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-c31cb9b44c404c10ba3aa533aa079e2b | ord-98677e01beff4b8bbb96121da42bc441 | CCC(N)=O.CN(C)C=O.COC(=O)C(=C[O-])C(OC)OC>>CCc1ncc(C(=O)OC)cn1 | Cl.C(CC)(=O)N.COC(C(=C[O-])C(=O)OC)OC.[Na+].CN(C=O)C>>C(C)C1=NC=C(C=N1)C(=O)OC | O=[C:3]([CH2:2][CH3:1])[NH2:4].C[N:12](C=O)[CH3:11].COC(OC)[C:6](=[CH:5][O-])[C:7](=[O:8])[O:9][CH3:10]>>[CH3:1][CH2:2][c:3]1[n:4][cH:5][c:6]([C:7](=[O:8])[O:9][CH3:10])[cH:11][n:12]1 | CCC(N)=O.CN(C)C=O.COC(=O)C(=C[O-])C(OC)OC | CCc1ncc(C(=O)OC)cn1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 554905dd0726ab9b8bf1398cb0b1f704ef8bf25116ab148e9b1372d40b65d6ee | dbacf31bb69f371354272123fd193a0e85c2e18c8f446f20b941bc4930bb8551 | c1cncnc1 | C-O-C(-O-C)-[C;H0;D3;+0:1](=[CH;D2;+0:2]-[O-])-[C:3](=[O;D1;H0:4])-[#8:5]-[C;D1;H3:6].C-[N;H0;D3;+0:7](-[CH3;D1;+0:8])-C=O.O=[C;H0;D3;+0:9](-[NH2;D1;+0:10])-[C:11]-[C;D1;H3:12]>>[C;D1;H3:6]-[#8:5]-[C:3](=[O;D1;H0:4])-[c;H0;D3;+0:1]1:[cH;D2;+0:8]:[n;H0;D2;+0:7]:[c;H0;D3;+0:9](-[C:11]-[C;D1;H3:12]):[n;H0;D2;+0:10]:[cH;D2... | null | [] | 100 | CELSIUS | null | null | N-(4-chlorophenyl)-N-{(2S,4R)-1-[(2-ethylpyrimidin-5-yl)carbonyl]-2-methyl-1,2,3,4-tetrahydroquinolin-4-yl}acetamide was prepared following general procedure H, substituting 2-ethylpyrimidine-5-carbonyl chloride for 6-trifluoromethyl nicotinyl chloride. (2-ethylpyrimidine-5-carbonyl chloride was prepared in four steps.... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ether.Ether.Primary amide.Tertiary amide | Ester | null | c1cncnc1 | c1cncnc1 | HO- | null | 100 | null | CCC(N)=O.CN(C)C=O.COC(=O)C(=C[O-])C(OC)OC>>CCc1ncc(C(=O)OC)cn1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-4bae080c67874a25912e0c4ce7d90cac | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(O)cc2)c2ccccc21.CCOC(=O)c1c(C)ncn1CCCBr>>CCOC(=O)c1c(C)ncn1CCCOc1ccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccc(Cl)cc3)C[C@@H]2C)cc1 | N1C=NC=C1.[H-].[Na+].C(=O)([O-])[O-].[K+].[K+].C(C)OC(=O)C=1N(C=NC1C)CCCBr.ClC1=CC=C(C=C1)N(C(C)=O)[C@@H]1C[C@@H](N(C2=CC=CC=C12)C(C1=CC=C(C=C1)O)=O)C>>C(C)OC(=O)C=1N(C=NC1C)CCCOC1=CC=C(C=C1)C(=O)N1[C@H](C[C@H](C2=CC=CC=C12)N(C1=CC=C(C=C1)Cl)C(C)=O)C | [OH:15][c:16]1[cH:17][cH:18][c:19]([C:20](=[O:21])[N:22]2[c:23]3[cH:24][cH:25][cH:26][cH:27][c:28]3[C@H:29]([N:30]([C:31]([CH3:32])=[O:33])[c:34]3[cH:35][cH:36][c:37]([Cl:38])[cH:39][cH:40]3)[CH2:41][C@@H:42]2[CH3:43])[cH:44][cH:45]1.Br[CH2:14][CH2:13][CH2:12][n:11]1[c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[c:7]([CH3:8])... | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(O)cc2)c2ccccc21.CCOC(=O)c1c(C)ncn1CCCBr | CCOC(=O)c1c(C)ncn1CCCOc1ccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccc(Cl)cc3)C[C@@H]2C)cc1 | null | null | CN(C)C=O.C1CCOC1 | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | O=C(c1ccc(OCCCn2ccnc2)cc1)N1CC[C@@H](Nc2ccccc2)c2ccccc21 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[OH;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:4]-[c:5](:[c:6]):[c:7] | null | [] | 80 | CELSIUS | null | null | (2S,4R)-N-(4-Chloro-phenyl)-N-[1-(4-hydroxy-benzoyl)-2-methyl-1,2,3,4-tetrahydro-quinolin-4-yl]-acetamide was dissolved in DMF at room temperature and K2CO3 was added. 3-(3-Bromo-propyl)-5-methyl-3H-imidazole-4-carboxylic acid ethyl ester (prepared from the dibromide and the corresponding imidazole with NaH in THF) was... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1c[nH]cn1.c1ccccc1.c1ccccc1.c1ccc2c(c1)CCC[NH]2 | HBr | CN(C)C=O.C1CCOC1 | 80 | null | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(O)cc2)c2ccccc21.CCOC(=O)c1c(C)ncn1CCCBr>CN(C)C=O.C1CCOC1>CCOC(=O)c1c(C)ncn1CCCOc1ccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccc(Cl)cc3)C[C@@H]2C)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-df515fa8651a471380cf6635929a49d5 | CCOC(=O)c1c(C)ncn1CCCOc1ccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccc(Cl)cc3)C[C@@H]2C)cc1>>CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(OCCCn3cnc(C)c3C(=O)O)cc2)c2ccccc21 | C(C)OC(=O)C=1N(C=NC1C)CCCOC1=CC=C(C=C1)C(=O)N1[C@H](C[C@H](C2=CC=CC=C12)N(C1=CC=C(C=C1)Cl)C(C)=O)C.C(C)O.[OH-].[Na+]>>C(C)(=O)N([C@@H]1C[C@@H](N(C2=CC=CC=C12)C(=O)C1=CC=C(OCCCN2C=NC(=C2C(=O)O)C)C=C1)C)C1=CC=C(C=C1)Cl | CC[O:35][C:33]([c:32]1[n:27]([CH2:26][CH2:25][CH2:24][O:23][c:22]2[cH:21][cH:20][c:19]([C:17]([N:16]3[C@@H:14]([CH3:15])[CH2:13][C@@H:12]([N:4]([C:2]([CH3:1])=[O:3])[c:5]4[cH:6][cH:7][c:8]([Cl:9])[cH:10][cH:11]4)[c:43]4[c:38]3[cH:39][cH:40][cH:41][cH:42]4)=[O:18])[cH:37][cH:36]2)[cH:28][n:29][c:30]1[CH3:31])=[O:34]>>[C... | CCOC(=O)c1c(C)ncn1CCCOc1ccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccc(Cl)cc3)C[C@@H]2C)cc1 | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(OCCCn3cnc(C)c3C(=O)O)cc2)c2ccccc21 | null | null | O1CCCC1 | Deprotection | Ester saponification (alkyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | O=C(c1ccc(OCCCn2ccnc2)cc1)N1CC[C@@H](Nc2ccccc2)c2ccccc21 | C-C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4](:[#7;a:5]):[c:6]:[#7;a:7]>>[#7;a:5]:[c:4](-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1]):[c:6]:[#7;a:7] | 61 | [{"value": 61.0, "product": "C(C)(=O)N([C@@H]1C[C@@H](N(C2=CC=CC=C12)C(=O)C1=CC=C(OCCCN2C=NC(=C2C(=O)O)C)C=C1)C)C1=CC=C(C=C1)Cl", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 16 | HOUR | (2S,4R)-N-(4-Chloro-phenyl)-N-[1-(4-hydroxy-benzoyl)-2-methyl-1,2,3,4-tetrahydro-quinolin-4-yl]-acetamide was dissolved in DMF at room temperature and K2CO3 was added. 3-(3-Bromo-propyl)-5-methyl-3H-imidazole-4-carboxylic acid ethyl ester (prepared from the dibromide and the corresponding imidazole with NaH in THF) was... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1.c1ccccc1.c1c[nH]cn1.c1ccc2c(c1)CCC[NH]2 | Other | O1CCCC1 | null | 16 | CCOC(=O)c1c(C)ncn1CCCOc1ccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccc(Cl)cc3)C[C@@H]2C)cc1>O1CCCC1>CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(OCCCn3cnc(C)c3C(=O)O)cc2)c2ccccc21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e068d883520640a5909f8a4952974228 | COC(=O)c1ccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccc(Cl)cc3)C[C@@H]2C)s1>>CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(C(=O)O)s2)c2ccccc21 | C(C)(=O)N([C@@H]1C[C@@H](N(C2=CC=CC=C12)C(=O)C1=CC=C(S1)C(=O)OC)C)C1=CC=C(C=C1)Cl.C([O-])([O-])=O.[K+].[K+]>>C(C)(=O)N([C@@H]1C[C@@H](N(C2=CC=CC=C12)C(=O)C1=CC=C(S1)C(=O)O)C)C1=CC=C(C=C1)Cl | C[O:25][C:23]([c:22]1[cH:21][cH:20][c:19]([C:17]([N:16]2[C@@H:14]([CH3:15])[CH2:13][C@@H:12]([N:4]([C:2]([CH3:1])=[O:3])[c:5]3[cH:6][cH:7][c:8]([Cl:9])[cH:10][cH:11]3)[c:32]3[c:27]2[cH:28][cH:29][cH:30][cH:31]3)=[O:18])[s:26]1)=[O:24]>>[CH3:1][C:2](=[O:3])[N:4]([c:5]1[cH:6][cH:7][c:8]([Cl:9])[cH:10][cH:11]1)[C@@H:12]1[... | COC(=O)c1ccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccc(Cl)cc3)C[C@@H]2C)s1 | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(C(=O)O)s2)c2ccccc21 | null | null | O.CO | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | O=C(c1cccs1)N1CC[C@@H](Nc2ccccc2)c2ccccc21 | C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]:[#16;a:5]>>[#16;a:5]:[c:4]-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1] | 99 | [{"value": 99.0, "product": "C(C)(=O)N([C@@H]1C[C@@H](N(C2=CC=CC=C12)C(=O)C1=CC=C(S1)C(=O)O)C)C1=CC=C(C=C1)Cl", "details": "PERCENTYIELD", "is_desired": false}, {"value": 95.3, "product": "C(C)(=O)N([C@@H]1C[C@@H](N(C2=CC=CC=C12)C(=O)C1=CC=C(S1)C(=O)O)C)C1=CC=C(C=C1)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired... | null | null | 20 | HOUR | Methyl 5-{[(2S,4R)-4-[acetyl(4-chlorophenyl)amino]-2-methyl-3,4-dihydroquinolin-1(2H)-yl]carbonyl}thiophene-2-carboxylate (80 mg, 0.17 mmol, 1 eq.) was dissolved in methanol (6 ml). A solution of potassium carbonate (200 mg, 1.4 mmol, 8 eq.) in water (2 ml) was added and reaction mixture was stirred at room temperature... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1.c1ccsc1.c1ccc2c(c1)CCC[NH]2 | Other | O.CO | null | 20 | COC(=O)c1ccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccc(Cl)cc3)C[C@@H]2C)s1>O.CO>CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(C(=O)O)s2)c2ccccc21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ae1f9b380e7349e2a92c334b994826ea | CC(=O)N(c1ccc(Cl)cc1)C1CC(C)N(C(=O)c2ccc(N)cc2)c2ccccc21.O=C(Cl)OCCBr>>CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(N3CCOC3=O)cc2)c2ccccc21 | C(=O)([O-])[O-].[Cs+].[Cs+].C(C)N(CC)CC.NC1=CC=C(C(=O)N2C(CC(C3=CC=CC=C23)N(C(C)=O)C2=CC=C(C=C2)Cl)C)C=C1.BrCCOC(=O)Cl>>ClC1=CC=C(C=C1)N(C(C)=O)[C@@H]1C[C@@H](N(C2=CC=CC=C12)C(C1=CC=C(C=C1)N1C(OCC1)=O)=O)C | [CH3:1][C:2](=[O:3])[N:4]([c:5]1[cH:6][cH:7][c:8]([Cl:9])[cH:10][cH:11]1)[CH:12]1[CH2:13][CH:14]([CH3:15])[N:16]([C:17](=[O:18])[c:19]2[cH:20][cH:21][c:22]([NH2:23])[cH:29][cH:30]2)[c:31]2[cH:32][cH:33][cH:34][cH:35][c:36]21.Cl[C:27]([O:26][CH2:25][CH2:24]Br)=[O:28]>>[CH3:1][C:2](=[O:3])[N:4]([c:5]1[cH:6][cH:7][c:8]([C... | CC(=O)N(c1ccc(Cl)cc1)C1CC(C)N(C(=O)c2ccc(N)cc2)c2ccccc21.O=C(Cl)OCCBr | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(N3CCOC3=O)cc2)c2ccccc21 | null | null | C(Cl)Cl.CN(C)C=O | Protection | OtherReaction | 15613fb2a10be402bb909c91fd72914a5bd3a21a9fe5a928a138d607049bdc15 | 2c78a61345fd52f9bd102038239c266d368f2005df51acc4baccc29a58dd2e3c | O=C1OCCN1c1ccc(C(=O)N2CC[C@@H](Nc3ccccc3)c3ccccc32)cc1 | Br-[CH2;D2;+0:1]-[C:2]-[#8:3]-[C;H0;D3;+0:4](-Cl)=[O;D1;H0:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[O;D1;H0:5]=[C;H0;D3;+0:4]1-[#8:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:6]-1-[c:7](:[c:8]):[c:9] | null | [] | null | null | 1 | HOUR | N-[1-(4-Amino-benzoyl)-2-methyl-1,2,3,4-tetrahydroquinolin-4-yl]-N-(4-chloro-phenyl)-acetamide (61 mg, 0.142 mmol) was dissolved in methylene chloride (2 mL) and was added triethylamine (0.100 mL, 0.700 mmol). 2-Bromoethylchloroformate (0.023 mL, 0.213 mmol) was added and the reaction was allowed to warm to room temper... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary halide.Ether.Primary amine | Carbamic ester.Ether | null | C1COC[NH]1 | c1ccccc1.c1ccccc1.C1COC[NH]1.c1ccc2c(c1)CCC[NH]2 | HCl.Br- | C(Cl)Cl.CN(C)C=O | null | 1 | CC(=O)N(c1ccc(Cl)cc1)C1CC(C)N(C(=O)c2ccc(N)cc2)c2ccccc21.O=C(Cl)OCCBr>C(Cl)Cl.CN(C)C=O>CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(N3CCOC3=O)cc2)c2ccccc21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-5ce92dc187844cc28977b7bd81bea19d | CC(C)(C)OC(=O)NC(CCO)C(=O)O.C[Si](C)(C)C=[N+]=[N-]>>COC(=O)C(CCO)NC(=O)OC(C)(C)C | C(C)(C)(C)OC(=O)NC(C(=O)O)CCO.C[Si](C)(C)C=[N+]=[N-]>>COC(C(CCO)NC(=O)OC(C)(C)C)=O | [OH:2][C:3](=[O:4])[CH:5]([CH2:6][CH2:7][OH:8])[NH:9][C:10](=[O:11])[O:12][C:13]([CH3:14])([CH3:15])[CH3:16].C[Si](C)(C)[CH:1]=[N+]=[N-]>>[CH3:1][O:2][C:3](=[O:4])[CH:5]([CH2:6][CH2:7][OH:8])[NH:9][C:10](=[O:11])[O:12][C:13]([CH3:14])([CH3:15])[CH3:16] | CC(C)(C)OC(=O)NC(CCO)C(=O)O.C[Si](C)(C)C=[N+]=[N-] | COC(=O)C(CCO)NC(=O)OC(C)(C)C | null | null | CO | Heteroatom Alkylation and Arylation | O-alkylation of carboxylic acids with diazo compounds | 39589be0e9a30df66714fe618d22a8ac0fb24901dbf2ead1ab33e31556c7ac64 | 8b539baf7aeb5ab868833e33306bad77200a853d562904197e13de2e27e229d7 | null | C-[Si](-C)(-C)-[CH;D2;+0:1]=[N+]=[N-].[C:2]-[C:3](=[O;D1;H0:4])-[OH;D1;+0:5]>>[C:2]-[C:3](=[O;D1;H0:4])-[O;H0;D2;+0:5]-[CH3;D1;+0:1] | null | [] | null | null | null | null | 2-tert-Butoxycarbonylamino-4-hydroxy-butyric acid (0.79 g, 3.6 mmol) was dissolved in 15 ml methanol at room temperature and (trimethylsilyl)diazomethane (2M solution in hexane) was added till solution become yellow. The mixture was concentrated down to afford crude 2-tert-butoxycarbonylamino-4-hydroxy-butyric acid met... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Diazo.Silyl protective group | Ester | null | null | null | Other | CO | null | null | CC(C)(C)OC(=O)NC(CCO)C(=O)O.C[Si](C)(C)C=[N+]=[N-]>CO>COC(=O)C(CCO)NC(=O)OC(C)(C)C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-20811cdd034b4ad690392bfa44b54a5f | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(O)cc2)c2ccccc21.COC(=O)C(CCO)NC(=O)OC(C)(C)C>>COC(=O)C(CCOc1ccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccc(Cl)cc3)C[C@@H]2C)cc1)NC(=O)OC(C)(C)C | CCOC(=O)/N=N/C(=O)OCC.ClC1=CC=C(C=C1)N(C(C)=O)[C@@H]1C[C@@H](N(C2=CC=CC=C12)C(C1=CC=C(C=C1)O)=O)C.COC(C(CCO)NC(=O)OC(C)(C)C)=O.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3>>C(C)(=O)N([C@@H]1C[C@@H](N(C2=CC=CC=C12)C(=O)C1=CC=C(OCCC(C(=O)OC)NC(=O)OC(C)(C)C)C=C1)C)C1=CC=C(C=C1)Cl | O[c:9]1[cH:10][cH:11][c:12]([C:13](=[O:14])[N:15]2[c:16]3[cH:17][cH:18][cH:19][cH:20][c:21]3[C@H:22]([N:23]([C:24]([CH3:25])=[O:26])[c:27]3[cH:28][cH:29][c:30]([Cl:31])[cH:32][cH:33]3)[CH2:34][C@@H:35]2[CH3:36])[cH:37][cH:38]1.[CH3:1][O:2][C:3](=[O:4])[CH:5]([CH2:6][CH2:7][OH:8])[NH:39][C:40](=[O:41])[O:42][C:43]([CH3:... | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(O)cc2)c2ccccc21.COC(=O)C(CCO)NC(=O)OC(C)(C)C | COC(=O)C(CCOc1ccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccc(Cl)cc3)C[C@@H]2C)cc1)NC(=O)OC(C)(C)C | null | null | C1(=CC=CC=C1)C | Heteroatom Alkylation and Arylation | Mitsunobu aryl ether | 8915084acbaaf997bf0f89ff5187cb2f89c25dc683fffc57b3391298c8430dd9 | 2258bd14c3b5449b92dc09cf9fa522f88d5071b4af20f7e968b60aa1ae6db0cf | O=C(c1ccccc1)N1CC[C@@H](Nc2ccccc2)c2ccccc21 | O-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[C:6]-[C:7]-[OH;D1;+0:8]>>[C:6]-[C:7]-[O;H0;D2;+0:8]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5] | null | [] | null | null | 18 | HOUR | The ester was dissolved in 20 ml toluene at room temperature with PPh3 (0.94 g, 3.6 mmol), then added N-(4-chlorophenyl)-N-[(2S,4R)-1-(4-hydroxybenzoyl)-2-methyl-1,2,3,4-tetrahydroquinolin-4-yl]acetamide (0.31 g, 0.71 mmol) and stirred for 5 min. DEAD (0.626 g, 3.6 mmol) was added and the reaction was stirred for 18 h ... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Aromatic alcohol | Ether | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1.c1ccc2c(c1)CCC[NH]2 | HO- | C1(=CC=CC=C1)C | null | 18 | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(O)cc2)c2ccccc21.COC(=O)C(CCO)NC(=O)OC(C)(C)C>C1(=CC=CC=C1)C>COC(=O)C(CCOc1ccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccc(Cl)cc3)C[C@@H]2C)cc1)NC(=O)OC(C)(C)C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d95e765282f44d56bf005c74a09506bf | CC(=O)O[BH-](OC(C)=O)OC(C)=O.CC=O.COC(=O)C(CCOc1ccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccc(Cl)cc3)C[C@@H]2C)cc1)NC(=O)OC(C)(C)C>>CCN(CC)C(CCOc1ccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccc(Cl)cc3)C[C@@H]2C)cc1)C(=O)OC | C(C)(=O)N([C@@H]1C[C@@H](N(C2=CC=CC=C12)C(=O)C1=CC=C(OCCC(C(=O)OC)NC(=O)OC(C)(C)C)C=C1)C)C1=CC=C(C=C1)Cl.ClCCl.Cl.C(C)(=O)O[BH-](OC(C)=O)OC(C)=O.[Na+].C(C)=O>>C(C)(=O)N([C@@H]1C[C@@H](N(C2=CC=CC=C12)C(=O)C1=CC=C(OCCC(C(=O)OC)N(CC)CC)C=C1)C)C1=CC=C(C=C1)Cl | CC(=O)O[BH-](OC(C)=O)OC(=O)[CH3:5].O=[CH:2][CH3:1].CC(C)(C)OC(=O)[NH:3][CH:6]([CH2:7][CH2:8][O:9][c:10]1[cH:11][cH:12][c:13]([C:14](=[O:15])[N:16]2[c:17]3[cH:18][cH:19][cH:20][cH:21][c:22]3[C@H:23]([N:24]([C:25]([CH3:26])=[O:27])[c:28]3[cH:29][cH:30][c:31]([Cl:32])[cH:33][cH:34]3)[CH2:35][C@@H:36]2[CH3:37])[cH:38][cH:3... | CC(=O)O[BH-](OC(C)=O)OC(C)=O.CC=O.COC(=O)C(CCOc1ccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccc(Cl)cc3)C[C@@H]2C)cc1)NC(=O)OC(C)(C)C | CCN(CC)C(CCOc1ccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccc(Cl)cc3)C[C@@H]2C)cc1)C(=O)OC | null | null | O1CCOCC1 | Heteroatom Alkylation and Arylation | OtherReaction | 66d6e4353e65ac821a9549421bacb60851c805b034828bf4c3f1113fdee13676 | cf54569061a197ba9f3cab07727ad571966e8f550ff4245a3fd82ef36fe97477 | O=C(c1ccccc1)N1CC[C@@H](Nc2ccccc2)c2ccccc21 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[C:2](-[C:3])-[C:4](=[O;D1;H0:5])-[#8:6]-[C;D1;H3:7].C-C(=O)-O-[BH-](-O-C(-C)=O)-O-C(=O)-[CH3;D1;+0:8].O=[CH;D2;+0:9]-[C;D1;H3:10]>>[C:3]-[C:2](-[C:4](=[O;D1;H0:5])-[#8:6]-[C;D1;H3:7])-[N;H0;D3;+0:1](-[C:11]-[CH3;D1;+0:8])-[CH2;D2;+0:9]-[C;D1;H3:10] | 17 | [{"value": 17.0, "product": "C(C)(=O)N([C@@H]1C[C@@H](N(C2=CC=CC=C12)C(=O)C1=CC=C(OCCC(C(=O)OC)N(CC)CC)C=C1)C)C1=CC=C(C=C1)Cl", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | Methyl 4-(4-{[(2S,4R)-4-[acetyl(4-chlorophenyl)amino]-2-methyl-3,4-dihydroquinolin-1(2H)-yl]carbonyl}phenoxy)-2-[(tert-butoxycarbonyl)amino]butanoate was dissolved in 20 ml dichloromethane and 4 ml HCl in dioxane (4M) was added. The mixture was stirred 2 hours and concentrated down. The residue was washed with ether, t... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Carbamic ester.Ether.Boc | Tertiary amine | null | null | c1ccccc1.c1ccccc1.c1ccc2c(c1)CCC[NH]2 | HO-.B | O1CCOCC1 | null | 2 | CC(=O)O[BH-](OC(C)=O)OC(C)=O.CC=O.COC(=O)C(CCOc1ccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccc(Cl)cc3)C[C@@H]2C)cc1)NC(=O)OC(C)(C)C>O1CCOCC1>CCN(CC)C(CCOc1ccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccc(Cl)cc3)C[C@@H]2C)cc1)C(=O)OC |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-41a7afebb8de40dc819fe91dbbc286c1 | CCN(CC)C(CCOc1ccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccc(Cl)cc3)C[C@@H]2C)cc1)C(=O)OC>>CCN(CC)C(CCOc1ccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccc(Cl)cc3)C[C@@H]2C)cc1)C(=O)O | C(C)(=O)N([C@@H]1C[C@@H](N(C2=CC=CC=C12)C(=O)C1=CC=C(OCCC(C(=O)OC)N(CC)CC)C=C1)C)C1=CC=C(C=C1)Cl.[OH-].[K+]>>C(C)(=O)N([C@@H]1C[C@@H](N(C2=CC=CC=C12)C(=O)C1=CC=C(OCCC(C(=O)O)N(CC)CC)C=C1)C)C1=CC=C(C=C1)Cl | C[O:42][C:40]([CH:6]([N:3]([CH2:2][CH3:1])[CH2:4][CH3:5])[CH2:7][CH2:8][O:9][c:10]1[cH:11][cH:12][c:13]([C:14](=[O:15])[N:16]2[c:17]3[cH:18][cH:19][cH:20][cH:21][c:22]3[C@H:23]([N:24]([C:25]([CH3:26])=[O:27])[c:28]3[cH:29][cH:30][c:31]([Cl:32])[cH:33][cH:34]3)[CH2:35][C@@H:36]2[CH3:37])[cH:38][cH:39]1)=[O:41]>>[CH3:1][... | CCN(CC)C(CCOc1ccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccc(Cl)cc3)C[C@@H]2C)cc1)C(=O)OC | CCN(CC)C(CCOc1ccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccc(Cl)cc3)C[C@@H]2C)cc1)C(=O)O | null | null | O1CCCC1.CO | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | O=C(c1ccccc1)N1CC[C@@H](Nc2ccccc2)c2ccccc21 | C-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4]>>[C:3]-[C:2](=[O;D1;H0:4])-[OH;D1;+0:1] | 55 | [{"value": 55.0, "product": "C(C)(=O)N([C@@H]1C[C@@H](N(C2=CC=CC=C12)C(=O)C1=CC=C(OCCC(C(=O)O)N(CC)CC)C=C1)C)C1=CC=C(C=C1)Cl", "details": "PERCENTYIELD", "is_desired": false}] | 50 | CELSIUS | null | null | Methyl 4-(4-{[(2S,4R)-4-[acetyl(4-chlorophenyl)amino]-2-methyl-3,4-dihydro-quinolin-1(2H)-yl]carbonyl}phenoxy)-2-(diethylamino)butanoate was hydrolyzed to the acid by dissolving in 6 ml tetrahydrofuran/methanol (1/1) and potassium hydroxide (0.04 g in 2 ml water) was added. The mixture was heated to 50° C. for 18 hours... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1.c1ccccc1.c1ccc2c(c1)CCC[NH]2 | Other | O1CCCC1.CO | 50 | null | CCN(CC)C(CCOc1ccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccc(Cl)cc3)C[C@@H]2C)cc1)C(=O)OC>O1CCCC1.CO>CCN(CC)C(CCOc1ccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccc(Cl)cc3)C[C@@H]2C)cc1)C(=O)O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-b8d38a654c4443819c1a1305a4ea8781 | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(C3CCCN3C(=O)OCc3ccccc3)cc2)c2ccccc21>>CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(C3CCCN3)cc2)c2ccccc21 | C(C)(=O)N([C@@H]1C[C@@H](N(C2=CC=CC=C12)C(=O)C1=CC=C(C=C1)C1N(CCC1)C(=O)OCC1=CC=CC=C1)C)C1=CC=C(C=C1)Cl>>ClC1=CC=C(C=C1)N(C(C)=O)[C@@H]1C[C@@H](N(C2=CC=CC=C12)C(C1=CC=C(C=C1)C1NCCC1)=O)C | O=C(OCc1ccccc1)[N:27]1[CH:23]([c:22]2[cH:21][cH:20][c:19]([C:17]([N:16]3[C@@H:14]([CH3:15])[CH2:13][C@@H:12]([N:4]([C:2]([CH3:1])=[O:3])[c:5]4[cH:6][cH:7][c:8]([Cl:9])[cH:10][cH:11]4)[c:35]4[c:30]3[cH:31][cH:32][cH:33][cH:34]4)=[O:18])[cH:29][cH:28]2)[CH2:24][CH2:25][CH2:26]1>>[CH3:1][C:2](=[O:3])[N:4]([c:5]1[cH:6][cH:... | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(C3CCCN3C(=O)OCc3ccccc3)cc2)c2ccccc21 | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(C3CCCN3)cc2)c2ccccc21 | null | null | Br.C(C)(=O)O | Reduction | Hydrogenolysis of tertiary amines | 44c9fb2a48470f3336defb4c38dd5fbd27204582d3ee3e148a578920a57d483d | 20c36f41eeb07c3ba4437b51ba72e8ff3c22d0b27e7197b0e9af3127f331149f | O=C(c1ccc(C2CCCN2)cc1)N1CC[C@@H](Nc2ccccc2)c2ccccc21 | O=C(-O-C-c1:c:c:c:c:c:1)-[N;H0;D3;+0:1]1-[C:2]-[C:3]-[C:4]-[C:5]-1-[c:6]>>[c:6]-[C:5]1-[C:4]-[C:3]-[C:2]-[NH;D2;+0:1]-1 | 91.4 | [{"value": 91.0, "product": "ClC1=CC=C(C=C1)N(C(C)=O)[C@@H]1C[C@@H](N(C2=CC=CC=C12)C(C1=CC=C(C=C1)C1NCCC1)=O)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 91.4, "product": "ClC1=CC=C(C=C1)N(C(C)=O)[C@@H]1C[C@@H](N(C2=CC=CC=C12)C(C1=CC=C(C=C1)C1NCCC1)=O)C", "details": "CALCULATEDPERCENTYIELD", "is_desir... | null | null | 2 | HOUR | Benzyl 2-(4-{[(2S,4R)-4-[acetyl(4-chlorophenyl)amino]-2-methyl-3,4-dihydroquinolin-1(2H)-yl]carbonyl}phenyl)pyrrolidine-1-carboxylate (237 mg, 0.381 mmol) was dissolved in HBr/Acetic acid (5 mL) and stirred for 2 h. The reddish slurry was partitioned between Et2O and 1N HCl. The HCl/water layer was washed 3× with Et2O ... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether | Secondary amine | c1ccccc1.C1CC[NH]C1 | C1CCNC1 | c1ccccc1.c1ccccc1.C1CCNC1.c1ccc2c(c1)CCC[NH]2 | HO- | Br.C(C)(=O)O | null | 2 | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(C3CCCN3C(=O)OCc3ccccc3)cc2)c2ccccc21>Br.C(C)(=O)O>CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(C3CCCN3)cc2)c2ccccc21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-f87f3573c9554627adb678ba79085bae | CI.COC(=O)CCC(=O)Nc1ccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccc(Cl)cc3)C[C@@H]2C)cc1>>COC(=O)CCC(=O)N(C)c1ccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccc(Cl)cc3)C[C@@H]2C)cc1 | IC.COC(CCC(=O)NC1=CC=C(C=C1)C(=O)N1[C@H](C[C@H](C2=CC=CC=C12)N(C1=CC=C(C=C1)Cl)C(C)=O)C)=O.[H-].[Na+]>>COC(CCC(=O)N(C)C1=CC=C(C=C1)C(=O)N1[C@H](C[C@H](C2=CC=CC=C12)N(C1=CC=C(C=C1)Cl)C(C)=O)C)=O | I[CH3:10].[CH3:1][O:2][C:3](=[O:4])[CH2:5][CH2:6][C:7](=[O:8])[NH:9][c:11]1[cH:12][cH:13][c:14]([C:15](=[O:16])[N:17]2[c:18]3[cH:19][cH:20][cH:21][cH:22][c:23]3[C@H:24]([N:25]([C:26]([CH3:27])=[O:28])[c:29]3[cH:30][cH:31][c:32]([Cl:33])[cH:34][cH:35]3)[CH2:36][C@@H:37]2[CH3:38])[cH:39][cH:40]1>>[CH3:1][O:2][C:3](=[O:4]... | CI.COC(=O)CCC(=O)Nc1ccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccc(Cl)cc3)C[C@@H]2C)cc1 | COC(=O)CCC(=O)N(C)c1ccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccc(Cl)cc3)C[C@@H]2C)cc1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 780d850c4b8333c4b07101ff526eea0725c627f5cbcabe141bddc514762f1fac | 0a16658309ac5595448433dd7ef49294830b145345df0b202ccd54727262e629 | O=C(c1ccccc1)N1CC[C@@H](Nc2ccccc2)c2ccccc21 | I-[CH3;D1;+0:1].[C:2]-[C:3](=[O;D1;H0:4])-[NH;D2;+0:5]-[c:6](:[c:7]):[c:8]>>[C:2]-[C:3](=[O;D1;H0:4])-[N;H0;D3;+0:5](-[CH3;D1;+0:1])-[c:6](:[c:7]):[c:8] | 28.5 | [{"value": 26.0, "product": "COC(CCC(=O)N(C)C1=CC=C(C=C1)C(=O)N1[C@H](C[C@H](C2=CC=CC=C12)N(C1=CC=C(C=C1)Cl)C(C)=O)C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 28.5, "product": "COC(CCC(=O)N(C)C1=CC=C(C=C1)C(=O)N1[C@H](C[C@H](C2=CC=CC=C12)N(C1=CC=C(C=C1)Cl)C(C)=O)C)=O", "details": "CALCULATEDPERCEN... | null | null | 30 | MINUTE | To a solution of (2S,4R)-N-(4-{4-[Acetyl-(4-chloro-phenyl)-amino]-2-methyl-3,4-dihydro-2H-quinoline-1-carbonyl}-phenyl)-succinamic acid methyl ester (55 mg, 0.100 mmoles) in DMF was added sodium hydride (60% dispersion in oil). After 30 minutes, iodomethane (16 uL, 0.11 mmoles) was added to the reaction mixture and sti... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide | Tertiary amide | null | null | c1ccccc1.c1ccccc1.c1ccc2c(c1)CCC[NH]2 | HI | CN(C)C=O | null | 0.5 | CI.COC(=O)CCC(=O)Nc1ccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccc(Cl)cc3)C[C@@H]2C)cc1>CN(C)C=O>COC(=O)CCC(=O)N(C)c1ccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccc(Cl)cc3)C[C@@H]2C)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d2b854be4ea149d3a10eb70199f80773 | BrCCCn1cccc1.CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(O)cc2)c2ccccc21>>CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(OCCCn3cccc3)cc2)c2ccccc21 | ClC1=CC=C(C=C1)N(C(C)=O)[C@@H]1C[C@@H](N(C2=CC=CC=C12)C(C1=CC=C(C=C1)O)=O)C.C(=O)([O-])[O-].[K+].[K+].BrCCCN1C=CC=C1>>ClC1=CC=C(C=C1)N(C(C)=O)[C@@H]1C[C@@H](N(C2=CC=CC=C12)C(C1=CC=C(C=C1)OCCCN1C=CC=C1)=O)C | Br[CH2:24][CH2:25][CH2:26][n:27]1[cH:28][cH:29][cH:30][cH:31]1.[CH3:1][C:2](=[O:3])[N:4]([c:5]1[cH:6][cH:7][c:8]([Cl:9])[cH:10][cH:11]1)[C@@H:12]1[CH2:13][C@H:14]([CH3:15])[N:16]([C:17](=[O:18])[c:19]2[cH:20][cH:21][c:22]([OH:23])[cH:32][cH:33]2)[c:34]2[cH:35][cH:36][cH:37][cH:38][c:39]21>>[CH3:1][C:2](=[O:3])[N:4]([c:... | BrCCCn1cccc1.CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(O)cc2)c2ccccc21 | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(OCCCn3cccc3)cc2)c2ccccc21 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | O=C(c1ccc(OCCCn2cccc2)cc1)N1CC[C@@H](Nc2ccccc2)c2ccccc21 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[OH;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:4]-[c:5](:[c:6]):[c:7] | null | [] | 70 | CELSIUS | 3 | HOUR | (2S,4R)-N-(4-Chloro-phenyl)-N-[1-(4-hydroxy-benzoyl)-2-methyl-1,2,3,4-tetrahydro-quinolin-4-yl]-acetamide (75 mg, 0.17 mmol) was dissolved in DMF (1 mL) at room temperature. K2CO3 (47 mg, 0.34 mmol) was added followed by 1-(3-bromopropyl)-pyrrole and the reaction was allowed to stir at 70° C. for 3 hrs. The reaction mi... