dataset_id large_stringclasses 414
values | reaction_id large_stringlengths 36 36 | reaction_smiles large_stringlengths 4 873 | rxn_insight_reaction large_stringlengths 19 1.07k | mapped_reaction_smiles large_stringlengths 14 3.37k | reactant_smiles large_stringlengths 1 581 | product_smiles large_stringlengths 1 433 | reagent_smiles large_stringclasses 634
values | catalyst_smiles large_stringlengths 1 683 ⌀ | solvent_smiles large_stringlengths 1 245 ⌀ | rxn_insight_class large_stringclasses 11
values | rxn_insight_name large_stringclasses 346
values | rxn_insight_tag large_stringlengths 64 64 | rxn_insight_tag2 large_stringlengths 64 64 | rxn_insight_scaffold large_stringlengths 5 288 ⌀ | rxn_insight_template large_stringlengths 24 2.64k ⌀ | yield_percent float64 -0.8 90,205,160,000B ⌀ | yield_measurements large_stringlengths 2 864 | temperature_value float64 -230 30.1k ⌀ | temperature_units large_stringclasses 3
values | reaction_time_value float64 0 4k ⌀ | time_units large_stringclasses 4
values | procedure_details large_stringlengths 1 23.6k ⌀ | reference large_stringclasses 96
values | doi large_stringclasses 19
values | functional_groups_reactants large_stringlengths 3 716 ⌀ | functional_groups_products large_stringlengths 3 539 ⌀ | participating_rings_reactants large_stringlengths 5 293 ⌀ | participating_rings_products large_stringlengths 5 271 ⌀ | all_rings_products large_stringlengths 5 271 ⌀ | byproduct_smiles large_stringclasses 176
values | agent_smiles large_stringlengths 1 712 ⌀ | temperature_c float64 -230 30.1k ⌀ | reaction_time_hours float64 0 2.16k ⌀ | reaction_smiles_with_agents large_stringlengths 4 882 |
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-2e4f1814c45a4d49ad767afa4112ca37 | COC(=O)c1cc(-c2ccc(C(F)(F)F)cc2)oc1C>>COC(=O)c1cc(-c2ccc(C(F)(F)F)cc2)oc1CBr | S(=O)(O)[O-].[Na+].Br(=O)(=O)[O-].[Na+].CC=1OC(=CC1C(=O)OC)C1=CC=C(C=C1)C(F)(F)F.CC=1OC(=CC1C(=O)OC)C1=CC=C(C=C1)C(F)(F)F.C(C)OCC>>BrCC=1OC(=CC1C(=O)OC)C1=CC=C(C=C1)C(F)(F)F | [CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7](-[c:8]2[cH:9][cH:10][c:11]([C:12]([F:13])([F:14])[F:15])[cH:16][cH:17]2)[o:18][c:19]1[CH3:20]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7](-[c:8]2[cH:9][cH:10][c:11]([C:12]([F:13])([F:14])[F:15])[cH:16][cH:17]2)[o:18][c:19]1[CH2:20][Br:21] | COC(=O)c1cc(-c2ccc(C(F)(F)F)cc2)oc1C | COC(=O)c1cc(-c2ccc(C(F)(F)F)cc2)oc1CBr | null | null | C1CCCCC1.O | Functional Group Addition | Bromination | ca537da020427de460728e4a46844f31fb9ac78bacba6b64ec890c6a63cf7c56 | 814107e7eb6098cbc76bc1ba0b008fd579e7d14ef25761860dc78b2c0289c23e | c1ccc(-c2ccco2)cc1 | [#8:1]-[C:2](=[O;D1;H0:3])-[c:4]:[c:5](-[CH3;D1;+0:6]):[#8;a:7]:[c:8]>>[#8:1]-[C:2](=[O;D1;H0:3])-[c:4]:[c:5](-[CH2;D2;+0:6]-[Br;D1;H0:9]):[#8;a:7]:[c:8] | null | [] | 10 | CELSIUS | null | null | A solution of sodium bromate (8.14 g) in water (27 ml) was treated with a suspension of methyl 2-methyl-5-[4-(trifluoromethyl)phenyl]-3-furoate (intermediate 23, 5.12 g) in cyclohexane (36 ml). The system was cooled to <10° C. in ice/water bath and treated with a solution of sodium hydrogen sulfite (9.4 g) in water (54... | 10.6084/m9.figshare.5104873.v1 | null | null | Primary halide | null | null | c1ccoc1.c1ccccc1 | Other | C1CCCCC1.O | 10 | null | COC(=O)c1cc(-c2ccc(C(F)(F)F)cc2)oc1C>C1CCCCC1.O>COC(=O)c1cc(-c2ccc(C(F)(F)F)cc2)oc1CBr |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-dd4a8782106f4e99b7bf266d0a434e30 | CCOC(=O)c1sc(-c2ccc(C(F)(F)F)cc2)cc1CBr.SCc1ccccc1>>CCOC(=O)c1sc(-c2ccc(C(F)(F)F)cc2)cc1CSCc1ccccc1 | BrCC1=C(SC(=C1)C1=CC=C(C=C1)C(F)(F)F)C(=O)OCC.BrCC1=C(SC(=C1)C1=CC=C(C=C1)C(F)(F)F)C(=O)OCC.C(C1=CC=CC=C1)S.C([O-])([O-])=O.[K+].[K+]>>C(C1=CC=CC=C1)SCC1=C(SC(=C1)C1=CC=C(C=C1)C(F)(F)F)C(=O)OCC | Br[CH2:21][c:20]1[c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[s:7][c:8](-[c:9]2[cH:10][cH:11][c:12]([C:13]([F:14])([F:15])[F:16])[cH:17][cH:18]2)[cH:19]1.[SH:22][CH2:23][c:24]1[cH:25][cH:26][cH:27][cH:28][cH:29]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[s:7][c:8](-[c:9]2[cH:10][cH:11][c:12]([C:13]([F:14])([F:15])[F:16])[cH:1... | CCOC(=O)c1sc(-c2ccc(C(F)(F)F)cc2)cc1CBr.SCc1ccccc1 | CCOC(=O)c1sc(-c2ccc(C(F)(F)F)cc2)cc1CSCc1ccccc1 | null | null | C(C)#N | Heteroatom Alkylation and Arylation | S-alkylation of thiols (ethyl) | 77cd742b5ba20df0e225494f6e5f3d958ee82ce9a1b16fd99a2d9f8350b4fdc8 | b05f7dda7dad719ae1868a84c33eeaf5bf649036fc64173cf4774a5eb4d70181 | c1ccc(CSCc2csc(-c3ccccc3)c2)cc1 | Br-[CH2;D2;+0:1]-[c:2]1:[c:3]:[c:4]:[#16;a:5]:[c:6]:1-[C:7](-[#8:8])=[O;D1;H0:9].[SH;D1;+0:10]-[C:11]-[c:12]>>[#8:8]-[C:7](=[O;D1;H0:9])-[c:6]1:[#16;a:5]:[c:4]:[c:3]:[c:2]:1-[CH2;D2;+0:1]-[S;H0;D2;+0:10]-[C:11]-[c:12] | null | [] | null | null | 8 | HOUR | A solution of ethyl 3-(bromomethyl)-5-[4-(trifluoromethyl)phenyl]thiophene-2-carboxylate (intermediate 43, 0.100 g) and benzyl mercaptan (0.30 g) in acetonitrile (10 ml) was treated with potassium carbonate (0.46 g) and the mixture stirred at ambient temperature overnight. The reaction mixture was partitioned between e... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aliphatic thiol | Monosulfide | null | null | c1ccsc1.c1ccccc1.c1ccccc1 | HBr | C(C)#N | null | 8 | CCOC(=O)c1sc(-c2ccc(C(F)(F)F)cc2)cc1CBr.SCc1ccccc1>C(C)#N>CCOC(=O)c1sc(-c2ccc(C(F)(F)F)cc2)cc1CSCc1ccccc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-970f584521ce4e678ff7c29f9c38f8c9 | CCOC(=O)c1sc(-c2ccc(C(F)(F)F)cc2)cc1CSCc1ccccc1>>OCc1sc(-c2ccc(C(F)(F)F)cc2)cc1CSCc1ccccc1 | O.C(C1=CC=CC=C1)SCC1=C(SC(=C1)C1=CC=C(C=C1)C(F)(F)F)C(=O)OCC.C(C1=CC=CC=C1)SCC1=C(SC(=C1)C1=CC=C(C=C1)C(F)(F)F)C(=O)OCC.[H-].[Al+3].[Li+].[H-].[H-].[H-].Cl>>C(C1=CC=CC=C1)SCC1=C(SC(=C1)C1=CC=C(C=C1)C(F)(F)F)CO | CCO[C:2](=[O:1])[c:3]1[s:4][c:5](-[c:6]2[cH:7][cH:8][c:9]([C:10]([F:11])([F:12])[F:13])[cH:14][cH:15]2)[cH:16][c:17]1[CH2:18][S:19][CH2:20][c:21]1[cH:22][cH:23][cH:24][cH:25][cH:26]1>>[OH:1][CH2:2][c:3]1[s:4][c:5](-[c:6]2[cH:7][cH:8][c:9]([C:10]([F:11])([F:12])[F:13])[cH:14][cH:15]2)[cH:16][c:17]1[CH2:18][S:19][CH2:20]... | CCOC(=O)c1sc(-c2ccc(C(F)(F)F)cc2)cc1CSCc1ccccc1 | OCc1sc(-c2ccc(C(F)(F)F)cc2)cc1CSCc1ccccc1 | null | null | O1CCCC1.CCOCC | Reduction | Reduction of ester to primary alcohol | 21d61543c6ec8a8cebe1b3ef55ef3dd20acbf79a4f1c12a7fb51e32be7a3248a | 1fbcd628a0426673c5d10aa49a977cd2d1ae02a8cdf57bbb10d94aa03a94e937 | c1ccc(CSCc2csc(-c3ccccc3)c2)cc1 | C-C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[c:3](:[c:4]):[#16;a:5]:[c:6]>>[OH;D1;+0:2]-[CH2;D2;+0:1]-[c:3](:[c:4]):[#16;a:5]:[c:6] | null | [] | null | null | null | null | A solution of ethyl 3-[(benzylthio)methyl]-5-[4-(trifluoromethyl)phenyl]thiophene-2-carboxylate (intermediate 45, 0.87 g) in dry tetrahydrofuran (5 ml) was cooled to 0° C. and 1M lithium aluminium hydride solution in diethyl, ether (0.299 ml) added. The reaction mixture as stirred with cooling for 3 hours. Water (0.5 m... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary alcohol | null | null | c1ccsc1.c1ccccc1.c1ccccc1 | HO- | O1CCCC1.CCOCC | null | null | CCOC(=O)c1sc(-c2ccc(C(F)(F)F)cc2)cc1CSCc1ccccc1>O1CCCC1.CCOCC>OCc1sc(-c2ccc(C(F)(F)F)cc2)cc1CSCc1ccccc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-2e95888c3ff84a0fb8e3c2a881c4f9d9 | CCOC(=O)c1sc(-c2ccc(C(F)(F)F)cc2)cc1CBr.Oc1ccccc1>>OCc1sc(-c2ccc(C(F)(F)F)cc2)cc1COc1ccccc1 | BrCC1=C(SC(=C1)C1=CC=C(C=C1)C(F)(F)F)C(=O)OCC.C1(=CC=CC=C1)O>>O(C1=CC=CC=C1)CC1=C(SC(=C1)C1=CC=C(C=C1)C(F)(F)F)CO | CCO[C:2](=[O:1])[c:3]1[s:4][c:5](-[c:6]2[cH:7][cH:8][c:9]([C:10]([F:11])([F:12])[F:13])[cH:14][cH:15]2)[cH:16][c:17]1[CH2:18]Br.[OH:19][c:20]1[cH:21][cH:22][cH:23][cH:24][cH:25]1>>[OH:1][CH2:2][c:3]1[s:4][c:5](-[c:6]2[cH:7][cH:8][c:9]([C:10]([F:11])([F:12])[F:13])[cH:14][cH:15]2)[cH:16][c:17]1[CH2:18][O:19][c:20]1[cH:2... | CCOC(=O)c1sc(-c2ccc(C(F)(F)F)cc2)cc1CBr.Oc1ccccc1 | OCc1sc(-c2ccc(C(F)(F)F)cc2)cc1COc1ccccc1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | c176f489b2a0aec18a165134f247edbb416190f25898c2d4da2a773f18aac4b8 | c53e40ba1eff467f03d6efc966ae7bc0310980572b314c3d58e1697358a3b316 | c1ccc(OCc2csc(-c3ccccc3)c2)cc1 | Br-[CH2;D2;+0:1]-[c:2]1:[c:3]:[c:4]:[#16;a:5]:[c:6]:1-[C;H0;D3;+0:7](=[O;H0;D1;+0:8])-O-C-C.[OH;D1;+0:9]-[c:10](:[c:11]):[c:12]>>[OH;D1;+0:8]-[CH2;D2;+0:7]-[c:6]1:[#16;a:5]:[c:4]:[c:3]:[c:2]:1-[CH2;D2;+0:1]-[O;H0;D2;+0:9]-[c:10](:[c:11]):[c:12] | null | [] | null | null | null | null | Prepared from intermediate 43 and phenol
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester.Aromatic alcohol | Ether.Primary alcohol | null | null | c1ccsc1.c1ccccc1.c1ccccc1 | HBr | null | null | null | CCOC(=O)c1sc(-c2ccc(C(F)(F)F)cc2)cc1CBr.Oc1ccccc1>>OCc1sc(-c2ccc(C(F)(F)F)cc2)cc1COc1ccccc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-ae8b6db692d04441a65dd7b35c322628 | CC(C)S.CCOC(=O)c1sc(-c2ccc(C(F)(F)F)cc2)cc1CBr>>CC(C)SCc1cc(-c2ccc(C(F)(F)F)cc2)sc1CO | BrCC1=C(SC(=C1)C1=CC=C(C=C1)C(F)(F)F)C(=O)OCC.CC(C)S>>C(C)(C)SCC1=C(SC(=C1)C1=CC=C(C=C1)C(F)(F)F)CO | [CH3:1][CH:2]([CH3:3])[SH:4].CCO[C:21]([c:20]1[c:6]([CH2:5]Br)[cH:7][c:8](-[c:9]2[cH:10][cH:11][c:12]([C:13]([F:14])([F:15])[F:16])[cH:17][cH:18]2)[s:19]1)=[O:22]>>[CH3:1][CH:2]([CH3:3])[S:4][CH2:5][c:6]1[cH:7][c:8](-[c:9]2[cH:10][cH:11][c:12]([C:13]([F:14])([F:15])[F:16])[cH:17][cH:18]2)[s:19][c:20]1[CH2:21][OH:22] | CC(C)S.CCOC(=O)c1sc(-c2ccc(C(F)(F)F)cc2)cc1CBr | CC(C)SCc1cc(-c2ccc(C(F)(F)F)cc2)sc1CO | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | e449c424d502450e30627dd5bf732dc7c8a0a639dd86e0480f8c88fd6617a92f | 70fdc9d517f1bd60ca2a96b9128763fe511b02c2db4dd31afe5f6d010faf6a3a | c1ccc(-c2cccs2)cc1 | Br-[CH2;D2;+0:1]-[c:2]1:[c:3]:[c:4]:[#16;a:5]:[c:6]:1-[C;H0;D3;+0:7](=[O;H0;D1;+0:8])-O-C-C.[C;D1;H3:9]-[C:10](-[C;D1;H3:11])-[SH;D1;+0:12]>>[C;D1;H3:9]-[C:10](-[C;D1;H3:11])-[S;H0;D2;+0:12]-[CH2;D2;+0:1]-[c:2]1:[c:3]:[c:4]:[#16;a:5]:[c:6]:1-[CH2;D2;+0:7]-[OH;D1;+0:8] | null | [] | null | null | null | null | Prepared from intermediate 43 and isopropylthiol
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester.Aliphatic thiol | Primary alcohol.Monosulfide | null | null | c1ccsc1.c1ccccc1 | HBr | null | null | null | CC(C)S.CCOC(=O)c1sc(-c2ccc(C(F)(F)F)cc2)cc1CBr>>CC(C)SCc1cc(-c2ccc(C(F)(F)F)cc2)sc1CO |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b23a0f8e590a4f68ab5573dd18023026 | CCOC(=O)c1sc(-c2ccc(C(F)(F)F)cc2)cc1CBr.Oc1ccc(C(F)(F)F)cc1>>OCc1sc(-c2ccc(C(F)(F)F)cc2)cc1COc1ccc(C(F)(F)F)cc1 | BrCC1=C(SC(=C1)C1=CC=C(C=C1)C(F)(F)F)C(=O)OCC.FC(C1=CC=C(C=C1)O)(F)F>>FC(C1=CC=C(OCC2=C(SC(=C2)C2=CC=C(C=C2)C(F)(F)F)CO)C=C1)(F)F | CCO[C:2](=[O:1])[c:3]1[s:4][c:5](-[c:6]2[cH:7][cH:8][c:9]([C:10]([F:11])([F:12])[F:13])[cH:14][cH:15]2)[cH:16][c:17]1[CH2:18]Br.[OH:19][c:20]1[cH:21][cH:22][c:23]([C:24]([F:25])([F:26])[F:27])[cH:28][cH:29]1>>[OH:1][CH2:2][c:3]1[s:4][c:5](-[c:6]2[cH:7][cH:8][c:9]([C:10]([F:11])([F:12])[F:13])[cH:14][cH:15]2)[cH:16][c:1... | CCOC(=O)c1sc(-c2ccc(C(F)(F)F)cc2)cc1CBr.Oc1ccc(C(F)(F)F)cc1 | OCc1sc(-c2ccc(C(F)(F)F)cc2)cc1COc1ccc(C(F)(F)F)cc1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | c176f489b2a0aec18a165134f247edbb416190f25898c2d4da2a773f18aac4b8 | c53e40ba1eff467f03d6efc966ae7bc0310980572b314c3d58e1697358a3b316 | c1ccc(OCc2csc(-c3ccccc3)c2)cc1 | Br-[CH2;D2;+0:1]-[c:2]1:[c:3]:[c:4]:[#16;a:5]:[c:6]:1-[C;H0;D3;+0:7](=[O;H0;D1;+0:8])-O-C-C.[OH;D1;+0:9]-[c:10](:[c:11]):[c:12]>>[OH;D1;+0:8]-[CH2;D2;+0:7]-[c:6]1:[#16;a:5]:[c:4]:[c:3]:[c:2]:1-[CH2;D2;+0:1]-[O;H0;D2;+0:9]-[c:10](:[c:11]):[c:12] | null | [] | null | null | null | null | Prepared from intermediate 43 and 4-(trifluoromethyl)phenol
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester.Aromatic alcohol | Ether.Primary alcohol | null | null | c1ccsc1.c1ccccc1.c1ccccc1 | HBr | null | null | null | CCOC(=O)c1sc(-c2ccc(C(F)(F)F)cc2)cc1CBr.Oc1ccc(C(F)(F)F)cc1>>OCc1sc(-c2ccc(C(F)(F)F)cc2)cc1COc1ccc(C(F)(F)F)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-f6ddaba673be4decb2b45330286d6069 | COC(=O)c1cc(-c2ccc(C(F)(F)F)cc2)oc1CBr.c1ccc(P(c2ccccc2)c2ccccc2)cc1>>COC(=O)c1cc(-c2ccc(C(F)(F)F)cc2)oc1C[P+](c1ccccc1)(c1ccccc1)c1ccccc1.[Br-] | BrCC=1OC(=CC1C(=O)OC)C1=CC=C(C=C1)C(F)(F)F.BrCC=1OC(=CC1C(=O)OC)C1=CC=C(C=C1)C(F)(F)F.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1>>[Br-].COC(=O)C1=C(OC(=C1)C1=CC=C(C=C1)C(F)(F)F)C[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1 | [CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7](-[c:8]2[cH:9][cH:10][c:11]([C:12]([F:13])([F:14])[F:15])[cH:16][cH:17]2)[o:18][c:19]1[CH2:20][Br:40].[P:21]([c:22]1[cH:23][cH:24][cH:25][cH:26][cH:27]1)([c:28]1[cH:29][cH:30][cH:31][cH:32][cH:33]1)[c:34]1[cH:35][cH:36][cH:37][cH:38][cH:39]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:... | COC(=O)c1cc(-c2ccc(C(F)(F)F)cc2)oc1CBr.c1ccc(P(c2ccccc2)c2ccccc2)cc1 | COC(=O)c1cc(-c2ccc(C(F)(F)F)cc2)oc1C[P+](c1ccccc1)(c1ccccc1)c1ccccc1.[Br-] | null | null | C1(=CC=CC=C1)C | Functional Group Interconversion | OtherReaction | 72a5231b07f184f0ef4a0648badd4176f521b95f1ba3340a0f90d8894af47260 | 47a659f5704a5b7ca1b92ff731f18f109c6bde1d45152a3a393eefbd10265508 | c1ccc(-c2ccc(C[P+](c3ccccc3)(c3ccccc3)c3ccccc3)o2)cc1 | [#8:1]-[C:2](=[O;D1;H0:3])-[c:4]:[c:5](-[CH2;D2;+0:6]-[Br;H0;D1;+0:7]):[#8;a:8]:[c:9].[c:10]:[c:11](-[P;H0;D3;+0:12](-[c:13](:[c:14]):[c:15])-[c:16](:[c:17]):[c:18]):[c:19]>>[#8:1]-[C:2](=[O;D1;H0:3])-[c:4]:[c:5](-[CH2;D2;+0:6]-[P+;H0;D4:12](-[c:11](:[c:10]):[c:19])(-[c:13](:[c:14]):[c:15])-[c:16](:[c:17]):[c:18]):[#8;... | null | [] | null | null | null | null | Methyl 2-bromomethyl-5-[4-(trifluoromethyl)phenyl]-3-furoate (intermediate 44, 0.20 g) was dissolved in toluene (3 ml) treated with triphenylphosphine (0.159 g) and heated to reflux for 1 hour. The reaction was allowed to cool and the white precipitate was collected by filtration, washed with fresh toluene to give the ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | null | null | c1ccoc1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | null | C1(=CC=CC=C1)C | null | null | COC(=O)c1cc(-c2ccc(C(F)(F)F)cc2)oc1CBr.c1ccc(P(c2ccccc2)c2ccccc2)cc1>C1(=CC=CC=C1)C>COC(=O)c1cc(-c2ccc(C(F)(F)F)cc2)oc1C[P+](c1ccccc1)(c1ccccc1)c1ccccc1.[Br-] |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-23f9c05e875c4e10a0232c503746efde | COC(=O)c1cc(-c2ccc(C(F)(F)F)cc2)oc1C[P+](c1ccccc1)(c1ccccc1)c1ccccc1.Cc1ccc(C=O)cc1>>Cc1ccc(CCc2oc(-c3ccc(C(F)(F)F)cc3)cc2CO)cc1 | [Br-].COC(=O)C1=C(OC(=C1)C1=CC=C(C=C1)C(F)(F)F)C[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1.CC1=CC=C(C=O)C=C1>>CC1=CC=C(C=C1)CCC=1OC(=CC1CO)C1=CC=C(C=C1)C(F)(F)F | CO[C:23]([c:22]1[c:8]([CH2:7][P+](c2ccccc2)(c2ccccc2)c2ccccc2)[o:9][c:10](-[c:11]2[cH:12][cH:13][c:14]([C:15]([F:16])([F:17])[F:18])[cH:19][cH:20]2)[cH:21]1)=[O:24].O=[CH:6][c:5]1[cH:4][cH:3][c:2]([CH3:1])[cH:26][cH:25]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([CH2:6][CH2:7][c:8]2[o:9][c:10](-[c:11]3[cH:12][cH:13][c:14]([C:15]... | COC(=O)c1cc(-c2ccc(C(F)(F)F)cc2)oc1C[P+](c1ccccc1)(c1ccccc1)c1ccccc1.Cc1ccc(C=O)cc1 | Cc1ccc(CCc2oc(-c3ccc(C(F)(F)F)cc3)cc2CO)cc1 | null | null | null | C-C Coupling | OtherReaction | 62b1b322a1b2e1bb83754804ce01ec391c66448d4d981c83298f602e5a93b8fb | 99b676a1125583618650e22572a8036417759cffe7bda8f653e4f22bf25a50a4 | c1ccc(CCc2ccc(-c3ccccc3)o2)cc1 | C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[c:3]1:[c:4]:[c:5]:[#8;a:6]:[c:7]:1-[CH2;D2;+0:8]-[P+](-c1:c:c:c:c:c:1)(-c1:c:c:c:c:c:1)-c1:c:c:c:c:c:1.O=[CH;D2;+0:9]-[c:10](:[c:11]):[c:12]>>[OH;D1;+0:2]-[CH2;D2;+0:1]-[c:3]1:[c:4]:[c:5]:[#8;a:6]:[c:7]:1-[CH2;D2;+0:8]-[CH2;D2;+0:9]-[c:10](:[c:11]):[c:12] | null | [] | null | null | null | null | prepare from intermediate 62 and 4-methylbenzaldehyde
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ester | Primary alcohol | c1ccccc1.c1ccccc1.c1ccccc1 | null | c1ccccc1.c1ccoc1.c1ccccc1 | HO- | null | null | null | COC(=O)c1cc(-c2ccc(C(F)(F)F)cc2)oc1C[P+](c1ccccc1)(c1ccccc1)c1ccccc1.Cc1ccc(C=O)cc1>>Cc1ccc(CCc2oc(-c3ccc(C(F)(F)F)cc3)cc2CO)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-04cb01da013e4d209aa3a8604394347d | CC(C)C=O.COC(=O)c1cc(-c2ccc(C(F)(F)F)cc2)oc1C[P+](c1ccccc1)(c1ccccc1)c1ccccc1>>CC(C)CCc1oc(-c2ccc(C(F)(F)F)cc2)cc1CO | [Br-].COC(=O)C1=C(OC(=C1)C1=CC=C(C=C1)C(F)(F)F)C[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1.CC(C=O)C>>C(CC(C)C)C=1OC(=CC1CO)C1=CC=C(C=C1)C(F)(F)F | O=[CH:4][CH:2]([CH3:1])[CH3:3].CO[C:21]([c:20]1[c:6]([CH2:5][P+](c2ccccc2)(c2ccccc2)c2ccccc2)[o:7][c:8](-[c:9]2[cH:10][cH:11][c:12]([C:13]([F:14])([F:15])[F:16])[cH:17][cH:18]2)[cH:19]1)=[O:22]>>[CH3:1][CH:2]([CH3:3])[CH2:4][CH2:5][c:6]1[o:7][c:8](-[c:9]2[cH:10][cH:11][c:12]([C:13]([F:14])([F:15])[F:16])[cH:17][cH:18]2... | CC(C)C=O.COC(=O)c1cc(-c2ccc(C(F)(F)F)cc2)oc1C[P+](c1ccccc1)(c1ccccc1)c1ccccc1 | CC(C)CCc1oc(-c2ccc(C(F)(F)F)cc2)cc1CO | null | null | null | C-C Coupling | OtherReaction | 62b1b322a1b2e1bb83754804ce01ec391c66448d4d981c83298f602e5a93b8fb | 99b676a1125583618650e22572a8036417759cffe7bda8f653e4f22bf25a50a4 | c1ccc(-c2ccco2)cc1 | C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[c:3]1:[c:4]:[c:5]:[#8;a:6]:[c:7]:1-[CH2;D2;+0:8]-[P+](-c1:c:c:c:c:c:1)(-c1:c:c:c:c:c:1)-c1:c:c:c:c:c:1.O=[CH;D2;+0:9]-[C:10](-[C;D1;H3:11])-[C;D1;H3:12]>>[C;D1;H3:11]-[C:10](-[C;D1;H3:12])-[CH2;D2;+0:9]-[CH2;D2;+0:8]-[c:7]1:[#8;a:6]:[c:5]:[c:4]:[c:3]:1-[CH2;D2;+0:1]-[OH;D1;+0:2] | null | [] | null | null | null | null | Prepared from intermediate 62 and 2-methylpropanal
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ester | Primary alcohol | c1ccccc1.c1ccccc1.c1ccccc1 | null | c1ccoc1.c1ccccc1 | HO- | null | null | null | CC(C)C=O.COC(=O)c1cc(-c2ccc(C(F)(F)F)cc2)oc1C[P+](c1ccccc1)(c1ccccc1)c1ccccc1>>CC(C)CCc1oc(-c2ccc(C(F)(F)F)cc2)cc1CO |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-eac842baaa6b4a0a9a150ca3464ed4ce | CC(C)=O.COC(=O)c1cc(-c2ccc(C(F)(F)F)cc2)oc1C[P+](c1ccccc1)(c1ccccc1)c1ccccc1>>CC(C)Cc1oc(-c2ccc(C(F)(F)F)cc2)cc1CO | [Br-].COC(=O)C1=C(OC(=C1)C1=CC=C(C=C1)C(F)(F)F)C[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1.CC(C)=O>>C(C(C)C)C=1OC(=CC1CO)C1=CC=C(C=C1)C(F)(F)F | O=[C:2]([CH3:1])[CH3:3].CO[C:20]([c:19]1[c:5]([CH2:4][P+](c2ccccc2)(c2ccccc2)c2ccccc2)[o:6][c:7](-[c:8]2[cH:9][cH:10][c:11]([C:12]([F:13])([F:14])[F:15])[cH:16][cH:17]2)[cH:18]1)=[O:21]>>[CH3:1][CH:2]([CH3:3])[CH2:4][c:5]1[o:6][c:7](-[c:8]2[cH:9][cH:10][c:11]([C:12]([F:13])([F:14])[F:15])[cH:16][cH:17]2)[cH:18][c:19]1[... | CC(C)=O.COC(=O)c1cc(-c2ccc(C(F)(F)F)cc2)oc1C[P+](c1ccccc1)(c1ccccc1)c1ccccc1 | CC(C)Cc1oc(-c2ccc(C(F)(F)F)cc2)cc1CO | null | null | null | C-C Coupling | OtherReaction | 709f5067b2a1f4d7df436c597f6b545aa9c6148b1a54a9b22c13e9ad78e1a2ca | 03ce0f79dd1bf09d7a4e3217e7cf3f758239a05b7189623cdf31ec04660bbcaf | c1ccc(-c2ccco2)cc1 | C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[c:3]1:[c:4]:[c:5]:[#8;a:6]:[c:7]:1-[CH2;D2;+0:8]-[P+](-c1:c:c:c:c:c:1)(-c1:c:c:c:c:c:1)-c1:c:c:c:c:c:1.O=[C;H0;D3;+0:9](-[C;D1;H3:10])-[C;D1;H3:11]>>[C;D1;H3:10]-[CH;D3;+0:9](-[C;D1;H3:11])-[CH2;D2;+0:8]-[c:7]1:[#8;a:6]:[c:5]:[c:4]:[c:3]:1-[CH2;D2;+0:1]-[OH;D1;+0:2] | null | [] | null | null | null | null | Prepared from intermediate 62 and propanone
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ester | Primary alcohol | c1ccccc1.c1ccccc1.c1ccccc1 | null | c1ccoc1.c1ccccc1 | HO- | null | null | null | CC(C)=O.COC(=O)c1cc(-c2ccc(C(F)(F)F)cc2)oc1C[P+](c1ccccc1)(c1ccccc1)c1ccccc1>>CC(C)Cc1oc(-c2ccc(C(F)(F)F)cc2)cc1CO |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-ae8f35505a5f42f7845c7a23a233be40 | CCOC(=O)COc1ccc(O)cc1C.OCCc1cccs1>>CCOC(=O)COc1ccc(OCCc2cccs2)cc1C | C(C)OC(COC1=C(C=C(C=C1)O)C)=O.C(C)OC(COC1=C(C=C(C=C1)O)C)=O.S1C(=CC=C1)CCO.C(CCC)P(CCCC)CCCC>>C(C)OC(COC1=C(C=C(C=C1)OCCC=1SC=CC1)C)=O | O[c:11]1[cH:10][cH:9][c:8]([O:7][CH2:6][C:4]([O:3][CH2:2][CH3:1])=[O:5])[c:21]([CH3:22])[cH:20]1.[OH:12][CH2:13][CH2:14][c:15]1[cH:16][cH:17][cH:18][s:19]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][O:7][c:8]1[cH:9][cH:10][c:11]([O:12][CH2:13][CH2:14][c:15]2[cH:16][cH:17][cH:18][s:19]2)[cH:20][c:21]1[CH3:22] | CCOC(=O)COc1ccc(O)cc1C.OCCc1cccs1 | CCOC(=O)COc1ccc(OCCc2cccs2)cc1C | null | null | O1CCCC1 | Heteroatom Alkylation and Arylation | Mitsunobu aryl ether | 8915084acbaaf997bf0f89ff5187cb2f89c25dc683fffc57b3391298c8430dd9 | 2258bd14c3b5449b92dc09cf9fa522f88d5071b4af20f7e968b60aa1ae6db0cf | c1ccc(OCCc2cccs2)cc1 | O-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[C:6]-[C:7]-[OH;D1;+0:8]>>[C:6]-[C:7]-[O;H0;D2;+0:8]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5] | null | [] | null | null | 3 | DAY | A solution of ethyl(4-hydroxy-2-methylphenoxy)acetate (intermediate 7, 1.05 g) and 2-(2-thienyl)ethanol (0.64 g) in dry tetrahydrofuran was treated with tri-n-butyl phosphine (1.2 g) and azodicarbonyldimorpholide (1.53 g) and the mixture stirred at ambient temperature for 3 days. The reaction mixture was concentrated a... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Aromatic alcohol | Ether | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccsc1 | HO- | O1CCCC1 | null | 72 | CCOC(=O)COc1ccc(O)cc1C.OCCc1cccs1>O1CCCC1>CCOC(=O)COc1ccc(OCCc2cccs2)cc1C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-7637624903df403d86dd6f4ca5b896ea | BrBr.CCOC(=O)COc1ccc(OCCc2cccs2)cc1C>>CCOC(=O)COc1ccc(OCCc2ccc(Br)s2)cc1C | O.C(C)OC(COC1=C(C=C(C=C1)OCCC=1SC=CC1)C)=O.C(C)OC(COC1=C(C=C(C=C1)OCCC=1SC=CC1)C)=O.BrBr>>C(C)OC(COC1=C(C=C(C=C1)OCCC=1SC(=CC1)Br)C)=O | Br[Br:19].[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][O:7][c:8]1[cH:9][cH:10][c:11]([O:12][CH2:13][CH2:14][c:15]2[cH:16][cH:17][cH:18][s:20]2)[cH:21][c:22]1[CH3:23]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][O:7][c:8]1[cH:9][cH:10][c:11]([O:12][CH2:13][CH2:14][c:15]2[cH:16][cH:17][c:18]([Br:19])[s:20]2)[cH:21][c:22]1[CH3:23] | BrBr.CCOC(=O)COc1ccc(OCCc2cccs2)cc1C | CCOC(=O)COc1ccc(OCCc2ccc(Br)s2)cc1C | null | null | C(C)(=O)O | Functional Group Interconversion | Bromination | 4c699ee9b1951af9f1cb735a87e324fa1208b45d074146a138e8c7ebdaaf12cc | 3c4065ab4a8681675e06a527dcad54d701c7bfdcac9f73f87773b05034108934 | c1ccc(OCCc2cccs2)cc1 | Br-[Br;H0;D1;+0:1].[#16;a:2]1:[c:3]:[c:4]:[c:5]:[cH;D2;+0:6]:1>>[Br;H0;D1;+0:1]-[c;H0;D3;+0:6]1:[#16;a:2]:[c:3]:[c:4]:[c:5]:1 | null | [] | null | null | 15 | MINUTE | A solution of ethyl[2-methyl-4-(2-thien-2-ylethoxy)phenoxy]acetate (intermediate 69, 0.306 g) in acetic acid (5 ml) was treated with bromine (0.180 g) at ambient temperature and the mixture stirred for 15 minutes. The mixture was poured into water and the resulting suspension extracted with diethyl ether. The organic l... | 10.6084/m9.figshare.5104873.v1 | null | null | Aromatic halide | c1ccsc1 | c1ccsc1 | c1ccccc1.c1ccsc1 | HBr | C(C)(=O)O | null | 0.25 | BrBr.CCOC(=O)COc1ccc(OCCc2cccs2)cc1C>C(C)(=O)O>CCOC(=O)COc1ccc(OCCc2ccc(Br)s2)cc1C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-74b822405f8e419aaae0449610e9ed3b | Cc1ccsc1C=O.OCCO>>Cc1ccsc1C1OCCO1 | CC1=C(SC=C1)C=O.C(CO)O.C1(=CC=C(C=C1)S(=O)(=O)O)C>>CC1=C(SC=C1)C1OCCO1 | [CH3:1][c:2]1[cH:3][cH:4][s:5][c:6]1[CH:7]=[O:8].O[CH2:9][CH2:10][OH:11]>>[CH3:1][c:2]1[cH:3][cH:4][s:5][c:6]1[CH:7]1[O:8][CH2:9][CH2:10][O:11]1 | Cc1ccsc1C=O.OCCO | Cc1ccsc1C1OCCO1 | null | null | C1(=CC=CC=C1)C | Heteroatom Alkylation and Arylation | OtherReaction | fe0fbb45a87f24c1e456c6b4e41101562cd8f0af3ec376bb6115e7c1555d997b | 7ac65b5a5f576337ce8e86e0130eb9b4757ca21b2419a0e82bbdfd5def30ee73 | c1csc(C2OCCO2)c1 | O-[CH2;D2;+0:1]-[C:2]-[OH;D1;+0:3].