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-c5d9bebb04b040e391a8be4021bce133 | CNC.O=Cc1ccc(F)cc1Cl.O=[N+]([O-])c1cccc2[nH]ccc12>>CN(C)C(c1ccc(F)cc1Cl)c1c[nH]c2cccc([N+](=O)[O-])c12 | [N+](=O)([O-])C1=C2C=CNC2=CC=C1.[Cl-].ClC1=C(C=[N+](C)C)C=CC(=C1)F.ClC1=C(C=O)C=CC(=C1)F.CNC>>ClC1=C(C=CC(=C1)F)C(C1=CNC2=CC=CC(=C12)[N+](=O)[O-])N(C)C | [CH3:1][NH:2][CH3:3].O=[CH:4][c:5]1[cH:6][cH:7][c:8]([F:9])[cH:10][c:11]1[Cl:12].[cH:13]1[cH:14][nH:15][c:16]2[cH:17][cH:18][cH:19][c:20]([N+:21](=[O:22])[O-:23])[c:24]12>>[CH3:1][N:2]([CH3:3])[CH:4]([c:5]1[cH:6][cH:7][c:8]([F:9])[cH:10][c:11]1[Cl:12])[c:13]1[cH:14][nH:15][c:16]2[cH:17][cH:18][cH:19][c:20]([N+:21](=[O:... | CNC.O=Cc1ccc(F)cc1Cl.O=[N+]([O-])c1cccc2[nH]ccc12 | CN(C)C(c1ccc(F)cc1Cl)c1c[nH]c2cccc([N+](=O)[O-])c12 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 1e887ffc9d31747076f97173ff8dc6f44b0480e2cfa9f6a88ab0a775ac92e3d5 | 2d03f38884b1fbb0c0d6e6f2de31afb25102fec87f347c3a123e064c1bfef0ad | c1ccc(Cc2c[nH]c3ccccc23)cc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[C;D1;H3:5]-[NH;D2;+0:6]-[C;D1;H3:7].[c:8]:[c:9]1:[#7;a:10]:[c:11]:[cH;D2;+0:12]:[c:13]:1:[c:14]>>[C;D1;H3:5]-[N;H0;D3;+0:6](-[C;D1;H3:7])-[CH;D3;+0:1](-[c:2](:[c:3]):[c:4])-[c;H0;D3;+0:12]1:[c:11]:[#7;a:10]:[c:9](:[c:8]):[c:13]:1:[c:14] | null | [] | null | null | null | null | The preparation was carried out in accordance with general synthesis instructions 4 from 4-nitroindole and (2-chloro-4-fluoro-benzylidene)-dimethyl-ammonium chloride, which had been prepared in accordance with example 24 from 2-chloro-4-fluoro-benzaldehyde and dimethylamine.
Conditions: See reaction.notes.procedure_det... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Secondary amine | Tertiary amine | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1 | c1ccccc1.c1ccc2[nH]ccc2c1 | HO- | null | null | null | CNC.O=Cc1ccc(F)cc1Cl.O=[N+]([O-])c1cccc2[nH]ccc12>>CN(C)C(c1ccc(F)cc1Cl)c1c[nH]c2cccc([N+](=O)[O-])c12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-9c25bc003cb249c8bfbc584f2f7916cd | CNC.Cc1cccc2[nH]ccc12.O=Cc1ccc(F)cc1Cl>>Cc1cccc2[nH]cc(C(c3ccc(F)cc3Cl)N(C)C)c12 | CC1=C2C=CNC2=CC=C1.[Cl-].ClC1=C(C=[N+](C)C)C=CC(=C1)F.ClC1=C(C=O)C=CC(=C1)F.CNC>>ClC1=C(C=CC(=C1)F)C(C1=CNC2=CC=CC(=C12)C)N(C)C | [NH:19]([CH3:20])[CH3:21].[CH3:1][c:2]1[cH:3][cH:4][cH:5][c:6]2[nH:7][cH:8][cH:9][c:22]12.O=[CH:10][c:11]1[cH:12][cH:13][c:14]([F:15])[cH:16][c:17]1[Cl:18]>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][c:6]2[nH:7][cH:8][c:9]([CH:10]([c:11]3[cH:12][cH:13][c:14]([F:15])[cH:16][c:17]3[Cl:18])[N:19]([CH3:20])[CH3:21])[c:22]12 | CNC.Cc1cccc2[nH]ccc12.O=Cc1ccc(F)cc1Cl | Cc1cccc2[nH]cc(C(c3ccc(F)cc3Cl)N(C)C)c12 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 1e887ffc9d31747076f97173ff8dc6f44b0480e2cfa9f6a88ab0a775ac92e3d5 | 2d03f38884b1fbb0c0d6e6f2de31afb25102fec87f347c3a123e064c1bfef0ad | c1ccc(Cc2c[nH]c3ccccc23)cc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[C;D1;H3:5]-[NH;D2;+0:6]-[C;D1;H3:7].[c:8]:[c:9]1:[cH;D2;+0:10]:[c:11]:[#7;a:12]:[c:13]:1:[c:14]>>[C;D1;H3:5]-[N;H0;D3;+0:6](-[C;D1;H3:7])-[CH;D3;+0:1](-[c:2](:[c:3]):[c:4])-[c;H0;D3;+0:10]1:[c:11]:[#7;a:12]:[c:13](:[c:14]):[c:9]:1:[c:8] | null | [] | null | null | null | null | The preparation was carried out in accordance with general synthesis instructions 4 from 4-methylindole and (2-chloro-4-fluoro-benzylidene)-dimethyl-ammonium chloride, which had been prepared in accordance with example 24 from 2-chloro-4-fluoro-benzaldehyde and dimethylamine.
Conditions: See reaction.notes.procedure_de... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Secondary amine | Tertiary amine | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1.c1ccccc1 | HO- | null | null | null | CNC.Cc1cccc2[nH]ccc12.O=Cc1ccc(F)cc1Cl>>Cc1cccc2[nH]cc(C(c3ccc(F)cc3Cl)N(C)C)c12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-024ef80f0453487d912adea4ad07485b | CNC.O=Cc1c(F)cccc1Cl.c1ccc(-c2cc3ccccc3[nH]2)cc1>>CN(C)C(c1c(F)cccc1Cl)c1c(-c2ccccc2)[nH]c2ccccc12 | C1(=CC=CC=C1)C=1NC2=CC=CC=C2C1.[Cl-].ClC1=C(C=[N+](C)C)C(=CC=C1)F.ClC1=C(C=O)C(=CC=C1)F.CNC>>ClC1=C(C(=CC=C1)F)C(C1=C(NC2=CC=CC=C12)C1=CC=CC=C1)N(C)C | [CH3:1][NH:2][CH3:3].O=[CH:4][c:5]1[c:6]([F:7])[cH:8][cH:9][cH:10][c:11]1[Cl:12].[cH:13]1[c:14](-[c:15]2[cH:16][cH:17][cH:18][cH:19][cH:20]2)[nH:21][c:22]2[cH:23][cH:24][cH:25][cH:26][c:27]12>>[CH3:1][N:2]([CH3:3])[CH:4]([c:5]1[c:6]([F:7])[cH:8][cH:9][cH:10][c:11]1[Cl:12])[c:13]1[c:14](-[c:15]2[cH:16][cH:17][cH:18][cH:... | CNC.O=Cc1c(F)cccc1Cl.c1ccc(-c2cc3ccccc3[nH]2)cc1 | CN(C)C(c1c(F)cccc1Cl)c1c(-c2ccccc2)[nH]c2ccccc12 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 1e887ffc9d31747076f97173ff8dc6f44b0480e2cfa9f6a88ab0a775ac92e3d5 | 2d03f38884b1fbb0c0d6e6f2de31afb25102fec87f347c3a123e064c1bfef0ad | c1ccc(Cc2c(-c3ccccc3)[nH]c3ccccc23)cc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[C;D1;H3:5]-[NH;D2;+0:6]-[C;D1;H3:7].[c:8]-[c:9]1:[#7;a:10]:[c:11](:[c:12]):[c:13](:[c:14]):[cH;D2;+0:15]:1>>[C;D1;H3:5]-[N;H0;D3;+0:6](-[C;D1;H3:7])-[CH;D3;+0:1](-[c:2](:[c:3]):[c:4])-[c;H0;D3;+0:15]1:[c:9](-[c:8]):[#7;a:10]:[c:11](:[c:12]):[c:13]:1:[c:14] | null | [] | null | null | null | null | The preparation was carried out in accordance with general synthesis instructions 4 from 2-phenylindole and (2-chloro-6-fluoro-benzylidene)-dimethyl-ammonium chloride, which had been prepared in accordance with example 24 from 2-chloro-6-fluoro-benzaldehyde and dimethylamine.
Conditions: See reaction.notes.procedure_de... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Secondary amine | Tertiary amine | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1 | c1ccccc1.c1ccccc1.c1ccc2[nH]ccc2c1 | HO- | null | null | null | CNC.O=Cc1c(F)cccc1Cl.c1ccc(-c2cc3ccccc3[nH]2)cc1>>CN(C)C(c1c(F)cccc1Cl)c1c(-c2ccccc2)[nH]c2ccccc12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-481423226194464382ed5e4c678c6fee | CNC.Clc1ccc(-c2cc3ccccc3[nH]2)cc1.O=Cc1c(F)cccc1Cl>>CN(C)C(c1c(F)cccc1Cl)c1c(-c2ccc(Cl)cc2)[nH]c2ccccc12 | ClC1=CC=C(C=C1)C=1NC2=CC=CC=C2C1.[Cl-].ClC1=C(C=[N+](C)C)C(=CC=C1)F.ClC1=C(C=O)C(=CC=C1)F.CNC>>ClC1=C(C(=CC=C1)F)C(C1=C(NC2=CC=CC=C12)C1=CC=C(C=C1)Cl)N(C)C | [CH3:1][NH:2][CH3:3].[cH:13]1[c:14](-[c:15]2[cH:16][cH:17][c:18]([Cl:19])[cH:20][cH:21]2)[nH:22][c:23]2[cH:24][cH:25][cH:26][cH:27][c:28]12.O=[CH:4][c:5]1[c:6]([F:7])[cH:8][cH:9][cH:10][c:11]1[Cl:12]>>[CH3:1][N:2]([CH3:3])[CH:4]([c:5]1[c:6]([F:7])[cH:8][cH:9][cH:10][c:11]1[Cl:12])[c:13]1[c:14](-[c:15]2[cH:16][cH:17][c:... | CNC.Clc1ccc(-c2cc3ccccc3[nH]2)cc1.O=Cc1c(F)cccc1Cl | CN(C)C(c1c(F)cccc1Cl)c1c(-c2ccc(Cl)cc2)[nH]c2ccccc12 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 1e887ffc9d31747076f97173ff8dc6f44b0480e2cfa9f6a88ab0a775ac92e3d5 | 2d03f38884b1fbb0c0d6e6f2de31afb25102fec87f347c3a123e064c1bfef0ad | c1ccc(Cc2c(-c3ccccc3)[nH]c3ccccc23)cc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[C;D1;H3:5]-[NH;D2;+0:6]-[C;D1;H3:7].[c:8]-[c:9]1:[#7;a:10]:[c:11](:[c:12]):[c:13](:[c:14]):[cH;D2;+0:15]:1>>[C;D1;H3:5]-[N;H0;D3;+0:6](-[C;D1;H3:7])-[CH;D3;+0:1](-[c:2](:[c:3]):[c:4])-[c;H0;D3;+0:15]1:[c:9](-[c:8]):[#7;a:10]:[c:11](:[c:12]):[c:13]:1:[c:14] | null | [] | null | null | null | null | The preparation was carried out in accordance with general synthesis instructions 4 from 2-(4-chlorophenyl)-indole and (2-chloro-6-fluoro-benzylidene)-dimethyl-ammonium chloride, which had been prepared in accordance with example 24 from 2-chloro-6-fluoro-benzaldehyde and dimethylamine.
Conditions: See reaction.notes.p... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Secondary amine | Tertiary amine | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1 | c1ccccc1.c1ccccc1.c1ccc2[nH]ccc2c1 | HO- | null | null | null | CNC.Clc1ccc(-c2cc3ccccc3[nH]2)cc1.O=Cc1c(F)cccc1Cl>>CN(C)C(c1c(F)cccc1Cl)c1c(-c2ccc(Cl)cc2)[nH]c2ccccc12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-f731be15c2084b7ab542d00f6022ab25 | CNC.Cn1ccc2ccccc21.O=Cc1c(F)cccc1Cl>>CN(C)C(c1c(F)cccc1Cl)c1cn(C)c2ccccc12 | CN1C=CC2=CC=CC=C12.[Cl-].ClC1=C(C=[N+](C)C)C(=CC=C1)F.ClC1=C(C=O)C(=CC=C1)F.CNC>>ClC1=C(C(=CC=C1)F)C(C1=CN(C2=CC=CC=C12)C)N(C)C | [CH3:1][NH:2][CH3:3].[cH:13]1[cH:14][n:15]([CH3:16])[c:17]2[cH:18][cH:19][cH:20][cH:21][c:22]12.O=[CH:4][c:5]1[c:6]([F:7])[cH:8][cH:9][cH:10][c:11]1[Cl:12]>>[CH3:1][N:2]([CH3:3])[CH:4]([c:5]1[c:6]([F:7])[cH:8][cH:9][cH:10][c:11]1[Cl:12])[c:13]1[cH:14][n:15]([CH3:16])[c:17]2[cH:18][cH:19][cH:20][cH:21][c:22]12 | CNC.Cn1ccc2ccccc21.O=Cc1c(F)cccc1Cl | CN(C)C(c1c(F)cccc1Cl)c1cn(C)c2ccccc12 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 05894bd812613f52cf9c1620f3154e6ca08db53b10e13d8864b239f8fa88e3d5 | 2d03f38884b1fbb0c0d6e6f2de31afb25102fec87f347c3a123e064c1bfef0ad | c1ccc(Cc2c[nH]c3ccccc23)cc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[C;D1;H3:5]-[#7;a:6]1:[c:7]:[cH;D2;+0:8]:[c:9](:[c:10]):[c:11]:1:[c:12].[C;D1;H3:13]-[NH;D2;+0:14]-[C;D1;H3:15]>>[C;D1;H3:5]-[#7;a:6]1:[c:7]:[c;H0;D3;+0:8](-[CH;D3;+0:1](-[N;H0;D3;+0:14](-[C;D1;H3:13])-[C;D1;H3:15])-[c:2](:[c:3]):[c:4]):[c:9](:[c:10]):[c:11]:1:[c:12] | null | [] | null | null | null | null | The preparation was carried out in accordance with general synthesis instructions 4 from 1-methylindole and (2-chloro-6-fluoro-benzylidene)-dimethyl-ammonium chloride, which had been prepared in accordance with example 24 from 2-chloro-6-fluoro-benzaldehyde and dimethylamine.
Conditions: See reaction.notes.procedure_de... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Secondary amine | Tertiary amine | c1ccc2[nH]ccc2c1 | c1c[nH]c2ccccc12 | c1ccccc1.c1c[nH]c2ccccc12 | HO- | null | null | null | CNC.Cn1ccc2ccccc21.O=Cc1c(F)cccc1Cl>>CN(C)C(c1c(F)cccc1Cl)c1cn(C)c2ccccc12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-a0d8c1eff92f4c29b36ecbd3a0dc11aa | CNC.Cn1ccc2ccccc21.O=Cc1cccc(Cl)c1>>CN(C)C(c1cccc(Cl)c1)c1cn(C)c2ccccc12 | CN1C=CC2=CC=CC=C12.[Cl-].ClC=1C=C(C=[N+](C)C)C=CC1.ClC=1C=C(C=O)C=CC1.CNC>>ClC=1C=C(C=CC1)C(C1=CN(C2=CC=CC=C12)C)N(C)C | [CH3:1][NH:2][CH3:3].[cH:12]1[cH:13][n:14]([CH3:15])[c:16]2[cH:17][cH:18][cH:19][cH:20][c:21]12.O=[CH:4][c:5]1[cH:6][cH:7][cH:8][c:9]([Cl:10])[cH:11]1>>[CH3:1][N:2]([CH3:3])[CH:4]([c:5]1[cH:6][cH:7][cH:8][c:9]([Cl:10])[cH:11]1)[c:12]1[cH:13][n:14]([CH3:15])[c:16]2[cH:17][cH:18][cH:19][cH:20][c:21]12 | CNC.Cn1ccc2ccccc21.O=Cc1cccc(Cl)c1 | CN(C)C(c1cccc(Cl)c1)c1cn(C)c2ccccc12 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 05894bd812613f52cf9c1620f3154e6ca08db53b10e13d8864b239f8fa88e3d5 | 2d03f38884b1fbb0c0d6e6f2de31afb25102fec87f347c3a123e064c1bfef0ad | c1ccc(Cc2c[nH]c3ccccc23)cc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[C;D1;H3:5]-[#7;a:6]1:[c:7]:[cH;D2;+0:8]:[c:9](:[c:10]):[c:11]:1:[c:12].[C;D1;H3:13]-[NH;D2;+0:14]-[C;D1;H3:15]>>[C;D1;H3:5]-[#7;a:6]1:[c:7]:[c;H0;D3;+0:8](-[CH;D3;+0:1](-[N;H0;D3;+0:14](-[C;D1;H3:13])-[C;D1;H3:15])-[c:2](:[c:3]):[c:4]):[c:9](:[c:10]):[c:11]:1:[c:12] | null | [] | null | null | null | null | The preparation was carried out in accordance with general synthesis instructions 4 from 1-methylindole and (3-chloro-benzylidene)-dimethyl-ammonium chloride, which had been prepared in accordance with example 24 from 3-chloro-benzaldehyde and dimethylamine.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Secondary amine | Tertiary amine | c1ccc2[nH]ccc2c1 | c1c[nH]c2ccccc12 | c1ccccc1.c1c[nH]c2ccccc12 | HO- | null | null | null | CNC.Cn1ccc2ccccc21.O=Cc1cccc(Cl)c1>>CN(C)C(c1cccc(Cl)c1)c1cn(C)c2ccccc12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-e628563da2734892a93257119bfd4b8e | CNC.C[N+](C)=Cc1cccc(Cl)c1Cl.Cn1ccc2ccccc21>>CN(C)C(c1cccc(Cl)c1Cl)c1cn(C)c2ccccc12 | CN1C=CC2=CC=CC=C12.[Cl-].ClC1=C(C=[N+](C)C)C=CC=C1Cl.ClC1=C(C=O)C=CC=C1Cl.CNC>>ClC1=C(C=CC=C1Cl)C(C1=CN(C2=CC=CC=C12)C)N(C)C | [CH3:1][NH:2][CH3:3].C[N+](C)=[CH:4][c:5]1[cH:6][cH:7][cH:8][c:9]([Cl:10])[c:11]1[Cl:12].[cH:13]1[cH:14][n:15]([CH3:16])[c:17]2[cH:18][cH:19][cH:20][cH:21][c:22]12>>[CH3:1][N:2]([CH3:3])[CH:4]([c:5]1[cH:6][cH:7][cH:8][c:9]([Cl:10])[c:11]1[Cl:12])[c:13]1[cH:14][n:15]([CH3:16])[c:17]2[cH:18][cH:19][cH:20][cH:21][c:22]12 | CNC.C[N+](C)=Cc1cccc(Cl)c1Cl.Cn1ccc2ccccc21 | CN(C)C(c1cccc(Cl)c1Cl)c1cn(C)c2ccccc12 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 85aaf23583cdcf64b6fe54d87d17427b47bda7376efe96f2fd1dd9ad1df13e69 | 7cc25fba33369069673bac5bd8fc404dc064da8d6c8cf4a77f21f4df0a617fe3 | c1ccc(Cc2c[nH]c3ccccc23)cc1 | C-[N+](-C)=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[C;D1;H3:5]-[#7;a:6]1:[c:7]:[cH;D2;+0:8]:[c:9](:[c:10]):[c:11]:1:[c:12].[C;D1;H3:13]-[NH;D2;+0:14]-[C;D1;H3:15]>>[C;D1;H3:5]-[#7;a:6]1:[c:7]:[c;H0;D3;+0:8](-[CH;D3;+0:1](-[N;H0;D3;+0:14](-[C;D1;H3:13])-[C;D1;H3:15])-[c:2](:[c:3]):[c:4]):[c:9](:[c:10]):[c:11]:1:[c:12] | null | [] | null | null | null | null | The preparation was carried out in accordance with general synthesis instructions 4 from 1-methylindole and (2,3-dichloro-benzylidene)-dimethyl-ammonium chloride, which had been prepared in accordance with example 24 from 2,3-dichloro-benzaldehyde and dimethylamine.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Secondary amine | Tertiary amine | c1ccc2[nH]ccc2c1 | c1c[nH]c2ccccc12 | c1ccccc1.c1c[nH]c2ccccc12 | Other | null | null | null | CNC.C[N+](C)=Cc1cccc(Cl)c1Cl.Cn1ccc2ccccc21>>CN(C)C(c1cccc(Cl)c1Cl)c1cn(C)c2ccccc12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-a77eb8032c0644bdbcdf6b13a2b295cc | CNC.Cn1ccc2ccccc21.O=Cc1ccc(Cl)cc1Cl>>CN(C)C(c1ccc(Cl)cc1Cl)c1cn(C)c2ccccc12 | CN1C=CC2=CC=CC=C12.[Cl-].ClC1=C(C=[N+](C)C)C=CC(=C1)Cl.ClC1=C(C=O)C=CC(=C1)Cl.CNC>>ClC1=C(C=CC(=C1)Cl)C(C1=CN(C2=CC=CC=C12)C)N(C)C | [CH3:1][NH:2][CH3:3].[cH:13]1[cH:14][n:15]([CH3:16])[c:17]2[cH:18][cH:19][cH:20][cH:21][c:22]12.O=[CH:4][c:5]1[cH:6][cH:7][c:8]([Cl:9])[cH:10][c:11]1[Cl:12]>>[CH3:1][N:2]([CH3:3])[CH:4]([c:5]1[cH:6][cH:7][c:8]([Cl:9])[cH:10][c:11]1[Cl:12])[c:13]1[cH:14][n:15]([CH3:16])[c:17]2[cH:18][cH:19][cH:20][cH:21][c:22]12 | CNC.Cn1ccc2ccccc21.O=Cc1ccc(Cl)cc1Cl | CN(C)C(c1ccc(Cl)cc1Cl)c1cn(C)c2ccccc12 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 05894bd812613f52cf9c1620f3154e6ca08db53b10e13d8864b239f8fa88e3d5 | 2d03f38884b1fbb0c0d6e6f2de31afb25102fec87f347c3a123e064c1bfef0ad | c1ccc(Cc2c[nH]c3ccccc23)cc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[C;D1;H3:5]-[#7;a:6]1:[c:7]:[cH;D2;+0:8]:[c:9](:[c:10]):[c:11]:1:[c:12].[C;D1;H3:13]-[NH;D2;+0:14]-[C;D1;H3:15]>>[C;D1;H3:5]-[#7;a:6]1:[c:7]:[c;H0;D3;+0:8](-[CH;D3;+0:1](-[N;H0;D3;+0:14](-[C;D1;H3:13])-[C;D1;H3:15])-[c:2](:[c:3]):[c:4]):[c:9](:[c:10]):[c:11]:1:[c:12] | null | [] | null | null | null | null | The preparation was carried out in accordance with general synthesis instructions 4 from 1-methylindole and (2,4-dichloro-benzylidene)-dimethyl-ammonium chloride, which had been prepared in accordance with example 24 from 2,4-dichloro-benzaldehyde and dimethylamine.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Secondary amine | Tertiary amine | c1ccc2[nH]ccc2c1 | c1c[nH]c2ccccc12 | c1ccccc1.c1c[nH]c2ccccc12 | HO- | null | null | null | CNC.Cn1ccc2ccccc21.O=Cc1ccc(Cl)cc1Cl>>CN(C)C(c1ccc(Cl)cc1Cl)c1cn(C)c2ccccc12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-599298268d6341939a695a9b3cc6a7f0 | CC(C)(C)c1ccc(C=O)cc1.CCn1c(-c2ccccc2)cc2ccccc21.CNC>>CCn1c(-c2ccccc2)c(C(c2ccc(C(C)(C)C)cc2)N(C)C)c2ccccc21 | C(C)N1C(=CC2=CC=CC=C12)C1=CC=CC=C1.[Cl-].C(C)(C)(C)C1=CC=C(C=[N+](C)C)C=C1.C(C)(C)(C)C1=CC=C(C=O)C=C1.CNC>>C(C)(C)(C)C1=CC=C(C=C1)C(C1=C(N(C2=CC=CC=C12)CC)C1=CC=CC=C1)N(C)C | O=[CH:12][c:13]1[cH:14][cH:15][c:16]([C:17]([CH3:18])([CH3:19])[CH3:20])[cH:21][cH:22]1.[CH3:1][CH2:2][n:3]1[c:4](-[c:5]2[cH:6][cH:7][cH:8][cH:9][cH:10]2)[cH:11][c:26]2[cH:27][cH:28][cH:29][cH:30][c:31]12.[NH:23]([CH3:24])[CH3:25]>>[CH3:1][CH2:2][n:3]1[c:4](-[c:5]2[cH:6][cH:7][cH:8][cH:9][cH:10]2)[c:11]([CH:12]([c:13]2... | CC(C)(C)c1ccc(C=O)cc1.CCn1c(-c2ccccc2)cc2ccccc21.CNC | CCn1c(-c2ccccc2)c(C(c2ccc(C(C)(C)C)cc2)N(C)C)c2ccccc21 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | bec24864ceecfec904d98640b3bb3caa9d35fa656dcbdac3c55c0dacb43b50eb | 2d03f38884b1fbb0c0d6e6f2de31afb25102fec87f347c3a123e064c1bfef0ad | c1ccc(Cc2c(-c3ccccc3)[nH]c3ccccc23)cc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[C;D1;H3:5]-[NH;D2;+0:6]-[C;D1;H3:7].[C:8]-[#7;a:9]1:[c:10](:[c:11]):[c:12](:[c:13]):[cH;D2;+0:14]:[c:15]:1-[c:16]>>[C:8]-[#7;a:9]1:[c:10](:[c:11]):[c:12](:[c:13]):[c;H0;D3;+0:14](-[CH;D3;+0:1](-[N;H0;D3;+0:6](-[C;D1;H3:5])-[C;D1;H3:7])-[c:2](:[c:3]):[c:4]):[c:15]:1-[c:16] | null | [] | null | null | null | null | The preparation was carried out in accordance with general synthesis instructions 4 from 1-ethyl-2-phenyl-1H-indole and (4-tert-butyl-benzylidene)-dimethylammonium chloride, which had been prepared in accordance with example 44 from 4-tert-butylbenzaldehyde and dimethylamine.
Conditions: See reaction.notes.procedure_de... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Secondary amine | Tertiary amine | c1cc2ccccc2[nH]1 | c1cc2ccccc2[nH]1 | c1ccccc1.c1ccccc1.c1cc2ccccc2[nH]1 | HO- | null | null | null | CC(C)(C)c1ccc(C=O)cc1.CCn1c(-c2ccccc2)cc2ccccc21.CNC>>CCn1c(-c2ccccc2)c(C(c2ccc(C(C)(C)C)cc2)N(C)C)c2ccccc21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-f9cc66bc533c45fc829f8836d582b65f | CNC.Cc1cc2ccccc2[nH]1.O=Cc1ccc(F)cc1Cl>>Cc1[nH]c2ccccc2c1C(c1ccc(F)cc1Cl)N(C)C | CC=1NC2=CC=CC=C2C1.[Cl-].ClC1=C(C=[N+](C)C)C=CC(=C1)F.ClC1=C(C=O)C=CC(=C1)F.CNC>>ClC1=C(C=CC(=C1)F)C(C1=C(NC2=CC=CC=C12)C)N(C)C | [NH:20]([CH3:21])[CH3:22].[CH3:1][c:2]1[nH:3][c:4]2[cH:5][cH:6][cH:7][cH:8][c:9]2[cH:10]1.O=[CH:11][c:12]1[cH:13][cH:14][c:15]([F:16])[cH:17][c:18]1[Cl:19]>>[CH3:1][c:2]1[nH:3][c:4]2[cH:5][cH:6][cH:7][cH:8][c:9]2[c:10]1[CH:11]([c:12]1[cH:13][cH:14][c:15]([F:16])[cH:17][c:18]1[Cl:19])[N:20]([CH3:21])[CH3:22] | CNC.Cc1cc2ccccc2[nH]1.O=Cc1ccc(F)cc1Cl | Cc1[nH]c2ccccc2c1C(c1ccc(F)cc1Cl)N(C)C | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 1e887ffc9d31747076f97173ff8dc6f44b0480e2cfa9f6a88ab0a775ac92e3d5 | 2d03f38884b1fbb0c0d6e6f2de31afb25102fec87f347c3a123e064c1bfef0ad | c1ccc(Cc2c[nH]c3ccccc23)cc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[C;D1;H3:5]-[NH;D2;+0:6]-[C;D1;H3:7].[C;D1;H3:8]-[c:9]1:[#7;a:10]:[c:11](:[c:12]):[c:13](:[c:14]):[cH;D2;+0:15]:1>>[C;D1;H3:8]-[c:9]1:[#7;a:10]:[c:11](:[c:12]):[c:13](:[c:14]):[c;H0;D3;+0:15]:1-[CH;D3;+0:1](-[N;H0;D3;+0:6](-[C;D1;H3:5])-[C;D1;H3:7])-[c:2](:[c:3]):[c:4] | null | [] | null | null | null | null | The preparation was carried out in accordance with general synthesis instructions 4 from 2-methyl-1H-indole and (2-chloro-4-fluoro-benzylidene)-dimethylammonium chloride, which had been prepared in accordance with example 44 from 2-chloro-4-fluoro-benzaldehyde and dimethylamine.
Conditions: See reaction.notes.procedure... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Secondary amine | Tertiary amine | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1.c1ccccc1 | HO- | null | null | null | CNC.Cc1cc2ccccc2[nH]1.O=Cc1ccc(F)cc1Cl>>Cc1[nH]c2ccccc2c1C(c1ccc(F)cc1Cl)N(C)C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-f85e5808d5ab42c3a61017baad9dc05f | CNC.Cc1cc2ccccc2[nH]1.O=Cc1c(F)cccc1Cl>>Cc1[nH]c2ccccc2c1C(c1c(F)cccc1Cl)N(C)C | CC=1NC2=CC=CC=C2C1.[Cl-].ClC1=C(C=[N+](C)C)C(=CC=C1)F.ClC1=C(C=O)C(=CC=C1)F.CNC>>ClC1=C(C(=CC=C1)F)C(C1=C(NC2=CC=CC=C12)C)N(C)C | [NH:20]([CH3:21])[CH3:22].[CH3:1][c:2]1[nH:3][c:4]2[cH:5][cH:6][cH:7][cH:8][c:9]2[cH:10]1.O=[CH:11][c:12]1[c:13]([F:14])[cH:15][cH:16][cH:17][c:18]1[Cl:19]>>[CH3:1][c:2]1[nH:3][c:4]2[cH:5][cH:6][cH:7][cH:8][c:9]2[c:10]1[CH:11]([c:12]1[c:13]([F:14])[cH:15][cH:16][cH:17][c:18]1[Cl:19])[N:20]([CH3:21])[CH3:22] | CNC.Cc1cc2ccccc2[nH]1.O=Cc1c(F)cccc1Cl | Cc1[nH]c2ccccc2c1C(c1c(F)cccc1Cl)N(C)C | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 1e887ffc9d31747076f97173ff8dc6f44b0480e2cfa9f6a88ab0a775ac92e3d5 | 2d03f38884b1fbb0c0d6e6f2de31afb25102fec87f347c3a123e064c1bfef0ad | c1ccc(Cc2c[nH]c3ccccc23)cc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[C;D1;H3:5]-[NH;D2;+0:6]-[C;D1;H3:7].[C;D1;H3:8]-[c:9]1:[#7;a:10]:[c:11](:[c:12]):[c:13](:[c:14]):[cH;D2;+0:15]:1>>[C;D1;H3:8]-[c:9]1:[#7;a:10]:[c:11](:[c:12]):[c:13](:[c:14]):[c;H0;D3;+0:15]:1-[CH;D3;+0:1](-[N;H0;D3;+0:6](-[C;D1;H3:5])-[C;D1;H3:7])-[c:2](:[c:3]):[c:4] | null | [] | null | null | null | null | The preparation was carried out in accordance with general synthesis instructions 4 from 2-methyl-1H-indole and (2-chloro-6-fluoro-benzylidene)-dimethylammonium chloride, which had been prepared in accordance with example 44 from 2-chloro-6-fluoro-benzaldehyde and dimethylamine.
Conditions: See reaction.notes.procedure... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Secondary amine | Tertiary amine | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1.c1ccccc1 | HO- | null | null | null | CNC.Cc1cc2ccccc2[nH]1.O=Cc1c(F)cccc1Cl>>Cc1[nH]c2ccccc2c1C(c1c(F)cccc1Cl)N(C)C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-587b5a90563d478ba07650bd7b8c540a | CNC.COc1cccc(C=O)c1OC.O=[N+]([O-])c1cccc2[nH]ccc12>>COc1cccc(C(c2c[nH]c3cccc([N+](=O)[O-])c23)N(C)C)c1OC | [N+](=O)([O-])C1=C2C=CNC2=CC=C1.[Cl-].COC1=C(C=[N+](C)C)C=CC=C1OC.COC1=C(C=O)C=CC=C1OC.CNC>>COC1=C(C=CC=C1OC)C(C1=CNC2=CC=CC(=C12)[N+](=O)[O-])N(C)C | [NH:21]([CH3:22])[CH3:23].O=[CH:8][c:7]1[cH:6][cH:5][cH:4][c:3]([O:2][CH3:1])[c:24]1[O:25][CH3:26].[cH:9]1[cH:10][nH:11][c:12]2[cH:13][cH:14][cH:15][c:16]([N+:17](=[O:18])[O-:19])[c:20]12>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]([CH:8]([c:9]2[cH:10][nH:11][c:12]3[cH:13][cH:14][cH:15][c:16]([N+:17](=[O:18])[O-:19])[c:... | CNC.COc1cccc(C=O)c1OC.O=[N+]([O-])c1cccc2[nH]ccc12 | COc1cccc(C(c2c[nH]c3cccc([N+](=O)[O-])c23)N(C)C)c1OC | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 1e887ffc9d31747076f97173ff8dc6f44b0480e2cfa9f6a88ab0a775ac92e3d5 | 2d03f38884b1fbb0c0d6e6f2de31afb25102fec87f347c3a123e064c1bfef0ad | c1ccc(Cc2c[nH]c3ccccc23)cc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[C;D1;H3:5]-[NH;D2;+0:6]-[C;D1;H3:7].[c:8]:[c:9]1:[#7;a:10]:[c:11]:[cH;D2;+0:12]:[c:13]:1:[c:14]>>[C;D1;H3:5]-[N;H0;D3;+0:6](-[C;D1;H3:7])-[CH;D3;+0:1](-[c:2](:[c:3]):[c:4])-[c;H0;D3;+0:12]1:[c:11]:[#7;a:10]:[c:9](:[c:8]):[c:13]:1:[c:14] | null | [] | null | null | null | null | The preparation was carried out in accordance with general synthesis instructions 4 from 4-nitro-1H-indole and (2,3-dimethoxy-benzylidene)-dimethylammonium chloride, which had been prepared in accordance with example 44 from 2,3-dimethoxy-benzaldehyde and dimethylamine.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Secondary amine | Tertiary amine | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1 | c1ccccc1.c1ccc2[nH]ccc2c1 | HO- | null | null | null | CNC.COc1cccc(C=O)c1OC.O=[N+]([O-])c1cccc2[nH]ccc12>>COc1cccc(C(c2c[nH]c3cccc([N+](=O)[O-])c23)N(C)C)c1OC |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-354e6617f7a94d3ab81859a0b3502e64 | CNC.COc1cccc(C=[N+](C)C)c1OC.O=C(O)c1ccc2cc[nH]c2c1>>COc1cccc(C(c2c[nH]c3c2CC=C(C(=O)O)C3)N(C)C)c1OC | N1C=CC2=CC=C(C=C12)C(=O)O.[Cl-].COC1=C(C=[N+](C)C)C=CC=C1OC.COC1=C(C=O)C=CC=C1OC.CNC>>COC1=C(C=CC=C1OC)C(C1=CNC=2CC(=CCC12)C(=O)O)N(C)C | [NH:21]([CH3:22])[CH3:23].C[N+](C)=[CH:8][c:7]1[cH:6][cH:5][cH:4][c:3]([O:2][CH3:1])[c:24]1[O:25][CH3:26].[cH:9]1[cH:10][nH:11][c:12]2[c:13]1[cH:14][cH:15][c:16]([C:17](=[O:18])[OH:19])[cH:20]2>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]([CH:8]([c:9]2[cH:10][nH:11][c:12]3[c:13]2[CH2:14][CH:15]=[C:16]([C:17](=[O:18])[OH:... | CNC.COc1cccc(C=[N+](C)C)c1OC.O=C(O)c1ccc2cc[nH]c2c1 | COc1cccc(C(c2c[nH]c3c2CC=C(C(=O)O)C3)N(C)C)c1OC | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 3679d5ed704df7b735c63b1b3947eed592489fe8de1a08e47fd7328e6b27130f | 7cc25fba33369069673bac5bd8fc404dc064da8d6c8cf4a77f21f4df0a617fe3 | C1=CCc2c(Cc3ccccc3)c[nH]c2C1 | C-[N+](-C)=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[C;D1;H3:5]-[NH;D2;+0:6]-[C;D1;H3:7].[O;D1;H0:8]=[C:9](-[O;D1;H1:10])-[c;H0;D3;+0:11]1:[cH;D2;+0:12]:[cH;D2;+0:13]:[c:14]2:[cH;D2;+0:15]:[c:16]:[#7;a:17]:[c:18]:2:[cH;D2;+0:19]:1>>[C;D1;H3:5]-[N;H0;D3;+0:6](-[C;D1;H3:7])-[CH;D3;+0:1](-[c:2](:[c:3]):[c:4])-[c;H0;D3;+0:15]1:[c:... | null | [] | null | null | null | null | The preparation was carried out in accordance with general synthesis instructions 4 from 1H-indole-6-carboxylic acid and (2,3-dimethoxy-benzylidene)-dimethylammonium chloride, which had been prepared in accordance with example 44 from 2,3-dimethoxy-benzaldehyde and dimethylamine.
