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-02ee2261663048188cf6d85d2cc96e3f | ord-dd987d53ad42490d9a6acf8aa6747c75 | CC(C)(C)C(=O)SCC1CCCCCCCSC[C@@H](C(=O)N2C[C@H](O)C[C@H]2C(=O)OCc2ccccc2)NC1=O>>O=C1N[C@H](C(=O)N2C[C@H](O)C[C@H]2C(=O)O)CSCCCCCCCC1CS | C(C1=CC=CC=C1)OC([C@H]1N(C[C@@H](C1)O)C(=O)[C@@H]1CSCCCCCCCC(C(N1)=O)CSC(C(C)(C)C)=O)=O.O.[OH-].[Li+].Cl>>SCC1C(N[C@@H](CSCCCCCCC1)C(=O)N1[C@H](C(=O)O)C[C@H](C1)O)=O | CC(C)(C)C(=O)[S:27][CH2:26][CH:25]1[C:2](=[O:1])[NH:3][C@H:4]([C:5](=[O:6])[N:7]2[CH2:8][C@H:9]([OH:10])[CH2:11][C@H:12]2[C:13](=[O:14])[O:15]Cc2ccccc2)[CH2:16][S:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24]1>>[O:1]=[C:2]1[NH:3][C@H:4]([C:5](=[O:6])[N:7]2[CH2:8][C@H:9]([OH:10])[CH2:11][C@H:12]2[C:13](=[O... | CC(C)(C)C(=O)SCC1CCCCCCCSC[C@@H](C(=O)N2C[C@H](O)C[C@H]2C(=O)OCc2ccccc2)NC1=O | O=C1N[C@H](C(=O)N2C[C@H](O)C[C@H]2C(=O)O)CSCCCCCCCC1CS | null | null | null | Reduction | OtherReaction | 9c1561f26e08dcf94e55cba03a37555a322ed44fbf66938d068aefab558be121 | 5654c46fe4cb226f88ec3c899c7f9be1825c357673ea686958f9ef4883ee1db3 | O=C1CCCCCCCCSC[C@@H](C(=O)N2CCCC2)N1 | C-C(-C)(-C)-C(=O)-[S;H0;D2;+0:1]-[C:2]-[C:3]-[C:4](=[O;D1;H0:5])-[#7:6].[#7:7]-[C:8]-[C:9](=[O;D1;H0:10])-[O;H0;D2;+0:11]-C-c1:c:c:c:c:c:1>>[#7:6]-[C:4](=[O;D1;H0:5])-[C:3]-[C:2]-[SH;D1;+0:1].[#7:7]-[C:8]-[C:9](=[O;D1;H0:10])-[OH;D1;+0:11] | null | [] | null | null | 2.5 | HOUR | Trans-N-[(3R)-6-(pivaloylthiomethyl)-5-oxo-1-thia-4-azacyclotridecan-3-yl-carbonyl]-4-hydroxy-L-proline benzyl ester (0.30 g, 0.05 mmol) is dissolved in nitrogen degassed tetrahydrofuran (1 ml) and water (0.5 ml). Lithium hydroxide monohydrate (0.006 g, 0.15 mmol) is added and the mixture is stirred at room temperature... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Carbo-thioester | Carboxylic acid.Aliphatic thiol | c1ccccc1 | null | C1CCCCNCCSCCCC1.C1CC[NH]C1 | HO- | null | null | 2.5 | CC(C)(C)C(=O)SCC1CCCCCCCSC[C@@H](C(=O)N2C[C@H](O)C[C@H]2C(=O)OCc2ccccc2)NC1=O>>O=C1N[C@H](C(=O)N2C[C@H](O)C[C@H]2C(=O)O)CSCCCCCCCC1CS |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-87d288d6baf14569856e62b2735e05e2 | CC(=O)SCC1CCCCCCCCSC[C@@H](C(=O)OCc2ccccc2)NC1=O>>O=C1N[C@H](C(=O)O)CSCCCCCCCCC1CS | C(C)(=O)SCC1C(N[C@@H](CSCCCCCCCC1)C(=O)OCC1=CC=CC=C1)=O.O.[OH-].[Li+].Cl>>SCC1C(N[C@@H](CSCCCCCCCC1)C(=O)O)=O | CC(=O)[S:20][CH2:19][CH:18]1[C:2](=[O:1])[NH:3][C@H:4]([C:5](=[O:6])[O:7]Cc2ccccc2)[CH2:8][S:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]1>>[O:1]=[C:2]1[NH:3][C@H:4]([C:5](=[O:6])[OH:7])[CH2:8][S:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH:18]1[CH2:19][SH:20] | CC(=O)SCC1CCCCCCCCSC[C@@H](C(=O)OCc2ccccc2)NC1=O | O=C1N[C@H](C(=O)O)CSCCCCCCCCC1CS | null | null | null | Reduction | OtherReaction | 9c1561f26e08dcf94e55cba03a37555a322ed44fbf66938d068aefab558be121 | 5654c46fe4cb226f88ec3c899c7f9be1825c357673ea686958f9ef4883ee1db3 | O=C1CCCCCCCCCSCCN1 | C-C(=O)-[S;H0;D2;+0:1]-[C:2]-[C:3]-[C:4](=[O;D1;H0:5])-[#7:6]-[C:7]-[C:8](=[O;D1;H0:9])-[O;H0;D2;+0:10]-C-c1:c:c:c:c:c:1>>[O;D1;H0:5]=[C:4](-[#7:6]-[C:7]-[C:8](=[O;D1;H0:9])-[OH;D1;+0:10])-[C:3]-[C:2]-[SH;D1;+0:1] | null | [] | null | null | 3 | HOUR | Benzyl (3R)-6-(acetylthiomethyl)-5-oxo-1-thia-4-azacyclotetradecane-3-carboxylate (Isomer A), (0.11 g, 0.25 mmol) is dissolved in nitrogen degassed tetrahydrofuran (5 ml) and water (1 ml). Lithium hydroxide monohydrate (0.032 g, 0.75 mmol) is added and the mixture is stirred for 3 hours at room temperature. The mixture... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Carbo-thioester | Carboxylic acid.Aliphatic thiol | c1ccccc1 | null | C1CCCCCSCCNCCCC1 | HO- | null | null | 3 | CC(=O)SCC1CCCCCCCCSC[C@@H](C(=O)OCc2ccccc2)NC1=O>>O=C1N[C@H](C(=O)O)CSCCCCCCCCC1CS |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-db09bc9101ed4996bc3154e23a36a8ee | CCCN(CCC)C1Cc2c(C#N)ccc3c2C(C1)CN3C(=O)c1ccccc1>>CCCN(CCC)C1Cc2c(C#N)ccc3c2C(CN3)C1 | Cl.C(CCC)[Li].C(C1=CC=CC=C1)(=O)N1CC2C=3C(=C(C=CC13)C#N)CC(C2)N(CCC)CCC>>C(#N)C1=C2C=3C(CNC3C=C1)CC(C2)N(CCC)CCC | O=C(c1ccccc1)[N:20]1[c:16]2[cH:15][cH:14][c:11]([C:12]#[N:13])[c:10]3[c:17]2[CH:18]([CH2:19]1)[CH2:21][CH:8]([N:4]([CH2:3][CH2:2][CH3:1])[CH2:5][CH2:6][CH3:7])[CH2:9]3>>[CH3:1][CH2:2][CH2:3][N:4]([CH2:5][CH2:6][CH3:7])[CH:8]1[CH2:9][c:10]2[c:11]([C:12]#[N:13])[cH:14][cH:15][c:16]3[c:17]2[CH:18]([CH2:19][NH:20]3)[CH2:21... | CCCN(CCC)C1Cc2c(C#N)ccc3c2C(C1)CN3C(=O)c1ccccc1 | CCCN(CCC)C1Cc2c(C#N)ccc3c2C(CN3)C1 | null | null | CCCCCC.C1CCOC1 | Reduction | Hydrogenolysis of tertiary amines | 99f0a6dc5611581d1d7a71900cee1ca5de3aaa1efd3b5fccc3b6d24420f211d3 | 62cf08a8ae6315067a063b5b3495125ccbdaff6b2340ce1d3e1c7b6cde962ae4 | c1cc2c3c(c1)NCC3CCC2 | O=C(-[N;H0;D3;+0:1]1-[C:2]-[C:3]-[c:4]:[c:5]-1:[c:6])-c1:c:c:c:c:c:1>>[c:6]:[c:5]1:[c:4]-[C:3]-[C:2]-[NH;D2;+0:1]-1 | 113.8 | [{"value": 113.8, "product": "C(#N)C1=C2C=3C(CNC3C=C1)CC(C2)N(CCC)CCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -78 | CELSIUS | 30 | MINUTE | To a stirred solution of 4.8 g (0.0124 mol) of (±)-1-benzoyl-6- cyano-4-(di-n-propylamino)-1,2,2a,3,4,5-hexahydrobenz[cd]indole in 200 mL of THF cooled to -78° C. under a N2 atmosphere were added 16 mL (0.025 mol) of 1.6 M solution of n-butyl lithium in hexane. The reaction mixture was stirred at -78° C. for 30 minutes... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide | Secondary amine | c1ccccc1.c1cc2c3c(c1)[NH]CC3CCC2 | c1cc2c3c(c1)NCC3CCC2 | c1cc2c3c(c1)NCC3CCC2 | HO- | CCCCCC.C1CCOC1 | -78 | 0.5 | CCCN(CCC)C1Cc2c(C#N)ccc3c2C(C1)CN3C(=O)c1ccccc1>CCCCCC.C1CCOC1>CCCN(CCC)C1Cc2c(C#N)ccc3c2C(CN3)C1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-42b89d4ecc9c4ad3a03f64ca5c2ac1f8 | CCCN(CCC)C1Cc2c(C#N)ccc3c2C(C1)CN3C(c1ccccc1)(c1ccccc1)c1ccccc1>>CCCN(CCC)[C@H]1Cc2c(C(C)=O)ccc3c2[C@@H](CN3)C1 | C(C1=CC=CC=C1)(C1=CC=CC=C1)(C1=CC=CC=C1)N1CC2C=3C(=C(C=CC13)C#N)CC(C2)N(CCC)CCC.C[Mg]Br.C1CCOC1.[NH4+].[Cl-]>>C(C)(=O)C1=C2C=3[C@@H](CNC3C=C1)C[C@H](C2)N(CCC)CCC | N#[C:12][c:11]1[c:10]2[c:18]3[c:17]([cH:16][cH:15]1)[N:21](C(c1ccccc1)(c1ccccc1)c1ccccc1)[CH2:20][CH:19]3[CH2:22][CH:8]([N:4]([CH2:3][CH2:2][CH3:1])[CH2:5][CH2:6][CH3:7])[CH2:9]2>>[CH3:1][CH2:2][CH2:3][N:4]([CH2:5][CH2:6][CH3:7])[C@H:8]1[CH2:9][c:10]2[c:11]([C:12]([CH3:13])=[O:14])[cH:15][cH:16][c:17]3[c:18]2[C@@H:19](... | CCCN(CCC)C1Cc2c(C#N)ccc3c2C(C1)CN3C(c1ccccc1)(c1ccccc1)c1ccccc1 | CCCN(CCC)[C@H]1Cc2c(C(C)=O)ccc3c2[C@@H](CN3)C1 | null | null | C(C)OCC | Miscellaneous | OtherReaction | ecb2c7ecd60da8f4a8e976558493b8c43ae8b650cc9a832ab767e6d065fd638a | 96775e2ed91ef48429f2b64f1940bbfa5c55ad2bf2c43eeba523730fdf438d71 | c1cc2c3c(c1)NC[C@H]3CCC2 | N#[C;H0;D2;+0:1]-[c:2]1:[c:3]:[c:4]2:[c:5](:[c:6]:[c:7]:1)-[N;H0;D3;+0:8](-C(-c1:c:c:c:c:c:1)(-c1:c:c:c:c:c:1)-c1:c:c:c:c:c:1)-[C:9]-[C:10]-2>>[C;D1;H3:11]-[C;H0;D3;+0:1](=[O;D1;H0:12])-[c:2]1:[c:3]:[c:4]2:[c:5](:[c:6]:[c:7]:1)-[NH;D2;+0:8]-[C:9]-[C:10]-2 | null | [] | null | null | 30 | MINUTE | A solution of 2.4 g (4.6 mmol) (+)-1-trityl-6-cyano-4-(di-n-propylamino)-1,2,2a,3,4,5-hexahydrobenz[cd]indole in 100 mL of THF was treated with 25 mL of 2.0M methylmagnesium bromide in diethyl ether. The reaction mixture was refluxed for 16 hr. The reaction mixture was cooled and excess Grignard reagent was decomposed ... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile.Tertiary amine | Ketone.Secondary amine | c1ccccc1.c1ccccc1.c1ccccc1.c1cc2c3c(c1)[NH]CC3CCC2 | c1cc2c3c(c1)NC[C@H]3CCC2 | c1cc2c3c(c1)NC[C@H]3CCC2 | Other | C(C)OCC | null | 0.5 | CCCN(CCC)C1Cc2c(C#N)ccc3c2C(C1)CN3C(c1ccccc1)(c1ccccc1)c1ccccc1>C(C)OCC>CCCN(CCC)[C@H]1Cc2c(C(C)=O)ccc3c2[C@@H](CN3)C1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-cf44fca8e26c4721af668d5b0310d621 | CCCN(CCC)C1Cc2c(C#N)ccc3c2C(CN3)C1>>CCCN(CCC)C1Cc2c(C(C)=O)ccc3c2C(CN3)C1 | C(#N)C1=C2C=3C(CNC3C=C1)CC(C2)N(CCC)CCC.C[Mg]Br.C(C)OCC.[NH4+].[Cl-]>>C(C)(=O)C1=C2C=3C(CNC3C=C1)CC(C2)N(CCC)CCC | N#[C:12][c:11]1[c:10]2[c:18]3[c:17]([cH:16][cH:15]1)[NH:21][CH2:20][CH:19]3[CH2:22][CH:8]([N:4]([CH2:3][CH2:2][CH3:1])[CH2:5][CH2:6][CH3:7])[CH2:9]2>>[CH3:1][CH2:2][CH2:3][N:4]([CH2:5][CH2:6][CH3:7])[CH:8]1[CH2:9][c:10]2[c:11]([C:12]([CH3:13])=[O:14])[cH:15][cH:16][c:17]3[c:18]2[CH:19]([CH2:20][NH:21]3)[CH2:22]1 | CCCN(CCC)C1Cc2c(C#N)ccc3c2C(CN3)C1 | CCCN(CCC)C1Cc2c(C(C)=O)ccc3c2C(CN3)C1 | null | null | C1=CC=CC=C1 | Miscellaneous | OtherReaction | 54622de249eb9a5622e28710a02d261b08e09c3ee957106ef84a0e4751ccb30f | 957d5e0aaa82a4f5b73d699040cb2acd7f615417c9e400cbb7a63fa4c133449a | c1cc2c3c(c1)NCC3CCC2 | N#[C;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[C;D1;H3:5]-[C;H0;D3;+0:1](=[O;D1;H0:6])-[c:2](:[c:3]):[c:4] | null | [] | null | null | 30 | MINUTE | A solution of 0.5 g (1.8 mmol) of (±)-6-cyano-4-(di-n-propylamino)-1,2,2a,3,4,5-hexahydrobenz[cd]indole in 75 mL of benzene was treated with 5 mL of 2.0M methylmagnesium bromide in diethyl ether. The reaction mixture was refluxed for 2 days. The reaction mixture was cooled and excess Grignard reagent was decomposed wit... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile | Ketone | null | null | c1cc2c3c(c1)NCC3CCC2 | null | C1=CC=CC=C1 | null | 0.5 | CCCN(CCC)C1Cc2c(C#N)ccc3c2C(CN3)C1>C1=CC=CC=C1>CCCN(CCC)C1Cc2c(C(C)=O)ccc3c2C(CN3)C1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-39c6db17ee584deba9aaa702687d55e0 | CCCN(CCC)C1Cc2c(C(C)=O)ccc3c2C(CN3)C1.O=C(Cl)OCC(Cl)(Cl)Cl>>NC(=O)N1CCc2ccccc21 | C(C)(=O)C1=C2C=3C(CNC3C=C1)CC(C2)N(CCC)CCC.C(C)N(CC)CC.ClC(=O)OCC(Cl)(Cl)Cl>>C(N)(=O)N1CCC2=CC=CC=C12 | CCCN(CCC)C1C[CH:6]2[CH2:5][NH:4][c:12]3[c:7]2[c:8]([c:9](C(C)=O)[cH:10][cH:11]3)C1.ClC(Cl)(Cl)CO[C:2](Cl)=[O:3]>>[NH2:1][C:2](=[O:3])[N:4]1[CH2:5][CH2:6][c:7]2[cH:8][cH:9][cH:10][cH:11][c:12]21 | CCCN(CCC)C1Cc2c(C(C)=O)ccc3c2C(CN3)C1.O=C(Cl)OCC(Cl)(Cl)Cl | NC(=O)N1CCc2ccccc21 | null | null | C(Cl)Cl | Acylation | OtherReaction | 6a9ab0c72d3ef4f5776b87b216245ab6ebe0245f6ae66f5b216d5863946ee678 | 1fea30f316824198e233dc7d7d5f0ed1a4a322c4c89c24d4336ce38c6250dbb8 | c1ccc2c(c1)CCN2 | C-C-C-N(-C-C-C)-C1-C-[CH;D3;+0:1]2-[C:2]-[NH;D2;+0:3]-[c:4]3:[c:5]:[c:6]:[c;H0;D3;+0:7](-C(-C)=O):[c;H0;D3;+0:8](:[c:9]:3-2)-C-1.Cl-[C;H0;D3;+0:10](=[O;D1;H0:11])-O-C-C(-Cl)(-Cl)-Cl>>[N;D1;H2:12]-[C;H0;D3;+0:10](=[O;D1;H0:11])-[N;H0;D3;+0:3]1-[C:2]-[CH2;D2;+0:1]-[c:9]2:[cH;D2;+0:8]:[cH;D2;+0:7]:[c:6]:[c:5]:[c:4]:2-1 | null | [] | null | null | 1 | HOUR | To a solution of (±)-6-acetyl-4-(di-n-propylamino)-1,2,2a,3,4,5-hexahydrobenz[cd]indole (2.3 g, 7.7 mmol) and triethylamine (1.1 ml, 8 mmol) in 90 ml CH2Cl2 under N2 was added dropwise a solution of 2,2,2-trichloroethyl chloroformate. The reaction mixture was stirred at RT for 1 hr. The CH2Cl2 solution was extracted wi... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Trichloro group.Ketone.Ether.Secondary amine.Tertiary amine | Urea | c1cc2c3c(c1)NCC3CCC2 | c1ccc2c(c1)CC[NH]2 | c1ccc2c(c1)CC[NH]2 | HCl | C(Cl)Cl | null | 1 | CCCN(CCC)C1Cc2c(C(C)=O)ccc3c2C(CN3)C1.O=C(Cl)OCC(Cl)(Cl)Cl>C(Cl)Cl>NC(=O)N1CCc2ccccc21 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-aac0c1f80f444f1e85571cb9c0058d96 | CCOC(=O)C(=O)CBr.Nc1cccc(Cl)n1>>CCOC(=O)c1cn2c(Cl)cccc2n1 | NC1=NC(=CC=C1)Cl.BrCC(C(=O)OCC)=O>>C(C)OC(=O)C=1N=C2N(C(=CC=C2)Cl)C1 | O=[C:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[CH2:7]Br.[n:8]1[c:9]([Cl:10])[cH:11][cH:12][cH:13][c:14]1[NH2:15]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][n:8]2[c:9]([Cl:10])[cH:11][cH:12][cH:13][c:14]2[n:15]1 | CCOC(=O)C(=O)CBr.Nc1cccc(Cl)n1 | CCOC(=O)c1cn2c(Cl)cccc2n1 | null | null | C(C)O | Aromatic Heterocycle Formation | OtherReaction | d3be5f205f769cfbcd36c6b3c07b14ecde02aad10f74db526231235b2a6ee955 | 9db5e3e6f9ecdf6e7efe58729c5de8c8b341b06179a94217349f28a43071e423 | c1ccn2ccnc2c1 | Br-[CH2;D2;+0:1]-[C;H0;D3;+0:2](=O)-[C:3](=[O;D1;H0:4])-[#8:5]-[C:6].[Cl;D1;H0:7]-[c:8](:[c:9]):[n;H0;D2;+0:10]:[c:11](-[NH2;D1;+0:12]):[c:13]>>[C:6]-[#8:5]-[C:3](=[O;D1;H0:4])-[c;H0;D3;+0:2]1:[cH;D2;+0:1]:[n;H0;D3;+0:10](:[c:11](:[c:13]):[n;H0;D2;+0:12]:1):[c:8](-[Cl;D1;H0:7]):[c:9] | 67.7 | [{"value": 67.6, "product": "C(C)OC(=O)C=1N=C2N(C(=CC=C2)Cl)C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 67.7, "product": "C(C)OC(=O)C=1N=C2N(C(=CC=C2)Cl)C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 2-amino-6-chloropyridine (6.43 g, 50 mmoles) and ethyl bromopyruvate (9.75 g, 50 mmoles) in ethanol (150 ml) was heated at reflux for 4 hours. After the solvent was removed, chloroform was added to the residue, which was washed in turn with saturated sodium bicarbonate and saturated saline, and then dried... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ketone.Ester.Primary amine | Ester | c1ccncc1 | c1ccn2ccnc2c1 | c1ccn2ccnc2c1 | HBr | C(C)O | null | null | CCOC(=O)C(=O)CBr.Nc1cccc(Cl)n1>C(C)O>CCOC(=O)c1cn2c(Cl)cccc2n1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-56786f33a9bf4fdaa5b52ea804ea60fd | Cc1cn2c(Cl)cccc2n1.NCCS>>Cc1cn2c(SCCN)cccc2n1 | Cl.NCCS.[H-].[Na+].ClC1=CC=CC=2N1C=C(N2)C>>NCCSC1=CC=CC=2N1C=C(N2)C | Cl[c:5]1[n:4]2[cH:3][c:2]([CH3:1])[n:14][c:13]2[cH:12][cH:11][cH:10]1.[SH:6][CH2:7][CH2:8][NH2:9]>>[CH3:1][c:2]1[cH:3][n:4]2[c:5]([S:6][CH2:7][CH2:8][NH2:9])[cH:10][cH:11][cH:12][c:13]2[n:14]1 | Cc1cn2c(Cl)cccc2n1.NCCS | Cc1cn2c(SCCN)cccc2n1 | null | null | C(C)O | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution thiol | c3736b0fc6b205c84b2f6fa175f2c2a6173b89138ca9975bda063f8b3911cf9e | b7fe376f7aad2517725eef26ab981e4baa6c31c5f38fdf89e7c52a4a2c6cc1d2 | c1ccn2ccnc2c1 | Cl-[c;H0;D3;+0:1](:[c:2]:[c:3]):[#7;a:4]1:[c:5]:[#7;a:6]:[c:7]:[c:8]:1.[C:9]-[C:10]-[SH;D1;+0:11]>>[C:9]-[C:10]-[S;H0;D2;+0:11]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[#7;a:4]1:[c:5]:[#7;a:6]:[c:7]:[c:8]:1 | 53.6 | [{"value": 53.6, "product": "NCCSC1=CC=CC=2N1C=C(N2)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 53.1, "product": "NCCSC1=CC=CC=2N1C=C(N2)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a suspension of cysteamine hydrochloride (2.95 g, 26 mmoles) in ethanol (100 ml) was added 60% sodium hydride (oily; 2.08 g, 26 mmoles) with stirring under ice-cooling and the mixture was stirred for 5 minutes. 5-chloro-2-methylimidazo[1,2-a]pyridine (3.33 g, 20 mmoles) was added to the mixture, followed by heating ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aliphatic thiol | Monosulfide | c1ccn2ccnc2c1 | c1ccn2ccnc2c1 | c1ccn2ccnc2c1 | HCl | C(C)O | null | null | Cc1cn2c(Cl)cccc2n1.NCCS>C(C)O>Cc1cn2c(SCCN)cccc2n1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-0f285cb157234f1fa10f07e2d940a71c | Clc1cccc2nccn12.NCCCCO>>NCCCCOc1cccc2nccn12 | C(=O)(OC(C)(C)C)OC(=O)[O-].ClC1=CC=CC=2N1C=CN2.NCCCCO.[H-].[Na+]>>NCCCCOC1=CC=CC=2N1C=CN2 | Cl[c:7]1[cH:8][cH:9][cH:10][c:11]2[n:12][cH:13][cH:14][n:15]12.[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][OH:6]>>[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][O:6][c:7]1[cH:8][cH:9][cH:10][c:11]2[n:12][cH:13][cH:14][n:15]12 | Clc1cccc2nccn12.NCCCCO | NCCCCOc1cccc2nccn12 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 86a14d8c65c7d47a74ee6f255350fe1cca98e47302e41723756ed1ac172a15be | a4cafa7bcd156e21cca6eaac1b32e28ec8540642a31181122e6957f3d7559631 | c1ccn2ccnc2c1 | Cl-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[c:5]2:[#7;a:6]:[c:7]:[c:8]:[#7;a:9]:2:1.[C:10]-[C:11]-[OH;D1;+0:12]>>[C:10]-[C:11]-[O;H0;D2;+0:12]-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[c:5]2:[#7;a:6]:[c:7]:[c:8]:[#7;a:9]:2:1 | 41 | [{"value": 40.9, "product": "NCCCCOC1=CC=CC=2N1C=CN2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 41.0, "product": "NCCCCOC1=CC=CC=2N1C=CN2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a suspension of 60% sodium hydride (oily; 1.32 g, 33 mmloes) in DMF (60 ml) was added a solution of 5-chloroimidazo[1,2-a]pyridine (4.59 g, 30.1 mmoles) and 4-aminobutanol (2.68 g, 30.1 mmoles) in DMF (60 ml) at room temperature with stirring and the mixture was stirred at the same temperature for 5 hours. Tert-buty... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary alcohol | Ether | c1ccn2ccnc2c1 | c1ccn2ccnc2c1 | c1ccn2ccnc2c1 | HCl | CN(C)C=O | null | null | Clc1cccc2nccn12.NCCCCO>CN(C)C=O>NCCCCOc1cccc2nccn12 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-61e62a7adec145119c408b8a0df3ef86 | O=C(Cl)Oc1ccccc1.OCCSc1cccc2nccn12>>O=C(OCCSc1cccc2nccn12)Oc1ccccc1 | OCCSC1=CC=CC=2N1C=CN2.N1=CC=CC=C1.ClC(=O)OC1=CC=CC=C1>>O(C1=CC=CC=C1)C(=O)OCCSC1=CC=CC=2N1C=CN2 | Cl[C:2](=[O:1])[O:16][c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1.[OH:3][CH2:4][CH2:5][S:6][c:7]1[cH:8][cH:9][cH:10][c:11]2[n:12][cH:13][cH:14][n:15]12>>[O:1]=[C:2]([O:3][CH2:4][CH2:5][S:6][c:7]1[cH:8][cH:9][cH:10][c:11]2[n:12][cH:13][cH:14][n:15]12)[O:16][c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1 | O=C(Cl)Oc1ccccc1.OCCSc1cccc2nccn12 | O=C(OCCSc1cccc2nccn12)Oc1ccccc1 | null | null | C(Cl)Cl | Acylation | Schotten-Baumann to ester | c7a3e8873fc25f3519e40d98cf7a48f9e19cf51f2928c1b7217b087e636631b6 | 025f705bf83a5228860243b04919f20e0b9a7bfb249341effd2e1aa6465736d3 | O=C(OCCSc1cccc2nccn12)Oc1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[c:4].[C:5]-[C:6]-[OH;D1;+0:7]>>[C:5]-[C:6]-[O;H0;D2;+0:7]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[c:4] | 91.3 | [{"value": 91.3, "product": "O(C1=CC=CC=C1)C(=O)OCCSC1=CC=CC=2N1C=CN2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 91.3, "product": "O(C1=CC=CC=C1)C(=O)OCCSC1=CC=CC=2N1C=CN2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 5-[2-(hydroxy)ethylthio]imidazo[1,2-a]pyridine (5.83 g, 30 mmoles) and pyridine (4.36 ml, 60 mmoles) in methylene chloride (120 ml) was added phenyl chloroformate (7.53 ml, 60 mmoles) with stirring under ice-cooling and the mixture was stirred under ice-cooling for 30 minutes. The reaction solution was... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Ether.Primary alcohol | Ether.Ether | null | null | c1ccn2ccnc2c1.c1ccccc1 | HCl | C(Cl)Cl | null | null | O=C(Cl)Oc1ccccc1.OCCSc1cccc2nccn12>C(Cl)Cl>O=C(OCCSc1cccc2nccn12)Oc1ccccc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-c14424b657b147a5b1cf7290b793d4e0 | CS(=O)(=O)Cl.OCCSc1cccc2nccn12>>CS(=O)(=O)OCCSc1cccc2nccn12 | OCCSC1=CC=CC=2N1C=CN2.C(C)N(CC)CC.CS(=O)(=O)Cl>>CS(=O)(=O)OCCSC1=CC=CC=2N1C=CN2 | Cl[S:2]([CH3:1])(=[O:3])=[O:4].[OH:5][CH2:6][CH2:7][S:8][c:9]1[cH:10][cH:11][cH:12][c:13]2[n:14][cH:15][cH:16][n:17]12>>[CH3:1][S:2](=[O:3])(=[O:4])[O:5][CH2:6][CH2:7][S:8][c:9]1[cH:10][cH:11][cH:12][c:13]2[n:14][cH:15][cH:16][n:17]12 | CS(=O)(=O)Cl.OCCSc1cccc2nccn12 | CS(=O)(=O)OCCSc1cccc2nccn12 | null | null | C(Cl)Cl | Acylation | Formation of Sulfonic Esters | 2fa969eb2c954bb96793348a1b2335ec63fbd290dadec6e3e02295e1768e64cf | cb77b899e4adf980b1def97230ef2861660fd7f9602260ec64747d9afd3a795a | c1ccn2ccnc2c1 | Cl-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4].[C:5]-[C:6]-[OH;D1;+0:7]>>[C:5]-[C:6]-[O;H0;D2;+0:7]-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4] | 99.9 | [{"value": 99.9, "product": "CS(=O)(=O)OCCSC1=CC=CC=2N1C=CN2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 5-[2-(hydroxy)ethylthio]imidazo[1,2-a]pyridine (9.71 g, 50 mmoles) and triethylamine (10.5 ml, 75.3 mmoles) in methylene chloride (300 ml) was added methanesulfonyl chloride (4.26 ml, 55 mmoles) with stirring under ice-cooling and the mixture was stirred under ice-cooling for 2 hours. The reaction solu... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Sulfonyl halide | Mesylate | null | null | c1ccn2ccnc2c1 | HCl | C(Cl)Cl | null | null | CS(=O)(=O)Cl.OCCSc1cccc2nccn12>C(Cl)Cl>CS(=O)(=O)OCCSc1cccc2nccn12 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-824f8a15b5d240dc96f33facfa1f2b99 | CN.CS(=O)(=O)OCCSc1cccc2nccn12>>CNCCSc1cccc2nccn12 | CS(=O)(=O)OCCSC1=CC=CC=2N1C=CN2.C(C)N(CC)CC.CN.CO>>CNCCSC1=CC=CC=2N1C=CN2 | [CH3:1][NH2:2].CS(=O)(=O)O[CH2:3][CH2:4][S:5][c:6]1[cH:7][cH:8][cH:9][c:10]2[n:11][cH:12][cH:13][n:14]12>>[CH3:1][NH:2][CH2:3][CH2:4][S:5][c:6]1[cH:7][cH:8][cH:9][c:10]2[n:11][cH:12][cH:13][n:14]12 | CN.CS(=O)(=O)OCCSc1cccc2nccn12 | CNCCSc1cccc2nccn12 | null | null | C(Cl)(Cl)Cl | Heteroatom Alkylation and Arylation | Alkylation of amines | 8445343b2fb2fd8a9bc06f8532794f2ba6b99565a6e05a3bb9a4344ce2671186 | 7e6303acde8be57b43b4c6a673e1c7537b1efde90f08932e09e153dbba53a700 | c1ccn2ccnc2c1 | C-S(=O)(=O)-O-[CH2;D2;+0:1]-[C:2]-[#16:3].[C;D1;H3:4]-[NH2;D1;+0:5]>>[#16:3]-[C:2]-[CH2;D2;+0:1]-[NH;D2;+0:5]-[C;D1;H3:4] | 47.1 | [{"value": 47.1, "product": "CNCCSC1=CC=CC=2N1C=CN2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 47.1, "product": "CNCCSC1=CC=CC=2N1C=CN2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 5-[2-(methylsulfonyloxy)ethylthio]imidazo[1,2-a]pyridine (2.18 g, 8 mmoles), triethylamine (2.24 ml, 16 mmoles) and a 40% methylamine-methanol solution (20 ml) in chloroform (20 ml) was heated at reflux for 3 hours. The reaction solution was washed with an aqueous 3N-sodium hydroxide solution and dried ov... | 10.6084/m9.figshare.5104873.v1 | null | Mesylate.Primary amine | Secondary amine | null | null | c1ccn2ccnc2c1 | MsOH.HO- | C(Cl)(Cl)Cl | null | null | CN.CS(=O)(=O)OCCSc1cccc2nccn12>C(Cl)(Cl)Cl>CNCCSc1cccc2nccn12 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-689b4b2ef67943d4b073104bea7fe4b7 | CC(C)(C)OC(=O)NCCCNc1cccc2nccn12>>Cl.NCCCNc1cccc2nccn12 | C(C)(C)(C)OC(=O)NCCCNC1=CC=CC=2N1C=CN2.Cl.CO>>Cl.Cl.NCCCNC1=CC=CC=2N1C=CN2 | CC(C)(C)OC(=O)[NH:3][CH2:4][CH2:5][CH2:6][NH:7][c:8]1[cH:9][cH:10][cH:11][c:12]2[n:13][cH:14][cH:15][n:16]12>>[ClH:2].