[O;H0;D1;+0:4]=[CH;D2;+0:5]-[c:6](:[c:7]):[#16;a:8]:[c:9]>>[c:7]:[c:6](-[CH;D3;+0:5]1-[O;H0;D2;+0:3]-[C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:4]-1):[#16;a:8]:[c:9] | null | [] | null | null | null | null | A mixture of 3-methylthiophene carboxaldehyde (6.8 g), ethylene glycol (10 ml) and p-toluenesulfonic acid (0.30 g) in toluene (125 ml) was heated at reflux for 18 hours. The reaction mixture was cooled; extracted with 2M aqueous sodium carbonate and then dried with brine and over magnesium sulfate. Analysis of the crud... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Primary alcohol.Primary alcohol | Ether.Ether | null | C1COCO1 | c1ccsc1.C1COCO1 | HO- | C1(=CC=CC=C1)C | null | null | Cc1ccsc1C=O.OCCO>C1(=CC=CC=C1)C>Cc1ccsc1C1OCCO1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-bdd6a74b4fde4fe1a64ca556ea6560a2 | CCC[CH2][Sn]([Cl])([CH2]CCC)[CH2]CCC.Cc1ccsc1C1OCCO1>>CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[c]1cc(C)c(C2OCCO2)s1 | C(CCC)[Sn](CCCC)(CCCC)Cl.CC1=C(SC=C1)C1OCCO1.CC1=C(SC=C1)C1OCCO1.C(CCC)[Li]>>C(CCC)[Sn](C=1SC(=C(C1)C)C1OCCO1)(CCCC)CCCC | [Cl][Sn:5]([CH2:4][CH2:3][CH2:2][CH3:1])([CH2:6][CH2:7][CH2:8][CH3:9])[CH2:10][CH2:11][CH2:12][CH3:13].[cH:14]1[cH:15][c:16]([CH3:17])[c:18]([CH:19]2[O:20][CH2:21][CH2:22][O:23]2)[s:24]1>>[CH3:1][CH2:2][CH2:3][CH2:4][Sn:5]([CH2:6][CH2:7][CH2:8][CH3:9])([CH2:10][CH2:11][CH2:12][CH3:13])[c:14]1[cH:15][c:16]([CH3:17])[c:1... | CCC[CH2][Sn]([Cl])([CH2]CCC)[CH2]CCC.Cc1ccsc1C1OCCO1 | CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[c]1cc(C)c(C2OCCO2)s1 | null | null | O1CCCC1.C(C)OCC | Functional Group Interconversion | OtherReaction | c7834bb64a0b822f74ee40d731e5e52ca4910d9ebd5fd19ee81e8742e3acaec8 | 8ed099106fd03cd2d2d78800a2ee5fc34a9ebd85fa643ab7cdafec1855cc2f69 | c1csc(C2OCCO2)c1 | [#16;a:1]1:[c:2]:[c:3]:[c:4]:[cH;D2;+0:5]:1.[C:6]-[C:7]-[Sn;H0;D4;+0:8](-[Cl])(-[C:9]-[C:10])-[C:11]-[C:12]>>[C:6]-[C:7]-[Sn;H0;D4;+0:8](-[C:9]-[C:10])(-[C:11]-[C:12])-[c;H0;D3;+0:5]1:[#16;a:1]:[c:2]:[c:3]:[c:4]:1 | null | [] | -60 | CELSIUS | 1 | HOUR | A mixture of 2-(3-methylthien-2-yl)-1,3-dioxolane (intermediate 75, 1.5 g) in tetrahydrofuran (50 ml), stirred at −60° C. under a nitrogen atmosphere, was treated drop-wise with 1.6M n-butyl lithium in hexanes (6.1 ml). The reaction mixture was stirred at this temperature for 1 hour and tributyltin chloride (2.6 ml) wa... | 10.6084/m9.figshare.5104873.v1 | null | Tin | Tin | c1ccsc1 | c1ccsc1 | c1ccsc1.C1COCO1 | HCl | O1CCCC1.C(C)OCC | -60 | 1 | CCC[CH2][Sn]([Cl])([CH2]CCC)[CH2]CCC.Cc1ccsc1C1OCCO1>O1CCCC1.C(C)OCC>CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[c]1cc(C)c(C2OCCO2)s1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-c4e70ab5a3954c6f92ec92114990c273 | CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[c]1cc(C)c(C2OCCO2)s1>>CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[c]1cc(C)c(C=O)s1 | C(CCC)[Sn](C=1SC(=C(C1)C)C1OCCO1)(CCCC)CCCC.C(CCC)[Sn](C=1SC(=C(C1)C)C1OCCO1)(CCCC)CCCC.Cl>>CC1=C(SC(=C1)[Sn](CCCC)(CCCC)CCCC)C=O | C1C[O:20][CH:19]([c:18]2[c:16]([CH3:17])[cH:15][c:14]([Sn:5]([CH2:4][CH2:3][CH2:2][CH3:1])([CH2:6][CH2:7][CH2:8][CH3:9])[CH2:10][CH2:11][CH2:12][CH3:13])[s:21]2)O1>>[CH3:1][CH2:2][CH2:3][CH2:4][Sn:5]([CH2:6][CH2:7][CH2:8][CH3:9])([CH2:10][CH2:11][CH2:12][CH3:13])[c:14]1[cH:15][c:16]([CH3:17])[c:18]([CH:19]=[O:20])[s:21... | CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[c]1cc(C)c(C2OCCO2)s1 | CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[c]1cc(C)c(C=O)s1 | null | null | O1CCCC1 | Miscellaneous | Acetal hydrolysis to aldehyde | f12636b09f9df336ccc8fe82b927db0e267bccc7cae0970f1f91c7ceed085225 | 84d5a69453aa750f462aa94a6bf2116fc17c5d88a9619aaa9eefb74b0c09848d | c1ccsc1 | [c:1]:[#16;a:2]:[c:3](-[CH;D3;+0:4]1-O-C-C-[O;H0;D2;+0:5]-1):[c:6]>>[O;H0;D1;+0:5]=[CH;D2;+0:4]-[c:3](:[c:6]):[#16;a:2]:[c:1] | null | [] | null | null | null | null | A mixture of tributyl[5-(1,3-dioxolan-2-yl)4-methylthien-2-yl]stannane (intermediate 76, 2.92 g), 1M aqueous hydrochloric acid (3 ml) and tetrahydrofuran (10 ml) was stirred at reflux for 30 minutes. The reaction mixture was cooled, extracted thrice with diethylether. The organic solutions were combined, extracted with... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether | Aldehyde | C1COCO1 | null | c1ccsc1 | HO- | O1CCCC1 | null | null | CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[c]1cc(C)c(C2OCCO2)s1>O1CCCC1>CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[c]1cc(C)c(C=O)s1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-c4c7b667259941398d24acbf3497c507 | Cc1cc(-c2ccc(C(F)(F)F)cn2)sc1C=O>>Cc1cc(-c2ccc(C(F)(F)F)cn2)sc1CO | CC1=C(SC(=C1)C1=NC=C(C=C1)C(F)(F)F)C=O.CC1=C(SC(=C1)C1=NC=C(C=C1)C(F)(F)F)C=O.[BH4-].[Na+]>>CC1=C(SC(=C1)C1=NC=C(C=C1)C(F)(F)F)CO | [CH3:1][c:2]1[cH:3][c:4](-[c:5]2[cH:6][cH:7][c:8]([C:9]([F:10])([F:11])[F:12])[cH:13][n:14]2)[s:15][c:16]1[CH:17]=[O:18]>>[CH3:1][c:2]1[cH:3][c:4](-[c:5]2[cH:6][cH:7][c:8]([C:9]([F:10])([F:11])[F:12])[cH:13][n:14]2)[s:15][c:16]1[CH2:17][OH:18] | Cc1cc(-c2ccc(C(F)(F)F)cn2)sc1C=O | Cc1cc(-c2ccc(C(F)(F)F)cn2)sc1CO | null | null | O.O1CCCC1 | Reduction | Reduction of aldehydes and ketones to alcohols | e7895795cd3f75445716c94697823c5929dcd4b5344525875fe75d36bca2f9d7 | 21bb81d5469aaaca71ab12c186bea4016451717fad8780cf288858a7d8fbc55a | c1ccc(-c2cccs2)nc1 | [O;H0;D1;+0:1]=[CH;D2;+0:2]-[c:3](:[c:4]):[#16;a:5]:[c:6]>>[OH;D1;+0:1]-[CH2;D2;+0:2]-[c:3](:[c:4]):[#16;a:5]:[c:6] | null | [] | null | null | 30 | MINUTE | A mixture of 3-methyl-5-[5-(trifluoromethyl)pyridin-2-yl]thiophene-2-carbaldehyde (intermediate 78, 0.144 g) in tetrahydrofuran (10 ml) and water (15 ml) was treated with sodium borohydride (0.03 g). The reaction was stirred at room temperature for 30 minutes, extracted with ethyl acetate and the organic layer washed w... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | Primary alcohol | null | null | c1ccsc1.c1ccncc1 | null | O.O1CCCC1 | null | 0.5 | Cc1cc(-c2ccc(C(F)(F)F)cn2)sc1C=O>O.O1CCCC1>Cc1cc(-c2ccc(C(F)(F)F)cn2)sc1CO |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-68d53e10beee4f048db9f744e8204245 | BrBr.Cc1ccsc1C=O>>Cc1cc(Br)sc1C=O | CC1=C(SC=C1)C=O.BrBr>>BrC1=CC(=C(S1)C=O)C | Br[Br:5].[CH3:1][c:2]1[cH:3][cH:4][s:6][c:7]1[CH:8]=[O:9]>>[CH3:1][c:2]1[cH:3][c:4]([Br:5])[s:6][c:7]1[CH:8]=[O:9] | BrBr.Cc1ccsc1C=O | Cc1cc(Br)sc1C=O | null | null | C(Cl)(Cl)Cl | Functional Group Interconversion | Bromination | 4c699ee9b1951af9f1cb735a87e324fa1208b45d074146a138e8c7ebdaaf12cc | 3c4065ab4a8681675e06a527dcad54d701c7bfdcac9f73f87773b05034108934 | c1ccsc1 | Br-[Br;H0;D1;+0:1].[O;D1;H0:2]=[C:3]-[c:4]1:[#16;a:5]:[cH;D2;+0:6]:[c:7]:[c:8]:1>>[Br;H0;D1;+0:1]-[c;H0;D3;+0:6]1:[#16;a:5]:[c:4](-[C:3]=[O;D1;H0:2]):[c:8]:[c:7]:1 | null | [] | 100 | CELSIUS | null | null | A solution of 3-methyl-thiophene-2-carboxaldehyde (12.0 g) in chloroform (50 ml) was added drop-wise to bromine (5.1 ml) in chloroform over 30 minutes and then heated to 100° C. for 140 minutes. The reaction mixture was diluted with chloroform and washed with 10% aqueous sodium thiosulfate solution, saturated aqueous b... | 10.6084/m9.figshare.5104873.v1 | null | null | Aromatic halide | c1ccsc1 | c1ccsc1 | c1ccsc1 | HBr | C(Cl)(Cl)Cl | 100 | null | BrBr.Cc1ccsc1C=O>C(Cl)(Cl)Cl>Cc1cc(Br)sc1C=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-52cc4b26200a4c778030d3f61d23cf78 | CC(=O)c1sc(Br)cc1C>>Cc1cc(Br)sc1CO | Cl.BrC1=CC(=C(S1)C(C)=O)C.BrC1=CC(=C(S1)C(C)=O)C.[BH4-].[Na+]>>BrC1=CC(=C(S1)CO)C | C[C:8]([c:7]1[c:2]([CH3:1])[cH:3][c:4]([Br:5])[s:6]1)=[O:9]>>[CH3:1][c:2]1[cH:3][c:4]([Br:5])[s:6][c:7]1[CH2:8][OH:9] | CC(=O)c1sc(Br)cc1C | Cc1cc(Br)sc1CO | null | null | C(C)O | Miscellaneous | OtherReaction | a43fad546b2cb05323f351cd9cca06d38248729da7429b0dafab2ef9a6bed33d | 04190f81a1769ff9dcfacc394437dbb7cd186b6d1b4798d5532105ccb82af62a | c1ccsc1 | C-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[c:3](:[c:4]):[#16;a:5]:[c:6]>>[OH;D1;+0:2]-[CH2;D2;+0:1]-[c:3](:[c:4]):[#16;a:5]:[c:6] | null | [] | 0 | CELSIUS | 60 | MINUTE | A mixture of 1-(5-bromo-3-methylthien-2-yl)ethanone (intermediate 82, 5.13 g) in ethanol (50 ml) was treated with sodium borohydride (0.947 g). The reaction was stirred at 0° C. for 60 minutes and warmed to room temp for 30 minutes. 2M Aqueous hydrochloric acid was added and the reaction mixture was extracted with ethy... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Primary alcohol | null | null | c1ccsc1 | Other | C(C)O | 0 | 1 | CC(=O)c1sc(Br)cc1C>C(C)O>Cc1cc(Br)sc1CO |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-35fbf77d81c9458bb2baceb830e52f52 | COC(=O)Cc1cc(-c2ccc(Cl)cc2)oc1C(F)(F)F>>OCCc1cc(-c2ccc(Cl)cc2)oc1C(F)(F)F | [H-].C(C(C)C)[Al+]CC(C)C.COC(CC1=C(OC(=C1)C1=CC=C(C=C1)Cl)C(F)(F)F)=O.COC(CC1=C(OC(=C1)C1=CC=C(C=C1)Cl)C(F)(F)F)=O>>ClC1=CC=C(C=C1)C1=CC(=C(O1)C(F)(F)F)CCO | CO[C:2](=[O:1])[CH2:3][c:4]1[cH:5][c:6](-[c:7]2[cH:8][cH:9][c:10]([Cl:11])[cH:12][cH:13]2)[o:14][c:15]1[C:16]([F:17])([F:18])[F:19]>>[OH:1][CH2:2][CH2:3][c:4]1[cH:5][c:6](-[c:7]2[cH:8][cH:9][c:10]([Cl:11])[cH:12][cH:13]2)[o:14][c:15]1[C:16]([F:17])([F:18])[F:19] | COC(=O)Cc1cc(-c2ccc(Cl)cc2)oc1C(F)(F)F | OCCc1cc(-c2ccc(Cl)cc2)oc1C(F)(F)F | null | null | O1CCCC1.C1(=CC=CC=C1)C | Reduction | Reduction of ester to primary alcohol | 21d61543c6ec8a8cebe1b3ef55ef3dd20acbf79a4f1c12a7fb51e32be7a3248a | 1fbcd628a0426673c5d10aa49a977cd2d1ae02a8cdf57bbb10d94aa03a94e937 | c1ccc(-c2ccco2)cc1 | C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[C:3]-[c:4]:[c:5]:[#8;a:6]>>[#8;a:6]:[c:5]:[c:4]-[C:3]-[CH2;D2;+0:1]-[OH;D1;+0:2] | null | [] | null | null | 2.5 | HOUR | 1.5 M Diisobutylaluminium hydride in toluene (0.8 ml) was added to a solution of methyl[5-(4-chlorophenyl)-2-(trifluoromethyl)-3-furyl]acetate (intermediate 86, 0.10 g) in tetrahydrofuran (5 ml) at 0° C. under nitrogen. The solution was allowed to stir thus for 2.5 hours then was quenched with methanol and allowed to w... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary alcohol | null | null | c1ccoc1.c1ccccc1 | Other | O1CCCC1.C1(=CC=CC=C1)C | null | 2.5 | COC(=O)Cc1cc(-c2ccc(Cl)cc2)oc1C(F)(F)F>O1CCCC1.C1(=CC=CC=C1)C>OCCc1cc(-c2ccc(Cl)cc2)oc1C(F)(F)F |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-0859d51250d044c38378d9f0c267c973 | CNC(C)C.COC(=O)c1cc(-c2ccc(C(F)(F)F)cc2)oc1CBr>>CC(C)N(C)Cc1oc(-c2ccc(C(F)(F)F)cc2)cc1CO | BrCC=1OC(=CC1C(=O)OC)C1=CC=C(C=C1)C(F)(F)F.CNC(C)C>>C(C)(C)N(C)CC=1OC(=CC1CO)C1=CC=C(C=C1)C(F)(F)F | [CH3:1][CH:2]([CH3:3])[NH:4][CH3:5].CO[C:22]([c:21]1[c:7]([CH2:6]Br)[o:8][c:9](-[c:10]2[cH:11][cH:12][c:13]([C:14]([F:15])([F:16])[F:17])[cH:18][cH:19]2)[cH:20]1)=[O:23]>>[CH3:1][CH:2]([CH3:3])[N:4]([CH3:5])[CH2:6][c:7]1[o:8][c:9](-[c:10]2[cH:11][cH:12][c:13]([C:14]([F:15])([F:16])[F:17])[cH:18][cH:19]2)[cH:20][c:21]1[... | CNC(C)C.COC(=O)c1cc(-c2ccc(C(F)(F)F)cc2)oc1CBr | CC(C)N(C)Cc1oc(-c2ccc(C(F)(F)F)cc2)cc1CO | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | ab720d4700c7f1eb26bdcdc8b8e0dadc114b8b8054da409c36959a09d81908a4 | 5185a8f5e4b71d0234a3b03cc63e26b3b068dc9422b0dde6b5591d1d0b54c0f7 | c1ccc(-c2ccco2)cc1 | Br-[CH2;D2;+0:1]-[c:2]1:[#8;a:3]:[c:4]:[c:5]:[c:6]:1-[C;H0;D3;+0:7](=[O;H0;D1;+0:8])-O-C.[C;D1;H3:9]-[C:10](-[C;D1;H3:11])-[NH;D2;+0:12]-[C;D1;H3:13]>>[C;D1;H3:9]-[C:10](-[C;D1;H3:11])-[N;H0;D3;+0:12](-[C;D1;H3:13])-[CH2;D2;+0:1]-[c:2]1:[#8;a:3]:[c:4]:[c:5]:[c:6]:1-[CH2;D2;+0:7]-[OH;D1;+0:8] | null | [] | null | null | null | null | Prepared using intermediate 44 and N-methylisopropylamine. This compound was used directly without collection of analytical data for the preparation of Example 75.
Conditions: See reaction.notes.procedure_details.
Workup: Prepared; This compound was used directly without collection of analytical data for the preparatio... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester.Secondary amine | Primary alcohol.Tertiary amine | null | null | c1ccoc1.c1ccccc1 | HBr | null | null | null | CNC(C)C.COC(=O)c1cc(-c2ccc(C(F)(F)F)cc2)oc1CBr>>CC(C)N(C)Cc1oc(-c2ccc(C(F)(F)F)cc2)cc1CO |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-bbf60a1608b144aa8738c2f4a555aa79 | CNCCc1ccccc1.COC(=O)c1cc(-c2ccc(C(F)(F)F)cc2)oc1CBr>>CN(CCc1ccccc1)Cc1oc(-c2ccc(C(F)(F)F)cc2)cc1CO | BrCC=1OC(=CC1C(=O)OC)C1=CC=C(C=C1)C(F)(F)F.CNCCC1=CC=CC=C1>>CN(CCC1=CC=CC=C1)CC=1OC(=CC1CO)C1=CC=C(C=C1)C(F)(F)F | [CH3:1][NH:2][CH2:3][CH2:4][c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1.CO[C:27]([c:26]1[c:12]([CH2:11]Br)[o:13][c:14](-[c:15]2[cH:16][cH:17][c:18]([C:19]([F:20])([F:21])[F:22])[cH:23][cH:24]2)[cH:25]1)=[O:28]>>[CH3:1][N:2]([CH2:3][CH2:4][c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1)[CH2:11][c:12]1[o:13][c:14](-[c:15]2[cH:16][cH:17... | CNCCc1ccccc1.COC(=O)c1cc(-c2ccc(C(F)(F)F)cc2)oc1CBr | CN(CCc1ccccc1)Cc1oc(-c2ccc(C(F)(F)F)cc2)cc1CO | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | ab720d4700c7f1eb26bdcdc8b8e0dadc114b8b8054da409c36959a09d81908a4 | 5185a8f5e4b71d0234a3b03cc63e26b3b068dc9422b0dde6b5591d1d0b54c0f7 | c1ccc(CCNCc2ccc(-c3ccccc3)o2)cc1 | Br-[CH2;D2;+0:1]-[c:2]1:[#8;a:3]:[c:4]:[c:5]:[c:6]:1-[C;H0;D3;+0:7](=[O;H0;D1;+0:8])-O-C.[C:9]-[C:10]-[NH;D2;+0:11]-[C;D1;H3:12]>>[C:9]-[C:10]-[N;H0;D3;+0:11](-[C;D1;H3:12])-[CH2;D2;+0:1]-[c:2]1:[#8;a:3]:[c:4]:[c:5]:[c:6]:1-[CH2;D2;+0:7]-[OH;D1;+0:8] | null | [] | null | null | null | null | Prepared using intermediate 44 and N-methylphenethylamine.
Conditions: See reaction.notes.procedure_details.
Workup: Prepared | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester.Secondary amine | Primary alcohol.Tertiary amine | null | null | c1ccccc1.c1ccoc1.c1ccccc1 | HBr | null | null | null | CNCCc1ccccc1.COC(=O)c1cc(-c2ccc(C(F)(F)F)cc2)oc1CBr>>CN(CCc1ccccc1)Cc1oc(-c2ccc(C(F)(F)F)cc2)cc1CO |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-22738bd0ee6c4942bad63a5abef978f4 | CNC1CCCCC1.COC(=O)c1cc(-c2ccc(C(F)(F)F)cc2)oc1CBr>>CN(Cc1oc(-c2ccc(C(F)(F)F)cc2)cc1CO)C1CCCCC1 | BrCC=1OC(=CC1C(=O)OC)C1=CC=C(C=C1)C(F)(F)F.CNC1CCCCC1>>C1(CCCCC1)N(C)CC=1OC(=CC1CO)C1=CC=C(C=C1)C(F)(F)F | [CH3:1][NH:2][CH:21]1[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26]1.CO[C:19]([c:18]1[c:4]([CH2:3]Br)[o:5][c:6](-[c:7]2[cH:8][cH:9][c:10]([C:11]([F:12])([F:13])[F:14])[cH:15][cH:16]2)[cH:17]1)=[O:20]>>[CH3:1][N:2]([CH2:3][c:4]1[o:5][c:6](-[c:7]2[cH:8][cH:9][c:10]([C:11]([F:12])([F:13])[F:14])[cH:15][cH:16]2)[cH:17][c:18]1[CH... | CNC1CCCCC1.COC(=O)c1cc(-c2ccc(C(F)(F)F)cc2)oc1CBr | CN(Cc1oc(-c2ccc(C(F)(F)F)cc2)cc1CO)C1CCCCC1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | ab720d4700c7f1eb26bdcdc8b8e0dadc114b8b8054da409c36959a09d81908a4 | 5185a8f5e4b71d0234a3b03cc63e26b3b068dc9422b0dde6b5591d1d0b54c0f7 | c1ccc(-c2ccc(CNC3CCCCC3)o2)cc1 | Br-[CH2;D2;+0:1]-[c:2]1:[#8;a:3]:[c:4]:[c:5]:[c:6]:1-[C;H0;D3;+0:7](=[O;H0;D1;+0:8])-O-C.[C:9]-[C:10](-[NH;D2;+0:11]-[C;D1;H3:12])-[C:13]>>[C:9]-[C:10](-[N;H0;D3;+0:11](-[C;D1;H3:12])-[CH2;D2;+0:1]-[c:2]1:[#8;a:3]:[c:4]:[c:5]:[c:6]:1-[CH2;D2;+0:7]-[OH;D1;+0:8])-[C:13] | null | [] | null | null | null | null | Prepared using intermediate 44 and N-methylcyclohexylamine.
Conditions: See reaction.notes.procedure_details.
Workup: Prepared | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester.Secondary amine | Primary alcohol.Tertiary amine | null | null | c1ccoc1.c1ccccc1.C1CCCCC1 | HBr | null | null | null | CNC1CCCCC1.COC(=O)c1cc(-c2ccc(C(F)(F)F)cc2)oc1CBr>>CN(Cc1oc(-c2ccc(C(F)(F)F)cc2)cc1CO)C1CCCCC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-29ab68ec7fbd4c80a56aeb3f91a16063 | CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[c]1cc(C)c(CCc2ccc(OCC34OCC(C)(CO3)CO4)c(C)c2)s1.N#Cc1ccc(Br)cc1F>>Cc1cc(CCc2sc(-c3ccc(C#N)c(F)c3)cc2C)ccc1OCC12OCC(C)(CO1)CO2 | C(CCC)[Sn](C=1SC(=C(C1)C)CCC1=CC(=C(C=C1)OCC12OCC(CO1)(CO2)C)C)(CCCC)CCCC.C(CCC)[Sn](C=1SC(=C(C1)C)CCC1=CC(=C(C=C1)OCC12OCC(CO1)(CO2)C)C)(CCCC)CCCC.FC1=C(C#N)C=CC(=C1)Br.O1C(=CC=C1)P(C=1OC=CC1)C=1OC=CC1>>FC1=C(C#N)C=CC(=C1)C=1SC(=C(C1)C)CCC1=CC(=C(C=C1)OCC12OCC(CO1)(CO2)C)C | CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[c:9]1[s:8][c:7]([CH2:6][CH2:5][c:4]2[cH:3][c:2]([CH3:1])[c:24]([O:25][CH2:26][C:27]34[O:28][CH2:29][C:30]([CH3:31])([CH2:32][O:33]3)[CH2:34][O:35]4)[cH:23][cH:22]2)[c:20]([CH3:21])[cH:19]1.Br[c:10]1[cH:11][cH:12][c:13]([C:14]#[N:15])[c:16]([F:17])[cH:18]1>>[CH3:1][c:2]1[cH:3][c:4]([CH2:... | CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[c]1cc(C)c(CCc2ccc(OCC34OCC(C)(CO3)CO4)c(C)c2)s1.N#Cc1ccc(Br)cc1F | Cc1cc(CCc2sc(-c3ccc(C#N)c(F)c3)cc2C)ccc1OCC12OCC(C)(CO1)CO2 | null | C(C1=CC=CC=C1)=CC(=O)C=CC1=CC=CC=C1.C(C1=CC=CC=C1)=CC(=O)C=CC1=CC=CC=C1.[Pd] | O1CCCC1 | C-C Coupling | Stille reaction_aryl | 841e59629d4b06d582b64a1032c03def5b35c04a7fe524fc094f49f9f59f23d3 | db27eeefac0475c6d74fa10b3167e95a61caaae74e8bbafd45892452c0c3d4d6 | c1ccc(-c2ccc(CCc3ccc(OCC45OCC(CO4)CO5)cc3)s2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].C-C-C-[CH2]-[Sn](-[CH2]-C-C-C)(-[CH2]-C-C-C)-[c;H0;D3;+0:6]1:[#16;a:7]:[c:8]:[c:9]:[c:10]:1>>[c:3]:[c:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:6]1:[#16;a:7]:[c:8]:[c:9]:[c:10]:1):[c:4]:[c:5] | null | [] | null | null | null | null | A mixture of tributyl[4-methyl-5-(2-{3-methyl-4-[(4-methyl-2,6,7-trioxabicyclo[2.2.2]oct-1-yl)methoxy]phenyl}ethyl)thien-2-yl]stannane (intermediate 100, 0.037 g) and 2-fluoro-4-bromobenzonitrile (0.011 g) in tetrahydrofuran (2 ml) was treated with palladium bis(dibenzylideneacetone) (0.0035 g) and trifuranyl phosphine... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Tin | null | c1ccsc1.c1ccccc1 | c1ccsc1.c1ccccc1 | c1ccsc1.c1ccccc1.c1ccccc1.C1OC2OCC1CO2 | HBr.Sn | C(C1=CC=CC=C1)=CC(=O)C=CC1=CC=CC=C1.C(C1=CC=CC=C1)=CC(=O)C=CC1=CC=CC=C1.[Pd].O1CCCC1 | null | null | CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[c]1cc(C)c(CCc2ccc(OCC34OCC(C)(CO3)CO4)c(C)c2)s1.N#Cc1ccc(Br)cc1F>C(C1=CC=CC=C1)=CC(=O)C=CC1=CC=CC=C1.C(C1=CC=CC=C1)=CC(=O)C=CC1=CC=CC=C1.[Pd].O1CCCC1>Cc1cc(CCc2sc(-c3ccc(C#N)c(F)c3)cc2C)ccc1OCC12OCC(C)(CO1)CO2 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-15ae2bc802194632a49a178c7691a128 | Cc1ccsc1.FC(F)(F)c1ccc(Br)cc1>>Cc1csc(-c2ccc(C(F)(F)F)cc2)c1 | BrC1=CC=C(C=C1)C(F)(F)F.CC1=CSC=C1.[Li]CCCC>>CC=1C=C(SC1)C1=CC=C(C=C1)C(F)(F)F | [CH3:1][c:2]1[cH:3][s:4][cH:5][cH:16]1.Br[c:6]1[cH:7][cH:8][c:9]([C:10]([F:11])([F:12])[F:13])[cH:14][cH:15]1>>[CH3:1][c:2]1[cH:3][s:4][c:5](-[c:6]2[cH:7][cH:8][c:9]([C:10]([F:11])([F:12])[F:13])[cH:14][cH:15]2)[cH:16]1 | Cc1ccsc1.FC(F)(F)c1ccc(Br)cc1 | Cc1csc(-c2ccc(C(F)(F)F)cc2)c1 | null | C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.[Pd].[Cl-].[Zn+2].[Cl-] | C1CCOC1 | C-C Coupling | OtherReaction | e5445f3ecaa01a9bed902018228404d32b3f8940d6fb5083b33cee2c97effce7 | 48892094855745f5c51f8910c27ce7c101e08ad3f9da2a58d5512e3d9c1b432f | c1ccc(-c2cccs2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[#16;a:6]1:[c:7]:[c:8]:[c:9]:[cH;D2;+0:10]:1>>[c:3]:[c:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:10]1:[#16;a:6]:[c:7]:[c:8]:[c:9]:1):[c:4]:[c:5] | null | [] | 0 | CELSIUS | 30 | MINUTE | To a solution of 3-methylthiophene (2.31 ml) in anhydrous THF (75 ml) at −78° C. under N2 was added dropwise n-BuLi (1.6 M in hexanes, 15 ml). Thirty minutes after the addition was complete, the reaction mixture was allowed to warm to 0° C. and stirred for a further 30 minutes. Zinc chloride (0.5 M in THF, 48 ml) was a... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | null | c1ccsc1.c1ccccc1 | c1ccsc1.c1ccccc1 | c1ccsc1.c1ccccc1 | HBr | C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.[Pd].[Cl-].[Zn+2].[Cl-].C1CCOC1 | 0 | 0.5 | Cc1ccsc1.FC(F)(F)c1ccc(Br)cc1>C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.[Pd].[Cl-].[Zn+2].[Cl-].C1CCOC1>Cc1csc(-c2ccc(C(F)(F)F)cc2)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-450d571946b54fa997b752c94963e482 | COc1ccc(CC(=O)O)cc1C.Cc1csc(-c2ccc(C(F)(F)F)cc2)c1>>COc1ccc(CC(=O)c2sc(-c3ccc(C(F)(F)F)cc3)cc2C)cc1C | C(=O)(O)[O-].[Na+].COC1=C(C=C(C=C1)CC(=O)O)C.CC=1C=C(SC1)C1=CC=C(C=C1)C(F)(F)F.CC=1C=C(SC1)C1=CC=C(C=C1)C(F)(F)F.CS(=O)(=O)O.O=P12OP3(=O)OP(=O)(O1)OP(=O)(O2)O3>>COC1=C(C=C(C=C1)CC(=O)C=1SC(=CC1C)C1=CC=C(C=C1)C(F)(F)F)C | O[C:8]([CH2:7][c:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[c:27]([CH3:28])[cH:26]1)=[O:9].[cH:10]1[s:11][c:12](-[c:13]2[cH:14][cH:15][c:16]([C:17]([F:18])([F:19])[F:20])[cH:21][cH:22]2)[cH:23][c:24]1[CH3:25]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][C:8](=[O:9])[c:10]2[s:11][c:12](-[c:13]3[cH:14][cH:15][c:16]([C:17]([F:18]... | COc1ccc(CC(=O)O)cc1C.Cc1csc(-c2ccc(C(F)(F)F)cc2)c1 | COc1ccc(CC(=O)c2sc(-c3ccc(C(F)(F)F)cc3)cc2C)cc1C | null | null | O | C-C Coupling | Friedel-Crafts acylation | 363ca2865515cfbf2edd007677f50d15717a0300f801981c42cfa582583d7414 | a49756d2995b35bf1c4b6840928f031562470ef5bd676447fb43ce2575147daa | O=C(Cc1ccccc1)c1ccc(-c2ccccc2)s1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[c:4].[C;D1;H3:5]-[c:6]1:[c:7]:[c:8]:[#16;a:9]:[cH;D2;+0:10]:1>>[C;D1;H3:5]-[c:6]1:[c:7]:[c:8]:[#16;a:9]:[c;H0;D3;+0:10]:1-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[c:4] | null | [] | 60 | CELSIUS | null | null | To methanesulfonic acid (8 ml) in a flask under N2 was added P2O5 (0.56 g), the resulting suspension was heated to 60° C. until a clear solution formed. The mixture was cooled to room temperature prior to addition of 4-methoxy-3-methyl-phenylacetic acid (0.3549) and 4-methyl-2-[4-(trifluoromethyl)phenyl]thiophene (inte... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Ketone | c1ccsc1 | c1ccsc1 | c1ccccc1.c1ccsc1.c1ccccc1 | HO- | O | 60 | null | COc1ccc(CC(=O)O)cc1C.Cc1csc(-c2ccc(C(F)(F)F)cc2)c1>O>COc1ccc(CC(=O)c2sc(-c3ccc(C(F)(F)F)cc3)cc2C)cc1C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-a446494c32bd4380ab4328862f822cd6 | COc1ccc(C(C)(C)C(=O)c2sc(-c3ccc(C(F)(F)F)cc3)cc2C)cc1C>>Cc1cc(C(C)(C)C(=O)c2sc(-c3ccc(C(F)(F)F)cc3)cc2C)ccc1O | O.COC1=C(C=C(C=C1)C(C(=O)C=1SC(=CC1C)C1=CC=C(C=C1)C(F)(F)F)(C)C)C.COC1=C(C=C(C=C1)C(C(=O)C=1SC(=CC1C)C1=CC=C(C=C1)C(F)(F)F)(C)C)C.Cl.N1=CC=CC=C1>>OC1=C(C=C(C=C1)C(C(=O)C=1SC(=CC1C)C1=CC=C(C=C1)C(F)(F)F)(C)C)C | C[O:29][c:28]1[c:2]([CH3:1])[cH:3][c:4]([C:5]([CH3:6])([CH3:7])[C:8](=[O:9])[c:10]2[s:11][c:12](-[c:13]3[cH:14][cH:15][c:16]([C:17]([F:18])([F:19])[F:20])[cH:21][cH:22]3)[cH:23][c:24]2[CH3:25])[cH:26][cH:27]1>>[CH3:1][c:2]1[cH:3][c:4]([C:5]([CH3:6])([CH3:7])[C:8](=[O:9])[c:10]2[s:11][c:12](-[c:13]3[cH:14][cH:15][c:16](... | COc1ccc(C(C)(C)C(=O)c2sc(-c3ccc(C(F)(F)F)cc3)cc2C)cc1C | Cc1cc(C(C)(C)C(=O)c2sc(-c3ccc(C(F)(F)F)cc3)cc2C)ccc1O | null | null | C(Cl)Cl | Deprotection | Cleavage of methoxy ethers to alcohols | c5320c7dfa4f544d4900efcae9b3262bf0d5286bcf39c86109232351f35b23d5 | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | O=C(Cc1ccccc1)c1ccc(-c2ccccc2)s1 | C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[OH;D1;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | 150 | CELSIUS | null | null | To 2-(4-methoxy-3-methylphenyl)-2-methyl-1-{3-methyl-5-[4-(trifluoromethyl)phenyl]thien-2-yl}propan-1-one (intermediate 104, 0.35 g) in a pressure vessel was added pyridine hydrochloride (10 g), the vessel was sealed and heated to 150° C. for 72 hours. The reaction vessel was then allowed to cool to room temperature an... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | null | null | c1ccccc1.c1ccsc1.c1ccccc1 | Other | C(Cl)Cl | 150 | null | COc1ccc(C(C)(C)C(=O)c2sc(-c3ccc(C(F)(F)F)cc3)cc2C)cc1C>C(Cl)Cl>Cc1cc(C(C)(C)C(=O)c2sc(-c3ccc(C(F)(F)F)cc3)cc2C)ccc1O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-0d961a5452df42c8855de61b7e83107b | CCOC(=O)CBr.Cc1cc(C(C)(C)C(=O)c2sc(-c3ccc(C(F)(F)F)cc3)cc2C)ccc1O>>CCOC(=O)COc1ccc(C(C)(C)C(=O)c2sc(-c3ccc(C(F)(F)F)cc3)cc2C)cc1C | OC1=C(C=C(C=C1)C(C(=O)C=1SC(=CC1C)C1=CC=C(C=C1)C(F)(F)F)(C)C)C.OC1=C(C=C(C=C1)C(C(=O)C=1SC(=CC1C)C1=CC=C(C=C1)C(F)(F)F)(C)C)C.C([O-])([O-])=O.[Cs+].[Cs+].BrCC(=O)OCC>>C(C)OC(COC1=C(C=C(C=C1)C(C(=O)C=1SC(=CC1C)C1=CC=C(C=C1)C(F)(F)F)(C)C)C)=O | Br[CH2:6][C:4]([O:3][CH2:2][CH3:1])=[O:5].[OH:7][c:8]1[cH:9][cH:10][c:11]([C:12]([CH3:13])([CH3:14])[C:15](=[O:16])[c:17]2[s:18][c:19](-[c:20]3[cH:21][cH:22][c:23]([C:24]([F:25])([F:26])[F:27])[cH:28][cH:29]3)[cH:30][c:31]2[CH3:32])[cH:33][c:34]1[CH3:35]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][O:7][c:8]1[cH:9][cH:10][... | CCOC(=O)CBr.Cc1cc(C(C)(C)C(=O)c2sc(-c3ccc(C(F)(F)F)cc3)cc2C)ccc1O | CCOC(=O)COc1ccc(C(C)(C)C(=O)c2sc(-c3ccc(C(F)(F)F)cc3)cc2C)cc1C | null | null | C(C)#N | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 50d675b335c583a6ce22e1164b27a78b18b9ca447d45137820c344bcb6369217 | 0865de4e1853c59ac25437e36fd18b03329566cb9eff4b4f0ce70d5714692fd3 | O=C(Cc1ccccc1)c1ccc(-c2ccccc2)s1 | Br-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#8:4]-[C:5].[OH;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[C: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 | 20 | HOUR | To a solution of 2-(4-hydroxy-3-methylphenyl)-2-methyl-1-{3-methyl-5-[4-(trifluoromethyl)phenyl]thien-2-yl}propan-1-one (intermediate 105, 62.0 mg) in anhydrous acetonitrile (2 ml) was added caesium carbonate (106 mg) and ethyl bromoacetate (18 μl) and the reaction stirred at room temperature under nitrogen for 20 hour... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester.Aromatic alcohol | Ester.Ether | null | null | c1ccccc1.c1ccsc1.c1ccccc1 | HBr | C(C)#N | null | 20 | CCOC(=O)CBr.Cc1cc(C(C)(C)C(=O)c2sc(-c3ccc(C(F)(F)F)cc3)cc2C)ccc1O>C(C)#N>CCOC(=O)COc1ccc(C(C)(C)C(=O)c2sc(-c3ccc(C(F)(F)F)cc3)cc2C)cc1C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-9cda42749fb643e8a2f6c6ec8e8fcd8b | CCOC(=O)CBr.CCc1ccccc1O>>CCOC(=O)COc1ccccc1CC | C(C)C1=C(C=CC=C1)O.C([O-])([O-])=O.[Cs+].[Cs+].BrCC(=O)OCC>>C(C)OC(COC1=C(C=CC=C1)CC)=O | Br[CH2:6][C:4]([O:3][CH2:2][CH3:1])=[O:5].[OH:7][c:8]1[cH:9][cH:10][cH:11][cH:12][c:13]1[CH2:14][CH3:15]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][O:7][c:8]1[cH:9][cH:10][cH:11][cH:12][c:13]1[CH2:14][CH3:15] | CCOC(=O)CBr.CCc1ccccc1O | CCOC(=O)COc1ccccc1CC | null | null | C(C)(=O)OCC.C(C)#N | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 50d675b335c583a6ce22e1164b27a78b18b9ca447d45137820c344bcb6369217 | 0865de4e1853c59ac25437e36fd18b03329566cb9eff4b4f0ce70d5714692fd3 | c1ccccc1 | Br-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#8:4]-[C:5].[OH;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[C: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 | [] | 60 | CELSIUS | 6 | HOUR | A mixture of 2-ethylphenol (244 mg) in acetonitrile (20 ml) was treated with cesium carbonate (650 mg) and ethyl bromoacetate (0.221 ml) and the mixture stirred at 60° C. for 6 hours and then at ambient temperature for 17 hours. The reaction mixture was diluted with ethyl acetate; the suspension filtered and the title ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester.Aromatic alcohol | Ester.Ether | null | null | c1ccccc1 | HBr | C(C)(=O)OCC.C(C)#N | 60 | 6 | CCOC(=O)CBr.CCc1ccccc1O>C(C)(=O)OCC.C(C)#N>CCOC(=O)COc1ccccc1CC |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-1f39594965174048aec2d27ed501f246 | CCOC(=O)COc1ccccc1CC.O=S(=O)(O)Cl>>CCOC(=O)COc1ccc(S(=O)(=O)Cl)cc1CC | C(C)OC(COC1=C(C=CC=C1)CC)=O.C(C)OC(COC1=C(C=CC=C1)CC)=O.ClS(=O)(=O)O>>C(C)OC(COC1=C(C=C(C=C1)S(=O)(=O)Cl)CC)=O | [CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][O:7][c:8]1[cH:9][cH:10][cH:11][cH:16][c:17]1[CH2:18][CH3:19].O=[S:12]([OH:13])(=[O:14])[Cl:15]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][O:7][c:8]1[cH:9][cH:10][c:11]([S:12](=[O:13])(=[O:14])[Cl:15])[cH:16][c:17]1[CH2:18][CH3:19] | CCOC(=O)COc1ccccc1CC.O=S(=O)(O)Cl | CCOC(=O)COc1ccc(S(=O)(=O)Cl)cc1CC | null | null | C(Cl)(Cl)Cl | Protection | Aromatic sulfonyl chlorination | c55ee9a7393fdf3f247a23f751c8b9bb8a24c2b053414c59e6d87cc0f6e27124 | c731d053565135be022f3edbe36cf28a9b4364ca579bdb183b2db9578bab4695 | c1ccccc1 | O=[S;H0;D4;+0:1](-[Cl;D1;H0:2])(=[O;D1;H0:3])-[OH;D1;+0:4].[c:5]:[c:6]:[cH;D2;+0:7]:[c:8]:[c:9]>>[Cl;D1;H0:2]-[S;H0;D4;+0:1](=[O;D1;H0:3])(=[O;H0;D1;+0:4])-[c;H0;D3;+0:7](:[c:8]:[c:9]):[c:6]:[c:5] | null | [] | null | null | null | null | A solution of crude ethyl(2-ethylphenoxy)acetate (intermediate 107) in chloroform (6 ml) was stirred with chlorosulfonic acid (1.33 ml) at ambient temperature for 4 hours. The reaction mixture was quenched by the addition of ice and the organic mixture separated by using a hydrophobic frit. The title compound was isola... | 10.6084/m9.figshare.5104873.v1 | null | null | Sulfonyl halide | c1ccccc1 | c1ccccc1 | c1ccccc1 | HO- | C(Cl)(Cl)Cl | null | null | CCOC(=O)COc1ccccc1CC.O=S(=O)(O)Cl>C(Cl)(Cl)Cl>CCOC(=O)COc1ccc(S(=O)(=O)Cl)cc1CC |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-bb369774dd52483faa7fe8c2c2fb6a6b | CC(C)[Si](Cl)(C(C)C)C(C)C.Cc1ccsc1CO>>Cc1ccsc1CO[Si](C(C)C)(C(C)C)C(C)C | C(C)(C)[Si](C(C)C)(C(C)C)Cl.CC1=C(SC=C1)CO.[H-].[Na+].[H][H]>>C(C)(C)[Si](OCC=1SC=CC1C)(C(C)C)C(C)C | Cl[Si:9]([CH:10]([CH3:11])[CH3:12])([CH:13]([CH3:14])[CH3:15])[CH:16]([CH3:17])[CH3:18].[CH3:1][c:2]1[cH:3][cH:4][s:5][c:6]1[CH2:7][OH:8]>>[CH3:1][c:2]1[cH:3][cH:4][s:5][c:6]1[CH2:7][O:8][Si:9]([CH:10]([CH3:11])[CH3:12])([CH:13]([CH3:14])[CH3:15])[CH:16]([CH3:17])[CH3:18] | CC(C)[Si](Cl)(C(C)C)C(C)C.Cc1ccsc1CO | Cc1ccsc1CO[Si](C(C)C)(C(C)C)C(C)C | null | null | C(C)(=O)OCC.O1CCCC1 | Protection | Alcohol protection with silyl ethers | 16b089e75ae0faeb6299d6901714a961ddf80ba40eb5191df04d4efe8b4a1af5 | a12fb6ee4294c877f426f603ce64d893e39b302f1553f4ca246c599e7a8e7068 | c1ccsc1 | Cl-[Si;H0;D4;+0:1](-[C:2](-[C;D1;H3:3])-[C;D1;H3:4])(-[C:5](-[C;D1;H3:6])-[C;D1;H3:7])-[C:8](-[C;D1;H3:9])-[C;D1;H3:10].[#16;a:11]:[c:12]-[C:13]-[OH;D1;+0:14]>>[#16;a:11]:[c:12]-[C:13]-[O;H0;D2;+0:14]-[Si;H0;D4;+0:1](-[C:2](-[C;D1;H3:3])-[C;D1;H3:4])(-[C:5](-[C;D1;H3:6])-[C;D1;H3:7])-[C:8](-[C;D1;H3:9])-[C;D1;H3:10] | null | [] | null | null | 2 | HOUR | A solution of (3-methylthien-2-yl)methanol (3.20 g) in tetrahydrofuran (10 ml) was added to a mixture of sodium hydride (60% dispersion in mineral oil, 1.05 g) in tetrahydrofuran (40 ml). After the evolution of hydrogen had subsided triisopropylsilyl chloride (5.2 ml) was added. The reaction mixture was stirred for 2 h... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Silyl protective group | Silyl protective group | null | null | c1ccsc1 | HCl | C(C)(=O)OCC.O1CCCC1 | null | 2 | CC(C)[Si](Cl)(C(C)C)C(C)C.Cc1ccsc1CO>C(C)(=O)OCC.O1CCCC1>Cc1ccsc1CO[Si](C(C)C)(C(C)C)C(C)C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-cc8ff98036344a30b32617317c2cefd3 | CC(C)OB1OC(C)(C)C(C)(C)O1.Cc1ccsc1CO[Si](C(C)C)(C(C)C)C(C)C>>Cc1cc(B2OC(C)(C)C(C)(C)O2)sc1CO[Si](C(C)C)(C(C)C)C(C)C | C(C)(C)OB1OC(C(O1)(C)C)(C)C.C(C)(C)[Si](OCC=1SC=CC1C)(C(C)C)C(C)C.C(C)(C)[Si](OCC=1SC=CC1C)(C(C)C)C(C)C.C(CCC)[Li].[Cl-].[NH4+]>>C(C)(C)[Si](OCC=1SC(=CC1C)B1OC(C(O1)(C)C)(C)C)(C(C)C)C(C)C | CC(C)O[B:5]1[O:6][C:7]([CH3:8])([CH3:9])[C:10]([CH3:11])([CH3:12])[O:13]1.[CH3:1][c:2]1[cH:3][cH:4][s:14][c:15]1[CH2:16][O:17][Si:18]([CH:19]([CH3:20])[CH3:21])([CH:22]([CH3:23])[CH3:24])[CH:25]([CH3:26])[CH3:27]>>[CH3:1][c:2]1[cH:3][c:4]([B:5]2[O:6][C:7]([CH3:8])([CH3:9])[C:10]([CH3:11])([CH3:12])[O:13]2)[s:14][c:15]1... | CC(C)OB1OC(C)(C)C(C)(C)O1.Cc1ccsc1CO[Si](C(C)C)(C(C)C)C(C)C | Cc1cc(B2OC(C)(C)C(C)(C)O2)sc1CO[Si](C(C)C)(C(C)C)C(C)C | null | null | O1CCCC1 | Functional Group Interconversion | OtherReaction | a067202df3f80ebc79b5bc6345d891acb3b2dd93f74049428fee7a79a23e965b | 55b2480301cea859d1218f23e11281559f3dfc2ef4b9f2ac7f38d4293c2fe6cc | c1csc(B2OCCO2)c1 | C-C(-C)-O-[B;H0;D3;+0:1]1-[#8:2]-[C:3]-[C:4]-[#8:5]-1.[#16;a:6]1:[c:7]:[c:8]:[c:9]:[cH;D2;+0:10]:1>>[#16;a:6]1:[c:7]:[c:8]:[c:9]:[c;H0;D3;+0:10]:1-[B;H0;D3;+0:1]1-[#8:2]-[C:3]-[C:4]-[#8:5]-1 | null | [] | -78 | CELSIUS | 2 | HOUR | A mixture of triisopropyl[(3-methylthien-2-yl)methoxy]silane (intermediate 115, 1.42 g) in tetrahydrofuran (20 ml), stirred at −78° C. under nitrogen, was treated with 1.6M butyllithium in hexanes (3.9 ml). The reaction temperature was slowly allowed to rise to 0° C. over 2 hours and then re-cooled to −78° C. 2-Isoprop... | 10.6084/m9.figshare.5104873.v1 | null | null | Boronic ester | [B]1OCCO1.c1ccsc1 | c1ccsc1.[B]1OCCO1 | c1ccsc1.[B]1OCCO1 | HO- | O1CCCC1 | -78 | 2 | CC(C)OB1OC(C)(C)C(C)(C)O1.Cc1ccsc1CO[Si](C(C)C)(C(C)C)C(C)C>O1CCCC1>Cc1cc(B2OC(C)(C)C(C)(C)O2)sc1CO[Si](C(C)C)(C(C)C)C(C)C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-e03a93a17363478b889d4c03be0565a7 | Cc1cc(B2OC(C)(C)C(C)(C)O2)sc1CO[Si](C(C)C)(C(C)C)C(C)C.FC(F)(F)Oc1ccc(Br)cc1>>Cc1cc(-c2ccc(OC(F)(F)F)cc2)sc1CO[Si](C(C)C)(C(C)C)C(C)C | BrC1=CC=C(C=C1)OC(F)(F)F.C([O-])([O-])=O.[Na+].[Na+].C(C)(C)[Si](OCC=1SC(=CC1C)B1OC(C(O1)(C)C)(C)C)(C(C)C)C(C)C.C(C)(C)[Si](OCC=1SC(=CC1C)B1OC(C(O1)(C)C)(C)C)(C(C)C)C(C)C>>C(C)(C)[Si](OCC=1SC(=CC1C)C1=CC=C(C=C1)OC(F)(F)F)(C(C)C)C(C)C | CC1(C)OB([c:4]2[cH:3][c:2]([CH3:1])[c:17]([CH2:18][O:19][Si:20]([CH:21]([CH3:22])[CH3:23])([CH:24]([CH3:25])[CH3:26])[CH:27]([CH3:28])[CH3:29])[s:16]2)OC1(C)C.Br[c:5]1[cH:6][cH:7][c:8]([O:9][C:10]([F:11])([F:12])[F:13])[cH:14][cH:15]1>>[CH3:1][c:2]1[cH:3][c:4](-[c:5]2[cH:6][cH:7][c:8]([O:9][C:10]([F:11])([F:12])[F:13])... | Cc1cc(B2OC(C)(C)C(C)(C)O2)sc1CO[Si](C(C)C)(C(C)C)C(C)C.FC(F)(F)Oc1ccc(Br)cc1 | Cc1cc(-c2ccc(OC(F)(F)F)cc2)sc1CO[Si](C(C)C)(C(C)C)C(C)C | null | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1 | O.COCCOC | C-C Coupling | Suzuki coupling with boronic esters | d812c27edf47313e10d7c32b9eb79a42d8424f8f283ec7c9c8f6647d7e81312c | b42efb3b6a7742d5af594c6a3031e487327e58e9f8c2f428ee68996c98377910 | c1ccc(-c2cccs2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].C-C1(-C)-O-B(-[c;H0;D3;+0:6]2:[#16;a:7]:[c:8]:[c:9]:[c:10]:2)-O-C-1(-C)-C>>[c:3]:[c:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:6]1:[#16;a:7]:[c:8]:[c:9]:[c:10]:1):[c:4]:[c:5] | null | [] | null | null | null | null | A mixture of triisopropyl{[3-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thien-2-yl]methoxy}silane (intermediate 116, 0.40 g) in 1,2-dimethoxyethane (12 ml) and water (6 ml) was treated with 4-bromo-trifluoromethoxybenzene (0.26 g), sodium carbonate (0.26 g) and tetrakis(triphenylphosphine)palladium (0) (0.12... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic ester | null | B1OCCO1.c1ccsc1.c1ccccc1 | c1ccsc1.c1ccccc1 | c1ccsc1.c1ccccc1 | HBr.B | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.O.COCCOC | null | null | Cc1cc(B2OC(C)(C)C(C)(C)O2)sc1CO[Si](C(C)C)(C(C)C)C(C)C.FC(F)(F)Oc1ccc(Br)cc1>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.O.COCCOC>Cc1cc(-c2ccc(OC(F)(F)F)cc2)sc1CO[Si](C(C)C)(C(C)C)C(C)C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-edda2177b7974f31a0a1889e8a802dc0 | Cc1cc(-c2ccc(OC(F)(F)F)cc2)sc1CO[Si](C(C)C)(C(C)C)C(C)C>>Cc1cc(-c2ccc(OC(F)(F)F)cc2)sc1CO | C(C)(C)[Si](OCC=1SC(=CC1C)C1=CC=C(C=C1)OC(F)(F)F)(C(C)C)C(C)C.C(C)(C)[Si](OCC=1SC(=CC1C)C1=CC=C(C=C1)OC(F)(F)F)(C(C)C)C(C)C.[F-].C(C)[N+](CC)(CC)CC>>CC1=C(SC(=C1)C1=CC=C(C=C1)OC(F)(F)F)CO | CC(C)[Si](C(C)C)(C(C)C)[O:19][CH2:18][c:17]1[c:2]([CH3:1])[cH:3][c:4](-[c:5]2[cH:6][cH:7][c:8]([O:9][C:10]([F:11])([F:12])[F:13])[cH:14][cH:15]2)[s:16]1>>[CH3:1][c:2]1[cH:3][c:4](-[c:5]2[cH:6][cH:7][c:8]([O:9][C:10]([F:11])([F:12])[F:13])[cH:14][cH:15]2)[s:16][c:17]1[CH2:18][OH:19] | Cc1cc(-c2ccc(OC(F)(F)F)cc2)sc1CO[Si](C(C)C)(C(C)C)C(C)C | Cc1cc(-c2ccc(OC(F)(F)F)cc2)sc1CO | null | null | O1CCCC1 | Deprotection | Alcohol deprotection from silyl ethers | 488547c1043a845c08188be7baa01e2ee1f8d7661927552d481c2d214b18b6c0 | 5c02ee98cb6b210a313993bea9e102110eb73637a50746f5457590f98613069b | c1ccc(-c2cccs2)cc1 | C-C(-C)-[Si](-[O;H0;D2;+0:1]-[C:2]-[c:3]:[#16;a:4])(-C(-C)-C)-C(-C)-C>>[#16;a:4]:[c:3]-[C:2]-[OH;D1;+0:1] | null | [] | null | null | 1 | HOUR | A mixture of triisopropyl({3-methyl-5-[4-(trifluoromethoxy)phenyl]thien-2-yl}methoxy)silane (intermediate 117, 0.97 g) in tetrahydrofuran (30 ml) was treated with tetraethylammonium fluoride (0.392 g) and the reaction mixture stirred at ambient temperature for 1 hour. The solvent was evaporated and the residue purified... | 10.6084/m9.figshare.5104873.v1 | null | Silyl protective group | Primary alcohol | null | null | c1ccsc1.c1ccccc1 | Other | O1CCCC1 | null | 1 | Cc1cc(-c2ccc(OC(F)(F)F)cc2)sc1CO[Si](C(C)C)(C(C)C)C(C)C>O1CCCC1>Cc1cc(-c2ccc(OC(F)(F)F)cc2)sc1CO |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-05058ab149f7447fac1844993e48d435 | Cc1cc(-c2cc(F)c(C(F)(F)F)cc2F)sc1CO[Si](C(C)C)(C(C)C)C(C)C>>Cc1cc(-c2cc(F)c(C(F)(F)F)cc2F)sc1CO | FC1=C(C=C(C(=C1)C(F)(F)F)F)C1=CC(=C(S1)CO[Si](C(C)C)(C(C)C)C(C)C)C.CC1=C(SC(=C1)C1=CC=C(C=C1)OC(F)(F)F)CO.CC1=C(SC(=C1)C1=CC=C(C=C1)OC(F)(F)F)CO.FC1=C(C=C(C(=C1)C(F)(F)F)F)C1=CC(=C(S1)CO[Si](C(C)C)(C(C)C)C(C)C)C>>FC1=C(C=C(C(=C1)C(F)(F)F)F)C1=CC(=C(S1)CO)C | CC(C)[Si](C(C)C)(C(C)C)[O:20][CH2:19][c:18]1[c:2]([CH3:1])[cH:3][c:4](-[c:5]2[cH:6][c:7]([F:8])[c:9]([C:10]([F:11])([F:12])[F:13])[cH:14][c:15]2[F:16])[s:17]1>>[CH3:1][c:2]1[cH:3][c:4](-[c:5]2[cH:6][c:7]([F:8])[c:9]([C:10]([F:11])([F:12])[F:13])[cH:14][c:15]2[F:16])[s:17][c:18]1[CH2:19][OH:20] | Cc1cc(-c2cc(F)c(C(F)(F)F)cc2F)sc1CO[Si](C(C)C)(C(C)C)C(C)C | Cc1cc(-c2cc(F)c(C(F)(F)F)cc2F)sc1CO | null | null | null | Deprotection | Alcohol deprotection from silyl ethers | 488547c1043a845c08188be7baa01e2ee1f8d7661927552d481c2d214b18b6c0 | 5c02ee98cb6b210a313993bea9e102110eb73637a50746f5457590f98613069b | c1ccc(-c2cccs2)cc1 | C-C(-C)-[Si](-[O;H0;D2;+0:1]-[C:2]-[c:3]:[#16;a:4])(-C(-C)-C)-C(-C)-C>>[#16;a:4]:[c:3]-[C:2]-[OH;D1;+0:1] | null | [] | null | null | null | null | The title compound was prepared using a method analogous to that used for the preparation of {3-methyl-5-[4-(trifluoromethoxy)phenyl]thien-2-yl}methanol (intermediate 118) using ({5-[2,5-difluoro-4-(trifluoromethyl)phenyl]-3-methylthien-2-yl}methoxy)(triisopropyl)silane (intermediate 119).
Conditions: See reaction.note... | 10.6084/m9.figshare.5104873.v1 | null | Silyl protective group | Primary alcohol | null | null | c1ccsc1.c1ccccc1 | Other | null | null | null | Cc1cc(-c2cc(F)c(C(F)(F)F)cc2F)sc1CO[Si](C(C)C)(C(C)C)C(C)C>>Cc1cc(-c2cc(F)c(C(F)(F)F)cc2F)sc1CO |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-2e228b351c7c43fba1014b597e7acab5 | Cc1cc(-c2cc(F)c(C(F)(F)F)cc2F)sc1CO[Si](C(C)C)(C(C)C)C(C)C>>Cc1cc(-c2ccc(C(F)(F)F)c(F)c2F)sc1CO | FC1=C(C=C(C(=C1)C(F)(F)F)F)C1=CC(=C(S1)CO[Si](C(C)C)(C(C)C)C(C)C)C.CC1=C(SC(=C1)C1=CC=C(C=C1)OC(F)(F)F)CO.CC1=C(SC(=C1)C1=CC=C(C=C1)OC(F)(F)F)CO.FC1=C(C=C(C(=C1)C(F)(F)F)F)C1=CC(=C(S1)CO[Si](C(C)C)(C(C)C)C(C)C)C>>FC1=C(C=CC(=C1F)C(F)(F)F)C1=CC(=C(S1)CO)C | CC(C)[Si](C(C)C)(C(C)C)[O:20][CH2:19][c:18]1[c:2]([CH3:1])[cH:3][c:4](-[c:5]2[c:6]([F:16])[cH:7][c:8]([C:9]([F:10])([F:11])[F:12])[c:13]([F:14])[cH:15]2)[s:17]1>>[CH3:1][c:2]1[cH:3][c:4](-[c:5]2[cH:6][cH:7][c:8]([C:9]([F:10])([F:11])[F:12])[c:13]([F:14])[c:15]2[F:16])[s:17][c:18]1[CH2:19][OH:20] | Cc1cc(-c2cc(F)c(C(F)(F)F)cc2F)sc1CO[Si](C(C)C)(C(C)C)C(C)C | Cc1cc(-c2ccc(C(F)(F)F)c(F)c2F)sc1CO | null | null | null | Miscellaneous | OtherReaction | a69cfbe9cd8c3b9c482ce2fa797e7f4eb193c04720e0d3fb137e9b29501f4888 | 4c1930bdfb04403033b414bd12305881e8f5c54d0ef1f4cac95d5142fc5cbb55 | c1ccc(-c2cccs2)cc1 | C-C(-C)-[Si](-[O;H0;D2;+0:1]-[C:2]-[c:3]:[#16;a:4]:[c:5]-[c:6]1:[cH;D2;+0:7]:[c:8](-[F;D1;H0:9]):[c:10]:[c:11]:[c;H0;D3;+0:12]:1-[F;H0;D1;+0:13])(-C(-C)-C)-C(-C)-C>>[F;D1;H0:9]-[c:8]1:[c:10]:[c:11]:[cH;D2;+0:12]:[c:6](-[c:5]:[#16;a:4]:[c:3]-[C:2]-[OH;D1;+0:1]):[c;H0;D3;+0:7]:1-[F;H0;D1;+0:13] | null | [] | null | null | null | null | The title compound was prepared using a method analogous to that used for the preparation of {3-methyl-5-[4-(trifluoromethoxy)phenyl]thien-2-yl}methanol (intermediate 118) using ({5-[2,5-difluoro-4-(trifluoromethyl)phenyl]-3-methylthien-2-yl}methoxy)(triisopropyl)silane (intermediate 121).
Conditions: See reaction.note... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Silyl protective group | Aromatic halide.Primary alcohol | c1ccccc1 | c1ccccc1 | c1ccsc1.c1ccccc1 | Other | null | null | null | Cc1cc(-c2cc(F)c(C(F)(F)F)cc2F)sc1CO[Si](C(C)C)(C(C)C)C(C)C>>Cc1cc(-c2ccc(C(F)(F)F)c(F)c2F)sc1CO |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-ab42de0f5742458eae6065e2d141c665 | Cc1cc(-c2ccc(C(F)(F)F)cc2F)sc1CO[Si](C(C)C)(C(C)C)C(C)C>>Cc1cc(-c2ccc(C(F)(F)F)cc2F)sc1CO | FC1=C(C=CC(=C1)C(F)(F)F)C1=CC(=C(S1)CO[Si](C(C)C)(C(C)C)C(C)C)C.CC1=C(SC(=C1)C1=CC=C(C=C1)OC(F)(F)F)CO.CC1=C(SC(=C1)C1=CC=C(C=C1)OC(F)(F)F)CO.FC1=C(C=CC(=C1)C(F)(F)F)C1=CC(=C(S1)CO[Si](C(C)C)(C(C)C)C(C)C)C>>FC1=C(C=CC(=C1)C(F)(F)F)C1=CC(=C(S1)CO)C | CC(C)[Si](C(C)C)(C(C)C)[O:19][CH2:18][c:17]1[c:2]([CH3:1])[cH:3][c:4](-[c:5]2[cH:6][cH:7][c:8]([C:9]([F:10])([F:11])[F:12])[cH:13][c:14]2[F:15])[s:16]1>>[CH3:1][c:2]1[cH:3][c:4](-[c:5]2[cH:6][cH:7][c:8]([C:9]([F:10])([F:11])[F:12])[cH:13][c:14]2[F:15])[s:16][c:17]1[CH2:18][OH:19] | Cc1cc(-c2ccc(C(F)(F)F)cc2F)sc1CO[Si](C(C)C)(C(C)C)C(C)C | Cc1cc(-c2ccc(C(F)(F)F)cc2F)sc1CO | null | null | null | Deprotection | Alcohol deprotection from silyl ethers | 488547c1043a845c08188be7baa01e2ee1f8d7661927552d481c2d214b18b6c0 | 5c02ee98cb6b210a313993bea9e102110eb73637a50746f5457590f98613069b | c1ccc(-c2cccs2)cc1 | C-C(-C)-[Si](-[O;H0;D2;+0:1]-[C:2]-[c:3]:[#16;a:4])(-C(-C)-C)-C(-C)-C>>[#16;a:4]:[c:3]-[C:2]-[OH;D1;+0:1] | null | [] | null | null | null | null | The title compound was prepared using a method analogous to that used for the preparation of {{3-methyl-5-[4-(trifluoromethoxy)phenyl]thien-2-yl}methanol (intermediate 118) using ({5-[2-fluoro-4-(trifluoromethyl)phenyl]-3-methylthien-2-yl}methoxy)(triisopropyl)silane (intermediate 123).
Conditions: See reaction.notes.p... | 10.6084/m9.figshare.5104873.v1 | null | Silyl protective group | Primary alcohol | null | null | c1ccsc1.c1ccccc1 | Other | null | null | null | Cc1cc(-c2ccc(C(F)(F)F)cc2F)sc1CO[Si](C(C)C)(C(C)C)C(C)C>>Cc1cc(-c2ccc(C(F)(F)F)cc2F)sc1CO |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-2336788b038b41e689f66b799d3c2b1d | CC(O)c1csc(-c2ccc(C(F)(F)F)cc2)c1.[Br][Mg][c]1ccccc1>>OC(c1ccccc1)c1csc(-c2ccc(C(F)(F)F)cc2)c1 | FC(C1=CC=C(C=C1)C=1C(=CSC1)C=O)(F)F.C1(=CC=CC=C1)[Mg]Br.FC(C1=CC=C(C=C1)C1=CC(=CS1)C(C)O)(F)F.FC(C1=CC=C(C=C1)C1=CC(=CS1)C(C)O)(F)F.FC(C1=CC=C(C=C1)C=1C(=CSC1)C=O)(F)F>>C1(=CC=CC=C1)C(O)C1=CSC(=C1)C1=CC=C(C=C1)C(F)(F)F | C[CH:2]([OH:1])[c:9]1[cH:10][s:11][c:12](-[c:13]2[cH:14][cH:15][c:16]([C:17]([F:18])([F:19])[F:20])[cH:21][cH:22]2)[cH:23]1.[Br][Mg][c:3]1[cH:4][cH:5][cH:6][cH:7][cH:8]1>>[OH:1][CH:2]([c:3]1[cH:4][cH:5][cH:6][cH:7][cH:8]1)[c:9]1[cH:10][s:11][c:12](-[c:13]2[cH:14][cH:15][c:16]([C:17]([F:18])([F:19])[F:20])[cH:21][cH:22]... | CC(O)c1csc(-c2ccc(C(F)(F)F)cc2)c1.[Br][Mg][c]1ccccc1 | OC(c1ccccc1)c1csc(-c2ccc(C(F)(F)F)cc2)c1 | null | null | null | C-C Coupling | OtherReaction | 97d004edafcc2073041f60bd00e5c8ac47754ac330afd7d5495d7af05ebe729b | 8cd2e90aff044290b2df896ce234b2bf51c5a7d767f17c971665e1a1e863ebc8 | c1ccc(Cc2csc(-c3ccccc3)c2)cc1 | C-[CH;D3;+0:1](-[O;D1;H1:2])-[c:3]1:[c:4]:[#16;a:5]:[c:6]:[c:7]:1.[Br]-[Mg]-[c;H0;D3;+0:8](:[c:9]:[c:10]):[c:11]:[c:12]>>[O;D1;H1:2]-[CH;D3;+0:1](-[c:3]1:[c:4]:[#16;a:5]:[c:6]:[c:7]:1)-[c;H0;D3;+0:8](:[c:9]:[c:10]):[c:11]:[c:12] | null | [] | null | null | null | null | The title compound was prepared using a method analogous to that used for the preparation of 1-{5-[4-(trifluoromethyl)phenyl]thien-3-yl}ethanol (intermediate 126) using 4-[4-(trifluoromethyl)phenyl]thiophene-3-carbaldehyde (intermediate 125) and phenyl magnesium bromide.
Conditions: See reaction.notes.procedure_details... | 10.6084/m9.figshare.5104873.v1 | null | Magnesium halide.Secondary alcohol | Secondary alcohol | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccsc1.c1ccccc1 | HBr.Mg | null | null | null | CC(O)c1csc(-c2ccc(C(F)(F)F)cc2)c1.[Br][Mg][c]1ccccc1>>OC(c1ccccc1)c1csc(-c2ccc(C(F)(F)F)cc2)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-11e7000f7bdf4162a75e44daa17cdd60 | Cc1cc(-c2ccc(C(F)(F)F)cc2)sc1C=O>>Cc1cc(-c2ccc(C(F)(F)F)cc2)sc1C(C)O | CC1=C(SC(=C1)C1=CC=C(C=C1)C(F)(F)F)C=O.C[Mg]Br.FC(C1=CC=C(C=C1)C1=CC(=CS1)C(C)O)(F)F.FC(C1=CC=C(C=C1)C1=CC(=CS1)C(C)O)(F)F.CC1=C(SC(=C1)C1=CC=C(C=C1)C(F)(F)F)C=O>>CC1=C(SC(=C1)C1=CC=C(C=C1)C(F)(F)F)C(C)O | [CH3:1][c:2]1[cH:3][c:4](-[c:5]2[cH:6][cH:7][c:8]([C:9]([F:10])([F:11])[F:12])[cH:13][cH:14]2)[s:15][c:16]1[CH:17]=[O:19]>>[CH3:1][c:2]1[cH:3][c:4](-[c:5]2[cH:6][cH:7][c:8]([C:9]([F:10])([F:11])[F:12])[cH:13][cH:14]2)[s:15][c:16]1[CH:17]([CH3:18])[OH:19] | Cc1cc(-c2ccc(C(F)(F)F)cc2)sc1C=O | Cc1cc(-c2ccc(C(F)(F)F)cc2)sc1C(C)O | null | null | null | Miscellaneous | OtherReaction | 1ffaf80f172e20da969364a5d2977299bc51b204f2262675c45c8ec58ff36ac0 | e005d650d08e61fc67b766830eb53235a9bc084cc3667d2f8a73c2fb8bb34277 | c1ccc(-c2cccs2)cc1 | [O;H0;D1;+0:1]=[CH;D2;+0:2]-[c:3](:[c:4]):[#16;a:5]:[c:6]>>[C;D1;H3:7]-[CH;D3;+0:2](-[OH;D1;+0:1])-[c:3](:[c:4]):[#16;a:5]:[c:6] | null | [] | null | null | null | null | The title compound was prepared using a method analogous to that used for the preparation of 1-{5-[4-(trifluoromethyl)phenyl]thien-3-yl}ethanol (intermediate 126) using 3-methyl-5-[4-(trifluoromethyl)phenyl]thiophene-2-carbaldehyde (intermediate 74) and methyl magnesium bromide.