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccccc1.c1ccccc1.c1cc[nH]c1.c1ccc2c(c1)CCC[NH]2 | HBr | CN(C)C=O | 70 | 3 | BrCCCn1cccc1.CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(O)cc2)c2ccccc21>CN(C)C=O>CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(OCCCn3cccc3)cc2)c2ccccc21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-84c8442227934d18a3910544430738a3 | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(O)cc2)c2ccccc21.CC(C)(C)OC(=O)N1CCC(CCO)CC1>>CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(OCCC3CCN(C(=O)OC(C)(C)C)CC3)cc2)c2ccccc21 | CCOC(=O)/N=N/C(=O)OCC.ClC1=CC=C(C=C1)N(C(C)=O)[C@@H]1C[C@@H](N(C2=CC=CC=C12)C(C1=CC=C(C=C1)O)=O)C.C(C)(C)(C)OC(=O)N1CCC(CC1)CCO.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3>>C(C)(C)(C)OC(=O)N1CCC(CC1)CCOC1=CC=C(C=C1)C(=O)N1[C@H](C[C@H](C2=CC=CC=C12)N(C1=CC=C(C=C1)Cl)C(C)=O)C | [CH3:1][C:2](=[O:3])[N:4]([c:5]1[cH:6][cH:7][c:8]([Cl:9])[cH:10][cH:11]1)[C@@H:12]1[CH2:13][C@H:14]([CH3:15])[N:16]([C:17](=[O:18])[c:19]2[cH:20][cH:21][c:22]([OH:23])[cH:39][cH:40]2)[c:41]2[cH:42][cH:43][cH:44][cH:45][c:46]21.O[CH2:24][CH2:25][CH:26]1[CH2:27][CH2:28][N:29]([C:30](=[O:31])[O:32][C:33]([CH3:34])([CH3:35... | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(O)cc2)c2ccccc21.CC(C)(C)OC(=O)N1CCC(CCO)CC1 | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(OCCC3CCN(C(=O)OC(C)(C)C)CC3)cc2)c2ccccc21 | null | null | C1(=CC=CC=C1)C | Heteroatom Alkylation and Arylation | Mitsunobu aryl ether | 86bfb73617450d22f9456ed5ce4d96a73f1f8fc0c016bebae57fda68e2da86a2 | 2258bd14c3b5449b92dc09cf9fa522f88d5071b4af20f7e968b60aa1ae6db0cf | O=C(c1ccc(OCCC2CCNCC2)cc1)N1CC[C@@H](Nc2ccccc2)c2ccccc21 | O-[CH2;D2;+0:1]-[C:2]-[C:3].[OH;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:4]-[c:5](:[c:6]):[c:7] | 90 | [{"value": 90.0, "product": "C(C)(C)(C)OC(=O)N1CCC(CC1)CCOC1=CC=C(C=C1)C(=O)N1[C@H](C[C@H](C2=CC=CC=C12)N(C1=CC=C(C=C1)Cl)C(C)=O)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 88.4, "product": "C(C)(C)(C)OC(=O)N1CCC(CC1)CCOC1=CC=C(C=C1)C(=O)N1[C@H](C[C@H](C2=CC=CC=C12)N(C1=CC=C(C=C1)Cl)C(C)=O)C", "detai... | null | null | 18 | HOUR | 4-(2-Hydroxy-ethyl)-piperidine-1-carboxylic acid tert-butyl ester (0.119 g, 0.52 mmol) was dissolved in toluene at room temperature with PPh3 (0.136 g, 0.52 mmol), then added (2S,4R)-N-(4-chloro-phenyl)-N-[1-(4-hydroxy-benzoyl)-2-methyl-1,2,3,4-tetrahydro-quinolin-4-yl]-acetamide (0.150 g, 0.35 mmol) and stirred for 5 ... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Aromatic alcohol | Ether | null | null | c1ccccc1.c1ccccc1.C1CC[NH]CC1.c1ccc2c(c1)CCC[NH]2 | HO- | C1(=CC=CC=C1)C | null | 18 | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(O)cc2)c2ccccc21.CC(C)(C)OC(=O)N1CCC(CCO)CC1>C1(=CC=CC=C1)C>CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(OCCC3CCN(C(=O)OC(C)(C)C)CC3)cc2)c2ccccc21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-cf5deae96dc442349f5390276ac934ac | CCC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(OCCC(C)(C)C(=O)OC)cc2)c2ccccc21>>CCC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(OCCC(C)(C)C(=O)O)cc2)c2ccccc21 | ClC1=CC=C(C=C1)N([C@@H]1C[C@@H](N(C2=CC=CC=C12)C(=O)C1=CC=C(OCCC(C(=O)OC)(C)C)C=C1)C)C(CC)=O.[OH-].[Na+]>>ClC1=CC=C(C=C1)N([C@@H]1C[C@@H](N(C2=CC=CC=C12)C(=O)C1=CC=C(OCCC(C(=O)O)(C)C)C=C1)C)C(CC)=O | C[O:32][C:30]([C:27]([CH2:26][CH2:25][O:24][c:23]1[cH:22][cH:21][c:20]([C:18]([N:17]2[C@@H:15]([CH3:16])[CH2:14][C@@H:13]([N:5]([C:3]([CH2:2][CH3:1])=[O:4])[c:6]3[cH:7][cH:8][c:9]([Cl:10])[cH:11][cH:12]3)[c:40]3[c:35]2[cH:36][cH:37][cH:38][cH:39]3)=[O:19])[cH:34][cH:33]1)([CH3:28])[CH3:29])=[O:31]>>[CH3:1][CH2:2][C:3](... | CCC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(OCCC(C)(C)C(=O)OC)cc2)c2ccccc21 | CCC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(OCCC(C)(C)C(=O)O)cc2)c2ccccc21 | null | null | CO.O1CCCC1.O | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | O=C(c1ccccc1)N1CC[C@@H](Nc2ccccc2)c2ccccc21 | C-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4]>>[C:3]-[C:2](=[O;D1;H0:4])-[OH;D1;+0:1] | null | [] | 40 | CELSIUS | 8 | HOUR | Methyl 4-(4-{[(2S,4R)-4-[(4-chlorophenyl)(propionyl)amino]-2-methyl-3,4-dihydroquinolin-1(2H)-yl]carbonyl}phenoxy)-2,2-dimethylbutanoate was dissolved in methanol/tetrahydrofuran/water (2/1/1) then sodium hydroxide (3 equivalents) was added and reaction mixture stirred at 40° C. overnight. The mixture was concentrated,... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1.c1ccccc1.c1ccc2c(c1)CCC[NH]2 | Other | CO.O1CCCC1.O | 40 | 8 | CCC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(OCCC(C)(C)C(=O)OC)cc2)c2ccccc21>CO.O1CCCC1.O>CCC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(OCCC(C)(C)C(=O)O)cc2)c2ccccc21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a5ea1284cdf642f9a09944db69b01634 | COC(=O)c1cccc(COc2ccc(C(=O)N3c4ccccc4[C@H](N(C(C)=O)c4ccc(Cl)cc4)C[C@@H]3C)cc2)c1>>CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(OCc3cccc(C(=O)O)c3)cc2)c2ccccc21 | COC(C1=CC(=CC=C1)COC1=CC=C(C=C1)C(=O)N1[C@H](C[C@H](C2=CC=CC=C12)N(C1=CC=C(C=C1)Cl)C(C)=O)C)=O.[Li+].[OH-]>>C(C)(=O)N([C@@H]1C[C@@H](N(C2=CC=CC=C12)C(=O)C1=CC=C(OCC=2C=C(C(=O)O)C=CC2)C=C1)C)C1=CC=C(C=C1)Cl | C[O:32][C:30]([c:29]1[cH:28][cH:27][cH:26][c:25]([CH2:24][O:23][c:22]2[cH:21][cH:20][c:19]([C:17]([N:16]3[C@@H:14]([CH3:15])[CH2:13][C@@H:12]([N:4]([C:2]([CH3:1])=[O:3])[c:5]4[cH:6][cH:7][c:8]([Cl:9])[cH:10][cH:11]4)[c:41]4[c:36]3[cH:37][cH:38][cH:39][cH:40]4)=[O:18])[cH:35][cH:34]2)[cH:33]1)=[O:31]>>[CH3:1][C:2](=[O:3... | COC(=O)c1cccc(COc2ccc(C(=O)N3c4ccccc4[C@H](N(C(C)=O)c4ccc(Cl)cc4)C[C@@H]3C)cc2)c1 | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(OCc3cccc(C(=O)O)c3)cc2)c2ccccc21 | null | null | CO.C1CCOC1 | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | O=C(c1ccc(OCc2ccccc2)cc1)N1CC[C@@H](Nc2ccccc2)c2ccccc21 | 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] | 100 | [{"value": 100.0, "product": "C(C)(=O)N([C@@H]1C[C@@H](N(C2=CC=CC=C12)C(=O)C1=CC=C(OCC=2C=C(C(=O)O)C=CC2)C=C1)C)C1=CC=C(C=C1)Cl", "details": "PERCENTYIELD", "is_desired": false}, {"value": 98.8, "product": "C(C)(=O)N([C@@H]1C[C@@H](N(C2=CC=CC=C12)C(=O)C1=CC=C(OCC=2C=C(C(=O)O)C=CC2)C=C1)C)C1=CC=C(C=C1)Cl", "details": "C... | null | null | 18 | HOUR | (2S,4R)-3-(4-{4-[Acetyl-(4-chloro-phenyl)-amino]-2-methyl-3,4-dihydro-2H-quinoline-1-carbonyl}-phenoxymethyl)-benzoic acid methyl ester (93 mg, 0.16 mmol) was dissolved in MeOH/THF (2:1, 3 mL). To this solution was added LiOH (2M in H2O, 2 mL). The reaction was stirred at room temperature for 18 hours. The reaction mix... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1.c1ccccc1.c1ccccc1.c1ccc2c(c1)CCC[NH]2 | Other | CO.C1CCOC1 | null | 18 | COC(=O)c1cccc(COc2ccc(C(=O)N3c4ccccc4[C@H](N(C(C)=O)c4ccc(Cl)cc4)C[C@@H]3C)cc2)c1>CO.C1CCOC1>CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(OCc3cccc(C(=O)O)c3)cc2)c2ccccc21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-bb96459e667c4734b487e0ff7fa7a488 | COC(=O)C(C)(C)CCn1cc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccc(Cl)cc3)C[C@@H]2C)ccc1=O>>CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(=O)n(CCC(C)(C)C(=O)O)c2)c2ccccc21 | Cl.C(C)(=O)N([C@@H]1C[C@@H](N(C2=CC=CC=C12)C(=O)C=1C=CC(N(C1)CCC(C(=O)OC)(C)C)=O)C)C1=CC=C(C=C1)Cl.CO.[OH-].[Na+].C(C)(=O)N([C@@H]1C[C@@H](N(C2=CC=CC=C12)C(=O)C=1C=CC(N(C1)CCC(C(=O)OC)(C)C)=O)C)C1=CC=C(C=C1)Cl>>C(C)(=O)N([C@@H]1C[C@@H](N(C2=CC=CC=C12)C(=O)C=1C=CC(N(C1)CCC(C(=O)O)(C)C)=O)C)C1=CC=C(C=C1)Cl | C[O:32][C:30]([C:27]([CH2:26][CH2:25][n:24]1[c:22](=[O:23])[cH:21][cH:20][c:19]([C:17]([N:16]2[C@@H:14]([CH3:15])[CH2:13][C@@H:12]([N:4]([C:2]([CH3:1])=[O:3])[c:5]3[cH:6][cH:7][c:8]([Cl:9])[cH:10][cH:11]3)[c:39]3[c:34]2[cH:35][cH:36][cH:37][cH:38]3)=[O:18])[cH:33]1)([CH3:28])[CH3:29])=[O:31]>>[CH3:1][C:2](=[O:3])[N:4](... | COC(=O)C(C)(C)CCn1cc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccc(Cl)cc3)C[C@@H]2C)ccc1=O | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(=O)n(CCC(C)(C)C(=O)O)c2)c2ccccc21 | null | null | O1CCCC1 | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | O=C(c1ccc(=O)[nH]c1)N1CC[C@@H](Nc2ccccc2)c2ccccc21 | C-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4]>>[C:3]-[C:2](=[O;D1;H0:4])-[OH;D1;+0:1] | 63 | [{"value": 63.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | 4-[5-{[(2S,4R)-4-[acetyl(4-chlorophenyl)amino]-2-methyl-3,4-dihydroquinolin-1(2H)-yl]carbonyl}-2-oxopyridin-1(2H)-yl]-2,2-dimethylbutanoic acid was prepared from methyl 4-[5-{[(2S,4R)-4-[acetyl(4-chlorophenyl)amino]-2-methyl-3,4-dihydroquinolin-1(2H)-yl]carbonyl}-2-oxopyridin-1(2H)-yl]-2,2-dimethylbutanoate. methyl 4-[... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1.c1ccncc1.c1ccc2c(c1)CCC[NH]2 | Other | O1CCCC1 | null | 8 | COC(=O)C(C)(C)CCn1cc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccc(Cl)cc3)C[C@@H]2C)ccc1=O>O1CCCC1>CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(=O)n(CCC(C)(C)C(=O)O)c2)c2ccccc21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d48e91603a944558b4a6ae793cffb568 | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(O)cc2)c2ccccc21.CCOC(=O)C1(CCBr)CCC1>>CCOC(=O)C1(CCOc2ccc(C(=O)N3c4ccccc4C(N(C(C)=O)c4ccc(Cl)cc4)CC3C)cc2)CCC1 | ClC1=CC=C(C=C1)N(C(C)=O)[C@@H]1C[C@@H](N(C2=CC=CC=C12)C(C1=CC=C(C=C1)O)=O)C.C(=O)([O-])[O-].[K+].[K+].C(C)OC(=O)C1(CCC1)CCBr>>C(C)OC(=O)C1(CCC1)CCOC1=CC=C(C=C1)C(=O)N1C(CC(C2=CC=CC=C12)N(C1=CC=C(C=C1)Cl)C(C)=O)C | [OH:9][c:10]1[cH:11][cH:12][c:13]([C:14](=[O:15])[N:16]2[c:17]3[cH:18][cH:19][cH:20][cH:21][c:22]3[C@H:23]([N:24]([C:25]([CH3:26])=[O:27])[c:28]3[cH:29][cH:30][c:31]([Cl:32])[cH:33][cH:34]3)[CH2:35][C@@H:36]2[CH3:37])[cH:38][cH:39]1.Br[CH2:8][CH2:7][C:6]1([C:4]([O:3][CH2:2][CH3:1])=[O:5])[CH2:40][CH2:41][CH2:42]1>>[CH3... | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(O)cc2)c2ccccc21.CCOC(=O)C1(CCBr)CCC1 | CCOC(=O)C1(CCOc2ccc(C(=O)N3c4ccccc4C(N(C(C)=O)c4ccc(Cl)cc4)CC3C)cc2)CCC1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | O=C(c1ccc(OCCC2CCC2)cc1)N1CCC(Nc2ccccc2)c2ccccc21 | Br-[CH2;D2;+0:1]-[C:2]-[C:3]-[C:4](-[#8:5])=[O;D1;H0:6].[OH;D1;+0:7]-[c:8](:[c:9]):[c:10]>>[#8:5]-[C:4](=[O;D1;H0:6])-[C:3]-[C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:7]-[c:8](:[c:9]):[c:10] | 67.5 | [{"value": 67.0, "product": "C(C)OC(=O)C1(CCC1)CCOC1=CC=C(C=C1)C(=O)N1C(CC(C2=CC=CC=C12)N(C1=CC=C(C=C1)Cl)C(C)=O)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 67.5, "product": "C(C)OC(=O)C1(CCC1)CCOC1=CC=C(C=C1)C(=O)N1C(CC(C2=CC=CC=C12)N(C1=CC=C(C=C1)Cl)C(C)=O)C", "details": "CALCULATEDPERCENTYIELD", "... | 80 | CELSIUS | null | null | (2S,4R)-N-(4-Chloro-phenyl)-N-[1-(4-hydroxy-benzoyl)-2-methyl-1,2,3,4-tetrahydro-quinolin-4-yl]-acetamide (0.17 g, 0.39 mmol) was dissolved in 5 ml DMF at room temperature and K2CO3 (0.323 g, 2.34 mmol) was added. 1-(2-Bromo-ethyl)-cyclobutanecarboxylic acid ethyl ester (0.184 g, 0.78 mmol) prepared according to the pr... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccccc1.c1ccccc1.c1ccc2c(c1)CCC[NH]2.C1CCC1 | HBr | CN(C)C=O | 80 | null | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(O)cc2)c2ccccc21.CCOC(=O)C1(CCBr)CCC1>CN(C)C=O>CCOC(=O)C1(CCOc2ccc(C(=O)N3c4ccccc4C(N(C(C)=O)c4ccc(Cl)cc4)CC3C)cc2)CCC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-260b2ae7b890435895894e0d4a23f224 | COC(=O)c1cccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccc(Cl)cc3)C[C@@H]2C)c1>>CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2cccc(C(=O)O)c2)c2ccccc21 | C(C)(=O)N([C@@H]1C[C@@H](N(C2=CC=CC=C12)C(=O)C=1C=C(C(=O)OC)C=CC1)C)C1=CC=C(C=C1)Cl.[OH-].[Li+].O.CO>>C(C)(=O)N([C@@H]1C[C@@H](N(C2=CC=CC=C12)C(=O)C=1C=C(C(=O)O)C=CC1)C)C1=CC=C(C=C1)Cl | C[O:26][C:24]([c:23]1[cH:22][cH:21][cH:20][c:19]([C:17]([N:16]2[C@@H:14]([CH3:15])[CH2:13][C@@H:12]([N:4]([C:2]([CH3:1])=[O:3])[c:5]3[cH:6][cH:7][c:8]([Cl:9])[cH:10][cH:11]3)[c:33]3[c:28]2[cH:29][cH:30][cH:31][cH:32]3)=[O:18])[cH:27]1)=[O:25]>>[CH3:1][C:2](=[O:3])[N:4]([c:5]1[cH:6][cH:7][c:8]([Cl:9])[cH:10][cH:11]1)[C@... | COC(=O)c1cccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccc(Cl)cc3)C[C@@H]2C)c1 | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2cccc(C(=O)O)c2)c2ccccc21 | null | null | O1CCCC1 | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | O=C(c1ccccc1)N1CC[C@@H](Nc2ccccc2)c2ccccc21 | 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] | null | [] | null | null | null | null | 3-{[(2S,4R)-4-[acetyl(4-chlorophenyl)amino]-2-methyl-3,4-dihydroquinolin-1(2H)-yl]carbonyl}benzoic acid was prepared following general procedure H, substituting methyl 3-(chlorocarbonyl)benzoate for 6-trifluoromethyl nicotinyl chloride. (Methyl 3-(chlorocarbonyl)benzoate was prepared in one step from 3-(methoxycarbonyl... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1.c1ccccc1.c1ccc2c(c1)CCC[NH]2 | Other | O1CCCC1 | null | null | COC(=O)c1cccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccc(Cl)cc3)C[C@@H]2C)c1>O1CCCC1>CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2cccc(C(=O)O)c2)c2ccccc21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-6bc4df3b80f3467581d289cbfbfcf4b5 | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(O)cc2)c2ccccc21>>CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(OCCCC#N)cc2)c2ccccc21 | ClC1=CC=C(C=C1)N(C(C)=O)[C@@H]1C[C@@H](N(C2=CC=CC=C12)C(C1=CC=C(C=C1)O)=O)C.C(=O)([O-])[O-].[K+].[K+]>>ClC1=CC=C(C=C1)N(C(C)=O)[C@@H]1C[C@@H](N(C2=CC=CC=C12)C(C1=CC=C(C=C1)OCCCC#N)=O)C | [CH3:1][C:2](=[O:3])[N:4]([c:5]1[cH:6][cH:7][c:8]([Cl:9])[cH:10][cH:11]1)[C@@H:12]1[CH2:13][C@H:14]([CH3:15])[N:16]([C:17](=[O:18])[c:19]2[cH:20][cH:21][c:22]([OH:23])[cH:29][cH:30]2)[c:31]2[cH:32][cH:33][cH:34][cH:35][c:36]21>>[CH3:1][C:2](=[O:3])[N:4]([c:5]1[cH:6][cH:7][c:8]([Cl:9])[cH:10][cH:11]1)[C@@H:12]1[CH2:13][... | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(O)cc2)c2ccccc21 | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(OCCCC#N)cc2)c2ccccc21 | null | null | CN(C)C=O | Miscellaneous | OtherReaction | 62b3f87f872eb35b905023702f49c8ef0ec2acd47819559d34b013c192756273 | b9d79c839d920e1db10c76e866272cc5c1a63e96079f1b85ef5c22f374132958 | O=C(c1ccccc1)N1CC[C@@H](Nc2ccccc2)c2ccccc21 | [OH;D1;+0:1]-[c:2](:[c:3]):[c:4]>>[C:5]-[C:6]-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | 80 | CELSIUS | null | null | (2S,4R)-N-(4-Chloro-phenyl)-N-[1-(4-hydroxy-benzoyl)-2-methyl-1,2,3,4-tetrahydro-quinolin-4-yl]-acetamide was dissolved in DMF at room temperature and K2CO3 was added. 4-Bromobutylnitrile was added and the reaction was allowed to heat to 80° C. overnight. The reaction mixture was concentrated in vacuo. The residue was ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic alcohol | Ether.Nitrile | null | null | c1ccccc1.c1ccccc1.c1ccc2c(c1)CCC[NH]2 | Other | CN(C)C=O | 80 | null | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(O)cc2)c2ccccc21>CN(C)C=O>CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(OCCCC#N)cc2)c2ccccc21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-01523886e92d415fa9c90295677c09d3 | CC(N)=NO.COC(=O)CCCOc1ccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccc(Cl)cc3)C[C@@H]2C)cc1>>CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(OCCCc3nc(C)no3)cc2)c2ccccc21 | COC(CCCOC1=CC=C(C=C1)C(=O)N1[C@H](C[C@H](C2=CC=CC=C12)N(C1=CC=C(C=C1)Cl)C(C)=O)C)=O.COC(CCCOC1=CC=C(C=C1)C(=O)N1[C@H](C[C@H](C2=CC=CC=C12)N(C1=CC=C(C=C1)Cl)C(C)=O)C)=O.C(C)(N)=NO.[H-].[Na+]>>ClC1=CC=C(C=C1)N(C(C)=O)[C@@H]1C[C@@H](N(C2=CC=CC=C12)C(C1=CC=C(C=C1)OCCCC1=NC(=NO1)C)=O)C | [NH2:28][C:29]([CH3:30])=[N:31][OH:32].CO[C:27](=O)[CH2:26][CH2:25][CH2:24][O:23][c:22]1[cH:21][cH:20][c:19]([C:17]([N:16]2[C@@H:14]([CH3:15])[CH2:13][C@@H:12]([N:4]([C:2]([CH3:1])=[O:3])[c:5]3[cH:6][cH:7][c:8]([Cl:9])[cH:10][cH:11]3)[c:40]3[c:35]2[cH:36][cH:37][cH:38][cH:39]3)=[O:18])[cH:34][cH:33]1>>[CH3:1][C:2](=[O:... | CC(N)=NO.COC(=O)CCCOc1ccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccc(Cl)cc3)C[C@@H]2C)cc1 | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(OCCCc3nc(C)no3)cc2)c2ccccc21 | null | null | C1CCOC1 | Aromatic Heterocycle Formation | OtherReaction | 43e03f02d10dc54d85ee9781721c9d0221ebef30b72279800340401c6938699d | cebce5595aa07ce7d963d9bec7e14045a383ede1b91396cf2ab62ec00127af65 | O=C(c1ccc(OCCCc2ncno2)cc1)N1CC[C@@H](Nc2ccccc2)c2ccccc21 | C-O-[C;H0;D3;+0:1](=O)-[C:2]-[C:3].[C;D1;H3:4]-[C;H0;D3;+0:5](-[NH2;D1;+0:6])=[N;H0;D2;+0:7]-[OH;D1;+0:8]>>[C:3]-[C:2]-[c;H0;D3;+0:1]1:[n;H0;D2;+0:6]:[c;H0;D3;+0:5](-[C;D1;H3:4]):[n;H0;D2;+0:7]:[o;H0;D2;+0:8]:1 | null | [] | null | null | null | null | (2S,4R)-N-(4-Chloro-phenyl)-N-(2-methyl-1-{4-[3-(3-methyl-[1,2,4]oxadiazol-5-yl)-propoxy]-benzoyl}-1,2,3,4-tetrahydro-quinolin-4-yl)-acetamide was prepared from (2S,4R)-4-(4-{4-[acetyl(4-chloro-phenyl)-amino]-2-methyl-3,4-dihydro-2H-quinoline-1-carbonyl}-phenoxy)-butyric acid methyl ester. Acetamide oxime (0.043 g, 0.5... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Primary amine.Oxime | null | null | c1ncon1 | c1ccccc1.c1ccccc1.c1ncon1.c1ccc2c(c1)CCC[NH]2 | HO- | C1CCOC1 | null | null | CC(N)=NO.COC(=O)CCCOc1ccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccc(Cl)cc3)C[C@@H]2C)cc1>C1CCOC1>CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(OCCCc3nc(C)no3)cc2)c2ccccc21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a0f4868cd4cc4314a16ced02e1dfbba8 | CC(=O)Cl.CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(OCCCN3CCNCC3)cc2)c2ccccc21>>CC(=O)N1CCN(CCCOc2ccc(C(=O)N3c4ccccc4[C@H](N(C(C)=O)c4ccc(Cl)cc4)C[C@@H]3C)cc2)CC1 | ClC1=CC=C(C=C1)N(C(C)=O)[C@@H]1C[C@@H](N(C2=CC=CC=C12)C(C1=CC=C(C=C1)OCCCN1CCNCC1)=O)C.C(C)(=O)Cl.CCN(C(C)C)C(C)C>>C(C)(=O)N1CCN(CC1)CCCOC1=CC=C(C(=O)N2[C@H](C[C@H](C3=CC=CC=C23)N(C(C)=O)C2=CC=C(C=C2)Cl)C)C=C1 | Cl[C:2]([CH3:1])=[O:3].[NH:4]1[CH2:5][CH2:6][N:7]([CH2:8][CH2:9][CH2:10][O:11][c:12]2[cH:13][cH:14][c:15]([C:16](=[O:17])[N:18]3[c:19]4[cH:20][cH:21][cH:22][cH:23][c:24]4[C@H:25]([N:26]([C:27]([CH3:28])=[O:29])[c:30]4[cH:31][cH:32][c:33]([Cl:34])[cH:35][cH:36]4)[CH2:37][C@@H:38]3[CH3:39])[cH:40][cH:41]2)[CH2:42][CH2:43... | CC(=O)Cl.CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(OCCCN3CCNCC3)cc2)c2ccccc21 | CC(=O)N1CCN(CCCOc2ccc(C(=O)N3c4ccccc4[C@H](N(C(C)=O)c4ccc(Cl)cc4)C[C@@H]3C)cc2)CC1 | null | null | C(Cl)Cl | Acylation | N-alkylation of secondary amines with alkyl halides | 6dd420fad17fb719b6bd840e8952a8d7b2fb24721f86f8b8f9c697a36eb97ec3 | 96cb0a2fed10552c5770a45a2d6523b47ac3e38928b4a9c698d8577451182dcd | O=C(c1ccc(OCCCN2CCNCC2)cc1)N1CC[C@@H](Nc2ccccc2)c2ccccc21 | Cl-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[#7:4]1-[C:5]-[C:6]-[NH;D2;+0:7]-[C:8]-[C:9]-1>>[C;D1;H3:2]-[C;H0;D3;+0:1](=[O;D1;H0:3])-[N;H0;D3;+0:7]1-[C:6]-[C:5]-[#7:4]-[C:9]-[C:8]-1 | 57 | [{"value": 57.0, "product": "C(C)(=O)N1CCN(CC1)CCCOC1=CC=C(C(=O)N2[C@H](C[C@H](C3=CC=CC=C23)N(C(C)=O)C2=CC=C(C=C2)Cl)C)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 55.4, "product": "C(C)(=O)N1CCN(CC1)CCCOC1=CC=C(C(=O)N2[C@H](C[C@H](C3=CC=CC=C23)N(C(C)=O)C2=CC=C(C=C2)Cl)C)C=C1", "details": "CALCULAT... | null | null | 8 | HOUR | (2S,4R)-N-(4-Chloro-phenyl)-N-{2-methyl-1-[4-(3-piperazin-1-yl-propoxy)-benzoyl]-1,2,3,4-tetrahydro-quinolin-4-yl}-acetamide (168 mg) was dissolved in CH2Cl2 (2 mL). Acetic chloride (47 mg) and DIEA (52 uL) were added. The reaction mixture was stirred at room temperature overnight. The organic phase was washed with sat... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Secondary amine | Tertiary amide | C1CNCC[NH]1 | C1C[NH]CC[NH]1 | C1C[NH]CC[NH]1.c1ccccc1.c1ccccc1.c1ccc2c(c1)CCC[NH]2 | HCl | C(Cl)Cl | null | 8 | CC(=O)Cl.CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(OCCCN3CCNCC3)cc2)c2ccccc21>C(Cl)Cl>CC(=O)N1CCN(CCCOc2ccc(C(=O)N3c4ccccc4[C@H](N(C(C)=O)c4ccc(Cl)cc4)C[C@@H]3C)cc2)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-da5ab7e65d354a46b02cf5f73b6d7f4f | CCOC(=O)C1CCN(c2ccc(C(=O)N3c4ccccc4[C@H](N(C(C)=O)c4ccc(Cl)cc4)C[C@@H]3C)cc2)CC1>>CCOC(=O)C1CCCN(c2ccc(C(=O)N3c4ccccc4[C@H](N(C(C)=O)c4ccc(Cl)cc4)C[C@@H]3C)cc2)C1 | C(C)OC(=O)C1CCN(CC1)C1=CC=C(C=C1)C(=O)N1[C@H](C[C@H](C2=CC=CC=C12)N(C1=CC=C(C=C1)Cl)C(C)=O)C.C(C)OC(=O)C1CCNCC1>>C(C)OC(=O)C1CN(CCC1)C1=CC=C(C=C1)C(=O)N1[C@H](C[C@H](C2=CC=CC=C12)N(C1=CC=C(C=C1)Cl)C(C)=O)C | [CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:7]1[CH2:6][CH2:41][N:10]([c:11]2[cH:12][cH:13][c:14]([C:15](=[O:16])[N:17]3[c:18]4[cH:19][cH:20][cH:21][cH:22][c:23]4[C@H:24]([N:25]([C:26]([CH3:27])=[O:28])[c:29]4[cH:30][cH:31][c:32]([Cl:33])[cH:34][cH:35]4)[CH2:36][C@@H:37]3[CH3:38])[cH:39][cH:40]2)[CH2:9][CH2:8]1>>[CH3:1][CH2:2][... | CCOC(=O)C1CCN(c2ccc(C(=O)N3c4ccccc4[C@H](N(C(C)=O)c4ccc(Cl)cc4)C[C@@H]3C)cc2)CC1 | CCOC(=O)C1CCCN(c2ccc(C(=O)N3c4ccccc4[C@H](N(C(C)=O)c4ccc(Cl)cc4)C[C@@H]3C)cc2)C1 | null | null | null | Miscellaneous | OtherReaction | c3b087821465deb697aaff208f042e78b416b6b80a3796ec40945ef2f4da1646 | 6ad95641ddc9be155108cd2297ce15bcd8cb0ca25c68bfc4fce3cbf5009a236a | O=C(c1ccc(N2CCCCC2)cc1)N1CC[C@@H](Nc2ccccc2)c2ccccc21 | [C:1]-[#8:2]-[C;H0;D3;+0:3](=[O;D1;H0:4])-[CH;D3;+0:5]1-[C:6]-[C:7]-[#7:8](-[c:9])-[C:10]-[CH2;D2;+0:11]-1>>[C:1]-[#8:2]-[C;H0;D3;+0:3](=[O;D1;H0:4])-[CH;D3;+0:11]1-[C:10]-[#7:8](-[c:9])-[C:7]-[C:6]-[CH2;D2;+0:5]-1 | null | [] | null | null | null | null | (2S,4R)-1-(4-{4-[Acetyl-(4-chloro-phenyl)-amino]-2-methyl-3,4-dihydro-2H-quinoline-1-carbonyl}-phenyl)-piperidine-3-carboxylic acid ethyl ester was prepared following the procedure for (2S,4R)-1-(4-{4-[Acetyl-(4-chloro-phenyl)-amino]-2-methyl-3,4-dihydro-2H-quinoline-1-carbonyl}-phenyl)-piperidine-4-carboxylic acid eth... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Ester | C1CC[NH]CC1 | C1CC[NH]CC1 | C1CC[NH]CC1.c1ccccc1.c1ccccc1.c1ccc2c(c1)CCC[NH]2 | null | null | null | null | CCOC(=O)C1CCN(c2ccc(C(=O)N3c4ccccc4[C@H](N(C(C)=O)c4ccc(Cl)cc4)C[C@@H]3C)cc2)CC1>>CCOC(=O)C1CCCN(c2ccc(C(=O)N3c4ccccc4[C@H](N(C(C)=O)c4ccc(Cl)cc4)C[C@@H]3C)cc2)C1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-bfbc2ef26cca4def84023d5e23c5ce21 | COC(=O)C(C)(C)CCCc1ccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccc(Cl)cc3)C[C@@H]2C)cc1F>>CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(CCCC(C)(C)C(=O)O)c(F)c2)c2ccccc21 | C(C)(=O)N([C@@H]1C[C@@H](N(C2=CC=CC=C12)C(=O)C1=CC(=C(C=C1)CCCC(C(=O)OC)(C)C)F)C)C1=CC=C(C=C1)Cl.[OH-].[Na+]>>C(C)(=O)N([C@@H]1C[C@@H](N(C2=CC=CC=C12)C(=O)C1=CC(=C(C=C1)CCCC(C(=O)O)(C)C)F)C)C1=CC=C(C=C1)Cl | C[O:31][C:29]([C:26]([CH2:25][CH2:24][CH2:23][c:22]1[cH:21][cH:20][c:19]([C:17]([N:16]2[C@@H:14]([CH3:15])[CH2:13][C@@H:12]([N:4]([C:2]([CH3:1])=[O:3])[c:5]3[cH:6][cH:7][c:8]([Cl:9])[cH:10][cH:11]3)[c:40]3[c:35]2[cH:36][cH:37][cH:38][cH:39]3)=[O:18])[cH:34][c:32]1[F:33])([CH3:27])[CH3:28])=[O:30]>>[CH3:1][C:2](=[O:3])[... | COC(=O)C(C)(C)CCCc1ccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccc(Cl)cc3)C[C@@H]2C)cc1F | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(CCCC(C)(C)C(=O)O)c(F)c2)c2ccccc21 | null | null | O.CO.O1CCCC1 | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | O=C(c1ccccc1)N1CC[C@@H](Nc2ccccc2)c2ccccc21 | C-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4]>>[C:3]-[C:2](=[O;D1;H0:4])-[OH;D1;+0:1] | 84 | [{"value": 84.0, "product": "C(C)(=O)N([C@@H]1C[C@@H](N(C2=CC=CC=C12)C(=O)C1=CC(=C(C=C1)CCCC(C(=O)O)(C)C)F)C)C1=CC=C(C=C1)Cl", "details": "PERCENTYIELD", "is_desired": false}, {"value": 82.6, "product": "C(C)(=O)N([C@@H]1C[C@@H](N(C2=CC=CC=C12)C(=O)C1=CC(=C(C=C1)CCCC(C(=O)O)(C)C)F)C)C1=CC=C(C=C1)Cl", "details": "CALCUL... | 40 | CELSIUS | null | null | Methyl 5-(4-{[(2S,4R)-4-[acetyl(4-chlorophenyl)amino]-2-methyl-3,4-dihydroquinolin-1(2H)-yl]carbonyl}-2-fluorophenyl)-2,2-dimethylpentanoate (70 mg, 0.12 mmol, 1 eq.) was dissolved in methanol/tetrahydrofuran (2/1) (3 ml). A solution of sodium hydroxide (8 mg, 0.20 mmol, 1.7 eq.) in water (1 ml) was added and reaction ... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1.c1ccccc1.c1ccc2c(c1)CCC[NH]2 | Other | O.CO.O1CCCC1 | 40 | null | COC(=O)C(C)(C)CCCc1ccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccc(Cl)cc3)C[C@@H]2C)cc1F>O.CO.O1CCCC1>CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(CCCC(C)(C)C(=O)O)c(F)c2)c2ccccc21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-929131b2e5ac4ecea524a088d0a2322f | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(O)cc2)c2ccccc21.O=C1CCCN1CCCO>>CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(OCCCN3CCCC3=O)cc2)c2ccccc21 | CCOC(=O)/N=N/C(=O)OCC.ClC1=CC=C(C=C1)N(C(C)=O)[C@@H]1C[C@@H](N(C2=CC=CC=C12)C(C1=CC=C(C=C1)O)=O)C.OCCCN1C(CCC1)=O.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3>>ClC1=CC=C(C=C1)N(C(C)=O)[C@@H]1C[C@@H](N(C2=CC=CC=C12)C(C1=CC=C(C=C1)OCCCN1C(CCC1)=O)=O)C | O[c:22]1[cH:21][cH:20][c:19]([C:17]([N:16]2[C@@H:14]([CH3:15])[CH2:13][C@@H:12]([N:4]([C:2]([CH3:1])=[O:3])[c:5]3[cH:6][cH:7][c:8]([Cl:9])[cH:10][cH:11]3)[c:40]3[c:35]2[cH:36][cH:37][cH:38][cH:39]3)=[O:18])[cH:34][cH:33]1.[OH:23][CH2:24][CH2:25][CH2:26][N:27]1[CH2:28][CH2:29][CH2:30][C:31]1=[O:32]>>[CH3:1][C:2](=[O:3])... | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(O)cc2)c2ccccc21.O=C1CCCN1CCCO | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(OCCCN3CCCC3=O)cc2)c2ccccc21 | null | null | C1=CC=CC=C1 | Heteroatom Alkylation and Arylation | Mitsunobu aryl ether | 8915084acbaaf997bf0f89ff5187cb2f89c25dc683fffc57b3391298c8430dd9 | 2258bd14c3b5449b92dc09cf9fa522f88d5071b4af20f7e968b60aa1ae6db0cf | O=C1CCCN1CCCOc1ccc(C(=O)N2CC[C@@H](Nc3ccccc3)c3ccccc32)cc1 | O-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[C:6]-[C:7]-[OH;D1;+0:8]>>[C:6]-[C:7]-[O;H0;D2;+0:8]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5] | 45 | [{"value": 45.0, "product": "ClC1=CC=C(C=C1)N(C(C)=O)[C@@H]1C[C@@H](N(C2=CC=CC=C12)C(C1=CC=C(C=C1)OCCCN1C(CCC1)=O)=O)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 5 | MINUTE | N-(3-hydroxypropyl)-2-pyrrolidone was dissolved in benzene at room temperature with PPh3 (0.044 g, 0.16 mmol) added (2S,4R)-N-(4-chloro-phenyl)-N-[1-(4-hydroxy-benzoyl)-2-methyl-1,2,3,4-tetrahydro-quinolin-4-yl]-acetamide (0.100 g, 0.22 mmol) and stirred for 5 min. DEAD (0.029 g, 0.16 mmol) was added and the reaction w... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Aromatic alcohol | Ether | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1.C1CC[NH]C1.c1ccc2c(c1)CCC[NH]2 | HO- | C1=CC=CC=C1 | null | 0.083333 | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(O)cc2)c2ccccc21.O=C1CCCN1CCCO>C1=CC=CC=C1>CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(OCCCN3CCCC3=O)cc2)c2ccccc21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-03d10e81aa00494884e9c2c478e63a25 | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(O)cc2)c2ccccc21.COC(=O)C(C)CCCl>>COC(=O)[C@@H](C)CCOc1ccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccc(Cl)cc3)CC2C)cc1 | ClC1=CC=C(C=C1)N(C(C)=O)[C@@H]1C[C@@H](N(C2=CC=CC=C12)C(C1=CC=C(C=C1)O)=O)C.C(=O)([O-])[O-].[Cs+].[Cs+].COC(C(CCCl)C)=O>>COC([C@H](CCOC1=CC=C(C=C1)C(=O)N1C(C[C@H](C2=CC=CC=C12)N(C1=CC=C(C=C1)Cl)C(C)=O)C)C)=O | [OH:9][c:10]1[cH:11][cH:12][c:13]([C:14](=[O:15])[N:16]2[c:17]3[cH:18][cH:19][cH:20][cH:21][c:22]3[C@H:23]([N:24]([C:25]([CH3:26])=[O:27])[c:28]3[cH:29][cH:30][c:31]([Cl:32])[cH:33][cH:34]3)[CH2:35][C@@H:36]2[CH3:37])[cH:38][cH:39]1.Cl[CH2:8][CH2:7][CH:5]([C:3]([O:2][CH3:1])=[O:4])[CH3:6]>>[CH3:1][O:2][C:3](=[O:4])[C@@... | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(O)cc2)c2ccccc21.COC(=O)C(C)CCCl | COC(=O)[C@@H](C)CCOc1ccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccc(Cl)cc3)CC2C)cc1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | O=C(c1ccccc1)N1CC[C@@H](Nc2ccccc2)c2ccccc21 | Cl-[CH2;D2;+0:1]-[C:2]-[C:3]-[C:4](-[#8:5])=[O;D1;H0:6].[OH;D1;+0:7]-[c:8](:[c:9]):[c:10]>>[#8:5]-[C:4](=[O;D1;H0:6])-[C:3]-[C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:7]-[c:8](:[c:9]):[c:10] | null | [] | null | null | 8 | HOUR | (2S,4R)-N-(4-Chloro-phenyl)-N-[1-(4-hydroxy-benzoyl)-2-methyl-1,2,3,4-tetrahydro-quinolin-4-yl]-acetamide (230 mg, 0.531 mmol) was dissolved in DMF (5 mL) at room temperature. Cs2CO3 (433 mg, 1.33 mmol) was added followed by 4-chloro-2-methyl-butyric acid methyl ester (120 mg, 0.796 mmol) and the reaction was allowed t... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccccc1.c1ccccc1.c1ccc2c(c1)CCC[NH]2 | HCl | CN(C)C=O | null | 8 | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(O)cc2)c2ccccc21.COC(=O)C(C)CCCl>CN(C)C=O>COC(=O)[C@@H](C)CCOc1ccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccc(Cl)cc3)CC2C)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-852acf44da8446f3b94f42d23b72403a | COC(=O)C(C)(C)CCc1ccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccc(Cl)cc3)C[C@@H]2C)cc1>>CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(CCC(C)(C)C(=O)O)cc2)c2ccccc21 | C(C)(=O)N([C@@H]1C[C@@H](N(C2=CC=CC=C12)C(=O)C1=CC=C(C=C1)CCC(C(=O)OC)(C)C)C)C1=CC=C(C=C1)Cl.[OH-].[Na+]>>C(C)(=O)N([C@@H]1C[C@@H](N(C2=CC=CC=C12)C(=O)C1=CC=C(C=C1)CCC(C(=O)O)(C)C)C)C1=CC=C(C=C1)Cl | C[O:30][C:28]([C:25]([CH2:24][CH2:23][c:22]1[cH:21][cH:20][c:19]([C:17]([N:16]2[C@@H:14]([CH3:15])[CH2:13][C@@H:12]([N:4]([C:2]([CH3:1])=[O:3])[c:5]3[cH:6][cH:7][c:8]([Cl:9])[cH:10][cH:11]3)[c:38]3[c:33]2[cH:34][cH:35][cH:36][cH:37]3)=[O:18])[cH:32][cH:31]1)([CH3:26])[CH3:27])=[O:29]>>[CH3:1][C:2](=[O:3])[N:4]([c:5]1[c... | COC(=O)C(C)(C)CCc1ccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccc(Cl)cc3)C[C@@H]2C)cc1 | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(CCC(C)(C)C(=O)O)cc2)c2ccccc21 | null | null | CO.O1CCCC1.O | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | O=C(c1ccccc1)N1CC[C@@H](Nc2ccccc2)c2ccccc21 | C-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4]>>[C:3]-[C:2](=[O;D1;H0:4])-[OH;D1;+0:1] | null | [] | 40 | CELSIUS | 8 | HOUR | Methyl 4-(4-{[(2S,4R)-4-[acetyl(4-chlorophenyl)amino]-2-methyl-3,4-dihydroquinolin-1(2H)-yl]carbonyl}phenyl)-2,2-dimethylbutanoate was dissolved in methanol/tetrahydrofuran/water (2/1/1) then sodium hydroxide (3 equivalents) was added and reaction mixture stirred at 40° C. overnight. The mixture was concentrated, the r... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1.c1ccccc1.c1ccc2c(c1)CCC[NH]2 | Other | CO.O1CCCC1.O | 40 | 8 | COC(=O)C(C)(C)CCc1ccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccc(Cl)cc3)C[C@@H]2C)cc1>CO.O1CCCC1.O>CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(CCC(C)(C)C(=O)O)cc2)c2ccccc21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-4d8f0399fab14d8e912a54031e081cba | COC(=O)C(C)(C)CCCc1ccc(C(=O)N2c3ccccc3[C@H](N(C(=O)COC(C)=O)c3ccc(Cl)cc3)C[C@@H]2C)cc1>>C[C@H]1C[C@@H](N(C(=O)CO)c2ccc(Cl)cc2)c2ccccc2N1C(=O)c1ccc(CCCC(C)(C)C(=O)O)cc1 | C(C)(=O)OCC(=O)N([C@@H]1C[C@@H](N(C2=CC=CC=C12)C(=O)C1=CC=C(C=C1)CCCC(C(=O)OC)(C)C)C)C1=CC=C(C=C1)Cl.[OH-].[Na+]>>ClC1=CC=C(C=C1)N([C@@H]1C[C@@H](N(C2=CC=CC=C12)C(=O)C1=CC=C(C=C1)CCCC(C(=O)O)(C)C)C)C(CO)=O | CC(=O)[O:9][CH2:8][C:6]([N:5]([C@@H:4]1[CH2:3][C@H:2]([CH3:1])[N:23]([C:24](=[O:25])[c:26]2[cH:27][cH:28][c:29]([CH2:30][CH2:31][CH2:32][C:33]([CH3:34])([CH3:35])[C:36](=[O:37])[O:38]C)[cH:39][cH:40]2)[c:22]2[c:17]1[cH:18][cH:19][cH:20][cH:21]2)[c:10]1[cH:11][cH:12][c:13]([Cl:14])[cH:15][cH:16]1)=[O:7]>>[CH3:1][C@H:2]1... | COC(=O)C(C)(C)CCCc1ccc(C(=O)N2c3ccccc3[C@H](N(C(=O)COC(C)=O)c3ccc(Cl)cc3)C[C@@H]2C)cc1 | C[C@H]1C[C@@H](N(C(=O)CO)c2ccc(Cl)cc2)c2ccccc2N1C(=O)c1ccc(CCCC(C)(C)C(=O)O)cc1 | null | null | O.CO.O1CCCC1 | Reduction | OtherReaction | 79c1410c18eea607ff733540b2e9e80ec29f45607a2589972ab40239e908ada2 | 599ee09307730cd80040d089638003135f08dafff7f9560e5f7985624264521a | O=C(c1ccccc1)N1CC[C@@H](Nc2ccccc2)c2ccccc21 | C-C(=O)-[O;H0;D2;+0:1]-[C:2]-[C:3](=[O;D1;H0:4])-[#7:5](-[C:6])-[c:7].C-[O;H0;D2;+0:8]-[C:9](-[C:10])=[O;D1;H0:11]>>[C:6]-[#7:5](-[c:7])-[C:3](=[O;D1;H0:4])-[C:2]-[OH;D1;+0:1].[C:10]-[C:9](=[O;D1;H0:11])-[OH;D1;+0:8] | 70 | [{"value": 70.0, "product": "ClC1=CC=C(C=C1)N([C@@H]1C[C@@H](N(C2=CC=CC=C12)C(=O)C1=CC=C(C=C1)CCCC(C(=O)O)(C)C)C)C(CO)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 69.9, "product": "ClC1=CC=C(C=C1)N([C@@H]1C[C@@H](N(C2=CC=CC=C12)C(=O)C1=CC=C(C=C1)CCCC(C(=O)O)(C)C)C)C(CO)=O", "details": "CALCULATEDPERC... | 45 | CELSIUS | null | null | Methyl 5-(4-{[(2S,4R)-4-[[(acetyloxy)acetyl](4-chlorophenyl)amino]-2-methyl-3,4-dihydroquinolin-1(2H)-yl]carbonyl}phenyl)-2,2-dimethylpentanoate (100 mg, 0.16 mmol, 1 eq.) was dissolved in methanol/tetrahydrofuran (2/1) (2 ml). A solution of sodium hydroxide (32 mg, 0.81 mmol, 5 eq.) in water (1 ml) was added and react... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester | Carboxylic acid.Primary alcohol | null | null | c1ccccc1.c1ccc2c(c1)CCC[NH]2.c1ccccc1 | HO- | O.CO.O1CCCC1 | 45 | null | COC(=O)C(C)(C)CCCc1ccc(C(=O)N2c3ccccc3[C@H](N(C(=O)COC(C)=O)c3ccc(Cl)cc3)C[C@@H]2C)cc1>O.CO.O1CCCC1>C[C@H]1C[C@@H](N(C(=O)CO)c2ccc(Cl)cc2)c2ccccc2N1C(=O)c1ccc(CCCC(C)(C)C(=O)O)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-fb6089441de048dca7c3b8795d3d1cdd | COC(=O)[C@@H](C)CCOc1ccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccc(Cl)cc3)CC2C)cc1>>CC(=O)N(c1ccc(Cl)cc1)[C@@H]1CC(C)N(C(=O)c2ccc(OCC[C@H](C)C(=O)O)cc2)c2ccccc21 | COC([C@H](CCOC1=CC=C(C=C1)C(=O)N1C(C[C@H](C2=CC=CC=C12)N(C1=CC=C(C=C1)Cl)C(C)=O)C)C)=O.[OH-].[Li+]>>C(C)(=O)N([C@@H]1CC(N(C2=CC=CC=C12)C(=O)C1=CC=C(OCC[C@@H](C(=O)O)C)C=C1)C)C1=CC=C(C=C1)Cl | C[O:30][C:28]([C@H:26]([CH2:25][CH2:24][O:23][c:22]1[cH:21][cH:20][c:19]([C:17]([N:16]2[CH:14]([CH3:15])[CH2:13][C@@H:12]([N:4]([C:2]([CH3:1])=[O:3])[c:5]3[cH:6][cH:7][c:8]([Cl:9])[cH:10][cH:11]3)[c:38]3[c:33]2[cH:34][cH:35][cH:36][cH:37]3)=[O:18])[cH:32][cH:31]1)[CH3:27])=[O:29]>>[CH3:1][C:2](=[O:3])[N:4]([c:5]1[cH:6]... | COC(=O)[C@@H](C)CCOc1ccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccc(Cl)cc3)CC2C)cc1 | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1CC(C)N(C(=O)c2ccc(OCC[C@H](C)C(=O)O)cc2)c2ccccc21 | null | null | CO.C1CCOC1 | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | O=C(c1ccccc1)N1CC[C@@H](Nc2ccccc2)c2ccccc21 | C-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4]>>[C:3]-[C:2](=[O;D1;H0:4])-[OH;D1;+0:1] | null | [] | null | null | 1 | HOUR | (2S,4R)-4-(4-{4-[Acetyl-(4-chloro-phenyl)-amino]-2-methyl-3,4-dihydro-2H-quinoline-1-carbonyl}-phenoxy)-2-methyl-butyric acid methyl ester (100 mg) was dissolved in methanol/THF, and lithium hydroxide (1.0N, 2 mL) was added. After 1 hour, the reaction was acidified and extracted with methylene chloride. The organic lay... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1.c1ccccc1.c1ccc2c(c1)CCC[NH]2 | Other | CO.C1CCOC1 | null | 1 | COC(=O)[C@@H](C)CCOc1ccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccc(Cl)cc3)CC2C)cc1>CO.C1CCOC1>CC(=O)N(c1ccc(Cl)cc1)[C@@H]1CC(C)N(C(=O)c2ccc(OCC[C@H](C)C(=O)O)cc2)c2ccccc21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-56589fa1b6a84e58a53374ec330369d1 | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(O)cc2)c2ccccc21.O=S(=O)(CCCCl)N(Cc1ccccc1)Cc1ccccc1>>CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(OCCCS(=O)(=O)N(Cc3ccccc3)Cc3ccccc3)cc2)c2ccccc21 | ClC1=CC=C(C=C1)N(C(C)=O)[C@@H]1C[C@@H](N(C2=CC=CC=C12)C(C1=CC=C(C=C1)O)=O)C.C(=O)([O-])[O-].[Cs+].[Cs+].C(C1=CC=CC=C1)N(S(=O)(=O)CCCCl)CC1=CC=CC=C1>>ClC1=CC=C(C=C1)N(C(C)=O)[C@@H]1C[C@@H](N(C2=CC=CC=C12)C(C1=CC=C(C=C1)OCCCS(N(CC1=CC=CC=C1)CC1=CC=CC=C1)(=O)=O)=O)C | [CH3:1][C:2](=[O:3])[N:4]([c:5]1[cH:6][cH:7][c:8]([Cl:9])[cH:10][cH:11]1)[C@@H:12]1[CH2:13][C@H:14]([CH3:15])[N:16]([C:17](=[O:18])[c:19]2[cH:20][cH:21][c:22]([OH:23])[cH:45][cH:46]2)[c:47]2[cH:48][cH:49][cH:50][cH:51][c:52]21.Cl[CH2:24][CH2:25][CH2:26][S:27](=[O:28])(=[O:29])[N:30]([CH2:31][c:32]1[cH:33][cH:34][cH:35]... | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(O)cc2)c2ccccc21.O=S(=O)(CCCCl)N(Cc1ccccc1)Cc1ccccc1 | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(OCCCS(=O)(=O)N(Cc3ccccc3)Cc3ccccc3)cc2)c2ccccc21 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | O=C(c1ccc(OCCCS(=O)(=O)N(Cc2ccccc2)Cc2ccccc2)cc1)N1CC[C@@H](Nc2ccccc2)c2ccccc21 | Cl-[CH2;D2;+0:1]-[C:2]-[C:3].[OH;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:4]-[c:5](:[c:6]):[c:7] | null | [] | null | null | 8 | HOUR | (2S,4R)-N-(4-Chloro-phenyl)-N-[1-(4-hydroxy-benzoyl)-2-methyl-1,2,3,4-tetrahydro-quinolin-4-yl]-acetamide (300 mg, 0.693 mmol) was dissolved in DMF (10 mL) at room temperature. Cs2CO3 (1.12 g, 3.46 mmol) was added followed by 3-chloro-propane-1-sulfonic acid dibenzylamide (350 mg, 1.03 mmol) and the reaction was allowe... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccc2c(c1)CCC[NH]2 | HCl | CN(C)C=O | null | 8 | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(O)cc2)c2ccccc21.O=S(=O)(CCCCl)N(Cc1ccccc1)Cc1ccccc1>CN(C)C=O>CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(OCCCS(=O)(=O)N(Cc3ccccc3)Cc3ccccc3)cc2)c2ccccc21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-11996464a8d143ff8d16b798550d804a | BrCCCN1CCCC1.CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(O)cc2)c2ccccc21>>CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(OCCCN3CCCC3)cc2)c2ccccc21 | ClC1=CC=C(C=C1)N(C(C)=O)[C@@H]1C[C@@H](N(C2=CC=CC=C12)C(C1=CC=C(C=C1)O)=O)C.C(=O)([O-])[O-].[K+].[K+].BrCCCN1CCCC1>>ClC1=CC=C(C=C1)N(C(C)=O)[C@@H]1C[C@@H](N(C2=CC=CC=C12)C(C1=CC=C(C=C1)OCCCN1CCCC1)=O)C | Br[CH2:24][CH2:25][CH2:26][N:27]1[CH2:28][CH2:29][CH2:30][CH2:31]1.[CH3:1][C:2](=[O:3])[N:4]([c:5]1[cH:6][cH:7][c:8]([Cl:9])[cH:10][cH:11]1)[C@@H:12]1[CH2:13][C@H:14]([CH3:15])[N:16]([C:17](=[O:18])[c:19]2[cH:20][cH:21][c:22]([OH:23])[cH:32][cH:33]2)[c:34]2[cH:35][cH:36][cH:37][cH:38][c:39]21>>[CH3:1][C:2](=[O:3])[N:4]... | BrCCCN1CCCC1.CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(O)cc2)c2ccccc21 | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(OCCCN3CCCC3)cc2)c2ccccc21 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | O=C(c1ccc(OCCCN2CCCC2)cc1)N1CC[C@@H](Nc2ccccc2)c2ccccc21 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[OH;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:4]-[c:5](:[c:6]):[c:7] | 8 | [{"value": 8.0, "product": "ClC1=CC=C(C=C1)N(C(C)=O)[C@@H]1C[C@@H](N(C2=CC=CC=C12)C(C1=CC=C(C=C1)OCCCN1CCCC1)=O)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 8.0, "product": "ClC1=CC=C(C=C1)N(C(C)=O)[C@@H]1C[C@@H](N(C2=CC=CC=C12)C(C1=CC=C(C=C1)OCCCN1CCCC1)=O)C", "details": "CALCULATEDPERCENTYIELD", "is... | 80 | CELSIUS | null | null | (2S,4R)-N-(4-Chloro-phenyl)-N-[1-(4-hydroxy-benzoyl)-2-methyl-1,2,3,4-tetrahydro-quinolin-4-yl]-acetamide (0.1 g, 0.23 mmol) was dissolved in DMF (5 mL) at room temperature. K2CO3 (0.317 g, 2.3 mmol) was added. 1-(3-Bromo-propyl)-pyrrolidine (0.177 g, 0.92 mmol) was added and the reaction was allowed to heat to 80° C. ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccccc1.c1ccccc1.C1CC[NH]C1.c1ccc2c(c1)CCC[NH]2 | HBr | CN(C)C=O | 80 | null | BrCCCN1CCCC1.CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(O)cc2)c2ccccc21>CN(C)C=O>CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(OCCCN3CCCC3)cc2)c2ccccc21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-adc59ff1a427431fadd3ec78bed0fab1 | BrCCn1cccc1.CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(O)cc2)c2ccccc21>>CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(OCCn3cccc3)cc2)c2ccccc21 | ClC1=CC=C(C=C1)N(C(C)=O)[C@@H]1C[C@@H](N(C2=CC=CC=C12)C(C1=CC=C(C=C1)O)=O)C.C(=O)([O-])[O-].[K+].[K+].BrCCN1C=CC=C1>>ClC1=CC=C(C=C1)N(C(C)=O)[C@@H]1C[C@@H](N(C2=CC=CC=C12)C(C1=CC=C(C=C1)OCCN1C=CC=C1)=O)C | Br[CH2:24][CH2:25][n:26]1[cH:27][cH:28][cH:29][cH:30]1.[CH3:1][C:2](=[O:3])[N:4]([c:5]1[cH:6][cH:7][c:8]([Cl:9])[cH:10][cH:11]1)[C@@H:12]1[CH2:13][C@H:14]([CH3:15])[N:16]([C:17](=[O:18])[c:19]2[cH:20][cH:21][c:22]([OH:23])[cH:31][cH:32]2)[c:33]2[cH:34][cH:35][cH:36][cH:37][c:38]21>>[CH3:1][C:2](=[O:3])[N:4]([c:5]1[cH:6... | BrCCn1cccc1.CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(O)cc2)c2ccccc21 | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(OCCn3cccc3)cc2)c2ccccc21 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | O=C(c1ccc(OCCn2cccc2)cc1)N1CC[C@@H](Nc2ccccc2)c2ccccc21 | Br-[CH2;D2;+0:1]-[C:2]-[#7;a:3].[OH;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[#7;a:3]-[C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:4]-[c:5](:[c:6]):[c:7] | 86.4 | [{"value": 85.0, "product": "ClC1=CC=C(C=C1)N(C(C)=O)[C@@H]1C[C@@H](N(C2=CC=CC=C12)C(C1=CC=C(C=C1)OCCN1C=CC=C1)=O)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 86.4, "product": "ClC1=CC=C(C=C1)N(C(C)=O)[C@@H]1C[C@@H](N(C2=CC=CC=C12)C(C1=CC=C(C=C1)OCCN1C=CC=C1)=O)C", "details": "CALCULATEDPERCENTYIELD",... | 80 | CELSIUS | null | null | (2S,4R)-N-(4-Chloro-phenyl)-N-[1-(4-hydroxy-benzoyl)-2-methyl-1,2,3,4-tetrahydro-quinolin-4-yl]-acetamide (0.11 g, 0.25 mmol) was dissolved in DMF at room temperature and K2CO3 (0.207 g, 1.5 mmol) was added. 1-(2-Bromo-ethyl)-1H-pyrrole (0.088 g, 0.5 mmol) was added and the reaction was allowed to heat to 80° C. overni... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccccc1.c1ccccc1.c1cc[nH]c1.c1ccc2c(c1)CCC[NH]2 | HBr | CN(C)C=O | 80 | null | BrCCn1cccc1.CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(O)cc2)c2ccccc21>CN(C)C=O>CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(OCCn3cccc3)cc2)c2ccccc21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-b495b5570d75450dbb5cb5295166ab8f | COC(=O)CCc1ccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccc(Cl)cc3)C[C@@H]2C)cc1>>CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(CCC(=O)O)cc2)c2ccccc21 | C(C)(=O)N([C@@H]1C[C@@H](N(C2=CC=CC=C12)C(=O)C1=CC=C(C=C1)CCC(=O)OC)C)C1=CC=C(C=C1)Cl.[OH-].[Na+]>>C(C)(=O)N([C@@H]1C[C@@H](N(C2=CC=CC=C12)C(=O)C1=CC=C(C=C1)CCC(=O)O)C)C1=CC=C(C=C1)Cl | C[O:27][C:25]([CH2:24][CH2:23][c:22]1[cH:21][cH:20][c:19]([C:17]([N:16]2[C@@H:14]([CH3:15])[CH2:13][C@@H:12]([N:4]([C:2]([CH3:1])=[O:3])[c:5]3[cH:6][cH:7][c:8]([Cl:9])[cH:10][cH:11]3)[c:35]3[c:30]2[cH:31][cH:32][cH:33][cH:34]3)=[O:18])[cH:29][cH:28]1)=[O:26]>>[CH3:1][C:2](=[O:3])[N:4]([c:5]1[cH:6][cH:7][c:8]([Cl:9])[cH... | COC(=O)CCc1ccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccc(Cl)cc3)C[C@@H]2C)cc1 | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(CCC(=O)O)cc2)c2ccccc21 | null | null | O.CO.O1CCCC1 | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | O=C(c1ccccc1)N1CC[C@@H](Nc2ccccc2)c2ccccc21 | C-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4]>>[C:3]-[C:2](=[O;D1;H0:4])-[OH;D1;+0:1] | 97 | [{"value": 97.0, "product": "C(C)(=O)N([C@@H]1C[C@@H](N(C2=CC=CC=C12)C(=O)C1=CC=C(C=C1)CCC(=O)O)C)C1=CC=C(C=C1)Cl", "details": "PERCENTYIELD", "is_desired": false}, {"value": 96.7, "product": "C(C)(=O)N([C@@H]1C[C@@H](N(C2=CC=CC=C12)C(=O)C1=CC=C(C=C1)CCC(=O)O)C)C1=CC=C(C=C1)Cl", "details": "CALCULATEDPERCENTYIELD", "is... | null | null | 20 | HOUR | Methyl 3-(4-{[(2S,4R)-4-[acetyl(4-chlorophenyl)amino]-2-methyl-3,4-dihydroquinolin-1(2H)-yl]carbonyl}phenyl)propanoate (200 mg, 0.4 mmol, 1 equ.) was dissolved in methanol/tetrahydrofuran (2/1) (1.5 ml). A solution of sodium hydroxide (32 mg, 0.8 mmol, 2 eq.) in water (0.5 ml) was added and reaction mixture stirred at ... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1.c1ccccc1.c1ccc2c(c1)CCC[NH]2 | Other | O.CO.O1CCCC1 | null | 20 | COC(=O)CCc1ccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccc(Cl)cc3)C[C@@H]2C)cc1>O.CO.O1CCCC1>CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(CCC(=O)O)cc2)c2ccccc21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-3dd36c284a624496a87a2555a9706a99 | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(CCC(=O)O)cc2)c2ccccc21.O=C(Cl)C(=O)Cl>>CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(CCC(=O)Cl)cc2)c2ccccc21 | C(C(=O)Cl)(=O)Cl.C(C)(=O)N([C@@H]1C[C@@H](N(C2=CC=CC=C12)C(=O)C1=CC=C(C=C1)CCC(=O)O)C)C1=CC=C(C=C1)Cl>>C(C)(=O)N([C@@H]1C[C@@H](N(C2=CC=CC=C12)C(=O)C1=CC=C(C=C1)CCC(=O)Cl)C)C1=CC=C(C=C1)Cl | O[C:25]([CH2:24][CH2:23][c:22]1[cH:21][cH:20][c:19]([C:17]([N:16]2[C@@H:14]([CH3:15])[CH2:13][C@@H:12]([N:4]([C:2]([CH3:1])=[O:3])[c:5]3[cH:6][cH:7][c:8]([Cl:9])[cH:10][cH:11]3)[c:35]3[c:30]2[cH:31][cH:32][cH:33][cH:34]3)=[O:18])[cH:29][cH:28]1)=[O:26].O=C(Cl)C(=O)[Cl:27]>>[CH3:1][C:2](=[O:3])[N:4]([c:5]1[cH:6][cH:7][c... | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(CCC(=O)O)cc2)c2ccccc21.O=C(Cl)C(=O)Cl | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(CCC(=O)Cl)cc2)c2ccccc21 | null | null | C(Cl)Cl | Functional Group Interconversion | Alcohol to chloride_Other | 013cec2edeb273a7a148f349d36a52d99ff4e7bcf8eed78085df830088e387ac | aedb1f68dc5b7eb0583043e1125b741382b17974140a2f46554f0110e2ddc884 | O=C(c1ccccc1)N1CC[C@@H](Nc2ccccc2)c2ccccc21 | Cl-C(=O)-C(=O)-[Cl;H0;D1;+0:1].O-[C;H0;D3;+0:2](=[O;D1;H0:3])-[C:4]-[C:5]>>[C:5]-[C:4]-[C;H0;D3;+0:2](-[Cl;H0;D1;+0:1])=[O;D1;H0:3] | null | [] | null | null | null | null | To a suspension of 3-(4-{[(2S,4R)-4-[acetyl(4-chlorophenyl)amino]-2-methyl-3,4-dihydroquinolin-1(2H)-yl]carbonyl}phenyl)propanoic acid (50 mg, 0.10 mmol, 1 equ.) in methylene chloride (0.5 mL) was added a 2M solution of oxalyl chloride in methylene chloride (82 uL, 0.16 mmol, 1.6 equ.). Reaction mixture was stirred at ... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Acyl halide.Carboxylic acid | Acyl halide | null | null | c1ccccc1.c1ccccc1.c1ccc2c(c1)CCC[NH]2 | HCl | C(Cl)Cl | null | null | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(CCC(=O)O)cc2)c2ccccc21.O=C(Cl)C(=O)Cl>C(Cl)Cl>CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(CCC(=O)Cl)cc2)c2ccccc21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-17331d12cad54a429005a613b8ad811b | CCI.COC(=O)NCCCOc1ccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccc(Cl)cc3)C[C@@H]2C)cc1>>CCN(CCCOc1ccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccc(Cl)cc3)C[C@@H]2C)cc1)C(=O)OC | COC(NCCCOC1=CC=C(C=C1)C(=O)N1[C@H](C[C@H](C2=CC=CC=C12)N(C1=CC=C(C=C1)Cl)C(C)=O)C)=O.[H-].[Na+].C(C)I>>COC(N(CC)CCCOC1=CC=C(C=C1)C(=O)N1[C@H](C[C@H](C2=CC=CC=C12)N(C1=CC=C(C=C1)Cl)C(C)=O)C)=O | I[CH2:2][CH3:1].[NH:3]([CH2:4][CH2:5][CH2:6][O:7][c:8]1[cH:9][cH:10][c:11]([C:12](=[O:13])[N:14]2[c:15]3[cH:16][cH:17][cH:18][cH:19][c:20]3[C@H:21]([N:22]([C:23]([CH3:24])=[O:25])[c:26]3[cH:27][cH:28][c:29]([Cl:30])[cH:31][cH:32]3)[CH2:33][C@@H:34]2[CH3:35])[cH:36][cH:37]1)[C:38](=[O:39])[O:40][CH3:41]>>[CH3:1][CH2:2][... | CCI.COC(=O)NCCCOc1ccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccc(Cl)cc3)C[C@@H]2C)cc1 | CCN(CCCOc1ccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccc(Cl)cc3)C[C@@H]2C)cc1)C(=O)OC | null | null | C1CCOC1.CN(C)C=O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 5da873da5e065666521679df8db5a1d2754540edd93ae40997847c9a24dedeb3 | c05cd517c346aa4e8e8e58218c491edaea33d354b5dba9eb90dac8ad97104f73 | O=C(c1ccccc1)N1CC[C@@H](Nc2ccccc2)c2ccccc21 | I-[CH2;D2;+0:1]-[C;D1;H3:2].[C:3]-[C:4]-[NH;D2;+0:5]-[C:6](=[O;D1;H0:7])-[#8:8]-[C;D1;H3:9]>>[C:3]-[C:4]-[N;H0;D3;+0:5](-[CH2;D2;+0:1]-[C;D1;H3:2])-[C:6](=[O;D1;H0:7])-[#8:8]-[C;D1;H3:9] | 35.1 | [{"value": 35.0, "product": "COC(N(CC)CCCOC1=CC=C(C=C1)C(=O)N1[C@H](C[C@H](C2=CC=CC=C12)N(C1=CC=C(C=C1)Cl)C(C)=O)C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 35.1, "product": "COC(N(CC)CCCOC1=CC=C(C=C1)C(=O)N1[C@H](C[C@H](C2=CC=CC=C12)N(C1=CC=C(C=C1)Cl)C(C)=O)C)=O", "details": "CALCULATEDPERCENTYIE... | null | null | 7 | HOUR | (2S,4R)-[3-(4-{4-[Acetyl-(4-chloro-phenyl)-amino]-2-methyl-3,4-dihydro-2H-quinoline-1-carbonyl}-phenoxy)-propyl]-carbamic acid methyl ester (41 mg, 0.074 mmol) was dissolved in THF/DMF (10:1, 3 mL). To this solution was added Sodium Hydride (2 mg, 0.089 mmol), followed by ethyl iodide (14 mg, 0.089 mmol). The reaction ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Carbamic ester | Carbamic ester | null | null | c1ccccc1.c1ccccc1.c1ccc2c(c1)CCC[NH]2 | HI | C1CCOC1.CN(C)C=O | null | 7 | CCI.COC(=O)NCCCOc1ccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccc(Cl)cc3)C[C@@H]2C)cc1>C1CCOC1.CN(C)C=O>CCN(CCCOc1ccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccc(Cl)cc3)C[C@@H]2C)cc1)C(=O)OC |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-9e46bdd784874040a700a6bd4b91755e | CCOC(=O)c1nccn1CCCOc1ccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccc(Cl)cc3)C[C@@H]2C)cc1>>CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(OCCCn3ccnc3C(=O)O)cc2)c2ccccc21 | C(C)OC(=O)C=1N(C=CN1)CCCOC1=CC=C(C=C1)C(=O)N1[C@H](C[C@H](C2=CC=CC=C12)N(C1=CC=C(C=C1)Cl)C(C)=O)C.C(C)O.[OH-].[Na+]>>C(C)(=O)N([C@@H]1C[C@@H](N(C2=CC=CC=C12)C(=O)C1=CC=C(OCCCN2C(=NC=C2)C(=O)O)C=C1)C)C1=CC=C(C=C1)Cl | CC[O:34][C:32]([c:31]1[n:27]([CH2:26][CH2:25][CH2:24][O:23][c:22]2[cH:21][cH:20][c:19]([C:17]([N:16]3[C@@H:14]([CH3:15])[CH2:13][C@@H:12]([N:4]([C:2]([CH3:1])=[O:3])[c:5]4[cH:6][cH:7][c:8]([Cl:9])[cH:10][cH:11]4)[c:42]4[c:37]3[cH:38][cH:39][cH:40][cH:41]4)=[O:18])[cH:36][cH:35]2)[cH:28][cH:29][n:30]1)=[O:33]>>[CH3:1][C... | CCOC(=O)c1nccn1CCCOc1ccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccc(Cl)cc3)C[C@@H]2C)cc1 | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(OCCCn3ccnc3C(=O)O)cc2)c2ccccc21 | null | null | O1CCCC1 | Deprotection | Ester saponification (alkyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | O=C(c1ccc(OCCCn2ccnc2)cc1)N1CC[C@@H](Nc2ccccc2)c2ccccc21 | C-C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4](:[#7;a:5]):[#7;a:6]>>[#7;a:5]:[c:4](-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1]):[#7;a:6] | null | [] | null | null | 4 | HOUR | (2S,4R)-1-[3-(4-{4-[Acetyl-(4-chloro-phenyl)-amino]-2-methyl-3,4-dihydro-2H-quinoline-1-carbonyl}-phenoxy)-propyl]-1H-imidazole-2-carboxylic acid was prepared from (2S,4R)-1-[3-(4-{4-[Acetyl-(4-chloro-phenyl)-amino]-2-methyl-3,4-dihydro-2H-quinoline-1-carbonyl}-phenoxy)-propyl]-1H-imidazole-2-carboxylic acid ethyl este... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1.c1ccccc1.c1ncc[nH]1.c1ccc2c(c1)CCC[NH]2 | Other | O1CCCC1 | null | 4 | CCOC(=O)c1nccn1CCCOc1ccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccc(Cl)cc3)C[C@@H]2C)cc1>O1CCCC1>CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(OCCCn3ccnc3C(=O)O)cc2)c2ccccc21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-24036d097c5e4d478cc10670b5160b4a | COC(=O)C(C)(C)CCOc1ccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccc(Cl)cc3C)C[C@@H]2C)cc1>>CC(=O)N(c1ccc(Cl)cc1C)[C@@H]1C[C@H](C)N(C(=O)c2ccc(OCCC(C)(C)C(=O)O)cc2)c2ccccc21 | C(C)(=O)N([C@@H]1C[C@@H](N(C2=CC=CC=C12)C(=O)C1=CC=C(OCCC(C(=O)OC)(C)C)C=C1)C)C1=C(C=C(C=C1)Cl)C.[OH-].