[NH2:3][CH2:4][CH2:5][CH2:6][NH:7][c:8]1[cH:9][cH:10][cH:11][c:12]2[n:13][cH:14][cH:15][n:16]12 | CC(C)(C)OC(=O)NCCCNc1cccc2nccn12 | Cl.NCCCNc1cccc2nccn12 | null | null | C(Cl)Cl | Miscellaneous | Hydrogenolysis of amides/imides/carbamates | 4812e39fa209f57a5a2564677791e5e37790c829f5742d8c7df33806c5ba4ce0 | d7ecc2e7a68b8c20d378ac6004c3fdfc3efd09bbbd9efd577186f69427135737 | c1ccn2ccnc2c1 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[C:2]-[C:3]>>[C:3]-[C:2]-[NH2;D1;+0:1] | 83 | [{"value": 83.0, "product": "Cl.Cl.NCCCNC1=CC=CC=2N1C=CN2", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 20 | HOUR | To a suspension of 5-[3-(tert-butoxycarbonylamino)propylamino]imidazo[1,2-a]pyridine (1.742 g, 6 mmoles) in methylene chloride (40 ml) was added hydrogen chloride-methanol (6 ml) and the mixture was stirred at room temperature for 20 hours. After the solvent was distilled off, ethanol (15 ml) and ether (30 ml) were add... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Primary amine | null | null | c1ccn2ccnc2c1 | HO- | C(Cl)Cl | null | 20 | CC(C)(C)OC(=O)NCCCNc1cccc2nccn12>C(Cl)Cl>Cl.NCCCNc1cccc2nccn12 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-cb1bba4ddd074106a9df010f3e7867aa | Clc1cccc2nccn12.N=C(N)SCCCN>>NCCCSc1cccc2nccn12 | ClC1=CC=CC=2N1C=CN2.[OH-].[K+].CS(=O)C.Br.Br.NCCCSC(N)=N>>NCCCSC1=CC=CC=2N1C=CN2 | Cl[c:6]1[cH:7][cH:8][cH:9][c:10]2[n:11][cH:12][cH:13][n:14]12.N=C(N)[S:5][CH2:4][CH2:3][CH2:2][NH2:1]>>[NH2:1][CH2:2][CH2:3][CH2:4][S:5][c:6]1[cH:7][cH:8][cH:9][c:10]2[n:11][cH:12][cH:13][n:14]12 | Clc1cccc2nccn12.N=C(N)SCCCN | NCCCSc1cccc2nccn12 | null | null | O | Heteroatom Alkylation and Arylation | OtherReaction | 5c2ee1fbeb816b2281fc56b7a7c3dec1a003cfc961b24d42976d878151218e19 | a0db6fe3ed1c4fe8c413e334ea9e090fc70b5b1dbf83be67f74f657c2f41a45d | c1ccn2ccnc2c1 | Cl-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[c:5]2:[#7;a:6]:[c:7]:[c:8]:[#7;a:9]:2:1.N-C(=N)-[S;H0;D2;+0:10]-[C:11]-[C:12]>>[C:12]-[C:11]-[S;H0;D2;+0:10]-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[c:5]2:[#7;a:6]:[c:7]:[c:8]:[#7;a:9]:2:1 | 64.3 | [{"value": 64.3, "product": "NCCCSC1=CC=CC=2N1C=CN2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 64.2, "product": "NCCCSC1=CC=CC=2N1C=CN2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1.5 | HOUR | To a mixed solution of 10% potassium hydroxide (69.3 g, 105 mmoles) and dimethylsulfoxide (50 ml) was added S-[3-(amino)propyl]isothiourea.dihydrobromide (8.85 g, 39 mmoles) and the mixture was stirred at room temperature for 1.5 hours. To the reaction solution was added 5-chloroimidazo[1,2-a]pyridine (3.05 g, 20 mmole... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine.Monosulfide | Monosulfide | c1ccn2ccnc2c1 | c1ccn2ccnc2c1 | c1ccn2ccnc2c1 | HCl | O | null | 1.5 | Clc1cccc2nccn12.N=C(N)SCCCN>O>NCCCSc1cccc2nccn12 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-877f58037d2241b39b1ba3a388bcb737 | ClCCCBr.Sc1cccc2nccn12>>ClCCCSc1cccc2nccn12 | SC1=CC=CC=2N1C=CN2.BrCCCCl.C(C)N(CC)CC>>ClCCCSC1=CC=CC=2N1C=CN2 | Br[CH2:4][CH2:3][CH2:2][Cl:1].[SH:5][c:6]1[cH:7][cH:8][cH:9][c:10]2[n:11][cH:12][cH:13][n:14]12>>[Cl:1][CH2:2][CH2:3][CH2:4][S:5][c:6]1[cH:7][cH:8][cH:9][c:10]2[n:11][cH:12][cH:13][n:14]12 | ClCCCBr.Sc1cccc2nccn12 | ClCCCSc1cccc2nccn12 | null | null | C(C)O | Heteroatom Alkylation and Arylation | thioether_nucl_sub | 26df88c6a3f5f203c89584658be4e126cb42994c98a2e16bc812e1036cdae857 | 8b2f52296c3a93039174c980b6042ba15754e04d6892a1284c3a32985220b214 | c1ccn2ccnc2c1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[SH;D1;+0:4]-[c:5](:[c:6]):[#7;a:7]1:[c:8]:[#7;a:9]:[c:10]:[c:11]:1>>[C:3]-[C:2]-[CH2;D2;+0:1]-[S;H0;D2;+0:4]-[c:5](:[c:6]):[#7;a:7]1:[c:8]:[#7;a:9]:[c:10]:[c:11]:1 | 72.1 | [{"value": 72.0, "product": "ClCCCSC1=CC=CC=2N1C=CN2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 72.1, "product": "ClCCCSC1=CC=CC=2N1C=CN2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 17 | HOUR | To a suspension of 5-mercaptoimidazo[1,2-a]pyridine (5.02 g, 33.4 mmoles) and 1-bromo-3-chloropropane (5.26 g, 33.4 mmoles) in ethanol (100 ml) was added triethylamine (4.66 ml, 33.4 mmoles) and the mixture was stirred at room temperature for 17 hours. After the solvent was distilled off, chloroform was added to the re... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic thiol | Monosulfide | null | null | c1ccn2ccnc2c1 | HBr | C(C)O | null | 17 | ClCCCBr.Sc1cccc2nccn12>C(C)O>ClCCCSc1cccc2nccn12 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-0a019c1a317748ecb8ef899b9168024f | CS(=O)(=O)Cl.NCCSc1cccc2nccn12>>CS(=O)(=O)NCCSc1cccc2nccn12 | O.NCCSC1=CC=CC=2N1C=CN2.C(C)N(CC)CC.CS(=O)(=O)Cl>>CS(=O)(=O)NCCSC1=CC=CC=2N1C=CN2 | Cl[S:2]([CH3:1])(=[O:3])=[O:4].[NH2:5][CH2:6][CH2:7][S:8][c:9]1[cH:10][cH:11][cH:12][c:13]2[n:14][cH:15][cH:16][n:17]12>>[CH3:1][S:2](=[O:3])(=[O:4])[NH:5][CH2:6][CH2:7][S:8][c:9]1[cH:10][cH:11][cH:12][c:13]2[n:14][cH:15][cH:16][n:17]12 | CS(=O)(=O)Cl.NCCSc1cccc2nccn12 | CS(=O)(=O)NCCSc1cccc2nccn12 | null | null | C(Cl)Cl | Miscellaneous | Sulfonamide synthesis (Schotten-Baumann) primary amine | a86b0632821e188c0a5dc5a5a2aac298ab3eccaee8a52ba46078c3d5975a290d | 50f8fbf3d327483c3eeff8f6cbd4065e4c7600bb501fbe08958a5c79a0926428 | c1ccn2ccnc2c1 | Cl-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4].[C:5]-[C:6]-[NH2;D1;+0:7]>>[C:5]-[C:6]-[NH;D2;+0:7]-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4] | 78.1 | [{"value": 77.9, "product": "CS(=O)(=O)NCCSC1=CC=CC=2N1C=CN2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 78.1, "product": "CS(=O)(=O)NCCSC1=CC=CC=2N1C=CN2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 5-[2-(amino)ethylthio]imidazo[1,2-a]pyridine (9.63 g, 49.8 mmoles) and triethylamine (7.64 ml) in methylene chloride (150 ml) was added methanesulfonyl chloride (3.85 ml, 49.7 mmoles) with stirring under ice-cooling and was stirred under ice-cooling for 1 hour. The reaction solution was poured into wat... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Sulfonyl halide | Sulfonamide | null | null | c1ccn2ccnc2c1 | HCl | C(Cl)Cl | null | null | CS(=O)(=O)Cl.NCCSc1cccc2nccn12>C(Cl)Cl>CS(=O)(=O)NCCSc1cccc2nccn12 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-90e3544a7e8d48009be88fd306d4e8e7 | Cl>>Cl | CS(=O)(=O)NCCSC1=CC=CC=2N1C=CN2.Cl.CO>>Cl.CS(=O)(=O)NCCSC1=CC=CC=2N1C=CN2 | [ClH:18]>>[ClH:18] | Cl | Cl | null | null | CO | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | null | null | 89.3 | [{"value": 89.3, "product": "Cl.CS(=O)(=O)NCCSC1=CC=CC=2N1C=CN2", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A suspension of 5-[2-(methylsulfonylamino)ethylthio]imidazo[1,2-a]pyridine (543 g, 2 mmoles) in methanol (20 ml) was treated with hydrogen chloride-methanol. After the solvent was distilled off, the residue was crystallized from chloroform ether. Then, the crystals thus obtained were washed with ether and dried to obta... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | null | null | CO | null | null | Cl>CO>Cl |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-b37486258c7548529fd7103f125f8261 | CCS(=O)(=O)Cl.NCCSc1cccc2nccn12>>CCS(=O)(=O)NCCSc1cccc2nccn12 | NCCSC1=CC=CC=2N1C=CN2.C(C)N(CC)CC.C(C)S(=O)(=O)Cl>>C(C)S(=O)(=O)NCCSC1=CC=CC=2N1C=CN2 | Cl[S:3]([CH2:2][CH3:1])(=[O:4])=[O:5].[NH2:6][CH2:7][CH2:8][S:9][c:10]1[cH:11][cH:12][cH:13][c:14]2[n:15][cH:16][cH:17][n:18]12>>[CH3:1][CH2:2][S:3](=[O:4])(=[O:5])[NH:6][CH2:7][CH2:8][S:9][c:10]1[cH:11][cH:12][cH:13][c:14]2[n:15][cH:16][cH:17][n:18]12 | CCS(=O)(=O)Cl.NCCSc1cccc2nccn12 | CCS(=O)(=O)NCCSc1cccc2nccn12 | null | null | C(Cl)Cl | Miscellaneous | Sulfonamide synthesis (Schotten-Baumann) primary amine | a86b0632821e188c0a5dc5a5a2aac298ab3eccaee8a52ba46078c3d5975a290d | 50f8fbf3d327483c3eeff8f6cbd4065e4c7600bb501fbe08958a5c79a0926428 | c1ccn2ccnc2c1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[C:4]-[C;D1;H3:5].[C:6]-[C:7]-[NH2;D1;+0:8]>>[C:6]-[C:7]-[NH;D2;+0:8]-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[C:4]-[C;D1;H3:5] | 78.2 | [{"value": 78.2, "product": "C(C)S(=O)(=O)NCCSC1=CC=CC=2N1C=CN2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 78.1, "product": "C(C)S(=O)(=O)NCCSC1=CC=CC=2N1C=CN2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 5-[2-(amino)ethylthio]imidazo[1,2-a]pyridine (1.93 g, 10 mmoles) and triethylamine (1.53 ml, 11 mmoles) in methylene chloride (100 ml) was added ethanesulfonyl chloride (0.95 ml, 10 mmoles) at room temperature with stirring and the mixture was stirred at room temperature for 1 hour. The reaction mixtur... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Sulfonyl halide | Sulfonamide | null | null | c1ccn2ccnc2c1 | HCl | C(Cl)Cl | null | null | CCS(=O)(=O)Cl.NCCSc1cccc2nccn12>C(Cl)Cl>CCS(=O)(=O)NCCSc1cccc2nccn12 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-1c9d4fa8cda74077a9d8cdb9265be8ed | C1COCCN1.C=O.CS(=O)(=O)NCCSc1cccc2nccn12>>CS(=O)(=O)NCCSc1cccc2ncc(CN3CCOCC3)n12 | CS(=O)(=O)NCCSC1=CC=CC=2N1C=CN2.C=O.N1CCOCC1>>CS(=O)(=O)NCCSC1=CC=CC=2N1C(=CN2)CN2CCOCC2 | [NH:18]1[CH2:19][CH2:20][O:21][CH2:22][CH2:23]1.O=[CH2:17].[CH3:1][S:2](=[O:3])(=[O:4])[NH:5][CH2:6][CH2:7][S:8][c:9]1[cH:10][cH:11][cH:12][c:13]2[n:14][cH:15][cH:16][n:24]12>>[CH3:1][S:2](=[O:3])(=[O:4])[NH:5][CH2:6][CH2:7][S:8][c:9]1[cH:10][cH:11][cH:12][c:13]2[n:14][cH:15][c:16]([CH2:17][N:18]3[CH2:19][CH2:20][O:21]... | C1COCCN1.C=O.CS(=O)(=O)NCCSc1cccc2nccn12 | CS(=O)(=O)NCCSc1cccc2ncc(CN3CCOCC3)n12 | null | null | C(C)(=O)O | Heteroatom Alkylation and Arylation | OtherReaction | 6b4ae5aa80021261c6aaedaefa5d3defe26d9563ca80e76f1ce7765ec33cd64e | e1fdef8fde1c506d7c9deb8fd5e6f322eceea2abce3167abcf412a1fa4fd5443 | c1ccn2c(CN3CCOCC3)cnc2c1 | O=[CH2;D1;+0:1].[#8:2]1-[C:3]-[C:4]-[NH;D2;+0:5]-[C:6]-[C:7]-1.[c:8]:[c:9]1:[#7;a:10]:[c:11]:[cH;D2;+0:12]:[#7;a:13]:1:[c:14]>>[c:8]:[c:9]1:[#7;a:10]:[c:11]:[c;H0;D3;+0:12](-[CH2;D2;+0:1]-[N;H0;D3;+0:5]2-[C:4]-[C:3]-[#8:2]-[C:7]-[C:6]-2):[#7;a:13]:1:[c:14] | 71.5 | [{"value": 71.5, "product": "CS(=O)(=O)NCCSC1=CC=CC=2N1C(=CN2)CN2CCOCC2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 71.5, "product": "CS(=O)(=O)NCCSC1=CC=CC=2N1C(=CN2)CN2CCOCC2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 37% formalin (178 mg, 2.2 mmoles) in acetic acid (2 ml) was added morpholin (192 μl, 2.2 mmoles) under ice-cooling with stirring and the mixture was stirred at room temperature for 30 minutes. 5-[2-(methylsulfonylamino)ethylthio] imidazo[1,2-a]pyridine (543 mg, 2 mmoles) was added to the reaction mixtu... | 10.6084/m9.figshare.5104873.v1 | null | Formaldehyde.Secondary amine | Tertiary amine | C1COCCN1.c1ccn2ccnc2c1 | c1ccn2ccnc2c1.C1COCC[NH]1 | c1ccn2ccnc2c1.C1COCC[NH]1 | HO- | C(C)(=O)O | null | null | C1COCCN1.C=O.CS(=O)(=O)NCCSc1cccc2nccn12>C(C)(=O)O>CS(=O)(=O)NCCSc1cccc2ncc(CN3CCOCC3)n12 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-2d292e114dec4b6eaadaf6bd16d150d2 | CCOC(=O)c1cn2c(SCCNS(C)(=O)=O)cccc2n1.CO>>CS(=O)(=O)NCCSc1cccc2nc(CC(=O)O)cn12 | Cl.C(C)OC(=O)C=1N=C2N(C(=CC=C2)SCCNS(=O)(=O)C)C1.[OH-].[Na+].CO>>C(=O)(O)CC=1N=C2N(C(=CC=C2)SCCNS(=O)(=O)C)C1 | CCO[C:16]([c:15]1[n:14][c:13]2[cH:12][cH:11][cH:10][c:9]([S:8][CH2:7][CH2:6][NH:5][S:2]([CH3:1])(=[O:3])=[O:4])[n:21]2[cH:20]1)=[O:18].[CH3:17][OH:19]>>[CH3:1][S:2](=[O:3])(=[O:4])[NH:5][CH2:6][CH2:7][S:8][c:9]1[cH:10][cH:11][cH:12][c:13]2[n:14][c:15]([CH2:16][C:17](=[O:18])[OH:19])[cH:20][n:21]12 | CCOC(=O)c1cn2c(SCCNS(C)(=O)=O)cccc2n1.CO | CS(=O)(=O)NCCSc1cccc2nc(CC(=O)O)cn12 | null | null | C(Cl)Cl | C-C Coupling | OtherReaction | c824c18621d3de650ba03e259cc400ce2fba27cd91610d2d8234763184636296 | 8fb1dfe94a77e1d4cf0cd3e4e184a4d169bd9164a787c5974edec4da8a424e47 | c1ccn2ccnc2c1 | C-C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[c:3]1:[#7;a:4]:[c:5]:[#7;a:6](:[c:7]):[c:8]:1.[CH3;D1;+0:9]-[O;D1;H1:10]>>[O;D1;H1:10]-[C;H0;D3;+0:9](=[O;H0;D1;+0:2])-[CH2;D2;+0:1]-[c:3]1:[#7;a:4]:[c:5]:[#7;a:6](:[c:7]):[c:8]:1 | 51.1 | [{"value": 51.1, "product": "C(=O)(O)CC=1N=C2N(C(=CC=C2)SCCNS(=O)(=O)C)C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 2.5 | HOUR | To a solution of 2-ethoxycarbonyl-5-[2-(methylsulfonylamino)ethylthio]imidazo[1,2-a]pyridine (1.65 g, 4.62 mmoles) in methanol (5 ml) was added 1N NaOH (6.93 ml, 6.93 mmoles) and the mixture was stirred at room temperature for 2.5 hours. After the reaction mixture was washed with methylene chloride, 1N HCl (17.39 ml, 1... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Methanol | Carboxylic acid | null | null | c1ccn2ccnc2c1 | HO- | C(Cl)Cl | null | 2.5 | CCOC(=O)c1cn2c(SCCNS(C)(=O)=O)cccc2n1.CO>C(Cl)Cl>CS(=O)(=O)NCCSc1cccc2nc(CC(=O)O)cn12 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-c70f3f1b3dc840cb9734132ec78a68c7 | CC(=O)Cl.NCCSc1cccc2nccn12>>CC(=O)NCCSc1cccc2nccn12 | O.Cl.Cl.NCCSC1=CC=CC=2N1C=CN2.C(C)N(CC)CC.C(C)(=O)Cl>>C(C)(=O)NCCSC1=CC=CC=2N1C=CN2 | Cl[C:2]([CH3:1])=[O:3].[NH2:4][CH2:5][CH2:6][S:7][c:8]1[cH:9][cH:10][cH:11][c:12]2[n:13][cH:14][cH:15][n:16]12>>[CH3:1][C:2](=[O:3])[NH:4][CH2:5][CH2:6][S:7][c:8]1[cH:9][cH:10][cH:11][c:12]2[n:13][cH:14][cH:15][n:16]12 | CC(=O)Cl.NCCSc1cccc2nccn12 | CC(=O)NCCSc1cccc2nccn12 | null | null | CN(C=O)C | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | c1ccn2ccnc2c1 | Cl-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[C:4]-[C:5]-[NH2;D1;+0:6]>>[C:4]-[C:5]-[NH;D2;+0:6]-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3] | 66.8 | [{"value": 66.8, "product": "C(C)(=O)NCCSC1=CC=CC=2N1C=CN2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 66.7, "product": "C(C)(=O)NCCSC1=CC=CC=2N1C=CN2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 5-[2-(amino)ethylthio]imidazo[1,2-a]pyridine dihydrochloride (2.66 g, 10 mmoles) and triethylamine (4.32 ml, 31 mmoles) in N,N-dimethylformamide (24 ml) was added acetyl chloride (0.71 ml, 10 mmoles) under ice-cooling with stirring and the mixture was stirred at room temperature for 4 hours. The reacti... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccn2ccnc2c1 | HCl | CN(C=O)C | null | null | CC(=O)Cl.NCCSc1cccc2nccn12>CN(C=O)C>CC(=O)NCCSc1cccc2nccn12 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-201221c47b48468e8dcff804deda74d1 | NCCSc1cccc2nccn12.O=C1OC(=O)c2ccccc21>>O=C(O)c1ccccc1C(=O)NCCSc1cccc2nccn12 | NCCSC1=CC=CC=2N1C=CN2.C1(C=2C(C(=O)O1)=CC=CC2)=O>>C(=O)(O)C1=C(C(=O)NCCSC2=CC=CC=3N2C=CN3)C=CC=C1 | [NH2:12][CH2:13][CH2:14][S:15][c:16]1[cH:17][cH:18][cH:19][c:20]2[n:21][cH:22][cH:23][n:24]12.[O:1]=[C:2]1[O:3][C:10](=[O:11])[c:9]2[c:4]1[cH:5][cH:6][cH:7][cH:8]2>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][cH:6][cH:7][cH:8][c:9]1[C:10](=[O:11])[NH:12][CH2:13][CH2:14][S:15][c:16]1[cH:17][cH:18][cH:19][c:20]2[n:21][cH:22][cH:23][... | NCCSc1cccc2nccn12.O=C1OC(=O)c2ccccc21 | O=C(O)c1ccccc1C(=O)NCCSc1cccc2nccn12 | null | null | C(Cl)(Cl)Cl | Acylation | OtherReaction | 56370f0128472578db3eed92c09361daee495a283cbb2b2085e560c29e14b228 | 8f0bd214ca7de35d6d193b05238212653acafd72c87d8cc6af190f4acf79b4a4 | O=C(NCCSc1cccc2nccn12)c1ccccc1 | [C:1]-[C:2]-[NH2;D1;+0:3].[O;D1;H0:4]=[C;H0;D3;+0:5]1-[O;H0;D2;+0:6]-[C:7](=[O;D1;H0:8])-[c:9]:[c:10]-1:[c:11]>>[C:1]-[C:2]-[NH;D2;+0:3]-[C;H0;D3;+0:5](=[O;D1;H0:4])-[c:10](:[c:11]):[c:9]-[C:7](=[O;D1;H0:8])-[OH;D1;+0:6] | 84.8 | [{"value": 84.8, "product": "C(=O)(O)C1=C(C(=O)NCCSC2=CC=CC=3N2C=CN3)C=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 84.8, "product": "C(=O)(O)C1=C(C(=O)NCCSC2=CC=CC=3N2C=CN3)C=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 14 | HOUR | To a solution of 5-[2-(amino)ethylthio]imidazo[1,2-a]pyridine (1.12 g, 5.8 mmoles) in chloroform (58 ml) was added phthalic anhydride (1.12 g, 7.56 mmoles) and the mixture was stirred at room temperature for 14 hours and then heated at reflux for 5 hours. The reaction mixture was cooled by standing. The crystals precip... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Ester.Ester.Primary amine | Carboxylic acid.Secondary amide | c1ccc2c(c1)COC2 | null | c1ccccc1.c1ccn2ccnc2c1 | null | C(Cl)(Cl)Cl | null | 14 | NCCSc1cccc2nccn12.O=C1OC(=O)c2ccccc21>C(Cl)(Cl)Cl>O=C(O)c1ccccc1C(=O)NCCSc1cccc2nccn12 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-852f02fa664542a2bdf8f02b66d9841f | CN=C=O.NCCSc1cccc2nccn12>>CNC(=O)NCCSc1cccc2nccn12 | NCCSC1=CC=CC=2N1C=CN2.CN=C=O>>CNC(=O)NCCSC1=CC=CC=2N1C=CN2 | [CH3:1][N:2]=[C:3]=[O:4].[NH2:5][CH2:6][CH2:7][S:8][c:9]1[cH:10][cH:11][cH:12][c:13]2[n:14][cH:15][cH:16][n:17]12>>[CH3:1][NH:2][C:3](=[O:4])[NH:5][CH2:6][CH2:7][S:8][c:9]1[cH:10][cH:11][cH:12][c:13]2[n:14][cH:15][cH:16][n:17]12 | CN=C=O.NCCSc1cccc2nccn12 | CNC(=O)NCCSc1cccc2nccn12 | null | null | C(Cl)Cl | Acylation | Urea synthesis via isocyanate and primary amine | d39cd7dc52a79bb265ff8ef61ef7bf9dc7f7b5fb0150fcb4881bdfb18ab9c380 | a5dc801930c765d2a435a0a2973e50163c305ba8e7641d6adbcc1550b7b96de7 | c1ccn2ccnc2c1 | [C;D1;H3:1]-[N;H0;D2;+0:2]=[C;H0;D2;+0:3]=[O;D1;H0:4].[C:5]-[C:6]-[NH2;D1;+0:7]>>[C:5]-[C:6]-[NH;D2;+0:7]-[C;H0;D3;+0:3](=[O;D1;H0:4])-[NH;D2;+0:2]-[C;D1;H3:1] | 86 | [{"value": 86.0, "product": "CNC(=O)NCCSC1=CC=CC=2N1C=CN2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 85.9, "product": "CNC(=O)NCCSC1=CC=CC=2N1C=CN2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 5-[2-(amino)ethylthio]imidazo[1,2-a]pyridine (1.93 g, 10 mmoles) in methylene chloride (30 ml) was added methyl isocyanate (0.59 ml, 10 mmoles) under ice-cooling with stirring and the mixture was stirred under ice-cooling for 1 hour. After the solvent was distilled off, the residue was purified by colu... | 10.6084/m9.figshare.5104873.v1 | null | Isocyanate.Primary amine | Urea | null | null | c1ccn2ccnc2c1 | null | C(Cl)Cl | null | null | CN=C=O.NCCSc1cccc2nccn12>C(Cl)Cl>CNC(=O)NCCSc1cccc2nccn12 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-38cd054a169a4254b93577d431c563a5 | CN=C=O.OCCSc1cccc2nccn12>>CNC(=O)OCCSc1cccc2nccn12 | OCCSC1=CC=CC=2N1C=CN2.C(C)N(CC)CC.CN=C=O>>CNC(=O)OCCSC1=CC=CC=2N1C=CN2 | [CH3:1][N:2]=[C:3]=[O:4].[OH:5][CH2:6][CH2:7][S:8][c:9]1[cH:10][cH:11][cH:12][c:13]2[n:14][cH:15][cH:16][n:17]12>>[CH3:1][NH:2][C:3](=[O:4])[O:5][CH2:6][CH2:7][S:8][c:9]1[cH:10][cH:11][cH:12][c:13]2[n:14][cH:15][cH:16][n:17]12 | CN=C=O.OCCSc1cccc2nccn12 | CNC(=O)OCCSc1cccc2nccn12 | null | null | C(Cl)Cl | Protection | OtherReaction | 8d2aa5da7fec498749aba98cc9467e8d82c146f343570568bec74a92b10e0ae2 | e505c5de73b3f9ad0414c141c59109424d376f26a728bbd154d3edfd03d2f50a | c1ccn2ccnc2c1 | [C;D1;H3:1]-[N;H0;D2;+0:2]=[C;H0;D2;+0:3]=[O;D1;H0:4].[C:5]-[C:6]-[OH;D1;+0:7]>>[C:5]-[C:6]-[O;H0;D2;+0:7]-[C;H0;D3;+0:3](=[O;D1;H0:4])-[NH;D2;+0:2]-[C;D1;H3:1] | 85.2 | [{"value": 85.2, "product": "CNC(=O)OCCSC1=CC=CC=2N1C=CN2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 85.2, "product": "CNC(=O)OCCSC1=CC=CC=2N1C=CN2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 5-[2-(hydroxy)ethylthio]imidazo[1,2-a]pyridine (971 mg, 5 mmoles) and trietylamine (0.91 ml, 6.53 mmoles) in methylene chloride (40 ml) was added methyl isocyanate (0.65 ml, 11 mmoles) under ice-cooling with stirring and the mixture was stirred at room temperature for 12 hours. The reaction mixture was... | 10.6084/m9.figshare.5104873.v1 | null | Isocyanate.Primary alcohol | Carbamic ester | null | null | c1ccn2ccnc2c1 | null | C(Cl)Cl | null | null | CN=C=O.OCCSc1cccc2nccn12>C(Cl)Cl>CNC(=O)OCCSc1cccc2nccn12 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-349268ab472d46378b63207ed9f22d8d | NCCCO.O=C(OCCSc1cccc2nccn12)Oc1ccccc1>>O=C(NCCCO)OCCSc1cccc2nccn12 | O(C1=CC=CC=C1)C(=O)OCCSC1=CC=CC=2N1C=CN2.NCCCO>>OCCCNC(=O)OCCSC1=CC=CC=2N1C=CN2 | [NH2:3][CH2:4][CH2:5][CH2:6][OH:7].c1ccc(O[C:2](=[O:1])[O:8][CH2:9][CH2:10][S:11][c:12]2[cH:13][cH:14][cH:15][c:16]3[n:17][cH:18][cH:19][n:20]23)cc1>>[O:1]=[C:2]([NH:3][CH2:4][CH2:5][CH2:6][OH:7])[O:8][CH2:9][CH2:10][S:11][c:12]1[cH:13][cH:14][cH:15][c:16]2[n:17][cH:18][cH:19][n:20]12 | NCCCO.O=C(OCCSc1cccc2nccn12)Oc1ccccc1 | O=C(NCCCO)OCCSc1cccc2nccn12 | null | null | C(Cl)(Cl)Cl | Protection | OtherReaction | 75e82d9a40c04469947b4efd2c5b8b8e3256ce6fc9ac082e6a9d21beead59e34 | fe2735908374a286b2b645161b547a5da1873b2e6cda11bae9c60850cfba5b7d | c1ccn2ccnc2c1 | [C:1]-[#8:2]-[C;H0;D3;+0:3](=[O;D1;H0:4])-O-c1:c:c:c:c:c:1.[C:5]-[C:6]-[NH2;D1;+0:7]>>[C:5]-[C:6]-[NH;D2;+0:7]-[C;H0;D3;+0:3](=[O;D1;H0:4])-[#8:2]-[C:1] | 55.6 | [{"value": 55.6, "product": "OCCCNC(=O)OCCSC1=CC=CC=2N1C=CN2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 55.6, "product": "OCCCNC(=O)OCCSC1=CC=CC=2N1C=CN2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 120 | CELSIUS | 1.5 | HOUR | To 5-[2-(phenoxycarbonyloxy)ethylthio]imidazo[1,2-a]pyridine (1.10 g, 3.50 mmoles) was added 3-aminopropanol (0.27 ml, 3.52 mmoles) and the mixture was stirred at 120° C. for 1.5 hours. The reaction mixture was cooled by standing and chloroform was added thereto, which was washed with water and dried over anhydrous mag... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether.Primary amine | Carbamic ester | c1ccccc1 | null | c1ccn2ccnc2c1 | HO- | C(Cl)(Cl)Cl | 120 | 1.5 | NCCCO.O=C(OCCSc1cccc2nccn12)Oc1ccccc1>C(Cl)(Cl)Cl>O=C(NCCCO)OCCSc1cccc2nccn12 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-a1682d3d63114f3888105607aebf2126 | COC(=O)Cl.NCCSc1cccc2nccn12>>COC(=O)NCCSc1cccc2nccn12 | NCCSC1=CC=CC=2N1C=CN2.C(C)N(CC)CC.ClC(=O)OC>>COC(=O)NCCSC1=CC=CC=2N1C=CN2 | Cl[C:3]([O:2][CH3:1])=[O:4].[NH2:5][CH2:6][CH2:7][S:8][c:9]1[cH:10][cH:11][cH:12][c:13]2[n:14][cH:15][cH:16][n:17]12>>[CH3:1][O:2][C:3](=[O:4])[NH:5][CH2:6][CH2:7][S:8][c:9]1[cH:10][cH:11][cH:12][c:13]2[n:14][cH:15][cH:16][n:17]12 | COC(=O)Cl.NCCSc1cccc2nccn12 | COC(=O)NCCSc1cccc2nccn12 | null | null | C(Cl)Cl | Protection | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 038720aa61a7efa0f2a9ee6f2e0adf63a9ffdc2be4697c11a6215baef34f97b2 | 205f353513ce9506ab61831799da8fb73ec2ef5cfa927664496d3ce72c438860 | c1ccn2ccnc2c1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C;D1;H3:4].