C:10]-1 | 32.7 | [{"value": 32.7, "product": "C(#N)C=1C=NC2=CC(=C(C=C2C1NC1=C2C(=CC=C1)OCO2)OC)OC[C@@H](CN2CCOCC2)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | null | null | A mixture of 3-cyano-7-[(2R)-2,3-epoxypropoxy]-6-methoxy-4-(2,3-methylenedioxyanilino)quinoline (0.1 g), morpholine (0.11 g) and propanol (5 ml) was stirred and heated to 80° C. for 3 hours. The resultant mixture was evaporated and the residue was purified by column chromatography on silica using increasingly polar mix... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Secondary amine | Secondary alcohol.Tertiary amine | C1COCCN1.C1CO1 | C1COCC[NH]1 | c1ccc2c(c1)OCO2.c1ccc2ncccc2c1.C1COCC[NH]1 | null | C(CC)O | 80 | null | C1COCCN1.COc1cc2c(Nc3cccc4c3OCO4)c(C#N)cnc2cc1OC[C@H]1CO1>C(CC)O>COc1cc2c(Nc3cccc4c3OCO4)c(C#N)cnc2cc1OC[C@H](O)CN1CCOCC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e3042368d58241b8a674e5808d2771c7 | CC(=O)N1CCNCC1.COc1cc2c(Nc3cccc4c3OCO4)c(C#N)cnc2cc1OC[C@H]1CO1>>COc1cc2c(Nc3cccc4c3OCO4)c(C#N)cnc2cc1OC[C@H](O)CN1CCN(C(C)=O)CC1 | C(#N)C=1C=NC2=CC(=C(C=C2C1NC1=C2C(=CC=C1)OCO2)OC)OC[C@H]2CO2.C(C)(=O)N1CCNCC1>>C(C)(=O)N1CCN(CC1)C[C@H](COC1=C(C=C2C(=C(C=NC2=C1)C#N)NC1=C2C(=CC=C1)OCO2)OC)O | [NH:30]1[CH2:31][CH2:32][N:33]([C:34]([CH3:35])=[O:36])[CH2:37][CH2:38]1.[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([NH:7][c:8]3[cH:9][cH:10][cH:11][c:12]4[c:13]3[O:14][CH2:15][O:16]4)[c:17]([C:18]#[N:19])[cH:20][n:21][c:22]2[cH:23][c:24]1[O:25][CH2:26][C@@H:27]1[O:28][CH2:29]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([NH:7][c:8]... | CC(=O)N1CCNCC1.COc1cc2c(Nc3cccc4c3OCO4)c(C#N)cnc2cc1OC[C@H]1CO1 | COc1cc2c(Nc3cccc4c3OCO4)c(C#N)cnc2cc1OC[C@H](O)CN1CCN(C(C)=O)CC1 | null | null | null | Heteroatom Alkylation and Arylation | Ring opening of epoxide with amine | 17ab6d3921429d49d85a9af124942b034c73e1fe2f69930f0392bbbfc9046e12 | 97e758d6c4c8255d25541eb6c6a6f62e7dc30829ea162ca3392731efabc98a65 | c1cc(Nc2ccnc3cc(OCCCN4CCNCC4)ccc23)c2c(c1)OCO2 | [#7:1]1-[C:2]-[C:3]-[NH;D2;+0:4]-[C:5]-[C:6]-1.[#8:7]-[C:8]-[C@H;D3;+0:9]1-[CH2;D2;+0:10]-[O;H0;D2;+0:11]-1>>[#8:7]-[C:8]-[C@H;D3;+0:9](-[OH;D1;+0:11])-[CH2;D2;+0:10]-[N;H0;D3;+0:4]1-[C:3]-[C:2]-[#7:1]-[C:6]-[C:5]-1 | 35 | [{"value": 35.0, "product": "C(C)(=O)N1CCN(CC1)C[C@H](COC1=C(C=C2C(=C(C=NC2=C1)C#N)NC1=C2C(=CC=C1)OCO2)OC)O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Using an analogous procedure to that described in Example 11, 3-cyano-7-[(2R)-2,3-epoxypropoxy]-6-methoxy-4-(2,3-methylenedioxyanilino)quinoline was reacted with 1-acetylpiperazine to give the title compound in 35% yield; NMR Spectrum: (DMSOd6) 1.96 (s, 3H), 2.34-2.54 (m, 6H), 3.35-3.45 (m, 4H), 3.94 (s, 3H), 4.0-4.1 (... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Secondary amine | Secondary alcohol.Tertiary amine | C1CNCC[NH]1.C1CO1 | C1C[NH]CC[NH]1 | c1ccc2c(c1)OCO2.c1ccc2ncccc2c1.C1C[NH]CC[NH]1 | null | null | null | null | CC(=O)N1CCNCC1.COc1cc2c(Nc3cccc4c3OCO4)c(C#N)cnc2cc1OC[C@H]1CO1>>COc1cc2c(Nc3cccc4c3OCO4)c(C#N)cnc2cc1OC[C@H](O)CN1CCN(C(C)=O)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a5d66199e62444b397bafa9b4178fe74 | COc1cc2c(Cl)c(C#N)cnc2cc1OCCCN1CCN(C)CC1.Oc1cccc2c1OCO2>>COc1cc2c(Oc3cccc4c3OCO4)c(C#N)cnc2cc1OCCCN1CCN(C)CC1 | C([O-])([O-])=O.[K+].[K+].C1OC2=C(C=CC=C2O1)O.ClC1=C(C=NC2=CC(=C(C=C12)OC)OCCCN1CCN(CC1)C)C#N>>C(#N)C=1C=NC2=CC(=C(C=C2C1OC1=C2C(=CC=C1)OCO2)OC)OCCCN2CCN(CC2)C | Cl[c:6]1[c:5]2[cH:4][c:3]([O:2][CH3:1])[c:24]([O:25][CH2:26][CH2:27][CH2:28][N:29]3[CH2:30][CH2:31][N:32]([CH3:33])[CH2:34][CH2:35]3)[cH:23][c:22]2[n:21][cH:20][c:17]1[C:18]#[N:19].[OH:7][c:8]1[cH:9][cH:10][cH:11][c:12]2[c:13]1[O:14][CH2:15][O:16]2>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([O:7][c:8]3[cH:9][cH:10][cH:11][c:... | COc1cc2c(Cl)c(C#N)cnc2cc1OCCCN1CCN(C)CC1.Oc1cccc2c1OCO2 | COc1cc2c(Oc3cccc4c3OCO4)c(C#N)cnc2cc1OCCCN1CCN(C)CC1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 499018af6792b58a137ac4495e0c20acdc548a3418ba695c815cb38084ffd839 | 27e9a6bab4e3ed54aeb6be4d84cb1c0170208288795e252a46e57e44ecc064f0 | c1cc2c(c(Oc3ccnc4cc(OCCCN5CCNCC5)ccc34)c1)OCO2 | Cl-[c;H0;D3;+0:1]1:[c:2](-[C:3]#[N;D1;H0:4]):[c:5]:[#7;a:6]:[c:7](:[c:8]):[c:9]:1:[c:10].[#8:11]-[c:12]:[c:13](-[OH;D1;+0:14]):[c:15]>>[#8:11]-[c:12]:[c:13](-[O;H0;D2;+0:14]-[c;H0;D3;+0:1]1:[c:2](-[C:3]#[N;D1;H0:4]):[c:5]:[#7;a:6]:[c:7](:[c:8]):[c:9]:1:[c:10]):[c:15] | 54.3 | [{"value": 54.3, "product": "C(#N)C=1C=NC2=CC(=C(C=C2C1OC1=C2C(=CC=C1)OCO2)OC)OCCCN2CCN(CC2)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 10 | MINUTE | Potassium carbonate-(0.055 g) was added to a solution of 2,3-methylenedioxyphenol (0.041 g) in DMF (3 ml) and the mixture was stirred at ambient temperature for 10 minutes. 4-Chloro-3-cyano-6-methoxy-7-[3-(4-methylpiperazin-1-yl)propoxy]quinoline (0.1 g) was added and the mixture was stirred and heated to 95° C. for 2 ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic alcohol | Ether | c1ccc2ncccc2c1 | c1ccc2ncccc2c1 | c1ccc2c(c1)OCO2.c1ccc2ncccc2c1.C1C[NH]CC[NH]1 | HCl | CN(C)C=O | null | 0.166667 | COc1cc2c(Cl)c(C#N)cnc2cc1OCCCN1CCN(C)CC1.Oc1cccc2c1OCO2>CN(C)C=O>COc1cc2c(Oc3cccc4c3OCO4)c(C#N)cnc2cc1OCCCN1CCN(C)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-98ec8661d4f34030b2211a3fe72e4ddc | CN1CCNCC1.OCCCBr>>CN1CCN(CCCO)CC1 | BrCCCO.CN1CCNCC1.C([O-])([O-])=O.[K+].[K+]>>OCCCN1CCN(CC1)C | [CH3:1][N:2]1[CH2:3][CH2:4][NH:5][CH2:10][CH2:11]1.Br[CH2:6][CH2:7][CH2:8][OH:9]>>[CH3:1][N:2]1[CH2:3][CH2:4][N:5]([CH2:6][CH2:7][CH2:8][OH:9])[CH2:10][CH2:11]1 | CN1CCNCC1.OCCCBr | CN1CCN(CCCO)CC1 | null | null | C(C)O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | b703623ddc3b029d4716c15f5414f41773434bcc7e3f3853faf62273596bed77 | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | C1CNCCN1 | Br-[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 | A mixture of 3-bromopropanol (20 ml), N-methylpiperazine (29 ml), potassium carbonate (83 g) and ethanol (200 ml) was stirred and heated to reflux for 20 hours. The mixture was cooled to ambient temperature and filtered. The filtrate was evaporated and the residue was triturated under diethyl ether. The resultant mixtu... | 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 | HBr | C(C)O | null | null | CN1CCNCC1.OCCCBr>C(C)O>CN1CCN(CCCO)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-3944141735ad4ac9aaabaa3d9eb6575c | COc1cc2c(Cl)c(C#N)cnc2cc1OCCCN1CCN(C)CC1.Oc1c(Br)ccc2c1OCO2>>COc1cc2c(Oc3c(Br)ccc4c3OCO4)c(C#N)cnc2cc1OCCCN1CCN(C)CC1 | ClC1=C(C=NC2=CC(=C(C=C12)OC)OCCCN1CCN(CC1)C)C#N.BrC1=CC=C2C(=C1O)OCO2>>BrC1=CC=C2C(=C1OC1=C(C=NC3=CC(=C(C=C13)OC)OCCCN1CCN(CC1)C)C#N)OCO2 | Cl[c:6]1[c:5]2[cH:4][c:3]([O:2][CH3:1])[c:25]([O:26][CH2:27][CH2:28][CH2:29][N:30]3[CH2:31][CH2:32][N:33]([CH3:34])[CH2:35][CH2:36]3)[cH:24][c:23]2[n:22][cH:21][c:18]1[C:19]#[N:20].