Conditions: See reaction.notes.procedur... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amine | Tertiary amine | c1ccc2[nH]ccc2c1 | C1=CCc2[nH]ccc2C1 | c1ccccc1.C1=CCc2[nH]ccc2C1 | Other | null | null | null | CNC.COc1cccc(C=[N+](C)C)c1OC.O=C(O)c1ccc2cc[nH]c2c1>>COc1cccc(C(c2c[nH]c3c2CC=C(C(=O)O)C3)N(C)C)c1OC |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-df37569297e741cf9e39494a4a08895e | CNC.COc1ccc(C=[N+](C)C)cc1OC.Cc1cc2ccccc2[nH]1>>COc1ccc(C(c2c(C)[nH]c3ccccc23)N(C)C)cc1OC | CC=1NC2=CC=CC=C2C1.[Cl-].COC=1C=C(C=[N+](C)C)C=CC1OC.COC=1C=C(C=O)C=CC1OC.CNC>>COC=1C=C(C=CC1OC)C(C1=C(NC2=CC=CC=C12)C)N(C)C | [NH:18]([CH3:19])[CH3:20].C[N+](C)=[CH:7][c:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[c:22]([O:23][CH3:24])[cH:21]1.[cH:8]1[c:9]([CH3:10])[nH:11][c:12]2[cH:13][cH:14][cH:15][cH:16][c:17]12>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH:7]([c:8]2[c:9]([CH3:10])[nH:11][c:12]3[cH:13][cH:14][cH:15][cH:16][c:17]23)[N:18]([CH3:19])[CH3:2... | CNC.COc1ccc(C=[N+](C)C)cc1OC.Cc1cc2ccccc2[nH]1 | COc1ccc(C(c2c(C)[nH]c3ccccc23)N(C)C)cc1OC | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 4aae3a4ea1be485aab9d544da9fceb1ce060e1d3dd462597adbb05c8cde19188 | 7cc25fba33369069673bac5bd8fc404dc064da8d6c8cf4a77f21f4df0a617fe3 | c1ccc(Cc2c[nH]c3ccccc23)cc1 | C-[N+](-C)=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[C;D1;H3:5]-[NH;D2;+0:6]-[C;D1;H3:7].[C;D1;H3:8]-[c:9]1:[#7;a:10]:[c:11](:[c:12]):[c:13](:[c:14]):[cH;D2;+0:15]:1>>[C;D1;H3:8]-[c:9]1:[#7;a:10]:[c:11](:[c:12]):[c:13](:[c:14]):[c;H0;D3;+0:15]:1-[CH;D3;+0:1](-[N;H0;D3;+0:6](-[C;D1;H3:5])-[C;D1;H3:7])-[c:2](:[c:3]):[c:4] | null | [] | null | null | null | null | The preparation was carried out in accordance with general synthesis instructions 4 from 2-methyl-1H-indole and (3,4-dimethoxy-benzylidene)-dimethylammonium chloride, which had been prepared in accordance with example 44 from 3,4-dimethoxy-benzaldehyde and dimethylamine.
Conditions: See reaction.notes.procedure_details... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amine | Tertiary amine | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1 | c1ccccc1.c1ccc2[nH]ccc2c1 | Other | null | null | null | CNC.COc1ccc(C=[N+](C)C)cc1OC.Cc1cc2ccccc2[nH]1>>COc1ccc(C(c2c(C)[nH]c3ccccc23)N(C)C)cc1OC |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-26a3da5fe37a4979bafcc20f4b60700f | CNC.COc1ccc(C=[N+](C)C)cc1OC.Clc1ccc(-c2cc3ccccc3[nH]2)cc1>>COc1ccc(C(c2c(-c3ccc(Cl)cc3)[nH]c3ccccc23)N(C)C)cc1OC | ClC1=CC=C(C=C1)C=1NC2=CC=CC=C2C1.[Cl-].COC=1C=C(C=[N+](C)C)C=CC1OC.COC=1C=C(C=O)C=CC1OC.CNC>>ClC1=CC=C(C=C1)C=1NC2=CC=CC=C2C1C(C1=CC(=C(C=C1)OC)OC)N(C)C | [NH:24]([CH3:25])[CH3:26].C[N+](C)=[CH:7][c:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[c:28]([O:29][CH3:30])[cH:27]1.[cH:8]1[c:9](-[c:10]2[cH:11][cH:12][c:13]([Cl:14])[cH:15][cH:16]2)[nH:17][c:18]2[cH:19][cH:20][cH:21][cH:22][c:23]12>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH:7]([c:8]2[c:9](-[c:10]3[cH:11][cH:12][c:13]([Cl:14])[... | CNC.COc1ccc(C=[N+](C)C)cc1OC.Clc1ccc(-c2cc3ccccc3[nH]2)cc1 | COc1ccc(C(c2c(-c3ccc(Cl)cc3)[nH]c3ccccc23)N(C)C)cc1OC | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 4aae3a4ea1be485aab9d544da9fceb1ce060e1d3dd462597adbb05c8cde19188 | 7cc25fba33369069673bac5bd8fc404dc064da8d6c8cf4a77f21f4df0a617fe3 | c1ccc(Cc2c(-c3ccccc3)[nH]c3ccccc23)cc1 | C-[N+](-C)=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[C;D1;H3:5]-[NH;D2;+0:6]-[C;D1;H3:7].[c:8]-[c:9]1:[#7;a:10]:[c:11](:[c:12]):[c:13](:[c:14]):[cH;D2;+0:15]:1>>[C;D1;H3:5]-[N;H0;D3;+0:6](-[C;D1;H3:7])-[CH;D3;+0:1](-[c:2](:[c:3]):[c:4])-[c;H0;D3;+0:15]1:[c:13](:[c:14]):[c:11](:[c:12]):[#7;a:10]:[c:9]:1-[c:8] | null | [] | null | null | null | null | The preparation was carried out in accordance with general synthesis instructions 4 from 2-(4-chloro-phenyl)-1H-indole and (3,4-dimethoxy-benzylidene)-dimethylammonium chloride, which had been prepared in accordance with example 44 from 3,4-dimethoxy-benzaldehyde and dimethylamine.
Conditions: See reaction.notes.proced... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amine | Tertiary amine | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1 | c1ccccc1.c1ccccc1.c1ccc2[nH]ccc2c1 | Other | null | null | null | CNC.COc1ccc(C=[N+](C)C)cc1OC.Clc1ccc(-c2cc3ccccc3[nH]2)cc1>>COc1ccc(C(c2c(-c3ccc(Cl)cc3)[nH]c3ccccc23)N(C)C)cc1OC |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-8a5d2aadeeab4a9e83db1bfb5536dadd | CCn1c(-c2ccccc2)cc2ccccc21.CNC.COc1ccc(C=O)cc1OC>>CCn1c(-c2ccccc2)c(C(c2ccc(OC)c(OC)c2)N(C)C)c2ccccc21 | C(C)N1C(=CC2=CC=CC=C12)C1=CC=CC=C1.[Cl-].COC=1C=C(C=[N+](C)C)C=CC1OC.COC=1C=C(C=O)C=CC1OC.CNC>>COC=1C=C(C=CC1OC)C(C1=C(N(C2=CC=CC=C12)CC)C1=CC=CC=C1)N(C)C | [CH3:1][CH2:2][n:3]1[c:4](-[c:5]2[cH:6][cH:7][cH:8][cH:9][cH:10]2)[cH:11][c:26]2[cH:27][cH:28][cH:29][cH:30][c:31]12.[NH:23]([CH3:24])[CH3:25].O=[CH:12][c:13]1[cH:14][cH:15][c:16]([O:17][CH3:18])[c:19]([O:20][CH3:21])[cH:22]1>>[CH3:1][CH2:2][n:3]1[c:4](-[c:5]2[cH:6][cH:7][cH:8][cH:9][cH:10]2)[c:11]([CH:12]([c:13]2[cH:1... | CCn1c(-c2ccccc2)cc2ccccc21.CNC.COc1ccc(C=O)cc1OC | CCn1c(-c2ccccc2)c(C(c2ccc(OC)c(OC)c2)N(C)C)c2ccccc21 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | bec24864ceecfec904d98640b3bb3caa9d35fa656dcbdac3c55c0dacb43b50eb | 2d03f38884b1fbb0c0d6e6f2de31afb25102fec87f347c3a123e064c1bfef0ad | c1ccc(Cc2c(-c3ccccc3)[nH]c3ccccc23)cc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[C;D1;H3:5]-[NH;D2;+0:6]-[C;D1;H3:7].[C:8]-[#7;a:9]1:[c:10](:[c:11]):[c:12](:[c:13]):[cH;D2;+0:14]:[c:15]:1-[c:16]>>[C:8]-[#7;a:9]1:[c:10](:[c:11]):[c:12](:[c:13]):[c;H0;D3;+0:14](-[CH;D3;+0:1](-[N;H0;D3;+0:6](-[C;D1;H3:5])-[C;D1;H3:7])-[c:2](:[c:3]):[c:4]):[c:15]:1-[c:16] | null | [] | null | null | null | null | The preparation was carried out in accordance with general synthesis instructions 4 from 1-ethyl-2-phenyl-1H-indole and (3,4-dimethoxy-benzylidene)-dimethylammonium chloride, which had been prepared in accordance with example 44 from 3,4-dimethoxy-benzaldehyde and dimethylamine.
Conditions: See reaction.notes.procedure... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Secondary amine | Tertiary amine | c1cc2ccccc2[nH]1 | c1cc2ccccc2[nH]1 | c1ccccc1.c1ccccc1.c1cc2ccccc2[nH]1 | HO- | null | null | null | CCn1c(-c2ccccc2)cc2ccccc21.CNC.COc1ccc(C=O)cc1OC>>CCn1c(-c2ccccc2)c(C(c2ccc(OC)c(OC)c2)N(C)C)c2ccccc21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-e111e89002764368b426e6c6cee9123f | CCc1cccc2cc[nH]c12.CNC.COc1ccc(C=[N+](C)C)cc1OC>>CCc1cccc2c(C(c3ccc(OC)c(OC)c3)N(C)C)c[nH]c12 | C(C)C=1C=CC=C2C=CNC12.[Cl-].COC=1C=C(C=[N+](C)C)C=CC1OC.COC=1C=C(C=O)C=CC1OC.CNC>>COC=1C=C(C=CC1OC)C(C1=CNC2=C(C=CC=C12)CC)N(C)C | [CH3:1][CH2:2][c:3]1[cH:4][cH:5][cH:6][c:7]2[cH:8][cH:23][nH:24][c:25]12.[NH:20]([CH3:21])[CH3:22].C[N+](C)=[CH:9][c:10]1[cH:11][cH:12][c:13]([O:14][CH3:15])[c:16]([O:17][CH3:18])[cH:19]1>>[CH3:1][CH2:2][c:3]1[cH:4][cH:5][cH:6][c:7]2[c:8]([CH:9]([c:10]3[cH:11][cH:12][c:13]([O:14][CH3:15])[c:16]([O:17][CH3:18])[cH:19]3)... | CCc1cccc2cc[nH]c12.CNC.COc1ccc(C=[N+](C)C)cc1OC | CCc1cccc2c(C(c3ccc(OC)c(OC)c3)N(C)C)c[nH]c12 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 4aae3a4ea1be485aab9d544da9fceb1ce060e1d3dd462597adbb05c8cde19188 | 7cc25fba33369069673bac5bd8fc404dc064da8d6c8cf4a77f21f4df0a617fe3 | c1ccc(Cc2c[nH]c3ccccc23)cc1 | C-[N+](-C)=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[C;D1;H3:5]-[NH;D2;+0:6]-[C;D1;H3:7].[c:8]:[c:9]1:[#7;a:10]:[c:11]:[cH;D2;+0:12]:[c:13]:1:[c:14]>>[C;D1;H3:5]-[N;H0;D3;+0:6](-[C;D1;H3:7])-[CH;D3;+0:1](-[c:2](:[c:3]):[c:4])-[c;H0;D3;+0:12]1:[c:11]:[#7;a:10]:[c:9](:[c:8]):[c:13]:1:[c:14] | null | [] | null | null | null | null | The preparation was carried out in accordance with general synthesis instructions 4 from 7-ethyl-1H-indole and (3,4-dimethoxy-benzylidene)-dimethylammonium chloride, which had been prepared in accordance with example 44 from 3,4-dimethoxy-benzaldehyde and dimethylamine.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Secondary amine | Tertiary amine | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1 | c1ccccc1.c1ccc2[nH]ccc2c1 | Other | null | null | null | CCc1cccc2cc[nH]c12.CNC.COc1ccc(C=[N+](C)C)cc1OC>>CCc1cccc2c(C(c3ccc(OC)c(OC)c3)N(C)C)c[nH]c12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-0154d7bb83be47f2abfe9ae53b6686d5 | CNC.COc1ccc(C=[N+](C)C)cc1OC.Cn1ccc2ccccc21>>COc1ccc(C(c2cn(C)c3ccccc23)N(C)C)cc1OC | CN1C=CC2=CC=CC=C12.[Cl-].COC=1C=C(C=[N+](C)C)C=CC1OC.COC=1C=C(C=O)C=CC1OC.CNC>>COC=1C=C(C=CC1OC)C(C1=CN(C2=CC=CC=C12)C)N(C)C | [NH:18]([CH3:19])[CH3:20].C[N+](C)=[CH:7][c:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[c:22]([O:23][CH3:24])[cH:21]1.[cH:8]1[cH:9][n:10]([CH3:11])[c:12]2[cH:13][cH:14][cH:15][cH:16][c:17]12>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH:7]([c:8]2[cH:9][n:10]([CH3:11])[c:12]3[cH:13][cH:14][cH:15][cH:16][c:17]23)[N:18]([CH3:19])[CH3:2... | CNC.COc1ccc(C=[N+](C)C)cc1OC.Cn1ccc2ccccc21 | COc1ccc(C(c2cn(C)c3ccccc23)N(C)C)cc1OC | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 85aaf23583cdcf64b6fe54d87d17427b47bda7376efe96f2fd1dd9ad1df13e69 | 7cc25fba33369069673bac5bd8fc404dc064da8d6c8cf4a77f21f4df0a617fe3 | c1ccc(Cc2c[nH]c3ccccc23)cc1 | C-[N+](-C)=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[C;D1;H3:5]-[#7;a:6]1:[c:7]:[cH;D2;+0:8]:[c:9](:[c:10]):[c:11]:1:[c:12].[C;D1;H3:13]-[NH;D2;+0:14]-[C;D1;H3:15]>>[C;D1;H3:5]-[#7;a:6]1:[c:7]:[c;H0;D3;+0:8](-[CH;D3;+0:1](-[N;H0;D3;+0:14](-[C;D1;H3:13])-[C;D1;H3:15])-[c:2](:[c:3]):[c:4]):[c:9](:[c:10]):[c:11]:1:[c:12] | null | [] | null | null | null | null | The preparation was carried out in accordance with general synthesis instructions 4 from 1-methyl-1H-indole and (3,4-dimethoxy-benzylidene)-dimethylammonium chloride, which had been prepared in accordance with example 44 from 3,4-dimethoxy-benzaldehyde and dimethylamine.
Conditions: See reaction.notes.procedure_details... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amine | Tertiary amine | c1ccc2[nH]ccc2c1 | c1c[nH]c2ccccc12 | c1ccccc1.c1c[nH]c2ccccc12 | Other | null | null | null | CNC.COc1ccc(C=[N+](C)C)cc1OC.Cn1ccc2ccccc21>>COc1ccc(C(c2cn(C)c3ccccc23)N(C)C)cc1OC |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-17043a3bab16407eb42e2bd7bcec8beb | CNC.COc1ccc(C=[N+](C)C)cc1OC.Fc1ccc(-c2cc3ccccc3[nH]2)cc1>>COc1ccc(C(c2c(-c3ccc(F)cc3)[nH]c3ccccc23)N(C)C)cc1OC | FC1=CC=C(C=C1)C=1NC2=CC=CC=C2C1.[Cl-].COC=1C=C(C=[N+](C)C)C=CC1OC.COC=1C=C(C=O)C=CC1OC.CNC>>COC=1C=C(C=CC1OC)C(C1=C(NC2=CC=CC=C12)C1=CC=C(C=C1)F)N(C)C | [NH:24]([CH3:25])[CH3:26].C[N+](C)=[CH:7][c:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[c:28]([O:29][CH3:30])[cH:27]1.[cH:8]1[c:9](-[c:10]2[cH:11][cH:12][c:13]([F:14])[cH:15][cH:16]2)[nH:17][c:18]2[cH:19][cH:20][cH:21][cH:22][c:23]12>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH:7]([c:8]2[c:9](-[c:10]3[cH:11][cH:12][c:13]([F:14])[cH... | CNC.COc1ccc(C=[N+](C)C)cc1OC.Fc1ccc(-c2cc3ccccc3[nH]2)cc1 | COc1ccc(C(c2c(-c3ccc(F)cc3)[nH]c3ccccc23)N(C)C)cc1OC | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 4aae3a4ea1be485aab9d544da9fceb1ce060e1d3dd462597adbb05c8cde19188 | 7cc25fba33369069673bac5bd8fc404dc064da8d6c8cf4a77f21f4df0a617fe3 | c1ccc(Cc2c(-c3ccccc3)[nH]c3ccccc23)cc1 | C-[N+](-C)=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[C;D1;H3:5]-[NH;D2;+0:6]-[C;D1;H3:7].[c:8]-[c:9]1:[#7;a:10]:[c:11](:[c:12]):[c:13](:[c:14]):[cH;D2;+0:15]:1>>[C;D1;H3:5]-[N;H0;D3;+0:6](-[C;D1;H3:7])-[CH;D3;+0:1](-[c:2](:[c:3]):[c:4])-[c;H0;D3;+0:15]1:[c:13](:[c:14]):[c:11](:[c:12]):[#7;a:10]:[c:9]:1-[c:8] | null | [] | null | null | null | null | The preparation was carried out in accordance with general synthesis instructions 4 from 2-(4-fluoro-phenyl)-1H-indole and (3,4-dimethoxy-benzylidene)-dimethylammonium chloride, which had been prepared in accordance with example 44 from 3,4-dimethoxy-benzaldehyde and dimethylamine.
Conditions: See reaction.notes.proced... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amine | Tertiary amine | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1 | c1ccccc1.c1ccccc1.c1ccc2[nH]ccc2c1 | Other | null | null | null | CNC.COc1ccc(C=[N+](C)C)cc1OC.Fc1ccc(-c2cc3ccccc3[nH]2)cc1>>COc1ccc(C(c2c(-c3ccc(F)cc3)[nH]c3ccccc23)N(C)C)cc1OC |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-8fb4a0784c5e46a29b0b5a6f2dcabd3f | CNC.COc1ccc(C=[N+](C)C)cc1OC.Fc1ccc(-c2cc3ccccc3[nH]2)cc1Cl>>COc1ccc(C(c2c(-c3ccc(F)c(Cl)c3)[nH]c3ccccc23)N(C)C)cc1OC | ClC=1C=C(C=CC1F)C=1NC2=CC=CC=C2C1.[Cl-].COC=1C=C(C=[N+](C)C)C=CC1OC.COC=1C=C(C=O)C=CC1OC.CNC>>ClC=1C=C(C=CC1F)C=1NC2=CC=CC=C2C1C(C1=CC(=C(C=C1)OC)OC)N(C)C | [NH:25]([CH3:26])[CH3:27].C[N+](C)=[CH:7][c:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[c:29]([O:30][CH3:31])[cH:28]1.[cH:8]1[c:9](-[c:10]2[cH:11][cH:12][c:13]([F:14])[c:15]([Cl:16])[cH:17]2)[nH:18][c:19]2[cH:20][cH:21][cH:22][cH:23][c:24]12>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH:7]([c:8]2[c:9](-[c:10]3[cH:11][cH:12][c:13]([F... | CNC.COc1ccc(C=[N+](C)C)cc1OC.Fc1ccc(-c2cc3ccccc3[nH]2)cc1Cl | COc1ccc(C(c2c(-c3ccc(F)c(Cl)c3)[nH]c3ccccc23)N(C)C)cc1OC | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 4aae3a4ea1be485aab9d544da9fceb1ce060e1d3dd462597adbb05c8cde19188 | 7cc25fba33369069673bac5bd8fc404dc064da8d6c8cf4a77f21f4df0a617fe3 | c1ccc(Cc2c(-c3ccccc3)[nH]c3ccccc23)cc1 | C-[N+](-C)=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[C;D1;H3:5]-[NH;D2;+0:6]-[C;D1;H3:7].[c:8]-[c:9]1:[#7;a:10]:[c:11](:[c:12]):[c:13](:[c:14]):[cH;D2;+0:15]:1>>[C;D1;H3:5]-[N;H0;D3;+0:6](-[C;D1;H3:7])-[CH;D3;+0:1](-[c:2](:[c:3]):[c:4])-[c;H0;D3;+0:15]1:[c:13](:[c:14]):[c:11](:[c:12]):[#7;a:10]:[c:9]:1-[c:8] | null | [] | null | null | null | null | The preparation was carried out in accordance with general synthesis instructions 4 from 2-(3-chloro-4-fluoro-phenyl)-1H-indole and (3,4-dimethoxy-benzylidene)-dimethylammonium chloride, which had been prepared in accordance with example 44 from 3,4-dimethoxy-benzaldehyde and dimethylamine.
Conditions: See reaction.not... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amine | Tertiary amine | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1 | c1ccccc1.c1ccccc1.c1ccc2[nH]ccc2c1 | Other | null | null | null | CNC.COc1ccc(C=[N+](C)C)cc1OC.Fc1ccc(-c2cc3ccccc3[nH]2)cc1Cl>>COc1ccc(C(c2c(-c3ccc(F)c(Cl)c3)[nH]c3ccccc23)N(C)C)cc1OC |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-050cdd945ea044439f3df802c5f31ea6 | CNC.Clc1ccc2[nH]ccc2c1.O=Cc1ccccc1F>>CN(C)C(c1ccccc1F)c1c[nH]c2ccc(Cl)cc12 | ClC=1C=C2C=CNC2=CC1.[Cl-].FC1=C(C=[N+](C)C)C=CC=C1.FC1=C(C=O)C=CC=C1.CNC>>ClC=1C=C2C(=CNC2=CC1)C(C1=C(C=CC=C1)F)N(C)C | [CH3:1][NH:2][CH3:3].[cH:12]1[cH:13][nH:14][c:15]2[cH:16][cH:17][c:18]([Cl:19])[cH:20][c:21]12.O=[CH:4][c:5]1[cH:6][cH:7][cH:8][cH:9][c:10]1[F:11]>>[CH3:1][N:2]([CH3:3])[CH:4]([c:5]1[cH:6][cH:7][cH:8][cH:9][c:10]1[F:11])[c:12]1[cH:13][nH:14][c:15]2[cH:16][cH:17][c:18]([Cl:19])[cH:20][c:21]12 | CNC.Clc1ccc2[nH]ccc2c1.O=Cc1ccccc1F | CN(C)C(c1ccccc1F)c1c[nH]c2ccc(Cl)cc12 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 1e887ffc9d31747076f97173ff8dc6f44b0480e2cfa9f6a88ab0a775ac92e3d5 | 2d03f38884b1fbb0c0d6e6f2de31afb25102fec87f347c3a123e064c1bfef0ad | c1ccc(Cc2c[nH]c3ccccc23)cc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[C;D1;H3:5]-[NH;D2;+0:6]-[C;D1;H3:7].[c:8]:[c:9]1:[#7;a:10]:[c:11]:[cH;D2;+0:12]:[c:13]:1:[c:14]>>[C;D1;H3:5]-[N;H0;D3;+0:6](-[C;D1;H3:7])-[CH;D3;+0:1](-[c:2](:[c:3]):[c:4])-[c;H0;D3;+0:12]1:[c:11]:[#7;a:10]:[c:9](:[c:8]):[c:13]:1:[c:14] | null | [] | null | null | null | null | The preparation was carried out in accordance with general synthesis instructions 4 from 5-chloro-1H-indole and (2-fluoro-benzylidene)-dimethylammonium chloride, which had been prepared in accordance with example 44 from 2-fluoro-benzaldehyde and dimethylamine.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Secondary amine | Tertiary amine | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1 | c1ccccc1.c1ccc2[nH]ccc2c1 | HO- | null | null | null | CNC.Clc1ccc2[nH]ccc2c1.O=Cc1ccccc1F>>CN(C)C(c1ccccc1F)c1c[nH]c2ccc(Cl)cc12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-e8415c5d0b5f45968db469e1e4e5f5f1 | CNC.Cc1cccc2[nH]ccc12.O=Cc1ccc(F)cc1>>Cc1cccc2[nH]cc(C(c3ccc(F)cc3)N(C)C)c12 | CC1=C2C=CNC2=CC=C1.[Cl-].FC1=CC=C(C=[N+](C)C)C=C1.FC1=CC=C(C=O)C=C1.CNC>>FC1=CC=C(C=C1)C(C1=CNC2=CC=CC(=C12)C)N(C)C | [NH:18]([CH3:19])[CH3:20].[CH3:1][c:2]1[cH:3][cH:4][cH:5][c:6]2[nH:7][cH:8][cH:9][c:21]12.O=[CH:10][c:11]1[cH:12][cH:13][c:14]([F:15])[cH:16][cH:17]1>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][c:6]2[nH:7][cH:8][c:9]([CH:10]([c:11]3[cH:12][cH:13][c:14]([F:15])[cH:16][cH:17]3)[N:18]([CH3:19])[CH3:20])[c:21]12 | CNC.Cc1cccc2[nH]ccc12.O=Cc1ccc(F)cc1 | Cc1cccc2[nH]cc(C(c3ccc(F)cc3)N(C)C)c12 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 1e887ffc9d31747076f97173ff8dc6f44b0480e2cfa9f6a88ab0a775ac92e3d5 | 2d03f38884b1fbb0c0d6e6f2de31afb25102fec87f347c3a123e064c1bfef0ad | c1ccc(Cc2c[nH]c3ccccc23)cc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[C;D1;H3:5]-[NH;D2;+0:6]-[C;D1;H3:7].[c:8]:[c:9]1:[cH;D2;+0:10]:[c:11]:[#7;a:12]:[c:13]:1:[c:14]>>[C;D1;H3:5]-[N;H0;D3;+0:6](-[C;D1;H3:7])-[CH;D3;+0:1](-[c:2](:[c:3]):[c:4])-[c;H0;D3;+0:10]1:[c:11]:[#7;a:12]:[c:13](:[c:14]):[c:9]:1:[c:8] | null | [] | null | null | null | null | The preparation was carried out in accordance with general synthesis instructions 4 from 4-methyl-1H-indole and (4-fluoro-benzylidene)-dimethylammonium chloride, which had been prepared in accordance with example 44 from 4-fluoro-benzaldehyde and dimethylamine.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Secondary amine | Tertiary amine | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1.c1ccccc1 | HO- | null | null | null | CNC.Cc1cccc2[nH]ccc12.O=Cc1ccc(F)cc1>>Cc1cccc2[nH]cc(C(c3ccc(F)cc3)N(C)C)c12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-f851d4fe74e1437ea8d21be3e4172a3c | CCc1cccc2cc[nH]c12.CNC.COc1ccccc1C=O>>CCc1cccc2c(C(c3ccccc3OC)N(C)C)c[nH]c12 | C(C)C=1C=CC=C2C=CNC12.[Cl-].COC1=C(C=[N+](C)C)C=CC=C1.COC1=C(C=O)C=CC=C1.CNC>>C(C)C=1C=CC=C2C(=CNC12)C(C1=C(C=CC=C1)OC)N(C)C | [CH3:1][CH2:2][c:3]1[cH:4][cH:5][cH:6][c:7]2[cH:8][cH:21][nH:22][c:23]12.[NH:18]([CH3:19])[CH3:20].O=[CH:9][c:10]1[cH:11][cH:12][cH:13][cH:14][c:15]1[O:16][CH3:17]>>[CH3:1][CH2:2][c:3]1[cH:4][cH:5][cH:6][c:7]2[c:8]([CH:9]([c:10]3[cH:11][cH:12][cH:13][cH:14][c:15]3[O:16][CH3:17])[N:18]([CH3:19])[CH3:20])[cH:21][nH:22][c... | CCc1cccc2cc[nH]c12.CNC.COc1ccccc1C=O | CCc1cccc2c(C(c3ccccc3OC)N(C)C)c[nH]c12 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 1e887ffc9d31747076f97173ff8dc6f44b0480e2cfa9f6a88ab0a775ac92e3d5 | 2d03f38884b1fbb0c0d6e6f2de31afb25102fec87f347c3a123e064c1bfef0ad | c1ccc(Cc2c[nH]c3ccccc23)cc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[C;D1;H3:5]-[NH;D2;+0:6]-[C;D1;H3:7].[c:8]:[c:9]1:[#7;a:10]:[c:11]:[cH;D2;+0:12]:[c:13]:1:[c:14]>>[C;D1;H3:5]-[N;H0;D3;+0:6](-[C;D1;H3:7])-[CH;D3;+0:1](-[c:2](:[c:3]):[c:4])-[c;H0;D3;+0:12]1:[c:11]:[#7;a:10]:[c:9](:[c:8]):[c:13]:1:[c:14] | null | [] | null | null | null | null | The preparation was carried out in accordance with general synthesis instructions 4 from 7-ethyl-1H-indole and (2-methoxy-benzylidene)-dimethylammonium chloride, which had been prepared in accordance with example 44 from 2-methoxy-benzaldehyde and dimethylamine.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Secondary amine | Tertiary amine | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1 | c1ccccc1.c1ccc2[nH]ccc2c1 | HO- | null | null | null | CCc1cccc2cc[nH]c12.CNC.COc1ccccc1C=O>>CCc1cccc2c(C(c3ccccc3OC)N(C)C)c[nH]c12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-d2e25ad230874e0884226fde176b5733 | Cc1cc2ccccc2[nH]1.Cc1ccccc1C=[N+](C)C>>Cc1ccccc1C(c1c(C)[nH]c2ccccc12)N(C)C | CC=1NC2=CC=CC=C2C1.[Cl-].CC1=C(C=[N+](C)C)C=CC=C1.CC1=C(C=O)C=CC=C1.CNC>>CN(C(C1=C(C=CC=C1)C)C1=C(NC2=CC=CC=C12)C)C | [cH:9]1[c:10]([CH3:11])[nH:12][c:13]2[cH:14][cH:15][cH:16][cH:17][c:18]12.[CH3:1][c:2]1[cH:3][cH:4][cH:5][cH:6][c:7]1[CH:8]=[N+:19]([CH3:20])[CH3:21]>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][cH:6][c:7]1[CH:8]([c:9]1[c:10]([CH3:11])[nH:12][c:13]2[cH:14][cH:15][cH:16][cH:17][c:18]12)[N:19]([CH3:20])[CH3:21] | Cc1cc2ccccc2[nH]1.Cc1ccccc1C=[N+](C)C | Cc1ccccc1C(c1c(C)[nH]c2ccccc12)N(C)C | null | null | null | C-C Coupling | OtherReaction | 6f78ebae7a6e5f9c15e0d6ab78f58f64a17b670729ecfc39fbb9b9e11c788fae | 5c03404e5740858973798689d4be0a8ed62608f5043e578ba3cd6de4363e2dbe | c1ccc(Cc2c[nH]c3ccccc23)cc1 | [C;D1;H3:1]-[N+;H0;D3:2](-[C;D1;H3:3])=[CH;D2;+0:4]-[c:5](:[c:6]):[c:7].[C;D1;H3:8]-[c:9]1:[#7;a:10]:[c:11](:[c:12]):[c:13](:[c:14]):[cH;D2;+0:15]:1>>[C;D1;H3:8]-[c:9]1:[#7;a:10]:[c:11](:[c:12]):[c:13](:[c:14]):[c;H0;D3;+0:15]:1-[CH;D3;+0:4](-[N;H0;D3;+0:2](-[C;D1;H3:1])-[C;D1;H3:3])-[c:5](:[c:6]):[c:7] | null | [] | null | null | null | null | The preparation was carried out in accordance with general synthesis instructions 4 from 2-methyl-1H-indole and (2-methyl-benzylidene)-dimethylammonium chloride, which had been prepared in accordance with example 44 from 2-methyl-benzaldehyde and dimethylamine.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | null | Tertiary amine | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1 | c1ccccc1.c1ccc2[nH]ccc2c1 | null | null | null | null | Cc1cc2ccccc2[nH]1.Cc1ccccc1C=[N+](C)C>>Cc1ccccc1C(c1c(C)[nH]c2ccccc12)N(C)C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-867d92e2aac34594979eadeda21ac344 | CCc1cccc2cc[nH]c12.CNC.Cc1ccccc1C=O>>CCc1cccc2c(C(c3ccccc3C)N(C)C)c[nH]c12 | C(C)C=1C=CC=C2C=CNC12.[Cl-].CC1=C(C=[N+](C)C)C=CC=C1.CC1=C(C=O)C=CC=C1.CNC>>C(C)C=1C=CC=C2C(=CNC12)C(C1=C(C=CC=C1)C)N(C)C | [CH3:1][CH2:2][c:3]1[cH:4][cH:5][cH:6][c:7]2[cH:8][cH:20][nH:21][c:22]12.[NH:17]([CH3:18])[CH3:19].O=[CH:9][c:10]1[cH:11][cH:12][cH:13][cH:14][c:15]1[CH3:16]>>[CH3:1][CH2:2][c:3]1[cH:4][cH:5][cH:6][c:7]2[c:8]([CH:9]([c:10]3[cH:11][cH:12][cH:13][cH:14][c:15]3[CH3:16])[N:17]([CH3:18])[CH3:19])[cH:20][nH:21][c:22]12 | CCc1cccc2cc[nH]c12.CNC.Cc1ccccc1C=O | CCc1cccc2c(C(c3ccccc3C)N(C)C)c[nH]c12 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 1e887ffc9d31747076f97173ff8dc6f44b0480e2cfa9f6a88ab0a775ac92e3d5 | 2d03f38884b1fbb0c0d6e6f2de31afb25102fec87f347c3a123e064c1bfef0ad | c1ccc(Cc2c[nH]c3ccccc23)cc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[C;D1;H3:5]-[NH;D2;+0:6]-[C;D1;H3:7].[c:8]:[c:9]1:[#7;a:10]:[c:11]:[cH;D2;+0:12]:[c:13]:1:[c:14]>>[C;D1;H3:5]-[N;H0;D3;+0:6](-[C;D1;H3:7])-[CH;D3;+0:1](-[c:2](:[c:3]):[c:4])-[c;H0;D3;+0:12]1:[c:11]:[#7;a:10]:[c:9](:[c:8]):[c:13]:1:[c:14] | null | [] | null | null | null | null | The preparation was carried out in accordance with general synthesis instructions 4 from 7-ethyl-1H-indole and (2-methyl-benzylidene)-dimethylammonium chloride, which had been prepared in accordance with example 44 from 2-methyl-benzaldehyde and dimethylamine.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Secondary amine | Tertiary amine | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1 | c1ccccc1.c1ccc2[nH]ccc2c1 | HO- | null | null | null | CCc1cccc2cc[nH]c12.CNC.Cc1ccccc1C=O>>CCc1cccc2c(C(c3ccccc3C)N(C)C)c[nH]c12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-9f30dee72cee4b8e950846dc191f7f87 | CNC.Cc1ccccc1C=O.Cn1ccc2ccccc21>>Cc1ccccc1C(c1cn(C)c2ccccc12)N(C)C | CN1C=CC2=CC=CC=C12.[Cl-].CC1=C(C=[N+](C)C)C=CC=C1.CC1=C(C=O)C=CC=C1.CNC>>CN(C(C1=C(C=CC=C1)C)C1=CN(C2=CC=CC=C12)C)C | [NH:19]([CH3:20])[CH3:21].O=[CH:8][c:7]1[c:2]([CH3:1])[cH:3][cH:4][cH:5][cH:6]1.