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-018fd0e1351f4fd09b20fcddd97b4c7a | ord-61aad68a3b1947e1aaa4cb73733b890c | COc1ccc(N2CCNCC2)cc1.Clc1ccncc1>>COc1ccc(N2CCN(c3ccncc3)CC2)cc1 | N1(CCNCC1)C1=CC=C(C=C1)OC.Cl.ClC1=CC=NC=C1.N>>N1=CC=C(C=C1)N1CCN(CC1)C1=CC=C(C=C1)OC | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([N:7]2[CH2:8][CH2:9][NH:10][CH2:17][CH2:18]2)[cH:19][cH:20]1.Cl[c:11]1[cH:12][cH:13][n:14][cH:15][cH:16]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([N:7]2[CH2:8][CH2:9][N:10]([c:11]3[cH:12][cH:13][n:14][cH:15][cH:16]3)[CH2:17][CH2:18]2)[cH:19][cH:20]1 | COc1ccc(N2CCNCC2)cc1.Clc1ccncc1 | COc1ccc(N2CCN(c3ccncc3)CC2)cc1 | null | null | O | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | fa523b05de53c4b0abc4cfee73617ebc93929b0985f4e85a4f5201b7c9df83f1 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc(N2CCN(c3ccncc3)CC2)cc1 | Cl-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[#7;a:4]:[c:5]:[c:6]:1.[#7:7]1-[C:8]-[C:9]-[NH;D2;+0:10]-[C:11]-[C:12]-1>>[#7:7]1-[C:8]-[C:9]-[N;H0;D3;+0:10](-[c;H0;D3;+0:1]2:[c:2]:[c:3]:[#7;a:4]:[c:5]:[c:6]:2)-[C:11]-[C:12]-1 | 31 | [{"value": 31.0, "product": "N1=CC=C(C=C1)N1CCN(CC1)C1=CC=C(C=C1)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 4-(piperazin-1-yl)anisole (4.24 g) and 4-chloropyridine hydrochloride (3.35 g) were intimately mixed and heated at 160°-170° C. (bath temperature) for 7 minutes. The solid obtained on cooling was dissolved in water (75 ml) and the solution basified with aqueous ammonia. The solid precipitate was extracted into ethyl ac... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | C1C[NH]CCN1.c1ccncc1 | C1C[NH]CC[NH]1.c1ccncc1 | c1ccccc1.C1C[NH]CC[NH]1.c1ccncc1 | HCl | O | null | null | COc1ccc(N2CCNCC2)cc1.Clc1ccncc1>O>COc1ccc(N2CCN(c3ccncc3)CC2)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-9f122af1a0394a17b79d34afbf18a558 | COc1ccc(N2CCN(c3ccncc3)CC2)cc1>>Oc1ccc(N2CCN(c3ccncc3)CC2)cc1 | N1=CC=C(C=C1)N1CCN(CC1)C1=CC=C(C=C1)OC.O.N>>N1=CC=C(C=C1)N1CCN(CC1)C1=CC=C(C=C1)O | C[O:1][c:2]1[cH:3][cH:4][c:5]([N:6]2[CH2:7][CH2:8][N:9]([c:10]3[cH:11][cH:12][n:13][cH:14][cH:15]3)[CH2:16][CH2:17]2)[cH:18][cH:19]1>>[OH:1][c:2]1[cH:3][cH:4][c:5]([N:6]2[CH2:7][CH2:8][N:9]([c:10]3[cH:11][cH:12][n:13][cH:14][cH:15]3)[CH2:16][CH2:17]2)[cH:18][cH:19]1 | COc1ccc(N2CCN(c3ccncc3)CC2)cc1 | Oc1ccc(N2CCN(c3ccncc3)CC2)cc1 | null | null | Br | Deprotection | Cleavage of methoxy ethers to alcohols | c5320c7dfa4f544d4900efcae9b3262bf0d5286bcf39c86109232351f35b23d5 | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | c1ccc(N2CCN(c3ccncc3)CC2)cc1 | C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[OH;D1;+0:1]-[c:2](:[c:3]):[c:4] | 95.6 | [{"value": 95.6, "product": "N1=CC=C(C=C1)N1CCN(CC1)C1=CC=C(C=C1)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | The product from step (i) (1.5 g) in concentrated hydrobromic acid (30 ml) was heated under argon at 130°-135° C. for 21/2 hours. The solution was cooled, poured into water (150 ml) and basified with aqueous ammonia. The precipitate was filtered, washed with water and dried to give 4-[4-(4-pyridyl)piperazin-1-yl]phenol... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | null | null | c1ccccc1.C1C[NH]CC[NH]1.c1ccncc1 | Other | Br | null | null | COc1ccc(N2CCN(c3ccncc3)CC2)cc1>Br>Oc1ccc(N2CCN(c3ccncc3)CC2)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-f32c2189fde44a52a00908f735c49175 | Oc1ccc(N2CCN(c3ccncc3)CC2)cc1.[OH-]>>O=C(O)CCCOc1ccc(N2CCN(c3ccncc3)CC2)cc1 | N1=CC=C(C=C1)N1CCN(CC1)C1=CC=C(C=C1)O.[OH-].[Na+]>>N1=CC=C(C=C1)N1CCN(CC1)C1=CC=C(OCCCC(=O)O)C=C1 | [cH:2]1[c:8]([OH:7])[cH:25][cH:24][c:11]([N:12]2[CH2:13][CH2:14][N:15]([c:16]3[cH:17][cH:18][n:19][cH:20][cH:21]3)[CH2:22][CH2:23]2)[cH:10]1.[OH-:1]>>[O:1]=[C:2]([OH:3])[CH2:4][CH2:5][CH2:6][O:7][c:8]1[cH:9][cH:10][c:11]([N:12]2[CH2:13][CH2:14][N:15]([c:16]3[cH:17][cH:18][n:19][cH:20][cH:21]3)[CH2:22][CH2:23]2)[cH:24][... | Oc1ccc(N2CCN(c3ccncc3)CC2)cc1.[OH-] | O=C(O)CCCOc1ccc(N2CCN(c3ccncc3)CC2)cc1 | null | null | C(C)O | Acylation | OtherReaction | ac192a7dc474ed4813d5aad908f793ad61f8cd56c2f90ef0d5eff0e7af1c6bb0 | ae35dc17b368055949aa27e41379e21c68bbaeab7b7f6b9254542ec1d9d20a48 | c1ccc(N2CCN(c3ccncc3)CC2)cc1 | [#7:1]-[c:2]1:[c:3]:[c:4]:[c;H0;D3;+0:5](-[OH;D1;+0:6]):[cH;D2;+0:7]:[cH;D2;+0:8]:1.[OH-;D0:9]>>[#7:1]-[c:2]1:[c:3]:[c:4]:[c;H0;D3;+0:5](-[O;H0;D2;+0:6]-[C:10]-[C:11]-[C:12]-[C;H0;D3;+0:7](-[O;D1;H1:13])=[O;H0;D1;+0:9]):[c:14]:[cH;D2;+0:8]:1 | null | [] | null | null | null | null | A solution of the product of Example 25 (0.1 g) in aqueous sodium hydroxide (1N, 0.8 ml) and ethanol (2 ml) was kept for 2 hours. The solution was evaporated and the residue dissolved in water (5 ml). Hydrochloric acid (1N, 0.8 ml) was added and the precipitate was filtered and washed with water and ether to give the t... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic alcohol | Carboxylic acid.Ether | c1ccccc1 | c1ccccc1 | c1ccccc1.C1C[NH]CC[NH]1.c1ccncc1 | null | C(C)O | null | null | Oc1ccc(N2CCN(c3ccncc3)CC2)cc1.[OH-]>C(C)O>O=C(O)CCCOc1ccc(N2CCN(c3ccncc3)CC2)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-717e69902b0247adb593fabcb51078ca | O=C(Cl)C(=O)Cl.O=C(O)c1ccc(N2CCNCC2c2ccncc2)cc1>>O=C(Cl)c1ccc(N2CCNCC2c2ccncc2)cc1 | C(C(=O)Cl)(=O)Cl.N1=CC=C(C=C1)C1N(CCNC1)C1=CC=C(C(=O)O)C=C1>>N1=CC=C(C=C1)C1N(CCNC1)C1=CC=C(C(=O)Cl)C=C1 | O=C(Cl)C(=O)[Cl:3].O[C:2](=[O:1])[c:4]1[cH:5][cH:6][c:7]([N:8]2[CH2:9][CH2:10][NH:11][CH2:12][CH:13]2[c:14]2[cH:15][cH:16][n:17][cH:18][cH:19]2)[cH:20][cH:21]1>>[O:1]=[C:2]([Cl:3])[c:4]1[cH:5][cH:6][c:7]([N:8]2[CH2:9][CH2:10][NH:11][CH2:12][CH:13]2[c:14]2[cH:15][cH:16][n:17][cH:18][cH:19]2)[cH:20][cH:21]1 | O=C(Cl)C(=O)Cl.O=C(O)c1ccc(N2CCNCC2c2ccncc2)cc1 | O=C(Cl)c1ccc(N2CCNCC2c2ccncc2)cc1 | null | CN(C)C=O | ClCCl | Functional Group Interconversion | Alcohol to chloride_Other | 013cec2edeb273a7a148f349d36a52d99ff4e7bcf8eed78085df830088e387ac | aedb1f68dc5b7eb0583043e1125b741382b17974140a2f46554f0110e2ddc884 | c1ccc(N2CCNCC2c2ccncc2)cc1 | Cl-C(=O)-C(=O)-[Cl;H0;D1;+0:1].O-[C;H0;D3;+0:2](=[O;D1;H0:3])-[c:4](:[c:5]):[c:6]>>[Cl;H0;D1;+0:1]-[C;H0;D3;+0:2](=[O;D1;H0:3])-[c:4](:[c:5]):[c:6] | null | [] | null | null | 2 | HOUR | Oxalyl chloride (0.5 ml) was added to a stirred suspension of 4-((4-pyridyl)piperazin-1-yl)benzoic acid in dichloromethane (15 ml), followed by DMF (1 drop). The mixture was stirred for 2 hours and evaporated to dryness to give 4-[(4-pyridyl)piperazin-1-yl]benzoyl chloride which was used immediately.
Conditions: See re... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Acyl halide.Carboxylic acid | Acyl halide | null | null | c1ccccc1.C1C[NH]CCN1.c1ccncc1 | HCl | CN(C)C=O.ClCCl | null | 2 | O=C(Cl)C(=O)Cl.O=C(O)c1ccc(N2CCNCC2c2ccncc2)cc1>CN(C)C=O.ClCCl>O=C(Cl)c1ccc(N2CCNCC2c2ccncc2)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-fd61041e68a7434fbe024bb07200a8f8 | COC(=O)CC(N)c1ccc(OCC2CCN(c3ccncc3)CC2)cc1.Cc1ccc(S(=O)(=O)Cl)cc1>>COC(=O)CC(NS(=O)(=O)c1ccc(C)cc1)c1ccc(OCC2CCN(c3ccncc3)CC2)cc1 | Cl.Cl.NC(CC(=O)OC)C1=CC=C(C=C1)OCC1CCN(CC1)C1=CC=NC=C1.C1(=CC=C(C=C1)S(=O)(=O)Cl)C>>CC1=CC=C(C=C1)S(=O)(=O)NC(CC(=O)OC)C1=CC=C(C=C1)OCC1CCN(CC1)C1=CC=NC=C1 | [CH3:1][O:2][C:3](=[O:4])[CH2:5][CH:6]([NH2:7])[c:18]1[cH:19][cH:20][c:21]([O:22][CH2:23][CH:24]2[CH2:25][CH2:26][N:27]([c:28]3[cH:29][cH:30][n:31][cH:32][cH:33]3)[CH2:34][CH2:35]2)[cH:36][cH:37]1.Cl[S:8](=[O:9])(=[O:10])[c:11]1[cH:12][cH:13][c:14]([CH3:15])[cH:16][cH:17]1>>[CH3:1][O:2][C:3](=[O:4])[CH2:5][CH:6]([NH:7]... | COC(=O)CC(N)c1ccc(OCC2CCN(c3ccncc3)CC2)cc1.Cc1ccc(S(=O)(=O)Cl)cc1 | COC(=O)CC(NS(=O)(=O)c1ccc(C)cc1)c1ccc(OCC2CCN(c3ccncc3)CC2)cc1 | null | null | null | Acylation | Sulfonamide synthesis (Schotten-Baumann) primary amine | 84f0a2c480e4021adb28613388cdf35ca03a8bd65bbdad356e160a1b94684976 | 2988afdf4a13d931f021994343ac8648c6e63ca3a4c0ba598a4b99bbffc001c8 | O=S(=O)(NCc1ccc(OCC2CCN(c3ccncc3)CC2)cc1)c1ccccc1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6].[#8:7]-[C:8](=[O;D1;H0:9])-[C:10]-[C:11](-[NH2;D1;+0:12])-[c:13]>>[#8:7]-[C:8](=[O;D1;H0:9])-[C:10]-[C:11](-[c:13])-[NH;D2;+0:12]-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6] | null | [] | null | null | null | null | Using a procedure similar to that described in Example 19, but starting from the product of Example 61, step (iii) and p-toluenesulphonyl chloride, the title compound was prepared; NMR(CDCl3): 1.34-1.55(m,2H), 1.95(d,2H), 2.0-2.2(m,1H), 2.38(s,3H), 2.62-3.05(m,4H), 3.55(s,3H), 3.78(d,2H), 3.96(d,2H), 4.65(m,1H), 5.65(b... | 10.6084/m9.figshare.5104873.v1 | null | Tosylate.Primary amine.Sulfonyl halide | Sulfonamide | null | null | c1ccccc1.c1ccccc1.C1CC[NH]CC1.c1ccncc1 | HCl | null | null | null | COC(=O)CC(N)c1ccc(OCC2CCN(c3ccncc3)CC2)cc1.Cc1ccc(S(=O)(=O)Cl)cc1>>COC(=O)CC(NS(=O)(=O)c1ccc(C)cc1)c1ccc(OCC2CCN(c3ccncc3)CC2)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-a4b84c6d4bba48e5984768e434e83d60 | CC(=O)c1cc(Cl)c(O)c(Cl)c1.COC(=O)CBr>>COC(=O)COc1c(Cl)cc(C(C)=O)cc1Cl | BrCC(=O)OC.CC(=O)C1=CC(=C(C(=C1)Cl)O)Cl.[H-].[Na+].CCCCCC>>C(C)(=O)C1=CC(=C(OCC(=O)OC)C(=C1)Cl)Cl | [OH:6][c:7]1[c:8]([Cl:9])[cH:10][c:11]([C:12]([CH3:13])=[O:14])[cH:15][c:16]1[Cl:17].Br[CH2:5][C:3]([O:2][CH3:1])=[O:4]>>[CH3:1][O:2][C:3](=[O:4])[CH2:5][O:6][c:7]1[c:8]([Cl:9])[cH:10][c:11]([C:12]([CH3:13])=[O:14])[cH:15][c:16]1[Cl:17] | CC(=O)c1cc(Cl)c(O)c(Cl)c1.COC(=O)CBr | COC(=O)COc1c(Cl)cc(C(C)=O)cc1Cl | null | null | CN(C)C=O.O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 50d675b335c583a6ce22e1164b27a78b18b9ca447d45137820c344bcb6369217 | 0865de4e1853c59ac25437e36fd18b03329566cb9eff4b4f0ce70d5714692fd3 | c1ccccc1 | Br-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#8:4]-[C;D1;H3:5].[OH;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[C;D1;H3:5]-[#8:4]-[C:2](=[O;D1;H0:3])-[CH2;D2;+0:1]-[O;H0;D2;+0:6]-[c:7](:[c:8]):[c:9] | null | [] | null | null | 30 | MINUTE | Sodium hydride (50% w/w dispersion in mineral oil, 1.32 g) was treated under argon with repeated washes of hexane. The oil-free residue was suspended in dry DMF (10 ml) and, with stirring and cooling (ice-bath), a solution of 3,5-dichloro-4-hydroxyacetophenone (5.13 g) in dry DMF (15 ml) was added dropwise. Stirring wa... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester.Aromatic alcohol | Ester.Ether | null | null | c1ccccc1 | HBr | CN(C)C=O.O | null | 0.5 | CC(=O)c1cc(Cl)c(O)c(Cl)c1.COC(=O)CBr>CN(C)C=O.O>COC(=O)COc1c(Cl)cc(C(C)=O)cc1Cl |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-491033b17682484fae85e1aa872b7af9 | CC(=O)c1ccc(O)cc1C.COC(=O)CBr>>COC(=O)COc1ccc(C(C)=O)c(C)c1 | CC1=C(C=CC(=C1)O)C(=O)C.C([O-])([O-])=O.[K+].[K+].BrCC(=O)OC>>C(C)(=O)C1=C(C=C(OCC(=O)OC)C=C1)C | [OH:6][c:7]1[cH:8][cH:9][c:10]([C:11]([CH3:12])=[O:13])[c:14]([CH3:15])[cH:16]1.Br[CH2:5][C:3]([O:2][CH3:1])=[O:4]>>[CH3:1][O:2][C:3](=[O:4])[CH2:5][O:6][c:7]1[cH:8][cH:9][c:10]([C:11]([CH3:12])=[O:13])[c:14]([CH3:15])[cH:16]1 | CC(=O)c1ccc(O)cc1C.COC(=O)CBr | COC(=O)COc1ccc(C(C)=O)c(C)c1 | null | null | CC(=O)C | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 50d675b335c583a6ce22e1164b27a78b18b9ca447d45137820c344bcb6369217 | 0865de4e1853c59ac25437e36fd18b03329566cb9eff4b4f0ce70d5714692fd3 | c1ccccc1 | Br-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#8:4]-[C;D1;H3:5].[OH;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[C;D1;H3:5]-[#8:4]-[C:2](=[O;D1;H0:3])-[CH2;D2;+0:1]-[O;H0;D2;+0:6]-[c:7](:[c:8]):[c:9] | null | [] | null | null | 2 | DAY | A mixture of 4-hydroxy-2-methylacetophenone (4.8 g), anhydrous potassium carbonate (5.3 g) and methyl bromoacetate (3.55 ml) in anhydrous acetone (100 ml) was stirred for 2 days. The mixture, after filtration and evaporation of the solvent, gave methyl 4-acetyl-3-methylphenoxyacetate, 6.6 g, as a crystalline solid: m.p... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester.Aromatic alcohol | Ester.Ether | null | null | c1ccccc1 | HBr | CC(=O)C | null | 48 | CC(=O)c1ccc(O)cc1C.COC(=O)CBr>CC(=O)C>COC(=O)COc1ccc(C(C)=O)c(C)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-bee4694b03554b1caebf7d486567179e | CC(=O)c1ccc(O)c(C)c1.COC(=O)CBr>>COC(=O)COc1ccc(C(C)=O)cc1C | CC1=C(C=CC(=C1)C(=O)C)O.BrCC(=O)OC.C([O-])([O-])=O.[K+].[K+]>>C(C)(=O)C1=CC(=C(OCC(=O)OC)C=C1)C | [OH:6][c:7]1[cH:8][cH:9][c:10]([C:11]([CH3:12])=[O:13])[cH:14][c:15]1[CH3:16].Br[CH2:5][C:3]([O:2][CH3:1])=[O:4]>>[CH3:1][O:2][C:3](=[O:4])[CH2:5][O:6][c:7]1[cH:8][cH:9][c:10]([C:11]([CH3:12])=[O:13])[cH:14][c:15]1[CH3:16] | CC(=O)c1ccc(O)c(C)c1.COC(=O)CBr | COC(=O)COc1ccc(C(C)=O)cc1C | null | null | CC(=O)C | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 50d675b335c583a6ce22e1164b27a78b18b9ca447d45137820c344bcb6369217 | 0865de4e1853c59ac25437e36fd18b03329566cb9eff4b4f0ce70d5714692fd3 | c1ccccc1 | Br-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#8:4]-[C;D1;H3:5].[OH;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[C;D1;H3:5]-[#8:4]-[C:2](=[O;D1;H0:3])-[CH2;D2;+0:1]-[O;H0;D2;+0:6]-[c:7](:[c:8]):[c:9] | null | [] | null | null | 66 | HOUR | A mixture of 4-hydroxy-3-methylacetophenone (5 g), methyl bromoacetate (3.70 ml) and anhydrous potassium carbonate (5.52 g) in acetone (100 ml) was stirred for 66 hours. The mixture was filtered and the filtrate evaporated to give an oil which crystallised on standing giving methyl 4-acetyl-2-methylphenoxyacetate, 7.2 ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester.Aromatic alcohol | Ester.Ether | null | null | c1ccccc1 | HBr | CC(=O)C | null | 66 | CC(=O)c1ccc(O)c(C)c1.COC(=O)CBr>CC(=O)C>COC(=O)COc1ccc(C(C)=O)cc1C |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-f64bf02e0584457a9dbced6eafe6f5c3 | CCOC(=O)c1ccc(C(=O)CN2CCN(c3ccncc3)CC2)cc1>>O=C([O-])c1ccc(C(=O)CN2CCN(c3ccncc3)CC2)cc1 | N1=CC=C(C=C1)N1CCN(CC1)CC(=O)C1=CC=C(C(=O)OCC)C=C1.[OH-].[Na+]>>N1=CC=C(C=C1)N1CCN(CC1)CC(=O)C1=CC=C(C(=O)[O-])C=C1.[Na+] | CC[O:3][C:2](=[O:1])[c:4]1[cH:5][cH:6][c:7]([C:8](=[O:9])[CH2:10][N:11]2[CH2:12][CH2:13][N:14]([c:15]3[cH:16][cH:17][n:18][cH:19][cH:20]3)[CH2:21][CH2:22]2)[cH:23][cH:24]1>>[O:1]=[C:2]([O-:3])[c:4]1[cH:5][cH:6][c:7]([C:8](=[O:9])[CH2:10][N:11]2[CH2:12][CH2:13][N:14]([c:15]3[cH:16][cH:17][n:18][cH:19][cH:20]3)[CH2:21][C... | CCOC(=O)c1ccc(C(=O)CN2CCN(c3ccncc3)CC2)cc1 | O=C([O-])c1ccc(C(=O)CN2CCN(c3ccncc3)CC2)cc1 | null | null | CO | Functional Group Interconversion | Ester to carboxylate | 821210f6f99f2510a1cab460144f356df713620aaf5f176ae325aca686567da7 | 5e32b8721010c33cc6df2b6213aa79bfd72016baf9e10bd582a623b626f4f641 | O=C(CN1CCN(c2ccncc2)CC1)c1ccccc1 | C-C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]>>[O-;H0;D1:1]-[C:2](=[O;D1;H0:3])-[c:4] | null | [] | null | null | 2 | HOUR | A stirred suspension of the product of Example 77 (353 mg) in methanol (5 ml) was treated with a 1 molar sodium hydroxide solution (3 ml). After 2 hours, the cream coloured solid was collected, washed with a little methanol and dried to give the title compound, 240 mg, m.p.>300° C.; NMR (d6DMSO) δ 8.15 (2H, d), 8.05 (4... | 10.6084/m9.figshare.5104873.v1 | null | Ester | null | null | null | c1ccccc1.C1C[NH]CC[NH]1.c1ccncc1 | Other | CO | null | 2 | CCOC(=O)c1ccc(C(=O)CN2CCN(c3ccncc3)CC2)cc1>CO>O=C([O-])c1ccc(C(=O)CN2CCN(c3ccncc3)CC2)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-76266dbb7ecd40f78d7b97f8f4934f98 | COC(=O)C(C)(C)Oc1ccc(C(=O)CN2CCN(c3ccncc3)CC2)cc1>>Br.CC(C)(Oc1ccc(C(=O)CN2CCNCC2c2ccncc2)cc1)C(=O)O | N1=CC=C(C=C1)N1CCN(CC1)CC(=O)C1=CC=C(OC(C(=O)OC)(C)C)C=C1.Br.O1CCOCC1>>Br.Br.N1=CC=C(C=C1)C1N(CCNC1)CC(=O)C1=CC=C(OC(C(=O)O)(C)C)C=C1 | C[O:30][C:28]([C:4]([CH3:3])([CH3:5])[O:6][c:7]1[cH:8][cH:9][c:10]([C:11](=[O:12])[CH2:13][N:14]2[CH2:15][CH2:16][N:17]([c:20]3[cH:21][cH:22][n:23][cH:24][cH:25]3)[CH2:18][CH2:19]2)[cH:26][cH:27]1)=[O:29]>>[BrH:2].[CH3:3][C:4]([CH3:5])([O:6][c:7]1[cH:8][cH:9][c:10]([C:11](=[O:12])[CH2:13][N:14]2[CH2:15][CH2:16][NH:17][... | COC(=O)C(C)(C)Oc1ccc(C(=O)CN2CCN(c3ccncc3)CC2)cc1 | Br.CC(C)(Oc1ccc(C(=O)CN2CCNCC2c2ccncc2)cc1)C(=O)O | null | null | O | Miscellaneous | OtherReaction | 855fefea2852da09473b88e0fe8d107702d2d6073b29e6a2384e80b3fc562204 | 1dd3e21db7025a61ed446f4f58cbd6d5fa3f0d1bded532f4be35dd1da8185ea9 | O=C(CN1CCNCC1c1ccncc1)c1ccccc1 | C-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4].[O;D1;H0:5]=[C:6]-[C:7]-[#7:8]1-[C:9]-[C:10]-[N;H0;D3;+0:11](-[c;H0;D3;+0:12]2:[c:13]:[c:14]:[#7;a:15]:[c:16]:[c:17]:2)-[C:18]-[CH2;D2;+0:19]-1>>[C:3]-[C:2](=[O;D1;H0:4])-[OH;D1;+0:1].[O;D1;H0:5]=[C:6]-[C:7]-[#7:8]1-[C:9]-[C:10]-[NH;D2;+0:11]-[C:18]-[CH;D3;+0:19]-1-[c;H0;D3;+0... | null | [] | 95 | CELSIUS | null | null | A mixture of methyl 2-[4-[2-[4-(4-pyridyl)piperazin-1-yl]-acetyl]phenoxy]isobutyrate (50 mg), 48% w/v hydrobromic acid (0.74 ml), dioxane (1 ml) and water (3 ml) was heated at 95° C. for 4 hours. The solution was cooled, diluted with water and freeze-dried to give the title compound, 40 mg, as a pale yellow solid: m.p.... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Tertiary amine | Carboxylic acid.Secondary amine | C1C[NH]CC[NH]1.c1ccncc1 | C1C[NH]CCN1.c1ccncc1 | c1ccccc1.C1C[NH]CCN1.c1ccncc1 | null | O | 95 | null | COC(=O)C(C)(C)Oc1ccc(C(=O)CN2CCN(c3ccncc3)CC2)cc1>O>Br.CC(C)(Oc1ccc(C(=O)CN2CCNCC2c2ccncc2)cc1)C(=O)O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-f693e1231b194064866be7bc3c6466fb | COC(=O)C(C)(C)Oc1ccc(C(=O)CBr)cc1.c1cc(N2CCNCC2)ccn1>>COC(=O)C(C)(C)Oc1ccc(C(=O)CN2CCN(c3ccncc3)CC2)cc1 | C(C)OCC.BrCC(=O)C1=CC=C(OC(C(=O)OC)(C)C)C=C1.N1=CC=C(C=C1)N1CCNCC1.C(C)N(CC)CC>>N1=CC=C(C=C1)N1CCN(CC1)CC(=O)C1=CC=C(OC(C(=O)OC)(C)C)C=C1 | Br[CH2:15][C:13]([c:12]1[cH:11][cH:10][c:9]([O:8][C:5]([C:3]([O:2][CH3:1])=[O:4])([CH3:6])[CH3:7])[cH:29][cH:28]1)=[O:14].[NH:16]1[CH2:17][CH2:18][N:19]([c:20]2[cH:21][cH:22][n:23][cH:24][cH:25]2)[CH2:26][CH2:27]1>>[CH3:1][O:2][C:3](=[O:4])[C:5]([CH3:6])([CH3:7])[O:8][c:9]1[cH:10][cH:11][c:12]([C:13](=[O:14])[CH2:15][N... | COC(=O)C(C)(C)Oc1ccc(C(=O)CBr)cc1.c1cc(N2CCNCC2)ccn1 | COC(=O)C(C)(C)Oc1ccc(C(=O)CN2CCN(c3ccncc3)CC2)cc1 | null | null | C(C)#N | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | f26d51e2c774d81a020fc5d8715a5a6f6b06297cf3257cffbe63e8f82c8c4256 | 98b92c1800516dd6f2e7ad31e751bba9f02d8a8062f38a8945939bbe90ecca84 | O=C(CN1CCN(c2ccncc2)CC1)c1ccccc1 | Br-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4].[#7:5]1-[C:6]-[C:7]-[NH;D2;+0:8]-[C:9]-[C:10]-1>>[O;D1;H0:3]=[C:2](-[c:4])-[CH2;D2;+0:1]-[N;H0;D3;+0:8]1-[C:7]-[C:6]-[#7:5]-[C:10]-[C:9]-1 | null | [] | null | null | 8 | HOUR | The product from step (i) above (2.00 g) in acetonitrile (10 ml) was added dropwise over 15 minutes to a stirred solution of 1-(4-pyridyl)piperazine (1.04 g) and triethylamine (0.89 ml) in acetonitrile (15 ml) and the mixture stirred overnight. The precipitated solid was removed by filtration and the filtrate evaporate... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ketone.Secondary amine | Ketone.Tertiary amine | C1CNCC[NH]1 | C1C[NH]CC[NH]1 | c1ccccc1.C1C[NH]CC[NH]1.c1ccncc1 | HBr | C(C)#N | null | 8 | COC(=O)C(C)(C)Oc1ccc(C(=O)CBr)cc1.c1cc(N2CCNCC2)ccn1>C(C)#N>COC(=O)C(C)(C)Oc1ccc(C(=O)CN2CCN(c3ccncc3)CC2)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-f92e4a744b9845aba8f9beb80f6700fd | CCOC(=O)COc1ccc(C(=O)CBr)cc1.c1cc(N2CCNCC2)ccn1>>CCOC(=O)COc1ccc(C(=O)CN2CCN(c3ccncc3)CC2)cc1 | BrCC(=O)C1=CC=C(OCC(=O)OCC)C=C1.N1=CC=C(C=C1)N1CCNCC1>>N1=CC=C(C=C1)N1CCN(CC1)CC(=O)C1=CC=C(OCC(=O)OCC)C=C1 | Br[CH2:14][C:12]([c:11]1[cH:10][cH:9][c:8]([O:7][CH2:6][C:4]([O:3][CH2:2][CH3:1])=[O:5])[cH:28][cH:27]1)=[O:13].[NH:15]1[CH2:16][CH2:17][N:18]([c:19]2[cH:20][cH:21][n:22][cH:23][cH:24]2)[CH2:25][CH2:26]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][O:7][c:8]1[cH:9][cH:10][c:11]([C:12](=[O:13])[CH2:14][N:15]2[CH2:16][CH2:17... | CCOC(=O)COc1ccc(C(=O)CBr)cc1.c1cc(N2CCNCC2)ccn1 | CCOC(=O)COc1ccc(C(=O)CN2CCN(c3ccncc3)CC2)cc1 | null | null | C(C)#N | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | f26d51e2c774d81a020fc5d8715a5a6f6b06297cf3257cffbe63e8f82c8c4256 | 98b92c1800516dd6f2e7ad31e751bba9f02d8a8062f38a8945939bbe90ecca84 | O=C(CN1CCN(c2ccncc2)CC1)c1ccccc1 | Br-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4].[#7:5]1-[C:6]-[C:7]-[NH;D2;+0:8]-[C:9]-[C:10]-1>>[O;D1;H0:3]=[C:2](-[c:4])-[CH2;D2;+0:1]-[N;H0;D3;+0:8]1-[C:7]-[C:6]-[#7:5]-[C:10]-[C:9]-1 | null | [] | null | null | 1 | HOUR | Ethyl 4-bromoacetylphenoxyacetate (6.0 g) was added to a stirred, cooled (4° C.) solution of 1-(4-pyridyl)piperazine (6.5 g) in acetonitrile (225 ml). Stirring was continued for 1 hour at 4° C., then overnight at ambient temperature when the precipitated solid was removed by filtration. The filtrate was evaporated in v... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ketone.Secondary amine | Ketone.Tertiary amine | C1CNCC[NH]1 | C1C[NH]CC[NH]1 | c1ccccc1.C1C[NH]CC[NH]1.c1ccncc1 | HBr | C(C)#N | null | 1 | CCOC(=O)COc1ccc(C(=O)CBr)cc1.c1cc(N2CCNCC2)ccn1>C(C)#N>CCOC(=O)COc1ccc(C(=O)CN2CCN(c3ccncc3)CC2)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-c0b95ca8088a4d46af3551fafa170fb2 | CC(C)OC(=O)COc1ccc(C(=O)CBr)cc1.c1cc(N2CCNCC2)ccn1>>CC(C)OC(=O)COc1ccc(C(=O)CN2CCN(c3ccncc3)CC2)cc1 | BrCC(=O)C1=CC=C(OCC(=O)OC(C)C)C=C1.N1=CC=C(C=C1)N1CCNCC1>>N1=CC=C(C=C1)N1CCN(CC1)CC(=O)C1=CC=C(OCC(=O)OC(C)C)C=C1 | Br[CH2:15][C:13]([c:12]1[cH:11][cH:10][c:9]([O:8][CH2:7][C:5]([O:4][CH:2]([CH3:1])[CH3:3])=[O:6])[cH:29][cH:28]1)=[O:14].[NH:16]1[CH2:17][CH2:18][N:19]([c:20]2[cH:21][cH:22][n:23][cH:24][cH:25]2)[CH2:26][CH2:27]1>>[CH3:1][CH:2]([CH3:3])[O:4][C:5](=[O:6])[CH2:7][O:8][c:9]1[cH:10][cH:11][c:12]([C:13](=[O:14])[CH2:15][N:1... | CC(C)OC(=O)COc1ccc(C(=O)CBr)cc1.c1cc(N2CCNCC2)ccn1 | CC(C)OC(=O)COc1ccc(C(=O)CN2CCN(c3ccncc3)CC2)cc1 | null | null | C(C)#N | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | f26d51e2c774d81a020fc5d8715a5a6f6b06297cf3257cffbe63e8f82c8c4256 | 98b92c1800516dd6f2e7ad31e751bba9f02d8a8062f38a8945939bbe90ecca84 | O=C(CN1CCN(c2ccncc2)CC1)c1ccccc1 | Br-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4].[#7:5]1-[C:6]-[C:7]-[NH;D2;+0:8]-[C:9]-[C:10]-1>>[O;D1;H0:3]=[C:2](-[c:4])-[CH2;D2;+0:1]-[N;H0;D3;+0:8]1-[C:7]-[C:6]-[#7:5]-[C:10]-[C:9]-1 | null | [] | null | null | 1 | HOUR | iso-Propyl 4-bromoacetylphenoxyacetate (6.3 g) was added to a stirred, cooled (4° C.) solution of 1-(4-pyridyl)piperazine (6.5 g) in acetonitrile (225 ml). Stirring was continued for 1 hour at 4° C., then overnight at ambient temperature when the precipitated solid was removed. The filtrate was evaporated in vacuo and ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ketone.Secondary amine | Ketone.Tertiary amine | C1CNCC[NH]1 | C1C[NH]CC[NH]1 | c1ccccc1.C1C[NH]CC[NH]1.c1ccncc1 | HBr | C(C)#N | null | 1 | CC(C)OC(=O)COc1ccc(C(=O)CBr)cc1.c1cc(N2CCNCC2)ccn1>C(C)#N>CC(C)OC(=O)COc1ccc(C(=O)CN2CCN(c3ccncc3)CC2)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-e33d3c2da1e849fdb7d26db578a0da09 | COC(=O)COc1ccc(C(=O)CN2CCN(c3ccncc3)CC2)cc1.N>>NC(=O)COc1ccc(C(=O)CN2CCN(c3ccncc3)CC2)cc1 | N1=CC=C(C=C1)N1CCN(CC1)CC(=O)C1=CC=C(OCC(=O)OC)C=C1.N>>N1=CC=C(C=C1)N1CCN(CC1)CC(=O)C1=CC=C(OCC(=O)N)C=C1 | CO[C:2](=[O:3])[CH2:4][O:5][c:6]1[cH:7][cH:8][c:9]([C:10](=[O:11])[CH2:12][N:13]2[CH2:14][CH2:15][N:16]([c:17]3[cH:18][cH:19][n:20][cH:21][cH:22]3)[CH2:23][CH2:24]2)[cH:25][cH:26]1.