[Na+]>>C(C)(=O)N([C@@H]1C[C@@H](N(C2=CC=CC=C12)C(=O)C1=CC=C(OCCC(C(=O)O)(C)C)C=C1)C)C1=C(C=C(C=C1)Cl)C | C[O:32][C:30]([C:27]([CH2:26][CH2:25][O:24][c:23]1[cH:22][cH:21][c:20]([C:18]([N:17]2[C@@H:15]([CH3:16])[CH2:14][C@@H:13]([N:4]([C:2]([CH3:1])=[O:3])[c:5]3[cH:6][cH:7][c:8]([Cl:9])[cH:10][c:11]3[CH3:12])[c:40]3[c:35]2[cH:36][cH:37][cH:38][cH:39]3)=[O:19])[cH:34][cH:33]1)([CH3:28])[CH3:29])=[O:31]>>[CH3:1][C:2](=[O:3])[... | COC(=O)C(C)(C)CCOc1ccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccc(Cl)cc3C)C[C@@H]2C)cc1 | CC(=O)N(c1ccc(Cl)cc1C)[C@@H]1C[C@H](C)N(C(=O)c2ccc(OCCC(C)(C)C(=O)O)cc2)c2ccccc21 | null | null | O.CO.O1CCCC1 | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | O=C(c1ccccc1)N1CC[C@@H](Nc2ccccc2)c2ccccc21 | C-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4]>>[C:3]-[C:2](=[O;D1;H0:4])-[OH;D1;+0:1] | 89 | [{"value": 89.0, "product": "C(C)(=O)N([C@@H]1C[C@@H](N(C2=CC=CC=C12)C(=O)C1=CC=C(OCCC(C(=O)O)(C)C)C=C1)C)C1=C(C=C(C=C1)Cl)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 88.8, "product": "C(C)(=O)N([C@@H]1C[C@@H](N(C2=CC=CC=C12)C(=O)C1=CC=C(OCCC(C(=O)O)(C)C)C=C1)C)C1=C(C=C(C=C1)Cl)C", "details": "CALCUL... | 40 | CELSIUS | null | null | Methyl 4-(4-{[(2S,4R)-4-[acetyl(4-chloro-2-methylphenyl)amino]-2-methyl-3,4-dihydroquinolin-1(2H)-yl]carbonyl}phenoxy)-2,2-dimethylbutanoate (60 mg, 0.10 mmol, 1 equ.) was dissolved in methanol/tetrahydrofuran (2/1) (0.8 ml). A solution of sodium hydroxide (12 mg, 0.30 mmol, 3 eq.) in water (0.3 ml) was added and react... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1.c1ccccc1.c1ccc2c(c1)CCC[NH]2 | Other | O.CO.O1CCCC1 | 40 | null | COC(=O)C(C)(C)CCOc1ccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccc(Cl)cc3C)C[C@@H]2C)cc1>O.CO.O1CCCC1>CC(=O)N(c1ccc(Cl)cc1C)[C@@H]1C[C@H](C)N(C(=O)c2ccc(OCCC(C)(C)C(=O)O)cc2)c2ccccc21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-b70de0fb9b724dd1a566f43523d1135c | C=[CH][Sn]([CH2]CCC)([CH2]CCC)[CH2]CCC.COC(=O)c1ccc(Br)c(F)c1>>C=Cc1ccc(C(=O)OC)cc1F | BrC1=C(C=C(C(=O)OC)C=C1)F.C(=C)[Sn](CCCC)(CCCC)CCCC>>FC=1C=C(C(=O)OC)C=CC1C=C | CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[CH:2]=[CH2:1].Br[c:3]1[cH:4][cH:5][c:6]([C:7](=[O:8])[O:9][CH3:10])[cH:11][c:12]1[F:13]>>[CH2:1]=[CH:2][c:3]1[cH:4][cH:5][c:6]([C:7](=[O:8])[O:9][CH3:10])[cH:11][c:12]1[F:13] | C=[CH][Sn]([CH2]CCC)([CH2]CCC)[CH2]CCC.COC(=O)c1ccc(Br)c(F)c1 | C=Cc1ccc(C(=O)OC)cc1F | null | Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl | CN(C)C=O.C(C)(=O)OCC | C-C Coupling | Stille reaction_vinyl | 70c70ea31829ab76af60acb09a55c00bc191f62cf69589ba5bf99dde81769bb5 | ec03c739f58696d2a3659a73884744e1a490a20a587da6f115be382b663cf23d | c1ccccc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[F;D1;H0:5]):[c:6].C-C-C-[CH2]-[Sn](-[CH2]-C-C-C)(-[CH2]-C-C-C)-[CH;D2;+0:7]=[C;D1;H2:8]>>[C;D1;H2:8]=[CH;D2;+0:7]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[F;D1;H0:5]):[c:6] | 63 | [{"value": 63.0, "product": "FC=1C=C(C(=O)OC)C=CC1C=C", "details": "PERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | 30 | MINUTE | N-(4-chlorophenyl)-N-[(2S,4R)-1-(4-ethyl-3-fluorobenzoyl)-2-methyl-1,2,3,4-tetrahydroquinolin-4-yl]acetamide was prepared following general procedure B, substituting 4-ethyl-3-fluorobenzoyl chloride for 6-trifluoromethyl nicotinyl chloride. (4-ethyl-3-fluorobenzoyl chloride was prepared in five steps from commercially ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Vinyl.Tin | Vinyl | c1ccccc1 | c1ccccc1 | c1ccccc1 | HBr.Sn | Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl.CN(C)C=O.C(C)(=O)OCC | 80 | 0.5 | C=[CH][Sn]([CH2]CCC)([CH2]CCC)[CH2]CCC.COC(=O)c1ccc(Br)c(F)c1>Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl.CN(C)C=O.C(C)(=O)OCC>C=Cc1ccc(C(=O)OC)cc1F |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-3c9fe93ae3954a77a77e679d3adec348 | C=Cc1ccc(C(=O)OC)cc1F>>CCc1ccc(C(=O)OC)cc1F | FC=1C=C(C(=O)OC)C=CC1C=C>>C(C)C1=C(C=C(C(=O)OC)C=C1)F | [CH2:1]=[CH:2][c:3]1[cH:4][cH:5][c:6]([C:7](=[O:8])[O:9][CH3:10])[cH:11][c:12]1[F:13]>>[CH3:1][CH2:2][c:3]1[cH:4][cH:5][c:6]([C:7](=[O:8])[O:9][CH3:10])[cH:11][c:12]1[F:13] | C=Cc1ccc(C(=O)OC)cc1F | CCc1ccc(C(=O)OC)cc1F | null | [Pd] | C(C)O | Reduction | Hydrogenation (double to single) | 8276b4fb5ddc7d15dec6d92474e91e2dbb2fb8b81e5b5720762e5d89cb27aa69 | 1ccae9f2e86499601fc3421041ff4588c8e6fd53048e86c3b6ed12ae873609c0 | c1ccccc1 | [CH2;D1;+0:1]=[CH;D2;+0:2]-[c:3](:[c:4]):[c:5]>>[CH3;D1;+0:1]-[CH2;D2;+0:2]-[c:3](:[c:4]):[c:5] | 60.2 | [{"value": 59.0, "product": "C(C)C1=C(C=C(C(=O)OC)C=C1)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 60.2, "product": "C(C)C1=C(C=C(C(=O)OC)C=C1)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | N-(4-chlorophenyl)-N-[(2S,4R)-1-(4-ethyl-3-fluorobenzoyl)-2-methyl-1,2,3,4-tetrahydroquinolin-4-yl]acetamide was prepared following general procedure B, substituting 4-ethyl-3-fluorobenzoyl chloride for 6-trifluoromethyl nicotinyl chloride. (4-ethyl-3-fluorobenzoyl chloride was prepared in five steps from commercially ... | 10.6084/m9.figshare.5104873.v1 | null | Vinyl | null | null | null | c1ccccc1 | null | [Pd].C(C)O | null | null | C=Cc1ccc(C(=O)OC)cc1F>[Pd].C(C)O>CCc1ccc(C(=O)OC)cc1F |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-3d13f4cea48c43e998edb5ce8a00af64 | COC(=O)C(C)(C)CCOc1ccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccc(Cl)cc3)C[C@@H]2C)cn1>>CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(OCCC(C)(C)C(=O)O)nc2)c2ccccc21 | Cl.C(C)(=O)N([C@@H]1C[C@@H](N(C2=CC=CC=C12)C(=O)C=1C=CC(=NC1)OCCC(C(=O)OC)(C)C)C)C1=CC=C(C=C1)Cl.CO.[OH-].[Na+].C(C)(=O)N([C@@H]1C[C@@H](N(C2=CC=CC=C12)C(=O)C=1C=CC(=NC1)OCCC(C(=O)OC)(C)C)C)C1=CC=C(C=C1)Cl>>C(C)(=O)N([C@@H]1C[C@@H](N(C2=CC=CC=C12)C(=O)C=1C=CC(=NC1)OCCC(C(=O)O)(C)C)C)C1=CC=C(C=C1)Cl | C[O:31][C:29]([C:26]([CH2:25][CH2:24][O:23][c:22]1[cH:21][cH:20][c:19]([C:17]([N:16]2[C@@H:14]([CH3:15])[CH2:13][C@@H:12]([N:4]([C:2]([CH3:1])=[O:3])[c:5]3[cH:6][cH:7][c:8]([Cl:9])[cH:10][cH:11]3)[c:39]3[c:34]2[cH:35][cH:36][cH:37][cH:38]3)=[O:18])[cH:33][n:32]1)([CH3:27])[CH3:28])=[O:30]>>[CH3:1][C:2](=[O:3])[N:4]([c:... | COC(=O)C(C)(C)CCOc1ccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccc(Cl)cc3)C[C@@H]2C)cn1 | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(OCCC(C)(C)C(=O)O)nc2)c2ccccc21 | null | null | O1CCCC1 | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | O=C(c1cccnc1)N1CC[C@@H](Nc2ccccc2)c2ccccc21 | C-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4]>>[C:3]-[C:2](=[O;D1;H0:4])-[OH;D1;+0:1] | 42 | [{"value": 42.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | 4-[(5-{[(2S,4R)-4-[acetyl(4-chlorophenyl)amino]-2-methyl-3,4-dihydroquinolin-1(2H)-yl]carbonyl}pyridin-2-yl)oxy]-2,2-dimethylbutanoic acid was prepared from methyl 4-[(5-{[(2S,4R)-4-[acetyl(4-chlorophenyl)amino]-2-methyl-3,4-dihydroquinolin-1(2H)-yl]carbonyl}pyridin-2-yl)oxy]-2,2-dimethylbutanoate. methyl 4-[(5-{[(2S,4... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1.c1ccncc1.c1ccc2c(c1)CCC[NH]2 | Other | O1CCCC1 | null | 8 | COC(=O)C(C)(C)CCOc1ccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccc(Cl)cc3)C[C@@H]2C)cn1>O1CCCC1>CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(OCCC(C)(C)C(=O)O)nc2)c2ccccc21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-0dc935bc31f744fd9decd418eac7e97d | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)Nc2ccccc21.COC(=O)C(C)(C)CCCc1ccc(C(=O)Cl)cc1>>COC(=O)C(C)(C)CCCc1ccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccc(Cl)cc3)C[C@@H]2C)cc1 | ClC(=O)C1=CC=C(C=C1)CCCC(C(=O)OC)(C)C.ClC1=CC=C(C=C1)N(C(C)=O)[C@@H]1C[C@@H](NC2=CC=CC=C12)C.C(C)(C)N(CC)C(C)C>>COC(C(CCCC1=CC=C(C=C1)C(=O)N1[C@H](C[C@H](C2=CC=CC=C12)N(C1=CC=C(C=C1)Cl)C(C)=O)C)(C)C)=O | [NH:17]1[c:18]2[cH:19][cH:20][cH:21][cH:22][c:23]2[C@H:24]([N:25]([C:26]([CH3:27])=[O:28])[c:29]2[cH:30][cH:31][c:32]([Cl:33])[cH:34][cH:35]2)[CH2:36][C@@H:37]1[CH3:38].Cl[C:15]([c:14]1[cH:13][cH:12][c:11]([CH2:10][CH2:9][CH2:8][C:5]([C:3]([O:2][CH3:1])=[O:4])([CH3:6])[CH3:7])[cH:40][cH:39]1)=[O:16]>>[CH3:1][O:2][C:3](... | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)Nc2ccccc21.COC(=O)C(C)(C)CCCc1ccc(C(=O)Cl)cc1 | COC(=O)C(C)(C)CCCc1ccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccc(Cl)cc3)C[C@@H]2C)cc1 | null | null | C(Cl)Cl | Acylation | N-alkylation of secondary amines with alkyl halides | 20af49e2ebd8e13ce8273786fd70e980d9c80eb9362be37fe2fe9cf2d75c9b8d | 96cb0a2fed10552c5770a45a2d6523b47ac3e38928b4a9c698d8577451182dcd | O=C(c1ccccc1)N1CC[C@@H](Nc2ccccc2)c2ccccc21 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[C:6]-[C:7](-[C;D1;H3:8])-[NH;D2;+0:9]-[c:10](:[c:11]):[c:12]>>[C:6]-[C:7](-[C;D1;H3:8])-[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] | 50.1 | [{"value": 50.0, "product": "COC(C(CCCC1=CC=C(C=C1)C(=O)N1[C@H](C[C@H](C2=CC=CC=C12)N(C1=CC=C(C=C1)Cl)C(C)=O)C)(C)C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 50.1, "product": "COC(C(CCCC1=CC=C(C=C1)C(=O)N1[C@H](C[C@H](C2=CC=CC=C12)N(C1=CC=C(C=C1)Cl)C(C)=O)C)(C)C)=O", "details": "CALCULATEDPERCENTY... | null | null | 20 | HOUR | To the prepared methyl 5-[4-(chlorocarbonyl)phenyl]-2,2-dimethylpentanoate (2.9 mmol, 1.0 eq.) was added a solution of N-(4-chlorophenyl)-N-((2S,4R)-2-methyl-1,2,3,4-tetrahydroquinolin-4-yl)acetamide (754 mg, 2.4 mmol, 0.83 eq.) in methylene chloride (8 ml) followed by diisopropylethylamine (505 ul, 2.9 mmol, 1.0 eq.) ... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Secondary amine | Tertiary amide | c1ccc2c(c1)CCCN2 | c1ccc2c(c1)CCC[NH]2 | c1ccccc1.c1ccccc1.c1ccc2c(c1)CCC[NH]2 | HCl | C(Cl)Cl | null | 20 | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)Nc2ccccc21.COC(=O)C(C)(C)CCCc1ccc(C(=O)Cl)cc1>C(Cl)Cl>COC(=O)C(C)(C)CCCc1ccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccc(Cl)cc3)C[C@@H]2C)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-9bbab0f80c2948218b2f134492dfe5cf | BrCCCn1ccnc1.CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(O)cc2)c2ccccc21>>CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(OCCCn3ccnc3)cc2)c2ccccc21 | ClC1=CC=C(C=C1)N(C(C)=O)[C@@H]1C[C@@H](N(C2=CC=CC=C12)C(C1=CC=C(C=C1)O)=O)C.C(=O)([O-])[O-].[K+].[K+].BrCCCN1C=NC=C1>>ClC1=CC=C(C=C1)N(C(C)=O)[C@@H]1C[C@@H](N(C2=CC=CC=C12)C(C1=CC=C(C=C1)OCCCN1C=NC=C1)=O)C | Br[CH2:24][CH2:25][CH2:26][n:27]1[cH:28][cH:29][n:30][cH:31]1.[CH3:1][C:2](=[O:3])[N:4]([c:5]1[cH:6][cH:7][c:8]([Cl:9])[cH:10][cH:11]1)[C@@H:12]1[CH2:13][C@H:14]([CH3:15])[N:16]([C:17](=[O:18])[c:19]2[cH:20][cH:21][c:22]([OH:23])[cH:32][cH:33]2)[c:34]2[cH:35][cH:36][cH:37][cH:38][c:39]21>>[CH3:1][C:2](=[O:3])[N:4]([c:5... | BrCCCn1ccnc1.CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(O)cc2)c2ccccc21 | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(OCCCn3ccnc3)cc2)c2ccccc21 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | O=C(c1ccc(OCCCn2ccnc2)cc1)N1CC[C@@H](Nc2ccccc2)c2ccccc21 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[OH;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:4]-[c:5](:[c:6]):[c:7] | 16 | [{"value": 16.0, "product": "ClC1=CC=C(C=C1)N(C(C)=O)[C@@H]1C[C@@H](N(C2=CC=CC=C12)C(C1=CC=C(C=C1)OCCCN1C=NC=C1)=O)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 16.0, "product": "ClC1=CC=C(C=C1)N(C(C)=O)[C@@H]1C[C@@H](N(C2=CC=CC=C12)C(C1=CC=C(C=C1)OCCCN1C=NC=C1)=O)C", "details": "CALCULATEDPERCENTYIELD... | 80 | CELSIUS | null | null | (2S,4R)-N-(4-Chloro-phenyl)-N-[1-(4-hydroxy-benzoyl)-2-methyl-1,2,3,4-tetrahydro-quinolin-4-yl]-acetamide (0.1 g, 0.23 mmol) was dissolved in DMF (5 mL) at room temperature. K2CO3 (0.317 g, 2.3 mmol) was added. 1-(3-Bromo-propyl)-1H-imidazole (0.174 g, 0.92 mmol) was added and the reaction was allowed to heat to 80° C.... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccccc1.c1ccccc1.c1c[nH]cn1.c1ccc2c(c1)CCC[NH]2 | HBr | CN(C)C=O | 80 | null | BrCCCn1ccnc1.CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(O)cc2)c2ccccc21>CN(C)C=O>CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(OCCCn3ccnc3)cc2)c2ccccc21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-53f9f1eb473e4331b8cd505a7ed7e611 | COc1ccc(C(=O)N2c3ccccc3[C@H](N)C[C@@H]2C)cc1.O=C1CCCC1>>COc1ccc(C(=O)N2c3ccccc3[C@H](NC3CCCC3)C[C@@H]2C)cc1 | CC(=O)O.[BH-](OC(=O)C)(OC(=O)C)OC(=O)C.[Na+].COC1=CC=C(C(=O)N2[C@H](C[C@H](C3=CC=CC=C23)N)C)C=C1.C1(CCCC1)=O>>C1(CCCC1)N[C@@H]1C[C@@H](N(C2=CC=CC=C12)C(C1=CC=C(C=C1)OC)=O)C | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([C:7](=[O:8])[N:9]2[c:10]3[cH:11][cH:12][cH:13][cH:14][c:15]3[C@H:16]([NH2:17])[CH2:23][C@@H:24]2[CH3:25])[cH:26][cH:27]1.O=[C:18]1[CH2:19][CH2:20][CH2:21][CH2:22]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([C:7](=[O:8])[N:9]2[c:10]3[cH:11][cH:12][cH:13][cH:14][c:15]3[C@H:16]([NH:17][CH:1... | COc1ccc(C(=O)N2c3ccccc3[C@H](N)C[C@@H]2C)cc1.O=C1CCCC1 | COc1ccc(C(=O)N2c3ccccc3[C@H](NC3CCCC3)C[C@@H]2C)cc1 | null | null | CO | Heteroatom Alkylation and Arylation | Reductive amination with ketone | b85679fed5f5625b57908374666b40667904d1ae7fb913f5564f84f7e4e3c6f0 | 07faf85ffe990e88a1de7fd04a339bf226f78d8bfae9712ea59eebd76bb54b9f | O=C(c1ccccc1)N1CC[C@@H](NC2CCCC2)c2ccccc21 | O=[C;H0;D3;+0:1]1-[C:2]-[C:3]-[C:4]-[C:5]-1.[C:6]-[C:7](-[NH2;D1;+0:8])-[c:9]>>[C:6]-[C:7](-[NH;D2;+0:8]-[CH;D3;+0:1]1-[C:2]-[C:3]-[C:4]-[C:5]-1)-[c:9] | null | [] | null | null | null | null | To (2S,4R)-1-(4-methoxybenzoyl)-2-methyl-1,2,3,4-tetrahydroquinolin-4-amine (200 mg, 0.67 mmol) in MeOH was added cyclopentanone (0.073 mL, 0.74 mmol) followed Na(OAc)3BH (284 mg, 1.34 mmol) and catalytic amount of HOAc. The reaction mixture was stirred at room temperature over night. The reaction wash quenched by addi... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Primary amine | Secondary amine | C1CCCC1 | C1CCCC1 | c1ccccc1.C1CCCC1.c1ccc2c(c1)CCC[NH]2 | Other | CO | null | null | COc1ccc(C(=O)N2c3ccccc3[C@H](N)C[C@@H]2C)cc1.O=C1CCCC1>CO>COc1ccc(C(=O)N2c3ccccc3[C@H](NC3CCCC3)C[C@@H]2C)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-cdb556d8e55a4441ab25dc1e72e2e6dd | CC(=O)Cl.COc1ccc(C(=O)N2c3ccccc3[C@H](NC3CCCC3)C[C@@H]2C)cc1>>COc1ccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)C3CCCC3)C[C@@H]2C)cc1 | C(C)(=O)Cl.C1(CCCC1)N[C@@H]1C[C@@H](N(C2=CC=CC=C12)C(C1=CC=C(C=C1)OC)=O)C.C(C)(C)N(CC)C(C)C>>C1(CCCC1)N(C(C)=O)[C@@H]1C[C@@H](N(C2=CC=CC=C12)C(C1=CC=C(C=C1)OC)=O)C | Cl[C:18]([CH3:19])=[O:20].[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([C:7](=[O:8])[N:9]2[c:10]3[cH:11][cH:12][cH:13][cH:14][c:15]3[C@H:16]([NH:17][CH:21]3[CH2:22][CH2:23][CH2:24][CH2:25]3)[CH2:26][C@@H:27]2[CH3:28])[cH:29][cH:30]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([C:7](=[O:8])[N:9]2[c:10]3[cH:11][cH:12][cH:13][cH:14][c:15... | CC(=O)Cl.COc1ccc(C(=O)N2c3ccccc3[C@H](NC3CCCC3)C[C@@H]2C)cc1 | COc1ccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)C3CCCC3)C[C@@H]2C)cc1 | null | null | C(Cl)Cl | Acylation | N-alkylation of secondary amines with alkyl halides | b92e0bfd3d683c1f2a209adfe70a67ad7cb0d87749eb59e8fe0cf1689bc291e0 | 96cb0a2fed10552c5770a45a2d6523b47ac3e38928b4a9c698d8577451182dcd | O=C(c1ccccc1)N1CC[C@@H](NC2CCCC2)c2ccccc21 | Cl-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[C:4]-[C:5](-[NH;D2;+0:6]-[C:7](-[C:8])-[c:9])-[C:10]>>[C:4]-[C:5](-[N;H0;D3;+0:6](-[C:7](-[C:8])-[c:9])-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3])-[C:10] | 91 | [{"value": 91.0, "product": "C1(CCCC1)N(C(C)=O)[C@@H]1C[C@@H](N(C2=CC=CC=C12)C(C1=CC=C(C=C1)OC)=O)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 89.7, "product": "C1(CCCC1)N(C(C)=O)[C@@H]1C[C@@H](N(C2=CC=CC=C12)C(C1=CC=C(C=C1)OC)=O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 4 | HOUR | To a solution (2S,4R)-N-cyclopentyl-1-(4-methoxybenzoyl)-2-methyl-1,2,3,4-tetrahydroquinolin-4-amine (100 mg, 02.7 mmol) in methylene chloride (5 mL) was added diisopropylethylamine (120 uL, 0.70 mmol) followed by acetyl chloride (90 uL, 1.27 mmol). The mixture was stirred at r.t. for 4 h. The reaction mixture was conc... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Secondary amine | Tertiary amide | null | null | c1ccccc1.C1CCCC1.c1ccc2c(c1)CCC[NH]2 | HCl | C(Cl)Cl | null | 4 | CC(=O)Cl.COc1ccc(C(=O)N2c3ccccc3[C@H](NC3CCCC3)C[C@@H]2C)cc1>C(Cl)Cl>COc1ccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)C3CCCC3)C[C@@H]2C)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-fb69e9ba6442445fac86588a7bc8c173 | CC(=O)N(C1CC1)C1CC(C)N(C(=O)OCc2ccccc2)c2ccccc21>>CC(=O)N(C1CC1)C1CC(C)Nc2ccccc21 | C(C1=CC=CC=C1)OC(=O)N1C(CC(C2=CC=CC=C12)N(C1CC1)C(C)=O)C>>C1(CC1)N(C(C)=O)C1CC(NC2=CC=CC=C12)C | O=C(OCc1ccccc1)[N:12]1[CH:10]([CH3:11])[CH2:9][CH:8]([N:4]([C:2]([CH3:1])=[O:3])[CH:5]2[CH2:6][CH2:7]2)[c:18]2[c:13]1[cH:14][cH:15][cH:16][cH:17]2>>[CH3:1][C:2](=[O:3])[N:4]([CH:5]1[CH2:6][CH2:7]1)[CH:8]1[CH2:9][CH:10]([CH3:11])[NH:12][c:13]2[cH:14][cH:15][cH:16][cH:17][c:18]21 | CC(=O)N(C1CC1)C1CC(C)N(C(=O)OCc2ccccc2)c2ccccc21 | CC(=O)N(C1CC1)C1CC(C)Nc2ccccc21 | null | [Pd] | CO | Reduction | Hydrogenolysis of tertiary amines | 7812cd90425bf85db01af6f04ff691ae52b54dad7d40e20fac978418b9a17d98 | 20c36f41eeb07c3ba4437b51ba72e8ff3c22d0b27e7197b0e9af3127f331149f | c1ccc2c(c1)NCCC2NC1CC1 | O=C(-O-C-c1:c:c:c:c:c:1)-[N;H0;D3;+0:1](-[C:2](-[C;D1;H3:3])-[C:4])-[c:5](:[c:6]):[c:7]>>[C:4]-[C:2](-[C;D1;H3:3])-[NH;D2;+0:1]-[c:5](:[c:6]):[c:7] | null | [] | null | null | 8 | HOUR | Benzyl-4-[acetyl(cyclopropyl)amino]-2-methyl-3,4-dihydroquinoline-1(2H)-carboxylate was dissolved in MeOH and a catalytic amount of Palladium on Carbon (10%) was added. The round bottom flask in which resided the resulting solution was evacuated and backfilled with hydrogen. The reaction was stirred under the hydrogen ... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether | Secondary amine | c1ccccc1.c1ccc2c(c1)CCC[NH]2 | c1ccc2c(c1)CCCN2 | C1CC1.c1ccc2c(c1)CCCN2 | HO- | [Pd].CO | null | 8 | CC(=O)N(C1CC1)C1CC(C)N(C(=O)OCc2ccccc2)c2ccccc21>[Pd].CO>CC(=O)N(C1CC1)C1CC(C)Nc2ccccc21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-52d543bd840c486ca4af19ce8488adf5 | CC(=O)N(C1CC1)C1CC(C)Nc2ccccc21.O=C(Cl)c1cccnc1>>CC(=O)N(C1CC1)C1CC(C)N(C(=O)c2cccnc2)c2ccccc21 | CCN(C(C)C)C(C)C.C1(CC1)N(C(C)=O)C1CC(NC2=CC=CC=C12)C.Cl.C(C1=CN=CC=C1)(=O)Cl>>C1(CC1)N(C(C)=O)C1CC(N(C2=CC=CC=C12)C(=O)C=1C=NC=CC1)C | [CH3:1][C:2](=[O:3])[N:4]([CH:5]1[CH2:6][CH2:7]1)[CH:8]1[CH2:9][CH:10]([CH3:11])[NH:12][c:21]2[cH:22][cH:23][cH:24][cH:25][c:26]21.Cl[C:13](=[O:14])[c:15]1[cH:16][cH:17][cH:18][n:19][cH:20]1>>[CH3:1][C:2](=[O:3])[N:4]([CH:5]1[CH2:6][CH2:7]1)[CH:8]1[CH2:9][CH:10]([CH3:11])[N:12]([C:13](=[O:14])[c:15]2[cH:16][cH:17][cH:1... | CC(=O)N(C1CC1)C1CC(C)Nc2ccccc21.O=C(Cl)c1cccnc1 | CC(=O)N(C1CC1)C1CC(C)N(C(=O)c2cccnc2)c2ccccc21 | null | null | C(Cl)Cl | Acylation | N-alkylation of secondary amines with alkyl halides | 20af49e2ebd8e13ce8273786fd70e980d9c80eb9362be37fe2fe9cf2d75c9b8d | 96cb0a2fed10552c5770a45a2d6523b47ac3e38928b4a9c698d8577451182dcd | O=C(c1cccnc1)N1CCC(NC2CC2)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](-[C;D1;H3:10])-[NH;D2;+0:11]-[c:12](:[c:13]):[c:14]>>[C:8]-[C:9](-[C;D1;H3:10])-[N;H0;D3;+0:11](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5]:[#7;a:6]:[c:7])-[c:12](:[c:13]):[c:14] | 68.2 | [{"value": 68.0, "product": "C1(CC1)N(C(C)=O)C1CC(N(C2=CC=CC=C12)C(=O)C=1C=NC=CC1)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 68.2, "product": "C1(CC1)N(C(C)=O)C1CC(N(C2=CC=CC=C12)C(=O)C=1C=NC=CC1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | To the solution of N-cyclopropyl-N-(2-methyl-1,2,3,4-tetrahydro-quinolin-4-yl)-acetamide (82 mg, 0.34 mmol) in DCM (5 mL) was added nicotinoyl chloride hydrochloride (71 mg, 0.40 mmol), followed by DIPEA (104 mg, 0.80 mmol). The reaction mixture was stirred at r.t. for overnight. The mixture was concentrated under redu... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Secondary amine | Tertiary amide | c1ccc2c(c1)CCCN2 | c1ccc2c(c1)CCC[NH]2 | C1CC1.c1ccncc1.c1ccc2c(c1)CCC[NH]2 | HCl | C(Cl)Cl | null | 8 | CC(=O)N(C1CC1)C1CC(C)Nc2ccccc21.O=C(Cl)c1cccnc1>C(Cl)Cl>CC(=O)N(C1CC1)C1CC(C)N(C(=O)c2cccnc2)c2ccccc21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-96a1d62622154a9db43cd54b2b12573a | CC(=O)N(C1CC1)C1CC(C)N(C(=O)OCc2ccccc2)c2ccccc21>>CC(=O)N(C1CC1)C1CC(C)Nc2ccccc21 | C(C1=CC=CC=C1)OC(=O)N1C(CC(C2=CC=CC=C12)N(C1CC1)C(C)=O)C>>C1(CC1)N(C(C)=O)C1CC(NC2=CC=CC=C12)C | O=C(OCc1ccccc1)[N:12]1[CH:10]([CH3:11])[CH2:9][CH:8]([N:4]([C:2]([CH3:1])=[O:3])[CH:5]2[CH2:6][CH2:7]2)[c:18]2[c:13]1[cH:14][cH:15][cH:16][cH:17]2>>[CH3:1][C:2](=[O:3])[N:4]([CH:5]1[CH2:6][CH2:7]1)[CH:8]1[CH2:9][CH:10]([CH3:11])[NH:12][c:13]2[cH:14][cH:15][cH:16][cH:17][c:18]21 | CC(=O)N(C1CC1)C1CC(C)N(C(=O)OCc2ccccc2)c2ccccc21 | CC(=O)N(C1CC1)C1CC(C)Nc2ccccc21 | null | [Pd] | CO | Reduction | Hydrogenolysis of tertiary amines | 7812cd90425bf85db01af6f04ff691ae52b54dad7d40e20fac978418b9a17d98 | 20c36f41eeb07c3ba4437b51ba72e8ff3c22d0b27e7197b0e9af3127f331149f | c1ccc2c(c1)NCCC2NC1CC1 | O=C(-O-C-c1:c:c:c:c:c:1)-[N;H0;D3;+0:1](-[C:2](-[C;D1;H3:3])-[C:4])-[c:5](:[c:6]):[c:7]>>[C:4]-[C:2](-[C;D1;H3:3])-[NH;D2;+0:1]-[c:5](:[c:6]):[c:7] | null | [] | null | null | 8 | HOUR | Benzyl-4-[acetyl(cyclopropyl)amino]-2-methyl-3,4-dihydroquinoline-1(2H)-carboxylate was dissolved in MeOH and a catalytic amount of Palladium on Carbon (10%) was added. The round bottom flask in which resided the resulting solution was evacuated and backfilled with hydrogen. The reaction was stirred under the hydrogen ... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether | Secondary amine | c1ccccc1.c1ccc2c(c1)CCC[NH]2 | c1ccc2c(c1)CCCN2 | C1CC1.c1ccc2c(c1)CCCN2 | HO- | [Pd].CO | null | 8 | CC(=O)N(C1CC1)C1CC(C)N(C(=O)OCc2ccccc2)c2ccccc21>[Pd].CO>CC(=O)N(C1CC1)C1CC(C)Nc2ccccc21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ca3c439a6a7f4503845a00d22a83f646 | CC(=O)N(C1CC1)C1CC(C)Nc2ccccc21.COc1ccc(C(=O)Cl)cc1>>COc1ccc(C(=O)N2c3ccccc3C(N(C(C)=O)C3CC3)CC2C)cc1 | CCN(C(C)C)C(C)C.C1(CC1)N(C(C)=O)C1CC(NC2=CC=CC=C12)C.COC1=CC=C(C(=O)Cl)C=C1>>C1(CC1)N(C(C)=O)C1CC(N(C2=CC=CC=C12)C(C1=CC=C(C=C1)OC)=O)C | [NH:9]1[c:10]2[cH:11][cH:12][cH:13][cH:14][c:15]2[CH:16]([N:17]([C:18]([CH3:19])=[O:20])[CH:21]2[CH2:22][CH2:23]2)[CH2:24][CH:25]1[CH3:26].Cl[C:7]([c:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:28][cH:27]1)=[O:8]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([C:7](=[O:8])[N:9]2[c:10]3[cH:11][cH:12][cH:13][cH:14][c:15]3[CH:16]([N:17](... | CC(=O)N(C1CC1)C1CC(C)Nc2ccccc21.COc1ccc(C(=O)Cl)cc1 | COc1ccc(C(=O)N2c3ccccc3C(N(C(C)=O)C3CC3)CC2C)cc1 | null | null | C(Cl)Cl | Acylation | N-alkylation of secondary amines with alkyl halides | 20af49e2ebd8e13ce8273786fd70e980d9c80eb9362be37fe2fe9cf2d75c9b8d | 96cb0a2fed10552c5770a45a2d6523b47ac3e38928b4a9c698d8577451182dcd | O=C(c1ccccc1)N1CCC(NC2CC2)c2ccccc21 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[C:6]-[C:7](-[C;D1;H3:8])-[NH;D2;+0:9]-[c:10](:[c:11]):[c:12]>>[C:6]-[C:7](-[C;D1;H3:8])-[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] | 68 | [{"value": 68.0, "product": "C1(CC1)N(C(C)=O)C1CC(N(C2=CC=CC=C12)C(C1=CC=C(C=C1)OC)=O)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 62.9, "product": "C1(CC1)N(C(C)=O)C1CC(N(C2=CC=CC=C12)C(C1=CC=C(C=C1)OC)=O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | To the solution of N-cyclopropyl-N-(2-methyl-1,2,3,4-tetrahydroquinolin-4-yl)-acetamide (82 mg, 0.34 mmol) in DCM (5 mL) was added 4-methoxybenzoyl chloride (68 mg, 0.40 mmol), followed by DIPEA (104 mg, 0.80 mmol). The reaction mixture was stirred at r.t. overnight. The mixture was concentrated under reduced pressure ... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Secondary amine | Tertiary amide | c1ccc2c(c1)CCCN2 | c1ccc2c(c1)CCC[NH]2 | c1ccccc1.C1CC1.c1ccc2c(c1)CCC[NH]2 | HCl | C(Cl)Cl | null | 8 | CC(=O)N(C1CC1)C1CC(C)Nc2ccccc21.COc1ccc(C(=O)Cl)cc1>C(Cl)Cl>COc1ccc(C(=O)N2c3ccccc3C(N(C(C)=O)C3CC3)CC2C)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-4b18b52d33e240e49e431631b2bc0b9a | O=[N+]([O-])c1cccc(B(O)O)c1>>Nc1cccc(B(O)O)c1 | [N+](=O)([O-])C=1C=C(C=CC1)B(O)O.[Mg]>>NC=1C=C(C=CC1)B(O)O | O=[N+:1]([O-])[c:2]1[cH:3][cH:4][cH:5][c:6]([B:7]([OH:8])[OH:9])[cH:10]1>>[NH2:1][c:2]1[cH:3][cH:4][cH:5][c:6]([B:7]([OH:8])[OH:9])[cH:10]1 | O=[N+]([O-])c1cccc(B(O)O)c1 | Nc1cccc(B(O)O)c1 | null | null | C1CCOC1 | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccccc1 | 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 1-bromonaphthalene 1, magnesium powder in THF is irradiated for 15 min to produce Grignard reagent 2 which reacts with tributyl borate to yield the boronic ester 3. Hydrolysis of 3 with aqueous sulfuric acid affords 1-naphthalene boronic acid 4 (Song, Y; Ding, Z; Wang, Q; Tao, F. Syn. Comm. 1998, 28, 3757,... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1 | Other | C1CCOC1 | null | null | O=[N+]([O-])c1cccc(B(O)O)c1>C1CCOC1>Nc1cccc(B(O)O)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-5a7537a6923542f2ae530b3518c093d4 | CCOP(OCC)OCC.OCc1ccccc1O>>CCOP(=O)(Cc1ccccc1O)OCC | OC1=C(CO)C=CC=C1.C(C)OP(OCC)OCC>>OC1=C(CP(OCC)(OCC)=O)C=CC=C1 | CC[O:5][P:4]([O:3][CH2:2][CH3:1])[O:14][CH2:15][CH3:16].O[CH2:6][c:7]1[cH:8][cH:9][cH:10][cH:11][c:12]1[OH:13]>>[CH3:1][CH2:2][O:3][P:4](=[O:5])([CH2:6][c:7]1[cH:8][cH:9][cH:10][cH:11][c:12]1[OH:13])[O:14][CH2:15][CH3:16] | CCOP(OCC)OCC.OCc1ccccc1O | CCOP(=O)(Cc1ccccc1O)OCC | null | null | CC=1C=CC=CC1C | Miscellaneous | OtherReaction | f468963cd150795c559ea97eef415e4c6e817d5e41b8e41bf56e6fc6478dce9b | 0450d2d3d6169ebd913d75de6102597ba0029b73d4e4cd2ca50ccc23bda73392 | c1ccccc1 | C-C-[O;H0;D2;+0:1]-[P;H0;D3;+0:2](-[#8:3]-[C:4])-[#8:5]-[C:6].O-[CH2;D2;+0:7]-[c:8](:[c:9]):[c:10]>>[C:4]-[#8:3]-[P;H0;D4;+0:2](=[O;H0;D1;+0:1])(-[#8:5]-[C:6])-[CH2;D2;+0:7]-[c:8](:[c:9]):[c:10] | 90 | [{"value": 90.0, "product": "OC1=C(CP(OCC)(OCC)=O)C=CC=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | 38.4 g of 2-hydroxybenzylalcohol from TOKYO KASEI KOGYO Co., Ltd. and 80 ml of o-xylene were put in a reaction reservoir having a mixer, a thermometer and a dropping funnel. Under a nitrogen stream, 62.8 g of triethylphosphite were slowly dropped therein at 80° C., and the reaction therein is further performed for 1 hr... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | null | null | null | c1ccccc1 | HO- | CC=1C=CC=CC1C | null | 1 | CCOP(OCC)OCC.OCc1ccccc1O>CC=1C=CC=CC1C>CCOP(=O)(Cc1ccccc1O)OCC |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-93d3b439a7e54938901a24d41e4f933b | CCOP(=O)(Cc1ccccc1O)OCC.Cc1ccc(N(c2ccc(C)cc2)c2ccc(C=O)cc2)cc1>>Cc1ccc(N(c2ccc(C)cc2)c2ccc(C=Cc3ccccc3O)cc2)cc1 | [K].CC(C)([O-])C.Cl.OC1=C(CP(OCC)(OCC)=O)C=CC=C1.C1(=CC=C(C=C1)N(C1=CC=C(C=O)C=C1)C1=CC=C(C=C1)C)C>>OC1=C(C=CC=C1)C=CC1=CC=C(C=C1)N(C1=CC=C(C=C1)C)C1=CC=C(C=C1)C | CCOP(=O)(OCC)[CH2:19][c:20]1[cH:21][cH:22][cH:23][cH:24][c:25]1[OH:26].O=[CH:18][c:17]1[cH:16][cH:15][c:14]([N:6]([c:5]2[cH:4][cH:3][c:2]([CH3:1])[cH:30][cH:29]2)[c:7]2[cH:8][cH:9][c:10]([CH3:11])[cH:12][cH:13]2)[cH:28][cH:27]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([N:6]([c:7]2[cH:8][cH:9][c:10]([CH3:11])[cH:12][cH:13]2)[c:1... | CCOP(=O)(Cc1ccccc1O)OCC.Cc1ccc(N(c2ccc(C)cc2)c2ccc(C=O)cc2)cc1 | Cc1ccc(N(c2ccc(C)cc2)c2ccc(C=Cc3ccccc3O)cc2)cc1 | null | null | O1CCCC1.O | C-C Coupling | Wittig with Phosphonium | 43d4e2f03e758941ee99f59641d5d56e6475fe935434d251d75d5cdebbe19869 | cedc9d4b791e43eacf8e7ecfa6a98d1dc0438794e96e4f1c4bef436b78f82bd8 | C(=Cc1ccc(N(c2ccccc2)c2ccccc2)cc1)c1ccccc1 | C-C-O-P(=O)(-O-C-C)-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].O=[CH;D2;+0:5]-[c:6](:[c:7]):[c:8]>>[c:7]:[c:6](-[CH;D2;+0:5]=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4]):[c:8] | 72 | [{"value": 72.0, "product": "OC1=C(C=CC=C1)C=CC1=CC=C(C=C1)N(C1=CC=C(C=C1)C)C1=CC=C(C=C1)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | 14.8 g of kalium-tert-butoxide and 50 ml of tetrahydrofuran were put in a reaction reservoir having a mixer, a thermometer and a dropping funnel. Under a nitrogen stream, a solution wherein 9.90 g of the diethyl 2-hydroxybenzylphosphonate and 5.44 g of 4-(di-para-tolylamino) benzaldehyde were dissolved in tetrahydrofur... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | null | null | null | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | HO- | O1CCCC1.O | null | 2 | CCOP(=O)(Cc1ccccc1O)OCC.Cc1ccc(N(c2ccc(C)cc2)c2ccc(C=O)cc2)cc1>O1CCCC1.O>Cc1ccc(N(c2ccc(C)cc2)c2ccc(C=Cc3ccccc3O)cc2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-2d2b49ec38f0422ba41ce248eda1ccca | CCOP(OCC)OCC.COc1ccc(CCl)cc1>>CCOP(=O)(Cc1ccc(OC)cc1)OCC | COC1=CC=C(CCl)C=C1.P(OCC)(OCC)OCC>>COC1=CC=C(CP(OCC)(OCC)=O)C=C1 | CC[O:5][P:4]([O:3][CH2:2][CH3:1])[O:15][CH2:16][CH3:17].Cl[CH2:6][c:7]1[cH:8][cH:9][c:10]([O:11][CH3:12])[cH:13][cH:14]1>>[CH3:1][CH2:2][O:3][P:4](=[O:5])([CH2:6][c:7]1[cH:8][cH:9][c:10]([O:11][CH3:12])[cH:13][cH:14]1)[O:15][CH2:16][CH3:17] | CCOP(OCC)OCC.COc1ccc(CCl)cc1 | CCOP(=O)(Cc1ccc(OC)cc1)OCC | null | null | null | Miscellaneous | OtherReaction | 0cee6f48ecb82f0bf47fd5d9d42e2dd8fcb51b36e7641d6549e2ebcac266a3bf | 60e0209a3e01281b77ea7e07e181a846736713b5a4a90ae8d47a0480f9ce79e5 | c1ccccc1 | C-C-[O;H0;D2;+0:1]-[P;H0;D3;+0:2](-[#8:3]-[C:4])-[#8:5]-[C:6].Cl-[CH2;D2;+0:7]-[c:8](:[c:9]):[c:10]>>[C:4]-[#8:3]-[P;H0;D4;+0:2](=[O;H0;D1;+0:1])(-[#8:5]-[C:6])-[CH2;D2;+0:7]-[c:8](:[c:9]):[c:10] | null | [] | null | null | null | null | 4-methoxybenzylchloride and triethyl phosphite were reacted for 5 hrs at 150° C. Then the excessive triethylphosphite and a by product ethyl chloride were removed by reduced-pressure distillation to prepare diethyl 4-methoxybenzylphosphonate.