Conditions: See reaction.notes.procedure... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | Secondary alcohol | null | null | c1ccsc1.c1ccccc1 | Other | null | null | null | Cc1cc(-c2ccc(C(F)(F)F)cc2)sc1C=O>>Cc1cc(-c2ccc(C(F)(F)F)cc2)sc1C(C)O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b32d3278f4144988a796a1120977547e | Cc1cc(-c2ccc(C(F)(F)F)cc2)sc1C=O.O=C(O)c1cc(-c2ccc(C(F)(F)F)cc2)cs1>>Cc1cc(-c2ccc(C(F)(F)F)cc2)sc1C(=O)O | CC1=C(SC(=C1)C1=CC=C(C=C1)C(F)(F)F)C=O.CC1=C(SC(=C1)C1=CC=C(C=C1)C(F)(F)F)C=O.FC(C1=CC=C(C=C1)C=1C=C(SC1)C(=O)O)(F)F.FC(C1=CC=C(C=C1)C=1C=C(SC1)C(=O)O)(F)F>>CC1=C(SC(=C1)C1=CC=C(C=C1)C(F)(F)F)C(=O)O | [CH3:1][c:2]1[cH:3][c:4](-[c:5]2[cH:6][cH:7][c:8]([C:9]([F:10])([F:11])[F:12])[cH:13][cH:14]2)[s:15][c:16]1[CH:17]=[O:18].O=C(c1cc(-c2ccc(C(F)(F)F)cc2)cs1)[OH:19]>>[CH3:1][c:2]1[cH:3][c:4](-[c:5]2[cH:6][cH:7][c:8]([C:9]([F:10])([F:11])[F:12])[cH:13][cH:14]2)[s:15][c:16]1[C:17](=[O:18])[OH:19] | Cc1cc(-c2ccc(C(F)(F)F)cc2)sc1C=O.O=C(O)c1cc(-c2ccc(C(F)(F)F)cc2)cs1 | Cc1cc(-c2ccc(C(F)(F)F)cc2)sc1C(=O)O | null | null | null | Protection | OtherReaction | 1519bf4774f2f488a08f6c2235eb9d82b03e3e671166665bd5befb015e1effd7 | 1824559f36c8eea2b8faeb992e41baa366041ecd1c3a2aa96a20c0f7a34b0fd9 | c1ccc(-c2cccs2)cc1 | F-C(-F)(-F)-c1:c:c:c(-c2:c:s:c(-C(=O)-[OH;D1;+0:1]):c:2):c:c:1.[O;D1;H0:2]=[CH;D2;+0:3]-[c:4](:[c:5]):[#16;a:6]:[c:7]>>[O;D1;H0:2]=[C;H0;D3;+0:3](-[OH;D1;+0:1])-[c:4](:[c:5]):[#16;a:6]:[c:7] | null | [] | null | null | null | null | The title compound was prepared using 3-methyl-5-[4-(trifluoromethyl)phenyl]thiophene-2-carbaldehyde (intermediate 74) by a method analogous to the preparation of 4-[4-(trifluoromethyl)phenyl]thiophene-2-carboxylic acid (intermediate 38).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Trifluoro group.Aldehyde.Carboxylic acid | Carboxylic acid | c1ccsc1.c1ccccc1 | null | c1ccsc1.c1ccccc1 | HF | null | null | null | Cc1cc(-c2ccc(C(F)(F)F)cc2)sc1C=O.O=C(O)c1cc(-c2ccc(C(F)(F)F)cc2)cs1>>Cc1cc(-c2ccc(C(F)(F)F)cc2)sc1C(=O)O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-39764b49df2e448c85ecf3cdf691af3a | CO.Cc1cc(-c2ccc(C(F)(F)F)cc2)sc1C(=O)O>>COC(=O)c1sc(-c2ccc(C(F)(F)F)cc2)cc1C | CC1=C(SC(=C1)C1=CC=C(C=C1)C(F)(F)F)C(=O)O.CC1=C(SC(=C1)C1=CC=C(C=C1)C(F)(F)F)C(=O)O.CO>>CC1=C(SC(=C1)C1=CC=C(C=C1)C(F)(F)F)C(=O)OC | [CH3:1][OH:2].O[C:3](=[O:4])[c:5]1[s:6][c:7](-[c:8]2[cH:9][cH:10][c:11]([C:12]([F:13])([F:14])[F:15])[cH:16][cH:17]2)[cH:18][c:19]1[CH3:20]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[s:6][c:7](-[c:8]2[cH:9][cH:10][c:11]([C:12]([F:13])([F:14])[F:15])[cH:16][cH:17]2)[cH:18][c:19]1[CH3:20] | CO.Cc1cc(-c2ccc(C(F)(F)F)cc2)sc1C(=O)O | COC(=O)c1sc(-c2ccc(C(F)(F)F)cc2)cc1C | null | null | null | Protection | Esterification of Carboxylic Acids | 9cecdbd189c6f9c3648521d17154d013842a5498de4e76e65efb1d842973340b | af0b8064f2e82ebe66c4c29d2391785ac1b993104265ccdc4d67ca79e36fa3c8 | c1ccc(-c2cccs2)cc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[#16;a:5]:[c:6].[C;D1;H3:7]-[OH;D1;+0:8]>>[C;D1;H3:7]-[O;H0;D2;+0:8]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[#16;a:5]:[c:6] | null | [] | 30 | CELSIUS | null | null | A mixture of 3-methyl-5[4-(trifluoromethyl)phenyl]thiophene-2-carboxylic acid (intermediate 130, 8.1 g) in methanol (300 ml) was heated at 30° C. and hydrogen chloride gas bubbled through the mixture. The reaction mixture was then stirred at reflux for 21 hours; cooled and treated with further hydrogen chloride gas. Th... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Methanol | Ester | null | null | c1ccsc1.c1ccccc1 | HO- | null | 30 | null | CO.Cc1cc(-c2ccc(C(F)(F)F)cc2)sc1C(=O)O>>COC(=O)c1sc(-c2ccc(C(F)(F)F)cc2)cc1C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-6955e06f343f4d48a5b3006d7249844a | CC(C)S.COC(=O)c1sc(-c2ccc(C(F)(F)F)cc2)cc1CBr>>CC(C)SCc1cc(-c2ccc(C(F)(F)F)cc2)sc1CO | BrCC1=C(SC(=C1)C1=CC=C(C=C1)C(F)(F)F)C(=O)OC.BrCC1=C(SC(=C1)C1=CC=C(C=C1)C(F)(F)F)C(=O)OC.CC(C)S>>FC(C1=CC=C(C=C1)C1=CC(=C(S1)CO)CSC(C)C)(F)F | [CH3:1][CH:2]([CH3:3])[SH:4].CO[C:21]([c:20]1[c:6]([CH2:5]Br)[cH:7][c:8](-[c:9]2[cH:10][cH:11][c:12]([C:13]([F:14])([F:15])[F:16])[cH:17][cH:18]2)[s:19]1)=[O:22]>>[CH3:1][CH:2]([CH3:3])[S:4][CH2:5][c:6]1[cH:7][c:8](-[c:9]2[cH:10][cH:11][c:12]([C:13]([F:14])([F:15])[F:16])[cH:17][cH:18]2)[s:19][c:20]1[CH2:21][OH:22] | CC(C)S.COC(=O)c1sc(-c2ccc(C(F)(F)F)cc2)cc1CBr | CC(C)SCc1cc(-c2ccc(C(F)(F)F)cc2)sc1CO | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | e449c424d502450e30627dd5bf732dc7c8a0a639dd86e0480f8c88fd6617a92f | 70fdc9d517f1bd60ca2a96b9128763fe511b02c2db4dd31afe5f6d010faf6a3a | c1ccc(-c2cccs2)cc1 | Br-[CH2;D2;+0:1]-[c:2]1:[c:3]:[c:4]:[#16;a:5]:[c:6]:1-[C;H0;D3;+0:7](=[O;H0;D1;+0:8])-O-C.[C;D1;H3:9]-[C:10](-[C;D1;H3:11])-[SH;D1;+0:12]>>[C;D1;H3:9]-[C:10](-[C;D1;H3:11])-[S;H0;D2;+0:12]-[CH2;D2;+0:1]-[c:2]1:[c:3]:[c:4]:[#16;a:5]:[c:6]:1-[CH2;D2;+0:7]-[OH;D1;+0:8] | null | [] | null | null | null | null | The title compound was prepared using methyl 3-(bromomethyl)-5-[4-(trifluoromethyl)phenyl]thiophene-2-carboxylate (intermediate 132) and isopropylthiol.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester.Aliphatic thiol | Primary alcohol.Monosulfide | null | null | c1ccsc1.c1ccccc1 | HBr | null | null | null | CC(C)S.COC(=O)c1sc(-c2ccc(C(F)(F)F)cc2)cc1CBr>>CC(C)SCc1cc(-c2ccc(C(F)(F)F)cc2)sc1CO |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-2c1878949a1b4ee18a068a524f55b987 | COC(=O)c1sc(-c2ccc(C(F)(F)F)cc2)cc1CBr.Cc1ccc(C)c(O)c1C>>Cc1ccc(C)c(OCc2cc(-c3ccc(C(F)(F)F)cc3)sc2CO)c1C | BrCC1=C(SC(=C1)C1=CC=C(C=C1)C(F)(F)F)C(=O)OC.BrCC1=C(SC(=C1)C1=CC=C(C=C1)C(F)(F)F)C(=O)OC.CC1=C(C(=C(C=C1)C)C)O>>FC(C1=CC=C(C=C1)C1=CC(=C(S1)CO)COC1=C(C(=CC=C1C)C)C)(F)F | CO[C:25]([c:24]1[c:10]([CH2:9]Br)[cH:11][c:12](-[c:13]2[cH:14][cH:15][c:16]([C:17]([F:18])([F:19])[F:20])[cH:21][cH:22]2)[s:23]1)=[O:26].[CH3:1][c:2]1[cH:3][cH:4][c:5]([CH3:6])[c:7]([OH:8])[c:27]1[CH3:28]>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([CH3:6])[c:7]([O:8][CH2:9][c:10]2[cH:11][c:12](-[c:13]3[cH:14][cH:15][c:16]([C:17](... | COC(=O)c1sc(-c2ccc(C(F)(F)F)cc2)cc1CBr.Cc1ccc(C)c(O)c1C | Cc1ccc(C)c(OCc2cc(-c3ccc(C(F)(F)F)cc3)sc2CO)c1C | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | c176f489b2a0aec18a165134f247edbb416190f25898c2d4da2a773f18aac4b8 | c53e40ba1eff467f03d6efc966ae7bc0310980572b314c3d58e1697358a3b316 | c1ccc(OCc2csc(-c3ccccc3)c2)cc1 | Br-[CH2;D2;+0:1]-[c:2]1:[c:3]:[c:4]:[#16;a:5]:[c:6]:1-[C;H0;D3;+0:7](=[O;H0;D1;+0:8])-O-C.[OH;D1;+0:9]-[c:10](:[c:11]):[c:12]>>[OH;D1;+0:8]-[CH2;D2;+0:7]-[c:6]1:[#16;a:5]:[c:4]:[c:3]:[c:2]:1-[CH2;D2;+0:1]-[O;H0;D2;+0:9]-[c:10](:[c:11]):[c:12] | null | [] | null | null | null | null | The title compound was prepared using methyl 3-(bromomethyl)-5-[4-(trifluoromethyl)phenyl]thiophene-2-carboxylate (intermediate 132) and 2,5,6-trimethylphenol.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester.Aromatic alcohol | Ether.Primary alcohol | null | null | c1ccccc1.c1ccsc1.c1ccccc1 | HBr | null | null | null | COC(=O)c1sc(-c2ccc(C(F)(F)F)cc2)cc1CBr.Cc1ccc(C)c(O)c1C>>Cc1ccc(C)c(OCc2cc(-c3ccc(C(F)(F)F)cc3)sc2CO)c1C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-af55f1b94a2548bbb8c81307374898be | COC(=O)c1sc(-c2ccc(C(F)(F)F)cc2)cc1CBr.Cc1cc(O)nc(C(C)C)n1>>Cc1cc(OCc2cc(-c3ccc(C(F)(F)F)cc3)sc2CO)nc(C(C)C)n1 | BrCC1=C(SC(=C1)C1=CC=C(C=C1)C(F)(F)F)C(=O)OC.BrCC1=C(SC(=C1)C1=CC=C(C=C1)C(F)(F)F)C(=O)OC.C(C)(C)C1=NC(=CC(=N1)O)C>>C(C)(C)C1=NC(=CC(=N1)OCC1=C(SC(=C1)C1=CC=C(C=C1)C(F)(F)F)CO)C | CO[C:22]([c:21]1[c:7]([CH2:6]Br)[cH:8][c:9](-[c:10]2[cH:11][cH:12][c:13]([C:14]([F:15])([F:16])[F:17])[cH:18][cH:19]2)[s:20]1)=[O:23].[CH3:1][c:2]1[cH:3][c:4]([OH:5])[n:24][c:25]([CH:26]([CH3:27])[CH3:28])[n:29]1>>[CH3:1][c:2]1[cH:3][c:4]([O:5][CH2:6][c:7]2[cH:8][c:9](-[c:10]3[cH:11][cH:12][c:13]([C:14]([F:15])([F:16])... | COC(=O)c1sc(-c2ccc(C(F)(F)F)cc2)cc1CBr.Cc1cc(O)nc(C(C)C)n1 | Cc1cc(OCc2cc(-c3ccc(C(F)(F)F)cc3)sc2CO)nc(C(C)C)n1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | c176f489b2a0aec18a165134f247edbb416190f25898c2d4da2a773f18aac4b8 | c53e40ba1eff467f03d6efc966ae7bc0310980572b314c3d58e1697358a3b316 | c1ccc(-c2cc(COc3ccncn3)cs2)cc1 | Br-[CH2;D2;+0:1]-[c:2]1:[c:3]:[c:4]:[#16;a:5]:[c:6]:1-[C;H0;D3;+0:7](=[O;H0;D1;+0:8])-O-C.[OH;D1;+0:9]-[c:10]1:[#7;a:11]:[c:12]:[#7;a:13]:[c:14]:[c:15]:1>>[OH;D1;+0:8]-[CH2;D2;+0:7]-[c:6]1:[#16;a:5]:[c:4]:[c:3]:[c:2]:1-[CH2;D2;+0:1]-[O;H0;D2;+0:9]-[c:10]1:[#7;a:11]:[c:12]:[#7;a:13]:[c:14]:[c:15]:1 | null | [] | null | null | null | null | The title compound was prepared using methyl 3-(bromomethyl)-5-[4-(trifluoromethyl)phenyl]thiophene-2-carboxylate (intermediate 132) and 2-isopropyl-6-methyl-4-pyrimidinol.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester.Aromatic alcohol | Ether.Primary alcohol | null | null | c1cncnc1.c1ccsc1.c1ccccc1 | HBr | null | null | null | COC(=O)c1sc(-c2ccc(C(F)(F)F)cc2)cc1CBr.Cc1cc(O)nc(C(C)C)n1>>Cc1cc(OCc2cc(-c3ccc(C(F)(F)F)cc3)sc2CO)nc(C(C)C)n1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-2d49faf75f5843e2981edc18336faa55 | COC(=O)c1cc(-c2ccc(C(F)(F)F)cc2)oc1CBr.Sc1ccc2ccccc2n1>>OCc1cc(-c2ccc(C(F)(F)F)cc2)oc1CSc1ccc2ccccc2n1 | BrCC=1OC(=CC1C(=O)OC)C1=CC=C(C=C1)C(F)(F)F.BrCC=1OC(=CC1C(=O)OC)C1=CC=C(C=C1)C(F)(F)F.N1=C(C=CC2=CC=CC=C12)S>>N1=C(C=CC2=CC=CC=C12)SCC=1OC(=CC1CO)C1=CC=C(C=C1)C(F)(F)F | CO[C:2](=[O:1])[c:3]1[cH:4][c:5](-[c:6]2[cH:7][cH:8][c:9]([C:10]([F:11])([F:12])[F:13])[cH:14][cH:15]2)[o:16][c:17]1[CH2:18]Br.[SH:19][c:20]1[cH:21][cH:22][c:23]2[cH:24][cH:25][cH:26][cH:27][c:28]2[n:29]1>>[OH:1][CH2:2][c:3]1[cH:4][c:5](-[c:6]2[cH:7][cH:8][c:9]([C:10]([F:11])([F:12])[F:13])[cH:14][cH:15]2)[o:16][c:17]1... | COC(=O)c1cc(-c2ccc(C(F)(F)F)cc2)oc1CBr.Sc1ccc2ccccc2n1 | OCc1cc(-c2ccc(C(F)(F)F)cc2)oc1CSc1ccc2ccccc2n1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 08c77f11eaf4e36a7f23d9c96fdbea329e0e9e71c97093be41efc81e5897bb0b | 0bc700e9066b623dea760dcab4d553b1bf12ee99b5abde8134b45af4be775469 | c1ccc(-c2ccc(CSc3ccc4ccccc4n3)o2)cc1 | Br-[CH2;D2;+0:1]-[c:2]1:[#8;a:3]:[c:4]:[c:5]:[c:6]:1-[C;H0;D3;+0:7](=[O;H0;D1;+0:8])-O-C.[SH;D1;+0:9]-[c:10](:[c:11]):[#7;a:12]:[c:13]>>[OH;D1;+0:8]-[CH2;D2;+0:7]-[c:6]1:[c:5]:[c:4]:[#8;a:3]:[c:2]:1-[CH2;D2;+0:1]-[S;H0;D2;+0:9]-[c:10](:[c:11]):[#7;a:12]:[c:13] | null | [] | null | null | null | null | The title compound was prepared using methyl 2-(bromomethyl)-5-[4-(trifluoromethyl)phenyl]-3-furoate (intermediate 44) and 2-quinolinethiol.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester.Aromatic thiol | Primary alcohol.Monosulfide | null | null | c1ccoc1.c1ccccc1.c1ccc2ncccc2c1 | HBr | null | null | null | COC(=O)c1cc(-c2ccc(C(F)(F)F)cc2)oc1CBr.Sc1ccc2ccccc2n1>>OCc1cc(-c2ccc(C(F)(F)F)cc2)oc1CSc1ccc2ccccc2n1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-fc1c9bf03a1743779f6120cc7abf34b5 | COC(=O)c1cc(-c2ccc(C(F)(F)F)cc2)oc1CBr.Sc1nc(-c2ccccc2)n[nH]1>>OCc1cc(-c2ccc(C(F)(F)F)cc2)oc1CSc1nc(-c2ccccc2)n[nH]1 | BrCC=1OC(=CC1C(=O)OC)C1=CC=C(C=C1)C(F)(F)F.BrCC=1OC(=CC1C(=O)OC)C1=CC=C(C=C1)C(F)(F)F.C1(=CC=CC=C1)C1=NNC(=N1)S>>C1(=CC=CC=C1)C1=NNC(=N1)SCC=1OC(=CC1CO)C1=CC=C(C=C1)C(F)(F)F | CO[C:2](=[O:1])[c:3]1[cH:4][c:5](-[c:6]2[cH:7][cH:8][c:9]([C:10]([F:11])([F:12])[F:13])[cH:14][cH:15]2)[o:16][c:17]1[CH2:18]Br.[SH:19][c:20]1[n:21][c:22](-[c:23]2[cH:24][cH:25][cH:26][cH:27][cH:28]2)[n:29][nH:30]1>>[OH:1][CH2:2][c:3]1[cH:4][c:5](-[c:6]2[cH:7][cH:8][c:9]([C:10]([F:11])([F:12])[F:13])[cH:14][cH:15]2)[o:1... | COC(=O)c1cc(-c2ccc(C(F)(F)F)cc2)oc1CBr.Sc1nc(-c2ccccc2)n[nH]1 | OCc1cc(-c2ccc(C(F)(F)F)cc2)oc1CSc1nc(-c2ccccc2)n[nH]1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 08c77f11eaf4e36a7f23d9c96fdbea329e0e9e71c97093be41efc81e5897bb0b | 0bc700e9066b623dea760dcab4d553b1bf12ee99b5abde8134b45af4be775469 | c1ccc(-c2n[nH]c(SCc3ccc(-c4ccccc4)o3)n2)cc1 | Br-[CH2;D2;+0:1]-[c:2]1:[#8;a:3]:[c:4]:[c:5]:[c:6]:1-[C;H0;D3;+0:7](=[O;H0;D1;+0:8])-O-C.[SH;D1;+0:9]-[c:10]1:[#7;a:11]:[c:12]:[#7;a:13]:[#7;a:14]:1>>[OH;D1;+0:8]-[CH2;D2;+0:7]-[c:6]1:[c:5]:[c:4]:[#8;a:3]:[c:2]:1-[CH2;D2;+0:1]-[S;H0;D2;+0:9]-[c:10]1:[#7;a:11]:[c:12]:[#7;a:13]:[#7;a:14]:1 | null | [] | null | null | null | null | The title compound was prepared using methyl 2-(bromomethyl)-5-[4-(trifluoromethyl)phenyl]-3-furoate (intermediate 44) and 3-phenyl-1,2,4-triazole-5-thiol.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester.Aromatic thiol | Primary alcohol.Monosulfide | null | null | c1ccoc1.c1ccccc1.c1nnc[nH]1.c1ccccc1 | HBr | null | null | null | COC(=O)c1cc(-c2ccc(C(F)(F)F)cc2)oc1CBr.Sc1nc(-c2ccccc2)n[nH]1>>OCc1cc(-c2ccc(C(F)(F)F)cc2)oc1CSc1nc(-c2ccccc2)n[nH]1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b4b250cb2381419385197056ebaf170b | COC(=O)c1cc(-c2ccc(C(F)(F)F)cc2)oc1CBr.COc1ccc(N2CCNCC2)cc1>>COc1ccc(N2CCN(Cc3oc(-c4ccc(C(F)(F)F)cc4)cc3CO)CC2)cc1 | BrCC=1OC(=CC1C(=O)OC)C1=CC=C(C=C1)C(F)(F)F.BrCC=1OC(=CC1C(=O)OC)C1=CC=C(C=C1)C(F)(F)F.COC1=CC=C(C=C1)N1CCNCC1>>COC1=CC=C(C=C1)N1CCN(CC1)CC=1OC(=CC1CO)C1=CC=C(C=C1)C(F)(F)F | CO[C:27]([c:26]1[c:12]([CH2:11]Br)[o:13][c:14](-[c:15]2[cH:16][cH:17][c:18]([C:19]([F:20])([F:21])[F:22])[cH:23][cH:24]2)[cH:25]1)=[O:28].[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([N:7]2[CH2:8][CH2:9][NH:10][CH2:29][CH2:30]2)[cH:31][cH:32]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([N:7]2[CH2:8][CH2:9][N:10]([CH2:11][c:12]3[o:13]... | COC(=O)c1cc(-c2ccc(C(F)(F)F)cc2)oc1CBr.COc1ccc(N2CCNCC2)cc1 | COc1ccc(N2CCN(Cc3oc(-c4ccc(C(F)(F)F)cc4)cc3CO)CC2)cc1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 8ed24dcb359948ee8bb05de0e4343150638867081ea8833d8370039a2d480011 | 5185a8f5e4b71d0234a3b03cc63e26b3b068dc9422b0dde6b5591d1d0b54c0f7 | c1ccc(-c2ccc(CN3CCN(c4ccccc4)CC3)o2)cc1 | Br-[CH2;D2;+0:1]-[c:2]1:[#8;a:3]:[c:4]:[c:5]:[c:6]:1-[C;H0;D3;+0:7](=[O;H0;D1;+0:8])-O-C.[#7:9]1-[C:10]-[C:11]-[NH;D2;+0:12]-[C:13]-[C:14]-1>>[OH;D1;+0:8]-[CH2;D2;+0:7]-[c:6]1:[c:5]:[c:4]:[#8;a:3]:[c:2]:1-[CH2;D2;+0:1]-[N;H0;D3;+0:12]1-[C:11]-[C:10]-[#7:9]-[C:14]-[C:13]-1 | null | [] | null | null | null | null | The title compound was prepared using methyl 2-(bromomethyl)-5-[4-(trifluoromethyl)phenyl]-3-furoate (intermediate 44) and 1-(4-methoxyphenyl)piperazine.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester.Secondary amine | Primary alcohol.Tertiary amine | C1C[NH]CCN1 | C1C[NH]CC[NH]1 | c1ccccc1.C1C[NH]CC[NH]1.c1ccoc1.c1ccccc1 | HBr | null | null | null | COC(=O)c1cc(-c2ccc(C(F)(F)F)cc2)oc1CBr.COc1ccc(N2CCNCC2)cc1>>COc1ccc(N2CCN(Cc3oc(-c4ccc(C(F)(F)F)cc4)cc3CO)CC2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-e19001d0595c45359652e9e2aef71108 | CCOC(=O)COc1ccc(S)cc1C.OCc1coc(-c2ccc(C(F)(F)F)cc2)c1>>CCOC(=O)COc1ccc(SCc2coc(-c3ccc(C(F)(F)F)cc3)c2)cc1C | C(CCC)P(CCCC)CCCC.C(C)OC(COC1=C(C=C(C=C1)S)C)=O.FC(C1=CC=C(C=C1)C1=CC(=CO1)CO)(F)F>>C(C)OC(COC1=C(C=C(C=C1)SCC1=COC(=C1)C1=CC=C(C=C1)C(F)(F)F)C)=O | [CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][O:7][c:8]1[cH:9][cH:10][c:11]([SH:12])[cH:29][c:30]1[CH3:31].O[CH2:13][c:14]1[cH:15][o:16][c:17](-[c:18]2[cH:19][cH:20][c:21]([C:22]([F:23])([F:24])[F:25])[cH:26][cH:27]2)[cH:28]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][O:7][c:8]1[cH:9][cH:10][c:11]([S:12][CH2:13][c:14]2[cH:15][... | CCOC(=O)COc1ccc(S)cc1C.OCc1coc(-c2ccc(C(F)(F)F)cc2)c1 | CCOC(=O)COc1ccc(SCc2coc(-c3ccc(C(F)(F)F)cc3)c2)cc1C | null | null | O1CCCC1 | Heteroatom Alkylation and Arylation | S-alkylation of thiols with alcohols | c119424abb7b621e5fb126e8156c5e4310815e8f2d609f48f2eb427b327d29ac | c1ccf05c97341d9cf75acae4c03f7d5a8212340a35905af6c8d60b4ccc775d1f | c1ccc(SCc2coc(-c3ccccc3)c2)cc1 | O-[CH2;D2;+0:1]-[c:2]1:[c:3]:[#8;a:4]:[c:5]:[c:6]:1.[SH;D1;+0:7]-[c:8](:[c:9]):[c:10]>>[c:9]:[c:8](-[S;H0;D2;+0:7]-[CH2;D2;+0:1]-[c:2]1:[c:3]:[#8;a:4]:[c:5]:[c:6]:1):[c:10] | null | [] | null | null | 18 | HOUR | A solution of {5-[4-(trifluoromethyl)phenyl]-3-furyl}methanol (0.15 g) in tetrahydrofuran (15 ml) stirred at 0° C. was treated with tributylphosphine (0.2 ml), as solution of ethyl(4-mercapto-2-methylphenoxy)acetate (0.150 g) in tetrahydrofuran (2 ml) and finally azodicarbonyldimorpholide (0.204 g). The reaction was al... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Aromatic thiol | Monosulfide | null | null | c1ccccc1.c1ccoc1.c1ccccc1 | HO- | O1CCCC1 | null | 18 | CCOC(=O)COc1ccc(S)cc1C.OCc1coc(-c2ccc(C(F)(F)F)cc2)c1>O1CCCC1>CCOC(=O)COc1ccc(SCc2coc(-c3ccc(C(F)(F)F)cc3)c2)cc1C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-8b8bdbd070704040b63b19183de9bb48 | Cc1cc(CCc2sc(-c3ccc(C#N)c(F)c3)cc2C)ccc1OCC12OCC(C)(CO1)CO2>>Cc1cc(CCc2sc(-c3ccc(C#N)c(F)c3)cc2C)ccc1OCC(=O)O | FC1=C(C#N)C=CC(=C1)C=1SC(=C(C1)C)CCC1=CC(=C(C=C1)OCC12OCC(CO1)(CO2)C)C.FC1=C(C#N)C=CC(=C1)C=1SC(=C(C1)C)CCC1=CC(=C(C=C1)OCC12OCC(CO1)(CO2)C)C.Cl>>C(#N)C1=C(C=C(C=C1)C1=CC(=C(S1)CCC1=CC(=C(OCC(=O)O)C=C1)C)C)F | CC12CO[C:27]([CH2:26][O:25][c:24]3[c:2]([CH3:1])[cH:3][c:4]([CH2:5][CH2:6][c:7]4[s:8][c:9](-[c:10]5[cH:11][cH:12][c:13]([C:14]#[N:15])[c:16]([F:17])[cH:18]5)[cH:19][c:20]4[CH3:21])[cH:22][cH:23]3)([O:28]C1)[O:29]C2>>[CH3:1][c:2]1[cH:3][c:4]([CH2:5][CH2:6][c:7]2[s:8][c:9](-[c:10]3[cH:11][cH:12][c:13]([C:14]#[N:15])[c:16... | Cc1cc(CCc2sc(-c3ccc(C#N)c(F)c3)cc2C)ccc1OCC12OCC(C)(CO1)CO2 | Cc1cc(CCc2sc(-c3ccc(C#N)c(F)c3)cc2C)ccc1OCC(=O)O | null | null | CC(C)O | Miscellaneous | OtherReaction | 9a421d947dea5eabdf4dcc8c7ef55ce0da9fa99b6d09003e970a195b77da081d | 7e63373a06cc9d97f08182de270157c3e46bdd18ed9cbb9a10929ec6100114c0 | c1ccc(CCc2ccc(-c3ccccc3)s2)cc1 | C-C12-C-O-[C;H0;D4;+0:1](-[C:2]-[#8:3])(-[O;H0;D2;+0:4]-C-1)-[O;H0;D2;+0:5]-C-2>>[#8:3]-[C:2]-[C;H0;D3;+0:1](=[O;H0;D1;+0:4])-[OH;D1;+0:5] | null | [] | null | null | null | null | A mixture of 2-fluoro-4-[4-methyl-5-(2-{3-methyl-4-[(4-methyl-2,6,7-trioxabicyclo[2.2.2]oct-1-yl)methoxy]phenyl}ethyl)thien-2-yl]benzonitrile (intermediate 101, 0.016 g) in 2-propanol (2 ml) was treated with 2M aqueous hydrochloric acid (1 ml) and the mixture stirred at reflux for 2 hours. The solvent was removed and t... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether.Ether | Carboxylic acid | C1OC2OCC1CO2 | null | c1ccccc1.c1ccsc1.c1ccccc1 | HO- | CC(C)O | null | null | Cc1cc(CCc2sc(-c3ccc(C#N)c(F)c3)cc2C)ccc1OCC12OCC(C)(CO1)CO2>CC(C)O>Cc1cc(CCc2sc(-c3ccc(C#N)c(F)c3)cc2C)ccc1OCC(=O)O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-91be913968d14eb2aa60244378ae719c | CCOC(=O)COc1ccc(C(C)(C)C(=O)c2sc(-c3ccc(C(F)(F)F)cc3)cc2C)cc1C>>CCOC(=O)COc1ccc(C(C)(C)Cc2sc(-c3ccc(C(F)(F)F)cc3)cc2C)cc1C | C(C)OC(COC1=C(C=C(C=C1)C(C(=O)C=1SC(=CC1C)C1=CC=C(C=C1)C(F)(F)F)(C)C)C)=O.C(C)OC(COC1=C(C=C(C=C1)C(C(=O)C=1SC(=CC1C)C1=CC=C(C=C1)C(F)(F)F)(C)C)C)=O.FC(C(=O)O)(F)F.C(C)[SiH](CC)CC>>C(C)OC(COC1=C(C=C(C=C1)C(CC=1SC(=CC1C)C1=CC=C(C=C1)C(F)(F)F)(C)C)C)=O | O=[C:15]([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])[c:33]([CH3:34])[cH:32]1)([CH3:13])[CH3:14])[c:16]1[s:17][c:18](-[c:19]2[cH:20][cH:21][c:22]([C:23]([F:24])([F:25])[F:26])[cH:27][cH:28]2)[cH:29][c:30]1[CH3:31]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][O:7][c:8]1[cH:9][cH:10][c:11]([... | CCOC(=O)COc1ccc(C(C)(C)C(=O)c2sc(-c3ccc(C(F)(F)F)cc3)cc2C)cc1C | CCOC(=O)COc1ccc(C(C)(C)Cc2sc(-c3ccc(C(F)(F)F)cc3)cc2C)cc1C | null | null | null | Reduction | OtherReaction | bdac4f77103f4da1c5b42ea95e05b0b7b31176b78204db5f4144ffca7b3d54d5 | f9ba67182f94acd5fbe41487f8f71e26bccf898b8fc8091ef46f4363de5628d4 | c1ccc(CCc2ccc(-c3ccccc3)s2)cc1 | O=[C;H0;D3;+0:1](-[c:2](:[c:3]):[#16;a:4]:[c:5])-[C:6](-[C;D1;H3:7])(-[C;D1;H3:8])-[c:9]>>[C;D1;H3:7]-[C:6](-[C;D1;H3:8])(-[c:9])-[CH2;D2;+0:1]-[c:2](:[c:3]):[#16;a:4]:[c:5] | null | [] | 50 | CELSIUS | null | null | To a reactivial containing ethyl[4-(1,1-dimethyl-2-{3-methyl-5-[4-(trifluoromethyl)phenyl]thien-2-yl}-2-oxoethyl)-2-methylphenoxy]acetate (intermediate 106, 36 mg) was added trifluoroacetic acid (0.22 ml) and triethylsilane (0.11 ml). The vial was then sealed and heated at 50° C. for 18 hours. The reaction was then all... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | null | null | null | c1ccccc1.c1ccsc1.c1ccccc1 | Other | null | 50 | null | CCOC(=O)COc1ccc(C(C)(C)C(=O)c2sc(-c3ccc(C(F)(F)F)cc3)cc2C)cc1C>>CCOC(=O)COc1ccc(C(C)(C)Cc2sc(-c3ccc(C(F)(F)F)cc3)cc2C)cc1C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-226bde8a3698467aba4d78807100d28f | CCOC(=O)COc1ccc(S(=O)(=O)Cl)cc1CC.Cc1oc(-c2ccc(C(F)(F)F)cc2)cc1CO>>CCc1cc(SCc2cc(-c3ccc(C(F)(F)F)cc3)oc2C)ccc1OCC(=O)O | C(C)(=O)O.CC=1OC(=CC1CO)C1=CC=C(C=C1)C(F)(F)F.C(C)OC(COC1=C(C=C(C=C1)S(=O)(=O)Cl)CC)=O.Cl[Si](C)(C)Cl.C(C)OC(COC1=C(C=C(C=C1)S(=O)(=O)Cl)CC)=O>>C(C)C1=C(OCC(=O)O)C=CC(=C1)SCC1=C(OC(=C1)C1=CC=C(C=C1)C(F)(F)F)C | CC[O:31][C:29]([CH2:28][O:27][c:26]1[c:3]([CH2:2][CH3:1])[cH:4][c:5]([S:6](=O)(=O)Cl)[cH:24][cH:25]1)=[O:30].O[CH2:7][c:8]1[cH:9][c:10](-[c:11]2[cH:12][cH:13][c:14]([C:15]([F:16])([F:17])[F:18])[cH:19][cH:20]2)[o:21][c:22]1[CH3:23]>>[CH3:1][CH2:2][c:3]1[cH:4][c:5]([S:6][CH2:7][c:8]2[cH:9][c:10](-[c:11]3[cH:12][cH:13][c... | CCOC(=O)COc1ccc(S(=O)(=O)Cl)cc1CC.Cc1oc(-c2ccc(C(F)(F)F)cc2)cc1CO | CCc1cc(SCc2cc(-c3ccc(C(F)(F)F)cc3)oc2C)ccc1OCC(=O)O | null | [Zn] | C(C)(=O)OCC | Heteroatom Alkylation and Arylation | OtherReaction | 796de8ae1724781d9501ecc5cfc619ccf545f09732157544ed04f39547792bff | af6bf08ef497d457478dd38016632c485c242d26f5c95b44be208b12e02e0b95 | c1ccc(SCc2coc(-c3ccccc3)c2)cc1 | C-C-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4].Cl-[S;H0;D4;+0:5](=O)(=O)-[c:6](:[c:7]):[c:8].O-[CH2;D2;+0:9]-[c:10]1:[c:11]:[c:12]:[#8;a:13]:[c:14]:1-[C;D1;H3:15]>>[C;D1;H3:15]-[c:14]1:[#8;a:13]:[c:12]:[c:11]:[c:10]:1-[CH2;D2;+0:9]-[S;H0;D2;+0:5]-[c:6](:[c:7]):[c:8].[C:3]-[C:2](=[O;D1;H0:4])-[OH;D1;+0:1] | null | [] | 60 | CELSIUS | null | null | To a mixture of zinc (407 mg) in ethyl acetate (10 ml) stirred at 60° C. was added acetic acid (0.203 ml) followed by a solution of ethyl[4-(chlorosulfonyl)-2-ethylphenoxy]acetate (intermediate 111, 546 mg) in ethyl acetate. The reaction mixture was stirred 60° C. for 2 hours and then dichlorodimethylsilane (0.431 ml) ... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Primary alcohol.Sulfonyl halide | Carboxylic acid.Monosulfide | null | null | c1ccccc1.c1ccoc1.c1ccccc1 | HCl | [Zn].C(C)(=O)OCC | 60 | null | CCOC(=O)COc1ccc(S(=O)(=O)Cl)cc1CC.Cc1oc(-c2ccc(C(F)(F)F)cc2)cc1CO>[Zn].C(C)(=O)OCC>CCc1cc(SCc2cc(-c3ccc(C(F)(F)F)cc3)oc2C)ccc1OCC(=O)O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-08e0beb152404f3a8b4579a391103cbc | CCOC(=O)COc1ccc(S(=O)(=O)Cl)cc1Cl.CCc1cc(SCc2cc(-c3ccc(C(F)(F)F)cc3)oc2C)ccc1OCC(=O)O>>Cc1oc(-c2ccc(C(F)(F)F)cc2)cc1CSc1ccc(OCC(=O)O)c(Cl)c1 | C(C)OC(COC1=C(C=C(C=C1)S(=O)(=O)Cl)Cl)=O.C(C)OC(COC1=C(C=C(C=C1)S(=O)(=O)Cl)Cl)=O.C(C)C1=C(OCC(=O)O)C=CC(=C1)SCC1=C(OC(=C1)C1=CC=C(C=C1)C(F)(F)F)C>>ClC1=C(OCC(=O)O)C=CC(=C1)SCC1=C(OC(=C1)C1=CC=C(C=C1)C(F)(F)F)C | CCOC(=O)COc1ccc(S(=O)(=O)Cl)cc1[Cl:29].CC[c:28]1[c:22]([O:23][CH2:24][C:25](=[O:26])[OH:27])[cH:21][cH:20][c:19]([S:18][CH2:17][c:16]2[c:2]([CH3:1])[o:3][c:4](-[c:5]3[cH:6][cH:7][c:8]([C:9]([F:10])([F:11])[F:12])[cH:13][cH:14]3)[cH:15]2)[cH:30]1>>[CH3:1][c:2]1[o:3][c:4](-[c:5]2[cH:6][cH:7][c:8]([C:9]([F:10])([F:11])[F:... | CCOC(=O)COc1ccc(S(=O)(=O)Cl)cc1Cl.CCc1cc(SCc2cc(-c3ccc(C(F)(F)F)cc3)oc2C)ccc1OCC(=O)O | Cc1oc(-c2ccc(C(F)(F)F)cc2)cc1CSc1ccc(OCC(=O)O)c(Cl)c1 | null | null | null | Functional Group Interconversion | OtherReaction | 079ece6ffe0f8e31abc68b44ee5594524ea32786556f938601dc8ba0143ec5f2 | d0a67bafb905ad19599d4d110791289547583ba3125d257544a61772787d1b7e | c1ccc(SCc2coc(-c3ccccc3)c2)cc1 | C-C-O-C(=O)-C-O-c1:c:c:c(-S(-Cl)(=O)=O):c:c:1-[Cl;H0;D1;+0:1].C-C-[c;H0;D3;+0:2](:[c:3]:[c:4]):[c:5](-[#8:6]):[c:7]>>[#8:6]-[c:5](:[c:7]):[c;H0;D3;+0:2](-[Cl;H0;D1;+0:1]):[c:3]:[c:4] | null | [] | null | null | null | null | The title compound was prepared from ethyl[4-(chlorosulfonyl)-2-chlorophenoxy]acetate (intermediate 113) by a method analogous to that used for the preparation of {2-ethyl-4-[({2-methyl-5-[4-(trifluoromethyl)phenyl]-3-furyl}methyl)thio]phenoxy}acetic acid (example 145).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ester.Ether.Sulfonyl halide | Aromatic halide | c1ccccc1.c1ccccc1 | c1ccccc1 | c1ccoc1.c1ccccc1.c1ccccc1 | HCl | null | null | null | CCOC(=O)COc1ccc(S(=O)(=O)Cl)cc1Cl.CCc1cc(SCc2cc(-c3ccc(C(F)(F)F)cc3)oc2C)ccc1OCC(=O)O>>Cc1oc(-c2ccc(C(F)(F)F)cc2)cc1CSc1ccc(OCC(=O)O)c(Cl)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-7a45ae9fe9034a5182d6f166a7d872ad | CCOC(=O)COc1ccc(S(=O)(=O)Br)cc1Cl.CCc1cc(SCc2cc(-c3ccc(C(F)(F)F)cc3)oc2C)ccc1OCC(=O)O>>Cc1oc(-c2ccc(C(F)(F)F)cc2)cc1CSc1ccc(OCC(=O)O)c(Br)c1 | C(C)OC(COC1=C(C=C(C=C1)S(=O)(=O)Br)Cl)=O.C(C)OC(COC1=C(C=C(C=C1)S(=O)(=O)Br)Cl)=O.C(C)C1=C(OCC(=O)O)C=CC(=C1)SCC1=C(OC(=C1)C1=CC=C(C=C1)C(F)(F)F)C>>BrC1=C(OCC(=O)O)C=CC(=C1)SCC1=C(OC(=C1)C1=CC=C(C=C1)C(F)(F)F)C | CCOC(=O)COc1ccc(S(=O)(=O)[Br:29])cc1Cl.CC[c:28]1[c:22]([O:23][CH2:24][C:25](=[O:26])[OH:27])[cH:21][cH:20][c:19]([S:18][CH2:17][c:16]2[c:2]([CH3:1])[o:3][c:4](-[c:5]3[cH:6][cH:7][c:8]([C:9]([F:10])([F:11])[F:12])[cH:13][cH:14]3)[cH:15]2)[cH:30]1>>[CH3:1][c:2]1[o:3][c:4](-[c:5]2[cH:6][cH:7][c:8]([C:9]([F:10])([F:11])[F:... | CCOC(=O)COc1ccc(S(=O)(=O)Br)cc1Cl.CCc1cc(SCc2cc(-c3ccc(C(F)(F)F)cc3)oc2C)ccc1OCC(=O)O | Cc1oc(-c2ccc(C(F)(F)F)cc2)cc1CSc1ccc(OCC(=O)O)c(Br)c1 | null | null | null | Functional Group Interconversion | OtherReaction | 079ece6ffe0f8e31abc68b44ee5594524ea32786556f938601dc8ba0143ec5f2 | d0a67bafb905ad19599d4d110791289547583ba3125d257544a61772787d1b7e | c1ccc(SCc2coc(-c3ccccc3)c2)cc1 | C-C-O-C(=O)-C-O-c1:c:c:c(-S(=O)(=O)-[Br;H0;D1;+0:1]):c:c:1-Cl.C-C-[c;H0;D3;+0:2](:[c:3]:[c:4]):[c:5](-[#8:6]):[c:7]>>[#8:6]-[c:5](:[c:7]):[c;H0;D3;+0:2](-[Br;H0;D1;+0:1]):[c:3]:[c:4] | null | [] | null | null | null | null | The title compound was prepared from ethyl[4-(bromosulfonyl)-2-chlorophenoxy]acetate (intermediate 114) by a method analogous to that used for the preparation of {2-ethyl4-[({2-methyl-5-[4-(trifluoromethyl)phenyl]-3-furyl}methyl)thio]phenoxy}acetic acid (example 145).