[NH3:1]>>[NH2:1][C:2](=[O:3])[CH2:4][O:5][c:6]1[cH:7][cH:8][c:9]([C:10](=[O:11])[CH2:12][N:13]2[CH2:14][CH2:15][N:16]([c:17]3[cH:18][cH:19]... | COC(=O)COc1ccc(C(=O)CN2CCN(c3ccncc3)CC2)cc1.N | NC(=O)COc1ccc(C(=O)CN2CCN(c3ccncc3)CC2)cc1 | null | null | CO | Acylation | OtherReaction | d5b10d4f469e7a196a3b04a6a9e159a7d90514b6df5b50c1197d4b1b774c04e1 | adc0ef6f6c1340dd2dbab737c85bf17fc842769181c5db1a2b4f82b391b28f9f | O=C(CN1CCN(c2ccncc2)CC1)c1ccccc1 | C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[#8:4].[NH3;D0;+0:5]>>[#8:4]-[C:3]-[C;H0;D3;+0:1](-[NH2;D1;+0:5])=[O;D1;H0:2] | null | [] | null | null | 2 | DAY | A solution of the product of Example 1 (200 mg) in methanol (10 ml), prepared under argon, was cooled to 4° C. and saturated with dry ammonia gas, then sealed in a pressure bottle and kept for 2 days. The orange crystals which formed, after filtration and washing with a little methanol, gave the title compound, 140 mg:... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary amide | null | null | c1ccccc1.C1C[NH]CC[NH]1.c1ccncc1 | HO- | CO | null | 48 | COC(=O)COc1ccc(C(=O)CN2CCN(c3ccncc3)CC2)cc1.N>CO>NC(=O)COc1ccc(C(=O)CN2CCN(c3ccncc3)CC2)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-881c5d0cd109432183b9ebc50ee4284b | CN.COC(=O)COc1ccc(C(=O)CN2CCN(c3ccncc3)CC2)cc1>>CNC(=O)COc1ccc(C(=O)CN2CCN(c3ccncc3)CC2)cc1 | N1=CC=C(C=C1)N1CCN(CC1)CC(=O)C1=CC=C(OCC(=O)OC)C=C1.CN>>N1=CC=C(C=C1)N1CCN(CC1)CC(=O)C1=CC=C(OCC(=O)NC)C=C1 | [CH3:1][NH2:2].CO[C:3](=[O:4])[CH2:5][O:6][c:7]1[cH:8][cH:9][c:10]([C:11](=[O:12])[CH2:13][N:14]2[CH2:15][CH2:16][N:17]([c:18]3[cH:19][cH:20][n:21][cH:22][cH:23]3)[CH2:24][CH2:25]2)[cH:26][cH:27]1>>[CH3:1][NH:2][C:3](=[O:4])[CH2:5][O:6][c:7]1[cH:8][cH:9][c:10]([C:11](=[O:12])[CH2:13][N:14]2[CH2:15][CH2:16][N:17]([c:18]... | CN.COC(=O)COc1ccc(C(=O)CN2CCN(c3ccncc3)CC2)cc1 | CNC(=O)COc1ccc(C(=O)CN2CCN(c3ccncc3)CC2)cc1 | null | null | C(C)O | Acylation | Aminolysis of esters | 04c54ce22aa9bc0cea0de3d900446bcab51cf02bebeb606fa788a47dcd0e37ff | 4335147c9ad02004b7c12428d7eac0b2e7e0e2017adc471d01c387239de8017d | O=C(CN1CCN(c2ccncc2)CC1)c1ccccc1 | C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[#8:4].[C;D1;H3:5]-[NH2;D1;+0:6]>>[#8:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:6]-[C;D1;H3:5] | null | [] | null | null | 18 | HOUR | A suspension of the product of Example 1 (100 mg) in a 33% w/v solution of methylamine in ethanol (3 ml) was stirred for 18 hours. The solid formed, after filtration and washing with a little ethyl acetate, gave the title compound, 65 mg: m.p. 169°-171° C.; NMR (d6DMSO) δ 8.14 (2H, d), 8.06 (1H, bq), 8.00 (2H, d), 7.05... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Primary amine | Secondary amide | null | null | c1ccccc1.C1C[NH]CC[NH]1.c1ccncc1 | HO- | C(C)O | null | 18 | CN.COC(=O)COc1ccc(C(=O)CN2CCN(c3ccncc3)CC2)cc1>C(C)O>CNC(=O)COc1ccc(C(=O)CN2CCN(c3ccncc3)CC2)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-446b034cd2a240b1811399997a196a51 | COC(=O)COc1ccc(C(=O)CN2CCN(c3ccncc3)CC2)cc1.COCCN>>COCCNC(=O)COc1ccc(C(=O)CN2CCN(c3ccncc3)CC2)cc1 | N1=CC=C(C=C1)N1CCN(CC1)CC(=O)C1=CC=C(OCC(=O)OC)C=C1.COCCN>>N1=CC=C(C=C1)N1CCN(CC1)CC(=O)C1=CC=C(OCC(=O)NCCOC)C=C1 | CO[C:6](=[O:7])[CH2:8][O:9][c:10]1[cH:11][cH:12][c:13]([C:14](=[O:15])[CH2:16][N:17]2[CH2:18][CH2:19][N:20]([c:21]3[cH:22][cH:23][n:24][cH:25][cH:26]3)[CH2:27][CH2:28]2)[cH:29][cH:30]1.[CH3:1][O:2][CH2:3][CH2:4][NH2:5]>>[CH3:1][O:2][CH2:3][CH2:4][NH:5][C:6](=[O:7])[CH2:8][O:9][c:10]1[cH:11][cH:12][c:13]([C:14](=[O:15])... | COC(=O)COc1ccc(C(=O)CN2CCN(c3ccncc3)CC2)cc1.COCCN | COCCNC(=O)COc1ccc(C(=O)CN2CCN(c3ccncc3)CC2)cc1 | null | null | null | Acylation | Aminolysis of esters | 04c54ce22aa9bc0cea0de3d900446bcab51cf02bebeb606fa788a47dcd0e37ff | 4335147c9ad02004b7c12428d7eac0b2e7e0e2017adc471d01c387239de8017d | O=C(CN1CCN(c2ccncc2)CC1)c1ccccc1 | C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[#8:4].[C:5]-[C:6]-[NH2;D1;+0:7]>>[#8:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:7]-[C:6]-[C:5] | null | [] | null | null | 18 | HOUR | A suspension of the product of Example 1, (100 mg) in 2-methoxyethylamine (1 ml) was stirred for 18 hours. Filtration of the solid and washing with ethyl acetate gave the title compound, 70 mg, as a white crystalline solid: m.p. 142°-145° C.; NMR (d6DMSO+d4 acetic acid) δ 8.20 (2H, d), 8.00 (2H, d), 7.14 (2H, d), 7.06 ... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Primary amine | Secondary amide | null | null | c1ccccc1.C1C[NH]CC[NH]1.c1ccncc1 | HO- | null | null | 18 | COC(=O)COc1ccc(C(=O)CN2CCN(c3ccncc3)CC2)cc1.COCCN>>COCCNC(=O)COc1ccc(C(=O)CN2CCN(c3ccncc3)CC2)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-2f8da7ad30b2414dbbd1e045328ab620 | COC(=O)CNC(=O)COc1ccc(C(C)=O)cc1.O=C1CCC(=O)N1Br>>COC(=O)CNC(=O)COc1ccc(C(=O)CBr)cc1 | C(C)(=O)C1=CC=C(OCC(=O)NCC(=O)OC)C=C1.BrN1C(CCC1=O)=O>>BrCC(=O)C1=CC=C(OCC(=O)NCC(=O)OC)C=C1 | [CH3:1][O:2][C:3](=[O:4])[CH2:5][NH:6][C:7](=[O:8])[CH2:9][O:10][c:11]1[cH:12][cH:13][c:14]([C:15](=[O:16])[CH3:17])[cH:19][cH:20]1.O=C1CCC(=O)N1[Br:18]>>[CH3:1][O:2][C:3](=[O:4])[CH2:5][NH:6][C:7](=[O:8])[CH2:9][O:10][c:11]1[cH:12][cH:13][c:14]([C:15](=[O:16])[CH2:17][Br:18])[cH:19][cH:20]1 | COC(=O)CNC(=O)COc1ccc(C(C)=O)cc1.O=C1CCC(=O)N1Br | COC(=O)CNC(=O)COc1ccc(C(=O)CBr)cc1 | null | null | C(Cl)(Cl)(Cl)Cl | Functional Group Interconversion | Wohl-Ziegler bromination carbonyl primary | 649182132639cff0c011b2cad7a705a30754d73ba3f68a521e88611e90b8027f | aacae65ea79279bb4f8207a05afbc55ff3b90a4ca5365db2b32e1e9d9a2242d1 | c1ccccc1 | O=C1-C-C-C(=O)-N-1-[Br;H0;D1;+0:1].[CH3;D1;+0:2]-[C:3](=[O;D1;H0:4])-[c:5]>>[Br;H0;D1;+0:1]-[CH2;D2;+0:2]-[C:3](=[O;D1;H0:4])-[c:5] | null | [] | null | null | null | null | The product of step (i) (3.00 g) and N-bromosuccinimide (2.02 g) in carbon tetrachloride (50 ml) was heated at reflux temperature for 64 hours. The solvent was evaporated and the black residue dissolved in methanol/ethyl acetate, treated with charcoal, filtered and then evaporated. The resulting brown oil was purified ... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Tertiary amide.Tertiary amide | Primary halide | C1CCNC1 | null | c1ccccc1 | HO- | C(Cl)(Cl)(Cl)Cl | null | null | COC(=O)CNC(=O)COc1ccc(C(C)=O)cc1.O=C1CCC(=O)N1Br>C(Cl)(Cl)(Cl)Cl>COC(=O)CNC(=O)COc1ccc(C(=O)CBr)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-a4c192010f8d498c9feb99faee7fc4d5 | BrCc1ccccc1.O=C(O)Cc1ccc(O)cc1>>O=C(Cc1ccc(O)cc1)OCc1ccccc1 | C(C1=CC=CC=C1)Br.[H-].[Na+].CCCCCC.OC1=CC=C(C=C1)CC(=O)O>>OC1=CC=C(C=C1)CC(=O)OCC1=CC=CC=C1 | Br[CH2:12][c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1.[O:1]=[C:2]([CH2:3][c:4]1[cH:5][cH:6][c:7]([OH:8])[cH:9][cH:10]1)[OH:11]>>[O:1]=[C:2]([CH2:3][c:4]1[cH:5][cH:6][c:7]([OH:8])[cH:9][cH:10]1)[O:11][CH2:12][c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1 | BrCc1ccccc1.O=C(O)Cc1ccc(O)cc1 | O=C(Cc1ccc(O)cc1)OCc1ccccc1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 06c4f868ad4646eea8208ecb83f54ca035dd62d04f0d8101641a4f487f2c695c | 8446834f0edd1e71a2dcaffc09b80c7367abf3407263a8998354a2d20c1766bb | O=C(Cc1ccccc1)OCc1ccccc1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[C:5]-[C:6](=[O;D1;H0:7])-[OH;D1;+0:8]>>[C:5]-[C:6](=[O;D1;H0:7])-[O;H0;D2;+0:8]-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | 4 | CELSIUS | 30 | MINUTE | Sodium hydride (50% w/w dispersion in mineral oil, 3.7 g) was treated under argon with repeated washes of hexane. The oil-free residue was suspended in dry DMF (100 ml) and 4-hydroxyphenylacetic acid (13.0 g) was added portionwise to the stirred cooled (4° C.) mixture. After 30 minutes, benzyl bromide (9.2 ml) was adde... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Carboxylic acid | Ester | null | null | c1ccccc1.c1ccccc1 | HBr | CN(C)C=O | 4 | 0.5 | BrCc1ccccc1.O=C(O)Cc1ccc(O)cc1>CN(C)C=O>O=C(Cc1ccc(O)cc1)OCc1ccccc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-747ab4b04253405996f5d607424406f9 | CC(C)(C)OC(=O)CBr.O=C(Cc1ccc(O)cc1)OCc1ccccc1>>CC(C)(C)OC(=O)COc1ccc(CC(=O)OCc2ccccc2)cc1 | BrCC(=O)OC(C)(C)C.[H-].[Na+].CCCCCC.OC1=CC=C(C=C1)CC(=O)OCC1=CC=CC=C1>>C(C1=CC=CC=C1)OC(=O)CC1=CC=C(OCC(=O)OC(C)(C)C)C=C1 | Br[CH2:8][C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7].[OH:9][c:10]1[cH:11][cH:12][c:13]([CH2:14][C:15](=[O:16])[O:17][CH2:18][c:19]2[cH:20][cH:21][cH:22][cH:23][cH:24]2)[cH:25][cH:26]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[CH2:8][O:9][c:10]1[cH:11][cH:12][c:13]([CH2:14][C:15](=[O:16])[O:17][CH2:18][c:19... | CC(C)(C)OC(=O)CBr.O=C(Cc1ccc(O)cc1)OCc1ccccc1 | CC(C)(C)OC(=O)COc1ccc(CC(=O)OCc2ccccc2)cc1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 50d675b335c583a6ce22e1164b27a78b18b9ca447d45137820c344bcb6369217 | 0865de4e1853c59ac25437e36fd18b03329566cb9eff4b4f0ce70d5714692fd3 | O=C(Cc1ccccc1)OCc1ccccc1 | Br-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#8:4]-[C:5](-[C;D1;H3:6])(-[C;D1;H3:7])-[C;D1;H3:8].[OH;D1;+0:9]-[c:10](:[c:11]):[c:12]>>[C;D1;H3:6]-[C:5](-[C;D1;H3:7])(-[C;D1;H3:8])-[#8:4]-[C:2](=[O;D1;H0:3])-[CH2;D2;+0:1]-[O;H0;D2;+0:9]-[c:10](:[c:11]):[c:12] | null | [] | 4 | CELSIUS | 15 | MINUTE | Sodium hydride (50% w/w dispersion in mineral oil, 2.1 g) was treated under argon with repeated washes of hexane. The oil-free residue was suspended in dry DMF (130 ml) and the product from step (i) (10 g) added in three portions to the cooled (4° C.) stirred mixture. Stirring was continued for a further 15 minutes whe... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester.Aromatic alcohol | Ester.Ether | null | null | c1ccccc1.c1ccccc1 | HBr | CN(C)C=O | 4 | 0.25 | CC(C)(C)OC(=O)CBr.O=C(Cc1ccc(O)cc1)OCc1ccccc1>CN(C)C=O>CC(C)(C)OC(=O)COc1ccc(CC(=O)OCc2ccccc2)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-0b7d284c41804ff1aae25f00491e423c | COC(=O)COc1ccc(O)cc1.OC1CCN(c2ccncc2)CC1>>COC(=O)COc1ccc(OC2CCN(c3ccncc3)CC2)cc1 | CCOC(=O)/N=N/C(=O)OCC.N1=CC=C(C=C1)N1CCC(CC1)O.OC1=CC=C(OCC(=O)OC)C=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1>>N1=CC=C(C=C1)N1CCC(CC1)OC1=CC=C(OCC(=O)OC)C=C1 | [CH3:1][O:2][C:3](=[O:4])[CH2:5][O:6][c:7]1[cH:8][cH:9][c:10]([OH:11])[cH:24][cH:25]1.O[CH:12]1[CH2:13][CH2:14][N:15]([c:16]2[cH:17][cH:18][n:19][cH:20][cH:21]2)[CH2:22][CH2:23]1>>[CH3:1][O:2][C:3](=[O:4])[CH2:5][O:6][c:7]1[cH:8][cH:9][c:10]([O:11][CH:12]2[CH2:13][CH2:14][N:15]([c:16]3[cH:17][cH:18][n:19][cH:20][cH:21]... | COC(=O)COc1ccc(O)cc1.OC1CCN(c2ccncc2)CC1 | COC(=O)COc1ccc(OC2CCN(c3ccncc3)CC2)cc1 | null | null | C1CCOC1 | Heteroatom Alkylation and Arylation | Mitsunobu aryl ether | a9e936b0e9135225700edbab1c7696738b7f1f0756494b6ceeeda63b184d572f | 776ba735002e33225fbc578943016110c2c43efefd97bfeea4ec3cc2e2e1532f | c1ccc(OC2CCN(c3ccncc3)CC2)cc1 | O-[CH;D3;+0:1]1-[C:2]-[C:3]-[#7:4]-[C:5]-[C:6]-1.[OH;D1;+0:7]-[c:8](:[c:9]):[c:10]>>[c:9]:[c:8](-[O;H0;D2;+0:7]-[CH;D3;+0:1]1-[C:2]-[C:3]-[#7:4]-[C:5]-[C:6]-1):[c:10] | null | [] | 4 | CELSIUS | 1 | HOUR | Diethylazodicarboxylate (0.47 ml) was added dropwise over 30 minutes to a stirred mixture of 1-(4-pyridyl)-4-piperidinol (534 mg), methyl 4-hydroxyphenoxyacetate (546 mg), triphenylphosphine (787 mg) and dry THF (30 ml) in an atmosphere of argon and cooled to 4° C. After 1 hour at 4° C., the mixture was allowed to reac... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol.Aromatic alcohol | Ether | C1CC[NH]CC1 | C1CC[NH]CC1 | c1ccccc1.C1CC[NH]CC1.c1ccncc1 | HO- | C1CCOC1 | 4 | 1 | COC(=O)COc1ccc(O)cc1.OC1CCN(c2ccncc2)CC1>C1CCOC1>COC(=O)COc1ccc(OC2CCN(c3ccncc3)CC2)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-159bc692d5184caf89d71a09ee2cc756 | COC(=O)CCc1ccc(O)cc1.OCC1CCN(c2ccncc2)CC1>>COC(=O)CCc1ccc(OCC2CCN(c3ccncc3)CC2)cc1 | OCC1CCN(CC1)C1=CC=NC=C1.OC1=CC=C(C=C1)CCC(=O)OC>>N1=CC=C(C=C1)N1CCC(CC1)COC1=CC=C(C=C1)CCC(=O)OC | [CH3:1][O:2][C:3](=[O:4])[CH2:5][CH2:6][c:7]1[cH:8][cH:9][c:10]([OH:11])[cH:25][cH:26]1.O[CH2:12][CH:13]1[CH2:14][CH2:15][N:16]([c:17]2[cH:18][cH:19][n:20][cH:21][cH:22]2)[CH2:23][CH2:24]1>>[CH3:1][O:2][C:3](=[O:4])[CH2:5][CH2:6][c:7]1[cH:8][cH:9][c:10]([O:11][CH2:12][CH:13]2[CH2:14][CH2:15][N:16]([c:17]3[cH:18][cH:19]... | COC(=O)CCc1ccc(O)cc1.OCC1CCN(c2ccncc2)CC1 | COC(=O)CCc1ccc(OCC2CCN(c3ccncc3)CC2)cc1 | null | null | null | Heteroatom Alkylation and Arylation | Mitsunobu aryl ether | 86bfb73617450d22f9456ed5ce4d96a73f1f8fc0c016bebae57fda68e2da86a2 | 2258bd14c3b5449b92dc09cf9fa522f88d5071b4af20f7e968b60aa1ae6db0cf | c1ccc(OCC2CCN(c3ccncc3)CC2)cc1 | O-[CH2;D2;+0:1]-[C:2](-[C:3])-[C:4].[OH;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[C:3]-[C:2](-[CH2;D2;+0:1]-[O;H0;D2;+0:5]-[c:6](:[c:7]):[c:8])-[C:4] | 14 | [{"value": 14.0, "product": "N1=CC=C(C=C1)N1CCC(CC1)COC1=CC=C(C=C1)CCC(=O)OC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the method of Example 96, but starting from 4-(4-hydroxymethylpiperidin-1-yl)pyridine and methyl 3-(4-hydroxyphenyl)propionate, the title compound was prepared in 14% yield: m.p. 96.5°-98.5° C.; NMR (d6DMSO) δ 8.13(2H, d), 7.11(2H, d), 6.83(4H, m), 3.97(2H, dm), 3.81(2H, d), 3.56(3H, s), 2.87(2H, dr), 2.77(2H... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Aromatic alcohol | Ether | null | null | c1ccccc1.C1CC[NH]CC1.c1ccncc1 | HO- | null | null | null | COC(=O)CCc1ccc(O)cc1.OCC1CCN(c2ccncc2)CC1>>COC(=O)CCc1ccc(OCC2CCN(c3ccncc3)CC2)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-53468aff36b74b69af45a0218b9d4c73 | CC(=O)Cl.NC1CCN(Cc2ccccc2)CC1>>CC(=O)NC1CCN(Cc2ccccc2)CC1 | O.C(C)(=O)Cl.NC1CCN(CC1)CC1=CC=CC=C1.C(C)N(CC)CC>>C(C)(=O)NC1CCN(CC1)CC1=CC=CC=C1 | Cl[C:2]([CH3:1])=[O:3].[NH2:4][CH:5]1[CH2:6][CH2:7][N:8]([CH2:9][c:10]2[cH:11][cH:12][cH:13][cH:14][cH:15]2)[CH2:16][CH2:17]1>>[CH3:1][C:2](=[O:3])[NH:4][CH:5]1[CH2:6][CH2:7][N:8]([CH2:9][c:10]2[cH:11][cH:12][cH:13][cH:14][cH:15]2)[CH2:16][CH2:17]1 | CC(=O)Cl.NC1CCN(Cc2ccccc2)CC1 | CC(=O)NC1CCN(Cc2ccccc2)CC1 | null | null | ClCCl | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | c1ccc(CN2CCCCC2)cc1 | Cl-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[C:4]-[C:5](-[NH2;D1;+0:6])-[C:7]>>[C:4]-[C:5](-[NH;D2;+0:6]-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3])-[C:7] | null | [] | null | null | 16 | HOUR | Acetyl chloride (3.95 ml) was added dropwise to a stirred solution of 4-amino1-benzylpiperidine (10.0 g) and triethylamine (7.7 ml) in dry dichloromethane (100 ml) at 4° C. The mixture was allowed to reach ambient temperature and stirred for 16 hours. Water was then added, the organic phase separated and dried (MgSO4),... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | C1CC[NH]CC1.c1ccccc1 | HCl | ClCCl | null | 16 | CC(=O)Cl.NC1CCN(Cc2ccccc2)CC1>ClCCl>CC(=O)NC1CCN(Cc2ccccc2)CC1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-b74bffc65057435d9d7a9739ada92f3c | CC(=O)NC1CCN(Cc2ccccc2)CC1>>CC(=O)NC1CCNCC1 | C.C(C)(=O)NC1CCN(CC1)CC1=CC=CC=C1.Cl.[H][H]>>Cl.C(C)(=O)NC1CCNCC1 | c1ccc(C[N:8]2[CH2:7][CH2:6][CH:5]([NH:4][C:2]([CH3:1])=[O:3])[CH2:10][CH2:9]2)cc1>>[CH3:1][C:2](=[O:3])[NH:4][CH:5]1[CH2:6][CH2:7][NH:8][CH2:9][CH2:10]1 | CC(=O)NC1CCN(Cc2ccccc2)CC1 | CC(=O)NC1CCNCC1 | null | [Pd] | CO | Deprotection | Hydrogenolysis of tertiary amines | cd3c1aa319cad45f383f17cc0b8bfc8337d7078d779f654933f9a447e64292a5 | 1c99dd446c0bf4ae872cd8df8de34955be195747c234e9f3c49f46d1de614f66 | C1CCNCC1 | [C:1]-[C:2]-[N;H0;D3;+0:3](-C-c1:c:c:c:c:c:1)-[C:4]-[C:5]>>[C:1]-[C:2]-[NH;D2;+0:3]-[C:4]-[C:5] | null | [] | null | null | 1 | HOUR | 10% w/w Palladium on charcoal (1.5 g) was added to a solution of the product from step (i) (10.0 g), 1 molar hydrochloric acid (21.5 ml) and methanol (150 ml) and the mixture hydrogenated at room temperature and pressure until the theoretical amount of hydrogen had been taken up. Charcoal was added, the mixture stirred... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amine | Secondary amine | c1ccccc1.C1CC[NH]CC1 | C1CCNCC1 | C1CCNCC1 | Other | [Pd].CO | null | 1 | CC(=O)NC1CCN(Cc2ccccc2)CC1>[Pd].CO>CC(=O)NC1CCNCC1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-a48b81fc6740494aa3b8c87fee1bf7d7 | CC(=O)NC1CCNCC1.Clc1ccncc1>>CC(=O)NC1CCN(c2ccncc2)CC1 | Cl.C(C)(=O)NC1CCNCC1.Cl.ClC1=CC=NC=C1.C(O)([O-])=O.[Na+]>>C(C)(=O)NC1CCN(CC1)C1=CC=NC=C1 | [CH3:1][C:2](=[O:3])[NH:4][CH:5]1[CH2:6][CH2:7][NH:8][CH2:15][CH2:16]1.Cl[c:9]1[cH:10][cH:11][n:12][cH:13][cH:14]1>>[CH3:1][C:2](=[O:3])[NH:4][CH:5]1[CH2:6][CH2:7][N:8]([c:9]2[cH:10][cH:11][n:12][cH:13][cH:14]2)[CH2:15][CH2:16]1 | CC(=O)NC1CCNCC1.Clc1ccncc1 | CC(=O)NC1CCN(c2ccncc2)CC1 | null | null | CC(CCO)C | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | 10c6f9b26f855d26243e4771b69ba961e55fa770e633c60af6779c5e67cf6f43 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1cc(N2CCCCC2)ccn1 | Cl-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[#7;a:4]:[c:5]:[c:6]:1.[C:7]-[C:8]-[NH;D2;+0:9]-[C:10]-[C:11]>>[C:7]-[C:8]-[N;H0;D3;+0:9](-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[#7;a:4]:[c:5]:[c:6]:1)-[C:10]-[C:11] | null | [] | null | null | null | null | A mixture of the product from step (ii) (1.79 g), 4-chloropyridine hydrochloride (1.50 g), sodium hydrogen carbonate (2.86 g) in 3-methyl 1-butanol (25 ml) was heated at reflux temperature for 16 hours. The cooled mixture was filtered and the filtrate concentrated in vacuo. Purification of the residue by flash chromato... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | C1CCNCC1.c1ccncc1 | C1CC[NH]CC1.c1ccncc1 | C1CC[NH]CC1.c1ccncc1 | HCl | CC(CCO)C | null | null | CC(=O)NC1CCNCC1.Clc1ccncc1>CC(CCO)C>CC(=O)NC1CCN(c2ccncc2)CC1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-4564e7dbfb7f40f5b631cc194e2c0fe9 | CC(=O)NC1CCN(c2ccncc2)CC1>>Cl.Cl.NC1CCN(c2ccncc2)CC1.O | C(C)(=O)NC1CCN(CC1)C1=CC=NC=C1.Cl>>O.Cl.Cl.Cl.NC1CCN(CC1)C1=CC=NC=C1 | CC([NH:4][CH:5]1[CH2:6][CH2:7][N:8]([c:9]2[cH:10][cH:11][n:12][cH:13][cH:14]2)[CH2:15][CH2:16]1)=[O:17]>>[ClH:2].[ClH:3].[NH2:4][CH:5]1[CH2:6][CH2:7][N:8]([c:9]2[cH:10][cH:11][n:12][cH:13][cH:14]2)[CH2:15][CH2:16]1.[OH2:17] | CC(=O)NC1CCN(c2ccncc2)CC1 | Cl.Cl.NC1CCN(c2ccncc2)CC1.O | null | null | null | Functional Group Interconversion | Hydrogenolysis of amides/imides/carbamates | f49001251972600004e81a3baf51b0f8f1f5abd9a26f9edef2ad19f4e6e296cd | 894c26c70804ae93ffbb7522f5764194b6e4c7d25aff5099eea59e054a3ebd2a | c1cc(N2CCCCC2)ccn1 | C-C(=[O;H0;D1;+0:1])-[NH;D2;+0:2]-[C:3](-[C:4])-[C:5]>>[C:4]-[C:3](-[NH2;D1;+0:2])-[C:5].[OH2;D0;+0:1] | null | [] | null | null | null | null | The product from step (iii) (0.52 g) in 1 molar hydrochloric acid (11.9 ml) was heated at 95° C. for 5 hours. The solvent was evaporated and the residue, on drying over potassium hydroxide in vacuo gave 4-amino-1-(4-pyridyl)piperidine trihydrochloride hydrate, 0.70 g as a light brown solid: m.p. >300° C.; NMR (d6DMSO) ... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide | Primary amine | null | null | C1CC[NH]CC1.c1ccncc1 | null | null | null | null | CC(=O)NC1CCN(c2ccncc2)CC1>>Cl.Cl.NC1CCN(c2ccncc2)CC1.O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-ba03a2d2c49b4236818932f4fa781473 | COC(=O)COc1ccc(C(=O)C(C)(C)Br)cc1.c1cc(N2CCNCC2)ccn1>>COC(=O)COc1ccc(C(=O)C(C)(C)N2CCN(c3ccncc3)CC2)cc1 | CC(C(=O)C1=CC=C(OCC(=O)OC)C=C1)(C)Br.N1=CC=C(C=C1)N1CCNCC1>>N1=CC=C(C=C1)N1CCN(CC1)C(C(=O)C1=CC=C(OCC(=O)OC)C=C1)(C)C | Br[C:13]([C:11]([c:10]1[cH:9][cH:8][c:7]([O:6][CH2:5][C:3]([O:2][CH3:1])=[O:4])[cH:29][cH:28]1)=[O:12])([CH3:14])[CH3:15].[NH:16]1[CH2:17][CH2:18][N:19]([c:20]2[cH:21][cH:22][n:23][cH:24][cH:25]2)[CH2:26][CH2:27]1>>[CH3:1][O:2][C:3](=[O:4])[CH2:5][O:6][c:7]1[cH:8][cH:9][c:10]([C:11](=[O:12])[C:13]([CH3:14])([CH3:15])[N... | COC(=O)COc1ccc(C(=O)C(C)(C)Br)cc1.c1cc(N2CCNCC2)ccn1 | COC(=O)COc1ccc(C(=O)C(C)(C)N2CCN(c3ccncc3)CC2)cc1 | null | null | C(C)#N | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 991d0860ecc33e866762bd3aaf4c6d4d219c941351e42ccd75af51254d13229c | 33d1396f38c5e9df1464d5f7ae232caa1a83e08f9f8a7942734be1be4839a820 | O=C(CN1CCN(c2ccncc2)CC1)c1ccccc1 | Br-[C;H0;D4;+0:1](-[C;D1;H3:2])(-[C;D1;H3:3])-[C:4](=[O;D1;H0:5])-[c:6].[#7:7]1-[C:8]-[C:9]-[NH;D2;+0:10]-[C:11]-[C:12]-1>>[C;D1;H3:2]-[C;H0;D4;+0:1](-[C;D1;H3:3])(-[C:4](=[O;D1;H0:5])-[c:6])-[N;H0;D3;+0:10]1-[C:9]-[C:8]-[#7:7]-[C:12]-[C:11]-1 | null | [] | null | null | 34 | DAY | Methyl 4-(2,2-dimethylbromoacetyl)phenoxyacetate (1.58 g) was added to a stirred solution of 1-(4-pyridyl)piperazine (1.63 g) in acetonitrile (40 ml). After 34 days, the solid formed was removed by filtration and the filtrate evaporated to give an oil. Purification by flash chromatography on silica, eluting with 0.5 to... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary halide.Ketone.Secondary amine | Ketone.Tertiary amine | C1CNCC[NH]1 | C1C[NH]CC[NH]1 | c1ccccc1.C1C[NH]CC[NH]1.c1ccncc1 | HBr | C(C)#N | null | 816 | COC(=O)COc1ccc(C(=O)C(C)(C)Br)cc1.c1cc(N2CCNCC2)ccn1>C(C)#N>COC(=O)COc1ccc(C(=O)C(C)(C)N2CCN(c3ccncc3)CC2)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-045379b86e3a4189977f9bacd7189198 | BrBr.COC(=O)COc1ccc(C(=O)C(C)C)cc1>>COC(=O)COc1ccc(C(=O)C(C)(C)Br)cc1 | BrBr.CC(C(=O)C1=CC=C(OCC(=O)OC)C=C1)C>>BrC(C(=O)C1=CC=C(OCC(=O)OC)C=C1)(C)C | Br[Br:16].[CH3:1][O:2][C:3](=[O:4])[CH2:5][O:6][c:7]1[cH:8][cH:9][c:10]([C:11](=[O:12])[CH:13]([CH3:14])[CH3:15])[cH:17][cH:18]1>>[CH3:1][O:2][C:3](=[O:4])[CH2:5][O:6][c:7]1[cH:8][cH:9][c:10]([C:11](=[O:12])[C:13]([CH3:14])([CH3:15])[Br:16])[cH:17][cH:18]1 | BrBr.COC(=O)COc1ccc(C(=O)C(C)C)cc1 | COC(=O)COc1ccc(C(=O)C(C)(C)Br)cc1 | null | null | C(Cl)(Cl)(Cl)Cl | Functional Group Interconversion | Bromination | d3056545ad776e9c7ddc778233c4fddc58d054a01b75c1bcb69a741d62a992e8 | 6ec3f71a7b16ecb8b3d7f09ea088f160aabf7862c97e062437fea5d4b4e8602e | c1ccccc1 | Br-[Br;H0;D1;+0:1].[C;D1;H3:2]-[CH;D3;+0:3](-[C;D1;H3:4])-[C:5](=[O;D1;H0:6])-[c:7]>>[Br;H0;D1;+0:1]-[C;H0;D4;+0:3](-[C;D1;H3:2])(-[C;D1;H3:4])-[C:5](=[O;D1;H0:6])-[c:7] | null | [] | null | null | 16 | HOUR | Bromine (2.09 ml) was added dropwise over ten minutes to a stirred solution of the product of step (i) above (9.44 g) in carbon tetrachloride (200 ml). The solution was stirred for 16 hours, then the solvent was evaporated in vacuo to give an orange oil. A solution of this oil, in a small volume of dichloromethane, was... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Tertiary halide | null | null | c1ccccc1 | HBr | C(Cl)(Cl)(Cl)Cl | null | 16 | BrBr.COC(=O)COc1ccc(C(=O)C(C)C)cc1>C(Cl)(Cl)(Cl)Cl>COC(=O)COc1ccc(C(=O)C(C)(C)Br)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-9de51b647cd3468c9dd45ef82f58f9a0 | COC(=O)COc1ccc(C(=O)C(C)(C)Br)cc1.c1cc(N2CCNCC2)ccn1>>COC(=O)COc1ccc(C(=O)C(C)CN2CCN(c3ccncc3)CC2)cc1 | CC(C(=O)C1=CC=C(OCC(=O)OC)C=C1)(C)Br.N1=CC=C(C=C1)N1CCNCC1>>N1=CC=C(C=C1)N1CCN(CC1)CC(C(=O)C1=CC=C(OCC(=O)OC)C=C1)C | Br[C:13]([C:11]([c:10]1[cH:9][cH:8][c:7]([O:6][CH2:5][C:3]([O:2][CH3:1])=[O:4])[cH:29][cH:28]1)=[O:12])([CH3:14])[CH3:15].[NH:16]1[CH2:17][CH2:18][N:19]([c:20]2[cH:21][cH:22][n:23][cH:24][cH:25]2)[CH2:26][CH2:27]1>>[CH3:1][O:2][C:3](=[O:4])[CH2:5][O:6][c:7]1[cH:8][cH:9][c:10]([C:11](=[O:12])[CH:13]([CH3:14])[CH2:15][N:... | COC(=O)COc1ccc(C(=O)C(C)(C)Br)cc1.c1cc(N2CCNCC2)ccn1 | COC(=O)COc1ccc(C(=O)C(C)CN2CCN(c3ccncc3)CC2)cc1 | null | null | C(C)#N | Heteroatom Alkylation and Arylation | OtherReaction | 991d0860ecc33e866762bd3aaf4c6d4d219c941351e42ccd75af51254d13229c | 33d1396f38c5e9df1464d5f7ae232caa1a83e08f9f8a7942734be1be4839a820 | O=C(CCN1CCN(c2ccncc2)CC1)c1ccccc1 | Br-[C;H0;D4;+0:1](-[C;D1;H3:2])(-[CH3;D1;+0:3])-[C:4](=[O;D1;H0:5])-[c:6].[#7:7]1-[C:8]-[C:9]-[NH;D2;+0:10]-[C:11]-[C:12]-1>>[C;D1;H3:2]-[CH;D3;+0:1](-[CH2;D2;+0:3]-[N;H0;D3;+0:10]1-[C:9]-[C:8]-[#7:7]-[C:12]-[C:11]-1)-[C:4](=[O;D1;H0:5])-[c:6] | null | [] | null | null | null | null | A stirred mixture of methyl 4-(2,2-dimethylbromoacetyl)-phenoxyacetate (3.15 g), and 1-(4-pyridyl)piperazine (3.26 g) in acetonitrile (200 ml) was heated at reflux temperature for 4 days. The solvent was removed in vacuo and the residue partioned between dichloromethane/water. The organic phase was dried (MgSO4), evapo... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary halide.Ketone.Secondary amine | Ketone.Tertiary amine | C1CNCC[NH]1 | C1C[NH]CC[NH]1 | c1ccccc1.C1C[NH]CC[NH]1.c1ccncc1 | HBr | C(C)#N | null | null | COC(=O)COc1ccc(C(=O)C(C)(C)Br)cc1.c1cc(N2CCNCC2)ccn1>C(C)#N>COC(=O)COc1ccc(C(=O)C(C)CN2CCN(c3ccncc3)CC2)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-8cd1790f4528490e93ace90911d115bc | COC(=O)CCCc1ccc(CBr)cc1.c1cc(N2CCNCC2)ccn1>>COC(=O)CCCc1ccc(CN2CCN(c3ccncc3)CC2)cc1 | N1=CC=C(C=C1)N1CCNCC1.BrCC1=CC=C(C=C1)CCCC(=O)OC>>N1=CC=C(C=C1)N1CCN(CC1)CC1=CC=C(C=C1)CCCC(=O)OC | Br[CH2:12][c:11]1[cH:10][cH:9][c:8]([CH2:7][CH2:6][CH2:5][C:3]([O:2][CH3:1])=[O:4])[cH:26][cH:25]1.[NH:13]1[CH2:14][CH2:15][N:16]([c:17]2[cH:18][cH:19][n:20][cH:21][cH:22]2)[CH2:23][CH2:24]1>>[CH3:1][O:2][C:3](=[O:4])[CH2:5][CH2:6][CH2:7][c:8]1[cH:9][cH:10][c:11]([CH2:12][N:13]2[CH2:14][CH2:15][N:16]([c:17]3[cH:18][cH:... | COC(=O)CCCc1ccc(CBr)cc1.c1cc(N2CCNCC2)ccn1 | COC(=O)CCCc1ccc(CN2CCN(c3ccncc3)CC2)cc1 | null | null | C(C)#N | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | bad6b7d8e43c3debef0c262d60564e43415b41bcee72e526419c8c16be18fec1 | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | c1ccc(CN2CCN(c3ccncc3)CC2)cc1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[#7:5]1-[C:6]-[C:7]-[NH;D2;+0:8]-[C:9]-[C:10]-1>>[c:3]:[c:2](-[CH2;D2;+0:1]-[N;H0;D3;+0:8]1-[C:7]-[C:6]-[#7:5]-[C:10]-[C:9]-1):[c:4] | null | [] | 30 | CELSIUS | null | null | 1-(4-Pyridyl)piperazine (1.63 g) was dissolved in warm acetonitrile (25 ml), the solution cooled to 30° C. and with stirring, a solution of methyl 4-(4-bromomethylphenyl)butyrate in acetonitrile (5 ml) added. After 30 minutes the resulting precipitate was removed by filtration and the filtrate concentrated in vacuo to ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1CNCC[NH]1 | C1C[NH]CC[NH]1 | c1ccccc1.C1C[NH]CC[NH]1.c1ccncc1 | HBr | C(C)#N | 30 | null | COC(=O)CCCc1ccc(CBr)cc1.c1cc(N2CCNCC2)ccn1>C(C)#N>COC(=O)CCCc1ccc(CN2CCN(c3ccncc3)CC2)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-80e8ad99741f408593060a72e519d1ea | CCOC(=O)CCCCCOc1ccc(N(C(=O)OC(C)(C)C)c2ccncc2)cc1>>CCOC(=O)CCCCCOc1ccc(Nc2ccncc2)cc1 | FC(C(=O)O)(F)F.N1=CC=C(C=C1)N(C(=O)OC(C)(C)C)C1=CC=C(OCCCCCC(=O)OCC)C=C1>>N1=CC=C(C=C1)NC1=CC=C(OCCCCCC(=O)OCC)C=C1 | CC(C)(C)OC(=O)[N:16]([c:15]1[cH:14][cH:13][c:12]([O:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][C:4]([O:3][CH2:2][CH3:1])=[O:5])[cH:24][cH:23]1)[c:17]1[cH:18][cH:19][n:20][cH:21][cH:22]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][O:11][c:12]1[cH:13][cH:14][c:15]([NH:16][c:17]2[cH:18][cH:19][n:20]... | CCOC(=O)CCCCCOc1ccc(N(C(=O)OC(C)(C)C)c2ccncc2)cc1 | CCOC(=O)CCCCCOc1ccc(Nc2ccncc2)cc1 | null | null | ClCCl | Reduction | Boc amine deprotection | bbda4640db5f48af4538caded12fdadd56eacd6d4e5f7aefe46282d665df167e | a94b29c7264c852156fc1cdd4a0951a4fc26c06d0edc9e50c743825dbf79e3fd | c1ccc(Nc2ccncc2)cc1 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1](-[c:2](:[c:3]):[c:4])-[c:5]1:[c:6]:[c:7]:[#7;a:8]:[c:9]:[c:10]:1>>[c:3]:[c:2](-[NH;D2;+0:1]-[c:5]1:[c:6]:[c:7]:[#7;a:8]:[c:9]:[c:10]:1):[c:4] | null | [] | null | null | null | null | Trifluoroacetic acid (3 ml) was added to a stirred solution of ethyl 6-[4-[N-(4-pyridyl)-N-tertiary-butyloxycarbonylamino]-phenoxy]hexanoate (260 mg) dissolved in dichloromethane (3 ml). After 18 hours the solvents were removed in vacuo and the residual gum dissolved in dichloromethane. This solution was treated with a... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Secondary amine | null | null | c1ccccc1.c1ccncc1 | HO- | ClCCl | null | null | CCOC(=O)CCCCCOc1ccc(N(C(=O)OC(C)(C)C)c2ccncc2)cc1>ClCCl>CCOC(=O)CCCCCOc1ccc(Nc2ccncc2)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-88019f4b8c9b42769694053eccb9f705 | COc1ccc(N)cc1.Clc1ccncc1>>COc1ccc(Nc2ccncc2)cc1 | Cl.ClC1=CC=NC=C1.COC1=CC=C(N)C=C1>>N1=CC=C(C=C1)NC1=CC=C(C=C1)OC | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([NH2:7])[cH:14][cH:15]1.Cl[c:8]1[cH:9][cH:10][n:11][cH:12][cH:13]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([NH:7][c:8]2[cH:9][cH:10][n:11][cH:12][cH:13]2)[cH:14][cH:15]1 | COc1ccc(N)cc1.Clc1ccncc1 | COc1ccc(Nc2ccncc2)cc1 | null | null | ClCCl | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c026a7bf7aba66b20cf21a13c528689aaaa1c05901524d62b36ca0c3b0572cef | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2ccncc2)cc1 | Cl-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[#7;a:4]:[c:5]:[c:6]:1.[NH2;D1;+0:7]-[c:8](:[c:9]):[c:10]>>[c:9]:[c:8](-[NH;D2;+0:7]-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[#7;a:4]:[c:5]:[c:6]:1):[c:10] | null | [] | 140 | CELSIUS | null | null | A stirred mixture of 4-chloropyridine hydrochloride (2 g) and 4-methoxyaniline (4.9 g) was heated at 140° C. for 5 hours. After cooling the residue was dissolved in dichloromethane (250 ml), the solution extracted with water (2×100 ml). The aqueous extracts were treated with sodium hydroxide solution and then extracted... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccncc1 | c1ccncc1 | c1ccccc1.c1ccncc1 | HCl | ClCCl | 140 | null | COc1ccc(N)cc1.Clc1ccncc1>ClCCl>COc1ccc(Nc2ccncc2)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-406919881ea245cf8271f8faf8e54070 | CC(C)(C)OC(=O)N(c1ccncc1)c1ccc(O)cc1.CCOC(=O)CCCCCBr>>CCOC(=O)CCCCCOc1ccc(N(C(=O)OC(C)(C)C)c2ccncc2)cc1 | [H-].[Na+].N1=CC=C(C=C1)N(C(=O)OC(C)(C)C)C1=CC=C(C=C1)O.BrCCCCCC(=O)OCC>>N1=CC=C(C=C1)N(C(=O)OC(C)(C)C)C1=CC=C(OCCCCCC(=O)OCC)C=C1 | [OH:11][c:12]1[cH:13][cH:14][c:15]([N:16]([C:17](=[O:18])[O:19][C:20]([CH3:21])([CH3:22])[CH3:23])[c:24]2[cH:25][cH:26][n:27][cH:28][cH:29]2)[cH:30][cH:31]1.Br[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][C:4]([O:3][CH2:2][CH3:1])=[O:5]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][O:11][c:12]1[cH:13][cH... | CC(C)(C)OC(=O)N(c1ccncc1)c1ccc(O)cc1.CCOC(=O)CCCCCBr | CCOC(=O)CCCCCOc1ccc(N(C(=O)OC(C)(C)C)c2ccncc2)cc1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | c1ccc(Nc2ccncc2)cc1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[OH;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:4]-[c:5](:[c:6]):[c:7] | null | [] | null | null | 5 | MINUTE | Sodium hydride (50% w/w dispersion in mineral oil, 55 mg) was added under argon to a stirred solution of the product from step (iii) above (300 mg) in dry DMF (5 ml). After five minutes, ethyl 6-bromohexanoate (0.20 ml) was added and the mixture stirred for 16 hours. The DMF was evaporated in vacuo and the residue part... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccccc1.c1ccncc1 | HBr | CN(C)C=O | null | 0.083333 | CC(C)(C)OC(=O)N(c1ccncc1)c1ccc(O)cc1.CCOC(=O)CCCCCBr>CN(C)C=O>CCOC(=O)CCCCCOc1ccc(N(C(=O)OC(C)(C)C)c2ccncc2)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-468ebd3d0a054614b2598365cfd64b5d | CCN(C(C)C)C(C)C.CN(C)C(On1nnc2ccccc21)=[N+](C)C.CN(C)C=O.O=C(O)c1ccc(N2CCNCC2c2ccncc2)cc1>>CCOC(=O)CN(C)C(=O)c1ccc(N2CCNCC2c2ccncc2)cc1 | N1=CC=C(C=C1)C1N(CCNC1)C1=CC=C(C(=O)O)C=C1.C=1C=CC2=C(C1)N=NN2O.CN(C)C(=[N+](C)C)ON1C2=C(C=CC=C2)N=N1.F[P-](F)(F)(F)(F)F.C(C)(C)N(CC)C(C)C.CN(C)C=O>>N1=CC=C(C=C1)C1N(CCNC1)C1=CC=C(C(=O)N(CC(=O)OCC)C)C=C1 | CC(C)N(C(C)C)[CH2:2][CH3:1].C[N+](C)=C(On1nnc2ccccc21)[N:7]([CH3:6])[CH3:8].CN(C)[CH:4]=[O:5].[OH:3][C:9](=[O:10])[c:11]1[cH:12][cH:13][c:14]([N:15]2[CH2:16][CH2:17][NH:18][CH2:19][CH:20]2[c:21]2[cH:22][cH:23][n:24][cH:25][cH:26]2)[cH:27][cH:28]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][N:7]([CH3:8])[C:9](=[O:10])[c:11... | CCN(C(C)C)C(C)C.CN(C)C(On1nnc2ccccc21)=[N+](C)C.CN(C)C=O.O=C(O)c1ccc(N2CCNCC2c2ccncc2)cc1 | CCOC(=O)CN(C)C(=O)c1ccc(N2CCNCC2c2ccncc2)cc1 | null | null | O | Acylation | OtherReaction | 0f5b2bd652a38b3caf31d2a7fc586e8969388ce14a1ddcc6f848d469d918736c | 8e406f8697cd544c5989f43304cfe379b1745278eeeb7c24f63a2c38ad3b1803 | c1ccc(N2CCNCC2c2ccncc2)cc1 | C-C(-C)-N(-[CH2;D2;+0:1]-[C;D1;H3:2])-C(-C)-C.C-N(-C)-[CH;D2;+0:3]=[O;D1;H0:4].C-[N+](-C)=C(-O-n1:n:n:c2:c:c:c:c:c:2:1)-[N;H0;D3;+0:5](-[C;D1;H3:6])-[CH3;D1;+0:7].[O;D1;H0:8]=[C;H0;D3;+0:9](-[OH;D1;+0:10])-[c:11](:[c:12]):[c:13]>>[C;D1;H3:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:10]-[C;H0;D3;+0:3](=[O;D1;H0:4])-[CH2;D2;+0:7]-[N;H0... | null | [] | null | null | 15 | MINUTE | To a stirred mixture of 4-[(4-pyridyl)piperazin-1-yl]benzoic acid (prepared as in Example 30(i)) (311 mg), HOBt.H2O (170 mg) and HBTU (416 mg) in DMF (5 ml) at 0°-5° C. under argon was added diisopropylethylamine (0.75 ml). The ice-bath was removed and the reaction mixture was stirred at room temperature for 15 minutes... | 10.6084/m9.figshare.5104873.v1 | null | Amidinium.Carboxylic acid.Tertiary amide.Tertiary amine | Ester.Tertiary amide | c1ccc2[nH]nnc2c1 | null | c1ccccc1.C1C[NH]CCN1.c1ccncc1 | HO- | O | null | 0.25 | CCN(C(C)C)C(C)C.CN(C)C(On1nnc2ccccc21)=[N+](C)C.CN(C)C=O.O=C(O)c1ccc(N2CCNCC2c2ccncc2)cc1>O>CCOC(=O)CN(C)C(=O)c1ccc(N2CCNCC2c2ccncc2)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-8d6ceef34f4b4f019e54e9dd2e83cde8 | Nc1ccc(N2CCN(c3ccncc3)CC2)cc1.O=C1CCC(=O)O1>>NC(CC(=O)c1ccc(N2CCN(c3ccncc3)CC2)cc1)C(=O)O | NC1=CC=C(C=C1)N1CCN(CC1)C1=CC=NC=C1.C1(CCC(=O)O1)=O.CN(C)C=O>>O=C(CC(C(=O)O)N)C1=CC=C(C=C1)N1CCN(CC1)C1=CC=NC=C1 | [NH2:1][c:6]1[cH:7][cH:8][c:9]([N:10]2[CH2:11][CH2:12][N:13]([c:14]3[cH:15][cH:16][n:17][cH:18][cH:19]3)[CH2:20][CH2:21]2)[cH:22][cH:23]1.[CH2:2]1[CH2:3][C:4](=[O:5])[O:26][C:24]1=[O:25]>>[NH2:1][CH:2]([CH2:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][c:9]([N:10]2[CH2:11][CH2:12][N:13]([c:14]3[cH:15][cH:16][n:17][cH:18][cH:19]3)[... | Nc1ccc(N2CCN(c3ccncc3)CC2)cc1.O=C1CCC(=O)O1 | NC(CC(=O)c1ccc(N2CCN(c3ccncc3)CC2)cc1)C(=O)O | null | null | null | C-C Coupling | OtherReaction | e797d9d32d66f01479692bf50f523344fd4fe7b272fa3af1b60780dfc67046fa | 828b71c1c58f0218ecc1c56a40845f42dbec75d464a99d79fb9f49e731f34cb9 | c1ccc(N2CCN(c3ccncc3)CC2)cc1 | [NH2;D1;+0:1]-[c;H0;D3;+0:2](:[c:3]:[c:4]):[c:5]:[c:6].[O;D1;H0:7]=[C:8]1-[CH2;D2;+0:9]-[C:10]-[C;H0;D3;+0:11](=[O;D1;H0:12])-[O;H0;D2;+0:13]-1>>[NH2;D1;+0:1]-[CH;D3;+0:9](-[C:10]-[C;H0;D3;+0:11](=[O;D1;H0:12])-[c;H0;D3;+0:2](:[c:3]:[c:4]):[c:5]:[c:6])-[C:8](=[O;D1;H0:7])-[OH;D1;+0:13] | null | [] | null | null | 2.5 | HOUR | To a solution of 1-(4-aminophenyl)-4-(4-pyridyl)piperazine (100 mg) in DMF (8 ml) was added succinic anhydride (79 mg). The reaction mixture was stirred at room temperature for 2.5 hr and a precipitate was collected, washed with DMF and ethanol, then dried to give the title compound (106 mg) as a beige-coloured solid: ... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Primary amine | Carboxylic acid.Ketone.Primary amine | c1ccccc1.C1CCOC1 | c1ccccc1 | c1ccccc1.C1C[NH]CC[NH]1.c1ccncc1 | null | null | null | 2.5 | Nc1ccc(N2CCN(c3ccncc3)CC2)cc1.O=C1CCC(=O)O1>>NC(CC(=O)c1ccc(N2CCN(c3ccncc3)CC2)cc1)C(=O)O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-49e1ae57538b4195be3dcdaff27940ff | O=C(O)CCCOc1ccc(N2CCN(c3ccncc3)CC2)cc1>>O=C(O)CCCOc1ccc(N2CCN(c3ccncc3)CC2)cc1 | N1=CC=C(C=C1)N1CCN(CC1)C1=CC=C(OCCCC(=O)O)C=C1.CO.Cl.N1=CC=CC=C1>>Cl.N1=CC=C(C=C1)N1CCN(CC1)C1=CC=C(OCCCC(=O)O)C=C1 | [O:2]=[C:3]([OH:4])[CH2:5][CH2:6][CH2:7][O:8][c:9]1[cH:10][cH:11][c:12]([N:13]2[CH2:14][CH2:15][N:16]([c:17]3[cH:18][cH:19][n:20][cH:21][cH:22]3)[CH2:23][CH2:24]2)[cH:25][cH:26]1>>[O:2]=[C:3]([OH:4])[CH2:5][CH2:6][CH2:7][O:8][c:9]1[cH:10][cH:11][c:12]([N:13]2[CH2:14][CH2:15][N:16]([c:17]3[cH:18][cH:19][n:20][cH:21][cH:... | O=C(O)CCCOc1ccc(N2CCN(c3ccncc3)CC2)cc1 | O=C(O)CCCOc1ccc(N2CCN(c3ccncc3)CC2)cc1 | null | null | C(C)(=O)OCC | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | c1ccc(N2CCN(c3ccncc3)CC2)cc1 | null | 81.3 | [{"value": 81.3, "product": "Cl.N1=CC=C(C=C1)N1CCN(CC1)C1=CC=C(OCCCC(=O)O)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of the product from Example 26 (1.5 g) and methanol (80 ml) was heated to reflux with stirring, and solid pyridine hydrochloride (0.5 g) was added. Heating was stopped and ethyl acetate (10 ml) was added. The reaction mixture was evaporated until a slight turbidity was observed. On further cooling, a precipit... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | c1ccccc1.C1C[NH]CC[NH]1.c1ccncc1 | null | C(C)(=O)OCC | null | null | O=C(O)CCCOc1ccc(N2CCN(c3ccncc3)CC2)cc1>C(C)(=O)OCC>O=C(O)CCCOc1ccc(N2CCN(c3ccncc3)CC2)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-35a8c2a4b4bc4caeaaf6b411adca67fe | COC(=O)COc1ccc(C(=O)CN2CCNCC2=O)cc1.Clc1ccncc1>>O=C(O)COc1ccc(C(=O)CN2CCN(c3ccncc3)CC2=O)cc1 | N1(C(CNCC1)=O)CC(=O)C1=CC=C(OCC(=O)OC)C=C1.Cl.ClC1=CC=NC=C1.C(C)N(CC)CC>>Cl.N1=CC=C(C=C1)N1CC(N(CC1)CC(=O)C1=CC=C(OCC(=O)O)C=C1)=O | C[O:4][C:3](=[O:2])[CH2:5][O:6][c:7]1[cH:8][cH:9][c:10]([C:11](=[O:12])[CH2:13][N:14]2[CH2:15][CH2:16][NH:17][CH2:24][C:25]2=[O:26])[cH:27][cH:28]1.Cl[c:18]1[cH:19][cH:20][n:21][cH:22][cH:23]1>>[O:2]=[C:3]([OH:4])[CH2:5][O:6][c:7]1[cH:8][cH:9][c:10]([C:11](=[O:12])[CH2:13][N:14]2[CH2:15][CH2:16][N:17]([c:18]3[cH:19][cH... | COC(=O)COc1ccc(C(=O)CN2CCNCC2=O)cc1.Clc1ccncc1 | O=C(O)COc1ccc(C(=O)CN2CCN(c3ccncc3)CC2=O)cc1 | null | null | O.O1CCOCC1 | Heteroatom Alkylation and Arylation | OtherReaction | 0dc92487faaa569ac6006832d09aed0ca46c8a15f56d62d2cda16ba7e3dd0d5a | 154ad2504fb7aaca0f52c4b8eebdfca329f4106b95adc3c71ff059886f074b58 | O=C(CN1CCN(c2ccncc2)CC1=O)c1ccccc1 | C-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4].[O;D1;H0:5]=[C:6]-[C:7]-[#7:8]1-[C:9]-[C:10]-[NH;D2;+0:11]-[C:12]-[C:13]-1=[O;D1;H0:14].Cl-[c;H0;D3;+0:15]1:[c:16]:[c:17]:[#7;a:18]:[c:19]:[c:20]:1>>[C:3]-[C:2](=[O;D1;H0:4])-[OH;D1;+0:1].[O;D1;H0:5]=[C:6]-[C:7]-[#7:8]1-[C:9]-[C:10]-[N;H0;D3;+0:11](-[c;H0;D3;+0:15]2:[c:16]:[c:... | 40.7 | [{"value": 40.7, "product": "Cl.N1=CC=C(C=C1)N1CC(N(CC1)CC(=O)C1=CC=C(OCC(=O)O)C=C1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of methyl 4-[2-(piperazin-2-one-1-yl)acetyl]-phenoxyacetate (0.347 g), 4-chloropyridine hydrochloride (0.19 g) and triethylamine (0.178 g) in water (8 ml) and dioxan (1 ml) was heated on a steam bath for 2 hours and then evaporated to dryness. The residue was triturated with water (2 ml) and filtered. The so... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ester.Secondary amine | Carboxylic acid.Tertiary amine | C1C[NH]CCN1.c1ccncc1 | C1C[NH]CC[NH]1.c1ccncc1 | c1ccccc1.C1C[NH]CC[NH]1.c1ccncc1 | HCl | O.O1CCOCC1 | null | null | COC(=O)COc1ccc(C(=O)CN2CCNCC2=O)cc1.Clc1ccncc1>O.O1CCOCC1>O=C(O)COc1ccc(C(=O)CN2CCN(c3ccncc3)CC2=O)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-97fb1cd716ad44c38c1ac6b567ebd2cd | CCOC(=O)CC(C)CBr.Oc1ccc(N2CCN(c3ccncc3)CC2)cc1>>CCOC(=O)CC(C)COc1ccc(N2CCN(c3ccncc3)CC2)cc1 | N1=CC=C(C=C1)N1CCN(CC1)C1=CC=C(C=C1)O.[H-].[Na+].C(C)OC(CC(CBr)C)=O>>CC(CC(=O)OCC)COC1=CC=C(C=C1)N1CCN(CC1)C1=CC=NC=C1 | Br[CH2:9][CH:7]([CH2:6][C:4]([O:3][CH2:2][CH3:1])=[O:5])[CH3:8].[OH:10][c:11]1[cH:12][cH:13][c:14]([N:15]2[CH2:16][CH2:17][N:18]([c:19]3[cH:20][cH:21][n:22][cH:23][cH:24]3)[CH2:25][CH2:26]2)[cH:27][cH:28]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][CH:7]([CH3:8])[CH2:9][O:10][c:11]1[cH:12][cH:13][c:14]([N:15]2[CH2:16][CH... | CCOC(=O)CC(C)CBr.Oc1ccc(N2CCN(c3ccncc3)CC2)cc1 | CCOC(=O)CC(C)COc1ccc(N2CCN(c3ccncc3)CC2)cc1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | c1ccc(N2CCN(c3ccncc3)CC2)cc1 | Br-[CH2;D2;+0:1]-[C:2](-[C;D1;H3:3])-[C:4]-[C:5](-[#8:6])=[O;D1;H0:7].[OH;D1;+0:8]-[c:9](:[c:10]):[c:11]>>[#8:6]-[C:5](=[O;D1;H0:7])-[C:4]-[C:2](-[C;D1;H3:3])-[CH2;D2;+0:1]-[O;H0;D2;+0:8]-[c:9](:[c:10]):[c:11] | null | [] | null | null | 1 | HOUR | To a stirred suspension of 4-[4-(4-pyridyl)piperazin-1-yl]phenol (1.02 g) in dry DMF (10 ml) was added sodium hydride (60% dispersion in mineral oil, 0.16 g) and the mixture stirred for 1 hour at room temperature. To the resulting solution was added ethyl-4-bromo-3-methylbutyrate and the mixture stirred for 16 hours. S... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccccc1.C1C[NH]CC[NH]1.c1ccncc1 | HBr | CN(C)C=O | null | 1 | CCOC(=O)CC(C)CBr.Oc1ccc(N2CCN(c3ccncc3)CC2)cc1>CN(C)C=O>CCOC(=O)CC(C)COc1ccc(N2CCN(c3ccncc3)CC2)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-6b3a7cf777344097bf9b02589a8bd408 | C=CC1COC(=O)C1.CO>>C=CC(CO)CC(=O)OC | C(=C)C1CC(=O)OC1.C(C)(=O)[O-].[Na+].CO>>OCC(CC(=O)OC)C=C | [CH2:1]=[CH:2][CH:3]1[CH2:4][O:5][C:7](=[O:8])[CH2:6]1.[OH:9][CH3:10]>>[CH2:1]=[CH:2][CH:3]([CH2:4][OH:5])[CH2:6][C:7](=[O:8])[O:9][CH3:10] | C=CC1COC(=O)C1.CO | C=CC(CO)CC(=O)OC | null | null | null | Protection | OtherReaction | f65ecd86cf1b1f31309508be1adccc3f85ab0990ef2dc60a4a80301d46cae947 | a87b94e4ea3a93e5c94bd0993c5a90f9386746ba066362d4c8f843155ae3cfcd | null | [C;D1;H2:1]=[C:2]-[C:3]1-[C:4]-[O;H0;D2;+0:5]-[C;H0;D3;+0:6](=[O;D1;H0:7])-[C:8]-1.[C;D1;H3:9]-[OH;D1;+0:10]>>[C;D1;H2:1]=[C:2]-[C:3](-[C:4]-[OH;D1;+0:5])-[C:8]-[C;H0;D3;+0:6](=[O;D1;H0:7])-[O;H0;D2;+0:10]-[C;D1;H3:9] | null | [] | null | null | null | null | A solution of RS 3-vinylbutyrolactone (3.5 g) and sodium acetate (2.56 g) in methanol (30 ml) was kept for 20 hours. Solvent was evaporated and the residue was partitioned between water and ether. The aqueous layer was extracted twice more with ether and the extracts combined, filtered through phase separating paper an... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Methanol | Ester.Primary alcohol | C1CCOC1 | null | null | null | null | null | null | C=CC1COC(=O)C1.CO>>C=CC(CO)CC(=O)OC |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-8bb6c21c7a284b64a51177a5ee747c79 | C=CC(CO)CC(=O)OC.CCOC(=O)N=NC(=O)OCC.Oc1ccc(N2CCN(c3ccncc3)CC2)cc1>>C=CC(COc1ccc(N2CCN(c3ccncc3)CC2)cc1)CC(=O)OC.[NH4+].[OH-] | N(=NC(=O)OCC)C(=O)OCC.COC(CC(CO)C=C)=O.N1=CC=C(C=C1)N1CCN(CC1)C1=CC=C(C=C1)O.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1>>[OH-].[NH4+].N1=CC=C(C=C1)N1CCN(CC1)C1=CC=C(OCC(CC(=O)OC)C=C)C=C1 | [CH2:1]=[CH:2][CH:3]([CH2:4][OH:5])[CH2:24][C:25](=[O:26])[O:27][CH3:28].CCOC(=O)[N:29]=NC(=O)[O:30]CC.O[c:6]1[cH:7][cH:8][c:9]([N:10]2[CH2:11][CH2:12][N:13]([c:14]3[cH:15][cH:16][n:17][cH:18][cH:19]3)[CH2:20][CH2:21]2)[cH:22][cH:23]1>>[CH2:1]=[CH:2][CH:3]([CH2:4][O:5][c:6]1[cH:7][cH:8][c:9]([N:10]2[CH2:11][CH2:12][N:1... | C=CC(CO)CC(=O)OC.CCOC(=O)N=NC(=O)OCC.Oc1ccc(N2CCN(c3ccncc3)CC2)cc1 | C=CC(COc1ccc(N2CCN(c3ccncc3)CC2)cc1)CC(=O)OC.[NH4+].[OH-] | null | null | ClCCl | Heteroatom Alkylation and Arylation | OtherReaction | ff34bceabc454435fa99ab5cccc0f81a5bba1a327b229bd59c2918584e612836 | 777453315a160f3afb8d19efd268dbb89608e869705e1322d200b8b38ccdb23c | c1ccc(N2CCN(c3ccncc3)CC2)cc1 | C-C-O-C(=O)-[N;H0;D2;+0:1]=N-C(=O)-[O;H0;D2;+0:2]-C-C.O-[c;H0;D3;+0:3](:[c:4]:[c:5]):[c:6]:[c:7].[C;D1;H2:8]=[C:9]-[C:10]-[C:11]-[OH;D1;+0:12]>>[C;D1;H2:8]=[C:9]-[C:10]-[C:11]-[O;H0;D2;+0:12]-[c;H0;D3;+0:3](:[c:4]:[c:5]):[c:6]:[c:7].[NH4+;D0:1].[OH-;D0:2] | 19.6 | [{"value": 19.6, "product": "N1=CC=C(C=C1)N1CCN(CC1)C1=CC=C(OCC(CC(=O)OC)C=C)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a stirred suspension of 4-[4-(4-pyridyl)piperazin-1-yl]phenol (1.98 g) in dichloromethane (30 ml) at 15° C. was added triphenylphosphine (2.04 g) followed by dropwise addition of diethyl azodicarboxylate (1.35 g). The mixture was stirred until complete solution was obtained. Methyl-4-hydroxy-3-vinylbutyrate (1.12 g)... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether.Diazene.Primary alcohol.Aromatic alcohol | Ether | c1ccccc1 | c1ccccc1 | c1ccccc1.C1C[NH]CC[NH]1.c1ccncc1 | HO- | ClCCl | null | null | C=CC(CO)CC(=O)OC.CCOC(=O)N=NC(=O)OCC.Oc1ccc(N2CCN(c3ccncc3)CC2)cc1>ClCCl>C=CC(COc1ccc(N2CCN(c3ccncc3)CC2)cc1)CC(=O)OC.[NH4+].[OH-] |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-b7642883f03a44b1a3f521f0f19b94b6 | C=CCCl.Oc1ccc(N2CCN(c3ccncc3)CC2)cc1>>C=CCOc1ccc(N2CCN(c3ccncc3)CC2)cc1 | [H-].[Na+].N1=CC=C(C=C1)N1CCN(CC1)C1=CC=C(C=C1)O.C(C=C)Cl>>C(C=C)OC1=CC=C(C=C1)N1CCN(CC1)C1=CC=NC=C1 | Cl[CH2:3][CH:2]=[CH2:1].[OH:4][c:5]1[cH:6][cH:7][c:8]([N:9]2[CH2:10][CH2:11][N:12]([c:13]3[cH:14][cH:15][n:16][cH:17][cH:18]3)[CH2:19][CH2:20]2)[cH:21][cH:22]1>>[CH2:1]=[CH:2][CH2:3][O:4][c:5]1[cH:6][cH:7][c:8]([N:9]2[CH2:10][CH2:11][N:12]([c:13]3[cH:14][cH:15][n:16][cH:17][cH:18]3)[CH2:19][CH2:20]2)[cH:21][cH:22]1 | C=CCCl.Oc1ccc(N2CCN(c3ccncc3)CC2)cc1 | C=CCOc1ccc(N2CCN(c3ccncc3)CC2)cc1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | c1ccc(N2CCN(c3ccncc3)CC2)cc1 | Cl-[CH2;D2;+0:1]-[C:2]=[C;D1;H2:3].[OH;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[C;D1;H2:3]=[C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:4]-[c:5](:[c:6]):[c:7] | 85.7 | [{"value": 85.7, "product": "C(C=C)OC1=CC=C(C=C1)N1CCN(CC1)C1=CC=NC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 20 | MINUTE | Sodium hydride (60% dispersion in mineral oil, 0.4 g) was added to a stirred suspension of 4-[4-(4-pyridyl)piperazin-1-yl]phenol (2.55 g) in DMF (25 ml) and the mixture stirred for 20 minutes at room temperature. Allyl chloride (0.756 g) was added dropwise and stirring continued for 20 hours. Ice-water (75 ml) was adde... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccccc1.C1C[NH]CC[NH]1.c1ccncc1 | HCl | CN(C)C=O | null | 0.333333 | C=CCCl.Oc1ccc(N2CCN(c3ccncc3)CC2)cc1>CN(C)C=O>C=CCOc1ccc(N2CCN(c3ccncc3)CC2)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-4a4e1a71f02a49428dedef574eb2980f | C=CCOc1ccc(N2CCN(c3ccncc3)CC2)cc1>>C=CCc1cc(N2CCN(c3ccncc3)CC2)ccc1O | C(C=C)OC1=CC=C(C=C1)N1CCN(CC1)C1=CC=NC=C1.C1(=CC=CC=C1)OC1=CC=CC=C1>>C(C=C)C1=C(C=CC(=C1)N1CCN(CC1)C1=CC=NC=C1)O | [CH2:1]=[CH:2][CH2:3][O:22][c:21]1[cH:4][cH:5][c:6]([N:7]2[CH2:8][CH2:9][N:10]([c:11]3[cH:12][cH:13][n:14][cH:15][cH:16]3)[CH2:17][CH2:18]2)[cH:19][cH:20]1>>[CH2:1]=[CH:2][CH2:3][c:4]1[cH:5][c:6]([N:7]2[CH2:8][CH2:9][N:10]([c:11]3[cH:12][cH:13][n:14][cH:15][cH:16]3)[CH2:17][CH2:18]2)[cH:19][cH:20][c:21]1[OH:22] | C=CCOc1ccc(N2CCN(c3ccncc3)CC2)cc1 | C=CCc1cc(N2CCN(c3ccncc3)CC2)ccc1O | null | null | CCOCC | Miscellaneous | OtherReaction | f9046ab8287acad6d9b914f5f533866252d6845a323cc2516eb4a5b1de541a76 | 58578155da4647eafb0f18a2061753170490dc4f2b17890a513522e28d385731 | c1ccc(N2CCN(c3ccncc3)CC2)cc1 | [C;D1;H2:1]=[C:2]-[CH2;D2;+0:3]-[O;H0;D2;+0:4]-[c:5](:[c:6]):[cH;D2;+0:7]:[c:8]:[c:9]>>[C;D1;H2:1]=[C:2]-[CH2;D2;+0:3]-[c;H0;D3;+0:7](:[c:8]:[c:9]):[c:5](-[OH;D1;+0:4]):[c:6] | 17.6 | [{"value": 17.6, "product": "C(C=C)C1=C(C=CC(=C1)N1CCN(CC1)C1=CC=NC=C1)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | The product from step (i) (5 g) was heated under argon in gently refluxing diphenyl ether (15 g) for 21/2 hours. The mixture was cooled to room temperature and ether (70 ml) was added. The solid material was filtered and purified by flash chromatography on silica gel, eluting with methanol/dichloromethane (1/4 v/v) to ... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Allyl | Aromatic alcohol.Allyl | c1ccccc1 | c1ccccc1 | c1ccccc1.C1C[NH]CC[NH]1.c1ccncc1 | null | CCOCC | null | null | C=CCOc1ccc(N2CCN(c3ccncc3)CC2)cc1>CCOCC>C=CCc1cc(N2CCN(c3ccncc3)CC2)ccc1O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-372ee0766f514314a4177039bddb9fe0 | C=CCc1cc(N2CCN(c3ccncc3)CC2)ccc1O>>CCCc1cc(N2CCN(c3ccncc3)CC2)ccc1O | C(C=C)C1=C(C=CC(=C1)N1CCN(CC1)C1=CC=NC=C1)O.[H][H]>>C(CC)C1=C(C=CC(=C1)N1CCN(CC1)C1=CC=NC=C1)O | [CH2:1]=[CH:2][CH2:3][c:4]1[cH:5][c:6]([N:7]2[CH2:8][CH2:9][N:10]([c:11]3[cH:12][cH:13][n:14][cH:15][cH:16]3)[CH2:17][CH2:18]2)[cH:19][cH:20][c:21]1[OH:22]>>[CH3:1][CH2:2][CH2:3][c:4]1[cH:5][c:6]([N:7]2[CH2:8][CH2:9][N:10]([c:11]3[cH:12][cH:13][n:14][cH:15][cH:16]3)[CH2:17][CH2:18]2)[cH:19][cH:20][c:21]1[OH:22] | C=CCc1cc(N2CCN(c3ccncc3)CC2)ccc1O | CCCc1cc(N2CCN(c3ccncc3)CC2)ccc1O | null | [Pd] | C(C)O.Cl | Reduction | Hydrogenation (double to single) | bc16a674f12262641e5cd54edc2026446c884c0ddcda2374dddc2ac4d3dae2ab | 6afc5b4ad7d0f8b85f89bd805881fd9206fc3da38639abfb1c97bb82ede31c54 | c1ccc(N2CCN(c3ccncc3)CC2)cc1 | [CH2;D1;+0:1]=[CH;D2;+0:2]-[C:3]-[c:4]>>[CH3;D1;+0:1]-[CH2;D2;+0:2]-[C:3]-[c:4] | 94 | [{"value": 94.0, "product": "C(CC)C1=C(C=CC(=C1)N1CCN(CC1)C1=CC=NC=C1)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | The product from Example 134, step (ii) (0.74 g) in ethanol (25 ml) and 1N hydrochloric acid (2.5 ml) was hydrogenated at room temperature and atmospheric pressure over 10% palladium charcoal (0.15 g) until uptake of hydrogen was complete. Catalyst was removed by filtration through diatomaceous earth and the filtrate e... | 10.6084/m9.figshare.5104873.v1 | null | Allyl | null | null | null | c1ccccc1.C1C[NH]CC[NH]1.c1ccncc1 | null | [Pd].C(C)O.Cl | null | null | C=CCc1cc(N2CCN(c3ccncc3)CC2)ccc1O>[Pd].C(C)O.Cl>CCCc1cc(N2CCN(c3ccncc3)CC2)ccc1O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-bc4c5bfd0a2540ebba7d4dbbdd3411b3 | COC(=O)C(CCOc1ccc(N2CCN(c3ccncc3)CC2)cc1)NC(=O)OC(C)(C)C>>COC(=O)C(N)CCOc1ccc(N2CCN(c3ccncc3)CC2)cc1 | C(C)(C)(C)OC(=O)NC(C(=O)OC)CCOC1=CC=C(C=C1)N1CCN(CC1)C1=CC=NC=C1>>NC(C(=O)OC)CCOC1=CC=C(C=C1)N1CCN(CC1)C1=CC=NC=C1 | CC(C)(C)OC(=O)[NH:6][CH:5]([C:3]([O:2][CH3:1])=[O:4])[CH2:7][CH2:8][O:9][c:10]1[cH:11][cH:12][c:13]([N:14]2[CH2:15][CH2:16][N:17]([c:18]3[cH:19][cH:20][n:21][cH:22][cH:23]3)[CH2:24][CH2:25]2)[cH:26][cH:27]1>>[CH3:1][O:2][C:3](=[O:4])[CH:5]([NH2:6])[CH2:7][CH2:8][O:9][c:10]1[cH:11][cH:12][c:13]([N:14]2[CH2:15][CH2:16][N... | COC(=O)C(CCOc1ccc(N2CCN(c3ccncc3)CC2)cc1)NC(=O)OC(C)(C)C | COC(=O)C(N)CCOc1ccc(N2CCN(c3ccncc3)CC2)cc1 | null | null | C(=O)(C(F)(F)F)O | Reduction | Hydrogenolysis of amides/imides/carbamates | 3c33dd2a2d355ee5ba0287367e209aa147a39aa00607f0c95fb2bf1ade45d014 | c5b5dffe7dd8beebdc1baa8b5b05300a9f7079e65dcfd42ade6f8a77ff09537d | c1ccc(N2CCN(c3ccncc3)CC2)cc1 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[C:2](-[C:3])-[C:4](=[O;D1;H0:5])-[#8:6]-[C;D1;H3:7]>>[C:3]-[C:2](-[NH2;D1;+0:1])-[C:4](=[O;D1;H0:5])-[#8:6]-[C;D1;H3:7] | 74.1 | [{"value": 74.1, "product": "NC(C(=O)OC)CCOC1=CC=C(C=C1)N1CCN(CC1)C1=CC=NC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | The compound of Example 140 (0.96 g) in TFA (10 ml) was kept at room temperature for 2 hours. The solution was evaporated and the residue dissolved in water (15 ml) and the solution basified with sodium carbonate. The mixture was extracted three times with dichloromethane. Evaporation of the combined extracts gave the ... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Primary amine | null | null | c1ccccc1.C1C[NH]CC[NH]1.c1ccncc1 | HO- | C(=O)(C(F)(F)F)O | null | null | COC(=O)C(CCOc1ccc(N2CCN(c3ccncc3)CC2)cc1)NC(=O)OC(C)(C)C>C(=O)(C(F)(F)F)O>COC(=O)C(N)CCOc1ccc(N2CCN(c3ccncc3)CC2)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-b36ff282a19946cb9e1721c4f32fd0ac | CCO.O=C(O)COc1ccc(C(=O)CN2CCN(c3ccncc3)CC2=O)cc1>>CCOC(=O)COc1ccc(C(=O)CN2CCN(c3ccncc3)CC2=O)cc1 | N1=CC=C(C=C1)N1CC(N(CC1)CC(=O)C1=CC=C(OCC(=O)O)C=C1)=O.S(=O)(Cl)Cl.C(C)O>>N1=CC=C(C=C1)N1CC(N(CC1)CC(=O)C1=CC=C(OCC(=O)OCC)C=C1)=O | [CH3:1][CH2:2][OH:3].O[C:4](=[O:5])[CH2:6][O:7][c:8]1[cH:9][cH:10][c:11]([C:12](=[O:13])[CH2:14][N:15]2[CH2:16][CH2:17][N:18]([c:19]3[cH:20][cH:21][n:22][cH:23][cH:24]3)[CH2:25][C:26]2=[O:27])[cH:28][cH:29]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][O:7][c:8]1[cH:9][cH:10][c:11]([C:12](=[O:13])[CH2:14][N:15]2[CH2:16][CH... | CCO.O=C(O)COc1ccc(C(=O)CN2CCN(c3ccncc3)CC2=O)cc1 | CCOC(=O)COc1ccc(C(=O)CN2CCN(c3ccncc3)CC2=O)cc1 | null | null | null | Protection | Esterification of Carboxylic Acids | 070670f68a20c1021da94fabee54def4688122fb721af5f52cd5a03630845d0e | 0d8a72b7375d91aa7263e766e03a3cb7c4fa91e27abcd590409ff03b98eed690 | O=C(CN1CCN(c2ccncc2)CC1=O)c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[#8:4].[C;D1;H3:5]-[C:6]-[OH;D1;+0:7]>>[#8:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[O;H0;D2;+0:7]-[C:6]-[C;D1;H3:5] | null | [] | null | null | null | null | A crude sample of the product of Example 36 (3.4 g) was treated with a solution, at 0° C., made by adding thionyl chloride (2.25 g) dropwise to ethanol (45 ml) with stirring at below 0° C. The mixture was stirred at room temperature for 2 hours, heated at gentle reflux for 21/2 hours, and evaporated. The residue was tr... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary alcohol | Ester | null | null | c1ccccc1.C1C[NH]CC[NH]1.c1ccncc1 | HO- | null | null | null | CCO.O=C(O)COc1ccc(C(=O)CN2CCN(c3ccncc3)CC2=O)cc1>>CCOC(=O)COc1ccc(C(=O)CN2CCN(c3ccncc3)CC2=O)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-a15e323ae86247809988119f9d7b810a | Br.CCO.O=C1CC(Cc2ccccc2)CO1>>CCOC(=O)CC(Br)CCc1ccccc1 | C([O-])([O-])=O.[Na+].[Na+].Br.C(C1=CC=CC=C1)C1CC(=O)OC1.C(C)O.O>>C(C1=CC=CC=C1)CC(CC(=O)OCC)Br | [BrH:8].[CH3:1][CH2:2][OH:3].O1[C:4](=[O:5])[CH2:6][CH:7]([CH2:10][c:11]2[cH:12][cH:13][cH:14][cH:15][cH:16]2)[CH2:9]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][CH:7]([Br:8])[CH2:9][CH2:10][c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1 | Br.CCO.O=C1CC(Cc2ccccc2)CO1 | CCOC(=O)CC(Br)CCc1ccccc1 | null | null | null | Acylation | OtherReaction | e6d57e4979121bd97171788f69266800415ac2194f8a22ee644e1700d76bd3b5 | c37913cf10d0978a39cf88e0bd78595782663d17eb8a01f0d76920af32cf3d22 | c1ccccc1 | [BrH;D0;+0:1].[C;D1;H3:2]-[C:3]-[OH;D1;+0:4].[O;D1;H0:5]=[C;H0;D3;+0:6]1-O-[CH2;D2;+0:7]-[CH;D3;+0:8](-[CH2;D2;+0:9]-[c:10](:[c:11]):[c:12])-[C:13]-1>>[Br;H0;D1;+0:1]-[CH;D3;+0:8](-[C:13]-[C;H0;D3;+0:6](=[O;D1;H0:5])-[O;H0;D2;+0:4]-[C:3]-[C;D1;H3:2])-[CH2;D2;+0:7]-[CH2;D2;+0:9]-[c:10](:[c:11]):[c:12] | null | [] | null | null | 20 | HOUR | A solution of RS 3-benzylbutyrolactone (1.14 g) in ethanol (20 ml) was stirred at 5° C. and gassed for 4 hours with a slow stream of hydrogen bromide. The solution was kept at 5° C. for 20 hours and water (70 ml) added followed by sodium carbonate to neutralise the acid. The mixture was extracted with ethyl acetate and... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Primary alcohol | Secondary halide.Ester | C1CCOC1 | null | c1ccccc1 | HO- | null | null | 20 | Br.CCO.O=C1CC(Cc2ccccc2)CO1>>CCOC(=O)CC(Br)CCc1ccccc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-35c0a06e7c3d4c9f82f5835490d4df81 | Brc1ccc(OCc2ccccc2)cc1.O=C1CN(c2ccncc2)CCN1>>N.O=C1CN(c2ccncc2)CCN1c1ccc(OCc2ccccc2)cc1 | C(C1=CC=CC=C1)OC1=CC=C(C=C1)Br.N1=CC=C(C=C1)N1CC(NCC1)=O.[H-].[K+]>>N.C(C1=CC=CC=C1)OC1=CC=C(C=C1)N1C(CN(CC1)C1=CC=NC=C1)=O | Br[c:15]1[cH:16][cH:17][c:18]([O:19][CH2:20][c:21]2[cH:22][cH:23][cH:24][cH:25][cH:26]2)[cH:27][cH:28]1.[n:1]1[cH:8][cH:7][c:6]([N:5]2[CH2:4][C:3](=[O:2])[NH:14][CH2:13][CH2:12]2)[cH:11][cH:10]1>>[NH3:1].[O:2]=[C:3]1[CH2:4][N:5]([c:6]2[cH:7][cH:8][n:9][cH:10][cH:11]2)[CH2:12][CH2:13][N:14]1[c:15]1[cH:16][cH:17][c:18]([... | Brc1ccc(OCc2ccccc2)cc1.O=C1CN(c2ccncc2)CCN1 | N.O=C1CN(c2ccncc2)CCN1c1ccc(OCc2ccccc2)cc1 | null | [Cu]I | CN(C=O)C.[Cl-].[Na+].O.O | Functional Group Interconversion | Goldberg coupling | 194fc7bcf2b0c77d0d05fa51df46b479126eb6091c9681ac4e05786ff9ac1bbf | 5b40ff37472288821f196563d4810837d79fac64272cd0fd50b397a819a7c4b5 | O=C1CN(c2ccncc2)CCN1c1ccc(OCc2ccccc2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[O;D1;H0:6]=[C:7]1-[C:8]-[#7:9](-[c:10]2:[c:11]:[cH;D2;+0:12]:[n;H0;D2;+0:13]:[cH;D2;+0:14]:[c:15]:2)-[C:16]-[C:17]-[NH;D2;+0:18]-1>>[NH3;D0;+0:13].[O;D1;H0:6]=[C:7]1-[C:8]-[#7:9](-[c:10]2:[c:11]:[cH;D2;+0:12]:[#7;a:19]:[cH;D2;+0:14]:[c:15]:2)-[C:16]-[C:17]-[N;H0;D3;+0:18]-1-... | 123.3 | [{"value": 123.3, "product": "C(C1=CC=CC=C1)OC1=CC=C(C=C1)N1C(CN(CC1)C1=CC=NC=C1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 0.5 | HOUR | To a stirred suspension of 4-(4-pyridyl) piperazin-2-one (880 mg) in dimethyl formamide (20 ml) was added potassium hydride (1.0 ml of a 20% dispersion) and the mixture stirred for 0.5 hr, after which time was added copper (I) iodide (1.0 g). After 0.25 hr there was added 4-benzyloxybromobenzene (1.2 g) and the mixture... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amide | Tertiary amide | c1ccccc1.c1ccncc1.C1C[NH]CCN1 | C1C[NH]CC[NH]1.c1ccncc1.c1ccccc1 | C1C[NH]CC[NH]1.c1ccncc1.c1ccccc1.c1ccccc1 | null | [Cu]I.CN(C=O)C.[Cl-].[Na+].O.O | null | 0.5 | Brc1ccc(OCc2ccccc2)cc1.O=C1CN(c2ccncc2)CCN1>[Cu]I.CN(C=O)C.[Cl-].[Na+].O.O>N.O=C1CN(c2ccncc2)CCN1c1ccc(OCc2ccccc2)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-250c98292ed34b718eb34ce28332157b | Cc1ccc(S(=O)(=O)OC[C@H](C)CC(=O)OC(C)(C)C)cc1.Oc1ccc(N2CCN(c3ccncc3)CC2)cc1>>C[C@@H](COc1ccc(N2CCN(c3ccncc3)CC2)cc1)CC(=O)OC(C)(C)C | [H-].[Na+].N1=CC=C(C=C1)N1CCN(CC1)C1=CC=C(C=C1)O.C[C@H](CC(=O)OC(C)(C)C)COS(=O)(=O)C1=CC=C(C=C1)C>>C[C@H](CC(=O)OC(C)(C)C)COC1=CC=C(C=C1)N1CCN(CC1)C1=CC=NC=C1 | Cc1ccc(S(=O)(=O)O[CH2:3][C@H:2]([CH3:1])[CH2:23][C:24](=[O:25])[O:26][C:27]([CH3:28])([CH3:29])[CH3:30])cc1.[OH:4][c:5]1[cH:6][cH:7][c:8]([N:9]2[CH2:10][CH2:11][N:12]([c:13]3[cH:14][cH:15][n:16][cH:17][cH:18]3)[CH2:19][CH2:20]2)[cH:21][cH:22]1>>[CH3:1][C@@H:2]([CH2:3][O:4][c:5]1[cH:6][cH:7][c:8]([N:9]2[CH2:10][CH2:11][... | Cc1ccc(S(=O)(=O)OC[C@H](C)CC(=O)OC(C)(C)C)cc1.Oc1ccc(N2CCN(c3ccncc3)CC2)cc1 | C[C@@H](COc1ccc(N2CCN(c3ccncc3)CC2)cc1)CC(=O)OC(C)(C)C | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | OtherReaction | b5213736859cf91483a02f350869986d9b7674724716adef8a5d7a4bbdb79574 | 3d107e624e135e10014c7bf413dd0be27e1e4488f039e545b94cb1680b764158 | c1ccc(N2CCN(c3ccncc3)CC2)cc1 | C-c1:c:c:c(-S(=O)(=O)-O-[CH2;D2;+0:1]-[C:2](-[C;D1;H3:3])-[C:4]-[C:5](-[#8:6])=[O;D1;H0:7]):c:c:1.[OH;D1;+0:8]-[c:9](:[c:10]):[c:11]>>[#8:6]-[C:5](=[O;D1;H0:7])-[C:4]-[C:2](-[C;D1;H3:3])-[CH2;D2;+0:1]-[O;H0;D2;+0:8]-[c:9](:[c:10]):[c:11] | 42.4 | [{"value": 42.4, "product": "C[C@H](CC(=O)OC(C)(C)C)COC1=CC=C(C=C1)N1CCN(CC1)C1=CC=NC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 45 | MINUTE | Sodium hydride (60% dispersion in mineral oil, 2.44 g) was added to a stirred suspension of 4-[4-(4-pyridyl)piperazin-1-yl]phenol (15.5 g) in dry DMF (120 ml) and the mixture was stirred for 45 minutes at room temperature. tert-Butyl (3R)-3-methyl-4-(p-toluene-sulphonyloxy)butyrate (20 g) was added and the mixture was ... | 10.6084/m9.figshare.5104873.v1 | null | Tosylate.Aromatic alcohol | Ether | c1ccccc1 | null | c1ccccc1.C1C[NH]CC[NH]1.c1ccncc1 | TsOH.HO- | CN(C)C=O | null | 0.75 | Cc1ccc(S(=O)(=O)OC[C@H](C)CC(=O)OC(C)(C)C)cc1.Oc1ccc(N2CCN(c3ccncc3)CC2)cc1>CN(C)C=O>C[C@@H](COc1ccc(N2CCN(c3ccncc3)CC2)cc1)CC(=O)OC(C)(C)C |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-f546ef0358d64d9eb7bc59ad9f9555cd | C[C@H](CC(=O)OC(C)(C)C)C(=O)[O-]>>C[C@@H](CO)CC(=O)OC(C)(C)C | C[C@H](CC(=O)OC(C)(C)C)C(=O)[O-].C1CCOC1>>OC[C@@H](CC(=O)OC(C)(C)C)C | O=[C:3]([C@H:2]([CH3:1])[CH2:5][C:6](=[O:7])[O:8][C:9]([CH3:10])([CH3:11])[CH3:12])[O-:4]>>[CH3:1][C@@H:2]([CH2:3][OH:4])[CH2:5][C:6](=[O:7])[O:8][C:9]([CH3:10])([CH3:11])[CH3:12] | C[C@H](CC(=O)OC(C)(C)C)C(=O)[O-] | C[C@@H](CO)CC(=O)OC(C)(C)C | null | null | CO | Reduction | OtherReaction | 3ee00ae8302f5a9cabfd43f47c90c2bc696c7c0e2b77ca13873c453d0520692e | c2c13922fe3c9358e6ba38897f2383764691ea247b267e6643408d03716a3879 | null | O=[C;H0;D3;+0:1](-[O-;H0;D1:2])-[C:3](-[C;D1;H3:4])-[C:5]-[C:6](-[#8:7])=[O;D1;H0:8]>>[#8:7]-[C:6](=[O;D1;H0:8])-[C:5]-[C:3](-[C;D1;H3:4])-[CH2;D2;+0:1]-[OH;D1;+0:2] | 91.6 | [{"value": 91.6, "product": "OC[C@@H](CC(=O)OC(C)(C)C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -10 | CELSIUS | 30 | MINUTE | Borane-dimethyl sulphide complex (10M, 10.3 ml) was added during 15 minutes to a stirred mixture of 1-tert-butyl (3R)-3-methylsuccinate (12.9 g) and THF (200 ml) which had been cooled to -10° C. and placed under an atmosphere of argon. The mixture was stirred at -10° C. for 30 minutes. The mixture was allowed to warm t... | 10.6084/m9.figshare.5104873.v1 | null | null | Primary alcohol | null | null | null | Other | CO | -10 | 0.5 | C[C@H](CC(=O)OC(C)(C)C)C(=O)[O-]>CO>C[C@@H](CO)CC(=O)OC(C)(C)C |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-5075b6fc94804d6986741814d1b8f075 | C[C@@H](CO)CC(=O)OC(C)(C)C.Cc1ccc(S(=O)(=O)Cl)cc1>>Cc1ccc(S(=O)(=O)OC[C@H](C)CC(=O)OC(C)(C)C)cc1 | C1(=CC=C(C=C1)S(=O)(=O)Cl)C.OC[C@@H](CC(=O)OC(C)(C)C)C.C(C)N(CC)CC>>C[C@H](CC(=O)OC(C)(C)C)COS(=O)(=O)C1=CC=C(C=C1)C | [OH:9][CH2:10][C@H:11]([CH3:12])[CH2:13][C:14](=[O:15])[O:16][C:17]([CH3:18])([CH3:19])[CH3:20].Cl[S:6]([c:5]1[cH:4][cH:3][c:2]([CH3:1])[cH:22][cH:21]1)(=[O:7])=[O:8]>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([S:6](=[O:7])(=[O:8])[O:9][CH2:10][C@H:11]([CH3:12])[CH2:13][C:14](=[O:15])[O:16][C:17]([CH3:18])([CH3:19])[CH3:20])[cH:2... | C[C@@H](CO)CC(=O)OC(C)(C)C.Cc1ccc(S(=O)(=O)Cl)cc1 | Cc1ccc(S(=O)(=O)OC[C@H](C)CC(=O)OC(C)(C)C)cc1 | null | null | ClCCl | Acylation | Formation of Sulfonic Esters | d05d91207659f8fa672c205a316a670adfe2b92492fc9adad2ee3f241e574fb9 | a7748b0f3b0eba3868d0cf03ae67721db046202accaaea9cadb4edbc96ec8768 | c1ccccc1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6].[C:7]-[C:8]-[OH;D1;+0:9]>>[C:7]-[C:8]-[O;H0;D2;+0:9]-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6] | 96.5 | [{"value": 96.5, "product": "C[C@H](CC(=O)OC(C)(C)C)COS(=O)(=O)C1=CC=C(C=C1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 20 | HOUR | p-Toluenesulphonyl chloride (13.2 g) was added portionwise to a stirred mixture of tert-butyl (3R)-4-hydroxy-3-methylbutyrate (11 g), triethylamine (21 ml) and dichloromethane (120 ml) and the mixture was stirred at room temperature for 20 hours. The mixture was washed in turn with water and with a dilute aqueous sodiu... | 10.6084/m9.figshare.5104873.v1 | null | Tosylate.Primary alcohol.Sulfonyl halide | Tosylate | null | null | c1ccccc1 | HCl | ClCCl | null | 20 | C[C@@H](CO)CC(=O)OC(C)(C)C.Cc1ccc(S(=O)(=O)Cl)cc1>ClCCl>Cc1ccc(S(=O)(=O)OC[C@H](C)CC(=O)OC(C)(C)C)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-81e816ae13fd471baa1f76ede4d59949 | CC1=CC(=O)OC1=O.Nc1cccc(N)c1>>C/C(=C/C(=O)Nc1cccc(NC(=O)/C=C(/C)C(=O)O)c1)C(=O)O | C1(=CC(=CC=C1)N)N.C1(\C(\C)=C/C(=O)O1)=O>>C1(=CC(=CC=C1)NC(\C=C(/C(=O)O)\C)=O)NC(\C=C(/C(=O)O)\C)=O | [O:5]=[C:13]1[CH:15]=[C:16]([CH3:17])[C:18](=[O:20])[O:24]1.[cH:1]1[c:2]([NH2:6])[cH:21][c:11]([NH2:12])[cH:10][cH:9]1>>[CH3:1]/[C:2](=[CH:3]/[C:4](=[O:5])[NH:6][c:7]1[cH:8][cH:9][cH:10][c:11]([NH:12][C:13](=[O:14])/[CH:15]=[C:16](/[CH3:17])[C:18](=[O:19])[OH:20])[cH:21]1)[C:22](=[O:23])[OH:24] | CC1=CC(=O)OC1=O.Nc1cccc(N)c1 | C/C(=C/C(=O)Nc1cccc(NC(=O)/C=C(/C)C(=O)O)c1)C(=O)O | null | null | CC(=O)C | Functional Group Addition | OtherReaction | 731d10442574b1716b47b633060839a85a4097e88abb4841b4c7b5b3e1238dd7 | 69e8b0089afd77ed84408d90076e19214e551e9a287635195f085a236f7820ef | c1ccccc1 | [C;D1;H3:1]-[C:2]1=[C:3]-[C;H0;D3;+0:4](=[O;H0;D1;+0:5])-[O;H0;D2;+0:6]-[C;H0;D3;+0:7]-1=[O;H0;D1;+0:8].[NH2;D1;+0:9]-[c:10]1:[c:11]:[cH;D2;+0:12]:[cH;D2;+0:13]:[c;H0;D3;+0:14](-[NH2;D1;+0:15]):[cH;D2;+0:16]:1>>[C;D1;H3:1]/[C:2](=[C:3]/[C;H0;D3;+0:4](=[O;D1;H0:17])-[NH;D2;+0:9]-[c:10]1:[c:11]:[cH;D2;+0:12]:[c:18]:[c:19... | 99.9 | [{"value": 99.9, "product": "C1(=CC(=CC=C1)NC(\\C=C(/C(=O)O)\\C)=O)NC(\\C=C(/C(=O)O)\\C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A 3-liter, 3-neck round bottom flask was charged with 54 g (0.5 mole) of m-phenylenediamine and 500 ml of reagent acetone and flushed with nitrogen. The flask was fitted with a reflux condenser, mechanical stirrer and thermocouple. A dropping funnel containing 112 g (1.0 mole) of citraconic anhydride in 500 ml of reage... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Primary amine.Primary amine | Carboxylic acid.Carboxylic acid.Secondary amide.Secondary amide | C1=CCOC1.c1ccccc1 | c1ccccc1 | c1ccccc1 | Other | CC(=O)C | null | null | CC1=CC(=O)OC1=O.Nc1cccc(N)c1>CC(=O)C>C/C(=C/C(=O)Nc1cccc(NC(=O)/C=C(/C)C(=O)O)c1)C(=O)O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-f9e0a5c87bd84b7d80805188d5773375 | O=C1CCCCCO1>>O=C1CCCCCO1 | C1(CCCCCO1)=O.C[C@H]1C(=O)O[C@H](C(=O)O1)C.OCC(O)CO.CCCCC(CC)C(=O)[O-].CCCCC(CC)C(=O)[O-].[Sn+2]>>C1(CCCCCO1)=O.C[C@H]1C(=O)O[C@H](C(=O)O1)C | [O:11]=[C:12]1[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][O:18]1>>[O:11]=[C:12]1[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][O:18]1 | O=C1CCCCCO1 | O=C1CCCCCO1 | null | null | C1(=CC=CC=C1)C | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | O=C1CCCCCO1 | null | null | [] | 160 | CELSIUS | null | null | A flame dried, 250 mL, round bottom single neck flask was charged with 57.1 grams (0.50 mole) of ε-caprolactone, 72.1 grams (0.50 mole) of L-lactide, 4.00 mL (55 mmol) of distilled glycerol, and 0.10 mL (34 μmol) of a 0.33M stannous octoate solution in toluene. The flask was fitted with a flame dried mechanical stirrer... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | C1CCCOCC1 | null | C1(=CC=CC=C1)C | 160 | null | O=C1CCCCCO1>C1(=CC=CC=C1)C>O=C1CCCCCO1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-32f23f9ca43c4245993689b694a4b02b | CCCCC(CC)C(=O)[O-].CCCCC(CC)C(=O)[O-].CCCCCCCCCCCCO>>C[C@@H]1OC(=O)[C@H](C)OC1=O.O=C1CCCCCO1 | C(CCCCCCCCCCC)O.CCCCC(CC)C(=O)[O-].CCCCC(CC)C(=O)[O-].[Sn+2]>>C1(CCCCCO1)=O.C[C@H]1C(=O)O[C@H](C(=O)O1)C | C[CH2:7][CH:6](CCC[CH3:1])[C:4]([O-:3])=[O:5].CCCC[CH:2](CC)[C:9]([O-:8])=[O:10].CCCCCC[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][OH:18]>>[CH3:1][C@@H:2]1[O:3][C:4](=[O:5])[C@H:6]([CH3:7])[O:8][C:9]1=[O:10].[O:11]=[C:12]1[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][O:18]1 | CCCCC(CC)C(=O)[O-].CCCCC(CC)C(=O)[O-].CCCCCCCCCCCCO | C[C@@H]1OC(=O)[C@H](C)OC1=O.O=C1CCCCCO1 | null | null | null | Acylation | OtherReaction | 6cccf0b9f642cd3e374306b6d5d57d27cd4fe3f9f21f1534dc18d386bcb60164 | ca90d29787421863cb0619ee110100129b2d7d43de5cf379383215c2224dfccb | O=C1CCCCCO1.O=C1COC(=O)CO1 | C-C-C-C-C-C-[CH2;D2;+0:1]-[C:2]-[C:3].[C:4]-[C:5]-[OH;D1;+0:6].C-C-C-C-[CH;D3;+0:7](-C-C)-[C:8](-[O-;H0;D1:9])=[O;D1;H0:10].C-[CH2;D2;+0:11]-[CH;D3;+0:12](-C-C-C-[CH3;D1;+0:13])-[C:14](-[O-;H0;D1:15])=[O;D1;H0:16]>>[CH3;D1;+0:13]-[C@@H;D3;+0:7]1-[O;H0;D2;+0:15]-[C:14](=[O;D1;H0:16])-[C@H;D3;+0:12](-[CH3;D1;+0:11])-[O;H... | null | [] | null | null | null | null | The procedure in Example 1 was substantially repeated, except that 13.6 mL of 1-dodecanol instead of 4.00 mL of glycerol and 0.12 mL (40 μmol) instead of 0.10 mL of stannous octoate solution were used. The copolymer was dried under vacuum (0.1mm Hg) at 110° C. for about 16 hours to remove any unreacted monomer. The cop... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | Ester.Ester.Ester | null | C1COCCO1.C1CCCOCC1 | C1COCCO1.C1CCCOCC1 | Other | null | null | null | CCCCC(CC)C(=O)[O-].CCCCC(CC)C(=O)[O-].CCCCCCCCCCCCO>>C[C@@H]1OC(=O)[C@H](C)OC1=O.O=C1CCCCCO1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-e82a49eb230f455cbaf06730dd7d2f50 | CC(O)CO>>C[C@@H]1OC(=O)[C@H](C)OC1=O.O=C1CCCCCO1 | C(C(C)O)O>>C1(CCCCCO1)=O.C[C@H]1C(=O)O[C@H](C(=O)O1)C | [CH3:1][CH:2]([OH:3])[CH2:4][OH:5]>>[CH3:1][C@@H:2]1[O:3][C:4](=[O:5])[C@H:6]([CH3:7])[O:8][C:9]1=[O:10].[O:11]=[C:12]1[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][O:18]1 | CC(O)CO | C[C@@H]1OC(=O)[C@H](C)OC1=O.O=C1CCCCCO1 | null | null | C(C(F)(F)F)(C(F)(F)F)O | Heteroatom Alkylation and Arylation | OtherReaction | 1e2cd8ff1bd49e184ccd7881283329b37e5e9d4d1dbd18b48b1dc621f0c52cab | 743ddb0b329b42b92fa080d7d63498ec1d2fe019efcc27e8df26c2f76e6fd71b | O=C1CCCCCO1.O=C1COC(=O)CO1 | [C;D1;H3:1]-[CH;D3;+0:2](-[OH;D1;+0:3])-[CH2;D2;+0:4]-[OH;D1;+0:5]>>[C;D1;H3:1]-[C@@H;D3;+0:2]1-[O;H0;D2;+0:3]-[C;H0;D3;+0:4](=[O;H0;D1;+0:5])-[C:6](-[C;D1;H3:7])-[#8:8]-[C:9]-1=[O;D1;H0:10] | null | [] | null | null | null | null | The procedure in Example 3 was substantially repeated, except that 4.4 mL (60 mmol) propylene glycol (USP grade) was used instead of 5.6 mL of 1-dodecanol. The copolymer had an inherent viscosity of 0.17 dL/g in HFIP at 25° C.
Conditions: See reaction.notes.procedure_details.
