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-c3a75813d0b24864aa4f7cd526efd6aa | ord-ec77dfb64e5b43ed8c980fa971400be6 | CCc1nc2c(-c3ccc(C)cc3C)cc(C)nn2c1C(=O)OC>>CCc1nc2c(-c3ccc(C)cc3C)cc(C)nn2c1C(=O)O | [OH-].[Na+].COC(=O)C1=C(N=C2N1N=C(C=C2C2=C(C=C(C=C2)C)C)C)CC>>CC1=C(C=CC(=C1)C)C=1C=2N(N=C(C1)C)C(=C(N2)CC)C(=O)O | C[O:23][C:21]([c:20]1[c:3]([CH2:2][CH3:1])[n:4][c:5]2[c:6](-[c:7]3[cH:8][cH:9][c:10]([CH3:11])[cH:12][c:13]3[CH3:14])[cH:15][c:16]([CH3:17])[n:18][n:19]21)=[O:22]>>[CH3:1][CH2:2][c:3]1[n:4][c:5]2[c:6](-[c:7]3[cH:8][cH:9][c:10]([CH3:11])[cH:12][c:13]3[CH3:14])[cH:15][c:16]([CH3:17])[n:18][n:19]2[c:20]1[C:21](=[O:22])[OH... | CCc1nc2c(-c3ccc(C)cc3C)cc(C)nn2c1C(=O)OC | CCc1nc2c(-c3ccc(C)cc3C)cc(C)nn2c1C(=O)O | null | null | C(C)O | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccc(-c2ccnn3ccnc23)cc1 | C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4](:[#7;a:5]:[#7;a:6]):[c:7]:[#7;a:8]>>[#7;a:6]:[#7;a:5]:[c:4](-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1]):[c:7]:[#7;a:8] | null | [] | null | null | null | null | A 5N aqueous sodium hydroxide solution (20 mL) was added to a solution of the resulting 8-(2,4-dimethylphenyl)-2-ethyl-6-methylimidazo[1,2-b]pyridazin-3-carboxylic acid methyl ester in ethanol (100 mL), and the mixture was heated under reflux for 3 hours. The reaction mixture was evaporated as it was. Water was added t... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1.c1cnn2ccnc2c1 | Other | C(C)O | null | null | CCc1nc2c(-c3ccc(C)cc3C)cc(C)nn2c1C(=O)OC>C(C)O>CCc1nc2c(-c3ccc(C)cc3C)cc(C)nn2c1C(=O)O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-f219c0459560454a888fc84392da9705 | CC(C)(C)O.CCc1nc2c(-c3ccc(C)cc3C)cc(C)nn2c1C(=O)O.[N-]=[N+]=Nc1[pH]cc(-c2ccccc2)c1-c1ccccc1>>CCc1nc2c(-c3ccc(C)cc3C)cc(C)nn2c1NC(=O)OC(C)(C)C | O.C(C)N(CC)CC.C(C)(C)(C)O.C1(=CC=CC=C1)C=1C(=C(PC1)N=[N+]=[N-])C1=CC=CC=C1.CC1=C(C=CC(=C1)C)C=1C=2N(N=C(C1)C)C(=C(N2)CC)C(=O)O>>CC1=C(C=CC(=C1)C)C=1C=2N(N=C(C1)C)C(=C(N2)CC)NC(OC(C)(C)C)=O | [OH:24][C:25]([CH3:26])([CH3:27])[CH3:28].O[C:22]([c:20]1[c:3]([CH2:2][CH3:1])[n:4][c:5]2[c:6](-[c:7]3[cH:8][cH:9][c:10]([CH3:11])[cH:12][c:13]3[CH3:14])[cH:15][c:16]([CH3:17])[n:18][n:19]21)=[O:23].[N-]=[N+]=[N:21]c1[pH]cc(-c2ccccc2)c1-c1ccccc1>>[CH3:1][CH2:2][c:3]1[n:4][c:5]2[c:6](-[c:7]3[cH:8][cH:9][c:10]([CH3:11])[... | CC(C)(C)O.CCc1nc2c(-c3ccc(C)cc3C)cc(C)nn2c1C(=O)O.[N-]=[N+]=Nc1[pH]cc(-c2ccccc2)c1-c1ccccc1 | CCc1nc2c(-c3ccc(C)cc3C)cc(C)nn2c1NC(=O)OC(C)(C)C | null | null | C1(=CC=CC=C1)C | Protection | OtherReaction | 955039b1b29a15c4df8b7152053c3a2b3b9a3404b0b3f43d655c58d05cc605d1 | b944663b5278c281edc6c72611c69e4309c3f5728dcd63d51413085e18c1d2e7 | c1ccc(-c2ccnn3ccnc23)cc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c;H0;D3;+0:3]1:[#7;a:4](:[#7;a:5]:[c:6]):[c:7](:[c:8]):[#7;a:9]:[c:10]:1-[C:11].[C;D1;H3:12]-[C:13](-[C;D1;H3:14])(-[C;D1;H3:15])-[OH;D1;+0:16].[N-]=[N+]=[N;H0;D2;+0:17]-c1:[pH]:c:c(-c2:c:c:c:c:c:2):c:1-c1:c:c:c:c:c:1>>[C:11]-[c:10]1:[#7;a:9]:[c:7](:[c:8]):[#7;a:4](:[#7;a:5]:[c:6]):[c;H0... | null | [] | 140 | CELSIUS | null | null | Triethylamine (20 mL), tert-butyl alcohol (30 mL) and diphenylphospholylazide (1.95 mL, 9.05 mmol) were added to a solution of the resulting 8-(2,4-dimethylphenyl)-2-ethyl-6-methylimidazo[1,2-b]pyridazine-3-carboxylic acid (2.8 g, 9.05 mmol) in toluene (40 mL), and the mixture was heated at 140° C. for 6 hours. Water w... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Azide.Tertiary alcohol | Carbamic ester.Ether.Boc | c1cnn2ccnc2c1.c1cc[pH]c1.c1ccccc1.c1ccccc1 | c1cnn2ccnc2c1 | c1ccccc1.c1cnn2ccnc2c1 | HO- | C1(=CC=CC=C1)C | 140 | null | CC(C)(C)O.CCc1nc2c(-c3ccc(C)cc3C)cc(C)nn2c1C(=O)O.[N-]=[N+]=Nc1[pH]cc(-c2ccccc2)c1-c1ccccc1>C1(=CC=CC=C1)C>CCc1nc2c(-c3ccc(C)cc3C)cc(C)nn2c1NC(=O)OC(C)(C)C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-6c4d5a1da9ca485899cb2ced4ee490a0 | CCc1nc2c(-c3ccc(C)cc3C)cc(C)nn2c1NC(=O)OC(C)(C)C>>CCc1nc2c(-c3ccc(C)cc3C)cc(C)nn2c1N | Cl.C(C)(=O)OCC.CC1=C(C=CC(=C1)C)C=1C=2N(N=C(C1)C)C(=C(N2)CC)NC(OC(C)(C)C)=O.[OH-].[Na+]>>CC1=C(C=CC(=C1)C)C=1C=2N(N=C(C1)C)C(=C(N2)CC)N | CC(C)(C)OC(=O)[NH:21][c:20]1[c:3]([CH2:2][CH3:1])[n:4][c:5]2[c:6](-[c:7]3[cH:8][cH:9][c:10]([CH3:11])[cH:12][c:13]3[CH3:14])[cH:15][c:16]([CH3:17])[n:18][n:19]21>>[CH3:1][CH2:2][c:3]1[n:4][c:5]2[c:6](-[c:7]3[cH:8][cH:9][c:10]([CH3:11])[cH:12][c:13]3[CH3:14])[cH:15][c:16]([CH3:17])[n:18][n:19]2[c:20]1[NH2:21] | CCc1nc2c(-c3ccc(C)cc3C)cc(C)nn2c1NC(=O)OC(C)(C)C | CCc1nc2c(-c3ccc(C)cc3C)cc(C)nn2c1N | null | null | C(C)(=O)OCC | Reduction | Hydrogenolysis of amides/imides/carbamates | 3c33dd2a2d355ee5ba0287367e209aa147a39aa00607f0c95fb2bf1ade45d014 | c5b5dffe7dd8beebdc1baa8b5b05300a9f7079e65dcfd42ade6f8a77ff09537d | c1ccc(-c2ccnn3ccnc23)cc1 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[c:2]1:[#7;a:3](:[#7;a:4]:[c:5]):[c:6]:[#7;a:7]:[c:8]:1-[C:9]>>[C:9]-[c:8]1:[#7;a:7]:[c:6]:[#7;a:3](:[#7;a:4]:[c:5]):[c:2]:1-[NH2;D1;+0:1] | null | [] | null | null | 14 | HOUR | 4N hydrochloric acid/ethyl acetate (30 mL) was added to a solution of the resulting tert-butyl N-[8-(2,4-dimethylphenyl)-2-ethyl-6-methylimidazo[1,2-b]pyridazin-3-yl]carbamate in ethyl acetate (10 mL), and the mixture was stirred at room temperature for 14 hours. The mixture was neutralized by adding 5N aqueous sodium ... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Primary amine | null | null | c1ccccc1.c1cnn2ccnc2c1 | HO- | C(C)(=O)OCC | null | 14 | CCc1nc2c(-c3ccc(C)cc3C)cc(C)nn2c1NC(=O)OC(C)(C)C>C(C)(=O)OCC>CCc1nc2c(-c3ccc(C)cc3C)cc(C)nn2c1N |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-99953881eaed4d98867e50172ed72367 | CC(=O)O.CC(=O)O[BH-](OC(C)=O)OC(C)=O.CCC=O.CCc1nc2c(-c3ccc(C)cc3C)cc(C)nn2c1N>>CCCN(CCC)c1c(CC)nc2c(-c3ccc(C)cc3C)cc(C)nn12 | C(C)(=O)O.C(CC)=O.CC1=C(C=CC(=C1)C)C=1C=2N(N=C(C1)C)C(=C(N2)CC)N.C(C)(=O)O[BH-](OC(C)=O)OC(C)=O.[Na+]>>CC1=C(C=CC(=C1)C)C=1C=2N(N=C(C1)C)C(=C(N2)CC)N(CCC)CCC | O=[C:5](O)[CH3:6].CC(=O)O[BH-](OC(C)=O)OC(=O)[CH3:7].O=[CH:3][CH2:2][CH3:1].[NH2:4][c:8]1[c:9]([CH2:10][CH3:11])[n:12][c:13]2[c:14](-[c:15]3[cH:16][cH:17][c:18]([CH3:19])[cH:20][c:21]3[CH3:22])[cH:23][c:24]([CH3:25])[n:26][n:27]12>>[CH3:1][CH2:2][CH2:3][N:4]([CH2:5][CH2:6][CH3:7])[c:8]1[c:9]([CH2:10][CH3:11])[n:12][c:1... | CC(=O)O.CC(=O)O[BH-](OC(C)=O)OC(C)=O.CCC=O.CCc1nc2c(-c3ccc(C)cc3C)cc(C)nn2c1N | CCCN(CCC)c1c(CC)nc2c(-c3ccc(C)cc3C)cc(C)nn12 | null | null | ClCCl.O | Heteroatom Alkylation and Arylation | OtherReaction | 72e9da2aba1d8936b94244127c9bab45cbdbdb9e71f57cb28565a139dcef7a1d | 996df106b620b728ac5024cde06f3dbfda15a09e51d5e7ab9b342c86c263d13f | c1ccc(-c2ccnn3ccnc23)cc1 | C-C(=O)-O-[BH-](-O-C(-C)=O)-O-C(=O)-[CH3;D1;+0:1].O-[C;H0;D3;+0:2](=O)-[CH3;D1;+0:3].O=[CH;D2;+0:4]-[C:5]-[C;D1;H3:6].[C:7]-[c:8]1:[#7;a:9]:[c:10]:[#7;a:11](:[#7;a:12]:[c:13]):[c:14]:1-[NH2;D1;+0:15]>>[C:7]-[c:8]1:[#7;a:9]:[c:10]:[#7;a:11](:[#7;a:12]:[c:13]):[c:14]:1-[N;H0;D3;+0:15](-[CH2;D2;+0:4]-[C:5]-[C;D1;H3:6])-[C... | null | [] | null | null | 10 | MINUTE | Propionaldehyde (3.26 mL, 45.25 mmol) was added to a solution of the resulting 8-(2,4-dimethylphenyl)-2-ethyl-6-methylimidazo[1,2-b]pyridazin-3-amine (9.05 mmol) in dichloromethane (60 mL), and the mixture was stirred at room temperature for 10 minutes. Sodium triacetoxyborohydride (5.75 g, 27.15 mmol) was gradually ad... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Carboxylic acid.Primary amine | Tertiary amine | null | null | c1ccccc1.c1cnn2ccnc2c1 | HO-.B | ClCCl.O | null | 0.166667 | CC(=O)O.CC(=O)O[BH-](OC(C)=O)OC(C)=O.CCC=O.CCc1nc2c(-c3ccc(C)cc3C)cc(C)nn2c1N>ClCCl.O>CCCN(CCC)c1c(CC)nc2c(-c3ccc(C)cc3C)cc(C)nn12 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-2a6d8a1afc0e40998dc141f77e43efb9 | CCc1nc2c(-c3ccc(C)cc3C)ccnn2c1C(=O)OC>>CCc1nc2c(-c3ccc(C)cc3C)ccnn2c1C(=O)O | [OH-].[Na+].CC1=C(C=CC(=C1)C)C=1C=2N(N=CC1)C(=C(N2)CC)C(=O)OC.Cl>>CC1=C(C=CC(=C1)C)C=1C=2N(N=CC1)C(=C(N2)CC)C(=O)O | C[O:22][C:20]([c:19]1[c:3]([CH2:2][CH3:1])[n:4][c:5]2[c:6](-[c:7]3[cH:8][cH:9][c:10]([CH3:11])[cH:12][c:13]3[CH3:14])[cH:15][cH:16][n:17][n:18]21)=[O:21]>>[CH3:1][CH2:2][c:3]1[n:4][c:5]2[c:6](-[c:7]3[cH:8][cH:9][c:10]([CH3:11])[cH:12][c:13]3[CH3:14])[cH:15][cH:16][n:17][n:18]2[c:19]1[C:20](=[O:21])[OH:22] | CCc1nc2c(-c3ccc(C)cc3C)ccnn2c1C(=O)OC | CCc1nc2c(-c3ccc(C)cc3C)ccnn2c1C(=O)O | null | null | C(C)O | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccc(-c2ccnn3ccnc23)cc1 | C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4](:[#7;a:5]:[#7;a:6]):[c:7]:[#7;a:8]>>[#7;a:6]:[#7;a:5]:[c:4](-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1]):[c:7]:[#7;a:8] | null | [] | null | null | null | null | A 5N aqueous sodium hydroxide solution (0.603 mL, 3.0 mmol) was added to a solution of methyl 8-(2,4-dimethylphenyl)-2-ethylimidazo[1,2-b]pyridazine-3-carboxylate (373 mg, 1.20 mmol) in ethanol (15 mL), and the mixture was heated under reflux for 1 hour. 5N hydrochloric acid (0.603 mL) was added thereto under ice-cooli... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1.c1cnn2ccnc2c1 | Other | C(C)O | null | null | CCc1nc2c(-c3ccc(C)cc3C)ccnn2c1C(=O)OC>C(C)O>CCc1nc2c(-c3ccc(C)cc3C)ccnn2c1C(=O)O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-cfc37113527a4f9495b9846ad564c536 | CC(C)(C)O.CCc1nc2c(-c3ccc(C)cc3C)ccnn2c1C(=O)O.[N-]=[N+]=Nc1[pH]cc(-c2ccccc2)c1-c1ccccc1>>CCc1nc2c(-c3ccc(C)cc3C)ccnn2c1NC(=O)OC(C)(C)C | C(C)N(CC)CC.C(C)(C)(C)O.C1(=CC=CC=C1)C=1C(=C(PC1)N=[N+]=[N-])C1=CC=CC=C1.CC1=C(C=CC(=C1)C)C=1C=2N(N=CC1)C(=C(N2)CC)C(=O)O.O>>CC1=C(C=CC(=C1)C)C=1C=2N(N=CC1)C(=C(N2)CC)NC(OC(C)(C)C)=O | [OH:23][C:24]([CH3:25])([CH3:26])[CH3:27].O[C:21]([c:19]1[c:3]([CH2:2][CH3:1])[n:4][c:5]2[c:6](-[c:7]3[cH:8][cH:9][c:10]([CH3:11])[cH:12][c:13]3[CH3:14])[cH:15][cH:16][n:17][n:18]21)=[O:22].[N-]=[N+]=[N:20]c1[pH]cc(-c2ccccc2)c1-c1ccccc1>>[CH3:1][CH2:2][c:3]1[n:4][c:5]2[c:6](-[c:7]3[cH:8][cH:9][c:10]([CH3:11])[cH:12][c:... | CC(C)(C)O.CCc1nc2c(-c3ccc(C)cc3C)ccnn2c1C(=O)O.[N-]=[N+]=Nc1[pH]cc(-c2ccccc2)c1-c1ccccc1 | CCc1nc2c(-c3ccc(C)cc3C)ccnn2c1NC(=O)OC(C)(C)C | null | null | C1(=CC=CC=C1)C | Protection | OtherReaction | 955039b1b29a15c4df8b7152053c3a2b3b9a3404b0b3f43d655c58d05cc605d1 | b944663b5278c281edc6c72611c69e4309c3f5728dcd63d51413085e18c1d2e7 | c1ccc(-c2ccnn3ccnc23)cc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c;H0;D3;+0:3]1:[#7;a:4](:[#7;a:5]:[c:6]):[c:7](:[c:8]):[#7;a:9]:[c:10]:1-[C:11].[C;D1;H3:12]-[C:13](-[C;D1;H3:14])(-[C;D1;H3:15])-[OH;D1;+0:16].[N-]=[N+]=[N;H0;D2;+0:17]-c1:[pH]:c:c(-c2:c:c:c:c:c:2):c:1-c1:c:c:c:c:c:1>>[C:11]-[c:10]1:[#7;a:9]:[c:7](:[c:8]):[#7;a:4](:[#7;a:5]:[c:6]):[c;H0... | null | [] | 110 | CELSIUS | null | null | Triethylamine (0.202 mL, 1.4 mmol), t-butyl alcohol (5 mL) and diphenylphospholylazide (0.26 mL, 1.2 mmol) were added to a solution of the crude 8-(2,4-dimethylphenyl)-2-ethylimidazo[1,2-b]pyridazine-3-carboxylic acid (1.206 mmol) in toluene (10 mL), and the mixture was heated at 90° C. for 1 hour and 110° C. for 4 hou... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Azide.Tertiary alcohol | Carbamic ester.Ether.Boc | c1cnn2ccnc2c1.c1cc[pH]c1.c1ccccc1.c1ccccc1 | c1cnn2ccnc2c1 | c1ccccc1.c1cnn2ccnc2c1 | HO- | C1(=CC=CC=C1)C | 110 | null | CC(C)(C)O.CCc1nc2c(-c3ccc(C)cc3C)ccnn2c1C(=O)O.[N-]=[N+]=Nc1[pH]cc(-c2ccccc2)c1-c1ccccc1>C1(=CC=CC=C1)C>CCc1nc2c(-c3ccc(C)cc3C)ccnn2c1NC(=O)OC(C)(C)C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-d97d971ddf644182ba53ba7ae07aaca8 | CCc1nc2c(-c3ccc(C)cc3C)ccnn2c1NC(=O)OC(C)(C)C>>CCc1nc2c(-c3ccc(C)cc3C)ccnn2c1N | Cl.C(C)(=O)OCC.CC1=C(C=CC(=C1)C)C=1C=2N(N=CC1)C(=C(N2)CC)NC(OC(C)(C)C)=O.[OH-].[Na+]>>CC1=C(C=CC(=C1)C)C=1C=2N(N=CC1)C(=C(N2)CC)N | CC(C)(C)OC(=O)[NH:20][c:19]1[c:3]([CH2:2][CH3:1])[n:4][c:5]2[c:6](-[c:7]3[cH:8][cH:9][c:10]([CH3:11])[cH:12][c:13]3[CH3:14])[cH:15][cH:16][n:17][n:18]21>>[CH3:1][CH2:2][c:3]1[n:4][c:5]2[c:6](-[c:7]3[cH:8][cH:9][c:10]([CH3:11])[cH:12][c:13]3[CH3:14])[cH:15][cH:16][n:17][n:18]2[c:19]1[NH2:20] | CCc1nc2c(-c3ccc(C)cc3C)ccnn2c1NC(=O)OC(C)(C)C | CCc1nc2c(-c3ccc(C)cc3C)ccnn2c1N | null | null | C(C)(=O)OCC | Reduction | Hydrogenolysis of amides/imides/carbamates | 3c33dd2a2d355ee5ba0287367e209aa147a39aa00607f0c95fb2bf1ade45d014 | c5b5dffe7dd8beebdc1baa8b5b05300a9f7079e65dcfd42ade6f8a77ff09537d | c1ccc(-c2ccnn3ccnc23)cc1 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[c:2]1:[#7;a:3](:[#7;a:4]:[c:5]):[c:6]:[#7;a:7]:[c:8]:1-[C:9]>>[C:9]-[c:8]1:[#7;a:7]:[c:6]:[#7;a:3](:[#7;a:4]:[c:5]):[c:2]:1-[NH2;D1;+0:1] | null | [] | null | null | 15 | HOUR | 4N hydrochloric acid/ethyl acetate (15 mL) was added to a solution of the crude tert-butyl N-[8-(2,4-dimethylphenyl)-2-ethylimidazo[1,2-b]pyridazin-3-yl]carbamate in ethyl acetate (5 mL), and the mixture was stirred at room temperature for 15 hours. The mixture was neutralized by adding a 5N aqueous sodium hydroxide so... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Primary amine | null | null | c1ccccc1.c1cnn2ccnc2c1 | HO- | C(C)(=O)OCC | null | 15 | CCc1nc2c(-c3ccc(C)cc3C)ccnn2c1NC(=O)OC(C)(C)C>C(C)(=O)OCC>CCc1nc2c(-c3ccc(C)cc3C)ccnn2c1N |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-f4ed6574379d403ca88d1259381799ea | C1CCOC1.CCC=O.CCc1nc2c(-c3ccc(C)cc3C)ccnn2c1N>>CCCN(CCC)c1c(CC)nc2c(-c3ccc(C)cc3C)ccnn12 | [BH4-].[Na+].C(CC)=O.S(O)(O)(=O)=O.CC1=C(C=CC(=C1)C)C=1C=2N(N=CC1)C(=C(N2)CC)N.O1CCCC1.[OH-].[Na+]>>CC1=C(C=CC(=C1)C)C=1C=2N(N=CC1)C(=C(N2)CC)N(CCC)CCC | C1O[CH2:6][CH2:5][CH2:7]1.O=[CH:3][CH2:2][CH3:1].[NH2:4][c:8]1[c:9]([CH2:10][CH3:11])[n:12][c:13]2[c:14](-[c:15]3[cH:16][cH:17][c:18]([CH3:19])[cH:20][c:21]3[CH3:22])[cH:23][cH:24][n:25][n:26]12>>[CH3:1][CH2:2][CH2:3][N:4]([CH2:5][CH2:6][CH3:7])[c:8]1[c:9]([CH2:10][CH3:11])[n:12][c:13]2[c:14](-[c:15]3[cH:16][cH:17][c:1... | C1CCOC1.CCC=O.CCc1nc2c(-c3ccc(C)cc3C)ccnn2c1N | CCCN(CCC)c1c(CC)nc2c(-c3ccc(C)cc3C)ccnn12 | null | null | O | Heteroatom Alkylation and Arylation | OtherReaction | 6d53ba521f8dd859a1d027aff20a1f30229be42b36780b5882e61533b2cc295e | df535931b8059d394937514de5b7d3a229014cb8b85d7d4618a05bc841c21364 | c1ccc(-c2ccnn3ccnc23)cc1 | C1-O-[CH2;D2;+0:1]-[CH2;D2;+0:2]-[CH2;D2;+0:3]-1.O=[CH;D2;+0:4]-[C:5]-[C;D1;H3:6].[C:7]-[c:8]1:[#7;a:9]:[c:10]:[#7;a:11](:[#7;a:12]:[c:13]):[c:14]:1-[NH2;D1;+0:15]>>[C:7]-[c:8]1:[#7;a:9]:[c:10]:[#7;a:11](:[#7;a:12]:[c:13]):[c:14]:1-[N;H0;D3;+0:15](-[CH2;D2;+0:4]-[C:5]-[C;D1;H3:6])-[CH2;D2;+0:2]-[CH2;D2;+0:1]-[CH3;D1;+0... | 10 | [{"value": 10.0, "product": "CC1=C(C=CC(=C1)C)C=1C=2N(N=CC1)C(=C(N2)CC)N(CCC)CCC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | Propionaldehyde (0.435 mL, 6.0 mmol) and 3M sulfuric acid (2.01 mL, 6.0 mmol) were added to a solution of the crude 8-(2,4-dimethylphenyl)-2-ethylimidazo[1,2-b]pyridazin-3-amine (1.2 mmol) in tetrahydrofuran (10 mL) under ice-cooling, and sodium borohydride (182 mg, 4.8 mmol) was gradually added at the same temperature... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ether.Primary amine | Tertiary amine | C1CCOC1 | null | c1ccccc1.c1cnn2ccnc2c1 | HO- | O | null | 0.5 | C1CCOC1.CCC=O.CCc1nc2c(-c3ccc(C)cc3C)ccnn2c1N>O>CCCN(CCC)c1c(CC)nc2c(-c3ccc(C)cc3C)ccnn12 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-77c70f7d10ab4f73bd20ef27a44e65e9 | CCCN(CCC)c1c(SC)nc2c(Br)cc(C)cn12.OB(O)c1ccc(Cl)cc1Cl>>CCCN(CCC)c1c(SC)nc2c(-c3ccc(Cl)cc3Cl)cc(C)cn12 | BrC=1C=2N(C=C(C1)C)C(=C(N2)SC)N(CCC)CCC.ClC1=C(C=CC(=C1)Cl)B(O)O.O.O.O.O.O.O.O.O.[OH-].[Ba+2].[OH-]>>ClC1=C(C=CC(=C1)Cl)C=1C=2N(C=C(C1)C)C(=C(N2)SC)N(CCC)CCC | Br[c:14]1[c:13]2[n:12][c:9]([S:10][CH3:11])[c:8]([N:4]([CH2:3][CH2:2][CH3:1])[CH2:5][CH2:6][CH3:7])[n:27]2[cH:26][c:24]([CH3:25])[cH:23]1.OB(O)[c:15]1[cH:16][cH:17][c:18]([Cl:19])[cH:20][c:21]1[Cl:22]>>[CH3:1][CH2:2][CH2:3][N:4]([CH2:5][CH2:6][CH3:7])[c:8]1[c:9]([S:10][CH3:11])[n:12][c:13]2[c:14](-[c:15]3[cH:16][cH:17]... | CCCN(CCC)c1c(SC)nc2c(Br)cc(C)cn12.OB(O)c1ccc(Cl)cc1Cl | CCCN(CCC)c1c(SC)nc2c(-c3ccc(Cl)cc3Cl)cc(C)cn12 | null | null | O.COCCOC | C-C Coupling | Suzuki coupling with boronic acids | 6d2f92e38cbc7faf246cda8a4b8669001b5c18f23ff87160bd75535916dab019 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(-c2cccn3ccnc23)cc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[#7;a:5]2:[c:6]:[c:7]:[#7;a:8]:[c:9]:2:1.O-B(-O)-[c;H0;D3;+0:10](:[c:11]:[c:12]):[c:13](-[Cl;D1;H0:14]):[c:15]>>[Cl;D1;H0:14]-[c:13](:[c:15]):[c;H0;D3;+0:10](-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[#7;a:5]2:[c:6]:[c:7]:[#7;a:8]:[c:9]:2:1):[c:11]:[c:12] | 72.5 | [{"value": 72.5, "product": "ClC1=C(C=CC(=C1)Cl)C=1C=2N(C=C(C1)C)C(=C(N2)SC)N(CCC)CCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | N-[8-Bromo-6-methyl-2-(methylsulfanyl)imidazo[1,2-a]pyridin-3-yl]-N,N-dipropylamine (50 mg) was dissolved in a mixed solvent of 1,2-dimethoxyethane (6 mL) and water (1 mL). 2,4-Dichlorobenzeneboronic acid (53 mg), barium hydroxide octahydrate (88 mg) and tetrakistriphenylphosphine palladium complex (16 mg) were added t... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccn2ccnc2c1.c1ccccc1 | c1ccccc1.c1ccn2ccnc2c1 | c1ccccc1.c1ccn2ccnc2c1 | HBr.B | O.COCCOC | null | null | CCCN(CCC)c1c(SC)nc2c(Br)cc(C)cn12.OB(O)c1ccc(Cl)cc1Cl>O.COCCOC>CCCN(CCC)c1c(SC)nc2c(-c3ccc(Cl)cc3Cl)cc(C)cn12 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-453e93fc712446deb887ec2ae8b507a1 | CCCN(CC1CC1)c1c(SC)nc2c(-c3ccc(OC)cc3Cl)nccn12.O=C(OO)c1cccc(Cl)c1>>CCCN(CC1CC1)c1c(S(C)=O)nc2c(-c3ccc(OC)cc3Cl)nccn12 | ClC1=CC(=CC=C1)C(=O)OO.ClC1=C(C=CC(=C1)OC)C=1C=2N(C=CN1)C(=C(N2)SC)N(CCC)CC2CC2.S(=S)(=O)([O-])[O-].[Na+].[Na+].C([O-])(O)=O.[Na+]>>ClC1=C(C=CC(=C1)OC)C=1C=2N(C=CN1)C(=C(N2)S(=O)C)N(CCC)CC2CC2 | [CH3:1][CH2:2][CH2:3][N:4]([CH2:5][CH:6]1[CH2:7][CH2:8]1)[c:9]1[c:10]([S:11][CH3:12])[n:14][c:15]2[c:16](-[c:17]3[cH:18][cH:19][c:20]([O:21][CH3:22])[cH:23][c:24]3[Cl:25])[n:26][cH:27][cH:28][n:29]12.O=C(O[OH:13])c1cccc(Cl)c1>>[CH3:1][CH2:2][CH2:3][N:4]([CH2:5][CH:6]1[CH2:7][CH2:8]1)[c:9]1[c:10]([S:11]([CH3:12])=[O:13]... | CCCN(CC1CC1)c1c(SC)nc2c(-c3ccc(OC)cc3Cl)nccn12.O=C(OO)c1cccc(Cl)c1 | CCCN(CC1CC1)c1c(S(C)=O)nc2c(-c3ccc(OC)cc3Cl)nccn12 | null | null | ClCCl | Oxidation | Sulfanyl to sulfinyl_peroxide | 95b5106b07a173d8eafc1c9c8a6c938befe131c3d1caaf5886529b7aee55ea9d | 7652b53bb02130dccfe4b1e8905d7f3db7f05ff3a95a0003c1bab09b1ad4083e | c1ccc(-c2nccn3c(NCC4CC4)cnc23)cc1 | Cl-c1:c:c:c:c(-C(=O)-O-[OH;D1;+0:1]):c:1.[#7:2]-[c:3]1:[#7;a:4]2:[c:5]:[c:6]:[#7;a:7]:[c:8]:[c:9]:2:[#7;a:10]:[c:11]:1-[S;H0;D2;+0:12]-[C;D1;H3:13]>>[#7:2]-[c:3]1:[#7;a:4]2:[c:5]:[c:6]:[#7;a:7]:[c:8]:[c:9]:2:[#7;a:10]:[c:11]:1-[S;H0;D3;+0:12](-[C;D1;H3:13])=[O;H0;D1;+0:1] | 12.2 | [{"value": 12.2, "product": "ClC1=C(C=CC(=C1)OC)C=1C=2N(C=CN1)C(=C(N2)S(=O)C)N(CCC)CC2CC2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 20 | MINUTE | m-chloroperbenzoic acid (148 mg) was added to N-[8-(2-chloro-4-methoxyphenyl)-2-(methylsulfanyl)imidazo[1,2-a]pyrazin-3-yl]-N-cyclopropylmethyl-N-propylamine (166 mg) and dichloromethane (2 mL) at room temperature, and the mixture was stirred for 20 minutes. An aqueous sodium thiosulfate solution and an aqueous sodium ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Peroxide.Monosulfide | Sulfoxide | c1ccccc1 | null | C1CC1.c1ccccc1.c1cn2ccnc2cn1 | HCl | ClCCl | null | 0.333333 | CCCN(CC1CC1)c1c(SC)nc2c(-c3ccc(OC)cc3Cl)nccn12.O=C(OO)c1cccc(Cl)c1>ClCCl>CCCN(CC1CC1)c1c(S(C)=O)nc2c(-c3ccc(OC)cc3Cl)nccn12 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-43306c01351343a7af7f36e0fbd02133 | CCCN(CC1CC1)c1c(S(C)(=O)=O)nc2c(-c3ccc(OC)cc3Cl)nccn12.C[O-]>>CCCN(CC1CC1)c1c(OC)nc2c(-c3ccc(OC)cc3Cl)nccn12 | C[O-].[Na+].ClC1=C(C=CC(=C1)OC)C=1C=2N(C=CN1)C(=C(N2)S(=O)(=O)C)N(CCC)CC2CC2>>ClC1=C(C=CC(=C1)OC)C=1C=2N(C=CN1)C(=C(N2)OC)N(CCC)CC2CC2 | CS(=O)(=O)[c:10]1[c:9]([N:4]([CH2:3][CH2:2][CH3:1])[CH2:5][CH:6]2[CH2:7][CH2:8]2)[n:28]2[c:14]([n:13]1)[c:15](-[c:16]1[cH:17][cH:18][c:19]([O:20][CH3:21])[cH:22][c:23]1[Cl:24])[n:25][cH:26][cH:27]2.[O-:11][CH3:12]>>[CH3:1][CH2:2][CH2:3][N:4]([CH2:5][CH:6]1[CH2:7][CH2:8]1)[c:9]1[c:10]([O:11][CH3:12])[n:13][c:14]2[c:15](... | CCCN(CC1CC1)c1c(S(C)(=O)=O)nc2c(-c3ccc(OC)cc3Cl)nccn12.C[O-] | CCCN(CC1CC1)c1c(OC)nc2c(-c3ccc(OC)cc3Cl)nccn12 | null | null | O | Heteroatom Alkylation and Arylation | OtherReaction | b148c0e9c922e188ff12e3775bf2ce2f392116d80327cd58245aaf623e92a8db | 731c19b65b5c8b40ca2c449bc317006921ded977380fbf4f8e42c4e97b0a736b | c1ccc(-c2nccn3c(NCC4CC4)cnc23)cc1 | C-S(=O)(=O)-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]2:[c:4]:[#7;a:5]:[c:6]:[c:7]:[#7;a:8]:2:[c:9]:1-[#7:10].[C;D1;H3:11]-[O-;H0;D1:12]>>[#7:10]-[c:9]1:[#7;a:8]2:[c:7]:[c:6]:[#7;a:5]:[c:4]:[c:3]:2:[#7;a:2]:[c;H0;D3;+0:1]:1-[O;H0;D2;+0:12]-[C;D1;H3:11] | null | [] | null | null | 6 | HOUR | A 28% sodium methoxide solution (5 mL) was added to N[8-(2-chloro-4-methoxyphenyl)-2-(methylsulfonyl)imidazo[1,2-a]pyrazin-3-yl]-N-cyclopropylmethyl-N-propylamine (80 mg), and the mixture was stirred for 6 hours by heating under ref lux. After cooled to room temperature, water was added thereto, which was extracted wit... | 10.6084/m9.figshare.5104873.v1 | null | Sulfone | Ether | c1cn2ccnc2cn1 | c1cn2ccnc2cn1 | C1CC1.c1ccccc1.c1cn2ccnc2cn1 | HO- | O | null | 6 | CCCN(CC1CC1)c1c(S(C)(=O)=O)nc2c(-c3ccc(OC)cc3Cl)nccn12.C[O-]>O>CCCN(CC1CC1)c1c(OC)nc2c(-c3ccc(OC)cc3Cl)nccn12 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-8705baba14974396902114f7aa4c7592 | COc1ccc(-c2ccnn3c(C(=O)O)c(SC)nc23)c(C)c1.[N-]=[N+]=NP(=O)(c1ccccc1)c1ccccc1>>COc1ccc(-c2ccnn3c(N)c(SC)nc23)c(C)c1 | COC1=CC(=C(C=C1)C=1C=2N(N=CC1)C(=C(N2)SC)C(=O)O)C.C(C)(C)(C)O.C(C)N(CC)CC.C1(=CC=CC=C1)P(=O)(C1=CC=CC=C1)N=[N+]=[N-]>>COC1=CC(=C(C=C1)C=1C=2N(N=CC1)C(=C(N2)SC)N)C | O=C(O)[c:12]1[n:11]2[n:10][cH:9][cH:8][c:7](-[c:6]3[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:21][c:19]3[CH3:20])[c:18]2[n:17][c:14]1[S:15][CH3:16].[N-]=[N+]=[N:13]P(=O)(c1ccccc1)c1ccccc1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][cH:9][n:10][n:11]3[c:12]([NH2:13])[c:14]([S:15][CH3:16])[n:17][c:18]23)[c:19]([CH3:20])[c... | COc1ccc(-c2ccnn3c(C(=O)O)c(SC)nc23)c(C)c1.[N-]=[N+]=NP(=O)(c1ccccc1)c1ccccc1 | COc1ccc(-c2ccnn3c(N)c(SC)nc23)c(C)c1 | null | null | O.C1(=CC=CC=C1)C | Heteroatom Alkylation and Arylation | OtherReaction | 00fed900d6bd21ee71533bf1e36cf69742e05e0a6a646fdb0a4dd1b86bd1391b | c4869b2e15981984090372c3f8725c0a3f1a2d8cd3a4eec59edd04a0d3b2a386 | c1ccc(-c2ccnn3ccnc23)cc1 | O-C(=O)-[c;H0;D3;+0:1]1:[#7;a:2](:[#7;a:3]:[c:4]):[c:5]:[#7;a:6]:[c:7]:1-[#16:8].O=P(-[N;H0;D2;+0:9]=[N+]=[N-])(-c1:c:c:c:c:c:1)-c1:c:c:c:c:c:1>>[#16:8]-[c:7]1:[#7;a:6]:[c:5]:[#7;a:2](:[#7;a:3]:[c:4]):[c;H0;D3;+0:1]:1-[NH2;D1;+0:9] | null | [] | 100 | CELSIUS | 3 | HOUR | The resulting 8-(4-methoxy-2-methylphenyl)-2-(methylsulfanyl)imidazo[1,2-b]pyridazine-3-carboxylic acid was dissolved in toluene (10 mL), then tert-butyl alcohol (10 mL), triethylamine (0.49 mL) and diphenylphosphorylazide (0.38 mL) were added thereto, and the mixture was heated at 100° C. for 4 hours. After completion... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Azide | Primary amine | c1cnn2ccnc2c1.c1ccccc1.c1ccccc1 | c1cnn2ccnc2c1 | c1ccccc1.c1cnn2ccnc2c1 | HO- | O.C1(=CC=CC=C1)C | 100 | 3 | COc1ccc(-c2ccnn3c(C(=O)O)c(SC)nc23)c(C)c1.