[cH:9]1[cH:10][n:11]([CH3:12])[c:13]2[cH:14][cH:15][cH:16][cH:17][c:18]12>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][cH:6][c:7]1[CH:8]([c:9]1[cH:10][n:11]([CH3:12])[c:13]2[cH:14][cH:15][cH:16][cH:17][c:18]12)[N:19]([CH3:20])[CH3:21] | CNC.Cc1ccccc1C=O.Cn1ccc2ccccc21 | Cc1ccccc1C(c1cn(C)c2ccccc12)N(C)C | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 05894bd812613f52cf9c1620f3154e6ca08db53b10e13d8864b239f8fa88e3d5 | 2d03f38884b1fbb0c0d6e6f2de31afb25102fec87f347c3a123e064c1bfef0ad | c1ccc(Cc2c[nH]c3ccccc23)cc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[C;D1;H3:5]-[#7;a:6]1:[c:7]:[cH;D2;+0:8]:[c:9](:[c:10]):[c:11]:1:[c:12].[C;D1;H3:13]-[NH;D2;+0:14]-[C;D1;H3:15]>>[C;D1;H3:5]-[#7;a:6]1:[c:7]:[c;H0;D3;+0:8](-[CH;D3;+0:1](-[N;H0;D3;+0:14](-[C;D1;H3:13])-[C;D1;H3:15])-[c:2](:[c:3]):[c:4]):[c:9](:[c:10]):[c:11]:1:[c:12] | null | [] | null | null | null | null | The preparation was carried out in accordance with general synthesis instructions 4 from 1-methyl-1H-indole and (2-methyl-benzylidene)-dimethylammonium chloride, which had been prepared in accordance with example 44 from 2-methyl-benzaldehyde and dimethylamine.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Secondary amine | Tertiary amine | c1ccc2[nH]ccc2c1 | c1c[nH]c2ccccc12 | c1ccccc1.c1c[nH]c2ccccc12 | HO- | null | null | null | CNC.Cc1ccccc1C=O.Cn1ccc2ccccc21>>Cc1ccccc1C(c1cn(C)c2ccccc12)N(C)C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-2d8fffeb348e41d1964f1f9400476c80 | CNC.Cc1ccccc1C=O.Clc1ccc2[nH]ccc2c1>>Cc1ccccc1C(c1c[nH]c2ccc(Cl)cc12)N(C)C | ClC=1C=C2C=CNC2=CC1.[Cl-].CC1=C(C=[N+](C)C)C=CC=C1.CC1=C(C=O)C=CC=C1.CNC>>ClC=1C=C2C(=CNC2=CC1)C(C1=C(C=CC=C1)C)N(C)C | [NH:19]([CH3:20])[CH3:21].O=[CH:8][c:7]1[c:2]([CH3:1])[cH:3][cH:4][cH:5][cH:6]1.[cH:9]1[cH:10][nH:11][c:12]2[cH:13][cH:14][c:15]([Cl:16])[cH:17][c:18]12>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][cH:6][c:7]1[CH:8]([c:9]1[cH:10][nH:11][c:12]2[cH:13][cH:14][c:15]([Cl:16])[cH:17][c:18]12)[N:19]([CH3:20])[CH3:21] | CNC.Cc1ccccc1C=O.Clc1ccc2[nH]ccc2c1 | Cc1ccccc1C(c1c[nH]c2ccc(Cl)cc12)N(C)C | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 1e887ffc9d31747076f97173ff8dc6f44b0480e2cfa9f6a88ab0a775ac92e3d5 | 2d03f38884b1fbb0c0d6e6f2de31afb25102fec87f347c3a123e064c1bfef0ad | c1ccc(Cc2c[nH]c3ccccc23)cc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[C;D1;H3:5]-[NH;D2;+0:6]-[C;D1;H3:7].[c:8]:[c:9]1:[#7;a:10]:[c:11]:[cH;D2;+0:12]:[c:13]:1:[c:14]>>[C;D1;H3:5]-[N;H0;D3;+0:6](-[C;D1;H3:7])-[CH;D3;+0:1](-[c:2](:[c:3]):[c:4])-[c;H0;D3;+0:12]1:[c:11]:[#7;a:10]:[c:9](:[c:8]):[c:13]:1:[c:14] | null | [] | null | null | null | null | The preparation was carried out in accordance with general synthesis instructions 4 from 5-chloro-1H-indole and (2-methyl-benzylidene)-dimethylammonium chloride, which had been prepared in accordance with example 44 from 2-methyl-benzaldehyde and dimethylamine.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Secondary amine | Tertiary amine | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1 | c1ccccc1.c1ccc2[nH]ccc2c1 | HO- | null | null | null | CNC.Cc1ccccc1C=O.Clc1ccc2[nH]ccc2c1>>Cc1ccccc1C(c1c[nH]c2ccc(Cl)cc12)N(C)C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-76c370c1664845558d3cc239ce3bf4b9 | CNC.Cc1cccc(C=O)c1.Clc1ccc2[nH]ccc2c1>>Cc1cccc(C(c2c[nH]c3ccc(Cl)cc23)N(C)C)c1 | ClC=1C=C2C=CNC2=CC1.[Cl-].CC=1C=C(C=[N+](C)C)C=CC1.CC=1C=C(C=O)C=CC1.CNC>>ClC=1C=C2C(=CNC2=CC1)C(C=1C=C(C=CC1)C)N(C)C | [NH:18]([CH3:19])[CH3:20].O=[CH:7][c:6]1[cH:5][cH:4][cH:3][c:2]([CH3:1])[cH:21]1.[cH:8]1[cH:9][nH:10][c:11]2[cH:12][cH:13][c:14]([Cl:15])[cH:16][c:17]12>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][c:6]([CH:7]([c:8]2[cH:9][nH:10][c:11]3[cH:12][cH:13][c:14]([Cl:15])[cH:16][c:17]23)[N:18]([CH3:19])[CH3:20])[cH:21]1 | CNC.Cc1cccc(C=O)c1.Clc1ccc2[nH]ccc2c1 | Cc1cccc(C(c2c[nH]c3ccc(Cl)cc23)N(C)C)c1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 1e887ffc9d31747076f97173ff8dc6f44b0480e2cfa9f6a88ab0a775ac92e3d5 | 2d03f38884b1fbb0c0d6e6f2de31afb25102fec87f347c3a123e064c1bfef0ad | c1ccc(Cc2c[nH]c3ccccc23)cc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[C;D1;H3:5]-[NH;D2;+0:6]-[C;D1;H3:7].[c:8]:[c:9]1:[#7;a:10]:[c:11]:[cH;D2;+0:12]:[c:13]:1:[c:14]>>[C;D1;H3:5]-[N;H0;D3;+0:6](-[C;D1;H3:7])-[CH;D3;+0:1](-[c:2](:[c:3]):[c:4])-[c;H0;D3;+0:12]1:[c:11]:[#7;a:10]:[c:9](:[c:8]):[c:13]:1:[c:14] | null | [] | null | null | null | null | The preparation was carried out in accordance with general synthesis instructions 4 from 5-chloro-1H-indole and (3-methyl-benzylidene)-dimethylammonium chloride, which had been prepared in accordance with example 44 from 3-methyl-benzaldehyde and dimethylamine.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Secondary amine | Tertiary amine | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1 | c1ccccc1.c1ccc2[nH]ccc2c1 | HO- | null | null | null | CNC.Cc1cccc(C=O)c1.Clc1ccc2[nH]ccc2c1>>Cc1cccc(C(c2c[nH]c3ccc(Cl)cc23)N(C)C)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-64ec4af69c6f479089ad40c47495e9de | CNC.Cc1cc2ccccc2[nH]1.Cc1ccc(C=[N+](C)C)cc1>>Cc1ccc(C(c2c(C)[nH]c3ccccc23)N(C)C)cc1 | CC=1NC2=CC=CC=C2C1.[Cl-].CC1=CC=C(C=[N+](C)C)C=C1.CC1=CC=C(C=O)C=C1.CNC>>CN(C(C1=CC=C(C=C1)C)C1=C(NC2=CC=CC=C12)C)C | [NH:17]([CH3:18])[CH3:19].[cH:7]1[c:8]([CH3:9])[nH:10][c:11]2[cH:12][cH:13][cH:14][cH:15][c:16]12.C[N+](C)=[CH:6][c:5]1[cH:4][cH:3][c:2]([CH3:1])[cH:21][cH:20]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([CH:6]([c:7]2[c:8]([CH3:9])[nH:10][c:11]3[cH:12][cH:13][cH:14][cH:15][c:16]23)[N:17]([CH3:18])[CH3:19])[cH:20][cH:21]1 | CNC.Cc1cc2ccccc2[nH]1.Cc1ccc(C=[N+](C)C)cc1 | Cc1ccc(C(c2c(C)[nH]c3ccccc23)N(C)C)cc1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 4aae3a4ea1be485aab9d544da9fceb1ce060e1d3dd462597adbb05c8cde19188 | 7cc25fba33369069673bac5bd8fc404dc064da8d6c8cf4a77f21f4df0a617fe3 | c1ccc(Cc2c[nH]c3ccccc23)cc1 | C-[N+](-C)=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[C;D1;H3:5]-[NH;D2;+0:6]-[C;D1;H3:7].[C;D1;H3:8]-[c:9]1:[#7;a:10]:[c:11](:[c:12]):[c:13](:[c:14]):[cH;D2;+0:15]:1>>[C;D1;H3:5]-[N;H0;D3;+0:6](-[C;D1;H3:7])-[CH;D3;+0:1](-[c:2](:[c:3]):[c:4])-[c;H0;D3;+0:15]1:[c:13](:[c:14]):[c:11](:[c:12]):[#7;a:10]:[c:9]:1-[C;D1;H3:8] | null | [] | null | null | null | null | The preparation was carried out in accordance with general synthesis instructions 4 from 2-methyl-1H-indole and (4-methyl-benzylidene)-dimethylammonium chloride, which had been prepared in accordance with example 44 from 4-methyl-benzaldehyde and dimethylamine.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Secondary amine | Tertiary amine | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1 | c1ccccc1.c1ccc2[nH]ccc2c1 | Other | null | null | null | CNC.Cc1cc2ccccc2[nH]1.Cc1ccc(C=[N+](C)C)cc1>>Cc1ccc(C(c2c(C)[nH]c3ccccc23)N(C)C)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-d55d366996404928a78cd09f61c25cca | CNC.Cc1ccc(C=O)cc1.Clc1ccc2[nH]ccc2c1>>Cc1ccc(C(c2c[nH]c3ccc(Cl)cc23)N(C)C)cc1 | ClC=1C=C2C=CNC2=CC1.[Cl-].CC1=CC=C(C=[N+](C)C)C=C1.CC1=CC=C(C=O)C=C1.CNC>>ClC=1C=C2C(=CNC2=CC1)C(C1=CC=C(C=C1)C)N(C)C | [NH:17]([CH3:18])[CH3:19].O=[CH:6][c:5]1[cH:4][cH:3][c:2]([CH3:1])[cH:21][cH:20]1.[cH:7]1[cH:8][nH:9][c:10]2[cH:11][cH:12][c:13]([Cl:14])[cH:15][c:16]12>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([CH:6]([c:7]2[cH:8][nH:9][c:10]3[cH:11][cH:12][c:13]([Cl:14])[cH:15][c:16]23)[N:17]([CH3:18])[CH3:19])[cH:20][cH:21]1 | CNC.Cc1ccc(C=O)cc1.Clc1ccc2[nH]ccc2c1 | Cc1ccc(C(c2c[nH]c3ccc(Cl)cc23)N(C)C)cc1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 1e887ffc9d31747076f97173ff8dc6f44b0480e2cfa9f6a88ab0a775ac92e3d5 | 2d03f38884b1fbb0c0d6e6f2de31afb25102fec87f347c3a123e064c1bfef0ad | c1ccc(Cc2c[nH]c3ccccc23)cc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[C;D1;H3:5]-[NH;D2;+0:6]-[C;D1;H3:7].[c:8]:[c:9]1:[#7;a:10]:[c:11]:[cH;D2;+0:12]:[c:13]:1:[c:14]>>[C;D1;H3:5]-[N;H0;D3;+0:6](-[C;D1;H3:7])-[CH;D3;+0:1](-[c:2](:[c:3]):[c:4])-[c;H0;D3;+0:12]1:[c:11]:[#7;a:10]:[c:9](:[c:8]):[c:13]:1:[c:14] | null | [] | null | null | null | null | The preparation was carried out in accordance with general synthesis instructions 4 from 5-chloro-1H-indole and (4-methyl-benzylidene)-dimethylammonium chloride, which had been prepared in accordance with example 44 from 4-methyl-benzaldehyde and dimethylamine.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Secondary amine | Tertiary amine | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1 | c1ccccc1.c1ccc2[nH]ccc2c1 | HO- | null | null | null | CNC.Cc1ccc(C=O)cc1.Clc1ccc2[nH]ccc2c1>>Cc1ccc(C(c2c[nH]c3ccc(Cl)cc23)N(C)C)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-743e272d902a4863a523cebd7ee14efc | CNC.Cc1cc2ccccc2[nH]1.O=Cc1cccc(Oc2ccccc2)c1>>Cc1[nH]c2ccccc2c1C(c1cccc(Oc2ccccc2)c1)N(C)C | CC=1NC2=CC=CC=C2C1.[Cl-].O(C1=CC=CC=C1)C=1C=C(C=[N+](C)C)C=CC1.O(C1=CC=CC=C1)C=1C=C(C=O)C=CC1.CNC>>CN(C(C1=CC(=CC=C1)OC1=CC=CC=C1)C1=C(NC2=CC=CC=C12)C)C | [NH:25]([CH3:26])[CH3:27].[CH3:1][c:2]1[nH:3][c:4]2[cH:5][cH:6][cH:7][cH:8][c:9]2[cH:10]1.O=[CH:11][c:12]1[cH:13][cH:14][cH:15][c:16]([O:17][c:18]2[cH:19][cH:20][cH:21][cH:22][cH:23]2)[cH:24]1>>[CH3:1][c:2]1[nH:3][c:4]2[cH:5][cH:6][cH:7][cH:8][c:9]2[c:10]1[CH:11]([c:12]1[cH:13][cH:14][cH:15][c:16]([O:17][c:18]2[cH:19][... | CNC.Cc1cc2ccccc2[nH]1.O=Cc1cccc(Oc2ccccc2)c1 | Cc1[nH]c2ccccc2c1C(c1cccc(Oc2ccccc2)c1)N(C)C | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 1e887ffc9d31747076f97173ff8dc6f44b0480e2cfa9f6a88ab0a775ac92e3d5 | 2d03f38884b1fbb0c0d6e6f2de31afb25102fec87f347c3a123e064c1bfef0ad | c1ccc(Oc2cccc(Cc3c[nH]c4ccccc34)c2)cc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[C;D1;H3:5]-[NH;D2;+0:6]-[C;D1;H3:7].[C;D1;H3:8]-[c:9]1:[#7;a:10]:[c:11](:[c:12]):[c:13](:[c:14]):[cH;D2;+0:15]:1>>[C;D1;H3:8]-[c:9]1:[#7;a:10]:[c:11](:[c:12]):[c:13](:[c:14]):[c;H0;D3;+0:15]:1-[CH;D3;+0:1](-[N;H0;D3;+0:6](-[C;D1;H3:5])-[C;D1;H3:7])-[c:2](:[c:3]):[c:4] | null | [] | null | null | null | null | The preparation was carried out in accordance with general synthesis instructions 4 from 2-methyl-1H-indole and (3-phenoxy-benzylidene)-dimethylammonium chloride, which had been prepared in accordance with example 44 from 3-phenoxy-benzaldehyde and dimethylamine.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Secondary amine | Tertiary amine | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1.c1ccccc1.c1ccccc1 | HO- | null | null | null | CNC.Cc1cc2ccccc2[nH]1.O=Cc1cccc(Oc2ccccc2)c1>>Cc1[nH]c2ccccc2c1C(c1cccc(Oc2ccccc2)c1)N(C)C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-e97e9aacf01447ff9cb577b2ed4fcc56 | CCn1c(-c2ccccc2)cc2ccccc21.CNC.O=Cc1cccc(Oc2ccccc2)c1>>CCn1c(-c2ccccc2)c(C(c2cccc(Oc3ccccc3)c2)N(C)C)c2ccccc21 | C(C)N1C(=CC2=CC=CC=C12)C1=CC=CC=C1.[Cl-].O(C1=CC=CC=C1)C=1C=C(C=[N+](C)C)C=CC1.O(C1=CC=CC=C1)C=1C=C(C=O)C=CC1.CNC>>C(C)N1C(=C(C2=CC=CC=C12)C(C1=CC(=CC=C1)OC1=CC=CC=C1)N(C)C)C1=CC=CC=C1 | [CH3:1][CH2:2][n:3]1[c:4](-[c:5]2[cH:6][cH:7][cH:8][cH:9][cH:10]2)[cH:11][c:29]2[cH:30][cH:31][cH:32][cH:33][c:34]12.[NH:26]([CH3:27])[CH3:28].O=[CH:12][c:13]1[cH:14][cH:15][cH:16][c:17]([O:18][c:19]2[cH:20][cH:21][cH:22][cH:23][cH:24]2)[cH:25]1>>[CH3:1][CH2:2][n:3]1[c:4](-[c:5]2[cH:6][cH:7][cH:8][cH:9][cH:10]2)[c:11](... | CCn1c(-c2ccccc2)cc2ccccc21.CNC.O=Cc1cccc(Oc2ccccc2)c1 | CCn1c(-c2ccccc2)c(C(c2cccc(Oc3ccccc3)c2)N(C)C)c2ccccc21 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | bec24864ceecfec904d98640b3bb3caa9d35fa656dcbdac3c55c0dacb43b50eb | 2d03f38884b1fbb0c0d6e6f2de31afb25102fec87f347c3a123e064c1bfef0ad | c1ccc(Oc2cccc(Cc3c(-c4ccccc4)[nH]c4ccccc34)c2)cc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[C;D1;H3:5]-[NH;D2;+0:6]-[C;D1;H3:7].[C:8]-[#7;a:9]1:[c:10](:[c:11]):[c:12](:[c:13]):[cH;D2;+0:14]:[c:15]:1-[c:16]>>[C:8]-[#7;a:9]1:[c:10](:[c:11]):[c:12](:[c:13]):[c;H0;D3;+0:14](-[CH;D3;+0:1](-[N;H0;D3;+0:6](-[C;D1;H3:5])-[C;D1;H3:7])-[c:2](:[c:3]):[c:4]):[c:15]:1-[c:16] | null | [] | null | null | null | null | The preparation was carried out in accordance with general synthesis instructions 4 from 1-ethyl-2-phenyl-1H-indole and (3-phenoxy-benzylidene)-dimethylammonium chloride, which had been prepared in accordance with example 44 from 3-phenoxy-benzaldehyde and dimethylamine.
Conditions: See reaction.notes.procedure_details... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Secondary amine | Tertiary amine | c1cc2ccccc2[nH]1 | c1cc2ccccc2[nH]1 | c1ccccc1.c1ccccc1.c1ccccc1.c1cc2ccccc2[nH]1 | HO- | null | null | null | CCn1c(-c2ccccc2)cc2ccccc21.CNC.O=Cc1cccc(Oc2ccccc2)c1>>CCn1c(-c2ccccc2)c(C(c2cccc(Oc3ccccc3)c2)N(C)C)c2ccccc21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-e50db9293f9e4f3f9f2530c09171c21c | CCc1cccc2cc[nH]c12.CNC.O=Cc1cccc(Oc2ccccc2)c1>>CCc1cccc2c(C(c3cccc(Oc4ccccc4)c3)N(C)C)c[nH]c12 | C(C)C=1C=CC=C2C=CNC12.[Cl-].O(C1=CC=CC=C1)C=1C=C(C=[N+](C)C)C=CC1.O(C1=CC=CC=C1)C=1C=C(C=O)C=CC1.CNC>>C(C)C=1C=CC=C2C(=CNC12)C(C1=CC(=CC=C1)OC1=CC=CC=C1)N(C)C | [CH3:1][CH2:2][c:3]1[cH:4][cH:5][cH:6][c:7]2[cH:8][cH:26][nH:27][c:28]12.[NH:23]([CH3:24])[CH3:25].O=[CH:9][c:10]1[cH:11][cH:12][cH:13][c:14]([O:15][c:16]2[cH:17][cH:18][cH:19][cH:20][cH:21]2)[cH:22]1>>[CH3:1][CH2:2][c:3]1[cH:4][cH:5][cH:6][c:7]2[c:8]([CH:9]([c:10]3[cH:11][cH:12][cH:13][c:14]([O:15][c:16]4[cH:17][cH:18... | CCc1cccc2cc[nH]c12.CNC.O=Cc1cccc(Oc2ccccc2)c1 | CCc1cccc2c(C(c3cccc(Oc4ccccc4)c3)N(C)C)c[nH]c12 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 1e887ffc9d31747076f97173ff8dc6f44b0480e2cfa9f6a88ab0a775ac92e3d5 | 2d03f38884b1fbb0c0d6e6f2de31afb25102fec87f347c3a123e064c1bfef0ad | c1ccc(Oc2cccc(Cc3c[nH]c4ccccc34)c2)cc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[C;D1;H3:5]-[NH;D2;+0:6]-[C;D1;H3:7].[c:8]:[c:9]1:[#7;a:10]:[c:11]:[cH;D2;+0:12]:[c:13]:1:[c:14]>>[C;D1;H3:5]-[N;H0;D3;+0:6](-[C;D1;H3:7])-[CH;D3;+0:1](-[c:2](:[c:3]):[c:4])-[c;H0;D3;+0:12]1:[c:11]:[#7;a:10]:[c:9](:[c:8]):[c:13]:1:[c:14] | null | [] | null | null | null | null | The preparation was carried out in accordance with general synthesis instructions 4 from 7-ethyl-1H-indole and (3-phenoxy-benzylidene)-dimethylammonium chloride, which had been prepared in accordance with example 44 from 3-phenoxy-benzaldehyde and dimethylamine.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Secondary amine | Tertiary amine | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1 | c1ccccc1.c1ccccc1.c1ccc2[nH]ccc2c1 | HO- | null | null | null | CCc1cccc2cc[nH]c12.CNC.O=Cc1cccc(Oc2ccccc2)c1>>CCc1cccc2c(C(c3cccc(Oc4ccccc4)c3)N(C)C)c[nH]c12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-e867fb0a3eb245aeb3eef62e76496d76 | CNC.Cn1ccc2ccccc21.O=Cc1cccc(Oc2ccccc2)c1>>CN(C)C(c1cccc(Oc2ccccc2)c1)c1cn(C)c2ccccc12 | CN1C=CC2=CC=CC=C12.[Cl-].O(C1=CC=CC=C1)C=1C=C(C=[N+](C)C)C=CC1.O(C1=CC=CC=C1)C=1C=C(C=O)C=CC1.CNC>>CN(C(C1=CC(=CC=C1)OC1=CC=CC=C1)C1=CN(C2=CC=CC=C12)C)C | [CH3:1][NH:2][CH3:3].[cH:18]1[cH:19][n:20]([CH3:21])[c:22]2[cH:23][cH:24][cH:25][cH:26][c:27]12.O=[CH:4][c:5]1[cH:6][cH:7][cH:8][c:9]([O:10][c:11]2[cH:12][cH:13][cH:14][cH:15][cH:16]2)[cH:17]1>>[CH3:1][N:2]([CH3:3])[CH:4]([c:5]1[cH:6][cH:7][cH:8][c:9]([O:10][c:11]2[cH:12][cH:13][cH:14][cH:15][cH:16]2)[cH:17]1)[c:18]1[c... | CNC.Cn1ccc2ccccc21.O=Cc1cccc(Oc2ccccc2)c1 | CN(C)C(c1cccc(Oc2ccccc2)c1)c1cn(C)c2ccccc12 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 05894bd812613f52cf9c1620f3154e6ca08db53b10e13d8864b239f8fa88e3d5 | 2d03f38884b1fbb0c0d6e6f2de31afb25102fec87f347c3a123e064c1bfef0ad | c1ccc(Oc2cccc(Cc3c[nH]c4ccccc34)c2)cc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[C;D1;H3:5]-[#7;a:6]1:[c:7]:[cH;D2;+0:8]:[c:9](:[c:10]):[c:11]:1:[c:12].[C;D1;H3:13]-[NH;D2;+0:14]-[C;D1;H3:15]>>[C;D1;H3:13]-[N;H0;D3;+0:14](-[C;D1;H3:15])-[CH;D3;+0:1](-[c:2](:[c:3]):[c:4])-[c;H0;D3;+0:8]1:[c:7]:[#7;a:6](-[C;D1;H3:5]):[c:11](:[c:12]):[c:9]:1:[c:10] | null | [] | null | null | null | null | The preparation was carried out in accordance with general synthesis instructions 4 from 1-methyl-1H-indole and (3-phenoxy-benzylidene)-dimethylammonium chloride, which had been prepared in accordance with example 44 from 3-phenoxy-benzaldehyde and dimethylamine.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Secondary amine | Tertiary amine | c1ccc2[nH]ccc2c1 | c1c[nH]c2ccccc12 | c1ccccc1.c1ccccc1.c1c[nH]c2ccccc12 | HO- | null | null | null | CNC.Cn1ccc2ccccc21.O=Cc1cccc(Oc2ccccc2)c1>>CN(C)C(c1cccc(Oc2ccccc2)c1)c1cn(C)c2ccccc12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-8282e8e7abbb474d9be6f23017c76a92 | CNC.Fc1ccc(-c2cc3ccccc3[nH]2)cc1.O=Cc1cccc(Oc2ccccc2)c1>>CN(C)C(c1cccc(Oc2ccccc2)c1)c1c(-c2ccc(F)cc2)[nH]c2ccccc12 | FC1=CC=C(C=C1)C=1NC2=CC=CC=C2C1.[Cl-].O(C1=CC=CC=C1)C=1C=C(C=[N+](C)C)C=CC1.O(C1=CC=CC=C1)C=1C=C(C=O)C=CC1.CNC>>FC1=CC=C(C=C1)C=1NC2=CC=CC=C2C1C(C1=CC(=CC=C1)OC1=CC=CC=C1)N(C)C | [CH3:1][NH:2][CH3:3].[cH:18]1[c:19](-[c:20]2[cH:21][cH:22][c:23]([F:24])[cH:25][cH:26]2)[nH:27][c:28]2[cH:29][cH:30][cH:31][cH:32][c:33]12.O=[CH:4][c:5]1[cH:6][cH:7][cH:8][c:9]([O:10][c:11]2[cH:12][cH:13][cH:14][cH:15][cH:16]2)[cH:17]1>>[CH3:1][N:2]([CH3:3])[CH:4]([c:5]1[cH:6][cH:7][cH:8][c:9]([O:10][c:11]2[cH:12][cH:1... | CNC.Fc1ccc(-c2cc3ccccc3[nH]2)cc1.O=Cc1cccc(Oc2ccccc2)c1 | CN(C)C(c1cccc(Oc2ccccc2)c1)c1c(-c2ccc(F)cc2)[nH]c2ccccc12 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 1e887ffc9d31747076f97173ff8dc6f44b0480e2cfa9f6a88ab0a775ac92e3d5 | 2d03f38884b1fbb0c0d6e6f2de31afb25102fec87f347c3a123e064c1bfef0ad | c1ccc(Oc2cccc(Cc3c(-c4ccccc4)[nH]c4ccccc34)c2)cc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[C;D1;H3:5]-[NH;D2;+0:6]-[C;D1;H3:7].[c:8]-[c:9]1:[#7;a:10]:[c:11](:[c:12]):[c:13](:[c:14]):[cH;D2;+0:15]:1>>[C;D1;H3:5]-[N;H0;D3;+0:6](-[C;D1;H3:7])-[CH;D3;+0:1](-[c:2](:[c:3]):[c:4])-[c;H0;D3;+0:15]1:[c:9](-[c:8]):[#7;a:10]:[c:11](:[c:12]):[c:13]:1:[c:14] | null | [] | null | null | null | null | The preparation was carried out in accordance with general synthesis instructions 4 from 2-(4-fluoro-phenyl)-1H-indole and (3-phenoxy-benzylidene)-dimethylammonium chloride, which had been prepared in accordance with example 44 from 3-phenoxy-benzaldehyde and dimethylamine.
Conditions: See reaction.notes.procedure_deta... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Secondary amine | Tertiary amine | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1 | c1ccccc1.c1ccccc1.c1ccccc1.c1ccc2[nH]ccc2c1 | HO- | null | null | null | CNC.Fc1ccc(-c2cc3ccccc3[nH]2)cc1.O=Cc1cccc(Oc2ccccc2)c1>>CN(C)C(c1cccc(Oc2ccccc2)c1)c1c(-c2ccc(F)cc2)[nH]c2ccccc12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-a3acf54bec8b45b7a82a1278ef642df9 | Cn1c(-c2ccc(F)c(Cl)c2)cc2ccccc21.O=Cc1cccc(Oc2ccccc2)c1>>NC(c1cccc(Oc2ccccc2)c1)c1c(-c2ccc(F)c(Cl)c2)[nH]c2ccccc12 | ClC=1C=C(C=CC1F)C=1N(C2=CC=CC=C2C1)C.[Cl-].O(C1=CC=CC=C1)C=1C=C(C=[N+](C)C)C=CC1.O(C1=CC=CC=C1)C=1C=C(C=O)C=CC1.CNC>>ClC=1C=C(C=CC1F)C=1NC2=CC=CC=C2C1C(C1=CC(=CC=C1)OC1=CC=CC=C1)N | C[n:26]1[c:17](-[c:18]2[cH:19][cH:20][c:21]([F:22])[c:23]([Cl:24])[cH:25]2)[cH:16][c:32]2[c:27]1[cH:28][cH:29][cH:30][cH:31]2.O=[CH:2][c:3]1[cH:4][cH:5][cH:6][c:7]([O:8][c:9]2[cH:10][cH:11][cH:12][cH:13][cH:14]2)[cH:15]1>>[NH2:1][CH:2]([c:3]1[cH:4][cH:5][cH:6][c:7]([O:8][c:9]2[cH:10][cH:11][cH:12][cH:13][cH:14]2)[cH:15... | Cn1c(-c2ccc(F)c(Cl)c2)cc2ccccc21.O=Cc1cccc(Oc2ccccc2)c1 | NC(c1cccc(Oc2ccccc2)c1)c1c(-c2ccc(F)c(Cl)c2)[nH]c2ccccc12 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | a8afdafc7f0c759c2b4fc93e58f1765cda8faa3c8eae6dd29aba9ff10a17bf91 | 434eff7bf4fb77b67fd204a656cbb3f325fdb7557daa5d7ed8e2ca361ee90b8e | c1ccc(Oc2cccc(Cc3c(-c4ccccc4)[nH]c4ccccc34)c2)cc1 | C-[n;H0;D3;+0:1]1:[c:2](-[c:3]):[cH;D2;+0:4]:[c:5](:[c:6]):[c:7]:1:[c:8].O=[CH;D2;+0:9]-[c:10](:[c:11]):[c:12]>>[N;D1;H2:13]-[CH;D3;+0:9](-[c:10](:[c:11]):[c:12])-[c;H0;D3;+0:4]1:[c:2](-[c:3]):[nH;D2;+0:1]:[c:7](:[c:8]):[c:5]:1:[c:6] | null | [] | null | null | null | null | The preparation was carried out in accordance with general synthesis instructions 4 from 2-(3-chloro-4-fluoro-phenyl)-methyl-1H-indole and (3-phenoxy-benzylidene)-dimethylammonium chloride, which had been prepared in accordance with example 44 from 3-phenoxy-benzaldehyde and dimethylamine.
Conditions: See reaction.note... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | Primary amine | c1cc2ccccc2[nH]1 | c1ccc2[nH]ccc2c1 | c1ccccc1.c1ccccc1.c1ccccc1.c1ccc2[nH]ccc2c1 | HO- | null | null | null | Cn1c(-c2ccc(F)c(Cl)c2)cc2ccccc21.O=Cc1cccc(Oc2ccccc2)c1>>NC(c1cccc(Oc2ccccc2)c1)c1c(-c2ccc(F)c(Cl)c2)[nH]c2ccccc12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-687c0c1e420e46059158b481be04ab45 | CNC.Cc1cccc2[nH]ccc12.O=Cc1cccc(Oc2ccccc2)c1>>Cc1cccc2[nH]cc(C(c3cccc(Oc4ccccc4)c3)N(C)C)c12 | CC1=C2C=CNC2=CC=C1.[Cl-].O(C1=CC=CC=C1)C=1C=C(C=[N+](C)C)C=CC1.O(C1=CC=CC=C1)C=1C=C(C=O)C=CC1.CNC>>CN(C(C1=CC(=CC=C1)OC1=CC=CC=C1)C1=CNC2=CC=CC(=C12)C)C | [NH:24]([CH3:25])[CH3:26].[CH3:1][c:2]1[cH:3][cH:4][cH:5][c:6]2[nH:7][cH:8][cH:9][c:27]12.O=[CH:10][c:11]1[cH:12][cH:13][cH:14][c:15]([O:16][c:17]2[cH:18][cH:19][cH:20][cH:21][cH:22]2)[cH:23]1>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][c:6]2[nH:7][cH:8][c:9]([CH:10]([c:11]3[cH:12][cH:13][cH:14][c:15]([O:16][c:17]4[cH:18][cH:19][... | CNC.Cc1cccc2[nH]ccc12.O=Cc1cccc(Oc2ccccc2)c1 | Cc1cccc2[nH]cc(C(c3cccc(Oc4ccccc4)c3)N(C)C)c12 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 1e887ffc9d31747076f97173ff8dc6f44b0480e2cfa9f6a88ab0a775ac92e3d5 | 2d03f38884b1fbb0c0d6e6f2de31afb25102fec87f347c3a123e064c1bfef0ad | c1ccc(Oc2cccc(Cc3c[nH]c4ccccc34)c2)cc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[C;D1;H3:5]-[NH;D2;+0:6]-[C;D1;H3:7].[c:8]:[c:9]1:[cH;D2;+0:10]:[c:11]:[#7;a:12]:[c:13]:1:[c:14]>>[C;D1;H3:5]-[N;H0;D3;+0:6](-[C;D1;H3:7])-[CH;D3;+0:1](-[c:2](:[c:3]):[c:4])-[c;H0;D3;+0:10]1:[c:11]:[#7;a:12]:[c:13](:[c:14]):[c:9]:1:[c:8] | null | [] | null | null | null | null | The preparation was carried out in accordance with general synthesis instructions 4 from 4-methyl-1H-indole and (3-phenoxy-benzylidene)-dimethylammonium chloride, which had been prepared in accordance with example 44 from 3-phenoxy-benzaldehyde and dimethylamine.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Secondary amine | Tertiary amine | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1.c1ccccc1.c1ccccc1 | HO- | null | null | null | CNC.Cc1cccc2[nH]ccc12.O=Cc1cccc(Oc2ccccc2)c1>>Cc1cccc2[nH]cc(C(c3cccc(Oc4ccccc4)c3)N(C)C)c12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-dc4ce530f30448019d635106dfd1829c | CNC.Clc1ccc2[nH]ccc2c1.O=Cc1ccccc1C(F)(F)F>>CN(C)C(c1ccccc1C(F)(F)F)c1c[nH]c2ccc(Cl)cc12 | ClC=1C=C2C=CNC2=CC1.[Cl-].FC(C1=C(C=[N+](C)C)C=CC=C1)(F)F.FC(C1=C(C=O)C=CC=C1)(F)F.CNC>>ClC=1C=C2C(=CNC2=CC1)C(C1=C(C=CC=C1)C(F)(F)F)N(C)C | [CH3:1][NH:2][CH3:3].[cH:15]1[cH:16][nH:17][c:18]2[cH:19][cH:20][c:21]([Cl:22])[cH:23][c:24]12.O=[CH:4][c:5]1[cH:6][cH:7][cH:8][cH:9][c:10]1[C:11]([F:12])([F:13])[F:14]>>[CH3:1][N:2]([CH3:3])[CH:4]([c:5]1[cH:6][cH:7][cH:8][cH:9][c:10]1[C:11]([F:12])([F:13])[F:14])[c:15]1[cH:16][nH:17][c:18]2[cH:19][cH:20][c:21]([Cl:22]... | CNC.Clc1ccc2[nH]ccc2c1.O=Cc1ccccc1C(F)(F)F | CN(C)C(c1ccccc1C(F)(F)F)c1c[nH]c2ccc(Cl)cc12 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 1e887ffc9d31747076f97173ff8dc6f44b0480e2cfa9f6a88ab0a775ac92e3d5 | 2d03f38884b1fbb0c0d6e6f2de31afb25102fec87f347c3a123e064c1bfef0ad | c1ccc(Cc2c[nH]c3ccccc23)cc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[C;D1;H3:5]-[NH;D2;+0:6]-[C;D1;H3:7].[c:8]:[c:9]1:[#7;a:10]:[c:11]:[cH;D2;+0:12]:[c:13]:1:[c:14]>>[C;D1;H3:5]-[N;H0;D3;+0:6](-[C;D1;H3:7])-[CH;D3;+0:1](-[c:2](:[c:3]):[c:4])-[c;H0;D3;+0:12]1:[c:11]:[#7;a:10]:[c:9](:[c:8]):[c:13]:1:[c:14] | null | [] | null | null | null | null | The preparation was carried out in accordance with general synthesis instructions 4 from 5-chloro-1H-indole and (2-trifluoromethyl-benzylidene)-dimethylammonium chloride, which had been prepared in accordance with example 44 from 2-trifluoromethyl-benzaldehyde and dimethylamine.
