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-9b4501613ebb4ca9b57b37a0651b562c | COc1cc(-c2nc3sccn3c2C(=O)C=CN(C)C)ccc1F.[H]/N=C(/N)NC1CCN(C(=O)OC(C)(C)C)CC1>>COc1cc(-c2nc3sccn3c2-c2ccnc(NC3CCN(C(=O)OC(C)(C)C)CC3)n2)ccc1F | [O-]CC.[Na+].CN(C=CC(=O)C1=C(N=C2SC=CN21)C2=CC(=C(C=C2)F)OC)C.Cl.N/C(=N/[H])/NC1CCN(CC1)C(=O)OC(C)(C)C>>FC1=C(C=C(C=C1)C=1N=C2SC=CN2C1C1=NC(=NC=C1)NC1CCN(CC1)C(=O)OC(C)(C)C)OC | CN(C)[CH:16]=[CH:15][C:14](=O)[c:13]1[c:6](-[c:5]2[cH:4][c:3]([O:2][CH3:1])[c:36]([F:37])[cH:35][cH:34]2)[n:7][c:8]2[s:9][cH:10][cH:11][n:12]21.[H]/[N:17]=[C:18](\[NH:19][CH:20]1[CH2:21][CH2:22][N:23]([C:24](=[O:25])[O:26][C:27]([CH3:28])([CH3:29])[CH3:30])[CH2:31][CH2:32]1)[NH2:33]>>[CH3:1][O:2][c:3]1[cH:4][c:5](-[c:6... | COc1cc(-c2nc3sccn3c2C(=O)C=CN(C)C)ccc1F.[H]/N=C(/N)NC1CCN(C(=O)OC(C)(C)C)CC1 | COc1cc(-c2nc3sccn3c2-c2ccnc(NC3CCN(C(=O)OC(C)(C)C)CC3)n2)ccc1F | null | null | C(C)O | Aromatic Heterocycle Formation | OtherReaction | 78274536798da2b99a51ce47d0994df99b4d5455af910301779a9ae5938608b5 | 11da551d0a7bf93f6d300d0e461ec1d4a2060497908163f95323146dc93cd499 | c1ccc(-c2nc3sccn3c2-c2ccnc(NC3CCNCC3)n2)cc1 | C-N(-C)-[CH;D2;+0:1]=[CH;D2;+0:2]-[C;H0;D3;+0:3](=O)-[c;H0;D3;+0:4]1:[#7;a:5]2:[c:6]:[c:7]:[#16;a:8]:[c:9]:2:[#7;a:10]:[c:11]:1-[c:12].[C:13]-[#7:14]/[C;H0;D3;+0:15](-[NH2;D1;+0:16])=[N;H0;D2;+0:17]\[H]>>[C:13]-[#7:14]-[c;H0;D3;+0:15]1:[n;H0;D2;+0:17]:[cH;D2;+0:1]:[cH;D2;+0:2]:[c;H0;D3;+0:3](-[c;H0;D3;+0:4]2:[#7;a:5]3:... | 88 | [{"value": 88.0, "product": "FC1=C(C=C(C=C1)C=1N=C2SC=CN2C1C1=NC(=NC=C1)NC1CCN(CC1)C(=O)OC(C)(C)C)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 87.7, "product": "FC1=C(C=C(C=C1)C=1N=C2SC=CN2C1C1=NC(=NC=C1)NC1CCN(CC1)C(=O)OC(C)(C)C)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 3-(dimethylamino)-1-[6-(4-fluoro-3-methoxyphenyl)imidazo[2,1-b][1,3]thiazol-5-yl]prop-2-en-1-one (0.537 g, 1.55 mmol) and tert-butyl 4-{[(Z)-amino(imino)methyl]amino}piperidine-1-carboxylate hydrochloride (0.650 g, 2.33 mmol) was diluted with 13 ml of absolute ethanol and treated with 1.35 eq. of a 21% w/w... | 10.6084/m9.figshare.5104873.v1 | null | Enamine.Ketone.Primary amine | null | null | c1cncnc1 | c1ccccc1.c1cn2ccsc2n1.c1cncnc1.C1CC[NH]CC1 | HO- | C(C)O | null | null | COc1cc(-c2nc3sccn3c2C(=O)C=CN(C)C)ccc1F.[H]/N=C(/N)NC1CCN(C(=O)OC(C)(C)C)CC1>C(C)O>COc1cc(-c2nc3sccn3c2-c2ccnc(NC3CCN(C(=O)OC(C)(C)C)CC3)n2)ccc1F |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d24943ef497042baa68dee089eabafa4 | COc1cc(-c2nc3sccn3c2-c2ccnc(NC3CCN(C(=O)OC(C)(C)C)CC3)n2)ccc1F>>COc1cc(-c2nc3sccn3c2-c2ccnc(NC3CCNCC3)n2)ccc1F | FC1=C(C=C(C=C1)C=1N=C2SC=CN2C1C1=NC(=NC=C1)NC1CCN(CC1)C(=O)OC(C)(C)C)OC.Cl>>Cl.FC1=C(C=C(C=C1)C=1N=C2SC=CN2C1C1=NC(=NC=C1)NC1CCNCC1)OC | CC(C)(C)OC(=O)[N:23]1[CH2:22][CH2:21][CH:20]([NH:19][c:18]2[n:17][cH:16][cH:15][c:14](-[c:13]3[c:6](-[c:5]4[cH:4][c:3]([O:2][CH3:1])[c:29]([F:30])[cH:28][cH:27]4)[n:7][c:8]4[s:9][cH:10][cH:11][n:12]43)[n:26]2)[CH2:25][CH2:24]1>>[CH3:1][O:2][c:3]1[cH:4][c:5](-[c:6]2[n:7][c:8]3[s:9][cH:10][cH:11][n:12]3[c:13]2-[c:14]2[cH... | COc1cc(-c2nc3sccn3c2-c2ccnc(NC3CCN(C(=O)OC(C)(C)C)CC3)n2)ccc1F | COc1cc(-c2nc3sccn3c2-c2ccnc(NC3CCNCC3)n2)ccc1F | null | null | O1CCOCC1.CCOCC | Reduction | Boc amine deprotection | bf3cd5dc3e17e694d8665c89f5d7e08e8763b18436a633eb66e9bf530b8b0316 | a94b29c7264c852156fc1cdd4a0951a4fc26c06d0edc9e50c743825dbf79e3fd | c1ccc(-c2nc3sccn3c2-c2ccnc(NC3CCNCC3)n2)cc1 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1](-[C:2]-[C:3])-[C:4]-[C:5]>>[C:3]-[C:2]-[NH;D2;+0:1]-[C:4]-[C:5] | 96 | [{"value": 96.0, "product": "Cl.FC1=C(C=C(C=C1)C=1N=C2SC=CN2C1C1=NC(=NC=C1)NC1CCNCC1)OC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | The tert-butyl 4-({4-[6-(4-fluoro-3-methoxyphenyl)imidazo[2,1-b][1,3]thiazol-5-yl]pyrimidin-2-yl}amino)piperidine-1-carboxylate (0.713 g, 1.36 mmol) was dissolved in 15 ml of dioxane and treated with 7.5 ml of anhydrous 4N HCl in dioxane at room temperature (RT). The reaction mixture was stirred at room temperature for... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Secondary amine | C1CC[NH]CC1 | C1CCNCC1 | c1ccccc1.c1cn2ccsc2n1.c1cncnc1.C1CCNCC1 | HO- | O1CCOCC1.CCOCC | null | 2 | COc1cc(-c2nc3sccn3c2-c2ccnc(NC3CCN(C(=O)OC(C)(C)C)CC3)n2)ccc1F>O1CCOCC1.CCOCC>COc1cc(-c2nc3sccn3c2-c2ccnc(NC3CCNCC3)n2)ccc1F |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-099ff9a3f7c245db8c7687562bf78285 | COc1cc(-c2nc3sccn3c2-c2ccnc(NC3CCNCC3)n2)ccc1F.O=S(=O)(Cl)C1CC1>>COc1cc(-c2nc3sccn3c2-c2ccnc(NC3CCN(S(=O)(=O)C4CC4)CC3)n2)ccc1F | Cl.FC1=C(C=C(C=C1)C=1N=C2SC=CN2C1C1=NC(=NC=C1)NC1CCNCC1)OC.CCN(C(C)C)C(C)C.C1(CC1)S(=O)(=O)Cl>>C1(CC1)S(=O)(=O)N1CCC(CC1)NC1=NC=CC(=N1)C1=C(N=C2SC=CN21)C2=CC(=C(C=C2)F)OC | [CH3:1][O:2][c:3]1[cH:4][c:5](-[c:6]2[n:7][c:8]3[s:9][cH:10][cH:11][n:12]3[c:13]2-[c:14]2[cH:15][cH:16][n:17][c:18]([NH:19][CH:20]3[CH2:21][CH2:22][NH:23][CH2:30][CH2:31]3)[n:32]2)[cH:33][cH:34][c:35]1[F:36].Cl[S:24](=[O:25])(=[O:26])[CH:27]1[CH2:28][CH2:29]1>>[CH3:1][O:2][c:3]1[cH:4][c:5](-[c:6]2[n:7][c:8]3[s:9][cH:10... | COc1cc(-c2nc3sccn3c2-c2ccnc(NC3CCNCC3)n2)ccc1F.O=S(=O)(Cl)C1CC1 | COc1cc(-c2nc3sccn3c2-c2ccnc(NC3CCN(S(=O)(=O)C4CC4)CC3)n2)ccc1F | null | null | C(Cl)Cl | Acylation | Sulfonamide synthesis (Schotten-Baumann) secondary amine | d63e07b47df62aebedb35134f6d0504cfcbed5ccfdec31c2c42bba6875c15fe7 | b7aca5a5d690b0846685a854bc946849e1041bfc3965161290b5ffb2821af09e | O=S(=O)(C1CC1)N1CCC(Nc2nccc(-c3c(-c4ccccc4)nc4sccn34)n2)CC1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[C:4]1-[C:5]-[C:6]-1.