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ester.Ether.Sulfonyl halide | Aromatic halide | c1ccccc1.c1ccccc1 | c1ccccc1 | c1ccoc1.c1ccccc1.c1ccccc1 | HCl | null | null | null | CCOC(=O)COc1ccc(S(=O)(=O)Br)cc1Cl.CCc1cc(SCc2cc(-c3ccc(C(F)(F)F)cc3)oc2C)ccc1OCC(=O)O>>Cc1oc(-c2ccc(C(F)(F)F)cc2)cc1CSc1ccc(OCC(=O)O)c(Br)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-2e54c38b1900406b95a26d375bd2588c | CCOC(=O)COc1ccc(S)cc1C.Cc1cc(-c2ccc(OC(F)(F)F)cc2)sc1CO>>CCOC(=O)COc1ccc(SCc2sc(-c3ccc(OC(F)(F)F)cc3)cc2C)cc1C | CC1=C(SC(=C1)C1=CC=C(C=C1)OC(F)(F)F)CO.C(C)OC(COC1=C(C=C(C=C1)SCC1=COC(=C1)C1=CC=C(C=C1)C(F)(F)F)C)=O.C(C)OC(COC1=C(C=C(C=C1)S)C)=O.CC1=C(SC(=C1)C1=CC=C(C=C1)OC(F)(F)F)CO.C(C)OC(COC1=C(C=C(C=C1)S)C)=O>>C(C)OC(COC1=C(C=C(C=C1)SCC=1SC(=CC1C)C1=CC=C(C=C1)OC(F)(F)F)C)=O | [CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][O:7][c:8]1[cH:9][cH:10][c:11]([SH:12])[cH:31][c:32]1[CH3:33].O[CH2:13][c:14]1[s:15][c:16](-[c:17]2[cH:18][cH:19][c:20]([O:21][C:22]([F:23])([F:24])[F:25])[cH:26][cH:27]2)[cH:28][c:29]1[CH3:30]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][O:7][c:8]1[cH:9][cH:10][c:11]([S:12][CH2:13][c... | CCOC(=O)COc1ccc(S)cc1C.Cc1cc(-c2ccc(OC(F)(F)F)cc2)sc1CO | CCOC(=O)COc1ccc(SCc2sc(-c3ccc(OC(F)(F)F)cc3)cc2C)cc1C | null | null | null | Heteroatom Alkylation and Arylation | S-alkylation of thiols with alcohols | c119424abb7b621e5fb126e8156c5e4310815e8f2d609f48f2eb427b327d29ac | c1ccf05c97341d9cf75acae4c03f7d5a8212340a35905af6c8d60b4ccc775d1f | c1ccc(SCc2ccc(-c3ccccc3)s2)cc1 | O-[CH2;D2;+0:1]-[c:2](:[c:3]):[#16;a:4]:[c:5].[SH;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[c:8]:[c:7](-[S;H0;D2;+0:6]-[CH2;D2;+0:1]-[c:2](:[c:3]):[#16;a:4]:[c:5]):[c:9] | null | [] | null | null | null | null | The title compound was prepared by a method analogous to that used for the preparation of ethyl{2-methyl-4-[({5-[4-(trifluoromethyl)phenyl]-3-furyl}methyl)thio]phenoxy}acetate (example 1) using ethyl(4-mercapto-2-methylphenoxy)acetate (intermediate 4) and {3-methyl-5-[4-(trifluoromethoxy)phenyl]thien-2-yl}methanol (int... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Aromatic thiol | Monosulfide | null | null | c1ccccc1.c1ccsc1.c1ccccc1 | HO- | null | null | null | CCOC(=O)COc1ccc(S)cc1C.Cc1cc(-c2ccc(OC(F)(F)F)cc2)sc1CO>>CCOC(=O)COc1ccc(SCc2sc(-c3ccc(OC(F)(F)F)cc3)cc2C)cc1C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-ab08d73f10fa4a0ea110a92bbee126a5 | CCOC(=O)COc1ccc(O)cc1C.Cc1cc(-c2cc(F)c(C(F)(F)F)cc2F)sc1CO>>CCOC(=O)COc1ccc(OCc2sc(-c3cc(F)c(C(F)(F)F)cc3F)cc2C)cc1C | FC1=C(C=C(C(=C1)C(F)(F)F)F)C1=CC(=C(S1)CO)C.C(C)OC(COC1=C(C=C(C=C1)SCC1=COC(=C1)C1=CC=C(C=C1)C(F)(F)F)C)=O.C(C)OC(COC1=C(C=C(C=C1)O)C)=O.FC1=C(C=C(C(=C1)C(F)(F)F)F)C1=CC(=C(S1)CO)C.C(C)OC(COC1=C(C=C(C=C1)O)C)=O>>C(C)OC(COC1=C(C=C(C=C1)OCC=1SC(=CC1C)C1=C(C=C(C(=C1)F)C(F)(F)F)F)C)=O | O[c:11]1[cH:10][cH:9][c:8]([O:7][CH2:6][C:4]([O:3][CH2:2][CH3:1])=[O:5])[c:33]([CH3:34])[cH:32]1.[OH:12][CH2:13][c:14]1[s:15][c:16](-[c:17]2[cH:18][c:19]([F:20])[c:21]([C:22]([F:23])([F:24])[F:25])[cH:26][c:27]2[F:28])[cH:29][c:30]1[CH3:31]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][O:7][c:8]1[cH:9][cH:10][c:11]([O:12][C... | CCOC(=O)COc1ccc(O)cc1C.Cc1cc(-c2cc(F)c(C(F)(F)F)cc2F)sc1CO | CCOC(=O)COc1ccc(OCc2sc(-c3cc(F)c(C(F)(F)F)cc3F)cc2C)cc1C | null | null | null | Heteroatom Alkylation and Arylation | Mitsunobu aryl ether | 8915084acbaaf997bf0f89ff5187cb2f89c25dc683fffc57b3391298c8430dd9 | 2258bd14c3b5449b92dc09cf9fa522f88d5071b4af20f7e968b60aa1ae6db0cf | c1ccc(OCc2ccc(-c3ccccc3)s2)cc1 | O-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[#16;a:6]:[c:7]-[C:8]-[OH;D1;+0:9]>>[#16;a:6]:[c:7]-[C:8]-[O;H0;D2;+0:9]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5] | null | [] | null | null | null | null | The title compound was prepared by a method analogous to that used for the preparation of ethyl{2-methyl-4-[({5-[4-(trifluoromethyl)phenyl]-3-furyl}methyl)thio]phenoxy}acetate (example 1) using ethyl(4-hydroxy-2-methylphenoxy)acetate (intermediate 7) and {5-[2,5-difluoro-4-(trifluoromethyl)phenyl]-3-methylthien-2-yl}me... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Aromatic alcohol | Ether | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccsc1.c1ccccc1 | HO- | null | null | null | CCOC(=O)COc1ccc(O)cc1C.Cc1cc(-c2cc(F)c(C(F)(F)F)cc2F)sc1CO>>CCOC(=O)COc1ccc(OCc2sc(-c3cc(F)c(C(F)(F)F)cc3F)cc2C)cc1C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-76587a1d5d874959b2ba87d99a8c3da7 | CCOC(=O)COc1ccc(O)cc1C.Cc1cc(-c2ccc(C(F)(F)F)c(F)c2F)sc1CO>>CCOC(=O)COc1ccc(OCc2sc(-c3ccc(C(F)(F)F)c(F)c3F)cc2C)cc1C | FC1=C(C=CC(=C1F)C(F)(F)F)C1=CC(=C(S1)CO)C.C(C)OC(COC1=C(C=C(C=C1)SCC1=COC(=C1)C1=CC=C(C=C1)C(F)(F)F)C)=O.C(C)OC(COC1=C(C=C(C=C1)O)C)=O.FC1=C(C=CC(=C1F)C(F)(F)F)C1=CC(=C(S1)CO)C.C(C)OC(COC1=C(C=C(C=C1)O)C)=O>>C(C)OC(COC1=C(C=C(C=C1)OCC=1SC(=CC1C)C1=C(C(=C(C=C1)C(F)(F)F)F)F)C)=O | O[c:11]1[cH:10][cH:9][c:8]([O:7][CH2:6][C:4]([O:3][CH2:2][CH3:1])=[O:5])[c:33]([CH3:34])[cH:32]1.[OH:12][CH2:13][c:14]1[s:15][c:16](-[c:17]2[cH:18][cH:19][c:20]([C:21]([F:22])([F:23])[F:24])[c:25]([F:26])[c:27]2[F:28])[cH:29][c:30]1[CH3:31]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][O:7][c:8]1[cH:9][cH:10][c:11]([O:12][C... | CCOC(=O)COc1ccc(O)cc1C.Cc1cc(-c2ccc(C(F)(F)F)c(F)c2F)sc1CO | CCOC(=O)COc1ccc(OCc2sc(-c3ccc(C(F)(F)F)c(F)c3F)cc2C)cc1C | null | null | null | Heteroatom Alkylation and Arylation | Mitsunobu aryl ether | 8915084acbaaf997bf0f89ff5187cb2f89c25dc683fffc57b3391298c8430dd9 | 2258bd14c3b5449b92dc09cf9fa522f88d5071b4af20f7e968b60aa1ae6db0cf | c1ccc(OCc2ccc(-c3ccccc3)s2)cc1 | O-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[#16;a:6]:[c:7]-[C:8]-[OH;D1;+0:9]>>[#16;a:6]:[c:7]-[C:8]-[O;H0;D2;+0:9]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5] | null | [] | null | null | null | null | The title compound was prepared by a method analogous to that used for the preparation of ethyl{2-methyl-4-[({5-[4-(trifluoromethyl)phenyl]-3-furyl}methyl)thio]phenoxy}acetate (example 1) using ethyl(4-hydroxy-2-methylphenoxy)acetate (intermediate 7) and {5-[2,3-difluoro-4-(trifluoromethyl)phenyl]-3-methylthien-2-yl}me... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Aromatic alcohol | Ether | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccsc1.c1ccccc1 | HO- | null | null | null | CCOC(=O)COc1ccc(O)cc1C.Cc1cc(-c2ccc(C(F)(F)F)c(F)c2F)sc1CO>>CCOC(=O)COc1ccc(OCc2sc(-c3ccc(C(F)(F)F)c(F)c3F)cc2C)cc1C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-a1c3917ecc264ee88309357cfcc15257 | CCOC(=O)COc1ccc(O)cc1C.Cc1cc(-c2ccc(C(F)(F)F)cc2F)sc1CO>>CCOC(=O)COc1ccc(OCc2sc(-c3ccc(C(F)(F)F)cc3F)cc2C)cc1C | FC1=C(C=CC(=C1)C(F)(F)F)C1=CC(=C(S1)CO)C.C(C)OC(COC1=C(C=C(C=C1)SCC1=COC(=C1)C1=CC=C(C=C1)C(F)(F)F)C)=O.C(C)OC(COC1=C(C=C(C=C1)O)C)=O.FC1=C(C=CC(=C1)C(F)(F)F)C1=CC(=C(S1)CO)C.C(C)OC(COC1=C(C=C(C=C1)O)C)=O>>C(C)OC(COC1=C(C=C(C=C1)OCC=1SC(=CC1C)C1=C(C=C(C=C1)C(F)(F)F)F)C)=O | O[c:11]1[cH:10][cH:9][c:8]([O:7][CH2:6][C:4]([O:3][CH2:2][CH3:1])=[O:5])[c:32]([CH3:33])[cH:31]1.[OH:12][CH2:13][c:14]1[s:15][c:16](-[c:17]2[cH:18][cH:19][c:20]([C:21]([F:22])([F:23])[F:24])[cH:25][c:26]2[F:27])[cH:28][c:29]1[CH3:30]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][O:7][c:8]1[cH:9][cH:10][c:11]([O:12][CH2:13][... | CCOC(=O)COc1ccc(O)cc1C.Cc1cc(-c2ccc(C(F)(F)F)cc2F)sc1CO | CCOC(=O)COc1ccc(OCc2sc(-c3ccc(C(F)(F)F)cc3F)cc2C)cc1C | null | null | null | Heteroatom Alkylation and Arylation | Mitsunobu aryl ether | 8915084acbaaf997bf0f89ff5187cb2f89c25dc683fffc57b3391298c8430dd9 | 2258bd14c3b5449b92dc09cf9fa522f88d5071b4af20f7e968b60aa1ae6db0cf | c1ccc(OCc2ccc(-c3ccccc3)s2)cc1 | O-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[#16;a:6]:[c:7]-[C:8]-[OH;D1;+0:9]>>[#16;a:6]:[c:7]-[C:8]-[O;H0;D2;+0:9]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5] | null | [] | null | null | null | null | The title compound was prepared by a method analogous to that used for the preparation of ethyl{2-methyl-4-[({5-[4-(trifluoromethyl)phenyl]-3-furyl}methyl)thio]phenoxy}acetate (example 1) using ethyl(4-hydroxy-2-methylphenoxy)acetate (intermediate 7) and {5-[2-fluoro-4-(trifluoromethyl)phenyl]-3-methylthien-2-yl}methan... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Aromatic alcohol | Ether | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccsc1.c1ccccc1 | HO- | null | null | null | CCOC(=O)COc1ccc(O)cc1C.Cc1cc(-c2ccc(C(F)(F)F)cc2F)sc1CO>>CCOC(=O)COc1ccc(OCc2sc(-c3ccc(C(F)(F)F)cc3F)cc2C)cc1C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-6f988cea8bdb463dbc69ed0a7151a8a4 | CCOC(=O)C(C)(C)Oc1ccc(O)cc1C.OC(c1ccccc1)c1csc(-c2ccc(C(F)(F)F)cc2)c1>>CCOC(=O)C(C)(C)Oc1ccc(OC(c2ccccc2)c2csc(-c3ccc(C(F)(F)F)cc3)c2)cc1C | C1(=CC=CC=C1)C(O)C1=CSC(=C1)C1=CC=C(C=C1)C(F)(F)F.C(C)OC(COC1=C(C=C(C=C1)SCC1=COC(=C1)C1=CC=C(C=C1)C(F)(F)F)C)=O.OC1=CC(=C(OC(C(=O)OCC)(C)C)C=C1)C.C1(=CC=CC=C1)C(O)C1=CSC(=C1)C1=CC=C(C=C1)C(F)(F)F.OC1=CC(=C(OC(C(=O)OCC)(C)C)C=C1)C>>CC(C(=O)OCC)(C)OC1=C(C=C(C=C1)OC(C1=CSC(=C1)C1=CC=C(C=C1)C(F)(F)F)C1=CC=CC=C1)C | O[c:13]1[cH:12][cH:11][c:10]([O:9][C:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])([CH3:7])[CH3:8])[c:38]([CH3:39])[cH:37]1.[OH:14][CH:15]([c:16]1[cH:17][cH:18][cH:19][cH:20][cH:21]1)[c:22]1[cH:23][s:24][c:25](-[c:26]2[cH:27][cH:28][c:29]([C:30]([F:31])([F:32])[F:33])[cH:34][cH:35]2)[cH:36]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[C:... | CCOC(=O)C(C)(C)Oc1ccc(O)cc1C.OC(c1ccccc1)c1csc(-c2ccc(C(F)(F)F)cc2)c1 | CCOC(=O)C(C)(C)Oc1ccc(OC(c2ccccc2)c2csc(-c3ccc(C(F)(F)F)cc3)c2)cc1C | null | null | null | Heteroatom Alkylation and Arylation | Mitsunobu aryl ether | de817abd28aa0a6201a692784d613d548e53f67c49ed49b6eff382c8e9e7a9e4 | 776ba735002e33225fbc578943016110c2c43efefd97bfeea4ec3cc2e2e1532f | c1ccc(OC(c2ccccc2)c2csc(-c3ccccc3)c2)cc1 | O-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[#16;a:6]:[c:7]:[c:8]-[C:9](-[OH;D1;+0:10])-[c:11]>>[#16;a:6]:[c:7]:[c:8]-[C:9](-[c:11])-[O;H0;D2;+0:10]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5] | null | [] | null | null | null | null | The title compound was prepared by a method analogous to that used for the preparation of ethyl{2-methyl-4-[({5-[4-(trifluoromethyl)phenyl]-3-furyl}methyl)thio]phenoxy}acetate (example 1) using ethyl 2-(4-hydroxy-2-methylphenoxy)-2-methylpropanoate (intermediate 10) and phenyl{5-[4-(trifluoromethyl)phenyl]thien-3-yl}me... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol.Aromatic alcohol | Ether | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1.c1ccsc1.c1ccccc1 | HO- | null | null | null | CCOC(=O)C(C)(C)Oc1ccc(O)cc1C.OC(c1ccccc1)c1csc(-c2ccc(C(F)(F)F)cc2)c1>>CCOC(=O)C(C)(C)Oc1ccc(OC(c2ccccc2)c2csc(-c3ccc(C(F)(F)F)cc3)c2)cc1C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-ef292f5548cf455d9ca50f896ef61a98 | CCOC(=O)C(C)(C)Br.CCOC(=O)COc1ccc(S)cc1C>>CCOC(=O)COc1ccc(C(C)=O)cc1C | BrC(C(=O)OCC)(C)C.C(C)OC(COC1=C(C=C(C=C1)S)C)=O.C(=O)([O-])[O-].[K+].[K+]>>C(C)OC(COC1=C(C=C(C=C1)C(C)=O)C)=O | CCO[C:12]([C:13](C)(C)Br)=[O:14].S[c:11]1[cH:10][cH:9][c:8]([O:7][CH2:6][C:4]([O:3][CH2:2][CH3:1])=[O:5])[c:16]([CH3:17])[cH:15]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]([CH3:13])=[O:14])[cH:15][c:16]1[CH3:17] | CCOC(=O)C(C)(C)Br.CCOC(=O)COc1ccc(S)cc1C | CCOC(=O)COc1ccc(C(C)=O)cc1C | null | null | CN(C)C=O | C-C Coupling | OtherReaction | 47bc1c5ebaa21b501b95661d24a495c8f929f1889d203d224f3d831e6d17cc4e | b406da8c336ad5ec437cfa31e8d0c468778167c3d6c955911a35ee5b11adf9b0 | c1ccccc1 | Br-[C;H0;D4;+0:1](-C)(-C)-[C;H0;D3;+0:2](=[O;D1;H0:3])-O-C-C.S-[c;H0;D3;+0:4](:[c:5]:[c:6]):[c:7]:[c:8]>>[CH3;D1;+0:1]-[C;H0;D3;+0:2](=[O;D1;H0:3])-[c;H0;D3;+0:4](:[c:5]:[c:6]):[c:7]:[c:8] | 159 | [{"value": 77.0, "product": "C(C)OC(COC1=C(C=C(C=C1)C(C)=O)C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 159.0, "product": "C(C)OC(COC1=C(C=C(C=C1)C(C)=O)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | 18 | HOUR | To intermediate 4 (710 mg, 1.81 mmol) in DMF (50 mL) was added the K2CO3 (275 mg, 1.99 mmol) followed by the ethyl 2-bromo-2-methylpropanate (280 μL, 1.91 mmol; Aldrich) and the reaction heated to 80° C. After 18 h, the reaction cooled to rt and the solvent removed in vacuo. The residue treated with water (200 mL), ext... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary halide.Ester.Aromatic thiol | Ketone | c1ccccc1 | c1ccccc1 | c1ccccc1 | HBr | CN(C)C=O | 80 | 18 | CCOC(=O)C(C)(C)Br.CCOC(=O)COc1ccc(S)cc1C>CN(C)C=O>CCOC(=O)COc1ccc(C(C)=O)cc1C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-63c05866145e472c88a3d838aafd9c42 | O=C(c1ccccc1)c1ccc(O)cc1>>C=COc1ccc(C(=O)c2ccccc2)cc1 | OC1=CC=C(C(=O)C2=CC=CC=C2)C=C1.CN1C(CCC1)=O>>C(=C)OC1=CC=C(C(=O)C2=CC=CC=C2)C=C1 | [OH:3][c:4]1[cH:5][cH:6][c:7]([C:8](=[O:9])[c:10]2[cH:11][cH:12][cH:13][cH:14][cH:15]2)[cH:16][cH:17]1>>[CH2:1]=[CH:2][O:3][c:4]1[cH:5][cH:6][c:7]([C:8](=[O:9])[c:10]2[cH:11][cH:12][cH:13][cH:14][cH:15]2)[cH:16][cH:17]1 | O=C(c1ccccc1)c1ccc(O)cc1 | C=COc1ccc(C(=O)c2ccccc2)cc1 | null | C1=CC=C2C=C(C=CC2=C1)C(=O)[O-].C1=CC=C2C=C(C=CC2=C1)C(=O)[O-].[Zn+2] | null | Miscellaneous | OtherReaction | 0b539ac0802cb789660ce0cc70ae8bc9786407ca4ff8a05c93c4348f8f2e76e1 | 1a00be42b4344440ff37c1e785c89edf1b876e1a8b1bf9225eb60588fafccf76 | O=C(c1ccccc1)c1ccccc1 | [OH;D1;+0:1]-[c:2](:[c:3]):[c:4]>>[C;D1;H2:5]=[C:6]-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | 190 | CELSIUS | null | null | A mixture of 650 g of 4-hydroxybenzophenone (98% by weight, Avocado, Research Chemicals Ltd.), 750 ml of N-methylpyrrolidone (>99% by weight, BASF AG) and 60 g of zinc naphthenate (Nusa; zinc salts of naphthenic acids, zinc content 12% by weight) was charged with stirring to a 2.5 l autoclave and flushed with nitrogen.... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic alcohol | Ether.Vinyl | null | null | c1ccccc1.c1ccccc1 | Other | C1=CC=C2C=C(C=CC2=C1)C(=O)[O-].C1=CC=C2C=C(C=CC2=C1)C(=O)[O-].[Zn+2] | 190 | null | O=C(c1ccccc1)c1ccc(O)cc1>C1=CC=C2C=C(C=CC2=C1)C(=O)[O-].C1=CC=C2C=C(C=CC2=C1)C(=O)[O-].[Zn+2]>C=COc1ccc(C(=O)c2ccccc2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-8cda2c9114054d9c960cc6d973d5c6a6 | CO[Si](CCl)(OC)OC.C[O-]>>COC[Si](OC)(OC)OC | ClC[Si](OC)(OC)OC.C[O-].[Na+].[SiH4].[Cl-].[Na+]>>COC[Si](OC)(OC)OC | Cl[CH2:3][Si:4]([O:5][CH3:6])([O:7][CH3:8])[O:9][CH3:10].[CH3:1][O-:2]>>[CH3:1][O:2][CH2:3][Si:4]([O:5][CH3:6])([O:7][CH3:8])[O:9][CH3:10] | CO[Si](CCl)(OC)OC.C[O-] | COC[Si](OC)(OC)OC | null | null | CO | Heteroatom Alkylation and Arylation | OtherReaction | 3dd6ea90858eede84ece2f60931b760bd509d5f421f2feb2b0fe7a2c006d84f0 | 62c7c72c35b09d63ca1131e6cd8c0b88a31e29901d660456b77319cfd78354c7 | null | Cl-[CH2;D2;+0:1]-[#14:2](-[#8:3]-[C;D1;H3:4])(-[#8:5]-[C;D1;H3:6])-[#8:7]-[C;D1;H3:8].[C;D1;H3:9]-[O-;H0;D1:10]>>[C;D1;H3:8]-[#8:7]-[#14:2](-[#8:3]-[C;D1;H3:4])(-[#8:5]-[C;D1;H3:6])-[CH2;D2;+0:1]-[O;H0;D2;+0:10]-[C;D1;H3:9] | null | [] | null | null | 30 | MINUTE | 340 g (6.3 mol) of sodium methylate (95% strength) are dissolved in portions in 2.5 l of methanol in a laboratory reactor blanketed with nitrogen. During this procedure, the solution heats up to 65° C. Thereafter, 995 g (5.8 mol) of chloromethyltrimethoxysilane are added dropwise over 1.5 h and stirring is effected for... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | Ether | null | null | null | Other | CO | null | 0.5 | CO[Si](CCl)(OC)OC.C[O-]>CO>COC[Si](OC)(OC)OC |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-2b9cd45206bd483889c44f0a2aa70c02 | Brc1c2ccccc2cc2ccccc12>>c1ccc2cc3ccccc3cc2c1 | BrC=1C2=CC=CC=C2C=C2C=CC=CC12.BrC1=C(C=CC=C1)O>>C1=CC=CC2=CC3=CC=CC=C3C=C12 | Br[c:5]1[c:4]2[cH:3][cH:2][cH:1][cH:14][c:13]2[cH:12][c:11]2[c:6]1[cH:7][cH:8][cH:9][cH:10]2>>[cH:1]1[cH:2][cH:3][c:4]2[cH:5][c:6]3[cH:7][cH:8][cH:9][cH:10][c:11]3[cH:12][c:13]2[cH:14]1 | Brc1c2ccccc2cc2ccccc12 | c1ccc2cc3ccccc3cc2c1 | null | CC(C)([P](C(C)(C)C)([Pd][P](C(C)(C)C)(C(C)(C)C)C(C)(C)C)C(C)(C)C)C.[Cl-].[Cl-].[Zn+2] | CCOCC.CCCCCC | Functional Group Interconversion | Aromatic dehalogenation | 310e0ad7d37610c1c6c21ab0d226f1b6ec5899334d78721f67eb050fd6bad48a | 56de34d4a44cb25d9380269ee5e138b0f24b40a3a0db22c5508049dc775a861f | c1ccc2cc3ccccc3cc2c1 | Br-[c;H0;D3;+0:1](:[c:2](:[c:3]):[c:4]):[c:5](:[c:6]):[c:7]>>[c:6]:[c:5](:[c:7]):[cH;D2;+0:1]:[c:2](:[c:3]):[c:4] | null | [] | -30 | CELSIUS | 20 | MINUTE | A solution of 9-bromoanthracene (0.67 g, 2.6 mmol, 1.2 eq) in dry Et2O (13 mL) under N2 was cooled to −30° C. and nBuli (1.6 M in hexane, 1.6 mL, 2.6 mmol, 1.2 eq) was added dropwise. The solution was stirred for 20 min. at −30° C. followed by dropwise addition of ZnCl2 (0.50 M in THF, 5.2 mL, 2.6 mmol, 1.2 eq). The re... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | null | c1ccc2cc3ccccc3cc2c1 | c1ccc2cc3ccccc3cc2c1 | c1ccc2cc3ccccc3cc2c1 | Br- | CC(C)([P](C(C)(C)C)([Pd][P](C(C)(C)C)(C(C)(C)C)C(C)(C)C)C(C)(C)C)C.[Cl-].[Cl-].[Zn+2].CCOCC.CCCCCC | -30 | 0.333333 | Brc1c2ccccc2cc2ccccc12>CC(C)([P](C(C)(C)C)([Pd][P](C(C)(C)C)(C(C)(C)C)C(C)(C)C)C(C)(C)C)C.[Cl-].[Cl-].[Zn+2].CCOCC.CCCCCC>c1ccc2cc3ccccc3cc2c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-2c17127e70e542a9b0255cbe6dba7bc2 | NC(=O)C[C@H](N)C(=O)O>>[NH4+].[NH4+] | N[C@@H](CC(=O)[O-])C(=O)[O-].N[C@@H](CC(N)=O)C(=O)O>>N[C@@H](CC(=O)[O-])C(=O)[O-].[NH4+].[NH4+] | O=C(O)[C@H](CC(=O)[NH2:10])[NH2:11]>>[NH4+:10].[NH4+:11] | NC(=O)C[C@H](N)C(=O)O | [NH4+].[NH4+] | null | null | null | Reduction | OtherReaction | 4e097eee029da2bac5192f43982771bdcbbf7c48da7dee640ff8775d16fff86f | b2286f9296e1425d9328db213e418354a5dd29cad2a3df36f0b19f7aa7f120bb | null | O-C(=O)-[C@H](-[NH2;D1;+0:1])-C-C(=O)-[NH2;D1;+0:2]>>[NH4+;D0:2].[NH4+;D0:1] | null | [] | 180 | CELSIUS | null | null | The IR spectrum of the product obtained after heating at 180° C. for three hours showed the peaks associated with polymers of aspartate, e.g. at 1391 (carboxylate), 1533 and 1589 (primary amide doublet), and 3300 cm−1 (carboxylate), as well as signals characteristic of asparagine residues, at 1648 cm−1 and 3072 cm−1 (s... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amide.Primary amine | null | null | null | null | Other | null | 180 | null | NC(=O)C[C@H](N)C(=O)O>>[NH4+].[NH4+] |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-e9f0bef708674089b4baba65dc3ddbb7 | N[C@@H](CC(=O)O)C(=O)O.[Na+].[OH-].[OH-]>>N[C@@H](CC(=O)[O-])C(=O)[O-].N[C@@H](CC(=O)[O-])C(=O)[O-].[NH4+].[Na+].[Na+] | [OH-].[Na+].N[C@@H](CC(=O)O)C(=O)O.[NH4+].[OH-].N[C@@H](CC(=O)O)C(=O)O>>N[C@@H](CC(=O)O)C(=O)O.N[C@@H](CC(=O)[O-])C(=O)[O-].[NH4+].[NH4+].N[C@@H](CC(=O)[O-])C(=O)[O-].[Na+].[Na+] | [C@H:11]([CH2:12][C:13](=[O:14])[OH:15])([C:16](=[O:17])[OH:18])[NH2:28].[Na+:30].[OH-:23].[OH-:24]>>[NH2:10][C@@H:11]([CH2:12][C:13](=[O:14])[O-:15])[C:16](=[O:17])[O-:18].[NH2:19][C@@H:20]([CH2:21][C:22](=[O:23])[O-:24])[C:25](=[O:26])[O-:27].[NH4+:28].[Na+:30].[Na+:31] | N[C@@H](CC(=O)O)C(=O)O.[Na+].[OH-].[OH-] | N[C@@H](CC(=O)[O-])C(=O)[O-].N[C@@H](CC(=O)[O-])C(=O)[O-].[NH4+].[Na+].[Na+] | null | null | null | Acylation | OtherReaction | ef2e54ea56226d17a3bda7226c779d90be4a19126aecd069c8f0ccc285197b15 | 3485e543eb51f12a156d7452009ff34714cdfffacac3df3fbdeb661b3b5aeec0 | null | [NH2;D1;+0:1]-[C@@H;D3;+0:2](-[C:3]-[C:4](=[O;D1;H0:5])-[OH;D1;+0:6])-[C:7](=[O;D1;H0:8])-[OH;D1;+0:9].[OH-;D0:10].[OH-;D0:11]>>[C:12]-[C:13](-[O-;H0;D1:11])=[O;H0;D1;+0:10].[N;D1;H2:14]-[C@@H;D3;+0:2](-[C:3]-[C:4](-[O-;H0;D1:6])=[O;D1;H0:5])-[C:7](-[O-;H0;D1:9])=[O;D1;H0:8].[NH4+;D0:1] | null | [] | null | null | 8 | HOUR | A sample of 13.3 g (100 mmol) of aspartic acid was slurried in 100 ml distilled water with stirring, and the aspartic acid was partially neutralized with 5 ml of 10 N NaOH (50 mmol). Conc. NH4OH (3.38 ml, 14.8 N, 50 mmol) was pipetted into the beaker, fully neutralizing and solubilizing the aspartic acid. The beaker wa... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Carboxylic acid.Primary amine | Primary amine.Primary amine | null | null | null | null | null | null | 8 | N[C@@H](CC(=O)O)C(=O)O.[Na+].[OH-].[OH-]>>N[C@@H](CC(=O)[O-])C(=O)[O-].N[C@@H](CC(=O)[O-])C(=O)[O-].[NH4+].[Na+].[Na+] |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-1aabd38412ae479badeec4cd7eb6e36c | N[C@@H](CC(=O)[O-])C(=O)[O-].[NH4+].[Na+]>>O=C1CCC(=O)N1.[Na+] | N[C@@H](CC(=O)[O-])C(=O)[O-].[NH4+].[NH4+].N[C@@H](CC(=O)[O-])C(=O)[O-].[Na+].[Na+]>>N[C@@H](CC(=O)[O-])C(=O)[O-].[Na+].[Na+].C1(CCC(N1)=O)=O | N[C@H:12]([C:11]([O-])=[O:10])[CH2:13][C:14]([O-])=[O:15].[NH4+:16].[Na+:18]>>[O:10]=[C:11]1[CH2:12][CH2:13][C:14](=[O:15])[NH:16]1.[Na+:18] | N[C@@H](CC(=O)[O-])C(=O)[O-].[NH4+].[Na+] | O=C1CCC(=O)N1.[Na+] | null | null | null | Acylation | OtherReaction | 85e23db170895656c7d8f37e4a918c5f10cfc4f0a3c799fa686ce695a0094dde | 4235fe62ea1d70a32b899f5bf28f64fa318b467d2a5a57a751c3b1a6dac43d71 | O=C1CCC(=O)N1 | N-[C@@H;D3;+0:1](-[C:2]-[C;H0;D3;+0:3](-[O-])=[O;D1;H0:4])-[C;H0;D3;+0:5](-[O-])=[O;D1;H0:6].[NH4+;D0:7]>>[O;D1;H0:6]=[C;H0;D3;+0:5]1-[CH2;D2;+0:1]-[C:2]-[C;H0;D3;+0:3](=[O;D1;H0:4])-[NH;D2;+0:7]-1 | null | [] | null | null | null | null | The reactions and procedures of this Example were repeated, except that the monomer ratios of ammonium aspartate and sodium aspartate were adjusted (in part A) to produce a 1:2 copolymer of sodium aspartate and succinimide. A solution of this copolymer was titrated to pH 4.0 and ring-closed as above. The resulting terp... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | Unsubstituted dicarboximide | null | C1CCNC1 | C1CCNC1 | HO- | null | null | null | N[C@@H](CC(=O)[O-])C(=O)[O-].[NH4+].[Na+]>>O=C1CCC(=O)N1.[Na+] |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-2f3cd46004c1483d8835a009998eb43c | O=C1CCC(=O)N1.[Na+]>>O=C1CCC(=O)N1.[Na+] | N[C@@H](CC(=O)[O-])C(=O)[O-].[Na+].[Na+].N[C@@H](CC(N)=O)C(=O)O.C1(CCC(N1)=O)=O>>N[C@@H](CC(=O)[O-])C(=O)[O-].[Na+].[Na+].C1(CCC(N1)=O)=O | [O:10]=[C:11]1[CH2:12][CH2:13][C:14](=[O:15])[NH:16]1.[Na+:18]>>[O:10]=[C:11]1[CH2:12][CH2:13][C:14](=[O:15])[NH:16]1.[Na+:18] | O=C1CCC(=O)N1.[Na+] | O=C1CCC(=O)N1.[Na+] | null | null | O | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | O=C1CCC(=O)N1 | null | null | [] | null | null | null | null | The reactions and procedures of this Example were repeated, except that the monomer ratios of ammonium aspartate and sodium aspartate were adjusted (in part A) to produce a 1:2 copolymer of sodium aspartate and succinimide. A solution of this copolymer was titrated to pH 4.0 and ring-closed as above. The resulting terp... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | C1CCNC1 | null | O | null | null | O=C1CCC(=O)N1.[Na+]>O>O=C1CCC(=O)N1.[Na+] |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-9b97e0b01ff54db5b0b5a0234ecca14d | N[C@@H](CCCNC(=O)OCc1ccccc1)C(=O)O.O=CO>>O=CN[C@@H](CCCNC(=O)OCc1ccccc1)C(=O)O | N[C@@H](CCCNC(=O)OCC1=CC=CC=C1)C(=O)O.C(=O)O.C(C)(=O)OC(C)=O>>N([C@@H](CCCNC(=O)OCC1=CC=CC=C1)C(=O)O)C=O | [NH2:3][C@@H:4]([CH2:5][CH2:6][CH2:7][NH:8][C:9](=[O:10])[O:11][CH2:12][c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1)[C:19](=[O:20])[OH:21].O[CH:2]=[O:1]>>[O:1]=[CH:2][NH:3][C@@H:4]([CH2:5][CH2:6][CH2:7][NH:8][C:9](=[O:10])[O:11][CH2:12][c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1)[C:19](=[O:20])[OH:21] | N[C@@H](CCCNC(=O)OCc1ccccc1)C(=O)O.O=CO | O=CN[C@@H](CCCNC(=O)OCc1ccccc1)C(=O)O | null | null | O | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | c1ccccc1 | O-[CH;D2;+0:1]=[O;D1;H0:2].[C:3]-[C:4](-[NH2;D1;+0:5])-[C:6](=[O;D1;H0:7])-[O;D1;H1:8]>>[C:3]-[C:4](-[NH;D2;+0:5]-[CH;D2;+0:1]=[O;D1;H0:2])-[C:6](=[O;D1;H0:7])-[O;D1;H1:8] | 88 | [{"value": 88.0, "product": "N([C@@H](CCCNC(=O)OCC1=CC=CC=C1)C(=O)O)C=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | 444.7 g (1.67 mole) of commercially available H-Orn(Z)-OH was dissolved in 3.5 L (93 moles) of formic acid. The solution was cooled in an ice bath, and 1.17 L (12 moles) of acetic anhydride was subsequently added in dropwise fashion over two hours while the temperature of the reaction mixture was maintained between abo... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1 | HO- | O | null | 2 | N[C@@H](CCCNC(=O)OCc1ccccc1)C(=O)O.O=CO>O>O=CN[C@@H](CCCNC(=O)OCc1ccccc1)C(=O)O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-0254ce23dea8486095efb817b0675e5b | O=C(NCCC[C@H](NC(=O)OCC1c2ccccc2-c2ccccc21)C(=O)O)OCc1ccccc1>>O=C(NCCC[C@@H](CO)NC(=O)OCC1c2ccccc2-c2ccccc21)OCc1ccccc1 | N([C@@H](CCCNC(=O)OCC1=CC=CC=C1)C(=O)O)C(=O)OCC1C2=CC=CC=C2C2=CC=CC=C12.[BH4-].[Na+]>>N([C@@H](CCCNC(=O)OCC1=CC=CC=C1)CO)C(=O)OCC1C2=CC=CC=C2C2=CC=CC=C12 | O=[C:8]([C@H:7]([CH2:6][CH2:5][CH2:4][NH:3][C:2](=[O:1])[O:28][CH2:29][c:30]1[cH:31][cH:32][cH:33][cH:34][cH:35]1)[NH:10][C:11](=[O:12])[O:13][CH2:14][CH:15]1[c:16]2[cH:17][cH:18][cH:19][cH:20][c:21]2-[c:22]2[cH:23][cH:24][cH:25][cH:26][c:27]21)[OH:9]>>[O:1]=[C:2]([NH:3][CH2:4][CH2:5][CH2:6][C@@H:7]([CH2:8][OH:9])[NH:1... | O=C(NCCC[C@H](NC(=O)OCC1c2ccccc2-c2ccccc21)C(=O)O)OCc1ccccc1 | O=C(NCCC[C@@H](CO)NC(=O)OCC1c2ccccc2-c2ccccc21)OCc1ccccc1 | null | null | null | Reduction | Reduction of carboxylic acid to primary alcohol | 0db83a5ebe1e318b78b55461cf7eb8f7c004eef0f9e3b6666d3df4c96b5f665e | 93b4621647b04d2ad2f2825215b1567f171ba61fe10d136b5db6ea0470aa4932 | O=C(NCCCCNC(=O)OCC1c2ccccc2-c2ccccc21)OCc1ccccc1 | O=[C;H0;D3;+0:1](-[O;D1;H1:2])-[C:3](-[C:4])-[#7:5]-[C:6]=[O;D1;H0:7]>>[C:4]-[C:3](-[#7:5]-[C:6]=[O;D1;H0:7])-[CH2;D2;+0:1]-[O;D1;H1:2] | null | [] | null | null | null | null | Commercially available Fmoc-Orn(Z) was converted to the alcohol by reduction of its mixed anhydride with sodium borohydride. After crystallization from EtOAc, the compound was thereafter used without further purification.