Workup: at 25° C. | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Secondary alcohol | Ester.Ester.Ester | null | C1COCCO1.C1CCCOCC1 | C1COCCO1.C1CCCOCC1 | Other | C(C(F)(F)F)(C(F)(F)F)O | null | null | CC(O)CO>C(C(F)(F)F)(C(F)(F)F)O>C[C@@H]1OC(=O)[C@H](C)OC1=O.O=C1CCCCCO1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-2f67cb89cb8f4479a6231aded45cb5b0 | O=C1COCCO1>>O=C1COCCO1 | C1(CCCCCO1)=O.O1C(COCC1)=O.OCC(O)CO.CCCCC(CC)C(=O)[O-].CCCCC(CC)C(=O)[O-].[Sn+2]>>C1(CCCCCO1)=O.O1C(COCC1)=O | [O:9]=[C:10]1[CH2:11][O:12][CH2:13][CH2:14][O:15]1>>[O:9]=[C:10]1[CH2:11][O:12][CH2:13][CH2:14][O:15]1 | O=C1COCCO1 | O=C1COCCO1 | null | null | C1(=CC=CC=C1)C | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | O=C1COCCO1 | null | null | [] | 140 | CELSIUS | null | null | A flame dried, 250 mL, round bottom single neck flask was charged with 57.1 grams (0.50 mole) of ε-caprolactone, 51.0 grams (0.50 mole) of p-dioxanone, 4.00 mL (55 mmol) of distilled glycerol, and 0.12 mL (40 μmol) of a 0.33M stannous octoate solution in toluene. The flask was fitted with a flame dried mechanical stirr... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | C1COCCO1 | null | C1(=CC=CC=C1)C | 140 | null | O=C1COCCO1>C1(=CC=CC=C1)C>O=C1COCCO1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-1ec4e94fc0484fc2880ad3dbed35b55d | O=C1COCCO1>>O=C1COCCO1 | C1(CCCCCO1)=O.O1C(COCC1)=O.C(C(C)O)O.CCCCC(CC)C(=O)[O-].CCCCC(CC)C(=O)[O-].[Sn+2]>>C1(CCCCCO1)=O.O1C(COCC1)=O | [O:9]=[C:10]1[CH2:11][O:12][CH2:13][CH2:14][O:15]1>>[O:9]=[C:10]1[CH2:11][O:12][CH2:13][CH2:14][O:15]1 | O=C1COCCO1 | O=C1COCCO1 | null | null | C1(=CC=CC=C1)C | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | O=C1COCCO1 | null | null | [] | 140 | CELSIUS | null | null | A flame dried, 250 mL, round bottom single neck flask was charged with 57.1 g (0.50 mole) of ε-caprolactone, 51.0 grams (0.50 mole) of p-dioxanone, 3.7 mL (50 mmol) of propylene glycol (USP), and 0.12 mL (34 μmol) of a 0.33M stannous octoate solution in toluene. The flask was fitted with a flame dried mechanical stirre... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | C1COCCO1 | null | C1(=CC=CC=C1)C | 140 | null | O=C1COCCO1>C1(=CC=CC=C1)C>O=C1COCCO1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-d7d2ca3c29b649f5856b09db139c04ce | O=C1COCCO1>>O=C1COCCO1 | C1(CCCCCO1)=O.O1C(COCC1)=O>>C1(CCCCCO1)=O.O1C(COCC1)=O | [O:9]=[C:10]1[CH2:11][O:12][CH2:13][CH2:14][O:15]1>>[O:9]=[C:10]1[CH2:11][O:12][CH2:13][CH2:14][O:15]1 | O=C1COCCO1 | O=C1COCCO1 | null | null | null | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | O=C1COCCO1 | null | null | [] | null | null | null | null | The procedure in Example 5A was substantially repeated, except that 68.48 grams (0.60 mole) of ε-caprolactone and 40.83 grams (0.40 mole) of p-dioxanone were used. The copolymer was dried under vacuum (0.1 mm Hg) at 80° C. for about 80 hours to remove any unreacted monomer. The copolymer had an inherent viscosity of 0.... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | C1COCCO1 | null | null | null | null | O=C1COCCO1>>O=C1COCCO1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-38955b7c995840b4ae3dced0500d7938 | O=C1COCCO1>>O=C1COCCO1 | C1(CCCCCO1)=O.O1C(COCC1)=O>>C1(CCCCCO1)=O.O1C(COCC1)=O | [O:9]=[C:10]1[CH2:11][O:12][CH2:13][CH2:14][O:15]1>>[O:9]=[C:10]1[CH2:11][O:12][CH2:13][CH2:14][O:15]1 | O=C1COCCO1 | O=C1COCCO1 | null | null | null | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | O=C1COCCO1 | null | null | [] | null | null | null | null | The procedure in Example 5A is substantially repeated except that 45.7 grams (0.40 mole) of ε-caprolactone and 61.3 grams (0.60 mole) of p-dioxanone were used. The copolymer was dried under vacuum (0.1 mm Hg) at 80° C. for about 80 hours to remove any unreacted monomer. The copolymer had an inherent viscosity of 0.18 d... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | C1COCCO1 | null | null | null | null | O=C1COCCO1>>O=C1COCCO1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-a39ac505275c4aed98cfeb34fa86c787 | O=C1OCCCO1>>O=C1OCCCO1 | C1(CCCCCO1)=O.C1(OCCCO1)=O.C(C(C)O)O.CCCCC(CC)C(=O)[O-].CCCCC(CC)C(=O)[O-].[Sn+2]>>C1(CCCCCO1)=O.C1(OCCCO1)=O | [O:9]=[C:10]1[O:11][CH2:12][CH2:13][CH2:14][O:15]1>>[O:9]=[C:10]1[O:11][CH2:12][CH2:13][CH2:14][O:15]1 | O=C1OCCCO1 | O=C1OCCCO1 | null | null | C1(=CC=CC=C1)C | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | O=C1OCCCO1 | null | null | [] | 160 | CELSIUS | null | null | A flame dried, 250 mL, round bottom single neck flask was charged with 57.1 grams (0.50 mole) of ε-caprolactone, 51.0 grams (0.50 mole) of trimethylene carbonate, 4.4 mL (60mmol) of propylene glycol (USP), and 0.10 mL (34 μmol) of a 0.33M solution of stannous octoate in toluene. The flask was fitted with a flame dried ... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | C1COCOC1 | null | C1(=CC=CC=C1)C | 160 | null | O=C1OCCCO1>C1(=CC=CC=C1)C>O=C1OCCCO1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-8ed745f48d774f70a727a25216a3f78b | O=C1OCCCO1>>O=C1OCCCO1 | C1(CCCCCO1)=O.C1(OCCCO1)=O.C(C(C)O)O.CCCCC(CC)C(=O)[O-].CCCCC(CC)C(=O)[O-].[Sn+2]>>C1(CCCCCO1)=O.C1(OCCCO1)=O | [O:9]=[C:10]1[O:11][CH2:12][CH2:13][CH2:14][O:15]1>>[O:9]=[C:10]1[O:11][CH2:12][CH2:13][CH2:14][O:15]1 | O=C1OCCCO1 | O=C1OCCCO1 | null | null | C1(=CC=CC=C1)C | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | O=C1OCCCO1 | null | null | [] | 160 | CELSIUS | null | null | A flame dried, 250 mL, round bottom single neck flask was charged with 102.7 grams (0.90 mole) of ε-caprolactone, 10.2 grams (0.10 mole) of trimethylene carbonate, 2.9 mL (40 mmol) of propylene glycol (USP), and 0.10 mL (34 μmol) of a 0.33M stannous octoate solution in toluene. The flask was fitted with a flame dried m... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | C1COCOC1 | null | C1(=CC=CC=C1)C | 160 | null | O=C1OCCCO1>C1(=CC=CC=C1)C>O=C1OCCCO1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-68b5d1780faa448bb947e87b6999fd2f | COc1cccc(Oc2c(Cl)ncnc2NS(=O)(=O)c2ccc(C(C)(C)C)cc2)c1.OCc1ccccn1>>COc1cccc(Oc2c(NS(=O)(=O)c3ccc(C(C)(C)C)cc3)ncnc2OCc2ccccn2)c1 | [Cl-].[NH4+].C(C)(C)(C)C1=CC=C(C=C1)S(=O)(=O)NC1=NC=NC(=C1OC1=CC(=CC=C1)OC)Cl.N1=C(C=CC=C1)CO.[H-].[Na+]>>C(C)(C)(C)C1=CC=C(C=C1)S(=O)(=O)NC1=NC=NC(=C1OC1=CC(=CC=C1)OC)OCC1=NC=CC=C1 | Cl[c:28]1[c:9]([O:8][c:7]2[cH:6][cH:5][cH:4][c:3]([O:2][CH3:1])[cH:37]2)[c:10]([NH:11][S:12](=[O:13])(=[O:14])[c:15]2[cH:16][cH:17][c:18]([C:19]([CH3:20])([CH3:21])[CH3:22])[cH:23][cH:24]2)[n:25][cH:26][n:27]1.[OH:29][CH2:30][c:31]1[cH:32][cH:33][cH:34][cH:35][n:36]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]([O:8][c:9... | COc1cccc(Oc2c(Cl)ncnc2NS(=O)(=O)c2ccc(C(C)(C)C)cc2)c1.OCc1ccccn1 | COc1cccc(Oc2c(NS(=O)(=O)c3ccc(C(C)(C)C)cc3)ncnc2OCc2ccccn2)c1 | null | null | CC(=O)N(C)C | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | a445000eb5ed501274d93689ad5b9d45095af02deca02b6b541c8a834890a276 | a4cafa7bcd156e21cca6eaac1b32e28ec8540642a31181122e6957f3d7559631 | O=S(=O)(Nc1ncnc(OCc2ccccn2)c1Oc1ccccc1)c1ccccc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](-[#7:6]):[c:7]:1-[#8:8].[#7;a:9]:[c:10]-[C:11]-[OH;D1;+0:12]>>[#7:6]-[c:5]1:[#7;a:4]:[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[O;H0;D2;+0:12]-[C:11]-[c:10]:[#7;a:9]):[c:7]:1-[#8:8] | 94.6 | [{"value": 94.6, "product": "C(C)(C)(C)C1=CC=C(C=C1)S(=O)(=O)NC1=NC=NC(=C1OC1=CC(=CC=C1)OC)OCC1=NC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a stirred solution of pyridine-2-methanol (130 mg) in dimethylacetamide (0.5 ml) is added gradually with stirring sodium hydride (62.7% dispersion-type, 60 mg) under ice-cooling, and thereto is added 4-tert-butyl-N-{6-chloro-5-(3-methoxyphenoxy)pyrimidin-4-yl}benzenesulfonamide (100 mg). The mixture is reacted at 10... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary alcohol | Ether | c1cncnc1 | c1cncnc1 | c1ccccc1.c1ccccc1.c1cncnc1.c1ccncc1 | HCl | CC(=O)N(C)C | null | null | COc1cccc(Oc2c(Cl)ncnc2NS(=O)(=O)c2ccc(C(C)(C)C)cc2)c1.OCc1ccccn1>CC(=O)N(C)C>COc1cccc(Oc2c(NS(=O)(=O)c3ccc(C(C)(C)C)cc3)ncnc2OCc2ccccn2)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-4a09bd49475f4cefbcfd376d11afcf86 | COc1cccc(Oc2c(Cl)ncnc2NS(=O)(=O)c2ccc(C(C)(C)C)cc2)c1.NCCO>>COc1cccc(Oc2c(NS(=O)(=O)c3ccc(C(C)(C)C)cc3)ncnc2OCCN)c1 | C(C)(C)(C)C1=CC=C(C=C1)S(=O)(=O)NC1=NC=NC(=C1OC1=CC(=CC=C1)OC)Cl.NCCO.Cl>>Cl.NCCOC1=C(C(=NC=N1)NS(=O)(=O)C1=CC=C(C=C1)C(C)(C)C)OC1=CC(=CC=C1)OC | Cl[c:28]1[c:9]([O:8][c:7]2[cH:6][cH:5][cH:4][c:3]([O:2][CH3:1])[cH:33]2)[c:10]([NH:11][S:12](=[O:13])(=[O:14])[c:15]2[cH:16][cH:17][c:18]([C:19]([CH3:20])([CH3:21])[CH3:22])[cH:23][cH:24]2)[n:25][cH:26][n:27]1.[OH:29][CH2:30][CH2:31][NH2:32]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]([O:8][c:9]2[c:10]([NH:11][S:12](=[O... | COc1cccc(Oc2c(Cl)ncnc2NS(=O)(=O)c2ccc(C(C)(C)C)cc2)c1.NCCO | COc1cccc(Oc2c(NS(=O)(=O)c3ccc(C(C)(C)C)cc3)ncnc2OCCN)c1 | null | null | null | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | a445000eb5ed501274d93689ad5b9d45095af02deca02b6b541c8a834890a276 | a4cafa7bcd156e21cca6eaac1b32e28ec8540642a31181122e6957f3d7559631 | O=S(=O)(Nc1ncncc1Oc1ccccc1)c1ccccc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](-[#7:6]):[c:7]:1-[#8:8].[C:9]-[C:10]-[OH;D1;+0:11]>>[#7:6]-[c:5]1:[#7;a:4]:[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[O;H0;D2;+0:11]-[C:10]-[C:9]):[c:7]:1-[#8:8] | null | [] | null | null | null | null | After treating 4-tert-butyl-N-{6-chloro-5-(3-methoxyphenoxy)-pyrimidin-4-yl}benzenesulfonamide and 2-aminoethanol in the same manner as in Example 1, the precipitated crystals are converted into a hydrochloride thereof to give N-{6-(2-aminoethoxy)-5-(3-methoxyphenoxy)pyrimidin-4-yl}-4-tert-butylbenzenesulfonamide hydro... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary alcohol | Ether | c1cncnc1 | c1cncnc1 | c1ccccc1.c1ccccc1.c1cncnc1 | HCl | null | null | null | COc1cccc(Oc2c(Cl)ncnc2NS(=O)(=O)c2ccc(C(C)(C)C)cc2)c1.NCCO>>COc1cccc(Oc2c(NS(=O)(=O)c3ccc(C(C)(C)C)cc3)ncnc2OCCN)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-1febdfb0ad8749368c5d7d698e941579 | COc1cccc(Oc2c(NS(=O)(=O)c3ccc(C(C)(C)C)cc3)ncnc2OCCN)c1.Clc1ncccn1>>COc1cccc(Oc2c(NS(=O)(=O)c3ccc(C(C)(C)C)cc3)ncnc2OCCNc2ncccn2)c1.O | Cl.NCCOC1=C(C(=NC=N1)NS(=O)(=O)C1=CC=C(C=C1)C(C)(C)C)OC1=CC(=CC=C1)OC.ClC1=NC=CC=N1.C([O-])([O-])=O.[K+].[K+].CC(=O)N(C)C>>O.C(C)(C)(C)C1=CC=C(C=C1)S(=O)(=O)NC1=NC=NC(=C1OC1=CC(=CC=C1)OC)OCCNC1=NC=CC=N1 | [CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]([O:8][c:9]2[c:10]([NH:11][S:12](=[O:13])(=[O:14])[c:15]3[cH:16][cH:17][c:18]([C:19]([CH3:20])([CH3:21])[CH3:22])[cH:23][cH:24]3)[n:25][cH:26][n:27][c:28]2[O:29][CH2:30][CH2:31][NH2:32])[cH:39]1.Cl[c:33]1[n:34][cH:35][cH:36][cH:37][n:38]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:... | COc1cccc(Oc2c(NS(=O)(=O)c3ccc(C(C)(C)C)cc3)ncnc2OCCN)c1.Clc1ncccn1 | COc1cccc(Oc2c(NS(=O)(=O)c3ccc(C(C)(C)C)cc3)ncnc2OCCNc2ncccn2)c1.O | null | null | [Cl-].[NH4+] | Functional Group Interconversion | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | 819da00fc6cb7676e29b4c340e48014f8125618f87ac9035ea24e0c0aad0a9ee | a1c7958c0cedc0c150503c125707207ca303828b91d8ab1f136970a3b0c29de0 | O=S(=O)(Nc1ncnc(OCCNc2ncccn2)c1Oc1ccccc1)c1ccccc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5].[C:6]-[C:7]-[NH2;D1;+0:8]>>[C:6]-[C:7]-[NH;D2;+0:8]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5] | 161.1 | [{"value": 161.1, "product": "O.C(C)(C)(C)C1=CC=C(C=C1)S(=O)(=O)NC1=NC=NC(=C1OC1=CC(=CC=C1)OC)OCCNC1=NC=CC=N1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | 3 | DAY | A mixture of Compound A (150 mg), 2-chloropyrimidine (61 mg), potassium carbonate (122 mg) and dimethylacetamide (1.5 ml) is heated with stirring at 100° C. for three days. The reaction solution is diluted with aqueous ammonium chloride solution, and extracted with ethyl acetate. The extract is washed and dried. The so... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1ccccc1.c1ccccc1.c1cncnc1.c1cncnc1 | null | [Cl-].[NH4+] | 100 | 72 | COc1cccc(Oc2c(NS(=O)(=O)c3ccc(C(C)(C)C)cc3)ncnc2OCCN)c1.Clc1ncccn1>[Cl-].[NH4+]>COc1cccc(Oc2c(NS(=O)(=O)c3ccc(C(C)(C)C)cc3)ncnc2OCCNc2ncccn2)c1.O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-0320d2dcb5ab4ee2ac21fd0fa0ec9edb | COc1cccc(Oc2c(NCCO)ncnc2NS(=O)(=O)c2ccc(C(C)(C)C)cc2)c1.Clc1ncccn1>>COc1cccc(Oc2c(NCCOc3ncccn3)ncnc2NS(=O)(=O)c2ccc(C(C)(C)C)cc2)c1 | [Cl-].[NH4+].ClC1=NC=CC=N1.C(C)(C)(C)C1=CC=C(C=C1)S(=O)(=O)NC1=NC=NC(=C1OC1=CC(=CC=C1)OC)NCCO.[H-].[Na+]>>C(C)(C)(C)C1=CC=C(C=C1)S(=O)(=O)NC1=NC=NC(=C1OC1=CC(=CC=C1)OC)NCCOC1=NC=CC=N1 | [CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]([O:8][c:9]2[c:10]([NH:11][CH2:12][CH2:13][OH:14])[n:21][cH:22][n:23][c:24]2[NH:25][S:26](=[O:27])(=[O:28])[c:29]2[cH:30][cH:31][c:32]([C:33]([CH3:34])([CH3:35])[CH3:36])[cH:37][cH:38]2)[cH:39]1.Cl[c:15]1[n:16][cH:17][cH:18][cH:19][n:20]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:... | COc1cccc(Oc2c(NCCO)ncnc2NS(=O)(=O)c2ccc(C(C)(C)C)cc2)c1.Clc1ncccn1 | COc1cccc(Oc2c(NCCOc3ncccn3)ncnc2NS(=O)(=O)c2ccc(C(C)(C)C)cc2)c1 | null | null | CC(=O)N(C)C | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | a445000eb5ed501274d93689ad5b9d45095af02deca02b6b541c8a834890a276 | a4cafa7bcd156e21cca6eaac1b32e28ec8540642a31181122e6957f3d7559631 | O=S(=O)(Nc1ncnc(NCCOc2ncccn2)c1Oc1ccccc1)c1ccccc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5].[C:6]-[C:7]-[OH;D1;+0:8]>>[C:6]-[C:7]-[O;H0;D2;+0:8]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5] | 92.5 | [{"value": 92.5, "product": "C(C)(C)(C)C1=CC=C(C=C1)S(=O)(=O)NC1=NC=NC(=C1OC1=CC(=CC=C1)OC)NCCOC1=NC=CC=N1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | To a solution of Compound B (116 mg) obtained in Example 19-(1) in dimethylacetamide (2 ml) is added sodium hydride (60% dispersion-type, 33 mg), and thereto is added 2-chloropyrimidine (40 mg). The reaction solution is stirred at room temperature overnight, and the mixture is treated with saturated aqueous ammonium ch... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary alcohol | Ether | c1cncnc1 | c1cncnc1 | c1ccccc1.c1cncnc1.c1cncnc1.c1ccccc1 | HCl | CC(=O)N(C)C | null | 8 | COc1cccc(Oc2c(NCCO)ncnc2NS(=O)(=O)c2ccc(C(C)(C)C)cc2)c1.Clc1ncccn1>CC(=O)N(C)C>COc1cccc(Oc2c(NCCOc3ncccn3)ncnc2NS(=O)(=O)c2ccc(C(C)(C)C)cc2)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-46d9d32e459846fbbd2041dd10adb17e | COc1cccc(Oc2c(NS(=O)(=O)c3ccc(C(C)(C)C)cc3)ncnc2OCCO)c1.Clc1ncc(Br)cn1>>COc1cccc(Oc2c(NS(=O)(=O)c3ccc(C(C)(C)C)cc3)ncnc2OCCOc2ncc(Br)cn2)c1 | C(C)(C)(C)C1=CC=C(C=C1)S(=O)(=O)NC1=NC=NC(=C1OC1=CC(=CC=C1)OC)OCCO.[H-].[Na+].[Cl-].[NH4+].BrC=1C=NC(=NC1)Cl>>BrC=1C=NC(=NC1)OCCOC1=C(C(=NC=N1)NS(=O)(=O)C1=CC=C(C=C1)C(C)(C)C)OC1=CC(=CC=C1)OC | [CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]([O:8][c:9]2[c:10]([NH:11][S:12](=[O:13])(=[O:14])[c:15]3[cH:16][cH:17][c:18]([C:19]([CH3:20])([CH3:21])[CH3:22])[cH:23][cH:24]3)[n:25][cH:26][n:27][c:28]2[O:29][CH2:30][CH2:31][OH:32])[cH:40]1.Cl[c:33]1[n:34][cH:35][c:36]([Br:37])[cH:38][n:39]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c... | COc1cccc(Oc2c(NS(=O)(=O)c3ccc(C(C)(C)C)cc3)ncnc2OCCO)c1.Clc1ncc(Br)cn1 | COc1cccc(Oc2c(NS(=O)(=O)c3ccc(C(C)(C)C)cc3)ncnc2OCCOc2ncc(Br)cn2)c1 | null | null | CC(=O)N(C)C | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | a445000eb5ed501274d93689ad5b9d45095af02deca02b6b541c8a834890a276 | a4cafa7bcd156e21cca6eaac1b32e28ec8540642a31181122e6957f3d7559631 | O=S(=O)(Nc1ncnc(OCCOc2ncccn2)c1Oc1ccccc1)c1ccccc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5].[C:6]-[C:7]-[OH;D1;+0:8]>>[C:6]-[C:7]-[O;H0;D2;+0:8]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5] | 84.1 | [{"value": 84.1, "product": "BrC=1C=NC(=NC1)OCCOC1=C(C(=NC=N1)NS(=O)(=O)C1=CC=C(C=C1)C(C)(C)C)OC1=CC(=CC=C1)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 20 | MINUTE | To a solution of 4-tert-butyl-N-{6-(2-hydroxyethoxy)-5-(3-methoxyphenoxy)pyrimidin-4-yl}benzenesulfonamide (250 mg) in dimethylacetamide (5 ml) is added sodium hydride (60% dispersion-type, 64 mg) at room temperature, and the mixture is stirred for 20 minutes. To the reaction solution is added 5-bromo-2-chloropyrimidin... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary alcohol | Ether | c1cncnc1 | c1cncnc1 | c1ccccc1.c1ccccc1.c1cncnc1.c1cncnc1 | HCl | CC(=O)N(C)C | null | 0.333333 | COc1cccc(Oc2c(NS(=O)(=O)c3ccc(C(C)(C)C)cc3)ncnc2OCCO)c1.Clc1ncc(Br)cn1>CC(=O)N(C)C>COc1cccc(Oc2c(NS(=O)(=O)c3ccc(C(C)(C)C)cc3)ncnc2OCCOc2ncc(Br)cn2)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-50229f9f65b24c3fbf8cc4093165ef6b | CCC(C)(C)c1ccc(S(=O)(=O)Cl)cc1.Cc1ccc(-c2c(N)ncnc2OCCOc2ncc(Br)cn2)cc1.Cc1ccccc1>>CCC(C)(C)c1ccc(S(=O)(=O)Nc2ncnc(OCCOc3ccc(Br)cn3)c2-c2ccc(C)cc2)cc1 | BrC=1C=NC(=NC1)OCCOC1=C(C(=NC=N1)N)C1=CC=C(C=C1)C.C(C)(C)(CC)C1=CC=C(C=C1)S(=O)(=O)Cl.[OH-].[K+].C1(=CC=CC=C1)C>>C(C)(C)(CC)C1=CC=C(C=C1)S(=O)(=O)NC1=NC=NC(=C1C1=CC=C(C=C1)C)OCCOC1=NC=C(C=C1)Br | Cl[S:10]([c:9]1[cH:8][cH:7][c:6]([C:3]([CH2:2][CH3:1])([CH3:4])[CH3:5])[cH:39][cH:38]1)(=[O:11])=[O:12].n1[c:23]([O:22][CH2:21][CH2:20][O:19][c:18]2[n:17][cH:16][n:15][c:14]([NH2:13])[c:30]2-[c:31]2[cH:32][cH:33][c:34]([CH3:35])[cH:36][cH:37]2)[n:29][cH:28][c:26]([Br:27])[cH:25]1.Cc1cccc[cH:24]1>>[CH3:1][CH2:2][C:3]([C... | CCC(C)(C)c1ccc(S(=O)(=O)Cl)cc1.Cc1ccc(-c2c(N)ncnc2OCCOc2ncc(Br)cn2)cc1.Cc1ccccc1 | CCC(C)(C)c1ccc(S(=O)(=O)Nc2ncnc(OCCOc3ccc(Br)cn3)c2-c2ccc(C)cc2)cc1 | null | S(=O)(=O)(O)[O-].C(CCC)[N+](CCCC)(CCCC)CCCC | [Cl-].[NH4+] | Acylation | OtherReaction | 68960ea2fb053b53626a60b364b33c353b229261825bfebd4371e92b05572787 | c012f5d317428172f4a9e28261b0b62713c76cc5916784be443250a71553e511 | O=S(=O)(Nc1ncnc(OCCOc2ccccn2)c1-c1ccccc1)c1ccccc1 | C-c1:[cH;D2;+0:1]:c:c:c:c:1.Cl-[S;H0;D4;+0:2](=[O;D1;H0:3])(=[O;D1;H0:4])-[c:5](:[c:6]):[c:7].[Br;D1;H0:8]-[c:9]1:[c:10]:[#7;a:11]:[c;H0;D3;+0:12](-[#8:13]-[C:14]):n:[cH;D2;+0:15]:1.[NH2;D1;+0:16]-[c:17]1:[#7;a:18]:[c:19]:[#7;a:20]:[c:21]:[c:22]:1>>[Br;D1;H0:8]-[c:9]1:[c:10]:[#7;a:11]:[c;H0;D3;+0:12](-[#8:13]-[C:14]):[... | null | [] | null | null | 8 | HOUR | A mixture of 6-[2-(5-bromopyrimidin-2-yloxy)ethoxy]-5-(4-methylphenyl)pyrimidin-4-amine (150 mg), 4-tert-amylbenzenesulfonyl chloride (184 mg), 96% potassium hydroxide (powder, 300 mg), tetrabutylammonium hydrogen sulfate (34 mg) and toluene (10 ml) is stirred at room temperature overnight. The mixture is diluted with ... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Primary amine.Sulfonyl halide | Sulfonamide.Ether | c1cncnc1.c1ccccc1 | c1ccncc1 | c1ccccc1.c1cncnc1.c1ccncc1.c1ccccc1 | HCl | S(=O)(=O)(O)[O-].C(CCC)[N+](CCCC)(CCCC)CCCC.[Cl-].[NH4+] | null | 8 | CCC(C)(C)c1ccc(S(=O)(=O)Cl)cc1.Cc1ccc(-c2c(N)ncnc2OCCOc2ncc(Br)cn2)cc1.Cc1ccccc1>S(=O)(=O)(O)[O-].C(CCC)[N+](CCCC)(CCCC)CCCC.[Cl-].[NH4+]>CCC(C)(C)c1ccc(S(=O)(=O)Nc2ncnc(OCCOc3ccc(Br)cn3)c2-c2ccc(C)cc2)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-1a817c350a274f74a6c9e9de0ed1b599 | COc1cccc(Oc2c(NS(=O)(=O)c3ccc(C(C)(C)C)cc3)ncnc2OCCOc2ccnc(SC)n2)c1>>COc1cccc(Oc2c(NS(=O)(=O)c3ccc(C(C)(C)C)cc3)ncnc2OCCOc2ccncn2)c1 | C(C)(C)(C)C1=CC=C(C=C1)S(=O)(=O)NC1=NC=NC(=C1OC1=CC(=CC=C1)OC)OCCOC1=NC(=NC=C1)SC>>C(C)(C)(C)C1=CC=C(C=C1)S(=O)(=O)NC1=NC=NC(=C1OC1=CC(=CC=C1)OC)OCCOC1=NC=NC=C1 | CS[c:37]1[n:36][cH:35][cH:34][c:33]([O:32][CH2:31][CH2:30][O:29][c:28]2[c:9]([O:8][c:7]3[cH:6][cH:5][cH:4][c:3]([O:2][CH3:1])[cH:39]3)[c:10]([NH:11][S:12](=[O:13])(=[O:14])[c:15]3[cH:16][cH:17][c:18]([C:19]([CH3:20])([CH3:21])[CH3:22])[cH:23][cH:24]3)[n:25][cH:26][n:27]2)[n:38]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:... | COc1cccc(Oc2c(NS(=O)(=O)c3ccc(C(C)(C)C)cc3)ncnc2OCCOc2ccnc(SC)n2)c1 | COc1cccc(Oc2c(NS(=O)(=O)c3ccc(C(C)(C)C)cc3)ncnc2OCCOc2ccncn2)c1 | null | [Ni] | C(C)O | Reduction | OtherReaction | 2f887c6856c73bcc8c8e03d9499b4f130e1e3f94ebe4c422c097511ed52b18b9 | 32a5269109432865a866e9a2b5da238f4471b13dee7daf193dc4e8c41b091706 | O=S(=O)(Nc1ncnc(OCCOc2ccncn2)c1Oc1ccccc1)c1ccccc1 | C-S-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5]>>[c:5]:[#7;a:4]:[cH;D2;+0:1]:[#7;a:2]:[c:3] | 32.9 | [{"value": 32.9, "product": "C(C)(C)(C)C1=CC=C(C=C1)S(=O)(=O)NC1=NC=NC(=C1OC1=CC(=CC=C1)OC)OCCOC1=NC=NC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | A mixture of 4-tert-butyl-N-[5-(3-methoxyphenoxy)-6-{2-(2-methylthiopyrimidin-4-yloxy)ethoxy}pyrimidin-4-yl]benzenesulfonamide (250 mg), Raney-nickel (W-2) (2 g) and ethanol (5 ml) is stirred at room temperature overnight, and the mixture is refluxed for four hours. Raney-nickel is removed by filtration, and washed wit... | 10.6084/m9.figshare.5104873.v1 | null | Monosulfide | null | c1cncnc1 | c1cncnc1 | c1ccccc1.c1ccccc1.c1cncnc1.c1cncnc1 | Other | [Ni].C(C)O | null | 8 | COc1cccc(Oc2c(NS(=O)(=O)c3ccc(C(C)(C)C)cc3)ncnc2OCCOc2ccnc(SC)n2)c1>[Ni].C(C)O>COc1cccc(Oc2c(NS(=O)(=O)c3ccc(C(C)(C)C)cc3)ncnc2OCCOc2ccncn2)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-247f89c623c34222bcd61e153cb12689 | COc1cccc(Oc2c(NS(=O)(=O)c3ccc(C(C)(C)C)cc3)ncnc2OCCOc2ccc(Cl)nn2)c1>>COc1cccc(Oc2c(NS(=O)(=O)c3ccc(C(C)(C)C)cc3)ncnc2OCCOc2cccnn2)c1 | C(C)(C)(C)C1=CC=C(C=C1)S(=O)(=O)NC1=NC=NC(=C1OC1=CC(=CC=C1)OC)OCCOC=1N=NC(=CC1)Cl.C(C)N(CC)CC.CO>>C(C)(C)(C)C1=CC=C(C=C1)S(=O)(=O)NC1=NC=NC(=C1OC1=CC(=CC=C1)OC)OCCOC=1N=NC=CC1 | Cl[c:36]1[cH:35][cH:34][c:33]([O:32][CH2:31][CH2:30][O:29][c:28]2[c:9]([O:8][c:7]3[cH:6][cH:5][cH:4][c:3]([O:2][CH3:1])[cH:39]3)[c:10]([NH:11][S:12](=[O:13])(=[O:14])[c:15]3[cH:16][cH:17][c:18]([C:19]([CH3:20])([CH3:21])[CH3:22])[cH:23][cH:24]3)[n:25][cH:26][n:27]2)[n:38][n:37]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:... | COc1cccc(Oc2c(NS(=O)(=O)c3ccc(C(C)(C)C)cc3)ncnc2OCCOc2ccc(Cl)nn2)c1 | COc1cccc(Oc2c(NS(=O)(=O)c3ccc(C(C)(C)C)cc3)ncnc2OCCOc2cccnn2)c1 | null | [C].[Pd] | O1CCCC1 | Functional Group Interconversion | Aromatic dehalogenation | 11fec97dc22aabf340de6dd16bd9ed47791a1ff823f957f6e3aa8baf8018c49f | 56de34d4a44cb25d9380269ee5e138b0f24b40a3a0db22c5508049dc775a861f | O=S(=O)(Nc1ncnc(OCCOc2cccnn2)c1Oc1ccccc1)c1ccccc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[#7;a:3]:[c:4]:[c:5]:[c:6]:1>>[#7;a:2]1:[#7;a:3]:[c:4]:[c:5]:[c:6]:[cH;D2;+0:1]:1 | 78.6 | [{"value": 78.6, "product": "C(C)(C)(C)C1=CC=C(C=C1)S(=O)(=O)NC1=NC=NC(=C1OC1=CC(=CC=C1)OC)OCCOC=1N=NC=CC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 5 | HOUR | A mixture of 4-tert-butyl-N-[6-{2-(6-chloropyridazin-3-yloxy)ethoxy}-5-(3-methoxyphenoxy)pyrimidin-4-yl]benzenesulfonamide (150 mg), 10% palladium-carbon (30 mg), triethylamine (52 mg), methanol (8 ml) and tetrahydrofuran (6 ml) is stirred at room temperature for five hours under hydrogen atmosphere (1 atm), and the mi... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | null | c1ccnnc1 | c1ccnnc1 | c1ccccc1.c1ccccc1.c1cncnc1.c1ccnnc1 | Other | [C].[Pd].O1CCCC1 | null | 5 | COc1cccc(Oc2c(NS(=O)(=O)c3ccc(C(C)(C)C)cc3)ncnc2OCCOc2ccc(Cl)nn2)c1>[C].[Pd].O1CCCC1>COc1cccc(Oc2c(NS(=O)(=O)c3ccc(C(C)(C)C)cc3)ncnc2OCCOc2cccnn2)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-f020b163919949d6b3bb6451a5559a45 | C=C(OCC)c1cnc(OCCOc2ncnc(NS(=O)(=O)c3ccc(C(C)(C)C)cc3)c2Oc2cccc(OC)c2)nc1>>COc1cccc(Oc2c(NS(=O)(=O)c3ccc(C(C)(C)C)cc3)ncnc2OCCOc2ncc(C(C)=O)cn2)c1 | C(C)(C)(C)C1=CC=C(C=C1)S(=O)(=O)NC1=NC=NC(=C1OC1=CC(=CC=C1)OC)OCCOC1=NC=C(C=N1)C(=C)OCC.Cl.C(O)([O-])=O.[Na+]>>C(C)(=O)C=1C=NC(=NC1)OCCOC1=C(C(=NC=N1)NS(=O)(=O)C1=CC=C(C=C1)C(C)(C)C)OC1=CC(=CC=C1)OC | CC[O:39][C:37]([c:36]1[cH:35][n:34][c:33]([O:32][CH2:31][CH2:30][O:29][c:28]2[c:9]([O:8][c:7]3[cH:6][cH:5][cH:4][c:3]([O:2][CH3:1])[cH:42]3)[c:10]([NH:11][S:12](=[O:13])(=[O:14])[c:15]3[cH:16][cH:17][c:18]([C:19]([CH3:20])([CH3:21])[CH3:22])[cH:23][cH:24]3)[n:25][cH:26][n:27]2)[n:41][cH:40]1)=[CH2:38]>>[CH3:1][O:2][c:3... | C=C(OCC)c1cnc(OCCOc2ncnc(NS(=O)(=O)c3ccc(C(C)(C)C)cc3)c2Oc2cccc(OC)c2)nc1 | COc1cccc(Oc2c(NS(=O)(=O)c3ccc(C(C)(C)C)cc3)ncnc2OCCOc2ncc(C(C)=O)cn2)c1 | null | null | CC(=O)C | Miscellaneous | OtherReaction | 3e02cda7ca3208f28d8355e2c059d63c9e4eb2c7eba0cae088d693f3c74db23e | 215582e9637166736070a53bb588f4e45b0dfc6c974d1df4c97ac5a98451627c | O=S(=O)(Nc1ncnc(OCCOc2ncccn2)c1Oc1ccccc1)c1ccccc1 | C-C-[O;H0;D2;+0:1]-[C;H0;D3;+0:2](=[CH2;D1;+0:3])-[c:4]1:[c:5]:[#7;a:6]:[c:7]:[#7;a:8]:[c:9]:1>>[CH3;D1;+0:3]-[C;H0;D3;+0:2](=[O;H0;D1;+0:1])-[c:4]1:[c:5]:[#7;a:6]:[c:7]:[#7;a:8]:[c:9]:1 | 87 | [{"value": 87.0, "product": "C(C)(=O)C=1C=NC(=NC1)OCCOC1=C(C(=NC=N1)NS(=O)(=O)C1=CC=C(C=C1)C(C)(C)C)OC1=CC(=CC=C1)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 4-tert-butyl-N-[6-{2-(5-(1-ethoxyethenyl)pyrimidin-2-yloxy)ethoxy}-5-(3-methoxyphenoxy)pyrimidin-4-yl]benzenesulfonamide (1.022 g), 10% hydrochloric acid (1 ml) and acetone (20 ml) is reacted at room temperature for four hours. The pH value of the reaction solution is adjusted to pH 6 with aqueous sodium h... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Vinyl | Ketone | null | null | c1ccccc1.c1ccccc1.c1cncnc1.c1cncnc1 | Other | CC(=O)C | null | null | C=C(OCC)c1cnc(OCCOc2ncnc(NS(=O)(=O)c3ccc(C(C)(C)C)cc3)c2Oc2cccc(OC)c2)nc1>CC(=O)C>COc1cccc(Oc2c(NS(=O)(=O)c3ccc(C(C)(C)C)cc3)ncnc2OCCOc2ncc(C(C)=O)cn2)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-d12ed1b9d8ff40f987297e00a881f389 | COc1cccc(Oc2c(NS(=O)(=O)c3ccc(C(C)(C)C)cc3)ncnc2OCCOc2ncc(C(C)=O)cn2)c1>>COc1cccc(Oc2c(NS(=O)(=O)c3ccc(C(C)(C)C)cc3)ncnc2OCCOc2ncc(C(C)O)cn2)c1 | [BH4-].[Na+].C(C)(=O)C=1C=NC(=NC1)OCCOC1=C(C(=NC=N1)NS(=O)(=O)C1=CC=C(C=C1)C(C)(C)C)OC1=CC(=CC=C1)OC.O1CCCC1.C(C)(C)O.[BH4-].[Na+]>>C(C)(C)(C)C1=CC=C(C=C1)S(=O)(=O)NC1=NC=NC(=C1OC1=CC(=CC=C1)OC)OCCOC1=NC=C(C=N1)C(C)O | [CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]([O:8][c:9]2[c:10]([NH:11][S:12](=[O:13])(=[O:14])[c:15]3[cH:16][cH:17][c:18]([C:19]([CH3:20])([CH3:21])[CH3:22])[cH:23][cH:24]3)[n:25][cH:26][n:27][c:28]2[O:29][CH2:30][CH2:31][O:32][c:33]2[n:34][cH:35][c:36]([C:37]([CH3:38])=[O:39])[cH:40][n:41]2)[cH:42]1>>[CH3:1][O:2][c:3]1[c... | COc1cccc(Oc2c(NS(=O)(=O)c3ccc(C(C)(C)C)cc3)ncnc2OCCOc2ncc(C(C)=O)cn2)c1 | COc1cccc(Oc2c(NS(=O)(=O)c3ccc(C(C)(C)C)cc3)ncnc2OCCOc2ncc(C(C)O)cn2)c1 | null | null | O | Reduction | Reduction of ketone to secondary alcohol | 02790ac194d8bf7ccb13d6247c59412024d87f77d2c906ef7804f021f57d5070 | 1bd3cd74b454139c0a0068ac0135836499926b274bff569df163210c6c944a89 | O=S(=O)(Nc1ncnc(OCCOc2ncccn2)c1Oc1ccccc1)c1ccccc1 | [C;D1;H3:1]-[C;H0;D3;+0:2](=[O;H0;D1;+0:3])-[c:4]1:[c:5]:[#7;a:6]:[c:7]:[#7;a:8]:[c:9]:1>>[C;D1;H3:1]-[CH;D3;+0:2](-[OH;D1;+0:3])-[c:4]1:[c:5]:[#7;a:6]:[c:7]:[#7;a:8]:[c:9]:1 | 75.3 | [{"value": 75.3, "product": "C(C)(C)(C)C1=CC=C(C=C1)S(=O)(=O)NC1=NC=NC(=C1OC1=CC(=CC=C1)OC)OCCOC1=NC=C(C=N1)C(C)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 40 | MINUTE | To a mixture of N-[6-{2-(5-acetylpyrimidin-2-yloxy)ethoxy}-5-(3-methoxyphenoxy)pyrimidin-4-yl]-4-tert-butylbenzenesulfonamide (756 mg), tetrahydrofuran (10 ml) and isopropyl alcohol (10 ml) is added with stirring sodium borohydride (48 mg) under ice-cooling, and the mixture is stirred for 40 minutes under ice-cooling. ... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Secondary alcohol | null | null | c1ccccc1.c1ccccc1.c1cncnc1.c1cncnc1 | null | O | null | 0.666667 | COc1cccc(Oc2c(NS(=O)(=O)c3ccc(C(C)(C)C)cc3)ncnc2OCCOc2ncc(C(C)=O)cn2)c1>O>COc1cccc(Oc2c(NS(=O)(=O)c3ccc(C(C)(C)C)cc3)ncnc2OCCOc2ncc(C(C)O)cn2)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-77ecea47c92b4de49601a091efcd4b91 | COc1cccc(Oc2c(NS(=O)(=O)c3ccc(C(C)(C)C)cc3)ncnc2OCCOc2ncc(C(C)O)cn2)c1>>CCc1cnc(OCCOc2ncnc(NS(=O)(=O)c3ccc(C(C)(C)C)cc3)c2Oc2cccc(OC)c2)nc1 | C(C)(C)(C)C1=CC=C(C=C1)S(=O)(=O)NC1=NC=NC(=C1OC1=CC(=CC=C1)OC)OCCOC1=NC=C(C=N1)C(C)O.S(=O)(Cl)Cl>>C(C)(C)(C)C1=CC=C(C=C1)S(=O)(=O)NC1=NC=NC(=C1OC1=CC(=CC=C1)OC)OCCOC1=NC=C(C=N1)CC | O[CH:2]([CH3:1])[c:3]1[cH:4][n:5][c:6]([O:7][CH2:8][CH2:9][O:10][c:11]2[n:12][cH:13][n:14][c:15]([NH:16][S:17](=[O:18])(=[O:19])[c:20]3[cH:21][cH:22][c:23]([C:24]([CH3:25])([CH3:26])[CH3:27])[cH:28][cH:29]3)[c:30]2[O:31][c:32]2[cH:33][cH:34][cH:35][c:36]([O:37][CH3:38])[cH:39]2)[n:40][cH:41]1>>[CH3:1][CH2:2][c:3]1[cH:4... | COc1cccc(Oc2c(NS(=O)(=O)c3ccc(C(C)(C)C)cc3)ncnc2OCCOc2ncc(C(C)O)cn2)c1 | CCc1cnc(OCCOc2ncnc(NS(=O)(=O)c3ccc(C(C)(C)C)cc3)c2Oc2cccc(OC)c2)nc1 | null | null | C(Cl)Cl | Reduction | OtherReaction | 3c5af32aa639db2ebe4d9851942e9468e1838e06ae5b2c1669bca1d5e0922c33 | 46f8a11b80b06e754a5a34198d843342612a5e7ede950bda52ce3a500cedba0b | O=S(=O)(Nc1ncnc(OCCOc2ncccn2)c1Oc1ccccc1)c1ccccc1 | O-[CH;D3;+0:1](-[C;D1;H3:2])-[c:3]1:[c:4]:[#7;a:5]:[c:6]:[#7;a:7]:[c:8]:1>>[C;D1;H3:2]-[CH2;D2;+0:1]-[c:3]1:[c:4]:[#7;a:5]:[c:6]:[#7;a:7]:[c:8]:1 | 93.9 | [{"value": 93.9, "product": "C(C)(C)(C)C1=CC=C(C=C1)S(=O)(=O)NC1=NC=NC(=C1OC1=CC(=CC=C1)OC)OCCOC1=NC=C(C=N1)CC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | To a solution of 4-tert-butyl-N-[6-{2-(5-(1-hydroxyethyl)pyrimidin-2-yloxy)ethoxy}-5-(3-methoxyphenoxy)pyrimidin-4-yl]benzenesulfonamide (150 mg) in methylene chloride (3 ml) is added thionyl chloride (90 mg), and the mixture is reacted at room temperature for 0.5 hour. The reaction solution is concentrated to dryness ... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol | null | null | null | c1cncnc1.c1cncnc1.c1ccccc1.c1ccccc1 | Other | C(Cl)Cl | null | 2 | COc1cccc(Oc2c(NS(=O)(=O)c3ccc(C(C)(C)C)cc3)ncnc2OCCOc2ncc(C(C)O)cn2)c1>C(Cl)Cl>CCc1cnc(OCCOc2ncnc(NS(=O)(=O)c3ccc(C(C)(C)C)cc3)c2Oc2cccc(OC)c2)nc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-962a8cae74e94e06a885467f87289f79 | CC(C)=O.Cc1ccc(-c2c(NS(=O)(=O)c3ccc(C(C)(C)C)cc3)ncnc2OCCOc2ncc(Br)cn2)cc1>>Cc1ccc(-c2c(NS(=O)(=O)c3ccc(C(C)(C)C)cc3)ncnc2OCCOc2ncc(C(C)(C)O)cn2)cc1 | CC(=O)C.BrC=1C=NC(=NC1)OCCOC1=C(C(=NC=N1)NS(=O)(=O)C1=CC=C(C=C1)C(C)(C)C)C1=CC=C(C=C1)C.C(CCC)[Li].[Cl-].[NH4+]>>C(C)(C)(C)C1=CC=C(C=C1)S(=O)(=O)NC1=NC=NC(=C1C1=CC=C(C=C1)C)OCCOC1=NC=C(C=N1)C(C)(C)O | [C:34]([CH3:35])([CH3:36])=[O:37].Br[c:33]1[cH:32][n:31][c:30]([O:29][CH2:28][CH2:27][O:26][c:25]2[c:6](-[c:5]3[cH:4][cH:3][c:2]([CH3:1])[cH:41][cH:40]3)[c:7]([NH:8][S:9](=[O:10])(=[O:11])[c:12]3[cH:13][cH:14][c:15]([C:16]([CH3:17])([CH3:18])[CH3:19])[cH:20][cH:21]3)[n:22][cH:23][n:24]2)[n:39][cH:38]1>>[CH3:1][c:2]1[cH... | CC(C)=O.Cc1ccc(-c2c(NS(=O)(=O)c3ccc(C(C)(C)C)cc3)ncnc2OCCOc2ncc(Br)cn2)cc1 | Cc1ccc(-c2c(NS(=O)(=O)c3ccc(C(C)(C)C)cc3)ncnc2OCCOc2ncc(C(C)(C)O)cn2)cc1 | null | null | CCCCCC.O1CCCC1 | C-C Coupling | Grignard_alcohol | 39e787124c47cc58f4f89be35107a14c6ac496a68f4efe95b95a13b205eee2bb | b8801be51258f6ee39fb6aad45dd9677b1b9eed3d6e0018ffb065bca8e787abf | O=S(=O)(Nc1ncnc(OCCOc2ncccn2)c1-c1ccccc1)c1ccccc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[c:4]:[#7;a:5]:[c:6]:1.[C;D1;H3:7]-[C;H0;D3;+0:8](-[C;D1;H3:9])=[O;H0;D1;+0:10]>>[C;D1;H3:7]-[C;H0;D4;+0:8](-[C;D1;H3:9])(-[OH;D1;+0:10])-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[c:4]:[#7;a:5]:[c:6]:1 | 30.4 | [{"value": 30.4, "product": "C(C)(C)(C)C1=CC=C(C=C1)S(=O)(=O)NC1=NC=NC(=C1C1=CC=C(C=C1)C)OCCOC1=NC=C(C=N1)C(C)(C)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -78 | CELSIUS | 5 | MINUTE | To a solution of N-[6-{2-(5-bromopyrimidin-2-yloxy)ethoxy}-5-(4-methylphenyl)pyrimidin-4-yl]-4-tert-butylbenzenesulfonamide (300 mg) in tetetrahydrofuran (10 ml) is added a 1.6M solution of n-butyl lithium in n-hexane (0.75 ml) at -78° C. The mixture is stirred at -78° C. for 5 minutes, and thereto is added a solution ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ketone | Tertiary alcohol | c1cncnc1 | c1cncnc1 | c1ccccc1.c1ccccc1.c1cncnc1.c1cncnc1 | Br- | CCCCCC.O1CCCC1 | -78 | 0.083333 | CC(C)=O.Cc1ccc(-c2c(NS(=O)(=O)c3ccc(C(C)(C)C)cc3)ncnc2OCCOc2ncc(Br)cn2)cc1>CCCCCC.O1CCCC1>Cc1ccc(-c2c(NS(=O)(=O)c3ccc(C(C)(C)C)cc3)ncnc2OCCOc2ncc(C(C)(C)O)cn2)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-8cd0277d133e4a558c95fad0e057819e | Cc1ccc(-c2c(NS(=O)(=O)c3ccc(C(C)(C)C)cc3)ncnc2OCCOc2ncc(Br)cn2)cc1.O=Cc1ccccc1>>Cc1ccc(-c2c(NS(=O)(=O)c3ccc(C(C)(C)C)cc3)ncnc2OCCOc2ncc(C(O)c3ccccc3)cn2)cc1 | BrC=1C=NC(=NC1)OCCOC1=C(C(=NC=N1)NS(=O)(=O)C1=CC=C(C=C1)C(C)(C)C)C1=CC=C(C=C1)C.C(C1=CC=CC=C1)=O>>C(C)(C)(C)C1=CC=C(C=C1)S(=O)(=O)NC1=NC=NC(=C1C1=CC=C(C=C1)C)OCCOC1=NC=C(C=N1)C(C1=CC=CC=C1)O | Br[c:33]1[cH:32][n:31][c:30]([O:29][CH2:28][CH2:27][O:26][c:25]2[c:6](-[c:5]3[cH:4][cH:3][c:2]([CH3:1])[cH:45][cH:44]3)[c:7]([NH:8][S:9](=[O:10])(=[O:11])[c:12]3[cH:13][cH:14][c:15]([C:16]([CH3:17])([CH3:18])[CH3:19])[cH:20][cH:21]3)[n:22][cH:23][n:24]2)[n:43][cH:42]1.[CH:34](=[O:35])[c:36]1[cH:37][cH:38][cH:39][cH:40]... | Cc1ccc(-c2c(NS(=O)(=O)c3ccc(C(C)(C)C)cc3)ncnc2OCCOc2ncc(Br)cn2)cc1.O=Cc1ccccc1 | Cc1ccc(-c2c(NS(=O)(=O)c3ccc(C(C)(C)C)cc3)ncnc2OCCOc2ncc(C(O)c3ccccc3)cn2)cc1 | null | null | null | C-C Coupling | Grignard_alcohol | 75c787ac0d076cc302c3ae93129fb581fe4257a709ea4af6364d51ea4d30333d | 1c0bd0afc1d5e370e3c8193faf738f03752295e40fa0eb99c756011e9a4be26b | O=S(=O)(Nc1ncnc(OCCOc2ncc(Cc3ccccc3)cn2)c1-c1ccccc1)c1ccccc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[c:4]:[#7;a:5]:[c:6]:1.[O;H0;D1;+0:7]=[CH;D2;+0:8]-[c:9](:[c:10]):[c:11]>>[OH;D1;+0:7]-[CH;D3;+0:8](-[c:9](:[c:10]):[c:11])-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[c:4]:[#7;a:5]:[c:6]:1 | null | [] | null | null | null | null | N-[6-{2-(5-Bromopyrimidin-2-yloxy)ethoxy}-5-(4-methylphenyl)pyrimidin-4-yl]-4-tert-butylbenzenesulfonamide and benzaldehyde are treated in the same manner as in Example 129 to give 4-tert-butyl-N-[6-{2-(5-(α-hydroxybenzyl)primidin-2-yloxy)ethoxy}-5-(4-methylphenyl)pyrimidin-4-yl]-benzenesulfonamide.