Conditions: See reaction.notes.procedure... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Secondary amine | Tertiary amine | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1 | c1ccccc1.c1ccc2[nH]ccc2c1 | HO- | null | null | null | CNC.Clc1ccc2[nH]ccc2c1.O=Cc1ccccc1C(F)(F)F>>CN(C)C(c1ccccc1C(F)(F)F)c1c[nH]c2ccc(Cl)cc12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-4dfdeeb8dda1463f9bf2481d09e0218e | CNC.Cc1cc2ccccc2[nH]1.O=Cc1ccc(C(F)(F)F)cc1>>Cc1[nH]c2ccccc2c1C(c1ccc(C(F)(F)F)cc1)N(C)C | CC=1NC2=CC=CC=C2C1.[Cl-].FC(C1=CC=C(C=[N+](C)C)C=C1)(F)F.FC(C1=CC=C(C=O)C=C1)(F)F.CNC>>CN(C(C1=CC=C(C=C1)C(F)(F)F)C1=C(NC2=CC=CC=C12)C)C | [NH:22]([CH3:23])[CH3:24].[CH3:1][c:2]1[nH:3][c:4]2[cH:5][cH:6][cH:7][cH:8][c:9]2[cH:10]1.O=[CH:11][c:12]1[cH:13][cH:14][c:15]([C:16]([F:17])([F:18])[F:19])[cH:20][cH:21]1>>[CH3:1][c:2]1[nH:3][c:4]2[cH:5][cH:6][cH:7][cH:8][c:9]2[c:10]1[CH:11]([c:12]1[cH:13][cH:14][c:15]([C:16]([F:17])([F:18])[F:19])[cH:20][cH:21]1)[N:2... | CNC.Cc1cc2ccccc2[nH]1.O=Cc1ccc(C(F)(F)F)cc1 | Cc1[nH]c2ccccc2c1C(c1ccc(C(F)(F)F)cc1)N(C)C | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 1e887ffc9d31747076f97173ff8dc6f44b0480e2cfa9f6a88ab0a775ac92e3d5 | 2d03f38884b1fbb0c0d6e6f2de31afb25102fec87f347c3a123e064c1bfef0ad | c1ccc(Cc2c[nH]c3ccccc23)cc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[C;D1;H3:5]-[NH;D2;+0:6]-[C;D1;H3:7].[C;D1;H3:8]-[c:9]1:[#7;a:10]:[c:11](:[c:12]):[c:13](:[c:14]):[cH;D2;+0:15]:1>>[C;D1;H3:8]-[c:9]1:[#7;a:10]:[c:11](:[c:12]):[c:13](:[c:14]):[c;H0;D3;+0:15]:1-[CH;D3;+0:1](-[N;H0;D3;+0:6](-[C;D1;H3:5])-[C;D1;H3:7])-[c:2](:[c:3]):[c:4] | null | [] | null | null | null | null | The preparation was carried out in accordance with general synthesis instructions 4 from 2-methyl-1H-indole and (4-trifluoromethyl-benzylidene)-dimethylammonium chloride, which had been prepared in accordance with example 44 from 4-trifluoromethyl-benzaldehyde and dimethylamine.
Conditions: See reaction.notes.procedure... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Secondary amine | Tertiary amine | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1.c1ccccc1 | HO- | null | null | null | CNC.Cc1cc2ccccc2[nH]1.O=Cc1ccc(C(F)(F)F)cc1>>Cc1[nH]c2ccccc2c1C(c1ccc(C(F)(F)F)cc1)N(C)C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-1345b2679a1f4255af5f660665af3050 | NOCc1ccccc1.O=C(O)CCCCCCCBr>>O=C(CCCCCCCBr)NOCc1ccccc1 | O=C1OCCN1P(=O)(N1C(OCC1)=O)Cl.C(C)N(CC)CC.Cl.C(C1=CC=CC=C1)ON.BrCCCCCCCC(=O)O>>C(C1=CC=CC=C1)ONC(CCCCCCCBr)=O | [NH2:11][O:12][CH2:13][c:14]1[cH:15][cH:16][cH:17][cH:18][cH:19]1.O[C:2](=[O:1])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][Br:10]>>[O:1]=[C:2]([CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][Br:10])[NH:11][O:12][CH2:13][c:14]1[cH:15][cH:16][cH:17][cH:18][cH:19]1 | NOCc1ccccc1.O=C(O)CCCCCCCBr | O=C(CCCCCCCBr)NOCc1ccccc1 | null | null | ClCCl | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[C:5]-[#8:6]-[NH2;D1;+0:7]>>[C:5]-[#8:6]-[NH;D2;+0:7]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4] | 78 | [{"value": 78.0, "product": "C(C1=CC=CC=C1)ONC(CCCCCCCBr)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 77.7, "product": "C(C1=CC=CC=C1)ONC(CCCCCCCBr)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 18 | HOUR | In an ice bath, 14 ml triethylamine was added to a suspension of 3.2 g (20 mmol) O-benzylhydroxylamine hydrochloride in 150 ml dichloromethane. Stirring was continued until the solution became clear. Then, 4.5 g (20 mmol) 8-bromo octanoic acid was added, followed by 5.6 g (22 mmol) bis-(2-oxo-3-oxazolidinyl)-phosphoryl... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1 | HO- | ClCCl | null | 18 | NOCc1ccccc1.O=C(O)CCCCCCCBr>ClCCl>O=C(CCCCCCCBr)NOCc1ccccc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-2b702c2e3f184302b8ebff254e729685 | O=C(CCCCCCCN1c2cccc3cccc(c23)S1(=O)=O)NOCc1ccccc1>>O=C(CCCCCCCN1c2cccc3cccc(c23)S1(=O)=O)NO | C(C1=CC=CC=C1)ONC(CCCCCCCN1S(C=2C3=C1C=CC=C3C=CC2)(=O)=O)=O>>ONC(CCCCCCCN1S(C=2C3=C1C=CC=C3C=CC2)(=O)=O)=O | c1ccc(C[O:25][NH:24][C:2](=[O:1])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][N:10]2[c:11]3[cH:12][cH:13][cH:14][c:15]4[cH:16][cH:17][cH:18][c:19]([c:20]34)[S:21]2(=[O:22])=[O:23])cc1>>[O:1]=[C:2]([CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][N:10]1[c:11]2[cH:12][cH:13][cH:14][c:15]3[cH:16][cH:17][cH:18][c:19]... | O=C(CCCCCCCN1c2cccc3cccc(c23)S1(=O)=O)NOCc1ccccc1 | O=C(CCCCCCCN1c2cccc3cccc(c23)S1(=O)=O)NO | null | [Pd] | CO | Deprotection | OtherReaction | 94fa5e5ed4a5b32c4aba0dd3c8151bfdd08491d1bc6453e9fd01d7dc3e51cd0f | 30a26bc929988d0041b9998cdccd1d65eb125114a78065ed35d40f50c965c0a7 | O=S1(=O)Nc2cccc3cccc1c23 | [C:1]-[C:2](=[O;D1;H0:3])-[#7:4]-[O;H0;D2;+0:5]-C-c1:c:c:c:c:c:1>>[C:1]-[C:2](=[O;D1;H0:3])-[#7:4]-[OH;D1;+0:5] | null | [] | null | null | null | null | 8-(1,1-Dioxo-2H-naphtho[1,8-cd]isothiazol-2-yl)-octanoic acid benzyloxyamide (0.47 g) in methanol (30 ml) was hydrogenated for 1.5 h in the presence of palladium on barium sulfate at ambient temperature and pressure. The catalyst was removed by filtration and the solvent was evaporated. The residue was purified by colu... | 10.6084/m9.figshare.5104873.v1 | null | null | null | c1ccccc1 | null | c1cc2c3c(cccc3c1)S[NH]2 | Other | [Pd].CO | null | null | O=C(CCCCCCCN1c2cccc3cccc(c23)S1(=O)=O)NOCc1ccccc1>[Pd].CO>O=C(CCCCCCCN1c2cccc3cccc(c23)S1(=O)=O)NO |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-190bbd673a414296bb77ded29b4d23dd | O=C(CCCCCCBr)NOCc1ccccc1.O=S1(=O)Nc2cccc3cccc1c23>>O=C(CCCCCCN1c2cccc3cccc(c23)S1(=O)=O)NOCc1ccccc1 | C(C1=CC=CC=C1)ONC(CCCCCCBr)=O.C1=CC2=C3C(=C1)NS(=O)(=O)C3=CC=C2.C([O-])([O-])=O.[K+].[K+]>>C(C1=CC=CC=C1)ONC(CCCCCCN1S(C=2C3=C1C=CC=C3C=CC2)(=O)=O)=O | Br[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][C:2](=[O:1])[NH:23][O:24][CH2:25][c:26]1[cH:27][cH:28][cH:29][cH:30][cH:31]1.[NH:9]1[c:10]2[cH:11][cH:12][cH:13][c:14]3[cH:15][cH:16][cH:17][c:18]([c:19]23)[S:20]1(=[O:21])=[O:22]>>[O:1]=[C:2]([CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][N:9]1[c:10]2[cH:11][cH:12][cH:13][c:14]... | O=C(CCCCCCBr)NOCc1ccccc1.O=S1(=O)Nc2cccc3cccc1c23 | O=C(CCCCCCN1c2cccc3cccc(c23)S1(=O)=O)NOCc1ccccc1 | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | ed85001971e6b69caaa4e6ac714726e893cc7ff8ac09362f619ddbe41bb0c27c | 0b054affe7e4bb904ceae512aabc19d89c93551cb46dfbc6f220fc85e5eeff75 | O=C(CCCCCCN1c2cccc3cccc(c23)S1(=O)=O)NOCc1ccccc1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[O;D1;H0:4]=[#16:5]1(=[O;D1;H0:6])-[NH;D2;+0:7]-[c:8](:[c:9]):[c:10]:[c:11]-1>>[C:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:7]1-[c:8](:[c:9]):[c:10]:[c:11]-[#16:5]-1(=[O;D1;H0:4])=[O;D1;H0:6] | null | [] | null | null | null | null | In a manner analogous to that of example 1(b), 7-bromo-heptanoic acid benzyloxyamide 0.46 g, 1.5 mmol) was reacted with 1,8-naphthalenesultam (0.3 g, 1.5 mmol) in the presence of potassium carbonate (0.2 g, 1.4 mmol) to give 7-(1,1-dioxo-2H-naphtho[1,8-cd]isothiazol-2-yl)-heptanoic acid benzyloxyamide as an amorphous s... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonamide.Primary halide | Tertiary amine | c1cc2c3c(cccc3c1)SN2 | c1cc2c3c(cccc3c1)S[NH]2 | c1cc2c3c(cccc3c1)S[NH]2.c1ccccc1 | HBr | null | null | null | O=C(CCCCCCBr)NOCc1ccccc1.O=S1(=O)Nc2cccc3cccc1c23>>O=C(CCCCCCN1c2cccc3cccc(c23)S1(=O)=O)NOCc1ccccc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-dce42a25d6154aac814679c0cf4274dc | O=C(CCCCCCCBr)NOCc1ccccc1.O=C1Nc2cccc3cccc1c23>>O=C(CCCCCCCN1C(=O)c2cccc3cccc1c23)NOCc1ccccc1 | C(C1=CC=CC=C1)ONC(CCCCCCCBr)=O.N1C(C2=C3C(C=CC=C13)=CC=C2)=O.C([O-])([O-])=O.[K+].[K+]>>C(C1=CC=CC=C1)ONC(CCCCCCCN1C(C2=C3C(C=CC=C13)=CC=C2)=O)=O | Br[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][C:2](=[O:1])[NH:23][O:24][CH2:25][c:26]1[cH:27][cH:28][cH:29][cH:30][cH:31]1.[NH:10]1[C:11](=[O:12])[c:13]2[cH:20][cH:19][cH:18][c:17]3[cH:16][cH:15][cH:14][c:21]1[c:22]23>>[O:1]=[C:2]([CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][N:10]1[C:11](=[O:12])[c:13]2[cH:1... | O=C(CCCCCCCBr)NOCc1ccccc1.O=C1Nc2cccc3cccc1c23 | O=C(CCCCCCCN1C(=O)c2cccc3cccc1c23)NOCc1ccccc1 | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 57898719c69ec2e691a59084e883c7c6aecb533a494f23939bacaf45212e2c94 | 4a6c1e88c9e8bed487b746792f88d478ff36cc235f9a217d4632e6babdebdc9a | O=C(CCCCCCCN1C(=O)c2cccc3cccc1c23)NOCc1ccccc1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[O;D1;H0:4]=[C:5]1-[NH;D2;+0:6]-[c;H0;D3;+0:7]2:[cH;D2;+0:8]:[c:9]:[c:10]:[c:11]3:[c:12]:[c:13]:[cH;D2;+0:14]:[c;H0;D3;+0:15]-1:[c:16]:3:2>>[C:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:6]1-[C:5](=[O;D1;H0:4])-[c;H0;D3;+0:15]2:[cH;D2;+0:8]:[c:9]:[c:10]:[c:11]3:[c:12]:[c:13]:[cH;D2;+0:14]:[c;H0;D3;+... | null | [] | null | null | null | null | In a manner analogous to that of example 1(b), 8-bromo-octanoic acid benzyloxyamide 0.49 g, 1.5 mmol) was reacted with benzo[cd]indol-2(1H)-one (0.25 g, 1.5 mmol) in the presence of potassium carbonate (0.2 g, 1.4 mmol) to give 8-(2-oxo-2H-benzo[cd]indol-1-yl)-octanoic acid benzyloxyamide as an amorphous solid (yield 0... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amide | Tertiary amide | c1cc2c3c(cccc3c1)NC2 | c1cc2c3c(cccc3c1)[NH]C2 | c1cc2c3c(cccc3c1)[NH]C2.c1ccccc1 | HBr | null | null | null | O=C(CCCCCCCBr)NOCc1ccccc1.O=C1Nc2cccc3cccc1c23>>O=C(CCCCCCCN1C(=O)c2cccc3cccc1c23)NOCc1ccccc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-10c22954f0c8489195af41f93b71e584 | O=C(CCCCCCBr)NOCc1ccccc1.O=C1Nc2cccc3cccc1c23>>O=C(CCCCCCN1C(=O)c2cccc3cccc1c23)NOCc1ccccc1 | C(C1=CC=CC=C1)ONC(CCCCCCBr)=O.N1C(C2=C3C(C=CC=C13)=CC=C2)=O.C([O-])([O-])=O.[K+].[K+]>>C(C1=CC=CC=C1)ONC(CCCCCCN1C(C2=C3C(C=CC=C13)=CC=C2)=O)=O | Br[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][C:2](=[O:1])[NH:22][O:23][CH2:24][c:25]1[cH:26][cH:27][cH:28][cH:29][cH:30]1.[NH:9]1[C:10](=[O:11])[c:12]2[cH:19][cH:18][cH:17][c:16]3[cH:15][cH:14][cH:13][c:20]1[c:21]23>>[O:1]=[C:2]([CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][N:9]1[C:10](=[O:11])[c:12]2[cH:13][cH:14][cH:15]... | O=C(CCCCCCBr)NOCc1ccccc1.O=C1Nc2cccc3cccc1c23 | O=C(CCCCCCN1C(=O)c2cccc3cccc1c23)NOCc1ccccc1 | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 57898719c69ec2e691a59084e883c7c6aecb533a494f23939bacaf45212e2c94 | 4a6c1e88c9e8bed487b746792f88d478ff36cc235f9a217d4632e6babdebdc9a | O=C(CCCCCCN1C(=O)c2cccc3cccc1c23)NOCc1ccccc1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[O;D1;H0:4]=[C:5]1-[NH;D2;+0:6]-[c;H0;D3;+0:7]2:[cH;D2;+0:8]:[c:9]:[c:10]:[c:11]3:[c:12]:[c:13]:[cH;D2;+0:14]:[c;H0;D3;+0:15]-1:[c:16]:3:2>>[C:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:6]1-[C:5](=[O;D1;H0:4])-[c;H0;D3;+0:15]2:[cH;D2;+0:8]:[c:9]:[c:10]:[c:11]3:[c:12]:[c:13]:[cH;D2;+0:14]:[c;H0;D3;+... | null | [] | null | null | null | null | In a manner analogous to that of example 2(b), 7-bromo-heptanoic acid benzyloxy-amide 0.46 g, 1.5 mmol) was reacted with benzo[cd]indol-2(1H)-one (0.25 g, 1.5 mmol) in the presence of potassium carbonate (0.2 g, 1.4 mmol) to give 7-(2-oxo-2H-benzo[cd]indol-1-yl)-heptanoic acid benzyloxyamide as an amorphous solid (yiel... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amide | Tertiary amide | c1cc2c3c(cccc3c1)NC2 | c1cc2c3c(cccc3c1)[NH]C2 | c1cc2c3c(cccc3c1)[NH]C2.c1ccccc1 | HBr | null | null | null | O=C(CCCCCCBr)NOCc1ccccc1.O=C1Nc2cccc3cccc1c23>>O=C(CCCCCCN1C(=O)c2cccc3cccc1c23)NOCc1ccccc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-388534def69443b5861bd8642778f4f5 | CC(C)(C)OC(=O)OC(=O)OC(C)(C)C.CCOC(=O)c1sc(N)nc1C>>CCOC(=O)c1sc(NOC(=O)OC(C)(C)C)nc1C | C(C)OC(=O)C1=C(N=C(S1)N)C.C(C)(C)(C)OC(=O)OC(=O)OC(C)(C)C>>C(C)OC(=O)C1=C(N=C(S1)NOC(=O)OC(C)(C)C)C | CC(C)(C)OC(=O)[O:10][C:11](=[O:12])[O:13][C:14]([CH3:15])([CH3:16])[CH3:17].[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[s:7][c:8]([NH2:9])[n:18][c:19]1[CH3:20]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[s:7][c:8]([NH:9][O:10][C:11](=[O:12])[O:13][C:14]([CH3:15])([CH3:16])[CH3:17])[n:18][c:19]1[CH3:20] | CC(C)(C)OC(=O)OC(=O)OC(C)(C)C.CCOC(=O)c1sc(N)nc1C | CCOC(=O)c1sc(NOC(=O)OC(C)(C)C)nc1C | null | CN(C1=CC=NC=C1)C | O1CCCC1 | Miscellaneous | OtherReaction | 573d4841f3c12e78e6b12cf91f4d399dc4182819414ba565cbb5ba4d94db2872 | 6534c82b6e71666d74191826a188dd640b31790e5c8329ff0e4034ba8a3022e5 | c1cscn1 | C-C(-C)(-C)-O-C(=O)-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#8:4]-[C:5](-[C;D1;H3:6])(-[C;D1;H3:7])-[C;D1;H3:8].[#8:9]-[C:10](=[O;D1;H0:11])-[c:12]1:[#16;a:13]:[c:14](-[NH2;D1;+0:15]):[#7;a:16]:[c:17]:1>>[#8:9]-[C:10](=[O;D1;H0:11])-[c:12]1:[#16;a:13]:[c:14](-[NH;D2;+0:15]-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#8:4]-[C:5](-[... | 72 | [{"value": 72.0, "product": "C(C)OC(=O)C1=C(N=C(S1)NOC(=O)OC(C)(C)C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 66.1, "product": "C(C)OC(=O)C1=C(N=C(S1)NOC(=O)OC(C)(C)C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 18 | HOUR | A suspension of ethyl-2-amino-4-methyl-thiazole-5-carboxylate (18.6 g, 100 mmol), di-t-butyldicarbonate (26.2 g, 120 mmol) and 4-dimethylaminopyridine (800 mg, 6.55 mmol) in dry tetrahydrofuran (300 mL) was stirred under nitrogen for 18 h. The solvent was evaporated in vacuo. The residue was suspended in dichloromethan... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Carbonic Ester.Carbonic Ester.Primary amine.Boc | Secondary amine | null | null | c1cscn1 | HO- | CN(C1=CC=NC=C1)C.O1CCCC1 | null | 18 | CC(C)(C)OC(=O)OC(=O)OC(C)(C)C.CCOC(=O)c1sc(N)nc1C>CN(C1=CC=NC=C1)C.O1CCCC1>CCOC(=O)c1sc(NOC(=O)OC(C)(C)C)nc1C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-8e2c9bc4dca442bda6037a7be6b1f8b6 | CCOC(=O)c1sc(NOC(=O)OC(C)(C)C)nc1C>>Cc1nc(NOC(=O)OC(C)(C)C)sc1C(=O)O | Cl.C(C)OC(=O)C1=C(N=C(S1)NOC(=O)OC(C)(C)C)C.[OH-].[K+]>>C(C)(C)(C)OC(=O)ONC=1SC(=C(N1)C)C(=O)O | CC[O:18][C:16]([c:15]1[c:2]([CH3:1])[n:3][c:4]([NH:5][O:6][C:7](=[O:8])[O:9][C:10]([CH3:11])([CH3:12])[CH3:13])[s:14]1)=[O:17]>>[CH3:1][c:2]1[n:3][c:4]([NH:5][O:6][C:7](=[O:8])[O:9][C:10]([CH3:11])([CH3:12])[CH3:13])[s:14][c:15]1[C:16](=[O:17])[OH:18] | CCOC(=O)c1sc(NOC(=O)OC(C)(C)C)nc1C | Cc1nc(NOC(=O)OC(C)(C)C)sc1C(=O)O | null | null | O1C(CCC1)CCO | Deprotection | Ester saponification (alkyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1cscn1 | C-C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4](:[#16;a:5]):[c:6]:[#7;a:7]>>[#16;a:5]:[c:4](-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1]):[c:6]:[#7;a:7] | null | [] | 55 | CELSIUS | null | null | A stirred solution of ethyl-2-tert-butoxycarbonyloxyamino-4-methyl-thiazole-5-carboxylate (10 g, 34.95 mmol) in tetrahydrofuran-ethanol (250 mL, 2:3) was treated with a 6N KOH solution (250 mL). The mixture was heated to 55° C. overnight. The solution was cooled to 0° C. and acidified with concd. HCl to pH 1. The solve... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1cscn1 | Other | O1C(CCC1)CCO | 55 | null | CCOC(=O)c1sc(NOC(=O)OC(C)(C)C)nc1C>O1C(CCC1)CCO>Cc1nc(NOC(=O)OC(C)(C)C)sc1C(=O)O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-95939283827b413aa59601d91194e5dd | Cc1cc(C)c(NC(=O)c2sc(NC(=O)OC(C)(C)C)nc2C)c(C)c1>>Cc1cc(C)c(NC(=O)c2sc(N)nc2C)c(C)c1 | CC1=C(C(=CC(=C1)C)C)NC(=O)C1=C(N=C(S1)NC(OC(C)(C)C)=O)C>>NC=1SC(=C(N1)C)C(=O)NC1=C(C=C(C=C1C)C)C | CC(C)(C)OC(=O)[NH:13][c:12]1[s:11][c:10]([C:8]([NH:7][c:6]2[c:4]([CH3:5])[cH:3][c:2]([CH3:1])[cH:19][c:17]2[CH3:18])=[O:9])[c:15]([CH3:16])[n:14]1>>[CH3:1][c:2]1[cH:3][c:4]([CH3:5])[c:6]([NH:7][C:8](=[O:9])[c:10]2[s:11][c:12]([NH2:13])[n:14][c:15]2[CH3:16])[c:17]([CH3:18])[cH:19]1 | Cc1cc(C)c(NC(=O)c2sc(NC(=O)OC(C)(C)C)nc2C)c(C)c1 | Cc1cc(C)c(NC(=O)c2sc(N)nc2C)c(C)c1 | null | null | FC(C(=O)O)(F)F | Reduction | Hydrogenolysis of amides/imides/carbamates | 3c33dd2a2d355ee5ba0287367e209aa147a39aa00607f0c95fb2bf1ade45d014 | c5b5dffe7dd8beebdc1baa8b5b05300a9f7079e65dcfd42ade6f8a77ff09537d | O=C(Nc1ccccc1)c1cncs1 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[c:2]1:[#16;a:3]:[c:4](-[C:5](-[#7:6])=[O;D1;H0:7]):[c:8]:[#7;a:9]:1>>[#7:6]-[C:5](=[O;D1;H0:7])-[c:4]1:[#16;a:3]:[c:2](-[NH2;D1;+0:1]):[#7;a:9]:[c:8]:1 | 91.4 | [{"value": 91.0, "product": "NC=1SC(=C(N1)C)C(=O)NC1=C(C=C(C=C1C)C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 91.4, "product": "NC=1SC(=C(N1)C)C(=O)NC1=C(C=C(C=C1C)C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of [5-[[(2,4,6-Trimethylphenyl)amino]carbonyl]-4-methyl-2-thiazolyl]carbamic acid, 1,1-dimethylethyl ester (10 g, 26.63 mmol) in trifluoroacetic acid (100 mL) was stirred at rt for 3 h. The solution was concentrated under reduced pressure and the residue was diluted with EtOAc (700 mL), washed with 5% aq. KH... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Primary amine | null | null | c1ccccc1.c1cscn1 | HO- | FC(C(=O)O)(F)F | null | null | Cc1cc(C)c(NC(=O)c2sc(NC(=O)OC(C)(C)C)nc2C)c(C)c1>FC(C(=O)O)(F)F>Cc1cc(C)c(NC(=O)c2sc(N)nc2C)c(C)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-1489de592ed543aead9b9b3cc9eda428 | CC(C)(C)OC(=O)OC(=O)OC(C)(C)C.CCOC(=O)c1sc(N)nc1C(F)(F)F>>CCOC(=O)c1sc(NOC(=O)OC(C)(C)C)nc1C(F)(F)F | C(C)OC(=O)C1=C(N=C(S1)N)C(F)(F)F.C(C)(C)(C)OC(=O)OC(=O)OC(C)(C)C>>C(C)OC(=O)C1=C(N=C(S1)NOC(=O)OC(C)(C)C)C(F)(F)F | CC(C)(C)OC(=O)[O:10][C:11](=[O:12])[O:13][C:14]([CH3:15])([CH3:16])[CH3:17].[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[s:7][c:8]([NH2:9])[n:18][c:19]1[C:20]([F:21])([F:22])[F:23]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[s:7][c:8]([NH:9][O:10][C:11](=[O:12])[O:13][C:14]([CH3:15])([CH3:16])[CH3:17])[n:18][c:19]1[C:20]([F:21])... | CC(C)(C)OC(=O)OC(=O)OC(C)(C)C.CCOC(=O)c1sc(N)nc1C(F)(F)F | CCOC(=O)c1sc(NOC(=O)OC(C)(C)C)nc1C(F)(F)F | null | CN(C1=CC=NC=C1)C | ClCCl | Miscellaneous | OtherReaction | 573d4841f3c12e78e6b12cf91f4d399dc4182819414ba565cbb5ba4d94db2872 | 6534c82b6e71666d74191826a188dd640b31790e5c8329ff0e4034ba8a3022e5 | c1cscn1 | C-C(-C)(-C)-O-C(=O)-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#8:4]-[C:5](-[C;D1;H3:6])(-[C;D1;H3:7])-[C;D1;H3:8].[#8:9]-[C:10](=[O;D1;H0:11])-[c:12]1:[#16;a:13]:[c:14](-[NH2;D1;+0:15]):[#7;a:16]:[c:17]:1>>[#8:9]-[C:10](=[O;D1;H0:11])-[c:12]1:[#16;a:13]:[c:14](-[NH;D2;+0:15]-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#8:4]-[C:5](-[... | 92 | [{"value": 92.0, "product": "C(C)OC(=O)C1=C(N=C(S1)NOC(=O)OC(C)(C)C)C(F)(F)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 87.7, "product": "C(C)OC(=O)C1=C(N=C(S1)NOC(=O)OC(C)(C)C)C(F)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1.5 | HOUR | A suspension of ethyl-2-amino-4-trifluoromethyl-thiazole-5-carboxylate (5.05 g, 21.02 mmol), di-t-butyldicarbonate (4.82 g, 22.07 mmol) and 4-dimethylaminopyridine (260 mg, 2.1 mmol) in dichloromethane (209 mL) was stirred under nitrogen for 1.5 h. The solvent was evaporated in vacuo. The residue was chromatographed on... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Carbonic Ester.Carbonic Ester.Primary amine.Boc | Secondary amine | null | null | c1cscn1 | HO- | CN(C1=CC=NC=C1)C.ClCCl | null | 1.5 | CC(C)(C)OC(=O)OC(=O)OC(C)(C)C.CCOC(=O)c1sc(N)nc1C(F)(F)F>CN(C1=CC=NC=C1)C.ClCCl>CCOC(=O)c1sc(NOC(=O)OC(C)(C)C)nc1C(F)(F)F |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-9428c79723c14198955b974363dbc33e | CCOC(=O)c1sc(NOC(=O)OC(C)(C)C)nc1C(F)(F)F>>CC(C)(C)OC(=O)ONc1nc(C(F)(F)F)c(C(=O)O)s1 | Cl.C(C)OC(=O)C1=C(N=C(S1)NOC(=O)OC(C)(C)C)C(F)(F)F.[OH-].[Na+]>>C(C)(C)(C)OC(=O)ONC=1SC(=C(N1)C(F)(F)F)C(=O)O | CC[O:20][C:18]([c:17]1[c:12]([C:13]([F:14])([F:15])[F:16])[n:11][c:10]([NH:9][O:8][C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[s:21]1)=[O:19]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[O:8][NH:9][c:10]1[n:11][c:12]([C:13]([F:14])([F:15])[F:16])[c:17]([C:18](=[O:19])[OH:20])[s:21]1 | CCOC(=O)c1sc(NOC(=O)OC(C)(C)C)nc1C(F)(F)F | CC(C)(C)OC(=O)ONc1nc(C(F)(F)F)c(C(=O)O)s1 | null | null | CO | Deprotection | Ester saponification (alkyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1cscn1 | C-C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4](:[#16;a:5]):[c:6]:[#7;a:7]>>[#16;a:5]:[c:4](-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1]):[c:6]:[#7;a:7] | null | [] | null | null | 8 | HOUR | A stirred solution of ethyl-2-tert-butoxycarbonyloxyamino-4-trifluoromethyl-thiazole-5-carboxylate (6.5 g, 19.1 mmol) in methanol (100 mL) was treated with a 1N aq. NaOH solution (573 mL). The mixture was stirred at rt overnight. The solution was cooled to 0° C. and acidified with a 6 M aq. HCl solution to pH 1 and ext... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1cscn1 | Other | CO | null | 8 | CCOC(=O)c1sc(NOC(=O)OC(C)(C)C)nc1C(F)(F)F>CO>CC(C)(C)OC(=O)ONc1nc(C(F)(F)F)c(C(=O)O)s1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-f75c4e99532d4a508cd22f8965bec48f | CCOC(=O)c1sc(N)nc1C.O=C(Cl)OCc1ccccc1>>CCOC(=O)c1sc(NOC(=O)OCc2ccccc2)nc1C | ClC(=O)OCC1=CC=CC=C1.C(=O)(O)[O-].[Na+].C(C)OC(=O)C1=C(N=C(S1)N)C.ClC(=O)OCC1=CC=CC=C1>>C(C)OC(=O)C1=C(N=C(S1)NOC(=O)OCC1=CC=CC=C1)C | [CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[s:7][c:8]([NH2:9])[n:21][c:22]1[CH3:23].Cl[C:11](=[O:12])[O:13][CH2:14][c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[s:7][c:8]([NH:9][O:10][C:11](=[O:12])[O:13][CH2:14][c:15]2[cH:16][cH:17][cH:18][cH:19][cH:20]2)[n:21][c:22]1[CH3:23] | CCOC(=O)c1sc(N)nc1C.O=C(Cl)OCc1ccccc1 | CCOC(=O)c1sc(NOC(=O)OCc2ccccc2)nc1C | null | null | ClCCl.C1CCOC1.O | Acylation | OtherReaction | 45b9b0e25c597562683452adce8466688667b23f75e19af296c1a5a031c98ee1 | 464a9ef6461bb6ec6a8915b72ac7ce5008d5625d8040f6a6c7cc16c6435e26ae | O=C(OCc1ccccc1)ONc1nccs1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C:4].[#8:5]-[C:6](=[O;D1;H0:7])-[c:8]1:[#16;a:9]:[c:10](-[NH2;D1;+0:11]):[#7;a:12]:[c:13]:1>>[#8:5]-[C:6](=[O;D1;H0:7])-[c:8]1:[#16;a:9]:[c:10](-[NH;D2;+0:11]-[#8:14]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C:4]):[#7;a:12]:[c:13]:1 | 48 | [{"value": 48.0, "product": "C(C)OC(=O)C1=C(N=C(S1)NOC(=O)OCC1=CC=CC=C1)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | A 3 M aq. NaHCO3 solution (10 mL, 30 mmol) was added to a stirred solution of ethyl-2-amino-4-methyl-thiazole-5-carboxylate (372 mg, 2 mmol) in THF (20 mL) at 0–5° C. Benzyl chloroformate (500 μL) was added. After 2 h, additional benzyl chloroformate (500 μL) and the biphasic solution was stirred for an additional 2 h ... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Ether.Primary amine | Ether.Secondary amine | null | null | c1cscn1.c1ccccc1 | null | ClCCl.C1CCOC1.O | null | 2 | CCOC(=O)c1sc(N)nc1C.O=C(Cl)OCc1ccccc1>ClCCl.C1CCOC1.O>CCOC(=O)c1sc(NOC(=O)OCc2ccccc2)nc1C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-8e323e0dfaa24bf8871d0a446d323fd4 | CCOC(=O)c1sc(N)nc1C.CS(=O)(=O)Cl>>CCOC(=O)c1sc(NS(C)(=O)=O)nc1C | C(C)OC(=O)C1=C(N=C(S1)N)C.CS(=O)(=O)Cl>>C(C)OC(=O)C1=C(N=C(S1)NS(=O)(=O)C)C | [CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[s:7][c:8]([NH2:9])[n:14][c:15]1[CH3:16].Cl[S:10]([CH3:11])(=[O:12])=[O:13]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[s:7][c:8]([NH:9][S:10]([CH3:11])(=[O:12])=[O:13])[n:14][c:15]1[CH3:16] | CCOC(=O)c1sc(N)nc1C.CS(=O)(=O)Cl | CCOC(=O)c1sc(NS(C)(=O)=O)nc1C | null | null | ClCCl.N1=CC=CC=C1 | Acylation | Sulfonamide synthesis (Schotten-Baumann) primary amine | 4c44ef6d7646f6ef25dd125d2c32c713d8dcae7c603407faa5f0fb810631670e | 8fce8115d8a725afa92eb3910ded29d4c852e5133eba78a425054f41f7142603 | c1cscn1 | Cl-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4].[#8:5]-[C:6](=[O;D1;H0:7])-[c:8]1:[#16;a:9]:[c:10](-[NH2;D1;+0:11]):[#7;a:12]:[c:13]:1>>[#8:5]-[C:6](=[O;D1;H0:7])-[c:8]1:[#16;a:9]:[c:10](-[NH;D2;+0:11]-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4]):[#7;a:12]:[c:13]:1 | 87 | [{"value": 87.0, "product": "C(C)OC(=O)C1=C(N=C(S1)NS(=O)(=O)C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 86.6, "product": "C(C)OC(=O)C1=C(N=C(S1)NS(=O)(=O)C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A stirred solution of ethyl-2-amino-4-methyl-thiazole-5-carboxylate (558 mg, 3 mmol) in dichloromethane (15 mL) and pyridine (5 mL) was treated with methanesulfonyl chloride (687 mg, 6 mmol) at rt overnight. The solution was diluted with dichloromethane (50 mL) and washed with 2N aq. HCl solution (15 mL, 3×), dried (Mg... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Sulfonyl halide | Sulfonamide | null | null | c1cscn1 | HCl | ClCCl.N1=CC=CC=C1 | null | null | CCOC(=O)c1sc(N)nc1C.CS(=O)(=O)Cl>ClCCl.N1=CC=CC=C1>CCOC(=O)c1sc(NS(C)(=O)=O)nc1C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-59e03f216bec45e885b78045a0b57aed | CCOC(=O)c1sc(NS(C)(=O)=O)nc1C>>Cc1nc(NS(C)(=O)=O)sc1C(=O)O | Cl.C(C)OC(=O)C1=C(N=C(S1)NS(=O)(=O)C)C.[OH-].[Na+]>>CS(=O)(=O)NC=1SC(=C(N1)C)C(=O)O | CC[O:14][C:12]([c:11]1[c:2]([CH3:1])[n:3][c:4]([NH:5][S:6]([CH3:7])(=[O:8])=[O:9])[s:10]1)=[O:13]>>[CH3:1][c:2]1[n:3][c:4]([NH:5][S:6]([CH3:7])(=[O:8])=[O:9])[s:10][c:11]1[C:12](=[O:13])[OH:14] | CCOC(=O)c1sc(NS(C)(=O)=O)nc1C | Cc1nc(NS(C)(=O)=O)sc1C(=O)O | null | null | CO | Deprotection | Ester saponification (alkyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1cscn1 | C-C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4](:[#16;a:5]):[c:6]:[#7;a:7]>>[#16;a:5]:[c:4](-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1]):[c:6]:[#7;a:7] | null | [] | null | null | 8 | HOUR | A stirred solution of Ethyl-2-[(methylsulfonyl)amino]-4-methyl-thiazole-5-carboxylate (300 mg, 1.14 mmol) in methanol (9 mL) was treated with a 1N NaOH solution (28.4 mL, 28.4 mmol). The mixture was stirred at rt overnight. The solution was cooled to 0° C. and acidified with 6N aq. HCl solution to pH 1. The solution wa... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1cscn1 | Other | CO | null | 8 | CCOC(=O)c1sc(NS(C)(=O)=O)nc1C>CO>Cc1nc(NS(C)(=O)=O)sc1C(=O)O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-7b8cb11dcdcf4486a625205a9d01af52 | CC(C)(C)OC(=O)OC(=O)OC(C)(C)C.CCOC(=O)c1cnc(N)s1>>CCOC(=O)c1sc(NOC(=O)OC(C)(C)C)nc1C | C(C)OC(=O)C1=CN=C(S1)N.C(C)(C)(C)OC(=O)OC(=O)OC(C)(C)C.O1CCCC1>>C(C)OC(=O)C1=C(N=C(S1)NOC(=O)OC(C)(C)C)C | CC(C)(C)OC(=O)[O:10][C:11](=[O:12])[O:13][C:14]([CH3:15])([CH3:16])[CH3:17].[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[s:7][c:8]([NH2:9])[n:18][cH:19]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[s:7][c:8]([NH:9][O:10][C:11](=[O:12])[O:13][C:14]([CH3:15])([CH3:16])[CH3:17])[n:18][c:19]1[CH3:20] | CC(C)(C)OC(=O)OC(=O)OC(C)(C)C.CCOC(=O)c1cnc(N)s1 | CCOC(=O)c1sc(NOC(=O)OC(C)(C)C)nc1C | null | CN(C1=CC=NC=C1)C | null | C-C Coupling | OtherReaction | fc103691cbf8d10076de901c3ed38b08dd9e349f2a648885626a9e90fb13bfe5 | 718843329b9c43fc61f59e89f6a61edd702695d27eaeeab096d4a7bcb6000080 | c1cscn1 | C-C(-C)(-C)-O-C(=O)-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#8:4]-[C:5](-[C;D1;H3:6])(-[C;D1;H3:7])-[C;D1;H3:8].[C:9]-[#8:10]-[C:11](=[O;D1;H0:12])-[c:13]1:[#16;a:14]:[c:15](-[NH2;D1;+0:16]):[#7;a:17]:[cH;D2;+0:18]:1>>[C:9]-[#8:10]-[C:11](=[O;D1;H0:12])-[c:13]1:[#16;a:14]:[c:15](-[NH;D2;+0:16]-[O;H0;D2;+0:1]-[C:2](=[O;D1;H... | 70 | [{"value": 70.0, "product": "C(C)OC(=O)C1=C(N=C(S1)NOC(=O)OC(C)(C)C)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A suspension of ethyl-2-amino-thiazole-5-carboxylate (972 mg, 6 mmol, B. Plouvler, C. Bailly, R. Houssin, j-P. Henlchart Heterocyles 32(4), 693–701, 1991 and H. J. Becker, J. de Jonge Rec. Trav. Chim, 61, 463, 1942), di-t-butyldicarbonate (1.94 g, 9 mmol) and 4-dimethylaminopyridine (73 mg, 0.6 mmol) in dry tetrahydrof... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Carbonic Ester.Carbonic Ester.Primary amine.Boc | Secondary amine | c1cscn1 | c1cscn1 | c1cscn1 | HO- | CN(C1=CC=NC=C1)C | null | null | CC(C)(C)OC(=O)OC(=O)OC(C)(C)C.CCOC(=O)c1cnc(N)s1>CN(C1=CC=NC=C1)C>CCOC(=O)c1sc(NOC(=O)OC(C)(C)C)nc1C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-f30f6fee1bf24541893678b7a7c2463b | CCOC(=O)c1sc(NOC(=O)OC(C)(C)C)nc1C>>CC(C)(C)OC(=O)ONc1ncc(C(=O)O)s1 | C(C)OC(=O)C1=C(N=C(S1)NOC(=O)OC(C)(C)C)C.[OH-].[Na+]>>C(C)(C)(C)OC(=O)ONC=1SC(=CN1)C(=O)O | CC[O:16][C:14]([c:13]1[c:12](C)[n:11][c:10]([NH:9][O:8][C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[s:17]1)=[O:15]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[O:8][NH:9][c:10]1[n:11][cH:12][c:13]([C:14](=[O:15])[OH:16])[s:17]1 | CCOC(=O)c1sc(NOC(=O)OC(C)(C)C)nc1C | CC(C)(C)OC(=O)ONc1ncc(C(=O)O)s1 | null | null | O1C(CCC1)CO | Deprotection | OtherReaction | 0daaaff4e26641512f45c4a3a3599acca9d94cce9b964eb5e9d934cefb85f4c2 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1cscn1 | C-C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]1:[#16;a:5]:[c:6]:[#7;a:7]:[c;H0;D3;+0:8]:1-C>>[O;D1;H0:3]=[C:2](-[OH;D1;+0:1])-[c:4]1:[#16;a:5]:[c:6]:[#7;a:7]:[cH;D2;+0:8]:1 | null | [] | null | null | 24 | HOUR | A stirred solution of ethyl-2-tert-butoxycarbonyloxyamino-4-methyl-thiazole-5-carboxylate (1.1 g, 4.2 mmol) in tetrahydrofuran-methanol (80 mL, 1:1) was treated with a 6N aq. NaOH solution (20 mL, 120 mmol). The mixture was stirred at rt for 24 h. Most of THF and methanol were removed by distillation under reduced pres... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | c1cscn1 | c1cscn1 | c1cscn1 | Other | O1C(CCC1)CO | null | 24 | CCOC(=O)c1sc(NOC(=O)OC(C)(C)C)nc1C>O1C(CCC1)CO>CC(C)(C)OC(=O)ONc1ncc(C(=O)O)s1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-4cce3d012348490bb45fe8a36bc03cd3 | O=[N+]([O-])c1cccc(O)c1>>O=[N+]([O-])c1ccccc1 | [N+](=O)([O-])C=1C=C(C=CC1)O.C(=O)([O-])[O-].[K+].[K+].[Na+].[I-]>>[N+](=O)([O-])C1=CC=CC=C1 | O[c:8]1[cH:7][cH:6][cH:5][c:4]([N+:2](=[O:1])[O-:3])[cH:9]1>>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][cH:6][cH:7][cH:8][cH:9]1 | O=[N+]([O-])c1cccc(O)c1 | O=[N+]([O-])c1ccccc1 | null | null | CN(C)C=O | Reduction | OtherReaction | 0b15258bc3b0efb75716a15093f26f3ade1fb35d0d50493dcb65925b9449d16a | 27ebe27a5e17883303ac9a42d30f2cb918c0044de7ff3c79776e1ddb80cc53d9 | c1ccccc1 | O-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5]>>[c:5]:[c:4]:[cH;D2;+0:1]:[c:2]:[c:3] | null | [] | 120 | CELSIUS | null | null | A suspension of 3-nitrophenol (837 mg, 6.02 mmole), 1-chloro-3-[imidazo-1-yl]-propane (871 mg, 1 eq), K2CO3 (3.3 gm, 4 eq) and NaI (1.0 gm, 1.1 eq) in DMF was heated at 120° C. for 6 hr. After cooling to RT, the reaction was filtered and the filter cake was washed with DMF. The solvent was removed from the filtrate and... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic alcohol | null | c1ccccc1 | c1ccccc1 | c1ccccc1 | Other | CN(C)C=O | 120 | null | O=[N+]([O-])c1cccc(O)c1>CN(C)C=O>O=[N+]([O-])c1ccccc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-68f4737b6c484d558c81c99a24e5ed31 | CCN=C=O.Nc1nc2ccc(Cl)cc2s1>>CCNC(=O)Nc1nc2ccc(Cl)cc2s1 | ClC1=CC2=C(N=C(S2)N)C=C1.C(C)N=C=O.C(C)N(CC)CC>>ClC1=CC2=C(N=C(S2)NC(=O)NCC)C=C1 | [CH3:1][CH2:2][N:3]=[C:4]=[O:5].[NH2:6][c:7]1[n:8][c:9]2[cH:10][cH:11][c:12]([Cl:13])[cH:14][c:15]2[s:16]1>>[CH3:1][CH2:2][NH:3][C:4](=[O:5])[NH:6][c:7]1[n:8][c:9]2[cH:10][cH:11][c:12]([Cl:13])[cH:14][c:15]2[s:16]1 | CCN=C=O.Nc1nc2ccc(Cl)cc2s1 | CCNC(=O)Nc1nc2ccc(Cl)cc2s1 | null | null | CN(C)C=O | Acylation | Urea synthesis via isocyanate and primary amine | d39cd7dc52a79bb265ff8ef61ef7bf9dc7f7b5fb0150fcb4881bdfb18ab9c380 | a5dc801930c765d2a435a0a2973e50163c305ba8e7641d6adbcc1550b7b96de7 | c1ccc2scnc2c1 | [C;D1;H3:1]-[C:2]-[N;H0;D2;+0:3]=[C;H0;D2;+0:4]=[O;D1;H0:5].[NH2;D1;+0:6]-[c:7]1:[#16;a:8]:[c:9]:[c:10]:[#7;a:11]:1>>[C;D1;H3:1]-[C:2]-[NH;D2;+0:3]-[C;H0;D3;+0:4](=[O;D1;H0:5])-[NH;D2;+0:6]-[c:7]1:[#16;a:8]:[c:9]:[c:10]:[#7;a:11]:1 | null | [] | null | null | null | null | Three grams of 6-chloro-1,3-benzothiazol-2-amine was dissolved in about 50 mL DMF. Next, about 2.5 mL of EtNCO was added followed by about 3.2 mL of triethylamine. The solution was allowed to react at about 80° C. for about 8 hours. The reaction solvent was then removed in vacuo and the crude oil was taken up in ether.... | 10.6084/m9.figshare.5104873.v1 | null | Isocyanate.Primary amine | Urea | null | null | c1ccc2scnc2c1 | null | CN(C)C=O | null | null | CCN=C=O.Nc1nc2ccc(Cl)cc2s1>CN(C)C=O>CCNC(=O)Nc1nc2ccc(Cl)cc2s1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-8fdf60b6ede54c5a9ab0db4f301291f1 | CCNC(=O)Nc1nc2ccc(Cl)cc2s1.O=[N+]([O-])O>>CCNC(=O)Nc1nc2cc([N+](=O)[O-])c(Cl)cc2s1 | ClC1=CC2=C(N=C(S2)NC(=O)NCC)C=C1.[N+](=O)(O)[O-]>>ClC1=CC2=C(N=C(S2)NC(=O)NCC)C=C1[N+](=O)[O-] | [CH3:1][CH2:2][NH:3][C:4](=[O:5])[NH:6][c:7]1[n:8][c:9]2[cH:10][cH:11][c:15]([Cl:16])[cH:17][c:18]2[s:19]1.O[N+:12](=[O:13])[O-:14]>>[CH3:1][CH2:2][NH:3][C:4](=[O:5])[NH:6][c:7]1[n:8][c:9]2[cH:10][c:11]([N+:12](=[O:13])[O-:14])[c:15]([Cl:16])[cH:17][c:18]2[s:19]1 | CCNC(=O)Nc1nc2ccc(Cl)cc2s1.O=[N+]([O-])O | CCNC(=O)Nc1nc2cc([N+](=O)[O-])c(Cl)cc2s1 | null | null | S(O)(O)(=O)=O | Functional Group Addition | Aromatic nitration with HNO3 | 668b9c8f526506609a3c1bae67dc3186759376057ca0511251a32d7865e504f8 | ddce49825c02b8965f10c8d99e3c841d26e1f136da6037b417c09313e6d73097 | c1ccc2scnc2c1 | O-[N+;H0;D3:1](-[O;-;D1;H0:2])=[O;D1;H0:3].[Cl;D1;H0:4]-[c:5]1:[c:6]:[c:7]2:[#16;a:8]:[c:9]:[#7;a:10]:[c:11]:2:[c:12]:[cH;D2;+0:13]:1>>[Cl;D1;H0:4]-[c:5]1:[c:6]:[c:7]2:[#16;a:8]:[c:9]:[#7;a:10]:[c:11]:2:[c:12]:[c;H0;D3;+0:13]:1-[N+;H0;D3:1](-[O;-;D1;H0:2])=[O;D1;H0:3] | null | [] | null | null | 1 | HOUR | Three grams of N-(6-chloro-1,3-benzothiazol-2-yl)-N′-ethylurea was dissolved in about 15 mL of concentrated sulfuric acid (about 92–94%). The solution was cooled to about 0–5° C. About 1.5 g of ice cooled nitric acid (70% concentration was used, though this is not necessary) was added dropwise. The reaction was held at... | 10.6084/m9.figshare.5104873.v1 | null | Nitrate | Nitro group | c1ccc2scnc2c1 | c1ccc2scnc2c1 | c1ccc2scnc2c1 | HO- | S(O)(O)(=O)=O | null | 1 | CCNC(=O)Nc1nc2ccc(Cl)cc2s1.O=[N+]([O-])O>S(O)(O)(=O)=O>CCNC(=O)Nc1nc2cc([N+](=O)[O-])c(Cl)cc2s1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-6eca5615015f4ce68df2769bea908bce | N#C[S-].N#Cc1ccc(N)cc1>>N#Cc1ccc2nc(N)sc2c1 | C(C1=CC=CC=C1)#N.[S-]C#N.[K+].NC1=CC=C(C#N)C=C1.BrBr>>NC=1SC2=C(N1)C=CC(=C2)C#N | [C:8](#[N:9])[S-:10].[N:1]#[C:2][c:3]1[cH:4][cH:5][c:6]([NH2:7])[cH:11][cH:12]1>>[N:1]#[C:2][c:3]1[cH:4][cH:5][c:6]2[n:7][c:8]([NH2:9])[s:10][c:11]2[cH:12]1 | N#C[S-].N#Cc1ccc(N)cc1 | N#Cc1ccc2nc(N)sc2c1 | null | null | O.C(C)(=O)O | Aromatic Heterocycle Formation | OtherReaction | 09d23668c864254f076a396c221fe470e495edd36b92b7e2edc27fa4162c1052 | c7c78474f6971eeaa7d180c68d4a8af29cb23110025e531bca1233dc3931475c | c1ccc2scnc2c1 | [N;H0;D1;+0:1]#[C;H0;D2;+0:2]-[S-;H0;D1:3].[NH2;D1;+0:4]-[c:5](:[c:6]):[cH;D2;+0:7]:[c:8]:[c:9]>>[NH2;D1;+0:1]-[c;H0;D3;+0:2]1:[n;H0;D2;+0:4]:[c:5](:[c:6]):[c;H0;D3;+0:7](:[c:8]:[c:9]):[s;H0;D2;+0:3]:1 | null | [] | null | null | 16 | HOUR | 4-Aminobenzonitrile is dissolved in acetic acid (or a weak protic acid) and the solution is cooled to about 16–30° C., preferably 16–18° C. Potassium thiocyanate is added and the flask is then equipped with an addition funnel. The addition funnel is charged with bromine and acetic acid. This dark solution is then added... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile.Primary amine | Primary amine | c1ccccc1 | c1ccc2scnc2c1 | c1ccc2scnc2c1 | null | O.C(C)(=O)O | null | 16 | N#C[S-].N#Cc1ccc(N)cc1>O.C(C)(=O)O>N#Cc1ccc2nc(N)sc2c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-0c848bca2734433db737a84e3267c158 | CCN(CC)CC.CN(C)C=O.N#Cc1ccc2nc(N)sc2c1>>CCNC(=O)Nc1nc2ccc(C#N)cc2s1 | C(C)N(CC)CC.NC=1SC2=C(N1)C=CC(=C2)C#N.CN(C=O)C>>C(#N)C1=CC2=C(N=C(S2)NC(=O)NCC)C=C1 | CC[N:3](CC)[CH2:2][CH3:1].CN(C)[CH:4]=[O:5].[NH2:6][c:7]1[n:8][c:9]2[cH:10][cH:11][c:12]([C:13]#[N:14])[cH:15][c:16]2[s:17]1>>[CH3:1][CH2:2][NH:3][C:4](=[O:5])[NH:6][c:7]1[n:8][c:9]2[cH:10][cH:11][c:12]([C:13]#[N:14])[cH:15][c:16]2[s:17]1 | CCN(CC)CC.CN(C)C=O.N#Cc1ccc2nc(N)sc2c1 | CCNC(=O)Nc1nc2ccc(C#N)cc2s1 | null | null | null | Acylation | OtherReaction | e77d698eff83e8794b05b3ce5fedd9ef96c82455e86eba1122b49fc0626d6db2 | bcb50edc2d59fe372b4cfb78843db7d4062ca25f84556b960638045f86f9e947 | c1ccc2scnc2c1 | C-C-[N;H0;D3;+0:1](-C-C)-[C:2]-[C;D1;H3:3].C-N(-C)-[CH;D2;+0:4]=[O;D1;H0:5].[NH2;D1;+0:6]-[c:7]1:[#16;a:8]:[c:9]:[c:10]:[#7;a:11]:1>>[C;D1;H3:3]-[C:2]-[NH;D2;+0:1]-[C;H0;D3;+0:4](=[O;D1;H0:5])-[NH;D2;+0:6]-[c:7]1:[#16;a:8]:[c:9]:[c:10]:[#7;a:11]:1 | null | [] | 80 | CELSIUS | 4 | HOUR | 2-Amino-1,3-benzothiazole-6-carbonitrile is dissolved in a polar aprotic solvent, preferrably dimethylformamide. R3NCO is added, followed by an alkyl amine base, preferably triethylamine and the solution is heated to about 70–90° C., preferably about 80° C., under good agitation. The solution is allowed to stir for abo... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Primary amine.Tertiary amine | Urea | null | null | c1ccc2scnc2c1 | Other | null | 80 | 4 | CCN(CC)CC.CN(C)C=O.N#Cc1ccc2nc(N)sc2c1>>CCNC(=O)Nc1nc2ccc(C#N)cc2s1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-5037c9c33a5a49e9b0b5c20797e25f9c | N#C[S-].N#Cc1ccc(N)cc1>>N#Cc1ccc2nc(N)sc2c1 | C(C1=CC=CC=C1)#N.[S-]C#N.[K+].NC1=CC=C(C#N)C=C1.BrBr>>NC=1SC2=C(N1)C=CC(=C2)C#N | [C:8](#[N:9])[S-:10].[N:1]#[C:2][c:3]1[cH:4][cH:5][c:6]([NH2:7])[cH:11][cH:12]1>>[N:1]#[C:2][c:3]1[cH:4][cH:5][c:6]2[n:7][c:8]([NH2:9])[s:10][c:11]2[cH:12]1 | N#C[S-].N#Cc1ccc(N)cc1 | N#Cc1ccc2nc(N)sc2c1 | null | null | O.C(C)(=O)O | Aromatic Heterocycle Formation | OtherReaction | 09d23668c864254f076a396c221fe470e495edd36b92b7e2edc27fa4162c1052 | c7c78474f6971eeaa7d180c68d4a8af29cb23110025e531bca1233dc3931475c | c1ccc2scnc2c1 | [N;H0;D1;+0:1]#[C;H0;D2;+0:2]-[S-;H0;D1:3].[NH2;D1;+0:4]-[c:5](:[c:6]):[cH;D2;+0:7]:[c:8]:[c:9]>>[NH2;D1;+0:1]-[c;H0;D3;+0:2]1:[n;H0;D2;+0:4]:[c:5](:[c:6]):[c;H0;D3;+0:7](:[c:8]:[c:9]):[s;H0;D2;+0:3]:1 | 67.4 | [{"value": 67.4, "product": "NC=1SC2=C(N1)C=CC(=C2)C#N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 16 | CELSIUS | 16 | HOUR | Two grams of 4-aminobenzonitrile was dissolved in about 40 mL acetic acid and the solution was cooled to about 16° C. About 3.3 g of potassium thiocyanate was added and the flask was equipped with an addition funnel. The addition funnel was charged with about 2.7 g bromine and about 5 mL acetic acid. This dark solution... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile.Primary amine | Primary amine | c1ccccc1 | c1ccc2scnc2c1 | c1ccc2scnc2c1 | null | O.C(C)(=O)O | 16 | 16 | N#C[S-].N#Cc1ccc(N)cc1>O.C(C)(=O)O>N#Cc1ccc2nc(N)sc2c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-4bb201544c5043cd978fe2b16f5062ab | CCN=C=O.N#Cc1ccc2nc(N)sc2c1>>CCNC(=O)Nc1nc2ccc(C#N)cc2s1 | NC=1SC2=C(N1)C=CC(=C2)C#N.C(C)N=C=O.C(C)N(CC)CC>>C(#N)C1=CC2=C(N=C(S2)NC(=O)NCC)C=C1 | [CH3:1][CH2:2][N:3]=[C:4]=[O:5].[NH2:6][c:7]1[n:8][c:9]2[cH:10][cH:11][c:12]([C:13]#[N:14])[cH:15][c:16]2[s:17]1>>[CH3:1][CH2:2][NH:3][C:4](=[O:5])[NH:6][c:7]1[n:8][c:9]2[cH:10][cH:11][c:12]([C:13]#[N:14])[cH:15][c:16]2[s:17]1 | CCN=C=O.N#Cc1ccc2nc(N)sc2c1 | CCNC(=O)Nc1nc2ccc(C#N)cc2s1 | null | null | CN(C=O)C | Acylation | Urea synthesis via isocyanate and primary amine | d39cd7dc52a79bb265ff8ef61ef7bf9dc7f7b5fb0150fcb4881bdfb18ab9c380 | a5dc801930c765d2a435a0a2973e50163c305ba8e7641d6adbcc1550b7b96de7 | c1ccc2scnc2c1 | [C;D1;H3:1]-[C:2]-[N;H0;D2;+0:3]=[C;H0;D2;+0:4]=[O;D1;H0:5].[NH2;D1;+0:6]-[c:7]1:[#16;a:8]:[c:9]:[c:10]:[#7;a:11]:1>>[C;D1;H3:1]-[C:2]-[NH;D2;+0:3]-[C;H0;D3;+0:4](=[O;D1;H0:5])-[NH;D2;+0:6]-[c:7]1:[#16;a:8]:[c:9]:[c:10]:[#7;a:11]:1 | null | [] | 80 | CELSIUS | 4 | HOUR | 2-Amino-1,3-benzothiazole-6-carbonitrile (0.2 g) was dissolved in about 5 mL dimethylformamide. About 0.2 mL of ethylisocyanate was added, followed by about 0.3 mL triethylamine and the solution was heated to about 80° C. under good agitation. The solution was allowed to stir for about 4 hours then cooled to room tempe... | 10.6084/m9.figshare.5104873.v1 | null | Isocyanate.Primary amine | Urea | null | null | c1ccc2scnc2c1 | null | CN(C=O)C | 80 | 4 | CCN=C=O.N#Cc1ccc2nc(N)sc2c1>CN(C=O)C>CCNC(=O)Nc1nc2ccc(C#N)cc2s1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-e8b7ee04ec75448d86e69b5a0568d5fc | C=O.CCN1CN(C)CN(c2nc3ccc([N+](=O)[O-])cc3s2)C1=O.CCNC(=O)Nc1nc2ccc([N+](=O)[O-])cc2s1.CN>>N#Cc1ccc2nc(NC(=O)NCc3cccnc3)sc2c1 | CN1CCOCC1.C(C)N1C(N(CN(C1)C)C=1SC2=C(N1)C=CC(=C2)[N+](=O)[O-])=O.C(C)NC(=O)NC=1SC2=C(N1)C=CC(=C2)[N+](=O)[O-].C=O.CN>>C(#N)C1=CC2=C(N=C(S2)NC(=O)NCC=2C=NC=CC2)C=C1 | O=[CH2:2].CC[N:18]1[C:17](=O)N(c2nc3c(cc([N+](=O)[O-])[cH:16][cH:15]3)s2)CN(C)[CH2:19]1.O=[N+]([O-])[c:3]1[cH:4][cH:5][c:6]2[n:7][c:8]([NH:9][C:10](=[O:11])[NH:12][CH2:13][CH3:14])[s:20][c:21]2[cH:22]1.C[NH2:1]>>[N:1]#[C:2][c:3]1[cH:4][cH:5][c:6]2[n:7][c:8]([NH:9][C:10](=[O:11])[NH:12][CH2:13][c:14]3[cH:15][cH:16][cH:1... | C=O.CCN1CN(C)CN(c2nc3ccc([N+](=O)[O-])cc3s2)C1=O.CCNC(=O)Nc1nc2ccc([N+](=O)[O-])cc2s1.CN | N#Cc1ccc2nc(NC(=O)NCc3cccnc3)sc2c1 | null | null | CO.CCO.O | Functional Group Interconversion | OtherReaction | 5131c57603f6750f0299e6e79c282d38f1ab637874a31291b2d136aedfeeef39 | d624d8d96fc6f2378b9c81de01f9c2535d63f3cc0df91d45260c67c5efe7890e | O=C(NCc1cccnc1)Nc1nc2ccccc2s1 | C-C-[N;H0;D3;+0:1]1-[CH2;D2;+0:2]-N(-C)-C-N(-c2:n:c3:[cH;D2;+0:3]:[cH;D2;+0:4]:c(-[N+](=O)-[O-]):c:c:3:s:2)-[C;H0;D3;+0:5]-1=O.C-[NH2;D1;+0:6].O=[CH2;D1;+0:7].O=[N+](-[O-])-[c;H0;D3;+0:8]1:[c:9]:[c:10]2:[#16;a:11]:[c:12](-[#7:13]-[C:14](=[O;D1;H0:15])-[#7:16]-[C:17]-[CH3;D1;+0:18]):[#7;a:19]:[c:20]:2:[c:21]:[c:22]:1>>[... | null | [] | 80 | CELSIUS | 4 | HOUR | General procedure for synthesizing 1-ethyl-5-methyl-3-(6-nitro-1,3-benzothiazol-2-yl)-1,3,5-triazinan-2-one: N-Ethyl-N′-(6-nitro-1,3-benzothiazol-2-yl)urea is suspended in an alkanol/water mixture, preferably 1:1 EtOH/H2O at room temperature. A 37% aqueous solution of formaldehyde is added followed by addition of a 2M ... | 10.6084/m9.figshare.5104873.v1 | null | Formaldehyde.Urea.Nitro group.Nitro group.Primary amine.Tertiary amine | Nitrile | C1NCNC[NH]1.c1ccc2scnc2c1.c1ccc2scnc2c1 | c1ccc2scnc2c1.c1ccncc1 | c1ccc2scnc2c1.c1ccncc1 | Other | CO.CCO.O | 80 | 4 | C=O.CCN1CN(C)CN(c2nc3ccc([N+](=O)[O-])cc3s2)C1=O.CCNC(=O)Nc1nc2ccc([N+](=O)[O-])cc2s1.CN>CO.CCO.O>N#Cc1ccc2nc(NC(=O)NCc3cccnc3)sc2c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-3d6f07f08bd342b498abd6f7a943c2cb | C=O.CCNC(=O)Nc1nc2ccc([N+](=O)[O-])cc2s1.CN>>CCN1CN(C)CN(c2nc3ccc([N+](=O)[O-])cc3s2)C1=O | CN1CCOCC1.C(C)NC(=O)NC=1SC2=C(N1)C=CC(=C2)[N+](=O)[O-].C=O.CN>>C(C)N1C(N(CN(C1)C)C=1SC2=C(N1)C=CC(=C2)[N+](=O)[O-])=O | O=[CH2:7].[CH3:1][CH2:2][NH:3][C:21]([NH:8][c:9]1[n:10][c:11]2[cH:12][cH:13][c:14]([N+:15](=[O:16])[O-:17])[cH:18][c:19]2[s:20]1)=[O:22].[NH2:5][CH3:6]>>[CH3:1][CH2:2][N:3]1[CH2:4][N:5]([CH3:6])[CH2:7][N:8]([c:9]2[n:10][c:11]3[cH:12][cH:13][c:14]([N+:15](=[O:16])[O-:17])[cH:18][c:19]3[s:20]2)[C:21]1=[O:22] | C=O.CCNC(=O)Nc1nc2ccc([N+](=O)[O-])cc2s1.CN | CCN1CN(C)CN(c2nc3ccc([N+](=O)[O-])cc3s2)C1=O | null | null | CO.CCO.O | Heteroatom Alkylation and Arylation | OtherReaction | bdea82356d1d675fe90b0ec07e79d17a706b5b14db216d1856803977c01f0274 | 2bbb8aef114a0ee542edb20042bb6d63f1fdf5f603b0aa000dfbb71b18ea52a0 | O=C1NCNCN1c1nc2ccccc2s1 | O=[CH2;D1;+0:1].[C;D1;H3:2]-[C:3]-[NH;D2;+0:4]-[C:5](=[O;D1;H0:6])-[NH;D2;+0:7]-[c:8]1:[#16;a:9]:[c:10]:[c:11]:[#7;a:12]:1.[C;D1;H3:13]-[NH2;D1;+0:14]>>[C;D1;H3:2]-[C:3]-[N;H0;D3;+0:4]1-[C:15]-[N;H0;D3;+0:14](-[C;D1;H3:13])-[CH2;D2;+0:1]-[N;H0;D3;+0:7](-[c:8]2:[#16;a:9]:[c:10]:[c:11]:[#7;a:12]:2)-[C:5]-1=[O;D1;H0:6] | null | [] | 80 | CELSIUS | 16 | HOUR | N-Ethyl-N′-(6-nitro-1,3-benzothiazol-2-yl)urea (2.8 g) was suspended in about 100 mL 1:1 EtOH/H2O at room temperature. About 8 mL of a 37% aqueous solution of formaldehyde is added followed by addition of about 15 mL of a 2M solution of MeNH2 in MeOH, then about 2.2 mL of N-methylmorpholine. The solution was warmed to ... | 10.6084/m9.figshare.5104873.v1 | null | Formaldehyde.Urea.Primary amine | Urea.Tertiary amine | null | C1[NH]C[NH]C[NH]1 | C1[NH]C[NH]C[NH]1.c1ccc2scnc2c1 | null | CO.CCO.O | 80 | 16 | C=O.CCNC(=O)Nc1nc2ccc([N+](=O)[O-])cc2s1.CN>CO.CCO.O>CCN1CN(C)CN(c2nc3ccc([N+](=O)[O-])cc3s2)C1=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-0f07a300f177487084962573f64fed09 | CCN=C=O.Nc1nc2c(s1)C(=O)CCC2>>CCNC(=O)Nc1nc2c(s1)C(=O)CCC2 | CCOCC.NC=1SC2=C(N1)CCCC2=O.C(C)N(CC)CC.C(C)N=C=O>>O=C1CCCC=2N=C(SC21)NC(=O)NCC | [CH3:1][CH2:2][N:3]=[C:4]=[O:5].[NH2:6][c:7]1[n:8][c:9]2[c:10]([s:11]1)[C:12](=[O:13])[CH2:14][CH2:15][CH2:16]2>>[CH3:1][CH2:2][NH:3][C:4](=[O:5])[NH:6][c:7]1[n:8][c:9]2[c:10]([s:11]1)[C:12](=[O:13])[CH2:14][CH2:15][CH2:16]2 | CCN=C=O.Nc1nc2c(s1)C(=O)CCC2 | CCNC(=O)Nc1nc2c(s1)C(=O)CCC2 | null | null | CN(C)C=O | Acylation | Urea synthesis via isocyanate and primary amine | d39cd7dc52a79bb265ff8ef61ef7bf9dc7f7b5fb0150fcb4881bdfb18ab9c380 | a5dc801930c765d2a435a0a2973e50163c305ba8e7641d6adbcc1550b7b96de7 | O=C1CCCc2ncsc21 | [C;D1;H3:1]-[C:2]-[N;H0;D2;+0:3]=[C;H0;D2;+0:4]=[O;D1;H0:5].