Conditions: See reaction.notes.procedure_details.
Workup: Then the excessive ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | null | null | c1ccccc1 | HCl | null | null | null | CCOP(OCC)OCC.COc1ccc(CCl)cc1>>CCOP(=O)(Cc1ccc(OC)cc1)OCC |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-57acaef74f0849538fd1280d535629f9 | CCOP(=O)(Cc1ccc(OC)cc1)OCC.Cc1ccc(N(c2ccc(C)cc2)c2ccc(C=O)cc2)cc1>>COc1ccc(C=Cc2ccc(N(c3ccc(C)cc3)c3ccc(C)cc3)cc2)cc1 | COC1=CC=C(CP(OCC)(OCC)=O)C=C1.C1(=CC=C(C=C1)N(C1=CC=C(C=O)C=C1)C1=CC=C(C=C1)C)C.C(C)(C)(C)O[K].O.O>>COC1=CC=C(C=C1)C=CC1=CC=C(C=C1)N(C1=CC=C(C=C1)C)C1=CC=C(C=C1)C | CCOP(=O)(OCC)[CH2:7][c:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:31][cH:30]1.O=[CH:8][c:9]1[cH:10][cH:11][c:12]([N:13]([c:14]2[cH:15][cH:16][c:17]([CH3:18])[cH:19][cH:20]2)[c:21]2[cH:22][cH:23][c:24]([CH3:25])[cH:26][cH:27]2)[cH:28][cH:29]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH:7]=[CH:8][c:9]2[cH:10][cH:11][c:12]([N:13]... | CCOP(=O)(Cc1ccc(OC)cc1)OCC.Cc1ccc(N(c2ccc(C)cc2)c2ccc(C=O)cc2)cc1 | COc1ccc(C=Cc2ccc(N(c3ccc(C)cc3)c3ccc(C)cc3)cc2)cc1 | null | null | CN(C=O)C | C-C Coupling | Wittig with Phosphonium | 43d4e2f03e758941ee99f59641d5d56e6475fe935434d251d75d5cdebbe19869 | cedc9d4b791e43eacf8e7ecfa6a98d1dc0438794e96e4f1c4bef436b78f82bd8 | C(=Cc1ccc(N(c2ccccc2)c2ccccc2)cc1)c1ccccc1 | C-C-O-P(=O)(-O-C-C)-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].O=[CH;D2;+0:5]-[c:6](:[c:7]):[c:8]>>[c:7]:[c:6](-[CH;D2;+0:5]=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4]):[c:8] | null | [] | null | null | null | null | Same mol of the diethyl 4-methoxybenzylphosphonate and 4-(di-para-tolylamino)benzaldehyde were dissolved in N.N-dimethylformamide, and tert-butoxy kalium was gradually added to the solution while water-cooled and stirred. After stirred for 5 hrs at a room temperature, water was added thereto to acidize the solution and... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | null | null | null | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | HO- | CN(C=O)C | null | null | CCOP(=O)(Cc1ccc(OC)cc1)OCC.Cc1ccc(N(c2ccc(C)cc2)c2ccc(C=O)cc2)cc1>CN(C=O)C>COc1ccc(C=Cc2ccc(N(c3ccc(C)cc3)c3ccc(C)cc3)cc2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e8c066fbe35f48b196d35f6a4ecf26b4 | C1=C2CCC(=C1)C2>>OC1C2C=CC(C2)C1O | [O-][Si](=O)[O-].[Mg+2].Cl.C12=CC=C(CC1)C2.C[N+]1(CCOCC1)[O-]>>OC1C2C=CC(C1O)C2 | [CH2:2]1[C:3]2=[CH:4][CH:5]=[C:6]([CH2:7]2)[CH2:8]1>>[OH:1][CH:2]1[CH:3]2[CH:4]=[CH:5][CH:6]([CH2:7]2)[CH:8]1[OH:9] | C1=C2CCC(=C1)C2 | OC1C2C=CC(C2)C1O | null | S(=O)([O-])S(=O)[O-].[Na+].[Na+].[Os](=O)(=O)(=O)=O | N1=CC=CC=C1.C(C)(C)(C)O | Functional Group Addition | OtherReaction | 222e448e6a55e21328ef44ec7f961ae9a2c0d1fa07135c8ebe522d21ba21f125 | be15e8747a6f2e7be8ce0aa6f5b2fbbf1ded944443931e5b6ced663ad65d2c98 | C1=CC2CCC1C2 | [C:1]1-[C;H0;D3;+0:2]2=[CH;D2;+0:3]-[CH;D2;+0:4]=[C;H0;D3;+0:5]-1-[CH2;D2;+0:6]-[CH2;D2;+0:7]-2>>[O;D1;H1:8]-[CH;D3;+0:7]1-[CH;D3;+0:2]2-[C:1]-[CH;D3;+0:5](-[CH;D2;+0:4]=[CH;D2;+0:3]-2)-[CH;D3;+0:6]-1-[O;D1;H1:9] | 52 | [{"value": 52.0, "product": "OC1C2C=CC(C1O)C2", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A 1-L round bottom flask was charged under nitrogen with 450 mL of tert-butanol, 30 mL pyridine, 92 g (1 mol) of norbornadiene, 257.4 g of a 50% aqueous solution of 4-methylmorpholine-N-oxide (Sigma-Aldrich Chemical Company, Milwaukee, Wis.) and 6 mL of a 4% aqueous solution of osmium tetroxide (Sigma-Aldrich Chemical ... | 10.6084/m9.figshare.5104873.v1 | null | Conjugated diene | Secondary alcohol.Secondary alcohol | C1=C2CCC(=C1)C2 | C1=CC2CCC1C2 | C1=CC2CCC1C2 | Other | S(=O)([O-])S(=O)[O-].[Na+].[Na+].[Os](=O)(=O)(=O)=O.N1=CC=CC=C1.C(C)(C)(C)O | null | null | C1=C2CCC(=C1)C2>S(=O)([O-])S(=O)[O-].[Na+].[Na+].[Os](=O)(=O)(=O)=O.N1=CC=CC=C1.C(C)(C)(C)O>OC1C2C=CC(C2)C1O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-1146a0a96dd4414cbeb104144e1738c9 | CC(C)(C)OC(=O)N[C@@H](Cc1ccc(O)cc1)C(=O)O.CCN(C(C)C)C(C)C.CN(C)C=O.O.On1nnc2ccccc21>>CNC(=O)C(Cc1ccc([N+](=O)[O-])cc1)NC(=O)C(Cc1ccc(O)cc1)NC(=O)OC(C)(C)C | CN(C)C=O.C(C)(C)N(CC)C(C)C.C(CCl)Cl.O.N([C@@H](CC1=CC=C(C=C1)O)C(=O)O)C(=O)OC(C)(C)C.C=1C=CC2=C(C1)N=NN2O>>C(C)(C)(C)OC(NC(CC1=CC=C(C=C1)O)C(NC(CC1=CC=C(C=C1)[N+](=O)[O-])C(NC)=O)=O)=O | O[C:17](=[O:18])[C@H:19]([CH2:20][c:21]1[cH:22][cH:23][c:24]([OH:25])[cH:26][cH:27]1)[NH:28][C:29](=[O:30])[O:31][C:32]([CH3:33])([CH3:34])[CH3:35].CC(C)N(C(C)C)[CH2:6][CH3:5].C[N:2]([CH3:1])[CH:3]=[O:4].[OH2:12].n1[c:9]2[cH:8][cH:7][cH:15][cH:14][c:10]2[n:11]([OH:13])[n:16]1>>[CH3:1][NH:2][C:3](=[O:4])[CH:5]([CH2:6][c... | CC(C)(C)OC(=O)N[C@@H](Cc1ccc(O)cc1)C(=O)O.CCN(C(C)C)C(C)C.CN(C)C=O.O.On1nnc2ccccc21 | CNC(=O)C(Cc1ccc([N+](=O)[O-])cc1)NC(=O)C(Cc1ccc(O)cc1)NC(=O)OC(C)(C)C | null | null | null | C-C Coupling | OtherReaction | 3258a27fc659001dcb7eb9cacb040d6aa7732fbf3911f0356107a4419a10c80d | fc96388c61b7d26d2cf56e3817b88ff8a8607f39c7b419d7244aecb3f797635e | O=C(CCc1ccccc1)NCCc1ccccc1 | C-C(-C)-N(-[CH2;D2;+0:1]-[CH3;D1;+0:2])-C(-C)-C.C-[N;H0;D3;+0:3](-[C;D1;H3:4])-[CH;D2;+0:5]=[O;D1;H0:6].O-[C;H0;D3;+0:7](=[O;D1;H0:8])-[C@@H;D3;+0:9](-[#7:10]-[C:11](=[O;D1;H0:12])-[#8:13]-[C:14](-[C;D1;H3:15])(-[C;D1;H3:16])-[C;D1;H3:17])-[C:18]-[c:19].[OH2;D0;+0:20].[OH;D1;+0:21]-[n;H0;D3;+0:22]1:[n;H0;D2;+0:23]:n:[c... | null | [] | null | null | 18 | HOUR | H-L-Phe(4-NO2)-NMe (200 mg, 0.770 mmol) is dissolved in 1 mL DMF. Diisopropylethylamine (209 mg, 1.62 mmol), EDC (162 mg, 0.847 mmol), HOBt.H2O (130 mg, 0.847 mmol), and Boc-Tyr (238 mg, 0.847 mmol) are added and the mixture is stirred for 18 hr. at 20 ° C. The mixture is partitioned between water and EtOAc (2×60 mL). ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Tertiary amide.Tertiary amine | Nitro group.Secondary amide.Secondary amide | c1ccc2[nH]nnc2c1 | c1ccccc1 | c1ccccc1.c1ccccc1 | HO- | null | null | 18 | CC(C)(C)OC(=O)N[C@@H](Cc1ccc(O)cc1)C(=O)O.CCN(C(C)C)C(C)C.CN(C)C=O.O.On1nnc2ccccc21>>CNC(=O)C(Cc1ccc([N+](=O)[O-])cc1)NC(=O)C(Cc1ccc(O)cc1)NC(=O)OC(C)(C)C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-9ad645f4c3a44b38ad4afc7d2f00546d | O=C[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO>>OC[C@@H](O)[C@H](O)[C@@H](O)CO | O=C[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO.NC(=O)N>>C([C@H](O)[C@@H](O)[C@H](O)CO)O | O=C[C@@H:9]([C@H:7]([C@@H:5]([C@@H:3]([CH2:2][OH:1])[OH:4])[OH:6])[OH:8])[OH:10]>>[OH:1][CH2:2][C@@H:3]([OH:4])[C@H:5]([OH:6])[C@@H:7]([OH:8])[CH2:9][OH:10] | O=C[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO | OC[C@@H](O)[C@H](O)[C@@H](O)CO | null | null | null | Reduction | OtherReaction | e7895795cd3f75445716c94697823c5929dcd4b5344525875fe75d36bca2f9d7 | 21bb81d5469aaaca71ab12c186bea4016451717fad8780cf288858a7d8fbc55a | null | O=C-[C@H;D3;+0:1](-[O;D1;H1:2])-[C:3](-[C:4])-[O;D1;H1:5]>>[C:4]-[C:3](-[O;D1;H1:5])-[CH2;D2;+0:1]-[O;D1;H1:2] | null | [] | null | null | null | null | Approximately 2000 strains of osmophilic bacteria obtained as described above are cultured in individual microfermentors within a microfermentor array in a medium containing 20% (w/v) D-glucose, 0.1% urea, and 0.5% yeast extract at 30° C. for periods ranging from 12 hours to 5 days. The microfermentors have a working v... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | Primary alcohol | null | null | null | Other | null | null | null | O=C[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO>>OC[C@@H](O)[C@H](O)[C@@H](O)CO |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d675fd71c5f64e3aa5cff22a2210eb43 | Cn1ccnc1CO.O=S(Cl)Cl>>Cl.Cn1ccnc1CCl | CN1C(=NC=C1)CO.O=S(Cl)Cl>>Cl.ClCC=1N(C=CN1)C | O[CH2:8][c:7]1[n:3]([CH3:2])[cH:4][cH:5][n:6]1.O=S([Cl:1])[Cl:9]>>[ClH:1].[CH3:2][n:3]1[cH:4][cH:5][n:6][c:7]1[CH2:8][Cl:9] | Cn1ccnc1CO.O=S(Cl)Cl | Cl.Cn1ccnc1CCl | null | null | null | Functional Group Interconversion | Alcohol to chloride_SOCl2 | bb752b9027dc4488ba075e5955118a819f80cabd751a7497b67c2eeb1db6b071 | cbf41c7cf9fe6b47a243b1674d74ed5bf46a151f7f3a71d206e23176e158facf | c1c[nH]cn1 | O-[CH2;D2;+0:1]-[c:2]1:[#7;a:3]:[c:4]:[c:5]:[#7;a:6]:1-[C;D1;H3:7].O=S(-[Cl;H0;D1;+0:8])-[Cl;H0;D1;+0:9]>>[C;D1;H3:7]-[#7;a:6]1:[c:5]:[c:4]:[#7;a:3]:[c:2]:1-[CH2;D2;+0:1]-[Cl;H0;D1;+0:9].[ClH;D0;+0:8] | 69 | [{"value": 69.0, "product": "Cl.ClCC=1N(C=CN1)C", "details": "PERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | null | null | 20 g (0.179 mol) of (1-methyl-1H-imidazol-2-yl)methanol were added to 25 ml of SOCl2 under stirring at 0° C. The solution obtained was refluxed for 30 min and then the excess SOCl2 removed under vacuum. The thus obtained residue was recrystallized from 45 ml of EtOH to give 20.5 g (69%) of 2-(chloromethyl)-1-methyl-1H-... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | Primary halide | null | null | c1ncc[nH]1 | Other | null | 0 | null | Cn1ccnc1CO.O=S(Cl)Cl>>Cl.Cn1ccnc1CCl |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-fa8097b807c14de7b81d4f21f81fc12b | C1=Cc2ccccc2C1.Cn1ccnc1CCl>>Cn1ccnc1CC1=CCc2ccccc21 | Cl.C(CCC)[Li].C1C=CC2=CC=CC=C12.Cl.ClCC=1N(C=CN1)C>>C1C=C(C2=CC=CC=C12)CC=1N(C=CN1)C | [CH:8]1=[CH:9][CH2:10][c:11]2[cH:12][cH:13][cH:14][cH:15][c:16]21.Cl[CH2:7][c:6]1[n:2]([CH3:1])[cH:3][cH:4][n:5]1>>[CH3:1][n:2]1[cH:3][cH:4][n:5][c:6]1[CH2:7][C:8]1=[CH:9][CH2:10][c:11]2[cH:12][cH:13][cH:14][cH:15][c:16]21 | C1=Cc2ccccc2C1.Cn1ccnc1CCl | Cn1ccnc1CC1=CCc2ccccc21 | null | null | O1CCCC1 | C-C Coupling | OtherReaction | ee93cac7990a00c1dd3a845ddbd566fe7d8a8ffc7df7c031c0125f10973487d9 | f5e5e22797736d188bba28deb76a4cee8e4fee4dca04fe24f733d2ee68a23361 | C1=C(Cc2ncc[nH]2)c2ccccc2C1 | Cl-[CH2;D2;+0:1]-[c:2]1:[#7;a:3]:[c:4]:[c:5]:[#7;a:6]:1-[C;D1;H3:7].[c:8]:[c:9]1:[c:10]-[C:11]-[C:12]=[CH;D2;+0:13]-1>>[C;D1;H3:7]-[#7;a:6]1:[c:5]:[c:4]:[#7;a:3]:[c:2]:1-[CH2;D2;+0:1]-[C;H0;D3;+0:13]1=[C:12]-[C:11]-[c:10]:[c:9]-1:[c:8] | 76.7 | [{"value": 76.7, "product": "C1C=C(C2=CC=CC=C12)CC=1N(C=CN1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 17.4 ml of indene (0.1497 mol) in 150 ml of tetrahydrofuran (THF) was cooled to −60° C. and 61.8 ml of n-butyllithium (2M in hexane, 0.136 mol) were subsequently added while stirring. The mixture was allowed to warm to room temperature while stirring for 3 h and 5 g (0.0299 mol) of 2-(chloromethyl)-1-meth... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | C1=Cc2ccccc2C1 | C1=Cc2ccccc2C1 | c1ncc[nH]1.C1=Cc2ccccc2C1 | HCl | O1CCCC1 | null | null | C1=Cc2ccccc2C1.Cn1ccnc1CCl>O1CCCC1>Cn1ccnc1CC1=CCc2ccccc21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-c203e45701fe42a9b1d05b7dac5069b2 | O=S(Cl)Cl.OCc1nccn1-c1ccccc1>>Cl.ClCc1nccn1-c1ccccc1 | C1(=CC=CC=C1)N1C(=NC=C1)CO.O=S(Cl)Cl>>Cl.ClCC=1N(C=CN1)C1=CC=CC=C1 | O=S([Cl:1])[Cl:2].O[CH2:3][c:4]1[n:5][cH:6][cH:7][n:8]1-[c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1>>[ClH:1].[Cl:2][CH2:3][c:4]1[n:5][cH:6][cH:7][n:8]1-[c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1 | O=S(Cl)Cl.OCc1nccn1-c1ccccc1 | Cl.ClCc1nccn1-c1ccccc1 | null | null | null | Functional Group Interconversion | Alcohol to chloride_SOCl2 | bb752b9027dc4488ba075e5955118a819f80cabd751a7497b67c2eeb1db6b071 | cbf41c7cf9fe6b47a243b1674d74ed5bf46a151f7f3a71d206e23176e158facf | c1ccc(-n2ccnc2)cc1 | O-[CH2;D2;+0:1]-[c:2]1:[#7;a:3]:[c:4]:[c:5]:[#7;a:6]:1-[c:7].O=S(-[Cl;H0;D1;+0:8])-[Cl;H0;D1;+0:9]>>[Cl;H0;D1;+0:9]-[CH2;D2;+0:1]-[c:2]1:[#7;a:3]:[c:4]:[c:5]:[#7;a:6]:1-[c:7].[ClH;D0;+0:8] | 74 | [{"value": 74.0, "product": "Cl.ClCC=1N(C=CN1)C1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | null | null | 27 g (0.179 mol) of (1-phenyl-1H-imidazol-2-yl)methanol were added to 25 ml of SOCl2 under stirring at 0° C. The solution obtained was refluxed for 30 min and then the excess SOCl2 removed under vacuum. The thus obtained residue was recrystallized from 50 ml of a mixture of toluene:EtOH=5:1 to give 16.6 g (74%) of 2-(c... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | Primary halide | null | null | c1ncc[nH]1.c1ccccc1 | Other | null | 0 | null | O=S(Cl)Cl.OCc1nccn1-c1ccccc1>>Cl.ClCc1nccn1-c1ccccc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-17afaee4abcc4b988216604a3d7a1f85 | CCCCCCCCCCOCC(O)CN1CCc2ccccc2C1.O=S(=O)(O)Cl>>CCCCCCCCCCOCC(CN1CCc2ccccc2C1)OS(=O)(=O)O | ClS(=O)(=O)O.C(CCCCCCCCC)OCC(CN1CC2=CC=CC=C2CC1)O>>C1N(CCC2=CC=CC=C12)CC(COCCCCCCCCCC)OS(O)(=O)=O | [CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][O:11][CH2:12][CH:13]([CH2:14][N:15]1[CH2:16][CH2:17][c:18]2[cH:19][cH:20][cH:21][cH:22][c:23]2[CH2:24]1)[OH:25].Cl[S:26](=[O:27])(=[O:28])[OH:29]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][O:11][CH2:12][CH:13]([CH2:14]... | CCCCCCCCCCOCC(O)CN1CCc2ccccc2C1.O=S(=O)(O)Cl | CCCCCCCCCCOCC(CN1CCc2ccccc2C1)OS(=O)(=O)O | null | null | null | Acylation | Formation of Sulfonic Esters | 009ae016329697dc1c7131ed397afd8a2e6a9dd1daf66bc92cc2aea73f5fb91d | 9fc68dcbcf4de3cd14a88d39e0d10b781cdff74f48a12909566359cf74c25eff | c1ccc2c(c1)CCNC2 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[O;D1;H1:4].[C:5]-[C:6](-[C:7])-[OH;D1;+0:8]>>[C:5]-[C:6](-[C:7])-[O;H0;D2;+0:8]-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[O;D1;H1:4] | null | [] | null | null | null | null | 2-Decyloxymethyl-oxirane (1 equiv.), prepared according to Example 1 (except 1-decanol is substituted for 2-ethylhexanol), is dissolved in acetonitrile and warmed to 70° C. Stannic chloride (0.1 equiv.) is added to the reaction, which is maintained at 70° C. with stirring for 24-48 hours to give the oxazolidine. The re... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol | Sulfate | null | null | c1ccc2c(c1)CC[NH]C2 | HCl | null | null | null | CCCCCCCCCCOCC(O)CN1CCc2ccccc2C1.O=S(=O)(O)Cl>>CCCCCCCCCCOCC(CN1CCc2ccccc2C1)OS(=O)(=O)O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-c226dfd0b3a249e6993d3cfb1ff6271d | CCOC(=O)Cl.N#Cc1cc(Br)ccc1N>>CCOC(=O)Nc1ccc(Br)cc1C#N | NC1=C(C#N)C=C(C=C1)Br.ClC(=O)OCC>>C(C)OC(NC1=C(C=C(C=C1)Br)C#N)=O | Cl[C:4]([O:3][CH2:2][CH3:1])=[O:5].[NH2:6][c:7]1[cH:8][cH:9][c:10]([Br:11])[cH:12][c:13]1[C:14]#[N:15]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[NH:6][c:7]1[cH:8][cH:9][c:10]([Br:11])[cH:12][c:13]1[C:14]#[N:15] | CCOC(=O)Cl.N#Cc1cc(Br)ccc1N | CCOC(=O)Nc1ccc(Br)cc1C#N | null | null | null | Protection | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 038720aa61a7efa0f2a9ee6f2e0adf63a9ffdc2be4697c11a6215baef34f97b2 | 205f353513ce9506ab61831799da8fb73ec2ef5cfa927664496d3ce72c438860 | c1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C:4].[NH2;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[C:4]-[#8:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:5]-[c:6](:[c:7]):[c:8] | 68 | [{"value": 68.0, "product": "C(C)OC(NC1=C(C=C(C=C1)Br)C#N)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 67.9, "product": "C(C)OC(NC1=C(C=C(C=C1)Br)C#N)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A suspension of 2-amino-5-bromobenzonitrile (58.5 g, 297 mmol) in ethyl chloroformate (141 mL, 1.48 mol) was heated at reflux for 5 h. The excess ethyl chloroformate (99 mL) was distilled off and toluene (96 mL) was added. Slow addition of cyclohexane (228 mL) induced crystallization. The resulting solid was collected ... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Ether.Primary amine | Carbamic ester | null | null | c1ccccc1 | HCl | null | null | null | CCOC(=O)Cl.N#Cc1cc(Br)ccc1N>>CCOC(=O)Nc1ccc(Br)cc1C#N |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-271bca5206bf4b1ca62ec2973902481e | CCOC(=O)Nc1ccc(Br)cc1C#N.NNC=O>>O=c1[nH]c2ccc(Br)cc2c2ncnn12 | O.C(C)OC(NC1=C(C=C(C=C1)Br)C#N)=O.C(=O)NN.CN1CCCC1=O>>BrC1=CC=2C=3N(C(NC2C=C1)=O)N=CN3 | CCO[C:2](=[O:1])[NH:3][c:4]1[cH:5][cH:6][c:7]([Br:8])[cH:9][c:10]1[C:11]#[N:12].O=[CH:13][NH:14][NH2:15]>>[O:1]=[c:2]1[nH:3][c:4]2[cH:5][cH:6][c:7]([Br:8])[cH:9][c:10]2[c:11]2[n:12][cH:13][n:14][n:15]12 | CCOC(=O)Nc1ccc(Br)cc1C#N.NNC=O | O=c1[nH]c2ccc(Br)cc2c2ncnn12 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | d2308f602e6dc11b4ba0f40919f5bd5c726c02babdc9c30ca500a3550bcd8e7b | 5614a0a0aead52e65295238e6475465c8f3e5bdda31aa14a8bf980584483e473 | O=c1[nH]c2ccccc2c2ncnn12 | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:3]-[c:4](:[c:5]):[c:6](-[C;H0;D2;+0:7]#[N;H0;D1;+0:8]):[c:9].O=[CH;D2;+0:10]-[NH;D2;+0:11]-[NH2;D1;+0:12]>>[O;D1;H0:2]=[c;H0;D3;+0:1]1:[nH;D2;+0:3]:[c:4](:[c:5]):[c:6](:[c:9]):[c;H0;D3;+0:7]2:[n;H0;D2;+0:8]:[cH;D2;+0:10]:[n;H0;D2;+0:11]:[n;H0;D3;+0:12]:2:1 | 81 | [{"value": 81.0, "product": "BrC1=CC=2C=3N(C(NC2C=C1)=O)N=CN3", "details": "PERCENTYIELD", "is_desired": false}] | 160 | CELSIUS | 1.5 | HOUR | To a solution of (4-bromo-2-cyano-phenyl)-carbamic acid ethyl ester (40.4 g, 150 mmol) in NMP (170 mL) was added formylhydrazine (10.0 g, 150 mmol). The resulting mixture was stirred for 1.5 h at 160° C. under a gentle nitrogen sweep. It was cooled to below 100° C. and water (340 mL) was added slowly. The resulting slu... | 10.6084/m9.figshare.5104873.v1 | null | Acylhydrazine.Carbamic ester.Ether.Nitrile | null | c1ccccc1 | c1ccc2ncn3ncnc3c2c1 | c1ccc2ncn3ncnc3c2c1 | HO- | null | 160 | 1.5 | CCOC(=O)Nc1ccc(Br)cc1C#N.NNC=O>>O=c1[nH]c2ccc(Br)cc2c2ncnn12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-f1676d3cb5184b028f71fce2467eb385 | O=c1[nH]c2ccc(Br)cc2c2ncnn12>>Nc1ccc(Br)cc1-c1ncn[nH]1 | BrC1=CC=2C=3N(C(NC2C=C1)=O)N=CN3.[OH-].[Na+]>>BrC1=CC(=C(C=C1)N)C=1NN=CN1 | O=c1[nH:1][c:2]2[cH:3][cH:4][c:5]([Br:6])[cH:7][c:8]2[c:9]2[n:10][cH:11][n:12][n:13]12>>[NH2:1][c:2]1[cH:3][cH:4][c:5]([Br:6])[cH:7][c:8]1-[c:9]1[n:10][cH:11][n:12][nH:13]1 | O=c1[nH]c2ccc(Br)cc2c2ncnn12 | Nc1ccc(Br)cc1-c1ncn[nH]1 | null | null | C(CO)O | Reduction | OtherReaction | b8c88d2efcc054802d36031bc2f34013d2ef407151431abc6468f52811024052 | f4ea0365445c3397e612b814f46606587238bdfc396964fde128f445018666fe | c1ccc(-c2ncn[nH]2)cc1 | O=c1:[nH;D2;+0:1]:[c:2](:[c:3]):[c;H0;D3;+0:4](:[c:5]:[c:6]):[c;H0;D3;+0:7]2:[#7;a:8]:[c:9]:[#7;a:10]:[n;H0;D3;+0:11]:2:1>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c;H0;D3;+0:4](-[c;H0;D3;+0:7]1:[#7;a:8]:[c:9]:[#7;a:10]:[nH;D2;+0:11]:1):[c:5]:[c:6] | 87 | [{"value": 87.0, "product": "BrC1=CC(=C(C=C1)N)C=1NN=CN1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 61.6, "product": "BrC1=CC(=C(C=C1)N)C=1NN=CN1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 140 | CELSIUS | 30 | MINUTE | To a well stirred slurry of 9-bromo-6H-[1,2,4]triazolo[1,5-c]quinazolin-5-one (32.0 g, 171 mmol) in ethylene glycol (146 mL) which was heated at 100° C., was added aqeous NaOH (32%, 22.4 mL, 241 mmol). The slurry was heated at 140° C. for 17.5 h. The resulting solution was cooled to 27° C. and the product began to crys... | 10.6084/m9.figshare.5104873.v1 | null | null | Primary amine | c1ccc2ncn3ncnc3c2c1 | c1ccccc1.c1nnc[nH]1 | c1ccccc1.c1nnc[nH]1 | Other | C(CO)O | 140 | 0.5 | O=c1[nH]c2ccc(Br)cc2c2ncnn12>C(CO)O>Nc1ccc(Br)cc1-c1ncn[nH]1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-2ce53487c5244855b95576b2b30e34ca | Nc1ccc(Br)cc1-c1ncn[nH]1>>O=C1Cn2ncnc2-c2cc(Br)ccc2N1 | Cl.BrC1=CC(=C(C=C1)N)C=1NN=CN1.ClCC(=O)Cl.[OH-].[Na+]>>BrC=1C=CC2=C(C3=NC=NN3CC(N2)=O)C1 | [nH:4]1[n:5][cH:6][n:7][c:8]1-[c:9]1[cH:10][c:11]([Br:12])[cH:13][cH:14][c:15]1[NH2:16]>>[O:1]=[C:2]1[CH2:3][n:4]2[n:5][cH:6][n:7][c:8]2-[c:9]2[cH:10][c:11]([Br:12])[cH:13][cH:14][c:15]2[NH:16]1 | Nc1ccc(Br)cc1-c1ncn[nH]1 | O=C1Cn2ncnc2-c2cc(Br)ccc2N1 | null | null | O1CCOCC1.N1=CC=CC=C1.C(C)OCC | Heteroatom Alkylation and Arylation | OtherReaction | 3061731bbe7c4d65edb84f79cdb21c7724c1444461c7a74c6cb4109501b58fee | afdc35c0b9bc6721279627216295916722564d5171b6640e3413043af9d3c810 | O=C1Cn2ncnc2-c2ccccc2N1 | [NH2;D1;+0:1]-[c:2](:[c:3]):[c:4]-[c:5]1:[#7;a:6]:[c:7]:[#7;a:8]:[nH;D2;+0:9]:1>>[O;D1;H0:10]=[C:11]1-[C:12]-[n;H0;D3;+0:9]2:[#7;a:8]:[c:7]:[#7;a:6]:[c:5]:2-[c:4]:[c:2](:[c:3])-[NH;D2;+0:1]-1 | 46 | [{"value": 46.0, "product": "BrC=1C=CC2=C(C3=NC=NN3CC(N2)=O)C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 45.7, "product": "BrC=1C=CC2=C(C3=NC=NN3CC(N2)=O)C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 11 | CELSIUS | 75 | MINUTE | A solution of 4-bromo-2-(2H-[1,2,4]triazol-3-yl)-phenylamine (25.0 g, 105 mmol) in dioxane (870 mL) and pyridine (10.0 mL) was cooled to 12° C. A solution of chloroacetyl chloride (9.56 mL, 121 mmol) in diethylether (34.7 mL) was added dropwise over a period of 8 min. The mixture was stirred at 10-12° C. for 75 min and... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | Secondary amide | c1nc[nH]n1 | c1ccc2c(c1)NCCn1ncnc21 | c1ccc2c(c1)NCCn1ncnc21 | Other | O1CCOCC1.N1=CC=CC=C1.C(C)OCC | 11 | 1.25 | Nc1ccc(Br)cc1-c1ncn[nH]1>O1CCOCC1.N1=CC=CC=C1.C(C)OCC>O=C1Cn2ncnc2-c2cc(Br)ccc2N1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ec18a15bd4fc4b058d1a72ba5728363a | Cc1nc2c3cc(Cl)ccc3[nH]c(=O)n2n1>>Cc1n[nH]c(-c2cc(Cl)ccc2N)n1 | ClC1=CC=2C=3N(C(NC2C=C1)=O)N=C(N3)C.BrC1=CC=2C=3N(C(NC2C=C1)=O)N=CN3>>ClC1=CC(=C(C=C1)N)C=1NN=C(N1)C | O=c1[n:4]2[n:3][c:2]([CH3:1])[n:14][c:5]2[c:6]2[cH:7][c:8]([Cl:9])[cH:10][cH:11][c:12]2[nH:13]1>>[CH3:1][c:2]1[n:3][nH:4][c:5](-[c:6]2[cH:7][c:8]([Cl:9])[cH:10][cH:11][c:12]2[NH2:13])[n:14]1 | Cc1nc2c3cc(Cl)ccc3[nH]c(=O)n2n1 | Cc1n[nH]c(-c2cc(Cl)ccc2N)n1 | null | null | null | Reduction | OtherReaction | ddc0e92aa6f3d6549b695733411e0176a0a7729e91b959e11a5e5d4eca230934 | f4ea0365445c3397e612b814f46606587238bdfc396964fde128f445018666fe | c1ccc(-c2ncn[nH]2)cc1 | O=c1:[nH;D2;+0:1]:[c:2](:[c:3]):[c;H0;D3;+0:4](:[c:5]:[c:6]):[c;H0;D3;+0:7]2:[#7;a:8]:[c:9](-[C;D1;H3:10]):[#7;a:11]:[n;H0;D3;+0:12]:2:1>>[C;D1;H3:10]-[c:9]1:[#7;a:8]:[c;H0;D3;+0:7](-[c;H0;D3;+0:4](:[c:5]:[c:6]):[c:2](-[NH2;D1;+0:1]):[c:3]):[nH;D2;+0:12]:[#7;a:11]:1 | 76.4 | [{"value": 76.0, "product": "ClC1=CC(=C(C=C1)N)C=1NN=C(N1)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 76.4, "product": "ClC1=CC(=C(C=C1)N)C=1NN=C(N1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | As described for example 21c) 9-chloro-2-methyl-6H-[1,2,4]triazolo[1,5-c]quinazolin-5-one (9.67 g, 41.2 mmol), instead of 9-bromo-6H-[1,2,4]triazolo[1,5-c]quinazolin-5-one, was converted to the title compound (6.57 g, 76%) which was obtained as an off-white solid. MS: m/e=209.0 [M+H]+.