Conditions: See reaction.notes.procedure_details.
Workup: After crystallization from EtOAc; the co... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Primary alcohol | null | null | c1ccccc1.c1ccc2c(c1)Cc1ccccc12 | Other | null | null | null | O=C(NCCC[C@H](NC(=O)OCC1c2ccccc2-c2ccccc21)C(=O)O)OCc1ccccc1>>O=C(NCCC[C@@H](CO)NC(=O)OCC1c2ccccc2-c2ccccc21)OCc1ccccc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-2635a3a0c47f4c8d9e9782d14c61bc34 | COC(=O)c1cc(N=Nc2ccc(O)c(C(=O)OC)c2)ccc1O>>O=C([O-])c1cc(N=Nc2ccc(O)c(C(=O)[O-])c2)ccc1O.[Na+] | [OH-].[Na+].N(=NC=1C=C(C(=O)OC)C(=CC1)O)C=1C=C(C(=O)OC)C(=CC1)O>>[Na+].[Na+].N(=NC=1C=C(C(=O)[O-])C(=CC1)O)C=1C=C(C(=O)[O-])C(=CC1)O | C[O:3][C:2](=[O:1])[c:4]1[cH:5][c:6]([N:7]=[N:8][c:9]2[cH:10][cH:11][c:12]([OH:13])[c:14]([C:15](=[O:16])[O:17]C)[cH:18]2)[cH:19][cH:20][c:21]1[OH:22]>>[O:1]=[C:2]([O-:3])[c:4]1[cH:5][c:6]([N:7]=[N:8][c:9]2[cH:10][cH:11][c:12]([OH:13])[c:14]([C:15](=[O:16])[O-:17])[cH:18]2)[cH:19][cH:20][c:21]1[OH:22].[Na+:24] | COC(=O)c1cc(N=Nc2ccc(O)c(C(=O)OC)c2)ccc1O | O=C([O-])c1cc(N=Nc2ccc(O)c(C(=O)[O-])c2)ccc1O.[Na+] | null | null | null | Functional Group Interconversion | OtherReaction | 3d0c4a15f37850238014ea9cf5b9e777f9dd70f2d2ae5ebb7adda479f489012b | a87e633d4c15ade1dd31860f7c44fc378e0d7a7b518b924ae010ea4c26986bb4 | c1ccc(N=Nc2ccccc2)cc1 | C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4].C-[O;H0;D2;+0:5]-[C:6](=[O;D1;H0:7])-[c:8]>>[O-;H0;D1:1]-[C:2](=[O;D1;H0:3])-[c:4].[O-;H0;D1:5]-[C:6](=[O;D1;H0:7])-[c:8] | 65 | [{"value": 65.0, "product": "[Na+].[Na+].N(=NC=1C=C(C(=O)[O-])C(=CC1)O)C=1C=C(C(=O)[O-])C(=CC1)O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 90 | MINUTE | To a solution of sodium hydroxide (48 g, 1.2 mol in 800 ml of water) was charged compound 1c (80 g, 0.24 mol) at 25–30° C. The resulting dark black-red coloured solution was heated to mild reflux (reaction mixture temperature ˜85–90° C.) and was held for 90 minutes. This was then treated with activated carbon and reflu... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester | null | null | null | c1ccccc1.c1ccccc1 | Other | null | null | 1.5 | COC(=O)c1cc(N=Nc2ccc(O)c(C(=O)OC)c2)ccc1O>>O=C([O-])c1cc(N=Nc2ccc(O)c(C(=O)[O-])c2)ccc1O.[Na+] |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-99cff4f5665f49449cfff0f103010c1f | CC(C)(C)OC(=O)CC[C@H](NC(=O)OCc1ccccc1)C(=O)N[C@@H](CCC(=O)OCC[Si](C)(C)C)C(=O)OC(C)(C)C>>CC(C)(C)OC(=O)CC[C@H](N)C(=O)N[C@@H](CCC(=O)OCC[Si](C)(C)C)C(=O)OC(C)(C)C | C(C)(C)(C)OC(=O)CC[C@@H](C(=O)N[C@H](C(=O)OC(C)(C)C)CCC(=O)OCC[Si](C)(C)C)NC(=O)OCC1=CC=CC=C1>>N[C@H](C(=O)N[C@H](C(=O)OC(C)(C)C)CCC(=O)OCC[Si](C)(C)C)CCC(=O)OC(C)(C)C | O=C(OCc1ccccc1)[NH:11][C@@H:10]([CH2:9][CH2:8][C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[C:12](=[O:13])[NH:14][C@@H:15]([CH2:16][CH2:17][C:18](=[O:19])[O:20][CH2:21][CH2:22][Si:23]([CH3:24])([CH3:25])[CH3:26])[C:27](=[O:28])[O:29][C:30]([CH3:31])([CH3:32])[CH3:33]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7]... | CC(C)(C)OC(=O)CC[C@H](NC(=O)OCc1ccccc1)C(=O)N[C@@H](CCC(=O)OCC[Si](C)(C)C)C(=O)OC(C)(C)C | CC(C)(C)OC(=O)CC[C@H](N)C(=O)N[C@@H](CCC(=O)OCC[Si](C)(C)C)C(=O)OC(C)(C)C | null | [Pd] | CC(C)O | Reduction | Hydrogenolysis of amides/imides/carbamates | 087b6600ba91d3df931fe6979f2445c192cbfd59e04fd2d8a10f7c7573ac669f | 4e549866ec1acadec4c84aaf8495992a28ec78d8ea5ef1b9f44dd843b0dcb7d4 | null | O=C(-O-C-c1:c:c:c:c:c:1)-[NH;D2;+0:1]-[C:2](-[C:3])-[C:4](=[O;D1;H0:5])-[#7:6]-[C:7]-[C:8](-[#8:9])=[O;D1;H0:10]>>[#8:9]-[C:8](=[O;D1;H0:10])-[C:7]-[#7:6]-[C:4](=[O;D1;H0:5])-[C:2](-[C:3])-[NH2;D1;+0:1] | 94 | [{"value": 94.0, "product": "N[C@H](C(=O)N[C@H](C(=O)OC(C)(C)C)CCC(=O)OCC[Si](C)(C)C)CCC(=O)OC(C)(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 93.9, "product": "N[C@H](C(=O)N[C@H](C(=O)OC(C)(C)C)CCC(=O)OCC[Si](C)(C)C)CCC(=O)OC(C)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | The product of step 7G (1.09 g) was dissolved in 2-propanol (75 mL) with 10% palladium on carbon (300 mg) and hydrogenated on a Parr shaker at 45 psi for one hour. The reaction mixture was filtered on a bed of Celite, washed with 2-propanol, and concentrated to yield the product (803 mg, 94%) as a clear oil. LRMS (ES):... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether | Primary amine | c1ccccc1 | null | null | HO- | [Pd].CC(C)O | null | 1 | CC(C)(C)OC(=O)CC[C@H](NC(=O)OCc1ccccc1)C(=O)N[C@@H](CCC(=O)OCC[Si](C)(C)C)C(=O)OC(C)(C)C>[Pd].CC(C)O>CC(C)(C)OC(=O)CC[C@H](N)C(=O)N[C@@H](CCC(=O)OCC[Si](C)(C)C)C(=O)OC(C)(C)C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-ffa80996e43c4aaca4a7d4ff337d019a | CC(C)(C)OC(=O)CC[C@H](N)C(=O)N[C@@H](CCC(=O)OCC[Si](C)(C)C)C(=O)OC(C)(C)C.O=C(Br)CBr>>CC(C)(C)OC(=O)CC[C@H](NC(=O)CBr)C(=O)N[C@@H](CCC(=O)OCC[Si](C)(C)C)C(=O)OC(C)(C)C | CO.BrCC(=O)Br.N[C@H](C(=O)N[C@H](C(=O)OC(C)(C)C)CCC(=O)OCC[Si](C)(C)C)CCC(=O)OC(C)(C)C.C(C)(C)N(CC)C(C)C>>C(C)(C)(C)OC(=O)CC[C@@H](C(=O)N[C@H](C(=O)OC(C)(C)C)CCC(=O)OCC[Si](C)(C)C)NC(CBr)=O | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[CH2:8][CH2:9][C@H:10]([NH2:11])[C:16](=[O:17])[NH:18][C@@H:19]([CH2:20][CH2:21][C:22](=[O:23])[O:24][CH2:25][CH2:26][Si:27]([CH3:28])([CH3:29])[CH3:30])[C:31](=[O:32])[O:33][C:34]([CH3:35])([CH3:36])[CH3:37].Br[C:12](=[O:13])[CH2:14][Br:15]>>[CH3:1][C:2]([CH3:3])([CH3:4]... | CC(C)(C)OC(=O)CC[C@H](N)C(=O)N[C@@H](CCC(=O)OCC[Si](C)(C)C)C(=O)OC(C)(C)C.O=C(Br)CBr | CC(C)(C)OC(=O)CC[C@H](NC(=O)CBr)C(=O)N[C@@H](CCC(=O)OCC[Si](C)(C)C)C(=O)OC(C)(C)C | null | null | O1CCCC1 | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | null | Br-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[Br;D1;H0:4].[#8:5]-[C:6](=[O;D1;H0:7])-[C:8]-[#7:9]-[C:10](=[O;D1;H0:11])-[C:12](-[C:13])-[NH2;D1;+0:14]>>[#8:5]-[C:6](=[O;D1;H0:7])-[C:8]-[#7:9]-[C:10](=[O;D1;H0:11])-[C:12](-[C:13])-[NH;D2;+0:14]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[Br;D1;H0:4] | 78.3 | [{"value": 78.0, "product": "C(C)(C)(C)OC(=O)CC[C@@H](C(=O)N[C@H](C(=O)OC(C)(C)C)CCC(=O)OCC[Si](C)(C)C)NC(CBr)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 78.3, "product": "C(C)(C)(C)OC(=O)CC[C@@H](C(=O)N[C@H](C(=O)OC(C)(C)C)CCC(=O)OCC[Si](C)(C)C)NC(CBr)=O", "details": "CALCULATEDPERCENTYIELD", "is_d... | null | null | 1.5 | HOUR | The product of step 7H (397 mg, 0.813 mmol) was dissolved in dry tetrahydrofuran (5 mL) with diisopropylethylamine (180 μL, 1.05 mmol) and cooled to —10° C. under nitrogen. Bromoacetyl bromide (85 μL, 0.98 mmol), dissolved in 10 mL tetrahydrofuran, was added dropwise to the cold solution, keeping T≦−5° C. The reaction ... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | null | HBr | O1CCCC1 | null | 1.5 | CC(C)(C)OC(=O)CC[C@H](N)C(=O)N[C@@H](CCC(=O)OCC[Si](C)(C)C)C(=O)OC(C)(C)C.O=C(Br)CBr>O1CCCC1>CC(C)(C)OC(=O)CC[C@H](NC(=O)CBr)C(=O)N[C@@H](CCC(=O)OCC[Si](C)(C)C)C(=O)OC(C)(C)C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-273ecbc82a3a49628633bb22c5aef4ba | COC(=O)[C@H](CCC(=O)NC[C@@H](O)[C@H](O)[C@@H](O)[C@@H](O)CO)NC(=O)[C@H](CCC(=O)NC[C@@H](O)[C@H](O)[C@@H](O)[C@@H](O)CO)NC(=O)OCc1ccccc1>>O=C(CC[C@H](NC(=O)[C@H](CCC(=O)NC[C@@H](O)[C@H](O)[C@@H](O)[C@@H](O)CO)NC(=O)OCc1ccccc1)C(=O)O)NC[C@@H](O)[C@H](O)[C@@H](O)[C@@H](O)CO | O[C@H](CNC(=O)CC[C@@H](C(=O)OC)NC([C@H](CCC(NC[C@H]([C@@H]([C@H]([C@H](CO)O)O)O)O)=O)NC(=O)OCC1=CC=CC=C1)=O)[C@@H]([C@H]([C@H](CO)O)O)O.[OH-].[Li+]>>O[C@H](CNC(=O)CC[C@@H](C(=O)O)NC([C@H](CCC(NC[C@H]([C@@H]([C@H]([C@H](CO)O)O)O)O)=O)NC(=O)OCC1=CC=CC=C1)=O)[C@@H]([C@H]([C@H](CO)O)O)O | C[O:39][C:37]([C@H:5]([CH2:4][CH2:3][C:2](=[O:1])[NH:40][CH2:41][C@@H:42]([OH:43])[C@H:44]([OH:45])[C@@H:46]([OH:47])[C@@H:48]([OH:49])[CH2:50][OH:51])[NH:6][C:7](=[O:8])[C@H:9]([CH2:10][CH2:11][C:12](=[O:13])[NH:14][CH2:15][C@@H:16]([OH:17])[C@H:18]([OH:19])[C@@H:20]([OH:21])[C@@H:22]([OH:23])[CH2:24][OH:25])[NH:26][C... | COC(=O)[C@H](CCC(=O)NC[C@@H](O)[C@H](O)[C@@H](O)[C@@H](O)CO)NC(=O)[C@H](CCC(=O)NC[C@@H](O)[C@H](O)[C@@H](O)[C@@H](O)CO)NC(=O)OCc1ccccc1 | O=C(CC[C@H](NC(=O)[C@H](CCC(=O)NC[C@@H](O)[C@H](O)[C@@H](O)[C@@H](O)CO)NC(=O)OCc1ccccc1)C(=O)O)NC[C@@H](O)[C@H](O)[C@@H](O)[C@@H](O)CO | null | null | O1CCCC1.CO | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccccc1 | 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 | null | null | The product of step 11B is dissolved in tetrahydrofuran/methanol (1:1) and treated with excess 3N aqueous lithium hydroxide. The reaction is followed by HPLC for disappearance of starting material. The reaction is concentrated, diluted with additional water, and purified by passage down an acidic ion exchange column. T... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1 | Other | O1CCCC1.CO | null | null | COC(=O)[C@H](CCC(=O)NC[C@@H](O)[C@H](O)[C@@H](O)[C@@H](O)CO)NC(=O)[C@H](CCC(=O)NC[C@@H](O)[C@H](O)[C@@H](O)[C@@H](O)CO)NC(=O)OCc1ccccc1>O1CCCC1.CO>O=C(CC[C@H](NC(=O)[C@H](CCC(=O)NC[C@@H](O)[C@H](O)[C@@H](O)[C@@H](O)CO)NC(=O)OCc1ccccc1)C(=O)O)NC[C@@H](O)[C@H](O)[C@@H](O)[C@@H](O)CO |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-2ffa187e136f4a9ab49197498d8921d6 | O=C(n1ccnc1)n1ccnc1.O=c1ccn([C@@H]2O[C@H](COP(=O)(O)O)[C@@H](O)[C@H]2O)c(=O)[nH]1.O=c1ccn([C@@H]2O[C@H](COP(=O)(O)OP(=O)(O)OP(=O)(O)O)[C@@H](O)[C@H]2O)c(=O)[nH]1>>O=P(O)(O)OP(=O)(O)OP(=O)(O)OP(=O)(O)O.O=c1ccn([C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)c(=O)[nH]1.O=c1ccn([C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)c(=O)[nH]1 | P(O)(=O)(OP(=O)(O)OP(=O)(O)O)OC[C@@H]1[C@H]([C@H]([C@@H](O1)N1C(=O)NC(=O)C=C1)O)O.C(CCC)[NH+](CCCC)CCCC.P(=O)(O)(O)OC[C@@H]1[C@H]([C@H]([C@@H](O1)N1C(=O)NC(=O)C=C1)O)O.C(=O)(N1C=NC=C1)N1C=NC=C1>>OP(O)(=O)OP(=O)(O)OP(=O)(O)OP(=O)(O)O.[C@@H]1([C@H](O)[C@H](O)[C@@H](CO)O1)N1C(=O)NC(=O)C=C1.[C@@H]1([C@H](O)[C@H](O)[C@@H](C... | c1cn(C(n2ccnc2)=[O:5])cn1.[O:1]=[P:2]([OH:3])([OH:4])[O:27][CH2:26][C@H:25]1[O:24][C@@H:23]([n:22]2[cH:21][cH:20][c:19](=[O:18])[nH:34][c:32]2=[O:33])[C@H:30]([OH:31])[C@@H:28]1[OH:29].[P:6](=[O:7])([OH:8])([O:9][P:10](=[O:11])([OH:12])[O:13][P:14](=[O:15])([OH:16])[OH:17])[O:44][CH2:43][C@H:42]1[O:41][C@@H:40]([n:39]2... | O=C(n1ccnc1)n1ccnc1.O=c1ccn([C@@H]2O[C@H](COP(=O)(O)O)[C@@H](O)[C@H]2O)c(=O)[nH]1.O=c1ccn([C@@H]2O[C@H](COP(=O)(O)OP(=O)(O)OP(=O)(O)O)[C@@H](O)[C@H]2O)c(=O)[nH]1 | O=P(O)(O)OP(=O)(O)OP(=O)(O)OP(=O)(O)O.O=c1ccn([C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)c(=O)[nH]1.O=c1ccn([C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)c(=O)[nH]1 | null | null | C(CCC)N(CCCC)CCCC.CN(C)C=O | Miscellaneous | OtherReaction | 62a10c67bc13db216395b647e180b9757adaea24652e441e0cba263367224e86 | 9cdcf10a0e31e8609617410d8d4ee2916174601aef0f233bcf1f33a1fd7e9df7 | O=c1ccn([C@H]2CCCO2)c(=O)[nH]1.O=c1ccn([C@H]2CCCO2)c(=O)[nH]1 | [#15:1]-[#8:2]-[P;H0;D4;+0:3](=[O;D1;H0:4])(-[O;D1;H1:5])-[O;H0;D2;+0:6]-[C:7]-[C:8]-[#8:9].[#8:10]-[C:11]-[C:12]-[O;H0;D2;+0:13]-[P;H0;D4;+0:14](=[O;D1;H0:15])(-[O;D1;H1:16])-[O;D1;H1:17].[O;H0;D1;+0:18]=C(-n1:c:c:n:c:1)-n1:c:c:n:c:1>>[#15:1]-[#8:2]-[P;H0;D4;+0:3](=[O;D1;H0:4])(-[O;D1;H1:5])-[O;H0;D2;+0:18]-[P;H0;D4;+... | 30 | [{"value": 30.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | 50 | CELSIUS | 3 | DAY | Uridine 5′-monophosphate (Sigma, Milwaukee, 3.0 g, 9.26 mmol) was dissolved in dry DMF (10 mL) and tributylamine (Aldrich, 2 mL). The solution was evaporated in vacuo at 40° C. to an oil. The residue was dissolved in dry DMF (Aldrich, 8 mL) to form a solution. Carbonyldiimidazole (Aldrich, 1.65 g, 10.18 mmol) was added... | 10.6084/m9.figshare.5104873.v1 | null | Phosphate ester | Primary alcohol.Primary alcohol.Phosphate ester | c1c[nH]cn1.c1c[nH]cn1 | null | c1ccncn1.C1CCOC1.c1ccncn1.C1CCOC1 | Other | C(CCC)N(CCCC)CCCC.CN(C)C=O | 50 | 72 | O=C(n1ccnc1)n1ccnc1.O=c1ccn([C@@H]2O[C@H](COP(=O)(O)O)[C@@H](O)[C@H]2O)c(=O)[nH]1.O=c1ccn([C@@H]2O[C@H](COP(=O)(O)OP(=O)(O)OP(=O)(O)O)[C@@H](O)[C@H]2O)c(=O)[nH]1>C(CCC)N(CCCC)CCCC.CN(C)C=O>O=P(O)(O)OP(=O)(O)OP(=O)(O)OP(=O)(O)O.O=c1ccn([C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)c(=O)[nH]1.O=c1ccn([C@@H]2O[C@H](CO)[C@@H](O)[C@H]2... |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-f7642185c55d4f79854bb03e5e344c61 | COC1=Cc2ccccc2Nc2ccccc21.c1cc[nH+]cc1>>C1=Cc2ccccc2Nc2ccccc21.COC1=Cc2ccccc2Nc2ccccc21 | COC1=CC2=C(NC3=C1C=CC=C3)C=CC=C2.O.[Br-].[NH+]1=CC=CC=C1>>COC1=CC2=C(NC3=C1C=CC=C3)C=CC=C2.C=1C=CC2=C(C1)C=CC=3C=CC=CC3N2 | [cH:7]1[c:8]2[c:32]([cH:31][cH:30][cH:29]1)[C:18]([O:17][CH3:16])=[CH:19][c:20]1[cH:21][cH:22][cH:23][cH:24][c:25]1[NH:9]2.[cH:1]1[cH:14][cH:13][cH:28][cH:27][nH+:26]1>>[CH:1]1=[CH:2][c:3]2[cH:4][cH:5][cH:6][cH:7][c:8]2[NH:9][c:10]2[cH:11][cH:12][cH:13][cH:14][c:15]21.[CH3:16][O:17][C:18]1=[CH:19][c:20]2[cH:21][cH:22][... | COC1=Cc2ccccc2Nc2ccccc21.c1cc[nH+]cc1 | C1=Cc2ccccc2Nc2ccccc21.COC1=Cc2ccccc2Nc2ccccc21 | null | null | C1(=CC=CC=C1)C | Aromatic Heterocycle Formation | OtherReaction | 8a4f3e10d0caf1721f58749302b4650de5ba1fecadc12ea8dadf8ade54f27a33 | ecca787566927a700c1086e53bae62cab2378b40824774a07224b4a25a745c77 | C1=Cc2ccccc2Nc2ccccc21.C1=Cc2ccccc2Nc2ccccc21 | [#8:1]-[C:2]1=[C:3]-[c:4](:[c:5]):[c;H0;D3;+0:6](:[c:7]:[c:8])-[NH;D2;+0:9]-[c;H0;D3;+0:10]2:[cH;D2;+0:11]:[cH;D2;+0:12]:[c:13]:[c:14]:[c;H0;D3;+0:15]:2-1.[cH;D2;+0:16]1:[cH;D2;+0:17]:[cH;D2;+0:18]:[nH+;D2:19]:[cH;D2;+0:20]:[cH;D2;+0:21]:1>>[#8:1]-[C:2]1=[C:3]-[c:4](:[c:5]):[c;H0;D3;+0:6](:[c:7]:[c:8])-[NH;D2;+0:19]-[c... | null | [] | 22 | CELSIUS | 10 | MINUTE | In a three-neck flask (500 ml), equipped with a mechanical stirring apparatus, 15 ml water was introduced, followed by pyridinium bromide (71.75 g, 0.45 mole; Chemadaa' (Nir Yitshak, Israel)). The mixture was stirred at room temperature (22° C.) for about 10 minutes. Then 250 ml toluene was added, followed by 50 g (0.2... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amine | Secondary amine.Secondary amine | C1=Cc2ccccc2Nc2ccccc21.c1cc[n+]cc1 | C1=Cc2ccccc2Nc2ccccc21.C1=Cc2ccccc2Nc2ccccc21 | C1=Cc2ccccc2Nc2ccccc21.C1=Cc2ccccc2Nc2ccccc21 | Other | C1(=CC=CC=C1)C | 22 | 0.166667 | COC1=Cc2ccccc2Nc2ccccc21.c1cc[nH+]cc1>C1(=CC=CC=C1)C>C1=Cc2ccccc2Nc2ccccc21.COC1=Cc2ccccc2Nc2ccccc21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-5cb6d0f152d044ee8dc9a054a97d110f | COC1=Cc2ccccc2Nc2ccccc21>>NC(=O)N1c2ccccc2CC(=O)c2ccccc21 | Cl.[Br-].[NH+]1=CC=CC=C1.COC1=CC2=C(NC3=C1C=CC=C3)C=CC=C2.O([Na])C#N>>C=1C=CC2=C(C1)CC(=O)C=3C=CC=CC3N2C(=O)N | C[O:13][C:12]1=[CH:11][c:10]2[c:5]([cH:6][cH:7][cH:8][cH:9]2)[NH:4][c:19]2[c:14]1[cH:15][cH:16][cH:17][cH:18]2>>[NH2:1][C:2](=[O:3])[N:4]1[c:5]2[cH:6][cH:7][cH:8][cH:9][c:10]2[CH2:11][C:12](=[O:13])[c:14]2[cH:15][cH:16][cH:17][cH:18][c:19]21 | COC1=Cc2ccccc2Nc2ccccc21 | NC(=O)N1c2ccccc2CC(=O)c2ccccc21 | null | null | O.C1(=CC=CC=C1)C | Functional Group Interconversion | OtherReaction | 6685a86fbc173eac13f9e84f31c4dbcedf3634a9dcd91624b9193223a3e6798f | ee391d49f6bd1401de1e408529bfd3c20ba8cdde097a364714383e8fb1f9dee4 | O=C1Cc2ccccc2Nc2ccccc21 | C-[O;H0;D2;+0:1]-[C;H0;D3;+0:2]1=[CH;D2;+0:3]-[c:4](:[c:5]):[c:6](:[c:7])-[NH;D2;+0:8]-[c:9](:[c:10]):[c:11]-1:[c:12]>>[N;D1;H2:13]-[C:14](=[O;D1;H0:15])-[N;H0;D3;+0:8]1-[c:9](:[c:10]):[c:11](:[c:12])-[C;H0;D3;+0:2](=[O;H0;D1;+0:1])-[CH2;D2;+0:3]-[c:4](:[c:5]):[c:6]-1:[c:7] | 58 | [{"value": 58.0, "product": "C=1C=CC2=C(C1)CC(=O)C=3C=CC=CC3N2C(=O)N", "details": "PERCENTYIELD", "is_desired": false}] | 89 | CELSIUS | null | null | The carbamoylation reaction was performed as in Example 1. After about 7–8 hours of stirring the carbamoylation reaction mixture (containing pyridinium bromide, 10-methoxy-5H-dibenz[b,f]azepine, water, toluene, and NaOCN) at room temperature (22° C.), the mixture was heated to 55–60° C., and 500 ml of 10% HCl was added... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Secondary amine | Ketone.Urea | C1=Cc2ccccc2Nc2ccccc21 | c1ccc2c(c1)CCc1ccccc1[NH]2 | c1ccc2c(c1)CCc1ccccc1[NH]2 | Other | O.C1(=CC=CC=C1)C | 89 | null | COC1=Cc2ccccc2Nc2ccccc21>O.C1(=CC=CC=C1)C>NC(=O)N1c2ccccc2CC(=O)c2ccccc21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-ce0dd8900c0f4904b3ae6c61be0151bc | COC1=Cc2ccccc2Nc2ccccc21>>COC1=Cc2ccccc2N(C(N)=O)c2ccccc21 | C1(=CC=C(C=C1)S(=O)(=O)[O-])C.[NH+]1=CC=CC=C1.COC1=CC2=C(NC3=C1C=CC=C3)C=CC=C2.COC1=CC2=C(NC3=C1C=CC=C3)C=CC=C2.C(C)#N.O([Na])C#N>>COC1=CC2=C(N(C3=C1C=CC=C3)C(=O)N)C=CC=C2 | [CH3:1][O:2][C:3]1=[CH:4][c:5]2[cH:6][cH:7][cH:8][cH:9][c:10]2[NH:11][c:15]2[cH:16][cH:17][cH:18][cH:19][c:20]21>>[CH3:1][O:2][C:3]1=[CH:4][c:5]2[cH:6][cH:7][cH:8][cH:9][c:10]2[N:11]([C:12]([NH2:13])=[O:14])[c:15]2[cH:16][cH:17][cH:18][cH:19][c:20]21 | COC1=Cc2ccccc2Nc2ccccc21 | COC1=Cc2ccccc2N(C(N)=O)c2ccccc21 | null | null | O | Functional Group Addition | OtherReaction | 0e1534f0aef27a6e419d4f0726aabfebe96b6ed55fc894c6e3f08b3cceaa3003 | 8edd034797066ebe5a10823ba4110338f6f7ad9e6f97c67a80b466fdef329ac0 | C1=Cc2ccccc2Nc2ccccc21 | [c:1]:[c:2]1:[c:3]-[C:4]=[C:5]-[c:6]:[c:7](:[c:8])-[NH;D2;+0:9]-1>>[N;D1;H2:10]-[C:11](=[O;D1;H0:12])-[N;H0;D3;+0:9]1-[c:7](:[c:8]):[c:6]-[C:5]=[C:4]-[c:3]:[c:2]-1:[c:1] | 50.7 | [{"value": 50.0, "product": "COC1=CC2=C(N(C3=C1C=CC=C3)C(=O)N)C=CC=C2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 50.7, "product": "COC1=CC2=C(N(C3=C1C=CC=C3)C(=O)N)C=CC=C2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 15 | MINUTE | 10-methoxy-5H-dibenz(b,f)azepine (29.9 g, 0.134 mol) was added to 300 ml acetonitrile in a three-neck flask (500 ml) equipped with a mechanical stirring apparatus. The mixture was stirred at room temperature for 15 minutes, and then NaOCN (18 g, 0.277 mol) was added, followed by pyridinium p-toluenesulfonate (75 g, 0.3... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amine | Urea | C1=Cc2ccccc2Nc2ccccc21 | C1=Cc2ccccc2[NH]c2ccccc21 | C1=Cc2ccccc2[NH]c2ccccc21 | Other | O | null | 0.25 | COC1=Cc2ccccc2Nc2ccccc21>O>COC1=Cc2ccccc2N(C(N)=O)c2ccccc21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-8f6706cc574948029bb2a0abec2abc5c | O=S1(=O)CCOc2ccccc21.O=[N+]([O-])O>>O=[N+]([O-])c1ccc2c(c1)S(=O)(=O)CCO2 | O1CCS(C2=C1C=CC=C2)(=O)=O.OS(=O)(=O)O.[N+](=O)(O)[O-]>>[N+](=O)([O-])C=1C=CC2=C(S(CCO2)(=O)=O)C1 | [cH:4]1[cH:5][cH:6][c:7]2[c:8]([cH:9]1)[S:10](=[O:11])(=[O:12])[CH2:13][CH2:14][O:15]2.O[N+:2](=[O:1])[O-:3]>>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][cH:6][c:7]2[c:8]([cH:9]1)[S:10](=[O:11])(=[O:12])[CH2:13][CH2:14][O:15]2 | O=S1(=O)CCOc2ccccc21.O=[N+]([O-])O | O=[N+]([O-])c1ccc2c(c1)S(=O)(=O)CCO2 | null | null | O | Functional Group Addition | Aromatic nitration with HNO3 | a6924fda0e48a6abe35a46350eec107fbdce369769299546235486f88097d624 | ddce49825c02b8965f10c8d99e3c841d26e1f136da6037b417c09313e6d73097 | O=S1(=O)CCOc2ccccc21 | O-[N+;H0;D3:1](-[O;-;D1;H0:2])=[O;D1;H0:3].[#16:4]-[c:5]:[c:6]:[cH;D2;+0:7]:[c:8]:[c:9]>>[#16:4]-[c:5]:[c:6]:[c;H0;D3;+0:7](-[N+;H0;D3:1](-[O;-;D1;H0:2])=[O;D1;H0:3]):[c:8]:[c:9] | 53.7 | [{"value": 53.7, "product": "[N+](=O)([O-])C=1C=CC2=C(S(CCO2)(=O)=O)C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | 2.554 g 66% H2SO4 and 1.454 g 65% nitric acid were mixed at 0° C. 2.395 g 2,3-dihydro-benzo[1,4]oxathiine-4,4-dioxide were added in portions at 0° C. After stirring for 30 min. the mixture was diluted with water and the product isolated by filtration. Chromatography on silica yielded 1.6 g of the title compound and 0.3... | 10.6084/m9.figshare.5104873.v1 | null | Nitrate | Nitro group | c1ccc2c(c1)OCCS2 | c1ccc2c(c1)OCCS2 | c1ccc2c(c1)OCCS2 | HO- | O | null | 0.5 | O=S1(=O)CCOc2ccccc21.O=[N+]([O-])O>O>O=[N+]([O-])c1ccc2c(c1)S(=O)(=O)CCO2 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-f629534e45f24ca1b3eebffb5d964052 | O=[N+]([O-])c1ccc2c(c1)S(=O)(=O)CCO2>>Nc1ccc2c(c1)S(=O)(=O)CCO2 | [N+](=O)([O-])C=1C=CC2=C(S(CCO2)(=O)=O)C1.[H][H]>>NC=1C=CC2=C(S(CCO2)(=O)=O)C1 | O=[N+:1]([O-])[c:2]1[cH:3][cH:4][c:5]2[c:6]([cH:7]1)[S:8](=[O:9])(=[O:10])[CH2:11][CH2:12][O:13]2>>[NH2:1][c:2]1[cH:3][cH:4][c:5]2[c:6]([cH:7]1)[S:8](=[O:9])(=[O:10])[CH2:11][CH2:12][O:13]2 | O=[N+]([O-])c1ccc2c(c1)S(=O)(=O)CCO2 | Nc1ccc2c(c1)S(=O)(=O)CCO2 | null | [Pd] | CO.C1CCOC1 | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | O=S1(=O)CCOc2ccccc21 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | 46.4 | [{"value": 46.4, "product": "NC=1C=CC2=C(S(CCO2)(=O)=O)C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 0.917 g 6-Nitro-2,3-dihydro-benzo[1,4]oxathiine-4,4-dioxide (from g)) were hydrogenated in a mixture of 20 ml THF and 20 ml MeOH with 0.90 g 5% Pd—C at atmospheric hydrogen pressure for 90 min. at room temperature. The catalyst was filtered off, the filtrate evaporated and the residue chromatographed on silica to yield... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccc2c(c1)OCCS2 | Other | [Pd].CO.C1CCOC1 | null | null | O=[N+]([O-])c1ccc2c(c1)S(=O)(=O)CCO2>[Pd].CO.C1CCOC1>Nc1ccc2c(c1)S(=O)(=O)CCO2 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-ae7541c76b774e8fa0cc87517c966110 | CI.Nc1ccc2c(c1)NC(=O)CS2>>CN1C(=O)CSc2ccc(N)cc21 | [Cl-].[NH4+].CI.NC=1C=CC2=C(NC(CS2)=O)C1.[H-].[Na+]>>NC=1C=CC2=C(N(C(CS2)=O)C)C1 | I[CH3:1].[NH:2]1[C:3](=[O:4])[CH2:5][S:6][c:7]2[cH:8][cH:9][c:10]([NH2:11])[cH:12][c:13]21>>[CH3:1][N:2]1[C:3](=[O:4])[CH2:5][S:6][c:7]2[cH:8][cH:9][c:10]([NH2:11])[cH:12][c:13]21 | CI.Nc1ccc2c(c1)NC(=O)CS2 | CN1C(=O)CSc2ccc(N)cc21 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 3dcdd0f63c6f65280ef1417e5974c03c4962153dd603958f95a5c7b87a06fb8a | 0a16658309ac5595448433dd7ef49294830b145345df0b202ccd54727262e629 | O=C1CSc2ccccc2N1 | I-[CH3;D1;+0:1].[O;D1;H0:2]=[C:3]1-[C:4]-[#16:5]-[c:6]:[c:7](:[c:8])-[NH;D2;+0:9]-1>>[CH3;D1;+0:1]-[N;H0;D3;+0:9]1-[C:3](=[O;D1;H0:2])-[C:4]-[#16:5]-[c:6]:[c:7]-1:[c:8] | 63.9 | [{"value": 63.9, "product": "NC=1C=CC2=C(N(C(CS2)=O)C)C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | 4.5 g 6-Amino-4H-benzo[1,4]thiazin-3-one in 50 ml DMF was treated in portions with 0.695 g 95% sodium hydride at room temperature. After 30 min, 3.548 g methyl iodide were added dropwise at 0° C. and stirring was continued for another 30 min. The mixture was poured into ice and ammonium chloride solution and extracted ... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide | Tertiary amide | c1ccc2c(c1)NCCS2 | c1ccc2c(c1)[NH]CCS2 | c1ccc2c(c1)[NH]CCS2 | HI | CN(C)C=O | null | 0.5 | CI.Nc1ccc2c(c1)NC(=O)CS2>CN(C)C=O>CN1C(=O)CSc2ccc(N)cc21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-0de7095bd6ab45469c4e0d001ceb86a0 | CI.O=C1CSc2cc([N+](=O)[O-])ccc2N1>>CN1C(=O)CSc2cc([N+](=O)[O-])ccc21 | [N+](=O)([O-])C1=CC2=C(NC(CS2)=O)C=C1.[H-].[Na+].CI>>[N+](=O)([O-])C1=CC2=C(N(C(CS2)=O)C)C=C1 | I[CH3:1].[NH:2]1[C:3](=[O:4])[CH2:5][S:6][c:7]2[cH:8][c:9]([N+:10](=[O:11])[O-:12])[cH:13][cH:14][c:15]21>>[CH3:1][N:2]1[C:3](=[O:4])[CH2:5][S:6][c:7]2[cH:8][c:9]([N+:10](=[O:11])[O-:12])[cH:13][cH:14][c:15]21 | CI.O=C1CSc2cc([N+](=O)[O-])ccc2N1 | CN1C(=O)CSc2cc([N+](=O)[O-])ccc21 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 3dcdd0f63c6f65280ef1417e5974c03c4962153dd603958f95a5c7b87a06fb8a | 0a16658309ac5595448433dd7ef49294830b145345df0b202ccd54727262e629 | O=C1CSc2ccccc2N1 | I-[CH3;D1;+0:1].[O;D1;H0:2]=[C:3]1-[C:4]-[#16:5]-[c:6]:[c:7](:[c:8])-[NH;D2;+0:9]-1>>[CH3;D1;+0:1]-[N;H0;D3;+0:9]1-[C:3](=[O;D1;H0:2])-[C:4]-[#16:5]-[c:6]:[c:7]-1:[c:8] | null | [] | null | null | null | null | 7.3 g 7-Nitro-4H-benzo[1,4]thiazin-3-one was suspended in 65 ml DMF and treated in portions with 1.6 g of 55% sodium hydride. Stirring a room temperature was continued for 0.5 hrs, than 5.2 g methyl iodide in 15 ml DMF were added dropwise. After another 3 hrs the mixture was poured into ice water and the title product ... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide | Tertiary amide | c1ccc2c(c1)NCCS2 | c1ccc2c(c1)[NH]CCS2 | c1ccc2c(c1)[NH]CCS2 | HI | CN(C)C=O | null | null | CI.O=C1CSc2cc([N+](=O)[O-])ccc2N1>CN(C)C=O>CN1C(=O)CSc2cc([N+](=O)[O-])ccc21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-6bad55cfa06a4e3ca987226d8d6dc084 | CN1C(=O)CSc2cc([N+](=O)[O-])ccc21>>CN1C=CSc2cc([N+](=O)[O-])ccc21 | [N+](=O)([O-])C1=CC2=C(N(C(CS2)=O)C)C=C1.C([O-])(O)=O.[Na+]>>[N+](=O)([O-])C1=CC2=C(N(C=CS2)C)C=C1 | O=[C:3]1[N:2]([CH3:1])[c:14]2[c:6]([cH:7][c:8]([N+:9](=[O:10])[O-:11])[cH:12][cH:13]2)[S:5][CH2:4]1>>[CH3:1][N:2]1[CH:3]=[CH:4][S:5][c:6]2[cH:7][c:8]([N+:9](=[O:10])[O-:11])[cH:12][cH:13][c:14]21 | CN1C(=O)CSc2cc([N+](=O)[O-])ccc21 | CN1C=CSc2cc([N+](=O)[O-])ccc21 | null | null | C1CCOC1 | Miscellaneous | OtherReaction | ff8e9072d6613a442bfc6a71bebdbcf8c257f0f19d7dd4af91e529f0a2ac6b86 | c5ca2f05580df3dad1ca2fea341e56ff49c071d2f384356870952d345b0231fe | C1=CSc2ccccc2N1 | O=[C;H0;D3;+0:1]1-[CH2;D2;+0:2]-[#16:3]-[c:4]:[c:5]-[#7:6]-1-[C;D1;H3:7]>>[C;D1;H3:7]-[#7:6]1-[CH;D2;+0:1]=[CH;D2;+0:2]-[#16:3]-[c:4]:[c:5]-1 | null | [] | null | null | null | null | 7 g 7-Nitro-4-methyl-4H-benzo[1,4]thiazin-3-one (from j)) in 10 ml THF were treated dropwise with 67.57 ml 2M borane dimethyl sulfide complex in THF at room temperature. After 16 hrs the mixture was poured into saturated aqueous sodium bicarbonate and extracted with ethyl acetate. The solvent was evaporated and the sol... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Monosulfide | Enamine | c1ccc2c(c1)[NH]CCS2 | C1=CSc2ccccc2[NH]1 | C1=CSc2ccccc2[NH]1 | Other | C1CCOC1 | null | null | CN1C(=O)CSc2cc([N+](=O)[O-])ccc21>C1CCOC1>CN1C=CSc2cc([N+](=O)[O-])ccc21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-a2cdac2f4a86442e912f0760f5d995ae | CN1C(=O)c2ccc(N)cc2C1=O>>CN1Cc2ccc(N)cc2C1 | NC=1C=C2C(C(=O)N(C2=O)C)=CC1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>>CN1CC2=CC=C(C=C2C1)N | O=[C:3]1[N:2]([CH3:1])[C:11](=O)[c:10]2[c:4]1[cH:5][cH:6][c:7]([NH2:8])[cH:9]2>>[CH3:1][N:2]1[CH2:3][c:4]2[cH:5][cH:6][c:7]([NH2:8])[cH:9][c:10]2[CH2:11]1 | CN1C(=O)c2ccc(N)cc2C1=O | CN1Cc2ccc(N)cc2C1 | null | null | C1CCOC1 | Reduction | OtherReaction | 832b56260d6802f9d64a6466431f89dc633b4a5ea12baf231a1621ca4337a5da | 5c48d2345eb2fa995a1eb3dce1782e140f14b5faddfaad3c600fc635c2b998a2 | c1ccc2c(c1)CNC2 | O=[C;H0;D3;+0:1]1-[#7:2](-[C;D1;H3:3])-[C;H0;D3;+0:4](=O)-[c:5](:[c:6]):[c:7]-1:[c:8]>>[C;D1;H3:3]-[#7:2]1-[CH2;D2;+0:1]-[c:7](:[c:8]):[c:5](:[c:6])-[CH2;D2;+0:4]-1 | 72 | [{"value": 72.0, "product": "CN1CC2=CC=C(C=C2C1)N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | DAY | 2.643 g 4-Amino-N-methylphthalimide was suspended in 50 ml THF and added to 1.328 g lithium aluminum hydride in 50 ml THF at room temperature. The mixture was refluxed for 3 hrs, then stirred a further 3 days at room temperature. Excess LAH was destroyed by addition of water and the mixture filtered over celite. An aqu... | 10.6084/m9.figshare.5104873.v1 | null | Substituted dicarboximide | null | c1ccc2c(c1)C[NH]C2 | c1ccc2c(c1)C[NH]C2 | c1ccc2c(c1)C[NH]C2 | Other | C1CCOC1 | null | 72 | CN1C(=O)c2ccc(N)cc2C1=O>C1CCOC1>CN1Cc2ccc(N)cc2C1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-a28dfc986e8549b3bda0a7e2c9a0bc50 | CC(C)(N)CO.O=C1OC(=O)c2cc([N+](=O)[O-])ccc21>>CC(C)(CO)N1Cc2ccc([N+](=O)[O-])cc2C1 | [N+](=O)([O-])C=1C=C2C(C(=O)OC2=O)=CC1.NC(CO)(C)C.O>>CC(CO)(C)N1CC2=CC=C(C=C2C1)[N+](=O)[O-] | [CH3:1][C:2]([CH3:3])([CH2:4][OH:5])[NH2:6].O=[C:7]1O[C:17](=O)[c:16]2[c:8]1[cH:9][cH:10][c:11]([N+:12](=[O:13])[O-:14])[cH:15]2>>[CH3:1][C:2]([CH3:3])([CH2:4][OH:5])[N:6]1[CH2:7][c:8]2[cH:9][cH:10][c:11]([N+:12](=[O:13])[O-:14])[cH:15][c:16]2[CH2:17]1 | CC(C)(N)CO.O=C1OC(=O)c2cc([N+](=O)[O-])ccc21 | CC(C)(CO)N1Cc2ccc([N+](=O)[O-])cc2C1 | null | null | C(Cl)Cl | Functional Group Addition | OtherReaction | 7e07ed7b8e56c2045350a2bcda7b2e654a1186bdfe53440088d45d2b3c14fd50 | a34d1a6335e73a6d460fb28a9056dd81485068f46955f3c2a3d5c420295826cc | c1ccc2c(c1)CNC2 | O=[C;H0;D3;+0:1]1-O-[C;H0;D3;+0:2](=O)-[c:3](:[c:4]):[c:5]-1:[c:6].[C:7]-[C:8](-[C;D1;H3:9])(-[C;D1;H3:10])-[NH2;D1;+0:11]>>[C:7]-[C:8](-[C;D1;H3:9])(-[C;D1;H3:10])-[N;H0;D3;+0:11]1-[CH2;D2;+0:1]-[c:5](:[c:6]):[c:3](:[c:4])-[CH2;D2;+0:2]-1 | null | [] | null | null | null | null | 20 g of 4-Nitro-phthalic anhydride and 8.94 g of 2-amino-2-methylpropanol were heated to 170° C. for 30 min. After cooling, water and CH2Cl2 were added, and the organic phase separated, concentrated and purified by chromatography on silica (eluent CH2Cl2/MeOH 97/3).
Conditions: See reaction.notes.procedure_details.
Wor... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Ester.Ester.Primary amine | Tertiary amine | c1ccc2c(c1)COC2 | c1ccc2c(c1)C[NH]C2 | c1ccc2c(c1)C[NH]C2 | Other | C(Cl)Cl | null | null | CC(C)(N)CO.O=C1OC(=O)c2cc([N+](=O)[O-])ccc21>C(Cl)Cl>CC(C)(CO)N1Cc2ccc([N+](=O)[O-])cc2C1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-c30e63ee47dc475e94aad2aa23ea7648 | CNc1nc(SC)ncc1C=O>>CNc1nc(SC)ncc1C(C)O | C[Mg]Br.CNC1=NC(=NC=C1C=O)SC>>CNC1=NC(=NC=C1C(C)O)SC | [CH3:1][NH:2][c:3]1[n:4][c:5]([S:6][CH3:7])[n:8][cH:9][c:10]1[CH:11]=[O:13]>>[CH3:1][NH:2][c:3]1[n:4][c:5]([S:6][CH3:7])[n:8][cH:9][c:10]1[CH:11]([CH3:12])[OH:13] | CNc1nc(SC)ncc1C=O | CNc1nc(SC)ncc1C(C)O | null | null | C1CCOC1.CCOCC | Miscellaneous | OtherReaction | 1ffaf80f172e20da969364a5d2977299bc51b204f2262675c45c8ec58ff36ac0 | e005d650d08e61fc67b766830eb53235a9bc084cc3667d2f8a73c2fb8bb34277 | c1cncnc1 | [#7:1]-[c:2]1:[#7;a:3]:[c:4]:[#7;a:5]:[c:6]:[c:7]:1-[CH;D2;+0:8]=[O;H0;D1;+0:9]>>[#7:1]-[c:2]1:[#7;a:3]:[c:4]:[#7;a:5]:[c:6]:[c:7]:1-[CH;D3;+0:8](-[C;D1;H3:10])-[OH;D1;+0:9] | null | [] | 0 | CELSIUS | 1 | HOUR | 1.5 g 4-Methylamino-2-methylsulfanyl-pyrimidine-5-carbaldehyde were dissolved in 30 ml THF and 14 ml of a 1.4 M solution of methyl magnesium bromide in ether were added dropwise below 5° C. After stirring for 1 hr at 0° C., another 14 ml Grignard solution were added within 30 min. Stirring was continued for 30 min at 0... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | Secondary alcohol | null | null | c1cncnc1 | Other | C1CCOC1.CCOCC | 0 | 1 | CNc1nc(SC)ncc1C=O>C1CCOC1.CCOCC>CNc1nc(SC)ncc1C(C)O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-bc98e3ec676947a9ac1de87fe6360973 | BrCC1CO1.O=[N+]([O-])c1ccc(O)c(O)c1>>O=[N+]([O-])c1ccc2c(c1)OC(CO)CO2 | C(Br)C1CO1.[N+](=O)([O-])C=1C=C(C(O)=CC1)O.C([O-])(O)=O.[K+]>>OCC1COC2=C(O1)C=C(C=C2)[N+](=O)[O-] | Br[CH2:14][CH:11]1[CH2:12][O:13]1.[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][cH:6][c:7]([OH:15])[c:8]([OH:10])[cH:9]1>>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][cH:6][c:7]2[c:8]([cH:9]1)[O:10][CH:11]([CH2:12][OH:13])[CH2:14][O:15]2 | BrCC1CO1.O=[N+]([O-])c1ccc(O)c(O)c1 | O=[N+]([O-])c1ccc2c(c1)OC(CO)CO2 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | OtherReaction | 66372ae14f6b05e39df1c82df4473dad91be49352f5aed3bcd657357bdc2f039 | b2e94afc01d47e15b6a937be7072d0be95f8948a00689f8bd85b6727db250985 | c1ccc2c(c1)OCCO2 | Br-[CH2;D2;+0:1]-[CH;D3;+0:2]1-[C:3]-[O;H0;D2;+0:4]-1.[OH;D1;+0:5]-[c:6](:[c:7]):[c:8](-[OH;D1;+0:9]):[c:10]>>[OH;D1;+0:4]-[C:3]-[CH;D3;+0:2]1-[CH2;D2;+0:1]-[O;H0;D2;+0:9]-[c:8](:[c:10]):[c:6](:[c:7])-[O;H0;D2;+0:5]-1 | 3.5 | [{"value": 3.5, "product": "OCC1COC2=C(O1)C=C(C=C2)[N+](=O)[O-]", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 90 | CELSIUS | 17 | HOUR | 17.6 g 4-nitrocatechol and 11.0 g potassium bicarbonate were stirred in 200 ml DMF at 10° C. 13.99 g epibromohydrin in 10 ml DMF were added dropwise and stirring was continued at 60° C. for another 17 hrs. DMF was evaporated and the residue diluted with 50 ml water and extracted with ethyl acetate. The combined organic... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ether.Aromatic alcohol.Aromatic alcohol | Ether.Ether.Primary alcohol | C1CO1 | c1ccc2c(c1)OCCO2 | c1ccc2c(c1)OCCO2 | HBr | CN(C)C=O | 90 | 17 | BrCC1CO1.O=[N+]([O-])c1ccc(O)c(O)c1>CN(C)C=O>O=[N+]([O-])c1ccc2c(c1)OC(CO)CO2 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-c8ca5c2aedfc4492935406ddebc1bfe5 | CN1C(=O)N(c2ccccc2Br)Cc2cnc(S(C)(=O)=O)nc21.Nc1ccc2c(c1)OCC(CO)O2>>CN1C(=O)N(c2ccccc2Br)Cc2cnc(Nc3ccc4c(c3)OCC(CO)O4)nc21 | BrC1=C(C=CC=C1)N1C(N(C2=NC(=NC=C2C1)S(=O)(=O)C)C)=O.OCC1COC2=C(O1)C=CC(=C2)N.OCC1COC2=C(O1)C=CC(=C2)N.Cl.C(=O)(C(F)(F)F)O>>BrC1=C(C=CC=C1)N1C(N(C2=NC(=NC=C2C1)NC1=CC2=C(OC(CO2)CO)C=C1)C)=O | CS(=O)(=O)[c:17]1[n:16][cH:15][c:14]2[c:32]([n:31]1)[N:2]([CH3:1])[C:3](=[O:4])[N:5]([c:6]1[cH:7][cH:8][cH:9][cH:10][c:11]1[Br:12])[CH2:13]2.[NH2:18][c:19]1[cH:20][cH:21][c:22]2[c:23]([cH:24]1)[O:25][CH2:26][CH:27]([CH2:28][OH:29])[O:30]2>>[CH3:1][N:2]1[C:3](=[O:4])[N:5]([c:6]2[cH:7][cH:8][cH:9][cH:10][c:11]2[Br:12])[C... | CN1C(=O)N(c2ccccc2Br)Cc2cnc(S(C)(=O)=O)nc21.Nc1ccc2c(c1)OCC(CO)O2 | CN1C(=O)N(c2ccccc2Br)Cc2cnc(Nc3ccc4c(c3)OCC(CO)O4)nc21 | null | null | CN1CCCC1=O | Heteroatom Alkylation and Arylation | OtherReaction | ee3efd3d452933cfc1f039815537283e74d04312087383f530a2f91f0b9760a5 | f263fb011eaf2f85af25e2af9b0908fb2797226f3495a5d6be9230bf229d4fae | O=C1Nc2nc(Nc3ccc4c(c3)OCCO4)ncc2CN1c1ccccc1 | C-S(=O)(=O)-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5]-[#7:6].[NH2;D1;+0:7]-[c:8](:[c:9]):[c:10]>>[#7:6]-[c:5]:[#7;a:4]:[c;H0;D3;+0:1](-[NH;D2;+0:7]-[c:8](:[c:9]):[c:10]):[#7;a:2]:[c:3] | null | [] | 140 | CELSIUS | null | null | 1.2 g 3-(2-bromo-phenyl)-3,4-dihydro-7-methanesulphonyl-1-methyl-pyrimido[4,5-d]pyrimidin-2(1H)-one and 1.54 g 2 hydroxymethyl-6-amino-1,4-benzodioxane (starting material b)) were mixed in 20 ml NMP. 0.348 g TFA were added and the mixture was heated to 140° C. for 7 hrs. The mixture was poured into 10% aqueous HCl and ... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Sulfone | Secondary amine | c1ncc2c(n1)[NH]C[NH]C2 | c1ncc2c(n1)[NH]C[NH]C2 | c1ccccc1.c1ncc2c(n1)[NH]C[NH]C2.c1ccc2c(c1)OCCO2 | HO- | CN1CCCC1=O | 140 | null | CN1C(=O)N(c2ccccc2Br)Cc2cnc(S(C)(=O)=O)nc21.Nc1ccc2c(c1)OCC(CO)O2>CN1CCCC1=O>CN1C(=O)N(c2ccccc2Br)Cc2cnc(Nc3ccc4c(c3)OCC(CO)O4)nc21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-2f4ba6433b594125bf21b306ef755b52 | CN1C(=O)N(c2ccccc2Br)Cc2cnc(Nc3ccc4c(c3)OCC(CO)O4)nc21.Cc1ccc(S(=O)(=O)Cl)cc1>>Cc1ccc(S(=O)(=O)OCC2COc3cc(Nc4ncc5c(n4)N(C)C(=O)N(c4ccccc4Br)C5)ccc3O2)cc1 | S(=O)(=O)(C1=CC=C(C)C=C1)Cl.BrC1=C(C=CC=C1)N1C(N(C2=NC(=NC=C2C1)NC1=CC2=C(OC(CO2)CO)C=C1)C)=O.S(=O)(=O)(C1=CC=C(C)C=C1)Cl.N1=CC=CC=C1>>BrC1=C(C=CC=C1)N1C(N(C2=NC(=NC=C2C1)NC1=CC2=C(OC(CO2)COS(=O)(=O)C2=CC=C(C=C2)C)C=C1)C)=O | [OH:9][CH2:10][CH:11]1[CH2:12][O:13][c:14]2[cH:15][c:16]([NH:17][c:18]3[n:19][cH:20][c:21]4[c:22]([n:23]3)[N:24]([CH3:25])[C:26](=[O:27])[N:28]([c:29]3[cH:30][cH:31][cH:32][cH:33][c:34]3[Br:35])[CH2:36]4)[cH:37][cH:38][c:39]2[O:40]1.Cl[S:6]([c:5]1[cH:4][cH:3][c:2]([CH3:1])[cH:42][cH:41]1)(=[O:7])=[O:8]>>[CH3:1][c:2]1[c... | CN1C(=O)N(c2ccccc2Br)Cc2cnc(Nc3ccc4c(c3)OCC(CO)O4)nc21.Cc1ccc(S(=O)(=O)Cl)cc1 | Cc1ccc(S(=O)(=O)OCC2COc3cc(Nc4ncc5c(n4)N(C)C(=O)N(c4ccccc4Br)C5)ccc3O2)cc1 | null | CN(C1=CC=NC=C1)C | C(Cl)(Cl)Cl | Acylation | Formation of Sulfonic Esters | d05d91207659f8fa672c205a316a670adfe2b92492fc9adad2ee3f241e574fb9 | a7748b0f3b0eba3868d0cf03ae67721db046202accaaea9cadb4edbc96ec8768 | O=C1Nc2nc(Nc3ccc4c(c3)OCC(COS(=O)(=O)c3ccccc3)O4)ncc2CN1c1ccccc1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6].[#8:7]-[C:8]-[C:9]-[OH;D1;+0:10]>>[#8:7]-[C:8]-[C:9]-[O;H0;D2;+0:10]-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6] | 26.4 | [{"value": 26.4, "product": "BrC1=C(C=CC=C1)N1C(N(C2=NC(=NC=C2C1)NC1=CC2=C(OC(CO2)COS(=O)(=O)C2=CC=C(C=C2)C)C=C1)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 5 | CELSIUS | 3 | HOUR | 520 mg of the product from example 1 were dissolved in 20 ml CHCl3. 213 mg tosyl chloride and 13 mg 4-dimethylaminopyridine were added and the mixture was cooled to 5° C. 166 mg pyridine were added dropwise and stirring was continued at room temperature for 3 hrs. The mixture was stirred 1 hr at 60° C., then another 10... | 10.6084/m9.figshare.5104873.v1 | null | Tosylate.Primary alcohol.Sulfonyl halide | Tosylate | null | null | c1ccccc1.c1ccc2c(c1)OCCO2.c1ncc2c(n1)[NH]C[NH]C2.c1ccccc1 | HCl | CN(C1=CC=NC=C1)C.C(Cl)(Cl)Cl | 5 | 3 | CN1C(=O)N(c2ccccc2Br)Cc2cnc(Nc3ccc4c(c3)OCC(CO)O4)nc21.Cc1ccc(S(=O)(=O)Cl)cc1>CN(C1=CC=NC=C1)C.C(Cl)(Cl)Cl>Cc1ccc(S(=O)(=O)OCC2COc3cc(Nc4ncc5c(n4)N(C)C(=O)N(c4ccccc4Br)C5)ccc3O2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-a19fcdf6ed754c9987d55b1d13e1762c | CNC.Cc1ccc(S(=O)(=O)OCC2COc3cc(Nc4ncc5c(n4)N(C)C(=O)N(c4ccccc4Br)C5)ccc3O2)cc1>>CN(C)CC1COc2cc(Nc3ncc4c(n3)N(C)C(=O)N(c3ccccc3Br)C4)ccc2O1 | BrC1=C(C=CC=C1)N1C(N(C2=NC(=NC=C2C1)NC1=CC2=C(OC(CO2)COS(=O)(=O)C2=CC=C(C=C2)C)C=C1)C)=O.CNC>>BrC1=C(C=CC=C1)N1C(N(C2=NC(=NC=C2C1)NC1=CC2=C(OC(CO2)CN(C)C)C=C1)C)=O | [CH3:1][NH:2][CH3:3].Cc1ccc(S(=O)(=O)O[CH2:4][CH:5]2[CH2:6][O:7][c:8]3[cH:9][c:10]([NH:11][c:12]4[n:13][cH:14][c:15]5[c:16]([n:17]4)[N:18]([CH3:19])[C:20](=[O:21])[N:22]([c:23]4[cH:24][cH:25][cH:26][cH:27][c:28]4[Br:29])[CH2:30]5)[cH:31][cH:32][c:33]3[O:34]2)cc1>>[CH3:1][N:2]([CH3:3])[CH2:4][CH:5]1[CH2:6][O:7][c:8]2[cH... | CNC.Cc1ccc(S(=O)(=O)OCC2COc3cc(Nc4ncc5c(n4)N(C)C(=O)N(c4ccccc4Br)C5)ccc3O2)cc1 | CN(C)CC1COc2cc(Nc3ncc4c(n3)N(C)C(=O)N(c3ccccc3Br)C4)ccc2O1 | null | null | CN1CCCC1=O.C1CCOC1 | Heteroatom Alkylation and Arylation | OtherReaction | fc30a8c6f38b0001d26cf97e5c444b361d5a5613178be1891358d67f564a3e90 | 71b4ac4449ece5e0df64e56caf0f1cbac76e83f802a92104cfb6c6c861b6a71c | O=C1Nc2nc(Nc3ccc4c(c3)OCCO4)ncc2CN1c1ccccc1 | C-c1:c:c:c(-S(=O)(=O)-O-[CH2;D2;+0:1]-[C:2](-[#8:3]-[c:4])-[C:5]-[#8:6]):c:c:1.[C;D1;H3:7]-[NH;D2;+0:8]-[C;D1;H3:9]>>[#8:6]-[C:5]-[C:2](-[CH2;D2;+0:1]-[N;H0;D3;+0:8](-[C;D1;H3:7])-[C;D1;H3:9])-[#8:3]-[c:4] | null | [] | null | null | 3 | DAY | 90 mg of the tosylate from example 4 in 8 ml NMP were treated with 0.62 ml 2 M dimethylamine in THF and stirred at room temperature for 3 d. The mixture was heated to 50° C. for 4 hrs, then to 65° C. for another 2 hrs. Stirring was continued at 45° C. over night. Separation by HPLC-MS yielded crude product contaminated... | 10.6084/m9.figshare.5104873.v1 | null | Tosylate.Secondary amine | Tertiary amine | c1ccccc1 | null | c1ccc2c(c1)OCCO2.c1ncc2c(n1)[NH]C[NH]C2.c1ccccc1 | TsOH.HO- | CN1CCCC1=O.C1CCOC1 | null | 72 | CNC.Cc1ccc(S(=O)(=O)OCC2COc3cc(Nc4ncc5c(n4)N(C)C(=O)N(c4ccccc4Br)C5)ccc3O2)cc1>CN1CCCC1=O.C1CCOC1>CN(C)CC1COc2cc(Nc3ncc4c(n3)N(C)C(=O)N(c3ccccc3Br)C4)ccc2O1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-93ea8c40085e468c80b7e223c1b1aa11 | CN1C(=O)N(c2c(F)cccc2Br)Cc2cnc(S(C)(=O)=O)nc21.Nc1ccc2c(c1)S(=O)(=O)CCO2>>CN1C(=O)N(c2c(F)cccc2Br)Cc2cnc(Nc3ccc4c(c3)S(=O)(=O)CCO4)nc21 | BrC1=C(C(=CC=C1)F)N1C(N(C2=NC(=NC=C2C1)S(=O)(=O)C)C)=O.NC=1C=CC2=C(S(CCO2)(=O)=O)C1.NC=1C=CC2=C(S(CCO2)(=O)=O)C1.Cl>>BrC1=C(C(=CC=C1)F)N1C(N(C2=NC(=NC=C2C1)NC=1C=CC2=C(S(CCO2)(=O)=O)C1)C)=O | CS(=O)(=O)[c:18]1[n:17][cH:16][c:15]2[c:33]([n:32]1)[N:2]([CH3:1])[C:3](=[O:4])[N:5]([c:6]1[c:7]([F:8])[cH:9][cH:10][cH:11][c:12]1[Br:13])[CH2:14]2.[NH2:19][c:20]1[cH:21][cH:22][c:23]2[c:24]([cH:25]1)[S:26](=[O:27])(=[O:28])[CH2:29][CH2:30][O:31]2>>[CH3:1][N:2]1[C:3](=[O:4])[N:5]([c:6]2[c:7]([F:8])[cH:9][cH:10][cH:11][... | CN1C(=O)N(c2c(F)cccc2Br)Cc2cnc(S(C)(=O)=O)nc21.Nc1ccc2c(c1)S(=O)(=O)CCO2 | CN1C(=O)N(c2c(F)cccc2Br)Cc2cnc(Nc3ccc4c(c3)S(=O)(=O)CCO4)nc21 | null | null | CN1CCCC1=O.CCOCC | Heteroatom Alkylation and Arylation | OtherReaction | ee3efd3d452933cfc1f039815537283e74d04312087383f530a2f91f0b9760a5 | f263fb011eaf2f85af25e2af9b0908fb2797226f3495a5d6be9230bf229d4fae | O=C1Nc2nc(Nc3ccc4c(c3)S(=O)(=O)CCO4)ncc2CN1c1ccccc1 | C-S(=O)(=O)-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5]-[#7:6].[NH2;D1;+0:7]-[c:8](:[c:9]):[c:10]>>[#7:6]-[c:5]:[#7;a:4]:[c;H0;D3;+0:1](-[NH;D2;+0:7]-[c:8](:[c:9]):[c:10]):[#7;a:2]:[c:3] | null | [] | 120 | CELSIUS | null | null | 83 mg 3-(2-bromo-6-fluorophenyl)-3,4-dihydro-7-methanesulphonyl-1-methyl-pyrimido[4,5-d]pyrimidin-2(1H)-one and 80 mg 6-Amino-2,3-dihydro-benzo[1,4]oxathiine-4,4-dioxide (starting material h)) in 0.8 ml NMP were treated with 0.2 ml 2M HCl in ether and heated to 120° C. for 6 hrs. From this mixture 21 mg of the title pr... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Sulfone | Secondary amine | c1ncc2c(n1)[NH]C[NH]C2 | c1ncc2c(n1)[NH]C[NH]C2 | c1ccccc1.c1ncc2c(n1)[NH]C[NH]C2.c1ccc2c(c1)OCCS2 | HO- | CN1CCCC1=O.CCOCC | 120 | null | CN1C(=O)N(c2c(F)cccc2Br)Cc2cnc(S(C)(=O)=O)nc21.Nc1ccc2c(c1)S(=O)(=O)CCO2>CN1CCCC1=O.CCOCC>CN1C(=O)N(c2c(F)cccc2Br)Cc2cnc(Nc3ccc4c(c3)S(=O)(=O)CCO4)nc21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-f840b6ad1baf4e27939b43cc47ae75b9 | CN1C(=O)CSc2cc(N)ccc21.CN1C(=O)N(c2ccccc2Br)Cc2cnc(S(C)(=O)=O)nc21>>CN1C(=O)CSc2cc(Nc3ncc4c(n3)N(C)C(=O)N(c3ccccc3Br)C4)ccc21 | BrC1=C(C=CC=C1)N1C(N(C2=NC(=NC=C2C1)S(=O)(=O)C)C)=O.NC1=CC2=C(N(C(CS2)=O)C)C=C1.NC1=CC2=C(N(C(CS2)=O)C)C=C1.C(=O)(C(F)(F)F)O>>BrC1=C(C=CC=C1)N1C(N(C2=NC(=NC=C2C1)NC1=CC2=C(N(C(CS2)=O)C)C=C1)C)=O | [CH3:1][N:2]1[C:3](=[O:4])[CH2:5][S:6][c:7]2[cH:8][c:9]([NH2:10])[cH:30][cH:31][c:32]21.CS(=O)(=O)[c:11]1[n:12][cH:13][c:14]2[c:15]([n:16]1)[N:17]([CH3:18])[C:19](=[O:20])[N:21]([c:22]1[cH:23][cH:24][cH:25][cH:26][c:27]1[Br:28])[CH2:29]2>>[CH3:1][N:2]1[C:3](=[O:4])[CH2:5][S:6][c:7]2[cH:8][c:9]([NH:10][c:11]3[n:12][cH:1... | CN1C(=O)CSc2cc(N)ccc21.CN1C(=O)N(c2ccccc2Br)Cc2cnc(S(C)(=O)=O)nc21 | CN1C(=O)CSc2cc(Nc3ncc4c(n3)N(C)C(=O)N(c3ccccc3Br)C4)ccc21 | null | null | CN1CCCC1=O.Cl | Heteroatom Alkylation and Arylation | OtherReaction | ee3efd3d452933cfc1f039815537283e74d04312087383f530a2f91f0b9760a5 | f263fb011eaf2f85af25e2af9b0908fb2797226f3495a5d6be9230bf229d4fae | O=C1CSc2cc(Nc3ncc4c(n3)NC(=O)N(c3ccccc3)C4)ccc2N1 | C-S(=O)(=O)-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5]-[#7:6].[NH2;D1;+0:7]-[c:8](:[c:9]):[c:10]>>[#7:6]-[c:5]:[#7;a:4]:[c;H0;D3;+0:1](-[NH;D2;+0:7]-[c:8](:[c:9]):[c:10]):[#7;a:2]:[c:3] | null | [] | 140 | CELSIUS | null | null | 320 mg 3-(2-bromo-phenyl)-3,4-dihydro-7-methanesulphonyl-1-methylpyrimido-[4,5-d]pyrimidin-2(1H)-one and 626 mg 7-amino-4-methyl-4H-benzo[1,4]thiazin-3-one (starting material k)) in 4 ml NMP were treated with 92 mg TFA and heated to 140° C. for 12 hrs. The mixture was diluted with aqueous HCl and the precipitated produ... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Sulfone | Secondary amine | c1ncc2c(n1)[NH]C[NH]C2 | c1ncc2c(n1)[NH]C[NH]C2 | c1ccc2c(c1)[NH]CCS2.c1ncc2c(n1)[NH]C[NH]C2.c1ccccc1 | HO- | CN1CCCC1=O.Cl | 140 | null | CN1C(=O)CSc2cc(N)ccc21.CN1C(=O)N(c2ccccc2Br)Cc2cnc(S(C)(=O)=O)nc21>CN1CCCC1=O.Cl>CN1C(=O)CSc2cc(Nc3ncc4c(n3)N(C)C(=O)N(c3ccccc3Br)C4)ccc21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-3217fe884c024c1793d25f2ce03d4619 | CN1C(=O)CSc2cc(Nc3ncc4c(n3)N(C)C(=O)N(c3ccccc3Br)C4)ccc21.CO>>COC1=CS(=O)c2cc(Nc3ncc4c(n3)N(C)C(=O)N(c3ccccc3Br)C4)ccc2N1C | BrC1=C(C=CC=C1)N1C(N(C2=NC(=NC=C2C1)NC1=CC2=C(N(C(CS2)=O)C)C=C1)C)=O.OOS(=O)[O-].[K+].CO>>BrC1=C(C=CC=C1)N1C(N(C2=NC(=NC=C2C1)NC1=CC2=C(N(C(=CS2=O)OC)C)C=C1)C)=O | [C:3]1(=[O:6])[CH2:4][S:5][c:7]2[cH:8][c:9]([NH:10][c:11]3[n:12][cH:13][c:14]4[c:15]([n:16]3)[N:17]([CH3:18])[C:19](=[O:20])[N:21]([c:22]3[cH:23][cH:24][cH:25][cH:26][c:27]3[Br:28])[CH2:29]4)[cH:30][cH:31][c:32]2[N:33]1[CH3:34].[CH3:1][OH:2]>>[CH3:1][O:2][C:3]1=[CH:4][S:5](=[O:6])[c:7]2[cH:8][c:9]([NH:10][c:11]3[n:12][... | CN1C(=O)CSc2cc(Nc3ncc4c(n3)N(C)C(=O)N(c3ccccc3Br)C4)ccc21.CO | COC1=CS(=O)c2cc(Nc3ncc4c(n3)N(C)C(=O)N(c3ccccc3Br)C4)ccc2N1C | null | null | null | Acylation | OtherReaction | 88491d3959184b9fdc1bdfc080e7820bef0fd45ec3e03ea233ddee800c7d5c2b | a0113c55de983d3cbfa88e2fc30cdc65301723d4844d5aa52fdf5db026d02416 | O=C1Nc2nc(Nc3ccc4c(c3)S(=O)C=CN4)ncc2CN1c1ccccc1 | [C;D1;H3:1]-[#7:2]1-[c:3]:[c:4](:[c:5])-[S;H0;D2;+0:6]-[CH2;D2;+0:7]-[C;H0;D3;+0:8]-1=[O;H0;D1;+0:9].[C;D1;H3:10]-[OH;D1;+0:11]>>[C;D1;H3:10]-[O;H0;D2;+0:11]-[C;H0;D3;+0:8]1=[CH;D2;+0:7]-[S;H0;D3;+0:6](=[O;H0;D1;+0:9])-[c:4](:[c:5]):[c:3]-[#7:2]-1-[C;D1;H3:1] | null | [] | null | null | null | null | 100 mg of the compound from example 9 and 108 mg oxone were stirred in 2 ml MeOH at room temperature for 17 hrs. The mixture was filtered and the residue washed with THF. The combined filtrates were concentrated and purified by preparative HPLC-MS to yield 10 mg of the title compound.