[N-]=[N+]=NP(=O)(c1ccccc1)c1ccccc1>O.C1(=CC=CC=C1)C>COc1ccc(-c2ccnn3c(N)c(SC)nc23)c(C)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-1b1c1eafe5ed40898117539f0993ce40 | CSc1nc2c(Br)cccn2c1CO>>CSc1nc2c(Br)cccn2c1C | BrC=1C=2N(C=CC1)C(=C(N2)SC)CO>>BrC=1C=2N(C=CC1)C(=C(N2)SC)C | O[CH2:13][c:12]1[c:3]([S:2][CH3:1])[n:4][c:5]2[c:6]([Br:7])[cH:8][cH:9][cH:10][n:11]21>>[CH3:1][S:2][c:3]1[n:4][c:5]2[c:6]([Br:7])[cH:8][cH:9][cH:10][n:11]2[c:12]1[CH3:13] | CSc1nc2c(Br)cccn2c1CO | CSc1nc2c(Br)cccn2c1C | null | [O-2].[Mn+4].[O-2] | CC(=O)C | Reduction | OtherReaction | 1deafbccd34c1d747dea179c0b63e48cd7fc76936d377fecabe099ecef578991 | 0a2c8330040d049ae67653e1474aff520bf8a2d8c908ffd7076f536576936945 | c1ccn2ccnc2c1 | O-[CH2;D2;+0:1]-[c:2]1:[#7;a:3](:[c:4]):[c:5]:[#7;a:6]:[c:7]:1-[#16:8]>>[#16:8]-[c:7]1:[#7;a:6]:[c:5]:[#7;a:3](:[c:4]):[c:2]:1-[CH3;D1;+0:1] | 19.9 | [{"value": 19.9, "product": "BrC=1C=2N(C=CC1)C(=C(N2)SC)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | The resulting [8-bromo-2-(methylsulfanyl)imidazo[1,2-a]pyridin-3-yl]methanol (640 mg) was dissolved in acetone (50 mL), then activated manganese (IV) oxide (4 g) was added thereto, and the mixture was stirred overnight. Manganese (IV) oxide was filtered off through Celite, and the filtrate was evaporated. The resulting... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | null | null | null | c1ccn2ccnc2c1 | Other | [O-2].[Mn+4].[O-2].CC(=O)C | null | 8 | CSc1nc2c(Br)cccn2c1CO>[O-2].[Mn+4].[O-2].CC(=O)C>CSc1nc2c(Br)cccn2c1C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-b5311dc1ba214541b9ac95bbd592e777 | Cc1ccccc1>>Cc1ccccc1 | C1(=CC=CC=C1)C.C1(=CC=CC=C1)C.CS(=O)C.[C@@H]1([C@H](O)[C@H](O)[C@@H](CO)O1)N1C(=O)N=C(N)N=C1.[C@@H]1([C@H](O)[C@H](O)[C@@H](CO)O1)N1C(=O)N=C(N)N=C1.CS(=O)C>>CS(=O)C.C1(=CC=CC=C1)C | [CH3:5][c:6]1[cH:7][cH:8][cH:9][cH:10][cH:11]1>>[CH3:5][c:6]1[cH:7][cH:8][cH:9][cH:10][cH:11]1 | Cc1ccccc1 | Cc1ccccc1 | null | null | null | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | c1ccccc1 | null | null | [] | null | null | null | null | Dimethyl sulfoxide (DMSO) was used as the primary solvent to solubilize Form I of 5-azacytidine and toluene was used as the co-solvent as follows. Approximately 250 mg of 5-azacytidine was dissolved with approximately 5 mL of DMSO, preheated to approximately 90° C., in separate 100-mL beakers. The solids were allowed t... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | c1ccccc1 | null | null | null | null | Cc1ccccc1>>Cc1ccccc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-eb7ccf59255147c7a30549f2cc940748 | FC(F)=C(F)CCBr.N#C[S-]>>N#CSCCC(F)=C(F)F | BrCCC(=C(F)F)F.[S-]C#N.[NH4+]>>FC(CCSC#N)=C(F)F | Br[CH2:4][CH2:5][C:6]([F:7])=[C:8]([F:9])[F:10].[N:1]#[C:2][S-:3]>>[N:1]#[C:2][S:3][CH2:4][CH2:5][C:6]([F:7])=[C:8]([F:9])[F:10] | FC(F)=C(F)CCBr.N#C[S-] | N#CSCCC(F)=C(F)F | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 4f905981579db6f2866cc0ae1b975a1e274bbb1d618959665eb6b8e4dd6684b9 | e26f642c2dc9d150597dcc73347fb476ddd5d717501944aafd09c0558413a369 | null | Br-[CH2;D2;+0:1]-[C:2]-[C:3](-[F;D1;H0:4])=[C:5](-[F;D1;H0:6])-[F;D1;H0:7].[N;D1;H0:8]#[C:9]-[S-;H0;D1:10]>>[F;D1;H0:6]-[C:5](-[F;D1;H0:7])=[C:3](-[F;D1;H0:4])-[C:2]-[CH2;D2;+0:1]-[S;H0;D2;+0:10]-[C:9]#[N;D1;H0:8] | null | [] | null | null | null | null | When, for example, 4-bromo-1,1,2-trifluoro-1-butene and ammonium thiocyanate are used, 3,4,4-trifluoro-3-butenyl thiocyanate is obtained which is then reacted with H2S to give 3,4,4-trifluoro-3-butenyl dithiocarbamate. Further reaction of 3,4,4-trifluoro-3-butenyl dithiocarbamate with chloroacetaldehyde then provides 2... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | Monosulfide | null | null | null | Br- | null | null | null | FC(F)=C(F)CCBr.N#C[S-]>>N#CSCCC(F)=C(F)F |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-56c0a4b08e76451d8ee60e988ae8266a | FC(F)=C(F)CCBr.NC(=S)[S-]>>NC(=S)SCCC(F)=C(F)F | C(N)([S-])=S.[NH4+].BrCCC(=C(F)F)F.C(N)([S-])=S.[NH4+]>>C(N)(SCCC(=C(F)F)F)=S | Br[CH2:5][CH2:6][C:7]([F:8])=[C:9]([F:10])[F:11].[NH2:1][C:2](=[S:3])[S-:4]>>[NH2:1][C:2](=[S:3])[S:4][CH2:5][CH2:6][C:7]([F:8])=[C:9]([F:10])[F:11] | FC(F)=C(F)CCBr.NC(=S)[S-] | NC(=S)SCCC(F)=C(F)F | null | null | C(C)O | Heteroatom Alkylation and Arylation | OtherReaction | 4f905981579db6f2866cc0ae1b975a1e274bbb1d618959665eb6b8e4dd6684b9 | e26f642c2dc9d150597dcc73347fb476ddd5d717501944aafd09c0558413a369 | null | Br-[CH2;D2;+0:1]-[C:2]-[C:3](-[F;D1;H0:4])=[C:5](-[F;D1;H0:6])-[F;D1;H0:7].[N;D1;H2:8]-[C:9](-[S-;H0;D1:10])=[S;D1;H0:11]>>[F;D1;H0:6]-[C:5](-[F;D1;H0:7])=[C:3](-[F;D1;H0:4])-[C:2]-[CH2;D2;+0:1]-[S;H0;D2;+0:10]-[C:9](-[N;D1;H2:8])=[S;D1;H0:11] | null | [] | 40 | CELSIUS | 3 | HOUR | 2.8 g (25 mmol) of ammonium dithiocarbamate in 40 ml of ethanol are admixed dropwise with 5.32 g (26.3 mmol; purity 93.2%) of 4-bromo-1,1,2-trifluoro-1-butene, stirred at 40° C. for 3 h, another 2.8 g of ammonium dithiocarbamate is added after 1 h, and everything is left to stand at room temperature for 8 h. The filtra... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | Monosulfide | null | null | null | Br- | C(C)O | 40 | 3 | FC(F)=C(F)CCBr.NC(=S)[S-]>C(C)O>NC(=S)SCCC(F)=C(F)F |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-2ce8de5ebde34b87b4c5c63a99ff1610 | NC(=S)SCCC(F)=C(F)F>>FC(F)=C(F)CCSc1nccs1 | ClCC=O.C(N)(SCCC(=C(F)F)F)=S.Cl.ClCC=O>>FC(CCSC=1SC=CN1)=C(F)F | [F:1][C:2]([F:3])=[C:4]([F:5])[CH2:6][CH2:7][S:8][C:9]([NH2:10])=[S:13]>>[F:1][C:2]([F:3])=[C:4]([F:5])[CH2:6][CH2:7][S:8][c:9]1[n:10][cH:11][cH:12][s:13]1 | NC(=S)SCCC(F)=C(F)F | FC(F)=C(F)CCSc1nccs1 | null | null | O1CCOCC1 | Aromatic Heterocycle Formation | OtherReaction | 3c75df89637ec99f54296354329f942342c89ae536c3288455dc37b1a7da8616 | c794985a515ce5755267f6637fcb87d41d311c11ef63b51f9b87e88d10f3069c | c1cscn1 | [C:1]-[#16:2]-[C;H0;D3;+0:3](-[NH2;D1;+0:4])=[S;H0;D1;+0:5]>>[C:1]-[#16:2]-[c;H0;D3;+0:3]1:[n;H0;D2;+0:4]:[c:6]:[c:7]:[s;H0;D2;+0:5]:1 | null | [] | null | null | 4 | HOUR | 15.1 g (64.8 mmol; purity 86.3%) of 3,4,4-trifluoro-3-butenyl dithiocarbamate in 100 ml of dioxane are admixed with 0.2 ml of conc. hydrochloric acid and 12.4 g (71.2 mmol) of 45% aqueous chloroacetaldehyde solution. The mixture is boiled for 4 h under argon, and another 1 ml of chloroacetaldehyde solution is added aft... | 10.6084/m9.figshare.5104873.v1 | null | Thioamide | Monosulfide | null | c1cscn1 | c1cscn1 | Other | O1CCOCC1 | null | 4 | NC(=S)SCCC(F)=C(F)F>O1CCOCC1>FC(F)=C(F)CCSc1nccs1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-ee4b179577564cf2a3db73ccda4e6fac | CCOC(CCl)OCC.NC(=S)SCCC(F)=C(F)F>>FC(F)=C(F)CCSc1nccs1 | C(N)(SCCC(=C(F)F)F)=S.C(C)OC(CCl)OCC.O.C1(=CC=C(C=C1)S(=O)(=O)O)C>>FC(CCSC=1SC=CN1)=C(F)F | CCO[CH:11](OCC)[CH2:12]Cl.[F:1][C:2]([F:3])=[C:4]([F:5])[CH2:6][CH2:7][S:8][C:9]([NH2:10])=[S:13]>>[F:1][C:2]([F:3])=[C:4]([F:5])[CH2:6][CH2:7][S:8][c:9]1[n:10][cH:11][cH:12][s:13]1 | CCOC(CCl)OCC.NC(=S)SCCC(F)=C(F)F | FC(F)=C(F)CCSc1nccs1 | null | null | C(C)(=O)O | Aromatic Heterocycle Formation | OtherReaction | 99b4763ff7b16f88720d53459ef736995aaa64d13ca13967d7f53851cba3e9f7 | 42d1ee8bd24936aec7c7b6a0e0cb3c7e317f16436defca54664117f832e663aa | c1cscn1 | C-C-O-[CH;D3;+0:1](-O-C-C)-[CH2;D2;+0:2]-Cl.[C:3]-[#16:4]-[C;H0;D3;+0:5](-[NH2;D1;+0:6])=[S;H0;D1;+0:7]>>[C:3]-[#16:4]-[c;H0;D3;+0:5]1:[n;H0;D2;+0:6]:[cH;D2;+0:1]:[cH;D2;+0:2]:[s;H0;D2;+0:7]:1 | null | [] | 95 | CELSIUS | 1.5 | HOUR | 3 g (14.9 mmol) of 3,4,4-trifluoro-3-butenyl dithiocarbamate in 15 ml of glacial acetic acid are admixed with 2.3 g (15.1 mmol) of chloroacetaldehyde diethyl acetal and 40 mg of p-toluenesulphonic acid monohydrate. The mixture is stirred at 95° C. for 1.5 h and, after cooling to room temperature, is then concentrated b... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ether.Ether.Thioamide.Monosulfide | Monosulfide | null | c1cscn1 | c1cscn1 | HCl | C(C)(=O)O | 95 | 1.5 | CCOC(CCl)OCC.NC(=S)SCCC(F)=C(F)F>C(C)(=O)O>FC(F)=C(F)CCSc1nccs1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-0e5e586dc80948d58ac7c0774a324757 | COc1ccc(CNc2nc(N3CCC[C@H]3CO)ncc2C=O)cc1Cl>>C=C[C@H](CO)c1cnc(N2CCCC2CO)nc1NCc1ccc(OC)c(Cl)c1 | OC[C@H]1N(CCC1)C1=NC=C(C(=N1)NCC1=CC(=C(C=C1)OC)Cl)C=O.C(=C)[Mg]Br.O1CCCC1.O1CCCC1.[Cl-].[NH4+]>>OCC1N(CCC1)C1=NC=C(C(=N1)NCC1=CC(=C(C=C1)OC)Cl)[C@H](C=C)CO | [CH:3](=[O:5])[c:6]1[cH:7][n:8][c:9]([N:10]2[CH2:11][CH2:12][CH2:13][C@H:14]2[CH2:15][OH:16])[n:17][c:18]1[NH:19][CH2:20][c:21]1[cH:22][cH:23][c:24]([O:25][CH3:26])[c:27]([Cl:28])[cH:29]1>>[CH2:1]=[CH:2][C@H:3]([CH2:4][OH:5])[c:6]1[cH:7][n:8][c:9]([N:10]2[CH2:11][CH2:12][CH2:13][CH:14]2[CH2:15][OH:16])[n:17][c:18]1[NH:... | COc1ccc(CNc2nc(N3CCC[C@H]3CO)ncc2C=O)cc1Cl | C=C[C@H](CO)c1cnc(N2CCCC2CO)nc1NCc1ccc(OC)c(Cl)c1 | null | null | null | Miscellaneous | OtherReaction | 155e7013e16dbd44eda1307fb1d28f7a05e58bf69dec69e6af17a470120ea006 | 2e5da6f4774f1c79021a74214574517f5452fdf09afdcef5a464ff4f1128a852 | c1ccc(CNc2ccnc(N3CCCC3)n2)cc1 | [#7:1]-[c:2]1:[#7;a:3]:[c:4]:[#7;a:5]:[c:6]:[c:7]:1-[CH;D2;+0:8]=[O;H0;D1;+0:9]>>[#7:1]-[c:2]1:[#7;a:3]:[c:4]:[#7;a:5]:[c:6]:[c:7]:1-[C@H;D3;+0:8](-[C:10]=[C;D1;H2:11])-[C:12]-[OH;D1;+0:9] | null | [] | 0 | CELSIUS | 1 | HOUR | A solution of (S)-2-(2-hydroxymethyl-1-pyrrolidinyl)-5-formyl-4-(3-chloro-4-methoxybenzylamino)pyrimidine (4.1 g) in tetrahydrofuran (30 ml) is added to a solution of vinyl magnesium bromide in tetrahydrofuran (43.5 ml) at 0° C., and the mixture is stirred at 0° C. for 1 hour. To the mixture is added a saturated aqueou... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | Primary alcohol.Vinyl | null | null | c1cncnc1.C1CC[NH]C1.c1ccccc1 | Other | null | 0 | 1 | COc1ccc(CNc2nc(N3CCC[C@H]3CO)ncc2C=O)cc1Cl>>C=C[C@H](CO)c1cnc(N2CCCC2CO)nc1NCc1ccc(OC)c(Cl)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-e5f8271f05a748aca5b142ffca477532 | CCCc1[nH]cnc1C(=O)OCC>>CCCc1[nH]cnc1C(=O)O | C(C)OC(=O)C=1N=CNC1CCC.Cl>>Cl.C(CC)C1=C(N=CN1)C(=O)O | CC[O:11][C:9]([c:8]1[c:4]([CH2:3][CH2:2][CH3:1])[nH:5][cH:6][n:7]1)=[O:10]>>[CH3:1][CH2:2][CH2:3][c:4]1[nH:5][cH:6][n:7][c:8]1[C:9](=[O:10])[OH:11] | CCCc1[nH]cnc1C(=O)OCC | CCCc1[nH]cnc1C(=O)O | null | null | O | Deprotection | Ester saponification (alkyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1c[nH]cn1 | C-C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4](:[#7;a:5]):[c:6]:[#7;a:7]>>[#7;a:7]:[c:6]:[c:4](-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1]):[#7;a:5] | 100 | [{"value": 100.0, "product": "Cl.C(CC)C1=C(N=CN1)C(=O)O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 24 | HOUR | 5-Propyl-1H-imidazole-4-carboxylic acid ethyl ester 2 (2.00 g; 11.0 mmol) and concentrated aqueous HCl (40 mL) were combined and heated to reflux with stirring for 24 h. After cooling to rt, the light tan solution was diluted with water (100 mL) and extracted with EtOAc. The aqueous layer was then evaporated under redu... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1c[nH]cn1 | Other | O | null | 24 | CCCc1[nH]cnc1C(=O)OCC>O>CCCc1[nH]cnc1C(=O)O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-dc241ef9e78942adaf22ff1337bff403 | CCCc1[nH]cnc1C(=O)O.O=C(Cl)C(=O)Cl>>CCCc1[nH]cnc1C(=O)Cl | Cl.C(CC)C1=C(N=CN1)C(=O)O.C(C(=O)Cl)(=O)Cl>>C(CC)C1=C(N=CN1)C(=O)Cl | O[C:9]([c:8]1[c:4]([CH2:3][CH2:2][CH3:1])[nH:5][cH:6][n:7]1)=[O:10].O=C(Cl)C(=O)[Cl:11]>>[CH3:1][CH2:2][CH2:3][c:4]1[nH:5][cH:6][n:7][c:8]1[C:9](=[O:10])[Cl:11] | CCCc1[nH]cnc1C(=O)O.O=C(Cl)C(=O)Cl | CCCc1[nH]cnc1C(=O)Cl | null | null | null | Functional Group Interconversion | Alcohol to chloride_Other | 013cec2edeb273a7a148f349d36a52d99ff4e7bcf8eed78085df830088e387ac | aedb1f68dc5b7eb0583043e1125b741382b17974140a2f46554f0110e2ddc884 | c1c[nH]cn1 | Cl-C(=O)-C(=O)-[Cl;H0;D1;+0:1].O-[C;H0;D3;+0:2](=[O;D1;H0:3])-[c:4]1:[#7;a:5]:[c:6]:[#7;a:7]:[c:8]:1-[C:9]>>[C:9]-[c:8]1:[#7;a:7]:[c:6]:[#7;a:5]:[c:4]:1-[C;H0;D3;+0:2](-[Cl;H0;D1;+0:1])=[O;D1;H0:3] | 71.1 | [{"value": 71.0, "product": "C(CC)C1=C(N=CN1)C(=O)Cl", "details": "PERCENTYIELD", "is_desired": false}, {"value": 71.1, "product": "C(CC)C1=C(N=CN1)C(=O)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 5-Propyl-1H-imidazole-4-carboxylic acid hydrochloride 3 (1.0 g; 5.3 mmol) was added to nitrogen-purged CH3CN (10 mL). Oxalyl chloride (2.5 ml; 29 mmol) was then added, and the mixture was heated to reflux under N2 for 1 h. The brown solution was then allowed to cool, and the product began to precipitate. Ice-cold dry E... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Acyl halide.Carboxylic acid | Acyl halide | null | null | c1c[nH]cn1 | HCl | null | null | null | CCCc1[nH]cnc1C(=O)O.O=C(Cl)C(=O)Cl>>CCCc1[nH]cnc1C(=O)Cl |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-c5c47ba74d2c4e2f8477997e73d47b11 | CCCc1[nH]c(I)nc1C(=O)NC>>CCCc1[nH]c(-c2nc(C(=O)NC)c(CCC)[nH]2)nc1C(=O)NC | CNC(=O)C=1N=C(NC1CCC)I>>CNC(=O)C=1N=C(NC1CCC)C=1NC(=C(N1)C(=O)NC)CCC | I[c:6]1[nH:5][c:4]([CH2:3][CH2:2][CH3:1])[c:20]([C:10](=[O:11])[NH:12][CH3:13])[n:8]1>>[CH3:1][CH2:2][CH2:3][c:4]1[nH:5][c:6](-[c:7]2[n:8][c:9]([C:10](=[O:11])[NH:12][CH3:13])[c:14]([CH2:15][CH2:16][CH3:17])[nH:18]2)[n:19][c:20]1[C:21](=[O:22])[NH:23][CH3:24] | CCCc1[nH]c(I)nc1C(=O)NC | CCCc1[nH]c(-c2nc(C(=O)NC)c(CCC)[nH]2)nc1C(=O)NC | null | null | CO | Aromatic Heterocycle Formation | OtherReaction | cf1d90069438d2f20a6c3db28aa27e3ffc2ce5318cd39d02979dd772a5545e51 | 75ef3d1db8ed5627cad9f1c04eeb05e1be73f58c43a4d9b45880972cbc9d3ec3 | c1c[nH]c(-c2ncc[nH]2)n1 | I-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3](-[C:4]):[c;H0;D3;+0:5](-[C;H0;D3;+0:6](=[O;D1;H0:7])-[#7:8]-[C;D1;H3:9]):[n;H0;D2;+0:10]:1>>[#7:11]-[C:12](=[O;D1;H0:13])-[c;H0;D3;+0:5]1:[#7;a:14]:[c;H0;D3;+0:1](-[c:15]2:[#7;a:16]:[c:17]:[c:18](-[C;H0;D3;+0:6](=[O;D1;H0:7])-[#7:8]-[C;D1;H3:9]):[n;H0;D2;+0:10]:2):[#7;a:2]:[c:3]:1-[C:4] | 43 | [{"value": 43.0, "product": "CNC(=O)C=1N=C(NC1CCC)C=1NC(=C(N1)C(=O)NC)CCC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 40.1, "product": "CNC(=O)C=1N=C(NC1CCC)C=1NC(=C(N1)C(=O)NC)CCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Iodide 6a (0.35 g; 1.2 mmol) was used as starting material. After cooling to rt, the reaction mixture was diluted with CH3OH and filtered. The filtrate was evaporated under vacuum, and the residue was dissolved in CH2Cl2. Upon standing, a white solid precipitated. This material was collected by filtration and was washe... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amide | Secondary amide.Secondary amide | c1c[nH]cn1 | c1c[nH]cn1.c1c[nH]cn1 | c1c[nH]cn1.c1c[nH]cn1 | I- | CO | null | null | CCCc1[nH]c(I)nc1C(=O)NC>CO>CCCc1[nH]c(-c2nc(C(=O)NC)c(CCC)[nH]2)nc1C(=O)NC |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-0530478446b848d8948fd58216e836f3 | CCCc1[nH]c(I)nc1C(=O)NCc1cc(F)cc(F)c1>>CCCc1[nH]c(-c2nc(C(=O)NCc3cc(F)cc(F)c3)c(CCC)[nH]2)nc1C(=O)NCc1cc(F)cc(F)c1 | FC=1C=C(CNC(=O)C=2N=C(NC2CCC)I)C=C(C1)F>>FC=1C=C(CNC(=O)C=2N=C(NC2CCC)C=2NC(=C(N2)C(=O)NCC2=CC(=CC(=C2)F)F)CCC)C=C(C1)F | I[c:7]1[nH:5][c:4]([CH2:3][CH2:2][CH3:1])[c:28]([C:10](=[O:11])[NH:12][CH2:13][c:14]2[cH:6][c:33]([F:17])[cH:18][c:19]([F:20])[cH:21]2)[n:8]1>>[CH3:1][CH2:2][CH2:3][c:4]1[nH:5][c:6](-[c:7]2[n:8][c:9]([C:10](=[O:11])[NH:12][CH2:13][c:14]3[cH:15][c:16]([F:17])[cH:18][c:19]([F:20])[cH:21]3)[c:22]([CH2:23][CH2:24][CH3:25])... | CCCc1[nH]c(I)nc1C(=O)NCc1cc(F)cc(F)c1 | CCCc1[nH]c(-c2nc(C(=O)NCc3cc(F)cc(F)c3)c(CCC)[nH]2)nc1C(=O)NCc1cc(F)cc(F)c1 | null | null | CO | Aromatic Heterocycle Formation | OtherReaction | cff40fbdd314028511f4604655acaaf7b0df6b4cf2cd2bce957aa6cbea338c87 | 28393239e30c0319b195347defa439702c27770d21b5c3de4f0075a7ffe10e1d | O=C(NCc1ccccc1)c1c[nH]c(-c2nc(C(=O)NCc3ccccc3)c[nH]2)n1 | I-[c;H0;D3;+0:1]1:[n;H0;D2;+0:2]:[c;H0;D3;+0:3](-[C;H0;D3;+0:4](=[O;D1;H0:5])-[#7:6]-[C:7]-[c;H0;D3;+0:8]2:[c:9]:[c:10](-[F;D1;H0:11]):[cH;D2;+0:12]:[c;H0;D3;+0:13](-[F;H0;D1;+0:14]):[cH;D2;+0:15]:2):[c:16](-[C:17]):[nH;D2;+0:18]:1>>[C:17]-[c:16]1:[nH;D2;+0:18]:[c;H0;D3;+0:15](-[c;H0;D3;+0:1]2:[#7;a:19]:[c:20]:[c:21](-... | 40 | [{"value": 40.0, "product": "FC=1C=C(CNC(=O)C=2N=C(NC2CCC)C=2NC(=C(N2)C(=O)NCC2=CC(=CC(=C2)F)F)CCC)C=C(C1)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 39.2, "product": "FC=1C=C(CNC(=O)C=2N=C(NC2CCC)C=2NC(=C(N2)C(=O)NCC2=CC(=CC(=C2)F)F)CCC)C=C(C1)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": f... | null | null | null | null | Iodide 6b (0.44 g; 1.1 mmol) was used as starting material. After cooling to rt, the reaction mixture was diluted with CH3OH and filtered. The filtrate was evaporated under vacuum, and the residue was dissolved in CHCl3. Slow addition of CH3CN caused a brown solid to precipitate. This material was collected by filtrati... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Secondary amide | Aromatic halide.Aromatic halide.Aromatic halide.Secondary amide.Secondary amide | c1c[nH]cn1.c1ccccc1 | c1c[nH]cn1.c1c[nH]cn1.c1ccccc1.c1ccccc1 | c1c[nH]cn1.c1c[nH]cn1.c1ccccc1.c1ccccc1 | I- | CO | null | null | CCCc1[nH]c(I)nc1C(=O)NCc1cc(F)cc(F)c1>CO>CCCc1[nH]c(-c2nc(C(=O)NCc3cc(F)cc(F)c3)c(CCC)[nH]2)nc1C(=O)NCc1cc(F)cc(F)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-3c49c3434b894b6baf6695c4233a0826 | CCCc1[nH]c(I)nc1C(=O)NCc1ccc(C)cc1>>CCCc1[nH]c(-c2nc(C(=O)NCc3ccc(C)cc3)c(CCC)[nH]2)nc1C(=O)NCc1ccc(C)cc1 | CC1=CC=C(CNC(=O)C=2N=C(NC2CCC)I)C=C1>>CC1=CC=C(CNC(=O)C=2N=C(NC2CCC)C=2NC(=C(N2)C(=O)NCC2=CC=C(C=C2)C)CCC)C=C1 | I[c:7]1[nH:5][c:4]([CH2:3][CH2:2][CH3:1])[c:27]([C:10](=[O:11])[NH:12][CH2:13][c:14]2[cH:6][cH:16][c:17]([CH3:18])[cH:19][cH:20]2)[n:8]1>>[CH3:1][CH2:2][CH2:3][c:4]1[nH:5][c:6](-[c:7]2[n:8][c:9]([C:10](=[O:11])[NH:12][CH2:13][c:14]3[cH:15][cH:16][c:17]([CH3:18])[cH:19][cH:20]3)[c:21]([CH2:22][CH2:23][CH3:24])[nH:25]2)[... | CCCc1[nH]c(I)nc1C(=O)NCc1ccc(C)cc1 | CCCc1[nH]c(-c2nc(C(=O)NCc3ccc(C)cc3)c(CCC)[nH]2)nc1C(=O)NCc1ccc(C)cc1 | null | null | CO | Aromatic Heterocycle Formation | OtherReaction | cd8f9849305f10187a62b17e80cb088e7ea2eb0c51b2f0b25cbf9ed71b37c27b | 75ef3d1db8ed5627cad9f1c04eeb05e1be73f58c43a4d9b45880972cbc9d3ec3 | O=C(NCc1ccccc1)c1c[nH]c(-c2nc(C(=O)NCc3ccccc3)c[nH]2)n1 | I-[c;H0;D3;+0:1]1:[n;H0;D2;+0:2]:[c;H0;D3;+0:3](-[C;H0;D3;+0:4](=[O;D1;H0:5])-[#7:6]-[C:7]-[c;H0;D3;+0:8]2:[c:9]:[c:10]:[c:11](-[C;D1;H3:12]):[cH;D2;+0:13]:[cH;D2;+0:14]:2):[c:15](-[C:16]):[nH;D2;+0:17]:1>>[#7:18]-[C:19](=[O;D1;H0:20])-[c;H0;D3;+0:3]1:[#7;a:21]:[c;H0;D3;+0:14](-[c;H0;D3;+0:1]2:[#7;a:22]:[c:23]:[c:24](-... | 97.5 | [{"value": 38.0, "product": "CC1=CC=C(CNC(=O)C=2N=C(NC2CCC)C=2NC(=C(N2)C(=O)NCC2=CC=C(C=C2)C)CCC)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 97.5, "product": "CC1=CC=C(CNC(=O)C=2N=C(NC2CCC)C=2NC(=C(N2)C(=O)NCC2=CC=C(C=C2)C)CCC)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Iodide 6c (0.45 g; 1.2 mmol) was used as starting material. After cooling to rt, the reaction mixture was diluted with CH3OH and filtered. The filtrate was evaporated under vacuum, and the residue was triturated with CH3CN. The solid that remained undissolved was collected by filtration and washed with CH3CN to afford ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amide | Secondary amide.Secondary amide | c1c[nH]cn1.c1ccccc1 | c1c[nH]cn1.c1c[nH]cn1.c1ccccc1.c1ccccc1 | c1c[nH]cn1.c1c[nH]cn1.c1ccccc1.c1ccccc1 | I- | CO | null | null | CCCc1[nH]c(I)nc1C(=O)NCc1ccc(C)cc1>CO>CCCc1[nH]c(-c2nc(C(=O)NCc3ccc(C)cc3)c(CCC)[nH]2)nc1C(=O)NCc1ccc(C)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-d2419e508c674da0968fc6df07f52955 | CCCCCCNC(=O)c1nc(I)[nH]c1CCC>>CCCCCCNC(=O)c1nc(-c2nc(C(=O)NCCCCCC)c(CCC)[nH]2)[nH]c1CCC | C(CCCCC)NC(=O)C=1N=C(NC1CCC)I>>C(CCCCC)NC(=O)C=1N=C(NC1CCC)C=1NC(=C(N1)C(=O)NCCCCCC)CCC | I[c:12]1[n:7][c:10]([C:8](=[O:9])[NH:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:1])[c:31]([CH2:32][CH2:33][CH3:34])[nH:30]1>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][NH:7][C:8](=[O:9])[c:10]1[n:11][c:12](-[c:13]2[n:14][c:15]([C:16](=[O:17])[NH:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[c:25]([CH2:26][C... | CCCCCCNC(=O)c1nc(I)[nH]c1CCC | CCCCCCNC(=O)c1nc(-c2nc(C(=O)NCCCCCC)c(CCC)[nH]2)[nH]c1CCC | null | null | CO | Aromatic Heterocycle Formation | OtherReaction | cf1d90069438d2f20a6c3db28aa27e3ffc2ce5318cd39d02979dd772a5545e51 | 75ef3d1db8ed5627cad9f1c04eeb05e1be73f58c43a4d9b45880972cbc9d3ec3 | c1c[nH]c(-c2ncc[nH]2)n1 | I-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3](-[C:4]):[c;H0;D3;+0:5](-[C;H0;D3;+0:6](=[O;D1;H0:7])-[NH;D2;+0:8]-[C:9]-[C:10]-[C:11]-[C:12]-[CH2;D2;+0:13]-[CH3;D1;+0:14]):[n;H0;D2;+0:15]:1>>[#7;a:16]:[c:17](-[c;H0;D3;+0:1]1:[#7;a:18]:[c;H0;D3;+0:5](-[C;H0;D3;+0:6](=[O;D1;H0:7])-[NH;D2;+0:15]-[C:19]-[C:20]):[c:3](-[C:4]):[#7;a:2]:1):... | 46.2 | [{"value": 45.0, "product": "C(CCCCC)NC(=O)C=1N=C(NC1CCC)C=1NC(=C(N1)C(=O)NCCCCCC)CCC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 46.2, "product": "C(CCCCC)NC(=O)C=1N=C(NC1CCC)C=1NC(=C(N1)C(=O)NCCCCCC)CCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Iodide 6d (0.45 g; 1.1 mmol) was used as starting material. After cooling to rt, the reaction mixture was diluted with CH3OH and filtered. The filtrate was evaporated under vacuum, and the residue was recrystallized from CH3OH to afford 0.12 g (45%) of 1d as a white solid. mp>260 C; TLC (CH2Cl2-EtOAc, 1:1): Rf=0.51; 1H... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amide | Secondary amide.Secondary amide | c1c[nH]cn1 | c1c[nH]cn1.c1c[nH]cn1 | c1c[nH]cn1.c1c[nH]cn1 | I- | CO | null | null | CCCCCCNC(=O)c1nc(I)[nH]c1CCC>CO>CCCCCCNC(=O)c1nc(-c2nc(C(=O)NCCCCCC)c(CCC)[nH]2)[nH]c1CCC |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-caba9355756548b0a75c50b05894c6a7 | CCCc1[nH]c(I)nc1C(=O)NCCCOC>>CCCc1[nH]c(-c2nc(C(=O)NCCCOC)c(CCC)[nH]2)nc1C(=O)NCCCOC | COCCCNC(=O)C=1N=C(NC1CCC)I>>COCCCNC(=O)C=1N=C(NC1CCC)C=1NC(=C(N1)C(=O)NCCCOC)CCC | I[c:6]1[nH:5][c:4]([CH2:3][CH2:2][CH3:1])[c:24]([C:25](=[O:11])[NH:27][CH2:28][CH2:29][CH2:30][O:31][CH3:32])[n:8]1>>[CH3:1][CH2:2][CH2:3][c:4]1[nH:5][c:6](-[c:7]2[n:8][c:9]([C:10](=[O:11])[NH:12][CH2:13][CH2:14][CH2:15][O:16][CH3:17])[c:18]([CH2:19][CH2:20][CH3:21])[nH:22]2)[n:23][c:24]1[C:25](=[O:26])[NH:27][CH2:28][... | CCCc1[nH]c(I)nc1C(=O)NCCCOC | CCCc1[nH]c(-c2nc(C(=O)NCCCOC)c(CCC)[nH]2)nc1C(=O)NCCCOC | null | null | CO | Aromatic Heterocycle Formation | OtherReaction | 26a5c7af5a9622d67ebeeec655718957946a08ae3f1b634d9ccb4d435f86813a | 4d88ea68dd05fb8223fde8371077f4656c83c406ef12a864fa6252b2c1c92346 | c1c[nH]c(-c2ncc[nH]2)n1 | I-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3](-[C:4]):[c;H0;D3;+0:5](-[C;H0;D3;+0:6](=[O;H0;D1;+0:7])-[#7:8]-[C:9]):[n;H0;D2;+0:10]:1>>[#7:11]-[C:12](=[O;H0;D1;+0:7])-[c:13]1:[c:14]:[#7;a:15]:[c:16](-[c;H0;D3;+0:1]2:[#7;a:17]:[c;H0;D3;+0:5](-[C;H0;D3;+0:6](=[O;D1;H0:18])-[#7:8]-[C:9]):[c:3](-[C:4]):[#7;a:2]:2):[n;H0;D2;+0:10]:1 | 36.2 | [{"value": 33.0, "product": "COCCCNC(=O)C=1N=C(NC1CCC)C=1NC(=C(N1)C(=O)NCCCOC)CCC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 36.2, "product": "COCCCNC(=O)C=1N=C(NC1CCC)C=1NC(=C(N1)C(=O)NCCCOC)CCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Iodide 6e (0.55 g; 1.6 mmol) was used as starting material. After cooling to rt, the reaction mixture was diluted with CH3OH and filtered. The filtrate was evaporated under vacuum, and the residue was recrystallized from EtOAc to afford 0.13 g (33%) of 1e as colorless prisms. mp>260 C; TLC (EtOAc): Rf=0.31; 1H NMR (CDC... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amide | Ether.Secondary amide.Secondary amide | c1c[nH]cn1 | c1c[nH]cn1.c1c[nH]cn1 | c1c[nH]cn1.c1c[nH]cn1 | I- | CO | null | null | CCCc1[nH]c(I)nc1C(=O)NCCCOC>CO>CCCc1[nH]c(-c2nc(C(=O)NCCCOC)c(CCC)[nH]2)nc1C(=O)NCCCOC |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-1471d6ffb8994112af60f9816c4686ad | CCCc1[nH]c(I)nc1C(=O)N1CCCC1>>CCCc1[nH]c(-c2nc(C(=O)N3CCCC3)c(CCC)[nH]2)nc1C(=O)N1CCCC1 | IC=1NC(=C(N1)C(=O)N1CCCC1)CCC>>C(CC)C1=C(N=C(N1)C=1NC(=C(N1)C(=O)N1CCCC1)CCC)C(=O)N1CCCC1 | I[c:6]1[nH:5][c:4]([CH2:3][CH2:2][CH3:1])[c:23]([C:10](=[O:11])[N:12]2[CH2:7][CH2:14][CH2:15][CH2:16]2)[n:8]1>>[CH3:1][CH2:2][CH2:3][c:4]1[nH:5][c:6](-[c:7]2[n:8][c:9]([C:10](=[O:11])[N:12]3[CH2:13][CH2:14][CH2:15][CH2:16]3)[c:17]([CH2:18][CH2:19][CH3:20])[nH:21]2)[n:22][c:23]1[C:24](=[O:25])[N:26]1[CH2:27][CH2:28][CH2... | CCCc1[nH]c(I)nc1C(=O)N1CCCC1 | CCCc1[nH]c(-c2nc(C(=O)N3CCCC3)c(CCC)[nH]2)nc1C(=O)N1CCCC1 | null | null | CO | Aromatic Heterocycle Formation | OtherReaction | b19d816bdadaa0452545a7bf101eb5b5fec54720ee6b6e7ab221b1b3f69f7e03 | 03a4c0e057232c9f8ddafedbd062feb799e61aa63113f7c9543c725ec07158be | O=C(c1c[nH]c(-c2nc(C(=O)N3CCCC3)c[nH]2)n1)N1CCCC1 | I-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3](-[C:4]):[c;H0;D3;+0:5](-[C;H0;D3;+0:6](=[O;D1;H0:7])-[N;H0;D3;+0:8]2-[C:9]-[C:10]-[CH2;D2;+0:11]-[CH2;D2;+0:12]-2):[n;H0;D2;+0:13]:1>>[#7:14]-[C:15](=[O;D1;H0:16])-[c;H0;D3;+0:5]1:[#7;a:17]:[c;H0;D3;+0:1](-[c;H0;D3;+0:12]2:[#7;a:18]:[c:19]:[c:20](-[C;H0;D3;+0:6](=[O;D1;H0:7])-[N;H0;D3;+... | 38.8 | [{"value": 38.0, "product": "C(CC)C1=C(N=C(N1)C=1NC(=C(N1)C(=O)N1CCCC1)CCC)C(=O)N1CCCC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 38.8, "product": "C(CC)C1=C(N=C(N1)C=1NC(=C(N1)C(=O)N1CCCC1)CCC)C(=O)N1CCCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Iodide 6f (0.34 g; 1.0 mmol) was used as starting material. After cooling to rt, the reaction mixture was diluted with CH3OH and filtered. The filtrate was evaporated under vacuum, and the residue was recrystallized from CH3OH to afford 0.080 g (38%) of 1f as yellow prisms. mp>260 C; TLC (EtOAc): Rf=0.14; 1H NMR (DMSO-... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Tertiary amide | Tertiary amide.Tertiary amide | c1c[nH]cn1.C1CC[NH]C1 | c1c[nH]cn1.c1c[nH]cn1.C1CC[NH]C1.C1CC[NH]C1 | c1c[nH]cn1.c1c[nH]cn1.C1CC[NH]C1.C1CC[NH]C1 | I- | CO | null | null | CCCc1[nH]c(I)nc1C(=O)N1CCCC1>CO>CCCc1[nH]c(-c2nc(C(=O)N3CCCC3)c(CCC)[nH]2)nc1C(=O)N1CCCC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-f4e0a65a32994fa48f9d8ab4994782e3 | CC(C)(C)OC(=O)NCCOCCO.CS(=O)(=O)Cl>>CC(C)(C)OC(=O)NCCOCCOS(C)(=O)=O | OCCOCCNC(OC(C)(C)C)=O.C(C)N(CC)CC.CS(=O)(=O)Cl>>CS(=O)(=O)OCCOCCNC(=O)OC(C)(C)C | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][CH2:9][CH2:10][O:11][CH2:12][CH2:13][OH:14].Cl[S:15]([CH3:16])(=[O:17])=[O:18]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][CH2:9][CH2:10][O:11][CH2:12][CH2:13][O:14][S:15]([CH3:16])(=[O:17])=[O:18] | CC(C)(C)OC(=O)NCCOCCO.CS(=O)(=O)Cl | CC(C)(C)OC(=O)NCCOCCOS(C)(=O)=O | null | null | C(Cl)Cl | Acylation | Formation of Sulfonic Esters | 2fa969eb2c954bb96793348a1b2335ec63fbd290dadec6e3e02295e1768e64cf | cb77b899e4adf980b1def97230ef2861660fd7f9602260ec64747d9afd3a795a | null | Cl-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4].[C:5]-[C:6]-[OH;D1;+0:7]>>[C:5]-[C:6]-[O;H0;D2;+0:7]-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4] | 97.4 | [{"value": 97.4, "product": "CS(=O)(=O)OCCOCCNC(=O)OC(C)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 22 | HOUR | A rapidly stirred solution of tert-butyl 2-(2-hydroxyethoxy)ethylcarbamate (47.1 g, 0.230 mol) in 1 L of anhydrous CH2Cl2 was cooled to 0° C. under N2 and treated with triethylamine (48.0 mL, 0.345 mol). Methanesulfonyl chloride (19.6 mL, 0.253 mol) was then added dropwise over 30 min. The reaction mixture was then all... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Sulfonyl halide | Mesylate | null | null | null | HCl | C(Cl)Cl | null | 22 | CC(C)(C)OC(=O)NCCOCCO.CS(=O)(=O)Cl>C(Cl)Cl>CC(C)(C)OC(=O)NCCOCCOS(C)(=O)=O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-38d8fd0ae2e647af882a24d804a170c3 | CC(C)(C)OC(=O)NCCOCCOS(C)(=O)=O.[N-]=[N+]=[N-]>>CC(C)(C)OC(=O)NCCOCCN=[N+]=[N-] | O.CS(=O)(=O)OCCOCCNC(=O)OC(C)(C)C.[N-]=[N+]=[N-].[Na+]>>N(=[N+]=[N-])CCOCCNC(OC(C)(C)C)=O | CS(=O)(=O)O[CH2:13][CH2:12][O:11][CH2:10][CH2:9][NH:8][C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7].[N-:14]=[N+:15]=[N-:16]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][CH2:9][CH2:10][O:11][CH2:12][CH2:13][N:14]=[N+:15]=[N-:16] | CC(C)(C)OC(=O)NCCOCCOS(C)(=O)=O.[N-]=[N+]=[N-] | CC(C)(C)OC(=O)NCCOCCN=[N+]=[N-] | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | OtherReaction | 341eb24906c58cd9cfdeec13febaf0724780d7854e6b6d7ec703218c4bcbe27b | 5f2cb2b9819a73a6855f5277f7fe9d5ce3871340baaebb59d42e38e1ca145c0a | null | C-S(=O)(=O)-O-[CH2;D2;+0:1]-[C:2]-[#8:3].[N-;H0;D1:4]=[#7;+:5]=[N;-;D1;H0:6]>>[#8:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D2;+0:4]=[#7;+:5]=[N;-;D1;H0:6] | 100.8 | [{"value": 100.8, "product": "N(=[N+]=[N-])CCOCCNC(OC(C)(C)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 90 | CELSIUS | 5 | HOUR | A stirred solution of 2-{2-[(tert-butoxycarbonyl)amino]ethoxy}ethyl methanesulfonate (63.5 g, 0.224 mol) in 400 mL of N,N-dimethylformamide (DMF) was treated with NaN3 (16.1 g, 0.247 mol) and the reaction mixture was heated to 90° C. under N2. After 5 h, the solution was cooled to room temperature and treated with 500 ... | 10.6084/m9.figshare.5104873.v1 | null | Mesylate | Azide | null | null | null | MsOH.HO- | CN(C=O)C | 90 | 5 | CC(C)(C)OC(=O)NCCOCCOS(C)(=O)=O.[N-]=[N+]=[N-]>CN(C=O)C>CC(C)(C)OC(=O)NCCOCCN=[N+]=[N-] |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-31b7aba47286438e835babc150ae9da8 | CC(C)(C)OC(=O)NCCOCCN=[N+]=[N-]>>CC(C)(C)OC(=O)NCCOCCN | N(=[N+]=[N-])CCOCCNC(OC(C)(C)C)=O>>NCCOCCNC(OC(C)(C)C)=O | [N-]=[N+]=[N:14][CH2:13][CH2:12][O:11][CH2:10][CH2:9][NH:8][C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][CH2:9][CH2:10][O:11][CH2:12][CH2:13][NH2:14] | CC(C)(C)OC(=O)NCCOCCN=[N+]=[N-] | CC(C)(C)OC(=O)NCCOCCN | null | [Pd] | CO | Reduction | Azide to amine reduction (Staudinger) | 4c9e4990dae2bb965dec06bd45e318560989ee3681b61e443f7aa363b7cfa222 | cd009d687d606bf351eac9390a176d16be38f2c8216a599b398641009c215027 | null | [C:1]-[C:2]-[N;H0;D2;+0:3]=[N+]=[N-]>>[C:1]-[C:2]-[NH2;D1;+0:3] | 84.7 | [{"value": 84.7, "product": "NCCOCCNC(OC(C)(C)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 24 | HOUR | A solution of tert-butyl 2-(2-azidoethoxy)ethylcarbamate (47.0 g, 0.204 mol) in MeOH was treated with 4 g of 10% Pd on carbon and shaken under H2 (3 Kg/cm2) for 24 h. The solution was then filtered through a Celite pad and concentrated to give 35.3 g of crude tert-butyl 2-(2-aminoethoxy)ethylcarbamate as a colorless li... | 10.6084/m9.figshare.5104873.v1 | null | Azide | Primary amine | null | null | null | Other | [Pd].CO | null | 24 | CC(C)(C)OC(=O)NCCOCCN=[N+]=[N-]>[Pd].CO>CC(C)(C)OC(=O)NCCOCCN |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-76cccbeb34944a19aefdb50e87f8a8b2 | CC(C)(C)OC(=O)NCCOCCN.O=[N+]([O-])c1cnc2ccccc2c1Cl>>CC(C)(C)OC(=O)NCCOCCNc1c([N+](=O)[O-])cnc2ccccc12 | ClC1=C(C=NC2=CC=CC=C12)[N+](=O)[O-].C(C)N(CC)CC.NCCOCCNC(OC(C)(C)C)=O>>[N+](=O)([O-])C=1C=NC2=CC=CC=C2C1NCCOCCNC(OC(C)(C)C)=O | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][CH2:9][CH2:10][O:11][CH2:12][CH2:13][NH2:14].Cl[c:15]1[c:16]([N+:17](=[O:18])[O-:19])[cH:20][n:21][c:22]2[cH:23][cH:24][cH:25][cH:26][c:27]12>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][CH2:9][CH2:10][O:11][CH2:12][CH2:13][NH:14][c:15]1[c:16]([N+:17](=[... | CC(C)(C)OC(=O)NCCOCCN.O=[N+]([O-])c1cnc2ccccc2c1Cl | CC(C)(C)OC(=O)NCCOCCNc1c([N+](=O)[O-])cnc2ccccc12 | null | null | C(Cl)Cl | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | 45e8470a78418ade39424f40732aa5ecf6717a7e5d47830a67429c5970ebd551 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc2ncccc2c1 | Cl-[c;H0;D3;+0:1]1:[c:2](-[#7;+:3]):[c:4]:[#7;a:5]:[c:6](:[c:7]):[c:8]:1:[c:9].[C:10]-[C:11]-[NH2;D1;+0:12]>>[#7;+:3]-[c:2]1:[c:4]:[#7;a:5]:[c:6](:[c:7]):[c:8](:[c:9]):[c;H0;D3;+0:1]:1-[NH;D2;+0:12]-[C:11]-[C:10] | 76.7 | [{"value": 76.7, "product": "[N+](=O)([O-])C=1C=NC2=CC=CC=C2C1NCCOCCNC(OC(C)(C)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | A stirred solution of 4-chloro-3-nitroquinoline (31.4 g, 0.151 mol) in 500 mL of anhydrous CH2Cl2, under N2, was treated with triethylamine (43 mL, 0.308 mol) and tert-butyl 2-(2-aminoethoxy)ethylcarbamate (0.151 mol). After stirring overnight, the reaction mixture was washed with H2O (2×300 mL) and brine (300 mL). The... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccc2ncccc2c1 | c1ccc2ncccc2c1 | c1ccc2ncccc2c1 | HCl | C(Cl)Cl | null | 8 | CC(C)(C)OC(=O)NCCOCCN.O=[N+]([O-])c1cnc2ccccc2c1Cl>C(Cl)Cl>CC(C)(C)OC(=O)NCCOCCNc1c([N+](=O)[O-])cnc2ccccc12 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-ffc2f0b837a140e68c0db5793f01c784 | CC(C)(C)OC(=O)NCCOCCNc1c([N+](=O)[O-])cnc2ccccc12>>CC(C)(C)OC(=O)NCCOCCNc1c(N)cnc2ccccc12 | [N+](=O)([O-])C=1C=NC2=CC=CC=C2C1NCCOCCNC(OC(C)(C)C)=O>>NC=1C=NC2=CC=CC=C2C1NCCOCCNC(OC(C)(C)C)=O | O=[N+:17]([O-])[c:16]1[c:15]([NH:14][CH2:13][CH2:12][O:11][CH2:10][CH2:9][NH:8][C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[c:25]2[c:20]([n:19][cH:18]1)[cH:21][cH:22][cH:23][cH:24]2>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][CH2:9][CH2:10][O:11][CH2:12][CH2:13][NH:14][c:15]1[c:16]([NH2:17])[cH:18][n:1... | CC(C)(C)OC(=O)NCCOCCNc1c([N+](=O)[O-])cnc2ccccc12 | CC(C)(C)OC(=O)NCCOCCNc1c(N)cnc2ccccc12 | null | [Pt] | C1(=CC=CC=C1)C | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccc2ncccc2c1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]:[#7;a:5]:[c:6]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4]:[#7;a:5]:[c:6] | 99.9 | [{"value": 99.9, "product": "NC=1C=NC2=CC=CC=C2C1NCCOCCNC(OC(C)(C)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 24 | HOUR | A solution of tert-butyl 2-{2-[(3-nitroquinolin-4-yl)amino]ethoxy}ethylcarbamate (7.52 g, 20.0 mmol) in toluene was treated with 1.5 g of 5% Pt on carbon and shaken under H2 (3 Kg/cm2) for 24 h. The solution was then filtered through a Celite pad and concentrated to give 6.92 g of crude tert-butyl 2-{2-[(3-aminoquinoli... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccc2ncccc2c1 | Other | [Pt].C1(=CC=CC=C1)C | null | 24 | CC(C)(C)OC(=O)NCCOCCNc1c([N+](=O)[O-])cnc2ccccc12>[Pt].C1(=CC=CC=C1)C>CC(C)(C)OC(=O)NCCOCCNc1c(N)cnc2ccccc12 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-9efc1cb544b0485cad9fea828694f51d | CC(C)(C)OC(=O)NCCOCCNc1c(N)cnc2ccccc12.COCCC(=O)Cl>>COCCc1nc2cnc3ccccc3c2n1CCOCCNC(=O)OC(C)(C)C | C.COCCC(=O)Cl.C(C)N(CC)CC.NC=1C=NC2=CC=CC=C2C1NCCOCCNC(OC(C)(C)C)=O.C(C)N(CC)CC>>COCCC=1N(C2=C(C=NC=3C=CC=CC23)N1)CCOCCNC(OC(C)(C)C)=O | [NH2:6][c:7]1[cH:8][n:9][c:10]2[cH:11][cH:12][cH:13][cH:14][c:15]2[c:16]1[NH:17][CH2:18][CH2:19][O:20][CH2:21][CH2:22][NH:23][C:24](=[O:25])[O:26][C:27]([CH3:28])([CH3:29])[CH3:30].O=[C:5](Cl)[CH2:4][CH2:3][O:2][CH3:1]>>[CH3:1][O:2][CH2:3][CH2:4][c:5]1[n:6][c:7]2[cH:8][n:9][c:10]3[cH:11][cH:12][cH:13][cH:14][c:15]3[c:1... | CC(C)(C)OC(=O)NCCOCCNc1c(N)cnc2ccccc12.COCCC(=O)Cl | COCCc1nc2cnc3ccccc3c2n1CCOCCNC(=O)OC(C)(C)C | null | null | CO.C(Cl)Cl.CCO | Aromatic Heterocycle Formation | OtherReaction | 2849961f1d737a23d71906fe74b0976730547255ac052bf4a7367ba2be72dd8e | 56ef83dfadec35a1cf1db968b807e178cc4924ce15bf36d774883783cef0f450 | c1ccc2c(c1)ncc1nc[nH]c12 | Cl-[C;H0;D3;+0:1](=O)-[C:2]-[C:3].[C:4]-[C:5]-[NH;D2;+0:6]-[c:7]1:[c:8]:[c:9]:[#7;a:10]:[c:11]:[c:12]:1-[NH2;D1;+0:13]>>[C:4]-[C:5]-[n;H0;D3;+0:6]1:[c:7]2:[c:8]:[c:9]:[#7;a:10]:[c:11]:[c:12]:2:[n;H0;D2;+0:13]:[c;H0;D3;+0:1]:1-[C:2]-[C:3] | 90.8 | [{"value": 90.8, "product": "COCCC=1N(C2=C(C=NC=3C=CC=CC23)N1)CCOCCNC(OC(C)(C)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | A solution of tert-butyl 2-{2-[(3-aminoquinolin-4-yl)amino]ethoxy}ethylcarbamate (10.2 g, 29.5 mmol) in 250 mL of anhydrous CH2Cl2 was cooled to 0° C. and treated with triethylamine (4.18 mL, 30.0 mmol). Methoxypropionyl chloride (3.30 mL, 30.3 mmol) was then added dropwise over 5 min. The reaction was then warmed to r... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine.Secondary amine | null | c1ccc2ncccc2c1 | c1nc2c(cnc3ccccc32)[nH]1 | c1nc2c(cnc3ccccc32)[nH]1 | HCl | CO.C(Cl)Cl.CCO | null | 1 | CC(C)(C)OC(=O)NCCOCCNc1c(N)cnc2ccccc12.COCCC(=O)Cl>CO.C(Cl)Cl.CCO>COCCc1nc2cnc3ccccc3c2n1CCOCCNC(=O)OC(C)(C)C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-5e6401fdcebf46d7b3a9fcdfea78a3c4 | COCCc1nc2cnc3ccccc3c2n1CCOCCNC(=O)OC(C)(C)C.O=C(OO)c1cccc(Cl)c1>>COCCc1nc2c[n+]([O-])c3ccccc3c2n1CCOCCNC(=O)OC(C)(C)C | COCCC=1N(C2=C(C=NC=3C=CC=CC23)N1)CCOCCNC(OC(C)(C)C)=O.ClC=1C=C(C(=O)OO)C=CC1>>COCCC=1N(C2=C(C=[N+](C=3C=CC=CC23)[O-])N1)CCOCCNC(OC(C)(C)C)=O | [CH3:1][O:2][CH2:3][CH2:4][c:5]1[n:6][c:7]2[cH:8][n:9][c:11]3[cH:12][cH:13][cH:14][cH:15][c:16]3[c:17]2[n:18]1[CH2:19][CH2:20][O:21][CH2:22][CH2:23][NH:24][C:25](=[O:26])[O:27][C:28]([CH3:29])([CH3:30])[CH3:31].O=C(O[OH:10])c1cccc(Cl)c1>>[CH3:1][O:2][CH2:3][CH2:4][c:5]1[n:6][c:7]2[cH:8][n+:9]([O-:10])[c:11]3[cH:12][cH:... | COCCc1nc2cnc3ccccc3c2n1CCOCCNC(=O)OC(C)(C)C.O=C(OO)c1cccc(Cl)c1 | COCCc1nc2c[n+]([O-])c3ccccc3c2n1CCOCCNC(=O)OC(C)(C)C | null | null | C(Cl)(Cl)Cl | Miscellaneous | OtherReaction | 86abb75bf448eea8ddd78de30fcfc7b06bb61e46f725af6f1625e0dd9537993c | 98b338a9d01476c0929fd5672e7509121bfe69600fd72e4d1cc6f1782e2d05d9 | c1ccc2c(c1)[nH+]cc1nc[nH]c12 | Cl-c1:c:c:c:c(-C(=O)-O-[OH;D1;+0:1]):c:1.[c:2]:[c:3]1:[c:4]:[c:5]2:[#7;a:6]:[c:7]:[#7;a:8]:[c:9]:2:[c:10]:[n;H0;D2;+0:11]:1>>[O-;H0;D1:1]-[n+;H0;D3:11]1:[c:10]:[c:9]2:[#7;a:8]:[c:7]:[#7;a:6]:[c:5]:2:[c:4]:[c:3]:1:[c:2] | 99.7 | [{"value": 99.7, "product": "COCCC=1N(C2=C(C=[N+](C=3C=CC=CC23)[O-])N1)CCOCCNC(OC(C)(C)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | A solution of tert-butyl 2-{2-[2-(2-methoxyethyl)-1H-imidazo[4,5-c]quinolin-1-yl]ethoxy}ethylcarbamate (10.22 g, 24.7 mmol) in 250 mL of CHCl3 was treated with 3-chloroperoxybenzoic acid (MCPBA, 77%, 9.12 g, 40.8 mmol). After stirring 30 min, the reaction mixture was washed with 1% Na2CO3 solution (2×75 mL) and brine. ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Peroxide | null | c1nc2c(cnc3ccccc32)[nH]1.c1ccccc1 | c1nc2c(c[n+]c3ccccc32)[nH]1 | c1nc2c(c[n+]c3ccccc32)[nH]1 | HCl | C(Cl)(Cl)Cl | null | 0.5 | COCCc1nc2cnc3ccccc3c2n1CCOCCNC(=O)OC(C)(C)C.O=C(OO)c1cccc(Cl)c1>C(Cl)(Cl)Cl>COCCc1nc2c[n+]([O-])c3ccccc3c2n1CCOCCNC(=O)OC(C)(C)C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-02b41cb13ed44b7f9c6e44032ec7ef5f | COCCc1nc2c[n+]([O-])c3ccccc3c2n1CCOCCNC(=O)OC(C)(C)C.[NH4+]>>COCCc1nc2c(N)nc3ccccc3c2n1CCOCCNC(=O)OC(C)(C)C | [NH4+].[OH-].COCCC=1N(C2=C(C=[N+](C=3C=CC=CC23)[O-])N1)CCOCCNC(OC(C)(C)C)=O.[NH4+].[OH-].C(Cl)(Cl)Cl.C1(=CC=C(C=C1)S(=O)(=O)Cl)C>>NC1=NC=2C=CC=CC2C2=C1N=C(N2CCOCCNC(OC(C)(C)C)=O)CCOC | [O-][n+:10]1[cH:8][c:7]2[n:6][c:5]([CH2:4][CH2:3][O:2][CH3:1])[n:18]([CH2:19][CH2:20][O:21][CH2:22][CH2:23][NH:24][C:25](=[O:26])[O:27][C:28]([CH3:29])([CH3:30])[CH3:31])[c:17]2[c:16]2[c:11]1[cH:12][cH:13][cH:14][cH:15]2.[NH4+:9]>>[CH3:1][O:2][CH2:3][CH2:4][c:5]1[n:6][c:7]2[c:8]([NH2:9])[n:10][c:11]3[cH:12][cH:13][cH:1... | COCCc1nc2c[n+]([O-])c3ccccc3c2n1CCOCCNC(=O)OC(C)(C)C.[NH4+] | COCCc1nc2c(N)nc3ccccc3c2n1CCOCCNC(=O)OC(C)(C)C | null | null | ClCCCl | Protection | OtherReaction | 1a3560ac88422fd247b995f02bc4ff4290625edd39947787fab7dac607ad70df | bf08eb59ebe808bce722373055de9689551bb60b2522898c82bc26646fc1fe40 | c1ccc2c(c1)ncc1nc[nH]c12 | [C:1]-[#7;a:2]1:[c:3]:[#7;a:4]:[c:5]2:[cH;D2;+0:6]:[n+;H0;D3:7](-[O-]):[c:8](:[c:9]):[c:10]:[c:11]:1:2.[NH4+;D0:12]>>[C:1]-[#7;a:2]1:[c:3]:[#7;a:4]:[c:5]2:[c:11]:1:[c:10]:[c:8](:[c:9]):[n;H0;D2;+0:7]:[c;H0;D3;+0:6]:2-[NH2;D1;+0:12] | null | [] | null | null | 2 | HOUR | A solution of tert-butyl 2-{2-[2-(2-methoxyethyl)-5-oxido-1H-imidazo[4,5-c]quinolin-1-yl]ethoxy}ethylcarbamate (10.6 g, 24.6 mmol) in 100 mL of 1,2-dichloroethane was heated to 60° C. and treated with 10 mL of concentrated NH4OH solution. To the rapidly stirred solution was added solid p-toluenesulfonyl chloride (7.05 ... | 10.6084/m9.figshare.5104873.v1 | null | null | Primary amine | c1nc2c(c[n+]c3ccccc32)[nH]1 | c1nc2c(cnc3ccccc32)[nH]1 | c1nc2c(cnc3ccccc32)[nH]1 | HO- | ClCCCl | null | 2 | COCCc1nc2c[n+]([O-])c3ccccc3c2n1CCOCCNC(=O)OC(C)(C)C.[NH4+]>ClCCCl>COCCc1nc2c(N)nc3ccccc3c2n1CCOCCNC(=O)OC(C)(C)C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-af6fc172b955434b92c98e3db4a7fd5e | COCCc1nc2c(N)nc3ccccc3c2n1CCOCCN.O=C=Nc1ccccc1>>COCCc1nc2c(N)nc3ccccc3c2n1CCOCCNC(=O)Nc1ccccc1 | NCCOCCN1C(=NC=2C(=NC=3C=CC=CC3C21)N)CCOC.C1(=CC=CC=C1)N=C=O.CCN(CC)CC>>NC1=NC=2C=CC=CC2C2=C1N=C(N2CCOCCNC(=O)NC2=CC=CC=C2)CCOC | [CH3:1][O:2][CH2:3][CH2:4][c:5]1[n:6][c:7]2[c:8]([NH2:9])[n:10][c:11]3[cH:12][cH:13][cH:14][cH:15][c:16]3[c:17]2[n:18]1[CH2:19][CH2:20][O:21][CH2:22][CH2:23][NH2:24].[C:25](=[O:26])=[N:27][c:28]1[cH:29][cH:30][cH:31][cH:32][cH:33]1>>[CH3:1][O:2][CH2:3][CH2:4][c:5]1[n:6][c:7]2[c:8]([NH2:9])[n:10][c:11]3[cH:12][cH:13][cH... | COCCc1nc2c(N)nc3ccccc3c2n1CCOCCN.O=C=Nc1ccccc1 | COCCc1nc2c(N)nc3ccccc3c2n1CCOCCNC(=O)Nc1ccccc1 | null | null | C(Cl)Cl.CCOC(=O)C | Acylation | Urea synthesis via isocyanate and primary amine | d39cd7dc52a79bb265ff8ef61ef7bf9dc7f7b5fb0150fcb4881bdfb18ab9c380 | a5dc801930c765d2a435a0a2973e50163c305ba8e7641d6adbcc1550b7b96de7 | O=C(NCCOCCn1cnc2cnc3ccccc3c21)Nc1ccccc1 | [C:1]-[C:2]-[NH2;D1;+0:3].[O;D1;H0:4]=[C;H0;D2;+0:5]=[N;H0;D2;+0:6]-[c:7](:[c:8]):[c:9]>>[C:1]-[C:2]-[NH;D2;+0:3]-[C;H0;D3;+0:5](=[O;D1;H0:4])-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9] | 12.3 | [{"value": 12.3, "product": "NC1=NC=2C=CC=CC2C2=C1N=C(N2CCOCCNC(=O)NC2=CC=CC=C2)CCOC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 2 | HOUR | 1-[2-(2-Aminoethoxy)ethyl]-2-(2-methoxyethyl)-1H-imidazo[4,5-c]quinolin-4-amine (750 mg, 2.28 mmol) was dissolved in 30 mL of anhydrous CH2Cl2 and cooled to 0° C. under N2. The reaction mixture was then treated with phenyl isocyanate (247 μL, 2.28 mmol) and Et3N (0.64 mL, 4.56 mmol) and allowed to warm slowly to room t... | 10.6084/m9.figshare.5104873.v1 | null | Isocyanate.Primary amine | Urea | null | null | c1nc2c(cnc3ccccc32)[nH]1.c1ccccc1 | null | C(Cl)Cl.CCOC(=O)C | 0 | 2 | COCCc1nc2c(N)nc3ccccc3c2n1CCOCCN.O=C=Nc1ccccc1>C(Cl)Cl.CCOC(=O)C>COCCc1nc2c(N)nc3ccccc3c2n1CCOCCNC(=O)Nc1ccccc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-a8d3be0f1d59427382222b78dfef6669 | COCCc1nc2c(N)nc3ccccc3c2n1CCOCCN>>COCCc1nc2c(N)nc3c(c2n1CCOCCN)CCCC3 | NCCOCCN1C(=NC=2C(=NC=3C=CC=CC3C21)N)CCOC.[OH-].[Na+]>>NCCOCCN1C(=NC=2C(=NC=3CCCCC3C21)N)CCOC | [CH3:1][O:2][CH2:3][CH2:4][c:5]1[n:6][c:7]2[c:8]([NH2:9])[n:10][c:11]3[c:12]([c:13]2[n:14]1[CH2:15][CH2:16][O:17][CH2:18][CH2:19][NH2:20])[cH:21][cH:22][cH:23][cH:24]3>>[CH3:1][O:2][CH2:3][CH2:4][c:5]1[n:6][c:7]2[c:8]([NH2:9])[n:10][c:11]3[c:12]([c:13]2[n:14]1[CH2:15][CH2:16][O:17][CH2:18][CH2:19][NH2:20])[CH2:21][CH2:... | COCCc1nc2c(N)nc3ccccc3c2n1CCOCCN | COCCc1nc2c(N)nc3c(c2n1CCOCCN)CCCC3 | null | O=[Pt]=O.O=[Pt]=O | O.FC(C(=O)O)(F)F | Reduction | OtherReaction | 0e4a6a9a13d238c6a8679b2fe0694b39c5876b5c67afff3fabe8c9f8991c0ff5 | 312e9350dcad67590617294c0eb017edf0b9fbfe6133c06a3f393b871a889092 | c1nc2cnc3c(c2[nH]1)CCCC3 | [C:1]-[#7;a:2]1:[c:3]:[#7;a:4]:[c:5]2:[c:6]:[#7;a:7]:[c:8]3:[cH;D2;+0:9]:[cH;D2;+0:10]:[cH;D2;+0:11]:[cH;D2;+0:12]:[c:13]:3:[c:14]:1:2>>[C:1]-[#7;a:2]1:[c:3]:[#7;a:4]:[c:5]2:[c:6]:[#7;a:7]:[c:8]3:[c:13](:[c:14]:1:2)-[CH2;D2;+0:12]-[CH2;D2;+0:11]-[CH2;D2;+0:10]-[CH2;D2;+0:9]-3 | 56.8 | [{"value": 56.8, "product": "NCCOCCN1C(=NC=2C(=NC=3CCCCC3C21)N)CCOC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 4 | DAY | 1-[2-(2-Aminoethoxy)ethyl]-2-(2-methoxyethyl)-1H-imidazo[4,5-c]quinolin-4-amine (10.0 g, 27.3 mmol) was dissolved in 50 mL of trifluoroacetic acid and treated with PtO2 (1.0 g). The reaction mixture was shaken under H2 (3 Kg/cm2). After 4 d, an additional 0.5 g of PtO2 was added and hydrogenation was continued for an a... | 10.6084/m9.figshare.5104873.v1 | null | null | null | c1nc2c(cnc3ccccc32)[nH]1 | c1nc2c3c(ncc2[nH]1)CCCC3 | c1nc2c3c(ncc2[nH]1)CCCC3 | null | O=[Pt]=O.O=[Pt]=O.O.FC(C(=O)O)(F)F | null | 96 | COCCc1nc2c(N)nc3ccccc3c2n1CCOCCN>O=[Pt]=O.O=[Pt]=O.O.FC(C(=O)O)(F)F>COCCc1nc2c(N)nc3c(c2n1CCOCCN)CCCC3 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-dad8df40988e4f31b87f0a164dd34f68 | COCCc1nc2c(N)nc3c(c2n1CCOCCN)CCCC3.O=C=Nc1ccccc1>>COCCc1nc2c(N)nc3c(c2n1CCOCCNC(=O)Nc1ccccc1)CCCC3 | NCCOCCN1C(=NC=2C(=NC=3CCCCC3C21)N)CCOC.C1(=CC=CC=C1)N=C=O.CCN(CC)CC>>NC1=NC=2CCCCC2C2=C1N=C(N2CCOCCNC(=O)NC2=CC=CC=C2)CCOC | [CH3:1][O:2][CH2:3][CH2:4][c:5]1[n:6][c:7]2[c:8]([NH2:9])[n:10][c:11]3[c:12]([c:13]2[n:14]1[CH2:15][CH2:16][O:17][CH2:18][CH2:19][NH2:20])[CH2:30][CH2:31][CH2:32][CH2:33]3.[C:21](=[O:22])=[N:23][c:24]1[cH:25][cH:26][cH:27][cH:28][cH:29]1>>[CH3:1][O:2][CH2:3][CH2:4][c:5]1[n:6][c:7]2[c:8]([NH2:9])[n:10][c:11]3[c:12]([c:1... | COCCc1nc2c(N)nc3c(c2n1CCOCCN)CCCC3.O=C=Nc1ccccc1 | COCCc1nc2c(N)nc3c(c2n1CCOCCNC(=O)Nc1ccccc1)CCCC3 | null | null | C(Cl)Cl | Acylation | Urea synthesis via isocyanate and primary amine | d39cd7dc52a79bb265ff8ef61ef7bf9dc7f7b5fb0150fcb4881bdfb18ab9c380 | a5dc801930c765d2a435a0a2973e50163c305ba8e7641d6adbcc1550b7b96de7 | O=C(NCCOCCn1cnc2cnc3c(c21)CCCC3)Nc1ccccc1 | [C:1]-[C:2]-[NH2;D1;+0:3].[O;D1;H0:4]=[C;H0;D2;+0:5]=[N;H0;D2;+0:6]-[c:7](:[c:8]):[c:9]>>[C:1]-[C:2]-[NH;D2;+0:3]-[C;H0;D3;+0:5](=[O;D1;H0:4])-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9] | 36.8 | [{"value": 36.8, "product": "NC1=NC=2CCCCC2C2=C1N=C(N2CCOCCNC(=O)NC2=CC=CC=C2)CCOC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 8 | HOUR | 1-[2-(2-Aminoethoxy)ethyl]-2-(2-methoxyethyl)-6,7,8,9-tetrahydro-1H-imidazo[4,5-c]quinolin-4-amine (919 mg, 2.76 mmol) was dissolved in 30 mL of anhydrous CH2Cl2 and cooled to 0° C. under N2. The reaction mixture was then treated with phenyl isocyanate (300 μL, 2.76 mmol) and Et3N (0.77 mL, 5.51 mmol) and allowed to wa... | 10.6084/m9.figshare.5104873.v1 | null | Isocyanate.Primary amine | Urea | null | null | c1ccccc1.c1nc2c3c(ncc2[nH]1)CCCC3 | null | C(Cl)Cl | 0 | 8 | COCCc1nc2c(N)nc3c(c2n1CCOCCN)CCCC3.O=C=Nc1ccccc1>C(Cl)Cl>COCCc1nc2c(N)nc3c(c2n1CCOCCNC(=O)Nc1ccccc1)CCCC3 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-025aabda249041eaa8d627746d8fa17c | CC(C)(C)OC(=O)NCCOCCN=[N+]=[N-].CI>>CN(CCOCCN=[N+]=[N-])C(=O)OC(C)(C)C | CI.[H-].[Na+].N(=[N+]=[N-])CCOCCNC(OC(C)(C)C)=O.[H-].[Na+]>>N(=[N+]=[N-])CCOCCN(C(OC(C)(C)C)=O)C | [NH:2]([CH2:3][CH2:4][O:5][CH2:6][CH2:7][N:8]=[N+:9]=[N-:10])[C:11](=[O:12])[O:13][C:14]([CH3:15])([CH3:16])[CH3:17].I[CH3:1]>>[CH3:1][N:2]([CH2:3][CH2:4][O:5][CH2:6][CH2:7][N:8]=[N+:9]=[N-:10])[C:11](=[O:12])[O:13][C:14]([CH3:15])([CH3:16])[CH3:17] | CC(C)(C)OC(=O)NCCOCCN=[N+]=[N-].CI | CN(CCOCCN=[N+]=[N-])C(=O)OC(C)(C)C | null | null | C1CCOC1 | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 29c841ae076cb6ee785aad2a4e3ce1a9b47357d7ad25657b8d9991b1347f5721 | c485eddcb40c5a0d396ffdb624041effa09ee4f5ca2ecce3fe13077cf65004ed | null | I-[CH3;D1;+0:1].