Conditions: See reaction.notes.pr... | 10.6084/m9.figshare.5104873.v1 | null | null | Primary amine | c1ccc2ncn3ncnc3c2c1 | c1nc[nH]n1.c1ccccc1 | c1nc[nH]n1.c1ccccc1 | Other | null | null | null | Cc1nc2c3cc(Cl)ccc3[nH]c(=O)n2n1>>Cc1n[nH]c(-c2cc(Cl)ccc2N)n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-5fb367e94c204c03a78477838c1bb55b | O=c1[nH]c2ccc(Cl)cc2c2nc(-c3ccccc3)nn12>>Nc1ccc(Cl)cc1-c1nc(-c2ccccc2)n[nH]1 | ClC1=CC=2C=3N(C(NC2C=C1)=O)N=C(N3)C3=CC=CC=C3.BrC1=CC=2C=3N(C(NC2C=C1)=O)N=CN3>>ClC1=CC(=C(C=C1)N)C=1NN=C(N1)C1=CC=CC=C1 | O=c1[nH:1][c:2]2[cH:3][cH:4][c:5]([Cl:6])[cH:7][c:8]2[c:9]2[n:10][c:11](-[c:12]3[cH:13][cH:14][cH:15][cH:16][cH:17]3)[n:18][n:19]12>>[NH2:1][c:2]1[cH:3][cH:4][c:5]([Cl:6])[cH:7][c:8]1-[c:9]1[n:10][c:11](-[c:12]2[cH:13][cH:14][cH:15][cH:16][cH:17]2)[n:18][nH:19]1 | O=c1[nH]c2ccc(Cl)cc2c2nc(-c3ccccc3)nn12 | Nc1ccc(Cl)cc1-c1nc(-c2ccccc2)n[nH]1 | null | null | null | Reduction | OtherReaction | b8c88d2efcc054802d36031bc2f34013d2ef407151431abc6468f52811024052 | f4ea0365445c3397e612b814f46606587238bdfc396964fde128f445018666fe | c1ccc(-c2n[nH]c(-c3ccccc3)n2)cc1 | O=c1:[nH;D2;+0:1]:[c:2](:[c:3]):[c;H0;D3;+0:4](:[c:5]:[c:6]):[c;H0;D3;+0:7]2:[#7;a:8]:[c:9](-[c:10]):[#7;a:11]:[n;H0;D3;+0:12]:2:1>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c;H0;D3;+0:4](-[c;H0;D3;+0:7]1:[#7;a:8]:[c:9](-[c:10]):[#7;a:11]:[nH;D2;+0:12]:1):[c:5]:[c:6] | 92.3 | [{"value": 92.0, "product": "ClC1=CC(=C(C=C1)N)C=1NN=C(N1)C1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 92.3, "product": "ClC1=CC(=C(C=C1)N)C=1NN=C(N1)C1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | As described for example 21c) 9-chloro-2-phenyl-6H-[1,2,4]triazolo[1,5-c]quinazolin-5-one (6.34 g, 21.4 mmol), instead of 9-bromo-6H-[1,2,4]triazolo[1,5-c]quinazolin-5-one, was converted to the title compound (5.35 g, 92%) which was obtained as a light brown solid. MS: m/e=271.0 [M+H]+.
Conditions: See reaction.notes.p... | 10.6084/m9.figshare.5104873.v1 | null | null | Primary amine | c1ccc2ncn3ncnc3c2c1 | c1ccccc1.c1nnc[nH]1 | c1ccccc1.c1nnc[nH]1.c1ccccc1 | Other | null | null | null | O=c1[nH]c2ccc(Cl)cc2c2nc(-c3ccccc3)nn12>>Nc1ccc(Cl)cc1-c1nc(-c2ccccc2)n[nH]1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-95a369dfe37b4db1a567ab92f3e75f15 | Cc1nc2c3cc(Br)ccc3[nH]c(=O)n2n1>>Cc1n[nH]c(-c2cc(Br)ccc2N)n1 | BrC1=CC=2C=3N(C(NC2C=C1)=O)N=C(N3)C.BrC1=CC=2C=3N(C(NC2C=C1)=O)N=CN3>>BrC1=CC(=C(C=C1)N)C=1NN=C(N1)C | O=c1[n:4]2[n:3][c:2]([CH3:1])[n:14][c:5]2[c:6]2[cH:7][c:8]([Br:9])[cH:10][cH:11][c:12]2[nH:13]1>>[CH3:1][c:2]1[n:3][nH:4][c:5](-[c:6]2[cH:7][c:8]([Br:9])[cH:10][cH:11][c:12]2[NH2:13])[n:14]1 | Cc1nc2c3cc(Br)ccc3[nH]c(=O)n2n1 | Cc1n[nH]c(-c2cc(Br)ccc2N)n1 | null | null | null | Reduction | OtherReaction | ddc0e92aa6f3d6549b695733411e0176a0a7729e91b959e11a5e5d4eca230934 | f4ea0365445c3397e612b814f46606587238bdfc396964fde128f445018666fe | c1ccc(-c2ncn[nH]2)cc1 | O=c1:[nH;D2;+0:1]:[c:2](:[c:3]):[c;H0;D3;+0:4](:[c:5]:[c:6]):[c;H0;D3;+0:7]2:[#7;a:8]:[c:9](-[C;D1;H3:10]):[#7;a:11]:[n;H0;D3;+0:12]:2:1>>[C;D1;H3:10]-[c:9]1:[#7;a:8]:[c;H0;D3;+0:7](-[c;H0;D3;+0:4](:[c:5]:[c:6]):[c:2](-[NH2;D1;+0:1]):[c:3]):[nH;D2;+0:12]:[#7;a:11]:1 | 99 | [{"value": 99.0, "product": "BrC1=CC(=C(C=C1)N)C=1NN=C(N1)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 98.8, "product": "BrC1=CC(=C(C=C1)N)C=1NN=C(N1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | As described for example 21c) 9-bromo-2-methyl-6H-[1,2,4]triazolo[1,5-c]quinazolin-5-one (28.5 g, 102 mmol), instead of 9-bromo-6H-[1,2,4]triazolo[1,5-c]quinazolin-5-one, was converted to the title compound (25.5 g, 99%) which was obtained as an off-white solid. MS: m/e=251.0/253.1 [M−H]−.
Conditions: See reaction.note... | 10.6084/m9.figshare.5104873.v1 | null | null | Primary amine | c1ccc2ncn3ncnc3c2c1 | c1nc[nH]n1.c1ccccc1 | c1nc[nH]n1.c1ccccc1 | Other | null | null | null | Cc1nc2c3cc(Br)ccc3[nH]c(=O)n2n1>>Cc1n[nH]c(-c2cc(Br)ccc2N)n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d1b03ab1bb2c4894a946937823c213bd | C=CCCCCCC(=O)Cl.O=C1N[C@@H](Cc2ccccc2)CO1>>C=CCCCCCC(=O)N1C(=O)OC[C@@H]1Cc1ccccc1 | C(CCCCCC=C)(=O)Cl.C(C1=CC=CC=C1)[C@@H]1NC(OC1)=O.[Li]CCCC>>C(CCCCCC=C)(=O)N1C(OC[C@@H]1CC1=CC=CC=C1)=O | Cl[C:8]([CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=[CH2:1])=[O:9].[NH:10]1[C:11](=[O:12])[O:13][CH2:14][C@@H:15]1[CH2:16][c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1>>[CH2:1]=[CH:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][C:8](=[O:9])[N:10]1[C:11](=[O:12])[O:13][CH2:14][C@@H:15]1[CH2:16][c:17]1[cH:18][cH:19][cH:20][cH:21][cH:... | C=CCCCCCC(=O)Cl.O=C1N[C@@H](Cc2ccccc2)CO1 | C=CCCCCCC(=O)N1C(=O)OC[C@@H]1Cc1ccccc1 | null | null | C1CCOC1 | Protection | N-alkylation of secondary amines with alkyl halides | 90b874b95a490ba678a8102349b0a4dbcd41213027fb4e6cf3a650d8fd23bd0d | 4e5209ce9341ab4af6dffbdfa22c50d4dc790b976013dec4e496751ff4457c48 | O=C1N[C@@H](Cc2ccccc2)CO1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[C:5]-[C:6]1-[C:7]-[#8:8]-[C:9](=[O;D1;H0:10])-[NH;D2;+0:11]-1>>[C:5]-[C:6]1-[C:7]-[#8:8]-[C:9](=[O;D1;H0:10])-[N;H0;D3;+0:11]-1-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4] | null | [] | 10 | CELSIUS | 30 | MINUTE | To a solution of (S)-(-)-4-benzyl-2-oxazolidinone (12.4 g, 69.79 mmol) in THF (200 mL) at −78° C. was added dropwise n-BuLi (30.7 mL, 2.5M solution in hexane, 76.77 mmol). After stirring for 30 min at the same temperature, the reaction mixture was then treated with 7-octenoyl chloride (11.21 g, 69.79 mmol). The reactio... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Carbamic ester | Carbamic ester.Substituted dicarboximide | C1COCN1 | C1COC[NH]1 | C1COC[NH]1.c1ccccc1 | HCl | C1CCOC1 | 10 | 0.5 | C=CCCCCCC(=O)Cl.O=C1N[C@@H](Cc2ccccc2)CO1>C1CCOC1>C=CCCCCCC(=O)N1C(=O)OC[C@@H]1Cc1ccccc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-5618ccfe2b564a5899e37e16dbe9e3fd | C=CCCCCCC(=O)N1C(=O)OC[C@@H]1Cc1ccccc1>>C=CCCCC[C@H](CO)C(=O)N1C(=O)OC[C@@H]1Cc1ccccc1 | C(CCCCCC=C)(=O)N1C(OC[C@@H]1CC1=CC=CC=C1)=O.C(C)(C)N(CC)C(C)C.O1OOCCC1>>OC[C@H](C(=O)N1C(OC[C@@H]1CC1=CC=CC=C1)=O)CCCCC=C | [CH2:1]=[CH:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][C:10](=[O:11])[N:12]1[C:13](=[O:14])[O:15][CH2:16][C@@H:17]1[CH2:18][c:19]1[cH:20][cH:21][cH:22][cH:23][cH:24]1>>[CH2:1]=[CH:2][CH2:3][CH2:4][CH2:5][CH2:6][C@H:7]([CH2:8][OH:9])[C:10](=[O:11])[N:12]1[C:13](=[O:14])[O:15][CH2:16][C@@H:17]1[CH2:18][c:19]1[cH:20][cH:21][cH... | C=CCCCCCC(=O)N1C(=O)OC[C@@H]1Cc1ccccc1 | C=CCCCC[C@H](CO)C(=O)N1C(=O)OC[C@@H]1Cc1ccccc1 | null | [Ti](Cl)(Cl)(Cl)Cl.[Ti](Cl)(Cl)(Cl)Cl | ClCCl | Miscellaneous | OtherReaction | f3b3e302df5ced319575d60f5b755b81b04cb30d0a89eb3d0296dfcceffce956 | 0607ce9ac404b7f992b14bf13602ccd36eb29bd5911f2b79cc25c0bfd203a764 | O=C1N[C@@H](Cc2ccccc2)CO1 | [#8:1]-[C:2](=[O;D1;H0:3])-[#7:4](-[C:5](=[O;D1;H0:6])-[CH2;D2;+0:7]-[C:8]-[C:9])-[C:10]>>[#8:1]-[C:2](=[O;D1;H0:3])-[#7:4](-[C:5](=[O;D1;H0:6])-[C@H;D3;+0:7](-[C:8]-[C:9])-[C:11]-[O;D1;H1:12])-[C:10] | null | [] | 0 | CELSIUS | 1 | HOUR | To a solution of (4S)-3-(7-octenoyl)-4-benzyl-1,3-oxazolidin-2-one (2.24 g, 7.59 mmol) and titanium (IV) chloride (1M in dichloromethane, 8.0 mL, 7.97 mmol) in dichloromethane (35 mL) at 0° C. was added dropwise diisopropylethylamine (1.5 mL, 8.35 mmol). After stirring at 0° C. for 1 hour, the resulting titanium enolat... | 10.6084/m9.figshare.5104873.v1 | null | null | Primary alcohol | null | null | C1COC[NH]1.c1ccccc1 | Other | [Ti](Cl)(Cl)(Cl)Cl.[Ti](Cl)(Cl)(Cl)Cl.ClCCl | 0 | 1 | C=CCCCCCC(=O)N1C(=O)OC[C@@H]1Cc1ccccc1>[Ti](Cl)(Cl)(Cl)Cl.[Ti](Cl)(Cl)(Cl)Cl.ClCCl>C=CCCCC[C@H](CO)C(=O)N1C(=O)OC[C@@H]1Cc1ccccc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-4ea1bc10d06342c9822afefbbd3f2334 | C=CCCCC[C@H](CO)C(=O)N1C(=O)OC[C@@H]1Cc1ccccc1.OO>>C=CCCCC[C@H](CO)C(=O)O | OO.OC[C@H](C(=O)N1C(OC[C@@H]1CC1=CC=CC=C1)=O)CCCCC=C.C1CCOC1.[Li+].[OH-]>>OC[C@H](C(=O)O)CCCCC=C | O=C1OC[C@H](Cc2ccccc2)N1[C:10]([C@H:7]([CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=[CH2:1])[CH2:8][OH:9])=[O:11].O[OH:12]>>[CH2:1]=[CH:2][CH2:3][CH2:4][CH2:5][CH2:6][C@H:7]([CH2:8][OH:9])[C:10](=[O:11])[OH:12] | C=CCCCC[C@H](CO)C(=O)N1C(=O)OC[C@@H]1Cc1ccccc1.OO | C=CCCCC[C@H](CO)C(=O)O | null | null | O | Acylation | OtherReaction | 7fefc4011edcbe1dffc93611e6aa33ad6e04d8cda971cf8f87e37d90bd4136c7 | e2c678181571c92a15078448ccb62575ef30480d579a3bf1599e99419fa7b1b3 | null | O-[OH;D1;+0:1].O=C1-O-C-[C@H](-C-c2:c:c:c:c:c:2)-N-1-[C;H0;D3;+0:2](=[O;D1;H0:3])-[C:4](-[C:5])-[C:6]>>[C:5]-[C:4](-[C:6])-[C;H0;D3;+0:2](=[O;D1;H0:3])-[OH;D1;+0:1] | null | [] | null | null | null | null | A 0.05 M solution of (4S)-3-[(2R)-2-(hydroxymethyl)-7-octenoyl]-4-benzyl-1,3-oxazolidin-2-one (2.55 g, 7.70 mmol) in a 4:1 mixture of THF and H2O was treated with 30% H2O2 (4.0 mL, 30.82 mmol), followed by LiOH (0.70 g, 15.41 mmol) at 0° C. The resulting mixture was stirred and allowed to warm to room temperature overn... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Substituted dicarboximide.Peroxide | Carboxylic acid | C1COCN1.c1ccccc1 | null | null | HO- | O | null | null | C=CCCCC[C@H](CO)C(=O)N1C(=O)OC[C@@H]1Cc1ccccc1.OO>O>C=CCCCC[C@H](CO)C(=O)O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-54a5d85e4adc4e3b924e02dda9e1f326 | C=CCCCC[C@H](CO)C(=O)O.NOCc1ccccc1>>C=CCCCC[C@H](CO)C(=O)NOCc1ccccc1 | OC[C@H](C(=O)O)CCCCC=C.Cl.C(C1=CC=CC=C1)ON.Cl.CN(CCCN=C=NCC)C>>OC[C@H](C(=O)NOCC1=CC=CC=C1)CCCCC=C | O[C:10]([C@H:7]([CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=[CH2:1])[CH2:8][OH:9])=[O:11].[NH2:12][O:13][CH2:14][c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1>>[CH2:1]=[CH:2][CH2:3][CH2:4][CH2:5][CH2:6][C@H:7]([CH2:8][OH:9])[C:10](=[O:11])[NH:12][O:13][CH2:14][c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1 | C=CCCCC[C@H](CO)C(=O)O.NOCc1ccccc1 | C=CCCCC[C@H](CO)C(=O)NOCc1ccccc1 | null | CN(C1=CC=NC=C1)C | ClCCl | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[C:5].[C:6]-[#8:7]-[NH2;D1;+0:8]>>[C:6]-[#8:7]-[NH;D2;+0:8]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[C:5] | null | [] | null | null | 8 | HOUR | To a mixture of (2R)-2-(hydroxymethyl)-7-octenoic acid (1.12 g, 6.51 mmol), O-benzyl hydroxylamine hydrochloride (1.04 g, 6.51 mmol) and 4-dimethylamino-pyridine (1.90 g, 15.62 mmol) in dichloromethane (30 mL) at 0° C. was added 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (1.50 g, 7.81 mmol). After st... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1 | HO- | CN(C1=CC=NC=C1)C.ClCCl | null | 8 | C=CCCCC[C@H](CO)C(=O)O.NOCc1ccccc1>CN(C1=CC=NC=C1)C.ClCCl>C=CCCCC[C@H](CO)C(=O)NOCc1ccccc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-c05e08bc207e426bbf7d1ad083546fd2 | C=CCCCC[C@H](CO)C(=O)NOCc1ccccc1>>C=CCCCC[C@@H]1CN(OCc2ccccc2)C1=O | OC[C@H](C(=O)NOCC1=CC=CC=C1)CCCCC=C.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.N(=NC(=O)OC(C)C)C(=O)OC(C)C>>C(CCCC=C)[C@H]1C(N(C1)OCC1=CC=CC=C1)=O | O[CH2:8][C@@H:7]([CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=[CH2:1])[C:18]([NH:9][O:10][CH2:11][c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1)=[O:19]>>[CH2:1]=[CH:2][CH2:3][CH2:4][CH2:5][CH2:6][C@@H:7]1[CH2:8][N:9]([O:10][CH2:11][c:12]2[cH:13][cH:14][cH:15][cH:16][cH:17]2)[C:18]1=[O:19] | C=CCCCC[C@H](CO)C(=O)NOCc1ccccc1 | C=CCCCC[C@@H]1CN(OCc2ccccc2)C1=O | null | null | C1CCOC1 | Heteroatom Alkylation and Arylation | OtherReaction | b69c6ce24f62fb81740e0df0b8fb42e56af8b5de1b619fe47b62ff730f66b9be | 53e9ea6bdc0d22524e13e79960e55c0106a6cc8b9aed21c29c8c6a7e9792ce5b | O=C1CCN1OCc1ccccc1 | O-[CH2;D2;+0:1]-[C:2](-[C:3])-[C:4](=[O;D1;H0:5])-[NH;D2;+0:6]-[#8:7]-[C:8]>>[C:8]-[#8:7]-[N;H0;D3;+0:6]1-[CH2;D2;+0:1]-[C:2](-[C:3])-[C:4]-1=[O;D1;H0:5] | null | [] | null | null | null | null | To a mixture of (2R)-2-(hydroxymethyl)-N-benzoxy-7-octenamide (1.51 g, 5.47 mmol) and triphenylphosphine (1.72 g, 6.56 mmol) in THF (50 mL) was added dropwise diisopropyl azodicarboxylate (1.3 mL, 6.56 mmol) at 0° C. The reaction mixture was stirred and allowed to warm to room temperature overnight. The reaction was th... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide.Primary alcohol | Tertiary amide | null | C1C[NH]C1 | C1C[NH]C1.c1ccccc1 | HO- | C1CCOC1 | null | null | C=CCCCC[C@H](CO)C(=O)NOCc1ccccc1>C1CCOC1>C=CCCCC[C@@H]1CN(OCc2ccccc2)C1=O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-9b98b35cfaaa4eef88ec2032037d7d01 | C=CCCCC[C@@H]1CN(OCc2ccccc2)C1=O.O>>C=CCCCC[C@H](CNOCc1ccccc1)C(=O)O | Cl.C(CCCC=C)[C@H]1C(N(C1)OCC1=CC=CC=C1)=O.O.[OH-].[Li+].O>>C(C1=CC=CC=C1)ONC[C@H](C(=O)O)CCCCC=C | [CH2:1]=[CH:2][CH2:3][CH2:4][CH2:5][CH2:6][C@@H:7]1[CH2:8][N:9]([O:10][CH2:11][c:12]2[cH:13][cH:14][cH:15][cH:16][cH:17]2)[C:18]1=[O:19].[OH2:20]>>[CH2:1]=[CH:2][CH2:3][CH2:4][CH2:5][CH2:6][C@H:7]([CH2:8][NH:9][O:10][CH2:11][c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1)[C:18](=[O:19])[OH:20] | C=CCCCC[C@@H]1CN(OCc2ccccc2)C1=O.O | C=CCCCC[C@H](CNOCc1ccccc1)C(=O)O | null | null | C1CCOC1.O.CO | Acylation | OtherReaction | d290be0e6c039da08f5a44a9bc2e5867109261941233b70d34efb0d142063595 | c913837cde051d545987d7a9645e266b6ab6214390a87b97a43298af2b6978fb | c1ccccc1 | [C:1]-[#8:2]-[N;H0;D3;+0:3]1-[C:4]-[C:5](-[C:6])-[C;H0;D3;+0:7]-1=[O;D1;H0:8].[OH2;D0;+0:9]>>[C:1]-[#8:2]-[NH;D2;+0:3]-[C:4]-[C:5](-[C:6])-[C;H0;D3;+0:7](=[O;D1;H0:8])-[OH;D1;+0:9] | null | [] | null | null | 8 | HOUR | To a mixture of (3R)-3-(5-hexen-1-yl)-N-benzoxy-2-azetidinone (0.39 g, 1.52 mmol) in a mixture of THF—H2O-MeOH (15 mL, 3:1:1 v/v) was added lithium hydroxide monohydrate (1.64 g, 15.2 mmol). After stirring at room temperature overnight, water (15 mL) was added to the mixture. The solution was acidified to pH 4 with 3N ... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide | Carboxylic acid.Secondary amine | C1C[NH]C1 | null | c1ccccc1 | null | C1CCOC1.O.CO | null | 8 | C=CCCCC[C@@H]1CN(OCc2ccccc2)C1=O.O>C1CCOC1.O.CO>C=CCCCC[C@H](CNOCc1ccccc1)C(=O)O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-bb2911321b244392b96e0bffada4221d | C=CCCCC[C@H](CNOCc1ccccc1)C(=O)O.O=CO>>C=CCCCC[C@H](CN(C=O)OCc1ccccc1)C(=O)O | C(C1=CC=CC=C1)ONC[C@H](C(=O)O)CCCCC=C.C(=O)O.C(C)(=O)OC(C)=O>>C(=O)N(OCC1=CC=CC=C1)C[C@H](C(=O)O)CCCCC=C | [CH2:1]=[CH:2][CH2:3][CH2:4][CH2:5][CH2:6][C@H:7]([CH2:8][NH:9][O:12][CH2:13][c:14]1[cH:15][cH:16][cH:17][cH:18][cH:19]1)[C:20](=[O:21])[OH:22].O[CH:10]=[O:11]>>[CH2:1]=[CH:2][CH2:3][CH2:4][CH2:5][CH2:6][C@H:7]([CH2:8][N:9]([CH:10]=[O:11])[O:12][CH2:13][c:14]1[cH:15][cH:16][cH:17][cH:18][cH:19]1)[C:20](=[O:21])[OH:22] | C=CCCCC[C@H](CNOCc1ccccc1)C(=O)O.O=CO | C=CCCCC[C@H](CN(C=O)OCc1ccccc1)C(=O)O | null | null | ClCCl | Acylation | Acylation of Nitrogen Nucleophiles by Carboxylic Acids | ac72df6259d5d7baee7abdbd4706ef4b4627f86ead9dc94f0cefcfcb37c21def | c5e4172490b2731ba9322b68af56376edadc31ce0bb9a3dfdea23a1817a852fd | c1ccccc1 | O-[CH;D2;+0:1]=[O;D1;H0:2].[C:3]-[#8:4]-[NH;D2;+0:5]-[C:6]-[C:7]-[C:8](=[O;D1;H0:9])-[O;D1;H1:10]>>[C:3]-[#8:4]-[N;H0;D3;+0:5](-[C:6]-[C:7]-[C:8](=[O;D1;H0:9])-[O;D1;H1:10])-[CH;D2;+0:1]=[O;D1;H0:2] | null | [] | 0 | CELSIUS | 1 | HOUR | To a cold solution of HCO2H (3.2 mL) and dichloromethane (10 mL) at 0° C. was added acetic anhydride (1.2 mL, 12.9 mmol). The mixture was stirred for 1 hour at 0° C. To the resulting mixture was added slowly a solution of (2R)-2-({N-benzoxy-amino}methyl)-7-octenoic acid (358 mg, 1.29 mmol) in dichloromethane (10 mL). T... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | Tertiary amide | null | null | c1ccccc1 | HO- | ClCCl | 0 | 1 | C=CCCCC[C@H](CNOCc1ccccc1)C(=O)O.O=CO>ClCCl>C=CCCCC[C@H](CN(C=O)OCc1ccccc1)C(=O)O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-df1d91d0ebde4ebe867f1af20cecb905 | C=CC[CH2][Mg][Br].CNC.Clc1nc(Cl)nc(Cl)n1.NN>>C=CCCc1nc(NN)nc(N(C)C)n1 | CNC.N1=C(Cl)N=C(Cl)N=C1Cl.C(CC=C)[Mg]Br.CCN(C(C)C)C(C)C.O.NN>>C(CC=C)C1=NC(=NC(=N1)N(C)C)NN | [Br][Mg][CH2:4][CH2:3][CH:2]=[CH2:1].[NH:12]([CH3:13])[CH3:14].Cl[c:5]1[n:6][c:7](Cl)[n:10][c:11](Cl)[n:15]1.[NH2:8][NH2:9]>>[CH2:1]=[CH:2][CH2:3][CH2:4][c:5]1[n:6][c:7]([NH:8][NH2:9])[n:10][c:11]([N:12]([CH3:13])[CH3:14])[n:15]1 | C=CC[CH2][Mg][Br].CNC.Clc1nc(Cl)nc(Cl)n1.NN | C=CCCc1nc(NN)nc(N(C)C)n1 | null | null | C1=CC=CC=C1.O1CCOCC1 | Heteroatom Alkylation and Arylation | OtherReaction | dc09b2db6ff8788cf99a15aa0fd3f7f397c312da58d5ed0c880b38db62ba69bb | 42fa9402ca46114c625b94c65af160ac5183454acaa6e5251605dc2051a72134 | c1ncncn1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c;H0;D3;+0:3](-Cl):[#7;a:4]:[c;H0;D3;+0:5](-Cl):[#7;a:6]:1.[Br]-[Mg]-[CH2;D2;+0:7]-[C:8]-[C:9]=[C;D1;H2:10].[C;D1;H3:11]-[NH;D2;+0:12]-[C;D1;H3:13].[N;D1;H2:14]-[NH2;D1;+0:15]>>[C;D1;H2:10]=[C:9]-[C:8]-[CH2;D2;+0:7]-[c;H0;D3;+0:5]1:[#7;a:6]:[c;H0;D3;+0:1](-[N;H0;D3;+0:12](-[C;D1;H3:11])-[C;... | null | [] | 0 | CELSIUS | 3 | HOUR | To a cyanuric chloride (1.07 g, 5.80 mmol) in anhydrous benzene (10.7 mL) was added at 0° C. dropwise a solution of 3-butenylmagnesium bromide (0.5M in THF, 12.8 mL, 6.38 mmol). The resulting mixture was stirred at 0° C. for 3 hrs. To the mixture were added 1,4-dioxane (10 mL), DIPEA (1.1 mL), followed by addition of d... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Magnesium halide.Aromatic halide.Aromatic halide.Aromatic halide.Secondary amine | Hydrazine.Tertiary amine | c1ncncn1 | c1ncncn1 | c1ncncn1 | HCl.Br-.Mg | C1=CC=CC=C1.O1CCOCC1 | 0 | 3 | C=CC[CH2][Mg][Br].CNC.Clc1nc(Cl)nc(Cl)n1.NN>C1=CC=CC=C1.O1CCOCC1>C=CCCc1nc(NN)nc(N(C)C)n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d5ad093626464c57994b39f46b92ea52 | C=CCCCC[C@H](CN(C=O)OCc1ccccc1)C(=O)O.C=CCCc1nc(NN)nc(N(C)C)n1>>C=CCCCC[C@H](CN(C=O)OCc1ccccc1)C(=O)NNc1nc(CCC=C)nc(N(C)C)n1 | C(=O)N(OCC1=CC=CC=C1)C[C@H](C(=O)O)CCCCC=C.C(CC=C)C1=NC(=NC(=N1)N(C)C)NN.CN1CCOCC1.C1=CC2=C(N=C1)N(N=N2)O.Cl.CN(CCCN=C=NCC)C>>C(CC=C)C1=NC(=NC(=N1)N(C)C)NNC(=O)[C@@H](CN(C=O)OCC1=CC=CC=C1)CCCCC=C | O[C:20]([C@H:7]([CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=[CH2:1])[CH2:8][N:9]([CH:10]=[O:11])[O:12][CH2:13][c:14]1[cH:15][cH:16][cH:17][cH:18][cH:19]1)=[O:21].[NH2:22][NH:23][c:24]1[n:25][c:26]([CH2:27][CH2:28][CH:29]=[CH2:30])[n:31][c:32]([N:33]([CH3:34])[CH3:35])[n:36]1>>[CH2:1]=[CH:2][CH2:3][CH2:4][CH2:5][CH2:6][C@H:7]([C... | C=CCCCC[C@H](CN(C=O)OCc1ccccc1)C(=O)O.C=CCCc1nc(NN)nc(N(C)C)n1 | C=CCCCC[C@H](CN(C=O)OCc1ccccc1)C(=O)NNc1nc(CCC=C)nc(N(C)C)n1 | null | null | CN(C)C=O | Acylation | Carboxylic acid with primary amine to amide | 87776deec7c8d787307af11af64c4c1226af5b5e46e4fe8124762f384e2eebf3 | 82203b4f77b2f7d17908f28dcc1ecc7f616d152f963b273ffea1254f61a0fe2d | O=C(CCNOCc1ccccc1)NNc1ncncn1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[C:5].