[C:7]-[C:8]-[NH;D2;+0:9]-[C:10]-[C:11]>>[C:7]-[C:8]-[N;H0;D3;+0:9](-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[C:4]1-[C:5]-[C:6]-1)-[C:10]-[C:11] | 96 | [{"value": 96.0, "product": "C1(CC1)S(=O)(=O)N1CCC(CC1)NC1=NC=CC(=N1)C1=C(N=C2SC=CN21)C2=CC(=C(C=C2)F)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 95.7, "product": "C1(CC1)S(=O)(=O)N1CCC(CC1)NC1=NC=CC(=N1)C1=C(N=C2SC=CN21)C2=CC(=C(C=C2)F)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | The 4-[6-(4-fluoro-3-methoxyphenyl)imidazo[2,1-b][1,3]thiazol-5-yl]-N-[piperidin-4-yl]pyrimidin-2-amine hydrochloride (0.25 g, 0.50 mmol) in methylene chloride (DCM) (12 ml) was cooled to 0° C. and was treated with Hunig's base (440 μl, 2.5 mmol). The mixture was kept at 0° C. for 30 minutes then the cyclopropyl-sulfon... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amine.Sulfonyl halide | Tertiary amine | C1CCNCC1 | C1CC[NH]CC1 | c1ccccc1.c1cn2ccsc2n1.c1cncnc1.C1CC[NH]CC1.C1CC1 | HCl | C(Cl)Cl | null | 0.5 | COc1cc(-c2nc3sccn3c2-c2ccnc(NC3CCNCC3)n2)ccc1F.O=S(=O)(Cl)C1CC1>C(Cl)Cl>COc1cc(-c2nc3sccn3c2-c2ccnc(NC3CCN(S(=O)(=O)C4CC4)CC3)n2)ccc1F |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e48581f19f644b8a9f2e315f6deca415 | COc1cc(-c2nc3sccn3c2-c2ccnc(NC3CCN(S(=O)(=O)C4CC4)CC3)n2)ccc1F>>O=S(=O)(C1CC1)N1CCC(Nc2nccc(-c3c(-c4ccc(F)c(O)c4)nc4sccn34)n2)CC1 | B(Br)(Br)Br.C1(CC1)S(=O)(=O)N1CCC(CC1)NC1=NC=CC(=N1)C1=C(N=C2SC=CN21)C2=CC(=C(C=C2)F)OC>>C1(CC1)S(=O)(=O)N1CCC(CC1)NC1=NC=CC(=N1)C1=C(N=C2SC=CN21)C=2C=CC(=C(C2)O)F | C[O:25][c:24]1[c:22]([F:23])[cH:21][cH:20][c:19](-[c:18]2[c:17](-[c:16]3[cH:15][cH:14][n:13][c:12]([NH:11][CH:10]4[CH2:9][CH2:8][N:7]([S:2](=[O:1])(=[O:3])[CH:4]5[CH2:5][CH2:6]5)[CH2:35][CH2:34]4)[n:33]3)[n:32]3[c:28]([n:27]2)[s:29][cH:30][cH:31]3)[cH:26]1>>[O:1]=[S:2](=[O:3])([CH:4]1[CH2:5][CH2:6]1)[N:7]1[CH2:8][CH2:9... | COc1cc(-c2nc3sccn3c2-c2ccnc(NC3CCN(S(=O)(=O)C4CC4)CC3)n2)ccc1F | O=S(=O)(C1CC1)N1CCC(Nc2nccc(-c3c(-c4ccc(F)c(O)c4)nc4sccn34)n2)CC1 | null | null | C(Cl)Cl | Deprotection | Cleavage of methoxy ethers to alcohols | c5320c7dfa4f544d4900efcae9b3262bf0d5286bcf39c86109232351f35b23d5 | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | O=S(=O)(C1CC1)N1CCC(Nc2nccc(-c3c(-c4ccccc4)nc4sccn34)n2)CC1 | C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[OH;D1;+0:1]-[c:2](:[c:3]):[c:4] | 86 | [{"value": 86.0, "product": "C1(CC1)S(=O)(=O)N1CCC(CC1)NC1=NC=CC(=N1)C1=C(N=C2SC=CN21)C=2C=CC(=C(C2)O)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 85.9, "product": "C1(CC1)S(=O)(=O)N1CCC(CC1)NC1=NC=CC(=N1)C1=C(N=C2SC=CN21)C=2C=CC(=C(C2)O)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | The N-[1-(cyclopropylsulfonyl)piperidin-4-yl]-4-[6-(4-fluoro-3-methoxyphenyl)imidazo[2,1-b][1,3]thiazol-5-yl]pyrimidin-2-amine (0.226 g, 0.43 mmol) in methylene chloride (8 ml) was cooled to −78° C. and slowly treated with 1 molar solution of boron tribromide in methylene chloride (3.4 ml). The reaction mixture was kep... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | null | null | C1CC1.C1CC[NH]CC1.c1cncnc1.c1ccccc1.c1cn2ccsc2n1 | Other | C(Cl)Cl | null | 1 | COc1cc(-c2nc3sccn3c2-c2ccnc(NC3CCN(S(=O)(=O)C4CC4)CC3)n2)ccc1F>C(Cl)Cl>O=S(=O)(C1CC1)N1CCC(Nc2nccc(-c3c(-c4ccc(F)c(O)c4)nc4sccn34)n2)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d81fd74075da410cb9bfee6494225657 | N#Cc1cccc(C(=O)CBr)c1.Nc1nccs1>>N#Cc1cccc(-c2cn3ccsc3n2)c1 | NC=1SC=CN1.BrCC(=O)C1=CC(=CC=C1)C#N.[OH-].[NH4+]>>C(#N)C=1C=C(C=CC1)C=1N=C2SC=CN2C1 | O=[C:8]([c:7]1[cH:6][cH:5][cH:4][c:3]([C:2]#[N:1])[cH:16]1)[CH2:9]Br.[n:10]1[cH:11][cH:12][s:13][c:14]1[NH2:15]>>[N:1]#[C:2][c:3]1[cH:4][cH:5][cH:6][c:7](-[c:8]2[cH:9][n:10]3[cH:11][cH:12][s:13][c:14]3[n:15]2)[cH:16]1 | N#Cc1cccc(C(=O)CBr)c1.Nc1nccs1 | N#Cc1cccc(-c2cn3ccsc3n2)c1 | null | null | C(C)O | Aromatic Heterocycle Formation | OtherReaction | fc4245e28231e2acdadf0a109add94d7bcbb15727aa9b3c4274dbbacfc4598a4 | 9e77d52183fdbe84f0d2ab96039aaf521caea9340e743bdc6436175f1a3bbdb6 | c1ccc(-c2cn3ccsc3n2)cc1 | Br-[CH2;D2;+0:1]-[C;H0;D3;+0:2](=O)-[c;H0;D3;+0:3](:[c:4]:[c:5]):[c:6]:[c:7].[NH2;D1;+0:8]-[c:9]1:[#16;a:10]:[c:11]:[c:12]:[n;H0;D2;+0:13]:1>>[c:5]:[c:4]:[c;H0;D3;+0:3](-[c;H0;D3;+0:2]1:[cH;D2;+0:1]:[n;H0;D3;+0:13]2:[c:12]:[c:11]:[#16;a:10]:[c:9]:2:[n;H0;D2;+0:8]:1):[c:6]:[c:7] | 81 | [{"value": 81.0, "product": "C(#N)C=1C=C(C=CC1)C=1N=C2SC=CN2C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 81.0, "product": "C(#N)C=1C=C(C=CC1)C=1N=C2SC=CN2C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 20 | HOUR | To a mixture of 2-aminothiazole (3.29 g, 32.9 mmol) and 2-bromo-3′-cyano-acetophenone (7.37 g, 32.9 mmol) was added absolute ethanol (250 mL). The reaction was allowed to reflux with vigorous stirring for 20 hours. The reaction mixture was reduced to half its original volume in vacuo. The remaining suspension was poure... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ketone.Primary amine | null | c1cscn1 | c1cn2ccsc2n1 | c1ccccc1.c1cn2ccsc2n1 | HBr | C(C)O | null | 20 | N#Cc1cccc(C(=O)CBr)c1.Nc1nccs1>C(C)O>N#Cc1cccc(-c2cn3ccsc3n2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-2e94214baf7e4db68f7e770b8b75e5a8 | CC(=O)OC(C)=O.N#Cc1cccc(-c2cn3ccsc3n2)c1>>CC(=O)c1c(-c2cccc(C#N)c2)nc2sccn12 | C(#N)C=1C=C(C=CC1)C=1N=C2SC=CN2C1.C(C)(=O)OC(C)=O.S(O)(O)(=O)=O>>C(#N)C=1C=C(C=CC1)C=1N=C2SC=CN2C1C(C)=O | CC(=O)O[C:2]([CH3:1])=[O:3].