dataset_id large_stringclasses 414
values | reaction_id large_stringlengths 36 36 | reaction_smiles large_stringlengths 4 873 | rxn_insight_reaction large_stringlengths 19 1.07k | mapped_reaction_smiles large_stringlengths 14 3.37k | reactant_smiles large_stringlengths 1 581 | product_smiles large_stringlengths 1 433 | reagent_smiles large_stringclasses 634
values | catalyst_smiles large_stringlengths 1 683 ⌀ | solvent_smiles large_stringlengths 1 245 ⌀ | rxn_insight_class large_stringclasses 11
values | rxn_insight_name large_stringclasses 346
values | rxn_insight_tag large_stringlengths 64 64 | rxn_insight_tag2 large_stringlengths 64 64 | rxn_insight_scaffold large_stringlengths 5 288 ⌀ | rxn_insight_template large_stringlengths 24 2.64k ⌀ | yield_percent float64 -0.8 90,205,160,000B ⌀ | yield_measurements large_stringlengths 2 864 | temperature_value float64 -230 30.1k ⌀ | temperature_units large_stringclasses 3
values | reaction_time_value float64 0 4k ⌀ | time_units large_stringclasses 4
values | procedure_details large_stringlengths 1 23.6k ⌀ | reference large_stringclasses 96
values | doi large_stringclasses 19
values | functional_groups_reactants large_stringlengths 3 716 ⌀ | functional_groups_products large_stringlengths 3 539 ⌀ | participating_rings_reactants large_stringlengths 5 293 ⌀ | participating_rings_products large_stringlengths 5 271 ⌀ | all_rings_products large_stringlengths 5 271 ⌀ | byproduct_smiles large_stringclasses 176
values | agent_smiles large_stringlengths 1 712 ⌀ | temperature_c float64 -230 30.1k ⌀ | reaction_time_hours float64 0 2.16k ⌀ | reaction_smiles_with_agents large_stringlengths 4 882 |
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-ad1ac3ae5a894c42a369e1a0f5415105 | O=C(O)c1ccccc1C(F)(F)F.O=S(Cl)Cl>>O=C(Cl)c1ccccc1C(F)(F)F | FC(C1=C(C(=O)O)C=CC=C1)(F)F.S(=O)(Cl)Cl>>FC(C1=C(C(=O)Cl)C=CC=C1)(F)F | O[C:2](=[O:1])[c:4]1[cH:5][cH:6][cH:7][cH:8][c:9]1[C:10]([F:11])([F:12])[F:13].O=S(Cl)[Cl:3]>>[O:1]=[C:2]([Cl:3])[c:4]1[cH:5][cH:6][cH:7][cH:8][c:9]1[C:10]([F:11])([F:12])[F:13] | O=C(O)c1ccccc1C(F)(F)F.O=S(Cl)Cl | O=C(Cl)c1ccccc1C(F)(F)F | null | null | null | Functional Group Interconversion | Alcohol to chloride_SOCl2 | c301c14a9dcd0670d52e8b77396cbe7fd8edeedd757bc43f4162ade1fc52fc93 | 787f545db5dc0b29dde55b5fbed7db8625b8055f49327f97ed4d83cc47c3af1d | c1ccccc1 | Cl-S(=O)-[Cl;H0;D1;+0:1].O-[C;H0;D3;+0:2](=[O;D1;H0:3])-[c:4](:[c:5]):[c:6]>>[Cl;H0;D1;+0:1]-[C;H0;D3;+0:2](=[O;D1;H0:3])-[c:4](:[c:5]):[c:6] | null | [] | null | null | null | null | A solution of 2.0 g of o-trifluoromethylbenzoic acid in 21 ml of thionyl chloride is heated at reflux for 1 hour. The volatiles are evaporated in vacuo to give a residue which is concentrated from toluene three times and dried under vacuum to give 2.1 g of the desired product as a residue.
Conditions: See reaction.note... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Acyl halide | null | null | c1ccccc1 | HCl | null | null | null | O=C(O)c1ccccc1C(F)(F)F.O=S(Cl)Cl>>O=C(Cl)c1ccccc1C(F)(F)F |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-7006a84674f645ed9bb0062876522446 | Cc1ccccc1CC(=O)Cl.Nc1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1>>Cc1ccccc1CC(=O)Nc1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1 | NC1=CC=C(C(=O)N2CC=3N(CC4=C2C=CC=C4)C=CC3)C=C1.CC1=C(C=CC=C1)CC(=O)Cl.C(C)N(CC)CC>>C=1C=CN2C1CN(C1=C(C2)C=CC=C1)C(=O)C1=CC=C(C=C1)NC(CC1=C(C=CC=C1)C)=O | Cl[C:9]([CH2:8][c:7]1[c:2]([CH3:1])[cH:3][cH:4][cH:5][cH:6]1)=[O:10].[NH2:11][c:12]1[cH:13][cH:14][c:15]([C:16](=[O:17])[N:18]2[CH2:19][c:20]3[cH:21][cH:22][cH:23][n:24]3[CH2:25][c:26]3[cH:27][cH:28][cH:29][cH:30][c:31]32)[cH:32][cH:33]1>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][cH:6][c:7]1[CH2:8][C:9](=[O:10])[NH:11][c:12]1[cH... | Cc1ccccc1CC(=O)Cl.Nc1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1 | Cc1ccccc1CC(=O)Nc1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1 | null | null | C(Cl)Cl | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=C(Cc1ccccc1)Nc1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[c:4].[NH2;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[C:3]-[c:4])-[NH;D2;+0:5]-[c:6](:[c:7]):[c:8] | 53.6 | [{"value": 53.6, "product": "C=1C=CN2C1CN(C1=C(C2)C=CC=C1)C(=O)C1=CC=C(C=C1)NC(CC1=C(C=CC=C1)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | MINUTE | To a stirred solution of 0.334 g of 2-methylphenylacetyl chloride 5 ml of methylene chloride is added 0.346 g of triethylamine at 0° C. After stirring for 3 minutes, 0.500 g of 10,11-dihydro-10-(4-aminobenzoyl)-5H-pyrrolo[2,1-c][1,4]benzodiazepine is added and stirring continued for 72 hours at room temperature. The re... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccccc1.c1ccc2c(c1)Cn1cccc1C[NH]2 | HCl | C(Cl)Cl | null | 0.05 | Cc1ccccc1CC(=O)Cl.Nc1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1>C(Cl)Cl>Cc1ccccc1CC(=O)Nc1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-657ec088ed714852a2e7b67e57d2bdba | Cc1cc(C(=O)N2Cc3cccn3Cc3ccccc32)ccc1[N+](=O)[O-]>>Cc1cc(C(=O)N2Cc3cccn3Cc3ccccc32)ccc1N | CC=1C=C(C(=O)N2CC=3N(CC4=C2C=CC=C4)C=CC3)C=CC1[N+](=O)[O-].NN>>NC1=C(C=C(C(=O)N2CC=3N(CC4=C2C=CC=C4)C=CC3)C=C1)C | O=[N+:24]([O-])[c:23]1[c:2]([CH3:1])[cH:3][c:4]([C:5](=[O:6])[N:7]2[CH2:8][c:9]3[cH:10][cH:11][cH:12][n:13]3[CH2:14][c:15]3[cH:16][cH:17][cH:18][cH:19][c:20]32)[cH:21][cH:22]1>>[CH3:1][c:2]1[cH:3][c:4]([C:5](=[O:6])[N:7]2[CH2:8][c:9]3[cH:10][cH:11][cH:12][n:13]3[CH2:14][c:15]3[cH:16][cH:17][cH:18][cH:19][c:20]32)[cH:21... | Cc1cc(C(=O)N2Cc3cccn3Cc3ccccc32)ccc1[N+](=O)[O-] | Cc1cc(C(=O)N2Cc3cccn3Cc3ccccc32)ccc1N | null | [Pd] | C(C)O | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | O=C(c1ccccc1)N1Cc2cccn2Cc2ccccc21 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | 85.2 | [{"value": 85.2, "product": "NC1=C(C=C(C(=O)N2CC=3N(CC4=C2C=CC=C4)C=CC3)C=C1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 1.22 g 10,11-dihydro-10-(3-methyl-4-nitro-benzoyl)-5H-pyrrolo[2,1-c][1,4]benzodiazepine, 0.2 g of 10% Pd/C and 0.35 g of anhydrous hydrazine in 50 ml of absolute ethyl alcohol is heated on a steam bath for 1 hour. The reaction mixture is filtered hot through diatomaceous earth and evaporated in vacuo to a ... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1.c1ccc2c(c1)Cn1cccc1C[NH]2 | Other | [Pd].C(C)O | null | null | Cc1cc(C(=O)N2Cc3cccn3Cc3ccccc32)ccc1[N+](=O)[O-]>[Pd].C(C)O>Cc1cc(C(=O)N2Cc3cccn3Cc3ccccc32)ccc1N |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-a0865d39ece04d7ca18701901cb148a2 | Cc1cc(C(=O)N2Cc3cccn3Cc3ccccc32)ccc1N.Cc1ccccc1C(=O)Cl>>Cc1cc(C(=O)N2Cc3cccn3Cc3ccccc32)ccc1NC(=O)c1ccccc1C | NC1=C(C=C(C(=O)N2CC=3N(CC4=C2C=CC=C4)C=CC3)C=C1)C.C(C)(C)N(C(C)C)CC.CC1=C(C(=O)Cl)C=CC=C1>>C=1C=CN2C1CN(C1=C(C2)C=CC=C1)C(=O)C1=CC(=C(C=C1)NC(C1=C(C=CC=C1)C)=O)C | [CH3:1][c:2]1[cH:3][c:4]([C:5](=[O:6])[N:7]2[CH2:8][c:9]3[cH:10][cH:11][cH:12][n:13]3[CH2:14][c:15]3[cH:16][cH:17][cH:18][cH:19][c:20]32)[cH:21][cH:22][c:23]1[NH2:24].Cl[C:25](=[O:26])[c:27]1[cH:28][cH:29][cH:30][cH:31][c:32]1[CH3:33]>>[CH3:1][c:2]1[cH:3][c:4]([C:5](=[O:6])[N:7]2[CH2:8][c:9]3[cH:10][cH:11][cH:12][n:13]... | Cc1cc(C(=O)N2Cc3cccn3Cc3ccccc32)ccc1N.Cc1ccccc1C(=O)Cl | Cc1cc(C(=O)N2Cc3cccn3Cc3ccccc32)ccc1NC(=O)c1ccccc1C | null | null | C(Cl)Cl | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=C(Nc1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1)c1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9])-[c:3](:[c:4]):[c:5] | 65.9 | [{"value": 65.9, "product": "C=1C=CN2C1CN(C1=C(C2)C=CC=C1)C(=O)C1=CC(=C(C=C1)NC(C1=C(C=CC=C1)C)=O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 0.83 g of 10,11-dihydro-10-(4-amino-3-methylbenzoyl)-5H-pyrrolo[2,1-c][1,4]benzodiazepine, 0.5 g of N,N-diisopropylethylamine and 0.6 g of 2-methylbenzoyl chloride in 50 ml of methylene chloride is stirred at room temperature for 18 hours. The reaction mixture is washed with water, the organic layer dried... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccc2c(c1)Cn1cccc1C[NH]2.c1ccccc1 | HCl | C(Cl)Cl | null | null | Cc1cc(C(=O)N2Cc3cccn3Cc3ccccc32)ccc1N.Cc1ccccc1C(=O)Cl>C(Cl)Cl>Cc1cc(C(=O)N2Cc3cccn3Cc3ccccc32)ccc1NC(=O)c1ccccc1C |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-3b609f87b5c246a3b15b45db6d0f89d5 | O=Cc1nccn1Cc1ccccc1[N+](=O)[O-]>>c1ccc2c(c1)Cn1ccnc1CN2 | [N+](=O)([O-])C1=C(CN2C(=NC=C2)C=O)C=CC=C1>>N=1C=CN2C1CNC1=C(C2)C=CC=C1 | O=[CH:13][c:12]1[n:8]([CH2:7][c:5]2[c:4]([N+:14](=O)[O-])[cH:3][cH:2][cH:1][cH:6]2)[cH:9][cH:10][n:11]1>>[cH:1]1[cH:2][cH:3][c:4]2[c:5]([cH:6]1)[CH2:7][n:8]1[cH:9][cH:10][n:11][c:12]1[CH2:13][NH:14]2 | O=Cc1nccn1Cc1ccccc1[N+](=O)[O-] | c1ccc2c(c1)Cn1ccnc1CN2 | null | null | C(C)O | Functional Group Interconversion | OtherReaction | 8ad7195897bf1d63c1fc85610caa816fda3f92772cbcb66265a6975e439e368b | 8d376a33ce625efea21a727d4a046134c1d759eb13efe5fa1e2683895e99352c | c1ccc2c(c1)Cn1ccnc1CN2 | O=[CH;D2;+0:1]-[c:2]1:[#7;a:3]:[c:4]:[c:5]:[#7;a:6]:1-[C:7]-[c:8]:[c:9](-[N+;H0;D3:10](=O)-[O-]):[c:11]>>[c:11]:[c:9]1:[c:8]-[C:7]-[#7;a:6]2:[c:5]:[c:4]:[#7;a:3]:[c:2]:2-[CH2;D2;+0:1]-[NH;D2;+0:10]-1 | null | [] | null | null | 4 | HOUR | A 5.0 g sample of 1-(o-nitrobenzyl)-imidazole-2-carboxaldehyde is dissolved in 150 ml of hot ethyl alcohol, cooled to room temperature and filtered. To the filtrate is added 0.5 g of 10% Pd/C and the mixture hydrogenated at 48 psi for 4 hours. An additional 0.5 g of 10% Pd/C is added and hydrogenation continued for 25 ... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Nitro group | Secondary amine | null | c1ccc2c(c1)Cn1ccnc1CN2 | c1ccc2c(c1)Cn1ccnc1CN2 | Other | C(C)O | null | 4 | O=Cc1nccn1Cc1ccccc1[N+](=O)[O-]>C(C)O>c1ccc2c(c1)Cn1ccnc1CN2 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-6cb8274916264f03afe3a0ef5dbc71ba | O=C1Nc2ccccc2Cn2ccnc21>>c1ccc2c(c1)Cn1ccnc1CN2 | O=C1NC2=C(CN3C1=NC=C3)C=CC=C2.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>>N=1C=CN2C1CNC1=C(C2)C=CC=C1 | O=[C:13]1[c:12]2[n:8]([cH:9][cH:10][n:11]2)[CH2:7][c:5]2[c:4]([cH:3][cH:2][cH:1][cH:6]2)[NH:14]1>>[cH:1]1[cH:2][cH:3][c:4]2[c:5]([cH:6]1)[CH2:7][n:8]1[cH:9][cH:10][n:11][c:12]1[CH2:13][NH:14]2 | O=C1Nc2ccccc2Cn2ccnc21 | c1ccc2c(c1)Cn1ccnc1CN2 | null | null | O1CCCC1 | Reduction | Reduction of secondary amides to amines | 210fc59cede1512da4e9b4d6cd6db7f332228e1f2796118fdc26baf979fbcc03 | ab40188eef2f825df7003af0ffae31d0ce53d126542122535627d3d354cbc9fe | c1ccc2c(c1)Cn1ccnc1CN2 | O=[C;H0;D3;+0:1](-[#7:2]-[c:3])-[c:4]1:[#7;a:5]:[c:6]:[c:7]:[#7;a:8]:1-[C:9]>>[C:9]-[#7;a:8]1:[c:7]:[c:6]:[#7;a:5]:[c:4]:1-[CH2;D2;+0:1]-[#7:2]-[c:3] | null | [] | 0 | CELSIUS | null | null | To a suspension of 4 mmol of lithium aluminum hydride in 20 ml of anhydrous tetrahydrofuran is added a 1 mmol solution of 10,11-dihydro-11-oxo-5H-imidazo-[2,1-c][1,4]benzodiazepine and the mixture is refluxed for 24 hours and cooled at 0° C. To the mixture is added dropwise 0.12 ml of water and 6 ml of 1N sodium hydrox... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide | null | c1ccc2c(c1)Cn1ccnc1CN2 | c1ccc2c(c1)Cn1ccnc1CN2 | c1ccc2c(c1)Cn1ccnc1CN2 | Other | O1CCCC1 | 0 | null | O=C1Nc2ccccc2Cn2ccnc21>O1CCCC1>c1ccc2c(c1)Cn1ccnc1CN2 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-e07587b1de2c4d5a8150e75521845099 | Cc1ccccc1C(=O)Nc1ccc(C(=O)Cl)cc1.c1ccc2c(c1)Cn1ccnc1CN2>>Cc1ccccc1C(=O)Nc1ccc(C(=O)N2Cc3nccn3Cc3ccccc32)cc1 | N=1C=CN2C1CNC1=C(C2)C=CC=C1.CC1=C(C(=O)NC2=CC=C(C(=O)Cl)C=C2)C=CC=C1.C(C)N(CC)CC>>N=1C=CN2C1CN(C1=C(C2)C=CC=C1)C(=O)C1=CC=C(C=C1)NC(C1=C(C=CC=C1)C)=O | Cl[C:15]([c:14]1[cH:13][cH:12][c:11]([NH:10][C:8]([c:7]2[c:2]([CH3:1])[cH:3][cH:4][cH:5][cH:6]2)=[O:9])[cH:32][cH:31]1)=[O:16].[NH:17]1[CH2:18][c:19]2[n:20][cH:21][cH:22][n:23]2[CH2:24][c:25]2[cH:26][cH:27][cH:28][cH:29][c:30]21>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][cH:6][c:7]1[C:8](=[O:9])[NH:10][c:11]1[cH:12][cH:13][c:14]... | Cc1ccccc1C(=O)Nc1ccc(C(=O)Cl)cc1.c1ccc2c(c1)Cn1ccnc1CN2 | Cc1ccccc1C(=O)Nc1ccc(C(=O)N2Cc3nccn3Cc3ccccc32)cc1 | null | null | C(Cl)Cl | Acylation | N-alkylation of secondary amines with alkyl halides | 6511e9594f4737dfd6f4c4f359ed58f3edbe4e84fa4a9c6fa940b8ef86be479e | 96cb0a2fed10552c5770a45a2d6523b47ac3e38928b4a9c698d8577451182dcd | O=C(Nc1ccc(C(=O)N2Cc3nccn3Cc3ccccc32)cc1)c1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[#7;a:6]:[c:7](:[#7;a:8])-[C:9]-[NH;D2;+0:10]-[c:11](:[c:12]):[c:13]>>[#7;a:6]:[c:7](:[#7;a:8])-[C:9]-[N;H0;D3;+0:10](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5])-[c:11](:[c:12]):[c:13] | null | [] | 0 | CELSIUS | 3 | MINUTE | To a mixture of 1.37 g (5 mmol) of 4-[(2-methylbenzoyl)amino]benzoyl chloride in 15 ml of methylene chloride, cooled to 0° C. is added 1.5 ml of triethylamine. After stirring for 3 minutes, 5 mmol of 10,11-dihydro-5H-imidazo[2,1-c][1,4]benzodiazepine in 5 ml of methylene chloride is added. The cooling bath is removed a... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Secondary amine | Tertiary amide | c1ccc2c(c1)Cn1ccnc1CN2 | c1ccc2c(c1)Cn1ccnc1C[NH]2 | c1ccccc1.c1ccccc1.c1ccc2c(c1)Cn1ccnc1C[NH]2 | HCl | C(Cl)Cl | 0 | 0.05 | Cc1ccccc1C(=O)Nc1ccc(C(=O)Cl)cc1.c1ccc2c(c1)Cn1ccnc1CN2>C(Cl)Cl>Cc1ccccc1C(=O)Nc1ccc(C(=O)N2Cc3nccn3Cc3ccccc32)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-bf3f22d548784dd98df4216671f83cda | O=C(Cl)c1ccc([N+](=O)[O-])cc1.c1ccc2c(c1)Cn1ccnc1CN2>>O=C(c1ccc([N+](=O)[O-])cc1)N1Cc2nccn2Cc2ccccc21 | [N+](=O)([O-])C1=CC=C(C(=O)Cl)C=C1.N=1C=CN2C1CNC1=C(C2)C=CC=C1.C(C)N(CC)CC>>[N+](=O)([O-])C1=CC=C(C(=O)N2CC=3N(CC4=C2C=CC=C4)C=CN3)C=C1 | Cl[C:2](=[O:1])[c:3]1[cH:4][cH:5][c:6]([N+:7](=[O:8])[O-:9])[cH:10][cH:11]1.[NH:12]1[CH2:13][c:14]2[n:15][cH:16][cH:17][n:18]2[CH2:19][c:20]2[cH:21][cH:22][cH:23][cH:24][c:25]21>>[O:1]=[C:2]([c:3]1[cH:4][cH:5][c:6]([N+:7](=[O:8])[O-:9])[cH:10][cH:11]1)[N:12]1[CH2:13][c:14]2[n:15][cH:16][cH:17][n:18]2[CH2:19][c:20]2[cH:... | O=C(Cl)c1ccc([N+](=O)[O-])cc1.c1ccc2c(c1)Cn1ccnc1CN2 | O=C(c1ccc([N+](=O)[O-])cc1)N1Cc2nccn2Cc2ccccc21 | null | null | C(Cl)Cl.C(C)(=O)OCC | Acylation | N-alkylation of secondary amines with alkyl halides | 6511e9594f4737dfd6f4c4f359ed58f3edbe4e84fa4a9c6fa940b8ef86be479e | 96cb0a2fed10552c5770a45a2d6523b47ac3e38928b4a9c698d8577451182dcd | O=C(c1ccccc1)N1Cc2nccn2Cc2ccccc21 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[#7;a:6]:[c:7](:[#7;a:8])-[C:9]-[NH;D2;+0:10]-[c:11](:[c:12]):[c:13]>>[#7;a:6]:[c:7](:[#7;a:8])-[C:9]-[N;H0;D3;+0:10](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5])-[c:11](:[c:12]):[c:13] | null | [] | null | null | 2 | HOUR | To a solution of 10 mmol of 10,11-dihydro-5H-imidazo[2,1-c][1,4]benzodiazepine in 50 ml of methylene chloride under argon is added 15 mmol of triethylamine followed by ice bath cooling. A solution of 10 mmol of 4-nitrobenzoyl chloride in 10 ml of methylene chloride is added dropwise. Following complete addition, the ic... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Secondary amine | Tertiary amide | c1ccc2c(c1)Cn1ccnc1CN2 | c1ccc2c(c1)Cn1ccnc1C[NH]2 | c1ccccc1.c1ccc2c(c1)Cn1ccnc1C[NH]2 | HCl | C(Cl)Cl.C(C)(=O)OCC | null | 2 | O=C(Cl)c1ccc([N+](=O)[O-])cc1.c1ccc2c(c1)Cn1ccnc1CN2>C(Cl)Cl.C(C)(=O)OCC>O=C(c1ccc([N+](=O)[O-])cc1)N1Cc2nccn2Cc2ccccc21 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-9b7f8c988c1346ab89148d00d0ed8b57 | O=C(c1ccc([N+](=O)[O-])cc1)N1Cc2nccn2Cc2ccccc21>>Nc1ccc(C(=O)N2Cc3nccn3Cc3ccccc32)cc1 | [N+](=O)([O-])C1=CC=C(C(=O)N2CC=3N(CC4=C2C=CC=C4)C=CN3)C=C1.C(C)(=O)OCC.[H][H]>>NC1=CC=C(C(=O)N2CC=3N(CC4=C2C=CC=C4)C=CN3)C=C1 | O=[N+:1]([O-])[c:2]1[cH:3][cH:4][c:5]([C:6](=[O:7])[N:8]2[CH2:9][c:10]3[n:11][cH:12][cH:13][n:14]3[CH2:15][c:16]3[cH:17][cH:18][cH:19][cH:20][c:21]32)[cH:22][cH:23]1>>[NH2:1][c:2]1[cH:3][cH:4][c:5]([C:6](=[O:7])[N:8]2[CH2:9][c:10]3[n:11][cH:12][cH:13][n:14]3[CH2:15][c:16]3[cH:17][cH:18][cH:19][cH:20][c:21]32)[cH:22][cH... | O=C(c1ccc([N+](=O)[O-])cc1)N1Cc2nccn2Cc2ccccc21 | Nc1ccc(C(=O)N2Cc3nccn3Cc3ccccc32)cc1 | null | [Pd] | C(C)O | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | O=C(c1ccccc1)N1Cc2nccn2Cc2ccccc21 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | null | null | A mixture of 5 mmol of 10,11-dihydro-10-(4-nitrobenzoyl)-5H-imidazo[2,1-c][1,4]benzodiazepine in 10 ml of ethyl alcohol and 10 ml of ethyl acetate containing 0.2 g of 10% Pd/C is hydrogenated for 5 hours in a Parr hydrogenator at 35 psi of hydrogen. The reaction mixture is filtered through a pad of diatomaceous earth. ... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1.c1ccc2c(c1)Cn1ccnc1C[NH]2 | Other | [Pd].C(C)O | null | null | O=C(c1ccc([N+](=O)[O-])cc1)N1Cc2nccn2Cc2ccccc21>[Pd].C(C)O>Nc1ccc(C(=O)N2Cc3nccn3Cc3ccccc32)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-f309c4cdf6ca4d63bfa6d98eeb89f86f | O=C(c1ccc([N+](=O)[O-])cc1)N1Cc2nccn2Cc2ccccc21>>Nc1ccc(C(=O)N2Cc3nccn3Cc3ccccc32)cc1 | [N+](=O)([O-])C1=CC=C(C(=O)N2CC=3N(CC4=C2C=CC=C4)C=CN3)C=C1.NN>>NC1=CC=C(C(=O)N2CC=3N(CC4=C2C=CC=C4)C=CN3)C=C1 | O=[N+:1]([O-])[c:2]1[cH:3][cH:4][c:5]([C:6](=[O:7])[N:8]2[CH2:9][c:10]3[n:11][cH:12][cH:13][n:14]3[CH2:15][c:16]3[cH:17][cH:18][cH:19][cH:20][c:21]32)[cH:22][cH:23]1>>[NH2:1][c:2]1[cH:3][cH:4][c:5]([C:6](=[O:7])[N:8]2[CH2:9][c:10]3[n:11][cH:12][cH:13][n:14]3[CH2:15][c:16]3[cH:17][cH:18][cH:19][cH:20][c:21]32)[cH:22][cH... | O=C(c1ccc([N+](=O)[O-])cc1)N1Cc2nccn2Cc2ccccc21 | Nc1ccc(C(=O)N2Cc3nccn3Cc3ccccc32)cc1 | null | [Pd] | C(C)O | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | O=C(c1ccccc1)N1Cc2nccn2Cc2ccccc21 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | null | null | To a solution of 5 mmol of 10,11-dihydro-10-(4-nitrobenzoyl)-5H-imidazo[2,1-c][1,4]benzodiazepine in 100 ml of ethyl alcohol is added 0.5 g of 10% Pd/C and 10 mmol of hydrazine followed by stirring and heating under reflux for 3 hours. The reaction mixture is filtered through diatomaceous earth. The filtrate is concent... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1.c1ccc2c(c1)Cn1ccnc1C[NH]2 | Other | [Pd].C(C)O | null | null | O=C(c1ccc([N+](=O)[O-])cc1)N1Cc2nccn2Cc2ccccc21>[Pd].C(C)O>Nc1ccc(C(=O)N2Cc3nccn3Cc3ccccc32)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-ed0adb1a440841d2ae69bafb2542dd69 | Cc1ccccc1C(=O)Cl.Nc1ccc(C(=O)N2Cc3nccn3Cc3ccccc32)cc1>>Cc1ccccc1C(=O)Nc1ccc(C(=O)N2Cc3nccn3Cc3ccccc32)cc1 | NC1=CC=C(C(=O)N2CC=3N(CC4=C2C=CC=C4)C=CN3)C=C1.CC1=C(C(=O)Cl)C=CC=C1.C(C)N(CC)CC>>N=1C=CN2C1CN(C1=C(C2)C=CC=C1)C(=O)C1=CC=C(C=C1)NC(C1=C(C=CC=C1)C)=O | Cl[C:8]([c:7]1[c:2]([CH3:1])[cH:3][cH:4][cH:5][cH:6]1)=[O:9].[NH2:10][c:11]1[cH:12][cH:13][c:14]([C:15](=[O:16])[N:17]2[CH2:18][c:19]3[n:20][cH:21][cH:22][n:23]3[CH2:24][c:25]3[cH:26][cH:27][cH:28][cH:29][c:30]32)[cH:31][cH:32]1>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][cH:6][c:7]1[C:8](=[O:9])[NH:10][c:11]1[cH:12][cH:13][c:14]... | Cc1ccccc1C(=O)Cl.Nc1ccc(C(=O)N2Cc3nccn3Cc3ccccc32)cc1 | Cc1ccccc1C(=O)Nc1ccc(C(=O)N2Cc3nccn3Cc3ccccc32)cc1 | null | null | C(Cl)Cl | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=C(Nc1ccc(C(=O)N2Cc3nccn3Cc3ccccc32)cc1)c1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9])-[c:3](:[c:4]):[c:5] | null | [] | null | null | 15 | MINUTE | To a stirred solution of 1 mmol of 2-methylbenzoyl chloride in 10 ml of methylene chloride is added 1.5 mmol of triethylamine. After stirring for 15 minutes, 1 mmol of 10,11-dihydro-10-(4-aminobenzoyl)-5H-imidazo[2,1-c][1,4]benzodiazepine is added and the mixture stirred for 5 hours. The reaction mixture is washed with... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccccc1.c1ccc2c(c1)Cn1ccnc1C[NH]2 | HCl | C(Cl)Cl | null | 0.25 | Cc1ccccc1C(=O)Cl.Nc1ccc(C(=O)N2Cc3nccn3Cc3ccccc32)cc1>C(Cl)Cl>Cc1ccccc1C(=O)Nc1ccc(C(=O)N2Cc3nccn3Cc3ccccc32)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-753e4a858f2c476d8ba39b9fa7affcdf | O=C(Cl)c1ccc([N+](=O)[O-])cc1.c1ccc2c(c1)NCc1cccn1-2>>O=C(c1ccc([N+](=O)[O-])cc1)N1Cc2cccn2-c2ccccc21 | [N+](=O)([O-])C1=CC=C(C(=O)Cl)C=C1.C1=CC=C2N1C1=CC=CC=C1NC2.C(C)N(CC)CC>>[N+](=O)([O-])C1=CC=C(C(=O)N2CC=3N(C4=CC=CC=C24)C=CC3)C=C1 | Cl[C:2](=[O:1])[c:3]1[cH:4][cH:5][c:6]([N+:7](=[O:8])[O-:9])[cH:10][cH:11]1.[NH:12]1[CH2:13][c:14]2[cH:15][cH:16][cH:17][n:18]2-[c:19]2[cH:20][cH:21][cH:22][cH:23][c:24]21>>[O:1]=[C:2]([c:3]1[cH:4][cH:5][c:6]([N+:7](=[O:8])[O-:9])[cH:10][cH:11]1)[N:12]1[CH2:13][c:14]2[cH:15][cH:16][cH:17][n:18]2-[c:19]2[cH:20][cH:21][c... | O=C(Cl)c1ccc([N+](=O)[O-])cc1.c1ccc2c(c1)NCc1cccn1-2 | O=C(c1ccc([N+](=O)[O-])cc1)N1Cc2cccn2-c2ccccc21 | null | null | C(Cl)Cl.C(C)(=O)OCC | Acylation | N-alkylation of secondary amines with alkyl halides | ec52d278830efdaee8ac897d4cca585d04ae9529b1822869284bce5446c8c555 | 96cb0a2fed10552c5770a45a2d6523b47ac3e38928b4a9c698d8577451182dcd | O=C(c1ccccc1)N1Cc2cccn2-c2ccccc21 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[c:6]:[c:7]1:[c:8]-[#7;a:9]:[c:10]-[C:11]-[NH;D2;+0:12]-1>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[N;H0;D3;+0:12]1-[C:11]-[c:10]:[#7;a:9]-[c:8]:[c:7]-1:[c:6])-[c:3](:[c:4]):[c:5] | null | [] | null | null | 2 | HOUR | To a solution of 5 mmol of 4,5-dihydropyrrolo[1,2-a]quinoxaline in 50 ml of methylene chloride under argon is added 10 mmol of triethylamine followed by ice bath cooling. A solution of 5 mmol of 4-nitrobenzoyl chloride in 10 ml of methylene chloride is added dropwise. Following complete addition, the ice bath is remove... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Secondary amine | Tertiary amide | c1ccc2c(c1)NCc1cccn12 | c1ccc2c(c1)[NH]Cc1cccn12 | c1ccccc1.c1ccc2c(c1)[NH]Cc1cccn12 | HCl | C(Cl)Cl.C(C)(=O)OCC | null | 2 | O=C(Cl)c1ccc([N+](=O)[O-])cc1.c1ccc2c(c1)NCc1cccn1-2>C(Cl)Cl.C(C)(=O)OCC>O=C(c1ccc([N+](=O)[O-])cc1)N1Cc2cccn2-c2ccccc21 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-5a48814bcd814c6ca7b5e64ce3c58be8 | O=C(c1ccc([N+](=O)[O-])cc1)N1Cc2cccn2-c2ccccc21>>Nc1ccc(C(=O)N2Cc3cccn3-c3ccccc32)cc1 | [N+](=O)([O-])C1=CC=C(C(=O)N2CC=3N(C4=CC=CC=C24)C=CC3)C=C1.C(C)(=O)OCC>>NC1=CC=C(C(=O)N2CC=3N(C4=CC=CC=C24)C=CC3)C=C1 | O=[N+:1]([O-])[c:2]1[cH:3][cH:4][c:5]([C:6](=[O:7])[N:8]2[CH2:9][c:10]3[cH:11][cH:12][cH:13][n:14]3-[c:15]3[cH:16][cH:17][cH:18][cH:19][c:20]32)[cH:21][cH:22]1>>[NH2:1][c:2]1[cH:3][cH:4][c:5]([C:6](=[O:7])[N:8]2[CH2:9][c:10]3[cH:11][cH:12][cH:13][n:14]3-[c:15]3[cH:16][cH:17][cH:18][cH:19][c:20]32)[cH:21][cH:22]1 | O=C(c1ccc([N+](=O)[O-])cc1)N1Cc2cccn2-c2ccccc21 | Nc1ccc(C(=O)N2Cc3cccn3-c3ccccc32)cc1 | null | [Pd] | C(C)O | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | O=C(c1ccccc1)N1Cc2cccn2-c2ccccc21 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | 5 | HOUR | A mixture of 1 mmol of 4,5-dihydro-5-(4-nitrobenzoyl)pyrrolo[1,2-a]quinoxaline in 10 ml of ethyl alcohol and 10 ml of ethyl acetate containing 0.2 g of 10% Pd/C is hydrogenated for 5 hours. The reaction mixture is filtered through a pad of diatomaceous earth. The filtrate is concentrated in vacuo to a solid which is pu... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1.c1ccc2c(c1)[NH]Cc1cccn12 | Other | [Pd].C(C)O | null | 5 | O=C(c1ccc([N+](=O)[O-])cc1)N1Cc2cccn2-c2ccccc21>[Pd].C(C)O>Nc1ccc(C(=O)N2Cc3cccn3-c3ccccc32)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-f8a9d90712124232849f597147bf6228 | O=C(c1ccc([N+](=O)[O-])cc1)N1Cc2cccn2-c2ccccc21>>Nc1ccc(C(=O)N2Cc3cccn3-c3ccccc32)cc1 | [N+](=O)([O-])C1=CC=C(C(=O)N2CC=3N(C4=CC=CC=C24)C=CC3)C=C1.NN>>NC1=CC=C(C(=O)N2CC=3N(C4=CC=CC=C24)C=CC3)C=C1 | O=[N+:1]([O-])[c:2]1[cH:3][cH:4][c:5]([C:6](=[O:7])[N:8]2[CH2:9][c:10]3[cH:11][cH:12][cH:13][n:14]3-[c:15]3[cH:16][cH:17][cH:18][cH:19][c:20]32)[cH:21][cH:22]1>>[NH2:1][c:2]1[cH:3][cH:4][c:5]([C:6](=[O:7])[N:8]2[CH2:9][c:10]3[cH:11][cH:12][cH:13][n:14]3-[c:15]3[cH:16][cH:17][cH:18][cH:19][c:20]32)[cH:21][cH:22]1 | O=C(c1ccc([N+](=O)[O-])cc1)N1Cc2cccn2-c2ccccc21 | Nc1ccc(C(=O)N2Cc3cccn3-c3ccccc32)cc1 | null | [Pd] | C(C)O | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | O=C(c1ccccc1)N1Cc2cccn2-c2ccccc21 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | null | null | To a solution of 1 mmol of 4,5-dihydro-5-(4-nitrobenzoyl)pyrrolo[1,2-a]quinoxaline in 20 ml of ethyl alcohol is added 0.2 g of 10% Pd/C and 2.5 mmol of hydrazine followed by stirring and heating under reflux for 2 hours. The hot reaction mixture is filtered through diatomaceous earth and the filter cake washed with hot... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1.c1ccc2c(c1)[NH]Cc1cccn12 | Other | [Pd].C(C)O | null | null | O=C(c1ccc([N+](=O)[O-])cc1)N1Cc2cccn2-c2ccccc21>[Pd].C(C)O>Nc1ccc(C(=O)N2Cc3cccn3-c3ccccc32)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-d12b56b5b20a4955b1708468ea38864a | Cc1ccccc1C(=O)Cl.Nc1ccc(C(=O)N2Cc3cccn3-c3ccccc32)cc1>>Cc1ccccc1C(=O)Nc1ccc(C(=O)N2Cc3cccn3-c3ccccc32)cc1 | NC1=CC=C(C(=O)N2CC=3N(C4=CC=CC=C24)C=CC3)C=C1.CC1=C(C(=O)Cl)C=CC=C1.C(C)N(CC)CC>>C1=CC=C2N1C1=CC=CC=C1N(C2)C(=O)C2=CC=C(C=C2)NC(C2=C(C=CC=C2)C)=O | Cl[C:8]([c:7]1[c:2]([CH3:1])[cH:3][cH:4][cH:5][cH:6]1)=[O:9].[NH2:10][c:11]1[cH:12][cH:13][c:14]([C:15](=[O:16])[N:17]2[CH2:18][c:19]3[cH:20][cH:21][cH:22][n:23]3-[c:24]3[cH:25][cH:26][cH:27][cH:28][c:29]32)[cH:30][cH:31]1>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][cH:6][c:7]1[C:8](=[O:9])[NH:10][c:11]1[cH:12][cH:13][c:14]([C:15... | Cc1ccccc1C(=O)Cl.Nc1ccc(C(=O)N2Cc3cccn3-c3ccccc32)cc1 | Cc1ccccc1C(=O)Nc1ccc(C(=O)N2Cc3cccn3-c3ccccc32)cc1 | null | null | C(Cl)Cl | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=C(Nc1ccc(C(=O)N2Cc3cccn3-c3ccccc32)cc1)c1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9])-[c:3](:[c:4]):[c:5] | null | [] | null | null | 15 | MINUTE | To a stirred solution of 1.5 mmol of 2-methylbenzoyl chloride in 10 ml of methylene chloride is added 3 mmol of triethylamine. After stirring for 15 minutes, 1.5 mmol of 4,5-dihydro-5-(4-aminobenzoyl)pyrrolo[1,2-a]quinoxaline is added and the mixture stirred for 5 hours. The reaction mixture is washed with water, 1N HC... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccccc1.c1ccc2c(c1)[NH]Cc1cccn12 | HCl | C(Cl)Cl | null | 0.25 | Cc1ccccc1C(=O)Cl.Nc1ccc(C(=O)N2Cc3cccn3-c3ccccc32)cc1>C(Cl)Cl>Cc1ccccc1C(=O)Nc1ccc(C(=O)N2Cc3cccn3-c3ccccc32)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-de286a678e6941c0b0d7eac1b51b1208 | O=C1Nc2occc2Cn2cccc21>>c1cc2n(c1)Cc1ccoc1NC2 | [OH-].[Na+].O1C=CC2=C1NC(C=1N(C2)C=CC1)=O.[H-].[Al+3].[Li+].[H-].[H-].[H-].O>>O1C=CC2=C1NCC=1N(C2)C=CC1 | O=[C:13]1[c:3]2[cH:2][cH:1][cH:5][n:4]2[CH2:6][c:7]2[cH:8][cH:9][o:10][c:11]2[NH:12]1>>[cH:1]1[cH:2][c:3]2[n:4]([cH:5]1)[CH2:6][c:7]1[cH:8][cH:9][o:10][c:11]1[NH:12][CH2:13]2 | O=C1Nc2occc2Cn2cccc21 | c1cc2n(c1)Cc1ccoc1NC2 | null | null | O1CCCC1 | Reduction | Reduction of secondary amides to amines | 77961be3a88f49ac9da98823ddbcc29be5366b96b3ba894a1d3c595efa47b921 | ab40188eef2f825df7003af0ffae31d0ce53d126542122535627d3d354cbc9fe | c1cc2n(c1)Cc1ccoc1NC2 | O=[C;H0;D3;+0:1](-[#7:2]-[c:3]:[#8;a:4])-[c:5](:[c:6]):[#7;a:7](:[c:8])-[C:9]>>[#8;a:4]:[c:3]-[#7:2]-[CH2;D2;+0:1]-[c:5](:[c:6]):[#7;a:7](:[c:8])-[C:9] | null | [] | null | null | 8 | HOUR | To a suspension of 4 mmol of lithium aluminum hydride in 25 ml of anhydrous tetrahydrofuran is added 1 mmol of 9,10-dihydro-4H-furo[2,3-e]pyrrolo[1,2-a][1,4]diazepin-9-one. The mixture is refluxed for 12 hours and allowed to stand overnight. To the mixture is added dropwise 0.12 ml of water and then 6 ml of 1N sodium h... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide | null | c1cc2n(c1)Cc1ccoc1NC2 | c1cc2n(c1)Cc1ccoc1NC2 | c1cc2n(c1)Cc1ccoc1NC2 | Other | O1CCCC1 | null | 8 | O=C1Nc2occc2Cn2cccc21>O1CCCC1>c1cc2n(c1)Cc1ccoc1NC2 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-dd593ac273974c248c661f856d06b2b8 | C1=Nc2occc2Cn2cccc21>>c1cc2n(c1)Cc1ccoc1NC2 | O1C=CC2=C1N=CC=1N(C2)C=CC1>>O1C=CC2=C1NCC=1N(C2)C=CC1 | [cH:1]1[cH:2][c:3]2[n:4]([cH:5]1)[CH2:6][c:7]1[cH:8][cH:9][o:10][c:11]1[N:12]=[CH:13]2>>[cH:1]1[cH:2][c:3]2[n:4]([cH:5]1)[CH2:6][c:7]1[cH:8][cH:9][o:10][c:11]1[NH:12][CH2:13]2 | C1=Nc2occc2Cn2cccc21 | c1cc2n(c1)Cc1ccoc1NC2 | null | [Pd] | C(C)O | Reduction | OtherReaction | f90e29859e738ab626c26ba6655b8134da27053959a22cf6e43571b4b2decc94 | 469efbca661320a0d72c32f19625ec46edbc3ad7686cf46fdd0591eb136a8d7e | c1cc2n(c1)Cc1ccoc1NC2 | [c:1]:[c:2]1:[#7;a:3](:[c:4])-[C:5]-[c:6]:[c:7](:[#8;a:8]:[c:9])-[N;H0;D2;+0:10]=[CH;D2;+0:11]-1>>[c:1]:[c:2]1:[#7;a:3](:[c:4])-[C:5]-[c:6]:[c:7](:[#8;a:8]:[c:9])-[NH;D2;+0:10]-[CH2;D2;+0:11]-1 | null | [] | null | null | null | null | A solution of 1 mmol of 4H-furo[2,3-e]pyrrolo[1,2-a][1,4]diazepine and 0.2 g of 10% Pd/C in 10 ml of 10 ml of ethanol is hydrogenated for 18 hours. The reaction mixture is filtered through diatomaceous earth and the filtrate is evaporated in vacuo to give the desired product as a solid.