[#7;a:6]:[c:7](-[#7:8]-[NH2;D1;+0:9]):[#7;a:10]>>[#7;a:6]:[c:7](-[#7:8]-[NH;D2;+0:9]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[C:5]):[#7;a:10] | null | [] | null | null | 8 | HOUR | To a mixture of (2R)-2-({N-formyl-N-benzoxy-amino}methyl)-7-octenoic acid (233 mg, 1.121 mmol), 4-(3-buten-1-yl)-6-(dimethylamino)-2-hydrazino-1,3,5-triazine (342 mg, 1.121 mmol), NMM (0.62 mL, 5.61 mmol) and HOAt (183 mg, 1.345 mmol) in DMF (11 mL) at room temperature was added 1-[3-(dimethylamino)-propyl]-3-ethylcarb... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Carboxylic acid | Acylhydrazine | null | null | c1ccccc1.c1ncncn1 | HO- | CN(C)C=O | null | 8 | C=CCCCC[C@H](CN(C=O)OCc1ccccc1)C(=O)O.C=CCCc1nc(NN)nc(N(C)C)n1>CN(C)C=O>C=CCCCC[C@H](CN(C=O)OCc1ccccc1)C(=O)NNc1nc(CCC=C)nc(N(C)C)n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-660ffe71a09d47239b277df2fbed2325 | C=CCCCC[C@H](CN(C=O)OCc1ccccc1)C(=O)NNc1nc(CCC=C)nc(N(C)C)n1>>CN(C)c1nc2nc(n1)NNC(=O)[C@@H](CN(C=O)OCc1ccccc1)CCCCC=CCC2 | C(CC=C)C1=NC(=NC(=N1)N(C)C)NNC(=O)[C@@H](CN(C=O)OCC1=CC=CC=C1)CCCCC=C>>CN(C=1N=C2CCC=CCCCC[C@@H](C(NNC(N1)=N2)=O)CN(C=O)OCC2=CC=CC=C2)C | C=[CH:31][CH2:30][CH2:29][CH2:28][CH2:27][C@@H:14]([C:12]([NH:11][NH:10][c:8]1[n:7][c:6]([CH2:34][CH2:33][CH:32]=C)[n:5][c:4]([N:2]([CH3:1])[CH3:3])[n:9]1)=[O:13])[CH2:15][N:16]([CH:17]=[O:18])[O:19][CH2:20][c:21]1[cH:22][cH:23][cH:24][cH:25][cH:26]1>>[CH3:1][N:2]([CH3:3])[c:4]1[n:5][c:6]2[n:7][c:8]([n:9]1)[NH:10][NH:1... | C=CCCCC[C@H](CN(C=O)OCc1ccccc1)C(=O)NNc1nc(CCC=C)nc(N(C)C)n1 | CN(C)c1nc2nc(n1)NNC(=O)[C@@H](CN(C=O)OCc1ccccc1)CCCCC=CCC2 | null | CC1=CC(=C(C(=C1)C)N2CCN([CH-]2)C3=C(C=C(C=C3C)C)C)C.C1CCC(CC1)[PH+](C2CCCCC2)C3CCCCC3.C1=CC=C(C=C1)C=[Ru](Cl)Cl | ClCCl | C-C Coupling | OtherReaction | 7e95cf5fdb5b4dd423464484391ad6277206585a3a2f0f5b98836b93e146d282 | 67a23c4de67c22dcd6bc1d4c033efdcf679af248440c3b10e6768679c5f73280 | O=C1NNc2ncnc(n2)CCC=CCCCC[C@@H]1CNOCc1ccccc1 | C=[CH;D2;+0:1]-[C:2]-[C:3].C=[CH;D2;+0:4]-[C:5]-[C:6]>>[C:3]-[C:2]-[CH;D2;+0:1]=[CH;D2;+0:4]-[C:5]-[C:6] | null | [] | null | null | null | null | To a solution of N-[(2R)-2-({2-[4-(3-buten-1-yl)-6-(dimethylamino)-1,3,5-triazin-2-yl]hydrazino}carbonyl)-7-octen-1-yl]-N-benzoxyformamide (280 mg, 0.566 mmol) in dichloromethane (225 mL, 0.0025M) at room temperature was added tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydro-imidazol-2-ylidene][benzyli... | 10.6084/m9.figshare.5104873.v1 | null | Allyl.Allyl | null | null | C1=CCCc2ncnc(n2)NNCCCCCC1 | C1=CCCc2ncnc(n2)NNCCCCCC1.c1ccccc1 | Other | CC1=CC(=C(C(=C1)C)N2CCN([CH-]2)C3=C(C=C(C=C3C)C)C)C.C1CCC(CC1)[PH+](C2CCCCC2)C3CCCCC3.C1=CC=C(C=C1)C=[Ru](Cl)Cl.ClCCl | null | null | C=CCCCC[C@H](CN(C=O)OCc1ccccc1)C(=O)NNc1nc(CCC=C)nc(N(C)C)n1>CC1=CC(=C(C(=C1)C)N2CCN([CH-]2)C3=C(C=C(C=C3C)C)C)C.C1CCC(CC1)[PH+](C2CCCCC2)C3CCCCC3.C1=CC=C(C=C1)C=[Ru](Cl)Cl.ClCCl>CN(C)c1nc2nc(n1)NNC(=O)[C@@H](CN(C=O)OCc1ccccc1)CCCCC=CCC2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-dedb3d67986d4c1899d103f65cd94a2e | C=CC[CH2][Mg][Br].CSc1nc(Cl)cc(Cl)n1>>C=CCCc1cc(Cl)nc(SC)n1 | ClC1=NC(=NC(=C1)Cl)SC.C(CC=C)[Mg]Br>>C(CC=C)C1=NC(=NC(=C1)Cl)SC | [Br][Mg][CH2:4][CH2:3][CH:2]=[CH2:1].Cl[c:5]1[cH:6][c:7]([Cl:8])[n:9][c:10]([S:11][CH3:12])[n:13]1>>[CH2:1]=[CH:2][CH2:3][CH2:4][c:5]1[cH:6][c:7]([Cl:8])[n:9][c:10]([S:11][CH3:12])[n:13]1 | C=CC[CH2][Mg][Br].CSc1nc(Cl)cc(Cl)n1 | C=CCCc1cc(Cl)nc(SC)n1 | null | null | C1CCOC1 | C-C Coupling | OtherReaction | 3a76f525d1068830f1765722344a1864af357b78c52e1b8d04f352a21b298abc | 7eab41b7d498a9b6e898b07b0e0d9b3528044390091411fce2a435b647d0bc46 | c1cncnc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3](-[#16:4]):[#7;a:5]:[c:6](-[Cl;D1;H0:7]):[c:8]:1.[Br]-[Mg]-[CH2;D2;+0:9]-[C:10]-[C:11]=[C;D1;H2:12]>>[#16:4]-[c:3]1:[#7;a:2]:[c;H0;D3;+0:1](-[CH2;D2;+0:9]-[C:10]-[C:11]=[C;D1;H2:12]):[c:8]:[c:6](-[Cl;D1;H0:7]):[#7;a:5]:1 | null | [] | null | null | 8 | HOUR | To a mixture of 4,6-dichloro-2-(methylthio)pyrimidine (5.20 g, 26.66 mmol) and tris(acetylacetonate)iron (III) (0.47 g, 1.33 mmol) in THF (130 mL) and DMP (13 mL) at 0° C. was added slowly 3-butenylmagnesium bromide (0.5M in THF, 56 mL, 28.0 mmol). The reaction mixture was stirred overnight. After the reaction was comp... | 10.6084/m9.figshare.5104873.v1 | null | Magnesium halide.Aromatic halide | null | c1cncnc1 | c1cncnc1 | c1cncnc1 | Br-.Mg | C1CCOC1 | null | 8 | C=CC[CH2][Mg][Br].CSc1nc(Cl)cc(Cl)n1>C1CCOC1>C=CCCc1cc(Cl)nc(SC)n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-389325d3b2fe4aee8d5dab8b664fcda2 | C1COCCN1.C=CCCc1cc(Cl)nc(SC)n1>>C=CCCc1cc(N2CCOCC2)nc(SC)n1 | C(CC=C)C1=NC(=NC(=C1)Cl)SC.CCN(C(C)C)C(C)C.N1CCOCC1>>C(CC=C)C1=CC(=NC(=N1)SC)N1CCOCC1 | [NH:8]1[CH2:9][CH2:10][O:11][CH2:12][CH2:13]1.Cl[c:7]1[cH:6][c:5]([CH2:4][CH2:3][CH:2]=[CH2:1])[n:18][c:15]([S:16][CH3:17])[n:14]1>>[CH2:1]=[CH:2][CH2:3][CH2:4][c:5]1[cH:6][c:7]([N:8]2[CH2:9][CH2:10][O:11][CH2:12][CH2:13]2)[n:14][c:15]([S:16][CH3:17])[n:18]1 | C1COCCN1.C=CCCc1cc(Cl)nc(SC)n1 | C=CCCc1cc(N2CCOCC2)nc(SC)n1 | null | null | O1CCOCC1 | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | b6ba2533a469a91b7ece94b4a523fa9d9d9bc584236787b5a2be96cdf7a917fc | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1cc(N2CCOCC2)ncn1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3](-[#16:4]):[#7;a:5]:[c:6](-[C:7]):[c:8]:1.[#8:9]1-[C:10]-[C:11]-[NH;D2;+0:12]-[C:13]-[C:14]-1>>[#16:4]-[c:3]1:[#7;a:2]:[c;H0;D3;+0:1](-[N;H0;D3;+0:12]2-[C:13]-[C:14]-[#8:9]-[C:10]-[C:11]-2):[c:8]:[c:6](-[C:7]):[#7;a:5]:1 | null | [] | 80 | CELSIUS | null | null | To a solution of 4-(3-buten-1-yl)-6-chloro-2-(methylthio)-pyrimidine (26.66 mmol) and DIPEA (5.1 mL, 29.33 mmol) in 1,4-dioxane (100 mL) at room temperature was added morpholine (2.6 mL, 29.33 mmol). The reaction mixture was stirred and heated at 80° C. overnight. After the reaction was completed, the volatiles were re... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | C1COCCN1.c1cncnc1 | c1cncnc1.C1COCC[NH]1 | c1cncnc1.C1COCC[NH]1 | HCl | O1CCOCC1 | 80 | null | C1COCCN1.C=CCCc1cc(Cl)nc(SC)n1>O1CCOCC1>C=CCCc1cc(N2CCOCC2)nc(SC)n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-1a6e6ce0e3514389981a3e1f29dc1e72 | C=CCCc1cc(Cl)nc(SC)n1.OB(O)c1ccco1>>C=CCCc1cc(-c2ccco2)nc(SC)n1 | C(CC=C)C1=NC(=NC(=C1)Cl)SC.O1C(=CC=C1)B(O)O.C(=O)([O-])[O-].[Na+].[Na+]>>C(CC=C)C1=NC(=NC(=C1)C=1OC=CC1)SC | Cl[c:7]1[cH:6][c:5]([CH2:4][CH2:3][CH:2]=[CH2:1])[n:17][c:14]([S:15][CH3:16])[n:13]1.OB(O)[c:8]1[cH:9][cH:10][cH:11][o:12]1>>[CH2:1]=[CH:2][CH2:3][CH2:4][c:5]1[cH:6][c:7](-[c:8]2[cH:9][cH:10][cH:11][o:12]2)[n:13][c:14]([S:15][CH3:16])[n:17]1 | C=CCCc1cc(Cl)nc(SC)n1.OB(O)c1ccco1 | C=CCCc1cc(-c2ccco2)nc(SC)n1 | null | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1 | O1CCOCC1 | C-C Coupling | Suzuki coupling with boronic acids | 10a97fb451331038632d4eab00d75ba2fa56f845cd92b47922f288fa162ae29c | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1coc(-c2ccncn2)c1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3](-[#16:4]):[#7;a:5]:[c:6](-[C:7]):[c:8]:1.O-B(-O)-[c;H0;D3;+0:9]1:[#8;a:10]:[c:11]:[c:12]:[c:13]:1>>[#16:4]-[c:3]1:[#7;a:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:9]2:[#8;a:10]:[c:11]:[c:12]:[c:13]:2):[c:8]:[c:6](-[C:7]):[#7;a:5]:1 | null | [] | 110 | CELSIUS | null | null | To a solution of 4-(3-buten-1-yl)-6-chloro-2-(methylthio)-pyrimidine (0.79 g, 3.69 mmol), 2-furanylboronic acid (0.45 g, 4.06 mmol), aq. Na2CO3 solution (2M, 4.1 mL) in dioxane (37 mL) at room temperature was added tetrakis(triphenylphosphine)palladium(0) (0.21 g, 0.185 mmol). The reaction mixture in sealed tube was st... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1cncnc1.c1ccoc1 | c1cncnc1.c1ccoc1 | c1cncnc1.c1ccoc1 | HCl.B | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.O1CCOCC1 | 110 | null | C=CCCc1cc(Cl)nc(SC)n1.OB(O)c1ccco1>C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.O1CCOCC1>C=CCCc1cc(-c2ccco2)nc(SC)n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-577eef1bc9404132ab499b9c76a4fe28 | C=CCCCCC(=O)O.C[Si](C)(C)C=[N+]=[N-]>>C=CCCCCC(=O)NN | C(CCCCC=C)(=O)O.[Si](C)(C)(C)C=[N+]=[N-]>>C(CCCCC=C)(=O)NN | O[C:7]([CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=[CH2:1])=[O:8].C[Si](C)(C)C=[N+:10]=[N-:9]>>[CH2:1]=[CH:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7](=[O:8])[NH:9][NH2:10] | C=CCCCCC(=O)O.C[Si](C)(C)C=[N+]=[N-] | C=CCCCCC(=O)NN | null | null | CO.C(Cl)Cl | Acylation | OtherReaction | c6980e6eff70c37c0f24a8a46e41a819374e00319a8586f7ae130852b5ed21ce | 72c4becb5afc76a64fbbdf5e0ed5153bbd3173b7bc483d3656908cebd84a52f7 | null | C-[Si](-C)(-C)-C=[N+;H0;D2:1]=[N-;H0;D1:2].O-[C;H0;D3;+0:3](=[O;D1;H0:4])-[C:5]-[C:6]>>[C:6]-[C:5]-[C;H0;D3;+0:3](=[O;D1;H0:4])-[NH;D2;+0:2]-[NH2;D1;+0:1] | null | [] | null | null | 30 | MINUTE | To a solution of 6-heptenoic acid (1.24 g, 9.68 mmol) in methylene chloride (40 mL) and MeOH (10 mL) was added slowly TMSCHN2 (2M, 12.1 mL) at room temperature. The reaction mixture was stirred for additional 30 minutes. After the reaction was completed, the mixture was evaporated in vacuo. The residue was directly use... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Diazo.Silyl protective group | Acylhydrazine | null | null | null | HO- | CO.C(Cl)Cl | null | 0.5 | C=CCCCCC(=O)O.C[Si](C)(C)C=[N+]=[N-]>CO.C(Cl)Cl>C=CCCCCC(=O)NN |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-7f785d9910ca43b9bfc8a79f71909a1e | CN(C)c1nc2nc(n1)NNC(=O)[C@@H](CN(C=O)OCc1ccccc1)CCCCC=CCC2>>CN(C)c1nc2nc(n1)NNC(=O)[C@@H](CN(O)C=O)CCCCCCCC2 | CN(C=1N=C2CCC=CCCCC[C@@H](C(NNC(N1)=N2)=O)CN(C=O)OCC2=CC=CC=C2)C>>CN(C=1N=C2CCCCCCCC[C@@H](C(NNC(N1)=N2)=O)CN(C=O)O)C | c1ccc(C[O:17][N:16]([CH2:15][C@@H:14]2[C:12](=[O:13])[NH:11][NH:10][c:8]3[n:7][c:6]([n:5][c:4]([N:2]([CH3:1])[CH3:3])[n:9]3)[CH2:27][CH2:26][CH:25]=[CH:24][CH2:23][CH2:22][CH2:21][CH2:20]2)[CH:18]=[O:19])cc1>>[CH3:1][N:2]([CH3:3])[c:4]1[n:5][c:6]2[n:7][c:8]([n:9]1)[NH:10][NH:11][C:12](=[O:13])[C@@H:14]([CH2:15][N:16]([... | CN(C)c1nc2nc(n1)NNC(=O)[C@@H](CN(C=O)OCc1ccccc1)CCCCC=CCC2 | CN(C)c1nc2nc(n1)NNC(=O)[C@@H](CN(O)C=O)CCCCCCCC2 | null | [Pd] | CO | Deprotection | OtherReaction | 94140a41b135fc0198b7ff12db5d26a2e31592111856f3efbe86fb5d66fd4946 | 30a26bc929988d0041b9998cdccd1d65eb125114a78065ed35d40f50c965c0a7 | O=C1CCCCCCCCCc2ncnc(n2)NN1 | [C:1]-[#7:2](-[C:3]=[O;D1;H0:4])-[O;H0;D2;+0:5]-C-c1:c:c:c:c:c:1.[C:6]-[C:7]-[CH;D2;+0:8]=[CH;D2;+0:9]-[C:10]-[C:11]>>[C:1]-[#7:2](-[OH;D1;+0:5])-[C:3]=[O;D1;H0:4].[C:6]-[C:7]-[CH2;D2;+0:8]-[CH2;D2;+0:9]-[C:10]-[C:11] | null | [] | null | null | 3 | HOUR | To a solution of N-{[(5R)-16-(dimethylamino)-4-oxo-2,3,15,17,18-pentaazabicyclo[12.3.1]octadeca-1(18),10,14,16-tetraen-5-yl]methyl}-N-benzoxyformamide (75 mg) in MeOH (15 mL) was added 10% Pd/C (15 mg, 20% w/w). The reaction mixture was subjected to hydrogenation for 3 hours at room temperature. The reaction mixture wa... | 10.6084/m9.figshare.5104873.v1 | null | null | null | c1ccccc1.C1=CCCc2ncnc(n2)NNCCCCCC1 | c1nc2nc(n1)NNCCCCCCCCCC2 | c1nc2nc(n1)NNCCCCCCCCCC2 | Other | [Pd].CO | null | 3 | CN(C)c1nc2nc(n1)NNC(=O)[C@@H](CN(C=O)OCc1ccccc1)CCCCC=CCC2>[Pd].CO>CN(C)c1nc2nc(n1)NNC(=O)[C@@H](CN(O)C=O)CCCCCCCC2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-acaf3c8ea1a74418ae4033db058a9924 | Cc1c(Cl)cccc1S(=O)(=O)Cl.Cc1nccc(N)n1>>Cc1nccc(NS(=O)(=O)c2cccc(Cl)c2C)n1 | CC1=NC=CC(=N1)N.ClC=1C(=C(C=CC1)S(=O)(=O)Cl)C>>ClC=1C(=C(C=CC1)S(=O)(=O)NC1=NC(=NC=C1)C)C | Cl[S:8](=[O:9])(=[O:10])[c:11]1[cH:12][cH:13][cH:14][c:15]([Cl:16])[c:17]1[CH3:18].[CH3:1][c:2]1[n:3][cH:4][cH:5][c:6]([NH2:7])[n:19]1>>[CH3:1][c:2]1[n:3][cH:4][cH:5][c:6]([NH:7][S:8](=[O:9])(=[O:10])[c:11]2[cH:12][cH:13][cH:14][c:15]([Cl:16])[c:17]2[CH3:18])[n:19]1 | Cc1c(Cl)cccc1S(=O)(=O)Cl.Cc1nccc(N)n1 | Cc1nccc(NS(=O)(=O)c2cccc(Cl)c2C)n1 | null | null | N1=CC=CC=C1 | Miscellaneous | Sulfonamide synthesis (Schotten-Baumann) primary amine | a86b0632821e188c0a5dc5a5a2aac298ab3eccaee8a52ba46078c3d5975a290d | 50f8fbf3d327483c3eeff8f6cbd4065e4c7600bb501fbe08958a5c79a0926428 | O=S(=O)(Nc1ccncn1)c1ccccc1 | 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]1:[#7;a:9]:[c:10]:[#7;a:11]:[c:12]:[c:13]:1>>[O;D1;H0:2]=[S;H0;D4;+0:1](=[O;D1;H0:3])(-[NH;D2;+0:7]-[c:8]1:[#7;a:9]:[c:10]:[#7;a:11]:[c:12]:[c:13]:1)-[c:4](:[c:5]):[c:6] | 9.3 | [{"value": 9.3, "product": "ClC=1C(=C(C=CC1)S(=O)(=O)NC1=NC(=NC=C1)C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 55 | CELSIUS | 48 | HOUR | 2-Methyl-pyrimidin-4-ylamine (91 mg, Gabriel, Chem. Ber. 37, 1904, 3641) and 3-chloro-2-methyl-benzenesulfonyl chloride (179 mg) were dissolved in pyridine (5 mL) and the resulting mixture was allowed to stir at 50 to 60° C. for 48 hours. The mixture was then evaporated in vacuo and the residue was dissolved in ethyl a... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Sulfonyl halide | Sulfonamide | null | null | c1cncnc1.c1ccccc1 | HCl | N1=CC=CC=C1 | 55 | 48 | Cc1c(Cl)cccc1S(=O)(=O)Cl.Cc1nccc(N)n1>N1=CC=CC=C1>Cc1nccc(NS(=O)(=O)c2cccc(Cl)c2C)n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-c04cd902f3dd427b9f372338b3870909 | C=C(Cl)C#N.N=C(N)C1CC1>>Nc1ccnc(C2CC2)n1 | C1CC1C(=N)N.Cl.C(C)N(CC)CC.ClC(C#N)=C>>C1(CC1)C1=NC=CC(=N1)N | Cl[C:2]([C:3]#[N:1])=[CH2:4].[NH:5]=[C:6]([CH:7]1[CH2:8][CH2:9]1)[NH2:10]>>[NH2:1][c:2]1[cH:3][cH:4][n:5][c:6]([CH:7]2[CH2:8][CH2:9]2)[n:10]1 | C=C(Cl)C#N.N=C(N)C1CC1 | Nc1ccnc(C2CC2)n1 | null | null | C(C)O | Aromatic Heterocycle Formation | OtherReaction | e15717fdab8a8ff5ba7d0f49a42b2f1ee70a42aaa6c6817caa99be24646dd604 | 3d45291949b890aada3eda520251ab6c726eca25b07da8e42f9c5cda12427181 | c1cnc(C2CC2)nc1 | Cl-[C;H0;D3;+0:1](=[CH2;D1;+0:2])-[C;H0;D2;+0:3]#[N;H0;D1;+0:4].[NH2;D1;+0:5]-[C;H0;D3;+0:6](=[NH;D1;+0:7])-[C:8]1-[C:9]-[C:10]-1>>[NH2;D1;+0:4]-[c;H0;D3;+0:1]1:[cH;D2;+0:3]:[cH;D2;+0:2]:[n;H0;D2;+0:7]:[c;H0;D3;+0:6](-[C:8]2-[C:9]-[C:10]-2):[n;H0;D2;+0:5]:1 | null | [] | null | null | null | null | Cyclopropylcarbamidine hydrochloride (7.61 g) was dissolved in ethanol (125 mL) and triethylamine (19.35 mL) and 2-chloro-acrylonitrile (5.52 mL) were added. The resulting orange-yellow solution was refluxed for 30 minutes. The mixture was cooled and left in a refrigerator over night. The solid was removed by filtratio... | 10.6084/m9.figshare.5104873.v1 | null | Alkenyl halide.Nitrile.Primary amine.Vinyl | Primary amine | null | c1cncnc1 | c1cncnc1.C1CC1 | HCl | C(C)O | null | null | C=C(Cl)C#N.N=C(N)C1CC1>C(C)O>Nc1ccnc(C2CC2)n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-3978ef0eda0643959c59e96f9ced050e | CCOC=CC#N.N=C(N)C1CC1>>CC(C)c1nccc(N)n1 | C1CC1C(=N)N.Cl.C(C)OC=CC#N>>C(C)(C)C1=NC=CC(=N1)N | CCO[CH:4]=[CH:7][C:6]#[N:5].[CH2:1]1[CH:2]([C:8]([NH2:9])=[NH:10])[CH2:3]1>>[CH3:1][CH:2]([CH3:3])[c:4]1[n:5][cH:6][cH:7][c:8]([NH2:9])[n:10]1 | CCOC=CC#N.N=C(N)C1CC1 | CC(C)c1nccc(N)n1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 33508e203dde007df155fc0717a5cb2960bb40ff31688dfd0dde702d62d9bce8 | 372c50c91d332beae53e28c42bae63d2e63d66cc79c0d384730f809c142c58bc | c1cncnc1 | C-C-O-[CH;D2;+0:1]=[CH;D2;+0:2]-[C;H0;D2;+0:3]#[N;H0;D1;+0:4].[N;D1;H2:5]-[C;H0;D3;+0:6](=[NH;D1;+0:7])-[CH;D3;+0:8]1-[CH2;D2;+0:9]-[CH2;D2;+0:10]-1>>[CH3;D1;+0:9]-[CH;D3;+0:8](-[CH3;D1;+0:10])-[c;H0;D3;+0:1]1:[n;H0;D2;+0:7]:[c;H0;D3;+0:6](-[N;D1;H2:5]):[cH;D2;+0:2]:[cH;D2;+0:3]:[n;H0;D2;+0:4]:1 | null | [] | null | null | null | null | This compound was made in analogy to example 2, step A] from cyclopropylcarbamidine hydrochloride (3 g) and 3-ethoxyacrylonitrile (2.5 mL) to give 2-isopropyl-pyrimidin-4-ylamine (1.36 g) as a light yellow foam. MS (ESI): 138.1 (MH+).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Ether.Nitrile | null | C1CC1 | c1cncnc1 | c1cncnc1 | HO- | null | null | null | CCOC=CC#N.N=C(N)C1CC1>>CC(C)c1nccc(N)n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-0ac0e58ac8c8447d8e38dfe034a3c657 | C=C(Cl)C#N.CCC(=N)N>>CCc1nccc(N)n1 | Cl.C(CC)(=N)N.ClC(C#N)=C>>C(C)C1=NC=CC(=N1)N | Cl[C:7](=[CH2:5])[C:6]#[N:8].[CH3:1][CH2:2][C:3](=[NH:4])[NH2:9]>>[CH3:1][CH2:2][c:3]1[n:4][cH:5][cH:6][c:7]([NH2:8])[n:9]1 | C=C(Cl)C#N.CCC(=N)N | CCc1nccc(N)n1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | e15717fdab8a8ff5ba7d0f49a42b2f1ee70a42aaa6c6817caa99be24646dd604 | 3d45291949b890aada3eda520251ab6c726eca25b07da8e42f9c5cda12427181 | c1cncnc1 | Cl-[C;H0;D3;+0:1](=[CH2;D1;+0:2])-[C;H0;D2;+0:3]#[N;H0;D1;+0:4].[C;D1;H3:5]-[C:6]-[C;H0;D3;+0:7](-[NH2;D1;+0:8])=[NH;D1;+0:9]>>[C;D1;H3:5]-[C:6]-[c;H0;D3;+0:7]1:[n;H0;D2;+0:9]:[cH;D2;+0:2]:[cH;D2;+0:3]:[c;H0;D3;+0:1](-[NH2;D1;+0:4]):[n;H0;D2;+0:8]:1 | null | [] | null | null | null | null | This intermediate was made according to example 2, step A] via the alternative preparation method from propionamidine hydrochloride (1.45 g, obtained from propionitrile in analogy to Synth. Commun. 12 (13), 1982, 989-993 and Tetrahedron Lett. 31 (14), 1990, 1969-1972) and 2-chloro-acrylonitrile (1.17 mL). 2-Ethyl-pyrim... | 10.6084/m9.figshare.5104873.v1 | null | Alkenyl halide.Nitrile.Primary amine.Vinyl | Primary amine | null | c1cncnc1 | c1cncnc1 | HCl | null | null | null | C=C(Cl)C#N.CCC(=N)N>>CCc1nccc(N)n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-3b73d4d4d4ee41bfa2cbeea7f5c4bc2a | CCc1nccc(N)n1.Cc1c(Cl)cccc1S(=O)(=O)Cl>>CCc1nccc(NS(=O)(=O)c2cccc(Cl)c2C)n1 | C(C)C1=NC=CC(=N1)N.ClC=1C(=C(C=CC1)S(=O)(=O)Cl)C>>ClC=1C(=C(C=CC1)S(=O)(=O)NC1=NC(=NC=C1)CC)C | [CH3:1][CH2:2][c:3]1[n:4][cH:5][cH:6][c:7]([NH2:8])[n:20]1.Cl[S:9](=[O:10])(=[O:11])[c:12]1[cH:13][cH:14][cH:15][c:16]([Cl:17])[c:18]1[CH3:19]>>[CH3:1][CH2:2][c:3]1[n:4][cH:5][cH:6][c:7]([NH:8][S:9](=[O:10])(=[O:11])[c:12]2[cH:13][cH:14][cH:15][c:16]([Cl:17])[c:18]2[CH3:19])[n:20]1 | CCc1nccc(N)n1.Cc1c(Cl)cccc1S(=O)(=O)Cl | CCc1nccc(NS(=O)(=O)c2cccc(Cl)c2C)n1 | null | null | null | Miscellaneous | Sulfonamide synthesis (Schotten-Baumann) primary amine | a86b0632821e188c0a5dc5a5a2aac298ab3eccaee8a52ba46078c3d5975a290d | 50f8fbf3d327483c3eeff8f6cbd4065e4c7600bb501fbe08958a5c79a0926428 | O=S(=O)(Nc1ccncn1)c1ccccc1 | 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]1:[#7;a:9]:[c:10]:[#7;a:11]:[c:12]:[c:13]:1>>[O;D1;H0:2]=[S;H0;D4;+0:1](=[O;D1;H0:3])(-[NH;D2;+0:7]-[c:8]1:[#7;a:9]:[c:10]:[#7;a:11]:[c:12]:[c:13]:1)-[c:4](:[c:5]):[c:6] | null | [] | null | null | null | null | This compound was obtained according to example 2, step B] from 2-ethyl-pyrimidin-4-ylamine (0.25 g), and 3-chloro-2-methyl-benzenesulfonyl chloride (0.55 g) as a colorless solid (86 mg). MS (ESI−): 310.0 ([M−H]−).
Conditions: See reaction.notes.procedure_details.