[C:5]-[C:6]-[NH2;D1;+0:7]>>[C:5]-[C:6]-[NH;D2;+0:7]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C;D1;H3:4] | 66.9 | [{"value": 66.9, "product": "COC(=O)NCCSC1=CC=CC=2N1C=CN2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 66.9, "product": "COC(=O)NCCSC1=CC=CC=2N1C=CN2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 5-[2-(amino)ethylthio]imidazo[1,2-a]pyridine (1.93 g, 10 mmoles) and triethylamine (1.53 ml, 11 mmoles) in methylene chloride (30 ml) was added methyl chloroformate (0.77 ml, 10 mmoles) under ice-cooling with stirring and the mixture was stirred at room temperature for 20 minutes. The reaction mixture ... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Ether.Primary amine | Carbamic ester | null | null | c1ccn2ccnc2c1 | HCl | C(Cl)Cl | null | null | COC(=O)Cl.NCCSc1cccc2nccn12>C(Cl)Cl>COC(=O)NCCSc1cccc2nccn12 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-831db6ca9bbd41e0aaa035a1763a8ec1 | O=C1c2ccccc2C(=O)N1CBr.Sc1cccc2nccn12>>O=C1c2ccccc2C(=O)N1CSc1cccc2nccn12 | SC1=CC=CC=2N1C=CN2.BrCN1C(C=2C(C1=O)=CC=CC2)=O.C(C)N(CC)CC>>C1(C=2C(C(N1CSC1=CC=CC=3N1C=CN3)=O)=CC=CC2)=O | Br[CH2:12][N:11]1[C:2](=[O:1])[c:3]2[cH:4][cH:5][cH:6][cH:7][c:8]2[C:9]1=[O:10].[SH:13][c:14]1[cH:15][cH:16][cH:17][c:18]2[n:19][cH:20][cH:21][n:22]12>>[O:1]=[C:2]1[c:3]2[cH:4][cH:5][cH:6][cH:7][c:8]2[C:9](=[O:10])[N:11]1[CH2:12][S:13][c:14]1[cH:15][cH:16][cH:17][c:18]2[n:19][cH:20][cH:21][n:22]12 | O=C1c2ccccc2C(=O)N1CBr.Sc1cccc2nccn12 | O=C1c2ccccc2C(=O)N1CSc1cccc2nccn12 | null | null | C(C)O | Heteroatom Alkylation and Arylation | thioether_nucl_sub | 670a330769b87d9fd3df1128eae04bdefd1a0d70c3e632885aa0e6a5b15fccc1 | fcd4bd1a4380f5eecf1a2477e13ea8343f264aec0388929401fe7448dc3025d8 | O=C1c2ccccc2C(=O)N1CSc1cccc2nccn12 | Br-[CH2;D2;+0:1]-[#7:2]1-[C:3](=[O;D1;H0:4])-[c:5]:[c:6]-[C:7]-1=[O;D1;H0:8].[SH;D1;+0:9]-[c:10](:[c:11]):[#7;a:12]1:[c:13]:[#7;a:14]:[c:15]:[c:16]:1>>[O;D1;H0:8]=[C:7]1-[c:6]:[c:5]-[C:3](=[O;D1;H0:4])-[#7:2]-1-[CH2;D2;+0:1]-[S;H0;D2;+0:9]-[c:10](:[c:11]):[#7;a:12]1:[c:13]:[#7;a:14]:[c:15]:[c:16]:1 | 69.4 | [{"value": 69.4, "product": "C1(C=2C(C(N1CSC1=CC=CC=3N1C=CN3)=O)=CC=CC2)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 69.3, "product": "C1(C=2C(C(N1CSC1=CC=CC=3N1C=CN3)=O)=CC=CC2)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | To a suspension of 5-mercaptoimidazo[1,2-a]pyridine (3.00 g, 20 mmoles) and N-bromomethylphthalimide (5.28 g, 22 mmoles) in ethanol (200 ml) was added triethylamine (4.2 ml, 30 mmoles) and the mixture was stirred at room temperature for 1 hour. After the solvent was distilled off, chloroform was added to the residue, w... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Substituted dicarboximide.Aromatic thiol | Substituted dicarboximide.Monosulfide | null | null | c1ccc2c(c1)C[NH]C2.c1ccn2ccnc2c1 | HBr | C(C)O | null | 1 | O=C1c2ccccc2C(=O)N1CBr.Sc1cccc2nccn12>C(C)O>O=C1c2ccccc2C(=O)N1CSc1cccc2nccn12 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-4e1bc24fc8084853ba0216a3bf0feced | O=C1c2ccccc2C(=O)N1CCBr.Sc1cccc2nccn12>>O=C1c2ccccc2C(=O)N1CCSc1cccc2nccn12 | SC1=CC=CC=2N1C=CN2.BrCCN1C(C=2C(C1=O)=CC=CC2)=O.C(C)N(CC)CC>>C1(C=2C(C(N1CCSC1=CC=CC=3N1C=CN3)=O)=CC=CC2)=O | Br[CH2:13][CH2:12][N:11]1[C:2](=[O:1])[c:3]2[cH:4][cH:5][cH:6][cH:7][c:8]2[C:9]1=[O:10].[SH:14][c:15]1[cH:16][cH:17][cH:18][c:19]2[n:20][cH:21][cH:22][n:23]12>>[O:1]=[C:2]1[c:3]2[cH:4][cH:5][cH:6][cH:7][c:8]2[C:9](=[O:10])[N:11]1[CH2:12][CH2:13][S:14][c:15]1[cH:16][cH:17][cH:18][c:19]2[n:20][cH:21][cH:22][n:23]12 | O=C1c2ccccc2C(=O)N1CCBr.Sc1cccc2nccn12 | O=C1c2ccccc2C(=O)N1CCSc1cccc2nccn12 | null | null | C(C)O | Heteroatom Alkylation and Arylation | thioether_nucl_sub | 26df88c6a3f5f203c89584658be4e126cb42994c98a2e16bc812e1036cdae857 | 8b2f52296c3a93039174c980b6042ba15754e04d6892a1284c3a32985220b214 | O=C1c2ccccc2C(=O)N1CCSc1cccc2nccn12 | Br-[CH2;D2;+0:1]-[C:2]-[#7:3](-[C:4]=[O;D1;H0:5])-[C:6]=[O;D1;H0:7].[SH;D1;+0:8]-[c:9](:[c:10]):[#7;a:11]1:[c:12]:[#7;a:13]:[c:14]:[c:15]:1>>[O;D1;H0:7]=[C:6]-[#7:3](-[C:2]-[CH2;D2;+0:1]-[S;H0;D2;+0:8]-[c:9](:[c:10]):[#7;a:11]1:[c:12]:[#7;a:13]:[c:14]:[c:15]:1)-[C:4]=[O;D1;H0:5] | 61.1 | [{"value": 61.1, "product": "C1(C=2C(C(N1CCSC1=CC=CC=3N1C=CN3)=O)=CC=CC2)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 61.1, "product": "C1(C=2C(C(N1CCSC1=CC=CC=3N1C=CN3)=O)=CC=CC2)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | To a suspension of 5-mercaptoimidazo[1,2-a]pyridine (3.00g, 20 mmoles) and N-[2-(bromo)ethyl]phthalimide (5.59 g, 22 mmoles) in ethanol (200 ml) was added triethylamine (4.2 ml, 30 mmoles) and the mixture was stirred at room temperature for 3 hours and heated at reflux for 4 hours. After the solvent was distilled off, ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic thiol | Monosulfide | null | null | c1ccc2c(c1)C[NH]C2.c1ccn2ccnc2c1 | HBr | C(C)O | null | 3 | O=C1c2ccccc2C(=O)N1CCBr.Sc1cccc2nccn12>C(C)O>O=C1c2ccccc2C(=O)N1CCSc1cccc2nccn12 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-2142af33e93641faaf0996e15f201439 | O=C1c2ccccc2C(=O)N1CCCBr.Sc1cccc2nccn12>>O=C1c2ccccc2C(=O)N1CCCSc1cccc2nccn12 | SC1=CC=CC=2N1C=CN2.BrCCCN1C(C=2C(C1=O)=CC=CC2)=O.C(C)N(CC)CC>>C1(C=2C(C(N1CCCSC1=CC=CC=3N1C=CN3)=O)=CC=CC2)=O | Br[CH2:14][CH2:13][CH2:12][N:11]1[C:2](=[O:1])[c:3]2[cH:4][cH:5][cH:6][cH:7][c:8]2[C:9]1=[O:10].[SH:15][c:16]1[cH:17][cH:18][cH:19][c:20]2[n:21][cH:22][cH:23][n:24]12>>[O:1]=[C:2]1[c:3]2[cH:4][cH:5][cH:6][cH:7][c:8]2[C:9](=[O:10])[N:11]1[CH2:12][CH2:13][CH2:14][S:15][c:16]1[cH:17][cH:18][cH:19][c:20]2[n:21][cH:22][cH:2... | O=C1c2ccccc2C(=O)N1CCCBr.Sc1cccc2nccn12 | O=C1c2ccccc2C(=O)N1CCCSc1cccc2nccn12 | null | null | C(C)O | Heteroatom Alkylation and Arylation | thioether_nucl_sub | 26df88c6a3f5f203c89584658be4e126cb42994c98a2e16bc812e1036cdae857 | 8b2f52296c3a93039174c980b6042ba15754e04d6892a1284c3a32985220b214 | O=C1c2ccccc2C(=O)N1CCCSc1cccc2nccn12 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[SH;D1;+0:4]-[c:5](:[c:6]):[#7;a:7]1:[c:8]:[#7;a:9]:[c:10]:[c:11]:1>>[C:3]-[C:2]-[CH2;D2;+0:1]-[S;H0;D2;+0:4]-[c:5](:[c:6]):[#7;a:7]1:[c:8]:[#7;a:9]:[c:10]:[c:11]:1 | 71.1 | [{"value": 71.1, "product": "C1(C=2C(C(N1CCCSC1=CC=CC=3N1C=CN3)=O)=CC=CC2)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 71.0, "product": "C1(C=2C(C(N1CCCSC1=CC=CC=3N1C=CN3)=O)=CC=CC2)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | To a suspension of 5-mercaptoimidazo[1,2-a]pyridine (3.00g, 20 mmoles) and N-[3-(bromo)propyl]phthalimide (5.90 g, 22 mmoles) in ethanol (200 ml) was added triethylamine (4.2 ml, 30 mmoles) and the mixture was stirred at room temperature for 1 hour and heated at reflux for 1 hour. After the solvent was distilled off, c... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic thiol | Monosulfide | null | null | c1ccc2c(c1)C[NH]C2.c1ccn2ccnc2c1 | HBr | C(C)O | null | 1 | O=C1c2ccccc2C(=O)N1CCCBr.Sc1cccc2nccn12>C(C)O>O=C1c2ccccc2C(=O)N1CCCSc1cccc2nccn12 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-50be1fc82c544b38bf6a4a6ff7e52623 | O=C1c2ccccc2C(=O)N1CCCCBr.Sc1cccc2nccn12>>O=C1c2ccccc2C(=O)N1CCCCSc1cccc2nccn12 | SC1=CC=CC=2N1C=CN2.BrCCCCN1C(C=2C(C1=O)=CC=CC2)=O.C(C)N(CC)CC>>C1(C=2C(C(N1CCCCSC1=CC=CC=3N1C=CN3)=O)=CC=CC2)=O | Br[CH2:15][CH2:14][CH2:13][CH2:12][N:11]1[C:2](=[O:1])[c:3]2[cH:4][cH:5][cH:6][cH:7][c:8]2[C:9]1=[O:10].[SH:16][c:17]1[cH:18][cH:19][cH:20][c:21]2[n:22][cH:23][cH:24][n:25]12>>[O:1]=[C:2]1[c:3]2[cH:4][cH:5][cH:6][cH:7][c:8]2[C:9](=[O:10])[N:11]1[CH2:12][CH2:13][CH2:14][CH2:15][S:16][c:17]1[cH:18][cH:19][cH:20][c:21]2[n... | O=C1c2ccccc2C(=O)N1CCCCBr.Sc1cccc2nccn12 | O=C1c2ccccc2C(=O)N1CCCCSc1cccc2nccn12 | null | null | C(C)O | Heteroatom Alkylation and Arylation | thioether_nucl_sub | 26df88c6a3f5f203c89584658be4e126cb42994c98a2e16bc812e1036cdae857 | 8b2f52296c3a93039174c980b6042ba15754e04d6892a1284c3a32985220b214 | O=C1c2ccccc2C(=O)N1CCCCSc1cccc2nccn12 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[SH;D1;+0:4]-[c:5](:[c:6]):[#7;a:7]1:[c:8]:[#7;a:9]:[c:10]:[c:11]:1>>[C:3]-[C:2]-[CH2;D2;+0:1]-[S;H0;D2;+0:4]-[c:5](:[c:6]):[#7;a:7]1:[c:8]:[#7;a:9]:[c:10]:[c:11]:1 | 64.1 | [{"value": 64.1, "product": "C1(C=2C(C(N1CCCCSC1=CC=CC=3N1C=CN3)=O)=CC=CC2)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 64.0, "product": "C1(C=2C(C(N1CCCCSC1=CC=CC=3N1C=CN3)=O)=CC=CC2)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | To a suspension of 5-mercaptoimidazo[1,2-a]pyridine (3.00g, 20 mmoles) and N-[4-(bromo)butyl]phthalimide (6.21 g, 22 mmoles) in ethanol (200 ml) was added triethylamine (4.2 ml, 30 mmoles) and the mixture was stirred at room temperature for 1 hour and heated at reflux for 45 minutes. After the solvent was distilled off... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic thiol | Monosulfide | null | null | c1ccc2c(c1)C[NH]C2.c1ccn2ccnc2c1 | HBr | C(C)O | null | 1 | O=C1c2ccccc2C(=O)N1CCCCBr.Sc1cccc2nccn12>C(C)O>O=C1c2ccccc2C(=O)N1CCCCSc1cccc2nccn12 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-27f5598901a84909a3b45c27115d5a04 | O=C1c2ccccc2C(=O)N1CCCCCCBr.Sc1cccc2nccn12>>O=C1c2ccccc2C(=O)N1CCCCCCSc1cccc2nccn12 | SC1=CC=CC=2N1C=CN2.BrCCCCCCN1C(C=2C(C1=O)=CC=CC2)=O.C(C)N(CC)CC>>C1(C=2C(C(N1CCCCCCSC1=CC=CC=3N1C=CN3)=O)=CC=CC2)=O | Br[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][N:11]1[C:2](=[O:1])[c:3]2[cH:4][cH:5][cH:6][cH:7][c:8]2[C:9]1=[O:10].[SH:18][c:19]1[cH:20][cH:21][cH:22][c:23]2[n:24][cH:25][cH:26][n:27]12>>[O:1]=[C:2]1[c:3]2[cH:4][cH:5][cH:6][cH:7][c:8]2[C:9](=[O:10])[N:11]1[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][S:18][c:19... | O=C1c2ccccc2C(=O)N1CCCCCCBr.Sc1cccc2nccn12 | O=C1c2ccccc2C(=O)N1CCCCCCSc1cccc2nccn12 | null | null | C(C)O | Heteroatom Alkylation and Arylation | thioether_nucl_sub | 26df88c6a3f5f203c89584658be4e126cb42994c98a2e16bc812e1036cdae857 | 8b2f52296c3a93039174c980b6042ba15754e04d6892a1284c3a32985220b214 | O=C1c2ccccc2C(=O)N1CCCCCCSc1cccc2nccn12 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[SH;D1;+0:4]-[c:5](:[c:6]):[#7;a:7]1:[c:8]:[#7;a:9]:[c:10]:[c:11]:1>>[C:3]-[C:2]-[CH2;D2;+0:1]-[S;H0;D2;+0:4]-[c:5](:[c:6]):[#7;a:7]1:[c:8]:[#7;a:9]:[c:10]:[c:11]:1 | 75.5 | [{"value": 75.5, "product": "C1(C=2C(C(N1CCCCCCSC1=CC=CC=3N1C=CN3)=O)=CC=CC2)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 75.4, "product": "C1(C=2C(C(N1CCCCCCSC1=CC=CC=3N1C=CN3)=O)=CC=CC2)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 12 | HOUR | To a suspension of 5-mercaptoimidazo[1,2-a]pyridine (1.50g, 10 mmoles) and N-[6-(bromo)hexyl]phthalimide (3.10 g, 10 mmoles) in ethanol (100 ml) was added triethylamine (2.1 ml, 15 mmoles) and the mixture was stirred at room temperature for 12 hours. After the solvent was distilled off, chloroform was added to the resi... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic thiol | Monosulfide | null | null | c1ccc2c(c1)C[NH]C2.c1ccn2ccnc2c1 | HBr | C(C)O | null | 12 | O=C1c2ccccc2C(=O)N1CCCCCCBr.Sc1cccc2nccn12>C(C)O>O=C1c2ccccc2C(=O)N1CCCCCCSc1cccc2nccn12 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-dedb6ba551c5410abf6790b1b72cd0d0 | O=C1c2ccccc2C(=O)N1CCOCCBr.Sc1cccc2nccn12>>O=C1c2ccccc2C(=O)N1CCOCCSc1cccc2nccn12 | SC1=CC=CC=2N1C=CN2.BrCCOCCN1C(C=2C(C1=O)=CC=CC2)=O.C(C)N(CC)CC>>C1(C=2C(C(N1CCOCCSC1=CC=CC=3N1C=CN3)=O)=CC=CC2)=O | Br[CH2:16][CH2:15][O:14][CH2:13][CH2:12][N:11]1[C:2](=[O:1])[c:3]2[cH:4][cH:5][cH:6][cH:7][c:8]2[C:9]1=[O:10].[SH:17][c:18]1[cH:19][cH:20][cH:21][c:22]2[n:23][cH:24][cH:25][n:26]12>>[O:1]=[C:2]1[c:3]2[cH:4][cH:5][cH:6][cH:7][c:8]2[C:9](=[O:10])[N:11]1[CH2:12][CH2:13][O:14][CH2:15][CH2:16][S:17][c:18]1[cH:19][cH:20][cH:... | O=C1c2ccccc2C(=O)N1CCOCCBr.Sc1cccc2nccn12 | O=C1c2ccccc2C(=O)N1CCOCCSc1cccc2nccn12 | null | null | C(C)O | Heteroatom Alkylation and Arylation | thioether_nucl_sub | 26df88c6a3f5f203c89584658be4e126cb42994c98a2e16bc812e1036cdae857 | 8b2f52296c3a93039174c980b6042ba15754e04d6892a1284c3a32985220b214 | O=C1c2ccccc2C(=O)N1CCOCCSc1cccc2nccn12 | Br-[CH2;D2;+0:1]-[C:2]-[#8:3].[SH;D1;+0:4]-[c:5](:[c:6]):[#7;a:7]1:[c:8]:[#7;a:9]:[c:10]:[c:11]:1>>[#8:3]-[C:2]-[CH2;D2;+0:1]-[S;H0;D2;+0:4]-[c:5](:[c:6]):[#7;a:7]1:[c:8]:[#7;a:9]:[c:10]:[c:11]:1 | 54.5 | [{"value": 54.5, "product": "C1(C=2C(C(N1CCOCCSC1=CC=CC=3N1C=CN3)=O)=CC=CC2)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 54.4, "product": "C1(C=2C(C(N1CCOCCSC1=CC=CC=3N1C=CN3)=O)=CC=CC2)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 12 | HOUR | To a suspension of 5-mercaptoimidazo[1,2-a]pyridine (3.00g, 20 mmoles) and N-[2-[2-(bromo)ethyloxy]ethyl]phthalimide (5.96 g, 20 mmoles) in ethanol (200 ml) was added triethylamine (4.2 ml, 30 mmoles) and the mixture was stirred at room temperature for 12 hours and heated at reflux for 3 hours. After the solvent was di... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic thiol | Monosulfide | null | null | c1ccc2c(c1)C[NH]C2.c1ccn2ccnc2c1 | HBr | C(C)O | null | 12 | O=C1c2ccccc2C(=O)N1CCOCCBr.Sc1cccc2nccn12>C(C)O>O=C1c2ccccc2C(=O)N1CCOCCSc1cccc2nccn12 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-d34a489740ed4a9e8f386753fe5c41ad | CC(=O)C1(O)C=CC=CC1C(=O)Cl.NCCSc1cccc2nccn12>>O=C(NCCSc1cccc2nccn12)c1ccccc1O | NCCSC1=CC=CC=2N1C=CN2.C(C)N(CC)CC.C(C)(=O)C1(C(C(=O)Cl)C=CC=C1)O>>OC1=C(C(=O)NCCSC2=CC=CC=3N2C=CN3)C=CC=C1 | CC(=O)[C:21]1([OH:22])[CH:16]([C:2](Cl)=[O:1])[CH:17]=[CH:18][CH:19]=[CH:20]1.[NH2:3][CH2:4][CH2:5][S:6][c:7]1[cH:8][cH:9][cH:10][c:11]2[n:12][cH:13][cH:14][n:15]12>>[O:1]=[C:2]([NH:3][CH2:4][CH2:5][S:6][c:7]1[cH:8][cH:9][cH:10][c:11]2[n:12][cH:13][cH:14][n:15]12)[c:16]1[cH:17][cH:18][cH:19][cH:20][c:21]1[OH:22] | CC(=O)C1(O)C=CC=CC1C(=O)Cl.NCCSc1cccc2nccn12 | O=C(NCCSc1cccc2nccn12)c1ccccc1O | null | null | C(Cl)Cl | Aromatic Heterocycle Formation | OtherReaction | a24c9fe03c2e7a6f24746c08255b47ea21ec4685ca0892b753ffc95760fc7862 | b8d75f0401b2143421a862cc692cf16ba771d890db7de2bbb2d853c3bb02469a | O=C(NCCSc1cccc2nccn12)c1ccccc1 | C-C(=O)-[C;H0;D4;+0:1]1(-[O;D1;H1:2])-[CH;D2;+0:3]=[CH;D2;+0:4]-[CH;D2;+0:5]=[CH;D2;+0:6]-[CH;D3;+0:7]-1-[C;H0;D3;+0:8](-Cl)=[O;D1;H0:9].[C:10]-[C:11]-[NH2;D1;+0:12]>>[C:10]-[C:11]-[NH;D2;+0:12]-[C;H0;D3;+0:8](=[O;D1;H0:9])-[c;H0;D3;+0:7]1:[cH;D2;+0:6]:[cH;D2;+0:5]:[cH;D2;+0:4]:[cH;D2;+0:3]:[c;H0;D3;+0:1]:1-[O;D1;H1:2] | 56 | [{"value": 56.0, "product": "OC1=C(C(=O)NCCSC2=CC=CC=3N2C=CN3)C=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 56.0, "product": "OC1=C(C(=O)NCCSC2=CC=CC=3N2C=CN3)C=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 5-[2-(amino)ethylthio]imidazo[1,2-a]pyridine (3.87 g, 20 mmoles) and triethylamine (5.58 ml, 40 mmoles) in methylene chloride (200 ml) was added o-acetylsalicyloyl chloride (4.77 g, 24 mmoles) under ice-cooling with stirring and the mixture was stirred at room temperature for 30 minutes. After the solv... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Ketone.Tertiary alcohol.Primary amine.Conjugated diene | Secondary amide.Aromatic alcohol | C1=CCCC=C1 | c1ccccc1 | c1ccn2ccnc2c1.c1ccccc1 | HCl | C(Cl)Cl | null | null | CC(=O)C1(O)C=CC=CC1C(=O)Cl.NCCSc1cccc2nccn12>C(Cl)Cl>O=C(NCCSc1cccc2nccn12)c1ccccc1O |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-7a110e2d9d2744ab950d8d0560459122 | O=C(NCCSc1cccc2nccn12)c1ccccc1O.O=C(n1ccnc1)n1ccnc1>>O=c1oc2ccccc2c(=O)n1CCSc1cccc2nccn12 | OC1=C(C(=O)NCCSC2=CC=CC=3N2C=CN3)C=CC=C1.C(=O)(N1C=NC=C1)N1C=NC=C1>>O1C(N(C(C2=C1C=CC=C2)=O)CCSC2=CC=CC=1N2C=CN1)=O | [OH:3][c:4]1[cH:5][cH:6][cH:7][cH:8][c:9]1[C:10](=[O:11])[NH:12][CH2:13][CH2:14][S:15][c:16]1[cH:17][cH:18][cH:19][c:20]2[n:21][cH:22][cH:23][n:24]12.c1cn([C:2](n2ccnc2)=[O:1])cn1>>[O:1]=[c:2]1[o:3][c:4]2[cH:5][cH:6][cH:7][cH:8][c:9]2[c:10](=[O:11])[n:12]1[CH2:13][CH2:14][S:15][c:16]1[cH:17][cH:18][cH:19][c:20]2[n:21][... | O=C(NCCSc1cccc2nccn12)c1ccccc1O.O=C(n1ccnc1)n1ccnc1 | O=c1oc2ccccc2c(=O)n1CCSc1cccc2nccn12 | null | null | O1CCCC1 | Miscellaneous | OtherReaction | 403d1f8be601e40a7e9f89387598dc0beb133de590adaf522ad05b748e927ebe | 35aeac806d92ed233ac4ba302882994a080e88a0a0d6344bfa500ac9440c391d | O=c1oc2ccccc2c(=O)n1CCSc1cccc2nccn12 | [C:1]-[C:2]-[NH;D2;+0:3]-[C;H0;D3;+0:4](=[O;D1;H0:5])-[c:6](:[c:7]):[c:8](-[OH;D1;+0:9]):[c:10].[O;D1;H0:11]=[C;H0;D3;+0:12](-n1:c:c:n:c:1)-n1:c:c:n:c:1>>[C:1]-[C:2]-[n;H0;D3;+0:3]1:[c;H0;D3;+0:4](=[O;D1;H0:5]):[c:6](:[c:7]):[c:8](:[c:10]):[o;H0;D2;+0:9]:[c;H0;D3;+0:12]:1=[O;D1;H0:11] | 77.8 | [{"value": 77.8, "product": "O1C(N(C(C2=C1C=CC=C2)=O)CCSC2=CC=CC=1N2C=CN1)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 77.8, "product": "O1C(N(C(C2=C1C=CC=C2)=O)CCSC2=CC=CC=1N2C=CN1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 15 | HOUR | To a solution of 5-[2-[2-(hydroxy)benzoylamino]ethylthio]imidazo[1,2-a]pyridine (627 mg, 2.00 mmoles) in dry tetrahydrofuran (30 ml) was added 1,1'-carbonyldiimidazole (649 mg, 4.00 mmoles) and the mixture was stirred at room temperature for 15 hours. After the solvent was distilled off, chloroform was added to the res... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide.Aromatic alcohol | null | c1ccccc1.c1c[nH]cn1.c1c[nH]cn1 | c1ncc2ccccc2o1 | c1ncc2ccccc2o1.c1ccn2ccnc2c1 | Other | O1CCCC1 | null | 15 | O=C(NCCSc1cccc2nccn12)c1ccccc1O.O=C(n1ccnc1)n1ccnc1>O1CCCC1>O=c1oc2ccccc2c(=O)n1CCSc1cccc2nccn12 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-9fd5a9c4f7704191a454c34da1b4dc2d | CS(=O)(=O)Cl.NCCCCSc1cccc2nccn12>>CS(=O)(=O)NCCCCSc1cccc2nccn12 | NCCCCSC1=CC=CC=2N1C=CN2.C(C)N(CC)CC.CS(=O)(=O)Cl>>CS(=O)(=O)NCCCCSC1=CC=CC=2N1C=CN2 | Cl[S:2]([CH3:1])(=[O:3])=[O:4].[NH2:5][CH2:6][CH2:7][CH2:8][CH2:9][S:10][c:11]1[cH:12][cH:13][cH:14][c:15]2[n:16][cH:17][cH:18][n:19]12>>[CH3:1][S:2](=[O:3])(=[O:4])[NH:5][CH2:6][CH2:7][CH2:8][CH2:9][S:10][c:11]1[cH:12][cH:13][cH:14][c:15]2[n:16][cH:17][cH:18][n:19]12 | CS(=O)(=O)Cl.NCCCCSc1cccc2nccn12 | CS(=O)(=O)NCCCCSc1cccc2nccn12 | null | null | C(Cl)Cl | Miscellaneous | Sulfonamide synthesis (Schotten-Baumann) primary amine | a86b0632821e188c0a5dc5a5a2aac298ab3eccaee8a52ba46078c3d5975a290d | 50f8fbf3d327483c3eeff8f6cbd4065e4c7600bb501fbe08958a5c79a0926428 | c1ccn2ccnc2c1 | Cl-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4].[C:5]-[C:6]-[NH2;D1;+0:7]>>[C:5]-[C:6]-[NH;D2;+0:7]-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4] | 50.8 | [{"value": 50.8, "product": "CS(=O)(=O)NCCCCSC1=CC=CC=2N1C=CN2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 50.7, "product": "CS(=O)(=O)NCCCCSC1=CC=CC=2N1C=CN2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 5-[4-(amino)butylthio]imidazo[1,2-a]pyridine (440 mg, 1.99 mmoles) and triethylamine (0.42 ml, 3.01 mmoles) in methylene chloride (20 ml) was added methanesulfonyl chloride (0.19 ml, 2.45 mmoles) under ice-cooling with stirring and the mixture was stirred under ice-cooling for 1 hour. The reaction mixt... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Sulfonyl halide | Sulfonamide | null | null | c1ccn2ccnc2c1 | HCl | C(Cl)Cl | null | null | CS(=O)(=O)Cl.NCCCCSc1cccc2nccn12>C(Cl)Cl>CS(=O)(=O)NCCCCSc1cccc2nccn12 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-60c2ecf6995d45a5aa4ac142f572040a | NCCCCSc1cccc2nccn12.O=S(=O)(Cl)c1cccc2ccccc12>>O=S(=O)(NCCCCSc1cccc2nccn12)c1cccc2ccccc12 | NCCCCSC1=CC=CC=2N1C=CN2.C(C)N(CC)CC.C1(=CC=CC2=CC=CC=C12)S(=O)(=O)Cl>>C1(=CC=CC2=CC=CC=C12)S(=O)(=O)NCCCCSC1=CC=CC=2N1C=CN2 | [NH2:4][CH2:5][CH2:6][CH2:7][CH2:8][S:9][c:10]1[cH:11][cH:12][cH:13][c:14]2[n:15][cH:16][cH:17][n:18]12.Cl[S:2](=[O:1])(=[O:3])[c:19]1[cH:20][cH:21][cH:22][c:23]2[cH:24][cH:25][cH:26][cH:27][c:28]12>>[O:1]=[S:2](=[O:3])([NH:4][CH2:5][CH2:6][CH2:7][CH2:8][S:9][c:10]1[cH:11][cH:12][cH:13][c:14]2[n:15][cH:16][cH:17][n:18]... | NCCCCSc1cccc2nccn12.O=S(=O)(Cl)c1cccc2ccccc12 | O=S(=O)(NCCCCSc1cccc2nccn12)c1cccc2ccccc12 | null | null | C(Cl)Cl | Miscellaneous | Sulfonamide synthesis (Schotten-Baumann) primary amine | a86b0632821e188c0a5dc5a5a2aac298ab3eccaee8a52ba46078c3d5975a290d | 50f8fbf3d327483c3eeff8f6cbd4065e4c7600bb501fbe08958a5c79a0926428 | O=S(=O)(NCCCCSc1cccc2nccn12)c1cccc2ccccc12 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6].[C:7]-[C:8]-[NH2;D1;+0:9]>>[C:7]-[C:8]-[NH;D2;+0:9]-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6] | 53.3 | [{"value": 53.0, "product": "C1(=CC=CC2=CC=CC=C12)S(=O)(=O)NCCCCSC1=CC=CC=2N1C=CN2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 53.3, "product": "C1(=CC=CC2=CC=CC=C12)S(=O)(=O)NCCCCSC1=CC=CC=2N1C=CN2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 5-[4-(amino)butylthio]imidazo[1,2-a]pyridine (300 mg, 1.36 mmoles) and triethylamine (0.29 ml, 2.08 mmoles) in methylene chloride (15 ml) was added 1-naphthalenesulfonyl chloride (307 mg, 1.35 mmoles) under ice-cooling with stirring and the mixture was stirred at room temperature for 1 hour. The reacti... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Sulfonyl halide | Sulfonamide | null | null | c1ccn2ccnc2c1.c1ccc2ccccc2c1 | HCl | C(Cl)Cl | null | null | NCCCCSc1cccc2nccn12.O=S(=O)(Cl)c1cccc2ccccc12>C(Cl)Cl>O=S(=O)(NCCCCSc1cccc2nccn12)c1cccc2ccccc12 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-ce3b6cc6c0d44d898ee55cbe4e28ea20 | CC(C)OC(=O)Cl.NCCCCSc1cccc2nccn12>>CC(C)OC(=O)NCCCCSc1cccc2nccn12 | NCCCCSC1=CC=CC=2N1C=CN2.C(C)N(CC)CC.ClC(=O)OC(C)C>>C(C)(C)OC(=O)NCCCCSC1=CC=CC=2N1C=CN2 | Cl[C:5]([O:4][CH:2]([CH3:1])[CH3:3])=[O:6].[NH2:7][CH2:8][CH2:9][CH2:10][CH2:11][S:12][c:13]1[cH:14][cH:15][cH:16][c:17]2[n:18][cH:19][cH:20][n:21]12>>[CH3:1][CH:2]([CH3:3])[O:4][C:5](=[O:6])[NH:7][CH2:8][CH2:9][CH2:10][CH2:11][S:12][c:13]1[cH:14][cH:15][cH:16][c:17]2[n:18][cH:19][cH:20][n:21]12 | CC(C)OC(=O)Cl.NCCCCSc1cccc2nccn12 | CC(C)OC(=O)NCCCCSc1cccc2nccn12 | null | null | C(Cl)Cl | Protection | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 038720aa61a7efa0f2a9ee6f2e0adf63a9ffdc2be4697c11a6215baef34f97b2 | 205f353513ce9506ab61831799da8fb73ec2ef5cfa927664496d3ce72c438860 | c1ccn2ccnc2c1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C:4].