[OH:7][c:8]1[c:9]([Br:10])[cH:11][cH:12][c:13]2[c:14]1[O:15][CH2:16][O:17]2>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([O:7][c:8]3[c:9]([Br:10])[... | COc1cc2c(Cl)c(C#N)cnc2cc1OCCCN1CCN(C)CC1.Oc1c(Br)ccc2c1OCO2 | COc1cc2c(Oc3c(Br)ccc4c3OCO4)c(C#N)cnc2cc1OCCCN1CCN(C)CC1 | null | null | null | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 499018af6792b58a137ac4495e0c20acdc548a3418ba695c815cb38084ffd839 | 27e9a6bab4e3ed54aeb6be4d84cb1c0170208288795e252a46e57e44ecc064f0 | c1cc2c(c(Oc3ccnc4cc(OCCCN5CCNCC5)ccc34)c1)OCO2 | Cl-[c;H0;D3;+0:1]1:[c:2](-[C:3]#[N;D1;H0:4]):[c:5]:[#7;a:6]:[c:7](:[c:8]):[c:9]:1:[c:10].[#8:11]-[c:12]:[c:13](-[OH;D1;+0:14]):[c:15]>>[#8:11]-[c:12]:[c:13](-[O;H0;D2;+0:14]-[c;H0;D3;+0:1]1:[c:2](-[C:3]#[N;D1;H0:4]):[c:5]:[#7;a:6]:[c:7](:[c:8]):[c:9]:1:[c:10]):[c:15] | 52 | [{"value": 52.0, "product": "BrC1=CC=C2C(=C1OC1=C(C=NC3=CC(=C(C=C13)OC)OCCCN1CCN(CC1)C)C#N)OCO2", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Using an analogous procedure to that described in Example 14, 4chloro-3-cyano-6-methoxy-7-[3-(4-methylpiperazin-1-yl)propoxy]quinoline was reacted with 6-bromo-2,3-methylenedioxyphenol to give the title compound as a solid in 52% yield; NMR Spectrum: (DMSOd6 and CF3CO2D) 2.25-2.4 (m, 2H), 2.95 (s, 3H), 3.24-4.0 (m, 8H)... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic alcohol | Ether | c1ccc2ncccc2c1 | c1ccc2ncccc2c1 | c1ccc2c(c1)OCO2.c1ccc2ncccc2c1.C1C[NH]CC[NH]1 | HCl | null | null | null | COc1cc2c(Cl)c(C#N)cnc2cc1OCCCN1CCN(C)CC1.Oc1c(Br)ccc2c1OCO2>>COc1cc2c(Oc3c(Br)ccc4c3OCO4)c(C#N)cnc2cc1OCCCN1CCN(C)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-73684015d8eb4a0593744711924a72c2 | COc1cc2ncc(C#N)c(Nc3c(I)cc(I)c4c3OCO4)c2cc1OC.COc1cc2ncc(C#N)c(Nc3c(I)ccc4c3OCO4)c2cc1OC>>COc1cc2ncc(C#N)c(Nc3c(C#N)ccc4c3OCO4)c2cc1OC | C(#N)C=1C=NC2=CC(=C(C=C2C1NC1=C2C(=CC=C1I)OCO2)OC)OC.C(#N)C=1C=NC2=CC(=C(C=C2C1NC1=C2C(=C(C=C1I)I)OCO2)OC)OC>>C(#N)C=1C=NC2=CC(=C(C=C2C1NC1=C2C(=CC=C1C#N)OCO2)OC)OC | I[c:14]1[c:13]([NH:12][c:11]2[c:8]([C:9]#[N:10])[cH:7][n:6][c:5]3[cH:4][c:3]([O:2][CH3:1])[c:26]([O:27][CH3:28])[cH:25][c:24]32)[c:20]2[c:19]([c:18](I)[cH:17]1)[O:23][CH2:22][O:21]2.COc1cc2ncc([C:15]#[N:16])c(Nc3c(I)ccc4c3OCO4)c2cc1OC>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[n:6][cH:7][c:8]([C:9]#[N:10])[c:11]([NH:12][c:13]3[c:... | COc1cc2ncc(C#N)c(Nc3c(I)cc(I)c4c3OCO4)c2cc1OC.COc1cc2ncc(C#N)c(Nc3c(I)ccc4c3OCO4)c2cc1OC | COc1cc2ncc(C#N)c(Nc3c(C#N)ccc4c3OCO4)c2cc1OC | null | C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].[C-]#N.[Zn+2].[C-]#N.C1(=CC=CC=C1)P(C1=CC=CC=C1)[C-]1C=CC=C1.[CH-]1C=CC=C1.[Fe+2].[Zn] | CC(=O)N(C)C | C-C Coupling | OtherReaction | 6e71d68a19a9c1405b1740f1d7d34d696cc355fb6e2f5b9734b3a5806431ff9e | 4879b197a369623a5eec53ab3e96948572566aae2614433d35281c86c0a600b3 | c1cc(Nc2ccnc3ccccc23)c2c(c1)OCO2 | C-O-c1:c:c2:n:c:c(-[C;H0;D2;+0:1]#[N;D1;H0:2]):c(-N-c3:c(-I):c:c:c4:c:3-O-C-O-4):c:2:c:c:1-O-C.I-[c;H0;D3;+0:3]1:[c:4]:[c;H0;D3;+0:5](-I):[c:6]2:[c:7](:[c:8]:1-[#7:9])-[#8:10]-[C:11]-[#8:12]-2>>[#7:9]-[c:8]1:[c:7]2:[c:6](:[cH;D2;+0:5]:[c:4]:[c;H0;D3;+0:3]:1-[C;H0;D2;+0:1]#[N;D1;H0:2])-[#8:12]-[C:11]-[#8:10]-2 | null | [] | 110 | CELSIUS | null | null | Tris(dibenzylideneacetone)dipalladium (0.039 g) was added to a mixture of a 4:1 mixture (0.25 g) of 3-cyano-4-(6-iodo-2,3-methylenedioxyanilino)-6,7-dimethoxyquinoline and 3-cyano-4-(4,6-diiodo-2,3-methylenedioxyanilino)-6,7-dimethoxyquinoline (Example 10, Note [11]), zinc cyanide (0.092 g), diphenylphosphinoferrocene ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Aromatic halide.Ether.Ether.Ether.Ether.Nitrile.Secondary amine | Nitrile | c1ccc2c(c1)OCO2.c1ccc2ncccc2c1.c1ccc2c(c1)OCO2 | c1ccc2c(c1)OCO2 | c1ccc2ncccc2c1.c1ccc2c(c1)OCO2 | HI | C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].[C-]#N.[Zn+2].[C-]#N.C1(=CC=CC=C1)P(C1=CC=CC=C1)[C-]1C=CC=C1.[CH-]1C=CC=C1.[Fe+2].[Zn].CC(=O)N(C)C | 110 | null | COc1cc2ncc(C#N)c(Nc3c(I)cc(I)c4c3OCO4)c2cc1OC.COc1cc2ncc(C#N)c(Nc3c(I)ccc4c3OCO4)c2cc1OC>C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].[C-]#N.[Zn+2].[C-]#N.C1(=CC=CC=C1)P(C1=CC=CC=C1)[C-]1C=CC=C1.[CH-]1C=CC=C1.[Fe+2].[Zn].CC(=O)N(C)C>CO... |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-3184a89c183a481bbd9ff639d1b3d240 | COc1cc2ncc(C#N)c(Nc3ccc(I)c4c3OCO4)c2cc1OC>>COc1cc2ncc(C#N)c(Nc3ccc(C#N)c4c3OCO4)c2cc1OC | C(#N)C=1C=NC2=CC(=C(C=C2C1NC1=C2C(=C(C=C1)I)OCO2)OC)OC.CC(=O)N(C)C>>C(#N)C=1C=NC2=CC(=C(C=C2C1NC1=C2C(=C(C=C1)C#N)OCO2)OC)OC | I[c:16]1[cH:15][cH:14][c:13]([NH:12][c:11]2[c:8]([C:9]#[N:10])[cH:7][n:6][c:5]3[cH:4][c:3]([O:2][CH3:1])[c:26]([O:27][CH3:28])[cH:25][c:24]32)[c:20]2[c:19]1[O:23][CH2:22][O:21]2>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[n:6][cH:7][c:8]([C:9]#[N:10])[c:11]([NH:12][c:13]3[cH:14][cH:15][c:16]([C:17]#[N:18])[c:19]4[c:20]3[O:21][CH2:... | COc1cc2ncc(C#N)c(Nc3ccc(I)c4c3OCO4)c2cc1OC | COc1cc2ncc(C#N)c(Nc3ccc(C#N)c4c3OCO4)c2cc1OC | null | C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].C1(=CC=CC=C1)P(C1=CC=CC=C1)[C-]1C=CC=C1.[CH-]1C=CC=C1.[Fe+2].[Zn] | null | Miscellaneous | OtherReaction | fb09649fd435e8f138dc0d7d983f4e059a414c031c70823708ee750a9e6b44c8 | 73a96fe5e833259ca394a42f82d6cc2ee7231bcde92d95030d2893b90c3fef76 | c1cc(Nc2ccnc3ccccc23)c2c(c1)OCO2 | I-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]1:[c:5]-[#8:6]-[C:7]-[#8:8]-1>>[N;D1;H0:9]#[C:10]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]1:[c:5]-[#8:6]-[C:7]-[#8:8]-1 | null | [] | 110 | CELSIUS | null | null | Tris(dibenzylideneacetone)dipalladium (0.0073 g) was added to a mixture of 3-cyano-4-(4-iodo-2,3methylenedioxyanilino)-6,7-dimethoxyquinoline (0.05 g) zinc cyanide (0.015 g), diphenylphosphinoferrocene (0.009 g), zinc powder (0.0035 g) and DMA (2 ml) and the resultant mixture was stirred and heated to 110° C. for 1 hou... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | Nitrile | c1ccc2c(c1)OCO2 | c1ccc2c(c1)OCO2 | c1ccc2ncccc2c1.c1ccc2c(c1)OCO2 | I- | C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].C1(=CC=CC=C1)P(C1=CC=CC=C1)[C-]1C=CC=C1.[CH-]1C=CC=C1.[Fe+2].[Zn] | 110 | null | COc1cc2ncc(C#N)c(Nc3ccc(I)c4c3OCO4)c2cc1OC>C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].C1(=CC=CC=C1)P(C1=CC=CC=C1)[C-]1C=CC=C1.[CH-]1C=CC=C1.[Fe+2].[Zn]>COc1cc2ncc(C#N)c(Nc3ccc(C#N)c4c3OCO4)c2cc1OC |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-8b17765db61143fe8ca1338418d2ef04 | CCO.Nc1cc(Cl)nc(N)n1>>CCOc1cc(N)nc(N)n1 | [Na].ClC1=NC(=NC(=C1)N)N.C(C)O>>NC1=NC(=CC(=N1)OCC)N | [CH3:1][CH2:2][OH:3].Cl[c:4]1[cH:5][c:6]([NH2:7])[n:8][c:9]([NH2:10])[n:11]1>>[CH3:1][CH2:2][O:3][c:4]1[cH:5][c:6]([NH2:7])[n:8][c:9]([NH2:10])[n:11]1 | CCO.Nc1cc(Cl)nc(N)n1 | CCOc1cc(N)nc(N)n1 | null | null | null | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | a445000eb5ed501274d93689ad5b9d45095af02deca02b6b541c8a834890a276 | a4cafa7bcd156e21cca6eaac1b32e28ec8540642a31181122e6957f3d7559631 | c1cncnc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3](-[N;D1;H2:4]):[#7;a:5]:[c:6](-[N;D1;H2:7]):[c:8]:1.[C;D1;H3:9]-[C:10]-[OH;D1;+0:11]>>[C;D1;H3:9]-[C:10]-[O;H0;D2;+0:11]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3](-[N;D1;H2:4]):[#7;a:5]:[c:6](-[N;D1;H2:7]):[c:8]:1 | 72 | [{"value": 72.0, "product": "NC1=NC(=CC(=N1)OCC)N", "details": "PERCENTYIELD", "is_desired": false}] | 160 | CELSIUS | null | null | To a solution of sodium (1.05 g) in ethanol (50 ml) was added 4-chloro-2,6-diaminopyrimidine (6 g, 41.4 mmoles). The resulting solution was heated in a reactor for 6 hours at 160° C. The reaction mixture was cooled down and the precipitated sodium chloride was filtered off. The filtrate was concentrated and precipitate... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary alcohol | Ether | c1cncnc1 | c1cncnc1 | c1cncnc1 | HCl | null | 160 | null | CCO.Nc1cc(Cl)nc(N)n1>>CCOc1cc(N)nc(N)n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-0e0e8be0a02f4c19bf09fd9226c5895a | CCOc1nc(N)nc(N)c1N=O>>CCOc1nc(N)nc(N)c1N | N(=O)C=1C(=NC(=NC1N)N)OCC.S(=O)([O-])S(=O)[O-].[Na+].[Na+].S(=O)([O-])S(=O)[O-].[Na+].[Na+]>>NC1=NC(=C(C(=N1)OCC)N)N | O=[N:12][c:11]1[c:4]([O:3][CH2:2][CH3:1])[n:5][c:6]([NH2:7])[n:8][c:9]1[NH2:10]>>[CH3:1][CH2:2][O:3][c:4]1[n:5][c:6]([NH2:7])[n:8][c:9]([NH2:10])[c:11]1[NH2:12] | CCOc1nc(N)nc(N)c1N=O | CCOc1nc(N)nc(N)c1N | null | null | O | Reduction | OtherReaction | 10bd501bc4fc8c6849398545fc18bd5f6b51ea4e37b15a00157d17550a6b88bf | 7085a0cec3cc6daaf2fab855d070c407558563b5b6837070687c0df0a552c6fe | c1cncnc1 | O=[N;H0;D2;+0:1]-[c:2]1:[c:3](-[#8:4]):[#7;a:5]:[c:6]:[#7;a:7]:[c:8]:1-[N;D1;H2:9]>>[#8:4]-[c:3]1:[#7;a:5]:[c:6]:[#7;a:7]:[c:8](-[N;D1;H2:9]):[c:2]:1-[NH2;D1;+0:1] | 61.1 | [{"value": 61.0, "product": "NC1=NC(=C(C(=N1)OCC)N)N", "details": "PERCENTYIELD", "is_desired": false}, {"value": 61.1, "product": "NC1=NC(=C(C(=N1)OCC)N)N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | 4 | HOUR | To a suspension of the compound of example 3 (7.12 g, 38.9 mmoles) in water (150 ml) at 60° C. was added sodium dithionite (46.7 mmol, 8.12 g). Additional sodium dithionite was added till the pink colour completely dis-appeared and a yellow solution was formed. The solution was stirred at 60° C. for another 4 hours. Wa... | 10.6084/m9.figshare.5104873.v1 | null | Nitroso | Primary amine | null | null | c1cncnc1 | Other | O | 60 | 4 | CCOc1nc(N)nc(N)c1N=O>O>CCOc1nc(N)nc(N)c1N |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ab953b8828c14caebd4e517da3330303 | CCOc1nc(N)nc(N)c1N>>CCOc1nc(N)nc2nccnc12 | NC1=NC(=C(C(=N1)OCC)N)N.C(=O)C=O>>NC1=NC2=NC=CN=C2C(=N1)OCC | [CH3:1][CH2:2][O:3][c:4]1[n:5][c:6]([NH2:7])[n:8][c:9]([NH2:10])[c:14]1[NH2:13]>>[CH3:1][CH2:2][O:3][c:4]1[n:5][c:6]([NH2:7])[n:8][c:9]2[n:10][cH:11][cH:12][n:13][c:14]12 | CCOc1nc(N)nc(N)c1N | CCOc1nc(N)nc2nccnc12 | null | null | C(C)O | Aromatic Heterocycle Formation | OtherReaction | fc8d78c77de84dd8af9389aacaf9f7ce807623ffdfe6a017dd3f1dcc98e11e6b | f6ca1788fc80057bd663c067fa50bcd2911a68a96991f331ace1350d4975ef8f | c1cnc2ncncc2n1 | [#8:1]-[c:2]1:[#7;a:3]:[c:4]:[#7;a:5]:[c:6](-[NH2;D1;+0:7]):[c:8]:1-[NH2;D1;+0:9]>>[#8:1]-[c:2]1:[#7;a:3]:[c:4]:[#7;a:5]:[c:6]2:[n;H0;D2;+0:7]:[c:10]:[c:11]:[n;H0;D2;+0:9]:[c:8]:1:2 | 206.4 | [{"value": 62.0, "product": "NC1=NC2=NC=CN=C2C(=N1)OCC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 206.4, "product": "NC1=NC2=NC=CN=C2C(=N1)OCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 2,5,6-triamino-4-ethoxy-pyrimidine (10.54 g, 62.37 mmoles) in ethanol (160 ml) was added glyoxal (40% solution in water, 2.7 ml, 18.6 mmoles). The reaction mixture was refluxed for 4 hours. Some insoluble material was filtered off. The filtrate was concentrated in vacuo and the residue purified by flas... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Primary amine | null | c1cncnc1 | c1cnc2ncncc2n1 | c1cnc2ncncc2n1 | Other | C(C)O | null | null | CCOc1nc(N)nc(N)c1N>C(C)O>CCOc1nc(N)nc2nccnc12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a7163506c3194da89333aab8dff5b037 | CCOc1nc(N)nc2nccnc12.OO>>CCOc1nc(N)nc2c1ncc[n+]2[O-] | NC1=NC2=NC=CN=C2C(=N1)OCC.OO.OO>>NC1=NC2=[N+](C=CN=C2C(=N1)OCC)[O-] | [CH3:1][CH2:2][O:3][c:4]1[n:5][c:6]([NH2:7])[n:8][c:9]2[c:10]1[n:11][cH:12][cH:13][n:14]2.O[OH:15]>>[CH3:1][CH2:2][O:3][c:4]1[n:5][c:6]([NH2:7])[n:8][c:9]2[c:10]1[n:11][cH:12][cH:13][n+:14]2[O-:15] | CCOc1nc(N)nc2nccnc12.OO | CCOc1nc(N)nc2c1ncc[n+]2[O-] | null | null | FC(C(=O)O)(F)F | Functional Group Interconversion | OtherReaction | 108dc977992bfe7c24471cfde5d789d737cc08dd2f50746be656adc9ce41a01c | bf536f3bf8ed7b8faf08cf1c004ccd0a5e7fe59339402dd73ac837bb4a52f2ba | c1c[nH+]c2ncncc2n1 | O-[OH;D1;+0:1].[#7;a:2]1:[c:3]:[c:4]:[n;H0;D2;+0:5]:[c:6]2:[#7;a:7]:[c:8]:[#7;a:9]:[c:10]:[c:11]:1:2>>[O-;H0;D1:1]-[n+;H0;D3:5]1:[c:4]:[c:3]:[#7;a:2]:[c:11]2:[c:10]:[#7;a:9]:[c:8]:[#7;a:7]:[c:6]:2:1 | 32 | [{"value": 32.0, "product": "NC1=NC2=[N+](C=CN=C2C(=N1)OCC)[O-]", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 2 | DAY | To a cooled (0° C.) solution of the compound of example 7 (2.47 g, 12.9 mmoles) in trifluoroacetic acid (53 ml) was added dropwise 2.53 ml of a 35% aqueous H2O2 solution. The reaction mixture was kept at 4° C. for two days in the refrigerator, whereby another 1.25 ml of the same H2O2 solution was added after 1 day. The... | 10.6084/m9.figshare.5104873.v1 | null | Peroxide | null | c1cnc2ncncc2n1 | C1=Nc2cncnc2[NH+]=C1 | C1=Nc2cncnc2[NH+]=C1 | HO- | FC(C(=O)O)(F)F | null | 48 | CCOc1nc(N)nc2nccnc12.OO>FC(C(=O)O)(F)F>CCOc1nc(N)nc2c1ncc[n+]2[O-] |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-3c88173537034105b7659e892ebb0d18 | Nc1cc(O)nc(N)n1>>Nc1nc(N)c(N=O)c(O)n1 | NC1=NC(=CC(=N1)O)N.C(C)(=O)O.N(=O)[O-].