[NH2;D1;+0:6]-[c:7]1:[#16;a:8]:[c:9](:[c:10]:[#7;a:11]:1)-[C:12]=[O;D1;H0:13]>>[C;D1;H3:1]-[C:2]-[NH;D2;+0:3]-[C;H0;D3;+0:4](=[O;D1;H0:5])-[NH;D2;+0:6]-[c:7]1:[#16;a:8]:[c:9](:[c:10]:[#7;a:11]:1)-[C:12]=[O;D1;H0:13] | 85 | [{"value": 85.0, "product": "O=C1CCCC=2N=C(SC21)NC(=O)NCC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 85.0, "product": "O=C1CCCC=2N=C(SC21)NC(=O)NCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 90 | CELSIUS | 3 | HOUR | A solution of 2-amino-7-oxo-4,5,6,7-tetrahydro-benzothiazole 3 (11.56 g, 68.7 mmol) in anhydrous DMF (200 mL) was treated with triethylamine (19.2 mL, 137 mmol, 2.0 eq) and ethyl isocyanate (10.9 nL, 137 mmol, 2.0 eq). The reaction mixture was heated at about 90° C. with stirring for about 3 hours. The DMF solvent was ... | 10.6084/m9.figshare.5104873.v1 | null | Isocyanate.Primary amine | Urea | null | null | c1nc2c(s1)CCCC2 | null | CN(C)C=O | 90 | 3 | CCN=C=O.Nc1nc2c(s1)C(=O)CCC2>CN(C)C=O>CCNC(=O)Nc1nc2c(s1)C(=O)CCC2 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-514fddbecd104874be43c28786f03d53 | BrBr.CCNC(=O)Nc1nc2c(s1)C(=O)CCC2>>CCNC(=O)Nc1nc2c(s1)C(=O)C(Br)(Br)CC2 | O=C1CCCC=2N=C(SC21)NC(=O)NCC.Br.BrBr>>BrC1(C(C2=C(N=C(S2)NC(=O)NCC)CC1)=O)Br | [Br:15][Br:16].[CH3:1][CH2:2][NH:3][C:4](=[O:5])[NH:6][c:7]1[n:8][c:9]2[c:10]([s:11]1)[C:12](=[O:13])[CH2:14][CH2:17][CH2:18]2>>[CH3:1][CH2:2][NH:3][C:4](=[O:5])[NH:6][c:7]1[n:8][c:9]2[c:10]([s:11]1)[C:12](=[O:13])[C:14]([Br:15])([Br:16])[CH2:17][CH2:18]2 | BrBr.CCNC(=O)Nc1nc2c(s1)C(=O)CCC2 | CCNC(=O)Nc1nc2c(s1)C(=O)C(Br)(Br)CC2 | null | null | CC(=O)O | Miscellaneous | OtherReaction | de7f1ef5007cd3b0cdd78b2b3829c93be31702b6b016757b5ad2ec7c305af598 | d7e0cb4138f465d209584b403eade9ac08ac7b78b08c53cd9ba80f59a0761110 | O=C1CCCc2ncsc21 | [#16;a:1]:[c:2]1:[c:3](:[#7;a:4])-[C:5]-[C:6]-[CH2;D2;+0:7]-[C:8]-1=[O;D1;H0:9].[Br;H0;D1;+0:10]-[Br;H0;D1;+0:11]>>[#16;a:1]:[c:2]1:[c:3](:[#7;a:4])-[C:5]-[C:6]-[C;H0;D4;+0:7](-[Br;H0;D1;+0:10])(-[Br;H0;D1;+0:11])-[C:8]-1=[O;D1;H0:9] | 937.5 | [{"value": 94.0, "product": "BrC1(C(C2=C(N=C(S2)NC(=O)NCC)CC1)=O)Br", "details": "PERCENTYIELD", "is_desired": false}, {"value": 937.5, "product": "BrC1(C(C2=C(N=C(S2)NC(=O)NCC)CC1)=O)Br", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 45 | CELSIUS | null | null | A solution of 1-(7-oxo-4,5,6,7-tetrahydro-2-benzothiazolyl)-3-ethyl-urea 4 (5.00 g, 20.9 mmol), 48% HBr (aq) (1.20 mL, 2.09 mmol, 0.1 eq) and AcOH (451 mL) was treated dropwise with a solution of Br2 (2.21 mL, 42.8 mmol, 2.05 eq) in AcOH (5 mL) with stirring. The reaction mixture was heated at about 45° C. with stirrin... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Tertiary halide.Tertiary halide | c1nc2c(s1)CCCC2 | c1nc2c(s1)CCCC2 | c1nc2c(s1)CCCC2 | null | CC(=O)O | 45 | null | BrBr.CCNC(=O)Nc1nc2c(s1)C(=O)CCC2>CC(=O)O>CCNC(=O)Nc1nc2c(s1)C(=O)C(Br)(Br)CC2 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-4f2e74aefc354a3f8e93f452a584a7ad | CCNC(=O)Nc1nc2c(s1)C(=O)C(Br)(Br)CC2>>CCNC(=O)Nc1nc2ccc(Br)c(O)c2s1 | BrC1(C(C2=C(N=C(S2)NC(=O)NCC)CC1)=O)Br.C1CCC2=NCCCN2CC1.C1CCC2=NCCCN2CC1>>BrC1=C(C2=C(N=C(S2)NC(=O)NCC)C=C1)O | Br[C:12]1([Br:13])[CH2:11][CH2:10][c:9]2[n:8][c:7]([NH:6][C:4]([NH:3][CH2:2][CH3:1])=[O:5])[s:17][c:16]2[C:14]1=[O:15]>>[CH3:1][CH2:2][NH:3][C:4](=[O:5])[NH:6][c:7]1[n:8][c:9]2[cH:10][cH:11][c:12]([Br:13])[c:14]([OH:15])[c:16]2[s:17]1 | CCNC(=O)Nc1nc2c(s1)C(=O)C(Br)(Br)CC2 | CCNC(=O)Nc1nc2ccc(Br)c(O)c2s1 | null | null | C1CCOC1 | Functional Group Interconversion | OtherReaction | 182ebab0a44dcfaa96f2549e00b7a0898ae20a92e3eb7bd3780b196f3b0a5fb9 | d41de2414b2cfa6a39168b2591625983cd73933a93e7987f54fa6db9b391c613 | c1ccc2scnc2c1 | Br-[C;H0;D4;+0:1]1(-[Br;D1;H0:2])-[CH2;D2;+0:3]-[CH2;D2;+0:4]-[c:5]2:[#7;a:6]:[c:7]:[#16;a:8]:[c:9]:2-[C;H0;D3;+0:10]-1=[O;H0;D1;+0:11]>>[Br;D1;H0:2]-[c;H0;D3;+0:1]1:[cH;D2;+0:3]:[cH;D2;+0:4]:[c:5]2:[#7;a:6]:[c:7]:[#16;a:8]:[c:9]:2:[c;H0;D3;+0:10]:1-[OH;D1;+0:11] | 78 | [{"value": 78.0, "product": "BrC1=C(C2=C(N=C(S2)NC(=O)NCC)C=C1)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 77.9, "product": "BrC1=C(C2=C(N=C(S2)NC(=O)NCC)C=C1)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 20 | CELSIUS | 18 | HOUR | A suspension of 1-(6,6-dibromo-7-oxo-4,5,6,7-tetrahydro-2-benzothiazolyl)-3-ethyl-urea 5 (7.78 g, 19.6 mmol) in THF (50 mL) was treated with DBU (8.79 mL, 58.8 mmol, 3.0 eq) dropwise at about 20° C. A dark green suspension was obtained while heat was generated upon addition of DBU. It was stirred at about 20° C. for ab... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary halide.Tertiary halide.Ketone | Aromatic halide.Aromatic alcohol | c1nc2c(s1)CCCC2 | c1ccc2scnc2c1 | c1ccc2scnc2c1 | HBr | C1CCOC1 | 20 | 18 | CCNC(=O)Nc1nc2c(s1)C(=O)C(Br)(Br)CC2>C1CCOC1>CCNC(=O)Nc1nc2ccc(Br)c(O)c2s1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-091d1065bf6a4e45857801ca9cde86da | BrBr.CCNC(=O)Nc1nc2c(s1)C(=O)CCC2>>CCNC(=O)Nc1nc2c(s1)C(=O)C(Br)CC2 | O=C1CCCC=2N=C(SC21)NC(=O)NCC.Br.BrBr>>BrC1C(C2=C(N=C(S2)NC(=O)NCC)CC1)=O | Br[Br:15].[CH3:1][CH2:2][NH:3][C:4](=[O:5])[NH:6][c:7]1[n:8][c:9]2[c:10]([s:11]1)[C:12](=[O:13])[CH2:14][CH2:16][CH2:17]2>>[CH3:1][CH2:2][NH:3][C:4](=[O:5])[NH:6][c:7]1[n:8][c:9]2[c:10]([s:11]1)[C:12](=[O:13])[CH:14]([Br:15])[CH2:16][CH2:17]2 | BrBr.CCNC(=O)Nc1nc2c(s1)C(=O)CCC2 | CCNC(=O)Nc1nc2c(s1)C(=O)C(Br)CC2 | null | null | CC(=O)O | Functional Group Interconversion | Bromination | c1da30deb3c2b1d2b15808c016938f0e62d86bb3f9dfee9bd96f482ea3a67ece | fe149a07f370bdd2ea40b2dff4f3462711fb34a60b8733c443efdeb5ab4d5c53 | O=C1CCCc2ncsc21 | Br-[Br;H0;D1;+0:1].[#16;a:2]:[c:3]1:[c:4](:[#7;a:5])-[C:6]-[C:7]-[CH2;D2;+0:8]-[C:9]-1=[O;D1;H0:10]>>[#16;a:2]:[c:3]1:[c:4](:[#7;a:5])-[C:6]-[C:7]-[CH;D3;+0:8](-[Br;H0;D1;+0:1])-[C:9]-1=[O;D1;H0:10] | 166.9 | [{"value": 83.0, "product": "BrC1C(C2=C(N=C(S2)NC(=O)NCC)CC1)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 166.9, "product": "BrC1C(C2=C(N=C(S2)NC(=O)NCC)CC1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 45 | CELSIUS | null | null | A solution of 1-(7-oxo-4,5,6,7-tetrahydro-2-benzothiazolyl)-3-ethyl-urea 4 (1.00 g, 4.18 mmol) and 48% HBr (aq) (0.24 mL, 2.09 mmol, 0.5 eq) in AcOH (18 mL) was treated dropwise with a solution of Br2 (0.23 mL, 4.39 mmol, 1.05 eq) in AcOH (1 mL) with stirring. The reaction mixture was heated at about 45° C. with stirri... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Secondary halide | c1nc2c(s1)CCCC2 | c1nc2c(s1)CCCC2 | c1nc2c(s1)CCCC2 | HBr | CC(=O)O | 45 | null | BrBr.CCNC(=O)Nc1nc2c(s1)C(=O)CCC2>CC(=O)O>CCNC(=O)Nc1nc2c(s1)C(=O)C(Br)CC2 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-f28c76dea7f44a58b87eb28465351440 | CCNC(=O)Nc1nc2c(s1)C(=O)C(Br)(Br)CC2>>CCNC(=O)Nc1nc2cccc(O)c2s1 | BrC1(C(C2=C(N=C(S2)NC(=O)NCC)CC1)=O)Br.C1CCC2=NCCCN2CC1.C1CCC2=NCCCN2CC1>>OC1=CC=CC=2N=C(SC21)NC(=O)NCC | Br[C:12]1(Br)[CH2:11][CH2:10][c:9]2[n:8][c:7]([NH:6][C:4]([NH:3][CH2:2][CH3:1])=[O:5])[s:16][c:15]2[C:13]1=[O:14]>>[CH3:1][CH2:2][NH:3][C:4](=[O:5])[NH:6][c:7]1[n:8][c:9]2[cH:10][cH:11][cH:12][c:13]([OH:14])[c:15]2[s:16]1 | CCNC(=O)Nc1nc2c(s1)C(=O)C(Br)(Br)CC2 | CCNC(=O)Nc1nc2cccc(O)c2s1 | null | null | C1CCOC1 | Miscellaneous | OtherReaction | ae229ce338b8acc1177e28dc753f0d19e887ebbc1f31e2eebcb619dbd23b7878 | fc192a81bb1b5ef7110cb68881e9a7f5a22c45e549875dffdc37c7a80468b788 | c1ccc2scnc2c1 | Br-[C;H0;D4;+0:1]1(-Br)-[CH2;D2;+0:2]-[CH2;D2;+0:3]-[c:4]2:[#7;a:5]:[c:6]:[#16;a:7]:[c:8]:2-[C;H0;D3;+0:9]-1=[O;H0;D1;+0:10]>>[OH;D1;+0:10]-[c;H0;D3;+0:9]1:[cH;D2;+0:1]:[cH;D2;+0:2]:[cH;D2;+0:3]:[c:4]2:[#7;a:5]:[c:6]:[#16;a:7]:[c:8]:2:1 | 32.2 | [{"value": 32.0, "product": "OC1=CC=CC=2N=C(SC21)NC(=O)NCC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 32.2, "product": "OC1=CC=CC=2N=C(SC21)NC(=O)NCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 20 | CELSIUS | 18 | HOUR | To a suspension of 1-(6-bromo-7-oxo-4,5,6,7-tetrahydro-2-benzothiazolyl)-3-ethyl-urea 5 (0.100 g, 0.314 mmol) in THF (1.0 mL) was added DBU (0.141 mL, 0.94 mmol, 3 eq) dropwise at about 20° C. A dark green suspension was obtained while heat was generated upon addition of DBU. It was stirred at about 20° C. for about 18... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary halide.Tertiary halide.Ketone | Aromatic alcohol | c1nc2c(s1)CCCC2 | c1ccc2scnc2c1 | c1ccc2scnc2c1 | Br- | C1CCOC1 | 20 | 18 | CCNC(=O)Nc1nc2c(s1)C(=O)C(Br)(Br)CC2>C1CCOC1>CCNC(=O)Nc1nc2cccc(O)c2s1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b7720941bb934e35991fd79ffdaedd76 | CCNC(=O)Nc1nc2ccc(Br)c(O)c2s1>>CCNC(=O)Nc1nc2cccc(O)c2s1 | BrC1=C(C2=C(N=C(S2)NC(=O)NCC)C=C1)O.C([O-])([O-])=O.[K+].[K+].CO>>OC1=CC=CC=2N=C(SC21)NC(=O)NCC | Br[c:12]1[cH:11][cH:10][c:9]2[n:8][c:7]([NH:6][C:4]([NH:3][CH2:2][CH3:1])=[O:5])[s:16][c:15]2[c:13]1[OH:14]>>[CH3:1][CH2:2][NH:3][C:4](=[O:5])[NH:6][c:7]1[n:8][c:9]2[cH:10][cH:11][cH:12][c:13]([OH:14])[c:15]2[s:16]1 | CCNC(=O)Nc1nc2ccc(Br)c(O)c2s1 | CCNC(=O)Nc1nc2cccc(O)c2s1 | null | null | CN(C)C=O | Functional Group Interconversion | Aromatic dehalogenation | 776c7f75e87bb735c9b3cad39517ab7ffb5754e38a78c449a72d14189b4df482 | 56de34d4a44cb25d9380269ee5e138b0f24b40a3a0db22c5508049dc775a861f | c1ccc2scnc2c1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]2:[#7;a:5]:[c:6]:[#16;a:7]:[c:8]:2:[c:9]:1-[O;D1;H1:10]>>[O;D1;H1:10]-[c:9]1:[cH;D2;+0:1]:[c:2]:[c:3]:[c:4]2:[#7;a:5]:[c:6]:[#16;a:7]:[c:8]:1:2 | null | [] | 20 | CELSIUS | 0.5 | HOUR | General Procedure for 1-(6-bromo-7-alkoxy-2-benzothiazolyl)-3-ethyl-urea compounds 9–13. A mixture of 1-(6-bromo-7-hydroxy-2-benzothiazolyl)-3-ethyl-urea 6 and potassium carbonate (1.05 eq) in anhydrous DMF was stirred at about 20° C. for about 0.5 hour, and was cooled down to about 0° C. The mixture was treated with a... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | null | c1ccc2scnc2c1 | c1ccc2scnc2c1 | c1ccc2scnc2c1 | Br- | CN(C)C=O | 20 | 0.5 | CCNC(=O)Nc1nc2ccc(Br)c(O)c2s1>CN(C)C=O>CCNC(=O)Nc1nc2cccc(O)c2s1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-c5baa1466eb64f28875bdeda9757c685 | BrCc1ccccc1.CCNC(=O)Nc1nc2ccc(Br)c(O)c2s1>>CCNC(=O)Nc1nc2ccc(Br)c(OCc3ccccc3)c2s1 | CO.BrC1=C(C2=C(N=C(S2)NC(=O)NCC)C=C1)O.C([O-])([O-])=O.[K+].[K+].C(C1=CC=CC=C1)Br>>BrC1=C(C2=C(N=C(S2)NC(=O)NCC)C=C1)OCC1=CC=CC=C1 | Br[CH2:16][c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1.[CH3:1][CH2:2][NH:3][C:4](=[O:5])[NH:6][c:7]1[n:8][c:9]2[cH:10][cH:11][c:12]([Br:13])[c:14]([OH:15])[c:23]2[s:24]1>>[CH3:1][CH2:2][NH:3][C:4](=[O:5])[NH:6][c:7]1[n:8][c:9]2[cH:10][cH:11][c:12]([Br:13])[c:14]([O:15][CH2:16][c:17]3[cH:18][cH:19][cH:20][cH:21][cH:22]3)... | BrCc1ccccc1.CCNC(=O)Nc1nc2ccc(Br)c(O)c2s1 | CCNC(=O)Nc1nc2ccc(Br)c(OCc3ccccc3)c2s1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | c1ccc(COc2cccc3ncsc23)cc1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[OH;D1;+0:5]-[c:6](:[c:7]):[c:8]1:[#16;a:9]:[c:10]:[#7;a:11]:[c:12]:1>>[c:7]:[c:6](-[O;H0;D2;+0:5]-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4]):[c:8]1:[#16;a:9]:[c:10]:[#7;a:11]:[c:12]:1 | 45 | [{"value": 45.0, "product": "BrC1=C(C2=C(N=C(S2)NC(=O)NCC)C=C1)OCC1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 44.6, "product": "BrC1=C(C2=C(N=C(S2)NC(=O)NCC)C=C1)OCC1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 20 | CELSIUS | 0.5 | HOUR | A mixture of 1-(6-bromo-7-hydroxy-2-benzothiazolyl)-3-ethyl-urea 6 (0.050 g, 0.16 mmol) and potassium carbonate (0.023 g, 0.17 mmol, 1.05 eq) in anhydrous DMF (1.6 mL) was stirred at about 20° C. for about 0.5 hour, and was cooled down to about 0° C. The reaction mixture was treated with benzyl bromide (0.019 mL, 0.16 ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccc2scnc2c1.c1ccccc1 | HBr | CN(C)C=O | 20 | 0.5 | BrCc1ccccc1.CCNC(=O)Nc1nc2ccc(Br)c(O)c2s1>CN(C)C=O>CCNC(=O)Nc1nc2ccc(Br)c(OCc3ccccc3)c2s1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-12cf03b2e2304f0c877426f44e1029ac | CCNC(=O)Nc1nc2ccc(Br)c(O)c2s1.CI>>CCNC(=O)Nc1nc2ccc(Br)c(OC)c2s1 | BrC1=C(C2=C(N=C(S2)NC(=O)NCC)C=C1)O.C([O-])([O-])=O.[K+].[K+].IC>>BrC1=C(C2=C(N=C(S2)NC(=O)NCC)C=C1)OC | [CH3:1][CH2:2][NH:3][C:4](=[O:5])[NH:6][c:7]1[n:8][c:9]2[cH:10][cH:11][c:12]([Br:13])[c:14]([OH:15])[c:17]2[s:18]1.I[CH3:16]>>[CH3:1][CH2:2][NH:3][C:4](=[O:5])[NH:6][c:7]1[n:8][c:9]2[cH:10][cH:11][c:12]([Br:13])[c:14]([O:15][CH3:16])[c:17]2[s:18]1 | CCNC(=O)Nc1nc2ccc(Br)c(O)c2s1.CI | CCNC(=O)Nc1nc2ccc(Br)c(OC)c2s1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | b8b041187bac58376aae824630608e7deb49a01db3d652291f8b379c10d4e434 | 0f0966e3597a58033417ecee71659f4d0c082f95d46b1e52c95541e6e4a59086 | c1ccc2scnc2c1 | I-[CH3;D1;+0:1].[OH;D1;+0:2]-[c:3](:[c:4]):[c:5]1:[#16;a:6]:[c:7]:[#7;a:8]:[c:9]:1>>[CH3;D1;+0:1]-[O;H0;D2;+0:2]-[c:3](:[c:4]):[c:5]1:[#16;a:6]:[c:7]:[#7;a:8]:[c:9]:1 | 2 | [{"value": 2.0, "product": "BrC1=C(C2=C(N=C(S2)NC(=O)NCC)C=C1)OC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 1-(6-bromo-7-hydroxy-2-benzothiazolyl)-3-ethyl-urea 6, potassium carbonate and iodomethane in DMF was reacted to give 0.0034 g (2%) of the desired compound 10. 1H NMR (DMSO) δ 10.88 (br s, 1H, NH), 7.55 (d, 1H, J=8.5 Hz, ArH), 7.33 (d, 1H, J=8.5 Hz, ArH), 6.82 (br s, 1H, NH), 3.93 (s, 3H, CH3), 3.18 (m, 2H... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic alcohol | Ether | null | null | c1ccc2scnc2c1 | HI | CN(C)C=O | null | null | CCNC(=O)Nc1nc2ccc(Br)c(O)c2s1.CI>CN(C)C=O>CCNC(=O)Nc1nc2ccc(Br)c(OC)c2s1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-a370cc9a12cf48bda09d8ac2cf6359f2 | CC(C)Br.CCNC(=O)Nc1nc2ccc(Br)c(O)c2s1>>CCNC(=O)Nc1nc2ccc(Br)c(OC(C)C)c2s1 | BrC1=C(C2=C(N=C(S2)NC(=O)NCC)C=C1)O.C([O-])([O-])=O.[K+].[K+].BrC(C)C>>BrC1=C(C2=C(N=C(S2)NC(=O)NCC)C=C1)OC(C)C | Br[CH:16]([CH3:17])[CH3:18].[CH3:1][CH2:2][NH:3][C:4](=[O:5])[NH:6][c:7]1[n:8][c:9]2[cH:10][cH:11][c:12]([Br:13])[c:14]([OH:15])[c:19]2[s:20]1>>[CH3:1][CH2:2][NH:3][C:4](=[O:5])[NH:6][c:7]1[n:8][c:9]2[cH:10][cH:11][c:12]([Br:13])[c:14]([O:15][CH:16]([CH3:17])[CH3:18])[c:19]2[s:20]1 | CC(C)Br.CCNC(=O)Nc1nc2ccc(Br)c(O)c2s1 | CCNC(=O)Nc1nc2ccc(Br)c(OC(C)C)c2s1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | bff4876be49b448135c783dd3eeeb68ab3cc5bdc91beadda8a9095106cd5c747 | cf768afb66ed5041aefdce1fa6d1e40995a1ab7c4b4a4ca47544fe49ee1e629f | c1ccc2scnc2c1 | Br-[CH;D3;+0:1](-[C;D1;H3:2])-[C;D1;H3:3].[OH;D1;+0:4]-[c:5](:[c:6]):[c:7]1:[#16;a:8]:[c:9]:[#7;a:10]:[c:11]:1>>[C;D1;H3:2]-[CH;D3;+0:1](-[C;D1;H3:3])-[O;H0;D2;+0:4]-[c:5](:[c:6]):[c:7]1:[#16;a:8]:[c:9]:[#7;a:10]:[c:11]:1 | 81 | [{"value": 81.0, "product": "BrC1=C(C2=C(N=C(S2)NC(=O)NCC)C=C1)OC(C)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 1-(6-bromo-7-hydroxy-2-benzothiazolyl)-3-ethyl-urea 6, potassium carbonate and 2-bromopropane in DMF was reacted to give 0.046 g (81%) of the desired compound 11. 1H NMR (DMSO) δ 10.83 (br s, 1H, NH), 7.55 (d, 1H, J=8.5 Hz, ArH), 7.31 (d, 1H, J=8.6 Hz, ArH), 6.71 (br s, 1H, NH), 4.69 (hept, 1H, J=6.0 Hz, C... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Aromatic alcohol | Ether | null | null | c1ccc2scnc2c1 | HBr | CN(C)C=O | null | null | CC(C)Br.CCNC(=O)Nc1nc2ccc(Br)c(O)c2s1>CN(C)C=O>CCNC(=O)Nc1nc2ccc(Br)c(OC(C)C)c2s1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-6994d4027fca4d73947eb9301277e302 | CCNC(=O)Nc1nc2ccc(Br)c(O)c2s1.COCCOCCBr>>CCNC(=O)Nc1nc2ccc(Br)c(OCCOCCOC)c2s1 | BrC1=C(C2=C(N=C(S2)NC(=O)NCC)C=C1)O.C([O-])([O-])=O.[K+].[K+].COCCOCCBr>>BrC1=C(C2=C(N=C(S2)NC(=O)NCC)C=C1)OCCOCCOC | [CH3:1][CH2:2][NH:3][C:4](=[O:5])[NH:6][c:7]1[n:8][c:9]2[cH:10][cH:11][c:12]([Br:13])[c:14]([OH:15])[c:23]2[s:24]1.Br[CH2:16][CH2:17][O:18][CH2:19][CH2:20][O:21][CH3:22]>>[CH3:1][CH2:2][NH:3][C:4](=[O:5])[NH:6][c:7]1[n:8][c:9]2[cH:10][cH:11][c:12]([Br:13])[c:14]([O:15][CH2:16][CH2:17][O:18][CH2:19][CH2:20][O:21][CH3:22... | CCNC(=O)Nc1nc2ccc(Br)c(O)c2s1.COCCOCCBr | CCNC(=O)Nc1nc2ccc(Br)c(OCCOCCOC)c2s1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | c1ccc2scnc2c1 | Br-[CH2;D2;+0:1]-[C:2]-[#8:3].[OH;D1;+0:4]-[c:5](:[c:6]):[c:7]1:[#16;a:8]:[c:9]:[#7;a:10]:[c:11]:1>>[#8:3]-[C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:4]-[c:5](:[c:6]):[c:7]1:[#16;a:8]:[c:9]:[#7;a:10]:[c:11]:1 | 39 | [{"value": 39.0, "product": "BrC1=C(C2=C(N=C(S2)NC(=O)NCC)C=C1)OCCOCCOC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 1-(6-bromo-7-hydroxy-2-benzothiazolyl)-3-ethyl-urea 6, potassium carbonate and 2-(2-methoxyethoxy)ethyl bromide in DMF was reacted to give 0.026 g (39%) of the desired compound 12. 1H NMR (DMSO) δ 10.65 (br s, 1H, NH), 7.54 (d, 1H, J=8.5 Hz, ArH), 7.32 (d, 1H, J=8.6 Hz, ArH), 6.73 (br s, 1H, NH), 4.24 (d, ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccc2scnc2c1 | HBr | CN(C)C=O | null | null | CCNC(=O)Nc1nc2ccc(Br)c(O)c2s1.COCCOCCBr>CN(C)C=O>CCNC(=O)Nc1nc2ccc(Br)c(OCCOCCOC)c2s1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-6778be28994349a58c0ea43b72428dba | CCNC(=O)Nc1nc2ccc(Br)c(O)c2s1.Fc1ccc(CBr)cc1>>CCNC(=O)Nc1nc2ccc(Br)c(OCc3ccc(F)cc3)c2s1 | BrC1=C(C2=C(N=C(S2)NC(=O)NCC)C=C1)O.C([O-])([O-])=O.[K+].[K+].FC1=CC=C(CBr)C=C1>>BrC1=C(C2=C(N=C(S2)NC(=O)NCC)C=C1)OCC1=CC=C(C=C1)F | [CH3:1][CH2:2][NH:3][C:4](=[O:5])[NH:6][c:7]1[n:8][c:9]2[cH:10][cH:11][c:12]([Br:13])[c:14]([OH:15])[c:24]2[s:25]1.Br[CH2:16][c:17]1[cH:18][cH:19][c:20]([F:21])[cH:22][cH:23]1>>[CH3:1][CH2:2][NH:3][C:4](=[O:5])[NH:6][c:7]1[n:8][c:9]2[cH:10][cH:11][c:12]([Br:13])[c:14]([O:15][CH2:16][c:17]3[cH:18][cH:19][c:20]([F:21])[c... | CCNC(=O)Nc1nc2ccc(Br)c(O)c2s1.Fc1ccc(CBr)cc1 | CCNC(=O)Nc1nc2ccc(Br)c(OCc3ccc(F)cc3)c2s1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | c1ccc(COc2cccc3ncsc23)cc1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[OH;D1;+0:5]-[c:6](:[c:7]):[c:8]1:[#16;a:9]:[c:10]:[#7;a:11]:[c:12]:1>>[c:7]:[c:6](-[O;H0;D2;+0:5]-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4]):[c:8]1:[#16;a:9]:[c:10]:[#7;a:11]:[c:12]:1 | 19 | [{"value": 19.0, "product": "BrC1=C(C2=C(N=C(S2)NC(=O)NCC)C=C1)OCC1=CC=C(C=C1)F", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 1-(6-bromo-7-hydroxy-2-benzothiazolyl)-3-ethyl-urea 6, potassium carbonate and p-fluoro-benzyl-bromide in DMF was reacted to give 0.013 g (19%) of the desired compound 13. 1H NMR (DMSO) δ 1.08 (t, 3H, J=8 Hz CH2CH3), 3.18 (m, 2H, CH2), 5.16 (s, 2H, OCH2Ar), 6.73 (br s, 1H, NH), 7.26 (dd, 2H, J=4, 4 Hz, ArH... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccc2scnc2c1.c1ccccc1 | HBr | CN(C)C=O | null | null | CCNC(=O)Nc1nc2ccc(Br)c(O)c2s1.Fc1ccc(CBr)cc1>CN(C)C=O>CCNC(=O)Nc1nc2ccc(Br)c(OCc3ccc(F)cc3)c2s1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-871ba8cd3b864435860dd69669537659 | CCNC(=O)Nc1nc2ccc(Br)c(O)c2s1.O=S(=O)(OS(=O)(=O)C(F)(F)F)C(F)(F)F>>CCNC(=O)Nc1nc2ccc(Br)c(S(=O)(=O)C(F)(F)F)c2s1 | BrC1=C(C2=C(N=C(S2)NC(=O)NCC)C=C1)O.O(S(=O)(=O)C(F)(F)F)S(=O)(=O)C(F)(F)F>>BrC1=C(C2=C(N=C(S2)NC(=O)NCC)C=C1)S(=O)(=O)C(F)(F)F | O[c:14]1[c:12]([Br:13])[cH:11][cH:10][c:9]2[n:8][c:7]([NH:6][C:4]([NH:3][CH2:2][CH3:1])=[O:5])[s:23][c:22]21.O=S(=O)(O[S:15](=[O:16])(=[O:17])[C:18]([F:19])([F:20])[F:21])C(F)(F)F>>[CH3:1][CH2:2][NH:3][C:4](=[O:5])[NH:6][c:7]1[n:8][c:9]2[cH:10][cH:11][c:12]([Br:13])[c:14]([S:15](=[O:16])(=[O:17])[C:18]([F:19])([F:20])[... | CCNC(=O)Nc1nc2ccc(Br)c(O)c2s1.O=S(=O)(OS(=O)(=O)C(F)(F)F)C(F)(F)F | CCNC(=O)Nc1nc2ccc(Br)c(S(=O)(=O)C(F)(F)F)c2s1 | null | null | N1=CC=CC=C1 | Heteroatom Alkylation and Arylation | OtherReaction | 7674ed2e5f64ab8fff3f27a750a5930306ccf9e2d3f773d1ecbf4ee9d29858d2 | 5f0ac2514d72d3f96bd6091be4d08699e506de1e84622ae8bde68f2cee9ab5d6 | c1ccc2scnc2c1 | F-C(-F)(-F)-S(=O)(=O)-O-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[C:4](-[F;D1;H0:5])(-[F;D1;H0:6])-[F;D1;H0:7].O-[c;H0;D3;+0:8]1:[c:9](-[Br;D1;H0:10]):[c:11]:[c:12]:[c:13]2:[#7;a:14]:[c:15]:[#16;a:16]:[c:17]:2:1>>[Br;D1;H0:10]-[c:9]1:[c:11]:[c:12]:[c:13]2:[#7;a:14]:[c:15]:[#16;a:16]:[c:17]:2:[c;H0;D3;+0:8]:1-[S;H0;D4... | null | [] | 35 | CELSIUS | 3 | HOUR | To a solution of 1-(6-bromo-7-hydroxy-2-benzothiazolyl)-3-ethyl-urea (50 mg, 0.158 mmol) in pyridine (1 mL) were added 3 portions of (CF3SO2)2O (29 μL, 0.174 mmol) about 45 minutes apart. The reaction mixture was stirred for about 3 hours at about 35° C. The solvent was then evaporated. The crude material was purified ... | 10.6084/m9.figshare.5104873.v1 | null | Triflate.Triflate.Aromatic alcohol | Sulfone | c1ccc2scnc2c1 | c1ccc2scnc2c1 | c1ccc2scnc2c1 | TfOH.HO- | N1=CC=CC=C1 | 35 | 3 | CCNC(=O)Nc1nc2ccc(Br)c(O)c2s1.O=S(=O)(OS(=O)(=O)C(F)(F)F)C(F)(F)F>N1=CC=CC=C1>CCNC(=O)Nc1nc2ccc(Br)c(S(=O)(=O)C(F)(F)F)c2s1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-c336b764197e420a978d946859501796 | CCNC(=O)Nc1nc2cccc(O)c2s1.O=[N+]=O>>CCNC(=O)Nc1nc2ccc([N+](=O)[O-])c(O)c2s1 | OC1=CC=CC=2N=C(SC21)NC(=O)NCC.F[B-](F)(F)F.O=[N+]=O>>OC1=C(C=CC=2N=C(SC21)NC(=O)NCC)[N+](=O)[O-] | [CH3:1][CH2:2][NH:3][C:4](=[O:5])[NH:6][c:7]1[n:8][c:9]2[cH:10][cH:11][cH:12][c:16]([OH:17])[c:18]2[s:19]1.[N+:13](=[O:14])=[O:15]>>[CH3:1][CH2:2][NH:3][C:4](=[O:5])[NH:6][c:7]1[n:8][c:9]2[cH:10][cH:11][c:12]([N+:13](=[O:14])[O-:15])[c:16]([OH:17])[c:18]2[s:19]1 | CCNC(=O)Nc1nc2cccc(O)c2s1.O=[N+]=O | CCNC(=O)Nc1nc2ccc([N+](=O)[O-])c(O)c2s1 | null | null | C(C)OCC.C(C)#N | Functional Group Addition | OtherReaction | 3db8a56438dbfcd47114c5d6aa6c6bdcd06ee8af429447c5f40cfdd0f6b6476a | 5c75a9bf759be9717d985245c85c84dbfff904ea5287869736b84fdaa57f1e27 | c1ccc2scnc2c1 | [O;D1;H0:1]=[N+;H0;D2:2]=[O;H0;D1;+0:3].[O;D1;H1:4]-[c:5]1:[cH;D2;+0:6]:[c:7]:[c:8]:[c:9]2:[#7;a:10]:[c:11]:[#16;a:12]:[c:13]:1:2>>[O-;H0;D1:3]-[N+;H0;D3:2](=[O;D1;H0:1])-[c;H0;D3;+0:6]1:[c:7]:[c:8]:[c:9]2:[#7;a:10]:[c:11]:[#16;a:12]:[c:13]:2:[c:5]:1-[O;D1;H1:4] | 10.4 | [{"value": 10.0, "product": "OC1=C(C=CC=2N=C(SC21)NC(=O)NCC)[N+](=O)[O-]", "details": "PERCENTYIELD", "is_desired": false}, {"value": 10.4, "product": "OC1=C(C=CC=2N=C(SC21)NC(=O)NCC)[N+](=O)[O-]", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 20 | CELSIUS | 5 | MINUTE | To a solution of 2-methylpyridone (0.020 mL, 0.20 mmol, 1.2 eq) in anhydrous acetonitrile (0.5 mL), nitronium tetrafluoroborate (0.045 g, 0.32 mmol, 1.9 eq) was added. The suspension was stirred at about 20° C. for about 5 minutes to get an orange solution. The solution was then transferred to a suspension of 1-(7-hydr... | 10.6084/m9.figshare.5104873.v1 | null | Nitroso.Nitroso | Nitro group | c1ccc2scnc2c1 | c1ccc2scnc2c1 | c1ccc2scnc2c1 | null | C(C)OCC.C(C)#N | 20 | 0.083333 | CCNC(=O)Nc1nc2cccc(O)c2s1.O=[N+]=O>C(C)OCC.C(C)#N>CCNC(=O)Nc1nc2ccc([N+](=O)[O-])c(O)c2s1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-2f5cc1a1e92a4c30a33e6ae5e6746e67 | BrBr.CCNC(=O)Nc1nc2ccc(Br)c(O)c2s1>>CCNC(=O)Nc1nc2c(Br)cc(Br)c(O)c2s1 | BrC1=C(C2=C(N=C(S2)NC(=O)NCC)C=C1)O.BrBr.C1(=CC=CC=C1)C>>BrC1=CC(=C(C2=C1N=C(S2)NC(=O)NCC)O)Br | Br[Br:11].[CH3:1][CH2:2][NH:3][C:4](=[O:5])[NH:6][c:7]1[n:8][c:9]2[cH:10][cH:12][c:13]([Br:14])[c:15]([OH:16])[c:17]2[s:18]1>>[CH3:1][CH2:2][NH:3][C:4](=[O:5])[NH:6][c:7]1[n:8][c:9]2[c:10]([Br:11])[cH:12][c:13]([Br:14])[c:15]([OH:16])[c:17]2[s:18]1 | BrBr.CCNC(=O)Nc1nc2ccc(Br)c(O)c2s1 | CCNC(=O)Nc1nc2c(Br)cc(Br)c(O)c2s1 | null | null | CC(=O)O | Functional Group Interconversion | Bromination | 42ba26ec59d66e34c4ffd51d0bc49d29a4fe2f80ce47b015ee1e31fc90c660cd | 3c4065ab4a8681675e06a527dcad54d701c7bfdcac9f73f87773b05034108934 | c1ccc2scnc2c1 | Br-[Br;H0;D1;+0:1].