[C:5]-[C:6]-[NH2;D1;+0:7]>>[C:4]-[#8:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:7]-[C:6]-[C:5] | 41.9 | [{"value": 41.8, "product": "C(C)(C)OC(=O)NCCCCSC1=CC=CC=2N1C=CN2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 41.9, "product": "C(C)(C)OC(=O)NCCCCSC1=CC=CC=2N1C=CN2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 5-[4-(amino)butylthio]imidazo[1,2-a]pyridine (370 mg, 1.67 mmoles) and triethylamine (0.35 ml, 2.51 mmoles) in metylene chloride (20 ml) was added isopropyl chloroformate (0.25 g, 2.04 mmoles) under ice-cooling with stirring and the mixture was stirred under ice-cooling for 1 hour. The reaction mixture... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Ether.Primary amine | Carbamic ester | null | null | c1ccn2ccnc2c1 | HCl | C(Cl)Cl | null | null | CC(C)OC(=O)Cl.NCCCCSc1cccc2nccn12>C(Cl)Cl>CC(C)OC(=O)NCCCCSc1cccc2nccn12 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-87ae7e60b3f94aeab00f82581b06295a | NCCCOc1cccc2nccn12.O=S(=O)(Cl)c1ccccc1>>O=S(=O)(NCCCOc1cccc2nccn12)c1ccccc1 | C1(=CC=CC=C1)S(=O)(=O)Cl.Cl.Cl.NCCCOC1=CC=CC=2N1C=CN2.C(C)N(CC)CC.C(C)#N>>C1(=CC=CC=C1)S(=O)(=O)NCCCOC1=CC=CC=2N1C=CN2 | [NH2:4][CH2:5][CH2:6][CH2:7][O:8][c:9]1[cH:10][cH:11][cH:12][c:13]2[n:14][cH:15][cH:16][n:17]12.Cl[S:2](=[O:1])(=[O:3])[c:18]1[cH:19][cH:20][cH:21][cH:22][cH:23]1>>[O:1]=[S:2](=[O:3])([NH:4][CH2:5][CH2:6][CH2:7][O:8][c:9]1[cH:10][cH:11][cH:12][c:13]2[n:14][cH:15][cH:16][n:17]12)[c:18]1[cH:19][cH:20][cH:21][cH:22][cH:23... | NCCCOc1cccc2nccn12.O=S(=O)(Cl)c1ccccc1 | O=S(=O)(NCCCOc1cccc2nccn12)c1ccccc1 | null | null | C(Cl)Cl | Acylation | Sulfonamide synthesis (Schotten-Baumann) primary amine | 4c44ef6d7646f6ef25dd125d2c32c713d8dcae7c603407faa5f0fb810631670e | 8fce8115d8a725afa92eb3910ded29d4c852e5133eba78a425054f41f7142603 | O=S(=O)(NCCCOc1cccc2nccn12)c1ccccc1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6].[C:7]-[C:8]-[NH2;D1;+0:9]>>[C:7]-[C:8]-[NH;D2;+0:9]-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6] | 59.5 | [{"value": 59.5, "product": "C1(=CC=CC=C1)S(=O)(=O)NCCCOC1=CC=CC=2N1C=CN2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 59.4, "product": "C1(=CC=CC=C1)S(=O)(=O)NCCCOC1=CC=CC=2N1C=CN2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a suspension of 5-[3-(amino)propyloxy]imidazo[1,2-a]pyridine dihydrochloride (2.64 g, 10 mmoles) and triethylamine (4.88 ml, 35 mmoles) in methylene chloride (100 ml)-acetonitrile (30 ml) was added benzenesulfonyl chloride (1.53 ml, 12 mmoles) under ice-cooling with stirring and the mixture was stirred at room tempe... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Sulfonyl halide | Sulfonamide | null | null | c1ccn2ccnc2c1.c1ccccc1 | HCl | C(Cl)Cl | null | null | NCCCOc1cccc2nccn12.O=S(=O)(Cl)c1ccccc1>C(Cl)Cl>O=S(=O)(NCCCOc1cccc2nccn12)c1ccccc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-d9e2fcc0263e44d98d5c9394e962dbc0 | CC(=O)OC(C)=O.OCCCSc1cccc2nccn12>>CC(=O)OCCCSc1cccc2nccn12 | OCCCSC1=CC=CC=2N1C=CN2.C(C)N(CC)CC.C(C)(=O)OC(C)=O>>C(C)(=O)OCCCSC1=CC=CC=2N1C=CN2 | CC(=O)O[C:2]([CH3:1])=[O:3].[OH:4][CH2:5][CH2:6][CH2:7][S:8][c:9]1[cH:10][cH:11][cH:12][c:13]2[n:14][cH:15][cH:16][n:17]12>>[CH3:1][C:2](=[O:3])[O:4][CH2:5][CH2:6][CH2:7][S:8][c:9]1[cH:10][cH:11][cH:12][c:13]2[n:14][cH:15][cH:16][n:17]12 | CC(=O)OC(C)=O.OCCCSc1cccc2nccn12 | CC(=O)OCCCSc1cccc2nccn12 | null | null | C(Cl)Cl | Acylation | Transesterification | f81e513b7b512b10157c16426844efd8d88e34c97987c1347c6ba8a688351205 | fc27d67c790d5fb520ba5d49de1490661fa5b822b714863734ce7e3029dfa84f | c1ccn2ccnc2c1 | C-C(=O)-O-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[C:4]-[C:5]-[OH;D1;+0:6]>>[C:4]-[C:5]-[O;H0;D2;+0:6]-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3] | 100 | [{"value": 100.0, "product": "C(C)(=O)OCCCSC1=CC=CC=2N1C=CN2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 99.9, "product": "C(C)(=O)OCCCSC1=CC=CC=2N1C=CN2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 5-[3-(hydroxy)propylthio]imidazo[1,2-a]pyridine (2.00 g, 9.60 mmoles) and triethylamine (1.60 ml, 11.5 mmoles) in methylene chloride (50 ml) was added acetic anhydride (1.10 ml, 11.6 mmoles) with stirring at room temperature and the mixture was further stirred at room temperature for 7.5 hours. The rea... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Primary alcohol | Ester | null | null | c1ccn2ccnc2c1 | HO- | C(Cl)Cl | null | null | CC(=O)OC(C)=O.OCCCSc1cccc2nccn12>C(Cl)Cl>CC(=O)OCCCSc1cccc2nccn12 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-e431e84515d848548ea5e98c8fead1b1 | O=C(Cl)c1ccccc1.OCCCSc1cccc2nccn12>>O=C(OCCCSc1cccc2nccn12)c1ccccc1 | OCCCSC1=CC=CC=2N1C=CN2.C(C)N(CC)CC.C(C1=CC=CC=C1)(=O)Cl>>C(C1=CC=CC=C1)(=O)OCCCSC1=CC=CC=2N1C=CN2 | Cl[C:2](=[O:1])[c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1.[OH:3][CH2:4][CH2:5][CH2:6][S:7][c:8]1[cH:9][cH:10][cH:11][c:12]2[n:13][cH:14][cH:15][n:16]12>>[O:1]=[C:2]([O:3][CH2:4][CH2:5][CH2:6][S:7][c:8]1[cH:9][cH:10][cH:11][c:12]2[n:13][cH:14][cH:15][n:16]12)[c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1 | O=C(Cl)c1ccccc1.OCCCSc1cccc2nccn12 | O=C(OCCCSc1cccc2nccn12)c1ccccc1 | null | null | C(Cl)Cl | Acylation | Schotten-Baumann to ester | 6cefe709828c5bd4655f254e75d5dff9e8876e192e7dd47256c1bc0067bc5291 | d8a7643b81ed07a6f633aa99465180dfa0565e61ae25aef36338ebb9837c9cef | O=C(OCCCSc1cccc2nccn12)c1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[C:6]-[C:7]-[OH;D1;+0:8]>>[C:6]-[C:7]-[O;H0;D2;+0:8]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5] | 88.1 | [{"value": 88.1, "product": "C(C1=CC=CC=C1)(=O)OCCCSC1=CC=CC=2N1C=CN2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 88.0, "product": "C(C1=CC=CC=C1)(=O)OCCCSC1=CC=CC=2N1C=CN2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 5-[3-(hydroxy)propylthio]imidazo[1,2-a]pyridine (1.00 g, 4.80 mmoles) and triethylamine (0.80 ml, 5.74 mmoles) in methylene chloride (25 ml) was added benzoyl chloride (1.10 ml, 11.6 mmoles) with stirring at room temperature and the mixture was further stirred at room temperature for 30 minutes. The re... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary alcohol | Ester | null | null | c1ccn2ccnc2c1.c1ccccc1 | HCl | C(Cl)Cl | null | null | O=C(Cl)c1ccccc1.OCCCSc1cccc2nccn12>C(Cl)Cl>O=C(OCCCSc1cccc2nccn12)c1ccccc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-2079fc0d693f44d2b7680a1a439cd964 | O=C(Cl)CCc1ccccc1.OCCCSc1cccc2nccn12>>O=C(CCc1ccccc1)OCCCSc1cccc2nccn12 | OCCCSC1=CC=CC=2N1C=CN2.C(C)N(CC)CC.C1(=CC=CC=C1)CCC(=O)Cl>>C1(=CC=CC=C1)CCC(=O)OCCCSC1=CC=CC=2N1C=CN2 | Cl[C:2](=[O:1])[CH2:3][CH2:4][c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1.[OH:11][CH2:12][CH2:13][CH2:14][S:15][c:16]1[cH:17][cH:18][cH:19][c:20]2[n:21][cH:22][cH:23][n:24]12>>[O:1]=[C:2]([CH2:3][CH2:4][c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1)[O:11][CH2:12][CH2:13][CH2:14][S:15][c:16]1[cH:17][cH:18][cH:19][c:20]2[n:21][cH:22][... | O=C(Cl)CCc1ccccc1.OCCCSc1cccc2nccn12 | O=C(CCc1ccccc1)OCCCSc1cccc2nccn12 | null | null | C(Cl)Cl | Acylation | Schotten-Baumann to ester | 6cefe709828c5bd4655f254e75d5dff9e8876e192e7dd47256c1bc0067bc5291 | d8a7643b81ed07a6f633aa99465180dfa0565e61ae25aef36338ebb9837c9cef | O=C(CCc1ccccc1)OCCCSc1cccc2nccn12 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[C:5]-[C:6]-[OH;D1;+0:7]>>[C:5]-[C:6]-[O;H0;D2;+0:7]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4] | 84.2 | [{"value": 84.2, "product": "C1(=CC=CC=C1)CCC(=O)OCCCSC1=CC=CC=2N1C=CN2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 83.8, "product": "C1(=CC=CC=C1)CCC(=O)OCCCSC1=CC=CC=2N1C=CN2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 5-[3-(hydroxy)propylthio]imidazo[1,2-a]pyridine (1.00 g, 4.80 mmoles) and triethylamine (0.80 ml, 5.74 mmoles) in methylene chloride (25 ml) was added 3-phenylpropionyl chloride (1.01 g, 5.99 mmoles) with stirring at room temperature and the mixture was further stirred at room temperature for 2 hours. ... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary alcohol | Ester | null | null | c1ccccc1.c1ccn2ccnc2c1 | HCl | C(Cl)Cl | null | null | O=C(Cl)CCc1ccccc1.OCCCSc1cccc2nccn12>C(Cl)Cl>O=C(CCc1ccccc1)OCCCSc1cccc2nccn12 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-c8302a01d03b4734bd887b2f15cf39ff | CS(=O)(=O)Cl.OCCCSc1cccc2nccn12>>CS(=O)(=O)OCCCSc1cccc2nccn12 | OCCCSC1=CC=CC=2N1C=CN2.C(C)N(CC)CC.CS(=O)(=O)Cl>>CS(=O)(=O)OCCCSC1=CC=CC=2N1C=CN2 | Cl[S:2]([CH3:1])(=[O:3])=[O:4].[OH:5][CH2:6][CH2:7][CH2:8][S:9][c:10]1[cH:11][cH:12][cH:13][c:14]2[n:15][cH:16][cH:17][n:18]12>>[CH3:1][S:2](=[O:3])(=[O:4])[O:5][CH2:6][CH2:7][CH2:8][S:9][c:10]1[cH:11][cH:12][cH:13][c:14]2[n:15][cH:16][cH:17][n:18]12 | CS(=O)(=O)Cl.OCCCSc1cccc2nccn12 | CS(=O)(=O)OCCCSc1cccc2nccn12 | null | null | C(Cl)Cl | Acylation | Formation of Sulfonic Esters | 2fa969eb2c954bb96793348a1b2335ec63fbd290dadec6e3e02295e1768e64cf | cb77b899e4adf980b1def97230ef2861660fd7f9602260ec64747d9afd3a795a | c1ccn2ccnc2c1 | Cl-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4].[C:5]-[C:6]-[OH;D1;+0:7]>>[C:5]-[C:6]-[O;H0;D2;+0:7]-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4] | null | [] | null | null | null | null | To a solution of 5-[3-(hydroxy)propylthio]imidazo[1,2-a]pyridine (1.030 g, 4.95 mmoles) and triethylamine (1.03 ml, 7.4 mmoles) in methylene chloride (30 ml) was added methanesulfonyl chloride (0.46 ml, 5.9 mmoles) with stirring under ice-cooling and the mixture was further stirred under ice-cooling for 10 minutes. The... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Sulfonyl halide | Mesylate | null | null | c1ccn2ccnc2c1 | HCl | C(Cl)Cl | null | null | CS(=O)(=O)Cl.OCCCSc1cccc2nccn12>C(Cl)Cl>CS(=O)(=O)OCCCSc1cccc2nccn12 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-eb8851427b2141259138fbc58018c19f | CS(=O)(=O)Cl.OCCOc1ccccc1>>CS(=O)(=O)OCCOc1ccccc1 | O(C1=CC=CC=C1)CCO.C(C)N(CC)CC.CS(=O)(=O)Cl>>CS(=O)(=O)OCCOC1=CC=CC=C1 | Cl[S:2]([CH3:1])(=[O:3])=[O:4].[OH:5][CH2:6][CH2:7][O:8][c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1>>[CH3:1][S:2](=[O:3])(=[O:4])[O:5][CH2:6][CH2:7][O:8][c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1 | CS(=O)(=O)Cl.OCCOc1ccccc1 | CS(=O)(=O)OCCOc1ccccc1 | null | null | C(Cl)Cl | Acylation | Formation of Sulfonic Esters | 2fa969eb2c954bb96793348a1b2335ec63fbd290dadec6e3e02295e1768e64cf | cb77b899e4adf980b1def97230ef2861660fd7f9602260ec64747d9afd3a795a | c1ccccc1 | Cl-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4].[C:5]-[C:6]-[OH;D1;+0:7]>>[C:5]-[C:6]-[O;H0;D2;+0:7]-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4] | null | [] | null | null | null | null | To a solution of 2-(phenoxy)ethanol (1.35 g, 9.78 mmoles) and triethylamine (2.04 ml, 14.7 mmoles) in methylene chloride (30 ml) was added methanesulfonyl chloride (0.91 ml, 12 mmoles) with stirring under ice-cooling and the mixture was further stirred under ice-cooling for 10 minutes. The reaction solution was washed ... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Sulfonyl halide | Mesylate | null | null | c1ccccc1 | HCl | C(Cl)Cl | null | null | CS(=O)(=O)Cl.OCCOc1ccccc1>C(Cl)Cl>CS(=O)(=O)OCCOc1ccccc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-f9658666c16f4e2d9c1027809e78ff12 | C1CCOC1.CC1=CC=C[IH]1.OCCCSc1cccc2nccn12>>c1ccc(CCCOCCCSc2cccc3nccn23)cc1 | CC=1[IH]C=CC1.OCCCSC1=CC=CC=2N1C=CN2.[H-].[Na+].O1CCCC1.O>>C1(=CC=CC=C1)CCCOCCCSC1=CC=CC=2N1C=CN2 | O1[CH2:5][CH2:4][CH2:6][CH2:7]1.[IH]1[C:2]([CH3:3])=[CH:1][CH:23]=[CH:22]1.[OH:8][CH2:9][CH2:10][CH2:11][S:12][c:13]1[cH:14][cH:15][cH:16][c:17]2[n:18][cH:19][cH:20][n:21]12>>[cH:1]1[cH:2][cH:3][c:4]([CH2:5][CH2:6][CH2:7][O:8][CH2:9][CH2:10][CH2:11][S:12][c:13]2[cH:14][cH:15][cH:16][c:17]3[n:18][cH:19][cH:20][n:21]23)[... | C1CCOC1.CC1=CC=C[IH]1.OCCCSc1cccc2nccn12 | c1ccc(CCCOCCCSc2cccc3nccn23)cc1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | efabf9fb4611c28dae69b3ba2410626a1ac2e9f3cbd3420d3142fc8e79195f3f | 921774a5b4a3445aa76c579135992d1dc8bf713704f7571760f1ca465f8d60bd | c1ccc(CCCOCCCSc2cccc3nccn23)cc1 | O1-[CH2;D2;+0:1]-[CH2;D2;+0:2]-[CH2;D2;+0:3]-[CH2;D2;+0:4]-1.[CH3;D1;+0:5]-[C;H0;D3;+0:6]1=[CH;D2;+0:7]-[CH;D2;+0:8]=[CH;D2;+0:9]-[IH]-1.[C:10]-[C:11]-[OH;D1;+0:12]>>[C:10]-[C:11]-[O;H0;D2;+0:12]-[CH2;D2;+0:4]-[CH2;D2;+0:3]-[CH2;D2;+0:1]-[c;H0;D3;+0:2]1:[cH;D2;+0:9]:[cH;D2;+0:8]:[cH;D2;+0:7]:[cH;D2;+0:6]:[cH;D2;+0:5]:1 | 58.9 | [{"value": 58.9, "product": "C1(=CC=CC=C1)CCCOCCCSC1=CC=CC=2N1C=CN2", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 5-[3-(hydroxy)propylthio]imidazo[1,2-a]pyridine (1.070 g, 5.137 mmoles) in tetrahydrofuran (30 ml) was added 60% sodium hydride in oil (0.25 g, 6.2 mmoles) with stirring under ice-cooling and the mixture was stirred under ice-cooling for 30 minutes. To the reaction mixture was added methyl iodie (1.53 ... | 10.6084/m9.figshare.5104873.v1 | null | Alkenyl halide.Ether.Primary alcohol.Conjugated diene | Ether | C1CCOC1.C1=C[IH]C=C1 | c1ccccc1 | c1ccccc1.c1ccn2ccnc2c1 | HI | null | null | null | C1CCOC1.CC1=CC=C[IH]1.OCCCSc1cccc2nccn12>>c1ccc(CCCOCCCSc2cccc3nccn23)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-4e2651d7658c4004854f8e9660ba034f | CS(=O)(=O)Cl.OCCCSc1cccc2nccn12>>CS(=O)(=O)OCCCSc1cccc2nccn12 | OCCCSC1=CC=CC=2N1C=CN2.C(C)N(CC)CC.CS(=O)(=O)Cl>>CS(=O)(=O)OCCCSC1=CC=CC=2N1C=CN2 | Cl[S:2]([CH3:1])(=[O:3])=[O:4].[OH:5][CH2:6][CH2:7][CH2:8][S:9][c:10]1[cH:11][cH:12][cH:13][c:14]2[n:15][cH:16][cH:17][n:18]12>>[CH3:1][S:2](=[O:3])(=[O:4])[O:5][CH2:6][CH2:7][CH2:8][S:9][c:10]1[cH:11][cH:12][cH:13][c:14]2[n:15][cH:16][cH:17][n:18]12 | CS(=O)(=O)Cl.OCCCSc1cccc2nccn12 | CS(=O)(=O)OCCCSc1cccc2nccn12 | null | null | C(Cl)Cl | Acylation | Formation of Sulfonic Esters | 2fa969eb2c954bb96793348a1b2335ec63fbd290dadec6e3e02295e1768e64cf | cb77b899e4adf980b1def97230ef2861660fd7f9602260ec64747d9afd3a795a | c1ccn2ccnc2c1 | Cl-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4].[C:5]-[C:6]-[OH;D1;+0:7]>>[C:5]-[C:6]-[O;H0;D2;+0:7]-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4] | null | [] | null | null | null | null | To a solution of 5-[3-(hydroxy)propylthio]imidazo[1,2-a]pyridine (2.003 g, 9.62 mmoles) and triethylamine (2.01 ml, 14.4 mmoles) in methylene chloride (30 ml) was added methanesulfonyl chloride (0.89 ml, 12 mmoles) with stirring under ice-cooling and the mixture was further stirred under ice-cooling for 10 minutes. The... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Sulfonyl halide | Mesylate | null | null | c1ccn2ccnc2c1 | HCl | C(Cl)Cl | null | null | CS(=O)(=O)Cl.OCCCSc1cccc2nccn12>C(Cl)Cl>CS(=O)(=O)OCCCSc1cccc2nccn12 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-7097224312844781b8a90c03bd6c28cf | CS(=O)(=O)Cl.c1ccc(NCCOCCCSc2cccc3nccn23)cc1>>CS(=O)(=O)N(CCOCCCSc1cccc2nccn12)c1ccccc1 | C1(=CC=CC=C1)NCCOCCCSC1=CC=CC=2N1C=CN2.C(C)N(CC)CC.CS(=O)(=O)Cl>>CS(=O)(=O)N(C1=CC=CC=C1)CCOCCCSC1=CC=CC=2N1C=CN2 | Cl[S:2]([CH3:1])(=[O:3])=[O:4].[NH:5]([CH2:6][CH2:7][O:8][CH2:9][CH2:10][CH2:11][S:12][c:13]1[cH:14][cH:15][cH:16][c:17]2[n:18][cH:19][cH:20][n:21]12)[c:22]1[cH:23][cH:24][cH:25][cH:26][cH:27]1>>[CH3:1][S:2](=[O:3])(=[O:4])[N:5]([CH2:6][CH2:7][O:8][CH2:9][CH2:10][CH2:11][S:12][c:13]1[cH:14][cH:15][cH:16][c:17]2[n:18][c... | CS(=O)(=O)Cl.c1ccc(NCCOCCCSc2cccc3nccn23)cc1 | CS(=O)(=O)N(CCOCCCSc1cccc2nccn12)c1ccccc1 | null | null | C(Cl)Cl | Acylation | Sulfonamide synthesis (Schotten-Baumann) secondary amine | abeb6d9a0c70fe5baef0a8e555c2cd55ac2317f763ce7a0831775db7a04777d8 | b7aca5a5d690b0846685a854bc946849e1041bfc3965161290b5ffb2821af09e | c1ccc(NCCOCCCSc2cccc3nccn23)cc1 | Cl-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4].[C:5]-[C:6]-[NH;D2;+0:7]-[c:8](:[c:9]):[c:10]>>[C:5]-[C:6]-[N;H0;D3;+0:7](-[c:8](:[c:9]):[c:10])-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4] | 1.2 | [{"value": 1.2, "product": "CS(=O)(=O)N(C1=CC=CC=C1)CCOCCCSC1=CC=CC=2N1C=CN2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 5-[3-[2-(phenylamino)ethyloxy]propylthio]imidazo[1,2-a]pyridine (1.034 g, 3.158 mmoles) and triethylamine (0.88 ml, 6.3 mmoles) in methylene chloride (30 ml) was added methanesulfonyl chloride (0.37 ml, 4.7 mmoles) with stirring under ice-cooling and the mixture was further stirred under ice-cooling fo... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amine.Sulfonyl halide | Tertiary amine | null | null | c1ccn2ccnc2c1.c1ccccc1 | HCl | C(Cl)Cl | null | null | CS(=O)(=O)Cl.c1ccc(NCCOCCCSc2cccc3nccn23)cc1>C(Cl)Cl>CS(=O)(=O)N(CCOCCCSc1cccc2nccn12)c1ccccc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-6cd90233a0574e0694fb51b47e183c97 | Clc1cccc2nccn12.O=C(c1cccs1)N1CCC(O)CC1>>O=C(c1cccs1)N1CCC(Oc2cccc3nccn23)CC1 | ClC1=CC=CC=2N1C=CN2.[H-].[Na+].O.S1C(=CC=C1)C(=O)N1CCC(CC1)O>>S1C(=CC=C1)C(=O)N1CCC(CC1)OC1=CC=CC=2N1C=CN2 | Cl[c:13]1[cH:14][cH:15][cH:16][c:17]2[n:18][cH:19][cH:20][n:21]12.[O:1]=[C:2]([c:3]1[cH:4][cH:5][cH:6][s:7]1)[N:8]1[CH2:9][CH2:10][CH:11]([OH:12])[CH2:22][CH2:23]1>>[O:1]=[C:2]([c:3]1[cH:4][cH:5][cH:6][s:7]1)[N:8]1[CH2:9][CH2:10][CH:11]([O:12][c:13]2[cH:14][cH:15][cH:16][c:17]3[n:18][cH:19][cH:20][n:21]23)[CH2:22][CH2:... | Clc1cccc2nccn12.O=C(c1cccs1)N1CCC(O)CC1 | O=C(c1cccs1)N1CCC(Oc2cccc3nccn23)CC1 | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | a3c24666dcc7591244ef0bfc8eff58c01a9bc3e8d1b581d90f8e8203e5b9ba3a | 1f70dbbaebc288b3a5d3f37803812d9d22b151831cd4b8351080508554b19875 | O=C(c1cccs1)N1CCC(Oc2cccc3nccn23)CC1 | Cl-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[c:5]2:[#7;a:6]:[c:7]:[c:8]:[#7;a:9]:2:1.[C:10]-[C:11](-[OH;D1;+0:12])-[C:13]>>[C:10]-[C:11](-[O;H0;D2;+0:12]-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[c:5]2:[#7;a:6]:[c:7]:[c:8]:[#7;a:9]:2:1)-[C:13] | 4.6 | [{"value": 4.6, "product": "S1C(=CC=C1)C(=O)N1CCC(CC1)OC1=CC=CC=2N1C=CN2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 4.6, "product": "S1C(=CC=C1)C(=O)N1CCC(CC1)OC1=CC=CC=2N1C=CN2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a suspension of 60% sodium hydride in oil (0.40 g, 10 mmoles) in dimethylformamide (30 ml) was added 1-(2-thienylcarbonyl)-4-hydroxypiperidine (2.11 g, 10 mmoles) with stirring under ice-cooling and the mixture was stirred at room temperature for 30 minutes. To this reaction mixture was added 5-chloroimidazo[1,2-a]p... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary alcohol | Ether | c1ccn2ccnc2c1 | c1ccn2ccnc2c1 | c1ccsc1.C1CC[NH]CC1.c1ccn2ccnc2c1 | HCl | CN(C=O)C | null | null | Clc1cccc2nccn12.O=C(c1cccs1)N1CCC(O)CC1>CN(C=O)C>O=C(c1cccs1)N1CCC(Oc2cccc3nccn23)CC1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-e3132aba721d4308b7846406e0b07587 | Clc1cccc2nccn12.O=S(=O)(CCc1ccccc1)NCCO>>O=S(=O)(CCc1ccccc1)NCCOc1cccc2nccn12 | ClC1=CC=CC=2N1C=CN2.[H-].[Na+].O.C(C1=CC=CC=C1)CS(=O)(=O)NCCO>>C(C1=CC=CC=C1)CS(=O)(=O)NCCOC1=CC=CC=2N1C=CN2 | Cl[c:16]1[cH:17][cH:18][cH:19][c:20]2[n:21][cH:22][cH:23][n:24]12.[O:1]=[S:2](=[O:3])([CH2:4][CH2:5][c:6]1[cH:7][cH:8][cH:9][cH:10][cH:11]1)[NH:12][CH2:13][CH2:14][OH:15]>>[O:1]=[S:2](=[O:3])([CH2:4][CH2:5][c:6]1[cH:7][cH:8][cH:9][cH:10][cH:11]1)[NH:12][CH2:13][CH2:14][O:15][c:16]1[cH:17][cH:18][cH:19][c:20]2[n:21][cH:... | Clc1cccc2nccn12.O=S(=O)(CCc1ccccc1)NCCO | O=S(=O)(CCc1ccccc1)NCCOc1cccc2nccn12 | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 86a14d8c65c7d47a74ee6f255350fe1cca98e47302e41723756ed1ac172a15be | a4cafa7bcd156e21cca6eaac1b32e28ec8540642a31181122e6957f3d7559631 | O=S(=O)(CCc1ccccc1)NCCOc1cccc2nccn12 | Cl-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[c:5]2:[#7;a:6]:[c:7]:[c:8]:[#7;a:9]:2:1.[C:10]-[C:11]-[OH;D1;+0:12]>>[C:10]-[C:11]-[O;H0;D2;+0:12]-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[c:5]2:[#7;a:6]:[c:7]:[c:8]:[#7;a:9]:2:1 | 39.4 | [{"value": 39.4, "product": "C(C1=CC=CC=C1)CS(=O)(=O)NCCOC1=CC=CC=2N1C=CN2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 39.4, "product": "C(C1=CC=CC=C1)CS(=O)(=O)NCCOC1=CC=CC=2N1C=CN2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a suspension of 60% sodium hydride in oil (0.20 g, 5 mmoles) in dimethylformamide (20 ml) was added 2-(N-benzylmethylsulfonylamino)-1-ethanol (1.14 g, 5 mmoles) with stirring under ice-cooling and the mixture was stirred at room temperature for 30 minutes. To this reaction mixture was added 5-chloroimidazo[1,2-a]pyr... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary alcohol | Ether | c1ccn2ccnc2c1 | c1ccn2ccnc2c1 | c1ccccc1.c1ccn2ccnc2c1 | HCl | CN(C=O)C | null | null | Clc1cccc2nccn12.O=S(=O)(CCc1ccccc1)NCCO>CN(C=O)C>O=S(=O)(CCc1ccccc1)NCCOc1cccc2nccn12 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-e88abdf757ee41b9b51549e401c0a380 | CCN(CC)CC.CS(=O)(=O)Cl.NCCCO>>CS(=O)(=O)NCCCOS(C)(=O)=O | NCCCO.C(C)N(CC)CC.CS(=O)(=O)Cl>>CS(=O)(=O)NCCCOS(=O)(=O)C | CCN(CC)C[CH3:11].Cl[S:2]([CH3:1])(=[O:3])=[O:13].[NH2:5][CH2:6][CH2:7][CH2:8][OH:9]>>[CH3:1][S:2](=[O:3])(=[O:4])[NH:5][CH2:6][CH2:7][CH2:8][O:9][S:10]([CH3:11])(=[O:12])=[O:13] | CCN(CC)CC.CS(=O)(=O)Cl.NCCCO | CS(=O)(=O)NCCCOS(C)(=O)=O | null | null | ClCCl | Oxidation | OtherReaction | f3b1ea102a404607e2b5b04447756cfa28aa1337552a146e81b821d83128d609 | a69efdf29aa0b3ff35df5537c38d5dafce973a6e175c0767a3a7924e11d13451 | null | C-C-N(-C-C)-C-[CH3;D1;+0:1].Cl-[S;H0;D4;+0:2](-[C;D1;H3:3])(=[O;D1;H0:4])=[O;H0;D1;+0:5].[NH2;D1;+0:6]-[C:7]-[C:8]-[C:9]-[OH;D1;+0:10]>>[C;D1;H3:3]-[S;H0;D4;+0:2](=[O;D1;H0:4])(=[O;D1;H0:11])-[NH;D2;+0:6]-[C:7]-[C:8]-[C:9]-[O;H0;D2;+0:10]-[#16:12](-[CH3;D1;+0:1])(=[O;D1;H0:13])=[O;H0;D1;+0:5] | 69.8 | [{"value": 69.8, "product": "CS(=O)(=O)NCCCOS(=O)(=O)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 69.8, "product": "CS(=O)(=O)NCCCOS(=O)(=O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 3-amino-1-propanol (11.47 ml, 150 mmoles) and triethylamine (46 ml, 330 mmoles) in dichloromethane (250 ml) was added methylsulfonyl chloride (25.5 ml, 330 mmoles) with stirring under ice-cooling and the mixture was stirred at room temperature for 30 minutes. The reaction mixture was washed in turn wit... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Primary amine.Tertiary amine.Sulfonyl halide | Sulfonamide.Mesylate | null | null | null | HCl | ClCCl | null | null | CCN(CC)CC.CS(=O)(=O)Cl.NCCCO>ClCCl>CS(=O)(=O)NCCCOS(C)(=O)=O |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-81bb6d68545c45f9ba9437d6d4437235 | CS(=O)(=O)NCCCOS(C)(=O)=O.Sc1cccc2nccn12>>CS(=O)(=O)NCCCSc1cccc2nccn12 | SC1=CC=CC=2N1C=CN2.C[O-].[Na+].CS(=O)(=O)NCCCOS(=O)(=O)C>>CS(=O)(=O)NCCCSC1=CC=CC=2N1C=CN2 | CS(=O)(=O)O[CH2:8][CH2:7][CH2:6][NH:5][S:2]([CH3:1])(=[O:3])=[O:4].[SH:9][c:10]1[cH:11][cH:12][cH:13][c:14]2[n:15][cH:16][cH:17][n:18]12>>[CH3:1][S:2](=[O:3])(=[O:4])[NH:5][CH2:6][CH2:7][CH2:8][S:9][c:10]1[cH:11][cH:12][cH:13][c:14]2[n:15][cH:16][cH:17][n:18]12 | CS(=O)(=O)NCCCOS(C)(=O)=O.Sc1cccc2nccn12 | CS(=O)(=O)NCCCSc1cccc2nccn12 | null | null | C(C)O | Heteroatom Alkylation and Arylation | OtherReaction | bb86271f960c642587dc900180f99bfb3d3eab3ca39b11b3cb70560d94f407f0 | 16472cd174cc2da3287c614705959a9f9d18ac963bc8ef0c26feb5dd489d747b | c1ccn2ccnc2c1 | C-S(=O)(=O)-O-[CH2;D2;+0:1]-[C:2]-[C:3].[SH;D1;+0:4]-[c:5](:[c:6]):[#7;a:7]1:[c:8]:[#7;a:9]:[c:10]:[c:11]:1>>[C:3]-[C:2]-[CH2;D2;+0:1]-[S;H0;D2;+0:4]-[c:5](:[c:6]):[#7;a:7]1:[c:8]:[#7;a:9]:[c:10]:[c:11]:1 | 47.5 | [{"value": 47.5, "product": "CS(=O)(=O)NCCCSC1=CC=CC=2N1C=CN2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 47.0, "product": "CS(=O)(=O)NCCCSC1=CC=CC=2N1C=CN2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 5-mercaptoimidazo[1,2-a]pyridine (1.50 g, 10 mmoles) and 4M sodium methylate (2.93 ml, 12 mmoles) in ethanol (50 ml) was added 3-methylsulfonylamino-1-methylsulfonyloxypropane (2.77 g, 12 mmoles) at room temperature and the mixture was heated under reflux for 16 hours. After cooling, the solvent was di... | 10.6084/m9.figshare.5104873.v1 | null | Mesylate.Aromatic thiol | Monosulfide | null | null | c1ccn2ccnc2c1 | MsOH.HO- | C(C)O | null | null | CS(=O)(=O)NCCCOS(C)(=O)=O.Sc1cccc2nccn12>C(C)O>CS(=O)(=O)NCCCSc1cccc2nccn12 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-3bef49f4277949b99b8d263b16800965 | O=C1c2ccccc2CN1CCBr.Sc1cccc2nccn12>>O=C1c2ccccc2CN1CCSc1cccc2nccn12 | SC1=CC=CC=2N1C=CN2.BrCCN1C(C2=CC=CC=C2C1)=O.C(C)N(CC)CC>>C1(N(CC2=CC=CC=C12)CCSC1=CC=CC=2N1C=CN2)=O | Br[CH2:12][CH2:11][N:10]1[C:2](=[O:1])[c:3]2[cH:4][cH:5][cH:6][cH:7][c:8]2[CH2:9]1.[SH:13][c:14]1[cH:15][cH:16][cH:17][c:18]2[n:19][cH:20][cH:21][n:22]12>>[O:1]=[C:2]1[c:3]2[cH:4][cH:5][cH:6][cH:7][c:8]2[CH2:9][N:10]1[CH2:11][CH2:12][S:13][c:14]1[cH:15][cH:16][cH:17][c:18]2[n:19][cH:20][cH:21][n:22]12 | O=C1c2ccccc2CN1CCBr.Sc1cccc2nccn12 | O=C1c2ccccc2CN1CCSc1cccc2nccn12 | null | null | C(C)O | Heteroatom Alkylation and Arylation | thioether_nucl_sub | 26df88c6a3f5f203c89584658be4e126cb42994c98a2e16bc812e1036cdae857 | 8b2f52296c3a93039174c980b6042ba15754e04d6892a1284c3a32985220b214 | O=C1c2ccccc2CN1CCSc1cccc2nccn12 | Br-[CH2;D2;+0:1]-[C:2]-[#7:3]-[C:4]=[O;D1;H0:5].[SH;D1;+0:6]-[c:7](:[c:8]):[#7;a:9]1:[c:10]:[#7;a:11]:[c:12]:[c:13]:1>>[O;D1;H0:5]=[C:4]-[#7:3]-[C:2]-[CH2;D2;+0:1]-[S;H0;D2;+0:6]-[c:7](:[c:8]):[#7;a:9]1:[c:10]:[#7;a:11]:[c:12]:[c:13]:1 | 77 | [{"value": 77.0, "product": "C1(N(CC2=CC=CC=C12)CCSC1=CC=CC=2N1C=CN2)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 76.9, "product": "C1(N(CC2=CC=CC=C12)CCSC1=CC=CC=2N1C=CN2)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 12 | HOUR | To a suspension of 5-mercaptoimidazo[1,2-a]pyridine (150 mg, 1 mmole) and 2-[2-(bromo)ethyl]isoindolin-1-one (240 mg, 1 mmole) in ethanol (15 ml) was added triethylamine (0.21 ml, 1.5 mmoles) and the mixture Was stirred at room temperature for 12 hours and heated at reflux for 2 hours. After the solvent was distilled o... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic thiol | Monosulfide | null | null | c1ccc2c(c1)C[NH]C2.c1ccn2ccnc2c1 | HBr | C(C)O | null | 12 | O=C1c2ccccc2CN1CCBr.Sc1cccc2nccn12>C(C)O>O=C1c2ccccc2CN1CCSc1cccc2nccn12 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-9476683574db42fea1b85ced5bf91a51 | CC(C)(C)OC(=O)NCCSc1cccc2ncc([N+](=O)[O-])n12>>Cl.NCCSc1cccc2ncc([N+](=O)[O-])n12 | C(C)(C)(C)OC(=O)NCCSC1=CC=CC=2N1C(=CN2)[N+](=O)[O-].Cl>>Cl.Cl.NCCSC1=CC=CC=2N1C(=CN2)[N+](=O)[O-] | CC(C)(C)OC(=O)[NH:3][CH2:4][CH2:5][S:6][c:7]1[cH:8][cH:9][cH:10][c:11]2[n:12][cH:13][c:14]([N+:15](=[O:16])[O-:17])[n:18]12>>[ClH:2].[NH2:3][CH2:4][CH2:5][S:6][c:7]1[cH:8][cH:9][cH:10][c:11]2[n:12][cH:13][c:14]([N+:15](=[O:16])[O-:17])[n:18]12 | CC(C)(C)OC(=O)NCCSc1cccc2ncc([N+](=O)[O-])n12 | Cl.NCCSc1cccc2ncc([N+](=O)[O-])n12 | null | null | CO | Miscellaneous | Hydrogenolysis of amides/imides/carbamates | 4812e39fa209f57a5a2564677791e5e37790c829f5742d8c7df33806c5ba4ce0 | d7ecc2e7a68b8c20d378ac6004c3fdfc3efd09bbbd9efd577186f69427135737 | c1ccn2ccnc2c1 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[C:2]-[C:3]>>[C:3]-[C:2]-[NH2;D1;+0:1] | null | [] | null | null | 1 | HOUR | To a suspension of 5-[2-(tert-butoxycarbonylamino)ethylthio]-3-nitroimidazo[1,2-a]pyridine (364 mg, 1.08 mmoles) in methanol (3 ml) was added conc. hydrochloric acid (2 ml) and the mixture was stirred at room temperature for 1 hour. Then, the solvent was distilled off to obtain 340 mg of the desired product (quantitati... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Primary amine | null | null | c1ccn2ccnc2c1 | HO- | CO | null | 1 | CC(C)(C)OC(=O)NCCSc1cccc2ncc([N+](=O)[O-])n12>CO>Cl.NCCSc1cccc2ncc([N+](=O)[O-])n12 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-80a191c764044e848a0c93a0841e8312 | CS(=O)(=O)N1CCC(O)CC1.O=[N+]([O-])c1cnc2cccc(Cl)n12>>CS(=O)(=O)N1CCC(Oc2cccc3ncc([N+](=O)[O-])n23)CC1 | ClC1=CC=CC=2N1C(=CN2)[N+](=O)[O-].OC1CCN(CC1)S(=O)(=O)C.[H-].[Na+].O>>CS(=O)(=O)N1CCC(CC1)OC1=CC=CC=2N1C(=CN2)[N+](=O)[O-] | [CH3:1][S:2](=[O:3])(=[O:4])[N:5]1[CH2:6][CH2:7][CH:8]([OH:9])[CH2:22][CH2:23]1.Cl[c:10]1[cH:11][cH:12][cH:13][c:14]2[n:15][cH:16][c:17]([N+:18](=[O:19])[O-:20])[n:21]12>>[CH3:1][S:2](=[O:3])(=[O:4])[N:5]1[CH2:6][CH2:7][CH:8]([O:9][c:10]2[cH:11][cH:12][cH:13][c:14]3[n:15][cH:16][c:17]([N+:18](=[O:19])[O-:20])[n:21]23)[... | CS(=O)(=O)N1CCC(O)CC1.O=[N+]([O-])c1cnc2cccc(Cl)n12 | CS(=O)(=O)N1CCC(Oc2cccc3ncc([N+](=O)[O-])n23)CC1 | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | a3c24666dcc7591244ef0bfc8eff58c01a9bc3e8d1b581d90f8e8203e5b9ba3a | 1f70dbbaebc288b3a5d3f37803812d9d22b151831cd4b8351080508554b19875 | c1cc(OC2CCNCC2)n2ccnc2c1 | Cl-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[c:5]2:[#7;a:6]:[c:7]:[c:8]:[#7;a:9]:2:1.[C:10]-[C:11](-[OH;D1;+0:12])-[C:13]>>[C:10]-[C:11](-[O;H0;D2;+0:12]-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[c:5]2:[#7;a:6]:[c:7]:[c:8]:[#7;a:9]:2:1)-[C:13] | 54.7 | [{"value": 54.7, "product": "CS(=O)(=O)N1CCC(CC1)OC1=CC=CC=2N1C(=CN2)[N+](=O)[O-]", "details": "PERCENTYIELD", "is_desired": false}, {"value": 54.7, "product": "CS(=O)(=O)N1CCC(CC1)OC1=CC=CC=2N1C(=CN2)[N+](=O)[O-]", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 4-hydroxy-1-methylsulfonylpiperidine (2.15 g, 12 mmoles) in dimethylformamide (3 ml) was added 60% sodium hydride in oil (0.48 g, 12 mmoles) with stirring under ice-cooling and the mixture was stirred at room temperature for 10 minutes. To the reaction mixture was added 5-chloro-3-nitroimidazo[1,2-a]py... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary alcohol | Ether | c1ccn2ccnc2c1 | c1ccn2ccnc2c1 | C1CC[NH]CC1.c1ccn2ccnc2c1 | HCl | CN(C=O)C | null | null | CS(=O)(=O)N1CCC(O)CC1.O=[N+]([O-])c1cnc2cccc(Cl)n12>CN(C=O)C>CS(=O)(=O)N1CCC(Oc2cccc3ncc([N+](=O)[O-])n23)CC1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-dc4408c63f6448a4b162d610549368c0 | CS(=O)(=O)N1CCC(Oc2cccc3ncc([N+](=O)[O-])n23)CC1>>CS(=O)(=O)N1CCC(Oc2cccc3ncc(N)n23)CC1 | CS(=O)(=O)N1CCC(CC1)OC1=CC=CC=2N1C(=CN2)[N+](=O)[O-]>>NC1=CN=C2N1C(=CC=C2)OC2CCN(CC2)S(=O)(=O)C | O=[N+:18]([O-])[c:17]1[cH:16][n:15][c:14]2[cH:13][cH:12][cH:11][c:10]([O:9][CH:8]3[CH2:7][CH2:6][N:5]([S:2]([CH3:1])(=[O:3])=[O:4])[CH2:21][CH2:20]3)[n:19]21>>[CH3:1][S:2](=[O:3])(=[O:4])[N:5]1[CH2:6][CH2:7][CH:8]([O:9][c:10]2[cH:11][cH:12][cH:13][c:14]3[n:15][cH:16][c:17]([NH2:18])[n:19]23)[CH2:20][CH2:21]1 | CS(=O)(=O)N1CCC(Oc2cccc3ncc([N+](=O)[O-])n23)CC1 | CS(=O)(=O)N1CCC(Oc2cccc3ncc(N)n23)CC1 | null | [C].[Pd] | [H][H].C(Cl)Cl | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1cc(OC2CCNCC2)n2ccnc2c1 | O=[N+;H0;D3:1](-[O-])-[c:2]1:[c:3]:[#7;a:4]:[c:5]:[#7;a:6]:1:[c:7]>>[NH2;D1;+0:1]-[c:2]1:[c:3]:[#7;a:4]:[c:5]:[#7;a:6]:1:[c:7] | 132.6 | [{"value": 30.0, "product": "NC1=CN=C2N1C(=CC=C2)OC2CCN(CC2)S(=O)(=O)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 132.6, "product": "NC1=CN=C2N1C(=CC=C2)OC2CCN(CC2)S(=O)(=O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 5-[1-(methylsulfonyl)-4-piperidyloxy]-3-nitroimidazo[1,2-a]pyridine (70 mg, 0.226 mmole) in methylene chloride (10 ml) was added 10% palladium-carbon (50 ml) and the mixture was stirred in hydrogen atmosphere at room temperature for 1.5 hours. After the reaction mixture was treated with Cellite, the so... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | C1CC[NH]CC1.c1ccn2ccnc2c1 | Other | [C].[Pd].[H][H].C(Cl)Cl | null | null | CS(=O)(=O)N1CCC(Oc2cccc3ncc([N+](=O)[O-])n23)CC1>[C].[Pd].[H][H].C(Cl)Cl>CS(=O)(=O)N1CCC(Oc2cccc3ncc(N)n23)CC1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-000317cc53274835920257e50a875bf5 | CCN(CC)CC.CS(=O)(=O)Cl.OC1CCNCC1>>CS(=O)(=O)OC1CCN(S(C)(=O)=O)CC1 | OC1CCNCC1.C(C)N(CC)CC.CS(=O)(=O)Cl>>CS(=O)(=O)N1CCC(CC1)OS(=O)(=O)C | CCN(CC)C[CH3:11].Cl[S:2]([CH3:1])(=[O:3])=[O:13].[OH:5][CH:6]1[CH2:7][CH2:8][NH:9][CH2:14][CH2:15]1>>[CH3:1][S:2](=[O:3])(=[O:4])[O:5][CH:6]1[CH2:7][CH2:8][N:9]([S:10]([CH3:11])(=[O:12])=[O:13])[CH2:14][CH2:15]1 | CCN(CC)CC.CS(=O)(=O)Cl.OC1CCNCC1 | CS(=O)(=O)OC1CCN(S(C)(=O)=O)CC1 | null | null | C(Cl)Cl | Oxidation | OtherReaction | 00ace9fbf2b165ec2c254f5ca4ec165bf11a3a89aae5154b73b21e6882af1ed2 | d42d2539074fe88314f9eefff3832ba539508726d7d6283abb938e17a28608f0 | C1CCNCC1 | C-C-N(-C-C)-C-[CH3;D1;+0:1].Cl-[S;H0;D4;+0:2](-[C;D1;H3:3])(=[O;D1;H0:4])=[O;H0;D1;+0:5].[OH;D1;+0:6]-[C:7]1-[C:8]-[C:9]-[NH;D2;+0:10]-[C:11]-[C:12]-1>>[C;D1;H3:3]-[S;H0;D4;+0:2](=[O;D1;H0:4])(=[O;D1;H0:13])-[O;H0;D2;+0:6]-[C:7]1-[C:8]-[C:9]-[N;H0;D3;+0:10](-[#16:14](-[CH3;D1;+0:1])(=[O;D1;H0:15])=[O;H0;D1;+0:5])-[C:11... | 89 | [{"value": 88.3, "product": "CS(=O)(=O)N1CCC(CC1)OS(=O)(=O)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 89.0, "product": "CS(=O)(=O)N1CCC(CC1)OS(=O)(=O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 4-hydroxypiperidine (5.10 g, 50 mmoles) and triethylamine (20.9 ml, 150 mmoles) in methylene chloride (150 ml) was added methanesulfonyl chloride (8.54 ml, 110 mmoles) with stirring under ice-cooling and the mixture was stirred at room temperature for 1 hour. The reaction mixture was washed in turn wit... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol.Secondary amine.Tertiary amine.Sulfonyl halide | Mesylate.Tertiary amine | C1CCNCC1 | C1CC[NH]CC1 | C1CC[NH]CC1 | HCl | C(Cl)Cl | null | null | CCN(CC)CC.CS(=O)(=O)Cl.OC1CCNCC1>C(Cl)Cl>CS(=O)(=O)OC1CCN(S(C)(=O)=O)CC1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-b41679ed788043cfae401763920430fc | CS(=O)(=O)OC1CCN(S(C)(=O)=O)CC1.Sc1cccc2nccn12>>CS(=O)(=O)N1CCC(Sc2cccc3nccn23)CC1 | SC1=CC=CC=2N1C=CN2.C[O-].[Na+].CS(=O)(=O)N1CCC(CC1)OS(=O)(=O)C>>CS(=O)(=O)N1CCC(CC1)SC1=CC=CC=2N1C=CN2 | CS(=O)(=O)O[CH:8]1[CH2:7][CH2:6][N:5]([S:2]([CH3:1])(=[O:3])=[O:4])[CH2:20][CH2:19]1.[SH:9][c:10]1[cH:11][cH:12][cH:13][c:14]2[n:15][cH:16][cH:17][n:18]12>>[CH3:1][S:2](=[O:3])(=[O:4])[N:5]1[CH2:6][CH2:7][CH:8]([S:9][c:10]2[cH:11][cH:12][cH:13][c:14]3[n:15][cH:16][cH:17][n:18]23)[CH2:19][CH2:20]1 | CS(=O)(=O)OC1CCN(S(C)(=O)=O)CC1.Sc1cccc2nccn12 | CS(=O)(=O)N1CCC(Sc2cccc3nccn23)CC1 | null | null | C(C)O.CO | Heteroatom Alkylation and Arylation | OtherReaction | 53281a2e1fd3bd2937c6e5540fdcc8432fab4a0ba59f75f402a5010732bdd740 | 16472cd174cc2da3287c614705959a9f9d18ac963bc8ef0c26feb5dd489d747b | c1cc(SC2CCNCC2)n2ccnc2c1 | C-S(=O)(=O)-O-[CH;D3;+0:1]1-[C:2]-[C:3]-[#7:4]-[C:5]-[C:6]-1.[SH;D1;+0:7]-[c:8](:[c:9]):[#7;a:10]1:[c:11]:[#7;a:12]:[c:13]:[c:14]:1>>[c:9]:[c:8](-[S;H0;D2;+0:7]-[CH;D3;+0:1]1-[C:2]-[C:3]-[#7:4]-[C:5]-[C:6]-1):[#7;a:10]1:[c:11]:[#7;a:12]:[c:13]:[c:14]:1 | 40.8 | [{"value": 40.8, "product": "CS(=O)(=O)N1CCC(CC1)SC1=CC=CC=2N1C=CN2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 40.8, "product": "CS(=O)(=O)N1CCC(CC1)SC1=CC=CC=2N1C=CN2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 10 | MINUTE | To a suspension of 5-mercaptoimidazo[1,2-a]pyridine (1.50 g, 10 mmoles) in ethanol (100 ml) was added a solution of 4.1M sodium methylate (2.44 ml, 10 mmoles) in methanol and the mixture was stirred at room temperature for 10 minutes. To the reaction mixture was added 1-methylsulfonyl-4-methylsulfonyloxypiperidine (2.8... | 10.6084/m9.figshare.5104873.v1 | null | Mesylate.Aromatic thiol | Monosulfide | C1CC[NH]CC1 | C1CC[NH]CC1 | C1CC[NH]CC1.c1ccn2ccnc2c1 | MsOH.HO- | C(C)O.CO | null | 0.166667 | CS(=O)(=O)OC1CCN(S(C)(=O)=O)CC1.Sc1cccc2nccn12>C(C)O.CO>CS(=O)(=O)N1CCC(Sc2cccc3nccn23)CC1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-13653be87d9a426aafa7e7ae72c1fdf7 | CS(=O)(=O)Cl.OCCSc1cccc2nccn12>>CS(=O)(=O)OCCSc1cccc2nccn12 | OCCSC1=CC=CC=2N1C=CN2.C(C)N(CC)CC.CS(=O)(=O)Cl>>CS(=O)(=O)OCCSC1=CC=CC=2N1C=CN2 | Cl[S:2]([CH3:1])(=[O:3])=[O:4].[OH:5][CH2:6][CH2:7][S:8][c:9]1[cH:10][cH:11][cH:12][c:13]2[n:14][cH:15][cH:16][n:17]12>>[CH3:1][S:2](=[O:3])(=[O:4])[O:5][CH2:6][CH2:7][S:8][c:9]1[cH:10][cH:11][cH:12][c:13]2[n:14][cH:15][cH:16][n:17]12 | CS(=O)(=O)Cl.OCCSc1cccc2nccn12 | CS(=O)(=O)OCCSc1cccc2nccn12 | null | null | C(Cl)Cl | Acylation | Formation of Sulfonic Esters | 2fa969eb2c954bb96793348a1b2335ec63fbd290dadec6e3e02295e1768e64cf | cb77b899e4adf980b1def97230ef2861660fd7f9602260ec64747d9afd3a795a | c1ccn2ccnc2c1 | Cl-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4].[C:5]-[C:6]-[OH;D1;+0:7]>>[C:5]-[C:6]-[O;H0;D2;+0:7]-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4] | 99.9 | [{"value": 99.9, "product": "CS(=O)(=O)OCCSC1=CC=CC=2N1C=CN2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 5-(2-hydroxy)ethylthioimidazo[1,2-a]pyridine (9.71 g, 50 mmoles) and triethylamine (10.5 ml, 75.3 mmoles) in methylene chloride (300 ml) was added methanesulfonyl chloride (4.26 ml, 55 mmoles) under ice-cooling with stirring and the mixture was stirred under ice-cooling for 2 hours. The reaction mixtur... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Sulfonyl halide | Mesylate | null | null | c1ccn2ccnc2c1 | HCl | C(Cl)Cl | null | null | CS(=O)(=O)Cl.OCCSc1cccc2nccn12>C(Cl)Cl>CS(=O)(=O)OCCSc1cccc2nccn12 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-7c20f62d01794f2e832a1780e09e3e32 | CN.CS(=O)(=O)OCCSc1cccc2nccn12>>CNCCSc1cccc2nccn12 | CS(=O)(=O)OCCSC1=CC=CC=2N1C=CN2.C(C)N(CC)CC.CN.CO>>CNCCSC1=CC=CC=2N1C=CN2 | [CH3:1][NH2:2].CS(=O)(=O)O[CH2:3][CH2:4][S:5][c:6]1[cH:7][cH:8][cH:9][c:10]2[n:11][cH:12][cH:13][n:14]12>>[CH3:1][NH:2][CH2:3][CH2:4][S:5][c:6]1[cH:7][cH:8][cH:9][c:10]2[n:11][cH:12][cH:13][n:14]12 | CN.CS(=O)(=O)OCCSc1cccc2nccn12 | CNCCSc1cccc2nccn12 | null | null | C(Cl)(Cl)Cl | Heteroatom Alkylation and Arylation | Alkylation of amines | 8445343b2fb2fd8a9bc06f8532794f2ba6b99565a6e05a3bb9a4344ce2671186 | 7e6303acde8be57b43b4c6a673e1c7537b1efde90f08932e09e153dbba53a700 | c1ccn2ccnc2c1 | C-S(=O)(=O)-O-[CH2;D2;+0:1]-[C:2]-[#16:3].[C;D1;H3:4]-[NH2;D1;+0:5]>>[#16:3]-[C:2]-[CH2;D2;+0:1]-[NH;D2;+0:5]-[C;D1;H3:4] | 47.1 | [{"value": 47.1, "product": "CNCCSC1=CC=CC=2N1C=CN2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 47.1, "product": "CNCCSC1=CC=CC=2N1C=CN2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 5-[2-(methylsulfonyloxy)etylthio]imidazo[1,2-a]pyridine (2.18 g, 8 mmoles), triethylamine (2.24 ml, 16 mmoles) and a 40% methylamine-methanol solution (20 ml) in chloroform (20 ml) was heated at reflux for 3 hours. The reaction mixture was washed with 3N NaOH and dried over anhydrous magnesium sulfate. Af... | 10.6084/m9.figshare.5104873.v1 | null | Mesylate.Primary amine | Secondary amine | null | null | c1ccn2ccnc2c1 | MsOH.HO- | C(Cl)(Cl)Cl | null | null | CN.CS(=O)(=O)OCCSc1cccc2nccn12>C(Cl)(Cl)Cl>CNCCSc1cccc2nccn12 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-c26cb13241bf43e2bb978f5ffb81ffc1 | Clc1cccc2nccn12.N=C(N)SCCCN>>NCCCSc1cccc2nccn12 | ClC1=CC=CC=2N1C=CN2.[OH-].[K+].CS(=O)C.Br.Br.NCCCSC(N)=N>>NCCCSC1=CC=CC=2N1C=CN2 | Cl[c:6]1[cH:7][cH:8][cH:9][c:10]2[n:11][cH:12][cH:13][n:14]12.N=C(N)[S:5][CH2:4][CH2:3][CH2:2][NH2:1]>>[NH2:1][CH2:2][CH2:3][CH2:4][S:5][c:6]1[cH:7][cH:8][cH:9][c:10]2[n:11][cH:12][cH:13][n:14]12 | Clc1cccc2nccn12.N=C(N)SCCCN | NCCCSc1cccc2nccn12 | null | null | O | Heteroatom Alkylation and Arylation | OtherReaction | 5c2ee1fbeb816b2281fc56b7a7c3dec1a003cfc961b24d42976d878151218e19 | a0db6fe3ed1c4fe8c413e334ea9e090fc70b5b1dbf83be67f74f657c2f41a45d | c1ccn2ccnc2c1 | Cl-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[c:5]2:[#7;a:6]:[c:7]:[c:8]:[#7;a:9]:2:1.N-C(=N)-[S;H0;D2;+0:10]-[C:11]-[C:12]>>[C:12]-[C:11]-[S;H0;D2;+0:10]-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[c:5]2:[#7;a:6]:[c:7]:[c:8]:[#7;a:9]:2:1 | 64.3 | [{"value": 64.3, "product": "NCCCSC1=CC=CC=2N1C=CN2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 64.2, "product": "NCCCSC1=CC=CC=2N1C=CN2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1.5 | HOUR | To a mixed solution of 10% (w/w) potassium hydroxide (69.3 g, 105 mmoles) and dimethylsulfoxide (50 ml) was added S-(3-aminopropyl)isothiourea dihydrobromide (8.85 g, 39 mmoles) and the mixture was stirred at room temperature for 1.5 hours. To the reaction mixture was added 5-chloroimidazo[1,2-a]pyridine (3.05 g, 20 mm... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine.Monosulfide | Monosulfide | c1ccn2ccnc2c1 | c1ccn2ccnc2c1 | c1ccn2ccnc2c1 | HCl | O | null | 1.5 | Clc1cccc2nccn12.N=C(N)SCCCN>O>NCCCSc1cccc2nccn12 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-153f77bc2a644cc5babb03217d5b3d48 | COC(=O)Cl.NCCSc1cccc2nccn12>>COC(=O)NCCSc1cccc2nccn12 | NCCSC1=CC=CC=2N1C=CN2.C(C)N(CC)CC.ClC(=O)OC>>COC(=O)NCCSC1=CC=CC=2N1C=CN2 | Cl[C:3]([O:2][CH3:1])=[O:4].[NH2:5][CH2:6][CH2:7][S:8][c:9]1[cH:10][cH:11][cH:12][c:13]2[n:14][cH:15][cH:16][n:17]12>>[CH3:1][O:2][C:3](=[O:4])[NH:5][CH2:6][CH2:7][S:8][c:9]1[cH:10][cH:11][cH:12][c:13]2[n:14][cH:15][cH:16][n:17]12 | COC(=O)Cl.NCCSc1cccc2nccn12 | COC(=O)NCCSc1cccc2nccn12 | null | null | C(Cl)Cl | Protection | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 038720aa61a7efa0f2a9ee6f2e0adf63a9ffdc2be4697c11a6215baef34f97b2 | 205f353513ce9506ab61831799da8fb73ec2ef5cfa927664496d3ce72c438860 | c1ccn2ccnc2c1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C;D1;H3:4].[C:5]-[C:6]-[NH2;D1;+0:7]>>[C:5]-[C:6]-[NH;D2;+0:7]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C;D1;H3:4] | 66.9 | [{"value": 66.9, "product": "COC(=O)NCCSC1=CC=CC=2N1C=CN2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 66.9, "product": "COC(=O)NCCSC1=CC=CC=2N1C=CN2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 5-[2-(amino)ethylthio]imidazo[1,2-a]pyridine (1.93 g, 10 mmoles) and triethylamine (1.53 ml, 11 mmoles) in methylene chloride (30 ml) was added methyl chloroformate (0.77 ml, 10 mmoles) under ice-cooling with stirring and the mixture was stirred at room temperature for 20 minutes. The reaction mixture ... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Ether.Primary amine | Carbamic ester | null | null | c1ccn2ccnc2c1 | HCl | C(Cl)Cl | null | null | COC(=O)Cl.NCCSc1cccc2nccn12>C(Cl)Cl>COC(=O)NCCSc1cccc2nccn12 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-af87d36622ea458291f1775ee5fc3fe3 | CC(C)OC(=O)NCCSc1cccc2nccn12.O=C1CCC(=O)N1Br>>CC(C)OC(=O)NCCSc1cccc2ncc(Br)n12 | C(C)(C)OC(=O)NCCSC1=CC=CC=2N1C=CN2.BrN1C(CCC1=O)=O>>BrC1=CN=C2N1C(=CC=C2)SCCNC(=O)OC(C)C | [CH3:1][CH:2]([CH3:3])[O:4][C:5](=[O:6])[NH:7][CH2:8][CH2:9][S:10][c:11]1[cH:12][cH:13][cH:14][c:15]2[n:16][cH:17][cH:18][n:20]12.O=C1CCC(=O)N1[Br:19]>>[CH3:1][CH:2]([CH3:3])[O:4][C:5](=[O:6])[NH:7][CH2:8][CH2:9][S:10][c:11]1[cH:12][cH:13][cH:14][c:15]2[n:16][cH:17][c:18]([Br:19])[n:20]12 | CC(C)OC(=O)NCCSc1cccc2nccn12.O=C1CCC(=O)N1Br | CC(C)OC(=O)NCCSc1cccc2ncc(Br)n12 | null | null | C(Cl)(Cl)Cl | Functional Group Interconversion | Bromination | 4574e733f80d194ce9380df52b6f0165984d072a1369f9c636a5ef16f4be8d67 | 0e444576b73669992a4073cc3f7b10ed52cb9df09f9f8e4042e39e6a602aa390 | c1ccn2ccnc2c1 | O=C1-C-C-C(=O)-N-1-[Br;H0;D1;+0:1].[c:2]:[#7;a:3]1:[cH;D2;+0:4]:[c:5]:[#7;a:6]:[c:7]:1:[c:8]>>[Br;H0;D1;+0:1]-[c;H0;D3;+0:4]1:[c:5]:[#7;a:6]:[c:7](:[c:8]):[#7;a:3]:1:[c:2] | 82.7 | [{"value": 82.7, "product": "BrC1=CN=C2N1C(=CC=C2)SCCNC(=O)OC(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 82.6, "product": "BrC1=CN=C2N1C(=CC=C2)SCCNC(=O)OC(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | To a solution of 5-[2-(isopropyloxycarbonylamino)ethylthio]imidazo[1,2-a]pyridine (279 mg, 1 mmole) in chloroform (5 ml) was added N-bromosuccinimide (187 ml, 1.05 mmoles) and the mixture was stirred at room temperature for 1 hour. The reaction solution was washed with water and dried over anhydrous magnesium sulfate. ... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Tertiary amide | Aromatic halide | c1ccn2ccnc2c1.C1CCNC1 | c1ccn2ccnc2c1 | c1ccn2ccnc2c1 | HO- | C(Cl)(Cl)Cl | null | 1 | CC(C)OC(=O)NCCSc1cccc2nccn12.O=C1CCC(=O)N1Br>C(Cl)(Cl)Cl>CC(C)OC(=O)NCCSc1cccc2ncc(Br)n12 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-9e25ae07e399492788ca461ed5c581a2 | C1COCCN1.C=O.CC(C)OC(=O)NCCSc1cccc2nccn12>>CC(C)OC(=O)NCCSc1cccc2ncc(CN3CCOCC3)n12 | C(C)(C)OC(=O)NCCSC1=CC=CC=2N1C=CN2.C=O.N1CCOCC1>>C(C)(C)OC(=O)NCCSC1=CC=CC=2N1C(=CN2)CN2CCOCC2 | [NH:20]1[CH2:21][CH2:22][O:23][CH2:24][CH2:25]1.O=[CH2:19].