[Na+]>>NC1=NC(=C(C(=N1)O)N=O)N | [NH2:1][c:2]1[n:3][c:4]([NH2:5])[cH:6][c:9]([OH:10])[n:11]1>>[NH2:1][c:2]1[n:3][c:4]([NH2:5])[c:6]([N:7]=[O:8])[c:9]([OH:10])[n:11]1 | Nc1cc(O)nc(N)n1 | Nc1nc(N)c(N=O)c(O)n1 | null | null | O | Functional Group Addition | OtherReaction | 37b5dbf927322d4de54944b07579e1c735be607324387f2bb7b266fb591d966b | c852dfd7a307035d7b21dc79db1d13bba1cfffe7578c3caa265be3f4f0c038c5 | c1cncnc1 | [N;D1;H2:1]-[c:2]1:[#7;a:3]:[c:4]:[#7;a:5]:[c:6](-[O;D1;H1:7]):[cH;D2;+0:8]:1>>[N;D1;H2:1]-[c:2]1:[#7;a:3]:[c:4]:[#7;a:5]:[c:6](-[O;D1;H1:7]):[c;H0;D3;+0:8]:1-[#7:9]=[O;D1;H0:10] | 97.3 | [{"value": 97.0, "product": "NC1=NC(=C(C(=N1)O)N=O)N", "details": "PERCENTYIELD", "is_desired": false}, {"value": 97.3, "product": "NC1=NC(=C(C(=N1)O)N=O)N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | 1 | HOUR | To a solution of 2,6-diamino-4-hydroxypyrimidine (12.9 g, 102.2 mmoles) in 200 ml of a 10% acetic acid solution in water at 80° C. was added dropwise a solution of NaNO2 (7.05 g, 102.2 mmoles) in 20 ml water. A pink precipitate was formed, which was further stirred for 1 hour at 80° C. The reaction mixture was cooled d... | 10.6084/m9.figshare.5104873.v1 | null | null | Nitroso | c1cncnc1 | c1cncnc1 | c1cncnc1 | Other | O | 80 | 1 | Nc1cc(O)nc(N)n1>O>Nc1nc(N)c(N=O)c(O)n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-f987076083aa44828852f22275108aee | Nc1nc(N)c(N=O)c(O)n1>>Nc1nc(N)c(N)c(O)n1 | NC1=NC(=C(C(=N1)O)N=O)N>>NC1=NC(=C(C(=N1)O)N)N | O=[N:7][c:6]1[c:4]([NH2:5])[n:3][c:2]([NH2:1])[n:10][c:8]1[OH:9]>>[NH2:1][c:2]1[n:3][c:4]([NH2:5])[c:6]([NH2:7])[c:8]([OH:9])[n:10]1 | Nc1nc(N)c(N=O)c(O)n1 | Nc1nc(N)c(N)c(O)n1 | null | null | null | Reduction | OtherReaction | 10bd501bc4fc8c6849398545fc18bd5f6b51ea4e37b15a00157d17550a6b88bf | 7085a0cec3cc6daaf2fab855d070c407558563b5b6837070687c0df0a552c6fe | c1cncnc1 | O=[N;H0;D2;+0:1]-[c:2]1:[c:3](-[N;D1;H2:4]):[#7;a:5]:[c:6]:[#7;a:7]:[c:8]:1-[O;D1;H1:9]>>[N;D1;H2:4]-[c:3]1:[#7;a:5]:[c:6]:[#7;a:7]:[c:8](-[O;D1;H1:9]):[c:2]:1-[NH2;D1;+0:1] | 83 | [{"value": 83.0, "product": "NC1=NC(=C(C(=N1)O)N)N", "details": "PERCENTYIELD", "is_desired": false}, {"value": 83.0, "product": "NC1=NC(=C(C(=N1)O)N)N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 50 | CELSIUS | 8 | HOUR | A suspension of the compound of example 46 (15 g, 96.7 mmoles) in an ammonium sulfide solution (20% in water, 200 ml) was stirred overnight at 50° C. The reaction mixture was cooled down in the refrigerator and the precipitate was filtered off, providing the title compound as a yellow powder (11.33 g, yield: 83%). The ... | 10.6084/m9.figshare.5104873.v1 | null | Nitroso | Primary amine | null | null | c1cncnc1 | Other | null | 50 | 8 | Nc1nc(N)c(N=O)c(O)n1>>Nc1nc(N)c(N)c(O)n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-42095b2608ea4e5298f1660f83f003b0 | CC(=O)OC(C)=O.COc1ccc(-c2cnc3c(n2)C(=O)NC(N)(N)N3)cc1OC>>COc1ccc(-c2cnc3c(n2)C(=O)NC(N)(NC(C)=O)N3)cc1OC | NC1(NC2=NC=C(N=C2C(N1)=O)C1=CC(=C(C=C1)OC)OC)N.C(C)(=O)OC(C)=O>>C(C)(=O)NC1(NC2=NC=C(N=C2C(N1)=O)C1=CC(=C(C=C1)OC)OC)N | CC(=O)O[C:19]([CH3:20])=[O:21].[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][n:9][c:10]3[c:11]([n:12]2)[C:13](=[O:14])[NH:15][C:16]([NH2:17])([NH2:18])[NH:22]3)[cH:23][c:24]1[O:25][CH3:26]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][n:9][c:10]3[c:11]([n:12]2)[C:13](=[O:14])[NH:15][C:16]([NH2:17])([NH:18][C:1... | CC(=O)OC(C)=O.COc1ccc(-c2cnc3c(n2)C(=O)NC(N)(N)N3)cc1OC | COc1ccc(-c2cnc3c(n2)C(=O)NC(N)(NC(C)=O)N3)cc1OC | null | null | C(C)(=O)O | Acylation | Aminolysis of esters | 87d35e51b477fc9a658a6f307eb56d84c8879182772c9dd3a42ec0d584fd2684 | 627cbc0550c9f51ad0105d9fcf46677e8c93bed87ee95bfe69292a82550c95b7 | O=C1NCNc2ncc(-c3ccccc3)nc21 | C-C(=O)-O-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[#7;a:4]:[c:5]1:[c:6](:[#7;a:7])-[#7:8]-[C:9](-[N;D1;H2:10])(-[NH2;D1;+0:11])-[#7:12]-[C:13]-1=[O;D1;H0:14]>>[#7;a:4]:[c:5]1:[c:6](:[#7;a:7])-[#7:8]-[C:9](-[N;D1;H2:10])(-[NH;D2;+0:11]-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3])-[#7:12]-[C:13]-1=[O;D1;H0:14] | 77 | [{"value": 77.0, "product": "C(C)(=O)NC1(NC2=NC=C(N=C2C(N1)=O)C1=CC(=C(C=C1)OC)OC)N", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A suspension of the compound of example 48 (10.46 g, 35 mmoles) in acetic anhydride (600 ml) and acetic acid (200 ml) was refluxed for 1 hour until a clear solution was formed. By cooling down the reaction mixture in the refrigerator, the precipitate formed was filtered off, washed with ethyl acetate and diethyl ether,... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Primary amine | Secondary amide | null | null | c1ccccc1.c1cnc2c(n1)CNCN2 | HO- | C(C)(=O)O | null | null | CC(=O)OC(C)=O.COc1ccc(-c2cnc3c(n2)C(=O)NC(N)(N)N3)cc1OC>C(C)(=O)O>COc1ccc(-c2cnc3c(n2)C(=O)NC(N)(NC(C)=O)N3)cc1OC |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-fefcc001835f4ee6b6412f976a63b3b9 | COc1ccc(-c2cnc3c(n2)C(=O)NC(N)(NC(C)=O)N3)cc1OC.c1nc[nH]n1>>COc1ccc(-c2cnc3nc(NC(C)=O)nc(-c4nc[nH]n4)c3n2)cc1OC | P(=O)(Cl)(Cl)Cl.N1N=CN=C1.C(C)(=O)NC1(NC2=NC=C(N=C2C(N1)=O)C1=CC(=C(C=C1)OC)OC)N>>C(C)(=O)NC1=NC2=NC=C(N=C2C(=N1)C1=NNC=N1)C1=CC(=C(C=C1)OC)OC | N[C:12]1([NH:13][C:14]([CH3:15])=[O:16])[NH:11][c:10]2[n:9][cH:8][c:7](-[c:6]3[cH:5][cH:4][c:3]([O:2][CH3:1])[c:27]([O:28][CH3:29])[cH:26]3)[n:25][c:24]2[C:18](=O)[NH:17]1.[cH:19]1[n:20][cH:21][nH:22][n:23]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][n:9][c:10]3[n:11][c:12]([NH:13][C:14]([CH3:15])=[O:16])[n:17]... | COc1ccc(-c2cnc3c(n2)C(=O)NC(N)(NC(C)=O)N3)cc1OC.c1nc[nH]n1 | COc1ccc(-c2cnc3nc(NC(C)=O)nc(-c4nc[nH]n4)c3n2)cc1OC | null | null | N1=CC=CC=C1 | C-C Coupling | OtherReaction | f1294a018bad143020ef05b115edad6e6dca734eacd2751311e9ec4df59cffcc | 045628bbd55aa829413baf872876e233d703de880ade8dc61e36dec47c687179 | c1ccc(-c2cnc3ncnc(-c4nc[nH]n4)c3n2)cc1 | N-[C;H0;D4;+0:1]1(-[#7:2]-[C:3](-[C;D1;H3:4])=[O;D1;H0:5])-[NH;D2;+0:6]-[c:7]2:[#7;a:8]:[c:9]:[c:10]:[#7;a:11]:[c:12]:2-[C;H0;D3;+0:13](=O)-[NH;D2;+0:14]-1.