Conditions: See rea... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aldehyde | Secondary alcohol | c1cncnc1 | c1cncnc1 | c1ccccc1.c1ccccc1.c1cncnc1.c1cncnc1.c1ccccc1 | Br- | null | null | null | Cc1ccc(-c2c(NS(=O)(=O)c3ccc(C(C)(C)C)cc3)ncnc2OCCOc2ncc(Br)cn2)cc1.O=Cc1ccccc1>>Cc1ccc(-c2c(NS(=O)(=O)c3ccc(C(C)(C)C)cc3)ncnc2OCCOc2ncc(C(O)c3ccccc3)cn2)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-46a2349036204912b3e748e1dead945d | C1COCCO1.C=[C](OCC)[Sn]([CH2]CCC)([CH2]CCC)[CH2]CCC.Cc1ccc(-c2c(NS(=O)(=O)c3ccc(C(C)(C)C)cc3)ncnc2OCCOc2ccc(Br)cc2)cc1>>CC(=O)c1ccc(OCCOc2ncnc(NS(=O)(=O)c3ccc(C(C)(C)C)cc3)c2-c2ccc(C)cc2)cc1.CCOC(=O)c1ccc(OCCOc2ncnc(NS(=O)(=O)c3ccc(C(C)(C)C)cc3)c2-c2ccc(C)cc2)cc1.Cc1ccc(-c2c(NS(=O)(=O)c3ccc(C(C)(C)C)cc3)ncnc2OCCOc2cccc... | [F-].[K+].BrC1=CC=C(OCCOC2=C(C(=NC=N2)NS(=O)(=O)C2=CC=C(C=C2)C(C)(C)C)C2=CC=C(C=C2)C)C=C1.C(C)OC(=C)[Sn](CCCC)(CCCC)CCCC.O1CCOCC1>>C(C)(C)(C)C1=CC=C(C=C1)S(=O)(=O)NC1=NC=NC(=C1C1=CC=C(C=C1)C)OCCOC1=CC=CC=C1.C(C)(=O)C1=CC=C(OCCOC2=C(C(=NC=N2)NS(=O)(=O)C2=CC=C(C=C2)C(C)(C)C)C2=CC=C(C=C2)C)C=C1.C(C)(C)(C)C1=CC=C(C=C1)S(=O... | [CH2:7]1[O:8][CH2:9][CH2:110][O:111][CH2:112]1.[Sn]([C:44](=[CH2:1])[O:43][CH2:42][CH3:41])([CH2:63][CH2:72][CH2:71][CH3:66])([CH2:67][CH2:70][CH2:2][CH3:49])[CH2:80][CH2:79][CH2:77][CH3:78].Br[c:87]1[cH:86][cH:85][c:12]([O:11][CH2:10][CH2:109][O:108][c:58]2[n:13][cH:14][n:15][c:16]([NH:17][S:18](=[O:3])(=[O:19])[c:21]... | C1COCCO1.C=[C](OCC)[Sn]([CH2]CCC)([CH2]CCC)[CH2]CCC.Cc1ccc(-c2c(NS(=O)(=O)c3ccc(C(C)(C)C)cc3)ncnc2OCCOc2ccc(Br)cc2)cc1 | CC(=O)c1ccc(OCCOc2ncnc(NS(=O)(=O)c3ccc(C(C)(C)C)cc3)c2-c2ccc(C)cc2)cc1.CCOC(=O)c1ccc(OCCOc2ncnc(NS(=O)(=O)c3ccc(C(C)(C)C)cc3)c2-c2ccc(C)cc2)cc1.Cc1ccc(-c2c(NS(=O)(=O)c3ccc(C(C)(C)C)cc3)ncnc2OCCOc2ccccc2)cc1 | null | C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.Cl[Pd]Cl | C(C)(=O)OCC | Aromatic Heterocycle Formation | OtherReaction | 3384d4ed98bccfbf5086e2f11673dbb479ddfb9b339f3d460c8967232a67da79 | 35fd948d77205d09b1c374fd9bc6f50dcd65f3f295597e118937a3c8e506d8cb | O=S(=O)(Nc1ncnc(OCCOc2ccccc2)c1-c1ccccc1)c1ccccc1.O=S(=O)(Nc1ncnc(OCCOc2ccccc2)c1-c1ccccc1)c1ccccc1.O=S(=O)(Nc1ncnc(OCCOc2ccccc2)c1-c1ccccc1)c1ccccc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[cH;D2;+0:3]:[c;H0;D3;+0:4](-[#8:5]-[CH2;D2;+0:6]-[CH2;D2;+0:7]-[O;H0;D2;+0:8]-[c;H0;D3;+0:9]2:[n;H0;D2;+0:10]:[c:11]:[#7;a:12]:[c:13](-[#7:14]-[S;H0;D4;+0:15](=[O;D1;H0:16])(=[O;H0;D1;+0:17])-[c:18]3:[c:19]:[c:20]:[c:21](-[C;H0;D4;+0:22](-[C;D1;H3:23])(-[C;D1;H3:24])-[CH3;D1;+0:25]):[c:26]:[c:... | null | [] | null | null | null | null | A mixture of N-[6-{2-(4-bromophenoxy)ethoxy}-5-(4-methylphenyl)pyrimidin-4-yl]-4-tert-butylbenzenesulfonamide (600 mg), (1-ethoxyvinyl)tributyltin (680 mg), bis(triphenylphosphine)palladium (II) chloride (35.5 mg) and dioxane (24 ml) is refluxed for 18 hours. The mixture is diluted with ethyl acetate, and thereto is ad... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonamide.Aromatic halide.Ether.Ether.Ether.Ether.Ether.Vinyl.Tin | Sulfonamide.Sulfonamide.Sulfonamide.Ketone.Ester.Ether.Ether.Ether.Ether.Ether.Ether | C1COCCO1.c1ccccc1.c1cncnc1 | c1ccccc1.c1cncnc1.c1ccccc1.c1cncnc1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1.c1cncnc1.c1ccccc1 | c1ccccc1.c1cncnc1.c1ccccc1.c1ccccc1.c1ccccc1.c1cncnc1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1.c1cncnc1.c1ccccc1 | Br-.Sn | C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.Cl[Pd]Cl.C(C)(=O)OCC | null | null | C1COCCO1.C=[C](OCC)[Sn]([CH2]CCC)([CH2]CCC)[CH2]CCC.Cc1ccc(-c2c(NS(=O)(=O)c3ccc(C(C)(C)C)cc3)ncnc2OCCOc2ccc(Br)cc2)cc1>C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.Cl[Pd]Cl.C(C)(=O)OCC>CC(=O)c1ccc(OCCOc2ncnc(NS(=O)(=O)c3ccc(C(C)(C)C)cc3)c2-c2ccc(C)cc2)cc1.CCOC(=O)c1ccc(OCCOc2ncnc(NS(=O)... |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-067eaf94fa2249c0960c6119d7d00e5f | Cc1ccc(-c2c(NS(=O)(=O)c3ccc(C(C)(C)C)cc3)ncnc2OCCOc2ccc([N+](=O)[O-])cn2)cc1>>Cc1ccc(-c2c(NS(=O)(=O)c3ccc(C(C)(C)C)cc3)ncnc2OCCOc2ccc(N)cn2)cc1 | C(C)(C)(C)C1=CC=C(C=C1)S(=O)(=O)NC1=NC=NC(=C1C1=CC=C(C=C1)C)OCCOC1=NC=C(C=C1)[N+](=O)[O-]>>NC=1C=CC(=NC1)OCCOC1=C(C(=NC=N1)NS(=O)(=O)C1=CC=C(C=C1)C(C)(C)C)C1=CC=C(C=C1)C | O=[N+:34]([O-])[c:33]1[cH:32][cH:31][c:30]([O:29][CH2:28][CH2:27][O:26][c:25]2[c:6](-[c:5]3[cH:4][cH:3][c:2]([CH3:1])[cH:38][cH:37]3)[c:7]([NH:8][S:9](=[O:10])(=[O:11])[c:12]3[cH:13][cH:14][c:15]([C:16]([CH3:17])([CH3:18])[CH3:19])[cH:20][cH:21]3)[n:22][cH:23][n:24]2)[n:36][cH:35]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5](-[c:6... | Cc1ccc(-c2c(NS(=O)(=O)c3ccc(C(C)(C)C)cc3)ncnc2OCCOc2ccc([N+](=O)[O-])cn2)cc1 | Cc1ccc(-c2c(NS(=O)(=O)c3ccc(C(C)(C)C)cc3)ncnc2OCCOc2ccc(N)cn2)cc1 | null | [C].[Pd] | C(C)(C)O.O1CCCC1 | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | O=S(=O)(Nc1ncnc(OCCOc2ccccn2)c1-c1ccccc1)c1ccccc1 | 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] | 89.8 | [{"value": 89.8, "product": "NC=1C=CC(=NC1)OCCOC1=C(C(=NC=N1)NS(=O)(=O)C1=CC=C(C=C1)C(C)(C)C)C1=CC=C(C=C1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1.5 | HOUR | To a solution of 4-tert-butyl-N-{5-(4-methylphenyl)-6-{2-(5-nitropyridin-2-yloxy)ethoxy}pyrimidin-4-yl}benzenesulfonamide (975 mg) in isopropanol/tetrahydrofuran (1:1) (20 ml) is added 10% palladium-carbon (200 mg), and the mixture is stirred at room temperature for 1.5 hour under hydrogen atmosphere (1 atm). The catal... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1.c1ccccc1.c1cncnc1.c1ccncc1 | Other | [C].[Pd].C(C)(C)O.O1CCCC1 | null | 1.5 | Cc1ccc(-c2c(NS(=O)(=O)c3ccc(C(C)(C)C)cc3)ncnc2OCCOc2ccc([N+](=O)[O-])cn2)cc1>[C].[Pd].C(C)(C)O.O1CCCC1>Cc1ccc(-c2c(NS(=O)(=O)c3ccc(C(C)(C)C)cc3)ncnc2OCCOc2ccc(N)cn2)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-120651b2204b4ad4a6559c00916cf891 | Cc1ccc(-c2c(NS(=O)(=O)c3ccc(C(C)(C)C)cc3)ncnc2OCCOc2ccc(N)cn2)cc1.O=C(Cl)c1ccccc1>>Cc1ccc(-c2c(NS(=O)(=O)c3ccc(C(C)(C)C)cc3)ncnc2OCCOc2ccc(NC(=O)c3ccccc3)cn2)cc1 | NC=1C=CC(=NC1)OCCOC1=C(C(=NC=N1)NS(=O)(=O)C1=CC=C(C=C1)C(C)(C)C)C1=CC=C(C=C1)C.C(C1=CC=CC=C1)(=O)Cl.Cl>>C(C)(C)(C)C1=CC=C(C=C1)S(=O)(=O)NC1=C(C(=NC=N1)OCCOC1=CC=C(C=N1)NC(C1=CC=CC=C1)=O)C1=CC=C(C=C1)C | [CH3:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[c:7]([NH:8][S:9](=[O:10])(=[O:11])[c:12]3[cH:13][cH:14][c:15]([C:16]([CH3:17])([CH3:18])[CH3:19])[cH:20][cH:21]3)[n:22][cH:23][n:24][c:25]2[O:26][CH2:27][CH2:28][O:29][c:30]2[cH:31][cH:32][c:33]([NH2:34])[cH:43][n:44]2)[cH:45][cH:46]1.Cl[C:35](=[O:36])[c:37]1[cH:38][cH:39][cH:40][... | Cc1ccc(-c2c(NS(=O)(=O)c3ccc(C(C)(C)C)cc3)ncnc2OCCOc2ccc(N)cn2)cc1.O=C(Cl)c1ccccc1 | Cc1ccc(-c2c(NS(=O)(=O)c3ccc(C(C)(C)C)cc3)ncnc2OCCOc2ccc(NC(=O)c3ccccc3)cn2)cc1 | null | null | C(Cl)Cl.N1=CC=CC=C1 | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=C(Nc1ccc(OCCOc2ncnc(NS(=O)(=O)c3ccccc3)c2-c2ccccc2)nc1)c1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]:[#7;a:10]:[c:11]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9]:[#7;a:10]:[c:11])-[c:3](:[c:4]):[c:5] | 89.8 | [{"value": 89.8, "product": "C(C)(C)(C)C1=CC=C(C=C1)S(=O)(=O)NC1=C(C(=NC=N1)OCCOC1=CC=C(C=N1)NC(C1=CC=CC=C1)=O)C1=CC=C(C=C1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | To a solution of N-{6-{2-(5-aminopyridin-2-yloxy)ethoxy}-5-(4-methylphenyl)pyrimidin-4-yl}-4-tert-butylbenzenesulfonamide (150 mg) in pyridine (2 ml) is added a solution of benzoyl chloride (43 mg) in methylene chloride (0.4 ml), and the mixture is stirred at room temperature for two hours. To the reaction solution is ... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccccc1.c1cncnc1.c1ccncc1.c1ccccc1 | HCl | C(Cl)Cl.N1=CC=CC=C1 | null | 2 | Cc1ccc(-c2c(NS(=O)(=O)c3ccc(C(C)(C)C)cc3)ncnc2OCCOc2ccc(N)cn2)cc1.O=C(Cl)c1ccccc1>C(Cl)Cl.N1=CC=CC=C1>Cc1ccc(-c2c(NS(=O)(=O)c3ccc(C(C)(C)C)cc3)ncnc2OCCOc2ccc(NC(=O)c3ccccc3)cn2)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-2b27766230944f8c824648b85c6e1690 | CC(=O)OC(C)=O.Cc1ccc(-c2c(NS(=O)(=O)c3ccc(C(C)(C)C)cc3)ncnc2OCCOc2ccc(N)cn2)cc1>>CC(=O)Nc1ccc(OCCOc2ncnc(NS(=O)(=O)c3ccc(C(C)(C)C)cc3)c2-c2ccc(C)cc2)nc1 | NC=1C=CC(=NC1)OCCOC1=C(C(=NC=N1)NS(=O)(=O)C1=CC=C(C=C1)C(C)(C)C)C1=CC=C(C=C1)C.C(C)(=O)OC(C)=O>>C(C)(C)(C)C1=CC=C(C=C1)S(=O)(=O)NC1=C(C(=NC=N1)OCCOC1=CC=C(C=N1)NC(C)=O)C1=CC=C(C=C1)C | CC(=O)O[C:2]([CH3:1])=[O:3].[NH2:4][c:5]1[cH:6][cH:7][c:8]([O:9][CH2:10][CH2:11][O:12][c:13]2[n:14][cH:15][n:16][c:17]([NH:18][S:19](=[O:20])(=[O:21])[c:22]3[cH:23][cH:24][c:25]([C:26]([CH3:27])([CH3:28])[CH3:29])[cH:30][cH:31]3)[c:32]2-[c:33]2[cH:34][cH:35][c:36]([CH3:37])[cH:38][cH:39]2)[n:40][cH:41]1>>[CH3:1][C:2](=... | CC(=O)OC(C)=O.Cc1ccc(-c2c(NS(=O)(=O)c3ccc(C(C)(C)C)cc3)ncnc2OCCOc2ccc(N)cn2)cc1 | CC(=O)Nc1ccc(OCCOc2ncnc(NS(=O)(=O)c3ccc(C(C)(C)C)cc3)c2-c2ccc(C)cc2)nc1 | null | null | null | Acylation | Aminolysis of esters | 87d35e51b477fc9a658a6f307eb56d84c8879182772c9dd3a42ec0d584fd2684 | 627cbc0550c9f51ad0105d9fcf46677e8c93bed87ee95bfe69292a82550c95b7 | O=S(=O)(Nc1ncnc(OCCOc2ccccn2)c1-c1ccccc1)c1ccccc1 | C-C(=O)-O-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[NH2;D1;+0:4]-[c:5](:[c:6]):[c:7]:[#7;a:8]:[c:9]>>[C;D1;H3:2]-[C;H0;D3;+0:1](=[O;D1;H0:3])-[NH;D2;+0:4]-[c:5](:[c:6]):[c:7]:[#7;a:8]:[c:9] | null | [] | null | null | null | null | N-{6-{2-(5-Aminopyridin-2-yloxy)ethoxy}-5-(4-methylphenyl)pyrimidin-4-yl}-4-tert-butylbenzenesulfonamide and acetic anhydride are treated in the same manner as in Example 135 to give N-[6-[2-{6-(4-tert-butylphenylsulfonylamino)-5-(4-methylphenyl)pyrimidin-4-yloxy}ethoxy]pyridin-3-yl]-acetamide.
Conditions: See reaction... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Primary amine | Secondary amide | null | null | c1ccncc1.c1cncnc1.c1ccccc1.c1ccccc1 | HO- | null | null | null | CC(=O)OC(C)=O.Cc1ccc(-c2c(NS(=O)(=O)c3ccc(C(C)(C)C)cc3)ncnc2OCCOc2ccc(N)cn2)cc1>>CC(=O)Nc1ccc(OCCOc2ncnc(NS(=O)(=O)c3ccc(C(C)(C)C)cc3)c2-c2ccc(C)cc2)nc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-84ab9eee49864e3bbbb3e0453ed88ab1 | CC(C)(C)C(=O)Cl.Cc1ccc(-c2c(NS(=O)(=O)c3ccc(C(C)(C)C)cc3)ncnc2OCCOc2ccc(N)cn2)cc1>>Cc1ccc(-c2c(NS(=O)(=O)c3ccc(C(C)(C)C)cc3)ncnc2OCCOc2ccc(NC(=O)C(C)(C)C)cn2)cc1 | NC=1C=CC(=NC1)OCCOC1=C(C(=NC=N1)NS(=O)(=O)C1=CC=C(C=C1)C(C)(C)C)C1=CC=C(C=C1)C.C(C(C)(C)C)(=O)Cl>>C(C)(C)(C)C1=CC=C(C=C1)S(=O)(=O)NC1=C(C(=NC=N1)OCCOC1=CC=C(C=N1)NC(C(C)(C)C)=O)C1=CC=C(C=C1)C | Cl[C:35](=[O:36])[C:37]([CH3:38])([CH3:39])[CH3:40].[CH3:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[c:7]([NH:8][S:9](=[O:10])(=[O:11])[c:12]3[cH:13][cH:14][c:15]([C:16]([CH3:17])([CH3:18])[CH3:19])[cH:20][cH:21]3)[n:22][cH:23][n:24][c:25]2[O:26][CH2:27][CH2:28][O:29][c:30]2[cH:31][cH:32][c:33]([NH2:34])[cH:41][n:42]2)[cH:43][cH... | CC(C)(C)C(=O)Cl.Cc1ccc(-c2c(NS(=O)(=O)c3ccc(C(C)(C)C)cc3)ncnc2OCCOc2ccc(N)cn2)cc1 | Cc1ccc(-c2c(NS(=O)(=O)c3ccc(C(C)(C)C)cc3)ncnc2OCCOc2ccc(NC(=O)C(C)(C)C)cn2)cc1 | null | null | null | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=S(=O)(Nc1ncnc(OCCOc2ccccn2)c1-c1ccccc1)c1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C;D1;H3:4])(-[C;D1;H3:5])-[C;D1;H3:6].[NH2;D1;+0:7]-[c:8](:[c:9]):[c:10]:[#7;a:11]:[c:12]>>[C;D1;H3:4]-[C:3](-[C;D1;H3:5])(-[C;D1;H3:6])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:7]-[c:8](:[c:9]):[c:10]:[#7;a:11]:[c:12] | null | [] | null | null | null | null | N-{6-{2-(5-Aminopyridin-2-yloxy)ethoxy}-5-(4-methylphenyl)pyrimidin-4-yl}-4-tert-butylbenzenesulfonamide and pivaloyl chloride are treated in the same manner as in Example 135 to give N-[6-[2-{6-(4-tert-butylphenylsulfonylamino)-5-(4-methylphenyl)pyrimidin-4-yloxy}ethoxy]pyridin-3-yl]pivalamide.