Conditions: See reaction.notes.pro... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Monosulfide.Methanol | Enamine.Ether.Sulfoxide | c1ccc2c(c1)[NH]CCS2 | C1=CSc2ccccc2[NH]1 | C1=CSc2ccccc2[NH]1.c1ncc2c(n1)[NH]C[NH]C2.c1ccccc1 | null | null | null | null | CN1C(=O)CSc2cc(Nc3ncc4c(n3)N(C)C(=O)N(c3ccccc3Br)C4)ccc21.CO>>COC1=CS(=O)c2cc(Nc3ncc4c(n3)N(C)C(=O)N(c3ccccc3Br)C4)ccc2N1C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-29b0fbe5e63c4c83a1b1bf1aabfd45bd | CN1C(=O)N(c2c(F)cccc2Br)Cc2cnc(S(C)(=O)=O)nc21.CN1C=CS(=O)(=O)c2cc(N)ccc21>>CN1CCS(=O)(=O)c2cc(Nc3ncc4c(n3)N(C)C(=O)N(c3c(F)cccc3Br)C4)ccc21 | BrC1=C(C(=CC=C1)F)N1C(N(C2=NC(=NC=C2C1)S(=O)(=O)C)C)=O.NC1=CC2=C(N(C=CS2(=O)=O)C)C=C1.NC1=CC2=C(N(C=CS2(=O)=O)C)C=C1.Cl>>BrC1=C(C(=CC=C1)F)N1C(N(C2=NC(=NC=C2C1)NC1=CC2=C(N(CCS2(=O)=O)C)C=C1)C)=O | CS(=O)(=O)[c:12]1[n:13][cH:14][c:15]2[c:16]([n:17]1)[N:18]([CH3:19])[C:20](=[O:21])[N:22]([c:23]1[c:24]([F:25])[cH:26][cH:27][cH:28][c:29]1[Br:30])[CH2:31]2.[CH3:1][N:2]1[CH:3]=[CH:4][S:5](=[O:6])(=[O:7])[c:8]2[cH:9][c:10]([NH2:11])[cH:32][cH:33][c:34]21>>[CH3:1][N:2]1[CH2:3][CH2:4][S:5](=[O:6])(=[O:7])[c:8]2[cH:9][c:1... | CN1C(=O)N(c2c(F)cccc2Br)Cc2cnc(S(C)(=O)=O)nc21.CN1C=CS(=O)(=O)c2cc(N)ccc21 | CN1CCS(=O)(=O)c2cc(Nc3ncc4c(n3)N(C)C(=O)N(c3c(F)cccc3Br)C4)ccc21 | null | null | CN1CCCC1=O.CCOCC | Heteroatom Alkylation and Arylation | OtherReaction | 7f97bbb76f1f9cd3dbe6d75e5a586f889a8f989cf6a55a649c3875b9f2d4f28e | 6ded126f3686d9a6d9c73ca3bae820abe632d743e4141a5b0b68f915c1a161b6 | O=C1Nc2nc(Nc3ccc4c(c3)S(=O)(=O)CCN4)ncc2CN1c1ccccc1 | C-S(=O)(=O)-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5]-[#7:6].[C;D1;H3:7]-[#7:8]1-[CH;D2;+0:9]=[CH;D2;+0:10]-[#16:11](=[O;D1;H0:12])(=[O;D1;H0:13])-[c:14](:[c:15]-1):[c:16]:[c:17](-[NH2;D1;+0:18]):[c:19]>>[#7:6]-[c:5]:[#7;a:4]:[c;H0;D3;+0:1](-[NH;D2;+0:18]-[c:17](:[c:19]):[c:16]:[c:14]1:[c:15]-[#7:8](-[C;D1;H3:7])-... | 31.1 | [{"value": 31.1, "product": "BrC1=C(C(=CC=C1)F)N1C(N(C2=NC(=NC=C2C1)NC1=CC2=C(N(CCS2(=O)=O)C)C=C1)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 120 | CELSIUS | null | null | 83 mg 3-(2-bromo-6-fluorophenyl)-3,4-dihydro-7-methanesulphonyl-1-methyl-pyrimido[4,5-d]pyrimidin-2(1H)-one and 85 mg 7-Amino-4-methyl-4H-benzo[1,4]thiazin-1,1-dioxide (starting material n)) in 0.8 ml NMP were treated with 0.2 ml 2M HCl in ether and heated to 120° C. for 6 hrs. The mixture was purified by preparative H... | 10.6084/m9.figshare.5104873.v1 | null | Enamine.Primary amine.Sulfone | Secondary amine | c1ncc2c(n1)[NH]C[NH]C2.C1=CSc2ccccc2[NH]1 | c1ccc2c(c1)[NH]CCS2.c1ncc2c(n1)[NH]C[NH]C2 | c1ccc2c(c1)[NH]CCS2.c1ncc2c(n1)[NH]C[NH]C2.c1ccccc1 | HO- | CN1CCCC1=O.CCOCC | 120 | null | CN1C(=O)N(c2c(F)cccc2Br)Cc2cnc(S(C)(=O)=O)nc21.CN1C=CS(=O)(=O)c2cc(N)ccc21>CN1CCCC1=O.CCOCC>CN1CCS(=O)(=O)c2cc(Nc3ncc4c(n3)N(C)C(=O)N(c3c(F)cccc3Br)C4)ccc21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-a9de6531ee9847a1bab8c6c69fe2b068 | CCOC(C)=O.Nc1cccc2c1OCCO2.OCCCl>>OCCN(CCO)c1cccc2c1OCCO2 | C(C)(=O)OCC.O1CCOC2=C1C=CC=C2N.ClCCO.CCN(C(C)C)C(C)C>>O1CCOC2=C1C=CC=C2N(CCO)CCO | CCO[C:2](=[O:1])[CH3:3].[NH2:4][c:8]1[cH:9][cH:10][cH:11][c:12]2[c:13]1[O:14][CH2:15][CH2:16][O:17]2.Cl[CH2:5][CH2:6][OH:7]>>[OH:1][CH2:2][CH2:3][N:4]([CH2:5][CH2:6][OH:7])[c:8]1[cH:9][cH:10][cH:11][c:12]2[c:13]1[O:14][CH2:15][CH2:16][O:17]2 | CCOC(C)=O.Nc1cccc2c1OCCO2.OCCCl | OCCN(CCO)c1cccc2c1OCCO2 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 20efb100b282e3e83bedec48d8d0b8c9f60a1d512b287506bf91cfd0e0f13774 | 682845fd6e4ee022263638cacc7e4d6916161ec23e7a3a9e98f71ea328ee90a2 | c1ccc2c(c1)OCCO2 | C-C-O-[C;H0;D3;+0:1](-[CH3;D1;+0:2])=[O;H0;D1;+0:3].Cl-[CH2;D2;+0:4]-[C:5]-[O;D1;H1:6].[#8:7]-[c:8]:[c:9](-[NH2;D1;+0:10]):[c:11]>>[#8:7]-[c:8]:[c:9](-[N;H0;D3;+0:10](-[CH2;D2;+0:2]-[CH2;D2;+0:1]-[OH;D1;+0:3])-[CH2;D2;+0:4]-[C:5]-[O;D1;H1:6]):[c:11] | 80 | [{"value": 80.0, "product": "O1CCOC2=C1C=CC=C2N(CCO)CCO", "details": "PERCENTYIELD", "is_desired": false}] | 120 | CELSIUS | 12.5 | HOUR | 2,3-Dihydro-benzo[1,4]dioxin-5-ylamine (31.1 g, 0.2 mol) is mixed with 2-chloroethanol (210 mL, 3.1 mol) and Hunigs base (105 mL, 0.6 mol). The resulting dark solution is heated to 120° C. and stirred at this temperature with continuous monitoring by HPLC. After 12.5 h, the reaction is stopped. Ethyl acetate (300 mL) i... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester.Primary amine | Primary alcohol.Tertiary amine | null | null | c1ccc2c(c1)OCCO2 | HCl | null | 120 | 12.5 | CCOC(C)=O.Nc1cccc2c1OCCO2.OCCCl>>OCCN(CCO)c1cccc2c1OCCO2 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-7de5138076c54710a85ef56f3fb895ce | CCN(CC)CC.CS(=O)(=O)Cl.OCCN(CCO)c1cccc2c1OCCO2>>CS(=O)(=O)OCCN(CCOS(C)(=O)=O)c1cccc2c1OCCO2 | S(=O)(=O)(C)Cl.O1CCOC2=C1C=CC=C2N(CCO)CCO.C(C)N(CC)CC>>O1CCOC2=C1C=CC=C2N(CCOS(=O)(=O)C)CCOS(=O)(=O)C | CCN(CC)C[CH3:13].Cl[S:2]([CH3:1])(=[O:4])=[O:15].[OH:3][CH2:10][CH2:9][N:8]([CH2:7][CH2:6][OH:5])[c:16]1[cH:17][cH:18][cH:19][c:20]2[c:21]1[O:22][CH2:23][CH2:24][O:25]2>>[CH3:1][S:2](=[O:3])(=[O:4])[O:5][CH2:6][CH2:7][N:8]([CH2:9][CH2:10][O:11][S:12]([CH3:13])(=[O:14])=[O:15])[c:16]1[cH:17][cH:18][cH:19][c:20]2[c:21]1[... | CCN(CC)CC.CS(=O)(=O)Cl.OCCN(CCO)c1cccc2c1OCCO2 | CS(=O)(=O)OCCN(CCOS(C)(=O)=O)c1cccc2c1OCCO2 | null | null | C(Cl)Cl | Oxidation | OtherReaction | f583fd126c5884f328510e6accbdcc692c64aca6a7316f9f31038b1598107fb9 | fc7b3469255771e7bdb4be1e17290b023aa82e438e44c1e0e14504d7b513ee23 | c1ccc2c(c1)OCCO2 | C-C-N(-C-C)-C-[CH3;D1;+0:1].Cl-[S;H0;D4;+0:2](-[C;D1;H3:3])(=[O;D1;H0:4])=[O;H0;D1;+0:5].[OH;D1;+0:6]-[CH2;D2;+0:7]-[C:8]-[#7:9]-[C:10]-[C:11]-[OH;D1;+0:12]>>[C;D1;H3:3]-[S;H0;D4;+0:2](=[O;D1;H0:4])(=[O;H0;D1;+0:6])-[O;H0;D2;+0:12]-[C:11]-[C:10]-[#7:9]-[C:8]-[CH2;D2;+0:7]-[#8:13]-[#16:14](-[CH3;D1;+0:1])(=[O;D1;H0:15])... | null | [] | null | null | 0.5 | HOUR | To a solution of II (39.6 g, 0.165 mol) and triethyl amine (69 mL, 0.5 mol) in methylene chloride (250 mL), chilled to 5° C. in an ice-bath, is added a solution of mesyl chloride (38 mL, 0.5 mol) in methylene chloride (50 mL). The addition is carried out over 0.5 h at temperature not exceeding 18° C. The ice-bath is re... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Primary alcohol.Tertiary amine.Sulfonyl halide | Mesylate.Mesylate | null | null | c1ccc2c(c1)OCCO2 | HCl | C(Cl)Cl | null | 0.5 | CCN(CC)CC.CS(=O)(=O)Cl.OCCN(CCO)c1cccc2c1OCCO2>C(Cl)Cl>CS(=O)(=O)OCCN(CCOS(C)(=O)=O)c1cccc2c1OCCO2 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-571c3a84051c458eaa66f8ab65574112 | CC#N.CS(=O)(=O)OCCN(CCOS(C)(=O)=O)c1cccc2c1OCCO2>>CC(CO)N1CCN(c2cccc3c2OCCO3)CC1 | O1CCOC2=C1C=CC=C2N(CCOS(=O)(=O)C)CCOS(=O)(=O)C.[Br-].[Li+].C([O-])([O-])=O.[K+].[K+].C(C)#N>>O1CCOC2=C1C=CC=C2N2CCN(CC2)C(CO)C | [CH3:1][C:2]#[N:5].CS(=O)(=O)O[CH2:6][CH2:7][N:8]([c:9]1[cH:10][cH:11][cH:12][c:13]2[c:14]1[O:15][CH2:16][CH2:17][O:18]2)[CH2:19][CH2:20]OS(C)(=O)=O>>[CH3:1][CH:2]([CH2:3][OH:4])[N:5]1[CH2:6][CH2:7][N:8]([c:9]2[cH:10][cH:11][cH:12][c:13]3[c:14]2[O:15][CH2:16][CH2:17][O:18]3)[CH2:19][CH2:20]1 | CC#N.CS(=O)(=O)OCCN(CCOS(C)(=O)=O)c1cccc2c1OCCO2 | CC(CO)N1CCN(c2cccc3c2OCCO3)CC1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 158c4849b26210adae1cebcad13a700376257a6d4743e456870967db90856d72 | cb2bf806bd966ca8fc4028f279edd8536e108ff663292844a98390b0004168a7 | c1cc2c(c(N3CCNCC3)c1)OCCO2 | C-S(=O)(=O)-O-[CH2;D2;+0:1]-[C:2]-[#7:3]-[C:4]-[CH2;D2;+0:5]-O-S(-C)(=O)=O.[C;D1;H3:6]-[C;H0;D2;+0:7]#[N;H0;D1;+0:8]>>[C;D1;H3:6]-[CH;D3;+0:7](-[C:9]-[O;D1;H1:10])-[N;H0;D3;+0:8]1-[CH2;D2;+0:1]-[C:2]-[#7:3]-[C:4]-[CH2;D2;+0:5]-1 | null | [] | 82 | CELSIUS | null | null | Dimesylate III (67.0 g, 0.17 mol), D-alaminol (14.0 g, 0.19 mol), lithium bromide (31.0 g, 0.35 mol), and potassium carbonate (74.8 g, 0.54 mol) are mixed together with acetonitrile (750 mL). The resulting suspension is refluxed (82° C.) for 27 h with monitoring by HPLC. The reaction mixture is cooled, filtered, and in... | 10.6084/m9.figshare.5104873.v1 | null | Mesylate.Mesylate.Nitrile | Primary alcohol.Tertiary amine | null | C1C[NH]CC[NH]1 | C1C[NH]CC[NH]1.c1ccc2c(c1)OCCO2 | MsOH.HO- | null | 82 | null | CC#N.CS(=O)(=O)OCCN(CCOS(C)(=O)=O)c1cccc2c1OCCO2>>CC(CO)N1CCN(c2cccc3c2OCCO3)CC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b76a6354ffcf4de38c61a0fa061d1f6a | CC(CO)N1CCN(c2cccc3c2OCCO3)CC1.CS(=O)(=O)Cl>>CC1C[N+]12CCN(c1cccc3c1OCCO3)CC2.[Cl-] | S(=O)(=O)(C)Cl.O1CCOC2=C1C=CC=C2N2CCN(CC2)C(CO)C.C(C)N(CC)CC>>[Cl-].O1CCOC2=C1C=CC=C2N2CC[N+]1(CC1C)CC2 | O[CH2:3][CH:2]([CH3:1])[N:4]1[CH2:5][CH2:6][N:7]([c:8]2[cH:9][cH:10][cH:11][c:12]3[c:13]2[O:14][CH2:15][CH2:16][O:17]3)[CH2:18][CH2:19]1.CS(=O)(=O)[Cl:20]>>[CH3:1][CH:2]1[CH2:3][N+:4]12[CH2:5][CH2:6][N:7]([c:8]1[cH:9][cH:10][cH:11][c:12]3[c:13]1[O:14][CH2:15][CH2:16][O:17]3)[CH2:18][CH2:19]2.[Cl-:20] | CC(CO)N1CCN(c2cccc3c2OCCO3)CC1.CS(=O)(=O)Cl | CC1C[N+]12CCN(c1cccc3c1OCCO3)CC2.[Cl-] | null | null | C(Cl)Cl | Heteroatom Alkylation and Arylation | OtherReaction | 1477f2a479ba29f67e84f441510537579437c9e651785f759cc0b1d053908a41 | 8fb6c0545b73d5595e1bfd94e1a50035393ac4a477df131ec53cc02ed6b57d9b | c1cc2c(c(N3CC[N+]4(CC3)CC4)c1)OCCO2 | C-S(=O)(=O)-[Cl;H0;D1;+0:1].O-[CH2;D2;+0:2]-[C:3](-[C;D1;H3:4])-[N;H0;D3;+0:5]1-[C:6]-[C:7]-[#7:8]-[C:9]-[C:10]-1>>[C;D1;H3:4]-[C:3]1-[CH2;D2;+0:2]-[N+;H0;D4:5]-12-[C:6]-[C:7]-[#7:8]-[C:9]-[C:10]-2.[Cl-;H0;D0:1] | null | [] | 10 | CELSIUS | 8 | HOUR | Crude compound IV (29.4 g, 0.106 mol), and triethyl amine (16.2 mL, 0.116 mol) are dissolved in CH2Cl2 (150 mL) and to this solution is added a solution of mesyl chloride (8.6 mL, 0.111 mol) in CH2Cl2 (50 mL) under cooling at 5 to 15° C. over 0.5 h. Stirring is continued overnight at ambient temperature resulting in cl... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Tertiary amine.Sulfonyl halide | null | C1C[NH]CC[NH]1 | C1C[N+]2(CC[NH]1)CC2 | C1C[N+]2(CC[NH]1)CC2.c1ccc2c(c1)OCCO2 | HO- | C(Cl)Cl | 10 | 8 | CC(CO)N1CCN(c2cccc3c2OCCO3)CC1.CS(=O)(=O)Cl>C(Cl)Cl>CC1C[N+]12CCN(c1cccc3c1OCCO3)CC2.[Cl-] |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-779b953e77fe402c909ac5a29593fac4 | CC(CN(C(=O)OC(C)(C)C)c1ccccn1)N1CCN(c2cccc3c2OCCO3)CC1>>CC(CNc1ccccn1)N1CCN(c2cccc3c2OCCO3)CC1 | Cl.C(C)(C)(C)OC(N(C1=NC=CC=C1)CC(C)N1CCN(CC1)C1=CC=CC=2OCCOC21)=O>>O1CCOC2=C1C=CC=C2N2CCN(CC2)C(CNC2=NC=CC=C2)C | CC(C)(C)OC(=O)[N:4]([CH2:3][CH:2]([CH3:1])[N:11]1[CH2:12][CH2:13][N:14]([c:15]2[cH:16][cH:17][cH:18][c:19]3[c:20]2[O:21][CH2:22][CH2:23][O:24]3)[CH2:25][CH2:26]1)[c:5]1[cH:6][cH:7][cH:8][cH:9][n:10]1>>[CH3:1][CH:2]([CH2:3][NH:4][c:5]1[cH:6][cH:7][cH:8][cH:9][n:10]1)[N:11]1[CH2:12][CH2:13][N:14]([c:15]2[cH:16][cH:17][cH... | CC(CN(C(=O)OC(C)(C)C)c1ccccn1)N1CCN(c2cccc3c2OCCO3)CC1 | CC(CNc1ccccn1)N1CCN(c2cccc3c2OCCO3)CC1 | null | null | C(C)O | Reduction | Boc amine deprotection | bbda4640db5f48af4538caded12fdadd56eacd6d4e5f7aefe46282d665df167e | a94b29c7264c852156fc1cdd4a0951a4fc26c06d0edc9e50c743825dbf79e3fd | c1ccc(NCCN2CCN(c3cccc4c3OCCO4)CC2)nc1 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1](-[C:2]-[C:3])-[c:4](:[c:5]):[#7;a:6]:[c:7]>>[C:3]-[C:2]-[NH;D2;+0:1]-[c:4](:[c:5]):[#7;a:6]:[c:7] | 49 | [{"value": 49.0, "product": "O1CCOC2=C1C=CC=C2N2CCN(CC2)C(CNC2=NC=CC=C2)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | Compound VII as a crude oil (49.0 g, 0.106 mol) is dissolved in ethanol (150 mL) and to this solution is added 1N HCl solution in ethanol (212 mL). The resulting solution is refluxed for 18 h, then concentrated in vacuum to a small volume (˜100 mL) until product starts to crystallize. Ether (100 mL) is added slowly to ... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Secondary amine | null | null | c1ccncc1.C1C[NH]CC[NH]1.c1ccc2c(c1)OCCO2 | HO- | C(C)O | null | 2 | CC(CN(C(=O)OC(C)(C)C)c1ccccn1)N1CCN(c2cccc3c2OCCO3)CC1>C(C)O>CC(CNc1ccccn1)N1CCN(c2cccc3c2OCCO3)CC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-fb0606f185084d1b8d67c80a921b4652 | C=CC(=O)OCC.CCC1CC(O)C(=O)O1>>C/C=C/C=C/C(=O)OCC | C(C=C)(=O)OCC.OC(C(=O)OCC)CC(CC)O.C(C)C1CC(C(=O)O1)O>>C(\C=C\C=C\C)(=O)OCC | [CH2:4]=[CH:5][C:6](=[O:7])[O:8][CH2:9][CH3:10].O=C1O[CH:3]([CH2:2][CH3:1])CC1O>>[CH3:1]/[CH:2]=[CH:3]/[CH:4]=[CH:5]/[C:6](=[O:7])[O:8][CH2:9][CH3:10] | C=CC(=O)OCC.CCC1CC(O)C(=O)O1 | C/C=C/C=C/C(=O)OCC | null | null | C(CC)O | C-C Coupling | OtherReaction | 05863aa458dfdd2f9a9c8e48495557f87e213b999a473b9142023c9077383b70 | 94bc7d13335f648a028b25b9386071a96909b7b4bc887b60ca6df890b110e0fe | null | O-C1-C-[CH;D3;+0:1](-[CH2;D2;+0:2]-[C;D1;H3:3])-O-C-1=O.[C:4]-[#8:5]-[C:6](=[O;D1;H0:7])-[C:8]=[CH2;D1;+0:9]>>[C:4]-[#8:5]-[C:6](=[O;D1;H0:7])/[C:8]=[CH;D2;+0:9]/[CH;D2;+0:1]=[CH;D2;+0:2]/[C;D1;H3:3] | null | [] | null | null | null | null | For example, when n-propyl alcohol is allowed to react with ethyl acrylate, ethyl 2,4-dihydroxyhexanoate corresponding to Formula (4) and 4-ethyl-2-hydroxy-γ-butyrolactone corresponding to Formula (6) are formed under some conditions in addition to the target ethyl sorbate.
Conditions: See reaction.notes.procedure_deta... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Secondary alcohol.Vinyl | Conjugated diene | C1CCOC1 | null | null | HO- | C(CC)O | null | null | C=CC(=O)OCC.CCC1CC(O)C(=O)O1>C(CC)O>C/C=C/C=C/C(=O)OCC |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-bd8297b3cf7f4124a97a04ca91aa86e8 | CC(=O)O.O=O.O=c1n(O)c(=O)n(O)c(=O)n1O>>O=C(O)c1ccc(C(=O)O)cc1 | O=O.C(C)(=O)O.ON1C(N(C(N(C1=O)O)=O)O)=O.CC=1C=CC(=CC1)C(=O)O>>C(C1=CC=C(C(=O)O)C=C1)(=O)O.CC=1C=CC(=CC1)C(=O)O | [O:11]=[C:12]([OH:13])[CH3:14].O=[O:20].O=[c:15]1n(O)[c:17](=O)n(O)[c:18](=[O:19])n1O>>[O:11]=[C:12]([OH:13])[c:14]1[cH:15][cH:16][c:17]([C:18](=[O:19])[OH:20])[cH:21][cH:22]1 | CC(=O)O.O=O.O=c1n(O)c(=O)n(O)c(=O)n1O | O=C(O)c1ccc(C(=O)O)cc1 | null | [Ti].C(C)(=O)[O-].[Co+2].C(C)(=O)[O-].C(C)(=O)[O-].[Mn+2].C(C)(=O)[O-] | O | Acylation | OtherReaction | b7fa0db7f1a76ad08bcbfd171ea83962b41786886f9223330a41d5c50554b663 | 903e48d04e4504a4fe6977f5e5582144adff237d0488a4542a1907161cf0134c | c1ccccc1 | O-n1:[c;H0;D3;+0:1](=O):n(-O):[c;H0;D3;+0:2](=[O;D1;H0:3]):n(-O):[c;H0;D3;+0:4]:1=O.O=[O;H0;D1;+0:5].[CH3;D1;+0:6]-[C:7](=[O;D1;H0:8])-[O;D1;H1:9]>>[O;D1;H0:8]=[C:7](-[O;D1;H1:9])-[c;H0;D3;+0:6]1:[c:10]:[c:11]:[c;H0;D3;+0:4](-[C;H0;D3;+0:2](=[O;D1;H0:3])-[OH;D1;+0:5]):[c:12]:[cH;D2;+0:1]:1 | null | [] | 150 | CELSIUS | 1 | HOUR | In a 500-ml titanium autoclave equipped with a stirrer and a pressure gauge, 15.36 g of p-toluic acid, 104.0 g of acetic acid, 0.066 g of hexahydro-1,3,5-trihydroxy-1,3,5-triazine-2,4,6-trione (1,3,5-trihydroxyisocyanuric acid) (0.33% by mole relative to p-toluic acid), 0.112 g of cobalt(II) acetate.4H2O and 0.277 g of... | 10.6084/m9.figshare.5104873.v1 | null | null | Carboxylic acid | c1ncncn1 | c1ccccc1 | c1ccccc1 | HO- | [Ti].C(C)(=O)[O-].[Co+2].C(C)(=O)[O-].C(C)(=O)[O-].[Mn+2].C(C)(=O)[O-].O | 150 | 1 | CC(=O)O.O=O.O=c1n(O)c(=O)n(O)c(=O)n1O>[Ti].C(C)(=O)[O-].[Co+2].C(C)(=O)[O-].C(C)(=O)[O-].[Mn+2].C(C)(=O)[O-].O>O=C(O)c1ccc(C(=O)O)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-3d5750931bd44381b0102746045a956c | CC(=O)O.CC(=O)On1c(=O)n(OC(C)=O)c(=O)n(OC(C)=O)c1=O>>O=C(O)c1ccc(C(=O)O)cc1 | O=O.C(C)(=O)O.C(C)(=O)ON1C(N(C(N(C1=O)OC(C)=O)=O)OC(C)=O)=O.CC=1C=CC(=CC1)C(=O)O>>C(C1=CC=C(C(=O)O)C=C1)(=O)O.CC=1C=CC(=CC1)C(=O)O | O=[C:22]([OH:20])[CH3:21].O=c1n(O[C:16](=O)[CH3:15])c(=O)n([O:13][C:12](=[O:11])[CH3:14])c(=O)n1O[C:18]([CH3:17])=[O:19]>>[O:11]=[C:12]([OH:13])[c:14]1[cH:15][cH:16][c:17]([C:18](=[O:19])[OH:20])[cH:21][cH:22]1 | CC(=O)O.CC(=O)On1c(=O)n(OC(C)=O)c(=O)n(OC(C)=O)c1=O | O=C(O)c1ccc(C(=O)O)cc1 | null | [Ti].C(C)(=O)[O-].[Co+2].C(C)(=O)[O-].C(C)(=O)[O-].[Mn+2].C(C)(=O)[O-] | O | Acylation | OtherReaction | 4837002bb2b893f5ccf3a6fd5f774854511cf58b7d7a9dbb4ce8cbe123093090 | 05b1e9e4110bc86f2bd7cbdf6b80dcc179cd6fe787ce74ddba60fa77e8ec4cfa | c1ccccc1 | O=[C;H0;D3;+0:1](-[CH3;D1;+0:2])-O-n1:c(=O):n(-O-[C;H0;D3;+0:3](-[CH3;D1;+0:4])=[O;D1;H0:5]):c(=O):n(-[O;H0;D2;+0:6]-[C:7](-[CH3;D1;+0:8])=[O;D1;H0:9]):c:1=O.O=[C;H0;D3;+0:10](-[CH3;D1;+0:11])-[OH;D1;+0:12]>>[O;D1;H0:9]=[C:7](-[OH;D1;+0:6])-[c;H0;D3;+0:8]1:[cH;D2;+0:2]:[cH;D2;+0:1]:[c;H0;D3;+0:4](-[C;H0;D3;+0:3](=[O;D1... | null | [] | 150 | CELSIUS | 1 | HOUR | In a 500-ml titanium autoclave equipped with a stirrer and a pressure gauge, 15.36 g of p-toluic acid, 104.0 g of acetic acid, 0.114 g of 1,3,5-triacetoxy-hexahydro-1,3,5-triazine-2,4,6-trione (1,3,5-triacetoxyisocyanuric acid) (0.33% by mole relative to p-toluic acid), 0.112 g of cobalt(II) acetate.4H2O and 0.277 g of... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Carboxylic acid.Carboxylic acid | c1ncncn1 | c1ccccc1 | c1ccccc1 | HO- | [Ti].C(C)(=O)[O-].[Co+2].C(C)(=O)[O-].C(C)(=O)[O-].[Mn+2].C(C)(=O)[O-].O | 150 | 1 | CC(=O)O.CC(=O)On1c(=O)n(OC(C)=O)c(=O)n(OC(C)=O)c1=O>[Ti].C(C)(=O)[O-].[Co+2].C(C)(=O)[O-].C(C)(=O)[O-].[Mn+2].C(C)(=O)[O-].O>O=C(O)c1ccc(C(=O)O)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-357e71c8313b4627985e801cce9d4fe8 | CCC(=O)O.O=c1n(O)c(=O)n(O)c(=O)n1O.c1ccc2c(c1)Cc1ccccc1-2>>O=C1C=CC=C2C1=Cc1ccccc12.Oc1cccc2c1Cc1ccccc1-2 | C1=CC=CC=2C3=CC=CC=C3CC12.ON1C(N(C(N(C1=O)O)=O)O)=O.C(CC)(=O)O.O=O>>C1(C=CC=C2C3=CC=CC=C3C=C12)=O.C1(=CC=CC=2C3=CC=CC=C3CC12)O | O=[C:16](O)[CH2:17][CH3:13].O=[c:12]1n([OH:15])[c:2](=[O:1])n(O)[c:14](=O)n1O.[cH:10]1[cH:11][cH:18][cH:19][c:20]2[c:21]1[CH2:22][c:23]1[cH:24][cH:25][cH:26][cH:27][c:28]1-2>>[O:1]=[C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:7]1=[CH:8][c:9]1[cH:10][cH:11][cH:12][cH:13][c:14]12.[OH:15][c:16]1[cH:17][cH:18][cH:19][c:20]2[c:21]1[C... | CCC(=O)O.O=c1n(O)c(=O)n(O)c(=O)n1O.c1ccc2c(c1)Cc1ccccc1-2 | O=C1C=CC=C2C1=Cc1ccccc12.Oc1cccc2c1Cc1ccccc1-2 | null | C(C)(=O)[O-].[Mn+2].C(C)(=O)[O-].C(C)(=O)[O-].[Co+2].C(C)(=O)[O-] | null | Aromatic Heterocycle Formation | OtherReaction | a1167484c92a5d40d6f8325938f4e3ae29bf61d15e92d835787ef9a512631d72 | 9cebe92661c328b75b6b8cd5de57144adc3144900a4a707395783ac58722aa41 | O=C1C=CC=C2C1=Cc1ccccc12.c1ccc2c(c1)Cc1ccccc1-2 | O-[C;H0;D3;+0:1](=O)-[CH2;D2;+0:2]-[CH3;D1;+0:3].O-n1:[c;H0;D3;+0:4](=O):n(-[OH;D1;+0:5]):[c;H0;D3;+0:6](=[O;D1;H0:7]):n(-O):[c;H0;D3;+0:8]:1=O.[C:9]1-[c:10]:[c:11]-[c:12]2:[c:13]:[cH;D2;+0:14]:[cH;D2;+0:15]:[cH;D2;+0:16]:[c;H0;D3;+0:17]:2-1>>[O;D1;H0:7]=[C;H0;D3;+0:6]1-[C:18]=[C:19]-[C:20]=[C:21]2-[C:22]-1=[C:23]-[c:2... | null | [] | null | null | null | null | A mixture of 1.00 g of fluorene, 0.036 g of hexahydro-1,3,5-trihydroxy-1,3,5-triazine-2,4,6-trione (3% by mole relative to fluorene), 9.0 g of propionic acid, 0.008 g of cobalt(II) acetate.4H2O and 0.008 g of manganese(II) acetate.4H2O was stirred at 120° C. in an atmosphere of oxygene gas (1 atm=0.1 MPa) for 5 hours. ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Ketone.Aromatic alcohol.Conjugated diene | c1ncncn1.c1ccc2c(c1)Cc1ccccc12 | C1=CCC2=Cc3ccccc3C2=C1.c1ccc2c(c1)Cc1ccccc12 | C1=CCC2=Cc3ccccc3C2=C1.c1ccc2c(c1)Cc1ccccc12 | HO- | C(C)(=O)[O-].[Mn+2].C(C)(=O)[O-].C(C)(=O)[O-].[Co+2].C(C)(=O)[O-] | null | null | CCC(=O)O.O=c1n(O)c(=O)n(O)c(=O)n1O.c1ccc2c(c1)Cc1ccccc1-2>C(C)(=O)[O-].[Mn+2].C(C)(=O)[O-].C(C)(=O)[O-].[Co+2].C(C)(=O)[O-]>O=C1C=CC=C2C1=Cc1ccccc12.Oc1cccc2c1Cc1ccccc1-2 |
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