[#7;a:15]1:[c:16]:[#7;a:17]:[#7;a:18]:[cH;D2;+0:19]:1>>[C;D1;H3:4]-[C:3](=[O;D1;H0:5])-[#7:2]-[c;H0;D3;+0:1]1:[n;H0;D2;+0:6]:[c:7]2:[#7;a:8]:[c:9]:[c:10]:[#7;a:11]:... | 80 | [{"value": 80.0, "product": "C(C)(=O)NC1=NC2=NC=C(N=C2C(=N1)C1=NNC=N1)C1=CC(=C(C=C1)OC)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 71.0, "product": "C(C)(=O)NC1=NC2=NC=C(N=C2C(=N1)C1=NNC=N1)C1=CC(=C(C=C1)OC)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 4 | HOUR | To a solution of phosphorus oxychloride (1.68 ml, 18 mmoles) and 1,2,4-triazole (4.96 g, 72 mmoles) in dry pyridine (110 ml) was added the compound of example 49 (2.45 g, 7.18 mmoles). The suspension was stirred at room temperature for 4 hours. The precipitate was filtered off, washed with pyridine, toluene and diethyl... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide.Primary amine.Secondary amine | null | c1cnc2c(n1)CNCN2.c1nnc[nH]1 | c1cnc2ncncc2n1.c1nnc[nH]1 | c1ccccc1.c1cnc2ncncc2n1.c1nnc[nH]1 | HO- | N1=CC=CC=C1 | null | 4 | COc1ccc(-c2cnc3c(n2)C(=O)NC(N)(NC(C)=O)N3)cc1OC.c1nc[nH]n1>N1=CC=CC=C1>COc1ccc(-c2cnc3nc(NC(C)=O)nc(-c4nc[nH]n4)c3n2)cc1OC |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-0613de76870a471481a9a851d9c28680 | CCOc1nc(N)nc2nc(-c3ccc(OC)c(OC)c3)cnc12>>COc1ccc(-c2cnc3c(OC)nc(N)nc3n2)cc1OC | COC=1C=C(C=CC1OC)C(=O)C=O.CO.NC1=NC2=NC(=CN=C2C(=N1)OCC)C1=CC(=C(C=C1)OC)OC>>NC1=NC2=NC(=CN=C2C(=N1)OC)C1=CC(=C(C=C1)OC)OC | C[CH2:13][O:12][c:11]1[c:10]2[n:9][cH:8][c:7](-[c:6]3[cH:5][cH:4][c:3]([O:2][CH3:1])[c:21]([O:22][CH3:23])[cH:20]3)[n:19][c:18]2[n:17][c:15]([NH2:16])[n:14]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][n:9][c:10]3[c:11]([O:12][CH3:13])[n:14][c:15]([NH2:16])[n:17][c:18]3[n:19]2)[cH:20][c:21]1[O:22][CH3:23] | CCOc1nc(N)nc2nc(-c3ccc(OC)c(OC)c3)cnc12 | COc1ccc(-c2cnc3c(OC)nc(N)nc3n2)cc1OC | null | null | C(C)(C)O | Miscellaneous | OtherReaction | 4aaa63d92793bb3347780900c7890c124a30137b2f711b41f0f3898a6907ad65 | bced64702950df7cf56df22d8c2487b007734fece951727fd2c8a1c63fbcf6cc | c1ccc(-c2cnc3cncnc3n2)cc1 | C-[CH2;D2;+0:1]-[#8:2]-[c:3](:[#7;a:4]):[c:5]:[#7;a:6]>>[#7;a:4]:[c:3](-[#8:2]-[CH3;D1;+0:1]):[c:5]:[#7;a:6] | null | [] | null | null | null | null | The sequence of reactions described in examples 53 to 57 was followed, however starting from 3,4-dimethoxyphenylglyoxal instead of 4-methoxyphenylglyoxal in the first step, and from methanol instead if isopropanol in the last step. This provided 2-amino-4-ethoxy-7-(3,4-dimethoxyphenyl) pteridine, a compound which was f... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Ether | null | null | c1ccccc1.c1cnc2ncncc2n1 | Other | C(C)(C)O | null | null | CCOc1nc(N)nc2nc(-c3ccc(OC)c(OC)c3)cnc12>C(C)(C)O>COc1ccc(-c2cnc3c(OC)nc(N)nc3n2)cc1OC |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-9cac5a6be1a440569a97960ad86d737e | [Cl-].[Cl-]>>Cl.Cl | C1(=CC=CC=C1)C.S(=O)(=O)(O)O.CSC1=NC(=C(C(=N1)N)N)N.O.O.[Cl-].[Ba+2].[Cl-]>>Cl.Cl.NC1=NC(=NC(=C1N)N)SC | [Cl-:13].[Cl-:12]>>[ClH:12].[ClH:13] | [Cl-].[Cl-] | Cl.Cl | null | null | O | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | null | [Cl-;H0;D0:1].[Cl-;H0;D0:2]>>[ClH;D0;+0:2].[ClH;D0;+0:1] | 209.9 | [{"value": 94.0, "product": "Cl.Cl.NC1=NC(=NC(=C1N)N)SC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 209.9, "product": "Cl.Cl.NC1=NC(=NC(=C1N)N)SC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | 30 | MINUTE | To a suspension of a 2-methylmercapto-4,5,6-triamino-pyrimidine sulfate (44.3 mmole), which may be prepared and characterised for instance as disclosed by Taylor et al. in J. Am. Chem. Soc. (1952) 74:1644-1647, in water (135 ml) at 80° C. was added dropwise a solution of barium chloride dihydrate (39.8 mmole) in water ... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | null | null | O | 80 | 0.5 | [Cl-].[Cl-]>O>Cl.Cl |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-2a52eb2a457545149d25ef6aa9099ef1 | C1COCCN1.Nc1cc(Cl)nc(N)n1>>Cl.Cl.Nc1nc(N)c(N)c(N2CCOCC2)n1 | NC1=NC(=CC(=N1)Cl)N.[OH-].[Na+].N(=O)[O-].[Na+].C(C)(=O)O.[O-]S(=O)S(=O)[O-].[Na+].[Na+].N1CCOCC1>>Cl.Cl.NC1=NC(=C(C(=N1)N1CCOCC1)N)N | [NH:11]1[CH2:12][CH2:13][O:14][CH2:15][CH2:16]1.[Cl:1][c:10]1[n:5][c:6]([NH2:7])[n:17][c:4]([NH2:3])[cH:8]1>>[ClH:1].[ClH:2].[NH2:3][c:4]1[n:5][c:6]([NH2:7])[c:8]([NH2:9])[c:10]([N:11]2[CH2:12][CH2:13][O:14][CH2:15][CH2:16]2)[n:17]1 | C1COCCN1.Nc1cc(Cl)nc(N)n1 | Cl.Cl.Nc1nc(N)c(N)c(N2CCOCC2)n1 | null | null | O | Functional Group Addition | OtherReaction | 5d919bfd9fb985f9b74c387511f1e5e568f78dc5a39a9fa80c2ae2f1613e3a9f | e0c2fc0877589be5a2f60d823fe4ba547f59cb9f5f6884aee9c9c03b2aa675f7 | c1cc(N2CCOCC2)ncn1 | [#8:1]1-[C:2]-[C:3]-[NH;D2;+0:4]-[C:5]-[C:6]-1.[Cl;H0;D1;+0:7]-[c;H0;D3;+0:8]1:[cH;D2;+0:9]:[c;H0;D3;+0:10](-[N;D1;H2:11]):[n;H0;D2;+0:12]:[c;H0;D3;+0:13](-[N;D1;H2:14]):[n;H0;D2;+0:15]:1>>[ClH;D0;+0:7].[N;D1;H2:11]-[c;H0;D3;+0:10]1:[n;H0;D2;+0:12]:[c;H0;D3;+0:8](-[N;H0;D3;+0:4]2-[C:3]-[C:2]-[#8:1]-[C:6]-[C:5]-2):[c;H0... | 141.3 | [{"value": 54.1, "product": "Cl.Cl.NC1=NC(=C(C(=N1)N1CCOCC1)N)N", "details": "PERCENTYIELD", "is_desired": false}, {"value": 141.3, "product": "Cl.Cl.NC1=NC(=C(C(=N1)N1CCOCC1)N)N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 21 | CELSIUS | null | null | In a 10 L 4-neck flask equipped with a mechanical stirrer, a thermometer and a heating mantle was placed 2,6-diamino-4-chloropyrimidine (870.5 g; 6.0 mol) In water (3190 ml). To the stirred resulting white suspension was added morpholine (1113 g; 12.8 moles) in one portion. The temperature raised from 14 to 28° C. and ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Primary amine.Tertiary amine | C1COCCN1.c1cncnc1 | c1cncnc1.C1COCC[NH]1 | c1cncnc1.C1COCC[NH]1 | Other | O | 21 | null | C1COCCN1.Nc1cc(Cl)nc(N)n1>O>Cl.Cl.Nc1nc(N)c(N)c(N2CCOCC2)n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-186682100cc14e9eb9f5399f077666f1 | COC(=O)C12CC3SC(C1)SC(C2)S3>>OCC12CC3SC(C1)SC(C2)S3 | COC(=O)C12CC3SC(SC(C1)S3)C2.C1(=CC=CC=C1)C.