Conditions: See reactio... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccccc1.c1cncnc1.c1ccncc1 | HCl | null | null | null | CC(C)(C)C(=O)Cl.Cc1ccc(-c2c(NS(=O)(=O)c3ccc(C(C)(C)C)cc3)ncnc2OCCOc2ccc(N)cn2)cc1>>Cc1ccc(-c2c(NS(=O)(=O)c3ccc(C(C)(C)C)cc3)ncnc2OCCOc2ccc(NC(=O)C(C)(C)C)cn2)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-a95cb73bbffa41a19d32814251cb5b39 | Cc1ccc(-c2c(NS(=O)(=O)c3ccc(C(C)(C)C)cc3)ncnc2OCCOc2ccc(OCc3ccccc3)cc2)cc1>>Cc1ccc(-c2c(NS(=O)(=O)c3ccc(C(C)(C)C)cc3)ncnc2OCCOc2ccc(O)cc2)cc1 | C(C)(C)(C)C1=CC=C(C=C1)S(=O)(=O)NC1=NC=NC(=C1C1=CC=C(C=C1)C)OCCOC1=CC=C(C=C1)OCC1=CC=CC=C1>>C(C)(C)(C)C1=CC=C(C=C1)S(=O)(=O)NC1=NC=NC(=C1C1=CC=C(C=C1)C)OCCOC1=CC=C(C=C1)O | c1ccc(C[O:34][c:33]2[cH:32][cH:31][c:30]([O:29][CH2:28][CH2:27][O:26][c:25]3[c:6](-[c:5]4[cH:4][cH:3][c:2]([CH3:1])[cH:38][cH:37]4)[c:7]([NH:8][S:9](=[O:10])(=[O:11])[c:12]4[cH:13][cH:14][c:15]([C:16]([CH3:17])([CH3:18])[CH3:19])[cH:20][cH:21]4)[n:22][cH:23][n:24]3)[cH:36][cH:35]2)cc1>>[CH3:1][c:2]1[cH:3][cH:4][c:5](-[... | Cc1ccc(-c2c(NS(=O)(=O)c3ccc(C(C)(C)C)cc3)ncnc2OCCOc2ccc(OCc3ccccc3)cc2)cc1 | Cc1ccc(-c2c(NS(=O)(=O)c3ccc(C(C)(C)C)cc3)ncnc2OCCOc2ccc(O)cc2)cc1 | null | [C].[Pd] | C(C)O.O1CCCC1 | Deprotection | Hydroxyl benzyl deprotection | 36869d1fe85185a14d9eb30bf05178c600a9b6eca277ffaf3803578c30e0bf5d | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | O=S(=O)(Nc1ncnc(OCCOc2ccccc2)c1-c1ccccc1)c1ccccc1 | [c:1]:[c:2](-[O;H0;D2;+0:3]-C-c1:c:c:c:c:c:1):[c:4]>>[OH;D1;+0:3]-[c:2](:[c:1]):[c:4] | 97.9 | [{"value": 97.9, "product": "C(C)(C)(C)C1=CC=C(C=C1)S(=O)(=O)NC1=NC=NC(=C1C1=CC=C(C=C1)C)OCCOC1=CC=C(C=C1)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 4-tert-butyl-N-{6-[2-(4-benzyloxyphenoxy)ethoxy]-5-(4-methylphenyl)pyrimidin-4-yl}benzensulfonamide (3.95 g), 10% palladium-carbon (1.5 g) and ethanol-tetrahydrofuran (80 ml-80 ml) is subjected to catalytic hydrogenation at room temperature under hydrogen atmosphere (1 atm) for 24 hours. The catalyst is re... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | c1ccccc1 | null | c1ccccc1.c1ccccc1.c1cncnc1.c1ccccc1 | Other | [C].[Pd].C(C)O.O1CCCC1 | null | null | Cc1ccc(-c2c(NS(=O)(=O)c3ccc(C(C)(C)C)cc3)ncnc2OCCOc2ccc(OCc3ccccc3)cc2)cc1>[C].[Pd].C(C)O.O1CCCC1>Cc1ccc(-c2c(NS(=O)(=O)c3ccc(C(C)(C)C)cc3)ncnc2OCCOc2ccc(O)cc2)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-fd3a00b2a8e54606872bbc2155f28bf9 | Cc1ccc(-c2c(NS(=O)(=O)c3ccc(C(C)(C)C)cc3)ncnc2OCCOc2ccc([N+](=O)[O-])cc2)cc1>>Cc1ccc(-c2c(NS(=O)(=O)c3ccc(C(C)(C)C)cc3)ncnc2OCCOc2ccc(N)cc2)cc1 | C(C)(C)(C)C1=CC=C(C=C1)S(=O)(=O)NC1=NC=NC(=C1C1=CC=C(C=C1)C)OCCOC1=CC=C(C=C1)[N+](=O)[O-]>>NC1=CC=C(OCCOC2=C(C(=NC=N2)NS(=O)(=O)C2=CC=C(C=C2)C(C)(C)C)C2=CC=C(C=C2)C)C=C1 | O=[N+:34]([O-])[c:33]1[cH:32][cH:31][c:30]([O:29][CH2:28][CH2:27][O:26][c:25]2[c:6](-[c:5]3[cH:4][cH:3][c:2]([CH3:1])[cH:38][cH:37]3)[c:7]([NH:8][S:9](=[O:10])(=[O:11])[c:12]3[cH:13][cH:14][c:15]([C:16]([CH3:17])([CH3:18])[CH3:19])[cH:20][cH:21]3)[n:22][cH:23][n:24]2)[cH:36][cH:35]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5](-[c:... | Cc1ccc(-c2c(NS(=O)(=O)c3ccc(C(C)(C)C)cc3)ncnc2OCCOc2ccc([N+](=O)[O-])cc2)cc1 | Cc1ccc(-c2c(NS(=O)(=O)c3ccc(C(C)(C)C)cc3)ncnc2OCCOc2ccc(N)cc2)cc1 | null | [C].[Pd] | C(C)O.O1CCCC1 | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | O=S(=O)(Nc1ncnc(OCCOc2ccccc2)c1-c1ccccc1)c1ccccc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | 98.7 | [{"value": 98.7, "product": "NC1=CC=C(OCCOC2=C(C(=NC=N2)NS(=O)(=O)C2=CC=C(C=C2)C(C)(C)C)C2=CC=C(C=C2)C)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 4-tert-butyl-N-{5-(4-methylphenyl)-6-[2-(4-nitrophenoxy)ethoxy]pyrimidin-4-yl}benzenesulfonamide (383 mg), 10% palladium-carbon (50 mg) and ethanol-tetrahydrofuran (6 ml-3 ml) is subjected to catalytic hydrogenation at room temperature under hydrogen atmosphere (1 atm) for two hours. The catalyst is remove... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1.c1ccccc1.c1cncnc1.c1ccccc1 | Other | [C].[Pd].C(C)O.O1CCCC1 | null | null | Cc1ccc(-c2c(NS(=O)(=O)c3ccc(C(C)(C)C)cc3)ncnc2OCCOc2ccc([N+](=O)[O-])cc2)cc1>[C].[Pd].C(C)O.O1CCCC1>Cc1ccc(-c2c(NS(=O)(=O)c3ccc(C(C)(C)C)cc3)ncnc2OCCOc2ccc(N)cc2)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-6e6b46e6e7624474a5402b0aba237034 | CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[N]=[N+]=[N-].Cc1ccc(-c2c(NS(=O)(=O)c3ccc(C(C)(C)C)cc3)ncnc2OCCOc2ccc(C#N)cc2)cc1>>Cc1ccc(-c2c(NS(=O)(=O)c3ccc(C(C)(C)C)cc3)ncnc2OCCOc2ccc(-c3nnn[nH]3)cc2)cc1 | C(C)(C)(C)C1=CC=C(C=C1)S(=O)(=O)NC1=NC=NC(=C1C1=CC=C(C=C1)C)OCCOC1=CC=C(C=C1)C#N.C(CCC)[Sn](CCCC)(CCCC)N=[N+]=[N-].C1(=CC=CC=C1)C.[F-].[K+]>>C(C)(C)(C)C1=CC=C(C=C1)S(=O)(=O)NC1=NC=NC(=C1C1=CC=C(C=C1)C)OCCOC1=CC=C(C=C1)C1=NN=NN1 | CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[N:38]=[N+:37]=[N-:36].[CH3:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[c:7]([NH:8][S:9](=[O:10])(=[O:11])[c:12]3[cH:13][cH:14][c:15]([C:16]([CH3:17])([CH3:18])[CH3:19])[cH:20][cH:21]3)[n:22][cH:23][n:24][c:25]2[O:26][CH2:27][CH2:28][O:29][c:30]2[cH:31][cH:32][c:33]([C:34]#[N:35])[cH:39][cH:40]2)[... | CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[N]=[N+]=[N-].Cc1ccc(-c2c(NS(=O)(=O)c3ccc(C(C)(C)C)cc3)ncnc2OCCOc2ccc(C#N)cc2)cc1 | Cc1ccc(-c2c(NS(=O)(=O)c3ccc(C(C)(C)C)cc3)ncnc2OCCOc2ccc(-c3nnn[nH]3)cc2)cc1 | null | null | C(C)(=O)OCC | Aromatic Heterocycle Formation | OtherReaction | d793d4dee9d5a39dbd122d04a35a5f691674657d5f6e422ae31ce158ea438a57 | 95e338ac8e3158e8ab88ebe03ba7338cec0c32ed80de2cb9f73834a6f54aede3 | O=S(=O)(Nc1ncnc(OCCOc2ccc(-c3nnn[nH]3)cc2)c1-c1ccccc1)c1ccccc1 | C-C-C-[CH2]-[Sn](-[CH2]-C-C-C)(-[CH2]-C-C-C)-[N;H0;D2;+0:1]=[N+;H0;D2:2]=[N-;H0;D1:3].[N;H0;D1;+0:4]#[C;H0;D2;+0:5]-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]>>[c:8]:[c:7]:[c;H0;D3;+0:6](-[c;H0;D3;+0:5]1:[n;H0;D2;+0:4]:[n;H0;D2;+0:3]:[n;H0;D2;+0:2]:[nH;D2;+0:1]:1):[c:9]:[c:10] | 89.1 | [{"value": 89.1, "product": "C(C)(C)(C)C1=CC=C(C=C1)S(=O)(=O)NC1=NC=NC(=C1C1=CC=C(C=C1)C)OCCOC1=CC=C(C=C1)C1=NN=NN1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 20 | MINUTE | A mixture of 4-tert-butyl-N-{6-[2-(4-cyanophenoxy)ethoxy]-5-(4-methylphenyl)pyrimidin-4-yl}benzensulfonamide (1.31 g), tributyltin azide (1.60 g) and toluene (13 ml) is refluxed under argon atmosphere for 24 hours. After cooling, ethyl acetate and 10% aqueous potassium fluoride solution are added to the reaction soluti... | 10.6084/m9.figshare.5104873.v1 | null | Azide.Nitrile.Tin | null | null | c1nnn[nH]1 | c1ccccc1.c1ccccc1.c1cncnc1.c1ccccc1.c1nnn[nH]1 | Sn | C(C)(=O)OCC | null | 0.333333 | CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[N]=[N+]=[N-].Cc1ccc(-c2c(NS(=O)(=O)c3ccc(C(C)(C)C)cc3)ncnc2OCCOc2ccc(C#N)cc2)cc1>C(C)(=O)OCC>Cc1ccc(-c2c(NS(=O)(=O)c3ccc(C(C)(C)C)cc3)ncnc2OCCOc2ccc(-c3nnn[nH]3)cc2)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-653524203536458e8c961daeac1d8d20 | CC(C)(C)OC(=O)CBr.Cc1ccc(-c2c(NS(=O)(=O)c3ccc(C(C)(C)C)cc3)ncnc2OCCOc2ccc(O)cc2)cc1>>Cc1ccc(-c2c(NS(=O)(=O)c3ccc(C(C)(C)C)cc3)ncnc2OCCOc2ccc(OCC(=O)OC(C)(C)C)cc2)cc1 | C(C)(C)(C)C1=CC=C(C=C1)S(=O)(=O)NC1=NC=NC(=C1C1=CC=C(C=C1)C)OCCOC1=CC=C(C=C1)O.[H-].[Na+].BrCC(=O)OC(C)(C)C.[Cl-].[NH4+]>>C(C)(C)(C)C1=CC=C(C=C1)S(=O)(=O)NC1=C(C(=NC=N1)OCCOC1=CC=C(OCC(=O)OC(C)(C)C)C=C1)C1=CC=C(C=C1)C | Br[CH2:35][C:36](=[O:37])[O:38][C:39]([CH3:40])([CH3:41])[CH3:42].[CH3:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[c:7]([NH:8][S:9](=[O:10])(=[O:11])[c:12]3[cH:13][cH:14][c:15]([C:16]([CH3:17])([CH3:18])[CH3:19])[cH:20][cH:21]3)[n:22][cH:23][n:24][c:25]2[O:26][CH2:27][CH2:28][O:29][c:30]2[cH:31][cH:32][c:33]([OH:34])[cH:43][cH:4... | CC(C)(C)OC(=O)CBr.Cc1ccc(-c2c(NS(=O)(=O)c3ccc(C(C)(C)C)cc3)ncnc2OCCOc2ccc(O)cc2)cc1 | Cc1ccc(-c2c(NS(=O)(=O)c3ccc(C(C)(C)C)cc3)ncnc2OCCOc2ccc(OCC(=O)OC(C)(C)C)cc2)cc1 | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 50d675b335c583a6ce22e1164b27a78b18b9ca447d45137820c344bcb6369217 | 0865de4e1853c59ac25437e36fd18b03329566cb9eff4b4f0ce70d5714692fd3 | O=S(=O)(Nc1ncnc(OCCOc2ccccc2)c1-c1ccccc1)c1ccccc1 | Br-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#8:4]-[C:5](-[C;D1;H3:6])(-[C;D1;H3:7])-[C;D1;H3:8].[OH;D1;+0:9]-[c:10](:[c:11]):[c:12]>>[C;D1;H3:6]-[C:5](-[C;D1;H3:7])(-[C;D1;H3:8])-[#8:4]-[C:2](=[O;D1;H0:3])-[CH2;D2;+0:1]-[O;H0;D2;+0:9]-[c:10](:[c:11]):[c:12] | 92.7 | [{"value": 92.7, "product": "C(C)(C)(C)C1=CC=C(C=C1)S(=O)(=O)NC1=C(C(=NC=N1)OCCOC1=CC=C(OCC(=O)OC(C)(C)C)C=C1)C1=CC=C(C=C1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | To a solution of 4-tert-butyl-N-{6-[2-(4-hydroxyphenoxy)ethoxy]-5-(4-methylphenyl)pyrimidin-4-yl}benzenesulfonamide (200 mg) in dimethylformamide (2 ml) is added sodium hydride (60% dispersion-type, 32 mg), and the mixture is stirred at room temperature for 30 minutes. To the mixture is added a solution of tert-butyl b... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester.Aromatic alcohol | Ester.Ether | null | null | c1ccccc1.c1ccccc1.c1cncnc1.c1ccccc1 | HBr | CN(C=O)C | null | 0.5 | CC(C)(C)OC(=O)CBr.Cc1ccc(-c2c(NS(=O)(=O)c3ccc(C(C)(C)C)cc3)ncnc2OCCOc2ccc(O)cc2)cc1>CN(C=O)C>Cc1ccc(-c2c(NS(=O)(=O)c3ccc(C(C)(C)C)cc3)ncnc2OCCOc2ccc(OCC(=O)OC(C)(C)C)cc2)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-43429fd94ced493985de03e3c778c47f | Cc1ccc(-c2c(NS(=O)(=O)c3ccc(C(C)(C)C)cc3)ncnc2OCCOc2ccc(OCC(=O)OC(C)(C)C)cc2)cc1>>Cc1ccc(-c2c(NS(=O)(=O)c3ccc(C(C)(C)C)cc3)ncnc2OCCOc2ccc(OCC(=O)O)cc2)cc1 | C(C)(C)(C)C1=CC=C(C=C1)S(=O)(=O)NC1=C(C(=NC=N1)OCCOC1=CC=C(OCC(=O)OC(C)(C)C)C=C1)C1=CC=C(C=C1)C.C1(=CC=CC=C1)OC.FC(C(=O)O)(F)F>>C(C)(C)(C)C1=CC=C(C=C1)S(=O)(=O)NC1=C(C(=NC=N1)OCCOC1=CC=C(OCC(=O)O)C=C1)C1=CC=C(C=C1)C | CC(C)(C)[O:38][C:36]([CH2:35][O:34][c:33]1[cH:32][cH:31][c:30]([O:29][CH2:28][CH2:27][O:26][c:25]2[c:6](-[c:5]3[cH:4][cH:3][c:2]([CH3:1])[cH:42][cH:41]3)[c:7]([NH:8][S:9](=[O:10])(=[O:11])[c:12]3[cH:13][cH:14][c:15]([C:16]([CH3:17])([CH3:18])[CH3:19])[cH:20][cH:21]3)[n:22][cH:23][n:24]2)[cH:40][cH:39]1)=[O:37]>>[CH3:1]... | Cc1ccc(-c2c(NS(=O)(=O)c3ccc(C(C)(C)C)cc3)ncnc2OCCOc2ccc(OCC(=O)OC(C)(C)C)cc2)cc1 | Cc1ccc(-c2c(NS(=O)(=O)c3ccc(C(C)(C)C)cc3)ncnc2OCCOc2ccc(OCC(=O)O)cc2)cc1 | null | null | ClCCl | Deprotection | Deprotection of carboxylic acid | 152e5537e48c95b4a3e767536b0f9f68d1308e5f484070828ab5ed951805157a | 7f019d4cfe9b3036d0a2d3a3209aa0e1fcb05418ebee15a4be5e125d315d5f01 | O=S(=O)(Nc1ncnc(OCCOc2ccccc2)c1-c1ccccc1)c1ccccc1 | C-C(-C)(-C)-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4]>>[C:3]-[C:2](=[O;D1;H0:4])-[OH;D1;+0:1] | null | [] | null | null | 5 | HOUR | To a solution of tert-butyl 4-{2-{6-(4-tert-butylbenzenesulfonylamino)-5-(4-methylphenyl)pyrimidin-4-yloxy]ethoxy}phenoxyacetate (1.25 g) in dichloromethane (120 ml) are added anisole (2.09 g) and trifluoroacetic acid (20 ml) under ice-cooling. The mixture is stirred at room temperature for five hours, washed with wate... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Boc | Carboxylic acid | null | null | c1ccccc1.c1ccccc1.c1cncnc1.c1ccccc1 | Other | ClCCl | null | 5 | Cc1ccc(-c2c(NS(=O)(=O)c3ccc(C(C)(C)C)cc3)ncnc2OCCOc2ccc(OCC(=O)OC(C)(C)C)cc2)cc1>ClCCl>Cc1ccc(-c2c(NS(=O)(=O)c3ccc(C(C)(C)C)cc3)ncnc2OCCOc2ccc(OCC(=O)O)cc2)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-671a4344bcc6404d855dd54d549761c1 | Cc1ccc(-c2c(NS(=O)(=O)c3ccc(C(C)(C)C)cc3)ncnc2OCCOc2ncc(Br)cn2)cc1>>Cc1ccc(-c2c(NS(=O)(=O)c3ccc(C(C)(C)C)cc3)ncnc2OCCOc2ncc(C=O)cn2)cc1 | [Cl-].[NH4+].BrC=1C=NC(=NC1)OCCOC1=C(C(=NC=N1)NS(=O)(=O)C1=CC=C(C=C1)C(C)(C)C)C1=CC=C(C=C1)C.C(CCC)[Li].O1CCCC1.Cl>>C(C)(C)(C)C1=CC=C(C=C1)S(=O)(=O)NC1=NC=NC(=C1C1=CC=C(C=C1)C)OCCOC1=NC=C(C=N1)C=O | Br[c:33]1[cH:32][n:31][c:30]([O:29][CH2:28][CH2:27][O:26][c:25]2[c:6](-[c:5]3[cH:4][cH:3][c:2]([CH3:1])[cH:39][cH:38]3)[c:7]([NH:8][S:9](=[O:10])(=[O:11])[c:12]3[cH:13][cH:14][c:15]([C:16]([CH3:17])([CH3:18])[CH3:19])[cH:20][cH:21]3)[n:22][cH:23][n:24]2)[n:37][cH:36]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[c:7]([NH:8]... | Cc1ccc(-c2c(NS(=O)(=O)c3ccc(C(C)(C)C)cc3)ncnc2OCCOc2ncc(Br)cn2)cc1 | Cc1ccc(-c2c(NS(=O)(=O)c3ccc(C(C)(C)C)cc3)ncnc2OCCOc2ncc(C=O)cn2)cc1 | null | null | CN(C=O)C.CCCCCC | Oxidation | OtherReaction | d8674018a38b996edb42097b0f3ddbee5bebab67cad5c9f8c4a257003d0bbd10 | c25c3c47812a3895da25740aba48490812213ba83ecb1b4955751c5b0488c20c | O=S(=O)(Nc1ncnc(OCCOc2ncccn2)c1-c1ccccc1)c1ccccc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[c:4]:[#7;a:5]:[c:6]:1>>[O;D1;H0:7]=[C:8]-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[c:4]:[#7;a:5]:[c:6]:1 | null | [] | -78 | CELSIUS | 15 | MINUTE | To a solution of N-[6-{2-(5-bromopyrimidin-2-yloxy)ethoxy}-5-(4-methylphenyl)pyrimidin-4-yl]-4-tert-butylbenzenesulfonamide (700 mg) in tetrahydrofuran (15 ml) is added dropwise a 1.6M solution of n-butyl lithium in n-hexane (1.46 ml) at -78° C. The mixture is stirred at -78° C. for 15 minutes, and thereto is added dim... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | Aldehyde | c1cncnc1 | c1cncnc1 | c1ccccc1.c1ccccc1.c1cncnc1.c1cncnc1 | Br- | CN(C=O)C.CCCCCC | -78 | 0.25 | Cc1ccc(-c2c(NS(=O)(=O)c3ccc(C(C)(C)C)cc3)ncnc2OCCOc2ncc(Br)cn2)cc1>CN(C=O)C.CCCCCC>Cc1ccc(-c2c(NS(=O)(=O)c3ccc(C(C)(C)C)cc3)ncnc2OCCOc2ncc(C=O)cn2)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-5de6d1807c9144ae99d943a1bf4482b7 | Cc1ccc(-c2c(NS(=O)(=O)c3ccc(C(C)(C)C)cc3)ncnc2OCCOc2ncc(C=O)cn2)cc1>>Cc1ccc(-c2c(NS(=O)(=O)c3ccc(C(C)(C)C)cc3)ncnc2OCCOc2ncc(CO)cn2)cc1 | [Cl-].[NH4+].C(C)(C)(C)C1=CC=C(C=C1)S(=O)(=O)NC1=NC=NC(=C1C1=CC=C(C=C1)C)OCCOC1=NC=C(C=N1)C=O.[BH4-].[Na+]>>C(C)(C)(C)C1=CC=C(C=C1)S(=O)(=O)NC1=NC=NC(=C1C1=CC=C(C=C1)C)OCCOC1=NC=C(C=N1)CO | [CH3:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[c:7]([NH:8][S:9](=[O:10])(=[O:11])[c:12]3[cH:13][cH:14][c:15]([C:16]([CH3:17])([CH3:18])[CH3:19])[cH:20][cH:21]3)[n:22][cH:23][n:24][c:25]2[O:26][CH2:27][CH2:28][O:29][c:30]2[n:31][cH:32][c:33]([CH:34]=[O:35])[cH:36][n:37]2)[cH:38][cH:39]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[c... | Cc1ccc(-c2c(NS(=O)(=O)c3ccc(C(C)(C)C)cc3)ncnc2OCCOc2ncc(C=O)cn2)cc1 | Cc1ccc(-c2c(NS(=O)(=O)c3ccc(C(C)(C)C)cc3)ncnc2OCCOc2ncc(CO)cn2)cc1 | null | null | O1CCCC1.C(C)(C)O | Reduction | Reduction of aldehydes and ketones to alcohols | e7895795cd3f75445716c94697823c5929dcd4b5344525875fe75d36bca2f9d7 | 21bb81d5469aaaca71ab12c186bea4016451717fad8780cf288858a7d8fbc55a | O=S(=O)(Nc1ncnc(OCCOc2ncccn2)c1-c1ccccc1)c1ccccc1 | [O;H0;D1;+0:1]=[CH;D2;+0:2]-[c:3]1:[c:4]:[#7;a:5]:[c:6]:[#7;a:7]:[c:8]:1>>[OH;D1;+0:1]-[CH2;D2;+0:2]-[c:3]1:[c:4]:[#7;a:5]:[c:6]:[#7;a:7]:[c:8]:1 | 66.9 | [{"value": 66.9, "product": "C(C)(C)(C)C1=CC=C(C=C1)S(=O)(=O)NC1=NC=NC(=C1C1=CC=C(C=C1)C)OCCOC1=NC=C(C=N1)CO", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 4-tert-butyl-N-[6-{2-(5-formylpyrimidin-2-yloxy)ethoxy}-5-(4-methylphenyl)pyrimidin-4-yl]benzenesulfonamide (143 mg) in tetrahydrofuran-isopropanol (4 ml-4 ml) is added sodium borohydride (13 mg) under ice-cooling, and the mixture is reacted for two hours. The mixture is treated with aqueous ammonium c... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | Primary alcohol | null | null | c1ccccc1.c1ccccc1.c1cncnc1.c1cncnc1 | null | O1CCCC1.C(C)(C)O | null | null | Cc1ccc(-c2c(NS(=O)(=O)c3ccc(C(C)(C)C)cc3)ncnc2OCCOc2ncc(C=O)cn2)cc1>O1CCCC1.C(C)(C)O>Cc1ccc(-c2c(NS(=O)(=O)c3ccc(C(C)(C)C)cc3)ncnc2OCCOc2ncc(CO)cn2)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-f0bfe7cb12de4449ad46b88945212348 | CCCc1nc(NS(=O)(=O)c2ccc(C(C)(C)C)cc2)c(-c2ccc(C)cc2)c(OCCO)n1.Clc1ncc(Br)cn1>>CCCc1nc(NS(=O)(=O)c2ccc(C(C)(C)C)cc2)c(-c2ccc(C)cc2)c(OCCOc2ncc(Br)cn2)n1 | ClC1=NC=C(C=N1)Br.[H-].[Na+].C(C)(C)(C)C1=CC=C(C=C1)S(=O)(=O)NC1=NC(=NC(=C1C1=CC=C(C=C1)C)OCCO)CCC>>C(C)(C)(C)C1=CC=C(C=C1)S(=O)(=O)NC1=NC(=NC(=C1C1=CC=C(C=C1)C)OCCOC1=NC=C(C=N1)Br)CCC | [CH3:1][CH2:2][CH2:3][c:4]1[n:5][c:6]([NH:7][S:8](=[O:9])(=[O:10])[c:11]2[cH:12][cH:13][c:14]([C:15]([CH3:16])([CH3:17])[CH3:18])[cH:19][cH:20]2)[c:21](-[c:22]2[cH:23][cH:24][c:25]([CH3:26])[cH:27][cH:28]2)[c:29]([O:30][CH2:31][CH2:32][OH:33])[n:41]1.Cl[c:34]1[n:35][cH:36][c:37]([Br:38])[cH:39][n:40]1>>[CH3:1][CH2:2][C... | CCCc1nc(NS(=O)(=O)c2ccc(C(C)(C)C)cc2)c(-c2ccc(C)cc2)c(OCCO)n1.Clc1ncc(Br)cn1 | CCCc1nc(NS(=O)(=O)c2ccc(C(C)(C)C)cc2)c(-c2ccc(C)cc2)c(OCCOc2ncc(Br)cn2)n1 | null | null | CC(=O)N(C)C.O1CCCC1 | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | a445000eb5ed501274d93689ad5b9d45095af02deca02b6b541c8a834890a276 | a4cafa7bcd156e21cca6eaac1b32e28ec8540642a31181122e6957f3d7559631 | O=S(=O)(Nc1ncnc(OCCOc2ncccn2)c1-c1ccccc1)c1ccccc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5].[C:6]-[C:7]-[OH;D1;+0:8]>>[C:6]-[C:7]-[O;H0;D2;+0:8]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5] | 91.4 | [{"value": 91.4, "product": "C(C)(C)(C)C1=CC=C(C=C1)S(=O)(=O)NC1=NC(=NC(=C1C1=CC=C(C=C1)C)OCCOC1=NC=C(C=N1)Br)CCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2.5 | HOUR | To a suspension of sodium hydride (0.25 g) in tetrahydrofuran (5 ml) is added dropwise a solution of 4-tert-butyl-N-[6-(2-hydroxyethoxy)-5-(4-methylphenyl)-2-n-propylpyrimidin-4-yl]benzenesulfonamide (1.00 g) in dimethylacetamide (3 ml) and tetrahydrofuran (10 ml) at room temperature, and thereto is added 2-chloro-5-br... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary alcohol | Ether | c1cncnc1 | c1cncnc1 | c1cncnc1.c1ccccc1.c1ccccc1.c1cncnc1 | HCl | CC(=O)N(C)C.O1CCCC1 | null | 2.5 | CCCc1nc(NS(=O)(=O)c2ccc(C(C)(C)C)cc2)c(-c2ccc(C)cc2)c(OCCO)n1.Clc1ncc(Br)cn1>CC(=O)N(C)C.O1CCCC1>CCCc1nc(NS(=O)(=O)c2ccc(C(C)(C)C)cc2)c(-c2ccc(C)cc2)c(OCCOc2ncc(Br)cn2)n1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-39c43a50322a4e8ebd23910cb724fcc3 | CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[c]1cccs1.CCCc1nc(NS(=O)(=O)c2ccc(C(C)(C)C)cc2)c(-c2ccc(C)cc2)c(OCCOc2ncc(Br)cn2)n1>>CCCc1nc(NS(=O)(=O)c2ccc(C(C)(C)C)cc2)c(-c2ccc(C)cc2)c(OCCOc2ncc(-c3cccs3)cn2)n1 | [F-].[K+].C(C)(C)(C)C1=CC=C(C=C1)S(=O)(=O)NC1=NC(=NC(=C1C1=CC=C(C=C1)C)OCCOC1=NC=C(C=N1)Br)CCC.S1C(=CC=C1)[Sn](CCCC)(CCCC)CCCC.O1CCOCC1>>C(C)(C)(C)C1=CC=C(C=C1)S(=O)(=O)NC1=NC(=NC(=C1C1=CC=C(C=C1)C)OCCOC1=NC=C(C=N1)C=1SC=CC1)CCC | CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[c:38]1[cH:39][cH:40][cH:41][s:42]1.Br[c:37]1[cH:36][n:35][c:34]([O:33][CH2:32][CH2:31][O:30][c:29]2[c:21](-[c:22]3[cH:23][cH:24][c:25]([CH3:26])[cH:27][cH:28]3)[c:6]([NH:7][S:8](=[O:9])(=[O:10])[c:11]3[cH:12][cH:13][c:14]([C:15]([CH3:16])([CH3:17])[CH3:18])[cH:19][cH:20]3)[n:5][c:4]([CH... | CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[c]1cccs1.CCCc1nc(NS(=O)(=O)c2ccc(C(C)(C)C)cc2)c(-c2ccc(C)cc2)c(OCCOc2ncc(Br)cn2)n1 | CCCc1nc(NS(=O)(=O)c2ccc(C(C)(C)C)cc2)c(-c2ccc(C)cc2)c(OCCOc2ncc(-c3cccs3)cn2)n1 | null | C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.Cl[Pd]Cl | C(C)(=O)OCC | C-C Coupling | Stille reaction_aryl | 199420dc5768b1af27f86d7ad18eaf1b793cb98fd661ec8a8f552e8c67ad2d1d | db27eeefac0475c6d74fa10b3167e95a61caaae74e8bbafd45892452c0c3d4d6 | O=S(=O)(Nc1ncnc(OCCOc2ncc(-c3cccs3)cn2)c1-c1ccccc1)c1ccccc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[c:4]:[#7;a:5]:[c:6]:1.C-C-C-[CH2]-[Sn](-[CH2]-C-C-C)(-[CH2]-C-C-C)-[c;H0;D3;+0:7]1:[#16;a:8]:[c:9]:[c:10]:[c:11]:1>>[#16;a:8]1:[c:9]:[c:10]:[c:11]:[c;H0;D3;+0:7]:1-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[c:4]:[#7;a:5]:[c:6]:1 | 69.3 | [{"value": 69.3, "product": "C(C)(C)(C)C1=CC=C(C=C1)S(=O)(=O)NC1=NC(=NC(=C1C1=CC=C(C=C1)C)OCCOC1=NC=C(C=N1)C=1SC=CC1)CCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | A mixture of 4-tert-butyl-N-[6-{2-(5-bromopyrimidin-2-yloxy)ethoxy}-5-(4-methylphenyl)-2-n-propylpyrimidin-4-yl]benzenesulfonamide (300 mg), 2-thienyltributyltin (670 mg), bis(triphenylphosphine)palladium (II) chloride (16 mg) and dioxane (5 ml) is refluxed for 80 minutes. After cooling, the reaction solution is dilute... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Tin | null | c1ccsc1.c1cncnc1 | c1cncnc1.c1ccsc1 | c1cncnc1.c1ccccc1.c1ccccc1.c1cncnc1.c1ccsc1 | HBr.Sn | C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.Cl[Pd]Cl.C(C)(=O)OCC | null | 1 | CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[c]1cccs1.CCCc1nc(NS(=O)(=O)c2ccc(C(C)(C)C)cc2)c(-c2ccc(C)cc2)c(OCCOc2ncc(Br)cn2)n1>C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.Cl[Pd]Cl.C(C)(=O)OCC>CCCc1nc(NS(=O)(=O)c2ccc(C(C)(C)C)cc2)c(-c2ccc(C)cc2)c(OCCOc2ncc(-c3cccs3)cn2)n1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-05c8185b891646e0a16d36d0fe17f2e9 | CC(=O)c1ccc(OCCO)cc1.COc1ccccc1Oc1c(Cl)nc(-c2ncccn2)nc1NS(=O)(=O)c1ccc(C(C)(C)C)cc1>>COc1ccccc1Oc1c(NS(=O)(=O)c2ccc(C(C)(C)C)cc2)nc(-c2ncccn2)nc1OCCOc1ccc(C(C)=O)cc1 | Cl.ClC1=C(C(=NC(=N1)C1=NC=CC=N1)NS(=O)(=O)C1=CC=C(C=C1)C(C)(C)C)OC1=C(C=CC=C1)OC.C(C)(=O)C1=CC=C(OCCO)C=C1.[H-].[Na+]>>C(C)(=O)C1=CC=C(OCCOC2=C(C(=NC(=N2)C2=NC=CC=N2)NS(=O)(=O)C2=CC=C(C=C2)C(C)(C)C)OC2=C(C=CC=C2)OC)C=C1 | [OH:36][CH2:37][CH2:38][O:39][c:40]1[cH:41][cH:42][c:43]([C:44]([CH3:45])=[O:46])[cH:47][cH:48]1.Cl[c:35]1[c:10]([O:9][c:8]2[c:3]([O:2][CH3:1])[cH:4][cH:5][cH:6][cH:7]2)[c:11]([NH:12][S:13](=[O:14])(=[O:15])[c:16]2[cH:17][cH:18][c:19]([C:20]([CH3:21])([CH3:22])[CH3:23])[cH:24][cH:25]2)[n:26][c:27](-[c:28]2[n:29][cH:30]... | CC(=O)c1ccc(OCCO)cc1.COc1ccccc1Oc1c(Cl)nc(-c2ncccn2)nc1NS(=O)(=O)c1ccc(C(C)(C)C)cc1 | COc1ccccc1Oc1c(NS(=O)(=O)c2ccc(C(C)(C)C)cc2)nc(-c2ncccn2)nc1OCCOc1ccc(C(C)=O)cc1 | null | null | CC(=O)N(C)C | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | a445000eb5ed501274d93689ad5b9d45095af02deca02b6b541c8a834890a276 | a4cafa7bcd156e21cca6eaac1b32e28ec8540642a31181122e6957f3d7559631 | O=S(=O)(Nc1nc(-c2ncccn2)nc(OCCOc2ccccc2)c1Oc1ccccc1)c1ccccc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3](-[c:4](:[#7;a:5]):[#7;a:6]):[#7;a:7]:[c:8](-[#7:9]):[c:10]:1-[#8:11].[C:12]-[C:13]-[OH;D1;+0:14]>>[#7:9]-[c:8]1:[#7;a:7]:[c:3](-[c:4](:[#7;a:5]):[#7;a:6]):[#7;a:2]:[c;H0;D3;+0:1](-[O;H0;D2;+0:14]-[C:13]-[C:12]):[c:10]:1-[#8:11] | 36.1 | [{"value": 36.1, "product": "C(C)(=O)C1=CC=C(OCCOC2=C(C(=NC(=N2)C2=NC=CC=N2)NS(=O)(=O)C2=CC=C(C=C2)C(C)(C)C)OC2=C(C=CC=C2)OC)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | To a solution of N-{6-chloro-2-(2-pyrimidyl)-5-(2-methoxyphenoxy)pyrimidin-4-yl}-4-tert-butylbenzenesulfonamide (1.05 g) and 2-(4-acetylphenoxy)ethanol (728 mg) in dimethylacetamide (12 ml) is added sodium hydride (240 mg) under ice-cooling, and the mixture is stirred at room temperature overnight. The reaction solutio... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary alcohol | Ether | c1cncnc1 | c1cncnc1 | c1ccccc1.c1ccccc1.c1cncnc1.c1cncnc1.c1ccccc1 | HCl | CC(=O)N(C)C | null | 8 | CC(=O)c1ccc(OCCO)cc1.COc1ccccc1Oc1c(Cl)nc(-c2ncccn2)nc1NS(=O)(=O)c1ccc(C(C)(C)C)cc1>CC(=O)N(C)C>COc1ccccc1Oc1c(NS(=O)(=O)c2ccc(C(C)(C)C)cc2)nc(-c2ncccn2)nc1OCCOc1ccc(C(C)=O)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-03150a25c8ef45f8af726aa939a0c7a8 | COc1ccccc1Oc1c(Cl)nc(-c2ncccn2)nc1NS(=O)(=O)c1ccc(C(C)(C)C)cc1.OCCOc1ccc(Br)cc1>>COc1ccccc1Oc1c(NS(=O)(=O)c2ccc(C(C)(C)C)cc2)nc(-c2ncccn2)nc1OCCOc1ccc(Br)cc1 | ClC1=C(C(=NC(=N1)C1=NC=CC=N1)NS(=O)(=O)C1=CC=C(C=C1)C(C)(C)C)OC1=C(C=CC=C1)OC.BrC1=CC=C(OCCO)C=C1>>BrC1=CC=C(OCCOC2=C(C(=NC(=N2)C2=NC=CC=N2)NS(=O)(=O)C2=CC=C(C=C2)C(C)(C)C)OC2=C(C=CC=C2)OC)C=C1 | Cl[c:35]1[c:10]([O:9][c:8]2[c:3]([O:2][CH3:1])[cH:4][cH:5][cH:6][cH:7]2)[c:11]([NH:12][S:13](=[O:14])(=[O:15])[c:16]2[cH:17][cH:18][c:19]([C:20]([CH3:21])([CH3:22])[CH3:23])[cH:24][cH:25]2)[n:26][c:27](-[c:28]2[n:29][cH:30][cH:31][cH:32][n:33]2)[n:34]1.[OH:36][CH2:37][CH2:38][O:39][c:40]1[cH:41][cH:42][c:43]([Br:44])[c... | COc1ccccc1Oc1c(Cl)nc(-c2ncccn2)nc1NS(=O)(=O)c1ccc(C(C)(C)C)cc1.OCCOc1ccc(Br)cc1 | COc1ccccc1Oc1c(NS(=O)(=O)c2ccc(C(C)(C)C)cc2)nc(-c2ncccn2)nc1OCCOc1ccc(Br)cc1 | null | null | null | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | a445000eb5ed501274d93689ad5b9d45095af02deca02b6b541c8a834890a276 | a4cafa7bcd156e21cca6eaac1b32e28ec8540642a31181122e6957f3d7559631 | O=S(=O)(Nc1nc(-c2ncccn2)nc(OCCOc2ccccc2)c1Oc1ccccc1)c1ccccc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3](-[c:4](:[#7;a:5]):[#7;a:6]):[#7;a:7]:[c:8](-[#7:9]):[c:10]:1-[#8:11].[C:12]-[C:13]-[OH;D1;+0:14]>>[#7:9]-[c:8]1:[#7;a:7]:[c:3](-[c:4](:[#7;a:5]):[#7;a:6]):[#7;a:2]:[c;H0;D3;+0:1](-[O;H0;D2;+0:14]-[C:13]-[C:12]):[c:10]:1-[#8:11] | null | [] | null | null | null | null | N-{6-Chloro-2-(2-pyrimidyl)-5-(2-methoxyphenoxy)pyrimidin-4-yl}-4-tert-butylbenzenesulfonamide and 2-(4-bromophenoxy)ethanol are treated in the same manner as in Example 192-(1) to give N-{6-{2-(4-bromophenoxy)ethoxy}-2-(2-pyrimidyl)-5-(2-methoxyphenoxy)pyrimidin-4-yl}-4-tert-butylbenzenesulfonamide.