[cH:4]1[c:5](-[c:6]2[cH:7][cH:8][cH:9][c:10]([C:11]#[N:12])[cH:13]2)[n:14][c:15]2[s:16][cH:17][cH:18][n:19]12>>[CH3:1][C:2](=[O:3])[c:4]1[c:5](-[c:6]2[cH:7][cH:8][cH:9][c:10]([C:11]#[N:12])[cH:13]2)[n:14][c:15]2[s:16][cH:17][cH:18][n:19]12 | CC(=O)OC(C)=O.N#Cc1cccc(-c2cn3ccsc3n2)c1 | CC(=O)c1c(-c2cccc(C#N)c2)nc2sccn12 | null | null | ClCCl | C-C Coupling | Friedel-Crafts acylation | 20e4fc8dbd319e0c49a94d48e9c26d09ea69cb91c825364825442124ee99bcaa | e8c3519869b9d5fd7c4ab2911407db4a86c645fb02749ed598ab3b129e3927f8 | c1ccc(-c2cn3ccsc3n2)cc1 | C-C(=O)-O-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[c:4]-[c:5]1:[#7;a:6]:[c:7]2:[#16;a:8]:[c:9]:[c:10]:[#7;a:11]:2:[cH;D2;+0:12]:1>>[C;D1;H3:2]-[C;H0;D3;+0:1](=[O;D1;H0:3])-[c;H0;D3;+0:12]1:[#7;a:11]2:[c:10]:[c:9]:[#16;a:8]:[c:7]:2:[#7;a:6]:[c:5]:1-[c:4] | 74 | [{"value": 74.0, "product": "C(#N)C=1C=C(C=CC1)C=1N=C2SC=CN2C1C(C)=O", "details": "PERCENTYIELD", "is_desired": false}] | 135 | CELSIUS | null | null | To a mixture of 6-(3-cyanophenyl)-imidazo[2,1-b]thiazole (5.50 g, 24.4 mmol) and acetic anhydride (50 mL) was added 0.6 mL of concentrated sulfuric acid. The reaction mixture was heated at 135° C. for 5 hours. After cooling to room temperature, the reaction mixture was diluted with dichloromethane (100 mL), washed with... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride | Ketone | c1cn2ccsc2n1 | c1cn2ccsc2n1 | c1ccccc1.c1cn2ccsc2n1 | HO- | ClCCl | 135 | null | CC(=O)OC(C)=O.N#Cc1cccc(-c2cn3ccsc3n2)c1>ClCCl>CC(=O)c1c(-c2cccc(C#N)c2)nc2sccn12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-175172ecebcc4f3781a0057d35e58ec1 | CC(=O)c1c(-c2cccc(C#N)c2)nc2sccn12>>CN(C)C=CC(=O)c1c(-c2cccc(C#N)c2)nc2sccn12 | C(#N)C=1C=C(C=CC1)C=1N=C2SC=CN2C1C(C)=O>>CN(C=CC(=O)C1=C(N=C2SC=CN21)C2=CC(=CC=C2)C#N)C | [cH:1]1[cH:4][n:2]2[c:8]([C:6]([CH3:5])=[O:7])[c:9](-[c:10]3[cH:11][cH:12][cH:13][c:14]([C:15]#[N:16])[cH:17]3)[n:18][c:19]2[s:20]1>>[CH3:1][N:2]([CH3:3])[CH:4]=[CH:5][C:6](=[O:7])[c:8]1[c:9](-[c:10]2[cH:11][cH:12][cH:13][c:14]([C:15]#[N:16])[cH:17]2)[n:18][c:19]2[s:20][cH:21][cH:22][n:23]12 | CC(=O)c1c(-c2cccc(C#N)c2)nc2sccn12 | CN(C)C=CC(=O)c1c(-c2cccc(C#N)c2)nc2sccn12 | null | null | COC(N(C)C)OC | Functional Group Addition | OtherReaction | d78592f81ffc52d8f66c1cf57f8590b6b3c504d4f17449a40395a3927942ea1f | 6230731b070dd3e80e820430f3c2d37c21f8df4c00e299dfe083db33f2adb1d0 | c1ccc(-c2cn3ccsc3n2)cc1 | [CH3;D1;+0:1]-[C:2](=[O;D1;H0:3])-[c;H0;D3;+0:4]1:[c:5](-[c:6]):[#7;a:7]:[c;H0;D3;+0:8]2:[s;H0;D2;+0:9]:[cH;D2;+0:10]:[cH;D2;+0:11]:[n;H0;D3;+0:12]:2:1>>[C;D1;H3:13]-[N;H0;D3;+0:12](-[CH3;D1;+0:10])-[CH;D2;+0:11]=[CH;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c;H0;D3;+0:4]1:[#7;a:14]2:[c:15]:[c:16]:[s;H0;D2;+0:9]:[c;H0;D3;+0:8]:2:[... | null | [] | null | null | null | null | A 100 mL round bottom flask was charged with the 1-[6-(3-cyanophenyl)imidazo [2,1-b][1,3]thiazol-5-yl]ethanone (4.30 g, 16.1 mmol) and dimethylformamide dimethylacetal (40 mL). The mixture was refluxed for 6 hours and then concentrated in vacuo to provide a dark solid. LCMS: 323 [M+H]; purity: 90% by UV at 254 nm. This... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Enamine.Ketone | c1cn2ccsc2n1 | c1cn2ccsc2n1 | c1ccccc1.c1cn2ccsc2n1 | Other | COC(N(C)C)OC | null | null | CC(=O)c1c(-c2cccc(C#N)c2)nc2sccn12>COC(N(C)C)OC>CN(C)C=CC(=O)c1c(-c2cccc(C#N)c2)nc2sccn12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-1ccb2bec977b4fe6830c810c9bb88847 | CC(C)(C)OC(=O)N1CCC[C@@H](Nc2nccc(-c3c(-c4cccc(C#N)c4)nc4sccn34)n2)C1>>N#Cc1cccc(-c2nc3sccn3c2-c2ccnc(N[C@@H]3CCCNC3)n2)c1 | C(#N)C=1C=C(C=CC1)C=1N=C2SC=CN2C1C1=NC(=NC=C1)N[C@H]1CN(CCC1)C(=O)OC(C)(C)C.Cl>>Cl.C(#N)C=1C=C(C=CC1)C=1N=C2SC=CN2C1C1=NC(=NC=C1)N[C@H]1CNCCC1 | CC(C)(C)OC(=O)[N:27]1[CH2:26][CH2:25][CH2:24][C@@H:23]([NH:22][c:21]2[n:20][cH:19][cH:18][c:17](-[c:16]3[c:9](-[c:8]4[cH:7][cH:6][cH:5][c:4]([C:3]#[N:2])[cH:30]4)[n:10][c:11]4[s:12][cH:13][cH:14][n:15]43)[n:29]2)[CH2:28]1>>[N:2]#[C:3][c:4]1[cH:5][cH:6][cH:7][c:8](-[c:9]2[n:10][c:11]3[s:12][cH:13][cH:14][n:15]3[c:16]2-[... | CC(C)(C)OC(=O)N1CCC[C@@H](Nc2nccc(-c3c(-c4cccc(C#N)c4)nc4sccn34)n2)C1 | N#Cc1cccc(-c2nc3sccn3c2-c2ccnc(N[C@@H]3CCCNC3)n2)c1 | null | null | C(C)(=O)OCC | Reduction | Boc amine deprotection | bf3cd5dc3e17e694d8665c89f5d7e08e8763b18436a633eb66e9bf530b8b0316 | a94b29c7264c852156fc1cdd4a0951a4fc26c06d0edc9e50c743825dbf79e3fd | c1ccc(-c2nc3sccn3c2-c2ccnc(N[C@@H]3CCCNC3)n2)cc1 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1](-[C:2]-[C:3])-[C:4]-[C:5]>>[C:5]-[C:4]-[NH;D2;+0:1]-[C:2]-[C:3] | null | [] | null | null | null | null | The tert-butyl (3R)-3-({4-[6-(3-cyanophenyl)imidazo[2,1-b][1,3]thiazol-5-yl]pyrimidin-2-yl}amino)piperidine-1-carboxylate (2.90 g, 5.79 mmol) was dissolved in 20 mL of ethyl acetate and treated with 30 mL of 3.0 M HCl in ethyl acetate at room temperature (RT) overnight. Solid product was filtered, washed with ethyl ace... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Secondary amine | C1CC[NH]CC1 | C1CCNCC1 | c1ccccc1.c1cn2ccsc2n1.c1cncnc1.C1CCNCC1 | HO- | C(C)(=O)OCC | null | null | CC(C)(C)OC(=O)N1CCC[C@@H](Nc2nccc(-c3c(-c4cccc(C#N)c4)nc4sccn34)n2)C1>C(C)(=O)OCC>N#Cc1cccc(-c2nc3sccn3c2-c2ccnc(N[C@@H]3CCCNC3)n2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-8779122588764ffb9c6fd39969a9d2bd | N#Cc1cccc(-c2nc3sccn3c2-c2ccnc(N[C@@H]3CCCNC3)n2)c1.O=S(=O)(Cl)c1ccc(Cl)cc1>>N#Cc1cccc(-c2nc3sccn3c2-c2ccnc(N[C@@H]3CCCN(S(=O)(=O)c4ccc(Cl)cc4)C3)n2)c1 | Cl.C(#N)C=1C=C(C=CC1)C=1N=C2SC=CN2C1C1=NC(=NC=C1)N[C@H]1CNCCC1.C(C)N(CC)CC.ClC1=CC=C(C=C1)S(=O)(=O)Cl>>ClC1=CC=C(C=C1)S(=O)(=O)N1C[C@@H](CCC1)NC1=NC=CC(=N1)C1=C(N=C2SC=CN21)C2=CC(=CC=C2)C#N | [N:1]#[C:2][c:3]1[cH:4][cH:5][cH:6][c:7](-[c:8]2[n:9][c:10]3[s:11][cH:12][cH:13][n:14]3[c:15]2-[c:16]2[cH:17][cH:18][n:19][c:20]([NH:21][C@@H:22]3[CH2:23][CH2:24][CH2:25][NH:26][CH2:37]3)[n:38]2)[cH:39]1.Cl[S:27](=[O:28])(=[O:29])[c:30]1[cH:31][cH:32][c:33]([Cl:34])[cH:35][cH:36]1>>[N:1]#[C:2][c:3]1[cH:4][cH:5][cH:6][c... | N#Cc1cccc(-c2nc3sccn3c2-c2ccnc(N[C@@H]3CCCNC3)n2)c1.O=S(=O)(Cl)c1ccc(Cl)cc1 | N#Cc1cccc(-c2nc3sccn3c2-c2ccnc(N[C@@H]3CCCN(S(=O)(=O)c4ccc(Cl)cc4)C3)n2)c1 | null | null | ClCCl | Miscellaneous | Sulfonamide synthesis (Schotten-Baumann) secondary amine | 62fd7aa7f6e9018b348378d99729021e7cfa3bdaf0ae446bbf1fdeb2c590422b | 971e620478d668662a3bf915b510f5704d42a595d6ca9c67de007bd5d7063a75 | O=S(=O)(c1ccccc1)N1CCC[C@@H](Nc2nccc(-c3c(-c4ccccc4)nc4sccn34)n2)C1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6].[C:7]-[C:8]-[NH;D2;+0:9]-[C:10]-[C:11]>>[C:7]-[C:8]-[N;H0;D3;+0:9](-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6])-[C:10]-[C:11] | 97 | [{"value": 97.0, "product": "ClC1=CC=C(C=C1)S(=O)(=O)N1C[C@@H](CCC1)NC1=NC=CC(=N1)C1=C(N=C2SC=CN21)C2=CC(=CC=C2)C#N", "details": "PERCENTYIELD", "is_desired": false}, {"value": 96.5, "product": "ClC1=CC=C(C=C1)S(=O)(=O)N1C[C@@H](CCC1)NC1=NC=CC(=N1)C1=C(N=C2SC=CN21)C2=CC(=CC=C2)C#N", "details": "CALCULATEDPERCENTYIELD",... | null | null | 1 | HOUR | The 4-[6-(3-cyanophenyl)imidazo[2,1-b][1,3]thiazol-5-yl]-N-[(3R)-piperidin-3-yl]pyrimidin-2-amine hydrochloride (˜5.79 mmol) in dichloromethane (DCM) (50 mL) was cooled to 0° C. and treated with triethylamine (4.0 mL, 28.9 mmol), then 4-chlorophenylsulfonyl chloride (1.34 g, 6.37 mmol) was added. The reaction mixture w... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amine.Sulfonyl halide | Tertiary amine | C1CCNCC1 | C1CC[NH]CC1 | c1ccccc1.c1cn2ccsc2n1.c1cncnc1.C1CC[NH]CC1.c1ccccc1 | HCl | ClCCl | null | 1 | N#Cc1cccc(-c2nc3sccn3c2-c2ccnc(N[C@@H]3CCCNC3)n2)c1.O=S(=O)(Cl)c1ccc(Cl)cc1>ClCCl>N#Cc1cccc(-c2nc3sccn3c2-c2ccnc(N[C@@H]3CCCN(S(=O)(=O)c4ccc(Cl)cc4)C3)n2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-565e1347ed214a0ab82f06521329a8dd | N#Cc1cccc(-c2nc3sccn3c2-c2ccnc(N[C@@H]3CCCN(S(=O)(=O)c4ccc(Cl)cc4)C3)n2)c1.NO>>NC(=NO)c1cccc(-c2nc3sccn3c2-c2ccnc(N[C@@H]3CCCN(S(=O)(=O)c4ccc(Cl)cc4)C3)n2)c1 | ClC1=CC=C(C=C1)S(=O)(=O)N1C[C@@H](CCC1)NC1=NC=CC(=N1)C1=C(N=C2SC=CN21)C2=CC(=CC=C2)C#N.Cl.NO.C([O-])([O-])=O.[Na+].[Na+]>>ClC1=CC=C(C=C1)S(=O)(=O)N1C[C@@H](CCC1)NC1=NC=CC(=N1)C1=C(N=C2SC=CN21)C=2C=C(C=CC2)C(N)=NO | [N:1]#[C:2][c:5]1[cH:6][cH:7][cH:8][c:9](-[c:10]2[n:11][c:12]3[s:13][cH:14][cH:15][n:16]3[c:17]2-[c:18]2[cH:19][cH:20][n:21][c:22]([NH:23][C@@H:24]3[CH2:25][CH2:26][CH2:27][N:28]([S:29](=[O:30])(=[O:31])[c:32]4[cH:33][cH:34][c:35]([Cl:36])[cH:37][cH:38]4)[CH2:39]3)[n:40]2)[cH:41]1.[NH2:3][OH:4]>>[NH2:1][C:2](=[N:3][OH:... | N#Cc1cccc(-c2nc3sccn3c2-c2ccnc(N[C@@H]3CCCN(S(=O)(=O)c4ccc(Cl)cc4)C3)n2)c1.NO | NC(=NO)c1cccc(-c2nc3sccn3c2-c2ccnc(N[C@@H]3CCCN(S(=O)(=O)c4ccc(Cl)cc4)C3)n2)c1 | null | null | C(C)O.O | Heteroatom Alkylation and Arylation | Amidoxime from nitrile and hydroxylamine | 5f2123b5002b6939ec57e4f55921371a47c78c3ff253c724d87881638fedcd4f | ad3f1127a4d99506976df608684863fb1e08b35faede2d4e31cf4ca96393cd2e | O=S(=O)(c1ccccc1)N1CCC[C@@H](Nc2nccc(-c3c(-c4ccccc4)nc4sccn34)n2)C1 | [N;H0;D1;+0:1]#[C;H0;D2;+0:2]-[c:3](:[c:4]):[c:5].