Workup: This compound was obtained | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Sulfonyl halide | Sulfonamide | null | null | c1cncnc1.c1ccccc1 | HCl | null | null | null | CCc1nccc(N)n1.Cc1c(Cl)cccc1S(=O)(=O)Cl>>CCc1nccc(NS(=O)(=O)c2cccc(Cl)c2C)n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-afc9e035799643efb9f2e283dffecc2a | CCOC=CC#N.N=C(N)C1CCC1>>Nc1ccnc(C2CCC2)n1 | Cl.C1(CCC1)C(=N)N.C(C)OC=CC#N>>C1(CCC1)C1=NC=CC(=N1)N | CCO[CH:4]=[CH:3][C:2]#[N:1].[NH:5]=[C:6]([CH:7]1[CH2:8][CH2:9][CH2:10]1)[NH2:11]>>[NH2:1][c:2]1[cH:3][cH:4][n:5][c:6]([CH:7]2[CH2:8][CH2:9][CH2:10]2)[n:11]1 | CCOC=CC#N.N=C(N)C1CCC1 | Nc1ccnc(C2CCC2)n1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 1e568f7e0e15482dde11fdfeccd63d6b9d6b5bc1f8269cd40cdfe5561fc41bcc | c6284da6d834238420f26e5398d63d6a0d74f532def882e624d78f4ac191261d | c1cnc(C2CCC2)nc1 | C-C-O-[CH;D2;+0:1]=[CH;D2;+0:2]-[C;H0;D2;+0:3]#[N;H0;D1;+0:4].[C:5]-[C:6](-[C;H0;D3;+0:7](-[NH2;D1;+0:8])=[NH;D1;+0:9])-[C:10]>>[C:5]-[C:6](-[c;H0;D3;+0:7]1:[n;H0;D2;+0:8]:[c;H0;D3;+0:3](-[NH2;D1;+0:4]):[cH;D2;+0:2]:[cH;D2;+0:1]:[n;H0;D2;+0:9]:1)-[C:10] | null | [] | null | null | null | null | This intermediate was made according to example 2, step A] method from cyclobutanecarboxamidine hydrochloride (0.3 g, obtained from cyclobutanecarbonitrile in analogy to Synth. Commun. 12 (13), 1982, 989-993 and Tetrahedron Lett. 31 (14), 1990, 1969-1972) and 3-ethoxy-acrylonitrile (0.3 g). 2-Cyclobutyl-pyrimidin-4-yla... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Nitrile.Primary amine | Primary amine | null | c1cncnc1 | c1cncnc1.C1CCC1 | HO- | null | null | null | CCOC=CC#N.N=C(N)C1CCC1>>Nc1ccnc(C2CCC2)n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-c1ad65b5ed734f73a3282ffb2f81586a | Cc1c(Cl)cccc1S(=O)(=O)Cl.Nc1ccnc(C2CCC2)n1>>Cc1c(Cl)cccc1S(=O)(=O)Nc1ccnc(C2CCC2)n1 | C1(CCC1)C1=NC=CC(=N1)N.ClC=1C(=C(C=CC1)S(=O)(=O)Cl)C>>ClC=1C(=C(C=CC1)S(=O)(=O)NC1=NC(=NC=C1)C1CCC1)C | Cl[S:9]([c:8]1[c:2]([CH3:1])[c:3]([Cl:4])[cH:5][cH:6][cH:7]1)(=[O:10])=[O:11].[NH2:12][c:13]1[cH:14][cH:15][n:16][c:17]([CH:18]2[CH2:19][CH2:20][CH2:21]2)[n:22]1>>[CH3:1][c:2]1[c:3]([Cl:4])[cH:5][cH:6][cH:7][c:8]1[S:9](=[O:10])(=[O:11])[NH:12][c:13]1[cH:14][cH:15][n:16][c:17]([CH:18]2[CH2:19][CH2:20][CH2:21]2)[n:22]1 | Cc1c(Cl)cccc1S(=O)(=O)Cl.Nc1ccnc(C2CCC2)n1 | Cc1c(Cl)cccc1S(=O)(=O)Nc1ccnc(C2CCC2)n1 | null | null | null | Miscellaneous | Sulfonamide synthesis (Schotten-Baumann) primary amine | a86b0632821e188c0a5dc5a5a2aac298ab3eccaee8a52ba46078c3d5975a290d | 50f8fbf3d327483c3eeff8f6cbd4065e4c7600bb501fbe08958a5c79a0926428 | O=S(=O)(Nc1ccnc(C2CCC2)n1)c1ccccc1 | 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]1:[#7;a:9]:[c:10]:[#7;a:11]:[c:12]:[c:13]:1>>[O;D1;H0:2]=[S;H0;D4;+0:1](=[O;D1;H0:3])(-[NH;D2;+0:7]-[c:8]1:[#7;a:9]:[c:10]:[#7;a:11]:[c:12]:[c:13]:1)-[c:4](:[c:5]):[c:6] | null | [] | null | null | null | null | This compound was obtained according to example 2, step B] from 2-cyclobutyl-pyrimidin-4-ylamine (0.15 g), and 3-chloro-2-methyl-benzenesulfonyl chloride (0.27 g) as a light brown solid (47 mg). MS (ESI): 338.1 (MH+).
Conditions: See reaction.notes.procedure_details.
Workup: This compound was obtained | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Sulfonyl halide | Sulfonamide | null | null | c1ccccc1.c1cncnc1.C1CCC1 | HCl | null | null | null | Cc1c(Cl)cccc1S(=O)(=O)Cl.Nc1ccnc(C2CCC2)n1>>Cc1c(Cl)cccc1S(=O)(=O)Nc1ccnc(C2CCC2)n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-9124b9c72cce48b38d8b470124738db6 | Nc1ccnc(CCl)n1.OCC1CC1>>Nc1ccnc(COCC2CC2)n1 | OCC1CC1.ClCC1=NC=CC(=N1)N.O>>C1(CC1)COCC1=NC=CC(=N1)N | Cl[CH2:7][c:6]1[n:5][cH:4][cH:3][c:2]([NH2:1])[n:13]1.[OH:8][CH2:9][CH:10]1[CH2:11][CH2:12]1>>[NH2:1][c:2]1[cH:3][cH:4][n:5][c:6]([CH2:7][O:8][CH2:9][CH:10]2[CH2:11][CH2:12]2)[n:13]1 | Nc1ccnc(CCl)n1.OCC1CC1 | Nc1ccnc(COCC2CC2)n1 | null | null | [H-].[Na+].C1CCOC1 | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | dd3f9c60e1f90d961a7c01d970ae213561355ee1451f276a3b04696e4b6fae5c | 46a6e883cf919b4006e69abfdfd883f458f55c08b3200960c6a5b57c4139fbca | c1cnc(COCC2CC2)nc1 | Cl-[CH2;D2;+0:1]-[c:2](:[#7;a:3]:[c:4]):[#7;a:5]:[c:6].[C:7]-[C:8]-[OH;D1;+0:9]>>[C:7]-[C:8]-[O;H0;D2;+0:9]-[CH2;D2;+0:1]-[c:2](:[#7;a:3]:[c:4]):[#7;a:5]:[c:6] | 21.6 | [{"value": 21.6, "product": "C1(CC1)COCC1=NC=CC(=N1)N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | Hydroxymethylcyclopropane (0.17 g) was dissolved in THF (2 mL) and at 0° C. sodium hydride dispersion (55% in oil, 0.1 g) was added. The mixture was allowed to stir for 30 minutes and subsequently, a solution of 2-chloromethyl-pyrimidin-4-ylamine (0.2 g, Eur. Pat. Appl. EP 61318 A2, 1982; Eur. Pat. Appl. 60094 A2, 1982... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary alcohol | Ether | null | null | c1cncnc1.C1CC1 | HCl | [H-].[Na+].C1CCOC1 | null | 0.5 | Nc1ccnc(CCl)n1.OCC1CC1>[H-].[Na+].C1CCOC1>Nc1ccnc(COCC2CC2)n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-57b0af428dac44a3a090d9dde4430d8c | C1COCCN1.Nc1ccnc(CCl)n1>>Nc1ccnc(CN2CCOCC2)n1 | ClCC1=NC=CC(=N1)N.C(C)N(CC)CC.N1CCOCC1>>N1(CCOCC1)CC1=NC=CC(=N1)N | [NH:8]1[CH2:9][CH2:10][O:11][CH2:12][CH2:13]1.Cl[CH2:7][c:6]1[n:5][cH:4][cH:3][c:2]([NH2:1])[n:14]1>>[NH2:1][c:2]1[cH:3][cH:4][n:5][c:6]([CH2:7][N:8]2[CH2:9][CH2:10][O:11][CH2:12][CH2:13]2)[n:14]1 | C1COCCN1.Nc1ccnc(CCl)n1 | Nc1ccnc(CN2CCOCC2)n1 | null | null | C(C)O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 2bad30dcdb0a20edb8ce877f072b133eedfd870621da393ec393128bfee00977 | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | c1cnc(CN2CCOCC2)nc1 | Cl-[CH2;D2;+0:1]-[c:2](:[#7;a:3]:[c:4]):[#7;a:5]:[c:6].[#8:7]1-[C:8]-[C:9]-[NH;D2;+0:10]-[C:11]-[C:12]-1>>[c:4]:[#7;a:3]:[c:2](-[CH2;D2;+0:1]-[N;H0;D3;+0:10]1-[C:11]-[C:12]-[#8:7]-[C:8]-[C:9]-1):[#7;a:5]:[c:6] | null | [] | null | null | null | null | Following a procedure from J. Chem. Soc. Perkin. Trans. I, 1996, 2925, 2-chloromethyl-pyrimidin-4-ylamine (0.35 g, Eur. Pat. Appl. EP 61318 A2, 1982; Eur. Pat. Appl. 60094 A2, 1982) was dissolved in ethanol (10 mL) and triethylamine (0.51 mL) and morpholine (0.21 mL) were added. The mixture was heated to reflux for 48 ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1COCCN1 | C1COCC[NH]1 | c1cncnc1.C1COCC[NH]1 | HCl | C(C)O | null | null | C1COCCN1.Nc1ccnc(CCl)n1>C(C)O>Nc1ccnc(CN2CCOCC2)n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-def97b4b51ed45a39e0d649f96977a22 | CCOC=CC#N.CCc1nc(C(=N)N)cs1>>CCc1nc(-c2nccc(N)n2)cs1 | C(C)OC=CC#N.Cl.C(C)C=1SC=C(N1)C(=N)N.[O-]CC.[Na+]>>C(C)C=1SC=C(N1)C1=NC=CC(=N1)N | CCO[CH:8]=[CH:9][C:10]#[N:11].[CH3:1][CH2:2][c:3]1[n:4][c:5]([C:6](=[NH:7])[NH2:12])[cH:13][s:14]1>>[CH3:1][CH2:2][c:3]1[n:4][c:5](-[c:6]2[n:7][cH:8][cH:9][c:10]([NH2:11])[n:12]2)[cH:13][s:14]1 | CCOC=CC#N.CCc1nc(C(=N)N)cs1 | CCc1nc(-c2nccc(N)n2)cs1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 1e568f7e0e15482dde11fdfeccd63d6b9d6b5bc1f8269cd40cdfe5561fc41bcc | c6284da6d834238420f26e5398d63d6a0d74f532def882e624d78f4ac191261d | c1cnc(-c2cscn2)nc1 | C-C-O-[CH;D2;+0:1]=[CH;D2;+0:2]-[C;H0;D2;+0:3]#[N;H0;D1;+0:4].[NH2;D1;+0:5]-[C;H0;D3;+0:6](=[NH;D1;+0:7])-[c;H0;D3;+0:8]1:[#7;a:9]:[c:10]:[#16;a:11]:[c:12]:1>>[NH2;D1;+0:4]-[c;H0;D3;+0:3]1:[cH;D2;+0:2]:[cH;D2;+0:1]:[n;H0;D2;+0:7]:[c;H0;D3;+0:6](-[c;H0;D3;+0:8]2:[#7;a:9]:[c:10]:[#16;a:11]:[c:12]:2):[n;H0;D2;+0:5]:1 | null | [] | null | null | null | null | This material was obtained as described in example 2, step A] from 2-ethyl-thiazole-4-carboxamidine hydrochloride (3 g) by treatment with sodium ethoxide (3.13 mL of a 5.4 M solution) and 3-ethoxyacrylonitrile (1.73 mL) to give 2-(2-ethyl-thiazol-4-yl)-pyrimidin-4-ylamine (2.56 g) as a brown solid. MS (ESI): 193.3 (MH+... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Nitrile.Primary amine | Primary amine | null | c1cncnc1 | c1cscn1.c1cncnc1 | HO- | null | null | null | CCOC=CC#N.CCc1nc(C(=N)N)cs1>>CCc1nc(-c2nccc(N)n2)cs1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ed006657a40f44eda58e4a60d4fc4091 | C=C(Cl)C#N.N=C(N)C1CCCC1>>Nc1ccnc(C2CCCC2)n1 | Cl.C1(CCCC1)C(=N)N.ClC(C#N)=C>>C1(CCCC1)C1=NC=CC(=N1)N | Cl[C:3]([C:2]#[N:1])=[CH2:4].[NH:5]=[C:6]([CH:7]1[CH2:8][CH2:9][CH2:10][CH2:11]1)[NH2:12]>>[NH2:1][c:2]1[cH:3][cH:4][n:5][c:6]([CH:7]2[CH2:8][CH2:9][CH2:10][CH2:11]2)[n:12]1 | C=C(Cl)C#N.N=C(N)C1CCCC1 | Nc1ccnc(C2CCCC2)n1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | e15717fdab8a8ff5ba7d0f49a42b2f1ee70a42aaa6c6817caa99be24646dd604 | 3d45291949b890aada3eda520251ab6c726eca25b07da8e42f9c5cda12427181 | c1cnc(C2CCCC2)nc1 | Cl-[C;H0;D3;+0:1](=[CH2;D1;+0:2])-[C;H0;D2;+0:3]#[N;H0;D1;+0:4].[C:5]-[C:6](-[C;H0;D3;+0:7](-[NH2;D1;+0:8])=[NH;D1;+0:9])-[C:10]>>[C:5]-[C:6](-[c;H0;D3;+0:7]1:[n;H0;D2;+0:8]:[c;H0;D3;+0:3](-[NH2;D1;+0:4]):[cH;D2;+0:1]:[cH;D2;+0:2]:[n;H0;D2;+0:9]:1)-[C:10] | 25.9 | [{"value": 25.9, "product": "C1(CCCC1)C1=NC=CC(=N1)N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | This material was obtained in analogy to example 2, step A] via the alternative preparation method from cyclopentanecarboxamidine hydrochloride (CAS 68284-02-6) (500 mg) and 2-chloroacrylonitrile (324 mg) to give 2-cyclopentyl-pyrimidin-4-ylamine as an amorphous glass (142 mg). MS (ESI): 164.6 (MH+). This material was ... | 10.6084/m9.figshare.5104873.v1 | null | Alkenyl halide.Nitrile.Primary amine.Vinyl | Primary amine | null | c1cncnc1 | c1cncnc1.C1CCCC1 | HCl | null | null | null | C=C(Cl)C#N.N=C(N)C1CCCC1>>Nc1ccnc(C2CCCC2)n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-234de0d245f14da2a7db17fad5bb1f8a | Nc1ccnc(Cl)n1.OCC1CC1>>Nc1ccnc(OCC2CC2)n1 | [Na+].[Cl-].NC1=NC(=NC=C1)Cl.C1(CC1)CO.[H-].[Na+]>>C1(CC1)COC1=NC=CC(=N1)N | Cl[c:6]1[n:5][cH:4][cH:3][c:2]([NH2:1])[n:12]1.[OH:7][CH2:8][CH:9]1[CH2:10][CH2:11]1>>[NH2:1][c:2]1[cH:3][cH:4][n:5][c:6]([O:7][CH2:8][CH:9]2[CH2:10][CH2:11]2)[n:12]1 | Nc1ccnc(Cl)n1.OCC1CC1 | Nc1ccnc(OCC2CC2)n1 | null | null | O.CN(C)C=O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | a445000eb5ed501274d93689ad5b9d45095af02deca02b6b541c8a834890a276 | a4cafa7bcd156e21cca6eaac1b32e28ec8540642a31181122e6957f3d7559631 | c1cnc(OCC2CC2)nc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5].[C:6]-[C:7]-[OH;D1;+0:8]>>[C:6]-[C:7]-[O;H0;D2;+0:8]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5] | null | [] | null | null | 1 | HOUR | Cyclopropylmethanol (724 mg) was dissolved in DMF (4 mL) and treated with sodium hydride (401 mg, 60% in mineral oil) at 0° C. for 30 minutes. Then, a solution of 4-amino-2-chloro-pyrimidine (260 mg, CAS 7461-50-9 or made according to J. Am. Chem. Soc. 1930, 52, 1152-1157) in DMF (4 mL) was added drop by drop. The mixt... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary alcohol | Ether | c1cncnc1 | c1cncnc1 | c1cncnc1.C1CC1 | HCl | O.CN(C)C=O | null | 1 | Nc1ccnc(Cl)n1.OCC1CC1>O.CN(C)C=O>Nc1ccnc(OCC2CC2)n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-38e55c372faf4483810a64036efa482b | CC(C)c1nccc(NS(=O)(=O)c2ccc(Cl)c(Cl)c2)n1.CN(C)C(=O)CCl>>CC(C)c1nccc(N(CC(=O)N(C)C)S(=O)(=O)c2ccc(Cl)c(Cl)c2)n1 | ClCC(=O)N(C)C.ClC=1C=C(C=CC1Cl)S(=O)(=O)NC1=NC(=NC=C1)C(C)C.C([O-])([O-])=O.[Cs+].[Cs+]>>ClC=1C=C(C=CC1Cl)S(=O)(=O)N(CC(=O)N(C)C)C1=NC(=NC=C1)C(C)C | [CH3:1][CH:2]([CH3:3])[c:4]1[n:5][cH:6][cH:7][c:8]([NH:9][S:16](=[O:17])(=[O:18])[c:19]2[cH:20][cH:21][c:22]([Cl:23])[c:24]([Cl:25])[cH:26]2)[n:27]1.Cl[CH2:10][C:11](=[O:12])[N:13]([CH3:14])[CH3:15]>>[CH3:1][CH:2]([CH3:3])[c:4]1[n:5][cH:6][cH:7][c:8]([N:9]([CH2:10][C:11](=[O:12])[N:13]([CH3:14])[CH3:15])[S:16](=[O:17])... | CC(C)c1nccc(NS(=O)(=O)c2ccc(Cl)c(Cl)c2)n1.CN(C)C(=O)CCl | CC(C)c1nccc(N(CC(=O)N(C)C)S(=O)(=O)c2ccc(Cl)c(Cl)c2)n1 | null | null | CN(C)C=O.C(C)(=O)OCC | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 0fe6648877a29ae177a907a0d252f35d8beab440bf428116c5424a67bc0e72cd | 0b054affe7e4bb904ceae512aabc19d89c93551cb46dfbc6f220fc85e5eeff75 | O=S(=O)(Nc1ccncn1)c1ccccc1 | Cl-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#7:4](-[C;D1;H3:5])-[C;D1;H3:6].[O;D1;H0:7]=[#16:8](=[O;D1;H0:9])(-[c:10])-[NH;D2;+0:11]-[c:12]1:[#7;a:13]:[c:14]:[#7;a:15]:[c:16]:[c:17]:1>>[C;D1;H3:5]-[#7:4](-[C;D1;H3:6])-[C:2](=[O;D1;H0:3])-[CH2;D2;+0:1]-[N;H0;D3;+0:11](-[c:12]1:[#7;a:13]:[c:14]:[#7;a:15]:[c:16]:[c:17]:1)-[#16:... | null | [] | null | null | 48 | HOUR | 3,4-Dichloro-N-(2-isopropyl-pyrimidin-4-yl)-benzenesulfonamide (80 mg, example 14) was dissolved in DMF (1 mL) and treated with cesium carbonate (113 mg). To the mixture was added 2-chloro-N,N-dimethylacetamide (37 mg) and the resulting suspension was allowed to stir at room temperature for 48 hours and then at 80° C. ... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonamide.Primary halide | Tertiary amine | null | null | c1cncnc1.c1ccccc1 | HCl | CN(C)C=O.C(C)(=O)OCC | null | 48 | CC(C)c1nccc(NS(=O)(=O)c2ccc(Cl)c(Cl)c2)n1.CN(C)C(=O)CCl>CN(C)C=O.C(C)(=O)OCC>CC(C)c1nccc(N(CC(=O)N(C)C)S(=O)(=O)c2ccc(Cl)c(Cl)c2)n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-54aafaa45c154292b6ad0b7c1774e8c1 | CC(=O)CCl.Fc1ccc(S)cc1>>CC(=O)CS(=O)(=O)c1ccc(F)cc1 | OOS(=O)[O-].[K+].[OH-].[Na+].FC1=CC=C(C=C1)S.ClCC(C)=O>>FC1=CC=C(C=C1)S(=O)(=O)CC(C)=O | Cl[CH2:4][C:2]([CH3:1])=[O:3].[SH:5][c:8]1[cH:9][cH:10][c:11]([F:12])[cH:13][cH:14]1>>[CH3:1][C:2](=[O:3])[CH2:4][S:5](=[O:6])(=[O:7])[c:8]1[cH:9][cH:10][c:11]([F:12])[cH:13][cH:14]1 | CC(=O)CCl.Fc1ccc(S)cc1 | CC(=O)CS(=O)(=O)c1ccc(F)cc1 | null | null | CO | Oxidation | OtherReaction | e29d3b0c69c555897af44696f6450211b24b7f035e08987feded8d00cd07bf86 | 8d35534209814511607f6299e9ab9d1ecf7bd491fa093a2c3995c4c0ed936011 | c1ccccc1 | Cl-[CH2;D2;+0:1]-[C:2](-[C;D1;H3:3])=[O;D1;H0:4].[SH;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[C;D1;H3:3]-[C:2](=[O;D1;H0:4])-[CH2;D2;+0:1]-[S;H0;D4;+0:5](=[O;D1;H0:9])(=[O;D1;H0:10])-[c:6](:[c:7]):[c:8] | null | [] | 0 | CELSIUS | 5 | MINUTE | NaOH (1.0M, 40.5 mL, 40.5 mmol) was added at 0° C. to a solution of 4-fluorothiophenol (5.20 g, 40.5 mmol) in methanol (100 mL) followed by addition of chloroacetone (3.87 mL, 48.6 mmol). The reaction was stirred at 0° C. for 5 minutes. Oxone (50 g, 81 mmol) was added all at once. The suspension was stirred at 0° C. an... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ketone.Aromatic thiol | Ketone.Sulfone | null | null | c1ccccc1 | HCl | CO | 0 | 0.083333 | CC(=O)CCl.Fc1ccc(S)cc1>CO>CC(=O)CS(=O)(=O)c1ccc(F)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-c935895953894e70b1c274db851ad23e | CC(=O)CS(=O)(=O)c1ccc(F)cc1.Cc1cc(N)[nH]n1.O=Cc1ccc(Cl)c(Cl)c1>>CC1=C(S(=O)(=O)c2ccc(F)cc2)C(c2ccc(Cl)c(Cl)c2)n2nc(C)cc2N1 | FC1=CC=C(C=C1)S(=O)(=O)CC(C)=O.CC1=NNC(=C1)N.ClC=1C=C(C=O)C=CC1Cl>>ClC=1C=C(C=CC1Cl)C1C(=C(NC=2N1N=C(C2)C)C)S(=O)(=O)C2=CC=C(C=C2)F | O=[C:2]([CH3:1])[CH2:3][S:4](=[O:5])(=[O:6])[c:7]1[cH:8][cH:9][c:10]([F:11])[cH:12][cH:13]1.[nH:23]1[n:24][c:25]([CH3:26])[cH:27][c:28]1[NH2:29].O=[CH:14][c:15]1[cH:16][cH:17][c:18]([Cl:19])[c:20]([Cl:21])[cH:22]1>>[CH3:1][C:2]1=[C:3]([S:4](=[O:5])(=[O:6])[c:7]2[cH:8][cH:9][c:10]([F:11])[cH:12][cH:13]2)[CH:14]([c:15]2[... | CC(=O)CS(=O)(=O)c1ccc(F)cc1.Cc1cc(N)[nH]n1.O=Cc1ccc(Cl)c(Cl)c1 | CC1=C(S(=O)(=O)c2ccc(F)cc2)C(c2ccc(Cl)c(Cl)c2)n2nc(C)cc2N1 | null | N1CCCCC1 | C1CCOC1 | Heteroatom Alkylation and Arylation | OtherReaction | c621ba864f656a559eb5849cd46ef70261d98951ba565d11bf39f9f8fcdc5da5 | bd2570d285dcbb89a92430e1ca5da930fc4b87af1197036ccf7a83f622f8a245 | O=S(=O)(C1=CNc2ccnn2C1c1ccccc1)c1ccccc1 | O=[C;H0;D3;+0:1](-[C;D1;H3:2])-[CH2;D2;+0:3]-[#16:4](=[O;D1;H0:5])(=[O;D1;H0:6])-[c:7].O=[CH;D2;+0:8]-[c:9](:[c:10]):[c:11].[NH2;D1;+0:12]-[c:13]1:[c:14]:[c:15]:[#7;a:16]:[nH;D2;+0:17]:1>>[C;D1;H3:2]-[C;H0;D3;+0:1]1=[C;H0;D3;+0:3](-[#16:4](=[O;D1;H0:5])(=[O;D1;H0:6])-[c:7])-[CH;D3;+0:8](-[c:9](:[c:10]):[c:11])-[n;H0;D3... | null | [] | 70 | CELSIUS | 48 | HOUR | 1-(4-Fluorophenylsulfonyl)propan-2-one (150 mg, 0.69 mmol), 3-methyl-1H-pyrazol-5-amine (67 mg, 0.69 mmol) and 3,4-dichlorobenzaldehyde (121 mg, 0.69 mmol) were dissolved in THF (5 mL), to which was added a catalytic amount of piperidine (3 drops). The reaction in a sealed tube was stirred at 70° C. for about 48 hrs. A... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ketone.Primary amine | Enamine | c1cn[nH]c1 | C1=CNc2ccnn2C1 | c1ccccc1.c1ccccc1.C1=CNc2ccnn2C1 | HO- | N1CCCCC1.C1CCOC1 | 70 | 48 | CC(=O)CS(=O)(=O)c1ccc(F)cc1.Cc1cc(N)[nH]n1.O=Cc1ccc(Cl)c(Cl)c1>N1CCCCC1.C1CCOC1>CC1=C(S(=O)(=O)c2ccc(F)cc2)C(c2ccc(Cl)c(Cl)c2)n2nc(C)cc2N1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-becfd463ab21483b9b9c997be6baa8ac | COc1ccc(NS(=O)(=O)[O-])cc1.ClP(Cl)(Cl)(Cl)Cl>>COc1ccc(NS(=O)(=O)Cl)cc1 | COC1=CC=C(C=C1)NS([O-])(=O)=O.[Na+].P(Cl)(Cl)(Cl)(Cl)Cl>>COC1=CC=C(C=C1)NS(=O)(=O)Cl | [O-][S:8]([NH:7][c:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:13][cH:12]1)(=[O:9])=[O:10].ClP(Cl)(Cl)(Cl)[Cl:11]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([NH:7][S:8](=[O:9])(=[O:10])[Cl:11])[cH:12][cH:13]1 | COc1ccc(NS(=O)(=O)[O-])cc1.ClP(Cl)(Cl)(Cl)Cl | COc1ccc(NS(=O)(=O)Cl)cc1 | null | null | C1=CC=CC=C1 | Functional Group Interconversion | OtherReaction | 877ce8a46446e27a8e9fce0d2ed351d5ab39567fe06f48514bd557ed275fe272 | 2d51380cb2f3dba7bea1307c1e64e6a1d3e9d4d3ee90d7fbc7612a8206e956fd | c1ccccc1 | Cl-P(-Cl)(-Cl)(-Cl)-[Cl;H0;D1;+0:1].[O-]-[S;H0;D4;+0:2](=[O;D1;H0:3])(=[O;D1;H0:4])-[#7:5]-[c:6]>>[Cl;H0;D1;+0:1]-[S;H0;D4;+0:2](=[O;D1;H0:3])(=[O;D1;H0:4])-[#7:5]-[c:6] | null | [] | null | null | null | null | To sodium 4-methoxyphenylsulfamate (10.0 g 44 mmol) suspended in benzene (100 mL) was added PCl5 (9.2 g, 44 mmol) cautiously. The mixture was slowly warmed up and refluxed for 15 hrs. After cooling to rt., the mixture was filtered through a pad of Celite and solvent was removed from filtrate to leave a brown oil as 4-m... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonamide | Sulfonamide | null | null | c1ccccc1 | Other | C1=CC=CC=C1 | null | null | COc1ccc(NS(=O)(=O)[O-])cc1.ClP(Cl)(Cl)(Cl)Cl>C1=CC=CC=C1>COc1ccc(NS(=O)(=O)Cl)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-3a4a80bca6e3486abb176dbee2bd8dd9 | C=C(C)O[Si](C)(C)C.COc1ccc(NS(=O)(=O)Cl)cc1>>COc1ccc(NS(=O)(=O)CC(C)=O)cc1 | COC1=CC=C(C=C1)NS(=O)(=O)Cl.C[Si](OC(=C)C)(C)C.C(C)N(CC)CC>>COC1=CC=C(C=C1)NS(=O)(=O)CC(C)=O | C[Si](C)(C)[O:14][C:12](=[CH2:11])[CH3:13].Cl[S:8]([NH:7][c:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:16][cH:15]1)(=[O:9])=[O:10]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([NH:7][S:8](=[O:9])(=[O:10])[CH2:11][C:12]([CH3:13])=[O:14])[cH:15][cH:16]1 | C=C(C)O[Si](C)(C)C.COc1ccc(NS(=O)(=O)Cl)cc1 | COc1ccc(NS(=O)(=O)CC(C)=O)cc1 | null | null | C(C)#N | Acylation | OtherReaction | 53b5a27e63f9f34cacd789ac7033a942fcfc16708a04b9b2e4b43a5249628f7c | 27e97297ea66ac465431742f86a91f905a63b830ee2750a791d0d4e316ef692b | c1ccccc1 | C-[Si](-C)(-C)-[O;H0;D2;+0:1]-[C;H0;D3;+0:2](-[C;D1;H3:3])=[CH2;D1;+0:4].Cl-[S;H0;D4;+0:5](=[O;D1;H0:6])(=[O;D1;H0:7])-[#7:8]-[c:9]>>[C;D1;H3:3]-[C;H0;D3;+0:2](=[O;H0;D1;+0:1])-[CH2;D2;+0:4]-[S;H0;D4;+0:5](=[O;D1;H0:6])(=[O;D1;H0:7])-[#7:8]-[c:9] | null | [] | null | null | null | null | 4-Methoxyphenylsulfamoyl chloride (11.0 g, crude from Step B) in acetonitrile (5.0 mL) was added to a mixture of trimethyl(prop-1-en-2-yloxy)silane (0.85 g, 85% purity, 5.56 mmol) and triethylamine (2.0 mL) in acetonitrile (10 mL) at rt. Upon addition, the reaction was warmed up and refluxed for 2 hrs. After cooling to... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonamide.Vinyl.Silyl protective group | Sulfonamide.Ketone | null | null | c1ccccc1 | HCl | C(C)#N | null | null | C=C(C)O[Si](C)(C)C.COc1ccc(NS(=O)(=O)Cl)cc1>C(C)#N>COc1ccc(NS(=O)(=O)CC(C)=O)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-8abaf50504aa403d8f2b6fc8485240d7 | COc1ccc(NS(=O)(=O)CC(C)=O)cc1.Cc1cc(N)[nH]n1.O=Cc1ccc(Cl)c(Cl)c1>>COc1ccc(NS(=O)(=O)C2=C(C)Nc3cc(C)nn3C2c2ccc(Cl)c(Cl)c2)cc1 | COC1=CC=C(C=C1)NS(=O)(=O)CC(C)=O.CC1=NNC(=C1)N.ClC=1C=C(C=O)C=CC1Cl>>ClC=1C=C(C=CC1Cl)C1C(=C(NC=2N1N=C(C2)C)C)S(=O)(=O)NC2=CC=C(C=C2)OC | O=[C:12]([CH2:11][S:8]([NH:7][c:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:31][cH:30]1)(=[O:9])=[O:10])[CH3:13].[NH2:14][c:15]1[cH:16][c:17]([CH3:18])[n:19][nH:20]1.O=[CH:21][c:22]1[cH:23][cH:24][c:25]([Cl:26])[c:27]([Cl:28])[cH:29]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([NH:7][S:8](=[O:9])(=[O:10])[C:11]2=[C:12]([CH3:13])[N... | COc1ccc(NS(=O)(=O)CC(C)=O)cc1.Cc1cc(N)[nH]n1.O=Cc1ccc(Cl)c(Cl)c1 | COc1ccc(NS(=O)(=O)C2=C(C)Nc3cc(C)nn3C2c2ccc(Cl)c(Cl)c2)cc1 | null | N1CCCCC1 | C1CCOC1 | Heteroatom Alkylation and Arylation | OtherReaction | c621ba864f656a559eb5849cd46ef70261d98951ba565d11bf39f9f8fcdc5da5 | bd2570d285dcbb89a92430e1ca5da930fc4b87af1197036ccf7a83f622f8a245 | O=S(=O)(Nc1ccccc1)C1=CNc2ccnn2C1c1ccccc1 | O=[C;H0;D3;+0:1](-[C;D1;H3:2])-[CH2;D2;+0:3]-[#16:4](-[#7:5])(=[O;D1;H0:6])=[O;D1;H0:7].O=[CH;D2;+0:8]-[c:9](:[c:10]):[c:11].[NH2;D1;+0:12]-[c:13]1:[c:14]:[c:15]:[#7;a:16]:[nH;D2;+0:17]:1>>[#7:5]-[#16:4](=[O;D1;H0:6])(=[O;D1;H0:7])-[C;H0;D3;+0:3]1=[C;H0;D3;+0:1](-[C;D1;H3:2])-[NH;D2;+0:12]-[c:13]2:[c:14]:[c:15]:[#7;a:1... | null | [] | 70 | CELSIUS | 36 | HOUR | N-(4-Methoxyphenyl)-2-oxopropane-1-sulfonamide (100 mg, 0.41 mmol, from Step C), 3-methyl-1H-pyrazol-5-amine (40 mg, 0.41 mmol) and 3,4-dichlorobenzaldehyde (72 mg, 0.41 mmol) were dissolved in THF (6 mL), to which was added a catalytic amount of piperidine (3 drops). The reaction in a sealed tube was stirred at 70° C.... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ketone.Primary amine | Enamine | c1cn[nH]c1 | C1=CNc2ccnn2C1 | c1ccccc1.C1=CNc2ccnn2C1.c1ccccc1 | HO- | N1CCCCC1.C1CCOC1 | 70 | 36 | COc1ccc(NS(=O)(=O)CC(C)=O)cc1.Cc1cc(N)[nH]n1.O=Cc1ccc(Cl)c(Cl)c1>N1CCCCC1.C1CCOC1>COc1ccc(NS(=O)(=O)C2=C(C)Nc3cc(C)nn3C2c2ccc(Cl)c(Cl)c2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-25d1460d8f074930a96f65e0a30e9f67 | C1CCNC1.CS(=O)(=O)Cl>>CS(=O)(=O)N1CCCC1 | CS(=O)(=O)Cl.N1CCCC1.C(C)N(CC)CC>>CS(=O)(=O)N1CCCC1 | [NH:5]1[CH2:6][CH2:7][CH2:8][CH2:9]1.Cl[S:2]([CH3:1])(=[O:3])=[O:4]>>[CH3:1][S:2](=[O:3])(=[O:4])[N:5]1[CH2:6][CH2:7][CH2:8][CH2:9]1 | C1CCNC1.CS(=O)(=O)Cl | CS(=O)(=O)N1CCCC1 | null | null | ClCCl | Miscellaneous | Sulfonamide synthesis (Schotten-Baumann) secondary amine | fad7fec5031576b1dfc4c6ce5d869057759c268623601223d448fbc99ad4c75b | 971e620478d668662a3bf915b510f5704d42a595d6ca9c67de007bd5d7063a75 | C1CCNC1 | Cl-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4].[C:5]1-[C:6]-[C:7]-[C:8]-[NH;D2;+0:9]-1>>[C;D1;H3:2]-[S;H0;D4;+0:1](=[O;D1;H0:3])(=[O;D1;H0:4])-[N;H0;D3;+0:9]1-[C:5]-[C:6]-[C:7]-[C:8]-1 | null | [] | null | null | null | null | To a solution of pyrrolidine (8.25 g, 116 mmol) in dichloromethane (120 mL) were added triethylamine (19.0 mL, 139 mmol) followed by addition of methanesulfonyl chloride (9.0 mL, 116 mmol) at 0° C. The reaction was allowed to stir while warming up to rt. overnight, which was transferred to a separatory funnel and washe... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amine.Sulfonyl halide | Tertiary amine | C1CCNC1 | C1CC[NH]C1 | C1CC[NH]C1 | HCl | ClCCl | null | null | C1CCNC1.CS(=O)(=O)Cl>ClCCl>CS(=O)(=O)N1CCCC1 |
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