[#16;a:2]1:[c:3]:[#7;a:4]:[c:5]2:[cH;D2;+0:6]:[c:7]:[c:8]:[c:9]:[c:10]:1:2>>[Br;H0;D1;+0:1]-[c;H0;D3;+0:6]1:[c:7]:[c:8]:[c:9]:[c:10]2:[#16;a:2]:[c:3]:[#7;a:4]:[c:5]:2:1 | null | [] | 20 | CELSIUS | 15 | MINUTE | To a suspension of 1-(6-bromo-7-hydroxy-2-benzothiazolyl)-3-ethyl-urea (50 mg, 0.158 mmol) in AcOH (2 mL) at about 20° C. was added Br2 (9 μl, 0.174 mmol). The reaction mixture was stirred at about 20° C. for about 15 minutes. Toluene (10 mL) was added and the solvents evaporated. The crude material was purified by pre... | 10.6084/m9.figshare.5104873.v1 | null | null | Aromatic halide | c1ccc2scnc2c1 | c1ccc2scnc2c1 | c1ccc2scnc2c1 | HBr | CC(=O)O | 20 | 0.25 | BrBr.CCNC(=O)Nc1nc2ccc(Br)c(O)c2s1>CC(=O)O>CCNC(=O)Nc1nc2c(Br)cc(Br)c(O)c2s1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-1a6875afea914c3fb284eeb3add847f4 | C#C[Si](C)(C)C.CCNC(=O)Nc1nc2cccc(S(=O)(=O)C(F)(F)F)c2s1>>CCNC(=O)Nc1nc2cccc(C#C[Si](C)(C)C)c2s1 | FC(S(=O)(=O)C1=CC=CC=2N=C(SC21)NC(=O)NCC)(F)F.C(C)N(CC)CC.C[Si](C)(C)C#C>>C[Si](C)(C)C#CC1=CC=CC=2N=C(SC21)NC(=O)NCC | [CH:14]#[C:15][Si:16]([CH3:17])([CH3:18])[CH3:19].O=S(=O)(C(F)(F)F)[c:13]1[cH:12][cH:11][cH:10][c:9]2[n:8][c:7]([NH:6][C:4]([NH:3][CH2:2][CH3:1])=[O:5])[s:21][c:20]21>>[CH3:1][CH2:2][NH:3][C:4](=[O:5])[NH:6][c:7]1[n:8][c:9]2[cH:10][cH:11][cH:12][c:13]([C:14]#[C:15][Si:16]([CH3:17])([CH3:18])[CH3:19])[c:20]2[s:21]1 | C#C[Si](C)(C)C.CCNC(=O)Nc1nc2cccc(S(=O)(=O)C(F)(F)F)c2s1 | CCNC(=O)Nc1nc2cccc(C#C[Si](C)(C)C)c2s1 | null | Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl | CO.CN(C)C=O | C-C Coupling | OtherReaction | b089807d2270da66e4017f883e8fc70aa59f7eb4c69322f959c73f607cbaa1f3 | 4e971c26e411eb96e6bdc2680fd74feac55fede1a4ae64a25e6a61867967b471 | c1ccc2scnc2c1 | F-C(-F)(-F)-S(=O)(=O)-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[c:5]2:[#7;a:6]:[c:7]:[#16;a:8]:[c:9]:2:1.[C;D1;H3:10]-[#14:11](-[C;D1;H3:12])(-[C;D1;H3:13])-[C:14]#[CH;D1;+0:15]>>[C;D1;H3:10]-[#14:11](-[C;D1;H3:12])(-[C;D1;H3:13])-[C:14]#[C;H0;D2;+0:15]-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[c:5]2:[#7;a:6]:[c:7]:[#16;a:8]:[c:9]:2... | 93 | [{"value": 93.0, "product": "C[Si](C)(C)C#CC1=CC=CC=2N=C(SC21)NC(=O)NCC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 92.6, "product": "C[Si](C)(C)C#CC1=CC=CC=2N=C(SC21)NC(=O)NCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | 18 | HOUR | A mixture of 1-(7-trifluoromethylsulfonyl-2-benzothiazolyl)-3-ethylurea (0.080 g, 80% pure, 0.17 mmol), Pd(PPh3)2Cl2 (0.010 g, 0.014 mmol, 0.08 eq), and triethylamine (0.102 mL, 0.73 mmol, 4.3 eq) in 1 mL of anhydrous DMF was bubbled with nitrogen gas for 5 minutes, followed by the addition of trimethylsilyl acetylene ... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary halide.Tertiary halide.Tertiary halide.Sulfone.Alkyne | Alkyne | c1ccc2scnc2c1 | c1ccc2scnc2c1 | c1ccc2scnc2c1 | HF | Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl.CO.CN(C)C=O | 100 | 18 | C#C[Si](C)(C)C.CCNC(=O)Nc1nc2cccc(S(=O)(=O)C(F)(F)F)c2s1>Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl.CO.CN(C)C=O>CCNC(=O)Nc1nc2cccc(C#C[Si](C)(C)C)c2s1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-8abe128357e5495cb8583bed1bcfdda2 | CCNC(=O)Nc1nc2cccc(C#C[Si](C)(C)C)c2s1>>C#Cc1cccc2nc(NC(=O)NCC)sc12 | C[Si](C)(C)C#CC1=CC=CC=2N=C(SC21)NC(=O)NCC.[OH-].[K+].CN(C)C=O.CO>>C(#C)C1=CC=CC=2N=C(SC21)NC(=O)NCC | C[Si](C)(C)[C:1]#[C:2][c:3]1[cH:4][cH:5][cH:6][c:7]2[n:8][c:9]([NH:10][C:11](=[O:12])[NH:13][CH2:14][CH3:15])[s:16][c:17]12>>[CH:1]#[C:2][c:3]1[cH:4][cH:5][cH:6][c:7]2[n:8][c:9]([NH:10][C:11](=[O:12])[NH:13][CH2:14][CH3:15])[s:16][c:17]12 | CCNC(=O)Nc1nc2cccc(C#C[Si](C)(C)C)c2s1 | C#Cc1cccc2nc(NC(=O)NCC)sc12 | null | null | CO.CCCCCCC | Deprotection | TMS deprotection from alkyne | e85676bb81da384790c9c858d44f182cdd01e3a79f77f7a239fe38487234cb96 | 56d526d7c9cb1bd7bee4940e216a9b1dd4597fd025a186b8d6e4675d8f4db26b | c1ccc2scnc2c1 | C-[Si](-C)(-C)-[C;H0;D2;+0:1]#[C:2]-[c:3]:[c:4]:[#16;a:5]>>[#16;a:5]:[c:4]:[c:3]-[C:2]#[CH;D1;+0:1] | 15.3 | [{"value": 15.0, "product": "C(#C)C1=CC=CC=2N=C(SC21)NC(=O)NCC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 15.3, "product": "C(#C)C1=CC=CC=2N=C(SC21)NC(=O)NCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | A mixture of 1-(7-trimethylsilylacetylenyl-2-benzothiazolyl)-3-ethylurea 2 (0.050 g, 0.16 mmol) and 1M aqueous KOH solution (0.16 mL, 0.16 mmol, 1.0 eq) in 1.5 mL of 2/1 mixture of DMF/MeOH was stirred at room temperature for about 2 hours. The mixture was taken up in 10 mL MeOH and the precipitation was filtered off. ... | 10.6084/m9.figshare.5104873.v1 | null | Alkyne.Silyl protective group | Alkyne | null | null | c1ccc2scnc2c1 | Other | CO.CCCCCCC | null | 2 | CCNC(=O)Nc1nc2cccc(C#C[Si](C)(C)C)c2s1>CO.CCCCCCC>C#Cc1cccc2nc(NC(=O)NCC)sc12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-9a4c0e1c1fc94c6586402782e0c32725 | CCNC(=O)Nc1nc2ccc(Br)c(OC(C)C)c2s1>>CCNC(=O)Nc1nc2cccc(OC(C)C)c2s1 | [Li]CCCC.BrC1=C(C2=C(N=C(S2)NC(=O)NCC)C=C1)OC(C)C.ClN1C(CCC1=O)=O>>C(C)(C)OC1=CC=CC=2N=C(SC21)NC(=O)NCC | Br[c:12]1[cH:11][cH:10][c:9]2[n:8][c:7]([NH:6][C:4]([NH:3][CH2:2][CH3:1])=[O:5])[s:19][c:18]2[c:13]1[O:14][CH:15]([CH3:16])[CH3:17]>>[CH3:1][CH2:2][NH:3][C:4](=[O:5])[NH:6][c:7]1[n:8][c:9]2[cH:10][cH:11][cH:12][c:13]([O:14][CH:15]([CH3:16])[CH3:17])[c:18]2[s:19]1 | CCNC(=O)Nc1nc2ccc(Br)c(OC(C)C)c2s1 | CCNC(=O)Nc1nc2cccc(OC(C)C)c2s1 | null | null | CO.COCCOC | Functional Group Interconversion | Aromatic dehalogenation | 776c7f75e87bb735c9b3cad39517ab7ffb5754e38a78c449a72d14189b4df482 | 56de34d4a44cb25d9380269ee5e138b0f24b40a3a0db22c5508049dc775a861f | c1ccc2scnc2c1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]2:[#7;a:5]:[c:6]:[#16;a:7]:[c:8]:2:[c:9]:1-[#8:10]>>[#8:10]-[c:9]1:[cH;D2;+0:1]:[c:2]:[c:3]:[c:4]2:[#7;a:5]:[c:6]:[#16;a:7]:[c:8]:1:2 | 25.1 | [{"value": 25.0, "product": "C(C)(C)OC1=CC=CC=2N=C(SC21)NC(=O)NCC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 25.1, "product": "C(C)(C)OC1=CC=CC=2N=C(SC21)NC(=O)NCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 20 | MINUTE | A solution of 1-(6-bromo-7-isopropoxy-2-benzothiazolyl)-3-ethylurea (0.036 g, 0.10 mmol) in 0.5 mL DME was cooled down to about −78° C., and was treated with a solution of 1.6 M n-BuLi in hexanes (0.16 mL, 0.26 mmol, 2.6 eq). It was stirred at the temperature for about 20 min, then a solution of N-chlorosuccinimide (NC... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | null | c1ccc2scnc2c1 | c1ccc2scnc2c1 | c1ccc2scnc2c1 | Br- | CO.COCCOC | 0 | 0.333333 | CCNC(=O)Nc1nc2ccc(Br)c(OC(C)C)c2s1>CO.COCCOC>CCNC(=O)Nc1nc2cccc(OC(C)C)c2s1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-1b2a9a1d73d34afbbad146c0399680cb | C=[CH][Sn]([CH]=C)([CH]=C)[CH]=C.CCNC(=O)Nc1nc2cccc(S(=O)(=O)C(F)(F)F)c2s1>>C=Cc1cccc2nc(NC(=O)NCC)sc12 | FC(S(=O)(=O)C1=CC=CC=2N=C(SC21)NC(=O)NCC)(F)F.[Cl-].[Li+].C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C(=C)[Sn](C=C)(C=C)C=C>>C(=C)C1=CC=CC=2N=C(SC21)NC(=O)NCC | C=[CH][Sn]([CH]=C)([CH]=C)[CH:2]=[CH2:1].O=S(=O)(C(F)(F)F)[c:3]1[cH:4][cH:5][cH:6][c:7]2[n:8][c:9]([NH:10][C:11](=[O:12])[NH:13][CH2:14][CH3:15])[s:16][c:17]12>>[CH2:1]=[CH:2][c:3]1[cH:4][cH:5][cH:6][c:7]2[n:8][c:9]([NH:10][C:11](=[O:12])[NH:13][CH2:14][CH3:15])[s:16][c:17]12 | C=[CH][Sn]([CH]=C)([CH]=C)[CH]=C.CCNC(=O)Nc1nc2cccc(S(=O)(=O)C(F)(F)F)c2s1 | C=Cc1cccc2nc(NC(=O)NCC)sc12 | null | Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl | null | C-C Coupling | OtherReaction | 3497ccc5b3feccb81acd801312140b9382eb1d91628704ea2f1b20a31f06a7d4 | 442c6cecbfc241ab3f8437ed659158a1c002809445f8019bc11d84c4a025a81d | c1ccc2scnc2c1 | C=[CH]-[Sn](-[CH;D2;+0:1]=[C;D1;H2:2])(-[CH]=C)-[CH]=C.F-C(-F)(-F)-S(=O)(=O)-[c;H0;D3;+0:3]1:[c:4]:[c:5]:[c:6]:[c:7]2:[#7;a:8]:[c:9]:[#16;a:10]:[c:11]:2:1>>[C;D1;H2:2]=[CH;D2;+0:1]-[c;H0;D3;+0:3]1:[c:4]:[c:5]:[c:6]:[c:7]2:[#7;a:8]:[c:9]:[#16;a:10]:[c:11]:2:1 | 24.5 | [{"value": 14.0, "product": "C(=C)C1=CC=CC=2N=C(SC21)NC(=O)NCC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 24.5, "product": "C(=C)C1=CC=CC=2N=C(SC21)NC(=O)NCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | null | null | Similar to the synthesis of Example 203, a mixture of 1-(7-trifluoromethylsulfonyl-2-benzothiazolyl)-3-ethylurea (0.050 g, 80% pure, 0.11 mmol), lithium chloride (0.039 g, 0.92 mmol, 8.4 eq), triphenylphosphine (0.017 g, 0.066 mmol, 0.6 eq), Pd(PPh3)2Cl2 (0.009 g, 0.013 mmol, 0.12 eq), tetravinyltin (0.040 mL, 0.22 mmo... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary halide.Tertiary halide.Tertiary halide.Sulfone.Vinyl.Vinyl.Vinyl.Vinyl.Tin | Vinyl | c1ccc2scnc2c1 | c1ccc2scnc2c1 | c1ccc2scnc2c1 | HF.Sn | Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl | 100 | null | C=[CH][Sn]([CH]=C)([CH]=C)[CH]=C.CCNC(=O)Nc1nc2cccc(S(=O)(=O)C(F)(F)F)c2s1>Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl>C=Cc1cccc2nc(NC(=O)NCC)sc12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-43344259a13143f2b751032583d652d5 | C=[CH][Sn]([CH]=C)([CH]=C)[CH]=C.CCNC(=O)Nc1nc2ccc(Br)c(S(=O)(=O)C(F)(F)F)c2s1>>C=Cc1ccc2nc(NC(=O)NCC)sc2c1C=C | BrC1=C(C2=C(N=C(S2)NC(=O)NCC)C=C1)S(=O)(=O)C(F)(F)F.[Cl-].[Li+].C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C(=C)[Sn](C=C)(C=C)C=C.[Sn]>>C(=C)C1=C(C2=C(N=C(S2)NC(=O)NCC)C=C1)C=C | C=[CH][Sn]([CH]=C)([CH:2]=[CH2:1])[CH:18]=[CH2:19].O=S(=O)(C(F)(F)F)[c:17]1[c:3](Br)[cH:4][cH:5][c:6]2[n:7][c:8]([NH:9][C:10](=[O:11])[NH:12][CH2:13][CH3:14])[s:15][c:16]21>>[CH2:1]=[CH:2][c:3]1[cH:4][cH:5][c:6]2[n:7][c:8]([NH:9][C:10](=[O:11])[NH:12][CH2:13][CH3:14])[s:15][c:16]2[c:17]1[CH:18]=[CH2:19] | C=[CH][Sn]([CH]=C)([CH]=C)[CH]=C.CCNC(=O)Nc1nc2ccc(Br)c(S(=O)(=O)C(F)(F)F)c2s1 | C=Cc1ccc2nc(NC(=O)NCC)sc2c1C=C | null | Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl | CO | C-C Coupling | OtherReaction | 1148c4f7a7eb27ea822712bcb7856d412139833bcbe1012c1bdb4acd80153df0 | dd54cc01242eb3808113b5ff0843c27c76ad02e5faff96f50dec9c764e22c4a5 | c1ccc2scnc2c1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]2:[#7;a:5]:[c:6]:[#16;a:7]:[c:8]:2:[c;H0;D3;+0:9]:1-S(=O)(=O)-C(-F)(-F)-F.C=[CH]-[Sn](-[CH;D2;+0:10]=[C;D1;H2:11])(-[CH;D2;+0:12]=[C;D1;H2:13])-[CH]=C>>[C;D1;H2:11]=[CH;D2;+0:10]-[c;H0;D3;+0:9]1:[c:8]2:[#16;a:7]:[c:6]:[#7;a:5]:[c:4]:2:[c:3]:[c:2]:[c;H0;D3;+0:1]:1-[CH;D2;+0:12]=[C;D1;... | 39.4 | [{"value": 23.0, "product": "C(=C)C1=C(C2=C(N=C(S2)NC(=O)NCC)C=C1)C=C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 39.4, "product": "C(=C)C1=C(C2=C(N=C(S2)NC(=O)NCC)C=C1)C=C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | null | null | Similar to the synthesis of Example 203, a mixture of 1-(6-bromo-7-trifluoromethylsulfonyl-2-benzothiazolyl)-3-ethylurea (0.100 g, 0.22 mmol), lithium chloride (0.078 g, 1.84 mmol, 8.4 eq), triphenylphosphine (0.034 g, 0.13 mmol, 0.6 eq), Pd(PPh3)2Cl2 (0.018 g, 0.026 mmol, 0.12 eq), tetravinyltin (0.080 mL, 0.44 mmol, ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Tertiary halide.Tertiary halide.Tertiary halide.Sulfone.Vinyl.Vinyl.Vinyl.Vinyl.Tin | Vinyl.Vinyl | c1ccc2scnc2c1 | c1ccc2scnc2c1 | c1ccc2scnc2c1 | HF.Br-.Sn | Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl.CO | 100 | null | C=[CH][Sn]([CH]=C)([CH]=C)[CH]=C.CCNC(=O)Nc1nc2ccc(Br)c(S(=O)(=O)C(F)(F)F)c2s1>Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl.CO>C=Cc1ccc2nc(NC(=O)NCC)sc2c1C=C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-74007a0173b8457e84bcfc9f8de348a6 | N#C[S-].Nc1ccc(Cc2ccccc2)cc1>>Nc1nc2ccc(Cc3ccccc3)cc2s1 | BrBr.C(C1=CC=CC=C1)C1=CC=C(N)C=C1.C(#N)[S-].[K+]>>NC=1SC2=C(N1)C=CC(=C2)CC2=CC=CC=C2 | [N:1]#[C:2][S-:17].[NH2:3][c:4]1[cH:5][cH:6][c:7]([CH2:8][c:9]2[cH:10][cH:11][cH:12][cH:13][cH:14]2)[cH:15][cH:16]1>>[NH2:1][c:2]1[n:3][c:4]2[cH:5][cH:6][c:7]([CH2:8][c:9]3[cH:10][cH:11][cH:12][cH:13][cH:14]3)[cH:15][c:16]2[s:17]1 | N#C[S-].Nc1ccc(Cc2ccccc2)cc1 | Nc1nc2ccc(Cc3ccccc3)cc2s1 | null | null | C(C)(=O)O | Aromatic Heterocycle Formation | OtherReaction | 09d23668c864254f076a396c221fe470e495edd36b92b7e2edc27fa4162c1052 | c7c78474f6971eeaa7d180c68d4a8af29cb23110025e531bca1233dc3931475c | c1ccc(Cc2ccc3ncsc3c2)cc1 | [N;H0;D1;+0:1]#[C;H0;D2;+0:2]-[S-;H0;D1:3].[NH2;D1;+0:4]-[c:5](:[c:6]):[cH;D2;+0:7]:[c:8]:[c:9]>>[NH2;D1;+0:1]-[c;H0;D3;+0:2]1:[n;H0;D2;+0:4]:[c:5](:[c:6]):[c;H0;D3;+0:7](:[c:8]:[c:9]):[s;H0;D2;+0:3]:1 | 88.2 | [{"value": 88.0, "product": "NC=1SC2=C(N1)C=CC(=C2)CC2=CC=CC=C2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 88.2, "product": "NC=1SC2=C(N1)C=CC(=C2)CC2=CC=CC=C2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | A solution of 4-benzylaniline (0.916 g, 5.00 mmol) and KSCN (0.97 g, 10.0 mmol, 2.0 eq) in 10 mL acetic acid was cooled at about 5° C., and was treated dropwise with a solution of bromine (0.258 mL, 5.00 mmol, 1.0 eq) in 2 mL acetic acid. The mixture was stirred at room temperature for about 1 hour. The precipitate was... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile.Primary amine | Primary amine | c1ccccc1 | c1ccc2scnc2c1 | c1ccc2scnc2c1.c1ccccc1 | null | C(C)(=O)O | null | 1 | N#C[S-].Nc1ccc(Cc2ccccc2)cc1>C(C)(=O)O>Nc1nc2ccc(Cc3ccccc3)cc2s1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-507cd915806547c7b328f3dffb50e852 | CCN=C=O.Nc1nc2ccc(Cc3ccccc3)cc2s1>>CCNC(=O)Nc1nc2ccc(Cc3ccccc3)cc2s1 | NC=1SC2=C(N1)C=CC(=C2)CC2=CC=CC=C2.C(C)N(CC)CC.C(C)N=C=O>>C(C1=CC=CC=C1)C1=CC2=C(N=C(S2)NC(=O)NCC)C=C1 | [CH3:1][CH2:2][N:3]=[C:4]=[O:5].[NH2:6][c:7]1[n:8][c:9]2[cH:10][cH:11][c:12]([CH2:13][c:14]3[cH:15][cH:16][cH:17][cH:18][cH:19]3)[cH:20][c:21]2[s:22]1>>[CH3:1][CH2:2][NH:3][C:4](=[O:5])[NH:6][c:7]1[n:8][c:9]2[cH:10][cH:11][c:12]([CH2:13][c:14]3[cH:15][cH:16][cH:17][cH:18][cH:19]3)[cH:20][c:21]2[s:22]1 | CCN=C=O.Nc1nc2ccc(Cc3ccccc3)cc2s1 | CCNC(=O)Nc1nc2ccc(Cc3ccccc3)cc2s1 | null | null | C1(=CC=CC=C1)C | Acylation | Urea synthesis via isocyanate and primary amine | d39cd7dc52a79bb265ff8ef61ef7bf9dc7f7b5fb0150fcb4881bdfb18ab9c380 | a5dc801930c765d2a435a0a2973e50163c305ba8e7641d6adbcc1550b7b96de7 | c1ccc(Cc2ccc3ncsc3c2)cc1 | [C;D1;H3:1]-[C:2]-[N;H0;D2;+0:3]=[C;H0;D2;+0:4]=[O;D1;H0:5].[NH2;D1;+0:6]-[c:7]1:[#16;a:8]:[c:9]:[c:10]:[#7;a:11]:1>>[C;D1;H3:1]-[C:2]-[NH;D2;+0:3]-[C;H0;D3;+0:4](=[O;D1;H0:5])-[NH;D2;+0:6]-[c:7]1:[#16;a:8]:[c:9]:[c:10]:[#7;a:11]:1 | 56 | [{"value": 56.0, "product": "C(C1=CC=CC=C1)C1=CC2=C(N=C(S2)NC(=O)NCC)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 54.8, "product": "C(C1=CC=CC=C1)C1=CC2=C(N=C(S2)NC(=O)NCC)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 95 | CELSIUS | null | null | A suspension of 2-amino-6-benzyl-benzothiazole (0.040 g, 0.17 mmol), triethylamine (0.104 mL, 0.77 mmol, 4.5 eq), and ethyl isocyanate (0.049 mL, 0.64 mmol, 3.8 eq) in 1 mL toluene was heated at about 95° C. for about 16 hours. The precipitate was filtered off, washed with Et2O and MeOH, and dried under vacuum to give ... | 10.6084/m9.figshare.5104873.v1 | null | Isocyanate.Primary amine | Urea | null | null | c1ccc2scnc2c1.c1ccccc1 | null | C1(=CC=CC=C1)C | 95 | null | CCN=C=O.Nc1nc2ccc(Cc3ccccc3)cc2s1>C1(=CC=CC=C1)C>CCNC(=O)Nc1nc2ccc(Cc3ccccc3)cc2s1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-39cabe140ee74440b053a8e259355b3d | N#C[S-].Nc1ccc(Oc2ccc(F)cc2)cc1>>Nc1nc2ccc(Oc3ccc(F)cc3)cc2s1 | BrBr.FC1=CC=C(OC2=CC=C(N)C=C2)C=C1.C(#N)[S-].[K+]>>NC=1SC2=C(N1)C=CC(=C2)OC2=CC=C(C=C2)F | [N:1]#[C:2][S-:18].[NH2:3][c:4]1[cH:5][cH:6][c:7]([O:8][c:9]2[cH:10][cH:11][c:12]([F:13])[cH:14][cH:15]2)[cH:16][cH:17]1>>[NH2:1][c:2]1[n:3][c:4]2[cH:5][cH:6][c:7]([O:8][c:9]3[cH:10][cH:11][c:12]([F:13])[cH:14][cH:15]3)[cH:16][c:17]2[s:18]1 | N#C[S-].Nc1ccc(Oc2ccc(F)cc2)cc1 | Nc1nc2ccc(Oc3ccc(F)cc3)cc2s1 | null | null | C(C)(=O)O | Aromatic Heterocycle Formation | OtherReaction | 09d23668c864254f076a396c221fe470e495edd36b92b7e2edc27fa4162c1052 | c7c78474f6971eeaa7d180c68d4a8af29cb23110025e531bca1233dc3931475c | c1ccc(Oc2ccc3ncsc3c2)cc1 | [N;H0;D1;+0:1]#[C;H0;D2;+0:2]-[S-;H0;D1:3].[NH2;D1;+0:4]-[c:5](:[c:6]):[cH;D2;+0:7]:[c:8]:[c:9]>>[NH2;D1;+0:1]-[c;H0;D3;+0:2]1:[n;H0;D2;+0:4]:[c:5](:[c:6]):[c;H0;D3;+0:7](:[c:8]:[c:9]):[s;H0;D2;+0:3]:1 | 103.2 | [{"value": 90.0, "product": "NC=1SC2=C(N1)C=CC(=C2)OC2=CC=C(C=C2)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 103.2, "product": "NC=1SC2=C(N1)C=CC(=C2)OC2=CC=C(C=C2)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | A solution of 4-(4′-fluorophenoxy)aniline (0.305 g, 1.50 mmol) and KSCN (0.29 g, 3.00 mmol, 2.0 eq) in 3 mL acetic acid was cooled at about 5° C., and was treated dropwise with a solution of bromine (0.077 mL, 1.50 mmol, 1.0 eq) in 2 mL acetic acid. The mixture was stirred at room temperature for about 2 hours. The pre... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile.Primary amine | Primary amine | c1ccccc1 | c1ccc2scnc2c1 | c1ccc2scnc2c1.c1ccccc1 | null | C(C)(=O)O | null | 2 | N#C[S-].Nc1ccc(Oc2ccc(F)cc2)cc1>C(C)(=O)O>Nc1nc2ccc(Oc3ccc(F)cc3)cc2s1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b5f2f4212b8240a4b4901953e91f7565 | CCN=C=O.Nc1nc2ccc(Br)cc2s1>>CCNC(=O)Nc1nc2ccc(Br)cc2s1 | NC=1SC2=C(N1)C=CC(=C2)Br.C(C)N(CC)CC.C(C)N=C=O>>BrC1=CC2=C(N=C(S2)NC(=O)NCC)C=C1 | [CH3:1][CH2:2][N:3]=[C:4]=[O:5].[NH2:6][c:7]1[n:8][c:9]2[cH:10][cH:11][c:12]([Br:13])[cH:14][c:15]2[s:16]1>>[CH3:1][CH2:2][NH:3][C:4](=[O:5])[NH:6][c:7]1[n:8][c:9]2[cH:10][cH:11][c:12]([Br:13])[cH:14][c:15]2[s:16]1 | CCN=C=O.Nc1nc2ccc(Br)cc2s1 | CCNC(=O)Nc1nc2ccc(Br)cc2s1 | null | null | C1(=CC=CC=C1)C | Acylation | Urea synthesis via isocyanate and primary amine | d39cd7dc52a79bb265ff8ef61ef7bf9dc7f7b5fb0150fcb4881bdfb18ab9c380 | a5dc801930c765d2a435a0a2973e50163c305ba8e7641d6adbcc1550b7b96de7 | c1ccc2scnc2c1 | [C;D1;H3:1]-[C:2]-[N;H0;D2;+0:3]=[C;H0;D2;+0:4]=[O;D1;H0:5].[NH2;D1;+0:6]-[c:7]1:[#16;a:8]:[c:9]:[c:10]:[#7;a:11]:1>>[C;D1;H3:1]-[C:2]-[NH;D2;+0:3]-[C;H0;D3;+0:4](=[O;D1;H0:5])-[NH;D2;+0:6]-[c:7]1:[#16;a:8]:[c:9]:[c:10]:[#7;a:11]:1 | 94 | [{"value": 94.0, "product": "BrC1=CC2=C(N=C(S2)NC(=O)NCC)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 94.0, "product": "BrC1=CC2=C(N=C(S2)NC(=O)NCC)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 90 | CELSIUS | null | null | A suspension of 2-amino-6-bromo-benzothiazole (6.12 g, 26.2 mmol), triethylamine (7.30 mL, 52.4 mmol, 2.0 eq), and ethyl isocyanate (4.15 mL, 52.4 mmol, 2.0 eq) in 50 mL toluene was heated at about 90° C. for about 15 hours. The precipitate was filtered off, washed with Et2O, and dried under vacuum to give the desired ... | 10.6084/m9.figshare.5104873.v1 | null | Isocyanate.Primary amine | Urea | null | null | c1ccc2scnc2c1 | null | C1(=CC=CC=C1)C | 90 | null | CCN=C=O.Nc1nc2ccc(Br)cc2s1>C1(=CC=CC=C1)C>CCNC(=O)Nc1nc2ccc(Br)cc2s1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-257621e7b77e496c8a6049834742adcb | C#C[Si](C)(C)C.CCNC(=O)Nc1nc2ccc(Br)cc2s1>>CCNC(=O)Nc1nc2ccc(C#C[Si](C)(C)C)cc2s1 | BrC1=CC2=C(N=C(S2)NC(=O)NCC)C=C1.C(C)N(CC)CC.C[Si](C)(C)C#C>>C[Si](C)(C)C#CC1=CC2=C(N=C(S2)NC(=O)NCC)C=C1 | [CH:13]#[C:14][Si:15]([CH3:16])([CH3:17])[CH3:18].Br[c:12]1[cH:11][cH:10][c:9]2[n:8][c:7]([NH:6][C:4]([NH:3][CH2:2][CH3:1])=[O:5])[s:21][c:20]2[cH:19]1>>[CH3:1][CH2:2][NH:3][C:4](=[O:5])[NH:6][c:7]1[n:8][c:9]2[cH:10][cH:11][c:12]([C:13]#[C:14][Si:15]([CH3:16])([CH3:17])[CH3:18])[cH:19][c:20]2[s:21]1 | C#C[Si](C)(C)C.CCNC(=O)Nc1nc2ccc(Br)cc2s1 | CCNC(=O)Nc1nc2ccc(C#C[Si](C)(C)C)cc2s1 | null | Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl | CO.CN(C)C=O | C-C Coupling | Sonogashira alkyne_aryl halide | 81a8d0200d6382de35d744789f5ef14526aa97a1d031cda8081b95243d0e45dd | 305eca0fd2975da49e7f69e4edfb9dc1cbce82513954bc5a73be3289e70e5f76 | c1ccc2scnc2c1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]2:[#7;a:5]:[c:6]:[#16;a:7]:[c:8]:2:[c:9]:1.[C;D1;H3:10]-[#14:11](-[C;D1;H3:12])(-[C;D1;H3:13])-[C:14]#[CH;D1;+0:15]>>[C;D1;H3:10]-[#14:11](-[C;D1;H3:12])(-[C;D1;H3:13])-[C:14]#[C;H0;D2;+0:15]-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]2:[#7;a:5]:[c:6]:[#16;a:7]:[c:8]:2:[c:9]:1 | 89 | [{"value": 89.0, "product": "C[Si](C)(C)C#CC1=CC2=C(N=C(S2)NC(=O)NCC)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 88.8, "product": "C[Si](C)(C)C#CC1=CC2=C(N=C(S2)NC(=O)NCC)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | 15 | HOUR | A mixture of 1-(6-bromo-2-benzothiazolyl)-3-ethylurea (0.100 g, 0.33 mmol), Pd(PPh3)2Cl2 (0.012 g, 0.017 mmol, 0.05 eq), and triethylamine (0.20 mL, 1.42 mmol, 4.3 eq) in 1 mL of anhydrous DMF was bubbled with nitrogen gas for about 5 minutes, followed by the addition of trimethylsilyl acetylene (0.23 mL, 1.65 mmol, 5.... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Alkyne | Alkyne | c1ccc2scnc2c1 | c1ccc2scnc2c1 | c1ccc2scnc2c1 | HBr | Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl.CO.CN(C)C=O | 80 | 15 | C#C[Si](C)(C)C.CCNC(=O)Nc1nc2ccc(Br)cc2s1>Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl.CO.CN(C)C=O>CCNC(=O)Nc1nc2ccc(C#C[Si](C)(C)C)cc2s1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-6e34ac8687504305874573b2b52188a8 | C#Cc1ccccc1.CCNC(=O)Nc1nc2ccc(Br)cc2s1>>CCNC(=O)Nc1nc2ccc(C#Cc3ccccc3)cc2s1 | BrC1=CC2=C(N=C(S2)NC(=O)NCC)C=C1.C(C)N(CC)CC.C1(=CC=CC=C1)C#C>>C1(=CC=CC=C1)C#CC1=CC2=C(N=C(S2)NC(=O)NCC)C=C1 | [CH:13]#[C:14][c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1.Br[c:12]1[cH:11][cH:10][c:9]2[n:8][c:7]([NH:6][C:4]([NH:3][CH2:2][CH3:1])=[O:5])[s:23][c:22]2[cH:21]1>>[CH3:1][CH2:2][NH:3][C:4](=[O:5])[NH:6][c:7]1[n:8][c:9]2[cH:10][cH:11][c:12]([C:13]#[C:14][c:15]3[cH:16][cH:17][cH:18][cH:19][cH:20]3)[cH:21][c:22]2[s:23]1 | C#Cc1ccccc1.CCNC(=O)Nc1nc2ccc(Br)cc2s1 | CCNC(=O)Nc1nc2ccc(C#Cc3ccccc3)cc2s1 | null | Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl | CN(C)C=O | C-C Coupling | Sonogashira alkyne_aryl halide | 81a8d0200d6382de35d744789f5ef14526aa97a1d031cda8081b95243d0e45dd | 305eca0fd2975da49e7f69e4edfb9dc1cbce82513954bc5a73be3289e70e5f76 | C(#Cc1ccc2ncsc2c1)c1ccccc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]2:[#7;a:5]:[c:6]:[#16;a:7]:[c:8]:2:[c:9]:1.[CH;D1;+0:10]#[C:11]-[c:12]>>[c:12]-[C:11]#[C;H0;D2;+0:10]-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]2:[#7;a:5]:[c:6]:[#16;a:7]:[c:8]:2:[c:9]:1 | 8 | [{"value": 8.0, "product": "C1(=CC=CC=C1)C#CC1=CC2=C(N=C(S2)NC(=O)NCC)C=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 1-(6-bromo-2-benzothiazolyl)-3-ethylurea, Pd(PPh3)2Cl2, triethylamine, and phenylacetylene in 1 mL of anhydrous DMF was reacted according to the procedure of Example 213 to give 0.008 g (8%) of the desired compound. LC/MS 322 (M+1); LC retention time 3.65 min.