[C:2]-[C:3]-[NH;D2;+0:4]-[C:5](=[O;D1;H0:6])-[#8:7]-[C:8](-[C;D1;H3:9])(-[C;D1;H3:10])-[C;D1;H3:11]>>[C:2]-[C:3]-[N;H0;D3;+0:4](-[CH3;D1;+0:1])-[C:5](=[O;D1;H0:6])-[#8:7]-[C:8](-[C;D1;H3:9])(-[C;D1;H3:10])-[C;D1;H3:11] | 94.2 | [{"value": 94.2, "product": "N(=[N+]=[N-])CCOCCN(C(OC(C)(C)C)=O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 20 | MINUTE | Sodium hydride (60% oil dispersion, 9.1 g, 228 mmol) was placed in a round bottom flask and washed with hexanes (3×) under N2. The dried sodium hydride was treated with 800 mL of anhydrous THF. A solution of tert-butyl 2-(2-azidoethoxy)ethylcarbamate (41.9 g, 182 mmol) in 200 mL of THF was then added to the stirred sod... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester | Carbamic ester | null | null | null | HI | C1CCOC1 | null | 0.333333 | CC(C)(C)OC(=O)NCCOCCN=[N+]=[N-].CI>C1CCOC1>CN(CCOCCN=[N+]=[N-])C(=O)OC(C)(C)C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-dc29b9fde43c4a0abefb56f46251793a | CN(CCOCCN=[N+]=[N-])C(=O)OC(C)(C)C>>CN(CCOCCN)C(=O)OC(C)(C)C | N(=[N+]=[N-])CCOCCN(C(OC(C)(C)C)=O)C>>NCCOCCN(C(OC(C)(C)C)=O)C | [N-]=[N+]=[N:8][CH2:7][CH2:6][O:5][CH2:4][CH2:3][N:2]([CH3:1])[C:9](=[O:10])[O:11][C:12]([CH3:13])([CH3:14])[CH3:15]>>[CH3:1][N:2]([CH2:3][CH2:4][O:5][CH2:6][CH2:7][NH2:8])[C:9](=[O:10])[O:11][C:12]([CH3:13])([CH3:14])[CH3:15] | CN(CCOCCN=[N+]=[N-])C(=O)OC(C)(C)C | CN(CCOCCN)C(=O)OC(C)(C)C | null | [Pd] | CO | Reduction | Azide to amine reduction (Staudinger) | 4c9e4990dae2bb965dec06bd45e318560989ee3681b61e443f7aa363b7cfa222 | cd009d687d606bf351eac9390a176d16be38f2c8216a599b398641009c215027 | null | [C:1]-[C:2]-[N;H0;D2;+0:3]=[N+]=[N-]>>[C:1]-[C:2]-[NH2;D1;+0:3] | 100.2 | [{"value": 100.2, "product": "NCCOCCN(C(OC(C)(C)C)=O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 24 | HOUR | A solution tert-butyl 2-(2-azidoethoxy)ethyl(methyl)carbamate (41.9 g, 170 mmol) in 600 mL of MeOH was treated with 2.5 g of 10% Pd on carbon and shaken under H2 (3 Kg/cm2) for 24 h. The solution was then filtered through a Celite pad and concentrated to give 37.2 g of crude tert-butyl 2-(2-aminoethoxy)ethyl(methyl)car... | 10.6084/m9.figshare.5104873.v1 | null | Azide | Primary amine | null | null | null | Other | [Pd].CO | null | 24 | CN(CCOCCN=[N+]=[N-])C(=O)OC(C)(C)C>[Pd].CO>CN(CCOCCN)C(=O)OC(C)(C)C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-c88ac23e2154438b9ed5a2f01284f5d4 | CN(CCOCCN)C(=O)OC(C)(C)C.O=[N+]([O-])c1cnc2ccccc2c1Cl>>CN(CCOCCNc1c([N+](=O)[O-])cnc2ccccc12)C(=O)OC(C)(C)C | ClC1=C(C=NC2=CC=CC=C12)[N+](=O)[O-].C(C)N(CC)CC.NCCOCCN(C(OC(C)(C)C)=O)C>>CN(C(OC(C)(C)C)=O)CCOCCNC1=C(C=NC2=CC=CC=C12)[N+](=O)[O-] | [CH3:1][N:2]([CH2:3][CH2:4][O:5][CH2:6][CH2:7][NH2:8])[C:22](=[O:23])[O:24][C:25]([CH3:26])([CH3:27])[CH3:28].Cl[c:9]1[c:10]([N+:11](=[O:12])[O-:13])[cH:14][n:15][c:16]2[cH:17][cH:18][cH:19][cH:20][c:21]12>>[CH3:1][N:2]([CH2:3][CH2:4][O:5][CH2:6][CH2:7][NH:8][c:9]1[c:10]([N+:11](=[O:12])[O-:13])[cH:14][n:15][c:16]2[cH:... | CN(CCOCCN)C(=O)OC(C)(C)C.O=[N+]([O-])c1cnc2ccccc2c1Cl | CN(CCOCCNc1c([N+](=O)[O-])cnc2ccccc12)C(=O)OC(C)(C)C | null | null | C(Cl)Cl | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | 45e8470a78418ade39424f40732aa5ecf6717a7e5d47830a67429c5970ebd551 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc2ncccc2c1 | Cl-[c;H0;D3;+0:1]1:[c:2](-[#7;+:3]):[c:4]:[#7;a:5]:[c:6](:[c:7]):[c:8]:1:[c:9].[C:10]-[C:11]-[NH2;D1;+0:12]>>[#7;+:3]-[c:2]1:[c:4]:[#7;a:5]:[c:6](:[c:7]):[c:8](:[c:9]):[c;H0;D3;+0:1]:1-[NH;D2;+0:12]-[C:11]-[C:10] | 77.2 | [{"value": 77.2, "product": "CN(C(OC(C)(C)C)=O)CCOCCNC1=C(C=NC2=CC=CC=C12)[N+](=O)[O-]", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | A stirred solution of 4-chloro-3-nitroquinoline (32.3 g, 155 mmol) in 400 mL of anhydrous CH2Cl2, under N2, was treated with triethylamine (43.1 mL, 310 mmol) and tert-butyl 2-(2-aminoethoxy)ethyl(methyl)carbamate (37.2 g, 171 mmol). After stirring overnight, the reaction mixture was washed with H2O (2×300 mL) and brin... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccc2ncccc2c1 | c1ccc2ncccc2c1 | c1ccc2ncccc2c1 | HCl | C(Cl)Cl | null | 8 | CN(CCOCCN)C(=O)OC(C)(C)C.O=[N+]([O-])c1cnc2ccccc2c1Cl>C(Cl)Cl>CN(CCOCCNc1c([N+](=O)[O-])cnc2ccccc12)C(=O)OC(C)(C)C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-790bffd1a5474b7e9bddf9f4c3316e68 | CN(CCOCCNc1c([N+](=O)[O-])cnc2ccccc12)C(=O)OC(C)(C)C>>CN(CCOCCNc1c(N)cnc2ccccc12)C(=O)OC(C)(C)C | CN(C(OC(C)(C)C)=O)CCOCCNC1=C(C=NC2=CC=CC=C12)[N+](=O)[O-]>>NC=1C=NC2=CC=CC=C2C1NCCOCCN(C(OC(C)(C)C)=O)C | O=[N+:11]([O-])[c:10]1[c:9]([NH:8][CH2:7][CH2:6][O:5][CH2:4][CH2:3][N:2]([CH3:1])[C:20](=[O:21])[O:22][C:23]([CH3:24])([CH3:25])[CH3:26])[c:19]2[c:14]([n:13][cH:12]1)[cH:15][cH:16][cH:17][cH:18]2>>[CH3:1][N:2]([CH2:3][CH2:4][O:5][CH2:6][CH2:7][NH:8][c:9]1[c:10]([NH2:11])[cH:12][n:13][c:14]2[cH:15][cH:16][cH:17][cH:18][... | CN(CCOCCNc1c([N+](=O)[O-])cnc2ccccc12)C(=O)OC(C)(C)C | CN(CCOCCNc1c(N)cnc2ccccc12)C(=O)OC(C)(C)C | null | [Pt] | C1(=CC=CC=C1)C | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccc2ncccc2c1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]:[#7;a:5]:[c:6]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4]:[#7;a:5]:[c:6] | 112.3 | [{"value": 112.3, "product": "NC=1C=NC2=CC=CC=C2C1NCCOCCN(C(OC(C)(C)C)=O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 24 | HOUR | A solution of tert-butyl methyl(2-{2-[(3-nitroquinolin-4-yl)amino]ethoxy}ethyl)carbamate (6.56 g, 16.8 mmol) in 75 mL of toluene was treated with 0.5 g of 5% Pt on carbon and shaken under H2 (3 Kg/cm2) for 24 h. The solution was then filtered through a Celite pad and concentrated to give 6.8 g of crude tert-butyl 2-{2-... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccc2ncccc2c1 | Other | [Pt].C1(=CC=CC=C1)C | null | 24 | CN(CCOCCNc1c([N+](=O)[O-])cnc2ccccc12)C(=O)OC(C)(C)C>[Pt].C1(=CC=CC=C1)C>CN(CCOCCNc1c(N)cnc2ccccc12)C(=O)OC(C)(C)C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-1ace2d11d6e444918f7af8a4b0dc9206 | CN(CCOCCNc1c(N)cnc2ccccc12)C(=O)OC(C)(C)C.COCCC(=O)Cl>>COCCc1nc2cnc3ccccc3c2n1CCOCCN(C)C(=O)OC(C)(C)C | C.COCCC(=O)Cl.C(C)N(CC)CC.NC=1C=NC2=CC=CC=C2C1NCCOCCN(C(OC(C)(C)C)=O)C.C(C)N(CC)CC>>COCCC=1N(C2=C(C=NC=3C=CC=CC23)N1)CCOCCN(C(OC(C)(C)C)=O)C | [NH2:6][c:7]1[cH:8][n:9][c:10]2[cH:11][cH:12][cH:13][cH:14][c:15]2[c:16]1[NH:17][CH2:18][CH2:19][O:20][CH2:21][CH2:22][N:23]([CH3:24])[C:25](=[O:26])[O:27][C:28]([CH3:29])([CH3:30])[CH3:31].O=[C:5](Cl)[CH2:4][CH2:3][O:2][CH3:1]>>[CH3:1][O:2][CH2:3][CH2:4][c:5]1[n:6][c:7]2[cH:8][n:9][c:10]3[cH:11][cH:12][cH:13][cH:14][c... | CN(CCOCCNc1c(N)cnc2ccccc12)C(=O)OC(C)(C)C.COCCC(=O)Cl | COCCc1nc2cnc3ccccc3c2n1CCOCCN(C)C(=O)OC(C)(C)C | null | null | CO.C(Cl)Cl.CCO | Aromatic Heterocycle Formation | OtherReaction | 2849961f1d737a23d71906fe74b0976730547255ac052bf4a7367ba2be72dd8e | 56ef83dfadec35a1cf1db968b807e178cc4924ce15bf36d774883783cef0f450 | c1ccc2c(c1)ncc1nc[nH]c12 | Cl-[C;H0;D3;+0:1](=O)-[C:2]-[C:3].[C:4]-[C:5]-[NH;D2;+0:6]-[c:7]1:[c:8]:[c:9]:[#7;a:10]:[c:11]:[c:12]:1-[NH2;D1;+0:13]>>[C:4]-[C:5]-[n;H0;D3;+0:6]1:[c:7]2:[c:8]:[c:9]:[#7;a:10]:[c:11]:[c:12]:2:[n;H0;D2;+0:13]:[c;H0;D3;+0:1]:1-[C:2]-[C:3] | 100 | [{"value": 100.0, "product": "COCCC=1N(C2=C(C=NC=3C=CC=CC23)N1)CCOCCN(C(OC(C)(C)C)=O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | A solution of tert-butyl 2-{2-[(3-aminoquinolin-4-yl)amino]ethoxy}ethyl(methyl)carbamate (6.05 g, 16.8 mmol) in 200 mL of anhydrous CH2Cl2 was cooled to 0° C. and treated with triethylamine (2.40 mL, 17.2 mmol). Methoxypropionyl chloride (1.72 mL, 17.2 mmol) was then added dropwise over 5 min. The reaction was then war... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine.Secondary amine | null | c1ccc2ncccc2c1 | c1nc2c(cnc3ccccc32)[nH]1 | c1nc2c(cnc3ccccc32)[nH]1 | HCl | CO.C(Cl)Cl.CCO | null | 3 | CN(CCOCCNc1c(N)cnc2ccccc12)C(=O)OC(C)(C)C.COCCC(=O)Cl>CO.C(Cl)Cl.CCO>COCCc1nc2cnc3ccccc3c2n1CCOCCN(C)C(=O)OC(C)(C)C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-da69ac99ee0a4b629e7ceb03ac1c3e56 | COCCc1nc2cnc3ccccc3c2n1CCOCCN(C)C(=O)OC(C)(C)C.O=C(OO)c1cccc(Cl)c1>>COCCc1nc2c[n+]([O-])c3ccccc3c2n1CCOCCN(C)C(=O)OC(C)(C)C | C(=O)(O)[O-].[Na+].COCCC=1N(C2=C(C=NC=3C=CC=CC23)N1)CCOCCN(C(OC(C)(C)C)=O)C.C1=CC(=CC(=C1)Cl)C(=O)OO>>COCCC=1N(C2=C(C=[N+](C=3C=CC=CC23)[O-])N1)CCOCCN(C(OC(C)(C)C)=O)C | [CH3:1][O:2][CH2:3][CH2:4][c:5]1[n:6][c:7]2[cH:8][n:9][c:11]3[cH:12][cH:13][cH:14][cH:15][c:16]3[c:17]2[n:18]1[CH2:19][CH2:20][O:21][CH2:22][CH2:23][N:24]([CH3:25])[C:26](=[O:27])[O:28][C:29]([CH3:30])([CH3:31])[CH3:32].O=C(O[OH:10])c1cccc(Cl)c1>>[CH3:1][O:2][CH2:3][CH2:4][c:5]1[n:6][c:7]2[cH:8][n+:9]([O-:10])[c:11]3[c... | COCCc1nc2cnc3ccccc3c2n1CCOCCN(C)C(=O)OC(C)(C)C.O=C(OO)c1cccc(Cl)c1 | COCCc1nc2c[n+]([O-])c3ccccc3c2n1CCOCCN(C)C(=O)OC(C)(C)C | null | null | C(Cl)Cl | Miscellaneous | OtherReaction | 86abb75bf448eea8ddd78de30fcfc7b06bb61e46f725af6f1625e0dd9537993c | 98b338a9d01476c0929fd5672e7509121bfe69600fd72e4d1cc6f1782e2d05d9 | c1ccc2c(c1)[nH+]cc1nc[nH]c12 | Cl-c1:c:c:c:c(-C(=O)-O-[OH;D1;+0:1]):c:1.[c:2]:[c:3]1:[c:4]:[c:5]2:[#7;a:6]:[c:7]:[#7;a:8]:[c:9]:2:[c:10]:[n;H0;D2;+0:11]:1>>[O-;H0;D1:1]-[n+;H0;D3:11]1:[c:10]:[c:9]2:[#7;a:8]:[c:7]:[#7;a:6]:[c:5]:2:[c:4]:[c:3]:1:[c:2] | 94.4 | [{"value": 94.4, "product": "COCCC=1N(C2=C(C=[N+](C=3C=CC=CC23)[O-])N1)CCOCCN(C(OC(C)(C)C)=O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 6 | HOUR | A solution of tert-butyl 2-{2-[2-(2-methoxyethyl)-1H-imidazo[4,5-c]quinolin-1-yl]ethoxy}ethyl(methyl)carbamate (7.20 g, 16.8 mmol) in 200 mL of CH2Cl2 was treated with MCPBA (77%, 4.32 g, 19.3 mmol). After stirring 6 h, the reaction mixture was treated with saturated NaHCO3 solution and the layers were separated. The o... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Peroxide | null | c1nc2c(cnc3ccccc32)[nH]1.c1ccccc1 | c1nc2c(c[n+]c3ccccc32)[nH]1 | c1nc2c(c[n+]c3ccccc32)[nH]1 | HCl | C(Cl)Cl | null | 6 | COCCc1nc2cnc3ccccc3c2n1CCOCCN(C)C(=O)OC(C)(C)C.O=C(OO)c1cccc(Cl)c1>C(Cl)Cl>COCCc1nc2c[n+]([O-])c3ccccc3c2n1CCOCCN(C)C(=O)OC(C)(C)C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-9764a74295d040ab920405ed2f5f78a5 | COCCc1nc2c[n+]([O-])c3ccccc3c2n1CCOCCN(C)C(=O)OC(C)(C)C.[NH4+]>>COCCc1nc2c(N)nc3ccccc3c2n1CCOCCN(C)C(=O)OC(C)(C)C | [NH4+].[OH-].COCCC=1N(C2=C(C=[N+](C=3C=CC=CC23)[O-])N1)CCOCCN(C(OC(C)(C)C)=O)C.[NH4+].[OH-].C(Cl)Cl.C1(=CC=C(C=C1)S(=O)(=O)Cl)C>>NC1=NC=2C=CC=CC2C2=C1N=C(N2CCOCCN(C(OC(C)(C)C)=O)C)CCOC | [O-][n+:10]1[cH:8][c:7]2[n:6][c:5]([CH2:4][CH2:3][O:2][CH3:1])[n:18]([CH2:19][CH2:20][O:21][CH2:22][CH2:23][N:24]([CH3:25])[C:26](=[O:27])[O:28][C:29]([CH3:30])([CH3:31])[CH3:32])[c:17]2[c:16]2[c:11]1[cH:12][cH:13][cH:14][cH:15]2.[NH4+:9]>>[CH3:1][O:2][CH2:3][CH2:4][c:5]1[n:6][c:7]2[c:8]([NH2:9])[n:10][c:11]3[cH:12][cH... | COCCc1nc2c[n+]([O-])c3ccccc3c2n1CCOCCN(C)C(=O)OC(C)(C)C.[NH4+] | COCCc1nc2c(N)nc3ccccc3c2n1CCOCCN(C)C(=O)OC(C)(C)C | null | null | ClCCCl | Protection | OtherReaction | 1a3560ac88422fd247b995f02bc4ff4290625edd39947787fab7dac607ad70df | bf08eb59ebe808bce722373055de9689551bb60b2522898c82bc26646fc1fe40 | c1ccc2c(c1)ncc1nc[nH]c12 | [C:1]-[#7;a:2]1:[c:3]:[#7;a:4]:[c:5]2:[cH;D2;+0:6]:[n+;H0;D3:7](-[O-]):[c:8](:[c:9]):[c:10]:[c:11]:1:2.[NH4+;D0:12]>>[C:1]-[#7;a:2]1:[c:3]:[#7;a:4]:[c:5]2:[c:11]:1:[c:10]:[c:8](:[c:9]):[n;H0;D2;+0:7]:[c;H0;D3;+0:6]:2-[NH2;D1;+0:12] | null | [] | null | null | 4 | HOUR | A solution of tert-butyl 2-{2-[2-(2-methoxyethyl)-5-oxido-1H-imidazo[4,5-c]quinolin-1-yl]ethoxy}ethyl(methyl)carbamate (7.05 g, 15.9 mmol) in 100 mL of 1,2-dichloroethane was heated to 80° C. and treated with 5 mL of concentrated NH4OH solution. To the rapidly stirred solution was added solid p-toluenesulfonyl chloride... | 10.6084/m9.figshare.5104873.v1 | null | null | Primary amine | c1nc2c(c[n+]c3ccccc32)[nH]1 | c1nc2c(cnc3ccccc32)[nH]1 | c1nc2c(cnc3ccccc32)[nH]1 | HO- | ClCCCl | null | 4 | COCCc1nc2c[n+]([O-])c3ccccc3c2n1CCOCCN(C)C(=O)OC(C)(C)C.[NH4+]>ClCCCl>COCCc1nc2c(N)nc3ccccc3c2n1CCOCCN(C)C(=O)OC(C)(C)C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-91a696e50c514cf2be058a01532b86ef | CNCCOCCn1c(CCOC)nc2c(N)nc3ccccc3c21>>CNCCOCCn1c(CCOC)nc2c(N)nc3c(c21)CCCC3 | COCCC=1N(C2=C(C(=NC=3C=CC=CC23)N)N1)CCOCCNC>>COCCC=1N(C2=C(C(=NC=3CCCCC23)N)N1)CCOCCNC | [CH3:1][NH:2][CH2:3][CH2:4][O:5][CH2:6][CH2:7][n:8]1[c:9]([CH2:10][CH2:11][O:12][CH3:13])[n:14][c:15]2[c:16]([NH2:17])[n:18][c:19]3[c:20]([c:21]12)[cH:22][cH:23][cH:24][cH:25]3>>[CH3:1][NH:2][CH2:3][CH2:4][O:5][CH2:6][CH2:7][n:8]1[c:9]([CH2:10][CH2:11][O:12][CH3:13])[n:14][c:15]2[c:16]([NH2:17])[n:18][c:19]3[c:20]([c:2... | CNCCOCCn1c(CCOC)nc2c(N)nc3ccccc3c21 | CNCCOCCn1c(CCOC)nc2c(N)nc3c(c21)CCCC3 | null | O=[Pt]=O.O=[Pt]=O | O.FC(C(=O)O)(F)F | Reduction | OtherReaction | 8818364208f28bd8959a2ecaa0a3d40df79a7089572c5d620cd44005e9183ac2 | 312e9350dcad67590617294c0eb017edf0b9fbfe6133c06a3f393b871a889092 | c1nc2cnc3c(c2[nH]1)CCCC3 | [C:1]-[#7;a:2]1:[c:3]:[#7;a:4]:[c:5]2:[c:6]:[#7;a:7]:[c:8]3:[cH;D2;+0:9]:[cH;D2;+0:10]:[cH;D2;+0:11]:[cH;D2;+0:12]:[c:13]:3:[c:14]:1:2>>[C:1]-[#7;a:2]1:[c:3]:[#7;a:4]:[c:5]2:[c:6]:[#7;a:7]:[c:8]3:[c:13](:[c:14]:1:2)-[CH2;D2;+0:12]-[CH2;D2;+0:11]-[CH2;D2;+0:10]-[CH2;D2;+0:9]-3 | 74.6 | [{"value": 74.6, "product": "COCCC=1N(C2=C(C(=NC=3CCCCC23)N)N1)CCOCCNC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 4 | DAY | 2-(2-Methoxyethyl)-1-{2-[2-(methylamino)ethoxy]ethyl}-1H-imidazo[4,5-c]quinolin-4-amine (4.22 g, 12.3 mmol) was dissolved in 25 mL of trifluoroacetic acid and treated with PtO2 (0.5 g). The reaction mixture was shaken under H2 (3 Kg/cm2). After 4 d, an additional 0.5 g of PtO2 was added and hydrogenation was continued ... | 10.6084/m9.figshare.5104873.v1 | null | null | null | c1nc2cnc3ccccc3c2[nH]1 | c1nc2cnc3c(c2[nH]1)CCCC3 | c1nc2cnc3c(c2[nH]1)CCCC3 | null | O=[Pt]=O.O=[Pt]=O.O.FC(C(=O)O)(F)F | null | 96 | CNCCOCCn1c(CCOC)nc2c(N)nc3ccccc3c21>O=[Pt]=O.O=[Pt]=O.O.FC(C(=O)O)(F)F>CNCCOCCn1c(CCOC)nc2c(N)nc3c(c21)CCCC3 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-5898e3f28521491e8bd3281da6e64dd3 | CNCCOCCn1c(CCOC)nc2c(N)nc3c(c21)CCCC3.O=C=Nc1ccccc1>>COCCc1nc2c(N)nc3c(c2n1CCOCCN(C)C(=O)Nc1ccccc1)CCCC3 | COCCC=1N(C2=C(C(=NC=3CCCCC23)N)N1)CCOCCNC.C1(=CC=CC=C1)N=C=O>>NC1=NC=2CCCCC2C2=C1N=C(N2CCOCCN(C(=O)NC2=CC=CC=C2)C)CCOC | [CH3:1][O:2][CH2:3][CH2:4][c:5]1[n:6][c:7]2[c:8]([NH2:9])[n:10][c:11]3[c:12]([c:13]2[n:14]1[CH2:15][CH2:16][O:17][CH2:18][CH2:19][NH:20][CH3:21])[CH2:31][CH2:32][CH2:33][CH2:34]3.[C:22](=[O:23])=[N:24][c:25]1[cH:26][cH:27][cH:28][cH:29][cH:30]1>>[CH3:1][O:2][CH2:3][CH2:4][c:5]1[n:6][c:7]2[c:8]([NH2:9])[n:10][c:11]3[c:1... | CNCCOCCn1c(CCOC)nc2c(N)nc3c(c21)CCCC3.O=C=Nc1ccccc1 | COCCc1nc2c(N)nc3c(c2n1CCOCCN(C)C(=O)Nc1ccccc1)CCCC3 | null | null | C(Cl)Cl | Acylation | Urea synthesis via isocyanate and secondary amine | 288f31369c46060b9009e57afc96d52a76d6a0243a2e1197ab47b0221bb8a3ee | 5272a383a93723269f1934f97993b0175b43cd993bcdf2f45add1dbb852d1e09 | O=C(NCCOCCn1cnc2cnc3c(c21)CCCC3)Nc1ccccc1 | [C:1]-[C:2]-[NH;D2;+0:3]-[C;D1;H3:4].[O;D1;H0:5]=[C;H0;D2;+0:6]=[N;H0;D2;+0:7]-[c:8](:[c:9]):[c:10]>>[C:1]-[C:2]-[N;H0;D3;+0:3](-[C;D1;H3:4])-[C;H0;D3;+0:6](=[O;D1;H0:5])-[NH;D2;+0:7]-[c:8](:[c:9]):[c:10] | 16.9 | [{"value": 16.9, "product": "NC1=NC=2CCCCC2C2=C1N=C(N2CCOCCN(C(=O)NC2=CC=CC=C2)C)CCOC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | 2-(2-Methoxyethyl)-1-{2-[2-(methylamino)ethoxy]ethyl}-6,7,8,9-tetrahydro-1H-imidazo[4,5-c]quinolin-4-amine (750 mg, 2.16 mmol) was dissolved in 30 mL of anhydrous CH2Cl2 and treated with phenyl isocyanate (239 μL, 2.20 mmol). After stirring under N2 overnight, the reaction mixture was concentrated under reduced pressur... | 10.6084/m9.figshare.5104873.v1 | null | Isocyanate.Secondary amine | Urea | null | null | c1ccccc1.c1nc2c3c(ncc2[nH]1)CCCC3 | null | C(Cl)Cl | null | 8 | CNCCOCCn1c(CCOC)nc2c(N)nc3c(c21)CCCC3.O=C=Nc1ccccc1>C(Cl)Cl>COCCc1nc2c(N)nc3c(c2n1CCOCCN(C)C(=O)Nc1ccccc1)CCCC3 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-c58d06a7b15144a099e79e0c7977f05d | COCCc1nc2c(N)nc3ccccc3c2n1CCOCCN.O=C(Cl)N1CCOCC1>>COCCc1nc2c(N)nc3ccccc3c2n1CCOCCNC(=O)N1CCOCC1 | NCCOCCN1C(=NC=2C(=NC=3C=CC=CC3C21)N)CCOC.C(C)N(CC)CC.N1(CCOCC1)C(=O)Cl>>NC1=NC=2C=CC=CC2C2=C1N=C(N2CCOCCNC(=O)N2CCOCC2)CCOC | [CH3:1][O:2][CH2:3][CH2:4][c:5]1[n:6][c:7]2[c:8]([NH2:9])[n:10][c:11]3[cH:12][cH:13][cH:14][cH:15][c:16]3[c:17]2[n:18]1[CH2:19][CH2:20][O:21][CH2:22][CH2:23][NH2:24].Cl[C:25](=[O:26])[N:27]1[CH2:28][CH2:29][O:30][CH2:31][CH2:32]1>>[CH3:1][O:2][CH2:3][CH2:4][c:5]1[n:6][c:7]2[c:8]([NH2:9])[n:10][c:11]3[cH:12][cH:13][cH:1... | COCCc1nc2c(N)nc3ccccc3c2n1CCOCCN.O=C(Cl)N1CCOCC1 | COCCc1nc2c(N)nc3ccccc3c2n1CCOCCNC(=O)N1CCOCC1 | null | null | ClCCl | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | b81fefae7607aa106605114867756af2924064950a2aea97200543849613e96a | 406c5893488430105533c87dfb5d625d8382e709e047cda9cfdc2235e742a9cf | O=C(NCCOCCn1cnc2cnc3ccccc3c21)N1CCOCC1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#7:3](-[C:4])-[C:5].[C:6]-[C:7]-[NH2;D1;+0:8]>>[C:6]-[C:7]-[NH;D2;+0:8]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#7:3](-[C:4])-[C:5] | 19.7 | [{"value": 19.7, "product": "NC1=NC=2C=CC=CC2C2=C1N=C(N2CCOCCNC(=O)N2CCOCC2)CCOC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 4 | HOUR | Under a nitrogen atmosphere, 1-[2-(2-aminoethoxy)ethyl]-2-(2-methoxyethyl)-1H-imidazo[4,5-c]quinolin-4-amine (0.75 g, 2.3 mmol) was dissolved in dichloromethane (30 mL) and triethylamine (0.64 mL, 4.6 mmol) using mild heat and vigorous stirring. The solution was chilled in an ice-water bath and 4-morpholinecarbonyl chl... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Tertiary amide.Primary amine | Urea | null | null | c1nc2c(cnc3ccccc32)[nH]1.C1COCC[NH]1 | HCl | ClCCl | null | 4 | COCCc1nc2c(N)nc3ccccc3c2n1CCOCCN.O=C(Cl)N1CCOCC1>ClCCl>COCCc1nc2c(N)nc3ccccc3c2n1CCOCCNC(=O)N1CCOCC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-f879e33c6a214b28b948da2d4183ca18 | CC(C)(C)OC(=O)NCCOCCNc1c(N)cnc2ccccc12.CCCCC(OCC)(OCC)OCC>>CCCCc1nc2cnc3ccccc3c2n1CCOCCNC(=O)OC(C)(C)C | C.Cl.[NH+]1=CC=CC=C1.NC=1C=NC2=CC=CC=C2C1NCCOCCNC(OC(C)(C)C)=O.C(C)OC(CCCC)(OCC)OCC>>C(CCC)C=1N(C2=C(C=NC=3C=CC=CC23)N1)CCOCCNC(OC(C)(C)C)=O | [NH2:6][c:7]1[cH:8][n:9][c:10]2[cH:11][cH:12][cH:13][cH:14][c:15]2[c:16]1[NH:17][CH2:18][CH2:19][O:20][CH2:21][CH2:22][NH:23][C:24](=[O:25])[O:26][C:27]([CH3:28])([CH3:29])[CH3:30].CCO[C:5](OCC)(OCC)[CH2:4][CH2:3][CH2:2][CH3:1]>>[CH3:1][CH2:2][CH2:3][CH2:4][c:5]1[n:6][c:7]2[cH:8][n:9][c:10]3[cH:11][cH:12][cH:13][cH:14]... | CC(C)(C)OC(=O)NCCOCCNc1c(N)cnc2ccccc12.CCCCC(OCC)(OCC)OCC | CCCCc1nc2cnc3ccccc3c2n1CCOCCNC(=O)OC(C)(C)C | null | null | C1(=CC=CC=C1)C.CO | Aromatic Heterocycle Formation | OtherReaction | af7d6de7ca5153ecd31a13d7075f2969261301df4b656bfec36bc67fd1ea176b | a60e703c3cf5c0d933aa031358d338c45d96ec82dec3fc2d9f5dce06b9dcc651 | c1ccc2c(c1)ncc1nc[nH]c12 | C-C-O-[C;H0;D4;+0:1](-O-C-C)(-O-C-C)-[C:2]-[C:3].[C:4]-[C:5]-[NH;D2;+0:6]-[c:7]1:[c:8]:[c:9]:[#7;a:10]:[c:11]:[c:12]:1-[NH2;D1;+0:13]>>[C:4]-[C:5]-[n;H0;D3;+0:6]1:[c:7]2:[c:8]:[c:9]:[#7;a:10]:[c:11]:[c:12]:2:[n;H0;D2;+0:13]:[c;H0;D3;+0:1]:1-[C:2]-[C:3] | 99.9 | [{"value": 99.9, "product": "C(CCC)C=1N(C2=C(C=NC=3C=CC=CC23)N1)CCOCCNC(OC(C)(C)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 4 | HOUR | A solution of tert-butyl 2-{2-[(3-aminoquinolin-4-yl)amino]ethoxy}ethylcarbamate (3.46 g, 10.0 mmol) in 50 mL of toluene was treated with triethylorthovalerate (2.5 mL, 14.5 mmol) and the reaction mixture was heated to reflux. A 25 mg portion of pyridinium hydrochloride was then added and refluxing was continued for 4 ... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether.Ether.Primary amine.Secondary amine | null | c1ccc2ncccc2c1 | c1nc2c(cnc3ccccc32)[nH]1 | c1nc2c(cnc3ccccc32)[nH]1 | HO- | C1(=CC=CC=C1)C.CO | null | 4 | CC(C)(C)OC(=O)NCCOCCNc1c(N)cnc2ccccc12.CCCCC(OCC)(OCC)OCC>C1(=CC=CC=C1)C.CO>CCCCc1nc2cnc3ccccc3c2n1CCOCCNC(=O)OC(C)(C)C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-607cc0f0838b42f2b1ca3aaabc9a99b1 | CCCCc1nc2cnc3ccccc3c2n1CCOCCNC(=O)OC(C)(C)C.O=C(OO)c1cccc(Cl)c1>>CCCCc1nc2c[n+]([O-])c3ccccc3c2n1CCOCCNC(=O)OC(C)(C)C | C(=O)(O)[O-].[Na+].C(CCC)C=1N(C2=C(C=NC=3C=CC=CC23)N1)CCOCCNC(OC(C)(C)C)=O.ClC=1C=C(C(=O)OO)C=CC1>>C(CCC)C=1N(C2=C(C=[N+](C=3C=CC=CC23)[O-])N1)CCOCCNC(OC(C)(C)C)=O | [CH3:1][CH2:2][CH2:3][CH2:4][c:5]1[n:6][c:7]2[cH:8][n:9][c:11]3[cH:12][cH:13][cH:14][cH:15][c:16]3[c:17]2[n:18]1[CH2:19][CH2:20][O:21][CH2:22][CH2:23][NH:24][C:25](=[O:26])[O:27][C:28]([CH3:29])([CH3:30])[CH3:31].O=C(O[OH:10])c1cccc(Cl)c1>>[CH3:1][CH2:2][CH2:3][CH2:4][c:5]1[n:6][c:7]2[cH:8][n+:9]([O-:10])[c:11]3[cH:12]... | CCCCc1nc2cnc3ccccc3c2n1CCOCCNC(=O)OC(C)(C)C.O=C(OO)c1cccc(Cl)c1 | CCCCc1nc2c[n+]([O-])c3ccccc3c2n1CCOCCNC(=O)OC(C)(C)C | null | null | C(Cl)Cl | Miscellaneous | OtherReaction | 86abb75bf448eea8ddd78de30fcfc7b06bb61e46f725af6f1625e0dd9537993c | 98b338a9d01476c0929fd5672e7509121bfe69600fd72e4d1cc6f1782e2d05d9 | c1ccc2c(c1)[nH+]cc1nc[nH]c12 | Cl-c1:c:c:c:c(-C(=O)-O-[OH;D1;+0:1]):c:1.[c:2]:[c:3]1:[c:4]:[c:5]2:[#7;a:6]:[c:7]:[#7;a:8]:[c:9]:2:[c:10]:[n;H0;D2;+0:11]:1>>[O-;H0;D1:1]-[n+;H0;D3:11]1:[c:10]:[c:9]2:[#7;a:8]:[c:7]:[#7;a:6]:[c:5]:2:[c:4]:[c:3]:1:[c:2] | 85.9 | [{"value": 85.9, "product": "C(CCC)C=1N(C2=C(C=[N+](C=3C=CC=CC23)[O-])N1)CCOCCNC(OC(C)(C)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 5 | HOUR | A solution of tert-butyl 2-[2-(2-butyl-1H-imidazo[4,5-c]quinolin-1-yl)ethoxy]ethylcarbamate (4.12 g, 10.0 mmol) in 50 mL of CH2Cl2 was treated with 3-chloroperoxybenzoic acid (MCPBA, 77%, 2.5 g, 11.2 mmol). After stirring for 5 h, the reaction mixture was treated with saturated NaHCO3 solution and the layers were separ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Peroxide | null | c1nc2c(cnc3ccccc32)[nH]1.c1ccccc1 | c1nc2c(c[n+]c3ccccc32)[nH]1 | c1nc2c(c[n+]c3ccccc32)[nH]1 | HCl | C(Cl)Cl | null | 5 | CCCCc1nc2cnc3ccccc3c2n1CCOCCNC(=O)OC(C)(C)C.O=C(OO)c1cccc(Cl)c1>C(Cl)Cl>CCCCc1nc2c[n+]([O-])c3ccccc3c2n1CCOCCNC(=O)OC(C)(C)C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-4d0031d66259482c8a402873a60126a9 | CCCCc1nc2c[n+]([O-])c3ccccc3c2n1CCOCCNC(=O)OC(C)(C)C.[NH4+]>>CCCCc1nc2c(N)nc3ccccc3c2n1CCOCCNC(=O)OC(C)(C)C | C(Cl)Cl.[NH4+].[OH-].C(CCC)C=1N(C2=C(C=[N+](C=3C=CC=CC23)[O-])N1)CCOCCNC(OC(C)(C)C)=O.C1(=CC=C(C=C1)S(=O)(=O)Cl)C>>NC1=NC=2C=CC=CC2C2=C1N=C(N2CCOCCNC(OC(C)(C)C)=O)CCCC | [O-][n+:10]1[cH:8][c:7]2[n:6][c:5]([CH2:4][CH2:3][CH2:2][CH3:1])[n:18]([CH2:19][CH2:20][O:21][CH2:22][CH2:23][NH:24][C:25](=[O:26])[O:27][C:28]([CH3:29])([CH3:30])[CH3:31])[c:17]2[c:16]2[c:11]1[cH:12][cH:13][cH:14][cH:15]2.[NH4+:9]>>[CH3:1][CH2:2][CH2:3][CH2:4][c:5]1[n:6][c:7]2[c:8]([NH2:9])[n:10][c:11]3[cH:12][cH:13][... | CCCCc1nc2c[n+]([O-])c3ccccc3c2n1CCOCCNC(=O)OC(C)(C)C.[NH4+] | CCCCc1nc2c(N)nc3ccccc3c2n1CCOCCNC(=O)OC(C)(C)C | null | null | ClCCCl | Protection | OtherReaction | 1a3560ac88422fd247b995f02bc4ff4290625edd39947787fab7dac607ad70df | bf08eb59ebe808bce722373055de9689551bb60b2522898c82bc26646fc1fe40 | c1ccc2c(c1)ncc1nc[nH]c12 | [C:1]-[#7;a:2]1:[c:3]:[#7;a:4]:[c:5]2:[cH;D2;+0:6]:[n+;H0;D3:7](-[O-]):[c:8](:[c:9]):[c:10]:[c:11]:1:2.