[CH3:1][CH:2]([CH3:3])[O:4][C:5](=[O:6])[NH:7][CH2:8][CH2:9][S:10][c:11]1[cH:12][cH:13][cH:14][c:15]2[n:16][cH:17][cH:18][n:26]12>>[CH3:1][CH:2]([CH3:3])[O:4][C:5](=[O:6])[NH:7][CH2:8][CH2:9][S:10][c:11]1[cH:12][cH:13][cH:14][c:15]2[n:16][cH:17][c:18]([CH2:19][... | C1COCCN1.C=O.CC(C)OC(=O)NCCSc1cccc2nccn12 | CC(C)OC(=O)NCCSc1cccc2ncc(CN3CCOCC3)n12 | null | null | C(C)(=O)O | Heteroatom Alkylation and Arylation | OtherReaction | 6b4ae5aa80021261c6aaedaefa5d3defe26d9563ca80e76f1ce7765ec33cd64e | e1fdef8fde1c506d7c9deb8fd5e6f322eceea2abce3167abcf412a1fa4fd5443 | c1ccn2c(CN3CCOCC3)cnc2c1 | O=[CH2;D1;+0:1].[#8:2]1-[C:3]-[C:4]-[NH;D2;+0:5]-[C:6]-[C:7]-1.[c:8]:[#7;a:9]1:[cH;D2;+0:10]:[c:11]:[#7;a:12]:[c:13]:1:[c:14]>>[c:8]:[#7;a:9]1:[c:13](:[c:14]):[#7;a:12]:[c:11]:[c;H0;D3;+0:10]:1-[CH2;D2;+0:1]-[N;H0;D3;+0:5]1-[C:4]-[C:3]-[#8:2]-[C:7]-[C:6]-1 | 50.1 | [{"value": 50.1, "product": "C(C)(C)OC(=O)NCCSC1=CC=CC=2N1C(=CN2)CN2CCOCC2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 50.1, "product": "C(C)(C)OC(=O)NCCSC1=CC=CC=2N1C(=CN2)CN2CCOCC2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 45 | MINUTE | To a solution of an aqueous 37% formalin solution (210 mg, 2.59 mmoles) in acetic acid (2 ml) was added morpholine (226 μl, 2.59 mmoles) under ice-cooling and the mixture was stirred at room temperature for 45 minutes. 5-[2-(isopropyloxycarbonylamino)ethylthio]imidazo[1,2-a]pyridine (651 mg, 2.33 mmoles) was added, fol... | 10.6084/m9.figshare.5104873.v1 | null | Formaldehyde.Secondary amine | Tertiary amine | C1COCCN1.c1ccn2ccnc2c1 | c1ccn2ccnc2c1.C1COCC[NH]1 | c1ccn2ccnc2c1.C1COCC[NH]1 | HO- | C(C)(=O)O | null | 0.75 | C1COCCN1.C=O.CC(C)OC(=O)NCCSc1cccc2nccn12>C(C)(=O)O>CC(C)OC(=O)NCCSc1cccc2ncc(CN3CCOCC3)n12 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-1b45aea4222d4467b64a679104b92b1b | CC(C)OC(=O)Cl.NCCCCSc1cccc2nccn12>>CC(C)OC(=O)NCCCCSc1cccc2nccn12 | NCCCCSC1=CC=CC=2N1C=CN2.C(C)N(CC)CC.ClC(=O)OC(C)C>>C(C)(C)OC(=O)NCCCCSC1=CC=CC=2N1C=CN2 | Cl[C:5]([O:4][CH:2]([CH3:1])[CH3:3])=[O:6].[NH2:7][CH2:8][CH2:9][CH2:10][CH2:11][S:12][c:13]1[cH:14][cH:15][cH:16][c:17]2[n:18][cH:19][cH:20][n:21]12>>[CH3:1][CH:2]([CH3:3])[O:4][C:5](=[O:6])[NH:7][CH2:8][CH2:9][CH2:10][CH2:11][S:12][c:13]1[cH:14][cH:15][cH:16][c:17]2[n:18][cH:19][cH:20][n:21]12 | CC(C)OC(=O)Cl.NCCCCSc1cccc2nccn12 | CC(C)OC(=O)NCCCCSc1cccc2nccn12 | null | null | C(Cl)Cl | Protection | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 038720aa61a7efa0f2a9ee6f2e0adf63a9ffdc2be4697c11a6215baef34f97b2 | 205f353513ce9506ab61831799da8fb73ec2ef5cfa927664496d3ce72c438860 | c1ccn2ccnc2c1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C:4].[C:5]-[C:6]-[NH2;D1;+0:7]>>[C:4]-[#8:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:7]-[C:6]-[C:5] | 41.9 | [{"value": 41.8, "product": "C(C)(C)OC(=O)NCCCCSC1=CC=CC=2N1C=CN2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 41.9, "product": "C(C)(C)OC(=O)NCCCCSC1=CC=CC=2N1C=CN2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To 5-(4-amino)butylthioimidazo[1,2-a]pyridine (370 mg, 1.67 mmoles) and triethylamine (0.35 ml, 2.51 mmoles) in methylene chloride (20 ml) was added isopropyl chloroformate (0.25 g, 2.04 mmoles) under ice-cooling with stirring and the mixture was stirred under ice-cooling for 1 hour. The reaction mixture was washed in ... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Ether.Primary amine | Carbamic ester | null | null | c1ccn2ccnc2c1 | HCl | C(Cl)Cl | null | null | CC(C)OC(=O)Cl.NCCCCSc1cccc2nccn12>C(Cl)Cl>CC(C)OC(=O)NCCCCSc1cccc2nccn12 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-7c77004a91ef499285caec4cc6c25cf0 | N#CCC#N.O=C1C=C(Cc2ccccc2)C(=O)c2ccccc21>>N#Cc1c(N)oc2c1c(Cc1ccccc1)c(O)c1ccccc12 | C(C1=CC=CC=C1)C=1C(C2=CC=CC=C2C(C1)=O)=O.C(CC#N)#N.[H-].[K+].CCCCCC>>NC1=C(C2=C(O1)C1=CC=CC=C1C(=C2CC2=CC=CC=C2)O)C#N | [N:1]#[C:2][CH2:3][C:4]#[N:5].[O:6]=[C:7]1[CH:8]=[C:9]([CH2:10][c:11]2[cH:12][cH:13][cH:14][cH:15][cH:16]2)[C:17](=[O:18])[c:19]2[cH:20][cH:21][cH:22][cH:23][c:24]21>>[N:1]#[C:2][c:3]1[c:4]([NH2:5])[o:6][c:7]2[c:8]1[c:9]([CH2:10][c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1)[c:17]([OH:18])[c:19]1[cH:20][cH:21][cH:22][cH:... | N#CCC#N.O=C1C=C(Cc2ccccc2)C(=O)c2ccccc21 | N#Cc1c(N)oc2c1c(Cc1ccccc1)c(O)c1ccccc12 | null | null | CCCCCC.C(C)(=O)OCC.O1CCCC1 | Aromatic Heterocycle Formation | OtherReaction | ff66067fe9faab15e641e756b026b86c21edcf52b37323dc352fa908309c6f8c | bead821aa406b28430e6b5d3ca2885db28a64c51ed08f88b8a360f4f62eccabf | c1ccc(Cc2cc3ccccc3c3occc23)cc1 | [N;D1;H0:1]#[C:2]-[CH2;D2;+0:3]-[C;H0;D2;+0:4]#[N;H0;D1;+0:5].[O;H0;D1;+0:6]=[C;H0;D3;+0:7]1-[C;H0;D3;+0:8](-[C:9]-[c:10])=[CH;D2;+0:11]-[C;H0;D3;+0:12](=[O;H0;D1;+0:13])-[c:14](:[c:15]):[c:16]-1:[c:17]>>[N;D1;H0:1]#[C:2]-[c;H0;D3;+0:3]1:[c;H0;D3;+0:4](-[NH2;D1;+0:5]):[o;H0;D2;+0:13]:[c;H0;D3;+0:12]2:[c:14](:[c:15]):[c... | 38 | [{"value": 38.0, "product": "NC1=C(C2=C(O1)C1=CC=CC=C1C(=C2CC2=CC=CC=C2)O)C#N", "details": "PERCENTYIELD", "is_desired": false}, {"value": 36.5, "product": "NC1=C(C2=C(O1)C1=CC=CC=C1C(=C2CC2=CC=CC=C2)O)C#N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of potassium hydride (7.56 g, 63 mmol, 35% oil dispersion) and hexane (250ml) was stirred at room temperature under nitrogen. Solvent was decanted off and substituted with dry tetrahydrofuran (250ml). Malononitrile (4.16 g, 63 mmol), dissolved in tetrahydrofuran (50 ml), was then added to the slurry dropwise.... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ketone.Nitrile | Aromatic alcohol.Primary amine | C1=CCc2ccccc2C1 | c1ccc2c(c1)ccc1ccoc12 | c1ccccc1.c1ccc2c(c1)ccc1ccoc12 | null | CCCCCC.C(C)(=O)OCC.O1CCCC1 | null | null | N#CCC#N.O=C1C=C(Cc2ccccc2)C(=O)c2ccccc21>CCCCCC.C(C)(=O)OCC.O1CCCC1>N#Cc1c(N)oc2c1c(Cc1ccccc1)c(O)c1ccccc12 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-684753ba46a94919aea239a16efe8f16 | COC(=O)CC#N.O=C1C=C(Cc2ccccc2)C(=O)c2ccccc21>>COC(=O)c1c(N)oc2c1c(Cc1ccccc1)c(O)c1ccccc12 | C(#N)CC(=O)OC.C(C1=CC=CC=C1)C=1C(C2=CC=CC=C2C(C1)=O)=O>>NC1=C(C2=C(O1)C1=CC=CC=C1C(=C2CC2=CC=CC=C2)O)C(=O)OC | [CH3:1][O:2][C:3](=[O:4])[CH2:5][C:6]#[N:7].[O:8]=[C:9]1[CH:10]=[C:11]([CH2:12][c:13]2[cH:14][cH:15][cH:16][cH:17][cH:18]2)[C:19](=[O:20])[c:21]2[cH:22][cH:23][cH:24][cH:25][c:26]21>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[c:6]([NH2:7])[o:8][c:9]2[c:10]1[c:11]([CH2:12][c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1)[c:19]([OH:20])... | COC(=O)CC#N.O=C1C=C(Cc2ccccc2)C(=O)c2ccccc21 | COC(=O)c1c(N)oc2c1c(Cc1ccccc1)c(O)c1ccccc12 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 0ef0f9059144747984f18c62223d2d47b335b095c93adbf381b4a518b85907a6 | 20fce4500035b9c037724752778092c2a5e9939c43d19285f880a1cff163a899 | c1ccc(Cc2cc3ccccc3c3occc23)cc1 | [C;D1;H3:1]-[#8:2]-[C:3](=[O;D1;H0:4])-[CH2;D2;+0:5]-[C;H0;D2;+0:6]#[N;H0;D1;+0:7].[O;H0;D1;+0:8]=[C;H0;D3;+0:9]1-[C;H0;D3;+0:10](-[C:11]-[c:12])=[CH;D2;+0:13]-[C;H0;D3;+0:14](=[O;H0;D1;+0:15])-[c:16](:[c:17]):[c:18]-1:[c:19]>>[C;D1;H3:1]-[#8:2]-[C:3](=[O;D1;H0:4])-[c;H0;D3;+0:5]1:[c;H0;D3;+0:13]2:[c;H0;D3;+0:10](-[C:1... | 55 | [{"value": 55.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The title compound was prepared by reaction of methyl cyanoacetate with 2-benzyl-1,4-naphthoquinone following the procedure outlined for example 1. Obtained as tan crystals (55%); m.p. 170°-171° C.; 1H NMR (CDCl3): 3.66(s, 3H), 4.05(s,2H), 5.07(s,2H), 7.17-7.53(m, 8H), 7.98(d, 1H), 8.10(d,1H); IR (nujol): 3309, 3479, 3... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ketone.Ester.Nitrile | Ester.Aromatic alcohol.Primary amine | C1=CCc2ccccc2C1 | c1ccc2c(c1)ccc1ccoc12 | c1ccccc1.c1ccc2c(c1)ccc1ccoc12 | null | null | null | null | COC(=O)CC#N.O=C1C=C(Cc2ccccc2)C(=O)c2ccccc21>>COC(=O)c1c(N)oc2c1c(Cc1ccccc1)c(O)c1ccccc12 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-439e786999cd49489670a20eafe0b9c6 | N=C(N)NCCC[C@H](N)C(=O)O>>N=C(N)NCCC[C@H](N)C(=O)O | C(C)O.SC(C)S(=O)(=O)[O-].[Na+].SC(C)S(=O)(=O)O.N[C@@H](CCCNC(N)=N)C(=O)O>>SC(C)S(=O)(=O)O.N[C@@H](CCCNC(N)=N)C(=O)O | [NH:8]=[C:9]([NH2:10])[NH:11][CH2:12][CH2:13][CH2:14][C@H:15]([NH2:16])[C:17](=[O:18])[OH:19]>>[NH:8]=[C:9]([NH2:10])[NH:11][CH2:12][CH2:13][CH2:14][C@H:15]([NH2:16])[C:17](=[O:18])[OH:19] | N=C(N)NCCC[C@H](N)C(=O)O | N=C(N)NCCC[C@H](N)C(=O)O | null | null | O | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | null | null | 98 | [{"value": 98.0, "product": "SC(C)S(=O)(=O)O.N[C@@H](CCCNC(N)=N)C(=O)O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | 12 g of sodium mercaptoethansulphonate are freed in aqueous solution and under nitrogen stream in a column, as described in the example 1. The mercaptoethansulphonic acid coming out of the column in aqueous solution, under nitrogen stream and at pH=1, is gradually added with arginine, in free base form, in stoichiometr... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | null | null | O | null | null | N=C(N)NCCC[C@H](N)C(=O)O>O>N=C(N)NCCC[C@H](N)C(=O)O |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-d9b3de0723254e4fba578335d794c091 | NCCC[C@H](N)C(=O)O>>NCCC[C@H](N)C(=O)O | SC(C)S(=O)(=O)O.N[C@@H](CCCN)C(=O)O.Cl>>SC(C)S(=O)(=O)O.N[C@@H](CCCN)C(=O)O | [NH2:8][CH2:9][CH2:10][CH2:11][C@H:12]([NH2:13])[C:14](=[O:15])[OH:16]>>[NH2:8][CH2:9][CH2:10][CH2:11][C@H:12]([NH2:13])[C:14](=[O:15])[OH:16] | NCCC[C@H](N)C(=O)O | NCCC[C@H](N)C(=O)O | null | null | CO | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | null | null | null | [] | null | null | null | null | The mercaptoethansulphonic acid coming out from the column, in aqueous solution, under nitrogen stream and at pH=1, is simultaneously added with the stoichiometrical amount of L-ornithine (0.64 g) freed from the hydrochloride through Kastel A 300 resin, in aqueous solution and under nitrogen stream. The addition is car... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | null | null | CO | null | null | NCCC[C@H](N)C(=O)O>CO>NCCC[C@H](N)C(=O)O |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-cb03feb9a3734441aae6f712cf1f69a9 | CC(C)(C)c1cccc(C(C)(C)C)c1O.N#C[S-]>>CC(C)(C)c1cc(SC#N)cc(C(C)(C)C)c1O | C(C)(C)(C)C1=C(C(=CC=C1)C(C)(C)C)O.[S-]C#N.[NH4+]>>CC(C)(C)C=1C=C(C=C(C1O)C(C)(C)C)SC#N | [CH3:1][C:2]([CH3:3])([CH3:4])[c:5]1[cH:6][cH:7][cH:11][c:12]([C:13]([CH3:14])([CH3:15])[CH3:16])[c:17]1[OH:18].[S-:8][C:9]#[N:10]>>[CH3:1][C:2]([CH3:3])([CH3:4])[c:5]1[cH:6][c:7]([S:8][C:9]#[N:10])[cH:11][c:12]([C:13]([CH3:14])([CH3:15])[CH3:16])[c:17]1[OH:18] | CC(C)(C)c1cccc(C(C)(C)C)c1O.N#C[S-] | CC(C)(C)c1cc(SC#N)cc(C(C)(C)C)c1O | null | null | CO | Heteroatom Alkylation and Arylation | OtherReaction | 29d483be92b78aea9894649c5ff004e9773d34416f95eeab1829acdbdeaacc59 | 21e67be598c63344ea1fea503581f1ce4855b092ed4079749b71ebb3b04166d6 | c1ccccc1 | [N;D1;H0:1]#[C:2]-[S-;H0;D1:3].[c:4]:[c:5]:[cH;D2;+0:6]:[c:7]:[c:8]>>[N;D1;H0:1]#[C:2]-[S;H0;D2;+0:3]-[c;H0;D3;+0:6](:[c:5]:[c:4]):[c:7]:[c:8] | null | [] | 0 | CELSIUS | null | null | To a three-necked, round bottom 5 L flask, equipped with a mechanical stirrer, gas inlet, thermometer and gas inlet, thermometer and gas outlet, was added 2,6-di-tert-butylphenol (474 g, 2.30 mole), ammonium thiocyanate (76.12 g, 4.83 mole) and methanol (1200 ml). The reaction mixture was stirred and cooled to 0° C. in... | 10.6084/m9.figshare.5104873.v1 | null | null | Monosulfide | c1ccccc1 | c1ccccc1 | c1ccccc1 | null | CO | 0 | null | CC(C)(C)c1cccc(C(C)(C)C)c1O.N#C[S-]>CO>CC(C)(C)c1cc(SC#N)cc(C(C)(C)C)c1O |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-1a30f638e6c14bbab25c98517e050aa1 | C1CCC(NC2CCCCC2)CC1.C=CC(=O)Cl>>C=CC(=O)N(C1CCCCC1)C1CCCCC1 | C(C=C)(=O)Cl.C1(CCCCC1)NC1CCCCC1.C(C)N(CC)CC>>C1(CCCCC1)N(C(C=C)=O)C1CCCCC1 | [NH:5]([CH:6]1[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11]1)[CH:12]1[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]1.Cl[C:3]([CH:2]=[CH2:1])=[O:4]>>[CH2:1]=[CH:2][C:3](=[O:4])[N:5]([CH:6]1[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11]1)[CH:12]1[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]1 | C1CCC(NC2CCCCC2)CC1.C=CC(=O)Cl | C=CC(=O)N(C1CCCCC1)C1CCCCC1 | null | null | C(C)OCC | Acylation | N-alkylation of secondary amines with alkyl halides | b92e0bfd3d683c1f2a209adfe70a67ad7cb0d87749eb59e8fe0cf1689bc291e0 | 96cb0a2fed10552c5770a45a2d6523b47ac3e38928b4a9c698d8577451182dcd | C1CCC(NC2CCCCC2)CC1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]=[C;D1;H2:4].[C:5]-[C:6](-[NH;D2;+0:7]-[C:8](-[C:9])-[C:10])-[C:11]>>[C:5]-[C:6](-[N;H0;D3;+0:7](-[C:8](-[C:9])-[C:10])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]=[C;D1;H2:4])-[C:11] | null | [] | null | null | 12 | HOUR | A solution of dicyclohexylamine (19.92 ml, 0.10 mole) and triethylamine (27.88 ml, 0.20 mole) in ethyl ether (100 ml) was cooled to 0° C. A solution of acryloyl chloride (7.93 ml, 0.1 mole) in ethyl ether (20 ml) was added and the solution was stirred for 12 hours, filtered and concentrated to obtain the product as a s... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Secondary amine | Tertiary amide | null | null | C1CCCCC1.C1CCCCC1 | HCl | C(C)OCC | null | 12 | C1CCC(NC2CCCCC2)CC1.C=CC(=O)Cl>C(C)OCC>C=CC(=O)N(C1CCCCC1)C1CCCCC1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-83a7fad34b684fd8a233fc5ded25c4c5 | C=CC(=O)N(C1CCCCC1)C1CCCCC1.CC(C)(C)c1cc(S)cc(C(C)(C)C)c1O>>CC(C)(C)c1cc(SCCC(=O)N(C2CCCCC2)C2CCCCC2)cc(C(C)(C)C)c1O | C1(CCCCC1)N(C(C=C)=O)C1CCCCC1.CC(C)(C)C1=C(C(=CC(=C1)S)C(C)(C)C)O.C(C)N(CC)CC>>CC(C)(C)C=1C=C(C=C(C1O)C(C)(C)C)SCCC(=O)N(C1CCCCC1)C1CCCCC1 | [CH2:9]=[CH:10][C:11](=[O:12])[N:13]([CH:14]1[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]1)[CH:20]1[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25]1.[CH3:1][C:2]([CH3:3])([CH3:4])[c:5]1[cH:6][c:7]([SH:8])[cH:26][c:27]([C:28]([CH3:29])([CH3:30])[CH3:31])[c:32]1[OH:33]>>[CH3:1][C:2]([CH3:3])([CH3:4])[c:5]1[cH:6][c:7]([S:8][CH2:9][CH... | C=CC(=O)N(C1CCCCC1)C1CCCCC1.CC(C)(C)c1cc(S)cc(C(C)(C)C)c1O | CC(C)(C)c1cc(SCCC(=O)N(C2CCCCC2)C2CCCCC2)cc(C(C)(C)C)c1O | null | null | CO | Heteroatom Alkylation and Arylation | thia-Michael addition | 9c1714ade80d0bfd6c4747e19bbd5e181aebdd6e70fcf1c4b03944a726aeaf5d | ff275b76dc1ff1d0f3afaf057f654852a0a807709b71c50992bfc9df07afc001 | O=C(CCSc1ccccc1)N(C1CCCCC1)C1CCCCC1 | [C:1]-[#7:2](-[C:3])-[C:4](=[O;D1;H0:5])-[CH;D2;+0:6]=[CH2;D1;+0:7].[SH;D1;+0:8]-[c:9](:[c:10]):[c:11]>>[C:1]-[#7:2](-[C:3])-[C:4](=[O;D1;H0:5])-[CH2;D2;+0:6]-[CH2;D2;+0:7]-[S;H0;D2;+0:8]-[c:9](:[c:10]):[c:11] | null | [] | null | null | null | null | The title compound of Example 3 (1.9 g, 0.008 mole), 2,6-bis(1,1-dimethylethyl)-4-mercaptophenol(2 g, 0.008 mole) and triethylamine (0.5 ml) were stirred in methanol (25 ml) for about 12 hours. The solvent was removed in vacuo on a rotary evaporator, the crude material purified by chromatography on silica and recrystal... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic thiol.Vinyl | Monosulfide | null | null | c1ccccc1.C1CCCCC1.C1CCCCC1 | null | CO | null | null | C=CC(=O)N(C1CCCCC1)C1CCCCC1.CC(C)(C)c1cc(S)cc(C(C)(C)C)c1O>CO>CC(C)(C)c1cc(SCCC(=O)N(C2CCCCC2)C2CCCCC2)cc(C(C)(C)C)c1O |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-d5fd9102081148d99300a6c311bae329 | C=CC(=O)Cl.NC12CC3CC(CC(C3)C1)C2>>C=CC(=O)NC12CC3CC(CC(C3)C1)C2 | C(C=C)(=O)Cl.C12(CC3CC(CC(C1)C3)C2)N.C(C)N(CC)CC>>C12(CC3CC(CC(C1)C3)C2)NC(C=C)=O | Cl[C:3]([CH:2]=[CH2:1])=[O:4].[NH2:5][C:6]12[CH2:7][CH:8]3[CH2:9][CH:10]([CH2:11][CH:12]([CH2:13]3)[CH2:14]1)[CH2:15]2>>[CH2:1]=[CH:2][C:3](=[O:4])[NH:5][C:6]12[CH2:7][CH:8]3[CH2:9][CH:10]([CH2:11][CH:12]([CH2:13]3)[CH2:14]1)[CH2:15]2 | C=CC(=O)Cl.NC12CC3CC(CC(C3)C1)C2 | C=CC(=O)NC12CC3CC(CC(C3)C1)C2 | null | null | C(C)OCC | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | C1C2CC3CC1CC(C2)C3 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]=[C;D1;H2:4].[C:5]-[C:6](-[NH2;D1;+0:7])(-[C:8])-[C:9]>>[C:5]-[C:6](-[NH;D2;+0:7]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]=[C;D1;H2:4])(-[C:8])-[C:9] | null | [] | null | null | 72 | HOUR | A solution of acryloyl chloride (4.05 ml, 0.05 mole) in ethyl ether (25 ml) was added to a cold (+5° C.) solution of 1-adamantaneamine (7.65 g, 0.05 mole) and triethylamine (15.3 ml, 0.11 mole) in ethyl ether (300 ml) and the solution stirred for 72 hours at room temperature. The solvent was removed on a rotary evapora... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | C1C2CC3CC1CC(C2)C3 | HCl | C(C)OCC | null | 72 | C=CC(=O)Cl.NC12CC3CC(CC(C3)C1)C2>C(C)OCC>C=CC(=O)NC12CC3CC(CC(C3)C1)C2 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-390ae00531e84ce6ba81f1cd2e927cdd | C=CC(=O)NC12CC3CC(CC(C3)C1)C2.CC(C)(C)c1cc(S)cc(C(C)(C)C)c1O>>CC(C)(C)c1cc(SCCC(=O)NC23CC4CC(CC(C4)C2)C3)cc(C(C)(C)C)c1O | CC(C)(C)C1=C(C(=CC(=C1)S)C(C)(C)C)O.C12(CC3CC(CC(C1)C3)C2)NC(C=C)=O.C(C)N(CC)CC>>CC(C)(C)C=1C=C(C=C(C1O)C(C)(C)C)SCCC(=O)NC12CC3CC(CC(C1)C3)C2 | [CH2:9]=[CH:10][C:11](=[O:12])[NH:13][C:14]12[CH2:15][CH:16]3[CH2:17][CH:18]([CH2:19][CH:20]([CH2:21]3)[CH2:22]1)[CH2:23]2.[CH3:1][C:2]([CH3:3])([CH3:4])[c:5]1[cH:6][c:7]([SH:8])[cH:24][c:25]([C:26]([CH3:27])([CH3:28])[CH3:29])[c:30]1[OH:31]>>[CH3:1][C:2]([CH3:3])([CH3:4])[c:5]1[cH:6][c:7]([S:8][CH2:9][CH2:10][C:11](=[... | C=CC(=O)NC12CC3CC(CC(C3)C1)C2.CC(C)(C)c1cc(S)cc(C(C)(C)C)c1O | CC(C)(C)c1cc(SCCC(=O)NC23CC4CC(CC(C4)C2)C3)cc(C(C)(C)C)c1O | null | null | CO | Heteroatom Alkylation and Arylation | thia-Michael addition | 9c1714ade80d0bfd6c4747e19bbd5e181aebdd6e70fcf1c4b03944a726aeaf5d | ff275b76dc1ff1d0f3afaf057f654852a0a807709b71c50992bfc9df07afc001 | O=C(CCSc1ccccc1)NC12CC3CC(CC(C3)C1)C2 | [C:1]-[#7:2]-[C:3](=[O;D1;H0:4])-[CH;D2;+0:5]=[CH2;D1;+0:6].[SH;D1;+0:7]-[c:8](:[c:9]):[c:10]>>[C:1]-[#7:2]-[C:3](=[O;D1;H0:4])-[CH2;D2;+0:5]-[CH2;D2;+0:6]-[S;H0;D2;+0:7]-[c:8](:[c:9]):[c:10] | null | [] | null | null | null | null | Following the method of Example 4, 2,6-bis(1,1-dimethylethyl)-4-mercaptophenol (1.19 g, 0.005 mole), the title compound of Example 5 (1.03 g, 0.005 mole) and triethylamine (0.5 ml) were stirred in methanol (100 ml) for 12 hours at room temperature under argon. The solvent and triethylamine were removed on a rotary evap... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic thiol.Vinyl | Monosulfide | null | null | c1ccccc1.C1C2CC3CC1CC(C2)C3 | null | CO | null | null | C=CC(=O)NC12CC3CC(CC(C3)C1)C2.CC(C)(C)c1cc(S)cc(C(C)(C)C)c1O>CO>CC(C)(C)c1cc(SCCC(=O)NC23CC4CC(CC(C4)C2)C3)cc(C(C)(C)C)c1O |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-0c853584f40147fcac7748a5dc4bc09f | C=CC(=O)Cl.CCN(CC)CC.NC12CCCC(C1)C2>>C=CC(=O)NC1CCC2CC1C2(C)C | C(C)N(CC)CC.C12(CCCC(C1)C2)N.C(C)OCC.C(C=C)(=O)Cl.C(C)OCC>>CC1(C2CCC(C1C2)NC(C=C)=O)C | Cl[C:3]([CH:2]=[CH2:1])=[O:4].CCN(C[CH3:13])C[CH3:14].[NH2:5][C:12]12[CH2:9][CH2:8][CH2:7][CH:6]([CH2:10]1)[CH2:11]2>>[CH2:1]=[CH:2][C:3](=[O:4])[NH:5][CH:6]1[CH2:7][CH2:8][CH:9]2[CH2:10][CH:11]1[C:12]2([CH3:13])[CH3:14] | C=CC(=O)Cl.CCN(CC)CC.NC12CCCC(C1)C2 | C=CC(=O)NC1CCC2CC1C2(C)C | null | null | null | Acylation | OtherReaction | 6c283f5a225acb578197d69066af8b35f236772aaebb88e01b308193792ee121 | dc53a24d0a75ead6936ba4bfea2aaa20482a3c074844b86c65edebf5b2d17cae | C1CC2CC(C1)C2 | C-C-N(-C-[CH3;D1;+0:1])-C-[CH3;D1;+0:2].Cl-[C;H0;D3;+0:3](=[O;D1;H0:4])-[C:5]=[C;D1;H2:6].[NH2;D1;+0:7]-[C;H0;D4;+0:8]12-[CH2;D2;+0:9]-[CH;D3;+0:10](-[C:11]-[C:12]-[CH2;D2;+0:13]-1)-[CH2;D2;+0:14]-2>>[C;D1;H2:6]=[C:5]-[C;H0;D3;+0:3](=[O;D1;H0:4])-[NH;D2;+0:7]-[CH;D3;+0:10]1-[C:11]-[C:12]-[CH;D3;+0:13]2-[CH2;D2;+0:9]-[C... | null | [] | null | null | 72 | HOUR | Following the procedure of Example 3, a solution of acryloyl chloride (4.05 ml, 0.05 mole) in ethyl ether (50 ml) was added dropwise to a cold 5° C. mixture of triethylamine (15.3 ml, 0.11 mole) and norpinylamine (6.96; g, 0.05 mole) in ethyl ether (400 ml). The reaction was allowed to warm to room temperature and stir... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine.Tertiary amine | Secondary amide | C1CC2CC(C1)C2 | C1CC2CC(C1)C2 | C1CC2CC(C1)C2 | HCl | null | null | 72 | C=CC(=O)Cl.CCN(CC)CC.NC12CCCC(C1)C2>>C=CC(=O)NC1CCC2CC1C2(C)C |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-2ab50f00f4ee40f3872001d53d2b0523 | C=CC(=O)Cl.NC1C2CC3CC(C2)CC1C3>>C=CC(=O)NC1C2CC3CC(C2)CC1C3 | C(C=C)(=O)Cl.Cl.C12C(C3CC(CC(C1)C3)C2)N.C(C)N(CC)CC>>C12C(C3CC(CC(C1)C3)C2)NC(C=C)=O | Cl[C:3]([CH:2]=[CH2:1])=[O:4].[NH2:5][CH:6]1[CH:7]2[CH2:8][CH:9]3[CH2:10][CH:11]([CH2:12]2)[CH2:13][CH:14]1[CH2:15]3>>[CH2:1]=[CH:2][C:3](=[O:4])[NH:5][CH:6]1[CH:7]2[CH2:8][CH:9]3[CH2:10][CH:11]([CH2:12]2)[CH2:13][CH:14]1[CH2:15]3 | C=CC(=O)Cl.NC1C2CC3CC(C2)CC1C3 | C=CC(=O)NC1C2CC3CC(C2)CC1C3 | null | null | C(Cl)Cl.C(C)OCC | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | C1C2CC3CC1CC(C2)C3 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]=[C;D1;H2:4].[C:5]-[C:6](-[NH2;D1;+0:7])-[C:8]>>[C:5]-[C:6](-[NH;D2;+0:7]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]=[C;D1;H2:4])-[C:8] | null | [] | null | null | 12 | HOUR | A solution of acryloyl chloride (4.52 g, 0.05 mole) in ethyl ether (20 ml) was added dropwise to a stirring mixture of 2-adamantylamine hydrochloride (9.35 g, 0.05 mole) and triethylamine (30.65 ml) in methylene chloride (200 ml) and ethyl ether (200 ml) over a 30 minute period. The solution was stirred for 12 hours, t... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | C1C2CC3CC1CC(C2)C3 | HCl | C(Cl)Cl.C(C)OCC | null | 12 | C=CC(=O)Cl.NC1C2CC3CC(C2)CC1C3>C(Cl)Cl.C(C)OCC>C=CC(=O)NC1C2CC3CC(C2)CC1C3 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-d9dbb8c843704e72b8d436d338439278 | C=CC(=O)NC1C2CC3CC(C2)CC1C3.CC(C)(C)c1cc(S)cc(C(C)(C)C)c1O>>CC(C)(C)c1cc(SCCC(=O)NC2C3CC4CC(C3)CC2C4)cc(C(C)(C)C)c1O | C(C)N(CC)CC.CC(C)(C)C1=C(C(=CC(=C1)S)C(C)(C)C)O.C12C(C3CC(CC(C1)C3)C2)NC(C=C)=O>>CC(C)(C)C=1C=C(C=C(C1O)C(C)(C)C)SCCC(=O)NC1C2CC3CC(CC1C3)C2 | [CH2:9]=[CH:10][C:11](=[O:12])[NH:13][CH:14]1[CH:15]2[CH2:16][CH:17]3[CH2:18][CH:19]([CH2:20]2)[CH2:21][CH:22]1[CH2:23]3.[CH3:1][C:2]([CH3:3])([CH3:4])[c:5]1[cH:6][c:7]([SH:8])[cH:24][c:25]([C:26]([CH3:27])([CH3:28])[CH3:29])[c:30]1[OH:31]>>[CH3:1][C:2]([CH3:3])([CH3:4])[c:5]1[cH:6][c:7]([S:8][CH2:9][CH2:10][C:11](=[O:... | C=CC(=O)NC1C2CC3CC(C2)CC1C3.CC(C)(C)c1cc(S)cc(C(C)(C)C)c1O | CC(C)(C)c1cc(SCCC(=O)NC2C3CC4CC(C3)CC2C4)cc(C(C)(C)C)c1O | null | null | CO | Heteroatom Alkylation and Arylation | thia-Michael addition | 9c1714ade80d0bfd6c4747e19bbd5e181aebdd6e70fcf1c4b03944a726aeaf5d | ff275b76dc1ff1d0f3afaf057f654852a0a807709b71c50992bfc9df07afc001 | O=C(CCSc1ccccc1)NC1C2CC3CC(C2)CC1C3 | [C:1]-[#7:2]-[C:3](=[O;D1;H0:4])-[CH;D2;+0:5]=[CH2;D1;+0:6].[SH;D1;+0:7]-[c:8](:[c:9]):[c:10]>>[C:1]-[#7:2]-[C:3](=[O;D1;H0:4])-[CH2;D2;+0:5]-[CH2;D2;+0:6]-[S;H0;D2;+0:7]-[c:8](:[c:9]):[c:10] | null | [] | null | null | null | null | Following the procedure of Example 4, triethylamine (0.5 ml) was added to a solution of 2,6-bis(1,1-dimethylethyl)-4-mercaptophenol (1.19 g, 0.005 mole) and the N-tricyclo[3.3.1.13,7 ]dec-2-yl-2-propenamide (1.02 g, 0.005 mole) in methanol (100 ml) and the solution stirred at room temperature for 12 hours. The solvent ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic thiol.Vinyl | Monosulfide | null | null | c1ccccc1.C1C2CC3CC1CC(C2)C3 | null | CO | null | null | C=CC(=O)NC1C2CC3CC(C2)CC1C3.CC(C)(C)c1cc(S)cc(C(C)(C)C)c1O>CO>CC(C)(C)c1cc(SCCC(=O)NC2C3CC4CC(C3)CC2C4)cc(C(C)(C)C)c1O |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-a4fca27471be4fcab54d8e506201a961 | C1CC2CCC1CNC2.C=CC(=O)Cl>>C=CC(=O)N1CC2CCC(CC2)C1 | C12CNCC(CC1)CC2.C(C)N(CC)CC.C(C=C)(=O)Cl>>O=C(C=C)N1CC2CCC(C1)CC2 | [NH:5]1[CH2:6][CH:7]2[CH2:8][CH2:9][CH:10]([CH2:11][CH2:12]2)[CH2:13]1.Cl[C:3]([CH:2]=[CH2:1])=[O:4]>>[CH2:1]=[CH:2][C:3](=[O:4])[N:5]1[CH2:6][CH:7]2[CH2:8][CH2:9][CH:10]([CH2:11][CH2:12]2)[CH2:13]1 | C1CC2CCC1CNC2.C=CC(=O)Cl | C=CC(=O)N1CC2CCC(CC2)C1 | null | null | C(C)OCC | Acylation | N-alkylation of secondary amines with alkyl halides | 0a2fca6ed239ebd7850f19f885f0ed20bcb9643e5d524100cfda4bb247ce5e8e | 96cb0a2fed10552c5770a45a2d6523b47ac3e38928b4a9c698d8577451182dcd | C1CC2CCC1CNC2 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]=[C;D1;H2:4].[C:5]-[C:6]-[NH;D2;+0:7]-[C:8]-[C:9]>>[C:5]-[C:6]-[N;H0;D3;+0:7](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]=[C;D1;H2:4])-[C:8]-[C:9] | null | [] | null | null | 72 | HOUR | A solution of acryloyl chloride (4.05 ml, 0.05 mole) in 50 ml of ethyl ether was added with stirring to a cold mixture of 3-azabicyclo[3.2.2]nonane (6.26 g, 0.05 mole) and triethylamine (15.3 ml, 0.11 mole) in 250 ml of ethyl ether. The ice bath was removed and the reaction was allowed to warm to room temperature and s... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Secondary amine | Tertiary amide | C1CC2CCC1CNC2 | C1CC2CCC1C[NH]C2 | C1CC2CCC1C[NH]C2 | HCl | C(C)OCC | null | 72 | C1CC2CCC1CNC2.C=CC(=O)Cl>C(C)OCC>C=CC(=O)N1CC2CCC(CC2)C1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-e382774d53ff40749e90ddad18853b83 | CC(C)(C)c1cc(S)cc(C(C)(C)C)c1O.CCOC(=O)CCCBr>>CC(C)(C)c1cc(SCCCC(=O)O)cc(C(C)(C)C)c1O | O.[OH-].[K+].CC(C)(C)C1=C(C(=CC(=C1)S)C(C)(C)C)O.C(C)OC(CCCBr)=O>>CC(C)(C)C=1C=C(C=C(C1O)C(C)(C)C)SCCCC(=O)O | [CH3:1][C:2]([CH3:3])([CH3:4])[c:5]1[cH:6][c:7]([SH:8])[cH:15][c:16]([C:17]([CH3:18])([CH3:19])[CH3:20])[c:21]1[OH:22].CC[O:14][C:12]([CH2:11][CH2:10][CH2:9]Br)=[O:13]>>[CH3:1][C:2]([CH3:3])([CH3:4])[c:5]1[cH:6][c:7]([S:8][CH2:9][CH2:10][CH2:11][C:12](=[O:13])[OH:14])[cH:15][c:16]([C:17]([CH3:18])([CH3:19])[CH3:20])[c:... | CC(C)(C)c1cc(S)cc(C(C)(C)C)c1O.CCOC(=O)CCCBr | CC(C)(C)c1cc(SCCCC(=O)O)cc(C(C)(C)C)c1O | null | null | CC(=O)C | Heteroatom Alkylation and Arylation | OtherReaction | 416f41029f1c89efe2c67ebec7aefbed322c00b82c0140525349959ca6b7e758 | ec959f8bc7e482c779a4753dcb04c15a7fd6788748d10fbc4f292f960558e0ba | c1ccccc1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3]-[C:4](=[O;D1;H0:5])-[O;H0;D2;+0:6]-C-C.[SH;D1;+0:7]-[c:8](:[c:9]):[c:10]>>[O;D1;H0:5]=[C:4](-[OH;D1;+0:6])-[C:3]-[C:2]-[CH2;D2;+0:1]-[S;H0;D2;+0:7]-[c:8](:[c:9]):[c:10] | null | [] | null | null | 1.5 | HOUR | Potassium hydroxide flakes (2.52 g, 0.045 mole) were added to a clear solution of 2,6-bis(1,1-dimethylethyl)-4-mercaptophenol (3.57 g, 0.0165 mole) and ethyl-4-bromo-butyrate (3.23 g, 0.0165 mole) in acetone (10 ml). Water (20 ml) was added and the solution stirred for 1.5 hours, the solvent removed on a rotary evapora... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester.Aromatic thiol | Carboxylic acid.Monosulfide | null | null | c1ccccc1 | HBr | CC(=O)C | null | 1.5 | CC(C)(C)c1cc(S)cc(C(C)(C)C)c1O.CCOC(=O)CCCBr>CC(=O)C>CC(C)(C)c1cc(SCCCC(=O)O)cc(C(C)(C)C)c1O |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-0036974a8e5f42138d995cc37559e5bb | NC1CN2CCC1CC2.O=C(Cl)CCl>>O=C(CCl)NC1CN2CCC1CC2 | [OH-].[K+].Cl.Cl.NC1CN2CCC1CC2.[Cl-].[Na+].ClCC(=O)Cl>>Cl.N12CC(C(CC1)CC2)NC(CCl)=O | [NH2:6][CH:7]1[CH2:8][N:9]2[CH2:10][CH2:11][CH:12]1[CH2:13][CH2:14]2.Cl[C:3](=[O:2])[CH2:4][Cl:5]>>[O:2]=[C:3]([CH2:4][Cl:5])[NH:6][CH:7]1[CH2:8][N:9]2[CH2:10][CH2:11][CH:12]1[CH2:13][CH2:14]2 | NC1CN2CCC1CC2.O=C(Cl)CCl | O=C(CCl)NC1CN2CCC1CC2 | null | null | C(Cl)Cl.O | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | C1CN2CCC1CC2 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[Cl;D1;H0:4].[#7:5]-[C:6]-[C:7](-[NH2;D1;+0:8])-[C:9]>>[#7:5]-[C:6]-[C:7](-[NH;D2;+0:8]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[Cl;D1;H0:4])-[C:9] | 144 | [{"value": 144.0, "product": "Cl.N12CC(C(CC1)CC2)NC(CCl)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | Potassium hydroxide (10 g) was added to a solution of 3-aminoquinuclidine dihydrochloride (10.45 g, 0.052 mole) in water (80 ml) saturated with sodium chloride. After stirring for 30 minutes, methylene chloride (75 ml) was added and the layers separated. The aqueous layer was washed with methylene chloride (2×75 ml), a... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | C1CN2CCC1CC2 | HCl | C(Cl)Cl.O | null | 0.5 | NC1CN2CCC1CC2.O=C(Cl)CCl>C(Cl)Cl.O>O=C(CCl)NC1CN2CCC1CC2 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-7c6e013327b6432ebdbce4d8fc732f65 | CC(C)(C)c1cc(S)cc(C(C)(C)C)c1O.O=C(CCl)NC1CN2CCC1CC2>>CC(C)(C)c1cc(SCC(=O)NC2CN3CCC2CC3)cc(C(C)(C)C)c1O | Cl.N12CC(C(CC1)CC2)NC(CCl)=O.CC(C)(C)C1=C(C(=CC(=C1)S)C(C)(C)C)O.C(C)N(CC)CC>>Cl.N12CC(C(CC1)CC2)NC(CSC2=CC(=C(C(=C2)C(C)(C)C)O)C(C)(C)C)=O | [CH3:1][C:2]([CH3:3])([CH3:4])[c:5]1[cH:6][c:7]([SH:8])[cH:21][c:22]([C:23]([CH3:24])([CH3:25])[CH3:26])[c:27]1[OH:28].Cl[CH2:9][C:10](=[O:11])[NH:12][CH:13]1[CH2:14][N:15]2[CH2:16][CH2:17][CH:18]1[CH2:19][CH2:20]2>>[CH3:1][C:2]([CH3:3])([CH3:4])[c:5]1[cH:6][c:7]([S:8][CH2:9][C:10](=[O:11])[NH:12][CH:13]2[CH2:14][N:15]... | CC(C)(C)c1cc(S)cc(C(C)(C)C)c1O.O=C(CCl)NC1CN2CCC1CC2 | CC(C)(C)c1cc(SCC(=O)NC2CN3CCC2CC3)cc(C(C)(C)C)c1O | null | null | C(C)#N | Heteroatom Alkylation and Arylation | thioether_nucl_sub | 26df88c6a3f5f203c89584658be4e126cb42994c98a2e16bc812e1036cdae857 | 8b2f52296c3a93039174c980b6042ba15754e04d6892a1284c3a32985220b214 | O=C(CSc1ccccc1)NC1CN2CCC1CC2 | Cl-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#7:4]-[C:5].[SH;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[C:5]-[#7:4]-[C:2](=[O;D1;H0:3])-[CH2;D2;+0:1]-[S;H0;D2;+0:6]-[c:7](:[c:8]):[c:9] | null | [] | null | null | 12 | HOUR | The title compound was prepared by dissolving the product of Example 17 (2.0 g, 0.0084 mole) and 2,6-bis(1,1-dimethylethyl)-4-mercaptophenol (1.99 g, 0.0084 mole) in acetonitrile (25 ml). Triethylamine (5 ml) was added to the mixture and the mixture stirred at room temperature for 12 hours then refluxed for 72 hours. T... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic thiol | Monosulfide | null | null | c1ccccc1.C1CN2CCC1CC2 | HCl | C(C)#N | null | 12 | CC(C)(C)c1cc(S)cc(C(C)(C)C)c1O.O=C(CCl)NC1CN2CCC1CC2>C(C)#N>CC(C)(C)c1cc(SCC(=O)NC2CN3CCC2CC3)cc(C(C)(C)C)c1O |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-9d58c3ea89d9414abd934e6ec8e46202 | N#C[S-].Oc1c(Cl)cccc1Cl>>N#CSc1cc(Cl)c(O)c(Cl)c1 | ClC1=C(C(=CC=C1)Cl)O.[S-]C#N.[NH4+]>>ClC=1C=C(C=C(C1O)Cl)SC#N | [N:1]#[C:2][S-:3].[cH:4]1[cH:5][c:6]([Cl:7])[c:8]([OH:9])[c:10]([Cl:11])[cH:12]1>>[N:1]#[C:2][S:3][c:4]1[cH:5][c:6]([Cl:7])[c:8]([OH:9])[c:10]([Cl:11])[cH:12]1 | N#C[S-].Oc1c(Cl)cccc1Cl | N#CSc1cc(Cl)c(O)c(Cl)c1 | null | null | CO | Heteroatom Alkylation and Arylation | OtherReaction | 29d483be92b78aea9894649c5ff004e9773d34416f95eeab1829acdbdeaacc59 | 21e67be598c63344ea1fea503581f1ce4855b092ed4079749b71ebb3b04166d6 | c1ccccc1 | [N;D1;H0:1]#[C:2]-[S-;H0;D1:3].[c:4]:[c:5]:[cH;D2;+0:6]:[c:7]:[c:8]>>[N;D1;H0:1]#[C:2]-[S;H0;D2;+0:3]-[c;H0;D3;+0:6](:[c:5]:[c:4]):[c:7]:[c:8] | 14.8 | [{"value": 14.8, "product": "ClC=1C=C(C=C(C1O)Cl)SC#N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 3 | HOUR | 2,6-Dichlorophenol (100 g, 0.613 mole) and ammonium thiocyanate (102.73 g, 1.350 mole) were mixed in methanol and the solution cooled to 0° C. Chlorine gas was bubbled through the reaction, maintaining the temperature below 10° C. The solution turned a pale yellow color. The reaction was stirred for a total of 3 hours ... | 10.6084/m9.figshare.5104873.v1 | null | null | Monosulfide | c1ccccc1 | c1ccccc1 | c1ccccc1 | null | CO | 0 | 3 | N#C[S-].Oc1c(Cl)cccc1Cl>CO>N#CSc1cc(Cl)c(O)c(Cl)c1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-f85390a039b44730a2251ea5bde13487 | N#C[S-].Oc1c(-c2ccccc2)cccc1-c1ccccc1>>N#CSc1cc(-c2ccccc2)c(O)c(-c2ccccc2)c1 | C1(=CC=CC=C1)C1=C(C(=CC=C1)C1=CC=CC=C1)O.[S-]C#N.[NH4+]>>OC1=C(C=C(C=C1C1=CC=CC=C1)SC#N)C1=CC=CC=C1 | [N:1]#[C:2][S-:3].[cH:4]1[cH:5][c:6](-[c:7]2[cH:8][cH:9][cH:10][cH:11][cH:12]2)[c:13]([OH:14])[c:15](-[c:16]2[cH:17][cH:18][cH:19][cH:20][cH:21]2)[cH:22]1>>[N:1]#[C:2][S:3][c:4]1[cH:5][c:6](-[c:7]2[cH:8][cH:9][cH:10][cH:11][cH:12]2)[c:13]([OH:14])[c:15](-[c:16]2[cH:17][cH:18][cH:19][cH:20][cH:21]2)[cH:22]1 | N#C[S-].Oc1c(-c2ccccc2)cccc1-c1ccccc1 | N#CSc1cc(-c2ccccc2)c(O)c(-c2ccccc2)c1 | null | null | CO | Heteroatom Alkylation and Arylation | OtherReaction | 29d483be92b78aea9894649c5ff004e9773d34416f95eeab1829acdbdeaacc59 | 21e67be598c63344ea1fea503581f1ce4855b092ed4079749b71ebb3b04166d6 | c1ccc(-c2cccc(-c3ccccc3)c2)cc1 | [N;D1;H0:1]#[C:2]-[S-;H0;D1:3].[c:4]:[c:5]:[cH;D2;+0:6]:[c:7]:[c:8]>>[N;D1;H0:1]#[C:2]-[S;H0;D2;+0:3]-[c;H0;D3;+0:6](:[c:5]:[c:4]):[c:7]:[c:8] | null | [] | -5 | CELSIUS | 12 | HOUR | 2,6-Diphenylphenol (100.0 g, 0.406 mole) and ammonium thiocyanate (76.99 g, 0.893 mole) were suspended in methanol (150 ml) in a three-necked round bottom flask equipped with magnetic stirrer, thermometer and gas inlet tube. The reaction mixture was cooled to -5° C. in an acetone/ice bath and chlorine gas bubbled throu... | 10.6084/m9.figshare.5104873.v1 | null | null | Monosulfide | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1 | null | CO | -5 | 12 | N#C[S-].Oc1c(-c2ccccc2)cccc1-c1ccccc1>CO>N#CSc1cc(-c2ccccc2)c(O)c(-c2ccccc2)c1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-da15063755aa4e6593c6276b75ed08d3 | Nc1cc([N+](=O)[O-])ccc1O>>Cc1nc2cc([N+](=O)[O-])ccc2o1 | NC1=C(C=CC(=C1)[N+](=O)[O-])O.N1=CC=CC=C1>>[N+](=O)([O-])C=1C=CC2=C(N=C(O2)C)C1 | [NH2:3][c:4]1[cH:5][c:6]([N+:7](=[O:8])[O-:9])[cH:10][cH:11][c:12]1[OH:13]>>[CH3:1][c:2]1[n:3][c:4]2[cH:5][c:6]([N+:7](=[O:8])[O-:9])[cH:10][cH:11][c:12]2[o:13]1 | Nc1cc([N+](=O)[O-])ccc1O | Cc1nc2cc([N+](=O)[O-])ccc2o1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 69607c2d59b5fead97afd71884d6be0e92f91671888bf411483c147dbce12794 | 3342e49c63e96450a989cd80ff0976d0f3053d9603daab2b16372a46a87ff644 | c1ccc2ocnc2c1 | [NH2;D1;+0:1]-[c:2](:[c:3]):[c:4](-[OH;D1;+0:5]):[c:6]>>[C;D1;H3:7]-[c:8]1:[n;H0;D2;+0:1]:[c:2](:[c:3]):[c:4](:[c:6]):[o;H0;D2;+0:5]:1 | null | [] | null | null | 8 | HOUR | A dye of the invention is prepared by dissolving about 369 parts of 2-amino-4-nitrophenol in about 600 ml of warm pyridine in a 2 liter three-necked flask equipped with a mechanical stirrer, a Dean & Stark adapter or glass trap to collect distilled off solvent, and a condenser. About 600 parts of triethyl orthoacetate ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic alcohol.Primary amine | null | c1ccccc1 | c1ccc2ocnc2c1 | c1ccc2ocnc2c1 | Other | null | null | 8 | Nc1cc([N+](=O)[O-])ccc1O>>Cc1nc2cc([N+](=O)[O-])ccc2o1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-cbdf37bd45334f7f8694cc9857bcf8c9 | C=CC(=O)Cl.Cc1nc2cc(N)ccc2o1>>C=CC(=O)Nc1ccc2oc(C)nc2c1 | C(C=C)(=O)Cl.NC=1C=CC2=C(N=C(O2)C)C1.C(C)N(CC)CC>>C(C=C)(=O)NC=1C=CC2=C(N=C(O2)C)C1 | Cl[C:3]([CH:2]=[CH2:1])=[O:4].[NH2:5][c:6]1[cH:7][cH:8][c:9]2[o:10][c:11]([CH3:12])[n:13][c:14]2[cH:15]1>>[CH2:1]=[CH:2][C:3](=[O:4])[NH:5][c:6]1[cH:7][cH:8][c:9]2[o:10][c:11]([CH3:12])[n:13][c:14]2[cH:15]1 | C=CC(=O)Cl.Cc1nc2cc(N)ccc2o1 | C=CC(=O)Nc1ccc2oc(C)nc2c1 | null | null | O1CCCC1 | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | c1ccc2ocnc2c1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]=[C;D1;H2:4].[#7;a:5]:[c:6]:[c:7]:[c:8](-[NH2;D1;+0:9]):[c:10]>>[#7;a:5]:[c:6]:[c:7]:[c:8](-[NH;D2;+0:9]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]=[C;D1;H2:4]):[c:10] | null | [] | 0 | CELSIUS | null | null | About 150 parts of (2) are dissolved in about 1200 ml of warm tetrahydrofuran in a 3 liter three-necked flask equipped with a mechanical stirrer and dropping funnel. About 113 parts of triethylamine are added to the flask and then cooled to 0° C. using an ice bath. About 100 parts of acryloyl chloride are combined with... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccc2ocnc2c1 | HCl | O1CCCC1 | 0 | null | C=CC(=O)Cl.Cc1nc2cc(N)ccc2o1>O1CCCC1>C=CC(=O)Nc1ccc2oc(C)nc2c1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-b701611ad3e041048caec74b4e9736d0 | C=CC(=O)Nc1ccc2oc(C)nc2c1.CCOS(=O)(=O)c1ccc(C)cc1>>C=CC(=O)Nc1ccc2oc(C)[n+](CC)c2c1.Cc1ccc(S(=O)(=O)[O-])cc1 | C(C=C)(=O)NC=1C=CC2=C(N=C(O2)C)C1.C1(=CC=C(C=C1)S(=O)(=O)OCC)C.CC(=O)N(C)C.C1=CC(=CC=C1[N+](=O)[O-])O>>C1(=CC=C(C=C1)S(=O)(=O)[O-])C.C(C)[N+]1=C(OC2=C1C=C(C=C2)NC(C=C)=O)C | [CH2:1]=[CH:2][C:3](=[O:4])[NH:5][c:6]1[cH:7][cH:8][c:9]2[o:10][c:11]([CH3:12])[n:13][c:16]2[cH:17]1.[CH2:14]([CH3:15])[O:26][S:23]([c:22]1[cH:21][cH:20][c:19]([CH3:18])[cH:28][cH:27]1)(=[O:24])=[O:25]>>[CH2:1]=[CH:2][C:3](=[O:4])[NH:5][c:6]1[cH:7][cH:8][c:9]2[o:10][c:11]([CH3:12])[n+:13]([CH2:14][CH3:15])[c:16]2[cH:17... | C=CC(=O)Nc1ccc2oc(C)nc2c1.CCOS(=O)(=O)c1ccc(C)cc1 | C=CC(=O)Nc1ccc2oc(C)[n+](CC)c2c1.Cc1ccc(S(=O)(=O)[O-])cc1 | null | null | C(C)OCC | Functional Group Interconversion | OtherReaction | 1f2a2d1f9557664c3df2497995934709c0dc996f98ef61b73ad7b116a5a69522 | f1bbf9aa3c82f5e49be9f6d53533b6bb152f359232b6d32090c168949766aa71 | c1ccc2oc[nH+]c2c1.c1ccccc1 | [C;D1;H3:1]-[CH2;D2;+0:2]-[O;H0;D2;+0:3]-[#16:4](=[O;D1;H0:5])(=[O;D1;H0:6])-[c:7]1:[c:8]:[c:9]:[c:10](-[C;D1;H3:11]):[c:12]:[c:13]:1.[C;D1;H3:14]-[c:15]1:[#8;a:16]:[c:17](:[c:18]):[c:19](:[c:20]):[n;H0;D2;+0:21]:1>>[C;D1;H3:14]-[c:15]1:[#8;a:16]:[c:17](:[c:18]):[c:19](:[c:20]):[n+;H0;D3:21]:1-[CH2;D2;+0:2]-[C;D1;H3:1]... | null | [] | 120 | CELSIUS | 8 | HOUR | About 100 parts of (3) are combined with about 109 parts of ethyl p-toluene sulfonate, 100 ml dimethylacetamide, and 5 ml p-nitrophenol (to inhibit polymerization) in a 500 ml three-necked flask equipped with a mechanical stirrer and condenser. The reaction mixture is heated at about 120° C. for about 5 hours while sti... | 10.6084/m9.figshare.5104873.v1 | null | null | null | c1ccc2ocnc2c1 | C1=[NH+]c2ccccc2O1 | C1=[NH+]c2ccccc2O1.c1ccccc1 | null | C(C)OCC | 120 | 8 | C=CC(=O)Nc1ccc2oc(C)nc2c1.CCOS(=O)(=O)c1ccc(C)cc1>C(C)OCC>C=CC(=O)Nc1ccc2oc(C)[n+](CC)c2c1.Cc1ccc(S(=O)(=O)[O-])cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-e8381d73f4f9423dbff70d4f1bb4f249 | C1CCNC1.CCOC(=O)CBr>>CCOC(=O)CN1CCCC1 | C1(=CC=CC=C1)C.N1CCCC1.BrCC(=O)OCC>>N1(CCCC1)CC(=O)OCC | [NH:7]1[CH2:8][CH2:9][CH2:10][CH2:11]1.Br[CH2:6][C:4]([O:3][CH2:2][CH3:1])=[O:5]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][N:7]1[CH2:8][CH2:9][CH2:10][CH2:11]1 | C1CCNC1.CCOC(=O)CBr | CCOC(=O)CN1CCCC1 | null | null | O1CCCC1 | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 03dab874eefa94dab455a5a338e9e6614242955d9fcbc8487ef03ad4144d84fb | e09591825c4808efe257024fb4bbe3690a7cda9ee664fef9727988761bae5b4a | C1CCNC1 | Br-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#8:4]-[C:5].[C:6]1-[C:7]-[NH;D2;+0:8]-[C:9]-[C:10]-1>>[C:5]-[#8:4]-[C:2](=[O;D1;H0:3])-[CH2;D2;+0:1]-[N;H0;D3;+0:8]1-[C:7]-[C:6]-[C:10]-[C:9]-1 | null | [] | null | null | null | null | To an ice bath-cooled solution of 213.4 g (3 mol) of pyrrolidine in 450 mL of tetrahydrofuran was added dropwise over about 2 hours 250.5 g (1.5 mol) of ethyl bromoacetate, maintaining the temperature below 30° C. To this solution was added 150 mL of toluene to precipitate pyrrolidinium bromide, which was separated by ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester.Secondary amine | Ester.Tertiary amine | C1CCNC1 | C1CC[NH]C1 | C1CC[NH]C1 | HBr | O1CCCC1 | null | null | C1CCNC1.CCOC(=O)CBr>O1CCCC1>CCOC(=O)CN1CCCC1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-f0f08fb4c13d448a91c7baff3cb35ade | CCOC(=O)CN1CCCC1.CN(C)CCO>>CN(C)CCOC(=O)CN1CCCC1 | N1(CCCC1)CC(=O)OCC.[H-].[Na+].CN(C)CCO>>N1(CCCC1)CC(=O)OCCN(C)C | CCO[C:7](=[O:8])[CH2:9][N:10]1[CH2:11][CH2:12][CH2:13][CH2:14]1.[CH3:1][N:2]([CH3:3])[CH2:4][CH2:5][OH:6]>>[CH3:1][N:2]([CH3:3])[CH2:4][CH2:5][O:6][C:7](=[O:8])[CH2:9][N:10]1[CH2:11][CH2:12][CH2:13][CH2:14]1 | CCOC(=O)CN1CCCC1.CN(C)CCO | CN(C)CCOC(=O)CN1CCCC1 | null | null | null | Protection | Transesterification | 1adccd25c595429871da3756142c075aac7032d22473ca1588e41d51e1a19040 | a6c84db4df003bced50681f216baba6e759c1d4451f21f814c7bb7ee782a7375 | C1CCNC1 | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[#7:4].[C:5]-[C:6]-[OH;D1;+0:7]>>[#7:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[O;H0;D2;+0:7]-[C:6]-[C:5] | null | [] | 150 | CELSIUS | null | null | To a mixture of 80 g (0.51 mol) of ethyl 1-pyrrolidineacetate and 0.5 g of sodium hydride (in the form of a 60% by weight suspension in mineral oil) was added 48 g (0.54 mol) of 2-(N,N-dimethylamino)ethanol. The mixture was purged with nitrogen gas, heated gradually and then maintained at about 150° C. while collecting... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Primary alcohol | Ester | null | null | C1CC[NH]C1 | HO- | null | 150 | null | CCOC(=O)CN1CCCC1.CN(C)CCO>>CN(C)CCOC(=O)CN1CCCC1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-c4df8ed7448a4eceb5456f490db7f354 | CCOC(=O)CN1CCCC1.OCCN1CCCC1>>O=C(CN1CCCC1)OCCN1CCCC1 | [H-].[Na+].N1(CCCC1)CC(=O)OCC.N1(CCCC1)CCO>>N1(CCCC1)CC(=O)OCCN1CCCC1 | CCO[C:2](=[O:1])[CH2:3][N:4]1[CH2:5][CH2:6][CH2:7][CH2:8]1.[OH:9][CH2:10][CH2:11][N:12]1[CH2:13][CH2:14][CH2:15][CH2:16]1>>[O:1]=[C:2]([CH2:3][N:4]1[CH2:5][CH2:6][CH2:7][CH2:8]1)[O:9][CH2:10][CH2:11][N:12]1[CH2:13][CH2:14][CH2:15][CH2:16]1 | CCOC(=O)CN1CCCC1.OCCN1CCCC1 | O=C(CN1CCCC1)OCCN1CCCC1 | null | null | null | Acylation | Transesterification | c42e047d71ad2593a6d29093d1fe2ca16ccfd6db7b15eecf1eab340181aef83e | cb08be6428b0a3737df44d00995165c06a05fb7dec4fab744c09315c4f7771d4 | O=C(CN1CCCC1)OCCN1CCCC1 | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[#7:4].[C:5]-[C:6]-[OH;D1;+0:7]>>[#7:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[O;H0;D2;+0:7]-[C:6]-[C:5] | null | [] | 225 | CELSIUS | null | null | To a mixture of 1.3 g of sodium hydride (in the form of a 60% by weight suspension in mineral oil) and 100 g (0.64 mol) of ethyl 1-pyrrolidineacetate was added 91 g of 2-(1-pyrrolidinyl)ethanol. The mixture was heated slowly to about 225° C., and the ethanol by-product was collected in a Dean-Stark trap. The reaction m... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Primary alcohol | Ester | null | null | C1CC[NH]C1.C1CC[NH]C1 | HO- | null | 225 | null | CCOC(=O)CN1CCCC1.OCCN1CCCC1>>O=C(CN1CCCC1)OCCN1CCCC1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-6a86b0c3c8d04f9588652776384b7532 | CCN(CC)CCO.CCOC(=O)CN1CCCC1>>CCN(CC)CCOC(=O)CN1CCCC1 | N1(CCCC1)CC(=O)OCC.C(C)N(CC)CCO>>N1(CCCC1)CC(=O)OCCN(CC)CC | [CH3:1][CH2:2][N:3]([CH2:4][CH3:5])[CH2:6][CH2:7][OH:8].CCO[C:9](=[O:10])[CH2:11][N:12]1[CH2:13][CH2:14][CH2:15][CH2:16]1>>[CH3:1][CH2:2][N:3]([CH2:4][CH3:5])[CH2:6][CH2:7][O:8][C:9](=[O:10])[CH2:11][N:12]1[CH2:13][CH2:14][CH2:15][CH2:16]1 | CCN(CC)CCO.CCOC(=O)CN1CCCC1 | CCN(CC)CCOC(=O)CN1CCCC1 | null | null | null | Acylation | Transesterification | c42e047d71ad2593a6d29093d1fe2ca16ccfd6db7b15eecf1eab340181aef83e | cb08be6428b0a3737df44d00995165c06a05fb7dec4fab744c09315c4f7771d4 | C1CCNC1 | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[#7:4].[C:5]-[C:6]-[OH;D1;+0:7]>>[#7:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[O;H0;D2;+0:7]-[C:6]-[C:5] | null | [] | null | null | null | null | Using the method of Example 5, ethyl 1-pyrrolidineacetate was reacted with 2-(N,N-diethylamino)ethanol to provide 2-(N,N-diethylamino)ethyl 1-pyrrolidineacetate, b.p. 92° C. at 250 μmHg.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Ester.Primary alcohol | Ester | null | null | C1CC[NH]C1 | HO- | null | null | null | CCN(CC)CCO.CCOC(=O)CN1CCCC1>>CCN(CC)CCOC(=O)CN1CCCC1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-5543a960e72d4b11830530e7308453a5 | CNC.O=C1CC(CCl)=NC=C1OCc1ccccc1>>CN(C)CC1=NC=C(OCc2ccccc2)C(=O)C1 | ClCC1=NC=C(C(C1)=O)OCC1=CC=CC=C1.O1CCCC1.Cl.CNC.