Conditions: See reaction.notes.procedure_detai... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Alkyne | Alkyne | c1ccc2scnc2c1 | c1ccc2scnc2c1 | c1ccc2scnc2c1.c1ccccc1 | HBr | Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl.CN(C)C=O | null | null | C#Cc1ccccc1.CCNC(=O)Nc1nc2ccc(Br)cc2s1>Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl.CN(C)C=O>CCNC(=O)Nc1nc2ccc(C#Cc3ccccc3)cc2s1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-e28f5a27454f477e9bdcf8a67a519fdf | CCNC(=O)Nc1nc2ccc(C#C[Si](C)(C)C)cc2s1>>C#Cc1ccc2nc(NC(=O)NCC)sc2c1 | C[Si](C)(C)C#CC1=CC2=C(N=C(S2)NC(=O)NCC)C=C1.[OH-].[K+].Cl>>C(#C)C1=CC2=C(N=C(S2)NC(=O)NCC)C=C1 | C[Si](C)(C)[C:1]#[C:2][c:3]1[cH:4][cH:5][c:6]2[n:7][c:8]([NH:9][C:10](=[O:11])[NH:12][CH2:13][CH3:14])[s:15][c:16]2[cH:17]1>>[CH:1]#[C:2][c:3]1[cH:4][cH:5][c:6]2[n:7][c:8]([NH:9][C:10](=[O:11])[NH:12][CH2:13][CH3:14])[s:15][c:16]2[cH:17]1 | CCNC(=O)Nc1nc2ccc(C#C[Si](C)(C)C)cc2s1 | C#Cc1ccc2nc(NC(=O)NCC)sc2c1 | null | null | CO.CCOC(=O)C | Deprotection | TMS deprotection from alkyne | e85676bb81da384790c9c858d44f182cdd01e3a79f77f7a239fe38487234cb96 | 56d526d7c9cb1bd7bee4940e216a9b1dd4597fd025a186b8d6e4675d8f4db26b | c1ccc2scnc2c1 | C-[Si](-C)(-C)-[C;H0;D2;+0:1]#[C:2]-[c:3]>>[CH;D1;+0:1]#[C:2]-[c:3] | 5.6 | [{"value": 5.0, "product": "C(#C)C1=CC2=C(N=C(S2)NC(=O)NCC)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 5.6, "product": "C(#C)C1=CC2=C(N=C(S2)NC(=O)NCC)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | A mixture of 1-(6-trimethylsilylacetylenyl-2-benzothiazolyl)-3-ethylurea (0.0710 g, 0.22 mmol) and 1M aqueous KOH solution (1.22 mL, 1.22 mmol, 5.5 eq) in 1.5 mL MeOH was stirred at room temperature for about 2 hours. The mixture acidified with 1 M HCl, then taken up in 20 mL AcOEt, and the aqueous phase was extracted ... | 10.6084/m9.figshare.5104873.v1 | null | Alkyne.Silyl protective group | Alkyne | null | null | c1ccc2scnc2c1 | Other | CO.CCOC(=O)C | null | 2 | CCNC(=O)Nc1nc2ccc(C#C[Si](C)(C)C)cc2s1>CO.CCOC(=O)C>C#Cc1ccc2nc(NC(=O)NCC)sc2c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-95e95ae24cd64ca5ba5ab0c7319f2bfb | CCNC(=O)Nc1nc2ccc(C#Cc3ccccc3)cc2s1>>CCNC(=O)Nc1nc2ccc(CCc3ccccc3)cc2s1 | C1(=CC=CC=C1)C#CC1=CC2=C(N=C(S2)NC(=O)NCC)C=C1>>C1(=CC=CC=C1)CCC1=CC2=C(N=C(S2)NC(=O)NCC)C=C1 | [CH3:1][CH2:2][NH:3][C:4](=[O:5])[NH:6][c:7]1[n:8][c:9]2[cH:10][cH:11][c:12]([C:13]#[C:14][c:15]3[cH:16][cH:17][cH:18][cH:19][cH:20]3)[cH:21][c:22]2[s:23]1>>[CH3:1][CH2:2][NH:3][C:4](=[O:5])[NH:6][c:7]1[n:8][c:9]2[cH:10][cH:11][c:12]([CH2:13][CH2:14][c:15]3[cH:16][cH:17][cH:18][cH:19][cH:20]3)[cH:21][c:22]2[s:23]1 | CCNC(=O)Nc1nc2ccc(C#Cc3ccccc3)cc2s1 | CCNC(=O)Nc1nc2ccc(CCc3ccccc3)cc2s1 | null | [Pd] | C(C)O | Reduction | OtherReaction | 2bb8d5b532a2781e0a7c069a5cd3e8a7e8d44660c0ec1d9e17c04d8ba2cb383b | 1990560e9c55934bde8ca0feaed9c61d80f37f94f0cf240a9929dc374d0a33aa | c1ccc(CCc2ccc3ncsc3c2)cc1 | [#16;a:1]:[c:2]:[c:3]:[c:4](-[C;H0;D2;+0:5]#[C;H0;D2;+0:6]-[c:7](:[c:8]):[c:9]):[c:10]>>[#16;a:1]:[c:2]:[c:3]:[c:4](-[CH2;D2;+0:5]-[CH2;D2;+0:6]-[c:7](:[c:8]):[c:9]):[c:10] | 76 | [{"value": 76.0, "product": "C1(=CC=CC=C1)CCC1=CC2=C(N=C(S2)NC(=O)NCC)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 75.8, "product": "C1(=CC=CC=C1)CCC1=CC2=C(N=C(S2)NC(=O)NCC)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 16 | HOUR | A suspension of 1-(6-phenylacetylenyl-2-benzothiazolyl)-3-ethylurea (0.048 g, 0.15 mmol) and 10% palladium on carbon (0.016 g, 10% weight purity, 0.015 mmol, 0.10 eq) in 2 mL ethanol was purged with nitrogen gas, followed by bubbling of hydrogen gas. It was stirred under hydrogen atmosphere for about 16 hours. The mixt... | 10.6084/m9.figshare.5104873.v1 | null | Alkyne | null | null | null | c1ccc2scnc2c1.c1ccccc1 | null | [Pd].C(C)O | null | 16 | CCNC(=O)Nc1nc2ccc(C#Cc3ccccc3)cc2s1>[Pd].C(C)O>CCNC(=O)Nc1nc2ccc(CCc3ccccc3)cc2s1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b034843c1eae49b58ee346d1b1960c87 | CCNC(=O)Nc1nc2ccc(C#Cc3ccccc3)cc2s1>>CCNC(=O)Nc1nc2ccc(/C=C\c3ccccc3)cc2s1 | C1(=CC=CC=C1)C#CC1=CC2=C(N=C(S2)NC(=O)NCC)C=C1>>C1(=CC=CC=C1)\C=C/C1=CC2=C(N=C(S2)NC(=O)NCC)C=C1 | [CH3:1][CH2:2][NH:3][C:4](=[O:5])[NH:6][c:7]1[n:8][c:9]2[cH:10][cH:11][c:12]([C:13]#[C:14][c:15]3[cH:16][cH:17][cH:18][cH:19][cH:20]3)[cH:21][c:22]2[s:23]1>>[CH3:1][CH2:2][NH:3][C:4](=[O:5])[NH:6][c:7]1[n:8][c:9]2[cH:10][cH:11][c:12](/[CH:13]=[CH:14]\[c:15]3[cH:16][cH:17][cH:18][cH:19][cH:20]3)[cH:21][c:22]2[s:23]1 | CCNC(=O)Nc1nc2ccc(C#Cc3ccccc3)cc2s1 | CCNC(=O)Nc1nc2ccc(/C=C\c3ccccc3)cc2s1 | null | [Pd].CC(=O)[O-].CC(=O)[O-].[Pb+2] | C(C)O | Reduction | Hydrogenation (triple to double) | 2bb8d5b532a2781e0a7c069a5cd3e8a7e8d44660c0ec1d9e17c04d8ba2cb383b | 1990560e9c55934bde8ca0feaed9c61d80f37f94f0cf240a9929dc374d0a33aa | C(=C\c1ccc2ncsc2c1)\c1ccccc1 | [#16;a:1]:[c:2]:[c:3]:[c:4](-[C;H0;D2;+0:5]#[C;H0;D2;+0:6]-[c:7](:[c:8]):[c:9]):[c:10]>>[#16;a:1]:[c:2]:[c:3]:[c:4](/[CH;D2;+0:5]=[CH;D2;+0:6]\[c:7](:[c:8]):[c:9]):[c:10] | 41 | [{"value": 41.0, "product": "C1(=CC=CC=C1)\\C=C/C1=CC2=C(N=C(S2)NC(=O)NCC)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 41.0, "product": "C1(=CC=CC=C1)\\C=C/C1=CC2=C(N=C(S2)NC(=O)NCC)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 36 | HOUR | A suspension of 1-(6-phenylacetylenyl-2-benzothiazolyl)-3-ethylurea (0.032 g, 83% purity by weight, 0.083 mmol) and Lindlar catalyst (0.030 g, 5% weight purity, 0.012 mmol, 0.15 eq) in 2 mL ethanol was purged with nitrogen gas, followed by bubbling of hydrogen gas. It was stirred under hydrogen atmosphere for about 36 ... | 10.6084/m9.figshare.5104873.v1 | null | Alkyne | null | null | null | c1ccc2scnc2c1.c1ccccc1 | null | [Pd].CC(=O)[O-].CC(=O)[O-].[Pb+2].C(C)O | null | 36 | CCNC(=O)Nc1nc2ccc(C#Cc3ccccc3)cc2s1>[Pd].CC(=O)[O-].CC(=O)[O-].[Pb+2].C(C)O>CCNC(=O)Nc1nc2ccc(/C=C\c3ccccc3)cc2s1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-e3c1889fcfaf4fb982b73eceaea5d2bc | C=Cc1ccccc1.CCNC(=O)Nc1nc2ccc(Br)cc2s1>>CCNC(=O)Nc1nc2ccc(/C=C/c3ccccc3)cc2s1 | BrC1=CC2=C(N=C(S2)NC(=O)NCC)C=C1.C=1C=CC(=CC1)P(CCCP(C=2C=CC=CC2)C=3C=CC=CC3)C=4C=CC=CC4.C(C)N(CC)CC.C=CC1=CC=CC=C1>>C1(=CC=CC=C1)/C=C/C1=CC2=C(N=C(S2)NC(=O)NCC)C=C1 | [CH2:13]=[CH:14][c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1.Br[c:12]1[cH:11][cH:10][c:9]2[n:8][c:7]([NH:6][C:4]([NH:3][CH2:2][CH3:1])=[O:5])[s:23][c:22]2[cH:21]1>>[CH3:1][CH2:2][NH:3][C:4](=[O:5])[NH:6][c:7]1[n:8][c:9]2[cH:10][cH:11][c:12](/[CH:13]=[CH:14]/[c:15]3[cH:16][cH:17][cH:18][cH:19][cH:20]3)[cH:21][c:22]2[s:23... | C=Cc1ccccc1.CCNC(=O)Nc1nc2ccc(Br)cc2s1 | CCNC(=O)Nc1nc2ccc(/C=C/c3ccccc3)cc2s1 | null | Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl | CN(C)C=O | C-C Coupling | Heck terminal vinyl | 75ca16f9fb0fbd5ca837ac801a3bf869050db64700b139faf9efed8ef9e02537 | 4b186811a4930853b446d93d9faa39b267bddb9ce0b8021bda5c5a3b2bc69f0b | C(=C/c1ccc2ncsc2c1)\c1ccccc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]2:[#7;a:5]:[c:6]:[#16;a:7]:[c:8]:2:[c:9]:1.[CH2;D1;+0:10]=[C:11]-[c:12]>>[c:12]/[C:11]=[CH;D2;+0:10]/[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]2:[#7;a:5]:[c:6]:[#16;a:7]:[c:8]:2:[c:9]:1 | 62 | [{"value": 62.0, "product": "C1(=CC=CC=C1)/C=C/C1=CC2=C(N=C(S2)NC(=O)NCC)C=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 1-(6-bromo-2-benzothiazolyl)-3-ethylurea, Pd(PPh3)2Cl2, dppp, triethylamine, styrene, and two crystals of BHT in anhydrous DMF was reacted according to the procedure of Example 225 to give the desired compound 0.201 g (62%). LC/MS 324.2 (M+1); LC retention time 2.87 min.
Conditions: See reaction.notes.proc... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Vinyl | null | c1ccc2scnc2c1 | c1ccc2scnc2c1 | c1ccc2scnc2c1.c1ccccc1 | HBr | Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl.CN(C)C=O | null | null | C=Cc1ccccc1.CCNC(=O)Nc1nc2ccc(Br)cc2s1>Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl.CN(C)C=O>CCNC(=O)Nc1nc2ccc(/C=C/c3ccccc3)cc2s1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-740e84ce00124f83a802a02af18c14b6 | COC(=S)Cl.Nc1nc2ccc(Oc3ccc(F)cc3)cc2s1>>CCOC(=S)Nc1nc2ccc(Oc3ccc(F)cc3)cc2s1 | Cl.ClC(=S)OC.NC=1SC2=C(N1)C=CC(=C2)OC2=CC=C(C=C2)F.N1=CC=CC=C1>>FC1=CC=C(OC2=CC3=C(N=C(S3)NC(OCC)=S)C=C2)C=C1 | Cl[C:4]([O:3][CH3:2])=[S:5].[NH2:6][c:7]1[n:8][c:9]2[cH:10][cH:11][c:12]([O:13][c:14]3[cH:15][cH:16][c:17]([F:18])[cH:19][cH:20]3)[cH:21][c:22]2[s:23]1>>[CH3:1][CH2:2][O:3][C:4](=[S:5])[NH:6][c:7]1[n:8][c:9]2[cH:10][cH:11][c:12]([O:13][c:14]3[cH:15][cH:16][c:17]([F:18])[cH:19][cH:20]3)[cH:21][c:22]2[s:23]1 | COC(=S)Cl.Nc1nc2ccc(Oc3ccc(F)cc3)cc2s1 | CCOC(=S)Nc1nc2ccc(Oc3ccc(F)cc3)cc2s1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 0a23a66795ec4b7fa0bd30742fc813ad896e669d9d6489e05f50db8a591c6b07 | 373750671fa9bcc9f846e7098fb90c60e0ea9e513d59381135c62cc38d06816d | c1ccc(Oc2ccc3ncsc3c2)cc1 | Cl-[C;H0;D3;+0:1](=[S;D1;H0:2])-[#8:3]-[CH3;D1;+0:4].[NH2;D1;+0:5]-[c:6]1:[#16;a:7]:[c:8]:[c:9]:[#7;a:10]:1>>[C;D1;H3:11]-[CH2;D2;+0:4]-[#8:3]-[C;H0;D3;+0:1](=[S;D1;H0:2])-[NH;D2;+0:5]-[c:6]1:[#16;a:7]:[c:8]:[c:9]:[#7;a:10]:1 | 65 | [{"value": 65.0, "product": "FC1=CC=C(OC2=CC3=C(N=C(S3)NC(OCC)=S)C=C2)C=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | A suspension of 2-amino-6-(4′-fluorophenoxy)-benzothiazole (associated with 2.0 eq of KBr salt, 2.50 g, 5.02 mmol) in 10 mL pyridine was treated dropwise with methyl chlorothioformate (0.65 mL, 7.53 mmol, 01.5 eq). It was stirred at room temperature for about 1 hour, and was poured into 40 mL ice water. The mixture was... | 10.6084/m9.figshare.5104873.v1 | null | Alkenyl halide.Ether.Primary amine | Ether.Thioamide | null | null | c1ccc2scnc2c1.c1ccccc1 | null | null | null | 1 | COC(=S)Cl.Nc1nc2ccc(Oc3ccc(F)cc3)cc2s1>>CCOC(=S)Nc1nc2ccc(Oc3ccc(F)cc3)cc2s1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-193af041f89c4a718cbabf830a9304dc | CCNC(=O)Nc1nc2ccc(Cc3ccccc3)cc2s1.CCOC(=O)c1ccc2nc(N)sc2c1>>CCNC(=O)Nc1nc2ccc(C(=O)OCC)cc2s1 | C(C1=CC=CC=C1)C1=CC2=C(N=C(S2)NC(=O)NCC)C=C1.NC=1SC2=C(N1)C=CC(=C2)C(=O)OCC.C(C)N(CC)CC.C(C)N=C=O>>C(C)OC(=O)C1=CC2=C(N=C(S2)NC(=O)NCC)C=C1 | c1ccc(Cc2ccc3nc(N[C:4]([NH:3][CH2:2][CH3:1])=[O:5])sc3c2)cc1.[NH2:6][c:7]1[n:8][c:9]2[cH:10][cH:11][c:12]([C:13](=[O:14])[O:15][CH2:16][CH3:17])[cH:18][c:19]2[s:20]1>>[CH3:1][CH2:2][NH:3][C:4](=[O:5])[NH:6][c:7]1[n:8][c:9]2[cH:10][cH:11][c:12]([C:13](=[O:14])[O:15][CH2:16][CH3:17])[cH:18][c:19]2[s:20]1 | CCNC(=O)Nc1nc2ccc(Cc3ccccc3)cc2s1.CCOC(=O)c1ccc2nc(N)sc2c1 | CCNC(=O)Nc1nc2ccc(C(=O)OCC)cc2s1 | null | null | C1(=CC=CC=C1)C | Acylation | OtherReaction | ba60c90fe4fc8b1bce2e75337f9f3b3b4a82100ebf9cf0bdc0393fc79ed9c761 | f17cc9fc6250903fc236407915f5767fca8f6b6242f886ce02918cf1cdfcba61 | c1ccc2scnc2c1 | [C:1]-[#7:2]-[C;H0;D3;+0:3](=[O;D1;H0:4])-N-c1:n:c2:c:c:c(-C-c3:c:c:c:c:c:3):c:c:2:s:1.[NH2;D1;+0:5]-[c:6]1:[#16;a:7]:[c:8]:[c:9]:[#7;a:10]:1>>[C:1]-[#7:2]-[C;H0;D3;+0:3](=[O;D1;H0:4])-[NH;D2;+0:5]-[c:6]1:[#16;a:7]:[c:8]:[c:9]:[#7;a:10]:1 | 82 | [{"value": 82.0, "product": "C(C)OC(=O)C1=CC2=C(N=C(S2)NC(=O)NCC)C=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | According to the General Procedure for 1-(6-substituted-2-benzothiazolyl)-3-ethylurea compounds, and similar to the synthesis of 1-(6-benzyl-2-benzothiazolyl)-3-ethylurea, a mixture of 2-amino-6-ethoxycarbonyl-benzothiazole, triethylamine and ethyl isocyanate in toluene was reacted to give the desired compound 2.40 g (... | 10.6084/m9.figshare.5104873.v1 | null | Urea.Primary amine | Urea | c1ccccc1.c1ccc2scnc2c1 | null | c1ccc2scnc2c1 | Other | C1(=CC=CC=C1)C | null | null | CCNC(=O)Nc1nc2ccc(Cc3ccccc3)cc2s1.CCOC(=O)c1ccc2nc(N)sc2c1>C1(=CC=CC=C1)C>CCNC(=O)Nc1nc2ccc(C(=O)OCC)cc2s1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-8549526be9da42f8b9e0ee50ad49b065 | CC#N.CCNC(=O)Nc1nc2ccc(C(=O)OCC)cc2s1>>CCNC(=O)Nc1nc2ccc(C(=O)CC#N)cc2s1 | C1CCOC1.C(C)OC(=O)C1=CC2=C(N=C(S2)NC(=O)NCC)C=C1.C(C)#N.[Li+].C[Si](C)(C)[N-][Si](C)(C)C.[Li+].C[Si](C)(C)[N-][Si](C)(C)C>>C(#N)CC(=O)C1=CC2=C(N=C(S2)NC(=O)NCC)C=C1 | [CH3:15][C:16]#[N:17].CCO[C:13]([c:12]1[cH:11][cH:10][c:9]2[n:8][c:7]([NH:6][C:4]([NH:3][CH2:2][CH3:1])=[O:5])[s:20][c:19]2[cH:18]1)=[O:14]>>[CH3:1][CH2:2][NH:3][C:4](=[O:5])[NH:6][c:7]1[n:8][c:9]2[cH:10][cH:11][c:12]([C:13](=[O:14])[CH2:15][C:16]#[N:17])[cH:18][c:19]2[s:20]1 | CC#N.CCNC(=O)Nc1nc2ccc(C(=O)OCC)cc2s1 | CCNC(=O)Nc1nc2ccc(C(=O)CC#N)cc2s1 | null | null | CN(C)C=O | C-C Coupling | OtherReaction | 8ce89878f5db9b98fa4633d16adf2407dbf79d96925d930c608f1ce0756e674e | f80cbbd7f2bfc042e62829b7de30498cf0880b808f2adad888ffdfe089982722 | c1ccc2scnc2c1 | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5]:[c:6]:[#16;a:7].[CH3;D1;+0:8]-[C:9]#[N;D1;H0:10]>>[#16;a:7]:[c:6]:[c:5]:[c:3](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[CH2;D2;+0:8]-[C:9]#[N;D1;H0:10]):[c:4] | 54 | [{"value": 54.0, "product": "C(#N)CC(=O)C1=CC2=C(N=C(S2)NC(=O)NCC)C=C1", "details": "PERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 0.5 | HOUR | A solution of 1-(6-ethoxycarbonyl-2-benzothiazolyl)-3-ethylurea (1.20 g, 4.09 mmol) in 5 mL of anhydrous DMF was treated with 2 mL of acetonitrile, cooled down to about 0° C., followed by treatment with 1 M LiHMDS in THF (13.1 mL, 13.1 mmol, 3.2 eq). It was stirred at the temperature for about 0.5 hour, then warmed up ... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Ketone | null | null | c1ccc2scnc2c1 | HO- | CN(C)C=O | 0 | 0.5 | CC#N.CCNC(=O)Nc1nc2ccc(C(=O)OCC)cc2s1>CN(C)C=O>CCNC(=O)Nc1nc2ccc(C(=O)CC#N)cc2s1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-ec7552d657b74d9cb90ee4e75ae57522 | CCNC(=O)Nc1nc2ccc(C(=O)CC#N)cc2s1>>CCNC(=O)Nc1nc2ccc(C(=O)CCN)cc2s1 | C(#N)CC(=O)C1=CC2=C(N=C(S2)NC(=O)NCC)C=C1.CO>>NCCC(=O)C1=CC2=C(N=C(S2)NC(=O)NCC)C=C1 | [CH3:1][CH2:2][NH:3][C:4](=[O:5])[NH:6][c:7]1[n:8][c:9]2[cH:10][cH:11][c:12]([C:13](=[O:14])[CH2:15][C:16]#[N:17])[cH:18][c:19]2[s:20]1>>[CH3:1][CH2:2][NH:3][C:4](=[O:5])[NH:6][c:7]1[n:8][c:9]2[cH:10][cH:11][c:12]([C:13](=[O:14])[CH2:15][CH2:16][NH2:17])[cH:18][c:19]2[s:20]1 | CCNC(=O)Nc1nc2ccc(C(=O)CC#N)cc2s1 | CCNC(=O)Nc1nc2ccc(C(=O)CCN)cc2s1 | null | [Pt](=O)=O | C(Cl)(Cl)Cl | Reduction | Reduction of nitrile to amine | 65bec2d9f430701d30dc9fcbe1c5418f3dfa174d67be035c50edfc71895dc9c7 | e8d1bc928b94bd4f5bf4b23363ce8f88b1ce7d146ba93829e7b8ad8dbe0007a7 | c1ccc2scnc2c1 | [N;H0;D1;+0:1]#[C;H0;D2;+0:2]-[C:3]-[C:4](=[O;D1;H0:5])-[c:6]>>[NH2;D1;+0:1]-[CH2;D2;+0:2]-[C:3]-[C:4](=[O;D1;H0:5])-[c:6] | 121.5 | [{"value": 121.5, "product": "NCCC(=O)C1=CC2=C(N=C(S2)NC(=O)NCC)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | DAY | A suspension of 1-(6-(2-cyanoacetyl)-2-benzothiazolyl)-3-ethylurea (0.56 g, 1.94 mmol) and platinum (IV) oxide (0.176 g, 0.78 mmol, 0.40 eq) in 50 mL of 2/3 mixture of MeOH and chloroform was purged and bubbled with hydrogen gas. It was stirred under hydrogen gas for about 2 days. The mixture was filtered and concentra... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile | Primary amine | null | null | c1ccc2scnc2c1 | null | [Pt](=O)=O.C(Cl)(Cl)Cl | null | 48 | CCNC(=O)Nc1nc2ccc(C(=O)CC#N)cc2s1>[Pt](=O)=O.C(Cl)(Cl)Cl>CCNC(=O)Nc1nc2ccc(C(=O)CCN)cc2s1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-d4a430f6fb924fac95a71637b5597afc | CCNC(=O)Nc1nc2ccc(C(=O)CCN)cc2s1.O=C(Cl)c1ccccc1>>CCNC(=O)Nc1nc2ccc(C(=O)CCNC(=O)c3ccccc3)cc2s1 | C(C1=CC=CC=C1)(=O)Cl.NCCC(=O)C1=CC2=C(N=C(S2)NC(=O)NCC)C=C1.C(C)N(CC)CC>>C(C)NC(=O)NC=1SC2=C(N1)C=CC(=C2)C(CCNC(C2=CC=CC=C2)=O)=O | [CH3:1][CH2:2][NH:3][C:4](=[O:5])[NH:6][c:7]1[n:8][c:9]2[cH:10][cH:11][c:12]([C:13](=[O:14])[CH2:15][CH2:16][NH2:17])[cH:26][c:27]2[s:28]1.Cl[C:18](=[O:19])[c:20]1[cH:21][cH:22][cH:23][cH:24][cH:25]1>>[CH3:1][CH2:2][NH:3][C:4](=[O:5])[NH:6][c:7]1[n:8][c:9]2[cH:10][cH:11][c:12]([C:13](=[O:14])[CH2:15][CH2:16][NH:17][C:1... | CCNC(=O)Nc1nc2ccc(C(=O)CCN)cc2s1.O=C(Cl)c1ccccc1 | CCNC(=O)Nc1nc2ccc(C(=O)CCNC(=O)c3ccccc3)cc2s1 | null | null | CN(C)C=O | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=C(CCNC(=O)c1ccccc1)c1ccc2ncsc2c1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[NH2;D1;+0:6]-[C:7]-[C:8]-[C:9]=[O;D1;H0:10]>>[O;D1;H0:10]=[C:9]-[C:8]-[C:7]-[NH;D2;+0:6]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5] | 28 | [{"value": 28.0, "product": "C(C)NC(=O)NC=1SC2=C(N1)C=CC(=C2)C(CCNC(C2=CC=CC=C2)=O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 27.7, "product": "C(C)NC(=O)NC=1SC2=C(N1)C=CC(=C2)C(CCNC(C2=CC=CC=C2)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 5 | MINUTE | A solution of 1-(6-(3-aminopropanoyl)-2-benzothiazolyl)-3-ethylurea (0.033 g, 0.10 mmol) in 1 mL anhydrous DMF was treated with triethylamine (0.028 mL, 0.20 mmol, 2.0 eq) at room temperature. It was stirred for about 5 min, followed by the addition of benzoyl chloride (0.014 mL, 0.12 mmol, 1.2 eq). It was stirred for ... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccc2scnc2c1.c1ccccc1 | HCl | CN(C)C=O | null | 0.083333 | CCNC(=O)Nc1nc2ccc(C(=O)CCN)cc2s1.O=C(Cl)c1ccccc1>CN(C)C=O>CCNC(=O)Nc1nc2ccc(C(=O)CCNC(=O)c3ccccc3)cc2s1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-7c11d59354d54b46b7c009458d9fc655 | CCNC(=O)Nc1nc2ccc(C(=O)CCN)cc2s1.O=C=Nc1ccccc1>>CCNC(=O)Nc1nc2ccc(C(=O)CCNC(=O)Nc3ccccc3)cc2s1 | C1(=CC=CC=C1)N=C=O.NCCC(=O)C1=CC2=C(N=C(S2)NC(=O)NCC)C=C1.C(C)N(CC)CC>>C1(=CC=CC=C1)NC(=O)NCCC(=O)C1=CC2=C(N=C(S2)NC(=O)NCC)C=C1 | [CH3:1][CH2:2][NH:3][C:4](=[O:5])[NH:6][c:7]1[n:8][c:9]2[cH:10][cH:11][c:12]([C:13](=[O:14])[CH2:15][CH2:16][NH2:17])[cH:27][c:28]2[s:29]1.[C:18](=[O:19])=[N:20][c:21]1[cH:22][cH:23][cH:24][cH:25][cH:26]1>>[CH3:1][CH2:2][NH:3][C:4](=[O:5])[NH:6][c:7]1[n:8][c:9]2[cH:10][cH:11][c:12]([C:13](=[O:14])[CH2:15][CH2:16][NH:17... | CCNC(=O)Nc1nc2ccc(C(=O)CCN)cc2s1.O=C=Nc1ccccc1 | CCNC(=O)Nc1nc2ccc(C(=O)CCNC(=O)Nc3ccccc3)cc2s1 | null | null | CN(C)C=O | Acylation | Urea synthesis via isocyanate and primary amine | d39cd7dc52a79bb265ff8ef61ef7bf9dc7f7b5fb0150fcb4881bdfb18ab9c380 | a5dc801930c765d2a435a0a2973e50163c305ba8e7641d6adbcc1550b7b96de7 | O=C(NCCC(=O)c1ccc2ncsc2c1)Nc1ccccc1 | [NH2;D1;+0:1]-[C:2]-[C:3]-[C:4]=[O;D1;H0:5].[O;D1;H0:6]=[C;H0;D2;+0:7]=[N;H0;D2;+0:8]-[c:9](:[c:10]):[c:11]>>[O;D1;H0:5]=[C:4]-[C:3]-[C:2]-[NH;D2;+0:1]-[C;H0;D3;+0:7](=[O;D1;H0:6])-[NH;D2;+0:8]-[c:9](:[c:10]):[c:11] | 22 | [{"value": 22.0, "product": "C1(=CC=CC=C1)NC(=O)NCCC(=O)C1=CC2=C(N=C(S2)NC(=O)NCC)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 21.9, "product": "C1(=CC=CC=C1)NC(=O)NCCC(=O)C1=CC2=C(N=C(S2)NC(=O)NCC)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 5 | MINUTE | A solution of 1-(6-(3-aminopropanoyl)-2-benzothiazolyl)-3-ethylurea (0.033 g, 0.10 mmol) in 1 mL anhydrous DMF was treated with triethylamine (0.028 mL, 0.20 mmol, 2.0 eq) at room temperature. It was stirred for about 5 min, followed by the addition of phenyl isocyanate (0.013 mL, 0.12 mmol, 1.2 eq). It was stirred for... | 10.6084/m9.figshare.5104873.v1 | null | Isocyanate.Primary amine | Urea | null | null | c1ccc2scnc2c1.c1ccccc1 | null | CN(C)C=O | null | 0.083333 | CCNC(=O)Nc1nc2ccc(C(=O)CCN)cc2s1.O=C=Nc1ccccc1>CN(C)C=O>CCNC(=O)Nc1nc2ccc(C(=O)CCNC(=O)Nc3ccccc3)cc2s1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-3b86cf3eeca34ce7947e49ad0db3feaf | CCN(CC)CC.CCNC(=O)Nc1nc2ccc(C(=O)CCN)cc2s1.[N-]=C=O>>CCNC(=O)Nc1nc2ccc(C(=O)CCNC(=O)Nc3cccc(C)c3)cc2s1 | NCCC(=O)C1=CC2=C(N=C(S2)NC(=O)NCC)C=C1.C(C)N(CC)CC.[N-]=C=O>>CC=1C=C(C=CC1)NC(=O)NCCC(=O)C1=CC2=C(N=C(S2)NC(=O)NCC)C=C1 | N([CH2:21][CH3:22])([CH2:25][CH3:26])[CH2:27][CH3:23].[CH3:1][CH2:2][NH:3][C:4](=[O:5])[NH:6][c:7]1[n:8][c:9]2[cH:10][cH:11][c:12]([C:13](=[O:14])[CH2:15][CH2:16][NH2:17])[cH:28][c:29]2[s:30]1.[C:18](=[O:19])=[N-:20]>>[CH3:1][CH2:2][NH:3][C:4](=[O:5])[NH:6][c:7]1[n:8][c:9]2[cH:10][cH:11][c:12]([C:13](=[O:14])[CH2:15][C... | CCN(CC)CC.CCNC(=O)Nc1nc2ccc(C(=O)CCN)cc2s1.[N-]=C=O | CCNC(=O)Nc1nc2ccc(C(=O)CCNC(=O)Nc3cccc(C)c3)cc2s1 | null | null | CN(C)C=O | Aromatic Heterocycle Formation | OtherReaction | ceeef5fff04fe6a7f7ce23912c40c6b56c48ab10b532da4166f49e27ddc6de5e | 442a18545a92795a137ffa2717869d0ab7cb2b1c39aa88d4f3af549ee08fea76 | O=C(NCCC(=O)c1ccc2ncsc2c1)Nc1ccccc1 | [C;D1;H3:1]-[CH2;D2;+0:2]-N(-[CH2;D2;+0:3]-[CH3;D1;+0:4])-[CH2;D2;+0:5]-[CH3;D1;+0:6].[N-;H0;D1:7]=[C;H0;D2;+0:8]=[O;D1;H0:9].[NH2;D1;+0:10]-[C:11]-[C:12]-[C:13]=[O;D1;H0:14]>>[C;D1;H3:1]-[c;H0;D3;+0:2]1:[c:15]:[cH;D2;+0:6]:[cH;D2;+0:4]:[c;H0;D3;+0:3](-[NH;D2;+0:7]-[C;H0;D3;+0:8](=[O;D1;H0:9])-[NH;D2;+0:10]-[C:11]-[C:1... | 25 | [{"value": 25.0, "product": "CC=1C=C(C=CC1)NC(=O)NCCC(=O)C1=CC2=C(N=C(S2)NC(=O)NCC)C=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Similar to the synthesis of Example 249, a mixture of 1-(6-(3-aminopropanoyl)-2-benzothiazolyl)-3-ethylurea, triethylamine and 3-methylphenhyl isocyanate in DMF was reacted to give the desired compound 0.021 g (25%). LC/MS 426.1 (M+1); LC retention time 2.94 min.
Conditions: See reaction.notes.procedure_details.
Workup... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Tertiary amine | Urea | null | c1ccccc1 | c1ccc2scnc2c1.c1ccccc1 | null | CN(C)C=O | null | null | CCN(CC)CC.CCNC(=O)Nc1nc2ccc(C(=O)CCN)cc2s1.[N-]=C=O>CN(C)C=O>CCNC(=O)Nc1nc2ccc(C(=O)CCNC(=O)Nc3cccc(C)c3)cc2s1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-6922b5b487d84e03beb86b2f7f9581c3 | CCNC(=O)Nc1nc2ccc(C(=O)CCN)cc2s1.CN(C)c1ccc(C(=O)Cl)cc1>>CCNC(=O)Nc1nc2ccc(C(=O)CCNC(=O)c3ccc(N(C)C)cc3)cc2s1 | C(C)(=O)O.NCCC(=O)C1=CC2=C(N=C(S2)NC(=O)NCC)C=C1.C(C)N(CC)CC.CN(C1=CC=C(C(=O)Cl)C=C1)C>>C(C)NC(=O)NC=1SC2=C(N1)C=CC(=C2)C(CCNC(C2=CC=C(C=C2)N(C)C)=O)=O | [CH3:1][CH2:2][NH:3][C:4](=[O:5])[NH:6][c:7]1[n:8][c:9]2[cH:10][cH:11][c:12]([C:13](=[O:14])[CH2:15][CH2:16][NH2:17])[cH:29][c:30]2[s:31]1.Cl[C:18](=[O:19])[c:20]1[cH:21][cH:22][c:23]([N:24]([CH3:25])[CH3:26])[cH:27][cH:28]1>>[CH3:1][CH2:2][NH:3][C:4](=[O:5])[NH:6][c:7]1[n:8][c:9]2[cH:10][cH:11][c:12]([C:13](=[O:14])[C... | CCNC(=O)Nc1nc2ccc(C(=O)CCN)cc2s1.CN(C)c1ccc(C(=O)Cl)cc1 | CCNC(=O)Nc1nc2ccc(C(=O)CCNC(=O)c3ccc(N(C)C)cc3)cc2s1 | null | null | CN(C)C=O | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=C(CCNC(=O)c1ccccc1)c1ccc2ncsc2c1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[NH2;D1;+0:6]-[C:7]-[C:8]-[C:9]=[O;D1;H0:10]>>[O;D1;H0:10]=[C:9]-[C:8]-[C:7]-[NH;D2;+0:6]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5] | 25 | [{"value": 25.0, "product": "C(C)NC(=O)NC=1SC2=C(N1)C=CC(=C2)C(CCNC(C2=CC=C(C=C2)N(C)C)=O)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Similar to the synthesis of Example 248, a mixture of 1-(6-(3-aminopropanoyl)-2-benzothiazolyl)-3-ethylurea, triethylamine and 4-dimethylaminobenzoyl chloride in DMF was reacted to give the desired compound 0.025 g (25%) as an acetic acid salt. LC/MS 440.1 (M+1); LC retention time 2.86 min.
Conditions: See reaction.not... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccc2scnc2c1.c1ccccc1 | HCl | CN(C)C=O | null | null | CCNC(=O)Nc1nc2ccc(C(=O)CCN)cc2s1.CN(C)c1ccc(C(=O)Cl)cc1>CN(C)C=O>CCNC(=O)Nc1nc2ccc(C(=O)CCNC(=O)c3ccc(N(C)C)cc3)cc2s1 |
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