[NH4+;D0:12]>>[C:1]-[#7;a:2]1:[c:3]:[#7;a:4]:[c:5]2:[c:11]:1:[c:10]:[c:8](:[c:9]):[n;H0;D2;+0:7]:[c;H0;D3;+0:6]:2-[NH2;D1;+0:12] | null | [] | null | null | 2 | HOUR | A solution of tert-butyl 2-[2-(2-butyl-5-oxido-1H-imidazo[4,5-c]quinolin-1-yl)ethoxy]ethylcarbamate (3.68 g, 8.60 mmol) in 100 mL of 1,2-dichloroethane was heated to 80° C. and treated with 10 mL of concentrated NH4OH solution. To the rapidly stirred solution was added solid p-toluenesulfonyl chloride (1.87 g, 9.81 mmo... | 10.6084/m9.figshare.5104873.v1 | null | null | Primary amine | c1nc2c(c[n+]c3ccccc32)[nH]1 | c1nc2c(cnc3ccccc32)[nH]1 | c1nc2c(cnc3ccccc32)[nH]1 | HO- | ClCCCl | null | 2 | CCCCc1nc2c[n+]([O-])c3ccccc3c2n1CCOCCNC(=O)OC(C)(C)C.[NH4+]>ClCCCl>CCCCc1nc2c(N)nc3ccccc3c2n1CCOCCNC(=O)OC(C)(C)C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-e01dd0b85c3048c5994888a54ce6b1ba | CC(C)(C)OC(=O)N1CCC(CCI)CC1.CCC(CO)n1cnc2cnc3ccccc3c21>>CCC(COCCC1CCN(C(=O)OC(C)(C)C)CC1)n1cnc2cnc3ccccc3c21 | [Cl-].[NH4+].N1(C=NC=2C=NC=3C=CC=CC3C21)C(CO)CC.[H-].[Na+].ICCC1CCN(CC1)C(=O)OC(C)(C)C>>N1(C=NC=2C=NC=3C=CC=CC3C21)C(COCCC2CCN(CC2)C(=O)OC(C)(C)C)CC | I[CH2:6][CH2:7][CH:8]1[CH2:9][CH2:10][N:11]([C:12](=[O:13])[O:14][C:15]([CH3:16])([CH3:17])[CH3:18])[CH2:19][CH2:20]1.[CH3:1][CH2:2][CH:3]([CH2:4][OH:5])[n:21]1[cH:22][n:23][c:24]2[cH:25][n:26][c:27]3[cH:28][cH:29][cH:30][cH:31][c:32]3[c:33]12>>[CH3:1][CH2:2][CH:3]([CH2:4][O:5][CH2:6][CH2:7][CH:8]1[CH2:9][CH2:10][N:11]... | CC(C)(C)OC(=O)N1CCC(CCI)CC1.CCC(CO)n1cnc2cnc3ccccc3c21 | CCC(COCCC1CCN(C(=O)OC(C)(C)C)CC1)n1cnc2cnc3ccccc3c21 | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | dd3f9c60e1f90d961a7c01d970ae213561355ee1451f276a3b04696e4b6fae5c | 46a6e883cf919b4006e69abfdfd883f458f55c08b3200960c6a5b57c4139fbca | c1ccc2c(c1)ncc1ncn(CCOCCC3CCNCC3)c12 | I-[CH2;D2;+0:1]-[C:2]-[C:3].[C:4]-[C:5]-[OH;D1;+0:6]>>[C:4]-[C:5]-[O;H0;D2;+0:6]-[CH2;D2;+0:1]-[C:2]-[C:3] | 18.1 | [{"value": 18.1, "product": "N1(C=NC=2C=NC=3C=CC=CC3C21)C(COCCC2CCN(CC2)C(=O)OC(C)(C)C)CC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | 45 | MINUTE | Under a nitrogen atmosphere, 2-(1H-imidazo[4,5-c]quinolin-1-yl)butan-1-ol (6.5 g, 26.9 mmol) was added in three portions to a suspension of sodium hydride (1.4 g of 60%, 35.0 mmol) in anhydrous N,N-dimethylformamide. The reaction mixture was allowed to stir for 45 minutes by which time gas evolution had ceased. Tert-bu... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary alcohol | Ether | null | null | C1CC[NH]CC1.c1ccc2c(c1)ncc1nc[nH]c12 | HI | CN(C=O)C | 100 | 0.75 | CC(C)(C)OC(=O)N1CCC(CCI)CC1.CCC(CO)n1cnc2cnc3ccccc3c21>CN(C=O)C>CCC(COCCC1CCN(C(=O)OC(C)(C)C)CC1)n1cnc2cnc3ccccc3c21 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-415921c8e7b844f19c8c633e71c1e7dc | CCC(COCCC1CCN(C(=O)OC(C)(C)C)CC1)n1cnc2c(N)nc3ccccc3c21>>CCC(COCCC1CCNCC1)n1cnc2c(N)nc3ccccc3c21 | NC1=NC=2C=CC=CC2C2=C1N=CN2C(COCCC2CCN(CC2)C(=O)OC(C)(C)C)CC.Cl>>N1CCC(CC1)CCOCC(CC)N1C=NC=2C(=NC=3C=CC=CC3C21)N | CC(C)(C)OC(=O)[N:11]1[CH2:10][CH2:9][CH:8]([CH2:7][CH2:6][O:5][CH2:4][CH:3]([CH2:2][CH3:1])[n:14]2[cH:15][n:16][c:17]3[c:18]([NH2:19])[n:20][c:21]4[cH:22][cH:23][cH:24][cH:25][c:26]4[c:27]23)[CH2:13][CH2:12]1>>[CH3:1][CH2:2][CH:3]([CH2:4][O:5][CH2:6][CH2:7][CH:8]1[CH2:9][CH2:10][NH:11][CH2:12][CH2:13]1)[n:14]1[cH:15][n... | CCC(COCCC1CCN(C(=O)OC(C)(C)C)CC1)n1cnc2c(N)nc3ccccc3c21 | CCC(COCCC1CCNCC1)n1cnc2c(N)nc3ccccc3c21 | null | null | null | Reduction | Boc amine deprotection | bf3cd5dc3e17e694d8665c89f5d7e08e8763b18436a633eb66e9bf530b8b0316 | a94b29c7264c852156fc1cdd4a0951a4fc26c06d0edc9e50c743825dbf79e3fd | c1ccc2c(c1)ncc1ncn(CCOCCC3CCNCC3)c12 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1](-[C:2]-[C:3])-[C:4]-[C:5]>>[C:5]-[C:4]-[NH;D2;+0:1]-[C:2]-[C:3] | 64.8 | [{"value": 64.8, "product": "N1CCC(CC1)CCOCC(CC)N1C=NC=2C(=NC=3C=CC=CC3C21)N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 14 | HOUR | Under a nitrogen atmosphere, tert-butyl 4-{2-[2-(4-amino-1H-imidazo[4,5-c]quinolin-1-yl)butoxy]ethyl}piperidine-1-carboxylate (1.00 g, 2.1 mmol) and 2N ethanolic hydrochloric acid (10 ml, 20 mmol) were combined and the solution was stirred at ambient temperature for 14 hours. The solvent was removed in vacuo and the re... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Secondary amine | C1CC[NH]CC1 | C1CCNCC1 | C1CCNCC1.c1nc2ccccc2c2[nH]cnc12 | HO- | null | null | 14 | CCC(COCCC1CCN(C(=O)OC(C)(C)C)CC1)n1cnc2c(N)nc3ccccc3c21>>CCC(COCCC1CCNCC1)n1cnc2c(N)nc3ccccc3c21 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-a71453b19c6d45048d89d67e928352f6 | CC(C)(C)OC(=O)NCCOCCNc1c(N)cnc2ccccc12>>CC(C)(C)OC(=O)NCCOCCn1cnc2cnc3ccccc3c21 | C.Cl.[NH+]1=CC=CC=C1.NC=1C=NC2=CC=CC=C2C1NCCOCCNC(OC(C)(C)C)=O.C(C)OC(OCC)OCC>>N1(C=NC=2C=NC=3C=CC=CC3C21)CCOCCNC(OC(C)(C)C)=O | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][CH2:9][CH2:10][O:11][CH2:12][CH2:13][NH:14][c:26]1[c:17]([NH2:16])[cH:18][n:19][c:20]2[cH:21][cH:22][cH:23][cH:24][c:25]21>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][CH2:9][CH2:10][O:11][CH2:12][CH2:13][n:14]1[cH:15][n:16][c:17]2[cH:18][n:19][c:20]3[cH... | CC(C)(C)OC(=O)NCCOCCNc1c(N)cnc2ccccc12 | CC(C)(C)OC(=O)NCCOCCn1cnc2cnc3ccccc3c21 | null | null | C1(=CC=CC=C1)C.CO | Aromatic Heterocycle Formation | OtherReaction | 26779edfcc2b370e3e3dc285e0fedfbcf04e6b6c7fd46f2674bab3f061a7b270 | c12bf4e666f812d0e692aca3756678364265d1c8b3469e9563c84f9ed1df94d2 | c1ccc2c(c1)ncc1nc[nH]c12 | [C:1]-[C:2]-[NH;D2;+0:3]-[c:4]1:[c:5]:[c:6]:[#7;a:7]:[c:8]:[c:9]:1-[NH2;D1;+0:10]>>[C:1]-[C:2]-[n;H0;D3;+0:3]1:[c:11]:[n;H0;D2;+0:10]:[c:9]2:[c:8]:[#7;a:7]:[c:6]:[c:5]:[c:4]:2:1 | 73.6 | [{"value": 73.6, "product": "N1(C=NC=2C=NC=3C=CC=CC3C21)CCOCCNC(OC(C)(C)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | A solution of tert-butyl 2-{2-[(3-aminoquinolin-4-yl)amino]ethoxy}ethylcarbamate (6.92 g, 20.0 mmol) in 100 mL of toluene was treated with triethylorthoformate (4.65 mL, 28.0 mmol) and the reaction mixture was heated to reflux. A 100 mg portion of pyridinium hydrochloride was then added and refluxing was continued for ... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Secondary amine | null | c1ccc2ncccc2c1 | c1ccc2c(c1)ncc1nc[nH]c12 | c1ccc2c(c1)ncc1nc[nH]c12 | Other | C1(=CC=CC=C1)C.CO | null | 2 | CC(C)(C)OC(=O)NCCOCCNc1c(N)cnc2ccccc12>C1(=CC=CC=C1)C.CO>CC(C)(C)OC(=O)NCCOCCn1cnc2cnc3ccccc3c21 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-3fbe7793ca8944c990104b91c939d97c | CC(C)(C)OC(=O)NCCOCCn1cnc2cnc3ccccc3c21.O=C(OO)c1cccc(Cl)c1>>CC(C)(C)OC(=O)NCCOCCn1cnc2c[n+]([O-])c3ccccc3c21 | C(=O)(O)[O-].[Na+].N1(C=NC=2C=NC=3C=CC=CC3C21)CCOCCNC(OC(C)(C)C)=O.C1=CC(=CC(=C1)Cl)C(=O)OO>>[O-][N+]1=CC2=C(C=3C=CC=CC13)N(C=N2)CCOCCNC(OC(C)(C)C)=O | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][CH2:9][CH2:10][O:11][CH2:12][CH2:13][n:14]1[cH:15][n:16][c:17]2[cH:18][n:19][c:21]3[cH:22][cH:23][cH:24][cH:25][c:26]3[c:27]12.O=C(O[OH:20])c1cccc(Cl)c1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][CH2:9][CH2:10][O:11][CH2:12][CH2:13][n:14]1[cH:15][n:16]... | CC(C)(C)OC(=O)NCCOCCn1cnc2cnc3ccccc3c21.O=C(OO)c1cccc(Cl)c1 | CC(C)(C)OC(=O)NCCOCCn1cnc2c[n+]([O-])c3ccccc3c21 | null | null | C(Cl)Cl | Miscellaneous | OtherReaction | cad786c9409a25c8ce82607722e58ecf517f297ff4b081be9d5601c67b613c7c | 98b338a9d01476c0929fd5672e7509121bfe69600fd72e4d1cc6f1782e2d05d9 | c1ccc2c(c1)[nH+]cc1nc[nH]c12 | Cl-c1:c:c:c:c(-C(=O)-O-[OH;D1;+0:1]):c:1.[c:2]:[c:3]1:[c:4]:[c:5]2:[#7;a:6]:[c:7]:[#7;a:8]:[c:9]:2:[c:10]:[n;H0;D2;+0:11]:1>>[O-;H0;D1:1]-[n+;H0;D3:11]1:[c:10]:[c:9]2:[#7;a:8]:[c:7]:[#7;a:6]:[c:5]:2:[c:4]:[c:3]:1:[c:2] | 84 | [{"value": 84.0, "product": "[O-][N+]1=CC2=C(C=3C=CC=CC13)N(C=N2)CCOCCNC(OC(C)(C)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | A solution of tert-butyl 2-[2-(1H-imidazo[4,5-c]quinolin-1-yl)ethoxy]ethylcarbamate (5.25 g, 14.7 mmol) in 200 mL of CH2Cl2 was treated with MCPBA (77%, 3.63 g, 16.3 mmol). After stirring overnight, the reaction mixture was treated with saturated NaHCO3 solution and the layers were separated. The organic portion was wa... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Peroxide | null | c1ccc2c(c1)ncc1nc[nH]c12.c1ccccc1 | c1ccc2c(c1)[n+]cc1nc[nH]c12 | c1ccc2c(c1)[n+]cc1nc[nH]c12 | HCl | C(Cl)Cl | null | 8 | CC(C)(C)OC(=O)NCCOCCn1cnc2cnc3ccccc3c21.O=C(OO)c1cccc(Cl)c1>C(Cl)Cl>CC(C)(C)OC(=O)NCCOCCn1cnc2c[n+]([O-])c3ccccc3c21 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-be86840fafae4e68922eca13ffd0dc40 | CC(C)(C)OC(=O)NCCOCCn1cnc2c[n+]([O-])c3ccccc3c21.[NH4+]>>CC(C)(C)OC(=O)NCCOCCn1cnc2c(N)nc3ccccc3c21 | [NH4+].[OH-].[O-][N+]1=CC2=C(C=3C=CC=CC13)N(C=N2)CCOCCNC(OC(C)(C)C)=O.[NH4+].[OH-].C(Cl)Cl.C1(=CC=C(C=C1)S(=O)(=O)Cl)C>>NC1=NC=2C=CC=CC2C2=C1N=CN2CCOCCNC(OC(C)(C)C)=O | [O-][n+:20]1[cH:18][c:17]2[n:16][cH:15][n:14]([CH2:13][CH2:12][O:11][CH2:10][CH2:9][NH:8][C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[c:27]2[c:26]2[c:21]1[cH:22][cH:23][cH:24][cH:25]2.[NH4+:19]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][CH2:9][CH2:10][O:11][CH2:12][CH2:13][n:14]1[cH:15][n:16][c:17]2[c... | CC(C)(C)OC(=O)NCCOCCn1cnc2c[n+]([O-])c3ccccc3c21.[NH4+] | CC(C)(C)OC(=O)NCCOCCn1cnc2c(N)nc3ccccc3c21 | null | null | ClCCCl | Protection | OtherReaction | 4cb72433be7a0d843d29843bff9411bfad039899e2cd9347e2313d8f7a557ce7 | bf08eb59ebe808bce722373055de9689551bb60b2522898c82bc26646fc1fe40 | c1ccc2c(c1)ncc1nc[nH]c12 | [C:1]-[#7;a:2]1:[c:3]:[#7;a:4]:[c:5]2:[cH;D2;+0:6]:[n+;H0;D3:7](-[O-]):[c:8](:[c:9]):[c:10]:[c:11]:1:2.[NH4+;D0:12]>>[C:1]-[#7;a:2]1:[c:3]:[#7;a:4]:[c:5]2:[c:11]:1:[c:10]:[c:8](:[c:9]):[n;H0;D2;+0:7]:[c;H0;D3;+0:6]:2-[NH2;D1;+0:12] | null | [] | null | null | 3 | HOUR | A solution of tert-butyl 2-[2-(5-oxido-1H-imidazo[4,5-c]quinolin-1-yl)ethoxy]ethylcarbamate (4.60 g, 12.4 mmol) in 150 mL of 1,2-dichloroethane was heated to 80° C. and treated with 10 mL of concentrated NH4OH solution. To the rapidly stirred solution was added solid p-toluenesulfonyl chloride (2.71 g, 14.2 mmol) over ... | 10.6084/m9.figshare.5104873.v1 | null | null | Primary amine | c1ccc2c(c1)[n+]cc1[nH]cnc12 | c1nc2ccccc2c2[nH]cnc12 | c1nc2ccccc2c2[nH]cnc12 | HO- | ClCCCl | null | 3 | CC(C)(C)OC(=O)NCCOCCn1cnc2c[n+]([O-])c3ccccc3c21.[NH4+]>ClCCCl>CC(C)(C)OC(=O)NCCOCCn1cnc2c(N)nc3ccccc3c21 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-1ce376451fa04f1bb3754c5fca6b00e9 | CC(C)(C)OC(=O)NCCOCCNc1c(N)cnc2ccccc12.COC(C)(OC)OC>>Cc1nc2cnc3ccccc3c2n1CCOCCNC(=O)OC(C)(C)C | Cl.[NH+]1=CC=CC=C1.NC=1C=NC2=CC=CC=C2C1NCCOCCNC(OC(C)(C)C)=O.C(C)(OC)(OC)OC>>CC=1N(C2=C(C=NC=3C=CC=CC23)N1)CCOCCNC(OC(C)(C)C)=O | [NH2:3][c:4]1[cH:5][n:6][c:7]2[cH:8][cH:9][cH:10][cH:11][c:12]2[c:13]1[NH:14][CH2:15][CH2:16][O:17][CH2:18][CH2:19][NH:20][C:21](=[O:22])[O:23][C:24]([CH3:25])([CH3:26])[CH3:27].CO[C:2](OC)(OC)[CH3:1]>>[CH3:1][c:2]1[n:3][c:4]2[cH:5][n:6][c:7]3[cH:8][cH:9][cH:10][cH:11][c:12]3[c:13]2[n:14]1[CH2:15][CH2:16][O:17][CH2:18]... | CC(C)(C)OC(=O)NCCOCCNc1c(N)cnc2ccccc12.COC(C)(OC)OC | Cc1nc2cnc3ccccc3c2n1CCOCCNC(=O)OC(C)(C)C | null | null | ClCCCl | Aromatic Heterocycle Formation | OtherReaction | af7d6de7ca5153ecd31a13d7075f2969261301df4b656bfec36bc67fd1ea176b | a60e703c3cf5c0d933aa031358d338c45d96ec82dec3fc2d9f5dce06b9dcc651 | c1ccc2c(c1)ncc1nc[nH]c12 | C-O-[C;H0;D4;+0:1](-[C;D1;H3:2])(-O-C)-O-C.[C:3]-[C:4]-[NH;D2;+0:5]-[c:6]1:[c:7]:[c:8]:[#7;a:9]:[c:10]:[c:11]:1-[NH2;D1;+0:12]>>[C:3]-[C:4]-[n;H0;D3;+0:5]1:[c:6]2:[c:7]:[c:8]:[#7;a:9]:[c:10]:[c:11]:2:[n;H0;D2;+0:12]:[c;H0;D3;+0:1]:1-[C;D1;H3:2] | 83.5 | [{"value": 83.5, "product": "CC=1N(C2=C(C=NC=3C=CC=CC23)N1)CCOCCNC(OC(C)(C)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 4 | HOUR | A solution of tert-butyl 2-{2-[(3-aminoquinolin-4-yl)amino]ethoxy}ethylcarbamate (12.05 g, 34.8 mmol) in 200 mL of 1,2-dichloroethane was treated with trimethyl orthoacetate (5.50 mL, 43.2 mmol) and the reaction mixture was heated to reflux. A 100 mg portion of pyridinium hydrochloride was then added and refluxing was ... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether.Ether.Primary amine.Secondary amine | null | c1ccc2ncccc2c1 | c1nc2c(cnc3ccccc32)[nH]1 | c1nc2c(cnc3ccccc32)[nH]1 | HO- | ClCCCl | null | 4 | CC(C)(C)OC(=O)NCCOCCNc1c(N)cnc2ccccc12.COC(C)(OC)OC>ClCCCl>Cc1nc2cnc3ccccc3c2n1CCOCCNC(=O)OC(C)(C)C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-9c2d1c90c4e84cef81a46bfd4a33ed83 | Cc1nc2cnc3ccccc3c2n1CCOCCNC(=O)OC(C)(C)C>>Cc1nc2c[n+]([O-])c3ccccc3c2n1CCOCCNC(=O)OC(C)(C)C | CC=1N(C2=C(C=NC=3C=CC=CC23)N1)CCOCCNC(OC(C)(C)C)=O.ClC=1C=C(C(=O)OO)C=CC1>>CC=1N(C2=C(C=[N+](C=3C=CC=CC23)[O-])N1)CCOCCNC(OC(C)(C)C)=O | [CH3:1][c:2]1[n:3][c:4]2[cH:5][n:6][c:8]3[cH:9][cH:10][cH:11][cH:12][c:13]3[c:14]2[n:15]1[CH2:16][CH2:17][O:18][CH2:19][CH2:20][NH:21][C:22](=[O:23])[O:24][C:25]([CH3:26])([CH3:27])[CH3:28]>>[CH3:1][c:2]1[n:3][c:4]2[cH:5][n+:6]([O-:7])[c:8]3[cH:9][cH:10][cH:11][cH:12][c:13]3[c:14]2[n:15]1[CH2:16][CH2:17][O:18][CH2:19][... | Cc1nc2cnc3ccccc3c2n1CCOCCNC(=O)OC(C)(C)C | Cc1nc2c[n+]([O-])c3ccccc3c2n1CCOCCNC(=O)OC(C)(C)C | null | null | C(Cl)(Cl)Cl | Functional Group Interconversion | OtherReaction | d6328bcdf13aade6d233961c67aa0027be57934158b58a73811db431a33571a7 | f1bbf9aa3c82f5e49be9f6d53533b6bb152f359232b6d32090c168949766aa71 | c1ccc2c(c1)[nH+]cc1nc[nH]c12 | [c:1]:[c:2]1:[c:3]:[c:4]2:[#7;a:5]:[c:6]:[#7;a:7]:[c:8]:2:[c:9]:[n;H0;D2;+0:10]:1>>[O;-;D1;H0:11]-[n+;H0;D3:10]1:[c:9]:[c:8]2:[#7;a:7]:[c:6]:[#7;a:5]:[c:4]:2:[c:3]:[c:2]:1:[c:1] | 100 | [{"value": 100.0, "product": "CC=1N(C2=C(C=[N+](C=3C=CC=CC23)[O-])N1)CCOCCNC(OC(C)(C)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1.5 | HOUR | A solution of tert-butyl 2-[2-(2-methyl-1H-imidazo[4,5-c]quinolin-1-yl)ethoxy]ethylcarbamate (10.75 g, 29.0 mmol) in 150 mL of CHCl3 was chilled in an ice water bath. The solution was treated with 3-chloroperoxybenzoic acid (MCPBA, 70%, 10.73 g, 43.5 mmol). After stirring for 1.5 h, the reaction mixture was washed with... | 10.6084/m9.figshare.5104873.v1 | null | null | null | c1nc2c(cnc3ccccc32)[nH]1 | c1nc2c(c[n+]c3ccccc32)[nH]1 | c1nc2c(c[n+]c3ccccc32)[nH]1 | null | C(Cl)(Cl)Cl | null | 1.5 | Cc1nc2cnc3ccccc3c2n1CCOCCNC(=O)OC(C)(C)C>C(Cl)(Cl)Cl>Cc1nc2c[n+]([O-])c3ccccc3c2n1CCOCCNC(=O)OC(C)(C)C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-ad22fad7618b47e8ab9aa84a2b90f1a4 | Cc1nc2c[n+]([O-])c3ccccc3c2n1CCOCCNC(=O)OC(C)(C)C.[NH4+]>>Cc1nc2c(N)nc3ccccc3c2n1CCOCCNC(=O)OC(C)(C)C | C1(=CC=C(C=C1)S(=O)(=O)Cl)C.O.CC=1N(C2=C(C=[N+](C=3C=CC=CC23)[O-])N1)CCOCCNC(OC(C)(C)C)=O.[NH4+].[OH-]>>NC1=NC=2C=CC=CC2C2=C1N=C(N2CCOCCNC(OC(C)(C)C)=O)C | [O-][n+:7]1[cH:5][c:4]2[n:3][c:2]([CH3:1])[n:15]([CH2:16][CH2:17][O:18][CH2:19][CH2:20][NH:21][C:22](=[O:23])[O:24][C:25]([CH3:26])([CH3:27])[CH3:28])[c:14]2[c:13]2[c:8]1[cH:9][cH:10][cH:11][cH:12]2.[NH4+:6]>>[CH3:1][c:2]1[n:3][c:4]2[c:5]([NH2:6])[n:7][c:8]3[cH:9][cH:10][cH:11][cH:12][c:13]3[c:14]2[n:15]1[CH2:16][CH2:1... | Cc1nc2c[n+]([O-])c3ccccc3c2n1CCOCCNC(=O)OC(C)(C)C.[NH4+] | Cc1nc2c(N)nc3ccccc3c2n1CCOCCNC(=O)OC(C)(C)C | null | null | C(Cl)Cl | Protection | OtherReaction | 1a3560ac88422fd247b995f02bc4ff4290625edd39947787fab7dac607ad70df | bf08eb59ebe808bce722373055de9689551bb60b2522898c82bc26646fc1fe40 | c1ccc2c(c1)ncc1nc[nH]c12 | [C:1]-[#7;a:2]1:[c:3]:[#7;a:4]:[c:5]2:[cH;D2;+0:6]:[n+;H0;D3:7](-[O-]):[c:8](:[c:9]):[c:10]:[c:11]:1:2.[NH4+;D0:12]>>[C:1]-[#7;a:2]1:[c:3]:[#7;a:4]:[c:5]2:[c:11]:1:[c:10]:[c:8](:[c:9]):[n;H0;D2;+0:7]:[c;H0;D3;+0:6]:2-[NH2;D1;+0:12] | null | [] | null | null | null | null | A solution of tert-butyl 2-[2-(2-methyl-5-oxido-1H-imidazo[4,5-c]quinolin-1-yl)ethoxy]ethylcarbamate (11.21 g, 29.0 mmol) in 75 mL of CH2Cl2 was treated with 75 mL of concentrated NH4OH solution. The mixture was chilled in an ice water bath. To the rapidly stirred mixture was added solid p-toluenesulfonyl chloride (5.5... | 10.6084/m9.figshare.5104873.v1 | null | null | Primary amine | c1nc2c(c[n+]c3ccccc32)[nH]1 | c1nc2c(cnc3ccccc32)[nH]1 | c1nc2c(cnc3ccccc32)[nH]1 | HO- | C(Cl)Cl | null | null | Cc1nc2c[n+]([O-])c3ccccc3c2n1CCOCCNC(=O)OC(C)(C)C.[NH4+]>C(Cl)Cl>Cc1nc2c(N)nc3ccccc3c2n1CCOCCNC(=O)OC(C)(C)C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-0569a42b9c0347a4bad5f00be9b86b7b | CC(C)(C)OC(=O)NCCOCCNc1c(N)cnc2ccccc12.CCC(=O)Cl>>CCC(=O)Nc1cnc2ccccc2c1NCCOCCNC(=O)OC(C)(C)C | O.C(CC)(=O)Cl.NC=1C=NC2=CC=CC=C2C1NCCOCCNC(OC(C)(C)C)=O.C(C)N(CC)CC>>C(CC)(=O)NC=1C=NC2=CC=CC=C2C1NCCOCCNC(OC(C)(C)C)=O | [NH2:5][c:6]1[cH:7][n:8][c:9]2[cH:10][cH:11][cH:12][cH:13][c:14]2[c:15]1[NH:16][CH2:17][CH2:18][O:19][CH2:20][CH2:21][NH:22][C:23](=[O:24])[O:25][C:26]([CH3:27])([CH3:28])[CH3:29].Cl[C:3]([CH2:2][CH3:1])=[O:4]>>[CH3:1][CH2:2][C:3](=[O:4])[NH:5][c:6]1[cH:7][n:8][c:9]2[cH:10][cH:11][cH:12][cH:13][c:14]2[c:15]1[NH:16][CH2... | CC(C)(C)OC(=O)NCCOCCNc1c(N)cnc2ccccc12.CCC(=O)Cl | CCC(=O)Nc1cnc2ccccc2c1NCCOCCNC(=O)OC(C)(C)C | null | null | C(Cl)Cl | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | c1ccc2ncccc2c1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C;D1;H3:4].[NH2;D1;+0:5]-[c:6](:[c:7]):[c:8]:[#7;a:9]:[c:10]>>[C;D1;H3:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:5]-[c:6](:[c:7]):[c:8]:[#7;a:9]:[c:10] | 44.6 | [{"value": 44.6, "product": "C(CC)(=O)NC=1C=NC2=CC=CC=C2C1NCCOCCNC(OC(C)(C)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 18 | HOUR | A solution of tert-butyl 2-{2-[(3-aminoquinolin-4-yl)amino]ethoxy}ethylcarbamate (32.0 g, 92.0 mmol) in 300 mL of CH2Cl2 was treated with triethylamine (19.2 mL, 138.0 mmol). The reaction was chilled in an ice water bath and then propionyl chloride (9.40 mL, 108.2 mmol) was added dropwise. After stirring for 18 h, the ... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccc2ncccc2c1 | HCl | C(Cl)Cl | null | 18 | CC(C)(C)OC(=O)NCCOCCNc1c(N)cnc2ccccc12.CCC(=O)Cl>C(Cl)Cl>CCC(=O)Nc1cnc2ccccc2c1NCCOCCNC(=O)OC(C)(C)C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-571380899b164b708bcd1efb417dc5c2 | CCC(=O)Nc1cnc2ccccc2c1NCCOCCNC(=O)OC(C)(C)C>>CCc1nc2cnc3ccccc3c2n1CCOCCNC(=O)OC(C)(C)C | C(CC)(=O)NC=1C=NC2=CC=CC=C2C1NCCOCCNC(OC(C)(C)C)=O.C(C)N(CC)CC>>C(C)C=1N(C2=C(C=NC=3C=CC=CC23)N1)CCOCCNC(OC(C)(C)C)=O | O=[C:3]([CH2:2][CH3:1])[NH:4][c:5]1[cH:6][n:7][c:8]2[cH:9][cH:10][cH:11][cH:12][c:13]2[c:14]1[NH:15][CH2:16][CH2:17][O:18][CH2:19][CH2:20][NH:21][C:22](=[O:23])[O:24][C:25]([CH3:26])([CH3:27])[CH3:28]>>[CH3:1][CH2:2][c:3]1[n:4][c:5]2[cH:6][n:7][c:8]3[cH:9][cH:10][cH:11][cH:12][c:13]3[c:14]2[n:15]1[CH2:16][CH2:17][O:18]... | CCC(=O)Nc1cnc2ccccc2c1NCCOCCNC(=O)OC(C)(C)C | CCc1nc2cnc3ccccc3c2n1CCOCCNC(=O)OC(C)(C)C | null | null | CCO | Aromatic Heterocycle Formation | OtherReaction | 048882f89ec680a0d34f3902d9572ee75568aa993a5f9bf900f7615492f9fa85 | 71fdeda1d5481ba7466e825735d29b5ffca597c091e9548c43a80a0aea31b8a0 | c1ccc2c(c1)ncc1nc[nH]c12 | O=[C;H0;D3;+0:1](-[C:2]-[C;D1;H3:3])-[NH;D2;+0:4]-[c:5]1:[c:6]:[#7;a:7]:[c:8]:[c:9]:[c:10]:1-[NH;D2;+0:11]-[C:12]-[C:13]>>[C:13]-[C:12]-[n;H0;D3;+0:11]1:[c:10]2:[c:9]:[c:8]:[#7;a:7]:[c:6]:[c:5]:2:[n;H0;D2;+0:4]:[c;H0;D3;+0:1]:1-[C:2]-[C;D1;H3:3] | 96.1 | [{"value": 96.1, "product": "C(C)C=1N(C2=C(C=NC=3C=CC=CC23)N1)CCOCCNC(OC(C)(C)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | DAY | A solution of tert-butyl 2-(2-{[3-(propionylamino)quinolin-4-yl]amino}ethoxy)ethylcarbamate (15.00 g, 37.3 mmol) in 200 mL of EtOH was treated with triethylamine (13.0 mL, 93.2 mmol). The reaction was heated to reflux with stirring. After 3 days, the reaction was concentrated, triturated with ether and filtered to yiel... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide.Secondary amine | null | c1ccc2ncccc2c1 | c1nc2c(cnc3ccccc32)[nH]1 | c1nc2c(cnc3ccccc32)[nH]1 | HO- | CCO | null | 72 | CCC(=O)Nc1cnc2ccccc2c1NCCOCCNC(=O)OC(C)(C)C>CCO>CCc1nc2cnc3ccccc3c2n1CCOCCNC(=O)OC(C)(C)C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-910b95784d7147cbbcbb86c388961372 | CCc1nc2cnc3ccccc3c2n1CCOCCNC(=O)OC(C)(C)C>>CCc1nc2c[n+]([O-])c3ccccc3c2n1CCOCCNC(=O)OC(C)(C)C | O.C(C)C=1N(C2=C(C=NC=3C=CC=CC23)N1)CCOCCNC(OC(C)(C)C)=O.ClC=1C=C(C(=O)OO)C=CC1>>C(C)C=1N(C2=C(C=[N+](C=3C=CC=CC23)[O-])N1)CCOCCNC(OC(C)(C)C)=O | [CH3:1][CH2:2][c:3]1[n:4][c:5]2[cH:6][n:7][c:9]3[cH:10][cH:11][cH:12][cH:13][c:14]3[c:15]2[n:16]1[CH2:17][CH2:18][O:19][CH2:20][CH2:21][NH:22][C:23](=[O:24])[O:25][C:26]([CH3:27])([CH3:28])[CH3:29]>>[CH3:1][CH2:2][c:3]1[n:4][c:5]2[cH:6][n+:7]([O-:8])[c:9]3[cH:10][cH:11][cH:12][cH:13][c:14]3[c:15]2[n:16]1[CH2:17][CH2:18... | CCc1nc2cnc3ccccc3c2n1CCOCCNC(=O)OC(C)(C)C | CCc1nc2c[n+]([O-])c3ccccc3c2n1CCOCCNC(=O)OC(C)(C)C | null | null | C(Cl)(Cl)Cl | Functional Group Interconversion | OtherReaction | d6328bcdf13aade6d233961c67aa0027be57934158b58a73811db431a33571a7 | f1bbf9aa3c82f5e49be9f6d53533b6bb152f359232b6d32090c168949766aa71 | c1ccc2c(c1)[nH+]cc1nc[nH]c12 | [c:1]:[c:2]1:[c:3]:[c:4]2:[#7;a:5]:[c:6]:[#7;a:7]:[c:8]:2:[c:9]:[n;H0;D2;+0:10]:1>>[O;-;D1;H0:11]-[n+;H0;D3:10]1:[c:9]:[c:8]2:[#7;a:7]:[c:6]:[#7;a:5]:[c:4]:2:[c:3]:[c:2]:1:[c:1] | 100.1 | [{"value": 100.1, "product": "C(C)C=1N(C2=C(C=[N+](C=3C=CC=CC23)[O-])N1)CCOCCNC(OC(C)(C)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | A solution of tert-butyl 2-[2-(2-ethyl-1H-imidazo[4,5-c]quinolin-1-yl)ethoxy]ethylcarbamate (13.78 g 35.8 mmol) in 175 mL of CHCl3 was treated with 3-chloroperoxybenzoic acid (MCPBA, 70%, 10.28 g, 41.7 mmol). After stirring for 3 h, the reaction mixture was treated with water (100 mL) and CHCl3 (50 mL) and the layers w... | 10.6084/m9.figshare.5104873.v1 | null | null | null | c1nc2c(cnc3ccccc32)[nH]1 | c1nc2c(c[n+]c3ccccc32)[nH]1 | c1nc2c(c[n+]c3ccccc32)[nH]1 | null | C(Cl)(Cl)Cl | null | 3 | CCc1nc2cnc3ccccc3c2n1CCOCCNC(=O)OC(C)(C)C>C(Cl)(Cl)Cl>CCc1nc2c[n+]([O-])c3ccccc3c2n1CCOCCNC(=O)OC(C)(C)C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-e3234ef3a01a4bbdb5857f11ce2d2695 | CCc1nc2c[n+]([O-])c3ccccc3c2n1CCOCCNC(=O)OC(C)(C)C.[NH4+]>>CCc1nc2c(N)nc3ccccc3c2n1CCOCCNC(=O)OC(C)(C)C | C1(=CC=C(C=C1)S(=O)(=O)Cl)C.O.C(C)C=1N(C2=C(C=[N+](C=3C=CC=CC23)[O-])N1)CCOCCNC(OC(C)(C)C)=O.[NH4+].[OH-]>>NC1=NC=2C=CC=CC2C2=C1N=C(N2CCOCCNC(OC(C)(C)C)=O)CC | [O-][n+:8]1[cH:6][c:5]2[n:4][c:3]([CH2:2][CH3:1])[n:16]([CH2:17][CH2:18][O:19][CH2:20][CH2:21][NH:22][C:23](=[O:24])[O:25][C:26]([CH3:27])([CH3:28])[CH3:29])[c:15]2[c:14]2[c:9]1[cH:10][cH:11][cH:12][cH:13]2.[NH4+:7]>>[CH3:1][CH2:2][c:3]1[n:4][c:5]2[c:6]([NH2:7])[n:8][c:9]3[cH:10][cH:11][cH:12][cH:13][c:14]3[c:15]2[n:16... | CCc1nc2c[n+]([O-])c3ccccc3c2n1CCOCCNC(=O)OC(C)(C)C.[NH4+] | CCc1nc2c(N)nc3ccccc3c2n1CCOCCNC(=O)OC(C)(C)C | null | null | C(Cl)Cl | Protection | OtherReaction | 1a3560ac88422fd247b995f02bc4ff4290625edd39947787fab7dac607ad70df | bf08eb59ebe808bce722373055de9689551bb60b2522898c82bc26646fc1fe40 | c1ccc2c(c1)ncc1nc[nH]c12 | [C:1]-[#7;a:2]1:[c:3]:[#7;a:4]:[c:5]2:[cH;D2;+0:6]:[n+;H0;D3:7](-[O-]):[c:8](:[c:9]):[c:10]:[c:11]:1:2.[NH4+;D0:12]>>[C:1]-[#7;a:2]1:[c:3]:[#7;a:4]:[c:5]2:[c:11]:1:[c:10]:[c:8](:[c:9]):[n;H0;D2;+0:7]:[c;H0;D3;+0:6]:2-[NH2;D1;+0:12] | null | [] | null | null | 30 | MINUTE | A solution of tert-butyl 2-[2-(2-ethyl-5-oxido-1H-imidazo[4,5-c]quinolin-1-yl)ethoxy]ethylcarbamate (14.3 g, 35.8 mmol) in 90 mL of CH2Cl2 was treated with 90 mL of concentrated NH4OH solution. The mixture was chilled in an ice water bath. To the rapidly stirred mixture was added solid p-toluenesulfonyl chloride (7.05 ... | 10.6084/m9.figshare.5104873.v1 | null | null | Primary amine | c1nc2c(c[n+]c3ccccc32)[nH]1 | c1nc2c(cnc3ccccc32)[nH]1 | c1nc2c(cnc3ccccc32)[nH]1 | HO- | C(Cl)Cl | null | 0.5 | CCc1nc2c[n+]([O-])c3ccccc3c2n1CCOCCNC(=O)OC(C)(C)C.