Conditions: See reaction.notes.p... | 10.6084/m9.figshare.5104873.v1 | null | Substituted imine | Secondary amine | C1=Nc2occc2Cn2cccc21 | c1cc2n(c1)Cc1ccoc1NC2 | c1cc2n(c1)Cc1ccoc1NC2 | null | [Pd].C(C)O | null | null | C1=Nc2occc2Cn2cccc21>[Pd].C(C)O>c1cc2n(c1)Cc1ccoc1NC2 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-5f938858357146d8a8d932bcaf02b969 | Cc1ccccc1C(=O)Nc1ccc(C(=O)Cl)cc1.c1cc2n(c1)Cc1ccoc1NC2>>Cc1ccccc1C(=O)Nc1ccc(C(=O)N2Cc3cccn3Cc3ccoc32)cc1 | CC1=C(C(=O)NC2=CC=C(C(=O)Cl)C=C2)C=CC=C1.C(C)N(CC)CC.O1C=CC2=C1NCC=1N(C2)C=CC1>>O1C=CC2=C1N(CC=1N(C2)C=CC1)C(=O)C1=CC=C(C=C1)NC(C1=C(C=CC=C1)C)=O | Cl[C:15]([c:14]1[cH:13][cH:12][c:11]([NH:10][C:8]([c:7]2[c:2]([CH3:1])[cH:3][cH:4][cH:5][cH:6]2)=[O:9])[cH:31][cH:30]1)=[O:16].[NH:17]1[CH2:18][c:19]2[cH:20][cH:21][cH:22][n:23]2[CH2:24][c:25]2[cH:26][cH:27][o:28][c:29]21>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][cH:6][c:7]1[C:8](=[O:9])[NH:10][c:11]1[cH:12][cH:13][c:14]([C:15]... | Cc1ccccc1C(=O)Nc1ccc(C(=O)Cl)cc1.c1cc2n(c1)Cc1ccoc1NC2 | Cc1ccccc1C(=O)Nc1ccc(C(=O)N2Cc3cccn3Cc3ccoc32)cc1 | null | null | C(Cl)Cl | Acylation | N-alkylation of secondary amines with alkyl halides | 3bfe8955617c13b212cca2f7a8d28865f2947fc6342e809e7f4cf02e9f1bcd8c | 96cb0a2fed10552c5770a45a2d6523b47ac3e38928b4a9c698d8577451182dcd | O=C(Nc1ccc(C(=O)N2Cc3cccn3Cc3ccoc32)cc1)c1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[#7;a:6]:[c:7]-[C:8]-[NH;D2;+0:9]-[c:10](:[c:11]):[#8;a:12]:[c:13]>>[#7;a:6]:[c:7]-[C:8]-[N;H0;D3;+0:9](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5])-[c:10](:[c:11]):[#8;a:12]:[c:13] | null | [] | 0 | CELSIUS | 2 | HOUR | To a mixture of 1.1 mmol of 4-[(2-methylbenzoyl)amino]benzoyl chloride in 10 ml of methylene chloride, cooled to 0° C. is added 1.5 mmol of triethylamine. To the mixture is added 1 mmol of 9,10-dihydro-4H-furo[2,3-e]pyrrolo[1,2-a][1,4]diazepine and the mixture stirred at room temperature for 2 hours. The reaction mixtu... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Secondary amine | Tertiary amide | c1cc2n(c1)Cc1ccoc1NC2 | c1cc2n(c1)Cc1ccoc1[NH]C2 | c1ccccc1.c1ccccc1.c1cc2n(c1)Cc1ccoc1[NH]C2 | HCl | C(Cl)Cl | 0 | 2 | Cc1ccccc1C(=O)Nc1ccc(C(=O)Cl)cc1.c1cc2n(c1)Cc1ccoc1NC2>C(Cl)Cl>Cc1ccccc1C(=O)Nc1ccc(C(=O)N2Cc3cccn3Cc3ccoc32)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-0ff801941ad246b7b032c76a3c9a277b | O=C(Cl)c1ccc([N+](=O)[O-])cc1.c1cc2n(c1)Cc1ccoc1NC2>>O=C(c1ccc([N+](=O)[O-])cc1)N1Cc2cccn2Cc2ccoc21 | [N+](=O)([O-])C1=CC=C(C(=O)Cl)C=C1.O1C=CC2=C1NCC=1N(C2)C=CC1.C(C)N(CC)CC>>[N+](=O)([O-])C1=CC=C(C(=O)N2CC=3N(CC4=C2OC=C4)C=CC3)C=C1 | Cl[C:2](=[O:1])[c:3]1[cH:4][cH:5][c:6]([N+:7](=[O:8])[O-:9])[cH:10][cH:11]1.[NH:12]1[CH2:13][c:14]2[cH:15][cH:16][cH:17][n:18]2[CH2:19][c:20]2[cH:21][cH:22][o:23][c:24]21>>[O:1]=[C:2]([c:3]1[cH:4][cH:5][c:6]([N+:7](=[O:8])[O-:9])[cH:10][cH:11]1)[N:12]1[CH2:13][c:14]2[cH:15][cH:16][cH:17][n:18]2[CH2:19][c:20]2[cH:21][cH... | O=C(Cl)c1ccc([N+](=O)[O-])cc1.c1cc2n(c1)Cc1ccoc1NC2 | O=C(c1ccc([N+](=O)[O-])cc1)N1Cc2cccn2Cc2ccoc21 | null | null | C(Cl)Cl.C(C)(=O)OCC | Acylation | N-alkylation of secondary amines with alkyl halides | 3bfe8955617c13b212cca2f7a8d28865f2947fc6342e809e7f4cf02e9f1bcd8c | 96cb0a2fed10552c5770a45a2d6523b47ac3e38928b4a9c698d8577451182dcd | O=C(c1ccccc1)N1Cc2cccn2Cc2ccoc21 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[#7;a:6]:[c:7]-[C:8]-[NH;D2;+0:9]-[c:10](:[c:11]):[#8;a:12]:[c:13]>>[#7;a:6]:[c:7]-[C:8]-[N;H0;D3;+0:9](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5])-[c:10](:[c:11]):[#8;a:12]:[c:13] | null | [] | null | null | 2 | HOUR | To a solution of 1.0 mmol of 9,10-dihydro-4H-furo[2,3-e]pyrrolo[1,2-a][1,4]diazepine in 10 ml of methylene chloride under argon is added 1.5 mmol of triethylamine followed by ice bath cooling. A solution of 1.1 mmol of 4-nitrobenzoyl chloride in 5 ml of methylene chloride is added dropwise. Following complete addition,... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Secondary amine | Tertiary amide | c1cc2n(c1)Cc1ccoc1NC2 | c1cc2n(c1)Cc1ccoc1[NH]C2 | c1ccccc1.c1cc2n(c1)Cc1ccoc1[NH]C2 | HCl | C(Cl)Cl.C(C)(=O)OCC | null | 2 | O=C(Cl)c1ccc([N+](=O)[O-])cc1.c1cc2n(c1)Cc1ccoc1NC2>C(Cl)Cl.C(C)(=O)OCC>O=C(c1ccc([N+](=O)[O-])cc1)N1Cc2cccn2Cc2ccoc21 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-e9c7287769a24e6b9530ad0b4b3bef5d | O=C(c1ccc([N+](=O)[O-])cc1)N1Cc2cccn2Cc2ccoc21>>Nc1ccc(C(=O)N2Cc3cccn3Cc3ccoc32)cc1 | [N+](=O)([O-])C1=CC=C(C(=O)N2CC=3N(CC4=C2OC=C4)C=CC3)C=C1.C(C)(=O)OCC>>NC1=CC=C(C(=O)N2CC=3N(CC4=C2OC=C4)C=CC3)C=C1 | O=[N+:1]([O-])[c:2]1[cH:3][cH:4][c:5]([C:6](=[O:7])[N:8]2[CH2:9][c:10]3[cH:11][cH:12][cH:13][n:14]3[CH2:15][c:16]3[cH:17][cH:18][o:19][c:20]32)[cH:21][cH:22]1>>[NH2:1][c:2]1[cH:3][cH:4][c:5]([C:6](=[O:7])[N:8]2[CH2:9][c:10]3[cH:11][cH:12][cH:13][n:14]3[CH2:15][c:16]3[cH:17][cH:18][o:19][c:20]32)[cH:21][cH:22]1 | O=C(c1ccc([N+](=O)[O-])cc1)N1Cc2cccn2Cc2ccoc21 | Nc1ccc(C(=O)N2Cc3cccn3Cc3ccoc32)cc1 | null | [Pd] | C(C)O | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | O=C(c1ccccc1)N1Cc2cccn2Cc2ccoc21 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | 5 | HOUR | A mixture of 1 mmol of 9,10-dihydro-10-(4-nitrobenzoyl)-4H-furo[2,3-e]pyrrolo[1,2-a][1,4]diazepine in 10 ml of ethyl alcohol and 10 ml of ethyl acetate containing 0.2 g of 10% Pd/C is hydrogenated for 5 hours. The reaction mixture is filtered through a pad of diatomaceous earth. The filtrate is concentrated in vacuo to... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1.c1cc2n(c1)Cc1ccoc1[NH]C2 | Other | [Pd].C(C)O | null | 5 | O=C(c1ccc([N+](=O)[O-])cc1)N1Cc2cccn2Cc2ccoc21>[Pd].C(C)O>Nc1ccc(C(=O)N2Cc3cccn3Cc3ccoc32)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-e3bdc34f4e1540a0adc207a4fc060fb9 | O=C(c1ccc([N+](=O)[O-])cc1)N1Cc2cccn2Cc2ccoc21>>Nc1ccc(C(=O)N2Cc3cccn3Cc3ccoc32)cc1 | [N+](=O)([O-])C1=CC=C(C(=O)N2CC=3N(CC4=C2OC=C4)C=CC3)C=C1.NN>>NC1=CC=C(C(=O)N2CC=3N(CC4=C2OC=C4)C=CC3)C=C1 | O=[N+:1]([O-])[c:2]1[cH:3][cH:4][c:5]([C:6](=[O:7])[N:8]2[CH2:9][c:10]3[cH:11][cH:12][cH:13][n:14]3[CH2:15][c:16]3[cH:17][cH:18][o:19][c:20]32)[cH:21][cH:22]1>>[NH2:1][c:2]1[cH:3][cH:4][c:5]([C:6](=[O:7])[N:8]2[CH2:9][c:10]3[cH:11][cH:12][cH:13][n:14]3[CH2:15][c:16]3[cH:17][cH:18][o:19][c:20]32)[cH:21][cH:22]1 | O=C(c1ccc([N+](=O)[O-])cc1)N1Cc2cccn2Cc2ccoc21 | Nc1ccc(C(=O)N2Cc3cccn3Cc3ccoc32)cc1 | null | [Pd] | C(C)O | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | O=C(c1ccccc1)N1Cc2cccn2Cc2ccoc21 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | null | null | To a solution of 1 mmol of 9,10-dihydro-10-(4-nitrobenzoyl)-4H-furo[2,3-e]pyrrolo[1,2-a][1,4]diazepine in 20 ml of ethyl alcohol is added 0.2 g of 10% Pd/C and 2.5 mmol of hydrazine followed by stirring and heating under reflux for 3 hours. The room temperature reaction mixture is filtered through diatomaceous earth an... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1.c1cc2n(c1)Cc1ccoc1[NH]C2 | Other | [Pd].C(C)O | null | null | O=C(c1ccc([N+](=O)[O-])cc1)N1Cc2cccn2Cc2ccoc21>[Pd].C(C)O>Nc1ccc(C(=O)N2Cc3cccn3Cc3ccoc32)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-7d2a5ee88619484c8d74a7550ba9b6d4 | Cc1ccccc1C(=O)Cl.Nc1ccc(C(=O)N2Cc3cccn3Cc3ccoc32)cc1>>Cc1ccccc1C(=O)Nc1ccc(C(=O)N2Cc3cccn3Cc3ccoc32)cc1 | NC1=CC=C(C(=O)N2CC=3N(CC4=C2OC=C4)C=CC3)C=C1.CC1=C(C(=O)Cl)C=CC=C1.C(C)N(CC)CC>>O1C=CC2=C1N(CC=1N(C2)C=CC1)C(=O)C1=CC=C(C=C1)NC(C1=C(C=CC=C1)C)=O | Cl[C:8]([c:7]1[c:2]([CH3:1])[cH:3][cH:4][cH:5][cH:6]1)=[O:9].[NH2:10][c:11]1[cH:12][cH:13][c:14]([C:15](=[O:16])[N:17]2[CH2:18][c:19]3[cH:20][cH:21][cH:22][n:23]3[CH2:24][c:25]3[cH:26][cH:27][o:28][c:29]32)[cH:30][cH:31]1>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][cH:6][c:7]1[C:8](=[O:9])[NH:10][c:11]1[cH:12][cH:13][c:14]([C:15]... | Cc1ccccc1C(=O)Cl.Nc1ccc(C(=O)N2Cc3cccn3Cc3ccoc32)cc1 | Cc1ccccc1C(=O)Nc1ccc(C(=O)N2Cc3cccn3Cc3ccoc32)cc1 | null | null | C(Cl)Cl | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=C(Nc1ccc(C(=O)N2Cc3cccn3Cc3ccoc32)cc1)c1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9])-[c:3](:[c:4]):[c:5] | null | [] | null | null | 5 | HOUR | To a stirred solution of 1.1 mmol of 2-methylbenzoyl chloride in 10 ml of methylene chloride is added 1.5 mmol of triethylamine. To the mixture is added 1.1 mmol of 9,10-dihydro-10-(4-aminobenzoyl)-4H-furo[2,3-e]pyrrolo[1,2-a][1,4]diazepine and the mixture is stirred for 5 hours. The reaction mixture is washed with wat... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccccc1.c1cc2n(c1)Cc1ccoc1[NH]C2 | HCl | C(Cl)Cl | null | 5 | Cc1ccccc1C(=O)Cl.Nc1ccc(C(=O)N2Cc3cccn3Cc3ccoc32)cc1>C(Cl)Cl>Cc1ccccc1C(=O)Nc1ccc(C(=O)N2Cc3cccn3Cc3ccoc32)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-640af18f5f2a4182aa628a6af14296b2 | Cc1ccccc1C(=O)Nc1ccc(C(=O)Cl)cc1.c1ccc2c(c1)Cn1nccc1CN2>>Cc1ccccc1C(=O)Nc1ccc(C(=O)N2Cc3ccnn3Cc3ccccc32)cc1 | CC1=C(C(=O)NC2=CC=C(C(=O)Cl)C=C2)C=CC=C1.C(C)N(CC)CC.N1=CC=C2CNC3=C(CN21)C=CC=C3>>N1=CC=C2CN(C3=C(CN21)C=CC=C3)C(=O)C3=CC=C(C=C3)NC(C3=C(C=CC=C3)C)=O | Cl[C:15]([c:14]1[cH:13][cH:12][c:11]([NH:10][C:8]([c:7]2[c:2]([CH3:1])[cH:3][cH:4][cH:5][cH:6]2)=[O:9])[cH:32][cH:31]1)=[O:16].[NH:17]1[CH2:18][c:19]2[cH:20][cH:21][n:22][n:23]2[CH2:24][c:25]2[cH:26][cH:27][cH:28][cH:29][c:30]21>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][cH:6][c:7]1[C:8](=[O:9])[NH:10][c:11]1[cH:12][cH:13][c:14]... | Cc1ccccc1C(=O)Nc1ccc(C(=O)Cl)cc1.c1ccc2c(c1)Cn1nccc1CN2 | Cc1ccccc1C(=O)Nc1ccc(C(=O)N2Cc3ccnn3Cc3ccccc32)cc1 | null | null | C(Cl)Cl.C(C)(=O)OCC | Acylation | N-alkylation of secondary amines with alkyl halides | 2a9d533c553c6efbbdf6d8d85d5ea4d91aac2ca9bfdcbb5bc6ecb14894c8ecc0 | 96cb0a2fed10552c5770a45a2d6523b47ac3e38928b4a9c698d8577451182dcd | O=C(Nc1ccc(C(=O)N2Cc3ccnn3Cc3ccccc32)cc1)c1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[#7;a:6]:[#7;a:7]:[c:8]-[C:9]-[NH;D2;+0:10]-[c:11](:[c:12]):[c:13]>>[#7;a:6]:[#7;a:7]:[c:8]-[C:9]-[N;H0;D3;+0:10](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5])-[c:11](:[c:12]):[c:13] | null | [] | 0 | CELSIUS | 48 | HOUR | To a mixture of 1.37 g of 4-[(2-methylbenzoyl)amino]benzoyl chloride in 15 ml of methylene chloride, cooled to 0° C. is added 1.5 ml of triethylamine. To the mixture is added 5 mmol of 5,10-dihydro-4H-pyrazolo[5,1-c][1,4]benzodiazepine. The reaction mixture is allowed to stir at room temperature for 48 hours and the vo... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Secondary amine | Tertiary amide | c1ccc2c(c1)Cn1nccc1CN2 | c1ccc2c(c1)Cn1nccc1C[NH]2 | c1ccccc1.c1ccccc1.c1ccc2c(c1)Cn1nccc1C[NH]2 | HCl | C(Cl)Cl.C(C)(=O)OCC | 0 | 48 | Cc1ccccc1C(=O)Nc1ccc(C(=O)Cl)cc1.c1ccc2c(c1)Cn1nccc1CN2>C(Cl)Cl.C(C)(=O)OCC>Cc1ccccc1C(=O)Nc1ccc(C(=O)N2Cc3ccnn3Cc3ccccc32)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-01f997ff48754e568e59523d12551630 | O=C(Cl)c1ccc([N+](=O)[O-])cc1.c1ccc2c(c1)Cn1nccc1CN2>>O=C(c1ccc([N+](=O)[O-])cc1)N1Cc2ccnn2Cc2ccccc21 | [N+](=O)([O-])C1=CC=C(C(=O)Cl)C=C1.N1=CC=C2CNC3=C(CN21)C=CC=C3.C(C)N(CC)CC>>[N+](=O)([O-])C1=CC=C(C(=O)N2CC=3N(CC4=C2C=CC=C4)N=CC3)C=C1 | Cl[C:2](=[O:1])[c:3]1[cH:4][cH:5][c:6]([N+:7](=[O:8])[O-:9])[cH:10][cH:11]1.[NH:12]1[CH2:13][c:14]2[cH:15][cH:16][n:17][n:18]2[CH2:19][c:20]2[cH:21][cH:22][cH:23][cH:24][c:25]21>>[O:1]=[C:2]([c:3]1[cH:4][cH:5][c:6]([N+:7](=[O:8])[O-:9])[cH:10][cH:11]1)[N:12]1[CH2:13][c:14]2[cH:15][cH:16][n:17][n:18]2[CH2:19][c:20]2[cH:... | O=C(Cl)c1ccc([N+](=O)[O-])cc1.c1ccc2c(c1)Cn1nccc1CN2 | O=C(c1ccc([N+](=O)[O-])cc1)N1Cc2ccnn2Cc2ccccc21 | null | null | C(Cl)Cl.C(C)(=O)OCC | Acylation | N-alkylation of secondary amines with alkyl halides | 2a9d533c553c6efbbdf6d8d85d5ea4d91aac2ca9bfdcbb5bc6ecb14894c8ecc0 | 96cb0a2fed10552c5770a45a2d6523b47ac3e38928b4a9c698d8577451182dcd | O=C(c1ccccc1)N1Cc2ccnn2Cc2ccccc21 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[#7;a:6]:[#7;a:7]:[c:8]-[C:9]-[NH;D2;+0:10]-[c:11](:[c:12]):[c:13]>>[#7;a:6]:[#7;a:7]:[c:8]-[C:9]-[N;H0;D3;+0:10](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5])-[c:11](:[c:12]):[c:13] | null | [] | null | null | 2 | HOUR | To a solution of 10 mmol of 5,10-dihydro-4H-pyrazolo[5,1-c][1,4]benzodiazepine in 50 ml of methylene chloride under argon is added 15 mmol of triethylamine followed by ice bath cooling. A solution of 11 mmol of 4-nitrobenzoyl chloride in 10 ml of methylene chloride is added dropwise. Following complete addition, the ic... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Secondary amine | Tertiary amide | c1ccc2c(c1)Cn1nccc1CN2 | c1ccc2c(c1)Cn1nccc1C[NH]2 | c1ccccc1.c1ccc2c(c1)Cn1nccc1C[NH]2 | HCl | C(Cl)Cl.C(C)(=O)OCC | null | 2 | O=C(Cl)c1ccc([N+](=O)[O-])cc1.c1ccc2c(c1)Cn1nccc1CN2>C(Cl)Cl.C(C)(=O)OCC>O=C(c1ccc([N+](=O)[O-])cc1)N1Cc2ccnn2Cc2ccccc21 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-451fabce79bd4397a69919d715a02dcb | O=C(c1ccc([N+](=O)[O-])cc1)N1Cc2ccnn2Cc2ccccc21>>Nc1ccc(C(=O)N2Cc3ccnn3Cc3ccccc32)cc1 | [N+](=O)([O-])C1=CC=C(C(=O)N2CC=3N(CC4=C2C=CC=C4)N=CC3)C=C1.C(C)(=O)OCC>>NC1=CC=C(C(=O)N2CC=3N(CC4=C2C=CC=C4)N=CC3)C=C1 | O=[N+:1]([O-])[c:2]1[cH:3][cH:4][c:5]([C:6](=[O:7])[N:8]2[CH2:9][c:10]3[cH:11][cH:12][n:13][n:14]3[CH2:15][c:16]3[cH:17][cH:18][cH:19][cH:20][c:21]32)[cH:22][cH:23]1>>[NH2:1][c:2]1[cH:3][cH:4][c:5]([C:6](=[O:7])[N:8]2[CH2:9][c:10]3[cH:11][cH:12][n:13][n:14]3[CH2:15][c:16]3[cH:17][cH:18][cH:19][cH:20][c:21]32)[cH:22][cH... | O=C(c1ccc([N+](=O)[O-])cc1)N1Cc2ccnn2Cc2ccccc21 | Nc1ccc(C(=O)N2Cc3ccnn3Cc3ccccc32)cc1 | null | [Pd] | C(C)O | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | O=C(c1ccccc1)N1Cc2ccnn2Cc2ccccc21 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | 5 | HOUR | A mixture of 5 mmol of 5,10-dihydro-5-(4-nitrobenzoyl)-4H-pyrazolo-[5,1-c][1,4]benzodiazepine in 25 ml of ethyl alcohol and 10 ml of ethyl acetate containing 0.2 g of 10% Pd/C is hydrogenated for 5 hours. The reaction mixture is filtered through a pad of diatomaceous earth. The filtrate is concentrated in vacuo to a so... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1.c1ccc2c(c1)Cn1nccc1C[NH]2 | Other | [Pd].C(C)O | null | 5 | O=C(c1ccc([N+](=O)[O-])cc1)N1Cc2ccnn2Cc2ccccc21>[Pd].C(C)O>Nc1ccc(C(=O)N2Cc3ccnn3Cc3ccccc32)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-3fa3ae243c4e4149abb49f53238ec971 | O=C(c1ccc([N+](=O)[O-])cc1)N1Cc2ccnn2Cc2ccccc21>>Nc1ccc(C(=O)N2Cc3ccnn3Cc3ccccc32)cc1 | [N+](=O)([O-])C1=CC=C(C(=O)N2CC=3N(CC4=C2C=CC=C4)N=CC3)C=C1.NN>>NC1=CC=C(C(=O)N2CC=3N(CC4=C2C=CC=C4)N=CC3)C=C1 | O=[N+:1]([O-])[c:2]1[cH:3][cH:4][c:5]([C:6](=[O:7])[N:8]2[CH2:9][c:10]3[cH:11][cH:12][n:13][n:14]3[CH2:15][c:16]3[cH:17][cH:18][cH:19][cH:20][c:21]32)[cH:22][cH:23]1>>[NH2:1][c:2]1[cH:3][cH:4][c:5]([C:6](=[O:7])[N:8]2[CH2:9][c:10]3[cH:11][cH:12][n:13][n:14]3[CH2:15][c:16]3[cH:17][cH:18][cH:19][cH:20][c:21]32)[cH:22][cH... | O=C(c1ccc([N+](=O)[O-])cc1)N1Cc2ccnn2Cc2ccccc21 | Nc1ccc(C(=O)N2Cc3ccnn3Cc3ccccc32)cc1 | null | [Pd] | C(C)O | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | O=C(c1ccccc1)N1Cc2ccnn2Cc2ccccc21 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | null | null | To a solution of 5 mmol of 5,10-dihydro-5-(4-nitrobenzoyl)-4H-pyrazolo-[5,1-c][1,4]benzodiazepine in 25 ml of ethyl alcohol is added 0.3 g of 10% Pd/C and 15 mmol of hydrazine. The mixture is heated under reflux for 3 hours, and the mixture is filtered through diatomaceous earth. The filtrate is concentrated in vacuo t... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1.c1ccc2c(c1)Cn1nccc1C[NH]2 | Other | [Pd].C(C)O | null | null | O=C(c1ccc([N+](=O)[O-])cc1)N1Cc2ccnn2Cc2ccccc21>[Pd].C(C)O>Nc1ccc(C(=O)N2Cc3ccnn3Cc3ccccc32)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-635b45d2248548ecadd2ea29f0ad9ceb | Cc1ccccc1C(=O)Cl.Nc1ccc(C(=O)N2Cc3ccnn3Cc3ccccc32)cc1>>Cc1ccccc1C(=O)Nc1ccc(C(=O)N2Cc3ccnn3Cc3ccccc32)cc1 | CC1=C(C(=O)Cl)C=CC=C1.C(C)N(CC)CC.NC1=CC=C(C(=O)N2CC=3N(CC4=C2C=CC=C4)N=CC3)C=C1>>N1=CC=C2CN(C3=C(CN21)C=CC=C3)C(=O)C3=CC=C(C=C3)NC(C3=C(C=CC=C3)C)=O | Cl[C:8]([c:7]1[c:2]([CH3:1])[cH:3][cH:4][cH:5][cH:6]1)=[O:9].[NH2:10][c:11]1[cH:12][cH:13][c:14]([C:15](=[O:16])[N:17]2[CH2:18][c:19]3[cH:20][cH:21][n:22][n:23]3[CH2:24][c:25]3[cH:26][cH:27][cH:28][cH:29][c:30]32)[cH:31][cH:32]1>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][cH:6][c:7]1[C:8](=[O:9])[NH:10][c:11]1[cH:12][cH:13][c:14]... | Cc1ccccc1C(=O)Cl.Nc1ccc(C(=O)N2Cc3ccnn3Cc3ccccc32)cc1 | Cc1ccccc1C(=O)Nc1ccc(C(=O)N2Cc3ccnn3Cc3ccccc32)cc1 | null | null | C(Cl)Cl | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=C(Nc1ccc(C(=O)N2Cc3ccnn3Cc3ccccc32)cc1)c1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9])-[c:3](:[c:4]):[c:5] | null | [] | null | null | 5 | HOUR | To a stirred solution of 3 mmol of 2-methylbenzoyl chloride in 10 ml of methylene chloride is added 5 mmol of triethylamine and 3 mmol of 5,10-dihydro-5-(4-aminobenzoyl)-4H-pyrazolo-[5,1-c][1,4]benzodiazepine. The mixture is stirred at room temperature for 5 hours and is then washed with water, NaHCO3, and brine. The o... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccccc1.c1ccc2c(c1)Cn1nccc1C[NH]2 | HCl | C(Cl)Cl | null | 5 | Cc1ccccc1C(=O)Cl.Nc1ccc(C(=O)N2Cc3ccnn3Cc3ccccc32)cc1>C(Cl)Cl>Cc1ccccc1C(=O)Nc1ccc(C(=O)N2Cc3ccnn3Cc3ccccc32)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-32fd6db828ef4aec857d090e69d7e31b | O=C1Nc2sccc2Cn2cccc21>>c1cc2n(c1)Cc1ccsc1NC2 | O=C1C=2N(CC3=C(N1)SC=C3)C=CC2.[B].CSC.CO>>S1C=CC2=C1NCC=1N(C2)C=CC1 | O=[C:13]1[c:3]2[cH:2][cH:1][cH:5][n:4]2[CH2:6][c:7]2[cH:8][cH:9][s:10][c:11]2[NH:12]1>>[cH:1]1[cH:2][c:3]2[n:4]([cH:5]1)[CH2:6][c:7]1[cH:8][cH:9][s:10][c:11]1[NH:12][CH2:13]2 | O=C1Nc2sccc2Cn2cccc21 | c1cc2n(c1)Cc1ccsc1NC2 | null | null | O1CCCC1 | Reduction | Reduction of secondary amides to amines | 9e91eacb74cbbf4130abb8d9752cfa9ba051e175e09dfd15ba3bdc56e16af65a | ab40188eef2f825df7003af0ffae31d0ce53d126542122535627d3d354cbc9fe | c1cc2n(c1)Cc1ccsc1NC2 | O=[C;H0;D3;+0:1](-[#7:2]-[c:3]:[#16;a:4])-[c:5](:[c:6]):[#7;a:7](:[c:8])-[C:9]>>[#16;a:4]:[c:3]-[#7:2]-[CH2;D2;+0:1]-[c:5](:[c:6]):[#7;a:7](:[c:8])-[C:9] | null | [] | null | null | null | null | To a mixture of 7.0 g of 9-oxo-9,10-dihydro-4H-pyrrolo[1,2-a]thieno[2,3-e][1,4]diazepin in 25 ml of anhydrous tetrahydrofuran is added 9 ml of 10 molar boron-dimethylsulfide in tetrahydrofuran. The mixture is refluxed for 6 hours. The solution is cooled to room temperature and 25 ml of methanol added dropwise. The vola... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide | null | c1cc2n(c1)Cc1ccsc1NC2 | c1cc2n(c1)Cc1ccsc1NC2 | c1cc2n(c1)Cc1ccsc1NC2 | Other | O1CCCC1 | null | null | O=C1Nc2sccc2Cn2cccc21>O1CCCC1>c1cc2n(c1)Cc1ccsc1NC2 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-35c9189d6c304adeac0dada394886b55 | O=C(Cl)c1ccc([N+](=O)[O-])cc1.c1cc2n(c1)Cc1ccsc1NC2>>O=C(c1ccc([N+](=O)[O-])cc1)N1Cc2cccn2Cc2ccsc21 | [N+](=O)([O-])C1=CC=C(C(=O)Cl)C=C1.S1C=CC2=C1NCC=1N(C2)C=CC1.C(C)N(CC)CC>>[N+](=O)([O-])C1=CC=C(C(=O)N2CC=3N(CC4=C2SC=C4)C=CC3)C=C1 | Cl[C:2](=[O:1])[c:3]1[cH:4][cH:5][c:6]([N+:7](=[O:8])[O-:9])[cH:10][cH:11]1.[NH:12]1[CH2:13][c:14]2[cH:15][cH:16][cH:17][n:18]2[CH2:19][c:20]2[cH:21][cH:22][s:23][c:24]21>>[O:1]=[C:2]([c:3]1[cH:4][cH:5][c:6]([N+:7](=[O:8])[O-:9])[cH:10][cH:11]1)[N:12]1[CH2:13][c:14]2[cH:15][cH:16][cH:17][n:18]2[CH2:19][c:20]2[cH:21][cH... | O=C(Cl)c1ccc([N+](=O)[O-])cc1.c1cc2n(c1)Cc1ccsc1NC2 | O=C(c1ccc([N+](=O)[O-])cc1)N1Cc2cccn2Cc2ccsc21 | null | null | C(Cl)Cl.C(C)(=O)OCC | Acylation | N-alkylation of secondary amines with alkyl halides | 73ac63548b13ea29e73f58282b6fc33111ae852874190ea481449cbeb677bfa0 | 96cb0a2fed10552c5770a45a2d6523b47ac3e38928b4a9c698d8577451182dcd | O=C(c1ccccc1)N1Cc2cccn2Cc2ccsc21 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[#7;a:6]:[c:7]-[C:8]-[NH;D2;+0:9]-[c:10](:[c:11]):[#16;a:12]:[c:13]>>[#7;a:6]:[c:7]-[C:8]-[N;H0;D3;+0:9](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5])-[c:10](:[c:11]):[#16;a:12]:[c:13] | null | [] | null | null | 2 | HOUR | To a solution of 10 mmol of 9,10-dihydro-4H-pyrrolo[1,2-a]thieno[2,3-e][1,4]diazepine in 50 ml of methylene chloride under argon is added 15 mmol of triethylamine followed by ice bath cooling. A solution of 11 mmol of 4-nitrobenzoyl chloride in 10 ml of methylene chloride is added dropwise. Following complete addition,... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Secondary amine | Tertiary amide | c1cc2n(c1)Cc1ccsc1NC2 | c1cc2n(c1)Cc1ccsc1[NH]C2 | c1ccccc1.c1cc2n(c1)Cc1ccsc1[NH]C2 | HCl | C(Cl)Cl.C(C)(=O)OCC | null | 2 | O=C(Cl)c1ccc([N+](=O)[O-])cc1.c1cc2n(c1)Cc1ccsc1NC2>C(Cl)Cl.C(C)(=O)OCC>O=C(c1ccc([N+](=O)[O-])cc1)N1Cc2cccn2Cc2ccsc21 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-d4de906a1456494992638f496b0deda5 | O=C(c1ccc([N+](=O)[O-])cc1)N1Cc2cccn2Cc2ccsc21>>Nc1ccc(C(=O)N2Cc3cccn3Cc3ccsc32)cc1 | [N+](=O)([O-])C1=CC=C(C(=O)N2CC=3N(CC4=C2SC=C4)C=CC3)C=C1.C(C)(=O)OCC>>NC1=CC=C(C(=O)N2CC=3N(CC4=C2SC=C4)C=CC3)C=C1 | O=[N+:1]([O-])[c:2]1[cH:3][cH:4][c:5]([C:6](=[O:7])[N:8]2[CH2:9][c:10]3[cH:11][cH:12][cH:13][n:14]3[CH2:15][c:16]3[cH:17][cH:18][s:19][c:20]32)[cH:21][cH:22]1>>[NH2:1][c:2]1[cH:3][cH:4][c:5]([C:6](=[O:7])[N:8]2[CH2:9][c:10]3[cH:11][cH:12][cH:13][n:14]3[CH2:15][c:16]3[cH:17][cH:18][s:19][c:20]32)[cH:21][cH:22]1 | O=C(c1ccc([N+](=O)[O-])cc1)N1Cc2cccn2Cc2ccsc21 | Nc1ccc(C(=O)N2Cc3cccn3Cc3ccsc32)cc1 | null | [Pd] | C(C)O | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | O=C(c1ccccc1)N1Cc2cccn2Cc2ccsc21 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | 5 | HOUR | A mixture of 2 g of 9,10-dihydro-10-(4-nitrobenzoyl)-4H-pyrrolo-[1,2-a]thieno[2,3-e][1,4]diazepine in 20 ml of ethyl alcohol and 20 ml of ethyl acetate containing 0.2 g of 10% Pd/C is hydrogenated for 5 hours. The reaction mixture is filtered through a pad of diatomaceous earth. The filtrate is concentrated in vacuo to... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1.c1cc2n(c1)Cc1ccsc1[NH]C2 | Other | [Pd].C(C)O | null | 5 | O=C(c1ccc([N+](=O)[O-])cc1)N1Cc2cccn2Cc2ccsc21>[Pd].C(C)O>Nc1ccc(C(=O)N2Cc3cccn3Cc3ccsc32)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-43cffe9ce3e24ed093b7efd697803931 | O=C(c1ccc([N+](=O)[O-])cc1)N1Cc2cccn2Cc2ccsc21>>Nc1ccc(C(=O)N2Cc3cccn3Cc3ccsc32)cc1 | [N+](=O)([O-])C1=CC=C(C(=O)N2CC=3N(CC4=C2SC=C4)C=CC3)C=C1.NN>>NC1=CC=C(C(=O)N2CC=3N(CC4=C2SC=C4)C=CC3)C=C1 | O=[N+:1]([O-])[c:2]1[cH:3][cH:4][c:5]([C:6](=[O:7])[N:8]2[CH2:9][c:10]3[cH:11][cH:12][cH:13][n:14]3[CH2:15][c:16]3[cH:17][cH:18][s:19][c:20]32)[cH:21][cH:22]1>>[NH2:1][c:2]1[cH:3][cH:4][c:5]([C:6](=[O:7])[N:8]2[CH2:9][c:10]3[cH:11][cH:12][cH:13][n:14]3[CH2:15][c:16]3[cH:17][cH:18][s:19][c:20]32)[cH:21][cH:22]1 | O=C(c1ccc([N+](=O)[O-])cc1)N1Cc2cccn2Cc2ccsc21 | Nc1ccc(C(=O)N2Cc3cccn3Cc3ccsc32)cc1 | null | [Pd] | C(C)O | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | O=C(c1ccccc1)N1Cc2cccn2Cc2ccsc21 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | null | null | To a solution of 5 mmol of 9,10-dihydro-10-(4-nitrobenzoyl)-4H-pyrrolo-[1,2-a]thieno[2,3-e][1,4]diazepine in 25 ml of ethyl alcohol is added 0.13 g of 10% Pd/C and 15 mmol of hydrazine followed by stirring and heating under reflux for 3 hours. The cooled reaction mixture is filtered through diatomaceous earth. The filt... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1.c1cc2n(c1)Cc1ccsc1[NH]C2 | Other | [Pd].C(C)O | null | null | O=C(c1ccc([N+](=O)[O-])cc1)N1Cc2cccn2Cc2ccsc21>[Pd].C(C)O>Nc1ccc(C(=O)N2Cc3cccn3Cc3ccsc32)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-e2444919c6b4455d88ef28dab32fb982 | Cc1ccccc1C(=O)Cl.Nc1ccc(C(=O)N2Cc3cccn3Cc3ccsc32)cc1>>Cc1ccccc1C(=O)Nc1ccc(C(=O)N2Cc3cccn3Cc3ccsc32)cc1 | CC1=C(C(=O)Cl)C=CC=C1.C(C)N(CC)CC.NC1=CC=C(C(=O)N2CC=3N(CC4=C2SC=C4)C=CC3)C=C1>>S1C=CC2=C1N(CC=1N(C2)C=CC1)C(=O)C1=CC=C(C=C1)NC(C1=C(C=CC=C1)C)=O | Cl[C:8]([c:7]1[c:2]([CH3:1])[cH:3][cH:4][cH:5][cH:6]1)=[O:9].[NH2:10][c:11]1[cH:12][cH:13][c:14]([C:15](=[O:16])[N:17]2[CH2:18][c:19]3[cH:20][cH:21][cH:22][n:23]3[CH2:24][c:25]3[cH:26][cH:27][s:28][c:29]32)[cH:30][cH:31]1>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][cH:6][c:7]1[C:8](=[O:9])[NH:10][c:11]1[cH:12][cH:13][c:14]([C:15]... | Cc1ccccc1C(=O)Cl.Nc1ccc(C(=O)N2Cc3cccn3Cc3ccsc32)cc1 | Cc1ccccc1C(=O)Nc1ccc(C(=O)N2Cc3cccn3Cc3ccsc32)cc1 | null | null | C(Cl)Cl | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=C(Nc1ccc(C(=O)N2Cc3cccn3Cc3ccsc32)cc1)c1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9])-[c:3](:[c:4]):[c:5] | null | [] | null | null | 5 | HOUR | To a stirred solution of 5 mmol of 2-methylbenzoyl chloride in 10 ml of methylene chloride is added 7 mmol of triethylamine and 5 mmol of 9,10-dihydro-10-(4-aminobenzoyl)-4H-pyrrolo-[1,2-a]thieno[2,3-e][1,4]diazepine and the mixture stirred for 5 hours. The reaction mixture is washed with water, 2N citric acid, NaHCO3,... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccccc1.c1cc2n(c1)Cc1ccsc1[NH]C2 | HCl | C(Cl)Cl | null | 5 | Cc1ccccc1C(=O)Cl.Nc1ccc(C(=O)N2Cc3cccn3Cc3ccsc32)cc1>C(Cl)Cl>Cc1ccccc1C(=O)Nc1ccc(C(=O)N2Cc3cccn3Cc3ccsc32)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-0a0788741821421fbc51f8d55f9a7706 | O=C1NC2=CCSC2=Cn2cccc21>>c1cc2n(c1)Cc1sccc1NC2 | O=C1C=2N(C=C3C(N1)=CCS3)C=CC2.B.CSC.CO>>S1C=CC=2NCC=3N(CC21)C=CC3 | O=[C:13]1[c:3]2[cH:2][cH:1][cH:5][n:4]2[CH:6]=[C:7]2[S:8][CH2:9][CH:10]=[C:11]2[NH:12]1>>[cH:1]1[cH:2][c:3]2[n:4]([cH:5]1)[CH2:6][c:7]1[s:8][cH:9][cH:10][c:11]1[NH:12][CH2:13]2 | O=C1NC2=CCSC2=Cn2cccc21 | c1cc2n(c1)Cc1sccc1NC2 | null | null | O1CCCC1 | Aromatic Heterocycle Formation | OtherReaction | 348f98fdf41a1f8f7538b65e735f11f3473bee41e42d076b6a1efceca74e3138 | 81c59fde38dc560f692a1c38df8f47b110fa16900b6cac6cae630b09c490945f | c1cc2n(c1)Cc1sccc1NC2 | O=[C;H0;D3;+0:1]1-[#7:2]-[C;H0;D3;+0:3]2=[CH;D2;+0:4]-[CH2;D2;+0:5]-[S;H0;D2;+0:6]-[C;H0;D3;+0:7]-2=[CH;D2;+0:8]-[#7;a:9](:[c:10]):[c:11]-1:[c:12]>>[c:12]:[c:11]1:[#7;a:9](:[c:10])-[CH2;D2;+0:8]-[c;H0;D3;+0:7]2:[s;H0;D2;+0:6]:[cH;D2;+0:5]:[cH;D2;+0:4]:[c;H0;D3;+0:3]:2-[#7:2]-[CH2;D2;+0:1]-1 | null | [] | null | null | null | null | To a suspension of 7.0 g of 5-oxo-4,5-dihydropyrrolo[1,2-a]thieno[3,2-e][1,4]diazepine in 25 ml of anhydrous tetrahydrofuran is added 9 ml of 10M borane-dimethylsulfide in tetrahydrofuran. The mixture is refluxed for 6 hours. The solution is cooled to room temperature and 25 ml of methanol added dropwise. The volatiles... | 10.6084/m9.figshare.5104873.v1 | null | Enamine.Secondary amide.Monosulfide | null | C1=C2NCc3cccn3C=C2SC1 | c1cc2n(c1)Cc1sccc1NC2 | c1cc2n(c1)Cc1sccc1NC2 | Other | O1CCCC1 | null | null | O=C1NC2=CCSC2=Cn2cccc21>O1CCCC1>c1cc2n(c1)Cc1sccc1NC2 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-080e88009fe4424789571d6359f4e214 | O=C(Cl)c1ccc([N+](=O)[O-])cc1.c1cc2n(c1)Cc1sccc1NC2>>O=C(c1ccc([N+](=O)[O-])cc1)N1Cc2cccn2Cc2sccc21 | [N+](=O)([O-])C1=CC=C(C(=O)Cl)C=C1.S1C=CC=2NCC=3N(CC21)C=CC3.C(C)N(CC)CC>>[N+](=O)([O-])C1=CC=C(C(=O)N2CC=3N(CC4=C2C=CS4)C=CC3)C=C1 | Cl[C:2](=[O:1])[c:3]1[cH:4][cH:5][c:6]([N+:7](=[O:8])[O-:9])[cH:10][cH:11]1.[NH:12]1[CH2:13][c:14]2[cH:15][cH:16][cH:17][n:18]2[CH2:19][c:20]2[s:21][cH:22][cH:23][c:24]21>>[O:1]=[C:2]([c:3]1[cH:4][cH:5][c:6]([N+:7](=[O:8])[O-:9])[cH:10][cH:11]1)[N:12]1[CH2:13][c:14]2[cH:15][cH:16][cH:17][n:18]2[CH2:19][c:20]2[s:21][cH:... | O=C(Cl)c1ccc([N+](=O)[O-])cc1.c1cc2n(c1)Cc1sccc1NC2 | O=C(c1ccc([N+](=O)[O-])cc1)N1Cc2cccn2Cc2sccc21 | null | null | C(Cl)Cl.C(C)(=O)OCC | Acylation | N-alkylation of secondary amines with alkyl halides | 023ca173c458ad900173ca1e79e60573399517321a60716a8355fd2ac7fa1a20 | 96cb0a2fed10552c5770a45a2d6523b47ac3e38928b4a9c698d8577451182dcd | O=C(c1ccccc1)N1Cc2cccn2Cc2sccc21 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[#16;a:6]1:[c:7]:[c:8]:[c:9]2:[c:10]:1-[C:11]-[#7;a:12]:[c:13]-[C:14]-[NH;D2;+0:15]-2>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[N;H0;D3;+0:15]1-[C:14]-[c:13]:[#7;a:12]-[C:11]-[c:10]2:[#16;a:6]:[c:7]:[c:8]:[c:9]:2-1)-[c:3](:[c:4]):[c:5] | null | [] | null | null | 2 | HOUR | To a solution of 3 mmol of 4,10-dihydro-5H-pyrrolo[1,2-a]thieno[3,2-e][1,4]diazepine in 10 ml of methylene chloride under argon is added 5 mmol of triethylamine followed by ice bath cooling. A solution of 3.3 mmol of 4-nitrobenzoyl chloride in 3 ml of methylene chloride is added dropwise. Following complete addition, t... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Secondary amine | Tertiary amide | c1cc2n(c1)Cc1sccc1NC2 | c1cc2n(c1)Cc1sccc1[NH]C2 | c1ccccc1.c1cc2n(c1)Cc1sccc1[NH]C2 | HCl | C(Cl)Cl.C(C)(=O)OCC | null | 2 | O=C(Cl)c1ccc([N+](=O)[O-])cc1.c1cc2n(c1)Cc1sccc1NC2>C(Cl)Cl.C(C)(=O)OCC>O=C(c1ccc([N+](=O)[O-])cc1)N1Cc2cccn2Cc2sccc21 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-776f8c6b427a45a6a33d6f8838f93d1c | O=C(c1ccc([N+](=O)[O-])cc1)N1Cc2cccn2Cc2sccc21>>Nc1ccc(C(=O)N2Cc3cccn3Cc3sccc32)cc1 | [N+](=O)([O-])C1=CC=C(C(=O)N2CC=3N(CC4=C2C=CS4)C=CC3)C=C1.C(C)(=O)OCC>>NC1=CC=C(C(=O)N2CC=3N(CC4=C2C=CS4)C=CC3)C=C1 | O=[N+:1]([O-])[c:2]1[cH:3][cH:4][c:5]([C:6](=[O:7])[N:8]2[CH2:9][c:10]3[cH:11][cH:12][cH:13][n:14]3[CH2:15][c:16]3[s:17][cH:18][cH:19][c:20]32)[cH:21][cH:22]1>>[NH2:1][c:2]1[cH:3][cH:4][c:5]([C:6](=[O:7])[N:8]2[CH2:9][c:10]3[cH:11][cH:12][cH:13][n:14]3[CH2:15][c:16]3[s:17][cH:18][cH:19][c:20]32)[cH:21][cH:22]1 | O=C(c1ccc([N+](=O)[O-])cc1)N1Cc2cccn2Cc2sccc21 | Nc1ccc(C(=O)N2Cc3cccn3Cc3sccc32)cc1 | null | [Pd] | C(C)O | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | O=C(c1ccccc1)N1Cc2cccn2Cc2sccc21 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | 5 | HOUR | A mixture of 5 mmol of 4,10-dihydro-4-(4-nitrobenzoyl)-5H-pyrrolo-[1,2-a]thieno[3,2-e][1,4]diazepine in 25 ml of ethyl alcohol and 25 ml of ethyl acetate containing 0.2 g of 10% Pd/C is hydrogenated for 5 hours. The reaction mixture is filtered through a pad of diatomaceous earth. The filtrate is concentrated in vacuo ... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1.c1cc2n(c1)Cc1sccc1[NH]C2 | Other | [Pd].C(C)O | null | 5 | O=C(c1ccc([N+](=O)[O-])cc1)N1Cc2cccn2Cc2sccc21>[Pd].C(C)O>Nc1ccc(C(=O)N2Cc3cccn3Cc3sccc32)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-560555af73dc47aab685f88cc2a775c6 | O=C(c1ccc([N+](=O)[O-])cc1)N1Cc2cccn2Cc2sccc21>>Nc1ccc(C(=O)N2Cc3cccn3Cc3sccc32)cc1 | NN.[N+](=O)([O-])C1=CC=C(C(=O)N2CC=3N(CC4=C2C=CS4)C=CC3)C=C1>>NC1=CC=C(C(=O)N2CC=3N(CC4=C2C=CS4)C=CC3)C=C1 | O=[N+:1]([O-])[c:2]1[cH:3][cH:4][c:5]([C:6](=[O:7])[N:8]2[CH2:9][c:10]3[cH:11][cH:12][cH:13][n:14]3[CH2:15][c:16]3[s:17][cH:18][cH:19][c:20]32)[cH:21][cH:22]1>>[NH2:1][c:2]1[cH:3][cH:4][c:5]([C:6](=[O:7])[N:8]2[CH2:9][c:10]3[cH:11][cH:12][cH:13][n:14]3[CH2:15][c:16]3[s:17][cH:18][cH:19][c:20]32)[cH:21][cH:22]1 | O=C(c1ccc([N+](=O)[O-])cc1)N1Cc2cccn2Cc2sccc21 | Nc1ccc(C(=O)N2Cc3cccn3Cc3sccc32)cc1 | null | [Pd] | C(C)O | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | O=C(c1ccccc1)N1Cc2cccn2Cc2sccc21 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | null | null | To a mixture of 5 mmol of 4,10-dihydro-4-(4-nitrobenzoyl)-5H-pyrrolo-[1,2-a]thieno[3,2-e][1,4]diazepine in 25 ml of ethyl alcohol is added 0.3 g of 10% Pd/C and 15 mmol of hydrazine followed by stirring and heating under reflux for 3 hours. The cooled reaction mixture is filtered through diatomaceous earth. The filtrat... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1.c1cc2n(c1)Cc1sccc1[NH]C2 | Other | [Pd].C(C)O | null | null | O=C(c1ccc([N+](=O)[O-])cc1)N1Cc2cccn2Cc2sccc21>[Pd].C(C)O>Nc1ccc(C(=O)N2Cc3cccn3Cc3sccc32)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-b2aca09294cd4507a7fd38eab4bba6a8 | Cc1ccccc1C(=O)Cl.Nc1ccc(C(=O)N2Cc3cccn3Cc3sccc32)cc1>>Cc1ccccc1C(=O)Nc1ccc(C(=O)N2Cc3cccn3Cc3sccc32)cc1 | CC1=C(C(=O)Cl)C=CC=C1.C(C)N(CC)CC.NC1=CC=C(C(=O)N2CC=3N(CC4=C2C=CS4)C=CC3)C=C1>>S1C=CC=2N(CC=3N(CC21)C=CC3)C(=O)C3=CC=C(C=C3)NC(C3=C(C=CC=C3)C)=O | Cl[C:8]([c:7]1[c:2]([CH3:1])[cH:3][cH:4][cH:5][cH:6]1)=[O:9].[NH2:10][c:11]1[cH:12][cH:13][c:14]([C:15](=[O:16])[N:17]2[CH2:18][c:19]3[cH:20][cH:21][cH:22][n:23]3[CH2:24][c:25]3[s:26][cH:27][cH:28][c:29]32)[cH:30][cH:31]1>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][cH:6][c:7]1[C:8](=[O:9])[NH:10][c:11]1[cH:12][cH:13][c:14]([C:15]... | Cc1ccccc1C(=O)Cl.Nc1ccc(C(=O)N2Cc3cccn3Cc3sccc32)cc1 | Cc1ccccc1C(=O)Nc1ccc(C(=O)N2Cc3cccn3Cc3sccc32)cc1 | null | null | C(Cl)Cl | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=C(Nc1ccc(C(=O)N2Cc3cccn3Cc3sccc32)cc1)c1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9])-[c:3](:[c:4]):[c:5] | null | [] | null | null | 5 | HOUR | To a stirred solution of 3 mmol of 2-methylbenzoyl chloride in 10 ml of methylene chloride is added 5 mmol of triethylamine and 3 mmol of 4,10-dihydro-4-(4-aminobenzoyl)-5H-pyrrolo-[1,2-a]thieno[3,2-e][1,4]diazepine. The mixture is stirred for 5 hours. The reaction mixture is washed with water, 2N citric acid, NaHCO3, ... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccccc1.c1cc2n(c1)Cc1sccc1[NH]C2 | HCl | C(Cl)Cl | null | 5 | Cc1ccccc1C(=O)Cl.Nc1ccc(C(=O)N2Cc3cccn3Cc3sccc32)cc1>C(Cl)Cl>Cc1ccccc1C(=O)Nc1ccc(C(=O)N2Cc3cccn3Cc3sccc32)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-3790b2a5481d44819f7ce4004894689f | O=C(Cl)c1ccc([N+](=O)[O-])cc1.c1ccc2c(c1)NCCc1cccn1-2>>O=C(c1ccc([N+](=O)[O-])cc1)N1CCc2cccn2-c2ccccc21 | [N+](=O)([O-])C1=CC=C(C(=O)Cl)C=C1.C1=CC=CC=2NCCC=3N(C21)C=CC3.C(C)N(CC)CC>>[N+](=O)([O-])C1=CC=C(C(=O)N2CCC=3N(C4=C2C=CC=C4)C=CC3)C=C1 | Cl[C:2](=[O:1])[c:3]1[cH:4][cH:5][c:6]([N+:7](=[O:8])[O-:9])[cH:10][cH:11]1.[NH:12]1[CH2:13][CH2:14][c:15]2[cH:16][cH:17][cH:18][n:19]2-[c:20]2[cH:21][cH:22][cH:23][cH:24][c:25]21>>[O:1]=[C:2]([c:3]1[cH:4][cH:5][c:6]([N+:7](=[O:8])[O-:9])[cH:10][cH:11]1)[N:12]1[CH2:13][CH2:14][c:15]2[cH:16][cH:17][cH:18][n:19]2-[c:20]2... | O=C(Cl)c1ccc([N+](=O)[O-])cc1.c1ccc2c(c1)NCCc1cccn1-2 | O=C(c1ccc([N+](=O)[O-])cc1)N1CCc2cccn2-c2ccccc21 | null | null | C(Cl)Cl.C(C)(=O)OCC | Acylation | N-alkylation of secondary amines with alkyl halides | cacede3ee7b9065bc38250c6b836fcccf2981bf26d370ef9023b706cddcb599c | 96cb0a2fed10552c5770a45a2d6523b47ac3e38928b4a9c698d8577451182dcd | O=C(c1ccccc1)N1CCc2cccn2-c2ccccc21 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[#7;a:6]-[c:7]:[c:8](:[c:9])-[NH;D2;+0:10]-[C:11]-[C:12]>>[#7;a:6]-[c:7]:[c:8](:[c:9])-[N;H0;D3;+0:10](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5])-[C:11]-[C:12] | null | [] | null | null | 2 | HOUR | To a solution of 10 mmol of 6,7-dihydro-5H-pyrrolo[1,2-a][1,5]benzodiazepine in 30 ml of methylene chloride under argon is added 15 mmol of triethylamine followed by ice bath cooling. A solution of 11 mmol of 4-nitrobenzoyl chloride in 10 ml of methylene chloride is added dropwise. Following complete addition, the ice ... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Secondary amine | Tertiary amide | c1ccc2c(c1)NCCc1cccn12 | c1ccc2c(c1)[NH]CCc1cccn12 | c1ccccc1.c1ccc2c(c1)[NH]CCc1cccn12 | HCl | C(Cl)Cl.C(C)(=O)OCC | null | 2 | O=C(Cl)c1ccc([N+](=O)[O-])cc1.c1ccc2c(c1)NCCc1cccn1-2>C(Cl)Cl.C(C)(=O)OCC>O=C(c1ccc([N+](=O)[O-])cc1)N1CCc2cccn2-c2ccccc21 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-2e933027ef334e4bab577fc495f3f973 | O=C(c1ccc([N+](=O)[O-])cc1)N1CCc2cccn2-c2ccccc21>>Nc1ccc(C(=O)N2CCc3cccn3-c3ccccc32)cc1 | [N+](=O)([O-])C1=CC=C(C(=O)N2CCC=3N(C4=C2C=CC=C4)C=CC3)C=C1.C(C)O>>NC1=CC=C(C(=O)N2CCC=3N(C4=C2C=CC=C4)C=CC3)C=C1 | O=[N+:1]([O-])[c:2]1[cH:3][cH:4][c:5]([C:6](=[O:7])[N:8]2[CH2:9][CH2:10][c:11]3[cH:12][cH:13][cH:14][n:15]3-[c:16]3[cH:17][cH:18][cH:19][cH:20][c:21]32)[cH:22][cH:23]1>>[NH2:1][c:2]1[cH:3][cH:4][c:5]([C:6](=[O:7])[N:8]2[CH2:9][CH2:10][c:11]3[cH:12][cH:13][cH:14][n:15]3-[c:16]3[cH:17][cH:18][cH:19][cH:20][c:21]32)[cH:22... | O=C(c1ccc([N+](=O)[O-])cc1)N1CCc2cccn2-c2ccccc21 | Nc1ccc(C(=O)N2CCc3cccn3-c3ccccc32)cc1 | null | [Pd] | C(C)(=O)OCC | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | O=C(c1ccccc1)N1CCc2cccn2-c2ccccc21 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | 5 | HOUR | A mixture of 2.0 g of 6,7-dihydro-5-(4-nitrobenzoyl)-5H-pyrrolo[1,2-a][1,5]benzodiazepine, 20 ml of ethyl alcohol and 20 ml of ethyl acetate containing 0.2 g of 10% Pd/C is hydrogenated for 5 hours. The reaction mixture is filtered through a pad of diatomaceous earth. The filtrate is concentrated in vacuo to a solid wh... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1.c1ccc2c(c1)[NH]CCc1cccn12 | Other | [Pd].C(C)(=O)OCC | null | 5 | O=C(c1ccc([N+](=O)[O-])cc1)N1CCc2cccn2-c2ccccc21>[Pd].C(C)(=O)OCC>Nc1ccc(C(=O)N2CCc3cccn3-c3ccccc32)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-8f3157e129004e4ebb3ee2889687de22 | O=C(c1ccc([N+](=O)[O-])cc1)N1CCc2cccn2-c2ccccc21>>Nc1ccc(C(=O)N2CCc3cccn3-c3ccccc32)cc1 | [N+](=O)([O-])C1=CC=C(C(=O)N2CCC=3N(C4=C2C=CC=C4)C=CC3)C=C1.NN>>NC1=CC=C(C(=O)N2CCC=3N(C4=C2C=CC=C4)C=CC3)C=C1 | O=[N+:1]([O-])[c:2]1[cH:3][cH:4][c:5]([C:6](=[O:7])[N:8]2[CH2:9][CH2:10][c:11]3[cH:12][cH:13][cH:14][n:15]3-[c:16]3[cH:17][cH:18][cH:19][cH:20][c:21]32)[cH:22][cH:23]1>>[NH2:1][c:2]1[cH:3][cH:4][c:5]([C:6](=[O:7])[N:8]2[CH2:9][CH2:10][c:11]3[cH:12][cH:13][cH:14][n:15]3-[c:16]3[cH:17][cH:18][cH:19][cH:20][c:21]32)[cH:22... | O=C(c1ccc([N+](=O)[O-])cc1)N1CCc2cccn2-c2ccccc21 | Nc1ccc(C(=O)N2CCc3cccn3-c3ccccc32)cc1 | null | [Pd] | C(C)O | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | O=C(c1ccccc1)N1CCc2cccn2-c2ccccc21 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | null | null | To a solution of 5 mmol of 6,7-dihydro-5-(4-nitrobenzoyl)-5H-pyrrolo[1,2-a][1,5]benzodiazepine in 25 ml of ethyl alcohol is added 0.3 g of 10% Pd/C and 15 mmol of hydrazine followed by stirring and heating under reflux for 3 hours. The reaction mixture is filtered through diatomaceous earth. The filtrate is concentrate... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1.c1ccc2c(c1)[NH]CCc1cccn12 | Other | [Pd].C(C)O | null | null | O=C(c1ccc([N+](=O)[O-])cc1)N1CCc2cccn2-c2ccccc21>[Pd].C(C)O>Nc1ccc(C(=O)N2CCc3cccn3-c3ccccc32)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-5681035ee10241e3b5bb6098bf1ffd50 | Cc1ccccc1C(=O)Nc1ccc(C(=O)Cl)cc1.c1ccc2c(c1)NCCc1cccn1-2>>Cc1ccccc1C(=O)Nc1ccc(C(=O)N2CCc3cccn3-c3ccccc32)cc1 | CC1=C(C(=O)NC2=CC=C(C(=O)Cl)C=C2)C=CC=C1.C(C)N(CC)CC.C1=CC=CC=2NCCC=3N(C21)C=CC3>>C1=CC=CC=2N(CCC=3N(C21)C=CC3)C(=O)C3=CC=C(C=C3)NC(C3=C(C=CC=C3)C)=O | Cl[C:15]([c:14]1[cH:13][cH:12][c:11]([NH:10][C:8]([c:7]2[c:2]([CH3:1])[cH:3][cH:4][cH:5][cH:6]2)=[O:9])[cH:32][cH:31]1)=[O:16].[NH:17]1[CH2:18][CH2:19][c:20]2[cH:21][cH:22][cH:23][n:24]2-[c:25]2[cH:26][cH:27][cH:28][cH:29][c:30]21>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][cH:6][c:7]1[C:8](=[O:9])[NH:10][c:11]1[cH:12][cH:13][c:1... | Cc1ccccc1C(=O)Nc1ccc(C(=O)Cl)cc1.c1ccc2c(c1)NCCc1cccn1-2 | Cc1ccccc1C(=O)Nc1ccc(C(=O)N2CCc3cccn3-c3ccccc32)cc1 | null | null | C(Cl)Cl.C(C)(=O)OCC | Acylation | N-alkylation of secondary amines with alkyl halides | cacede3ee7b9065bc38250c6b836fcccf2981bf26d370ef9023b706cddcb599c | 96cb0a2fed10552c5770a45a2d6523b47ac3e38928b4a9c698d8577451182dcd | O=C(Nc1ccc(C(=O)N2CCc3cccn3-c3ccccc32)cc1)c1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[#7;a:6]-[c:7]:[c:8](:[c:9])-[NH;D2;+0:10]-[C:11]-[C:12]>>[#7;a:6]-[c:7]:[c:8](:[c:9])-[N;H0;D3;+0:10](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5])-[C:11]-[C:12] | null | [] | 0 | CELSIUS | 48 | HOUR | To a mixture of 1.37 g (5 mmol) of 4-[(2-methylbenzoyl)amino]benzoyl chloride in 10 ml of methylene chloride, cooled to 0° C. is added 7 mmol of triethylamine and 5 mmol of 6,7-dihydro-5H-pyrrolo[1,2-a][1,5]benzodiazepine. The cooling bath is removed and the reaction mixture is allowed to stir at room temperature for 4... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Secondary amine | Tertiary amide | c1ccc2c(c1)NCCc1cccn12 | c1ccc2c(c1)[NH]CCc1cccn12 | c1ccccc1.c1ccccc1.c1ccc2c(c1)[NH]CCc1cccn12 | HCl | C(Cl)Cl.C(C)(=O)OCC | 0 | 48 | Cc1ccccc1C(=O)Nc1ccc(C(=O)Cl)cc1.c1ccc2c(c1)NCCc1cccn1-2>C(Cl)Cl.C(C)(=O)OCC>Cc1ccccc1C(=O)Nc1ccc(C(=O)N2CCc3cccn3-c3ccccc32)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-7ff22cdac5b94a6fa902c99d2482bd2d | Cc1ccccc1C(=O)Cl.Nc1ccc(C(=O)N2CCc3cccn3-c3ccccc32)cc1>>Cc1ccccc1C(=O)Nc1ccc(C(=O)N2CCc3cccn3-c3ccccc32)cc1 | CC1=C(C(=O)Cl)C=CC=C1.C(C)N(CC)CC.NC1=CC=C(C(=O)N2CCC=3N(C4=C2C=CC=C4)C=CC3)C=C1>>C1=CC=CC=2N(CCC=3N(C21)C=CC3)C(=O)C3=CC=C(C=C3)NC(C3=C(C=CC=C3)C)=O | Cl[C:8]([c:7]1[c:2]([CH3:1])[cH:3][cH:4][cH:5][cH:6]1)=[O:9].[NH2:10][c:11]1[cH:12][cH:13][c:14]([C:15](=[O:16])[N:17]2[CH2:18][CH2:19][c:20]3[cH:21][cH:22][cH:23][n:24]3-[c:25]3[cH:26][cH:27][cH:28][cH:29][c:30]32)[cH:31][cH:32]1>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][cH:6][c:7]1[C:8](=[O:9])[NH:10][c:11]1[cH:12][cH:13][c:1... | Cc1ccccc1C(=O)Cl.Nc1ccc(C(=O)N2CCc3cccn3-c3ccccc32)cc1 | Cc1ccccc1C(=O)Nc1ccc(C(=O)N2CCc3cccn3-c3ccccc32)cc1 | null | null | C(Cl)Cl | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=C(Nc1ccc(C(=O)N2CCc3cccn3-c3ccccc32)cc1)c1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9])-[c:3](:[c:4]):[c:5] | null | [] | null | null | null | null | To a stirred solution of 5 mmol of 2-methylbenzoyl chloride in 10 ml of methylene chloride is added 7 mmol of triethylamine and 5 mmol of 6,7-dihydro-5-(4-aminobenzoyl)-5H-pyrrolo[1,2-a][1,5]benzodiazepine. The reaction mixture is washed with water, 2M citric acid, NaHCO3, and brine. The organic layer is dried with Na2... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccccc1.c1ccc2c(c1)[NH]CCc1cccn12 | HCl | C(Cl)Cl | null | null | Cc1ccccc1C(=O)Cl.Nc1ccc(C(=O)N2CCc3cccn3-c3ccccc32)cc1>C(Cl)Cl>Cc1ccccc1C(=O)Nc1ccc(C(=O)N2CCc3cccn3-c3ccccc32)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-44ee38b3384d451c8b68f82532c2510d | O=C1Cc2nncn2-c2ccccc2N1>>c1ccc2c(c1)NCCc1nncn1-2 | C1=NN=C2N1C1=C(NC(C2)=O)C=CC=C1.B.CSC.CO>>C1=NN=C2N1C1=C(NCC2)C=CC=C1 | O=[C:8]1[NH:7][c:5]2[c:4]([cH:3][cH:2][cH:1][cH:6]2)-[n:14]2[c:10]([n:11][n:12][cH:13]2)[CH2:9]1>>[cH:1]1[cH:2][cH:3][c:4]2[c:5]([cH:6]1)[NH:7][CH2:8][CH2:9][c:10]1[n:11][n:12][cH:13][n:14]1-2 | O=C1Cc2nncn2-c2ccccc2N1 | c1ccc2c(c1)NCCc1nncn1-2 | null | null | O1CCCC1 | Reduction | Reduction of secondary amides to amines | b7f4e7ededfa692b00d717cf2c5499ad9de82e61994b4b39a11cb0e444602f4d | ab40188eef2f825df7003af0ffae31d0ce53d126542122535627d3d354cbc9fe | c1ccc2c(c1)NCCc1nncn1-2 | O=[C;H0;D3;+0:1](-[#7:2]-[c:3])-[C:4]-[c:5](:[#7;a:6]):[#7;a:7]:[#7;a:8]>>[#7;a:8]:[#7;a:7]:[c:5](:[#7;a:6])-[C:4]-[CH2;D2;+0:1]-[#7:2]-[c:3] | null | [] | null | null | null | null | A mixture of 7.0 g of 5,6-dihydro-4H-[1,2,4]-triazolo-[4,3-a][1,5]benzodiazepin-5-one in 25 ml of tetrahydrofuran is added 9 ml of 10M borane-dimethylsulfide in tetrahydrofuran. The mixture is refluxed for 6 hours, cooled to room temperature and 25 ml of methanol added dropwise. The volatiles are removed under vacuum a... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide | null | c1ccc2c(c1)NCCc1nncn12 | c1ccc2c(c1)NCCc1nncn12 | c1ccc2c(c1)NCCc1nncn12 | Other | O1CCCC1 | null | null | O=C1Cc2nncn2-c2ccccc2N1>O1CCCC1>c1ccc2c(c1)NCCc1nncn1-2 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-7eac7ed753114a31ad156b6030b93124 | Cc1ccccc1C(=O)Nc1ccc(C(=O)Cl)cc1.c1ccc2c(c1)NCCc1nncn1-2>>Cc1ccccc1C(=O)Nc1ccc(C(=O)N2CCc3nncn3-c3ccccc32)cc1 | C1=NN=C2N1C1=C(NCC2)C=CC=C1.CC1=C(C(=O)NC2=CC=C(C(=O)Cl)C=C2)C=CC=C1.C(C)N(CC)CC>>C1=NN=C2N1C1=C(N(CC2)C(=O)C2=CC=C(C=C2)NC(C2=C(C=CC=C2)C)=O)C=CC=C1 | Cl[C:15]([c:14]1[cH:13][cH:12][c:11]([NH:10][C:8]([c:7]2[c:2]([CH3:1])[cH:3][cH:4][cH:5][cH:6]2)=[O:9])[cH:32][cH:31]1)=[O:16].[NH:17]1[CH2:18][CH2:19][c:20]2[n:21][n:22][cH:23][n:24]2-[c:25]2[cH:26][cH:27][cH:28][cH:29][c:30]21>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][cH:6][c:7]1[C:8](=[O:9])[NH:10][c:11]1[cH:12][cH:13][c:14]... | Cc1ccccc1C(=O)Nc1ccc(C(=O)Cl)cc1.c1ccc2c(c1)NCCc1nncn1-2 | Cc1ccccc1C(=O)Nc1ccc(C(=O)N2CCc3nncn3-c3ccccc32)cc1 | null | null | ClCCl | Acylation | N-alkylation of secondary amines with alkyl halides | 02a9928a3e81bdc5f7b031d50a9ad183033ca559c7c5ab941ea14294ee4ea695 | 96cb0a2fed10552c5770a45a2d6523b47ac3e38928b4a9c698d8577451182dcd | O=C(Nc1ccc(C(=O)N2CCc3nncn3-c3ccccc32)cc1)c1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[#7;a:6]-[c:7]:[c:8](:[c:9])-[NH;D2;+0:10]-[C:11]-[C:12]>>[#7;a:6]-[c:7]:[c:8](:[c:9])-[N;H0;D3;+0:10](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5])-[C:11]-[C:12] | null | [] | null | null | 8 | HOUR | To a mixture of 5 mmol of 5,6-dihydro-4H-[1,2,4]triazolo[4,3-a][1,5]benzodiazepine in 20 ml of dichloromethane is added 5.5 mmol of 4-[(2-methylbenzoyl)amino]benzoyl chloride and then 7.5 mmol of triethylamine. The mixture is stirred at room temperature for 8 hours and then washed with water, aqueous NaHCO3 and brine. ... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Secondary amine | Tertiary amide | c1ccc2c(c1)NCCc1nncn12 | c1ccc2c(c1)[NH]CCc1nncn12 | c1ccccc1.c1ccccc1.c1ccc2c(c1)[NH]CCc1nncn12 | HCl | ClCCl | null | 8 | Cc1ccccc1C(=O)Nc1ccc(C(=O)Cl)cc1.c1ccc2c(c1)NCCc1nncn1-2>ClCCl>Cc1ccccc1C(=O)Nc1ccc(C(=O)N2CCc3nncn3-c3ccccc32)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-51928d820704485fb5ee2dc349f44abc | O=C(Cl)c1ccc([N+](=O)[O-])cc1.c1ccc2c(c1)NCCc1nncn1-2>>O=C(c1ccc([N+](=O)[O-])cc1)N1CCc2nncn2-c2ccccc21 | [N+](=O)([O-])C1=CC=C(C(=O)Cl)C=C1.C1=NN=C2N1C1=C(NCC2)C=CC=C1.C(C)N(CC)CC>>[N+](=O)([O-])C1=CC=C(C(=O)N2CCC=3N(C4=C2C=CC=C4)C=NN3)C=C1 | Cl[C:2](=[O:1])[c:3]1[cH:4][cH:5][c:6]([N+:7](=[O:8])[O-:9])[cH:10][cH:11]1.[NH:12]1[CH2:13][CH2:14][c:15]2[n:16][n:17][cH:18][n:19]2-[c:20]2[cH:21][cH:22][cH:23][cH:24][c:25]21>>[O:1]=[C:2]([c:3]1[cH:4][cH:5][c:6]([N+:7](=[O:8])[O-:9])[cH:10][cH:11]1)[N:12]1[CH2:13][CH2:14][c:15]2[n:16][n:17][cH:18][n:19]2-[c:20]2[cH:... | O=C(Cl)c1ccc([N+](=O)[O-])cc1.c1ccc2c(c1)NCCc1nncn1-2 | O=C(c1ccc([N+](=O)[O-])cc1)N1CCc2nncn2-c2ccccc21 | null | null | ClCCl | Acylation | N-alkylation of secondary amines with alkyl halides | 02a9928a3e81bdc5f7b031d50a9ad183033ca559c7c5ab941ea14294ee4ea695 | 96cb0a2fed10552c5770a45a2d6523b47ac3e38928b4a9c698d8577451182dcd | O=C(c1ccccc1)N1CCc2nncn2-c2ccccc21 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[#7;a:6]-[c:7]:[c:8](:[c:9])-[NH;D2;+0:10]-[C:11]-[C:12]>>[#7;a:6]-[c:7]:[c:8](:[c:9])-[N;H0;D3;+0:10](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5])-[C:11]-[C:12] | null | [] | null | null | 3 | HOUR | To a mixture of 3 mmol of 5,6-dihydro-4H-[1,2,4]-triazolo[4,3-a][1,5]benzodiazepine in 10 ml of dichloromethane under argon is added 5 mmol of triethylamine. To the mixture is added dropwise 3.3 mmol of 4-nitrobenzoyl chloride in 3 ml of dichloromethane. The mixture is stirred at room temperature 3 hours and then washe... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Secondary amine | Tertiary amide | c1ccc2c(c1)NCCc1nncn12 | c1ccc2c(c1)[NH]CCc1nncn12 | c1ccccc1.c1ccc2c(c1)[NH]CCc1nncn12 | HCl | ClCCl | null | 3 | O=C(Cl)c1ccc([N+](=O)[O-])cc1.c1ccc2c(c1)NCCc1nncn1-2>ClCCl>O=C(c1ccc([N+](=O)[O-])cc1)N1CCc2nncn2-c2ccccc21 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-3ff326e6707e4ac1885b28a452f5f0b4 | Cc1ccccc1C(=O)Nc1ccc(C(=O)Cl)cc1.Cc1nnc2n1-c1ccccc1NCC2>>Cc1ccccc1C(=O)Nc1ccc(C(=O)N2CCc3nnc(C)n3-c3ccccc32)cc1 | CC1=NN=C2N1C1=C(NCC2)C=CC=C1.CC1=C(C(=O)NC2=CC=C(C(=O)Cl)C=C2)C=CC=C1.C(C)N(CC)CC>>CC1=NN=C2N1C1=C(N(CC2)C(=O)C2=CC=C(C=C2)NC(C2=C(C=CC=C2)C)=O)C=CC=C1 | Cl[C:15]([c:14]1[cH:13][cH:12][c:11]([NH:10][C:8]([c:7]2[c:2]([CH3:1])[cH:3][cH:4][cH:5][cH:6]2)=[O:9])[cH:33][cH:32]1)=[O:16].[NH:17]1[CH2:18][CH2:19][c:20]2[n:21][n:22][c:23]([CH3:24])[n:25]2-[c:26]2[cH:27][cH:28][cH:29][cH:30][c:31]21>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][cH:6][c:7]1[C:8](=[O:9])[NH:10][c:11]1[cH:12][cH:... | Cc1ccccc1C(=O)Nc1ccc(C(=O)Cl)cc1.Cc1nnc2n1-c1ccccc1NCC2 | Cc1ccccc1C(=O)Nc1ccc(C(=O)N2CCc3nnc(C)n3-c3ccccc32)cc1 | null | null | ClCCl | Acylation | N-alkylation of secondary amines with alkyl halides | 02a9928a3e81bdc5f7b031d50a9ad183033ca559c7c5ab941ea14294ee4ea695 | 96cb0a2fed10552c5770a45a2d6523b47ac3e38928b4a9c698d8577451182dcd | O=C(Nc1ccc(C(=O)N2CCc3nncn3-c3ccccc32)cc1)c1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[#7;a:6]-[c:7]:[c:8](:[c:9])-[NH;D2;+0:10]-[C:11]-[C:12]>>[#7;a:6]-[c:7]:[c:8](:[c:9])-[N;H0;D3;+0:10](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5])-[C:11]-[C:12] | null | [] | null | null | 8 | HOUR | To a mixture of 5 mmol of 5,6-dihydro-1-methyl-4H-[1,2,4]triazolo[4,3-a][1,5]benzodiazepine in 20 ml of dichloromethane is added 5.5 mmol of 4-[(2-methylbenzoyl)amino]benzoyl chloride and 7.5 mmol of triethylamine. The mixture is stirred at room temperature for 8 hours and then washed with water, aqueous NaHCO3 and bri... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Secondary amine | Tertiary amide | c1ccc2c(c1)NCCc1nncn12 | c1ccc2c(c1)[NH]CCc1nncn12 | c1ccccc1.c1ccccc1.c1ccc2c(c1)[NH]CCc1nncn12 | HCl | ClCCl | null | 8 | Cc1ccccc1C(=O)Nc1ccc(C(=O)Cl)cc1.Cc1nnc2n1-c1ccccc1NCC2>ClCCl>Cc1ccccc1C(=O)Nc1ccc(C(=O)N2CCc3nnc(C)n3-c3ccccc32)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-486462ae5c224bae9e377bc9f20ec2d6 | Cc1nnc2n1-c1ccccc1NCC2.O=C(Cl)c1ccc(NC(=O)c2ccc(Cl)cc2Cl)cc1>>Cc1nnc2n1-c1ccccc1N(C(=O)c1ccc(NC(=O)c3ccc(Cl)cc3Cl)cc1)CC2 | CC1=NN=C2N1C1=C(NCC2)C=CC=C1.ClC1=C(C(=O)NC2=CC=C(C(=O)Cl)C=C2)C=CC(=C1)Cl.C(C)N(CC)CC>>CC1=NN=C2N1C1=C(N(CC2)C(=O)C2=CC=C(C=C2)NC(C2=C(C=C(C=C2)Cl)Cl)=O)C=CC=C1 | [CH3:1][c:2]1[n:3][n:4][c:5]2[n:6]1-[c:7]1[cH:8][cH:9][cH:10][cH:11][c:12]1[NH:13][CH2:33][CH2:34]2.Cl[C:14](=[O:15])[c:16]1[cH:17][cH:18][c:19]([NH:20][C:21](=[O:22])[c:23]2[cH:24][cH:25][c:26]([Cl:27])[cH:28][c:29]2[Cl:30])[cH:31][cH:32]1>>[CH3:1][c:2]1[n:3][n:4][c:5]2[n:6]1-[c:7]1[cH:8][cH:9][cH:10][cH:11][c:12]1[N:... | Cc1nnc2n1-c1ccccc1NCC2.O=C(Cl)c1ccc(NC(=O)c2ccc(Cl)cc2Cl)cc1 | Cc1nnc2n1-c1ccccc1N(C(=O)c1ccc(NC(=O)c3ccc(Cl)cc3Cl)cc1)CC2 | null | null | ClCCl | Acylation | N-alkylation of secondary amines with alkyl halides | 02a9928a3e81bdc5f7b031d50a9ad183033ca559c7c5ab941ea14294ee4ea695 | 96cb0a2fed10552c5770a45a2d6523b47ac3e38928b4a9c698d8577451182dcd | O=C(Nc1ccc(C(=O)N2CCc3nncn3-c3ccccc32)cc1)c1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[#7;a:6]-[c:7]:[c:8](:[c:9])-[NH;D2;+0:10]-[C:11]-[C:12]>>[#7;a:6]-[c:7]:[c:8](:[c:9])-[N;H0;D3;+0:10](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5])-[C:11]-[C:12] | null | [] | null | null | 8 | HOUR | To a mixture of 5 mmol of 5,6-dihydro-1-methyl-4H-[1,2,4]triazolo[4,3-a][1,5]benzodiazepine in 20 ml of dichloromethane is added 5.5 mmol of 4-[(2,4-dichlorobenzoyl)amino]benzoyl chloride and 7.5 mmol of triethylamine. The mixture is stirred at room temperature for 8 hours and then washed with water, aqueous NaHCO3 and... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Secondary amine | Tertiary amide | c1ccc2c(c1)NCCc1nncn12 | c1ccc2c(c1)[NH]CCc1nncn12 | c1ccccc1.c1ccccc1.c1ccc2c(c1)[NH]CCc1nncn12 | HCl | ClCCl | null | 8 | Cc1nnc2n1-c1ccccc1NCC2.O=C(Cl)c1ccc(NC(=O)c2ccc(Cl)cc2Cl)cc1>ClCCl>Cc1nnc2n1-c1ccccc1N(C(=O)c1ccc(NC(=O)c3ccc(Cl)cc3Cl)cc1)CC2 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-c95d79f1258e443d897cba074d004c76 | CCOC(=O)c1ccc(N(C)C(=O)c2ccccc2C)cc1>>Cc1ccccc1C(=O)N(C)c1ccc(C(=O)O)cc1 | CN(C(C1=C(C=CC=C1)C)=O)C1=CC=C(C(=O)OCC)C=C1.[OH-].[Na+]>>CN(C(C1=C(C=CC=C1)C)=O)C1=CC=C(C(=O)O)C=C1 | CC[O:18][C:16]([c:15]1[cH:14][cH:13][c:12]([N:10]([C:8]([c:7]2[c:2]([CH3:1])[cH:3][cH:4][cH:5][cH:6]2)=[O:9])[CH3:11])[cH:20][cH:19]1)=[O:17]>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][cH:6][c:7]1[C:8](=[O:9])[N:10]([CH3:11])[c:12]1[cH:13][cH:14][c:15]([C:16](=[O:17])[OH:18])[cH:19][cH:20]1 | CCOC(=O)c1ccc(N(C)C(=O)c2ccccc2C)cc1 | Cc1ccccc1C(=O)N(C)c1ccc(C(=O)O)cc1 | null | null | CO | Deprotection | Ester saponification (alkyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | O=C(Nc1ccccc1)c1ccccc1 | C-C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]>>[O;D1;H0:3]=[C:2](-[OH;D1;+0:1])-[c:4] | 67.5 | [{"value": 67.5, "product": "CN(C(C1=C(C=CC=C1)C)=O)C1=CC=C(C(=O)O)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A sample of 1.51 g of sodium hydride (60% in oil) is washed with hexane under argon to remove the oil. To the washed sodium hydride is added 5 ml of N,N-dimethylformamide. To this mixture is added dropwise a solution of 8.69 g of ethyl 4-[(2-methylbenzoyl)amino]benzoate in 20 ml of N,N-dimethylformamide. The mixture is... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1.c1ccccc1 | Other | CO | null | null | CCOC(=O)c1ccc(N(C)C(=O)c2ccccc2C)cc1>CO>Cc1ccccc1C(=O)N(C)c1ccc(C(=O)O)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-0df072498a024403b3a629783d25ae34 | Cc1ccccc1C(=O)N(C)c1ccc(C(=O)Cl)cc1.c1ccc2c(c1)Cn1cccc1CN2>>Cc1ccccc1C(=O)N(C)c1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1 | C=1C=CN2C1CNC1=C(C2)C=CC=C1.CN(C(C1=C(C=CC=C1)C)=O)C1=CC=C(C(=O)Cl)C=C1.C(C)N(CC)CC.O1CCCC1.CN(C(C1=C(C=CC=C1)C)=O)C1=CC=C(C(=O)Cl)C=C1.C(C)N(CC)CC>>C=1C=CN2C1CN(C1=C(C2)C=CC=C1)C(=O)C1=CC=C(C=C1)N(C(C1=C(C=CC=C1)C)=O)C | Cl[C:16]([c:15]1[cH:14][cH:13][c:12]([N:10]([C:8]([c:7]2[c:2]([CH3:1])[cH:3][cH:4][cH:5][cH:6]2)=[O:9])[CH3:11])[cH:33][cH:32]1)=[O:17].[NH:18]1[CH2:19][c:20]2[cH:21][cH:22][cH:23][n:24]2[CH2:25][c:26]2[cH:27][cH:28][cH:29][cH:30][c:31]21>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][cH:6][c:7]1[C:8](=[O:9])[N:10]([CH3:11])[c:12]1[... | Cc1ccccc1C(=O)N(C)c1ccc(C(=O)Cl)cc1.c1ccc2c(c1)Cn1cccc1CN2 | Cc1ccccc1C(=O)N(C)c1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1 | null | null | ClCCl.O | Acylation | N-alkylation of secondary amines with alkyl halides | fe674a41b285c5c1b016cd9c12dd41b3635fc90635e2c9974eeff0b8893e7755 | 96cb0a2fed10552c5770a45a2d6523b47ac3e38928b4a9c698d8577451182dcd | O=C(Nc1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1)c1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[#7;a:6]:[c:7]-[C:8]-[NH;D2;+0:9]-[c:10](:[c:11]):[c:12]>>[#7;a:6]:[c:7]-[C:8]-[N;H0;D3;+0:9](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5])-[c:10](:[c:11]):[c:12] | 59.5 | [{"value": 59.5, "product": "C=1C=CN2C1CN(C1=C(C2)C=CC=C1)C(=O)C1=CC=C(C=C1)N(C(C1=C(C=CC=C1)C)=O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | A mixture of 0.27 g of 10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine, 0,518 g of 4-[N-methyl-N-(2-methylbenzoyl)amino]benzoyl chloride, 0.182 g of triethylamine and 7 ml of tetrahydrofuran is stirred at room temperature for 3 hours. To the mixture is added 0.29 g of 4-[N-methyl-N-(2-methylbenzoyl)amino]benzoyl chl... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Secondary amine | Tertiary amide | c1ccc2c(c1)Cn1cccc1CN2 | c1ccc2c(c1)Cn1cccc1C[NH]2 | c1ccccc1.c1ccccc1.c1ccc2c(c1)Cn1cccc1C[NH]2 | HCl | ClCCl.O | null | 3 | Cc1ccccc1C(=O)N(C)c1ccc(C(=O)Cl)cc1.c1ccc2c(c1)Cn1cccc1CN2>ClCCl.O>Cc1ccccc1C(=O)N(C)c1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-f0f4f088cd0d48ca83f5762cc569ed4f | Cc1cc(C(=O)N2Cc3cccn3Cc3ccccc32)ccc1N.O=C(Cl)c1ccc(Cl)cc1Cl>>Cc1cc(C(=O)N2Cc3cccn3Cc3ccccc32)ccc1NC(=O)c1ccc(Cl)cc1Cl | CC=1C=C(C(=O)N2CC=3N(CC4=C2C=CC=C4)C=CC3)C=CC1N.ClC1=C(C(=O)Cl)C=CC(=C1)Cl.C(C)(C)N(CC)C(C)C>>C=1C=CN2C1CN(C1=C(C2)C=CC=C1)C(=O)C1=CC(=C(C=C1)NC(C1=C(C=C(C=C1)Cl)Cl)=O)C | [CH3:1][c:2]1[cH:3][c:4]([C:5](=[O:6])[N:7]2[CH2:8][c:9]3[cH:10][cH:11][cH:12][n:13]3[CH2:14][c:15]3[cH:16][cH:17][cH:18][cH:19][c:20]32)[cH:21][cH:22][c:23]1[NH2:24].Cl[C:25](=[O:26])[c:27]1[cH:28][cH:29][c:30]([Cl:31])[cH:32][c:33]1[Cl:34]>>[CH3:1][c:2]1[cH:3][c:4]([C:5](=[O:6])[N:7]2[CH2:8][c:9]3[cH:10][cH:11][cH:12... | Cc1cc(C(=O)N2Cc3cccn3Cc3ccccc32)ccc1N.O=C(Cl)c1ccc(Cl)cc1Cl | Cc1cc(C(=O)N2Cc3cccn3Cc3ccccc32)ccc1NC(=O)c1ccc(Cl)cc1Cl | null | null | ClCCl | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=C(Nc1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1)c1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9])-[c:3](:[c:4]):[c:5] | 84.1 | [{"value": 84.1, "product": "C=1C=CN2C1CN(C1=C(C2)C=CC=C1)C(=O)C1=CC(=C(C=C1)NC(C1=C(C=C(C=C1)Cl)Cl)=O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 16 | HOUR | A mixture of 0.40 g of 10,11-dihydro-10-(3-methyl-4-aminobenzoyl)-5H-pyrrolo[2,1-c][1,4]benzodiazepine, 0.40 g of 2,4-dichlorobenzoyl chloride and 0.75 g of diisopropylethylamine in 50 ml of dichloromethane is stirred at room temperature for 16 hours. The mixture is washed with water, dried (MgSO4) and the solution pas... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccc2c(c1)Cn1cccc1C[NH]2.c1ccccc1 | HCl | ClCCl | null | 16 | Cc1cc(C(=O)N2Cc3cccn3Cc3ccccc32)ccc1N.O=C(Cl)c1ccc(Cl)cc1Cl>ClCCl>Cc1cc(C(=O)N2Cc3cccn3Cc3ccccc32)ccc1NC(=O)c1ccc(Cl)cc1Cl |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-45712a7cc2764af2bb80289af78d8cd0 | COC(=O)CBr.N#Cc1ccccc1N>>COC(=O)CNc1ccccc1C#N | C(#N)C1=C(N)C=CC=C1.BrCC(=O)OC.C([O-])([O-])=O.[K+].[K+]>>C(#N)C1=C(C=CC=C1)NCC(=O)OC | Br[CH2:5][C:3]([O:2][CH3:1])=[O:4].[NH2:6][c:7]1[cH:8][cH:9][cH:10][cH:11][c:12]1[C:13]#[N:14]>>[CH3:1][O:2][C:3](=[O:4])[CH2:5][NH:6][c:7]1[cH:8][cH:9][cH:10][cH:11][c:12]1[C:13]#[N:14] | COC(=O)CBr.N#Cc1ccccc1N | COC(=O)CNc1ccccc1C#N | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | N-alkylation of primary amines with alkyl halides | 308780347cfd56717124ea78bf2bc5de380db774d7ce948246e279dfd7d8998b | d2327a8d30a39f085182e5e2f77f5b022ac99c077866b86103acfec639a8f73d | c1ccccc1 | Br-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#8:4]-[C;D1;H3:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[C;D1;H3:5]-[#8:4]-[C:2](=[O;D1;H0:3])-[CH2;D2;+0:1]-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9] | 80.4 | [{"value": 80.4, "product": "C(#N)C1=C(C=CC=C1)NCC(=O)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 2.2 g of 2-cyanoaniline, 2.0 g of methyl bromoacetate and 1.3 g of potassium carbonate in 12 ml of dry N,N-dimethylformamide is heated at 150°-155° C. for 40 minutes. The cooled mixture is poured into ice-water and the mixture filtered to give 2 g of methyl [N-(2-cyanophenyl)amino]acetate as a yellow solid... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester.Primary amine | Ester.Secondary amine | null | null | c1ccccc1 | HBr | CN(C=O)C | null | null | COC(=O)CBr.N#Cc1ccccc1N>CN(C=O)C>COC(=O)CNc1ccccc1C#N |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-b10c8b2565b240a1a2712a304e908573 | NNC=O.S=C1CCNc2ccccc2N1>>c1ccc2c(c1)NCCc1nncn1-2 | N1C(CCNC2=C1C=CC=C2)=S.C(=O)NN>>C1=NN=C2N1C1=C(NCC2)C=CC=C1 | O=[CH:13][NH:12][NH2:11].S=[C:10]1[CH2:9][CH2:8][NH:7][c:5]2[c:4]([cH:3][cH:2][cH:1][cH:6]2)[NH:14]1>>[cH:1]1[cH:2][cH:3][c:4]2[c:5]([cH:6]1)[NH:7][CH2:8][CH2:9][c:10]1[n:11][n:12][cH:13][n:14]1-2 | NNC=O.S=C1CCNc2ccccc2N1 | c1ccc2c(c1)NCCc1nncn1-2 | null | null | C(CCC)O | Aromatic Heterocycle Formation | OtherReaction | 97b2134a63cbce4c42e43246040717b7fecf4e4761acf980bd904fa52db33e66 | 1e7b5d45c28f5d1767d2abb0c78792aee2714d99002ea329b67f9a89a7e53301 | c1ccc2c(c1)NCCc1nncn1-2 | O=[CH;D2;+0:1]-[NH;D2;+0:2]-[NH2;D1;+0:3].S=[C;H0;D3;+0:4]1-[C:5]-[C:6]-[#7:7]-[c:8](:[c:9]):[c;H0;D3;+0:10](:[c:11]:[c:12])-[NH;D2;+0:13]-1>>[c:12]:[c:11]:[c;H0;D3;+0:10]1:[c:8](:[c:9])-[#7:7]-[C:6]-[C:5]-[c;H0;D3;+0:4]2:[n;H0;D2;+0:3]:[n;H0;D2;+0:2]:[cH;D2;+0:1]:[n;H0;D3;+0:13]:2-1 | 37.3 | [{"value": 37.3, "product": "C1=NN=C2N1C1=C(NCC2)C=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 2,3,4,5-tetrahydro-1H-1,5-benzodiazepin-2-thione (0.8 g) and 0.80 g of N-formylhydrazine in 8 ml of n-butanol is stirred and refluxed for 18 hours and the solvent removed under vacuum. Ice water is added to the residual solid and the mixture filtered to give 0.312 g of a gray solid, m.p. 162°-165° C.