[OH-].[Na+]>>C(C1=CC=CC=C1)OC=1C(CC(=NC1)CN(C)C)=O | [CH3:1][NH:2][CH3:3].Cl[CH2:4][C:5]1=[N:6][CH:7]=[C:8]([O:9][CH2:10][c:11]2[cH:12][cH:13][cH:14][cH:15][cH:16]2)[C:17](=[O:18])[CH2:19]1>>[CH3:1][N:2]([CH3:3])[CH2:4][C:5]1=[N:6][CH:7]=[C:8]([O:9][CH2:10][c:11]2[cH:12][cH:13][cH:14][cH:15][cH:16]2)[C:17](=[O:18])[CH2:19]1 | CNC.O=C1CC(CCl)=NC=C1OCc1ccccc1 | CN(C)CC1=NC=C(OCc2ccccc2)C(=O)C1 | null | null | O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 6d58cac08ccced0a33ed16fbca180bc12aa011288d6476106d98a7b2cbc3d709 | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | O=C1CC=NC=C1OCc1ccccc1 | Cl-[CH2;D2;+0:1]-[C:2]1=[#7:3]-[C:4]=[C:5]-[C:6](=[O;D1;H0:7])-[C:8]-1.[C;D1;H3:9]-[NH;D2;+0:10]-[C;D1;H3:11]>>[C;D1;H3:9]-[N;H0;D3;+0:10](-[C;D1;H3:11])-[CH2;D2;+0:1]-[C:2]1=[#7:3]-[C:4]=[C:5]-[C:6](=[O;D1;H0:7])-[C:8]-1 | 96.7 | [{"value": 96.7, "product": "C(C1=CC=CC=C1)OC=1C(CC(=NC1)CN(C)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1.5 | HOUR | To a mixture of 2-chloromethyl-5-benzyloxy-4-pyridone (1.0 g), tetrahydrofuran (10 ml) and water (10 ml) were added dimethylamine hydrochloride (1.31 g) and sodium hydroxide (0.64 g). After being stirred for 1.5 hours, the mixture was concentrated under reduced pressure to dryness. The residue was dissolved in methanol... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | null | null | C1=CN=CCC1.c1ccccc1 | HCl | O | null | 1.5 | CNC.O=C1CC(CCl)=NC=C1OCc1ccccc1>O>CN(C)CC1=NC=C(OCc2ccccc2)C(=O)C1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-882500f88033402bbab10d05d86712f8 | O=C1CC(CCl)=NC=C1OCc1ccccc1.c1ccc(P(c2ccccc2)c2ccccc2)cc1>>C=CC1=NC=C(OCc2ccccc2)C(=O)C1 | C(C1=CC=CC=C1)OC=1C(CC(=NC1)CCl)=O.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C(C)(=O)OCC>>C(C1=CC=CC=C1)OC=1C(CC(=NC1)C=C)=O | Cl[CH2:2][C:3]1=[N:4][CH:5]=[C:6]([O:7][CH2:8][c:9]2[cH:10][cH:11][cH:12][cH:13][cH:14]2)[C:15](=[O:16])[CH2:17]1.c1ccc(P(c2ccccc2)c2cccc[cH:1]2)cc1>>[CH2:1]=[CH:2][C:3]1=[N:4][CH:5]=[C:6]([O:7][CH2:8][c:9]2[cH:10][cH:11][cH:12][cH:13][cH:14]2)[C:15](=[O:16])[CH2:17]1 | O=C1CC(CCl)=NC=C1OCc1ccccc1.c1ccc(P(c2ccccc2)c2ccccc2)cc1 | C=CC1=NC=C(OCc2ccccc2)C(=O)C1 | null | null | CN(C=O)C | C-C Coupling | OtherReaction | 76985114059d0996f37105677c149f388110d82e90de594af76921f20e648f39 | 08ffc1e07ff461351b0acfd55b5eb04a63a8e2ff7ae3af7a250a8ce67da0b4aa | O=C1CC=NC=C1OCc1ccccc1 | Cl-[CH2;D2;+0:1]-[C:2]1=[#7:3]-[C:4]=[C:5]-[C:6](=[O;D1;H0:7])-[C:8]-1.[cH;D2;+0:9]1:c:c:c:c:c:1-P(-c1:c:c:c:c:c:1)-c1:c:c:c:c:c:1>>[CH2;D1;+0:9]=[CH;D2;+0:1]-[C:2]1=[#7:3]-[C:4]=[C:5]-[C:6](=[O;D1;H0:7])-[C:8]-1 | 66.2 | [{"value": 66.2, "product": "C(C1=CC=CC=C1)OC=1C(CC(=NC1)C=C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | A solution of 5-benzyloxy-2-chloromethyl-4-pyridone (10.0 g) and triphenylphosphine (10.5 g) in N,N-dimethylformamide (50 ml) was stirred for 5 hours at 90°-100° C. The resulting mixture was poured into ethyl acetate (800 ml). The precipitate was collected by filtration, washed with ethyl acetate and dissolved in dichl... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | Vinyl | c1ccccc1.c1ccccc1.c1ccccc1 | null | C1=CN=CCC1.c1ccccc1 | HCl | CN(C=O)C | null | 3 | O=C1CC(CCl)=NC=C1OCc1ccccc1.c1ccc(P(c2ccccc2)c2ccccc2)cc1>CN(C=O)C>C=CC1=NC=C(OCc2ccccc2)C(=O)C1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-03e7daa11f954f73ad1160c376faaee0 | C1CCNC1.C=CC1=NC=C(OCc2ccccc2)C(=O)C1>>O=C1CC(CCN2CCCC2)=NC=C1OCc1ccccc1 | C(C1=CC=CC=C1)OC=1C(CC(=NC1)C=C)=O.N1CCCC1>>C(C1=CC=CC=C1)OC=1C(CC(=NC1)CCN1CCCC1)=O | [NH:7]1[CH2:8][CH2:9][CH2:10][CH2:11]1.[O:1]=[C:2]1[CH2:3][C:4]([CH:5]=[CH2:6])=[N:12][CH:13]=[C:14]1[O:15][CH2:16][c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1>>[O:1]=[C:2]1[CH2:3][C:4]([CH2:5][CH2:6][N:7]2[CH2:8][CH2:9][CH2:10][CH2:11]2)=[N:12][CH:13]=[C:14]1[O:15][CH2:16][c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1 | C1CCNC1.C=CC1=NC=C(OCc2ccccc2)C(=O)C1 | O=C1CC(CCN2CCCC2)=NC=C1OCc1ccccc1 | null | null | C(C)(C)OC(C)C.O1CCCC1 | Heteroatom Alkylation and Arylation | aza-Michael addition secondary | dd05e02f89f4334a0cbf67e5033d2677d654bbf2f6f7ab2436d63d82eac8e490 | 828fcbb87adfef9f22c9a1e52b43c3df76cb2e49bfe62b57e8b79965772a2bed | O=C1CC(CCN2CCCC2)=NC=C1OCc1ccccc1 | [CH2;D1;+0:1]=[CH;D2;+0:2]-[C:3]1=[#7:4]-[C:5]=[C:6]-[C:7](=[O;D1;H0:8])-[C:9]-1.[C:10]1-[C:11]-[NH;D2;+0:12]-[C:13]-[C:14]-1>>[O;D1;H0:8]=[C:7]1-[C:6]=[C:5]-[#7:4]=[C:3](-[CH2;D2;+0:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:12]2-[C:11]-[C:10]-[C:14]-[C:13]-2)-[C:9]-1 | null | [] | null | null | null | null | A mixture of 5-benzyloxy-2-vinyl-4-pyridone (2.90 g) and pyrrolidine (5.33 ml) was heated and refluxed for an hour. The mixture was cooled and diluted with tetrahydrofuran (20 ml) and diisopropyl ether (80 ml). After being stirred for an hour at ambient temperature, the resulting precipitate was collected by filtration... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amine.Vinyl | Tertiary amine | C1CCNC1 | C1CC[NH]C1 | C1=CN=CCC1.C1CC[NH]C1.c1ccccc1 | null | C(C)(C)OC(C)C.O1CCCC1 | null | null | C1CCNC1.C=CC1=NC=C(OCc2ccccc2)C(=O)C1>C(C)(C)OC(C)C.O1CCCC1>O=C1CC(CCN2CCCC2)=NC=C1OCc1ccccc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-7c4e570c849a48728586d884ee0e0858 | C=CC1=NC=C(OCc2ccccc2)C(=O)C1.CNC>>CN(C)CCC1=NC=C(OCc2ccccc2)C(=O)C1 | C(C1=CC=CC=C1)OC=1C(CC(=NC1)C=C)=O.CNC>>C(C1=CC=CC=C1)OC=1C(CC(=NC1)CCN(C)C)=O | [CH2:4]=[CH:5][C:6]1=[N:7][CH:8]=[C:9]([O:10][CH2:11][c:12]2[cH:13][cH:14][cH:15][cH:16][cH:17]2)[C:18](=[O:19])[CH2:20]1.[CH3:1][NH:2][CH3:3]>>[CH3:1][N:2]([CH3:3])[CH2:4][CH2:5][C:6]1=[N:7][CH:8]=[C:9]([O:10][CH2:11][c:12]2[cH:13][cH:14][cH:15][cH:16][cH:17]2)[C:18](=[O:19])[CH2:20]1 | C=CC1=NC=C(OCc2ccccc2)C(=O)C1.CNC | CN(C)CCC1=NC=C(OCc2ccccc2)C(=O)C1 | null | null | C(C)O | Heteroatom Alkylation and Arylation | aza-Michael addition secondary | 8acf647a588bdc7347506dcd3290904024f41acb450fe55eb6c0af193ad82ab8 | 828fcbb87adfef9f22c9a1e52b43c3df76cb2e49bfe62b57e8b79965772a2bed | O=C1CC=NC=C1OCc1ccccc1 | [C;D1;H3:1]-[NH;D2;+0:2]-[C;D1;H3:3].[CH2;D1;+0:4]=[CH;D2;+0:5]-[C:6]1=[#7:7]-[C:8]=[C:9]-[C:10](=[O;D1;H0:11])-[C:12]-1>>[C;D1;H3:1]-[N;H0;D3;+0:2](-[C;D1;H3:3])-[CH2;D2;+0:4]-[CH2;D2;+0:5]-[C:6]1=[#7:7]-[C:8]=[C:9]-[C:10](=[O;D1;H0:11])-[C:12]-1 | null | [] | 100 | CELSIUS | null | null | A mixture of 5-benzyloxy-2-vinyl-4-pyridone (3.12 g), 50% aqueous solution of dimethylamine (15 ml) and ethanol (35 ml) was heated at 100° C. in a sealed tube for 8 hours. The resulting mixture was cooled and concentrated under reduced pressure to dryness. The residue was triturated with a mixture of ethyl acetate and ... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amine.Vinyl | Tertiary amine | null | null | C1=CN=CCC1.c1ccccc1 | null | C(C)O | 100 | null | C=CC1=NC=C(OCc2ccccc2)C(=O)C1.CNC>C(C)O>CN(C)CCC1=NC=C(OCc2ccccc2)C(=O)C1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-86c329b28e3749bb825d21bed239c9be | CN(C)CC1=NC=C(OCc2ccccc2)C(=O)C1>>CN(C)CC1=NC=C(O)C(=O)C1 | C(C1=CC=CC=C1)OC=1C(CC(=NC1)CN(C)C)=O>>CN(C)CC1=NC=C(C(C1)=O)O | c1ccc(C[O:9][C:8]2=[CH:7][N:6]=[C:5]([CH2:4][N:2]([CH3:1])[CH3:3])[CH2:12][C:10]2=[O:11])cc1>>[CH3:1][N:2]([CH3:3])[CH2:4][C:5]1=[N:6][CH:7]=[C:8]([OH:9])[C:10](=[O:11])[CH2:12]1 | CN(C)CC1=NC=C(OCc2ccccc2)C(=O)C1 | CN(C)CC1=NC=C(O)C(=O)C1 | null | [Pd] | CO | Deprotection | Carboxyl benzyl deprotection | a27a5c3b287ca67a74bdac4a49b9989699f9ec4115528b6b5610ee6a5429e1be | 46645286250e9e93c5ddee1ccf748780c29296c960f664cd41dc632ec0127ee0 | O=C1C=CN=CC1 | [O;D1;H0:1]=[C:2]1-[C:3]-[C:4]=[#7:5]-[C:6]=[C:7]-1-[O;H0;D2;+0:8]-C-c1:c:c:c:c:c:1>>[O;D1;H0:1]=[C:2]1-[C:3]-[C:4]=[#7:5]-[C:6]=[C:7]-1-[OH;D1;+0:8] | 147.4 | [{"value": 147.4, "product": "CN(C)CC1=NC=C(C(C1)=O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 5-Benzyloxy-2-(N,N-dimethylamino)methyl-4-pyridone 1.0 g) in methanol (15 ml) was subjected to catalytic reduction with 10% palladium on activated carbon (200 mg) at atmospheric pressure. After removal of catalyst, the solution was concentrated under reduced pressure to give 2-(N,N-dimethylamino)methyl-5-hydroxy-4-pyri... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Enol | c1ccccc1 | null | C1=CN=CCC1 | Other | [Pd].CO | null | null | CN(C)CC1=NC=C(OCc2ccccc2)C(=O)C1>[Pd].CO>CN(C)CC1=NC=C(O)C(=O)C1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-a1996d3323e84ceebe125fe52c63369e | CC(C)(ON=C(C(=O)N[C@@H]1C(=O)N2C(C(=O)O)=C(CCl)CS[C@H]12)c1nsc(N)n1)C(=O)O.CN(C)CC1=NC=C(O)C(=O)C1>>CC(C)(ON=C(C(=O)N[C@@H]1C(=O)N2C(C(=O)[O-])=C(C[N+](C)(C)Cc3cc(=O)c(O)c[nH]3)CS[C@H]12)c1nsc(N)n1)C(=O)O | C(C)(=O)OCC.FC(C(=O)O)(F)F.NC1=NC(=NS1)C(C(=O)N[C@H]1[C@@H]2N(C(=C(CS2)CCl)C(=O)O)C1=O)=NOC(C)(C)C(=O)O.CN(C)CC1=NC=C(C(C1)=O)O>>NC1=NC(=NS1)C(C(=O)N[C@H]1[C@@H]2N(C(=C(CS2)C[N+](CC=2NC=C(C(C2)=O)O)(C)C)C(=O)[O-])C1=O)=NOC(C)(C)C(=O)O | Cl[CH2:19][C:18]1=[C:14]([C:15](=[O:16])[OH:17])[N:13]2[C:11](=[O:12])[C@@H:10]([NH:9][C:7]([C:6](=[N:5][O:4][C:2]([CH3:1])([CH3:3])[C:41](=[O:42])[OH:43])[c:35]3[n:36][s:37][c:38]([NH2:39])[n:40]3)=[O:8])[C@H:34]2[S:33][CH2:32]1.[N:20]([CH3:21])([CH3:22])[CH2:23][C:24]1=[N:31][CH:30]=[C:28]([OH:29])[C:26](=[O:27])[CH2... | CC(C)(ON=C(C(=O)N[C@@H]1C(=O)N2C(C(=O)O)=C(CCl)CS[C@H]12)c1nsc(N)n1)C(=O)O.CN(C)CC1=NC=C(O)C(=O)C1 | CC(C)(ON=C(C(=O)N[C@@H]1C(=O)N2C(C(=O)[O-])=C(C[N+](C)(C)Cc3cc(=O)c(O)c[nH]3)CS[C@H]12)c1nsc(N)n1)C(=O)O | null | null | CN(C=O)C | Aromatic Heterocycle Formation | OtherReaction | a92ae7cc5a6cc1218da491009bbb97da57f1f49fd71d026d712f9f2d814492ec | f50b084a0dbab4b5174cbac06b35eb496fd34f7a7a43eae3feca34fdde8ff0e3 | N=C(C(=O)N[C@@H]1C(=O)N2C=C(C[NH2+]Cc3cc(=O)cc[nH]3)CS[C@H]12)c1ncsn1 | Cl-[CH2;D2;+0:1]-[C:2](=[C:3](-[C:4](=[O;D1;H0:5])-[OH;D1;+0:6])-[#7:7]-[C:8]=[O;D1;H0:9])-[C:10]-[#16:11].[C;D1;H3:12]-[N;H0;D3;+0:13](-[C;D1;H3:14])-[C:15]-[C;H0;D3;+0:16]1=[N;H0;D2;+0:17]-[CH;D2;+0:18]=[C;H0;D3;+0:19](-[O;D1;H1:20])-[C;H0;D3;+0:21](=[O;D1;H0:22])-[CH2;D2;+0:23]-1>>[#16:11]-[C:10]-[C:2](-[CH2;D2;+0:1... | 29.2 | [{"value": 29.2, "product": "NC1=NC(=NS1)C(C(=O)N[C@H]1[C@@H]2N(C(=C(CS2)C[N+](CC=2NC=C(C(C2)=O)O)(C)C)C(=O)[O-])C1=O)=NOC(C)(C)C(=O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 5 | HOUR | To a solution of 7β-[2-(5-amino-1,2,4-thiadiazol-3-yl)-2-(1-carboxy-1-methylethoxyimino)acetamido]-3-chloromethyl-3-cephem-4-carboxylic acid trifluoroacetate (syn isomer) (1.0 g) in N,N-dimethylformamide (10 ml) was added 2-(N,N-dimethylamino)methyl-5-hydroxy-4pyridone (1.09 g). After being stirred for 5 hours at ambie... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Carboxylic acid.Ketone.Substituted imine.Enol.Tertiary amine | Aromatic alcohol | C1=CN=CCC1 | c1ccncc1 | C1=CN2CC[C@H]2SC1.c1ccncc1.c1ncsn1 | HCl | CN(C=O)C | null | 5 | CC(C)(ON=C(C(=O)N[C@@H]1C(=O)N2C(C(=O)O)=C(CCl)CS[C@H]12)c1nsc(N)n1)C(=O)O.CN(C)CC1=NC=C(O)C(=O)C1>CN(C=O)C>CC(C)(ON=C(C(=O)N[C@@H]1C(=O)N2C(C(=O)[O-])=C(C[N+](C)(C)Cc3cc(=O)c(O)c[nH]3)CS[C@H]12)c1nsc(N)n1)C(=O)O |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-c5330d0eb2d04a46bc2e78047215f6c4 | O=C1CC(CO)=NC=C1OCc1ccccc1.O=S(Cl)Cl>>O=C1CC(CCl)=NC=C1OCc1ccccc1 | C(C1=CC=CC=C1)OC=1C(CC(=NC1)CO)=O.S(=O)(Cl)Cl>>C(C1=CC=CC=C1)OC=1C(CC(=NC1)CCl)=O | O[CH2:5][C:4]1=[N:7][CH:8]=[C:9]([O:10][CH2:11][c:12]2[cH:13][cH:14][cH:15][cH:16][cH:17]2)[C:2](=[O:1])[CH2:3]1.O=S(Cl)[Cl:6]>>[O:1]=[C:2]1[CH2:3][C:4]([CH2:5][Cl:6])=[N:7][CH:8]=[C:9]1[O:10][CH2:11][c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1 | O=C1CC(CO)=NC=C1OCc1ccccc1.O=S(Cl)Cl | O=C1CC(CCl)=NC=C1OCc1ccccc1 | null | null | C1=CC=CC=C1 | Functional Group Interconversion | Alcohol to chloride_SOCl2 | bb752b9027dc4488ba075e5955118a819f80cabd751a7497b67c2eeb1db6b071 | cbf41c7cf9fe6b47a243b1674d74ed5bf46a151f7f3a71d206e23176e158facf | O=C1CC=NC=C1OCc1ccccc1 | Cl-S(=O)-[Cl;H0;D1;+0:1].O-[CH2;D2;+0:2]-[C:3]1=[#7:4]-[C:5]=[C:6]-[C:7](=[O;D1;H0:8])-[C:9]-1>>[Cl;H0;D1;+0:1]-[CH2;D2;+0:2]-[C:3]1=[#7:4]-[C:5]=[C:6]-[C:7](=[O;D1;H0:8])-[C:9]-1 | null | [] | null | null | null | null | To a suspension of 5-benzyloxy-2-hydroxymethyl-4-pyridone (33 g) in benzene (500 ml) was added thionyl chloride (28.4 ml) at ambient temperature under stirring. After being stirred at the same temperature for 30 minutes, the mixture was refluxed for 4 hours. The resulting mixture was cooled to ambient temperature. The ... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | Primary halide | null | null | C1=CN=CCC1.c1ccccc1 | HCl | C1=CC=CC=C1 | null | null | O=C1CC(CO)=NC=C1OCc1ccccc1.O=S(Cl)Cl>C1=CC=CC=C1>O=C1CC(CCl)=NC=C1OCc1ccccc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-a802be13cec04c9b94c3bb91564a04a5 | C[N+](C)(CC1=C(C(=O)[O-])N2C(=O)[C@@H](NC=O)[C@H]2SC1)Cc1cc(=O)c(O)c[nH]1>>C[N+](C)(CC1=C(C(=O)[O-])N2C(=O)[C@@H](N)[C@H]2SC1)Cc1cc(=O)c(O)c[nH]1.Cl | C(C)(=O)OCC.C(=O)N[C@H]1[C@@H]2N(C(=C(CS2)C[N+](CC=2NC=C(C(C2)=O)O)(C)C)C(=O)[O-])C1=O.Cl>>Cl.Cl.N[C@H]1[C@@H]2N(C(=C(CS2)C[N+](CC=2NC=C(C(C2)=O)O)(C)C)C(=O)[O-])C1=O | O=C[NH:14][C@@H:13]1[C:11](=[O:12])[N:10]2[C:6]([C:7](=[O:8])[O-:9])=[C:5]([CH2:4][N+:2]([CH3:1])([CH3:3])[CH2:18][c:19]3[cH:20][c:21](=[O:22])[c:23]([OH:24])[cH:25][nH:26]3)[CH2:17][S:16][C@@H:15]21>>[CH3:1][N+:2]([CH3:3])([CH2:4][C:5]1=[C:6]([C:7](=[O:8])[O-:9])[N:10]2[C:11](=[O:12])[C@@H:13]([NH2:14])[C@H:15]2[S:16]... | C[N+](C)(CC1=C(C(=O)[O-])N2C(=O)[C@@H](NC=O)[C@H]2SC1)Cc1cc(=O)c(O)c[nH]1 | C[N+](C)(CC1=C(C(=O)[O-])N2C(=O)[C@@H](N)[C@H]2SC1)Cc1cc(=O)c(O)c[nH]1.Cl | null | null | C(=O)O | Miscellaneous | Reduction of primary amides to amines | 707d862673494df308d0498876d0cad3507dbc14401d385dbef5e48e25cb04ab | 9a852660e38a73253f286565bb98edc48afeded5895ee8b4d0c2bc8a5eeae729 | O=C1C[C@H]2SCC(C[NH2+]Cc3cc(=O)cc[nH]3)=CN12 | O=C-[NH;D2;+0:1]-[C:2]1-[C:3](=[O;D1;H0:4])-[#7:5](-[C:6]-1-[#16:7])-[C:8](-[C:9](-[O;-;D1;H0:10])=[O;D1;H0:11])=[C:12]>>[#16:7]-[C:6]1-[#7:5](-[C:3](=[O;D1;H0:4])-[C:2]-1-[NH2;D1;+0:1])-[C:8](-[C:9](-[O;-;D1;H0:10])=[O;D1;H0:11])=[C:12] | null | [] | null | null | 2.5 | HOUR | To a cooled solution of 7β-formamido-3-[N,N-dimethyl-N-{(5-hydroxy-4-oxo-1,4-dihydropyridin-2-yl)methyl}ammonio]methyl-3-cephem-4-carboxylate (4.084 g) in formic acid (8.1 ml) was added dropwise conc. hydrochloric acid (2.5 ml). The mixture was warmed to room temperature and stirred for 2.5 hours. The mixture was added... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide | Primary amine | null | null | C1=CN2CC[C@H]2SC1.c1ccncc1 | Other | C(=O)O | null | 2.5 | C[N+](C)(CC1=C(C(=O)[O-])N2C(=O)[C@@H](NC=O)[C@H]2SC1)Cc1cc(=O)c(O)c[nH]1>C(=O)O>C[N+](C)(CC1=C(C(=O)[O-])N2C(=O)[C@@H](N)[C@H]2SC1)Cc1cc(=O)c(O)c[nH]1.Cl |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-2ef62d98fe1447439390fdc1af915ab7 | CC(=O)Oc1cnc(C(=O)O)cc1OC(C)=O.ClP(Cl)(Cl)(Cl)Cl>>CC(=O)Oc1cnc(C(=O)Cl)cc1OC(C)=O.Cl | P(Cl)(Cl)(Cl)(Cl)Cl.C(C)(=O)OC1=CC(=NC=C1OC(C)=O)C(=O)O.C(C)(C)OC(C)C>>Cl.C(C)(=O)OC1=CC(=NC=C1OC(C)=O)C(=O)Cl | O[C:9]([c:8]1[n:7][cH:6][c:5]([O:4][C:2]([CH3:1])=[O:3])[c:13]([O:14][C:15]([CH3:16])=[O:17])[cH:12]1)=[O:10].ClP(Cl)(Cl)([Cl:11])[Cl:18]>>[CH3:1][C:2](=[O:3])[O:4][c:5]1[cH:6][n:7][c:8]([C:9](=[O:10])[Cl:11])[cH:12][c:13]1[O:14][C:15]([CH3:16])=[O:17].[ClH:18] | CC(=O)Oc1cnc(C(=O)O)cc1OC(C)=O.ClP(Cl)(Cl)(Cl)Cl | CC(=O)Oc1cnc(C(=O)Cl)cc1OC(C)=O.Cl | null | null | C(Cl)Cl | Functional Group Interconversion | Alcohol to chloride_Other | c301c14a9dcd0670d52e8b77396cbe7fd8edeedd757bc43f4162ade1fc52fc93 | 787f545db5dc0b29dde55b5fbed7db8625b8055f49327f97ed4d83cc47c3af1d | c1ccncc1 | Cl-P(-Cl)(-Cl)(-[Cl;H0;D1;+0:1])-[Cl;H0;D1;+0:2].O-[C;H0;D3;+0:3](=[O;D1;H0:4])-[c:5](:[c:6]):[#7;a:7]:[c:8]>>[Cl;H0;D1;+0:1]-[C;H0;D3;+0:3](=[O;D1;H0:4])-[c:5](:[c:6]):[#7;a:7]:[c:8].[ClH;D0;+0:2] | 158.5 | [{"value": 158.5, "product": "Cl.C(C)(=O)OC1=CC(=NC=C1OC(C)=O)C(=O)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a suspension of phosphorus pentachloride (4.6 g) in methylene chloride (40 ml) was added 4,5-diacetoxy-2-pyridinecarboxylic acid (4.5 g) at -20° C. with stirring. The stirring was continued for an hour at -18°~12° C. To the reaction mixture was added diisopropyl ether (80 ml) below 0° C. The resulting precipitates w... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Acyl halide | null | null | c1ccncc1 | Other | C(Cl)Cl | null | null | CC(=O)Oc1cnc(C(=O)O)cc1OC(C)=O.ClP(Cl)(Cl)(Cl)Cl>C(Cl)Cl>CC(=O)Oc1cnc(C(=O)Cl)cc1OC(C)=O.Cl |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-267ddbce90734d2f82315bf163cec8db | CN1CCNCC1.COC(=O)c1cc(O)c(OCc2ccccc2)cn1>>CN1CCN(C(=O)c2cc(O)c(OCc3ccccc3)cn2)CC1 | COC(=O)C1=NC=C(C(=C1)O)OCC1=CC=CC=C1.CN1CCNCC1>>CN1CCN(CC1)C(=O)C1=NC=C(C(=C1)O)OCC1=CC=CC=C1 | [CH3:1][N:2]1[CH2:3][CH2:4][NH:5][CH2:23][CH2:24]1.CO[C:6](=[O:7])[c:8]1[cH:9][c:10]([OH:11])[c:12]([O:13][CH2:14][c:15]2[cH:16][cH:17][cH:18][cH:19][cH:20]2)[cH:21][n:22]1>>[CH3:1][N:2]1[CH2:3][CH2:4][N:5]([C:6](=[O:7])[c:8]2[cH:9][c:10]([OH:11])[c:12]([O:13][CH2:14][c:15]3[cH:16][cH:17][cH:18][cH:19][cH:20]3)[cH:21][... | CN1CCNCC1.COC(=O)c1cc(O)c(OCc2ccccc2)cn1 | CN1CCN(C(=O)c2cc(O)c(OCc3ccccc3)cn2)CC1 | null | null | C(Cl)(Cl)Cl.CO | Acylation | Aminolysis of esters | 44054b0a720986552e2e8320be5bb048d66cc126b8a9f454ed6799b617547a88 | fa66342dd118fe5531ba6a998ac8fab92d2b0db4fd04688560eec7d04e9be0e4 | O=C(c1ccc(OCc2ccccc2)cn1)N1CCNCC1 | C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[#7;a:5]:[c:6].[#7:7]1-[C:8]-[C:9]-[NH;D2;+0:10]-[C:11]-[C:12]-1>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[N;H0;D3;+0:10]1-[C:9]-[C:8]-[#7:7]-[C:12]-[C:11]-1)-[c:3](:[c:4]):[#7;a:5]:[c:6] | 17.4 | [{"value": 17.4, "product": "CN1CCN(CC1)C(=O)C1=NC=C(C(=C1)O)OCC1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | null | null | To a suspension of 2-methoxycarbonyl-4-hydroxy-5-benzyloxypyridine (18.15 g) in N-methylpiperazine (21.04 g) was heated to 100° C. for 3.5 hours. The resulting viscous solution was cooled to room temperature, diluted with a mixture of chloroform (270 ml) and methanol (30 ml) and subjected to column chromatography on si... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Secondary amine | Tertiary amide | C1C[NH]CCN1 | C1C[NH]CC[NH]1 | C1C[NH]CC[NH]1.c1ccncc1.c1ccccc1 | HO- | C(Cl)(Cl)Cl.CO | 100 | null | CN1CCNCC1.COC(=O)c1cc(O)c(OCc2ccccc2)cn1>C(Cl)(Cl)Cl.CO>CN1CCN(C(=O)c2cc(O)c(OCc3ccccc3)cn2)CC1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-a8eca58fbacb432c81e4d18ca5413a11 | CC(=O)Oc1ccc(C(=O)N2CCN(C)CC2)cc1OC(C)=O>>CN1CCN(C(=O)c2ccc(O)c(O)c2)CC1 | Cl.CN1CCN(CC1)C(C1=CC(=C(C=C1)OC(C)=O)OC(C)=O)=O.C([O-])([O-])=O.[K+].[K+]>>CN1CCN(CC1)C(C1=CC(=C(C=C1)O)O)=O | CC(=O)[O:12][c:11]1[cH:10][cH:9][c:8]([C:6]([N:5]2[CH2:4][CH2:3][N:2]([CH3:1])[CH2:17][CH2:16]2)=[O:7])[cH:15][c:13]1[O:14]C(C)=O>>[CH3:1][N:2]1[CH2:3][CH2:4][N:5]([C:6](=[O:7])[c:8]2[cH:9][cH:10][c:11]([OH:12])[c:13]([OH:14])[cH:15]2)[CH2:16][CH2:17]1 | CC(=O)Oc1ccc(C(=O)N2CCN(C)CC2)cc1OC(C)=O | CN1CCN(C(=O)c2ccc(O)c(O)c2)CC1 | null | null | CO | Reduction | OtherReaction | 7b7e32f38c8a719ca98099bc0a6aa138d56231b7b04ad475d74b1a13991ac98f | e01d5791a75e3a08093f57d62c9c2d4bec3d7dc239371b69a4320a81141226de | O=C(c1ccccc1)N1CCNCC1 | C-C(=O)-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4](-[O;H0;D2;+0:5]-C(-C)=O):[c:6]>>[OH;D1;+0:1]-[c:2](:[c:3]):[c:4](-[OH;D1;+0:5]):[c:6] | 32.6 | [{"value": 32.6, "product": "CN1CCN(CC1)C(C1=CC(=C(C=C1)O)O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | To a solution of 1-methyl-4-(3,4-diacetoxybenzoyl)piperazine (295 mg) n methanol (3 ml) was added a saturated potassium carbonate solution is methanol (6 ml) and the mixture was stirred at room temperature for 30 minutes. The mixture was poured into ice water and adjusted to pH 9 with 1N hydrochloric acid. The mixture ... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester | Aromatic alcohol.Aromatic alcohol | null | null | C1C[NH]CC[NH]1.c1ccccc1 | HO- | CO | null | 0.5 | CC(=O)Oc1ccc(C(=O)N2CCN(C)CC2)cc1OC(C)=O>CO>CN1CCN(C(=O)c2ccc(O)c(O)c2)CC1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-fa733e47066d484ebd641ac406f9ee1d | CN1CCN(C(=O)c2cc(O)c(OCc3ccccc3)cn2)CC1>>CN1CCN(C(=O)c2cc(O)c(O)cn2)CC1 | CN1CCN(CC1)C(=O)C1=NC=C(C(=C1)O)OCC1=CC=CC=C1>>CN1CCN(CC1)C(=O)C1=NC=C(C(=C1)O)O | c1ccc(C[O:13][c:12]2[c:10]([OH:11])[cH:9][c:8]([C:6]([N:5]3[CH2:4][CH2:3][N:2]([CH3:1])[CH2:17][CH2:16]3)=[O:7])[n:15][cH:14]2)cc1>>[CH3:1][N:2]1[CH2:3][CH2:4][N:5]([C:6](=[O:7])[c:8]2[cH:9][c:10]([OH:11])[c:12]([OH:13])[cH:14][n:15]2)[CH2:16][CH2:17]1 | CN1CCN(C(=O)c2cc(O)c(OCc3ccccc3)cn2)CC1 | CN1CCN(C(=O)c2cc(O)c(O)cn2)CC1 | null | [C].[Pd] | CO | Deprotection | Hydroxyl benzyl deprotection | 36869d1fe85185a14d9eb30bf05178c600a9b6eca277ffaf3803578c30e0bf5d | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | O=C(c1ccccn1)N1CCNCC1 | [#7:1]-[C:2](=[O;D1;H0:3])-[c:4]:[#7;a:5]:[c:6]:[c:7](-[O;H0;D2;+0:8]-C-c1:c:c:c:c:c:1):[c:9]>>[#7:1]-[C:2](=[O;D1;H0:3])-[c:4]:[#7;a:5]:[c:6]:[c:7](-[OH;D1;+0:8]):[c:9] | 38.7 | [{"value": 38.7, "product": "CN1CCN(CC1)C(=O)C1=NC=C(C(=C1)O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 20 | MINUTE | To a solution of 1-methyl-4-(4-hydroxy-5-benzyloxy-2-pyridylcarbonyl)piperazine (4.71 g) in methanol (300 ml) was added 10 palladium-carbon (2.35 g) in a stream of nitrogen and the mixture was hydrogenated at atmospheric pressure for 20 minutes. After the catalyst was removed by filtration, the filtrate was evaporated ... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | c1ccccc1 | null | C1C[NH]CC[NH]1.c1ccncc1 | Other | [C].[Pd].CO | null | 0.333333 | CN1CCN(C(=O)c2cc(O)c(OCc3ccccc3)cn2)CC1>[C].[Pd].CO>CN1CCN(C(=O)c2cc(O)c(O)cn2)CC1 |
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