Conditions: See re... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary alcohol | Ether | c1cncnc1 | c1cncnc1 | c1ccccc1.c1ccccc1.c1cncnc1.c1cncnc1.c1ccccc1 | HCl | null | null | null | COc1ccccc1Oc1c(Cl)nc(-c2ncccn2)nc1NS(=O)(=O)c1ccc(C(C)(C)C)cc1.OCCOc1ccc(Br)cc1>>COc1ccccc1Oc1c(NS(=O)(=O)c2ccc(C(C)(C)C)cc2)nc(-c2ncccn2)nc1OCCOc1ccc(Br)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-36999e0228324fc28b461b37d57c6b5d | Cc1ccc(-c2c(NS(=O)(=O)c3ccc(C(C)(C)C)cc3)ncnc2OCCOc2ncc(S(C)=O)cn2)cc1>>Cc1ccc(-c2c(NS(=O)(=O)c3ccc(C(C)(C)C)cc3)ncnc2OCCOc2ncc(S)cn2)cc1 | C(C)(C)(C)C1=CC=C(C=C1)S(=O)(=O)NC1=NC=NC(=C1C1=CC=C(C=C1)C)OCCOC1=NC=C(C=N1)S(=O)C>>C(C)(C)(C)C1=CC=C(C=C1)S(=O)(=O)NC1=NC=NC(=C1C1=CC=C(C=C1)C)OCCOC1=NC=C(C=N1)S | C[S:34](=O)[c:33]1[cH:32][n:31][c:30]([O:29][CH2:28][CH2:27][O:26][c:25]2[c:6](-[c:5]3[cH:4][cH:3][c:2]([CH3:1])[cH:38][cH:37]3)[c:7]([NH:8][S:9](=[O:10])(=[O:11])[c:12]3[cH:13][cH:14][c:15]([C:16]([CH3:17])([CH3:18])[CH3:19])[cH:20][cH:21]3)[n:22][cH:23][n:24]2)[n:36][cH:35]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[c:... | Cc1ccc(-c2c(NS(=O)(=O)c3ccc(C(C)(C)C)cc3)ncnc2OCCOc2ncc(S(C)=O)cn2)cc1 | Cc1ccc(-c2c(NS(=O)(=O)c3ccc(C(C)(C)C)cc3)ncnc2OCCOc2ncc(S)cn2)cc1 | null | null | FC(C(=O)OC(C(F)(F)F)=O)(F)F.C(Cl)Cl | Miscellaneous | OtherReaction | eef2e1b5ff0f69ab6081f09517432c05434b0ab0589dc0e3684a9e4e2f78d988 | b886beeb8fbfa84bb0f92183b9fe913660dce69c18077df92371b7c354b5aef5 | O=S(=O)(Nc1ncnc(OCCOc2ncccn2)c1-c1ccccc1)c1ccccc1 | C-[S;H0;D3;+0:1](=O)-[c:2]1:[c:3]:[#7;a:4]:[c:5]:[#7;a:6]:[c:7]:1>>[SH;D1;+0:1]-[c:2]1:[c:3]:[#7;a:4]:[c:5]:[#7;a:6]:[c:7]:1 | 118.4 | [{"value": 118.4, "product": "C(C)(C)(C)C1=CC=C(C=C1)S(=O)(=O)NC1=NC=NC(=C1C1=CC=C(C=C1)C)OCCOC1=NC=C(C=N1)S", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 4-tert-butyl-N-{6-[2-(5-methylsulfinylpyrimidin-2-yloxy)ethoxy]-5-(4-methylphenyl)pyrimidin-4-yl}benzenesulfonamide (471 mg) in trifluoroacetic anhydride (5 ml) and methylene chloride (5 ml) is refluxed for 30 minutes, and the mixture is evaporated to remove the solvent. The residue is dissolved in methan... | 10.6084/m9.figshare.5104873.v1 | null | Sulfoxide | Aromatic thiol | null | null | c1ccccc1.c1ccccc1.c1cncnc1.c1cncnc1 | HO- | FC(C(=O)OC(C(F)(F)F)=O)(F)F.C(Cl)Cl | null | null | Cc1ccc(-c2c(NS(=O)(=O)c3ccc(C(C)(C)C)cc3)ncnc2OCCOc2ncc(S(C)=O)cn2)cc1>FC(C(=O)OC(C(F)(F)F)=O)(F)F.C(Cl)Cl>Cc1ccc(-c2c(NS(=O)(=O)c3ccc(C(C)(C)C)cc3)ncnc2OCCOc2ncc(S)cn2)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-71e8710276684d12a0219fa338a27605 | Cc1ccc(-c2c(NS(=O)(=O)c3ccc(C(C)(C)C)cc3)ncnc2OCCOc2ncc(Br)cn2)cc1>>Cc1ccc(-c2c(NS(=O)(=O)c3ccc(C(C)(C)C)cc3)ncnc2OCCOc2ncc(C#N)cn2)cc1 | C(C)(C)(C)C1=CC=C(C=C1)S(=O)(=O)NC1=NC=NC(=C1C1=CC=C(C=C1)C)OCCOC1=NC=C(C=N1)Br.CN1C(N(CC1)C)=O>>C(C)(C)(C)C1=CC=C(C=C1)S(=O)(=O)NC1=NC=NC(=C1C1=CC=C(C=C1)C)OCCOC1=NC=C(C=N1)C#N | Br[c:33]1[cH:32][n:31][c:30]([O:29][CH2:28][CH2:27][O:26][c:25]2[c:6](-[c:5]3[cH:4][cH:3][c:2]([CH3:1])[cH:39][cH:38]3)[c:7]([NH:8][S:9](=[O:10])(=[O:11])[c:12]3[cH:13][cH:14][c:15]([C:16]([CH3:17])([CH3:18])[CH3:19])[cH:20][cH:21]3)[n:22][cH:23][n:24]2)[n:37][cH:36]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[c:7]([NH:8]... | Cc1ccc(-c2c(NS(=O)(=O)c3ccc(C(C)(C)C)cc3)ncnc2OCCOc2ncc(Br)cn2)cc1 | Cc1ccc(-c2c(NS(=O)(=O)c3ccc(C(C)(C)C)cc3)ncnc2OCCOc2ncc(C#N)cn2)cc1 | null | [C-]#N.[Zn+2].[C-]#N.C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1 | [Cl-].[NH4+] | Miscellaneous | OtherReaction | befca4f7e44719fc2cef4b5066fb06593c9f7eec2590ef5c71573eb173d27428 | 73a96fe5e833259ca394a42f82d6cc2ee7231bcde92d95030d2893b90c3fef76 | O=S(=O)(Nc1ncnc(OCCOc2ncccn2)c1-c1ccccc1)c1ccccc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[c:4]:[#7;a:5]:[c:6]:1>>[N;D1;H0:7]#[C:8]-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[c:4]:[#7;a:5]:[c:6]:1 | null | [] | 80 | CELSIUS | 6 | HOUR | A mixture of 4-tert-butyl-N-{6-[2-(5-bromopyrimidin-2-yloxy)ethoxy]-5-(4-methylphenyl)pyrimidin-4-yl}benzenesulfonamide (1.00 g), zinc cyanide (784 mg), tetrakis(triphenylphosphine)palladium (250 mg) and 1,3-dimethyl-2-imidazolidinone (40 ml) is stirred at 80° C. for 6 hours under argon atmosphere. The mixture is coole... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | Nitrile | c1cncnc1 | c1cncnc1 | c1ccccc1.c1ccccc1.c1cncnc1.c1cncnc1 | Br- | [C-]#N.[Zn+2].[C-]#N.C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.[Cl-].[NH4+] | 80 | 6 | Cc1ccc(-c2c(NS(=O)(=O)c3ccc(C(C)(C)C)cc3)ncnc2OCCOc2ncc(Br)cn2)cc1>[C-]#N.[Zn+2].[C-]#N.C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.[Cl-].[NH4+]>Cc1ccc(-c2c(NS(=O)(=O)c3ccc(C(C)(C)C)cc3)ncnc2OC... |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-44df82bc06fd4ddbb31fd55df1a9fad3 | C#C[Si](C)(C)C.Cc1ccc(-c2c(NS(=O)(=O)c3ccc(C(C)(C)C)cc3)ncnc2OCCOc2ncc(Br)cn2)cc1>>Cc1ccc(-c2c(NS(=O)(=O)c3ccc(C(C)(C)C)cc3)ncnc2OCCOc2ncc(C#C[Si](C)(C)C)cn2)cc1 | C(C)(C)(C)C1=CC=C(C=C1)S(=O)(=O)NC1=NC=NC(=C1C1=CC=C(C=C1)C)OCCOC1=NC=C(C=N1)Br.C[Si](C)(C)C#C.C(C)N(CC)CC.CN(C=O)C>>C(C)(C)(C)C1=CC=C(C=C1)S(=O)(=O)NC1=NC=NC(=C1C1=CC=C(C=C1)C)OCCOC1=NC=C(C=N1)C#C[Si](C)(C)C | [CH:34]#[C:35][Si:36]([CH3:37])([CH3:38])[CH3:39].Br[c:33]1[cH:32][n:31][c:30]([O:29][CH2:28][CH2:27][O:26][c:25]2[c:6](-[c:5]3[cH:4][cH:3][c:2]([CH3:1])[cH:43][cH:42]3)[c:7]([NH:8][S:9](=[O:10])(=[O:11])[c:12]3[cH:13][cH:14][c:15]([C:16]([CH3:17])([CH3:18])[CH3:19])[cH:20][cH:21]3)[n:22][cH:23][n:24]2)[n:41][cH:40]1>>... | C#C[Si](C)(C)C.Cc1ccc(-c2c(NS(=O)(=O)c3ccc(C(C)(C)C)cc3)ncnc2OCCOc2ncc(Br)cn2)cc1 | Cc1ccc(-c2c(NS(=O)(=O)c3ccc(C(C)(C)C)cc3)ncnc2OCCOc2ncc(C#C[Si](C)(C)C)cn2)cc1 | null | C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.Cl[Pd]Cl.[Cu]I | [Cl-].[NH4+] | C-C Coupling | Sonogashira alkyne_aryl halide | 6c841971a35ffd50215936cda19c192218792b140679c95a1b7a8fa56d8a741b | 305eca0fd2975da49e7f69e4edfb9dc1cbce82513954bc5a73be3289e70e5f76 | O=S(=O)(Nc1ncnc(OCCOc2ncccn2)c1-c1ccccc1)c1ccccc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[c:4]:[#7;a:5]:[c:6]:1.[C;D1;H3:7]-[#14:8](-[C;D1;H3:9])(-[C;D1;H3:10])-[C:11]#[CH;D1;+0:12]>>[C;D1;H3:7]-[#14:8](-[C;D1;H3:9])(-[C;D1;H3:10])-[C:11]#[C;H0;D2;+0:12]-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[c:4]:[#7;a:5]:[c:6]:1 | 81.3 | [{"value": 81.3, "product": "C(C)(C)(C)C1=CC=C(C=C1)S(=O)(=O)NC1=NC=NC(=C1C1=CC=C(C=C1)C)OCCOC1=NC=C(C=N1)C#C[Si](C)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 50 | CELSIUS | 3 | HOUR | A mixture of 4-tert-butyl-N-{6-[2-(5-bromopyrimidin-2-yloxy)ethoxy]-5-(4-methylphenyl)pyrimidin-4-yl}benzenesulfonamide (1.00 g), trimethylsilylacetylene (330 mg), bis(triphenylphosphine)palladium (II) chloride (58 mg), copper (I) iodide (32 mg), triethylamine (420 mg) and dimethylformamide (5 ml) is stirred at 50° C. ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Alkyne | Alkyne | c1cncnc1 | c1cncnc1 | c1ccccc1.c1ccccc1.c1cncnc1.c1cncnc1 | HBr | C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.Cl[Pd]Cl.[Cu]I.[Cl-].[NH4+] | 50 | 3 | C#C[Si](C)(C)C.Cc1ccc(-c2c(NS(=O)(=O)c3ccc(C(C)(C)C)cc3)ncnc2OCCOc2ncc(Br)cn2)cc1>C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.Cl[Pd]Cl.[Cu]I.[Cl-].[NH4+]>Cc1ccc(-c2c(NS(=O)(=O)c3ccc(C(C)(C)C)cc3)ncnc2OCCOc2ncc(C#C[Si](C)(C)C)cn2)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-ef654fd56d444338b74762628d0ff15f | Cc1ccc(-c2c(NS(=O)(=O)c3ccc(C(C)(C)C)cc3)ncnc2OCCOc2ncc(C#C[Si](C)(C)C)cn2)cc1>>C#Cc1cnc(OCCOc2ncnc(NS(=O)(=O)c3ccc(C(C)(C)C)cc3)c2-c2ccc(C)cc2)nc1 | C(C)(C)(C)C1=CC=C(C=C1)S(=O)(=O)NC1=NC=NC(=C1C1=CC=C(C=C1)C)OCCOC1=NC=C(C=N1)C#C[Si](C)(C)C.C([O-])([O-])=O.[K+].[K+].CO>>C(C)(C)(C)C1=CC=C(C=C1)S(=O)(=O)NC1=NC=NC(=C1C1=CC=C(C=C1)C)OCCOC1=NC=C(C=N1)C#C | C[Si](C)(C)[C:1]#[C:2][c:3]1[cH:4][n:5][c:6]([O:7][CH2:8][CH2:9][O:10][c:11]2[n:12][cH:13][n:14][c:15]([NH:16][S:17](=[O:18])(=[O:19])[c:20]3[cH:21][cH:22][c:23]([C:24]([CH3:25])([CH3:26])[CH3:27])[cH:28][cH:29]3)[c:30]2-[c:31]2[cH:32][cH:33][c:34]([CH3:35])[cH:36][cH:37]2)[n:38][cH:39]1>>[CH:1]#[C:2][c:3]1[cH:4][n:5][... | Cc1ccc(-c2c(NS(=O)(=O)c3ccc(C(C)(C)C)cc3)ncnc2OCCOc2ncc(C#C[Si](C)(C)C)cn2)cc1 | C#Cc1cnc(OCCOc2ncnc(NS(=O)(=O)c3ccc(C(C)(C)C)cc3)c2-c2ccc(C)cc2)nc1 | null | null | [Cl-].[NH4+] | Deprotection | TMS deprotection from alkyne | e85676bb81da384790c9c858d44f182cdd01e3a79f77f7a239fe38487234cb96 | 56d526d7c9cb1bd7bee4940e216a9b1dd4597fd025a186b8d6e4675d8f4db26b | O=S(=O)(Nc1ncnc(OCCOc2ncccn2)c1-c1ccccc1)c1ccccc1 | C-[Si](-C)(-C)-[C;H0;D2;+0:1]#[C:2]-[c:3](:[c:4]:[#7;a:5]):[c:6]:[#7;a:7]>>[#7;a:5]:[c:4]:[c:3](-[C:2]#[CH;D1;+0:1]):[c:6]:[#7;a:7] | 85.3 | [{"value": 85.3, "product": "C(C)(C)(C)C1=CC=C(C=C1)S(=O)(=O)NC1=NC=NC(=C1C1=CC=C(C=C1)C)OCCOC1=NC=C(C=N1)C#C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 2 | HOUR | A mixture of 4-tert-butyl-N-{6-[2-(5-trimethylsilylethynylpyrimidin-2-yloxy)ethoxy]-5-(4-methylphenyl)pyrimidin-4-yl}benzenesulfonamide (667 mg), potassium carbonate (299 mg) and dry methanol (13 ml) is stirred at 0° C. for two hours, and diluted with saturated aqueous ammonium chloride solution, and extracted with eth... | 10.6084/m9.figshare.5104873.v1 | null | Alkyne.Silyl protective group | Alkyne | null | null | c1cncnc1.c1cncnc1.c1ccccc1.c1ccccc1 | Other | [Cl-].[NH4+] | 0 | 2 | Cc1ccc(-c2c(NS(=O)(=O)c3ccc(C(C)(C)C)cc3)ncnc2OCCOc2ncc(C#C[Si](C)(C)C)cn2)cc1>[Cl-].[NH4+]>C#Cc1cnc(OCCOc2ncnc(NS(=O)(=O)c3ccc(C(C)(C)C)cc3)c2-c2ccc(C)cc2)nc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-d5b502a9c1d04da5bcd8e0a9c3285742 | Cc1ccc(-c2c(NS(=O)(=O)c3ccc(C(C)(C)CO)cc3)ncnc2OCCO)cc1.Clc1ncc(Br)cn1>>Cc1ccc(-c2c(NS(=O)(=O)c3ccc(C(C)(C)COc4ncc(Br)cn4)cc3)ncnc2OCCOc2ncc(Br)cn2)cc1 | Cl.OCC(C)(C)C1=CC=C(C=C1)S(=O)(=O)NC1=NC=NC(=C1C1=CC=C(C=C1)C)OCCO.[H-].[Na+].BrC=1C=NC(=NC1)Cl>>BrC=1C=NC(=NC1)OCC(C)(C)C1=CC=C(C=C1)S(=O)(=O)NC1=NC=NC(=C1C1=CC=C(C=C1)C)OCCOC1=NC=C(C=N1)Br | [CH3:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[c:7]([NH:8][S:9](=[O:10])(=[O:11])[c:12]3[cH:13][cH:14][c:15]([C:16]([CH3:17])([CH2:19][OH:20])[CH3:43])[cH:28][cH:29]3)[n:30][cH:31][n:32][c:33]2[O:34][CH2:35][CH2:36][OH:37])[cH:45][cH:46]1.Cl[c:21]1[n:22][cH:23][c:24]([Br:25])[cH:26][n:27]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5](-[c:6... | Cc1ccc(-c2c(NS(=O)(=O)c3ccc(C(C)(C)CO)cc3)ncnc2OCCO)cc1.Clc1ncc(Br)cn1 | Cc1ccc(-c2c(NS(=O)(=O)c3ccc(C(C)(C)COc4ncc(Br)cn4)cc3)ncnc2OCCOc2ncc(Br)cn2)cc1 | null | null | C1CCOC1.CC(=O)N(C)C.O1CCCC1 | Aromatic Heterocycle Formation | OtherReaction | dcb76457b2f4185689a5217553a1c82e25a479e17489779887e701fb1ab895e3 | ae8aef24325f0ebf6d21edaa608061a01244b662088df87ba9ea47500cb313da | O=S(=O)(Nc1ncnc(OCCOc2ncccn2)c1-c1ccccc1)c1ccc(CCOc2ncccn2)cc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5].[C;D1;H3:6]-[C;H0;D4;+0:7](-[CH3;D1;+0:8])(-[C:9]-[OH;D1;+0:10])-[c:11](:[c:12]):[c:13].[C:14]-[C:15]-[OH;D1;+0:16]>>[Br;D1;H0:17]-[c:18]1:[c:19]:[#7;a:20]:[c:21](-[O;H0;D2;+0:16]-[C:15]-[C:14]):[#7;a:22]:[cH;D2;+0:8]:1.[C;D1;H3:6]-[C;H0;D4;+0:7](-[C;D1;H3:23])(-[C:9]-[... | 33.8 | [{"value": 33.8, "product": "BrC=1C=NC(=NC1)OCC(C)(C)C1=CC=C(C=C1)S(=O)(=O)NC1=NC=NC(=C1C1=CC=C(C=C1)C)OCCOC1=NC=C(C=N1)Br", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 6 | DAY | To a suspension of sodium hydride (65 mg) in dimethylacetamide (0.5 ml) and tetrahydrofuran (0.5 ml) is added dropwise a solution of 4-(2-hydroxy-1,1-dimethylethyl)-N-{6-[2-hydroxyethoxy]-5-(4-methylphenyl)pyrimidin-4-yl}benzenesulfonamide (135 mg) in dimethylacetamide (2 ml) and THF (2 ml) solution over period of 5 mi... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary alcohol.Primary alcohol | Aromatic halide.Ether.Ether | c1cncnc1 | c1cncnc1.c1cncnc1 | c1ccccc1.c1ccccc1.c1cncnc1.c1cncnc1.c1cncnc1 | null | C1CCOC1.CC(=O)N(C)C.O1CCCC1 | null | 144 | Cc1ccc(-c2c(NS(=O)(=O)c3ccc(C(C)(C)CO)cc3)ncnc2OCCO)cc1.Clc1ncc(Br)cn1>C1CCOC1.CC(=O)N(C)C.O1CCCC1>Cc1ccc(-c2c(NS(=O)(=O)c3ccc(C(C)(C)COc4ncc(Br)cn4)cc3)ncnc2OCCOc2ncc(Br)cn2)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-f9da1fb215d9480cbbff50ec311464de | Cc1ccc(-c2c(NS(=O)(=O)c3ccc(C(C)(C)C)cc3)ncnc2OCCOc2ncc(O)cn2)cc1.Clc1ncc(Br)cn1>>Cc1ccc(-c2c(NS(=O)(=O)c3ccc(C(C)(C)C)cc3)ncnc2OCCOc2ncc(Oc3ncc(Br)cn3)cn2)cc1 | Cl.C(C)(C)(C)C1=CC=C(C=C1)S(=O)(=O)NC1=NC=NC(=C1C1=CC=C(C=C1)C)OCCOC1=NC=C(C=N1)O.C([O-])([O-])=O.[K+].[K+].BrC=1C=NC(=NC1)Cl>>C(C)(C)(C)C1=CC=C(C=C1)S(=O)(=O)NC1=NC=NC(=C1C1=CC=C(C=C1)C)OCCOC1=NC=C(C=N1)OC1=NC=C(C=N1)Br | [CH3:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[c:7]([NH:8][S:9](=[O:10])(=[O:11])[c:12]3[cH:13][cH:14][c:15]([C:16]([CH3:17])([CH3:18])[CH3:19])[cH:20][cH:21]3)[n:22][cH:23][n:24][c:25]2[O:26][CH2:27][CH2:28][O:29][c:30]2[n:31][cH:32][c:33]([OH:34])[cH:42][n:43]2)[cH:44][cH:45]1.Cl[c:35]1[n:36][cH:37][c:38]([Br:39])[cH:40][n:4... | Cc1ccc(-c2c(NS(=O)(=O)c3ccc(C(C)(C)C)cc3)ncnc2OCCOc2ncc(O)cn2)cc1.Clc1ncc(Br)cn1 | Cc1ccc(-c2c(NS(=O)(=O)c3ccc(C(C)(C)C)cc3)ncnc2OCCOc2ncc(Oc3ncc(Br)cn3)cn2)cc1 | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 38da1e480b17968341fc50d07104da93d31f20765e3b36e5a0790cb6b1d88a10 | 27e9a6bab4e3ed54aeb6be4d84cb1c0170208288795e252a46e57e44ecc064f0 | O=S(=O)(Nc1ncnc(OCCOc2ncc(Oc3ncccn3)cn2)c1-c1ccccc1)c1ccccc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5].[OH;D1;+0:6]-[c:7]1:[c:8]:[#7;a:9]:[c:10]:[#7;a:11]:[c:12]:1>>[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[O;H0;D2;+0:6]-[c:7]1:[c:8]:[#7;a:9]:[c:10]:[#7;a:11]:[c:12]:1):[#7;a:4]:[c:5] | 92 | [{"value": 92.0, "product": "C(C)(C)(C)C1=CC=C(C=C1)S(=O)(=O)NC1=NC=NC(=C1C1=CC=C(C=C1)C)OCCOC1=NC=C(C=N1)OC1=NC=C(C=N1)Br", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 50 | CELSIUS | 2 | HOUR | To a solution of 4-tert-butyl-N-{6-[2-(5-hydroxypyrimidin-2-yloxy)ethoxy]-5-(4-methylphenyl)pyrimidin-4-yl}benzenesulfonamide (200 mg) in dimethylformamide (4 ml)is added potassium carbonate (154 mg), 5-bromo-2-chloropyrimidine (216 mg), and the mixture is stirred at 50° C. for two hours. The reaction mixture is acdifi... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic alcohol | Ether | c1cncnc1 | c1cncnc1 | c1ccccc1.c1ccccc1.c1cncnc1.c1cncnc1.c1cncnc1 | HCl | CN(C=O)C | 50 | 2 | Cc1ccc(-c2c(NS(=O)(=O)c3ccc(C(C)(C)C)cc3)ncnc2OCCOc2ncc(O)cn2)cc1.Clc1ncc(Br)cn1>CN(C=O)C>Cc1ccc(-c2c(NS(=O)(=O)c3ccc(C(C)(C)C)cc3)ncnc2OCCOc2ncc(Oc3ncc(Br)cn3)cn2)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-266991e5ffdc435fbe2ec8351449c640 | COc1cccc(Oc2c(Cl)ncnc2NS(=O)(=O)c2ccc(C(C)(C)C)cc2)c1.OCCCO>>COc1cccc(Oc2c(NS(=O)(=O)c3ccc(C(C)(C)C)cc3)ncnc2OCCCO)c1 | Cl.C(CCO)O.[H-].[Na+].C(C)(C)(C)C1=CC=C(C=C1)S(=O)(=O)NC1=NC=NC(=C1OC1=CC(=CC=C1)OC)Cl>>C(C)(C)(C)C1=CC=C(C=C1)S(=O)(=O)NC1=NC=NC(=C1OC1=CC(=CC=C1)OC)OCCCO | Cl[c:28]1[c:9]([O:8][c:7]2[cH:6][cH:5][cH:4][c:3]([O:2][CH3:1])[cH:34]2)[c:10]([NH:11][S:12](=[O:13])(=[O:14])[c:15]2[cH:16][cH:17][c:18]([C:19]([CH3:20])([CH3:21])[CH3:22])[cH:23][cH:24]2)[n:25][cH:26][n:27]1.[OH:29][CH2:30][CH2:31][CH2:32][OH:33]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]([O:8][c:9]2[c:10]([NH:11][S:... | COc1cccc(Oc2c(Cl)ncnc2NS(=O)(=O)c2ccc(C(C)(C)C)cc2)c1.OCCCO | COc1cccc(Oc2c(NS(=O)(=O)c3ccc(C(C)(C)C)cc3)ncnc2OCCCO)c1 | null | null | null | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | a445000eb5ed501274d93689ad5b9d45095af02deca02b6b541c8a834890a276 | a4cafa7bcd156e21cca6eaac1b32e28ec8540642a31181122e6957f3d7559631 | O=S(=O)(Nc1ncncc1Oc1ccccc1)c1ccccc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](-[#7:6]):[c:7]:1-[#8:8].[C:9]-[C:10]-[OH;D1;+0:11]>>[#7:6]-[c:5]1:[#7;a:4]:[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[O;H0;D2;+0:11]-[C:10]-[C:9]):[c:7]:1-[#8:8] | null | [] | null | null | null | null | To 1,3-propanediol (7 ml) is added sodium hydride (60% dispersion-type, 312 mg), and thereto is added 4-tert-butyl-N-{6-chloro-5-(3-methoxyphenoxy)pyrimidin-4-yl}benzenesulfonamide (707 mg). The reaction mixture is reacted at 90° C. for two hours, and then reacted at 130° C. for one hour. The reaction solution is acidi... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary alcohol | Ether | c1cncnc1 | c1cncnc1 | c1ccccc1.c1ccccc1.c1cncnc1 | HCl | null | null | null | COc1cccc(Oc2c(Cl)ncnc2NS(=O)(=O)c2ccc(C(C)(C)C)cc2)c1.OCCCO>>COc1cccc(Oc2c(NS(=O)(=O)c3ccc(C(C)(C)C)cc3)ncnc2OCCCO)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-c78f869bf2a74b75ba8846f932a65794 | Cc1ccc(-c2c(Cl)ncnc2OCCO)cc1.[N-]=[N+]=[N-]>>Cc1ccc(-c2c(N=[N+]=[N-])ncnc2OCCO)cc1 | ClC1=C(C(=NC=N1)OCCO)C1=CC=C(C=C1)C.[N-]=[N+]=[N-].[Na+].CN(C=O)C>>N(=[N+]=[N-])C1=C(C(=NC=N1)OCCO)C1=CC=C(C=C1)C | Cl[c:7]1[c:6](-[c:5]2[cH:4][cH:3][c:2]([CH3:1])[cH:20][cH:19]2)[c:14]([O:15][CH2:16][CH2:17][OH:18])[n:13][cH:12][n:11]1.[N-:8]=[N+:9]=[N-:10]>>[CH3:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[c:7]([N:8]=[N+:9]=[N-:10])[n:11][cH:12][n:13][c:14]2[O:15][CH2:16][CH2:17][OH:18])[cH:19][cH:20]1 | Cc1ccc(-c2c(Cl)ncnc2OCCO)cc1.[N-]=[N+]=[N-] | Cc1ccc(-c2c(N=[N+]=[N-])ncnc2OCCO)cc1 | null | null | O | Heteroatom Alkylation and Arylation | OtherReaction | 48465a5e07f474e518aa4021a9b68659838d8b370bfeed26501047d7c300e8e7 | df579c5e1cf1cc42720dad6dd16c8deec88e9170508fbd47357453cfc40bcb7a | c1ccc(-c2cncnc2)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](-[#8:6]):[c:7]:1-[c:8].[N-;H0;D1:9]=[#7;+:10]=[N;-;D1;H0:11]>>[#8:6]-[c:5]1:[#7;a:4]:[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[N;H0;D2;+0:9]=[#7;+:10]=[N;-;D1;H0:11]):[c:7]:1-[c:8] | 87.5 | [{"value": 87.5, "product": "N(=[N+]=[N-])C1=C(C(=NC=N1)OCCO)C1=CC=C(C=C1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | A mixture of 2-{6-chloro-5-(4-methylphenyl)pyrimidin-4-yloxy}-ethanol (21.85 g), sodium azide (10.7 g) and dimethyformamide (260 ml) is heated with stirring at 75°-80° C. overnight. After cooling, the mixture is treated with water, and extracted with ethyl acetate. The ethyl acetate layer is washed, dried, and evaporat... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | Azide | c1cncnc1 | c1cncnc1 | c1ccccc1.c1cncnc1 | Other | O | null | 8 | Cc1ccc(-c2c(Cl)ncnc2OCCO)cc1.[N-]=[N+]=[N-]>O>Cc1ccc(-c2c(N=[N+]=[N-])ncnc2OCCO)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-5cec6056ae4c4169bd4252bc117b2be6 | Cc1ccc(-c2c(N=[N+]=[N-])ncnc2OCCO)cc1>>Cc1ccc(-c2c(N)ncnc2OCCO)cc1 | N(=[N+]=[N-])C1=C(C(=NC=N1)OCCO)C1=CC=C(C=C1)C>>NC1=C(C(=NC=N1)OCCO)C1=CC=C(C=C1)C | [N-]=[N+]=[N:8][c:7]1[c:6](-[c:5]2[cH:4][cH:3][c:2]([CH3:1])[cH:18][cH:17]2)[c:12]([O:13][CH2:14][CH2:15][OH:16])[n:11][cH:10][n:9]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[c:7]([NH2:8])[n:9][cH:10][n:11][c:12]2[O:13][CH2:14][CH2:15][OH:16])[cH:17][cH:18]1 | Cc1ccc(-c2c(N=[N+]=[N-])ncnc2OCCO)cc1 | Cc1ccc(-c2c(N)ncnc2OCCO)cc1 | null | [C].[Pd] | C(C)O | Reduction | Azide to amine reduction (Staudinger) | 4c9e4990dae2bb965dec06bd45e318560989ee3681b61e443f7aa363b7cfa222 | cd009d687d606bf351eac9390a176d16be38f2c8216a599b398641009c215027 | c1ccc(-c2cncnc2)cc1 | [N-]=[N+]=[N;H0;D2;+0:1]-[c:2]1:[#7;a:3]:[c:4]:[#7;a:5]:[c:6]:[c:7]:1>>[NH2;D1;+0:1]-[c:2]1:[#7;a:3]:[c:4]:[#7;a:5]:[c:6]:[c:7]:1 | 89.7 | [{"value": 89.7, "product": "NC1=C(C(=NC=N1)OCCO)C1=CC=C(C=C1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 2-{6-azido-5-(4-methylphenyl)pyrimidin-4-yloxy}-ethanol (19.6 g), 10% palladium-carbon (50% moist) (4.0 g) and ethanol (240 ml) is subjected to catalytic hydrogenation at room temperature under hydrogen atmosphere (1 atm) for one hour. The catalyst is removed by filtration, and the filtrate is concentrated... | 10.6084/m9.figshare.5104873.v1 | null | Azide | Primary amine | null | null | c1ccccc1.c1cncnc1 | Other | [C].[Pd].C(C)O | null | null | Cc1ccc(-c2c(N=[N+]=[N-])ncnc2OCCO)cc1>[C].[Pd].C(C)O>Cc1ccc(-c2c(N)ncnc2OCCO)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-bd67cbfc2bdf4149825d464041c6164c | Cc1ccc(-c2c(Cl)ncnc2Cl)cc1.N>>Cc1ccc(-c2c(N)ncnc2Cl)cc1 | ClC1=NC=NC(=C1C1=CC=C(C=C1)C)Cl.N.C(C)O>>ClC1=C(C(=NC=N1)N)C1=CC=C(C=C1)C | Cl[c:7]1[c:6](-[c:5]2[cH:4][cH:3][c:2]([CH3:1])[cH:15][cH:14]2)[c:12]([Cl:13])[n:11][cH:10][n:9]1.[NH3:8]>>[CH3:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[c:7]([NH2:8])[n:9][cH:10][n:11][c:12]2[Cl:13])[cH:14][cH:15]1 | Cc1ccc(-c2c(Cl)ncnc2Cl)cc1.N | Cc1ccc(-c2c(N)ncnc2Cl)cc1 | null | null | CCOCC | Heteroatom Alkylation and Arylation | OtherReaction | 90f3138935f3ad06434c84a4ac47f6a17b2b61711b0b3fffea5d29513d5b1a76 | c5668f64a1395fa45312378ed819baaeafc354cdb673b20226ea2853ed14db5d | c1ccc(-c2cncnc2)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](-[Cl;D1;H0:6]):[c:7]:1-[c:8].[NH3;D0;+0:9]>>[Cl;D1;H0:6]-[c:5]1:[#7;a:4]:[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[NH2;D1;+0:9]):[c:7]:1-[c:8] | null | [] | null | null | null | null | To a solution of 4,6-dichloro-5-(4-methylphenyl)pyrimidine (4.14 g) in ether (20 ml) is added 27% ammonia-ethanol solution (30 ml), and the reaction mixture is reacted at room temperature in a sealed tube for three days. The mixture is concentrated under reduced pressure, and the residue is purified by silica gel colum... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | Primary amine | c1cncnc1 | c1cncnc1 | c1ccccc1.c1cncnc1 | HCl | CCOCC | null | null | Cc1ccc(-c2c(Cl)ncnc2Cl)cc1.N>CCOCC>Cc1ccc(-c2c(N)ncnc2Cl)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-c45d1e41cd734870bba0fc8cf09b8c4c | Cc1ccc(-c2c(N)ncnc2Cl)cc1.OCCO>>Cc1ccc(-c2c(N)ncnc2OCCO)cc1 | [Cl-].[NH4+].ClC1=C(C(=NC=N1)N)C1=CC=C(C=C1)C.[H-].[Na+].C(CO)O>>NC1=C(C(=NC=N1)OCCO)C1=CC=C(C=C1)C | Cl[c:12]1[c:6](-[c:5]2[cH:4][cH:3][c:2]([CH3:1])[cH:18][cH:17]2)[c:7]([NH2:8])[n:9][cH:10][n:11]1.[OH:13][CH2:14][CH2:15][OH:16]>>[CH3:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[c:7]([NH2:8])[n:9][cH:10][n:11][c:12]2[O:13][CH2:14][CH2:15][OH:16])[cH:17][cH:18]1 | Cc1ccc(-c2c(N)ncnc2Cl)cc1.OCCO | Cc1ccc(-c2c(N)ncnc2OCCO)cc1 | null | null | null | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | a445000eb5ed501274d93689ad5b9d45095af02deca02b6b541c8a834890a276 | a4cafa7bcd156e21cca6eaac1b32e28ec8540642a31181122e6957f3d7559631 | c1ccc(-c2cncnc2)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](-[N;D1;H2:6]):[c:7]:1-[c:8].[C:9]-[C:10]-[OH;D1;+0:11]>>[C:9]-[C:10]-[O;H0;D2;+0:11]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](-[N;D1;H2:6]):[c:7]:1-[c:8] | null | [] | null | null | null | null | A mixture of 6-chloro-5-(4-methylphenyl)pyrimidin-4-amine (500 mg), ethylene glycol (10 ml) and sodium hydride (60% dispersion-type, 0.46 g) is reacted at 70° C. for two hours, and reacted at 90° C. for five hours. The mixture is treated with saturated aqueous ammonium chloride solution, and extracted with ethyl acetat... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary alcohol | Ether | c1cncnc1 | c1cncnc1 | c1ccccc1.c1cncnc1 | HCl | null | null | null | Cc1ccc(-c2c(N)ncnc2Cl)cc1.OCCO>>Cc1ccc(-c2c(N)ncnc2OCCO)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-a7b7ef5f674140eda2b87b65e3637f7d | Cc1ccc(-c2c(N)ncnc2OCCO)cc1.Clc1ncc(Br)cn1>>Cc1ccc(-c2c(N)ncnc2OCCOc2ncc(Br)cn2)cc1 | [Cl-].[NH4+].BrC=1C=NC(=NC1)Cl.NC1=C(C(=NC=N1)OCCO)C1=CC=C(C=C1)C.[H-].[Na+]>>BrC=1C=NC(=NC1)OCCOC1=C(C(=NC=N1)N)C1=CC=C(C=C1)C | [CH3:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[c:7]([NH2:8])[n:9][cH:10][n:11][c:12]2[O:13][CH2:14][CH2:15][OH:16])[cH:24][cH:25]1.Cl[c:17]1[n:18][cH:19][c:20]([Br:21])[cH:22][n:23]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[c:7]([NH2:8])[n:9][cH:10][n:11][c:12]2[O:13][CH2:14][CH2:15][O:16][c:17]2[n:18][cH:19][c:20]([Br:21])[cH:... | Cc1ccc(-c2c(N)ncnc2OCCO)cc1.Clc1ncc(Br)cn1 | Cc1ccc(-c2c(N)ncnc2OCCOc2ncc(Br)cn2)cc1 | null | null | O1CCCC1 | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | a445000eb5ed501274d93689ad5b9d45095af02deca02b6b541c8a834890a276 | a4cafa7bcd156e21cca6eaac1b32e28ec8540642a31181122e6957f3d7559631 | c1ccc(-c2cncnc2OCCOc2ncccn2)cc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5].[C:6]-[C:7]-[OH;D1;+0:8]>>[C:6]-[C:7]-[O;H0;D2;+0:8]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5] | 91.1 | [{"value": 91.1, "product": "BrC=1C=NC(=NC1)OCCOC1=C(C(=NC=N1)N)C1=CC=C(C=C1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | To a solution of 2-{6-amino-5-(4-methylphenyl)pyrimidin-4-yloxy}-ethanol (7.54 g) in tetrahydrofuran (150 ml) is added sodium hydride (60% dispersion-type, 1.47 g), and thereto is added 5-bromo-2-chloropyrimidine (7.73 g), and the mixture is stirred at room temperature overnight. To the reaction solution is added satur... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary alcohol | Ether | c1cncnc1 | c1cncnc1 | c1ccccc1.c1cncnc1.c1cncnc1 | HCl | O1CCCC1 | null | 8 | Cc1ccc(-c2c(N)ncnc2OCCO)cc1.Clc1ncc(Br)cn1>O1CCCC1>Cc1ccc(-c2c(N)ncnc2OCCOc2ncc(Br)cn2)cc1 |
Subsets and Splits
No community queries yet
The top public SQL queries from the community will appear here once available.