Condi... | 10.6084/m9.figshare.5104873.v1 | null | Acylhydrazine.Thioamide | null | c1ccc2c(c1)NCCCN2 | c1ccc2c(c1)NCCc1nncn12 | c1ccc2c(c1)NCCc1nncn12 | Other | C(CCC)O | null | null | NNC=O.S=C1CCNc2ccccc2N1>C(CCC)O>c1ccc2c(c1)NCCc1nncn1-2 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-f70be6f27b64480db21f26322eb94066 | CCOC(=O)CI.O=[N+]([O-])c1ccccc1-n1cccc1>>CCOC(=O)Cc1cccn1-c1ccccc1[N+](=O)[O-] | OO.ICC(=O)OCC.OO.[N+](=O)([O-])C1=C(C=CC=C1)N1C=CC=C1.ICC(=O)OCC>>[N+](=O)([O-])C1=C(C=CC=C1)N1C(=CC=C1)CC(=O)OCC | I[CH2:6][C:4]([O:3][CH2:2][CH3:1])=[O:5].[cH:7]1[cH:8][cH:9][cH:10][n:11]1-[c:12]1[cH:13][cH:14][cH:15][cH:16][c:17]1[N+:18](=[O:19])[O-:20]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][c:7]1[cH:8][cH:9][cH:10][n:11]1-[c:12]1[cH:13][cH:14][cH:15][cH:16][c:17]1[N+:18](=[O:19])[O-:20] | CCOC(=O)CI.O=[N+]([O-])c1ccccc1-n1cccc1 | CCOC(=O)Cc1cccn1-c1ccccc1[N+](=O)[O-] | null | null | CS(=O)C.O | C-C Coupling | Friedel-Crafts alkylation with halide | 888c8b70bf440687faefdd2f36dfa76e1019407b57ef530c5599854e205163e6 | 0061a06af9fc64155952582b91b574e4abd8908ca14244f15179c2400b24dd08 | c1ccc(-n2cccc2)cc1 | I-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#8:4]-[C:5].[c:6]-[#7;a:7]1:[c:8]:[c:9]:[c:10]:[cH;D2;+0:11]:1>>[C:5]-[#8:4]-[C:2](=[O;D1;H0:3])-[CH2;D2;+0:1]-[c;H0;D3;+0:11]1:[c:10]:[c:9]:[c:8]:[#7;a:7]:1-[c:6] | 10.9 | [{"value": 10.9, "product": "[N+](=O)([O-])C1=C(C=CC=C1)N1C(=CC=C1)CC(=O)OCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | DAY | To a stirred mixture of 1.88 g of 1-(2-nitrophenyl)pyrrole, 4.80 g of ethyl iodoacetate and 2.22 g of FeSO4.7H2O in 40 ml of dimethyl sulfoxide is added dropwise 10 ml of 30% hydrogen peroxide while keeping the reaction mixture at room temperature with a cold water bath. The mixture is stirred at room temperature for o... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester | Ester | c1cc[nH]c1 | c1ccc[nH]1 | c1ccc[nH]1.c1ccccc1 | HI | CS(=O)C.O | null | 24 | CCOC(=O)CI.O=[N+]([O-])c1ccccc1-n1cccc1>CS(=O)C.O>CCOC(=O)Cc1cccn1-c1ccccc1[N+](=O)[O-] |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-71b7c25325774f938eaad758b0324b5c | CCOC(=O)Cc1cccn1-c1ccccc1[N+](=O)[O-]>>O=C1Cc2cccn2-c2ccccc2N1 | [N+](=O)([O-])C1=C(C=CC=C1)N1C(=CC=C1)CC(=O)OCC.O.O.[Cl-].C([O-])([O-])=O.[Na+].[Na+]>>C1=CC=CC=2NC(CC=3N(C21)C=CC3)=O | CCO[C:2](=[O:1])[CH2:3][c:4]1[cH:5][cH:6][cH:7][n:8]1-[c:9]1[cH:10][cH:11][cH:12][cH:13][c:14]1[N+:15](=O)[O-]>>[O:1]=[C:2]1[CH2:3][c:4]2[cH:5][cH:6][cH:7][n:8]2-[c:9]2[cH:10][cH:11][cH:12][cH:13][c:14]2[NH:15]1 | CCOC(=O)Cc1cccn1-c1ccccc1[N+](=O)[O-] | O=C1Cc2cccn2-c2ccccc2N1 | null | null | C(C)O.Cl | Functional Group Interconversion | OtherReaction | 382730e7bc9f0f9f9875e39a9ebb17b819696de424e359accb3d7515af55f20e | 42f24d3b25bb26f4d7fac0ebbebf6d046ea37d400eb2e6f47c39069d069d5e9d | O=C1Cc2cccn2-c2ccccc2N1 | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[c:4]:[#7;a:5]-[c:6]:[c:7](-[N+;H0;D3:8](=O)-[O-]):[c:9]>>[O;D1;H0:2]=[C;H0;D3;+0:1]1-[C:3]-[c:4]:[#7;a:5]-[c:6]:[c:7](:[c:9])-[NH;D2;+0:8]-1 | 100.9 | [{"value": 100.9, "product": "C1=CC=CC=2NC(CC=3N(C21)C=CC3)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 5 | HOUR | To a solution of 0.8 mmol of 1-(2-nitrophenyl)-2-pyrroleacetic acid, ethyl ester in 3 ml of ethanol is added stannus chloride dihydrate (SnCl2.2H2O) in 2 ml of concentrated hydrochloric acid (with cooling in water bath). The mixture is stirred at room temperature for 5 hours and chilled in an ice bath. To the mixture i... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Nitro group | Secondary amide | null | c1ccc2c(c1)NCCc1cccn12 | c1ccc2c(c1)NCCc1cccn12 | HO- | C(C)O.Cl | null | 5 | CCOC(=O)Cc1cccn1-c1ccccc1[N+](=O)[O-]>C(C)O.Cl>O=C1Cc2cccn2-c2ccccc2N1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-310bebf9d2934c12a445ff56372f07e9 | O=C1Cc2cccn2-c2ccccc2N1>>c1ccc2c(c1)NCCc1cccn1-2 | O.C1=CC=CC=2NC(CC=3N(C21)C=CC3)=O.B#B.CSC.[OH-].[Na+]>>C1=CC=CC=2NCCC=3N(C21)C=CC3 | O=[C:8]1[NH:7][c:5]2[c:4]([cH:3][cH:2][cH:1][cH:6]2)-[n:14]2[c:10]([cH:11][cH:12][cH:13]2)[CH2:9]1>>[cH:1]1[cH:2][cH:3][c:4]2[c:5]([cH:6]1)[NH:7][CH2:8][CH2:9][c:10]1[cH:11][cH:12][cH:13][n:14]1-2 | O=C1Cc2cccn2-c2ccccc2N1 | c1ccc2c(c1)NCCc1cccn1-2 | null | null | O1CCCC1 | Reduction | Reduction of secondary amides to amines | 1c4b2e29a0681c872bf984ec2fbbfddea6d48d616299c015790af1243a3d7c88 | ab40188eef2f825df7003af0ffae31d0ce53d126542122535627d3d354cbc9fe | c1ccc2c(c1)NCCc1cccn1-2 | O=[C;H0;D3;+0:1](-[#7:2]-[c:3])-[C:4]-[c:5]:[#7;a:6]>>[#7;a:6]:[c:5]-[C:4]-[CH2;D2;+0:1]-[#7:2]-[c:3] | 99.9 | [{"value": 99.9, "product": "C1=CC=CC=2NCCC=3N(C21)C=CC3", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 0.070 g of 6,7-dihydro-5H-pyrrolo[1,2-a][1,5]benzodiazepin-6-one in 2 ml of tetrahydrofuran is added 0.45 ml of a 2.0M solution of diborane-dimethylsulfide in tetrahydrofuran. The mixture is refluxed for 3 hours, poured into water and make basic with 2N NaOH. The tetrahydrofuran is removed under vacuum... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide | null | c1ccc2c(c1)NCCc1cccn12 | c1ccc2c(c1)NCCc1cccn12 | c1ccc2c(c1)NCCc1cccn12 | Other | O1CCCC1 | null | null | O=C1Cc2cccn2-c2ccccc2N1>O1CCCC1>c1ccc2c(c1)NCCc1cccn1-2 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-25c8ef28b32b437fb9da1f69778e6b37 | CCOC(=O)c1ccc(NC(=O)c2cc(F)ccc2C)cc1>>Cc1ccc(F)cc1C(=O)Nc1ccc(C(=O)O)cc1 | FC=1C=CC(=C(C(=O)NC2=CC=C(C(=O)OCC)C=C2)C1)C.[OH-].[Na+].O.C(C)O>>FC=1C=CC(=C(C(=O)NC2=CC=C(C(=O)O)C=C2)C1)C | CC[O:18][C:16]([c:15]1[cH:14][cH:13][c:12]([NH:11][C:9]([c:8]2[c:2]([CH3:1])[cH:3][cH:4][c:5]([F:6])[cH:7]2)=[O:10])[cH:20][cH:19]1)=[O:17]>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([F:6])[cH:7][c:8]1[C:9](=[O:10])[NH:11][c:12]1[cH:13][cH:14][c:15]([C:16](=[O:17])[OH:18])[cH:19][cH:20]1 | CCOC(=O)c1ccc(NC(=O)c2cc(F)ccc2C)cc1 | Cc1ccc(F)cc1C(=O)Nc1ccc(C(=O)O)cc1 | null | null | C(C)(=O)O | Deprotection | Ester saponification (alkyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | O=C(Nc1ccccc1)c1ccccc1 | C-C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]>>[O;D1;H0:3]=[C:2](-[OH;D1;+0:1])-[c:4] | 86.4 | [{"value": 86.4, "product": "FC=1C=CC(=C(C(=O)NC2=CC=C(C(=O)O)C=C2)C1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 0.60 g of ethyl 4-[(5-fluoro-2-methylbenzoyl)amino]benzoate 0.60 ml of 10N NaOH, 25 ml of water and 50 ml of absolute ethyl alcohol is heated on a steam bath for 1 hour, cooled and acidified with acetic acid. The resulting solid is filtered and dried in vacuo at 60°-80° C. to give 0.47 g of the desired pro... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1.c1ccccc1 | Other | C(C)(=O)O | null | null | CCOC(=O)c1ccc(NC(=O)c2cc(F)ccc2C)cc1>C(C)(=O)O>Cc1ccc(F)cc1C(=O)Nc1ccc(C(=O)O)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-1da5671a1bbe46e789d3388e15982cfa | ClCc1ccc(Cl)cc1Cl.Nc1ccc(C(=O)O)c(Cl)c1.O>>O=C(O)c1ccc(NC(=O)c2ccc(Cl)cc2Cl)cc1Cl | O.C(C)(C)N(C(C)C)CC.ClC1=C(CCl)C=CC(=C1)Cl.ClC1=C(C(=O)O)C=CC(=C1)N>>ClC1=C(C(=O)NC2=CC(=C(C(=O)O)C=C2)Cl)C=CC(=C1)Cl | Cl[CH2:9][c:11]1[cH:12][cH:13][c:14]([Cl:15])[cH:16][c:17]1[Cl:18].[O:1]=[C:2]([OH:3])[c:4]1[cH:5][cH:6][c:7]([NH2:8])[cH:19][c:20]1[Cl:21].[OH2:10]>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][cH:6][c:7]([NH:8][C:9](=[O:10])[c:11]2[cH:12][cH:13][c:14]([Cl:15])[cH:16][c:17]2[Cl:18])[cH:19][c:20]1[Cl:21] | ClCc1ccc(Cl)cc1Cl.Nc1ccc(C(=O)O)c(Cl)c1.O | O=C(O)c1ccc(NC(=O)c2ccc(Cl)cc2Cl)cc1Cl | null | null | C(Cl)Cl | Acylation | OtherReaction | a576a798671826ede762c9794dc0c4b7a0fb3db83f4a13f735c6c2ec52604205 | 27cc109b73410899f9238444201be69792d3e93a2d173166713dc968b67b8de3 | O=C(Nc1ccccc1)c1ccccc1 | Cl-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[NH2;D1;+0:5]-[c:6](:[c:7]):[c:8].[OH2;D0;+0:9]>>[O;H0;D1;+0:9]=[C;H0;D3;+0:1](-[NH;D2;+0:5]-[c:6](:[c:7]):[c:8])-[c:2](:[c:3]):[c:4] | null | [] | null | null | 18 | HOUR | To a stirred mixture of 5.19 g of 2-chloro-4-aminobenzoic acid in 150 ml of methylene chloride is added 7.86 g of N,N-diisopropylethylamine and 12.67 g of 2,4-dichlorobenzylchloride and stirring continued for 18 hours. Water is added to the filtrate and the organic layer dried with Na2 SO4 and concentrate in vacuo to g... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccccc1 | HCl | C(Cl)Cl | null | 18 | ClCc1ccc(Cl)cc1Cl.Nc1ccc(C(=O)O)c(Cl)c1.O>C(Cl)Cl>O=C(O)c1ccc(NC(=O)c2ccc(Cl)cc2Cl)cc1Cl |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-08380087dc6b4d579315e4dd8ce88d84 | COc1cc(C(=O)O)ccc1[N+](=O)[O-].O=S(Cl)Cl>>COc1cc(C(=O)Cl)ccc1[N+](=O)[O-] | COC=1C=C(C(=O)O)C=CC1[N+](=O)[O-].S(=O)(Cl)Cl>>COC=1C=C(C(=O)Cl)C=CC1[N+](=O)[O-] | O[C:6]([c:5]1[cH:4][c:3]([O:2][CH3:1])[c:11]([N+:12](=[O:13])[O-:14])[cH:10][cH:9]1)=[O:7].O=S(Cl)[Cl:8]>>[CH3:1][O:2][c:3]1[cH:4][c:5]([C:6](=[O:7])[Cl:8])[cH:9][cH:10][c:11]1[N+:12](=[O:13])[O-:14] | COc1cc(C(=O)O)ccc1[N+](=O)[O-].O=S(Cl)Cl | COc1cc(C(=O)Cl)ccc1[N+](=O)[O-] | null | null | null | Functional Group Interconversion | Alcohol to chloride_SOCl2 | c301c14a9dcd0670d52e8b77396cbe7fd8edeedd757bc43f4162ade1fc52fc93 | 787f545db5dc0b29dde55b5fbed7db8625b8055f49327f97ed4d83cc47c3af1d | c1ccccc1 | Cl-S(=O)-[Cl;H0;D1;+0:1].O-[C;H0;D3;+0:2](=[O;D1;H0:3])-[c:4](:[c:5]):[c:6]>>[Cl;H0;D1;+0:1]-[C;H0;D3;+0:2](=[O;D1;H0:3])-[c:4](:[c:5]):[c:6] | 52.1 | [{"value": 52.1, "product": "COC=1C=C(C(=O)Cl)C=CC1[N+](=O)[O-]", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 5.0 g of 3-methoxy-4-nitrobenzoic acid and 5.0 g of thionyl chloride is heated under argon for 1 hour. The volatiles are removed in vacuo to give 2.85 g of a 3-methoxy-4-nitrobenzoyl chloride as a residue which is dissolved in 50 ml of methylene chloride. To the preceding solution is added with stirring 1.... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Acyl halide | null | null | c1ccccc1 | HCl | null | null | null | COc1cc(C(=O)O)ccc1[N+](=O)[O-].O=S(Cl)Cl>>COc1cc(C(=O)Cl)ccc1[N+](=O)[O-] |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-a7ca964a2e774eab8f693684b5ac647a | COc1cc(C(=O)N2Cc3cccn3Cc3ccccc32)ccc1[N+](=O)[O-]>>COc1cc(C(=O)N2Cc3cccn3Cc3ccccc32)ccc1N | [N+](=O)([O-])C1=C(C=C(C(=O)N2CC=3N(CC4=C2C=CC=C4)C=CC3)C=C1)OC.NN>>NC1=C(C=C(C(=O)N2CC=3N(CC4=C2C=CC=C4)C=CC3)C=C1)OC | O=[N+:25]([O-])[c:24]1[c:3]([O:2][CH3:1])[cH:4][c:5]([C:6](=[O:7])[N:8]2[CH2:9][c:10]3[cH:11][cH:12][cH:13][n:14]3[CH2:15][c:16]3[cH:17][cH:18][cH:19][cH:20][c:21]32)[cH:22][cH:23]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([C:6](=[O:7])[N:8]2[CH2:9][c:10]3[cH:11][cH:12][cH:13][n:14]3[CH2:15][c:16]3[cH:17][cH:18][cH:19][cH:20][c:... | COc1cc(C(=O)N2Cc3cccn3Cc3ccccc32)ccc1[N+](=O)[O-] | COc1cc(C(=O)N2Cc3cccn3Cc3ccccc32)ccc1N | null | [Pd] | C(C)O | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | O=C(c1ccccc1)N1Cc2cccn2Cc2ccccc21 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | 67.3 | [{"value": 67.3, "product": "NC1=C(C=C(C(=O)N2CC=3N(CC4=C2C=CC=C4)C=CC3)C=C1)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 3.24 g of 10,11-dihydro-10-(4-nitro-3-methoxybenzoyl)-5H-pyrrolo[2,1-c][1,4]benzodiazepine, 0.35 g of 10% Pd/c and 0.60 g of anhydrous hydrazine in 100 ml of absolute ethyl alcohol and heated on a steam bath for 1 hour. The hot reaction mixture is filtered through diatomaceous earth and the filtrate evapor... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1.c1ccc2c(c1)Cn1cccc1C[NH]2 | Other | [Pd].C(C)O | null | null | COc1cc(C(=O)N2Cc3cccn3Cc3ccccc32)ccc1[N+](=O)[O-]>[Pd].C(C)O>COc1cc(C(=O)N2Cc3cccn3Cc3ccccc32)ccc1N |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-ad35d95b28874250afdb320d51226346 | Cc1ccc(F)cc1C(=O)Cl.Nc1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1>>Cc1ccc(F)cc1C(=O)Nc1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1 | CC1=C(C(=O)Cl)C=C(C=C1)F.NC1=CC=C(C(=O)N2CC=3N(CC4=C2C=CC=C4)C=CC3)C=C1.C(C)N(CC)CC>>C=1C=CN2C1CN(C1=C(C2)C=CC=C1)C(=O)C1=CC=C(C=C1)NC(C1=C(C=CC(=C1)F)C)=O | Cl[C:9]([c:8]1[c:2]([CH3:1])[cH:3][cH:4][c:5]([F:6])[cH:7]1)=[O:10].[NH2:11][c:12]1[cH:13][cH:14][c:15]([C:16](=[O:17])[N:18]2[CH2:19][c:20]3[cH:21][cH:22][cH:23][n:24]3[CH2:25][c:26]3[cH:27][cH:28][cH:29][cH:30][c:31]32)[cH:32][cH:33]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([F:6])[cH:7][c:8]1[C:9](=[O:10])[NH:11][c:12]1[cH:1... | Cc1ccc(F)cc1C(=O)Cl.Nc1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1 | Cc1ccc(F)cc1C(=O)Nc1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1 | null | null | C(Cl)Cl | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=C(Nc1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1)c1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9])-[c:3](:[c:4]):[c:5] | 40.7 | [{"value": 40.7, "product": "C=1C=CN2C1CN(C1=C(C2)C=CC=C1)C(=O)C1=CC=C(C=C1)NC(C1=C(C=CC(=C1)F)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 18 | HOUR | To a stirred solution of 500 mg of 10,11-dihydro-10-(4-aminobenzoyl)-5H-pyrrolo[2,1-c][1,4]benzodiazepine in 3 ml of methylene chloride, cooled to 0° C., under argon, is added 346 μl of triethylamine followed by the addition of 340 mg of 2-methyl-5-fluorobenzoyl chloride in 2 ml of methylene chloride. The cooling bath ... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccccc1.c1ccc2c(c1)Cn1cccc1C[NH]2 | HCl | C(Cl)Cl | 0 | 18 | Cc1ccc(F)cc1C(=O)Cl.Nc1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1>C(Cl)Cl>Cc1ccc(F)cc1C(=O)Nc1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-b059c77beaae4653998ed401d032340b | Cc1ccc(F)cc1C(=O)Nc1ccc(C(=O)Cl)c(Cl)c1.c1ccc2c(c1)Cn1cccc1CN2>>Cc1c(F)cccc1C(=O)Nc1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)c(Cl)c1 | O.CC1=C(C(=O)NC2=CC(=C(C(=O)Cl)C=C2)Cl)C=C(C=C1)F.C=1C=CN2C1CNC1=C(C2)C=CC=C1.C(C)(C)N(C(C)C)CC>>C=1C=CN2C1CN(C1=C(C2)C=CC=C1)C(=O)C1=C(C=C(C=C1)NC(C1=C(C(=CC=C1)F)C)=O)Cl | Cl[C:16]([c:15]1[cH:14][cH:13][c:12]([NH:11][C:9]([c:8]2[cH:2][c:3]([F:4])[cH:5][cH:6][c:7]2[CH3:1])=[O:10])[cH:34][c:32]1[Cl:33])=[O:17].[NH:18]1[CH2:19][c:20]2[cH:21][cH:22][cH:23][n:24]2[CH2:25][c:26]2[cH:27][cH:28][cH:29][cH:30][c:31]21>>[CH3:1][c:2]1[c:3]([F:4])[cH:5][cH:6][cH:7][c:8]1[C:9](=[O:10])[NH:11][c:12]1[... | Cc1ccc(F)cc1C(=O)Nc1ccc(C(=O)Cl)c(Cl)c1.c1ccc2c(c1)Cn1cccc1CN2 | Cc1c(F)cccc1C(=O)Nc1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)c(Cl)c1 | null | null | C(Cl)Cl | Acylation | OtherReaction | d9a26cee9924e63d0ba84c6a57146988fdb326037949e7fff4556fed2200a72d | 96cb0a2fed10552c5770a45a2d6523b47ac3e38928b4a9c698d8577451182dcd | O=C(Nc1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1)c1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[CH3;D1;+0:6]-[c;H0;D3;+0:7]1:[c:8]:[c:9]:[c:10](-[F;D1;H0:11]):[cH;D2;+0:12]:[c:13]:1-[C:14](=[O;D1;H0:15])-[#7:16]-[c:17].[#7;a:18]:[c:19]-[C:20]-[NH;D2;+0:21]-[c:22](:[c:23]):[c:24]>>[#7;a:18]:[c:19]-[C:20]-[N;H0;D3;+0:21](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]... | null | [] | null | null | 18 | HOUR | To a solution of 1.50 g of 10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine in 25 ml of methylene chloride is added 1.23 g of N,N-diisopropylethylamine. While cooling in an ice bath, a solution of 3.08 g of [4-[(2-methyl-5-fluorobenzoyl)amino]-2-chlorobenzoyl chloride in 50 ml of methylene chloride is added. The reac... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Secondary amine | Tertiary amide | c1ccccc1.c1ccc2c(c1)Cn1cccc1CN2 | c1ccccc1.c1ccc2c(c1)Cn1cccc1C[NH]2 | c1ccccc1.c1ccccc1.c1ccc2c(c1)Cn1cccc1C[NH]2 | HCl | C(Cl)Cl | null | 18 | Cc1ccc(F)cc1C(=O)Nc1ccc(C(=O)Cl)c(Cl)c1.c1ccc2c(c1)Cn1cccc1CN2>C(Cl)Cl>Cc1c(F)cccc1C(=O)Nc1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)c(Cl)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-eafc60f2c92c4628b1b98036979a993d | Cc1ccc(F)cc1C(=O)Nc1ccc(C(=O)Cl)c(Cl)c1.c1ccc2c(c1)Cn1cccc1CN2>>Cc1ccc(F)cc1C(=O)Nc1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)c(Cl)c1 | O.CC1=C(C(=O)NC2=CC(=C(C(=O)Cl)C=C2)Cl)C=C(C=C1)F.C=1C=CN2C1CNC1=C(C2)C=CC=C1.C(C)(C)N(C(C)C)CC>>C=1C=CN2C1CN(C1=C(C2)C=CC=C1)C(=O)C1=C(C=C(C=C1)NC(C1=C(C=CC(=C1)F)C)=O)Cl | Cl[C:16]([c:15]1[cH:14][cH:13][c:12]([NH:11][C:9]([c:8]2[c:2]([CH3:1])[cH:3][cH:4][c:5]([F:6])[cH:7]2)=[O:10])[cH:34][c:32]1[Cl:33])=[O:17].[NH:18]1[CH2:19][c:20]2[cH:21][cH:22][cH:23][n:24]2[CH2:25][c:26]2[cH:27][cH:28][cH:29][cH:30][c:31]21>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([F:6])[cH:7][c:8]1[C:9](=[O:10])[NH:11][c:12]... | Cc1ccc(F)cc1C(=O)Nc1ccc(C(=O)Cl)c(Cl)c1.c1ccc2c(c1)Cn1cccc1CN2 | Cc1ccc(F)cc1C(=O)Nc1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)c(Cl)c1 | null | null | C(Cl)Cl | Acylation | N-alkylation of secondary amines with alkyl halides | fe674a41b285c5c1b016cd9c12dd41b3635fc90635e2c9974eeff0b8893e7755 | 96cb0a2fed10552c5770a45a2d6523b47ac3e38928b4a9c698d8577451182dcd | O=C(Nc1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1)c1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[#7;a:6]:[c:7]-[C:8]-[NH;D2;+0:9]-[c:10](:[c:11]):[c:12]>>[#7;a:6]:[c:7]-[C:8]-[N;H0;D3;+0:9](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5])-[c:10](:[c:11]):[c:12] | null | [] | null | null | 5 | MINUTE | To a solution of 1.84 g of 10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine in 25 ml of methylene chloride is added 1.30 g of N,N-diisopropylethylamine. While cooling in an ice bath, a solution of 3.45 g of [4-[(2-methyl-5-fluorobenzoyl)amino]-2-chlorobenzoyl chloride in 50 ml of methylene chloride is added. The reac... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Secondary amine | Tertiary amide | c1ccc2c(c1)Cn1cccc1CN2 | c1ccc2c(c1)Cn1cccc1C[NH]2 | c1ccccc1.c1ccccc1.c1ccc2c(c1)Cn1cccc1C[NH]2 | HCl | C(Cl)Cl | null | 0.083333 | Cc1ccc(F)cc1C(=O)Nc1ccc(C(=O)Cl)c(Cl)c1.c1ccc2c(c1)Cn1cccc1CN2>C(Cl)Cl>Cc1ccc(F)cc1C(=O)Nc1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)c(Cl)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-4c868244e3744e8ba1d62fa5fdf18432 | Cc1ccccc1N.O=C(O)c1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1>>Cc1ccccc1NC(=O)c1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1 | C=1C=CN2C1CN(C1=C(C2)C=CC=C1)C(=O)C1=CC=C(C(=O)O)C=C1.C(C)N(CC)CC.NC=1C(=CC=CC1)C.C(C)P(=O)(CC)C#N>>CC1=C(C=CC=C1)NC(C1=CC=C(C=C1)C(=O)N1CC=2N(CC3=C1C=CC=C3)C=CC2)=O | [CH3:1][c:2]1[cH:3][cH:4][cH:5][cH:6][c:7]1[NH2:8].O[C:9](=[O:10])[c:11]1[cH:12][cH:13][c:14]([C:15](=[O:16])[N:17]2[CH2:18][c:19]3[cH:20][cH:21][cH:22][n:23]3[CH2:24][c:25]3[cH:26][cH:27][cH:28][cH:29][c:30]32)[cH:31][cH:32]1>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][cH:6][c:7]1[NH:8][C:9](=[O:10])[c:11]1[cH:12][cH:13][c:14]([... | Cc1ccccc1N.O=C(O)c1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1 | Cc1ccccc1NC(=O)c1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1 | null | null | ClCCl | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(Nc1ccccc1)c1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9])-[c:3](:[c:4]):[c:5] | 54.6 | [{"value": 54.6, "product": "CC1=C(C=CC=C1)NC(C1=CC=C(C=C1)C(=O)N1CC=2N(CC3=C1C=CC=C3)C=CC2)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 0.332 g of 4-(5H-pyrrolo[2,1-c][1,4]benzodiazepin-10(11H)-ylcarbonyl)benzoic acid, 0.111 g of triethylamine, 0.107 g of o-toluidine, and 0.15 ml of diethylphosphoryl cyanide in 20 ml of dichloromethane is heated on a steam bath overnight. The mixture is washed with water, 1M NaHCO3, 1N HCl, brine and dried... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccccc1.c1ccc2c(c1)Cn1cccc1C[NH]2 | HO- | ClCCl | null | null | Cc1ccccc1N.O=C(O)c1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1>ClCCl>Cc1ccccc1NC(=O)c1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-8f2e29c60c754f8292418f4dc28523d6 | Cc1cccc(N)c1C.O=C(O)c1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1>>Cc1cccc(NC(=O)c2ccc(C(=O)N3Cc4cccn4Cc4ccccc43)cc2)c1C | C=1C=CN2C1CN(C1=C(C2)C=CC=C1)C(=O)C1=CC=C(C(=O)O)C=C1.C(C)N(CC)CC.Cl.CC1=C(N)C=CC=C1C.C(C)P(=O)(CC)C#N>>CC1=C(C=CC=C1C)NC(C1=CC=C(C=C1)C(=O)N1CC=2N(CC3=C1C=CC=C3)C=CC2)=O | [CH3:1][c:2]1[cH:3][cH:4][cH:5][c:6]([NH2:7])[c:32]1[CH3:33].O[C:8](=[O:9])[c:10]1[cH:11][cH:12][c:13]([C:14](=[O:15])[N:16]2[CH2:17][c:18]3[cH:19][cH:20][cH:21][n:22]3[CH2:23][c:24]3[cH:25][cH:26][cH:27][cH:28][c:29]32)[cH:30][cH:31]1>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][c:6]([NH:7][C:8](=[O:9])[c:10]2[cH:11][cH:12][c:13]... | Cc1cccc(N)c1C.O=C(O)c1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1 | Cc1cccc(NC(=O)c2ccc(C(=O)N3Cc4cccn4Cc4ccccc43)cc2)c1C | null | null | ClCCl | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(Nc1ccccc1)c1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9])-[c:3](:[c:4]):[c:5] | 25.4 | [{"value": 25.4, "product": "CC1=C(C=CC=C1C)NC(C1=CC=C(C=C1)C(=O)N1CC=2N(CC3=C1C=CC=C3)C=CC2)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 0.332 g of 4-(5H-pyrrolo[2,1-c][1,4]benzodiazepin-10(11H)-ylcarbonyl)benzoic acid, 0.222 g of triethylamine, 0.157 g of 2,3-dimethylaniline hydrochloride, 0.15 ml of diethylphosphoryl cyanide in 20 ml of dichloromethane is heated on a steam bath for 3 hours. The mixture is washed with H2O, 1M NaHCO3, H2O, ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccccc1.c1ccc2c(c1)Cn1cccc1C[NH]2 | HO- | ClCCl | null | null | Cc1cccc(N)c1C.O=C(O)c1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1>ClCCl>Cc1cccc(NC(=O)c2ccc(C(=O)N3Cc4cccn4Cc4ccccc43)cc2)c1C |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-19075005e7214f38bc08e67939d9a779 | Nc1ccc(C(=O)N2Cc3cccn3-c3ccccc32)cc1.O=C(Cl)c1cccc(Cl)c1Cl>>O=C(Nc1ccc(C(=O)N2Cc3cccn3-c3ccccc32)cc1)c1cccc(Cl)c1Cl | NC1=CC=C(C(=O)N2CC=3N(C4=CC=CC=C24)C=CC3)C=C1.ClC1=C(C(=O)Cl)C=CC=C1Cl.ClC1=C(C(=O)Cl)C=CC=C1Cl.C(C)N(CC)CC.C(C)N(CC)CC>>C1=CC=C2N1C1=CC=CC=C1N(C2)C(=O)C2=CC=C(C=C2)NC(C2=C(C(=CC=C2)Cl)Cl)=O | [NH2:3][c:4]1[cH:5][cH:6][c:7]([C:8](=[O:9])[N:10]2[CH2:11][c:12]3[cH:13][cH:14][cH:15][n:16]3-[c:17]3[cH:18][cH:19][cH:20][cH:21][c:22]32)[cH:23][cH:24]1.Cl[C:2](=[O:1])[c:25]1[cH:26][cH:27][cH:28][c:29]([Cl:30])[c:31]1[Cl:32]>>[O:1]=[C:2]([NH:3][c:4]1[cH:5][cH:6][c:7]([C:8](=[O:9])[N:10]2[CH2:11][c:12]3[cH:13][cH:14]... | Nc1ccc(C(=O)N2Cc3cccn3-c3ccccc32)cc1.O=C(Cl)c1cccc(Cl)c1Cl | O=C(Nc1ccc(C(=O)N2Cc3cccn3-c3ccccc32)cc1)c1cccc(Cl)c1Cl | null | null | ClCCl | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=C(Nc1ccc(C(=O)N2Cc3cccn3-c3ccccc32)cc1)c1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9])-[c:3](:[c:4]):[c:5] | 13.3 | [{"value": 13.3, "product": "C1=CC=C2N1C1=CC=CC=C1N(C2)C(=O)C2=CC=C(C=C2)NC(C2=C(C(=CC=C2)Cl)Cl)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | As described for Example 157, 0.47 g of 4,5-dihydro-5-(4-aminobenzoyl)pyrrolo[1,2-a]quinoxaline, 346 μl of triethylamine and 5 ml of dichloromethane are chilled (ice bath) and 0.415 g of 2,3-dichlorobenzoyl chloride in 2 ml of dichloromethane added. After stirring overnight, an additional 346 μl of triethylamine is add... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccc2c(c1)[NH]Cc1cccn12.c1ccccc1 | HCl | ClCCl | null | 8 | Nc1ccc(C(=O)N2Cc3cccn3-c3ccccc32)cc1.O=C(Cl)c1cccc(Cl)c1Cl>ClCCl>O=C(Nc1ccc(C(=O)N2Cc3cccn3-c3ccccc32)cc1)c1cccc(Cl)c1Cl |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-7c16af30cf73497aa3d79a1cdf6d5488 | Nc1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1.O=S(=O)(Cl)c1ccccc1Cl>>O=C(c1ccc(NS(=O)(=O)c2ccccc2Cl)cc1)N1Cc2cccn2Cc2ccccc21 | ClC1=C(C=CC=C1)S(=O)(=O)Cl.NC1=CC=C(C(=O)N2CC=3N(CC4=C2C=CC=C4)C=CC3)C=C1.C(C)N(CC)CC>>ClC1=C(C=CC=C1)S(=O)(=O)NC1=CC=C(C(=O)N2CC=3N(CC4=C2C=CC=C4)C=CC3)C=C1 | [O:1]=[C:2]([c:3]1[cH:4][cH:5][c:6]([NH2:7])[cH:18][cH:19]1)[N:20]1[CH2:21][c:22]2[cH:23][cH:24][cH:25][n:26]2[CH2:27][c:28]2[cH:29][cH:30][cH:31][cH:32][c:33]21.Cl[S:8](=[O:9])(=[O:10])[c:11]1[cH:12][cH:13][cH:14][cH:15][c:16]1[Cl:17]>>[O:1]=[C:2]([c:3]1[cH:4][cH:5][c:6]([NH:7][S:8](=[O:9])(=[O:10])[c:11]2[cH:12][cH:1... | Nc1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1.O=S(=O)(Cl)c1ccccc1Cl | O=C(c1ccc(NS(=O)(=O)c2ccccc2Cl)cc1)N1Cc2cccn2Cc2ccccc21 | null | null | ClCCl | Acylation | Sulfonamide synthesis (Schotten-Baumann) primary amine | 4c44ef6d7646f6ef25dd125d2c32c713d8dcae7c603407faa5f0fb810631670e | 8fce8115d8a725afa92eb3910ded29d4c852e5133eba78a425054f41f7142603 | O=C(c1ccc(NS(=O)(=O)c2ccccc2)cc1)N1Cc2cccn2Cc2ccccc21 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6].[NH2;D1;+0:7]-[c:8](:[c:9]):[c:10]>>[O;D1;H0:2]=[S;H0;D4;+0:1](=[O;D1;H0:3])(-[NH;D2;+0:7]-[c:8](:[c:9]):[c:10])-[c:4](:[c:5]):[c:6] | 20.9 | [{"value": 20.9, "product": "ClC1=C(C=CC=C1)S(=O)(=O)NC1=CC=C(C(=O)N2CC=3N(CC4=C2C=CC=C4)C=CC3)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | To a solution of 0,418 g of 2-chlorobenzenesulfonyl chloride in 5 ml of dichloromethane, cooled to 0° C. is added 0.50 g of 10,11-dihydro-10-(4-aminobenzoyl)-5H-pyrrolo[2,1-c][1,4]benzodiazepine and 0.346 μl of triethylamine. The mixture is stirred at room temperature overnight and diluted with 50 ml of dichloromethane... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Sulfonyl halide | Sulfonamide | null | null | c1ccccc1.c1ccccc1.c1ccc2c(c1)Cn1cccc1C[NH]2 | HCl | ClCCl | null | 8 | Nc1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1.O=S(=O)(Cl)c1ccccc1Cl>ClCCl>O=C(c1ccc(NS(=O)(=O)c2ccccc2Cl)cc1)N1Cc2cccn2Cc2ccccc21 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-f622b83a3d264ad793a2b753b8ea0077 | CC=[N+]=CC.O=C(Nc1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1)c1ccc(Cl)cc1Cl>>CN(C)CN(C(=O)c1ccc(Cl)cc1Cl)c1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1 | [I-].CC=[N+]=CC.[H-].[Na+].C=1C=CN2C1CN(C1=C(C2)C=CC=C1)C(=O)C1=CC=C(C=C1)NC(C1=C(C=C(C=C1)Cl)Cl)=O.O1CCCC1>>CN(C)CN(C(C1=C(C=C(C=C1)Cl)Cl)=O)C1=CC=C(C=C1)C(=O)N1CC=2N(CC3=C1C=CC=C3)C=CC2 | C[CH:1]=[N+:2]=[CH:4][CH3:3].[NH:5]([C:6](=[O:7])[c:8]1[cH:9][cH:10][c:11]([Cl:12])[cH:13][c:14]1[Cl:15])[c:16]1[cH:17][cH:18][c:19]([C:20](=[O:21])[N:22]2[CH2:23][c:24]3[cH:25][cH:26][cH:27][n:28]3[CH2:29][c:30]3[cH:31][cH:32][cH:33][cH:34][c:35]32)[cH:36][cH:37]1>>[CH3:1][N:2]([CH3:3])[CH2:4][N:5]([C:6](=[O:7])[c:8]1... | CC=[N+]=CC.O=C(Nc1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1)c1ccc(Cl)cc1Cl | CN(C)CN(C(=O)c1ccc(Cl)cc1Cl)c1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1 | null | null | C(C)OCC | Functional Group Addition | OtherReaction | c7e959cc3f9d87adb81d5dba89931d9b65c9aca04b2a3be306c5ee7acb903f9f | 740321a1528b5b16d642698be500fb74329d379207d28edd4b87249c96c1b296 | O=C(Nc1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1)c1ccccc1 | C-[CH;D2;+0:1]=[N+;H0;D2:2]=[CH;D2;+0:3]-[CH3;D1;+0:4].[O;D1;H0:5]=[C:6](-[c:7])-[NH;D2;+0:8]-[c:9](:[c:10]):[c:11]>>[CH3;D1;+0:1]-[N;H0;D3;+0:2](-[CH3;D1;+0:4])-[CH2;D2;+0:3]-[N;H0;D3;+0:8](-[C:6](=[O;D1;H0:5])-[c:7])-[c:9](:[c:10]):[c:11] | null | [] | null | null | 1 | HOUR | To a suspension under argon of 0.072 g of sodium hydride (60% in oil) in 10 ml of tetrahydrofuran is added 0.71 g of N-[4-(5H-pyrrolo[2,1-c][1,4]benzodiazepin-10(11H)-ylcarbonyl)phenyl]-2,4-dichlorobenzamide and the mixture stirred at room temperature for 1 hour. To the mixture is added N,N-dimethylmethyleneammonium io... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide | Tertiary amide.Tertiary amine | null | null | c1ccccc1.c1ccccc1.c1ccc2c(c1)Cn1cccc1C[NH]2 | Other | C(C)OCC | null | 1 | CC=[N+]=CC.O=C(Nc1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1)c1ccc(Cl)cc1Cl>C(C)OCC>CN(C)CN(C(=O)c1ccc(Cl)cc1Cl)c1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-de0f1607b1fa4c449eebf6846c063d59 | Nc1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1.O=P(Cl)(c1ccccc1)c1ccccc1>>O=C(c1ccc(NP(=O)(c2ccccc2)c2ccccc2)cc1)N1Cc2cccn2Cc2ccccc21 | [OH-].[Na+].NC1=CC=C(C(=O)N2CC=3N(CC4=C2C=CC=C4)C=CC3)C=C1.C(C)N(CC)CC.C1(=CC=CC=C1)P(=O)(C1=CC=CC=C1)Cl>>C1(=CC=CC=C1)P(=O)(C1=CC=CC=C1)NC1=CC=C(C(=O)N2CC=3N(CC4=C2C=CC=C4)C=CC3)C=C1 | [O:1]=[C:2]([c:3]1[cH:4][cH:5][c:6]([NH2:7])[cH:22][cH:23]1)[N:24]1[CH2:25][c:26]2[cH:27][cH:28][cH:29][n:30]2[CH2:31][c:32]2[cH:33][cH:34][cH:35][cH:36][c:37]21.Cl[P:8](=[O:9])([c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1)[c:16]1[cH:17][cH:18][cH:19][cH:20][cH:21]1>>[O:1]=[C:2]([c:3]1[cH:4][cH:5][c:6]([NH:7][P:8](=[O:9... | Nc1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1.O=P(Cl)(c1ccccc1)c1ccccc1 | O=C(c1ccc(NP(=O)(c2ccccc2)c2ccccc2)cc1)N1Cc2cccn2Cc2ccccc21 | null | null | ClCCl | Miscellaneous | OtherReaction | fdd509933c98c9e4a0e99f159a4b170846e84266732e75f22ed2d14c2d05939b | df99da8e30f7a0cff27b58906548dfea78d3dbceda979e94f8fe07032644b0f4 | O=C(c1ccc(NP(=O)(c2ccccc2)c2ccccc2)cc1)N1Cc2cccn2Cc2ccccc21 | Cl-[P;H0;D4;+0:1](=[O;D1;H0:2])(-[c:3](:[c:4]):[c:5])-[c:6](:[c:7]):[c:8].[NH2;D1;+0:9]-[c:10](:[c:11]):[c:12]>>[O;D1;H0:2]=[P;H0;D4;+0:1](-[NH;D2;+0:9]-[c:10](:[c:11]):[c:12])(-[c:3](:[c:4]):[c:5])-[c:6](:[c:7]):[c:8] | 96.4 | [{"value": 96.4, "product": "C1(=CC=CC=C1)P(=O)(C1=CC=CC=C1)NC1=CC=C(C(=O)N2CC=3N(CC4=C2C=CC=C4)C=CC3)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | A mixture of 0.10 g of 10,11-dihydro-10-(4-aminobenzoyl)-5H-pyrrolo[2,1-c][1,4]benzodiazepine 0.060 g of triethylamine and 0.12 g of diphenylphosphinyl chloride in 2 ml of dichloromethane is stirred at room temperature for 2 hours and then 1N NaOH is added. The mixture is extracted with ethyl acetate and the extract wa... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | Secondary amine | null | null | c1ccccc1.c1ccccc1.c1ccccc1.c1ccc2c(c1)Cn1cccc1C[NH]2 | HCl | ClCCl | null | 2 | Nc1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1.O=P(Cl)(c1ccccc1)c1ccccc1>ClCCl>O=C(c1ccc(NP(=O)(c2ccccc2)c2ccccc2)cc1)N1Cc2cccn2Cc2ccccc21 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-abd443e5c2a645eca228490a19d17993 | Nc1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1.O=S(=O)(Cl)c1cc(Cl)ccc1Cl>>O=C(c1ccc(NS(=O)(=O)c2cc(Cl)ccc2Cl)cc1)N1Cc2cccn2Cc2ccccc21 | [OH-].[Na+].NC1=CC=C(C(=O)N2CC=3N(CC4=C2C=CC=C4)C=CC3)C=C1.C(C)N(CC)CC.ClC1=C(C=C(C=C1)Cl)S(=O)(=O)Cl.ClC1=C(C=C(C=C1)Cl)S(=O)(=O)Cl.C(C)N(CC)CC>>ClC1=C(C=C(C=C1)Cl)S(=O)(=O)NC1=CC=C(C(=O)N2CC=3N(CC4=C2C=CC=C4)C=CC3)C=C1 | [O:1]=[C:2]([c:3]1[cH:4][cH:5][c:6]([NH2:7])[cH:19][cH:20]1)[N:21]1[CH2:22][c:23]2[cH:24][cH:25][cH:26][n:27]2[CH2:28][c:29]2[cH:30][cH:31][cH:32][cH:33][c:34]21.Cl[S:8](=[O:9])(=[O:10])[c:11]1[cH:12][c:13]([Cl:14])[cH:15][cH:16][c:17]1[Cl:18]>>[O:1]=[C:2]([c:3]1[cH:4][cH:5][c:6]([NH:7][S:8](=[O:9])(=[O:10])[c:11]2[cH:... | Nc1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1.O=S(=O)(Cl)c1cc(Cl)ccc1Cl | O=C(c1ccc(NS(=O)(=O)c2cc(Cl)ccc2Cl)cc1)N1Cc2cccn2Cc2ccccc21 | null | CN(C)C1=CC=NC=C1 | ClCCl | Acylation | Sulfonamide synthesis (Schotten-Baumann) primary amine | 4c44ef6d7646f6ef25dd125d2c32c713d8dcae7c603407faa5f0fb810631670e | 8fce8115d8a725afa92eb3910ded29d4c852e5133eba78a425054f41f7142603 | O=C(c1ccc(NS(=O)(=O)c2ccccc2)cc1)N1Cc2cccn2Cc2ccccc21 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6].[NH2;D1;+0:7]-[c:8](:[c:9]):[c:10]>>[O;D1;H0:2]=[S;H0;D4;+0:1](=[O;D1;H0:3])(-[NH;D2;+0:7]-[c:8](:[c:9]):[c:10])-[c:4](:[c:5]):[c:6] | 177.6 | [{"value": 177.6, "product": "ClC1=C(C=C(C=C1)Cl)S(=O)(=O)NC1=CC=C(C(=O)N2CC=3N(CC4=C2C=CC=C4)C=CC3)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | A mixture of 0.10 g of 10,11-dihydro-10-(4-aminobenzoyl)-5H-pyrrolo[2,1-c][1,4]benzodiazepine, 0.050 g of triethylamine and 0.083 g of 2,5-dichlorobenzenesulfonyl chloride in 2 ml of dichloromethane is stirred at room temperature for 1 hour and then 4 mg of 4-(N,N-dimethylamino)pyridine is added. After another hour, 93... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Sulfonyl halide | Sulfonamide | null | null | c1ccccc1.c1ccccc1.c1ccc2c(c1)Cn1cccc1C[NH]2 | HCl | CN(C)C1=CC=NC=C1.ClCCl | null | 1 | Nc1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1.O=S(=O)(Cl)c1cc(Cl)ccc1Cl>CN(C)C1=CC=NC=C1.ClCCl>O=C(c1ccc(NS(=O)(=O)c2cc(Cl)ccc2Cl)cc1)N1Cc2cccn2Cc2ccccc21 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-ad9d485deb4a410790b440b0d8fd2a4a | CCOC(=O)c1ccc(N)cc1.O=C1CCC(=O)N1Cl>>CCOC(=O)c1ccc(N)c(Cl)c1 | NC1=CC=C(C(=O)OCC)C=C1.ClN1C(CCC1=O)=O>>ClC=1C=C(C(=O)OCC)C=CC1N | [CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][c:9]([NH2:10])[cH:11][cH:13]1.O=C1CCC(=O)N1[Cl:12]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][c:9]([NH2:10])[c:11]([Cl:12])[cH:13]1 | CCOC(=O)c1ccc(N)cc1.O=C1CCC(=O)N1Cl | CCOC(=O)c1ccc(N)c(Cl)c1 | null | null | ClCCl | Functional Group Interconversion | Chlorination | 48c1dcf50945076da40bbd7976060ec1ea74b3478ef8c25d67664232b218095c | 0e444576b73669992a4073cc3f7b10ed52cb9df09f9f8e4042e39e6a602aa390 | c1ccccc1 | O=C1-C-C-C(=O)-N-1-[Cl;H0;D1;+0:1].[#8:2]-[C:3](=[O;D1;H0:4])-[c:5]:[c:6]:[cH;D2;+0:7]:[c:8](-[N;D1;H2:9]):[c:10]>>[#8:2]-[C:3](=[O;D1;H0:4])-[c:5]:[c:6]:[c;H0;D3;+0:7](-[Cl;H0;D1;+0:1]):[c:8](-[N;D1;H2:9]):[c:10] | 73.9 | [{"value": 73.9, "product": "ClC=1C=C(C(=O)OCC)C=CC1N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 8.26 g of ethyl 4-aminobenzoate, 8.26 g of N-chlorosuccinimide in 50 ml of dichloromethane is refluxed overnight. The mixture is washed with saturated NaHCO3 solution and dried (Na2SO4). The solution is passed through a thin pad of hydrous magnesium silicate and the filter cake washed with dichloromethane.... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Tertiary amide | Aromatic halide | c1ccccc1.C1CCNC1 | c1ccccc1 | c1ccccc1 | HO- | ClCCl | null | null | CCOC(=O)c1ccc(N)cc1.O=C1CCC(=O)N1Cl>ClCCl>CCOC(=O)c1ccc(N)c(Cl)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-f52a5f30c1274583bbccaa857c73afbc | Cc1c(F)cccc1C(=O)O.O=S(Cl)Cl>>Cc1c(F)cccc1C(=O)Cl | FC=1C(=C(C(=O)O)C=CC1)C.S(=O)(Cl)Cl>>FC=1C(=C(C(=O)Cl)C=CC1)C | O[C:9]([c:8]1[c:2]([CH3:1])[c:3]([F:4])[cH:5][cH:6][cH:7]1)=[O:10].O=S(Cl)[Cl:11]>>[CH3:1][c:2]1[c:3]([F:4])[cH:5][cH:6][cH:7][c:8]1[C:9](=[O:10])[Cl:11] | Cc1c(F)cccc1C(=O)O.O=S(Cl)Cl | Cc1c(F)cccc1C(=O)Cl | null | null | null | Functional Group Interconversion | Alcohol to chloride_SOCl2 | c301c14a9dcd0670d52e8b77396cbe7fd8edeedd757bc43f4162ade1fc52fc93 | 787f545db5dc0b29dde55b5fbed7db8625b8055f49327f97ed4d83cc47c3af1d | c1ccccc1 | Cl-S(=O)-[Cl;H0;D1;+0:1].O-[C;H0;D3;+0:2](=[O;D1;H0:3])-[c:4](:[c:5]):[c:6]>>[Cl;H0;D1;+0:1]-[C;H0;D3;+0:2](=[O;D1;H0:3])-[c:4](:[c:5]):[c:6] | null | [] | null | null | null | null | A solution of 2.87 g of 3-fluoro-2-methylbenzoic acid in 25 ml of thionyl chloride is refluxed for 1.75 hour and the excess thionyl chloride removed under vacuum. To the residue is added toluene (several times) and the toluene removed under vacuum after each addition to give 3-fluoro-2-methylbenzoyl chloride.
Condition... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Acyl halide | null | null | c1ccccc1 | HCl | null | null | null | Cc1c(F)cccc1C(=O)O.O=S(Cl)Cl>>Cc1c(F)cccc1C(=O)Cl |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-919cf0c896304da792a6f642310fe0aa | Cc1c(F)cccc1C(=O)Cl.Nc1ccc(C(=O)N2Cc3ccnn3Cc3ccccc32)cc1>>Cc1c(F)cccc1C(=O)Nc1ccc(C(=O)N2Cc3ccnn3Cc3ccccc32)cc1 | NC1=CC=C(C(=O)N2CC=3N(CC4=C2C=CC=C4)N=CC3)C=C1.C(C)N(CC)CC.FC=1C(=C(C(=O)Cl)C=CC1)C>>N1=CC=C2CN(C3=C(CN21)C=CC=C3)C(=O)C3=CC=C(C=C3)NC(C3=C(C(=CC=C3)F)C)=O | Cl[C:9]([c:8]1[c:2]([CH3:1])[c:3]([F:4])[cH:5][cH:6][cH:7]1)=[O:10].[NH2:11][c:12]1[cH:13][cH:14][c:15]([C:16](=[O:17])[N:18]2[CH2:19][c:20]3[cH:21][cH:22][n:23][n:24]3[CH2:25][c:26]3[cH:27][cH:28][cH:29][cH:30][c:31]32)[cH:32][cH:33]1>>[CH3:1][c:2]1[c:3]([F:4])[cH:5][cH:6][cH:7][c:8]1[C:9](=[O:10])[NH:11][c:12]1[cH:13... | Cc1c(F)cccc1C(=O)Cl.Nc1ccc(C(=O)N2Cc3ccnn3Cc3ccccc32)cc1 | Cc1c(F)cccc1C(=O)Nc1ccc(C(=O)N2Cc3ccnn3Cc3ccccc32)cc1 | null | null | ClCCl | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=C(Nc1ccc(C(=O)N2Cc3ccnn3Cc3ccccc32)cc1)c1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9])-[c:3](:[c:4]):[c:5] | 105 | [{"value": 105.0, "product": "N1=CC=C2CN(C3=C(CN21)C=CC=C3)C(=O)C3=CC=C(C=C3)NC(C3=C(C(=CC=C3)F)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | To a solution of 0.25 g of 5,10-dihydro-5-(4-aminobenzoyl)-4H-pyrazolo[5,1-c][1,4]benzodiazepine and 0.0914 g of triethylamine in 6 ml of dichloromethane under argon is added a solution of 0.156 g of 3-fluoro-2-methylbenzoyl chloride in 1.5 ml of dichloromethane. The mixture is stirred overnight at room temperature and... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccccc1.c1ccc2c(c1)Cn1nccc1C[NH]2 | HCl | ClCCl | null | 8 | Cc1c(F)cccc1C(=O)Cl.Nc1ccc(C(=O)N2Cc3ccnn3Cc3ccccc32)cc1>ClCCl>Cc1c(F)cccc1C(=O)Nc1ccc(C(=O)N2Cc3ccnn3Cc3ccccc32)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-02ea72ab16be477a9f0a58c1ebfcfb1d | Cc1ccc(F)cc1C(=O)Nc1ccc(C(=O)Cl)c(Cl)c1.c1ccc2c(c1)Cn1nccc1CN2>>Cc1ccc(F)cc1C(=O)Nc1ccc(C(=O)N2Cc3ccnn3Cc3ccccc32)c(Cl)c1 | N1=CC=C2CNC3=C(CN21)C=CC=C3.FC=1C=CC(=C(C(=O)NC2=CC(=C(C(=O)Cl)C=C2)Cl)C1)C.C(C)(C)N(CC)C(C)C>>N1=CC=C2CN(C3=C(CN21)C=CC=C3)C(=O)C3=C(C=C(C=C3)NC(C3=C(C=CC(=C3)F)C)=O)Cl | Cl[C:16]([c:15]1[cH:14][cH:13][c:12]([NH:11][C:9]([c:8]2[c:2]([CH3:1])[cH:3][cH:4][c:5]([F:6])[cH:7]2)=[O:10])[cH:34][c:32]1[Cl:33])=[O:17].[NH:18]1[CH2:19][c:20]2[cH:21][cH:22][n:23][n:24]2[CH2:25][c:26]2[cH:27][cH:28][cH:29][cH:30][c:31]21>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([F:6])[cH:7][c:8]1[C:9](=[O:10])[NH:11][c:12]1... | Cc1ccc(F)cc1C(=O)Nc1ccc(C(=O)Cl)c(Cl)c1.c1ccc2c(c1)Cn1nccc1CN2 | Cc1ccc(F)cc1C(=O)Nc1ccc(C(=O)N2Cc3ccnn3Cc3ccccc32)c(Cl)c1 | null | null | ClCCl | Acylation | N-alkylation of secondary amines with alkyl halides | 2a9d533c553c6efbbdf6d8d85d5ea4d91aac2ca9bfdcbb5bc6ecb14894c8ecc0 | 96cb0a2fed10552c5770a45a2d6523b47ac3e38928b4a9c698d8577451182dcd | O=C(Nc1ccc(C(=O)N2Cc3ccnn3Cc3ccccc32)cc1)c1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[#7;a:6]:[#7;a:7]:[c:8]-[C:9]-[NH;D2;+0:10]-[c:11](:[c:12]):[c:13]>>[#7;a:6]:[#7;a:7]:[c:8]-[C:9]-[N;H0;D3;+0:10](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5])-[c:11](:[c:12]):[c:13] | null | [] | null | null | 8 | HOUR | A mixture of 0.185 g of 5,10-dihydro-4H-pyrazolo[5,1-c][1,4]benzodiazepine, 0.391 g of 4-[(5-fluoro-2-methylbenzoyl)amino]-2-chlorobenzoyl chloride and 0.158 g of diisopropylethylamine in 10 ml of dichloromethane is stirred at room temperature overnight. The mixture is washed with H2 O, 1N HCl, H2O, 1M NaHCO3, brine an... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Secondary amine | Tertiary amide | c1ccc2c(c1)Cn1nccc1CN2 | c1ccc2c(c1)Cn1nccc1C[NH]2 | c1ccccc1.c1ccccc1.c1ccc2c(c1)Cn1nccc1C[NH]2 | HCl | ClCCl | null | 8 | Cc1ccc(F)cc1C(=O)Nc1ccc(C(=O)Cl)c(Cl)c1.c1ccc2c(c1)Cn1nccc1CN2>ClCCl>Cc1ccc(F)cc1C(=O)Nc1ccc(C(=O)N2Cc3ccnn3Cc3ccccc32)c(Cl)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-7652de077fa448338717e7eedac5a806 | ClCCl.O=C(Cl)c1ccc(NC(=O)c2ccc(Cl)cc2Cl)cc1.c1ccc2c(c1)Cn1nccc1CN2>>O=C(Nc1ccc(C(=O)N2Cc3ccnn3Cc3ccccc32)c(Cl)c1)c1ccc(Cl)cc1Cl | N1=CC=C2CNC3=C(CN21)C=CC=C3.ClC1=C(C(=O)NC2=CC=C(C(=O)Cl)C=C2)C=CC(=C1)Cl.C(C)(C)N(CC)C(C)C.ClCCl>>N1=CC=C2CN(C3=C(CN21)C=CC=C3)C(=O)C3=C(C=C(C=C3)NC(C3=C(C=C(C=C3)Cl)Cl)=O)Cl | ClC[Cl:25].Cl[C:8]([c:7]1[cH:6][cH:5][c:4]([NH:3][C:2](=[O:1])[c:27]2[cH:28][cH:29][c:30]([Cl:31])[cH:32][c:33]2[Cl:34])[cH:26][cH:24]1)=[O:9].[NH:10]1[CH2:11][c:12]2[cH:13][cH:14][n:15][n:16]2[CH2:17][c:18]2[cH:19][cH:20][cH:21][cH:22][c:23]21>>[O:1]=[C:2]([NH:3][c:4]1[cH:5][cH:6][c:7]([C:8](=[O:9])[N:10]2[CH2:11][c:1... | ClCCl.O=C(Cl)c1ccc(NC(=O)c2ccc(Cl)cc2Cl)cc1.c1ccc2c(c1)Cn1nccc1CN2 | O=C(Nc1ccc(C(=O)N2Cc3ccnn3Cc3ccccc32)c(Cl)c1)c1ccc(Cl)cc1Cl | null | null | null | Acylation | OtherReaction | af11e953acbda4cd321a82fecab5dfbbfc6f684c47d7ce04d238eca2e925acd5 | d821f244a15a29412260bba10bbff42ba13174f3cebb7533dd26ced9e4c0c9da | O=C(Nc1ccc(C(=O)N2Cc3ccnn3Cc3ccccc32)cc1)c1ccccc1 | Cl-C-[Cl;H0;D1;+0:1].Cl-[C;H0;D3;+0:2](=[O;D1;H0:3])-[c:4](:[c:5]):[cH;D2;+0:6]:[c:7]:[c:8].[#7;a:9]:[#7;a:10]:[c:11]-[C:12]-[NH;D2;+0:13]-[c:14](:[c:15]):[c:16]>>[#7;a:9]:[#7;a:10]:[c:11]-[C:12]-[N;H0;D3;+0:13](-[C;H0;D3;+0:2](=[O;D1;H0:3])-[c:4](:[c:5]):[c;H0;D3;+0:6](-[Cl;H0;D1;+0:1]):[c:7]:[c:8])-[c:14](:[c:15]):[c... | null | [] | null | null | 8 | HOUR | As described for Example 518, a mixture of 0.185 g of 5,10-dihydro-4H-pyrazolo[5,1-c][1,4]benzodiazepine, 0.472 g of 4-[(2,4-dichlorobenzoyl)amino]benzoyl chloride and 0.158 g of diisopropylethylamine in 10 ml of dichloromethane is stirred at room temperature overnight to give the product (0.27 g) as a pale yellow glas... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary halide.Primary halide.Secondary amine | Aromatic halide.Tertiary amide | c1ccccc1.c1ccc2c(c1)Cn1nccc1CN2 | c1ccccc1.c1ccc2c(c1)Cn1nccc1C[NH]2 | c1ccccc1.c1ccc2c(c1)Cn1nccc1C[NH]2.c1ccccc1 | HCl | null | null | 8 | ClCCl.O=C(Cl)c1ccc(NC(=O)c2ccc(Cl)cc2Cl)cc1.c1ccc2c(c1)Cn1nccc1CN2>>O=C(Nc1ccc(C(=O)N2Cc3ccnn3Cc3ccccc32)c(Cl)c1)c1ccc(Cl)cc1Cl |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-8027944636f04a1bbee631edd4c8df45 | O=C(c1ccc([N+](=O)[O-])cc1Cl)N1Cc2ccnn2Cc2ccccc21>>Nc1ccc(C(=O)N2Cc3ccnn3Cc3ccccc32)c(Cl)c1 | C(C)(=O)O.[N+](=O)([O-])C1=CC(=C(C(=O)N2CC=3N(CC4=C2C=CC=C4)N=CC3)C=C1)Cl.C(=O)(O)[O-].[Na+]>>NC1=CC(=C(C(=O)N2CC=3N(CC4=C2C=CC=C4)N=CC3)C=C1)Cl | O=[N+:1]([O-])[c:2]1[cH:3][cH:4][c:5]([C:6](=[O:7])[N:8]2[CH2:9][c:10]3[cH:11][cH:12][n:13][n:14]3[CH2:15][c:16]3[cH:17][cH:18][cH:19][cH:20][c:21]32)[c:22]([Cl:23])[cH:24]1>>[NH2:1][c:2]1[cH:3][cH:4][c:5]([C:6](=[O:7])[N:8]2[CH2:9][c:10]3[cH:11][cH:12][n:13][n:14]3[CH2:15][c:16]3[cH:17][cH:18][cH:19][cH:20][c:21]32)[c... | O=C(c1ccc([N+](=O)[O-])cc1Cl)N1Cc2ccnn2Cc2ccccc21 | Nc1ccc(C(=O)N2Cc3ccnn3Cc3ccccc32)c(Cl)c1 | null | null | C(C)O | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | O=C(c1ccccc1)N1Cc2ccnn2Cc2ccccc21 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | 78.7 | [{"value": 78.7, "product": "NC1=CC(=C(C(=O)N2CC=3N(CC4=C2C=CC=C4)N=CC3)C=C1)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 0.5 | HOUR | A mixture of 0.553 g of 5,10-dihydro-5-(4-nitro-2-chlorobenzoyl)-4H-pyrazolo[5,1-c][1,4]benzodiazepine, 1.70 g of stannous chloride dihydrate in 20 ml of ethanol is heated at 70°-80° C. for 1 hour. The mixture is chilled, made basic with 1M NaHCO3 and then stirred at room temperature for 0.5 hour. The mixture is brough... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1.c1ccc2c(c1)Cn1nccc1C[NH]2 | Other | C(C)O | null | 0.5 | O=C(c1ccc([N+](=O)[O-])cc1Cl)N1Cc2ccnn2Cc2ccccc21>C(C)O>Nc1ccc(C(=O)N2Cc3ccnn3Cc3ccccc32)c(Cl)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-34153ce5c06943e3a08530200f7b8a3d | Cc1ccccc1C(=O)Nc1ccc(C(=O)Cl)cc1Cl.c1ccc2c(c1)Cn1cccc1CN2>>Cc1ccccc1C(=O)Nc1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1Cl | CC1=C(C(=O)NC2=C(C=C(C(=O)Cl)C=C2)Cl)C=CC=C1.C=1C=CN2C1CNC1=C(C2)C=CC=C1.C(C)(C)N(C(C)C)CC>>C=1C=CN2C1CN(C1=C(C2)C=CC=C1)C(=O)C1=CC(=C(C=C1)NC(C1=C(C=CC=C1)C)=O)Cl | Cl[C:15]([c:14]1[cH:13][cH:12][c:11]([NH:10][C:8]([c:7]2[c:2]([CH3:1])[cH:3][cH:4][cH:5][cH:6]2)=[O:9])[c:32]([Cl:33])[cH:31]1)=[O:16].[NH:17]1[CH2:18][c:19]2[cH:20][cH:21][cH:22][n:23]2[CH2:24][c:25]2[cH:26][cH:27][cH:28][cH:29][c:30]21>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][cH:6][c:7]1[C:8](=[O:9])[NH:10][c:11]1[cH:12][cH:... | Cc1ccccc1C(=O)Nc1ccc(C(=O)Cl)cc1Cl.c1ccc2c(c1)Cn1cccc1CN2 | Cc1ccccc1C(=O)Nc1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1Cl | null | null | ClCCl | Acylation | N-alkylation of secondary amines with alkyl halides | fe674a41b285c5c1b016cd9c12dd41b3635fc90635e2c9974eeff0b8893e7755 | 96cb0a2fed10552c5770a45a2d6523b47ac3e38928b4a9c698d8577451182dcd | O=C(Nc1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1)c1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[#7;a:6]:[c:7]-[C:8]-[NH;D2;+0:9]-[c:10](:[c:11]):[c:12]>>[#7;a:6]:[c:7]-[C:8]-[N;H0;D3;+0:9](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5])-[c:10](:[c:11]):[c:12] | 106 | [{"value": 106.0, "product": "C=1C=CN2C1CN(C1=C(C2)C=CC=C1)C(=O)C1=CC(=C(C=C1)NC(C1=C(C=CC=C1)C)=O)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | To a mixture of 1.38 g of 10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine, 1.11 g of N,N-diisopropylethylamine in 50 ml of dichloromethane is added 2.61 g of 4-[(2-methylbenzoyl)amino]-3-chlorobenzoyl chloride in 25 ml of dichloromethane. The mixture is stirred at room temperature overnight and then washed with H2O ... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Secondary amine | Tertiary amide | c1ccc2c(c1)Cn1cccc1CN2 | c1ccc2c(c1)Cn1cccc1C[NH]2 | c1ccccc1.c1ccccc1.c1ccc2c(c1)Cn1cccc1C[NH]2 | HCl | ClCCl | null | 8 | Cc1ccccc1C(=O)Nc1ccc(C(=O)Cl)cc1Cl.c1ccc2c(c1)Cn1cccc1CN2>ClCCl>Cc1ccccc1C(=O)Nc1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1Cl |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-e1104a14670241aeb4e8e0077b154812 | Nc1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1.O=C(Cl)C(Cl)c1ccccc1>>O=C(Nc1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1)C(Cl)c1ccccc1 | ClC(C(=O)Cl)C1=CC=CC=C1.NC1=CC=C(C(=O)N2CC=3N(CC4=C2C=CC=C4)C=CC3)C=C1.C(C)N(CC)CC>>ClC(C(=O)NC1=CC=C(C=C1)C(=O)N1CC=2N(CC3=C1C=CC=C3)C=CC2)C2=CC=CC=C2 | [NH2:3][c:4]1[cH:5][cH:6][c:7]([C:8](=[O:9])[N:10]2[CH2:11][c:12]3[cH:13][cH:14][cH:15][n:16]3[CH2:17][c:18]3[cH:19][cH:20][cH:21][cH:22][c:23]32)[cH:24][cH:25]1.Cl[C:2](=[O:1])[CH:26]([Cl:27])[c:28]1[cH:29][cH:30][cH:31][cH:32][cH:33]1>>[O:1]=[C:2]([NH:3][c:4]1[cH:5][cH:6][c:7]([C:8](=[O:9])[N:10]2[CH2:11][c:12]3[cH:1... | Nc1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1.O=C(Cl)C(Cl)c1ccccc1 | O=C(Nc1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1)C(Cl)c1ccccc1 | null | null | C(Cl)Cl.C(=O)(O)[O-].[Na+] | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=C(Cc1ccccc1)Nc1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[Cl;D1;H0:4])-[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[Cl;D1;H0:4]-[C:3](-[c:5])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9] | 106.9 | [{"value": 106.9, "product": "ClC(C(=O)NC1=CC=C(C=C1)C(=O)N1CC=2N(CC3=C1C=CC=C3)C=CC2)C2=CC=CC=C2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | To a solution of 0.61 g of 10,11-dihydro-10-(4-aminobenzoyl)-5H-pyrrolo[2,1-c][1,4]benzodiazepine in 8 ml of methylene chloride is added 0.30 g of triethylamine followed by 0.47 g of (±)-2-chloro-2-phenylacetyl chloride in 2 ml of methylene chloride. The mixture is stirred at room temperature for 1 hour and then dilute... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccc2c(c1)Cn1cccc1C[NH]2.c1ccccc1 | HCl | C(Cl)Cl.C(=O)(O)[O-].[Na+] | null | 1 | Nc1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1.O=C(Cl)C(Cl)c1ccccc1>C(Cl)Cl.C(=O)(O)[O-].[Na+]>O=C(Nc1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1)C(Cl)c1ccccc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-32280068ecb64f769769bd675ed7dae6 | CN(C)CCS.O=C(Nc1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1)C(Cl)c1ccccc1>>CN(C)CCSC(C(=O)Nc1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1)c1ccccc1 | ClC(C(=O)NC1=CC=C(C=C1)C(=O)N1CC=2N(CC3=C1C=CC=C3)C=CC2)C2=CC=CC=C2.Cl.CN(CCS)C.C(C)N(CC)CC.CN1C(N(CCC1)C)=O>>CN(CCSC(C(=O)NC1=CC=C(C=C1)C(=O)N1CC=2N(CC3=C1C=CC=C3)C=CC2)C2=CC=CC=C2)C | [CH3:1][N:2]([CH3:3])[CH2:4][CH2:5][SH:6].Cl[CH:7]([C:8](=[O:9])[NH:10][c:11]1[cH:12][cH:13][c:14]([C:15](=[O:16])[N:17]2[CH2:18][c:19]3[cH:20][cH:21][cH:22][n:23]3[CH2:24][c:25]3[cH:26][cH:27][cH:28][cH:29][c:30]32)[cH:31][cH:32]1)[c:33]1[cH:34][cH:35][cH:36][cH:37][cH:38]1>>[CH3:1][N:2]([CH3:3])[CH2:4][CH2:5][S:6][CH... | CN(C)CCS.O=C(Nc1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1)C(Cl)c1ccccc1 | CN(C)CCSC(C(=O)Nc1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1)c1ccccc1 | null | null | CO | Heteroatom Alkylation and Arylation | thioether_nucl_sub | 33911e859e6592d6f871c2001d0ee821d31ec9926111c5b2f3ef7209d6ab05ca | b79d3f6d229d7e360144ea29b140141b83222cf18153cb8c665e3bd28be113c6 | O=C(Cc1ccccc1)Nc1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1 | Cl-[CH;D3;+0:1](-[C:2](=[O;D1;H0:3])-[#7:4]-[c:5])-[c:6](:[c:7]):[c:8].[C:9]-[C:10]-[SH;D1;+0:11]>>[C:9]-[C:10]-[S;H0;D2;+0:11]-[CH;D3;+0:1](-[C:2](=[O;D1;H0:3])-[#7:4]-[c:5])-[c:6](:[c:7]):[c:8] | 93.1 | [{"value": 93.1, "product": "CN(CCSC(C(=O)NC1=CC=C(C=C1)C(=O)N1CC=2N(CC3=C1C=CC=C3)C=CC2)C2=CC=CC=C2)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | null | null | A mixture of 0.14 g of α-chloro-N-[4-(5H-pyrrolo[2,1-c][1,4]benzodiazepin-10(11H)-ylcarbonyl)phenyl]benzeneacetamide, 0.47 g of 2-dimethylaminoethanethiol hydrochloride in 2 ml of methyl alcohol, 0.30 g of triethylamine and 3 ml of 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone is heated at 60° C. for 48 hours. The... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Aliphatic thiol | Monosulfide | null | null | c1ccccc1.c1ccc2c(c1)Cn1cccc1C[NH]2.c1ccccc1 | HCl | CO | 60 | null | CN(C)CCS.O=C(Nc1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1)C(Cl)c1ccccc1>CO>CN(C)CCSC(C(=O)Nc1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1)c1ccccc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-10007385ab964c208a8b83d8c610f4fa | CNC.O=C(Nc1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1)C(Cl)c1ccccc1>>CN(C)C(C(=O)Nc1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1)c1ccccc1 | C(C)(=O)OCC.CCCCCC.ClC(C(=O)NC1=CC=C(C=C1)C(=O)N1CC=2N(CC3=C1C=CC=C3)C=CC2)C2=CC=CC=C2.CNC.CN1C(N(CCC1)C)=O>>CN(C(C(=O)NC1=CC=C(C=C1)C(=O)N1CC=2N(CC3=C1C=CC=C3)C=CC2)C2=CC=CC=C2)C | [CH3:1][NH:2][CH3:3].Cl[CH:4]([C:5](=[O:6])[NH:7][c:8]1[cH:9][cH:10][c:11]([C:12](=[O:13])[N:14]2[CH2:15][c:16]3[cH:17][cH:18][cH:19][n:20]3[CH2:21][c:22]3[cH:23][cH:24][cH:25][cH:26][c:27]32)[cH:28][cH:29]1)[c:30]1[cH:31][cH:32][cH:33][cH:34][cH:35]1>>[CH3:1][N:2]([CH3:3])[CH:4]([C:5](=[O:6])[NH:7][c:8]1[cH:9][cH:10][... | CNC.O=C(Nc1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1)C(Cl)c1ccccc1 | CN(C)C(C(=O)Nc1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1)c1ccccc1 | null | null | CO | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 7415c72f24e9b8534fd0cb3a2627a4a83a66246cf298a1bc23f59f647bedc118 | fb63ba09935e18320be03869002f6d5d0f0321fe7dbcd94a5ae956c3effd182d | O=C(Cc1ccccc1)Nc1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1 | Cl-[CH;D3;+0:1](-[C:2](=[O;D1;H0:3])-[#7:4]-[c:5])-[c:6](:[c:7]):[c:8].[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])-[CH;D3;+0:1](-[C:2](=[O;D1;H0:3])-[#7:4]-[c:5])-[c:6](:[c:7]):[c:8] | null | [] | null | null | 20 | HOUR | A partial solution of ?? g of α-chloro-N-[4-(5H-pyrrolo[2,1-c][1,4]benzodiazepin-10(11H)-ylcarbonyl)phenyl]benzeneacetamide in 1 ml of methanol is treated with 0.5 ml of dimethylamine and 1 ml of 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone and stirring continued for 20 hours. The methanol is evaporated and the r... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Secondary amine | Tertiary amine | null | null | c1ccccc1.c1ccc2c(c1)Cn1cccc1C[NH]2.c1ccccc1 | HCl | CO | null | 20 | CNC.O=C(Nc1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1)C(Cl)c1ccccc1>CO>CN(C)C(C(=O)Nc1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1)c1ccccc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-304e0847445947b383b809c5a452b282 | CCN(CC)CC.Nc1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1.O=C([O-])O>>CC(=O)OC(C(=O)Nc1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1)c1ccccc1 | C(=O)(O)[O-].[Na+].NC1=CC=C(C(=O)N2CC=3N(CC4=C2C=CC=C4)C=CC3)C=C1.C(C)N(CC)CC>>C(C)(=O)OC(C(=O)NC1=CC=C(C=C1)C(=O)N1CC=2N(CC3=C1C=CC=C3)C=CC2)C2=CC=CC=C2 | N([CH2:2][CH3:1])([CH2:5][CH3:33])[CH2:36][CH3:35].[NH2:8][c:9]1[cH:10][cH:11][c:12]([C:13](=[O:14])[N:15]2[CH2:16][c:17]3[cH:18][cH:19][cH:20][n:21]3[CH2:22][c:23]3[cH:24][cH:25][cH:26][cH:27][c:28]32)[cH:29][cH:30]1.[O-:3][C:6]([OH:4])=[O:7]>>[CH3:1][C:2](=[O:3])[O:4][CH:5]([C:6](=[O:7])[NH:8][c:9]1[cH:10][cH:11][c:1... | CCN(CC)CC.Nc1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1.O=C([O-])O | CC(=O)OC(C(=O)Nc1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1)c1ccccc1 | null | null | C(Cl)Cl | Aromatic Heterocycle Formation | OtherReaction | f0a83f1640322dd2511c5bd1f6c98429979a048c258edf9dc4f62ae977d3d4b5 | 57978846a026801a1470ce3443d59c46710f2b15b277823c63754bebf2d50c5e | O=C(Cc1ccccc1)Nc1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1 | [C;D1;H3:1]-[CH2;D2;+0:2]-N(-[CH2;D2;+0:3]-[CH3;D1;+0:4])-[CH2;D2;+0:5]-[CH3;D1;+0:6].[NH2;D1;+0:7]-[c:8](:[c:9]):[c:10].[O-;H0;D1:11]-[C;H0;D3;+0:12](=[O;D1;H0:13])-[OH;D1;+0:14]>>[C;D1;H3:1]-[C;H0;D3;+0:2](=[O;H0;D1;+0:11])-[O;H0;D2;+0:14]-[CH;D3;+0:5](-[C;H0;D3;+0:12](=[O;D1;H0:13])-[NH;D2;+0:7]-[c:8](:[c:9]):[c:10]... | null | [] | null | null | 1 | HOUR | To a solution of 0.30 g of 10,11-dihydro-10-(4-aminobenzoyl)-5H-pyrrolo[2,1-c][1,4]benzodiazepine in 5 ml of methylene chloride is added 0.15 g of triethylamine followed by 0.27 g of O-acetylmandelic acid chloride. The mixture is stirred at room temperature for 1 hour and then diluted with 50% NaHCO3. The methylene chl... | 10.6084/m9.figshare.5104873.v1 | null | Carbonic Acid.Primary amine.Tertiary amine | Ester.Secondary amide | null | c1ccccc1 | c1ccccc1.c1ccc2c(c1)Cn1cccc1C[NH]2.c1ccccc1 | null | C(Cl)Cl | null | 1 | CCN(CC)CC.Nc1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1.O=C([O-])O>C(Cl)Cl>CC(=O)OC(C(=O)Nc1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1)c1ccccc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-9bad5fecb8854a0b85e3651c3a658f21 | CC(=O)OC(C(=O)Nc1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1)c1ccccc1>>O=C(Nc1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1)C(O)c1ccccc1 | C(C)(=O)OC(C(=O)NC1=CC=C(C=C1)C(=O)N1CC=2N(CC3=C1C=CC=C3)C=CC2)C2=CC=CC=C2>>OC(C(=O)NC1=CC=C(C=C1)C(=O)N1CC=2N(CC3=C1C=CC=C3)C=CC2)C2=CC=CC=C2 | CC(=O)[O:27][CH:26]([C:2](=[O:1])[NH:3][c:4]1[cH:5][cH:6][c:7]([C:8](=[O:9])[N:10]2[CH2:11][c:12]3[cH:13][cH:14][cH:15][n:16]3[CH2:17][c:18]3[cH:19][cH:20][cH:21][cH:22][c:23]32)[cH:24][cH:25]1)[c:28]1[cH:29][cH:30][cH:31][cH:32][cH:33]1>>[O:1]=[C:2]([NH:3][c:4]1[cH:5][cH:6][c:7]([C:8](=[O:9])[N:10]2[CH2:11][c:12]3[cH:... | CC(=O)OC(C(=O)Nc1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1)c1ccccc1 | O=C(Nc1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1)C(O)c1ccccc1 | null | null | [OH-].[Na+].CO.O | Reduction | Hydrolysis or Hydrogenolysis of Carboxylic Esters or Thioesters | d7acfb2397f2b5b2a83b3bebf3698d6d984dd716982297f62a944222c79ce234 | 19dd58e0f83625e74b4b1375d88cb4c813ee60f593d812516d14eafc4ab68dc7 | O=C(Cc1ccccc1)Nc1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1 | C-C(=O)-[O;H0;D2;+0:1]-[C:2](-[c:3])-[C:4](=[O;D1;H0:5])-[#7:6]-[c:7]>>[O;D1;H0:5]=[C:4](-[#7:6]-[c:7])-[C:2](-[OH;D1;+0:1])-[c:3] | null | [] | null | null | null | null | A solution of 0.34 g of α-(acetyloxy)-N-[4-(5H-pyrrolo[2,1-c][1,4]benzodiazepin-10(11H)-ylcarbonyl)phenyl]benzeneacetamide in 2 ml of 1N NaOH and 4 ml of methyl alcohol is stirred at room temperature for 30 minutes, diluted with 2 ml of water and evaporated in vacuo. The aqueous suspension is extracted with 30 ml of et... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Secondary alcohol | null | null | c1ccccc1.c1ccc2c(c1)Cn1cccc1C[NH]2.c1ccccc1 | HO- | [OH-].[Na+].CO.O | null | null | CC(=O)OC(C(=O)Nc1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1)c1ccccc1>[OH-].[Na+].CO.O>O=C(Nc1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1)C(O)c1ccccc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-917010d59ebf4aef9603f2501a624c6d | Nc1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1.O=C(Cl)CCl>>O=C(CCl)Nc1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1 | ClCC(=O)Cl.NC1=CC=C(C(=O)N2CC=3N(CC4=C2C=CC=C4)C=CC3)C=C1.C(C)N(CC)CC>>ClCC(=O)NC1=CC=C(C=C1)C(=O)N1CC=2N(CC3=C1C=CC=C3)C=CC2 | [NH2:5][c:6]1[cH:7][cH:8][c:9]([C:10](=[O:11])[N:12]2[CH2:13][c:14]3[cH:15][cH:16][cH:17][n:18]3[CH2:19][c:20]3[cH:21][cH:22][cH:23][cH:24][c:25]32)[cH:26][cH:27]1.Cl[C:2](=[O:1])[CH2:3][Cl:4]>>[O:1]=[C:2]([CH2:3][Cl:4])[NH:5][c:6]1[cH:7][cH:8][c:9]([C:10](=[O:11])[N:12]2[CH2:13][c:14]3[cH:15][cH:16][cH:17][n:18]3[CH2:... | Nc1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1.O=C(Cl)CCl | O=C(CCl)Nc1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1 | null | CN(C)C1=NC=CC=C1 | C(Cl)Cl | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=C(c1ccccc1)N1Cc2cccn2Cc2ccccc21 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[Cl;D1;H0:4].[NH2;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[Cl;D1;H0:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:5]-[c:6](:[c:7]):[c:8] | 100.1 | [{"value": 100.1, "product": "ClCC(=O)NC1=CC=C(C=C1)C(=O)N1CC=2N(CC3=C1C=CC=C3)C=CC2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | To a stirred solution of 0.91 g of 10,11-dihydro-10-(4-aminobenzoyl)-5H-pyrrolo[2,1-c][1,4]-benzodiazepine in 10 ml of methylene chloride is added 0.46 g of triethylamine and 36 mg of dimethylaminopyridine followed by the slow addition of 0.42 g of chloroacetyl chloride in 5 ml of methylene chloride. The resulting mixt... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccc2c(c1)Cn1cccc1C[NH]2 | HCl | CN(C)C1=NC=CC=C1.C(Cl)Cl | null | 3 | Nc1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1.O=C(Cl)CCl>CN(C)C1=NC=CC=C1.C(Cl)Cl>O=C(CCl)Nc1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-b58a69d7ccb643e6b7543dcded01e2ce | C1COCCN1.O=C(CCl)Nc1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1>>O=C(CN1CCOCC1)Nc1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1 | ClCC(=O)NC1=CC=C(C=C1)C(=O)N1CC=2N(CC3=C1C=CC=C3)C=CC2.N1CCOCC1.CN1C(N(CCC1)C)=O>>C=1C=CN2C1CN(C1=C(C2)C=CC=C1)C(=O)C1=CC=C(C=C1)NC(CN1CCOCC1)=O | [NH:4]1[CH2:5][CH2:6][O:7][CH2:8][CH2:9]1.Cl[CH2:3][C:2](=[O:1])[NH:10][c:11]1[cH:12][cH:13][c:14]([C:15](=[O:16])[N:17]2[CH2:18][c:19]3[cH:20][cH:21][cH:22][n:23]3[CH2:24][c:25]3[cH:26][cH:27][cH:28][cH:29][c:30]32)[cH:31][cH:32]1>>[O:1]=[C:2]([CH2:3][N:4]1[CH2:5][CH2:6][O:7][CH2:8][CH2:9]1)[NH:10][c:11]1[cH:12][cH:13... | C1COCCN1.O=C(CCl)Nc1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1 | O=C(CN1CCOCC1)Nc1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1 | null | null | C(Cl)Cl | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 2bad30dcdb0a20edb8ce877f072b133eedfd870621da393ec393128bfee00977 | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | O=C(CN1CCOCC1)Nc1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1 | Cl-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#7:4]-[c:5].[#8:6]1-[C:7]-[C:8]-[NH;D2;+0:9]-[C:10]-[C:11]-1>>[O;D1;H0:3]=[C:2](-[#7:4]-[c:5])-[CH2;D2;+0:1]-[N;H0;D3;+0:9]1-[C:8]-[C:7]-[#8:6]-[C:11]-[C:10]-1 | 106.8 | [{"value": 106.8, "product": "C=1C=CN2C1CN(C1=C(C2)C=CC=C1)C(=O)C1=CC=C(C=C1)NC(CN1CCOCC1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 20 | HOUR | A stirred suspension of 0.19 g of 2-chloro-N-[4-(5H-pyrrolo[2,1-c][1,4]benzodiazepin-10(11H)-ylcarbonyl)phenyl]acetamide in 1 ml of methylene chloride is added 0.44 g of morpholine followed by 1 ml of 1,3-di-methyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone and stirring continued for 20 hours. The methylene chloride is evap... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1COCCN1 | C1COCC[NH]1 | C1COCC[NH]1.c1ccccc1.c1ccc2c(c1)Cn1cccc1C[NH]2 | HCl | C(Cl)Cl | null | 20 | C1COCCN1.O=C(CCl)Nc1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1>C(Cl)Cl>O=C(CN1CCOCC1)Nc1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-0377322d180742a7acad3e33e6f3f423 | Clc1ccccc1CBr.O=C(CN1CCOCC1)Nc1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1>>O=C(CN1CCOCC1)N(Cc1ccccc1Cl)c1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1 | C=1C=CN2C1CN(C1=C(C2)C=CC=C1)C(=O)C1=CC=C(C=C1)NC(CN1CCOCC1)=O.C1=CC=C(C(=C1)CBr)Cl.C1=CC=C(C(=C1)CBr)Cl.[H-].[Na+]>>ClC1=C(C=CC=C1)CN(C(CN1CCOCC1)=O)C1=CC=C(C=C1)C(=O)N1CC=2N(CC3=C1C=CC=C3)C=CC2 | Br[CH2:11][c:12]1[cH:13][cH:14][cH:15][cH:16][c:17]1[Cl:18].[O:1]=[C:2]([CH2:3][N:4]1[CH2:5][CH2:6][O:7][CH2:8][CH2:9]1)[NH:10][c:19]1[cH:20][cH:21][c:22]([C:23](=[O:24])[N:25]2[CH2:26][c:27]3[cH:28][cH:29][cH:30][n:31]3[CH2:32][c:33]3[cH:34][cH:35][cH:36][cH:37][c:38]32)[cH:39][cH:40]1>>[O:1]=[C:2]([CH2:3][N:4]1[CH2:5... | Clc1ccccc1CBr.O=C(CN1CCOCC1)Nc1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1 | O=C(CN1CCOCC1)N(Cc1ccccc1Cl)c1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1 | null | null | C(C)#N.O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | db9b1b8804b469c037e0a5ba95031d33e73dcd5fc2a6fa79163c623adf75f2a1 | 4a6c1e88c9e8bed487b746792f88d478ff36cc235f9a217d4632e6babdebdc9a | O=C(CN1CCOCC1)N(Cc1ccccc1)c1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[C:5]-[C:6](=[O;D1;H0:7])-[NH;D2;+0:8]-[c:9](:[c:10]):[c:11]>>[C:5]-[C:6](=[O;D1;H0:7])-[N;H0;D3;+0:8](-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4])-[c:9](:[c:10]):[c:11] | 126.9 | [{"value": 126.9, "product": "ClC1=C(C=CC=C1)CN(C(CN1CCOCC1)=O)C1=CC=C(C=C1)C(=O)N1CC=2N(CC3=C1C=CC=C3)C=CC2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 0.11 g of N-[4-(5H-pyrrolo[2,1-c][1,4]benzodiazepin-10(11H)-ylcarbonyl)phenyl]-4-morpholineacetamide, 56 mg of O-chlorobenzyl bromide and 0.41 g of K2 CO3 in 5 ml of acetonitrile is heated at reflux for 18 hours. An additional 30 mg of O-chlorobenzyl bromide and 0.4 mmol of sodium hydride is added followed... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amide | Tertiary amide | null | null | C1COCC[NH]1.c1ccccc1.c1ccccc1.c1ccc2c(c1)Cn1cccc1C[NH]2 | HBr | C(C)#N.O | null | null | Clc1ccccc1CBr.O=C(CN1CCOCC1)Nc1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1>C(C)#N.O>O=C(CN1CCOCC1)N(Cc1ccccc1Cl)c1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-cc4b68ef8db8421b815156d3cb52f80e | CCOC(=O)c1ccc2n1Cc1ccccc1N(C(=O)c1ccc(N)c(C)c1)C2.O=C(Cl)c1ccc(Cl)cc1Cl>>CCOC(=O)c1ccc2n1Cc1ccccc1N(C(=O)c1ccc(NC(=O)c3ccc(Cl)cc3Cl)c(C)c1)C2 | NC1=C(C=C(C(=O)N2CC=3N(CC4=C2C=CC=C4)C(=CC3)C(=O)OCC)C=C1)C.C(C)(C)N(C(C)C)CC.ClC1=C(C(=O)Cl)C=CC(=C1)Cl>>ClC1=C(C(=O)NC2=C(C=C(C(=O)N3CC=4N(CC5=C3C=CC=C5)C(=CC4)C(=O)OCC)C=C2)C)C=CC(=C1)Cl | [CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][c:9]2[n:10]1[CH2:11][c:12]1[cH:13][cH:14][cH:15][cH:16][c:17]1[N:18]([C:19](=[O:20])[c:21]1[cH:22][cH:23][c:24]([NH2:25])[c:36]([CH3:37])[cH:38]1)[CH2:39]2.Cl[C:26](=[O:27])[c:28]1[cH:29][cH:30][c:31]([Cl:32])[cH:33][c:34]1[Cl:35]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]... | CCOC(=O)c1ccc2n1Cc1ccccc1N(C(=O)c1ccc(N)c(C)c1)C2.O=C(Cl)c1ccc(Cl)cc1Cl | CCOC(=O)c1ccc2n1Cc1ccccc1N(C(=O)c1ccc(NC(=O)c3ccc(Cl)cc3Cl)c(C)c1)C2 | null | null | C(Cl)Cl | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=C(Nc1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1)c1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9])-[c:3](:[c:4]):[c:5] | 55.4 | [{"value": 55.4, "product": "ClC1=C(C(=O)NC2=C(C=C(C(=O)N3CC=4N(CC5=C3C=CC=C5)C(=CC4)C(=O)OCC)C=C2)C)C=CC(=C1)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 18 | HOUR | To a solution of 0.30 g of ethyl 10,11-dihydro-10-(4-amino-3-methylbenzoyl)-5H-pyrrolo[2,1-c][1,4]benzodiazepine-3-carboxylate in 20 ml of methylene chloride is added 0.15 g of N,N-diisopropylethylamine and 0.24 g of 2,4-dichlorobenzoyl chloride. The reaction mixture is stirred at room temperature for 18 hours and wash... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccc2c(c1)Cn1cccc1C[NH]2.c1ccccc1.c1ccccc1 | HCl | C(Cl)Cl | null | 18 | CCOC(=O)c1ccc2n1Cc1ccccc1N(C(=O)c1ccc(N)c(C)c1)C2.O=C(Cl)c1ccc(Cl)cc1Cl>C(Cl)Cl>CCOC(=O)c1ccc2n1Cc1ccccc1N(C(=O)c1ccc(NC(=O)c3ccc(Cl)cc3Cl)c(C)c1)C2 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-4913bed741254ca6990c0db4a7da2257 | Nc1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1.O=C(Cl)c1cc(Cl)cc(Cl)c1Cl>>O=C(Nc1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1)c1cc(Cl)cc(Cl)c1Cl | NC1=CC=C(C(=O)N2CC=3N(CC4=C2C=CC=C4)C=CC3)C=C1.ClC1=C(C(=O)Cl)C=C(C=C1Cl)Cl>>C=1C=CN2C1CN(C1=C(C2)C=CC=C1)C(=O)C1=CC=C(C=C1)NC(C1=C(C(=CC(=C1)Cl)Cl)Cl)=O | [NH2:3][c:4]1[cH:5][cH:6][c:7]([C:8](=[O:9])[N:10]2[CH2:11][c:12]3[cH:13][cH:14][cH:15][n:16]3[CH2:17][c:18]3[cH:19][cH:20][cH:21][cH:22][c:23]32)[cH:24][cH:25]1.Cl[C:2](=[O:1])[c:26]1[cH:27][c:28]([Cl:29])[cH:30][c:31]([Cl:32])[c:33]1[Cl:34]>>[O:1]=[C:2]([NH:3][c:4]1[cH:5][cH:6][c:7]([C:8](=[O:9])[N:10]2[CH2:11][c:12]... | Nc1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1.O=C(Cl)c1cc(Cl)cc(Cl)c1Cl | O=C(Nc1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1)c1cc(Cl)cc(Cl)c1Cl | null | null | null | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=C(Nc1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1)c1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9])-[c:3](:[c:4]):[c:5] | 81.5 | [{"value": 81.5, "product": "C=1C=CN2C1CN(C1=C(C2)C=CC=C1)C(=O)C1=CC=C(C=C1)NC(C1=C(C(=CC(=C1)Cl)Cl)Cl)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | As described for Example 8, 0.50 g of 10,11-dihydro-10-(4-aminobenzoyl)-5H-pyrrolo[2,1-c][1,4]benzodiazepine is reacted with 0.483 g of 2,3,5-trichlorobenzoyl chloride to give a glass which is crystallized from ethyl acetate to give 0.686 g of crystals, m.p. 231°-234° C.
Conditions: See reaction.notes.procedure_details... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccc2c(c1)Cn1cccc1C[NH]2.c1ccccc1 | HCl | null | null | null | Nc1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1.O=C(Cl)c1cc(Cl)cc(Cl)c1Cl>>O=C(Nc1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1)c1cc(Cl)cc(Cl)c1Cl |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-ae040de2c66a4ae688eaef7fb08c8c28 | Nc1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1.O=C(Cl)C1CCCO1>>O=C(Nc1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1)C1CCCO1 | NC1=CC=C(C(=O)N2CC=3N(CC4=C2C=CC=C4)C=CC3)C=C1.O1C(CCC1)C(=O)Cl>>C=1C=CN2C1CN(C1=C(C2)C=CC=C1)C(=O)C1=CC=C(C=C1)NC(=O)C1OCCC1 | [NH2:3][c:4]1[cH:5][cH:6][c:7]([C:8](=[O:9])[N:10]2[CH2:11][c:12]3[cH:13][cH:14][cH:15][n:16]3[CH2:17][c:18]3[cH:19][cH:20][cH:21][cH:22][c:23]32)[cH:24][cH:25]1.Cl[C:2](=[O:1])[CH:26]1[CH2:27][CH2:28][CH2:29][O:30]1>>[O:1]=[C:2]([NH:3][c:4]1[cH:5][cH:6][c:7]([C:8](=[O:9])[N:10]2[CH2:11][c:12]3[cH:13][cH:14][cH:15][n:1... | Nc1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1.O=C(Cl)C1CCCO1 | O=C(Nc1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1)C1CCCO1 | null | null | null | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=C(Nc1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1)C1CCCO1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[#8:5]-[C:6].[NH2;D1;+0:7]-[c:8](:[c:9]):[c:10]>>[C:4]-[C:3](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:7]-[c:8](:[c:9]):[c:10])-[#8:5]-[C:6] | 33.2 | [{"value": 33.2, "product": "C=1C=CN2C1CN(C1=C(C2)C=CC=C1)C(=O)C1=CC=C(C=C1)NC(=O)C1OCCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | As described for Example 8, 0.500 g of 10,11-dihydro-10-(4-aminobenzoyl)-5H-pyrrolo[2,1-c][1,4]benzodiazepine is reacted with 0.267 g of tetrahydrofurane-2-carbonyl chloride to give a glass which is crystallized from ethyl acetate to give 0.22 g of crystals, m.p. 208°-214° C.