[NH4+]>C(Cl)Cl>CCc1nc2c(N)nc3ccccc3c2n1CCOCCNC(=O)OC(C)(C)C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-026743350d314774b776e8b50d32dafc | CCc1nc2c(N)nc3ccccc3c2n1CCOCCNC(=O)OC(C)(C)C>>CCc1nc2c(N)nc3ccccc3c2n1CCOCCN | NC1=NC=2C=CC=CC2C2=C1N=C(N2CCOCCNC(OC(C)(C)C)=O)CC>>NCCOCCN1C(=NC=2C(=NC=3C=CC=CC3C21)N)CC | CC(C)(C)OC(=O)[NH:22][CH2:21][CH2:20][O:19][CH2:18][CH2:17][n:16]1[c:3]([CH2:2][CH3:1])[n:4][c:5]2[c:6]([NH2:7])[n:8][c:9]3[cH:10][cH:11][cH:12][cH:13][c:14]3[c:15]21>>[CH3:1][CH2:2][c:3]1[n:4][c:5]2[c:6]([NH2:7])[n:8][c:9]3[cH:10][cH:11][cH:12][cH:13][c:14]3[c:15]2[n:16]1[CH2:17][CH2:18][O:19][CH2:20][CH2:21][NH2:22] | CCc1nc2c(N)nc3ccccc3c2n1CCOCCNC(=O)OC(C)(C)C | CCc1nc2c(N)nc3ccccc3c2n1CCOCCN | null | null | Cl.CCO | Reduction | Hydrogenolysis of amides/imides/carbamates | 3c33dd2a2d355ee5ba0287367e209aa147a39aa00607f0c95fb2bf1ade45d014 | c5b5dffe7dd8beebdc1baa8b5b05300a9f7079e65dcfd42ade6f8a77ff09537d | c1ccc2c(c1)ncc1nc[nH]c12 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[C:2]-[C:3]>>[C:3]-[C:2]-[NH2;D1;+0:1] | 94.5 | [{"value": 94.5, "product": "NCCOCCN1C(=NC=2C(=NC=3C=CC=CC3C21)N)CC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | Tert-butyl 2-[2-(4-amino-2-ethyl-1H-imidazo[4,5-c]quinolin-1-yl)ethoxy]ethylcarbamate (9.35 g, 23.4 mmol) was suspended in 150 mL of 2M HCl in EtOH and the mixture was heated to reflux with stirring. After 2 h, the reaction was cooled to room temperature and the HCl salt of the product was collected by vacuum filtratio... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Primary amine | null | null | c1nc2c(cnc3ccccc32)[nH]1 | HO- | Cl.CCO | null | 2 | CCc1nc2c(N)nc3ccccc3c2n1CCOCCNC(=O)OC(C)(C)C>Cl.CCO>CCc1nc2c(N)nc3ccccc3c2n1CCOCCN |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-5961be4f5d6142b394967d6ed4ff22aa | CC(C)(C)OC(=O)NCCOCCNc1c(N)cnc2ccccc12.CCOCC(=O)Cl>>CCOCc1nc2cnc3ccccc3c2n1CCOCCNC(=O)OC(C)(C)C | NC=1C=NC2=CC=CC=C2C1NCCOCCNC(OC(C)(C)C)=O.C(C)OCC(=O)Cl>>C(C)OCC=1N(C2=C(C=NC=3C=CC=CC23)N1)CCOCCNC(OC(C)(C)C)=O | [NH2:6][c:7]1[cH:8][n:9][c:10]2[cH:11][cH:12][cH:13][cH:14][c:15]2[c:16]1[NH:17][CH2:18][CH2:19][O:20][CH2:21][CH2:22][NH:23][C:24](=[O:25])[O:26][C:27]([CH3:28])([CH3:29])[CH3:30].O=[C:5](Cl)[CH2:4][O:3][CH2:2][CH3:1]>>[CH3:1][CH2:2][O:3][CH2:4][c:5]1[n:6][c:7]2[cH:8][n:9][c:10]3[cH:11][cH:12][cH:13][cH:14][c:15]3[c:1... | CC(C)(C)OC(=O)NCCOCCNc1c(N)cnc2ccccc12.CCOCC(=O)Cl | CCOCc1nc2cnc3ccccc3c2n1CCOCCNC(=O)OC(C)(C)C | null | CN(C1=CC=NC=C1)C | N1=CC=CC=C1 | Aromatic Heterocycle Formation | OtherReaction | 2849961f1d737a23d71906fe74b0976730547255ac052bf4a7367ba2be72dd8e | 56ef83dfadec35a1cf1db968b807e178cc4924ce15bf36d774883783cef0f450 | c1ccc2c(c1)ncc1nc[nH]c12 | Cl-[C;H0;D3;+0:1](=O)-[C:2]-[#8:3].[C:4]-[C:5]-[NH;D2;+0:6]-[c:7]1:[c:8]:[c:9]:[#7;a:10]:[c:11]:[c:12]:1-[NH2;D1;+0:13]>>[#8:3]-[C:2]-[c;H0;D3;+0:1]1:[n;H0;D2;+0:13]:[c:12]2:[c:11]:[#7;a:10]:[c:9]:[c:8]:[c:7]:2:[n;H0;D3;+0:6]:1-[C:5]-[C:4] | 71.6 | [{"value": 71.6, "product": "C(C)OCC=1N(C2=C(C=NC=3C=CC=CC23)N1)CCOCCNC(OC(C)(C)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | A solution of tert-butyl 2-{2-[(3-aminoquinolin-4-yl)amino]ethoxy}ethylcarbamate (18.04 g, 52.1 mmol) in 180 mL of pyridine was treated with 50 mg of 4-dimethylaminopyridine and chilled in an ice water bath. 2-ethoxyacetyl chloride (6.44 g, 52.6 mmol) was added dropwise to the solution. The reaction was stirred at room... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine.Secondary amine | null | c1ccc2ncccc2c1 | c1nc2c(cnc3ccccc32)[nH]1 | c1nc2c(cnc3ccccc32)[nH]1 | HCl | CN(C1=CC=NC=C1)C.N1=CC=CC=C1 | null | 3 | CC(C)(C)OC(=O)NCCOCCNc1c(N)cnc2ccccc12.CCOCC(=O)Cl>CN(C1=CC=NC=C1)C.N1=CC=CC=C1>CCOCc1nc2cnc3ccccc3c2n1CCOCCNC(=O)OC(C)(C)C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-07073e660b9b4e25bfb17ed15f86f7c0 | CCOCc1nc2cnc3ccccc3c2n1CCOCCNC(=O)OC(C)(C)C.O=C(OO)c1cccc(Cl)c1>>CCOCc1nc2c[n+]([O-])c3ccccc3c2n1CCOCCNC(=O)OC(C)(C)C | O.C(C)OCC=1N(C2=C(C=NC=3C=CC=CC23)N1)CCOCCNC(OC(C)(C)C)=O.ClC=1C=C(C(=O)OO)C=CC1>>C(C)OCC=1N(C2=C(C=[N+](C=3C=CC=CC23)[O-])N1)CCOCCNC(OC(C)(C)C)=O | [CH3:1][CH2:2][O:3][CH2:4][c:5]1[n:6][c:7]2[cH:8][n:9][c:11]3[cH:12][cH:13][cH:14][cH:15][c:16]3[c:17]2[n:18]1[CH2:19][CH2:20][O:21][CH2:22][CH2:23][NH:24][C:25](=[O:26])[O:27][C:28]([CH3:29])([CH3:30])[CH3:31].O=C(O[OH:10])c1cccc(Cl)c1>>[CH3:1][CH2:2][O:3][CH2:4][c:5]1[n:6][c:7]2[cH:8][n+:9]([O-:10])[c:11]3[cH:12][cH:... | CCOCc1nc2cnc3ccccc3c2n1CCOCCNC(=O)OC(C)(C)C.O=C(OO)c1cccc(Cl)c1 | CCOCc1nc2c[n+]([O-])c3ccccc3c2n1CCOCCNC(=O)OC(C)(C)C | null | null | C(Cl)(Cl)Cl | Miscellaneous | OtherReaction | 86abb75bf448eea8ddd78de30fcfc7b06bb61e46f725af6f1625e0dd9537993c | 98b338a9d01476c0929fd5672e7509121bfe69600fd72e4d1cc6f1782e2d05d9 | c1ccc2c(c1)[nH+]cc1nc[nH]c12 | Cl-c1:c:c:c:c(-C(=O)-O-[OH;D1;+0:1]):c:1.[c:2]:[c:3]1:[c:4]:[c:5]2:[#7;a:6]:[c:7]:[#7;a:8]:[c:9]:2:[c:10]:[n;H0;D2;+0:11]:1>>[O-;H0;D1:1]-[n+;H0;D3:11]1:[c:10]:[c:9]2:[#7;a:8]:[c:7]:[#7;a:6]:[c:5]:2:[c:4]:[c:3]:1:[c:2] | 100 | [{"value": 100.0, "product": "C(C)OCC=1N(C2=C(C=[N+](C=3C=CC=CC23)[O-])N1)CCOCCNC(OC(C)(C)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1.5 | HOUR | A solution of tert-butyl 2-{2-[2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl]ethoxy}ethylcarbamate (15.47 g, 37.3 mmol) in 150 mL of CHCl3 was treated with 3-chloroperoxybenzoic acid (MCPBA, 70%, 15.12 g, 61.3 mmol). After stirring for 1.5 h, the reaction mixture was treated with water (100 mL) and CHCl3 (50 mL) and ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Peroxide | null | c1nc2c(cnc3ccccc32)[nH]1.c1ccccc1 | c1nc2c(c[n+]c3ccccc32)[nH]1 | c1nc2c(c[n+]c3ccccc32)[nH]1 | HCl | C(Cl)(Cl)Cl | null | 1.5 | CCOCc1nc2cnc3ccccc3c2n1CCOCCNC(=O)OC(C)(C)C.O=C(OO)c1cccc(Cl)c1>C(Cl)(Cl)Cl>CCOCc1nc2c[n+]([O-])c3ccccc3c2n1CCOCCNC(=O)OC(C)(C)C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-12ef87c0fecb4344b0ed4f6da7392c8a | CCOCc1nc2c[n+]([O-])c3ccccc3c2n1CCOCCNC(=O)OC(C)(C)C.[NH4+]>>CCOCc1nc2c(N)nc3ccccc3c2n1CCOCCNC(=O)OC(C)(C)C | C1(=CC=C(C=C1)S(=O)(=O)Cl)C.O.C(C)OCC=1N(C2=C(C=[N+](C=3C=CC=CC23)[O-])N1)CCOCCNC(OC(C)(C)C)=O.[NH4+].[OH-]>>NC1=NC=2C=CC=CC2C2=C1N=C(N2CCOCCNC(OC(C)(C)C)=O)COCC | [O-][n+:10]1[cH:8][c:7]2[n:6][c:5]([CH2:4][O:3][CH2:2][CH3:1])[n:18]([CH2:19][CH2:20][O:21][CH2:22][CH2:23][NH:24][C:25](=[O:26])[O:27][C:28]([CH3:29])([CH3:30])[CH3:31])[c:17]2[c:16]2[c:11]1[cH:12][cH:13][cH:14][cH:15]2.[NH4+:9]>>[CH3:1][CH2:2][O:3][CH2:4][c:5]1[n:6][c:7]2[c:8]([NH2:9])[n:10][c:11]3[cH:12][cH:13][cH:1... | CCOCc1nc2c[n+]([O-])c3ccccc3c2n1CCOCCNC(=O)OC(C)(C)C.[NH4+] | CCOCc1nc2c(N)nc3ccccc3c2n1CCOCCNC(=O)OC(C)(C)C | null | null | C(Cl)Cl | Protection | OtherReaction | 1a3560ac88422fd247b995f02bc4ff4290625edd39947787fab7dac607ad70df | bf08eb59ebe808bce722373055de9689551bb60b2522898c82bc26646fc1fe40 | c1ccc2c(c1)ncc1nc[nH]c12 | [C:1]-[#7;a:2]1:[c:3]:[#7;a:4]:[c:5]2:[cH;D2;+0:6]:[n+;H0;D3:7](-[O-]):[c:8](:[c:9]):[c:10]:[c:11]:1:2.[NH4+;D0:12]>>[C:1]-[#7;a:2]1:[c:3]:[#7;a:4]:[c:5]2:[c:11]:1:[c:10]:[c:8](:[c:9]):[n;H0;D2;+0:7]:[c;H0;D3;+0:6]:2-[NH2;D1;+0:12] | null | [] | null | null | 30 | MINUTE | A solution of tert-butyl 2-{2-[2-(ethoxymethyl)-5-oxido-1H-imidazo[4,5-c]quinolin-1-yl]ethoxy}ethylcarbamate (16.06 g, 37.3 mmol) in 75 mL of CH2Cl2 was treated with 75 mL of concentrated NH4OH solution. The mixture was chilled in an ice water bath. To the rapidly stirred mixture was added solid p-toluenesulfonyl chlor... | 10.6084/m9.figshare.5104873.v1 | null | null | Primary amine | c1nc2c(c[n+]c3ccccc32)[nH]1 | c1nc2c(cnc3ccccc32)[nH]1 | c1nc2c(cnc3ccccc32)[nH]1 | HO- | C(Cl)Cl | null | 0.5 | CCOCc1nc2c[n+]([O-])c3ccccc3c2n1CCOCCNC(=O)OC(C)(C)C.[NH4+]>C(Cl)Cl>CCOCc1nc2c(N)nc3ccccc3c2n1CCOCCNC(=O)OC(C)(C)C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-07358473e4244b4fbb6a1a0e0af73249 | CCOCc1nc2c(N)nc3ccccc3c2n1CCOCCNC(=O)OC(C)(C)C>>CCOCc1nc2c(N)nc3ccccc3c2n1CCOCCN | NC1=NC=2C=CC=CC2C2=C1N=C(N2CCOCCNC(OC(C)(C)C)=O)COCC.CCOCC.C>>NCCOCCN1C(=NC=2C(=NC=3C=CC=CC3C21)N)COCC | CC(C)(C)OC(=O)[NH:24][CH2:23][CH2:22][O:21][CH2:20][CH2:19][n:18]1[c:5]([CH2:4][O:3][CH2:2][CH3:1])[n:6][c:7]2[c:8]([NH2:9])[n:10][c:11]3[cH:12][cH:13][cH:14][cH:15][c:16]3[c:17]21>>[CH3:1][CH2:2][O:3][CH2:4][c:5]1[n:6][c:7]2[c:8]([NH2:9])[n:10][c:11]3[cH:12][cH:13][cH:14][cH:15][c:16]3[c:17]2[n:18]1[CH2:19][CH2:20][O:... | CCOCc1nc2c(N)nc3ccccc3c2n1CCOCCNC(=O)OC(C)(C)C | CCOCc1nc2c(N)nc3ccccc3c2n1CCOCCN | null | null | Cl.CCO.CO | Reduction | Hydrogenolysis of amides/imides/carbamates | 3c33dd2a2d355ee5ba0287367e209aa147a39aa00607f0c95fb2bf1ade45d014 | c5b5dffe7dd8beebdc1baa8b5b05300a9f7079e65dcfd42ade6f8a77ff09537d | c1ccc2c(c1)ncc1nc[nH]c12 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[C:2]-[C:3]>>[C:3]-[C:2]-[NH2;D1;+0:1] | null | [] | null | null | 3 | HOUR | Tert-butyl 2-{2-[4-amino-2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl]ethoxy}ethylcarbamate (14.45 g, 33.6 mmol) was dissolved in 50 mL of 2M HCl in EtOH and the mixture was heated to reflux with stirring. After 3 h, the reaction was cooled to room temperature and treated with ether (100 mL). The HCl salt of the pro... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Primary amine | null | null | c1nc2c(cnc3ccccc32)[nH]1 | HO- | Cl.CCO.CO | null | 3 | CCOCc1nc2c(N)nc3ccccc3c2n1CCOCCNC(=O)OC(C)(C)C>Cl.CCO.CO>CCOCc1nc2c(N)nc3ccccc3c2n1CCOCCN |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-3571e8c7e7a2428fb31e2a319cae278e | Cc1nc2c(N)nc3ccccc3c2n1CCOCCN.O=C=Nc1ccccc1>>Cc1nc2c(N)nc3ccccc3c2n1CCOCCNC(=O)Nc1ccccc1 | C1(=CC=CC=C1)N=C=O.NCCOCCN1C(=NC=2C(=NC=3C=CC=CC3C21)N)C.C(C)N(CC)CC>>NC1=NC=2C=CC=CC2C2=C1N=C(N2CCOCCNC(=O)NC2=CC=CC=C2)C | [CH3:1][c:2]1[n:3][c:4]2[c:5]([NH2:6])[n:7][c:8]3[cH:9][cH:10][cH:11][cH:12][c:13]3[c:14]2[n:15]1[CH2:16][CH2:17][O:18][CH2:19][CH2:20][NH2:21].[C:22](=[O:23])=[N:24][c:25]1[cH:26][cH:27][cH:28][cH:29][cH:30]1>>[CH3:1][c:2]1[n:3][c:4]2[c:5]([NH2:6])[n:7][c:8]3[cH:9][cH:10][cH:11][cH:12][c:13]3[c:14]2[n:15]1[CH2:16][CH2... | Cc1nc2c(N)nc3ccccc3c2n1CCOCCN.O=C=Nc1ccccc1 | Cc1nc2c(N)nc3ccccc3c2n1CCOCCNC(=O)Nc1ccccc1 | null | null | CN1C(CCC1)=O | Acylation | Urea synthesis via isocyanate and primary amine | d39cd7dc52a79bb265ff8ef61ef7bf9dc7f7b5fb0150fcb4881bdfb18ab9c380 | a5dc801930c765d2a435a0a2973e50163c305ba8e7641d6adbcc1550b7b96de7 | O=C(NCCOCCn1cnc2cnc3ccccc3c21)Nc1ccccc1 | [C:1]-[C:2]-[NH2;D1;+0:3].[O;D1;H0:4]=[C;H0;D2;+0:5]=[N;H0;D2;+0:6]-[c:7](:[c:8]):[c:9]>>[C:1]-[C:2]-[NH;D2;+0:3]-[C;H0;D3;+0:5](=[O;D1;H0:4])-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9] | 17.5 | [{"value": 17.5, "product": "NC1=NC=2C=CC=CC2C2=C1N=C(N2CCOCCNC(=O)NC2=CC=CC=C2)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 18 | HOUR | A solution of the compound of Example 45, 1-[2-(2-aminoethoxy)ethyl]-2-methyl-1H-imidazo[4,5-c]quinolin-4-amine (1.411 g, 4.95 mmol) in 40 mL of 1-methyl-2-pyrrolidinone was treated with triethylamine (1.38 mL, 9.89 mmol). With vigorous stirring, the solution was treated with phenyl isocyanate (0.538, 4.95 mmol). After... | 10.6084/m9.figshare.5104873.v1 | null | Isocyanate.Primary amine | Urea | null | null | c1nc2c(cnc3ccccc32)[nH]1.c1ccccc1 | null | CN1C(CCC1)=O | null | 18 | Cc1nc2c(N)nc3ccccc3c2n1CCOCCN.O=C=Nc1ccccc1>CN1C(CCC1)=O>Cc1nc2c(N)nc3ccccc3c2n1CCOCCNC(=O)Nc1ccccc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-d10c0e9f152c48619e590ba05d36faf3 | Cc1nc2c(N)nc3ccccc3c2n1CCOCCN.O=C=NC1CCCCC1>>Cc1nc2c(N)nc3ccccc3c2n1CCOCCNC(=O)NC1CCCCC1 | NCCOCCN1C(=NC=2C(=NC=3C=CC=CC3C21)N)C.C1(CCCCC1)N=C=O>>NC1=NC=2C=CC=CC2C2=C1N=C(N2CCOCCNC(=O)NC2CCCCC2)C | [CH3:1][c:2]1[n:3][c:4]2[c:5]([NH2:6])[n:7][c:8]3[cH:9][cH:10][cH:11][cH:12][c:13]3[c:14]2[n:15]1[CH2:16][CH2:17][O:18][CH2:19][CH2:20][NH2:21].[C:22](=[O:23])=[N:24][CH:25]1[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30]1>>[CH3:1][c:2]1[n:3][c:4]2[c:5]([NH2:6])[n:7][c:8]3[cH:9][cH:10][cH:11][cH:12][c:13]3[c:14]2[n:15]1[CH2:1... | Cc1nc2c(N)nc3ccccc3c2n1CCOCCN.O=C=NC1CCCCC1 | Cc1nc2c(N)nc3ccccc3c2n1CCOCCNC(=O)NC1CCCCC1 | null | null | N1=CC=CC=C1 | Acylation | Urea synthesis via isocyanate and primary amine | d39cd7dc52a79bb265ff8ef61ef7bf9dc7f7b5fb0150fcb4881bdfb18ab9c380 | a5dc801930c765d2a435a0a2973e50163c305ba8e7641d6adbcc1550b7b96de7 | O=C(NCCOCCn1cnc2cnc3ccccc3c21)NC1CCCCC1 | [C:1]-[C:2](-[N;H0;D2;+0:3]=[C;H0;D2;+0:4]=[O;D1;H0:5])-[C:6].[C:7]-[C:8]-[NH2;D1;+0:9]>>[C:7]-[C:8]-[NH;D2;+0:9]-[C;H0;D3;+0:4](=[O;D1;H0:5])-[NH;D2;+0:3]-[C:2](-[C:1])-[C:6] | 49.8 | [{"value": 49.8, "product": "NC1=NC=2C=CC=CC2C2=C1N=C(N2CCOCCNC(=O)NC2CCCCC2)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 18 | HOUR | A solution of the compound of Example 45, 1-[2-(2-aminoethoxy)ethyl]-2-methyl-1H-imidazo[4,5-c]quinolin-4-amine (1.00 g, 3.50 mmol) in 30 mL of pyridine was chilled in an ice water bath. With vigorous stirring, the solution was treated with cyclohexyl isocyanate (0.45 mL, 3.50 mmol). After 18 h, the reaction was concen... | 10.6084/m9.figshare.5104873.v1 | null | Isocyanate.Primary amine | Urea | null | null | c1nc2c(cnc3ccccc32)[nH]1.C1CCCCC1 | null | N1=CC=CC=C1 | null | 18 | Cc1nc2c(N)nc3ccccc3c2n1CCOCCN.O=C=NC1CCCCC1>N1=CC=CC=C1>Cc1nc2c(N)nc3ccccc3c2n1CCOCCNC(=O)NC1CCCCC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-f7c8e7283245442d9576f577b680b160 | CCc1nc2c(N)nc3ccccc3c2n1CCOCCN.O=C=Nc1ccccc1>>CCc1nc2c(N)nc3ccccc3c2n1CCOCCNC(=O)Nc1ccccc1 | NCCOCCN1C(=NC=2C(=NC=3C=CC=CC3C21)N)CC.C1(=CC=CC=C1)N=C=O>>NC1=NC=2C=CC=CC2C2=C1N=C(N2CCOCCNC(=O)NC2=CC=CC=C2)CC | [CH3:1][CH2:2][c:3]1[n:4][c:5]2[c:6]([NH2:7])[n:8][c:9]3[cH:10][cH:11][cH:12][cH:13][c:14]3[c:15]2[n:16]1[CH2:17][CH2:18][O:19][CH2:20][CH2:21][NH2:22].[C:23](=[O:24])=[N:25][c:26]1[cH:27][cH:28][cH:29][cH:30][cH:31]1>>[CH3:1][CH2:2][c:3]1[n:4][c:5]2[c:6]([NH2:7])[n:8][c:9]3[cH:10][cH:11][cH:12][cH:13][c:14]3[c:15]2[n:... | CCc1nc2c(N)nc3ccccc3c2n1CCOCCN.O=C=Nc1ccccc1 | CCc1nc2c(N)nc3ccccc3c2n1CCOCCNC(=O)Nc1ccccc1 | null | null | C(Cl)Cl | Acylation | Urea synthesis via isocyanate and primary amine | d39cd7dc52a79bb265ff8ef61ef7bf9dc7f7b5fb0150fcb4881bdfb18ab9c380 | a5dc801930c765d2a435a0a2973e50163c305ba8e7641d6adbcc1550b7b96de7 | O=C(NCCOCCn1cnc2cnc3ccccc3c21)Nc1ccccc1 | [C:1]-[C:2]-[NH2;D1;+0:3].[O;D1;H0:4]=[C;H0;D2;+0:5]=[N;H0;D2;+0:6]-[c:7](:[c:8]):[c:9]>>[C:1]-[C:2]-[NH;D2;+0:3]-[C;H0;D3;+0:5](=[O;D1;H0:4])-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9] | 50 | [{"value": 50.0, "product": "NC1=NC=2C=CC=CC2C2=C1N=C(N2CCOCCNC(=O)NC2=CC=CC=C2)CC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 18 | HOUR | A solution of the compound of Example 46, 1-[2-(2-aminoethoxy)ethyl]-2-ethyl-1H-imidazo[4,5-c]quinolin-4-amine (800 mg, 2.67 mmol) in 30 mL of CH2Cl2 was stirred vigorously and treated with phenyl isocyanate (0.290 mL, 2.67 mmol). After 18 h, the reaction was concentrated to yield an off white solid. Purification by co... | 10.6084/m9.figshare.5104873.v1 | null | Isocyanate.Primary amine | Urea | null | null | c1nc2c(cnc3ccccc32)[nH]1.c1ccccc1 | null | C(Cl)Cl | null | 18 | CCc1nc2c(N)nc3ccccc3c2n1CCOCCN.O=C=Nc1ccccc1>C(Cl)Cl>CCc1nc2c(N)nc3ccccc3c2n1CCOCCNC(=O)Nc1ccccc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-3fb82c96c7c047cb97bf2aef937dc8db | CCc1nc2c(N)nc3ccccc3c2n1CCOCCN.O=C=NC1CCCCC1>>CCc1nc2c(N)nc3ccccc3c2n1CCOCCNC(=O)NC1CCCCC1 | NCCOCCN1C(=NC=2C(=NC=3C=CC=CC3C21)N)CC.C1(CCCCC1)N=C=O>>NC1=NC=2C=CC=CC2C2=C1N=C(N2CCOCCNC(=O)NC2CCCCC2)CC | [CH3:1][CH2:2][c:3]1[n:4][c:5]2[c:6]([NH2:7])[n:8][c:9]3[cH:10][cH:11][cH:12][cH:13][c:14]3[c:15]2[n:16]1[CH2:17][CH2:18][O:19][CH2:20][CH2:21][NH2:22].[C:23](=[O:24])=[N:25][CH:26]1[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31]1>>[CH3:1][CH2:2][c:3]1[n:4][c:5]2[c:6]([NH2:7])[n:8][c:9]3[cH:10][cH:11][cH:12][cH:13][c:14]3[c:1... | CCc1nc2c(N)nc3ccccc3c2n1CCOCCN.O=C=NC1CCCCC1 | CCc1nc2c(N)nc3ccccc3c2n1CCOCCNC(=O)NC1CCCCC1 | null | null | N1=CC=CC=C1 | Acylation | Urea synthesis via isocyanate and primary amine | d39cd7dc52a79bb265ff8ef61ef7bf9dc7f7b5fb0150fcb4881bdfb18ab9c380 | a5dc801930c765d2a435a0a2973e50163c305ba8e7641d6adbcc1550b7b96de7 | O=C(NCCOCCn1cnc2cnc3ccccc3c21)NC1CCCCC1 | [C:1]-[C:2](-[N;H0;D2;+0:3]=[C;H0;D2;+0:4]=[O;D1;H0:5])-[C:6].[C:7]-[C:8]-[NH2;D1;+0:9]>>[C:7]-[C:8]-[NH;D2;+0:9]-[C;H0;D3;+0:4](=[O;D1;H0:5])-[NH;D2;+0:3]-[C:2](-[C:1])-[C:6] | 66 | [{"value": 66.0, "product": "NC1=NC=2C=CC=CC2C2=C1N=C(N2CCOCCNC(=O)NC2CCCCC2)CC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | A solution of the compound of Example 46, 1-[2-(2-aminoethoxy)ethyl]-2-ethyl-1H-imidazo[4,5-c]quinolin-4-amine (800 mg, 2.67 mmol) in 30 mL of pyridine was chilled in an ice water bath. With vigorous stirring, the solution was treated with cyclohexyl isocyanate (0.340 mL, 2.67 mmol). After 1 h, the reaction was concent... | 10.6084/m9.figshare.5104873.v1 | null | Isocyanate.Primary amine | Urea | null | null | c1nc2c(cnc3ccccc32)[nH]1.C1CCCCC1 | null | N1=CC=CC=C1 | null | 1 | CCc1nc2c(N)nc3ccccc3c2n1CCOCCN.O=C=NC1CCCCC1>N1=CC=CC=C1>CCc1nc2c(N)nc3ccccc3c2n1CCOCCNC(=O)NC1CCCCC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-bcd118c363164abaab40fe2ee9cec2d2 | CCc1nc2c(N)nc3ccccc3c2n1CCOCCN.O=C(Cl)N1CCOCC1>>CCc1nc2c(N)nc3ccccc3c2n1CCOCCNC(=O)N1CCOCC1 | NCCOCCN1C(=NC=2C(=NC=3C=CC=CC3C21)N)CC.N1(CCOCC1)C(=O)Cl>>NC1=NC=2C=CC=CC2C2=C1N=C(N2CCOCCNC(=O)N2CCOCC2)CC | [CH3:1][CH2:2][c:3]1[n:4][c:5]2[c:6]([NH2:7])[n:8][c:9]3[cH:10][cH:11][cH:12][cH:13][c:14]3[c:15]2[n:16]1[CH2:17][CH2:18][O:19][CH2:20][CH2:21][NH2:22].Cl[C:23](=[O:24])[N:25]1[CH2:26][CH2:27][O:28][CH2:29][CH2:30]1>>[CH3:1][CH2:2][c:3]1[n:4][c:5]2[c:6]([NH2:7])[n:8][c:9]3[cH:10][cH:11][cH:12][cH:13][c:14]3[c:15]2[n:16... | CCc1nc2c(N)nc3ccccc3c2n1CCOCCN.O=C(Cl)N1CCOCC1 | CCc1nc2c(N)nc3ccccc3c2n1CCOCCNC(=O)N1CCOCC1 | null | null | N1=CC=CC=C1 | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | b81fefae7607aa106605114867756af2924064950a2aea97200543849613e96a | 406c5893488430105533c87dfb5d625d8382e709e047cda9cfdc2235e742a9cf | O=C(NCCOCCn1cnc2cnc3ccccc3c21)N1CCOCC1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#7:3](-[C:4])-[C:5].[C:6]-[C:7]-[NH2;D1;+0:8]>>[C:6]-[C:7]-[NH;D2;+0:8]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#7:3](-[C:4])-[C:5] | 51.1 | [{"value": 51.1, "product": "NC1=NC=2C=CC=CC2C2=C1N=C(N2CCOCCNC(=O)N2CCOCC2)CC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | A solution of the compound of Example 46, 1-[2-(2-aminoethoxy)ethyl]-2-ethyl-1H-imidazo[4,5-c]quinolin-4-amine (800 mg, 2.67 mmol) in 30 mL of pyridine was chilled in an ice water bath. With vigorous stirring, the solution was treated with 4-morpholinecarbonyl chloride (0.310 mL, 2.67 mmol). After 1 h, the reaction was... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Tertiary amide.Primary amine | Urea | null | null | c1nc2c(cnc3ccccc32)[nH]1.C1COCC[NH]1 | HCl | N1=CC=CC=C1 | null | 1 | CCc1nc2c(N)nc3ccccc3c2n1CCOCCN.O=C(Cl)N1CCOCC1>N1=CC=CC=C1>CCc1nc2c(N)nc3ccccc3c2n1CCOCCNC(=O)N1CCOCC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-1625d23f71b84467a4005b078878a38c | CCOCc1nc2c(N)nc3ccccc3c2n1CCOCCN.O=C=Nc1ccccc1>>CCOCc1nc2c(N)nc3ccccc3c2n1CCOCCNC(=O)Nc1ccccc1 | NCCOCCN1C(=NC=2C(=NC=3C=CC=CC3C21)N)COCC.C1(=CC=CC=C1)N=C=O>>NC1=NC=2C=CC=CC2C2=C1N=C(N2CCOCCNC(=O)NC2=CC=CC=C2)COCC | [CH3:1][CH2:2][O:3][CH2:4][c:5]1[n:6][c:7]2[c:8]([NH2:9])[n:10][c:11]3[cH:12][cH:13][cH:14][cH:15][c:16]3[c:17]2[n:18]1[CH2:19][CH2:20][O:21][CH2:22][CH2:23][NH2:24].[C:25](=[O:26])=[N:27][c:28]1[cH:29][cH:30][cH:31][cH:32][cH:33]1>>[CH3:1][CH2:2][O:3][CH2:4][c:5]1[n:6][c:7]2[c:8]([NH2:9])[n:10][c:11]3[cH:12][cH:13][cH... | CCOCc1nc2c(N)nc3ccccc3c2n1CCOCCN.O=C=Nc1ccccc1 | CCOCc1nc2c(N)nc3ccccc3c2n1CCOCCNC(=O)Nc1ccccc1 | null | null | C(Cl)Cl | Acylation | Urea synthesis via isocyanate and primary amine | d39cd7dc52a79bb265ff8ef61ef7bf9dc7f7b5fb0150fcb4881bdfb18ab9c380 | a5dc801930c765d2a435a0a2973e50163c305ba8e7641d6adbcc1550b7b96de7 | O=C(NCCOCCn1cnc2cnc3ccccc3c21)Nc1ccccc1 | [C:1]-[C:2]-[NH2;D1;+0:3].[O;D1;H0:4]=[C;H0;D2;+0:5]=[N;H0;D2;+0:6]-[c:7](:[c:8]):[c:9]>>[C:1]-[C:2]-[NH;D2;+0:3]-[C;H0;D3;+0:5](=[O;D1;H0:4])-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9] | 39.6 | [{"value": 39.6, "product": "NC1=NC=2C=CC=CC2C2=C1N=C(N2CCOCCNC(=O)NC2=CC=CC=C2)COCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | A solution of the compound of Example 47, 1-[2-(2-aminoethoxy)ethyl]-2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-4-amine (980 mg, 2.98 mmol) in 20 mL of CH2Cl2 was chilled in an ice water bath. With vigorous stirring, the solution was treated with phenyl isocyanate (0.340 mL, 3.13 mmol). After 30 min, the reaction was c... | 10.6084/m9.figshare.5104873.v1 | null | Isocyanate.Primary amine | Urea | null | null | c1nc2c(cnc3ccccc32)[nH]1.c1ccccc1 | null | C(Cl)Cl | null | 0.5 | CCOCc1nc2c(N)nc3ccccc3c2n1CCOCCN.O=C=Nc1ccccc1>C(Cl)Cl>CCOCc1nc2c(N)nc3ccccc3c2n1CCOCCNC(=O)Nc1ccccc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-806811f7f51242b38aae9480947e1d1d | CCOCc1nc2c(N)nc3ccccc3c2n1CCOCCN.O=C=NC1CCCCC1>>CCOCc1nc2c(N)nc3ccccc3c2n1CCOCCNC(=O)NC1CCCCC1 | NCCOCCN1C(=NC=2C(=NC=3C=CC=CC3C21)N)COCC.C1(CCCCC1)N=C=O>>NC1=NC=2C=CC=CC2C2=C1N=C(N2CCOCCNC(=O)NC2CCCCC2)COCC | [CH3:1][CH2:2][O:3][CH2:4][c:5]1[n:6][c:7]2[c:8]([NH2:9])[n:10][c:11]3[cH:12][cH:13][cH:14][cH:15][c:16]3[c:17]2[n:18]1[CH2:19][CH2:20][O:21][CH2:22][CH2:23][NH2:24].[C:25](=[O:26])=[N:27][CH:28]1[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33]1>>[CH3:1][CH2:2][O:3][CH2:4][c:5]1[n:6][c:7]2[c:8]([NH2:9])[n:10][c:11]3[cH:12][cH:... | CCOCc1nc2c(N)nc3ccccc3c2n1CCOCCN.O=C=NC1CCCCC1 | CCOCc1nc2c(N)nc3ccccc3c2n1CCOCCNC(=O)NC1CCCCC1 | null | null | C(Cl)Cl | Acylation | Urea synthesis via isocyanate and primary amine | d39cd7dc52a79bb265ff8ef61ef7bf9dc7f7b5fb0150fcb4881bdfb18ab9c380 | a5dc801930c765d2a435a0a2973e50163c305ba8e7641d6adbcc1550b7b96de7 | O=C(NCCOCCn1cnc2cnc3ccccc3c21)NC1CCCCC1 | [C:1]-[C:2](-[N;H0;D2;+0:3]=[C;H0;D2;+0:4]=[O;D1;H0:5])-[C:6].[C:7]-[C:8]-[NH2;D1;+0:9]>>[C:7]-[C:8]-[NH;D2;+0:9]-[C;H0;D3;+0:4](=[O;D1;H0:5])-[NH;D2;+0:3]-[C:2](-[C:1])-[C:6] | 29.5 | [{"value": 29.5, "product": "NC1=NC=2C=CC=CC2C2=C1N=C(N2CCOCCNC(=O)NC2CCCCC2)COCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | A solution of the compound of Example 47, 1-[2-(2-aminoethoxy)ethyl]-2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-4-amine (980 mg, 2.98 mmol) in 20 mL of CH2Cl2 was chilled in an ice water bath. With vigorous stirring, the solution was treated with cyclohexyl isocyanate (0.400 mL, 3.13 mmol). After 30 min, the reaction w... | 10.6084/m9.figshare.5104873.v1 | null | Isocyanate.Primary amine | Urea | null | null | c1nc2c(cnc3ccccc32)[nH]1.C1CCCCC1 | null | C(Cl)Cl | null | 0.5 | CCOCc1nc2c(N)nc3ccccc3c2n1CCOCCN.O=C=NC1CCCCC1>C(Cl)Cl>CCOCc1nc2c(N)nc3ccccc3c2n1CCOCCNC(=O)NC1CCCCC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-398d20b3e2494afbae52c5075d30027e | CCOCc1nc2c(N)nc3ccccc3c2n1CCOCCN.O=C(Cl)N1CCOCC1>>CCOCc1nc2c(N)nc3ccccc3c2n1CCOCCNC(=O)N1CCOCC1 | N1(CCOCC1)C(=O)Cl.O.NCCOCCN1C(=NC=2C(=NC=3C=CC=CC3C21)N)COCC.C(C)N(CC)CC>>NC1=NC=2C=CC=CC2C2=C1N=C(N2CCOCCNC(=O)N2CCOCC2)COCC | [CH3:1][CH2:2][O:3][CH2:4][c:5]1[n:6][c:7]2[c:8]([NH2:9])[n:10][c:11]3[cH:12][cH:13][cH:14][cH:15][c:16]3[c:17]2[n:18]1[CH2:19][CH2:20][O:21][CH2:22][CH2:23][NH2:24].Cl[C:25](=[O:26])[N:27]1[CH2:28][CH2:29][O:30][CH2:31][CH2:32]1>>[CH3:1][CH2:2][O:3][CH2:4][c:5]1[n:6][c:7]2[c:8]([NH2:9])[n:10][c:11]3[cH:12][cH:13][cH:1... | CCOCc1nc2c(N)nc3ccccc3c2n1CCOCCN.O=C(Cl)N1CCOCC1 | CCOCc1nc2c(N)nc3ccccc3c2n1CCOCCNC(=O)N1CCOCC1 | null | null | C(Cl)Cl | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | b81fefae7607aa106605114867756af2924064950a2aea97200543849613e96a | 406c5893488430105533c87dfb5d625d8382e709e047cda9cfdc2235e742a9cf | O=C(NCCOCCn1cnc2cnc3ccccc3c21)N1CCOCC1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#7:3](-[C:4])-[C:5].