[H-].C(C(C)C)[Al+]CC(C)C>>OCC12CC3SC(SC(C1)S3)C2 | CO[C:2](=[O:1])[C:3]12[CH2:4][CH:5]3[S:6][CH:7]([CH2:8]1)[S:9][CH:10]([CH2:11]2)[S:12]3>>[OH:1][CH2:2][C:3]12[CH2:4][CH:5]3[S:6][CH:7]([CH2:8]1)[S:9][CH:10]([CH2:11]2)[S:12]3 | COC(=O)C12CC3SC(C1)SC(C2)S3 | OCC12CC3SC(C1)SC(C2)S3 | null | null | CCCCCC | Reduction | Reduction of ester to primary alcohol | 21d61543c6ec8a8cebe1b3ef55ef3dd20acbf79a4f1c12a7fb51e32be7a3248a | 1fbcd628a0426673c5d10aa49a977cd2d1ae02a8cdf57bbb10d94aa03a94e937 | C1C2CC3SC1SC(C2)S3 | C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[C:3](-[C:4])(-[C:5])-[C:6]>>[C:4]-[C:3](-[CH2;D2;+0:1]-[OH;D1;+0:2])(-[C:5])-[C:6] | 99 | [{"value": 97.0, "product": "OCC12CC3SC(SC(C1)S3)C2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 99.0, "product": "OCC12CC3SC(SC(C1)S3)C2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | null | null | A flame-dried, 25 mL round-bottomed flask equipped with a Teflon-coated magnetic bar and a septum with an argon inlet was charged with 270 mg (1.10 mmol) of 2,4,9-Trithia-tricyclo[3.3.1.13,7]decane-7-carboxylic acid methyl ester and 5 mL of dry toluene. Cooled by an ice bath, the solution was charged with 1.60 mL of 1.... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary alcohol | null | null | C1C2CC3SC1SC(C2)S3 | Other | CCCCCC | 0 | null | COC(=O)C12CC3SC(C1)SC(C2)S3>CCCCCC>OCC12CC3SC(C1)SC(C2)S3 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-6548c61644844463a0b82f95a1cc807e | COP(=O)(CC(C)=O)OC.CS(=O)(=O)N=[N+]=[N-]>>COP(=O)(OC)C(=[N+]=[N-])C(C)=O | [H-].[Na+].COP(OC)(=O)CC(C)=O.CS(=O)(=O)N=[N+]=[N-].CS(=O)(=O)Cl.[N-]=[N+]=[N-].[Na+]>>COP(OC)(=O)C(C(C)=O)=[N+]=[N-] | [CH3:1][O:2][P:3](=[O:4])([O:5][CH3:6])[CH2:7][C:10]([CH3:11])=[O:12].CS(=O)(=O)N=[N+:8]=[N-:9]>>[CH3:1][O:2][P:3](=[O:4])([O:5][CH3:6])[C:7](=[N+:8]=[N-:9])[C:10]([CH3:11])=[O:12] | COP(=O)(CC(C)=O)OC.CS(=O)(=O)N=[N+]=[N-] | COP(=O)(OC)C(=[N+]=[N-])C(C)=O | null | null | O1CCCC1.C1(=CC=CC=C1)C | Heteroatom Alkylation and Arylation | OtherReaction | f525e973623c74e01f3c5a05c7cc01f891477a2a97f7aa217686a22e249ae6e4 | de0f460205316603b40264b68ab409d0fff8afb864d7a608428f60cbfbf83e35 | null | C-S(=O)(=O)-N=[N+;H0;D2:1]=[N;-;D1;H0:2].[#8:3]-[#15:4](-[#8:5])(=[O;D1;H0:6])-[CH2;D2;+0:7]-[C:8](-[C;D1;H3:9])=[O;D1;H0:10]>>[#8:3]-[#15:4](-[#8:5])(=[O;D1;H0:6])-[C;H0;D3;+0:7](=[N+;H0;D2:1]=[N;-;D1;H0:2])-[C:8](-[C;D1;H3:9])=[O;D1;H0:10] | null | [] | null | null | 1 | HOUR | To an ice-cooled solution of sodium hydride in dry toluene, (2-oxo-propyl)-phosphonic acid dimethyl ester was added slowly. The solution mixture was stirred for 1 hour. Methanesulfonyl azide, prepared by the reaction of methanesulfonyl chloride and sodium azide, dissolved in dry toluene and dry tetrahydrofuran was adde... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Azide | Ketone.Diazo | null | null | null | HO- | O1CCCC1.C1(=CC=CC=C1)C | null | 1 | COP(=O)(CC(C)=O)OC.CS(=O)(=O)N=[N+]=[N-]>O1CCCC1.C1(=CC=CC=C1)C>COP(=O)(OC)C(=[N+]=[N-])C(C)=O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-9e724b691bf843049a0831ed12bdc474 | C=C(CC(=O)O)C(=O)O.Nc1ccc(OCc2cccc(F)c2)cc1>>O=C(O)C1CC(=O)N(c2ccc(OCc3cccc(F)c3)cc2)C1 | FC=1C=C(COC2=CC=C(C=C2)N)C=CC1.C(C(=C)CC(=O)O)(=O)O>>FC=1C=C(COC2=CC=C(C=C2)N2CC(CC2=O)C(=O)O)C=CC1 | O[C:6]([CH2:5][C:4]([C:2](=[O:1])[OH:3])=[CH2:24])=[O:7].[NH2:8][c:9]1[cH:10][cH:11][c:12]([O:13][CH2:14][c:15]2[cH:16][cH:17][cH:18][c:19]([F:20])[cH:21]2)[cH:22][cH:23]1>>[O:1]=[C:2]([OH:3])[CH:4]1[CH2:5][C:6](=[O:7])[N:8]([c:9]2[cH:10][cH:11][c:12]([O:13][CH2:14][c:15]3[cH:16][cH:17][cH:18][c:19]([F:20])[cH:21]3)[cH... | C=C(CC(=O)O)C(=O)O.Nc1ccc(OCc2cccc(F)c2)cc1 | O=C(O)C1CC(=O)N(c2ccc(OCc3cccc(F)c3)cc2)C1 | null | null | C(C)(=O)O.C1(=CC=CC=C1)C | Protection | OtherReaction | 37f4b8492750c7e46b0bee57601630c72bf8c7b6f749d4f241362f847080c4db | b19cad91dafaf954b8c8699d684122617f52c7d55786fc526451153a6a86c1ce | O=C1CCCN1c1ccc(OCc2ccccc2)cc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C;H0;D3;+0:4](=[CH2;D1;+0:5])-[C:6](=[O;D1;H0:7])-[O;D1;H1:8].[NH2;D1;+0:9]-[c:10](:[c:11]):[c:12]>>[O;D1;H0:7]=[C:6](-[O;D1;H1:8])-[CH;D3;+0:4]1-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[N;H0;D3;+0:9](-[c:10](:[c:11]):[c:12])-[CH2;D2;+0:5]-1 | 85.4 | [{"value": 85.4, "product": "FC=1C=C(COC2=CC=C(C=C2)N2CC(CC2=O)C(=O)O)C=CC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 101 | CELSIUS | 3 | HOUR | 4-(3-Fluoro-benzyloxy)-phenylamine (31.2 g, 144 mmol) was dissolved in toluene (208 mL) and acetic acid (52 mL). Itaconic acid (18.96 g, 144 mmol) was added to the stirred mixture. The mixture was heated to reflux (101° C.) and kept at this temperature for 3 h. On cooling, the product started to crystallize. At 10° C.,... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine.Vinyl | Tertiary amide | null | C1CC[NH]C1 | C1CC[NH]C1.c1ccccc1.c1ccccc1 | HO- | C(C)(=O)O.C1(=CC=CC=C1)C | 101 | 3 | C=C(CC(=O)O)C(=O)O.Nc1ccc(OCc2cccc(F)c2)cc1>C(C)(=O)O.C1(=CC=CC=C1)C>O=C(O)C1CC(=O)N(c2ccc(OCc3cccc(F)c3)cc2)C1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-72c2bd1bad3a4eaf8405910a86c23279 | O=C(O)C1CC(=O)N(c2ccc(OCc3cccc(F)c3)cc2)C1>>O=C(O)[C@H]1CC(=O)N(c2ccc(OCc3cccc(F)c3)cc2)C1 | C1(=CC=CC=C1)[C@@H](N)CO.FC=1C=C(COC2=CC=C(C=C2)N2CC(CC2=O)C(=O)O)C=CC1.C1(=CC=CC=C1)[C@@H](N)CO>>FC=1C=C(COC2=CC=C(C=C2)N2C[C@H](CC2=O)C(=O)O)C=CC1 | [O:1]=[C:2]([OH:3])[CH:4]1[CH2:5][C:6](=[O:7])[N:8]([c:9]2[cH:10][cH:11][c:12]([O:13][CH2:14][c:15]3[cH:16][cH:17][cH:18][c:19]([F:20])[cH:21]3)[cH:22][cH:23]2)[CH2:24]1>>[O:1]=[C:2]([OH:3])[C@H:4]1[CH2:5][C:6](=[O:7])[N:8]([c:9]2[cH:10][cH:11][c:12]([O:13][CH2:14][c:15]3[cH:16][cH:17][cH:18][c:19]([F:20])[cH:21]3)[cH:... | O=C(O)C1CC(=O)N(c2ccc(OCc3cccc(F)c3)cc2)C1 | O=C(O)[C@H]1CC(=O)N(c2ccc(OCc3cccc(F)c3)cc2)C1 | null | null | C(C)#N.O | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | O=C1CCCN1c1ccc(OCc2ccccc2)cc1 | null | 44.1 | [{"value": 44.0, "product": "FC=1C=C(COC2=CC=C(C=C2)N2C[C@H](CC2=O)C(=O)O)C=CC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 44.1, "product": "FC=1C=C(COC2=CC=C(C=C2)N2C[C@H](CC2=O)C(=O)O)C=CC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | The salt of the (S)-(II) compound with (R)-(−)-2-phenylglycinol was prepared in an analogous manner as described in Example 2a) from rac-1-[4-(3-fluoro-benzyloxy)-phenyl]-5-oxo-pyrrolidine-3-carboxylic acid (5 g, 15.2 mmol) in acetonitrile/water 95:5 (50 mL) using a solution of only 1.46 g (R)-(−)-2-phenylglycinol (10.... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | C1CC[NH]C1.c1ccccc1.c1ccccc1 | null | C(C)#N.O | null | null | O=C(O)C1CC(=O)N(c2ccc(OCc3cccc(F)c3)cc2)C1>C(C)#N.O>O=C(O)[C@H]1CC(=O)N(c2ccc(OCc3cccc(F)c3)cc2)C1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-3274c4ad445b487685d712c5420123db | O=C(O)[C@H]1CC(=O)N(c2ccc(OCc3cccc(F)c3)cc2)C1>>NC(=O)[C@H]1CC(=O)N(c2ccc(OCc3cccc(F)c3)cc2)C1 | C(=O)(N1C=NC=C1)N1C=NC=C1.FC=1C=C(COC2=CC=C(C=C2)N2C[C@H](CC2=O)C(=O)O)C=CC1>>FC=1C=C(COC2=CC=C(C=C2)N2C[C@H](CC2=O)C(=O)N)C=CC1 | O[C:2](=[O:3])[C@H:4]1[CH2:5][C:6](=[O:7])[N:8]([c:9]2[cH:10][cH:11][c:12]([O:13][CH2:14][c:15]3[cH:16][cH:17][cH:18][c:19]([F:20])[cH:21]3)[cH:22][cH:23]2)[CH2:24]1>>[NH2:1][C:2](=[O:3])[C@H:4]1[CH2:5][C:6](=[O:7])[N:8]([c:9]2[cH:10][cH:11][c:12]([O:13][CH2:14][c:15]3[cH:16][cH:17][cH:18][c:19]([F:20])[cH:21]3)[cH:22]... | O=C(O)[C@H]1CC(=O)N(c2ccc(OCc3cccc(F)c3)cc2)C1 | NC(=O)[C@H]1CC(=O)N(c2ccc(OCc3cccc(F)c3)cc2)C1 | null | null | O1CCCC1 | Functional Group Interconversion | OtherReaction | e1b1a1f71ee10336b9e90a021457b106dbfe08a22161aaad6804675a8134a46f | 5d384be3554a01fd49be5eb779c3b10075a4cc9a2373eb20aaa867286d4e28a9 | O=C1CCCN1c1ccc(OCc2ccccc2)cc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]1-[C:4]-[#7:5]-[C:6](=[O;D1;H0:7])-[C:8]-1>>[N;D1;H2:9]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]1-[C:4]-[#7:5]-[C:6](=[O;D1;H0:7])-[C:8]-1 | 96.7 | [{"value": 96.0, "product": "FC=1C=C(COC2=CC=C(C=C2)N2C[C@H](CC2=O)C(=O)N)C=CC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 96.7, "product": "FC=1C=C(COC2=CC=C(C=C2)N2C[C@H](CC2=O)C(=O)N)C=CC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 18 | CELSIUS | 15 | MINUTE | 1,1′-carbonyldiimidazole (8.27 g, 51.0 mmol) was suspended and partly dissolved in tetrahydrofuran (110 mL) at 18° C. (S)-1-[4-(3-fluoro-benzyloxy)-phenyl]-5-oxo-pyrrolidine-3-carboxylic acid (14.0 g, 42.5 mmol; enantiomeric purity (S):(R)=99.5:0.5) was added as a solid together with tetrahydrofuran (30 mL) used for ri... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Primary amide | null | null | C1CC[NH]C1.c1ccccc1.c1ccccc1 | null | O1CCCC1 | 18 | 0.25 | O=C(O)[C@H]1CC(=O)N(c2ccc(OCc3cccc(F)c3)cc2)C1>O1CCCC1>NC(=O)[C@H]1CC(=O)N(c2ccc(OCc3cccc(F)c3)cc2)C1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-99a3cd4705164cea8d3bb8067b7d2d30 | O=C(O)[C@H]1CC(=O)N(c2ccc(OCc3cccc(F)c3)cc2)C1>>NC(=O)[C@H]1CC(=O)N(c2ccc(OCc3cccc(F)c3)cc2)C1 | ClC(=O)OCC.FC=1C=C(COC2=CC=C(C=C2)N2C[C@H](CC2=O)C(=O)O)C=CC1.CN1CCOCC1>>FC=1C=C(COC2=CC=C(C=C2)N2C[C@H](CC2=O)C(=O)N)C=CC1 | O[C:2](=[O:3])[C@H:4]1[CH2:5][C:6](=[O:7])[N:8]([c:9]2[cH:10][cH:11][c:12]([O:13][CH2:14][c:15]3[cH:16][cH:17][cH:18][c:19]([F:20])[cH:21]3)[cH:22][cH:23]2)[CH2:24]1>>[NH2:1][C:2](=[O:3])[C@H:4]1[CH2:5][C:6](=[O:7])[N:8]([c:9]2[cH:10][cH:11][c:12]([O:13][CH2:14][c:15]3[cH:16][cH:17][cH:18][c:19]([F:20])[cH:21]3)[cH:22]... | O=C(O)[C@H]1CC(=O)N(c2ccc(OCc3cccc(F)c3)cc2)C1 | NC(=O)[C@H]1CC(=O)N(c2ccc(OCc3cccc(F)c3)cc2)C1 | null | null | O1CCCC1 | Functional Group Interconversion | OtherReaction | e1b1a1f71ee10336b9e90a021457b106dbfe08a22161aaad6804675a8134a46f | 5d384be3554a01fd49be5eb779c3b10075a4cc9a2373eb20aaa867286d4e28a9 | O=C1CCCN1c1ccc(OCc2ccccc2)cc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]1-[C:4]-[#7:5]-[C:6](=[O;D1;H0:7])-[C:8]-1>>[N;D1;H2:9]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]1-[C:4]-[#7:5]-[C:6](=[O;D1;H0:7])-[C:8]-1 | 88 | [{"value": 88.0, "product": "FC=1C=C(COC2=CC=C(C=C2)N2C[C@H](CC2=O)C(=O)N)C=CC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 87.8, "product": "FC=1C=C(COC2=CC=C(C=C2)N2C[C@H](CC2=O)C(=O)N)C=CC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 20 | MINUTE | To (S)-1-[4-(3-fluoro-benzyloxy)-phenyl]-5-oxo-pyrrolidine-3-carboxylic acid (2.0 g, 6.07 mmol; enantiomeric purity (S):(R)>99.9:0.1) in tetrahydrofuran (40 mL), N-methylmor-pholine (676 mg, 6.68 mmol) was added at 0° C. After stirring for 20 min, a solution of ethyl chloroformate (725 mg, 6.68 mmol) was added dropwise... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Primary amide | null | null | C1CC[NH]C1.c1ccccc1.c1ccccc1 | null | O1CCCC1 | null | 0.333333 | O=C(O)[C@H]1CC(=O)N(c2ccc(OCc3cccc(F)c3)cc2)C1>O1CCCC1>NC(=O)[C@H]1CC(=O)N(c2ccc(OCc3cccc(F)c3)cc2)C1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-9d5f7e23615a49bb80c50ab907f1f4fa | CC(C)=CC(C)CCCCC=O>>CC(C)=CC(C)CCCCCO | [BH4-].[Na+].CC(CCCCC=O)C=C(C)C.CC(=O)C>>CC(CCCCCO)C=C(C)C | [CH3:1][C:2]([CH3:3])=[CH:4][CH:5]([CH3:6])[CH2:7][CH2:8][CH2:9][CH2:10][CH:11]=[O:12]>>[CH3:1][C:2]([CH3:3])=[CH:4][CH:5]([CH3:6])[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][OH:12] | CC(C)=CC(C)CCCCC=O | CC(C)=CC(C)CCCCCO | null | null | C(C)O | Reduction | Reduction of aldehydes and ketones to alcohols | e7895795cd3f75445716c94697823c5929dcd4b5344525875fe75d36bca2f9d7 | 21bb81d5469aaaca71ab12c186bea4016451717fad8780cf288858a7d8fbc55a | null | [C:1]-[C:2]-[CH;D2;+0:3]=[O;H0;D1;+0:4]>>[C:1]-[C:2]-[CH2;D2;+0:3]-[OH;D1;+0:4] | 72.7 | [{"value": 72.7, "product": "CC(CCCCCO)C=C(C)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 16 | HOUR | 18 g (0.11 mol) of 6,8-dimethylnon-7-enal (1) and 96.0 g of ethanol are placed in a 500 ml round-bottomed flask equipped with a thermometer. Cooling is carried out to 5° C. and 2.0 g of sodium borohydride are added in small portions without exceeding a bulk temperature of 10° C. The mixture is stirred at ambient temper... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | Primary alcohol | null | null | null | null | C(C)O | null | 16 | CC(C)=CC(C)CCCCC=O>C(C)O>CC(C)=CC(C)CCCCCO |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-8a0cfead0535481bb11cf20b7fe8c21b | CC(=O)Cl.CC(C)=CC(C)CCCCCO>>CC(=O)OCCCCCC(C)C=C(C)C | Cl.C(C)(=O)Cl.CC(CCCCCO)C=C(C)C.C(C)N(CC)CC>>C(C)(=O)OCCCCCC(C=C(C)C)C | Cl[C:2]([CH3:1])=[O:3].