Conditions: See reaction.notes.procedure_de... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccc2c(c1)Cn1cccc1C[NH]2.C1CCOC1 | HCl | null | null | null | Nc1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1.O=C(Cl)C1CCCO1>>O=C(Nc1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1)C1CCCO1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-169b2f504f264086a66d2edfe51fb873 | CCOC(=O)c1ccc([N+](=O)[O-])c(CBr)c1.O=Cc1ccc[nH]1>>CCOC(=O)c1ccc([N+](=O)[O-])c(Cn2cccc2C=O)c1 | [H-].[Na+].N1C(=CC=C1)C=O.[N+](=O)([O-])C1=C(C=C(C(=O)OCC)C=C1)CBr>>[N+](=O)([O-])C1=C(CN2C(=CC=C2)C=O)C=C(C=C1)C(=O)OCC | Br[CH2:14][c:13]1[c:9]([N+:10](=[O:11])[O-:12])[cH:8][cH:7][c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[cH:22]1.[nH:15]1[cH:16][cH:17][cH:18][c:19]1[CH:20]=[O:21]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][c:9]([N+:10](=[O:11])[O-:12])[c:13]([CH2:14][n:15]2[cH:16][cH:17][cH:18][c:19]2[CH:20]=[O:21])[cH:22]1 | CCOC(=O)c1ccc([N+](=O)[O-])c(CBr)c1.O=Cc1ccc[nH]1 | CCOC(=O)c1ccc([N+](=O)[O-])c(Cn2cccc2C=O)c1 | null | null | O1CCCC1 | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 161a14961e9f1b305dfb4891994ad58540b58501680f8eb4ba76ad15e1e7cb96 | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | c1ccc(Cn2cccc2)cc1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[O;D1;H0:5]=[C:6]-[c:7]1:[c:8]:[c:9]:[c:10]:[nH;D2;+0:11]:1>>[O;D1;H0:5]=[C:6]-[c:7]1:[c:8]:[c:9]:[c:10]:[n;H0;D3;+0:11]:1-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4] | 83.9 | [{"value": 83.9, "product": "[N+](=O)([O-])C1=C(CN2C(=CC=C2)C=O)C=C(C=C1)C(=O)OCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 20 | CELSIUS | 8 | HOUR | To a stirred slurry of 2.2 g of sodium hydride (60% in oil, washed with hexane) in tetrahydrofuran is added at 0° C. a solution of 4.5 g of pyrrole-2-carboxaldehyde in 25 ml of tetrahydrofuran. After the addition is complete, a solution of 15 g of ethyl 4-nitro-3-bromomethylbenzoate in 30 ml of dry tetrahydrofuran is s... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1cc[nH]c1 | c1ccc[nH]1 | c1ccccc1.c1ccc[nH]1 | HBr | O1CCCC1 | 20 | 8 | CCOC(=O)c1ccc([N+](=O)[O-])c(CBr)c1.O=Cc1ccc[nH]1>O1CCCC1>CCOC(=O)c1ccc([N+](=O)[O-])c(Cn2cccc2C=O)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-3632dee499a345c98f0a864a80748938 | CCOC(=O)c1ccc([N+](=O)[O-])c(Cn2cccc2C=O)c1>>CCOC(=O)c1ccc2c(c1)Cn1cccc1CN2 | [N+](=O)([O-])C1=C(CN2C(=CC=C2)C=O)C=C(C=C1)C(=O)OCC.[H][H]>>C=1C=CN2C1CNC1=C(C2)C=C(C=C1)C(=O)OCC | O=[CH:18][c:17]1[n:13]([CH2:12][c:10]2[c:9]([N+:19](=O)[O-])[cH:8][cH:7][c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[cH:11]2)[cH:14][cH:15][cH:16]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][c:9]2[c:10]([cH:11]1)[CH2:12][n:13]1[cH:14][cH:15][cH:16][c:17]1[CH2:18][NH:19]2 | CCOC(=O)c1ccc([N+](=O)[O-])c(Cn2cccc2C=O)c1 | CCOC(=O)c1ccc2c(c1)Cn1cccc1CN2 | null | [Pd] | C(C)O | Functional Group Interconversion | OtherReaction | c1a0903850e5ee790d4c072add317d49699fb5d2a58f13379b43d3709958c227 | 8d376a33ce625efea21a727d4a046134c1d759eb13efe5fa1e2683895e99352c | c1ccc2c(c1)Cn1cccc1CN2 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[#7;a:4](-[C:5]-[c:6]:[c:7](-[N+;H0;D3:8](=O)-[O-]):[c:9]):[c:10]>>[c:10]:[#7;a:4]1:[c:2](:[c:3])-[CH2;D2;+0:1]-[NH;D2;+0:8]-[c:7](:[c:9]):[c:6]-[C:5]-1 | null | [] | null | null | null | null | A solution of 10.0 g of 1-[2-nitro-5-(ethoxycarbonyl)benzyl]-pyrrole-2-carboxaldehyde in 150 ml of absolute ethanol containing 1.0 g of 10% Pd/c is hydrogenated in a Parr apparatus for 16 hours under 40 psi of hydrogen. The reaction mixture is filtered through a pad of diatomaceous earth and the filtrate concentrated i... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Nitro group | Secondary amine | null | c1ccc2c(c1)Cn1cccc1CN2 | c1ccc2c(c1)Cn1cccc1CN2 | Other | [Pd].C(C)O | null | null | CCOC(=O)c1ccc([N+](=O)[O-])c(Cn2cccc2C=O)c1>[Pd].C(C)O>CCOC(=O)c1ccc2c(c1)Cn1cccc1CN2 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-9965c8ddeefc46de9909fc238a1926ed | CCOC(=O)c1ccc2c(c1)Cn1cccc1CN2.Cc1ccccc1C(=O)Nc1ccc(C(=O)Cl)cc1>>CCOC(=O)c1ccc2c(c1)Cn1cccc1CN2C(=O)c1ccc(NC(=O)c2ccccc2C)cc1 | C=1C=CN2C1CNC1=C(C2)C=C(C=C1)C(=O)OCC.C(C)N(CC)CC.CC1=C(C(=O)NC2=CC=C(C(=O)Cl)C=C2)C=CC=C1>>CC1=C(C(=O)NC2=CC=C(C(=O)N3CC=4N(CC5=C3C=CC(=C5)C(=O)OCC)C=CC4)C=C2)C=CC=C1 | [CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][c:9]2[c:10]([cH:11]1)[CH2:12][n:13]1[cH:14][cH:15][cH:16][c:17]1[CH2:18][NH:19]2.Cl[C:20](=[O:21])[c:22]1[cH:23][cH:24][c:25]([NH:26][C:27](=[O:28])[c:29]2[cH:30][cH:31][cH:32][cH:33][c:34]2[CH3:35])[cH:36][cH:37]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][c:... | CCOC(=O)c1ccc2c(c1)Cn1cccc1CN2.Cc1ccccc1C(=O)Nc1ccc(C(=O)Cl)cc1 | CCOC(=O)c1ccc2c(c1)Cn1cccc1CN2C(=O)c1ccc(NC(=O)c2ccccc2C)cc1 | null | null | C(Cl)Cl | Acylation | N-alkylation of secondary amines with alkyl halides | fe674a41b285c5c1b016cd9c12dd41b3635fc90635e2c9974eeff0b8893e7755 | 96cb0a2fed10552c5770a45a2d6523b47ac3e38928b4a9c698d8577451182dcd | O=C(Nc1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1)c1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[#7;a:6]:[c:7]-[C:8]-[NH;D2;+0:9]-[c:10](:[c:11]):[c:12]>>[#7;a:6]:[c:7]-[C:8]-[N;H0;D3;+0:9](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5])-[c:10](:[c:11]):[c:12] | 43.3 | [{"value": 43.3, "product": "CC1=C(C(=O)NC2=CC=C(C(=O)N3CC=4N(CC5=C3C=CC(=C5)C(=O)OCC)C=CC4)C=C2)C=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 18 | HOUR | A solution of 1.2 g of ethyl 10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine-7-carboxylate in 100 ml of methylene chloride is cooled to 0° C. and 10 ml of triethylamine added followed by 1.5 g of 4-[(2-methylbenzoyl)amino)benzoyl chloride. The reaction mixture is stirred at room temperature for 18 hours and concentr... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Secondary amine | Tertiary amide | c1ccc2c(c1)Cn1cccc1CN2 | c1ccc2c(c1)Cn1cccc1C[NH]2 | c1ccc2c(c1)Cn1cccc1C[NH]2.c1ccccc1.c1ccccc1 | HCl | C(Cl)Cl | null | 18 | CCOC(=O)c1ccc2c(c1)Cn1cccc1CN2.Cc1ccccc1C(=O)Nc1ccc(C(=O)Cl)cc1>C(Cl)Cl>CCOC(=O)c1ccc2c(c1)Cn1cccc1CN2C(=O)c1ccc(NC(=O)c2ccccc2C)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-2645c2c262564c698b845595cc95d126 | Nc1ccc(C(=O)N2Cc3nccn3Cc3ccccc32)cc1.O=C(Cl)c1ccc(Cl)cc1Cl>>O=C(Nc1ccc(C(=O)N2Cc3nccn3Cc3ccccc32)cc1)c1ccc(Cl)cc1Cl | ClC1=C(C(=O)Cl)C=CC(=C1)Cl.NC1=CC=C(C(=O)N2CC=3N(CC4=C2C=CC=C4)C=CN3)C=C1.[H-].[Na+]>>N=1C=CN2C1CN(C1=C(C2)C=CC=C1)C(=O)C1=CC=C(C=C1)NC(C1=C(C=C(C=C1)Cl)Cl)=O | [NH2:3][c:4]1[cH:5][cH:6][c:7]([C:8](=[O:9])[N:10]2[CH2:11][c:12]3[n:13][cH:14][cH:15][n:16]3[CH2:17][c:18]3[cH:19][cH:20][cH:21][cH:22][c:23]32)[cH:24][cH:25]1.Cl[C:2](=[O:1])[c:26]1[cH:27][cH:28][c:29]([Cl:30])[cH:31][c:32]1[Cl:33]>>[O:1]=[C:2]([NH:3][c:4]1[cH:5][cH:6][c:7]([C:8](=[O:9])[N:10]2[CH2:11][c:12]3[n:13][c... | Nc1ccc(C(=O)N2Cc3nccn3Cc3ccccc32)cc1.O=C(Cl)c1ccc(Cl)cc1Cl | O=C(Nc1ccc(C(=O)N2Cc3nccn3Cc3ccccc32)cc1)c1ccc(Cl)cc1Cl | null | null | O1CCOCC1 | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=C(Nc1ccc(C(=O)N2Cc3nccn3Cc3ccccc32)cc1)c1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9])-[c:3](:[c:4]):[c:5] | null | [] | null | null | 2 | DAY | A slurry of 0.330 g of 10,11-dihydro-10-(4-aminobenzoyl)-5H-imidazo[2,1-c][1,4]benzodiazepine in 15 ml of dioxane is stirred and warmed slightly to obtain a nearly complete solution. The reaction mixture is cooled to room temperature and 43 mg of sodium hydride in oil added. The mixture is warmed slightly. Gas evolutio... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccc2c(c1)Cn1ccnc1C[NH]2.c1ccccc1 | HCl | O1CCOCC1 | null | 48 | Nc1ccc(C(=O)N2Cc3nccn3Cc3ccccc32)cc1.O=C(Cl)c1ccc(Cl)cc1Cl>O1CCOCC1>O=C(Nc1ccc(C(=O)N2Cc3nccn3Cc3ccccc32)cc1)c1ccc(Cl)cc1Cl |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-fa4012fada9d450bb1c4694877c81d19 | O=C(Cl)c1ccc([N+](=O)[O-])cc1Cl.c1ccc2c(c1)NCCc1cccn1-2>>O=C(c1ccc([N+](=O)[O-])cc1Cl)N1CCc2cccn2-c2ccccc21 | ClC1=C(C(=O)Cl)C=CC(=C1)[N+](=O)[O-].C1=CC=CC=2NCCC=3N(C21)C=CC3.C(C)N(CC)CC>>ClC1=C(C(=O)N2CCC=3N(C4=C2C=CC=C4)C=CC3)C=CC(=C1)[N+](=O)[O-] | Cl[C:2](=[O:1])[c:3]1[cH:4][cH:5][c:6]([N+:7](=[O:8])[O-:9])[cH:10][c:11]1[Cl:12].[NH:13]1[CH2:14][CH2:15][c:16]2[cH:17][cH:18][cH:19][n:20]2-[c:21]2[cH:22][cH:23][cH:24][cH:25][c:26]21>>[O:1]=[C:2]([c:3]1[cH:4][cH:5][c:6]([N+:7](=[O:8])[O-:9])[cH:10][c:11]1[Cl:12])[N:13]1[CH2:14][CH2:15][c:16]2[cH:17][cH:18][cH:19][n:... | O=C(Cl)c1ccc([N+](=O)[O-])cc1Cl.c1ccc2c(c1)NCCc1cccn1-2 | O=C(c1ccc([N+](=O)[O-])cc1Cl)N1CCc2cccn2-c2ccccc21 | null | null | C(Cl)Cl | Acylation | N-alkylation of secondary amines with alkyl halides | cacede3ee7b9065bc38250c6b836fcccf2981bf26d370ef9023b706cddcb599c | 96cb0a2fed10552c5770a45a2d6523b47ac3e38928b4a9c698d8577451182dcd | O=C(c1ccccc1)N1CCc2cccn2-c2ccccc21 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[#7;a:6]-[c:7]:[c:8](:[c:9])-[NH;D2;+0:10]-[C:11]-[C:12]>>[#7;a:6]-[c:7]:[c:8](:[c:9])-[N;H0;D3;+0:10](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5])-[C:11]-[C:12] | 105.6 | [{"value": 105.6, "product": "ClC1=C(C(=O)N2CCC=3N(C4=C2C=CC=C4)C=CC3)C=CC(=C1)[N+](=O)[O-]", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | To a solution of 0.28 g of 6,7-dihydro-5H-pyrrolo[1,2-a][1,5]benzodiazepine in 6 ml of methylene chloride is added 0.30 g of triethylamine followed by 0.50 g of 2-chloro-4-nitrobenzoyl chloride in 0.5 ml of methylene chloride. The reaction mixture is stirred at room temperature for 1 hour then quenched with 5 ml of sat... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Secondary amine | Tertiary amide | c1ccc2c(c1)NCCc1cccn12 | c1ccc2c(c1)[NH]CCc1cccn12 | c1ccccc1.c1ccc2c(c1)[NH]CCc1cccn12 | HCl | C(Cl)Cl | null | 1 | O=C(Cl)c1ccc([N+](=O)[O-])cc1Cl.c1ccc2c(c1)NCCc1cccn1-2>C(Cl)Cl>O=C(c1ccc([N+](=O)[O-])cc1Cl)N1CCc2cccn2-c2ccccc21 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-5d66cdab1c794ab784689ff5a3d4e879 | O=C(c1ccc([N+](=O)[O-])cc1Cl)N1CCc2cccn2-c2ccccc21>>Nc1ccc(C(=O)N2CCc3cccn3-c3ccccc32)c(Cl)c1 | ClC1=C(C(=O)N2CCC=3N(C4=C2C=CC=C4)C=CC3)C=CC(=C1)[N+](=O)[O-].O.O.Cl[Sn]Cl>>NC1=CC(=C(C(=O)N2CCC=3N(C4=C2C=CC=C4)C=CC3)C=C1)Cl | O=[N+:1]([O-])[c:2]1[cH:3][cH:4][c:5]([C:6](=[O:7])[N:8]2[CH2:9][CH2:10][c:11]3[cH:12][cH:13][cH:14][n:15]3-[c:16]3[cH:17][cH:18][cH:19][cH:20][c:21]32)[c:22]([Cl:23])[cH:24]1>>[NH2:1][c:2]1[cH:3][cH:4][c:5]([C:6](=[O:7])[N:8]2[CH2:9][CH2:10][c:11]3[cH:12][cH:13][cH:14][n:15]3-[c:16]3[cH:17][cH:18][cH:19][cH:20][c:21]3... | O=C(c1ccc([N+](=O)[O-])cc1Cl)N1CCc2cccn2-c2ccccc21 | Nc1ccc(C(=O)N2CCc3cccn3-c3ccccc32)c(Cl)c1 | null | null | C(C)O.O1CCCC1 | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | O=C(c1ccccc1)N1CCc2cccn2-c2ccccc21 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | 102.3 | [{"value": 102.3, "product": "NC1=CC(=C(C(=O)N2CCC=3N(C4=C2C=CC=C4)C=CC3)C=C1)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 55 | CELSIUS | 30 | MINUTE | To a solution of 0,50 g of 6,7-dihydro-5-(2-chloro-4-nitrobenzoyl)-5H-pyrrolo[1,2-a][1,5]benzodiazepine in 10 ml of ethyl alcohol and 2 ml of tetrahydrofuran is added 2.35 g of SnCl2.2H2O and the mixture stirred at 55° C. for 30 minutes. The solvents are evaporated in vacuo to a residue which is stirred with 20 ml of 1... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1.c1ccc2c(c1)[NH]CCc1cccn12 | Other | C(C)O.O1CCCC1 | 55 | 0.5 | O=C(c1ccc([N+](=O)[O-])cc1Cl)N1CCc2cccn2-c2ccccc21>C(C)O.O1CCCC1>Nc1ccc(C(=O)N2CCc3cccn3-c3ccccc32)c(Cl)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-1058c1411e7545ab82db068cfac0a11f | Cc1c(F)cccc1C(=O)Cl.Nc1ccc(C(=O)N2CCc3cccn3-c3ccccc32)c(Cl)c1>>Cc1c(F)cccc1C(=O)Nc1ccc(C(=O)N2CCc3cccn3-c3ccccc32)c(Cl)c1 | [OH-].[Na+].NC1=CC(=C(C(=O)N2CCC=3N(C4=C2C=CC=C4)C=CC3)C=C1)Cl.C(C)N(CC)CC.FC=1C(=C(C(=O)Cl)C=CC1)C>>C1=CC=CC=2N(CCC=3N(C21)C=CC3)C(=O)C3=C(C=C(C=C3)NC(C3=C(C(=CC=C3)F)C)=O)Cl | Cl[C:9]([c:8]1[c:2]([CH3:1])[c:3]([F:4])[cH:5][cH:6][cH:7]1)=[O:10].[NH2:11][c:12]1[cH:13][cH:14][c:15]([C:16](=[O:17])[N:18]2[CH2:19][CH2:20][c:21]3[cH:22][cH:23][cH:24][n:25]3-[c:26]3[cH:27][cH:28][cH:29][cH:30][c:31]32)[c:32]([Cl:33])[cH:34]1>>[CH3:1][c:2]1[c:3]([F:4])[cH:5][cH:6][cH:7][c:8]1[C:9](=[O:10])[NH:11][c:... | Cc1c(F)cccc1C(=O)Cl.Nc1ccc(C(=O)N2CCc3cccn3-c3ccccc32)c(Cl)c1 | Cc1c(F)cccc1C(=O)Nc1ccc(C(=O)N2CCc3cccn3-c3ccccc32)c(Cl)c1 | null | null | ClCCl | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=C(Nc1ccc(C(=O)N2CCc3cccn3-c3ccccc32)cc1)c1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9])-[c:3](:[c:4]):[c:5] | 106.9 | [{"value": 106.9, "product": "C1=CC=CC=2N(CCC=3N(C21)C=CC3)C(=O)C3=C(C=C(C=C3)NC(C3=C(C(=CC=C3)F)C)=O)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | To a mixture of 0.10 g of 6,7-dihydro-5-(4-amino-2-chlorobenzoyl)-5H-pyrrolo-[1,2-a][1,5]benzodiazepine and 0.06 g of triethylamine in 6 ml of dichloromethane is added 0.08 g of 3-fluoro-2-methylbenzoyl chloride in 0.5 ml of dichloromethane. The mixture is stirred for 2 hours at room temperature and then 2 ml of 1N NaO... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccccc1.c1ccc2c(c1)[NH]CCc1cccn12 | HCl | ClCCl | null | 2 | Cc1c(F)cccc1C(=O)Cl.Nc1ccc(C(=O)N2CCc3cccn3-c3ccccc32)c(Cl)c1>ClCCl>Cc1c(F)cccc1C(=O)Nc1ccc(C(=O)N2CCc3cccn3-c3ccccc32)c(Cl)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-11dd793ef6d44dfb954c77ff0c37036a | Nc1ccc(C(=O)N2CCc3cccn3-c3ccccc32)c(Cl)c1.O=C(Cl)c1ccc(Cl)cc1Cl>>O=C(Nc1ccc(C(=O)N2CCc3cccn3-c3ccccc32)c(Cl)c1)c1ccc(Cl)cc1Cl | [OH-].[Na+].NC1=CC(=C(C(=O)N2CCC=3N(C4=C2C=CC=C4)C=CC3)C=C1)Cl.C(C)N(CC)CC.ClC1=C(C(=O)Cl)C=CC(=C1)Cl>>C1=CC=CC=2N(CCC=3N(C21)C=CC3)C(=O)C3=C(C=C(C=C3)NC(C3=C(C=C(C=C3)Cl)Cl)=O)Cl | [NH2:3][c:4]1[cH:5][cH:6][c:7]([C:8](=[O:9])[N:10]2[CH2:11][CH2:12][c:13]3[cH:14][cH:15][cH:16][n:17]3-[c:18]3[cH:19][cH:20][cH:21][cH:22][c:23]32)[c:24]([Cl:25])[cH:26]1.Cl[C:2](=[O:1])[c:27]1[cH:28][cH:29][c:30]([Cl:31])[cH:32][c:33]1[Cl:34]>>[O:1]=[C:2]([NH:3][c:4]1[cH:5][cH:6][c:7]([C:8](=[O:9])[N:10]2[CH2:11][CH2:... | Nc1ccc(C(=O)N2CCc3cccn3-c3ccccc32)c(Cl)c1.O=C(Cl)c1ccc(Cl)cc1Cl | O=C(Nc1ccc(C(=O)N2CCc3cccn3-c3ccccc32)c(Cl)c1)c1ccc(Cl)cc1Cl | null | null | ClCCl | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=C(Nc1ccc(C(=O)N2CCc3cccn3-c3ccccc32)cc1)c1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9])-[c:3](:[c:4]):[c:5] | 99.2 | [{"value": 99.2, "product": "C1=CC=CC=2N(CCC=3N(C21)C=CC3)C(=O)C3=C(C=C(C=C3)NC(C3=C(C=C(C=C3)Cl)Cl)=O)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | To a mixture of 0.10 g of 6,7-dihydro-5-(4-amino-2-chlorobenzoyl)-5H-pyrrolo[1,2-a][1,5]benzodiazepine and 0.06 g of triethylamine in 6 ml of dichloromethane is added 0.10 g of 2,4-dichlorobenzoyl chloride in 0.5 ml of dichloromethane. The mixture is stirred at room temperature for 2 hours and 2 ml of 1N NaOH is added.... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccc2c(c1)[NH]CCc1cccn12.c1ccccc1 | HCl | ClCCl | null | 2 | Nc1ccc(C(=O)N2CCc3cccn3-c3ccccc32)c(Cl)c1.O=C(Cl)c1ccc(Cl)cc1Cl>ClCCl>O=C(Nc1ccc(C(=O)N2CCc3cccn3-c3ccccc32)c(Cl)c1)c1ccc(Cl)cc1Cl |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-27feefa6854942528e6b616195b74210 | O=C(CCl)Nc1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1.c1nc[nH]n1>>O=C(Cn1cncn1)Nc1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1 | [Na].N1N=CN=C1.ClCC(=O)NC1=CC=C(C=C1)C(=O)N1CC=2N(CC3=C1C=CC=C3)C=CC2>>C=1C=CN2C1CN(C1=C(C2)C=CC=C1)C(=O)C1=CC=C(C=C1)NC(CN1N=CN=C1)=O | Cl[CH2:3][C:2](=[O:1])[NH:9][c:10]1[cH:11][cH:12][c:13]([C:14](=[O:15])[N:16]2[CH2:17][c:18]3[cH:19][cH:20][cH:21][n:22]3[CH2:23][c:24]3[cH:25][cH:26][cH:27][cH:28][c:29]32)[cH:30][cH:31]1.[nH:4]1[cH:5][n:6][cH:7][n:8]1>>[O:1]=[C:2]([CH2:3][n:4]1[cH:5][n:6][cH:7][n:8]1)[NH:9][c:10]1[cH:11][cH:12][c:13]([C:14](=[O:15])[... | O=C(CCl)Nc1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1.c1nc[nH]n1 | O=C(Cn1cncn1)Nc1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1 | null | null | CN1C(N(CCC1)C)=O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 9f47013937e839adceb07b7e24945feef9d8519d2c1c97fb8023b4a65c36ed06 | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | O=C(Cn1cncn1)Nc1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1 | Cl-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#7:4]-[c:5].[#7;a:6]1:[c:7]:[nH;D2;+0:8]:[#7;a:9]:[c:10]:1>>[O;D1;H0:3]=[C:2](-[#7:4]-[c:5])-[CH2;D2;+0:1]-[n;H0;D3;+0:8]1:[#7;a:9]:[c:10]:[#7;a:6]:[c:7]:1 | 64.5 | [{"value": 64.5, "product": "C=1C=CN2C1CN(C1=C(C2)C=CC=C1)C(=O)C1=CC=C(C=C1)NC(CN1N=CN=C1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | To a suspension of 0.20 g of 1,2,4-triazole sodium in 1 ml of 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone is added 0.10 g of 2-chloro-N-[4-(5H-pyrrolo[2,1-c][1,4]benzodiazepin-10(11H)-ylcarbonyl)phenyl]acetamide in 1 ml of 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone followed by stirring at room temperatur... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1nc[nH]n1 | c1nc[nH]n1 | c1nc[nH]n1.c1ccccc1.c1ccc2c(c1)Cn1cccc1C[NH]2 | HCl | CN1C(N(CCC1)C)=O | null | 3 | O=C(CCl)Nc1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1.c1nc[nH]n1>CN1C(N(CCC1)C)=O>O=C(Cn1cncn1)Nc1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-1b59e09c326a4a03910529e081276b80 | COC(=O)c1ccc(CC(=O)c2ccccc2Cl)cc1>>O=C(O)c1ccc(CC(=O)c2ccccc2Cl)cc1 | ClC1=C(C=CC=C1)C(CC1=CC=C(C(=O)OC)C=C1)=O.[OH-].[Na+].C(CC(O)(C(=O)O)CC(=O)O)(=O)O>>ClC1=C(C=CC=C1)C(CC1=CC=C(C(=O)O)C=C1)=O | C[O:3][C:2](=[O:1])[c:4]1[cH:5][cH:6][c:7]([CH2:8][C:9](=[O:10])[c:11]2[cH:12][cH:13][cH:14][cH:15][c:16]2[Cl:17])[cH:18][cH:19]1>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][cH:6][c:7]([CH2:8][C:9](=[O:10])[c:11]2[cH:12][cH:13][cH:14][cH:15][c:16]2[Cl:17])[cH:18][cH:19]1 | COC(=O)c1ccc(CC(=O)c2ccccc2Cl)cc1 | O=C(O)c1ccc(CC(=O)c2ccccc2Cl)cc1 | null | null | CO.O | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | O=C(Cc1ccccc1)c1ccccc1 | C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]>>[O;D1;H0:3]=[C:2](-[OH;D1;+0:1])-[c:4] | 96.7 | [{"value": 96.7, "product": "ClC1=C(C=CC=C1)C(CC1=CC=C(C(=O)O)C=C1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 18.78 g of methyl 4-[2-(2-chlorophenyl)-2-oxoethyl]benzoate in 288.8 ml of CH3OH, 72.2 ml of water and 5.2 g of NaOH is refluxed for 3 hours then acidified with 2N citric acid. The reaction mixture is evaporated in vacuo to remove the CH3OH. The aqueous phase is extracted with CH2Cl2 and acidified with 1N ... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1.c1ccccc1 | Other | CO.O | null | null | COC(=O)c1ccc(CC(=O)c2ccccc2Cl)cc1>CO.O>O=C(O)c1ccc(CC(=O)c2ccccc2Cl)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-bb6cde0faedc4e19ba217101110ea105 | COc1cc(C(=O)O)ccc1[N+](=O)[O-].O=S(Cl)Cl>>COc1cc(C(=O)Cl)ccc1[N+](=O)[O-] | COC=1C=C(C(=O)O)C=CC1[N+](=O)[O-].S(=O)(Cl)Cl>>COC=1C=C(C(=O)Cl)C=CC1[N+](=O)[O-] | O[C:6]([c:5]1[cH:4][c:3]([O:2][CH3:1])[c:11]([N+:12](=[O:13])[O-:14])[cH:10][cH:9]1)=[O:7].O=S(Cl)[Cl:8]>>[CH3:1][O:2][c:3]1[cH:4][c:5]([C:6](=[O:7])[Cl:8])[cH:9][cH:10][c:11]1[N+:12](=[O:13])[O-:14] | COc1cc(C(=O)O)ccc1[N+](=O)[O-].O=S(Cl)Cl | COc1cc(C(=O)Cl)ccc1[N+](=O)[O-] | null | null | C(C)(C)CC(C)(C)C | Functional Group Interconversion | Alcohol to chloride_SOCl2 | c301c14a9dcd0670d52e8b77396cbe7fd8edeedd757bc43f4162ade1fc52fc93 | 787f545db5dc0b29dde55b5fbed7db8625b8055f49327f97ed4d83cc47c3af1d | c1ccccc1 | Cl-S(=O)-[Cl;H0;D1;+0:1].O-[C;H0;D3;+0:2](=[O;D1;H0:3])-[c:4](:[c:5]):[c:6]>>[Cl;H0;D1;+0:1]-[C;H0;D3;+0:2](=[O;D1;H0:3])-[c:4](:[c:5]):[c:6] | null | [] | null | null | null | null | A stirred suspension of 1.0 g of 3-methoxy-4-nitrobenzoic acid and 1.40 ml of thionyl chloride is heated to reflux for 2 hours. The mixture is cooled to room temperature, 2 ml of iso-octane added and the mixture evaporated in vacuo to a solid residue. The residue is washed with iso-octane (2×2 ml), dried in vacuo to gi... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Acyl halide | null | null | c1ccccc1 | HCl | C(C)(C)CC(C)(C)C | null | null | COc1cc(C(=O)O)ccc1[N+](=O)[O-].O=S(Cl)Cl>C(C)(C)CC(C)(C)C>COc1cc(C(=O)Cl)ccc1[N+](=O)[O-] |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-d5f50f8cc3b945ebaaca53e2c5402643 | COc1cc(C(=O)Cl)ccc1[N+](=O)[O-].c1ccc2c(c1)Cn1cccc1CN2>>COc1cc(C(=O)N2Cc3cccn3Cc3ccccc32)ccc1[N+](=O)[O-] | COC=1C=C(C(=O)Cl)C=CC1[N+](=O)[O-].C=1C=CN2C1CNC1=C(C2)C=CC=C1.C(C)N(CC)CC>>[N+](=O)([O-])C1=C(C=C(C(=O)N2CC=3N(CC4=C2C=CC=C4)C=CC3)C=C1)OC | Cl[C:6]([c:5]1[cH:4][c:3]([O:2][CH3:1])[c:24]([N+:25](=[O:26])[O-:27])[cH:23][cH:22]1)=[O:7].[NH:8]1[CH2:9][c:10]2[cH:11][cH:12][cH:13][n:14]2[CH2:15][c:16]2[cH:17][cH:18][cH:19][cH:20][c:21]21>>[CH3:1][O:2][c:3]1[cH:4][c:5]([C:6](=[O:7])[N:8]2[CH2:9][c:10]3[cH:11][cH:12][cH:13][n:14]3[CH2:15][c:16]3[cH:17][cH:18][cH:1... | COc1cc(C(=O)Cl)ccc1[N+](=O)[O-].c1ccc2c(c1)Cn1cccc1CN2 | COc1cc(C(=O)N2Cc3cccn3Cc3ccccc32)ccc1[N+](=O)[O-] | null | null | C(Cl)Cl | Acylation | N-alkylation of secondary amines with alkyl halides | fe674a41b285c5c1b016cd9c12dd41b3635fc90635e2c9974eeff0b8893e7755 | 96cb0a2fed10552c5770a45a2d6523b47ac3e38928b4a9c698d8577451182dcd | O=C(c1ccccc1)N1Cc2cccn2Cc2ccccc21 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[#7;a:6]:[c:7]-[C:8]-[NH;D2;+0:9]-[c:10](:[c:11]):[c:12]>>[#7;a:6]:[c:7]-[C:8]-[N;H0;D3;+0:9](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5])-[c:10](:[c:11]):[c:12] | 104.2 | [{"value": 104.2, "product": "[N+](=O)([O-])C1=C(C=C(C(=O)N2CC=3N(CC4=C2C=CC=C4)C=CC3)C=C1)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | To a solution of 0.55 g of 10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine in 8 ml of methylene chloride is added 0.55 g of triethylamine followed by 0.97 g of 3-methoxy-4-nitrobenzoyl chloride. The reaction mixture is stirred at room temperature for 2 hours and then quenched with 10 ml of 1N NaOH. The methylene chl... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Secondary amine | Tertiary amide | c1ccc2c(c1)Cn1cccc1CN2 | c1ccc2c(c1)Cn1cccc1C[NH]2 | c1ccccc1.c1ccc2c(c1)Cn1cccc1C[NH]2 | HCl | C(Cl)Cl | null | 2 | COc1cc(C(=O)Cl)ccc1[N+](=O)[O-].c1ccc2c(c1)Cn1cccc1CN2>C(Cl)Cl>COc1cc(C(=O)N2Cc3cccn3Cc3ccccc32)ccc1[N+](=O)[O-] |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-f6499446098b4662863c12a5e1de6a7c | CC(C)COC(=O)Cl.CCOC(C)=O.Nc1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1>>CCCCOC(=O)Nc1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1 | C(C)(=O)OCC.C(Cl)Cl.NC1=CC=C(C(=O)N2CC=3N(CC4=C2C=CC=C4)C=CC3)C=C1.C(C)N(CC)CC.C(C(C)C)OC(=O)Cl>>CCCCOC(=O)NC1=CC=C(C(=O)N2CC=3N(CC4=C2C=CC=C4)C=CC3)C=C1 | C[CH:3]([CH3:2])[CH2:4][O:5][C:6](Cl)=[O:7].CC(=O)OC[CH3:1].[NH2:8][c:9]1[cH:10][cH:11][c:12]([C:13](=[O:14])[N:15]2[CH2:16][c:17]3[cH:18][cH:19][cH:20][n:21]3[CH2:22][c:23]3[cH:24][cH:25][cH:26][cH:27][c:28]32)[cH:29][cH:30]1>>[CH3:1][CH2:2][CH2:3][CH2:4][O:5][C:6](=[O:7])[NH:8][c:9]1[cH:10][cH:11][c:12]([C:13](=[O:14... | CC(C)COC(=O)Cl.CCOC(C)=O.Nc1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1 | CCCCOC(=O)Nc1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1 | null | null | C(Cl)Cl | C-C Coupling | OtherReaction | 9f4fff892fc0b8ec9eea5eb045c73c76bdce03dbeb7f1891c3dc21035a3e7210 | 2c44408735b6829573f872c64c216202733dd59202c9bfb2f0490eb1b5af6f44 | O=C(c1ccccc1)N1Cc2cccn2Cc2ccccc21 | C-C(=O)-O-C-[CH3;D1;+0:1].C-[CH;D3;+0:2](-[CH3;D1;+0:3])-[C:4]-[#8:5]-[C;H0;D3;+0:6](-Cl)=[O;D1;H0:7].[NH2;D1;+0:8]-[c:9](:[c:10]):[c:11]>>[CH3;D1;+0:1]-[CH2;D2;+0:3]-[CH2;D2;+0:2]-[C:4]-[#8:5]-[C;H0;D3;+0:6](=[O;D1;H0:7])-[NH;D2;+0:8]-[c:9](:[c:10]):[c:11] | null | [] | null | null | 3 | HOUR | To a stirred solution of 0.15 g of 10,11-dihydro-10-(4-aminobenzoyl)-5H-pyrrolo[2,1-c][1,4]benzodiazepine in 2 ml of methylene chloride is added 0.10 g of triethylamine followed by 0.10 g of isobutylchloroformate. The reaction mixture is stirred for 3 hours and then quenched with 1N NaOH. The organic layer is evaporate... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Ester.Ether.Primary amine | Carbamic ester.Ether | null | null | c1ccccc1.c1ccc2c(c1)Cn1cccc1C[NH]2 | HCl | C(Cl)Cl | null | 3 | CC(C)COC(=O)Cl.CCOC(C)=O.Nc1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1>C(Cl)Cl>CCCCOC(=O)Nc1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)cc1 |
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