[C:6]-[C:7]-[NH2;D1;+0:8]>>[C:6]-[C:7]-[NH;D2;+0:8]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#7:3](-[C:4])-[C:5] | 29.8 | [{"value": 29.8, "product": "NC1=NC=2C=CC=CC2C2=C1N=C(N2CCOCCNC(=O)N2CCOCC2)COCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 18 | HOUR | A solution of the compound of Example 47, 1-[2-(2-aminoethoxy)ethyl]-2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-4-amine (980 mg, 2.98 mmol) in 20 mL of CH2Cl2 was treated with triethylamine (1.04 mL, 7.45 mmol) and chilled in an ice water bath. With vigorous stirring, the solution was treated with 4-morpholinecarbonyl ... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Tertiary amide.Primary amine | Urea | null | null | c1nc2c(cnc3ccccc32)[nH]1.C1COCC[NH]1 | HCl | C(Cl)Cl | null | 18 | CCOCc1nc2c(N)nc3ccccc3c2n1CCOCCN.O=C(Cl)N1CCOCC1>C(Cl)Cl>CCOCc1nc2c(N)nc3ccccc3c2n1CCOCCNC(=O)N1CCOCC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-6ab0c792e2884cc19df6d6ecb4a193da | CC1(C)CN=C(Cc2ccccc2)C1.O=C(CBr)c1ccc(Cl)cc1>>CC1(C)Cc2c(-c3ccccc3)c(-c3ccc(Cl)cc3)cn2C1 | C1=CC(=CC=C1C(=O)CBr)Cl.C(C1=CC=CC=C1)C1=NCC(C1)(C)C>>ClC1=CC=C(C=C1)C1=CN2CC(CC2=C1C1=CC=CC=C1)(C)C | [CH3:1][C:2]1([CH3:3])[CH2:4][C:5]([CH2:6][c:7]2[cH:8][cH:9][cH:10][cH:11][cH:12]2)=[N:22][CH2:23]1.O=[C:13]([c:14]1[cH:15][cH:16][c:17]([Cl:18])[cH:19][cH:20]1)[CH2:21]Br>>[CH3:1][C:2]1([CH3:3])[CH2:4][c:5]2[c:6](-[c:7]3[cH:8][cH:9][cH:10][cH:11][cH:12]3)[c:13](-[c:14]3[cH:15][cH:16][c:17]([Cl:18])[cH:19][cH:20]3)[cH:... | CC1(C)CN=C(Cc2ccccc2)C1.O=C(CBr)c1ccc(Cl)cc1 | CC1(C)Cc2c(-c3ccccc3)c(-c3ccc(Cl)cc3)cn2C1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | b6a3fcda43f0dc538a3fb7598130630c97a7f6c654ec5e8d741fa2c8fffe2c2c | 5d16d986f2820f4a8c80dd26fbdf56b0677fe2763d9991e54a666fed55014ae0 | c1ccc(-c2cn3c(c2-c2ccccc2)CCC3)cc1 | Br-[CH2;D2;+0:1]-[C;H0;D3;+0:2](=O)-[c;H0;D3;+0:3](:[c:4]:[c:5]):[c:6]:[c:7].[c:8]:[c:9]:[c;H0;D3;+0:10](-[CH2;D2;+0:11]-[C;H0;D3;+0:12]1=[N;H0;D2;+0:13]-[C:14]-[C:15]-[C:16]-1):[c:17]:[c:18]>>[c:8]:[c:9]:[c;H0;D3;+0:10](-[c;H0;D3;+0:11]1:[c;H0;D3;+0:2](-[c;H0;D3;+0:3](:[c:4]:[c:5]):[c:6]:[c:7]):[cH;D2;+0:1]:[n;H0;D3;+... | null | [] | null | null | null | null | The 2-benzyl-4,4-dimethyl-1-pyrroline of the formula III is then cyclized with ω-bromo-4-chloroacetophenone to give the 6-(4-chlorophenyl)-2,2-dimethyl-7-phenyl-2,3-dihydro-1H-pyrrolizine of the formula II. The reaction is known from the prior art mentioned at the outset. ω-Bromo-4-chloroacetophenone can be obtained, f... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ketone.Substituted imine | null | C1=NCCC1 | c1cc2n(c1)CCC2 | c1ccccc1.c1ccccc1.c1cc2n(c1)CCC2 | HBr | null | null | null | CC1(C)CN=C(Cc2ccccc2)C1.O=C(CBr)c1ccc(Cl)cc1>>CC1(C)Cc2c(-c3ccccc3)c(-c3ccc(Cl)cc3)cn2C1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-238fae4e2e3046a0a1712d0feaaffa42 | Cn1cccc1.O=C(Cl)C(Cl)(Cl)Cl>>O=C(c1ccc[nH]1)C(Cl)(Cl)Cl | ClC(C(=O)Cl)(Cl)Cl.CN1C=CC=C1>>ClC(C(=O)C=1NC=CC1)(Cl)Cl | C[n:7]1[cH:3][cH:4][cH:5][cH:6]1.Cl[C:2](=[O:1])[C:8]([Cl:9])([Cl:10])[Cl:11]>>[O:1]=[C:2]([c:3]1[cH:4][cH:5][cH:6][nH:7]1)[C:8]([Cl:9])([Cl:10])[Cl:11] | Cn1cccc1.O=C(Cl)C(Cl)(Cl)Cl | O=C(c1ccc[nH]1)C(Cl)(Cl)Cl | null | null | C(C)OCC | C-C Coupling | OtherReaction | 701d21b652ce6d90463464dd21d4d87caf603bff2f60e1ad8fa59cfd59145f4f | fe2a4a0dfbb5b71b9a065e092364c64b22b4eb1ad4d6ba2a1e8edc9d31fce3e4 | c1cc[nH]c1 | C-[n;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[cH;D2;+0:5]:1.Cl-[C;H0;D3;+0:6](=[O;D1;H0:7])-[C:8](-[Cl;D1;H0:9])(-[Cl;D1;H0:10])-[Cl;D1;H0:11]>>[Cl;D1;H0:9]-[C:8](-[Cl;D1;H0:10])(-[Cl;D1;H0:11])-[C;H0;D3;+0:6](=[O;D1;H0:7])-[c;H0;D3;+0:5]1:[c:4]:[c:3]:[c:2]:[nH;D2;+0:1]:1 | 92.7 | [{"value": 92.7, "product": "ClC(C(=O)C=1NC=CC1)(Cl)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | To a well stirred solution of trichloroacetyl chloride (1 kg, 5.5 mole) in 1.5 liter ethyl ether in a 12 liter flask was added dropwise over a period of 3 h a solution of N-methylpyrrole (0.45 kg, 5.5 mole) in 1.5 liter anhydrous ethyl ether. The reaction was stirred for an additional 3 hours and quenched by the dropwi... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide | Ketone | c1cc[nH]c1 | c1cc[nH]c1 | c1cc[nH]c1 | HCl | C(C)OCC | null | 3 | Cn1cccc1.O=C(Cl)C(Cl)(Cl)Cl>C(C)OCC>O=C(c1ccc[nH]1)C(Cl)(Cl)Cl |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-8051ad50dff14c47a524be7692963636 | O=C(c1ccc[nH]1)C(Cl)(Cl)Cl.O=[N+]([O-])O>>Cn1cc([N+](=O)[O-])cc1C(=O)C(Cl)(Cl)Cl | ClC(C(=O)C=1NC=CC1)(Cl)Cl.[N+](=O)(O)[O-].C(C)(C)O>>[N+](=O)([O-])C=1C=C(N(C1)C)C(C(Cl)(Cl)Cl)=O | [nH:2]1[cH:3][cH:4][cH:8][c:9]1[C:10](=[O:11])[C:12]([Cl:13])([Cl:14])[Cl:15].O[N+:5](=[O:6])[O-:7]>>[CH3:1][n:2]1[cH:3][c:4]([N+:5](=[O:6])[O-:7])[cH:8][c:9]1[C:10](=[O:11])[C:12]([Cl:13])([Cl:14])[Cl:15] | O=C(c1ccc[nH]1)C(Cl)(Cl)Cl.O=[N+]([O-])O | Cn1cc([N+](=O)[O-])cc1C(=O)C(Cl)(Cl)Cl | null | null | C(C)(=O)OC(C)=O | Functional Group Addition | OtherReaction | 30eec259f0a5a093f09ad410d85904ad6868c9951a256c4a4c8946d22adaf24a | ddce49825c02b8965f10c8d99e3c841d26e1f136da6037b417c09313e6d73097 | c1cc[nH]c1 | O-[N+;H0;D3:1](-[O;-;D1;H0:2])=[O;D1;H0:3].[C:4]-[C:5](=[O;D1;H0:6])-[c:7]1:[c:8]:[cH;D2;+0:9]:[c:10]:[nH;D2;+0:11]:1>>[C:4]-[C:5](=[O;D1;H0:6])-[c:7]1:[c:8]:[c;H0;D3;+0:9](-[N+;H0;D3:1](-[O;-;D1;H0:2])=[O;D1;H0:3]):[c:10]:[n;H0;D3;+0:11]:1-[C;D1;H3:12] | 54 | [{"value": 54.0, "product": "[N+](=O)([O-])C=1C=C(N(C1)C)C(C(Cl)(Cl)Cl)=O", "details": "PERCENTYIELD", "is_desired": false}] | -40 | CELSIUS | 4 | HOUR | To a well stirred solution of trichloroacetyl chloride (1 kg, 5.5 mole) in 1.5 liter ethyl ether in a 12 liter flask was added dropwise over a period of 3 h a solution of N-methylpyrrole (0.45 kg, 5.5 mole) in 1.5 liter anhydrous ethyl ether. The reaction was stirred for an additional 3 hours and quenched by the dropwi... | 10.6084/m9.figshare.5104873.v1 | null | Nitrate | Nitro group | c1cc[nH]c1 | c1cc[nH]c1 | c1cc[nH]c1 | null | C(C)(=O)OC(C)=O | -40 | 4 | O=C(c1ccc[nH]1)C(Cl)(Cl)Cl.O=[N+]([O-])O>C(C)(=O)OC(C)=O>Cn1cc([N+](=O)[O-])cc1C(=O)C(Cl)(Cl)Cl |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-b9585db531774ec3bb0a2d3c2eeb1d60 | c1ccc(P(c2ccccc2)c2ccccc2)cc1>>O=P(c1ccccc1)(c1ccccc1)c1ccccc1 | CO.C(C)(C)(C)OC(=O)N([C@@H](C)CO)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.BrN1C(CCC1=O)=O>>C1(=CC=CC=C1)P(C1=CC=CC=C1)(C1=CC=CC=C1)=O | [P:2]([c:3]1[cH:4][cH:5][cH:6][cH:7][cH:8]1)([c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1)[c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1>>[O:1]=[P:2]([c:3]1[cH:4][cH:5][cH:6][cH:7][cH:8]1)([c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1)[c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1 | c1ccc(P(c2ccccc2)c2ccccc2)cc1 | O=P(c1ccccc1)(c1ccccc1)c1ccccc1 | null | null | CN(C)C=O | Functional Group Interconversion | OtherReaction | 42af6cdfb86a130c92365e01a31b50705eea7bdf12f67dc370bf24402f7ceedc | f1bbf9aa3c82f5e49be9f6d53533b6bb152f359232b6d32090c168949766aa71 | O=P(c1ccccc1)(c1ccccc1)c1ccccc1 | [c:1]:[c:2](-[P;H0;D3;+0:3](-[c:4](:[c:5]):[c:6])-[c:7](:[c:8]):[c:9]):[c:10]>>[O;D1;H0:11]=[P;H0;D4;+0:3](-[c:4](:[c:5]):[c:6])(-[c:7](:[c:8]):[c:9])-[c:2](:[c:1]):[c:10] | 85 | [{"value": 85.0, "product": "C1(=CC=CC=C1)P(C1=CC=CC=C1)(C1=CC=CC=C1)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 5 | MINUTE | To a solution of the N-tert-butoxycarbonyl phenyl alaninol (1.42 mmol) and triphenylphosphine (2 equiv) in DMF, N-bromosuccinimide (2 equiv) was slowly added. The reaction was warmed to 50° for 15 min and then cooled to 20°. Methanol (0.5 mL) was added to destroy the excess reagent. After 5 min, ether was added, and th... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | c1ccccc1.c1ccccc1.c1ccccc1 | null | CN(C)C=O | null | 0.083333 | c1ccc(P(c2ccccc2)c2ccccc2)cc1>CN(C)C=O>O=P(c1ccccc1)(c1ccccc1)c1ccccc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-ad1da34fdff74ffd8ff1cfc5f671ee2b | C1CCNCC1.CC(C)(C)OC(=O)NC(CCBr)c1ccccc1>>NC(CCN1CCCCC1)c1ccccc1 | BrCCC(C1=CC=CC=C1)NC(=O)OC(C)(C)C.N1CCCCC1>>C1(=CC=CC=C1)C(CCN1CCCCC1)N | [NH:5]1[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10]1.CC(C)(C)OC(=O)[NH:1][CH:2]([CH2:3][CH2:4]Br)[c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1>>[NH2:1][CH:2]([CH2:3][CH2:4][N:5]1[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10]1)[c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1 | C1CCNCC1.CC(C)(C)OC(=O)NC(CCBr)c1ccccc1 | NC(CCN1CCCCC1)c1ccccc1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | dbf8b9a06030f8030bf063f09fd042d89443a731c7712f62eb044a59b8cc9903 | 7617c42d56b550b3d1d0d0991f3f1bb85834fe99753d336fc35a923b06f52463 | c1ccc(CCCN2CCCCC2)cc1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3](-[c:4])-[NH;D2;+0:5]-C(=O)-O-C(-C)(-C)-C.[C:6]-[C:7]-[NH;D2;+0:8]-[C:9]-[C:10]>>[C:6]-[C:7]-[N;H0;D3;+0:8](-[CH2;D2;+0:1]-[C:2]-[C:3](-[NH2;D1;+0:5])-[c:4])-[C:9]-[C:10] | null | [] | null | null | null | null | The procedure given in Example 2 except for the formation of salts was followed using 3-bromo-1-(tert-butoxycarbonyl)amino-1-phenyl propane and piperidine as reactants, instead of d-1-bromo-2-(tert-butoxycarbonyl)amino-3-phenyl propane and hexamethyleneimine to give 1-Phenyl-3-(1-piperidinyl)-n-propylamine.
Conditions:... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Carbamic ester.Ether.Secondary amine.Boc | Primary amine.Tertiary amine | C1CCNCC1 | C1CC[NH]CC1 | C1CC[NH]CC1.c1ccccc1 | HBr | null | null | null | C1CCNCC1.CC(C)(C)OC(=O)NC(CCBr)c1ccccc1>>NC(CCN1CCCCC1)c1ccccc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-acd83b19b47d45b8a4f04bb5230bd5a2 | CC(C)(C)OC(=O)NC(CCBr)c1ccccc1.OC(c1ccccc1)C1CCNCC1>>NC(CCN1CCC(C(O)c2ccccc2)CC1)c1ccccc1 | BrCCC(C1=CC=CC=C1)NC(=O)OC(C)(C)C.C1(=CC=CC=C1)C(O)C1CCNCC1>>NC(CCN1CCC(CC1)C(O)C1=CC=CC=C1)C1=CC=CC=C1 | CC(C)(C)OC(=O)[NH:1][CH:2]([CH2:3][CH2:4]Br)[c:19]1[cH:20][cH:21][cH:22][cH:23][cH:24]1.[NH:5]1[CH2:6][CH2:7][CH:8]([CH:9]([OH:10])[c:11]2[cH:12][cH:13][cH:14][cH:15][cH:16]2)[CH2:17][CH2:18]1>>[NH2:1][CH:2]([CH2:3][CH2:4][N:5]1[CH2:6][CH2:7][CH:8]([CH:9]([OH:10])[c:11]2[cH:12][cH:13][cH:14][cH:15][cH:16]2)[CH2:17][CH2... | CC(C)(C)OC(=O)NC(CCBr)c1ccccc1.OC(c1ccccc1)C1CCNCC1 | NC(CCN1CCC(C(O)c2ccccc2)CC1)c1ccccc1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | dbf8b9a06030f8030bf063f09fd042d89443a731c7712f62eb044a59b8cc9903 | 7617c42d56b550b3d1d0d0991f3f1bb85834fe99753d336fc35a923b06f52463 | c1ccc(CCCN2CCC(Cc3ccccc3)CC2)cc1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3](-[c:4])-[NH;D2;+0:5]-C(=O)-O-C(-C)(-C)-C.[C:6]-[C:7]-[NH;D2;+0:8]-[C:9]-[C:10]>>[C:6]-[C:7]-[N;H0;D3;+0:8](-[CH2;D2;+0:1]-[C:2]-[C:3](-[NH2;D1;+0:5])-[c:4])-[C:9]-[C:10] | null | [] | null | null | null | null | The procedure given in Example 2 except for the formation of salts was followed using 3-bromo-1-(tert-butoxycarbonyl)amino-1-phenyl propane and phenyl-piperidin-4-yl-methanol as reactants, instead of d-1-bromo-2-(tert-butoxycarbonyl)amino-3-phenyl propane and hexamethyleneimine to give [1-(3-Amino-3-phenyl-propyl)-pipe... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Carbamic ester.Ether.Secondary amine.Boc | Primary amine.Tertiary amine | C1CCNCC1 | C1CC[NH]CC1 | C1CC[NH]CC1.c1ccccc1.c1ccccc1 | HBr | null | null | null | CC(C)(C)OC(=O)NC(CCBr)c1ccccc1.OC(c1ccccc1)C1CCNCC1>>NC(CCN1CCC(C(O)c2ccccc2)CC1)c1ccccc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-00b0281c50da4bacb5aa3150161bb91c | CC(C)(C)OC(=O)NC(CCBr)c1ccccc1.OC(c1ccc(F)cc1)C1CCNCC1>>NC(CCN1CCC(C(O)c2ccc(F)cc2)CC1)c1ccccc1 | BrCCC(C1=CC=CC=C1)NC(=O)OC(C)(C)C.FC1=CC=C(C=C1)C(O)C1CCNCC1>>NC(CCN1CCC(CC1)C(O)C1=CC=C(C=C1)F)C1=CC=CC=C1 | CC(C)(C)OC(=O)[NH:1][CH:2]([CH2:3][CH2:4]Br)[c:20]1[cH:21][cH:22][cH:23][cH:24][cH:25]1.[NH:5]1[CH2:6][CH2:7][CH:8]([CH:9]([OH:10])[c:11]2[cH:12][cH:13][c:14]([F:15])[cH:16][cH:17]2)[CH2:18][CH2:19]1>>[NH2:1][CH:2]([CH2:3][CH2:4][N:5]1[CH2:6][CH2:7][CH:8]([CH:9]([OH:10])[c:11]2[cH:12][cH:13][c:14]([F:15])[cH:16][cH:17]... | CC(C)(C)OC(=O)NC(CCBr)c1ccccc1.OC(c1ccc(F)cc1)C1CCNCC1 | NC(CCN1CCC(C(O)c2ccc(F)cc2)CC1)c1ccccc1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | dbf8b9a06030f8030bf063f09fd042d89443a731c7712f62eb044a59b8cc9903 | 7617c42d56b550b3d1d0d0991f3f1bb85834fe99753d336fc35a923b06f52463 | c1ccc(CCCN2CCC(Cc3ccccc3)CC2)cc1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3](-[c:4])-[NH;D2;+0:5]-C(=O)-O-C(-C)(-C)-C.[C:6]-[C:7]-[NH;D2;+0:8]-[C:9]-[C:10]>>[C:6]-[C:7]-[N;H0;D3;+0:8](-[CH2;D2;+0:1]-[C:2]-[C:3](-[NH2;D1;+0:5])-[c:4])-[C:9]-[C:10] | null | [] | null | null | null | null | The procedure given in Example 2 was followed using 3-bromo-1-(tert-butoxycarbonyl)amino-1-phenyl propane and (4-fluorophenyl)-piperidin-4-yl-methanol as reactants, instead of d-1-bromo-2-(tert-butoxycarbonyl)amino-3-phenyl propane and hexamethyleneimine to give [1-(3-Amino-3-phenyl-propyl)-piperidin-4-yl]-(4-fluoro-ph... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Carbamic ester.Ether.Secondary amine.Boc | Primary amine.Tertiary amine | C1CCNCC1 | C1CC[NH]CC1 | C1CC[NH]CC1.c1ccccc1.c1ccccc1 | HBr | null | null | null | CC(C)(C)OC(=O)NC(CCBr)c1ccccc1.OC(c1ccc(F)cc1)C1CCNCC1>>NC(CCN1CCC(C(O)c2ccc(F)cc2)CC1)c1ccccc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-d519d927b6524e8eba036b10bc73760b | NC1CCC1.O=[N+]([O-])c1cn([N+](=O)[O-])cn1>>O=[N+]([O-])c1cn(C2CCC2)cn1 | [N+](=O)([O-])N1C=NC(=C1)[N+](=O)[O-].C1(CCC1)N>>C1(CCC1)N1C=NC(=C1)[N+](=O)[O-] | N[CH:7]1[CH2:8][CH2:9][CH2:10]1.O=[N+]([O-])[n:6]1[cH:5][c:4]([N+:2](=[O:1])[O-:3])[n:12][cH:11]1>>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][n:6]([CH:7]2[CH2:8][CH2:9][CH2:10]2)[cH:11][n:12]1 | NC1CCC1.O=[N+]([O-])c1cn([N+](=O)[O-])cn1 | O=[N+]([O-])c1cn(C2CCC2)cn1 | null | null | CO | Functional Group Addition | OtherReaction | 46a51f8ca5a006fa0c7307aff9c47bbfab60ab29424e07318a72cc160ef81c35 | e44bfec7c64c2106b9732634e34828e6460a6db63dcf75ef4a78a1aabdfc680a | c1cn(C2CCC2)cn1 | N-[CH;D3;+0:1]1-[C:2]-[C:3]-[C:4]-1.O=[N+](-[O-])-[n;H0;D3;+0:5]1:[c:6]:[#7;a:7]:[c:8](-[#7;+:9]):[c:10]:1>>[#7;+:9]-[c:8]1:[#7;a:7]:[c:6]:[n;H0;D3;+0:5](-[CH;D3;+0:1]2-[C:2]-[C:3]-[C:4]-2):[c:10]:1 | 92 | [{"value": 92.0, "product": "C1(CCC1)N1C=NC(=C1)[N+](=O)[O-]", "details": "PERCENTYIELD", "is_desired": false}, {"value": 91.7, "product": "C1(CCC1)N1C=NC(=C1)[N+](=O)[O-]", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 16 | HOUR | 1,4-Dinitroimidazole (237 mg, 1.5 mmol, J. Phys. Chem. 1995, 99, 5009–5015) was added to a solution of cyclobutylamine (107 mg, 1.5 mmol) in methanol (10 mL) at 23° C. The reaction mixture was stirred for 16 h, then the solvent was removed in vacuo and the resulting residue was purified by silica gel chromatography (1:... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group.Primary amine | null | C1CCC1.c1c[nH]cn1 | c1c[nH]cn1.C1CCC1 | c1c[nH]cn1.C1CCC1 | HO- | CO | null | 16 | NC1CCC1.O=[N+]([O-])c1cn([N+](=O)[O-])cn1>CO>O=[N+]([O-])c1cn(C2CCC2)cn1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-394e4d26bd894add8e909419ab362dae | NC1CCCC1.O=[N+]([O-])c1cn([N+](=O)[O-])cn1>>O=[N+]([O-])c1cn(C2CCCC2)cn1 | C1(CCCC1)N.[N+](=O)([O-])N1C=NC(=C1)[N+](=O)[O-]>>C1(CCCC1)N1C=NC(=C1)[N+](=O)[O-] | N[CH:7]1[CH2:8][CH2:9][CH2:10][CH2:11]1.O=[N+]([O-])[n:6]1[cH:5][c:4]([N+:2](=[O:1])[O-:3])[n:13][cH:12]1>>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][n:6]([CH:7]2[CH2:8][CH2:9][CH2:10][CH2:11]2)[cH:12][n:13]1 | NC1CCCC1.O=[N+]([O-])c1cn([N+](=O)[O-])cn1 | O=[N+]([O-])c1cn(C2CCCC2)cn1 | null | null | null | Functional Group Addition | OtherReaction | e919eded286ceea592f7af5daf8bf9d98ce3e82e260913bddabbbd1919ae9b8e | e44bfec7c64c2106b9732634e34828e6460a6db63dcf75ef4a78a1aabdfc680a | c1cn(C2CCCC2)cn1 | N-[CH;D3;+0:1]1-[C:2]-[C:3]-[C:4]-[C:5]-1.O=[N+](-[O-])-[n;H0;D3;+0:6]1:[c:7]:[#7;a:8]:[c:9](-[#7;+:10]):[c:11]:1>>[#7;+:10]-[c:9]1:[#7;a:8]:[c:7]:[n;H0;D3;+0:6](-[CH;D3;+0:1]2-[C:2]-[C:3]-[C:4]-[C:5]-2):[c:11]:1 | 75 | [{"value": 75.0, "product": "C1(CCCC1)N1C=NC(=C1)[N+](=O)[O-]", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | This reaction was carried out using the procedure for Preparation 1 with cyclopentyl amine and 1,4-dinitroimidazole to afford 205 mg (75% yield) of 1-cyclopentyl-4-nitro-1H-imidazole; 1H NMR (400 MHz, CDCl3) δ 7.77 (s, 1H), 7.45 (s, 1H), 4.49 (m, 1H), 2.25 (m, 2H), 2.0–1.7 (m, 6H); MS (AP/CI): 182.2 (M+H)+.
Conditions:... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group.Primary amine | null | C1CCCC1.c1c[nH]cn1 | c1c[nH]cn1.C1CCCC1 | c1c[nH]cn1.C1CCCC1 | HO- | null | null | null | NC1CCCC1.O=[N+]([O-])c1cn([N+](=O)[O-])cn1>>O=[N+]([O-])c1cn(C2CCCC2)cn1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-1df8f83e785247e7b00c28cbc83a7c8b | N[C@H]1C[C@@H](c2ccccc2)C1.O=[N+]([O-])c1cn([N+](=O)[O-])cn1>>O=[N+]([O-])c1cn([C@H]2C[C@@H](c3ccccc3)C2)cn1 | C1(=CC=CC=C1)[C@H]1C[C@H](C1)N.[N+](=O)([O-])N1C=NC(=C1)[N+](=O)[O-]>>[N+](=O)([O-])C=1N=CN(C1)[C@@H]1C[C@@H](C1)C1=CC=CC=C1 | N[C@H:7]1[CH2:8][C@@H:9]([c:10]2[cH:11][cH:12][cH:13][cH:14][cH:15]2)[CH2:16]1.O=[N+]([O-])[n:6]1[cH:5][c:4]([N+:2](=[O:1])[O-:3])[n:18][cH:17]1>>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][n:6]([C@H:7]2[CH2:8][C@@H:9]([c:10]3[cH:11][cH:12][cH:13][cH:14][cH:15]3)[CH2:16]2)[cH:17][n:18]1 | N[C@H]1C[C@@H](c2ccccc2)C1.O=[N+]([O-])c1cn([N+](=O)[O-])cn1 | O=[N+]([O-])c1cn([C@H]2C[C@@H](c3ccccc3)C2)cn1 | null | null | null | Functional Group Addition | OtherReaction | 46a51f8ca5a006fa0c7307aff9c47bbfab60ab29424e07318a72cc160ef81c35 | e44bfec7c64c2106b9732634e34828e6460a6db63dcf75ef4a78a1aabdfc680a | c1ccc([C@H]2C[C@@H](n3ccnc3)C2)cc1 | N-[C@@H;D3;+0:1]1-[C:2]-[C:3]-[C:4]-1.O=[N+](-[O-])-[n;H0;D3;+0:5]1:[c:6]:[#7;a:7]:[c:8](-[#7;+:9]):[c:10]:1>>[#7;+:9]-[c:8]1:[#7;a:7]:[c:6]:[n;H0;D3;+0:5](-[C@@H;D3;+0:1]2-[C:2]-[C:3]-[C:4]-2):[c:10]:1 | 46 | [{"value": 46.0, "product": "[N+](=O)([O-])C=1N=CN(C1)[C@@H]1C[C@@H](C1)C1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | This reaction was carried out using the procedure for Preparation 1 with cis-3-phenylcyclobutylamine (J. Med. Pharm. Chem. 1960, 2, 687–691; ACIEE 1981, 20, 879–880) and 1,4-dinitroimidazole to afford 46 mg (46% yield) of 4-nitro-1-(cis-3-phenyl-cyclobutyl)-1H-imidazole; 1H NMR (300 MHz, CDCl3) δ 7.9 (s, 1H), 7.55 (s, ... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group.Primary amine | null | C1CCC1.c1c[nH]cn1 | c1c[nH]cn1.C1CCC1 | c1c[nH]cn1.C1CCC1.c1ccccc1 | HO- | null | null | null | N[C@H]1C[C@@H](c2ccccc2)C1.O=[N+]([O-])c1cn([N+](=O)[O-])cn1>>O=[N+]([O-])c1cn([C@H]2C[C@@H](c3ccccc3)C2)cn1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-ab61f7c1bcb940689fe79b727d5479f0 | O=C(O)Cc1ccc2ncccc2c1.O=[N+]([O-])c1cn(C2CCC2)cn1>>O=C(Cc1ccc2ncccc2c1)Nc1cn(C2CCC2)cn1 | N1=CC=CC2=CC(=CC=C12)CC(=O)O.C1(CCC1)N1C=NC(=C1)[N+](=O)[O-].C(C)(=O)OCC.CCN(CC)CC>>C1(CCC1)N1C=NC(=C1)NC(CC=1C=C2C=CC=NC2=CC1)=O | O[C:2](=[O:1])[CH2:3][c:4]1[cH:5][cH:6][c:7]2[n:8][cH:9][cH:10][cH:11][c:12]2[cH:13]1.O=[N+:14]([O-])[c:15]1[cH:16][n:17]([CH:18]2[CH2:19][CH2:20][CH2:21]2)[cH:22][n:23]1>>[O:1]=[C:2]([CH2:3][c:4]1[cH:5][cH:6][c:7]2[n:8][cH:9][cH:10][cH:11][c:12]2[cH:13]1)[NH:14][c:15]1[cH:16][n:17]([CH:18]2[CH2:19][CH2:20][CH2:21]2)[c... | O=C(O)Cc1ccc2ncccc2c1.O=[N+]([O-])c1cn(C2CCC2)cn1 | O=C(Cc1ccc2ncccc2c1)Nc1cn(C2CCC2)cn1 | null | [Pd] | C(Cl)Cl | Acylation | OtherReaction | 07d1695adb57fcbe166e427114577c880df19df2ee26bdadcbdf979c1785ff55 | 141f63f004bbbe912fc54e457ad7143d740953538a28293f72b74ca32c03fab9 | O=C(Cc1ccc2ncccc2c1)Nc1cn(C2CCC2)cn1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[c:4].O=[N+;H0;D3:5](-[O-])-[c:6]1:[#7;a:7]:[c:8]:[#7;a:9](-[C:10]):[c:11]:1>>[C:10]-[#7;a:9]1:[c:11]:[c:6](-[NH;D2;+0:5]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[c:4]):[#7;a:7]:[c:8]:1 | 47.1 | [{"value": 47.0, "product": "C1(CCC1)N1C=NC(=C1)NC(CC=1C=C2C=CC=NC2=CC1)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 47.1, "product": "C1(CCC1)N1C=NC(=C1)NC(CC=1C=C2C=CC=NC2=CC1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -10 | CELSIUS | 2 | HOUR | To a Parr hydrogenation bottle was added 1-cyclobutyl-4-nitro-1H-imidazole (Preparation 1, 150 mg, 0.9 mmol) and ethyl acetate (10 mL), followed by 10% Pd on carbon (250 mg). The reaction mixture was placed on a Parr hydrogenation apparatus and was reacted for 6 h under 50 psi H2 at 23° C. The contents of the bottle we... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Nitro group | Secondary amide | null | null | c1ccc2ncccc2c1.c1c[nH]cn1.C1CCC1 | Other | [Pd].C(Cl)Cl | -10 | 2 | O=C(O)Cc1ccc2ncccc2c1.O=[N+]([O-])c1cn(C2CCC2)cn1>[Pd].C(Cl)Cl>O=C(Cc1ccc2ncccc2c1)Nc1cn(C2CCC2)cn1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-bf88feb4393b4c36bcb3236484326876 | O=C(Cl)Oc1ccccc1.O=[N+]([O-])c1cn(C2CCC2)cn1>>O=C(Nc1cn(C2CCC2)cn1)Oc1ccccc1 | C1(=CC=CC=C1)OC(=O)Cl.C(C)(=O)O.C(C)(C)N(CC)C(C)C.C1(CCC1)N1C=NC(=C1)[N+](=O)[O-]>>C1(=CC=CC=C1)OC(NC=1N=CN(C1)C1CCC1)=O | Cl[C:2](=[O:1])[O:13][c:14]1[cH:15][cH:16][cH:17][cH:18][cH:19]1.O=[N+:3]([O-])[c:4]1[cH:5][n:6]([CH:7]2[CH2:8][CH2:9][CH2:10]2)[cH:11][n:12]1>>[O:1]=[C:2]([NH:3][c:4]1[cH:5][n:6]([CH:7]2[CH2:8][CH2:9][CH2:10]2)[cH:11][n:12]1)[O:13][c:14]1[cH:15][cH:16][cH:17][cH:18][cH:19]1 | O=C(Cl)Oc1ccccc1.O=[N+]([O-])c1cn(C2CCC2)cn1 | O=C(Nc1cn(C2CCC2)cn1)Oc1ccccc1 | null | [Pd] | CO.C(C)(=O)OCC | Functional Group Interconversion | OtherReaction | 621586d13f370c21d9c2ebcb2ff6f006e9ee7ea1c7077f0238750d1cd3d6b3c1 | 1634e3af8fcf6a1e120353a67242b0b2217479df5f77fe48e17bc4747cae1639 | O=C(Nc1cn(C2CCC2)cn1)Oc1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[c:4].O=[N+;H0;D3:5](-[O-])-[c:6]1:[#7;a:7]:[c:8]:[#7;a:9](-[C:10]):[c:11]:1>>[C:10]-[#7;a:9]1:[c:8]:[#7;a:7]:[c:6](-[NH;D2;+0:5]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[c:4]):[c:11]:1 | 72 | [{"value": 65.0, "product": "C1(=CC=CC=C1)OC(NC=1N=CN(C1)C1CCC1)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 72.0, "product": "C1(=CC=CC=C1)OC(NC=1N=CN(C1)C1CCC1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -78 | CELSIUS | 6 | HOUR | A Parr hydrogenation bottle was charged with 1-cyclobutyl-4-nitro-1H-imidazole (Preparation 1, 3 g, 18 mmol) and ethyl acetate (70 mL) followed by 10% Pd on carbon (1.2 g) under a nitrogen atmosphere. The mixture was hydrogenated for 6 h under 50 psi H2 at 23° C. The mixture was then filtered through a pad of celite wh... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Ether.Nitro group | Carbamic ester | null | null | c1c[nH]cn1.C1CCC1.c1ccccc1 | Other | [Pd].CO.C(C)(=O)OCC | -78 | 6 | O=C(Cl)Oc1ccccc1.O=[N+]([O-])c1cn(C2CCC2)cn1>[Pd].CO.C(C)(=O)OCC>O=C(Nc1cn(C2CCC2)cn1)Oc1ccccc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-93263c435c93462daf7f5cb4f36258a7 | Nc1cccc2cnccc12.O=C(Nc1cn(C2CCC2)cn1)Oc1ccccc1>>O=C(Nc1cn(C2CCC2)cn1)Nc1cccc2cnccc12 | C1(=CC=CC=C1)OC(NC=1N=CN(C1)C1CCC1)=O.NC1=C2C=CN=CC2=CC=C1>>C1(CCC1)N1C=NC(=C1)NC(=O)NC1=C2C=CN=CC2=CC=C1 | [NH2:13][c:14]1[cH:15][cH:16][cH:17][c:18]2[cH:19][n:20][cH:21][cH:22][c:23]12.c1ccc(O[C:2](=[O:1])[NH:3][c:4]2[cH:5][n:6]([CH:7]3[CH2:8][CH2:9][CH2:10]3)[cH:11][n:12]2)cc1>>[O:1]=[C:2]([NH:3][c:4]1[cH:5][n:6]([CH:7]2[CH2:8][CH2:9][CH2:10]2)[cH:11][n:12]1)[NH:13][c:14]1[cH:15][cH:16][cH:17][c:18]2[cH:19][n:20][cH:21][c... | Nc1cccc2cnccc12.O=C(Nc1cn(C2CCC2)cn1)Oc1ccccc1 | O=C(Nc1cn(C2CCC2)cn1)Nc1cccc2cnccc12 | null | null | O1CCOCC1.CN(C)C=O | Acylation | OtherReaction | f934f97c87bbca35fb6a2e4d8038127ebfc978d6e7ce352fd6acc2bdfa51d605 | d200d0a31426bb545e5b3d618baa98893432cc10661e9fc97221c430e6ae866e | O=C(Nc1cn(C2CCC2)cn1)Nc1cccc2cnccc12 | [#7;a:1]:[c:2](-[#7:3]-[C;H0;D3;+0:4](=[O;D1;H0:5])-O-c1:c:c:c:c:c:1):[c:6]:[#7;a:7].[NH2;D1;+0:8]-[c:9](:[c:10]):[c:11]>>[#7;a:1]:[c:2](-[#7:3]-[C;H0;D3;+0:4](=[O;D1;H0:5])-[NH;D2;+0:8]-[c:9](:[c:10]):[c:11]):[c:6]:[#7;a:7] | 52 | [{"value": 52.0, "product": "C1(CCC1)N1C=NC(=C1)NC(=O)NC1=C2C=CN=CC2=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 51.4, "product": "C1(CCC1)N1C=NC(=C1)NC(=O)NC1=C2C=CN=CC2=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 70 | CELSIUS | null | null | To a 1 dram vial with septa screw cap was added (1-cyclobutyl-1H-imidazol-4-yl)-carbamic acid phenyl ester (Example 4, 50 mg, 0.19 mmol), 5-aminoisoquinoline (30 mg, 0.21 mmol), and 1:1 dioxane-DMF (1 mL). The reaction mixture was heated at 70° C. for 2 h. The reaction mixture was adsorbed onto silica gel and was purif... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Primary amine | Urea | c1ccccc1 | null | c1c[nH]cn1.C1CCC1.c1ccc2cnccc2c1 | HO- | O1CCOCC1.CN(C)C=O | 70 | null | Nc1cccc2cnccc12.O=C(Nc1cn(C2CCC2)cn1)Oc1ccccc1>O1CCOCC1.CN(C)C=O>O=C(Nc1cn(C2CCC2)cn1)Nc1cccc2cnccc12 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-496b10fd4f3f4c06b178e187ca96e743 | Cc1ccc(S(=O)(=O)Cl)cc1.O=[N+]([O-])c1cn(C2CC(O)C2)cn1>>Cc1ccc(S(=O)(=O)O[C@@H]2C[C@@H](n3cnc([N+](=O)[O-])c3)C2)cc1 | [N+](=O)([O-])C=1N=CN(C1)C1CC(C1)O.CCN(CC)CC.C1(=CC=C(C=C1)S(=O)(=O)Cl)C>>[N+](=O)([O-])C=1N=CN(C1)[C@@H]1C[C@H](C1)OS(=O)(=O)C1=CC=C(C=C1)C | Cl[S:6]([c:5]1[cH:4][cH:3][c:2]([CH3:1])[cH:23][cH:22]1)(=[O:7])=[O:8].[OH:9][CH:10]1[CH2:11][CH:12]([n:13]2[cH:14][n:15][c:16]([N+:17](=[O:18])[O-:19])[cH:20]2)[CH2:21]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([S:6](=[O:7])(=[O:8])[O:9][C@H:10]2[CH2:11][C@H:12]([n:13]3[cH:14][n:15][c:16]([N+:17](=[O:18])[O-:19])[cH:20]3)[CH2:... | Cc1ccc(S(=O)(=O)Cl)cc1.O=[N+]([O-])c1cn(C2CC(O)C2)cn1 | Cc1ccc(S(=O)(=O)O[C@@H]2C[C@@H](n3cnc([N+](=O)[O-])c3)C2)cc1 | null | null | C(Cl)Cl | Acylation | Formation of Sulfonic Esters | ad3deb6f5d4dc7823aa3ad2bfe24985be1f3e6860ff8cc0ba215d7624074ef69 | ec645297cfd3107bffb1a4753ac125e48856598e58005e939bb2f0e91bf5e57c | O=S(=O)(O[C@H]1C[C@H](n2ccnc2)C1)c1ccccc1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6].[OH;D1;+0:7]-[CH;D3;+0:8]1-[C:9]-[C:10]-[C:11]-1>>[O;D1;H0:2]=[S;H0;D4;+0:1](=[O;D1;H0:3])(-[O;H0;D2;+0:7]-[C@@H;D3;+0:8]1-[C:9]-[C:10]-[C:11]-1)-[c:4](:[c:5]):[c:6] | 37 | [{"value": 37.0, "product": "[N+](=O)([O-])C=1N=CN(C1)[C@@H]1C[C@H](C1)OS(=O)(=O)C1=CC=C(C=C1)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 36.4, "product": "[N+](=O)([O-])C=1N=CN(C1)[C@@H]1C[C@H](C1)OS(=O)(=O)C1=CC=C(C=C1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 24 | HOUR | 3-(4-nitro-imidazol-1-yl)-cyclobutanol (Preparation 4, Step 1; 4 g, 22 mmol) was treated with Et3N (7.7 mL, 55 mmol) in methylene chloride (150 mL) followed by p-toluenesulfonyl chloride (TsCl) (5 g, 26.4 mmol) and 4-N,N-dimethylaminopyridine (DMAP) (268 mg, 2.2 mmol). The resulting mixture was stirred at room temperat... | 10.6084/m9.figshare.5104873.v1 | null | Tosylate.Secondary alcohol.Sulfonyl halide | Tosylate | null | null | c1ccccc1.C1CCC1.c1c[nH]cn1 | HCl | C(Cl)Cl | null | 24 | Cc1ccc(S(=O)(=O)Cl)cc1.O=[N+]([O-])c1cn(C2CC(O)C2)cn1>C(Cl)Cl>Cc1ccc(S(=O)(=O)O[C@@H]2C[C@@H](n3cnc([N+](=O)[O-])c3)C2)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-513e4b24fd25466eb922d5cf54934be7 | Cc1ccc(S(=O)(=O)O[C@@H]2C[C@H](n3cnc([N+](=O)[O-])c3)C2)cc1.O=C(O)Cc1cccc2ccccc12>>Cc1ccc(S(=O)(=O)O[C@@H]2C[C@@H](n3cnc(NC(=O)Cc4cccc5ccccc45)c3)C2)cc1 | [N+](=O)([O-])C=1N=CN(C1)[C@H]1C[C@H](C1)OS(=O)(=O)C1=CC=C(C=C1)C.CCN(CC)CC.C1(=CC=CC2=CC=CC=C12)CC(=O)O>>C1(=CC=CC2=CC=CC=C12)CC(=O)NC=1N=CN(C1)[C@@H]1C[C@H](C1)OS(=O)(=O)C1=CC=C(C=C1)C | O=[N+:17]([O-])[c:16]1[n:15][cH:14][n:13]([C@@H:12]2[CH2:11][C@H:10]([O:9][S:6]([c:5]3[cH:4][cH:3][c:2]([CH3:1])[cH:34][cH:33]3)(=[O:7])=[O:8])[CH2:32]2)[cH:31]1.O[C:18](=[O:19])[CH2:20][c:21]1[cH:22][cH:23][cH:24][c:25]2[cH:26][cH:27][cH:28][cH:29][c:30]12>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([S:6](=[O:7])(=[O:8])[O:9][C@H... | Cc1ccc(S(=O)(=O)O[C@@H]2C[C@H](n3cnc([N+](=O)[O-])c3)C2)cc1.O=C(O)Cc1cccc2ccccc12 | Cc1ccc(S(=O)(=O)O[C@@H]2C[C@@H](n3cnc(NC(=O)Cc4cccc5ccccc45)c3)C2)cc1 | null | [Pd] | C(C)(=O)OCC | Acylation | OtherReaction | 07d1695adb57fcbe166e427114577c880df19df2ee26bdadcbdf979c1785ff55 | 141f63f004bbbe912fc54e457ad7143d740953538a28293f72b74ca32c03fab9 | O=C(Cc1cccc2ccccc12)Nc1cn([C@H]2C[C@H](OS(=O)(=O)c3ccccc3)C2)cn1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[c:4].O=[N+;H0;D3:5](-[O-])-[c:6]1:[#7;a:7]:[c:8]:[#7;a:9](-[C:10]):[c:11]:1>>[C:10]-[#7;a:9]1:[c:8]:[#7;a:7]:[c:6](-[NH;D2;+0:5]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[c:4]):[c:11]:1 | 72.1 | [{"value": 72.0, "product": "C1(=CC=CC2=CC=CC=C12)CC(=O)NC=1N=CN(C1)[C@@H]1C[C@H](C1)OS(=O)(=O)C1=CC=C(C=C1)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 72.1, "product": "C1(=CC=CC2=CC=CC=C12)CC(=O)NC=1N=CN(C1)[C@@H]1C[C@H](C1)OS(=O)(=O)C1=CC=C(C=C1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired... | null | null | 1 | HOUR | trans-Toluene-4-sulfonic acid 3-(4-nitro-imidazol-1-yl)-cyclobutyl ester (Preparation 4, Step 2; 590 mg, 1.75 mmol) was mixed with 10% Pd on carbon (500 mg) in ethyl acetate (30 mL). The mixture was then reacted under 50 psi H2 at room temperature for 6 h. The mixture was filtered through celite into a flame-dried flas... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Nitro group | Secondary amide | null | null | c1ccccc1.C1CCC1.c1c[nH]cn1.c1ccc2ccccc2c1 | Other | [Pd].C(C)(=O)OCC | null | 1 | Cc1ccc(S(=O)(=O)O[C@@H]2C[C@H](n3cnc([N+](=O)[O-])c3)C2)cc1.O=C(O)Cc1cccc2ccccc12>[Pd].C(C)(=O)OCC>Cc1ccc(S(=O)(=O)O[C@@H]2C[C@@H](n3cnc(NC(=O)Cc4cccc5ccccc45)c3)C2)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-6b141b9602e2484784b713018045e405 | Cc1ccc(S(=O)(=O)O[C@@H]2C[C@@H](n3cnc(NC(=O)Cc4cccc5ccccc45)c3)C2)cc1.[N-]=[N+]=[N-]>>[N-]=[N+]=N[C@@H]1C[C@H](n2cnc(NC(=O)Cc3cccc4ccccc34)c2)C1 | C1(=CC=CC2=CC=CC=C12)CC(=O)NC=1N=CN(C1)[C@@H]1C[C@H](C1)OS(=O)(=O)C1=CC=C(C=C1)C.[N-]=[N+]=[N-].[Na+].C(Cl)(Cl)Cl>>N(=[N+]=[N-])[C@H]1C[C@H](C1)N1C=NC(=C1)NC(CC1=CC=CC2=CC=CC=C12)=O | Cc1ccc(S(=O)(=O)O[C@H:4]2[CH2:5][C@H:6]([n:7]3[cH:8][n:9][c:10]([NH:11][C:12](=[O:13])[CH2:14][c:15]4[cH:16][cH:17][cH:18][c:19]5[cH:20][cH:21][cH:22][cH:23][c:24]45)[cH:25]3)[CH2:26]2)cc1.[N-:1]=[N+:2]=[N-:3]>>[N-:1]=[N+:2]=[N:3][C@H:4]1[CH2:5][C@@H:6]([n:7]2[cH:8][n:9][c:10]([NH:11][C:12](=[O:13])[CH2:14][c:15]3[cH:1... | Cc1ccc(S(=O)(=O)O[C@@H]2C[C@@H](n3cnc(NC(=O)Cc4cccc5ccccc45)c3)C2)cc1.[N-]=[N+]=[N-] | [N-]=[N+]=N[C@@H]1C[C@H](n2cnc(NC(=O)Cc3cccc4ccccc34)c2)C1 | null | null | O.C(C)O | Heteroatom Alkylation and Arylation | OtherReaction | fe84f7dc4a5324b680ee11df06675b930381f67a207b8a43b5bbf96a6445c757 | 6961229e10e0db3c410e97098a5b94923cb09bb1c069f267ae4410afd98cc24e | O=C(Cc1cccc2ccccc12)Nc1cn(C2CCC2)cn1 | C-c1:c:c:c(-S(=O)(=O)-O-[C@@H;D3;+0:1]2-[C:2]-[C:3]-[C:4]-2):c:c:1.[N-;H0;D1:5]=[#7;+:6]=[N;-;D1;H0:7]>>[N;-;D1;H0:7]=[#7;+:6]=[N;H0;D2;+0:5]-[C@@H;D3;+0:1]1-[C:2]-[C:3]-[C:4]-1 | 79 | [{"value": 79.0, "product": "N(=[N+]=[N-])[C@H]1C[C@H](C1)N1C=NC(=C1)NC(CC1=CC=CC2=CC=CC=C12)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 78.5, "product": "N(=[N+]=[N-])[C@H]1C[C@H](C1)N1C=NC(=C1)NC(CC1=CC=CC2=CC=CC=C12)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 96 | HOUR | trans-Toluene-4-sulfonic acid 3-[4-(2-naphthalen-1-yl-acetylamino)-imidazol-1-yl]-cyclobutyl ester (Preparation 4, Step 3; 593 mg, 1.25 mmol) was mixed with sodium azide (813 mg, 12.5 mmol) in ethanol (15 mL), water (5 mL), and chloroform (5 mL). The mixture was then heated at reflux with stirring for 96 h. The solvent... | 10.6084/m9.figshare.5104873.v1 | null | Tosylate | Azide | c1ccccc1.C1CCC1 | C1CCC1 | C1CCC1.c1c[nH]cn1.c1ccc2ccccc2c1 | TsOH.HO- | O.C(C)O | null | 96 | Cc1ccc(S(=O)(=O)O[C@@H]2C[C@@H](n3cnc(NC(=O)Cc4cccc5ccccc45)c3)C2)cc1.[N-]=[N+]=[N-]>O.C(C)O>[N-]=[N+]=N[C@@H]1C[C@H](n2cnc(NC(=O)Cc3cccc4ccccc34)c2)C1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-2336ab26e4584b5fb49276c5b188bb19 | [N-]=[N+]=N[C@@H]1C[C@H](n2cnc(NC(=O)Cc3cccc4ccccc34)c2)C1>>N[C@H]1C[C@@H](n2cnc(NC(=O)Cc3cccc4ccccc34)c2)C1 | N(=[N+]=[N-])[C@H]1C[C@H](C1)N1C=NC(=C1)NC(CC1=CC=CC2=CC=CC=C12)=O.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1>>N[C@H]1C[C@H](C1)N1C=NC(=C1)NC(CC1=CC=CC2=CC=CC=C12)=O | [N-]=[N+]=[N:1][C@H:2]1[CH2:3][C@@H:4]([n:5]2[cH:6][n:7][c:8]([NH:9][C:10](=[O:11])[CH2:12][c:13]3[cH:14][cH:15][cH:16][c:17]4[cH:18][cH:19][cH:20][cH:21][c:22]34)[cH:23]2)[CH2:24]1>>[NH2:1][C@H:2]1[CH2:3][C@@H:4]([n:5]2[cH:6][n:7][c:8]([NH:9][C:10](=[O:11])[CH2:12][c:13]3[cH:14][cH:15][cH:16][c:17]4[cH:18][cH:19][cH:2... | [N-]=[N+]=N[C@@H]1C[C@H](n2cnc(NC(=O)Cc3cccc4ccccc34)c2)C1 | N[C@H]1C[C@@H](n2cnc(NC(=O)Cc3cccc4ccccc34)c2)C1 | null | null | O1CCCC1.O | Reduction | Azide to amine reduction (Staudinger) | 4c9e4990dae2bb965dec06bd45e318560989ee3681b61e443f7aa363b7cfa222 | cd009d687d606bf351eac9390a176d16be38f2c8216a599b398641009c215027 | O=C(Cc1cccc2ccccc12)Nc1cn(C2CCC2)cn1 | [C:1]-[C:2](-[N;H0;D2;+0:3]=[N+]=[N-])-[C:4]>>[C:1]-[C:2](-[NH2;D1;+0:3])-[C:4] | 95 | [{"value": 95.0, "product": "N[C@H]1C[C@H](C1)N1C=NC(=C1)NC(CC1=CC=CC2=CC=CC=C12)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 95.0, "product": "N[C@H]1C[C@H](C1)N1C=NC(=C1)NC(CC1=CC=CC2=CC=CC=C12)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 18 | HOUR | N-[1-(cis-3-azido-cyclobutyl)-1H-imidazol-4-yl]-2-naphthalen-1-yl-acetamide (Preparation 4, Step 4; 330 mg, 0.95 mmol) was treated with triphenylphosphine (301 mg, 1.15 mmol) in tetrahydrofuran (10 mL) and water (1 mL) at 23° C. The solution was stirred at room temperature for 18 h. The solvent was removed in vacuo and... | 10.6084/m9.figshare.5104873.v1 | null | Azide | Primary amine | null | null | C1CCC1.c1c[nH]cn1.c1ccc2ccccc2c1 | Other | O1CCCC1.O | null | 18 | [N-]=[N+]=N[C@@H]1C[C@H](n2cnc(NC(=O)Cc3cccc4ccccc34)c2)C1>O1CCCC1.O>N[C@H]1C[C@@H](n2cnc(NC(=O)Cc3cccc4ccccc34)c2)C1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-12cb8a95f5ef4ea8885b99cd70a92718 | Cc1cccc(C(=O)O)n1.N[C@H]1C[C@@H](n2cnc(NC(=O)Cc3cccc4ccccc34)c2)C1>>Cc1cccc(C(=O)NC2CC(n3cnc(NC(=O)Cc4cccc5ccccc45)c3)C2)n1 | [OH-].[Na+].CC1=CC=CC(=N1)C(=O)O.Cl.CN(CCCN=C=NCC)C.N[C@H]1C[C@H](C1)N1C=NC(=C1)NC(CC1=CC=CC2=CC=CC=C12)=O>>C1(=CC=CC2=CC=CC=C12)CC(=O)NC=1N=CN(C1)C1CC(C1)NC(=O)C1=NC(=CC=C1)C | O[C:7]([c:6]1[cH:5][cH:4][cH:3][c:2]([CH3:1])[n:33]1)=[O:8].[NH2:9][C@H:10]1[CH2:11][C@@H:12]([n:13]2[cH:14][n:15][c:16]([NH:17][C:18](=[O:19])[CH2:20][c:21]3[cH:22][cH:23][cH:24][c:25]4[cH:26][cH:27][cH:28][cH:29][c:30]34)[cH:31]2)[CH2:32]1>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][c:6]([C:7](=[O:8])[NH:9][CH:10]2[CH2:11][CH:1... | Cc1cccc(C(=O)O)n1.N[C@H]1C[C@@H](n2cnc(NC(=O)Cc3cccc4ccccc34)c2)C1 | Cc1cccc(C(=O)NC2CC(n3cnc(NC(=O)Cc4cccc5ccccc45)c3)C2)n1 | null | CN(C)C=1C=CN=CC1 | O.C(Cl)Cl | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(Cc1cccc2ccccc12)Nc1cn(C2CC(NC(=O)c3ccccn3)C2)cn1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[#7;a:5]:[c:6].[NH2;D1;+0:7]-[C@@H;D3;+0:8]1-[C:9]-[C:10]-[C:11]-1>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[NH;D2;+0:7]-[CH;D3;+0:8]1-[C:9]-[C:10]-[C:11]-1)-[c:3](:[c:4]):[#7;a:5]:[c:6] | 98.6 | [{"value": 95.0, "product": "C1(=CC=CC2=CC=CC=C12)CC(=O)NC=1N=CN(C1)C1CC(C1)NC(=O)C1=NC(=CC=C1)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 98.6, "product": "C1(=CC=CC2=CC=CC=C12)CC(=O)NC=1N=CN(C1)C1CC(C1)NC(=O)C1=NC(=CC=C1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 10 | MINUTE | A solution of 6-methylpicolinic acid (9.4 mg, 0.07 mmol) in methylene chloride was treated with 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (84 mg) and DMAP (2 mg) at 23° C. After stirring for 10 min, N-[1-(cis-3-amino-cyclobutyl)-1H-imidazol-4-yl]-2-naphthalen-1-yl-acetamide (Example 6, 20 mg, 0.06 mmo... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccncc1.C1CCC1.c1c[nH]cn1.c1ccc2ccccc2c1 | HO- | CN(C)C=1C=CN=CC1.O.C(Cl)Cl | null | 0.166667 | Cc1cccc(C(=O)O)n1.N[C@H]1C[C@@H](n2cnc(NC(=O)Cc3cccc4ccccc34)c2)C1>CN(C)C=1C=CN=CC1.O.C(Cl)Cl>Cc1cccc(C(=O)NC2CC(n3cnc(NC(=O)Cc4cccc5ccccc45)c3)C2)n1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-9f844d6be33f44678c9fb02776f3567e | Br.Nc1cccc2cnccc12>>Brc1cccc2cnccc12 | [OH-].[K+].N(=O)[O-].[Na+].NC1=C2C=CN=CC2=CC=C1.Br>>BrC1=C2C=CN=CC2=CC=C1 | [BrH:1].N[c:2]1[cH:3][cH:4][cH:5][c:6]2[cH:7][n:8][cH:9][cH:10][c:11]12>>[Br:1][c:2]1[cH:3][cH:4][cH:5][c:6]2[cH:7][n:8][cH:9][cH:10][c:11]12 | Br.Nc1cccc2cnccc12 | Brc1cccc2cnccc12 | null | [Cu] | O | Miscellaneous | OtherReaction | a80b46bfc720178a7247f763a2a5c279a0921fee09e9f9f15b3416ca42dac62e | 1129c10513c603d2647e51dd9713063aaf10bd8a364ed275b9b93c32624e3ba4 | c1ccc2cnccc2c1 | N-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]1:[c:5]:[c:6]:[#7;a:7]:[c:8]:[c:9]:1.[BrH;D0;+0:10]>>[Br;H0;D1;+0:10]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]1:[c:5]:[c:6]:[#7;a:7]:[c:8]:[c:9]:1 | 53 | [{"value": 53.0, "product": "BrC1=C2C=CN=CC2=CC=C1", "details": "PERCENTYIELD", "is_desired": false}] | -78 | CELSIUS | 15 | MINUTE | 5-Aminoisoquinoline (5.0 g, 34.7 mmol) was mixed with 48% aqueous HBr (65 mL) at −78° C. for 15 min. Sodium nitrite (3.1 g, 45 mmol) in water (6 mL) was then added dropwise. After stirring for 15 min at −78° C., the mixture was warmed to 0° C. Copper powder (0.3 g) was added very slowly to avoid excessive foaming. Afte... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | Aromatic halide | c1ccc2cnccc2c1 | c1ccc2cnccc2c1 | c1ccc2cnccc2c1 | Other | [Cu].O | -78 | 0.25 | Br.Nc1cccc2cnccc12>[Cu].O>Brc1cccc2cnccc12 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-45852c4d4052420286b592d39aa1fdb0 | Brc1cccc2cnccc12.C=C[CH2][Sn]([CH2]CCC)([CH2]CCC)[CH2]CCC>>C=CCc1cccc2cnccc12 | BrC1=C2C=CN=CC2=CC=C1.C(C=C)[Sn](CCCC)(CCCC)CCCC.[F-].[K+]>>C(C=C)C1=C2C=CN=CC2=CC=C1 | Br[c:4]1[cH:5][cH:6][cH:7][c:8]2[cH:9][n:10][cH:11][cH:12][c:13]12.CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[CH2:3][CH:2]=[CH2:1]>>[CH2:1]=[CH:2][CH2:3][c:4]1[cH:5][cH:6][cH:7][c:8]2[cH:9][n:10][cH:11][cH:12][c:13]12 | Brc1cccc2cnccc12.C=C[CH2][Sn]([CH2]CCC)([CH2]CCC)[CH2]CCC | C=CCc1cccc2cnccc12 | null | C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.Cl[Pd]Cl | C1(=CC=CC=C1)C | C-C Coupling | Stille reaction_allyl | 3d6f296cd1217b6cb0262306f30301e2261b84eea5090d90b511755d78d7700c | 1bc148b1555a9c8fc11becbecded2f430d1be44535a8bef8d1f9251cc75697a6 | c1ccc2cnccc2c1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]1:[c:5]:[c:6]:[#7;a:7]:[c:8]:[c:9]:1.C-C-C-[CH2]-[Sn](-[CH2;D2;+0:10]-[C:11]=[C;D1;H2:12])(-[CH2]-C-C-C)-[CH2]-C-C-C>>[C;D1;H2:12]=[C:11]-[CH2;D2;+0:10]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]1:[c:5]:[c:6]:[#7;a:7]:[c:8]:[c:9]:1 | 92 | [{"value": 92.0, "product": "C(C=C)C1=C2C=CN=CC2=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 91.9, "product": "C(C=C)C1=C2C=CN=CC2=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 15 | MINUTE | 5-Bromoisoquinoline (Preparation 6, Step 1, 1.04 g, 5.0 mmol) was mixed with allyltributyltin (1.7 mL, 5.5 mmol) and dichloropalladium bis(triphenylphosphine) (176 mg, 0.25 mmol) in toluene (20 mL) under a nitrogen atmosphere. The mixture was heated at reflux for 16 h. After cooling to room temperature, a saturated aqu... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Allyl.Tin | Allyl | c1ccc2cnccc2c1 | c1ccc2cnccc2c1 | c1ccc2cnccc2c1 | HBr.Sn | C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.Cl[Pd]Cl.C1(=CC=CC=C1)C | null | 0.25 | Brc1cccc2cnccc12.C=C[CH2][Sn]([CH2]CCC)([CH2]CCC)[CH2]CCC>C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.Cl[Pd]Cl.C1(=CC=CC=C1)C>C=CCc1cccc2cnccc12 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-5e769c17b7c64d7f898e6a8d4ec550c4 | C=CCc1cccc2cnccc12.CO.[O]=[Mn](=[O])(=[O])[O-]>>COC(=O)Cc1cccc2cnccc12 | [O-][Mn](=O)(=O)=O.[K+].C(C=C)C1=C2C=CN=CC2=CC=C1.O.CO.C(CO)O>>COC(CC1=C2C=CN=CC2=CC=C1)=O | C=[CH:3][CH2:5][c:6]1[cH:7][cH:8][cH:9][c:10]2[cH:11][n:12][cH:13][cH:14][c:15]12.[CH3:1][OH:2].[O]=[Mn](=[O])([O-])=[O:4]>>[CH3:1][O:2][C:3](=[O:4])[CH2:5][c:6]1[cH:7][cH:8][cH:9][c:10]2[cH:11][n:12][cH:13][cH:14][c:15]12 | C=CCc1cccc2cnccc12.CO.[O]=[Mn](=[O])(=[O])[O-] | COC(=O)Cc1cccc2cnccc12 | null | null | C(C)(=O)O.C(Cl)Cl | Acylation | OtherReaction | 51213de6b1433e32dc9d7d7afe9913992311eb89aa044c5216885e6b098219cb | 446cb7d8dc7cecea3abe2b1ac52def3cf663d88a77e1b0a85a7a3d919f272021 | c1ccc2cnccc2c1 | C=[CH;D2;+0:1]-[C:2]-[c:3].[C;D1;H3:4]-[OH;D1;+0:5].[O-]-[Mn](=[O;H0;D1;+0:6])(=[O])=[O]>>[C;D1;H3:4]-[O;H0;D2;+0:5]-[C;H0;D3;+0:1](=[O;H0;D1;+0:6])-[C:2]-[c:3] | null | [] | 0 | CELSIUS | 18 | HOUR | 5-Allylisoquinoline (Preparation 6, Step 2; 169 mg, 1.0 mmol) in methylene chloride (2 mL), acetic acid (0.5 mL), and water (0.5 mL) was treated with dimethyl polyethylene glycol (Mn ca. 500, 95 uL, 100 mg, 0.2 mmol) in methylene chloride (1 mL) at 23° C. The mixture was cooled to 0° C. and powdered KMnO4 (521 mg, 3.3 ... | 10.6084/m9.figshare.5104873.v1 | null | Allyl.Methanol | Ester | null | null | c1ccc2cnccc2c1 | HO- | C(C)(=O)O.C(Cl)Cl | 0 | 18 | C=CCc1cccc2cnccc12.CO.[O]=[Mn](=[O])(=[O])[O-]>C(C)(=O)O.C(Cl)Cl>COC(=O)Cc1cccc2cnccc12 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-cb8eabb9955f4cb8ac74a6e293ab6ba3 | COC(=O)Cc1cccc2cnccc12>>O=C(O)Cc1cccc2cnccc12 | COC(CC1=C2C=CN=CC2=CC=C1)=O.[OH-].[Na+]>>C1=NC=CC2=C(C=CC=C12)CC(=O)O | C[O:3][C:2](=[O:1])[CH2:4][c:5]1[cH:6][cH:7][cH:8][c:9]2[cH:10][n:11][cH:12][cH:13][c:14]12>>[O:1]=[C:2]([OH:3])[CH2:4][c:5]1[cH:6][cH:7][cH:8][c:9]2[cH:10][n:11][cH:12][cH:13][c:14]12 | COC(=O)Cc1cccc2cnccc12 | O=C(O)Cc1cccc2cnccc12 | null | null | C(C)(=O)O | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccc2cnccc2c1 | 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] | 47 | [{"value": 47.0, "product": "C1=NC=CC2=C(C=CC=C12)CC(=O)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 41.7, "product": "C1=NC=CC2=C(C=CC=C12)CC(=O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 50 | CELSIUS | 8 | HOUR | Isoquinolin-5-yl-acetic acid methyl ester (Preparation 6, Step 3; 90 mg, 0.448 mmol) was treated with aqueous sodium hydroxide (4N, 3 mL) and the solution was heated at 50° C. for 4 h. The solution was cooled to 0° C. and acetic acid (2 mL) was added dropwise, which resulted in the formation of a precipitate. The mixtu... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccc2cnccc2c1 | Other | C(C)(=O)O | 50 | 8 | COC(=O)Cc1cccc2cnccc12>C(C)(=O)O>O=C(O)Cc1cccc2cnccc12 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-a9dd66b024284e8ba5081694ebe1d0d1 | CCOC(=O)C1=CCCCC1S(=O)(=O)Nc1ccc(F)cc1F.SCc1ccccc1>>CCOC(=O)C1=CCCCC1SCc1ccccc1 | FC1=C(C=CC(=C1)F)NS(=O)(=O)C1CCCC=C1C(=O)OCC.C1(=CC=CC=C1)CS.C1CCC2=NCCCN2CC1>>C(C1=CC=CC=C1)SC1CCCC=C1C(=O)OCC | O=S(=O)(Nc1ccc(F)cc1F)[CH:11]1[C:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])=[CH:7][CH2:8][CH2:9][CH2:10]1.[SH:12][CH2:13][c:14]1[cH:15][cH:16][cH:17][cH:18][cH:19]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6]1=[CH:7][CH2:8][CH2:9][CH2:10][CH:11]1[S:12][CH2:13][c:14]1[cH:15][cH:16][cH:17][cH:18][cH:19]1 | CCOC(=O)C1=CCCCC1S(=O)(=O)Nc1ccc(F)cc1F.SCc1ccccc1 | CCOC(=O)C1=CCCCC1SCc1ccccc1 | null | null | CN(C=O)C.C(C)(=O)OCC | Heteroatom Alkylation and Arylation | OtherReaction | e004b55701497d7f887b0985a65eca3bb4adb702fb3d6e33c5b8a4e402b31ab3 | cfa39748e584de8627741a4eb08a3e46f3d1f6ce86fafef224e3e259ec2309d6 | C1=CC(SCc2ccccc2)CCC1 | F-c1:c:c:c(-N-S(=O)(=O)-[CH;D3;+0:1]2-[C:2]-[C:3]-[C:4]-[C:5]=[C:6]-2-[C:7](=[O;D1;H0:8])-[#8:9]-[C:10]):c(-F):c:1.[SH;D1;+0:11]-[C:12]-[c:13]>>[C:10]-[#8:9]-[C:7](=[O;D1;H0:8])-[C:6]1=[C:5]-[C:4]-[C:3]-[C:2]-[CH;D3;+0:1]-1-[S;H0;D2;+0:11]-[C:12]-[c:13] | null | [] | null | null | 18 | HOUR | To a solution of ethyl 6-[N-(2,4-difluorophenyl)sulfamoyl]-1-cyclohexene-1-carboxylate (1 g, synthesized according to the method disclosed in JP-A-10-056492) and phenylmethanethiol (719 mg) in N,N-dimethylformamide (20 ml) was added dropwise under ice-cooling 1,8-diazabicyclo[5,4,0]-7-undecene (441 mg) and the mixture ... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonamide.Aromatic halide.Aromatic halide.Aliphatic thiol | Monosulfide | c1ccccc1.C1=CCCCC1 | C1=CCCCC1 | C1=CCCCC1.c1ccccc1 | HF | CN(C=O)C.C(C)(=O)OCC | null | 18 | CCOC(=O)C1=CCCCC1S(=O)(=O)Nc1ccc(F)cc1F.SCc1ccccc1>CN(C=O)C.C(C)(=O)OCC>CCOC(=O)C1=CCCCC1SCc1ccccc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-1bdc4cc6fcb44052a3d901234294f8e6 | CCOC(=O)C1=CCCCC1S(=O)(=O)Nc1ccc(F)cc1F.COc1ccc(CS)cc1>>CCOC(=O)C1=CCCCC1SCc1ccc(OC)cc1 | FC1=C(C=CC(=C1)F)NS(=O)(=O)C1CCCC=C1C(=O)OCC.COC1=CC=C(C=C1)CS>>COC1=CC=C(CSC2CCCC=C2C(=O)OCC)C=C1 | O=S(=O)(Nc1ccc(F)cc1F)[CH:11]1[C:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])=[CH:7][CH2:8][CH2:9][CH2:10]1.[SH:12][CH2:13][c:14]1[cH:15][cH:16][c:17]([O:18][CH3:19])[cH:20][cH:21]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6]1=[CH:7][CH2:8][CH2:9][CH2:10][CH:11]1[S:12][CH2:13][c:14]1[cH:15][cH:16][c:17]([O:18][CH3:19])[cH:20][cH:21... | CCOC(=O)C1=CCCCC1S(=O)(=O)Nc1ccc(F)cc1F.COc1ccc(CS)cc1 | CCOC(=O)C1=CCCCC1SCc1ccc(OC)cc1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | e004b55701497d7f887b0985a65eca3bb4adb702fb3d6e33c5b8a4e402b31ab3 | cfa39748e584de8627741a4eb08a3e46f3d1f6ce86fafef224e3e259ec2309d6 | C1=CC(SCc2ccccc2)CCC1 | F-c1:c:c:c(-N-S(=O)(=O)-[CH;D3;+0:1]2-[C:2]-[C:3]-[C:4]-[C:5]=[C:6]-2-[C:7](=[O;D1;H0:8])-[#8:9]-[C:10]):c(-F):c:1.[SH;D1;+0:11]-[C:12]-[c:13]>>[C:10]-[#8:9]-[C:7](=[O;D1;H0:8])-[C:6]1=[C:5]-[C:4]-[C:3]-[C:2]-[CH;D3;+0:1]-1-[S;H0;D2;+0:11]-[C:12]-[c:13] | 95.6 | [{"value": 95.6, "product": "COC1=CC=C(CSC2CCCC=C2C(=O)OCC)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | In the same manner as in Reference Example 1, ethyl 6-[N-(2,4-difluorophenyl)sulfamoyl]-1-cyclohexene-1-carboxylate (1 g) and (4-methoxyphenyl)methanethiol (893 mg) were reacted to give ethyl 6-[(4-methoxybenzyl)-sulfanyl]-1-cyclohexene-1-carboxylate (848 mg) as a colorless oil.
Conditions: See reaction.notes.procedure... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonamide.Aromatic halide.Aromatic halide.Aliphatic thiol | Monosulfide | c1ccccc1.C1=CCCCC1 | C1=CCCCC1 | C1=CCCCC1.c1ccccc1 | HF | null | null | null | CCOC(=O)C1=CCCCC1S(=O)(=O)Nc1ccc(F)cc1F.COc1ccc(CS)cc1>>CCOC(=O)C1=CCCCC1SCc1ccc(OC)cc1 |
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