[OH:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH:10]([CH3:11])[CH:12]=[C:13]([CH3:14])[CH3:15]>>[CH3:1][C:2](=[O:3])[O:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH:10]([CH3:11])[CH:12]=[C:13]([CH3:14])[CH3:15] | CC(=O)Cl.CC(C)=CC(C)CCCCCO | CC(=O)OCCCCCC(C)C=C(C)C | null | null | CC(C)(C)OC.COC(C)(C)C | Acylation | Schotten-Baumann to ester | 6cefe709828c5bd4655f254e75d5dff9e8876e192e7dd47256c1bc0067bc5291 | d8a7643b81ed07a6f633aa99465180dfa0565e61ae25aef36338ebb9837c9cef | null | Cl-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[C:4]-[C:5]-[OH;D1;+0:6]>>[C:4]-[C:5]-[O;H0;D2;+0:6]-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3] | 76 | [{"value": 76.0, "product": "C(C)(=O)OCCCCCC(C=C(C)C)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 14 | HOUR | 13 g (76 mmol) of 6,8-dimethylnon-7-enol (2), 10.8 g (107 mmol) of triethylamine and 200 ml of t-butyl methyl ether (MTBE) are placed in a 500 ml round-bottomed flask equipped with a thermometer and with a dropping funnel. Cooling is carried out to 5° C. and 8.4 g (107 mmol) of acetylchloride diluted in 20 ml of MTBE a... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary alcohol | Ester | null | null | null | HCl | CC(C)(C)OC.COC(C)(C)C | null | 14 | CC(=O)Cl.CC(C)=CC(C)CCCCCO>CC(C)(C)OC.COC(C)(C)C>CC(=O)OCCCCCC(C)C=C(C)C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-9f255ad1273e447f8231f3257934c590 | C1=Cc2cc3ccc(cc4nc(cc5ccc(cc1n2)[nH]5)C=C4)[nH]3.O.O=C(O)C(F)(F)F>>O=Cc1c2nc(cc3ccc([nH]3)c(C=O)c3nc(cc4ccc1[nH]4)C=C3)C=C2 | C(Cl)Cl.C(=O)(C(F)(F)F)O.O.C12=CC=C(N1)C=C1C=CC(=N1)C=C1C=CC(N1)=CC=1C=CC(N1)=C2>>C(=O)C=1C2=CC=C(N2)C=C2C=CC(C(=C3C=CC(=CC=4C=CC1N4)N3)C=O)=N2 | [cH:3]1[c:4]2[n:12][c:11]([cH:13][c:8]3[nH:5][c:6]([cH:7][c:16]4[n:17][c:18]([cH:19][c:20]5[cH:21][cH:22][c:23]1[nH:24]5)[CH:25]=[CH:26]4)[cH:27][cH:9]3)[CH:14]=[CH:28]2.[OH2:15].O[C:2](C(F)(F)F)=[O:1]>>[O:1]=[CH:2][c:3]1[c:4]2[n:5][c:6]([cH:7][c:8]3[cH:9][cH:10][c:11]([nH:12]3)[c:13]([CH:14]=[O:15])[c:16]3[n:17][c:18]... | C1=Cc2cc3ccc(cc4nc(cc5ccc(cc1n2)[nH]5)C=C4)[nH]3.O.O=C(O)C(F)(F)F | O=Cc1c2nc(cc3ccc([nH]3)c(C=O)c3nc(cc4ccc1[nH]4)C=C3)C=C2 | null | null | null | C-C Coupling | OtherReaction | 443dd67cc9c01ed0795d185a67926577b0f416fb123913db5536a50fb92d4b8f | 7da96aa513b345413c024fd57b4b61b8e16a6aa46bc791df63a30112399db1fc | C1=Cc2cc3ccc(cc4nc(cc5ccc(cc1n2)[nH]5)C=C4)[nH]3 | F-C(-F)(-F)-[C;H0;D3;+0:1](-O)=[O;D1;H0:2].[OH2;D0;+0:3].[c:4]:[#7;a:5]:[c:6](:[c:7]):[cH;D2;+0:8]:[c;H0;D3;+0:9]1:[n;H0;D2;+0:10]:[c;H0;D3;+0:11](:[cH;D2;+0:12]:[c;H0;D3;+0:13]2:[cH;D2;+0:14]:[cH;D2;+0:15]:[c:16](:[cH;D2;+0:17]:[c;H0;D3;+0:18]3:[#7;a:19]:[c:20]-[C:21]=[C:22]-3):[nH;D2;+0:23]:2)-[CH;D2;+0:24]=[CH;D2;+0... | 90 | [{"value": 90.0, "product": "C(=O)C=1C2=CC=C(N2)C=C2C=CC(C(=C3C=CC(=CC=4C=CC1N4)N3)C=O)=N2", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The route that employs a dipyrromethane-monocarbinol bearing the acetal at the 5-position begins with dipyrromethane 2. Treatment of 2 under the standard conditions for 1-acylation16 with pyridyl thioester 6 afforded the 1-acyldipyrromethane 7 in 72% yield. Reduction of 7 with NaBH4 and self-condensation16,21 of the re... | 10.6084/m9.figshare.5104873.v1 | null | Trifluoro group.Carboxylic acid | Aldehyde.Aldehyde | C1=Cc2cc3ccc(cc4nc(cc5ccc(cc1n2)n5)C=C4)n3 | C1=Cc2cc3ccc(cc4nc(cc5ccc(cc1n2)n5)C=C4)n3 | C1=Cc2cc3ccc(cc4nc(cc5ccc(cc1n2)n5)C=C4)n3 | HF | null | null | null | C1=Cc2cc3ccc(cc4nc(cc5ccc(cc1n2)[nH]5)C=C4)[nH]3.O.O=C(O)C(F)(F)F>>O=Cc1c2nc(cc3ccc([nH]3)c(C=O)c3nc(cc4ccc1[nH]4)C=C3)C=C2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-4a1c97c9bb4c4b699f0f6ce0d76f9695 | CC(C)(CO)CO.O=CC=O>>CC1(C)COC(C=O)OC1 | [O-]S(=O)(=O)[O-].[Na+].[Na+].C(=O)C=O.CC(CO)(CO)C.C1(=CC=C(C=C1)S(=O)(=O)O)C.C(=O)(O)[O-].[Na+]>>C(=O)C1OCC(CO1)(C)C | O[CH2:10][C:2]([CH3:1])([CH3:3])[CH2:4][OH:5].[CH:6]([CH:7]=[O:8])=[O:9]>>[CH3:1][C:2]1([CH3:3])[CH2:4][O:5][CH:6]([CH:7]=[O:8])[O:9][CH2:10]1 | CC(C)(CO)CO.O=CC=O | CC1(C)COC(C=O)OC1 | null | null | C1=CC=CC=C1 | Heteroatom Alkylation and Arylation | OtherReaction | 73c19e1dd216070b15ec212a551c866306f9ce0633eef38c38086c49c4ffca15 | 84f906b915b11ab21e1cc1ae9ab26ccac04fa933222d2c0dda259055bdf62145 | C1COCOC1 | O-[CH2;D2;+0:1]-[C:2](-[C;D1;H3:3])(-[C;D1;H3:4])-[C:5]-[OH;D1;+0:6].[O;D1;H0:7]=[C:8]-[CH;D2;+0:9]=[O;H0;D1;+0:10]>>[C;D1;H3:3]-[C:2]1(-[C;D1;H3:4])-[C:5]-[O;H0;D2;+0:6]-[CH;D3;+0:9](-[C:8]=[O;D1;H0:7])-[O;H0;D2;+0:10]-[CH2;D2;+0:1]-1 | 4.1 | [{"value": 4.0, "product": "C(=O)C1OCC(CO1)(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 4.1, "product": "C(=O)C1OCC(CO1)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of glyoxal (10.0 g of 40 wt. % aqueous solution, 0.070 mol), 2,2-dimethyl-1,3-propanediol (7.28 g, 0.070 mol) and p-toluenesulfonic acid (0.260 g, 1.36 mmol) in benzene (140 mL) was refluxed for 4 h in a flask fitted with a Soxhlet extractor containing Na2SO4. Then the reaction mixture was treated with solid ... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Aldehyde.Primary alcohol.Primary alcohol | Aldehyde.Ether.Ether | null | C1COCOC1 | C1COCOC1 | HO- | C1=CC=CC=C1 | null | null | CC(C)(CO)CO.O=CC=O>C1=CC=CC=C1>CC1(C)COC(C=O)OC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d72dde9035f24cf9900e94d149553176 | CC(C)(CO)CO.O=CC=O>>CC1(C)COC(C=O)OC1 | C(=O)C=O.CC(CO)(CO)C.C1(=CC=C(C=C1)S(=O)(=O)O)C.C(=O)(O)[O-].[Na+].[O-]S(=O)(=O)[O-].[Na+].[Na+]>>C(=O)C1OCC(CO1)(C)C | O[CH2:10][C:2]([CH3:1])([CH3:3])[CH2:4][OH:5].[CH:6]([CH:7]=[O:8])=[O:9]>>[CH3:1][C:2]1([CH3:3])[CH2:4][O:5][CH:6]([CH:7]=[O:8])[O:9][CH2:10]1 | CC(C)(CO)CO.O=CC=O | CC1(C)COC(C=O)OC1 | null | null | C1=CC=CC=C1 | Heteroatom Alkylation and Arylation | OtherReaction | 73c19e1dd216070b15ec212a551c866306f9ce0633eef38c38086c49c4ffca15 | 84f906b915b11ab21e1cc1ae9ab26ccac04fa933222d2c0dda259055bdf62145 | C1COCOC1 | O-[CH2;D2;+0:1]-[C:2](-[C;D1;H3:3])(-[C;D1;H3:4])-[C:5]-[OH;D1;+0:6].[O;D1;H0:7]=[C:8]-[CH;D2;+0:9]=[O;H0;D1;+0:10]>>[C;D1;H3:3]-[C:2]1(-[C;D1;H3:4])-[C:5]-[O;H0;D2;+0:6]-[CH;D3;+0:9](-[C:8]=[O;D1;H0:7])-[O;H0;D2;+0:10]-[CH2;D2;+0:1]-1 | 50 | [{"value": 50.0, "product": "C(=O)C1OCC(CO1)(C)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Streamlined Synthesis of 5-(5,5-Dimethyl-1,3-dioxan-2-yl)dipyrromethane (2). A mixture of glyoxal (10.0 g of 40 wt. % aqueous solution, 0.070 mol), 2,2-dimethyl 1,3-propanediol (7.28 g, 0.070 mol) and p-toluenesulfonic acid (0.260 g, 1.36 mmol) in benzene (140 mL) was refluxed for 4 h in a flask fitted with a Soxhlet e... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Aldehyde.Primary alcohol.Primary alcohol | Aldehyde.Ether.Ether | null | C1COCOC1 | C1COCOC1 | HO- | C1=CC=CC=C1 | null | null | CC(C)(CO)CO.O=CC=O>C1=CC=CC=C1>CC1(C)COC(C=O)OC1 |
Subsets and Splits
No community queries yet
The top public SQL queries from the community will appear here once available.