[NH2;D1;+0:6]-[O;D1;H1:7]>>[NH2;D1;+0:1]-[C;H0;D3;+0:2](=[N;H0;D2;+0:6]-[O;D1;H1:7])-[c:3](:[c:4]):[c:5] | 48 | [{"value": 48.0, "product": "ClC1=CC=C(C=C1)S(=O)(=O)N1C[C@@H](CCC1)NC1=NC=CC(=N1)C1=C(N=C2SC=CN21)C=2C=C(C=CC2)C(N)=NO", "details": "PERCENTYIELD", "is_desired": false}, {"value": 47.7, "product": "ClC1=CC=C(C=C1)S(=O)(=O)N1C[C@@H](CCC1)NC1=NC=CC(=N1)C1=C(N=C2SC=CN21)C=2C=C(C=CC2)C(N)=NO", "details": "CALCULATEDPERCEN... | 80 | CELSIUS | null | null | To a suspension of N-{(3R)-1-[(4-chlorophenyl)sulfonyl]piperidin-3-yl}-4-[6-(3-cyano-phenyl)imidazo[2,1-b][1,3]thiazol-5-yl]pyrimidin-2-amine (0.050 g, 0.086 mmol) in 80% ethanol-water (2.5 mL) was added an aqueous solution (0.50 mL) containing 6.65 mg of hydroxylamine hydrochloride (1.1 equivalents) and 4.61 mg of sod... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile.Primary amine | Primary amine.Oxime | null | null | c1ccccc1.c1cn2ccsc2n1.c1cncnc1.C1CC[NH]CC1.c1ccccc1 | null | C(C)O.O | 80 | null | N#Cc1cccc(-c2nc3sccn3c2-c2ccnc(N[C@@H]3CCCN(S(=O)(=O)c4ccc(Cl)cc4)C3)n2)c1.NO>C(C)O.O>NC(=NO)c1cccc(-c2nc3sccn3c2-c2ccnc(N[C@@H]3CCCN(S(=O)(=O)c4ccc(Cl)cc4)C3)n2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ae10437384e8439c99f41ed7d0798448 | CO.N#Cc1cccc(-c2nc3sccn3c2-c2ccnc(N[C@@H]3CCCN(S(=O)(=O)c4ccc(Cl)cc4)C3)n2)c1>>NC(=O)c1cccc(-c2nc3sccn3c2-c2ccnc(N[C@@H]3CCCN(S(=O)(=O)c4ccc(Cl)cc4)C3)n2)c1 | CO.ClC1=CC=C(C=C1)S(=O)(=O)N1C[C@@H](CCC1)NC1=NC=CC(=N1)C1=C(N=C2SC=CN21)C2=CC(=CC=C2)C#N.[Br-].[Br-].[Br-].B>>ClC1=CC=C(C=C1)S(=O)(=O)N1C[C@@H](CCC1)NC1=NC=CC(=N1)C1=C(N=C2SC=CN21)C=2C=C(C(=O)N)C=CC2 | C[OH:3].[N:1]#[C:2][c:4]1[cH:5][cH:6][cH:7][c:8](-[c:9]2[n:10][c:11]3[s:12][cH:13][cH:14][n:15]3[c:16]2-[c:17]2[cH:18][cH:19][n:20][c:21]([NH:22][C@@H:23]3[CH2:24][CH2:25][CH2:26][N:27]([S:28](=[O:29])(=[O:30])[c:31]4[cH:32][cH:33][c:34]([Cl:35])[cH:36][cH:37]4)[CH2:38]3)[n:39]2)[cH:40]1>>[NH2:1][C:2](=[O:3])[c:4]1[cH:... | CO.N#Cc1cccc(-c2nc3sccn3c2-c2ccnc(N[C@@H]3CCCN(S(=O)(=O)c4ccc(Cl)cc4)C3)n2)c1 | NC(=O)c1cccc(-c2nc3sccn3c2-c2ccnc(N[C@@H]3CCCN(S(=O)(=O)c4ccc(Cl)cc4)C3)n2)c1 | null | null | ClCCl | Heteroatom Alkylation and Arylation | OtherReaction | d495ded17ccf763bf499487085da685ced0129c4d8aac1f3c7a8bd356d30cdc5 | 061bdd0b1a0b381cc74cb84c74d6bcc8f02d1ad39972a8ccea7635f858cacf30 | O=S(=O)(c1ccccc1)N1CCC[C@@H](Nc2nccc(-c3c(-c4ccccc4)nc4sccn34)n2)C1 | C-[OH;D1;+0:1].[N;H0;D1;+0:2]#[C;H0;D2;+0:3]-[c:4](:[c:5]):[c:6]>>[NH2;D1;+0:2]-[C;H0;D3;+0:3](=[O;H0;D1;+0:1])-[c:4](:[c:5]):[c:6] | 4 | [{"value": 4.0, "product": "ClC1=CC=C(C=C1)S(=O)(=O)N1C[C@@H](CCC1)NC1=NC=CC(=N1)C1=C(N=C2SC=CN21)C=2C=C(C(=O)N)C=CC2", "details": "PERCENTYIELD", "is_desired": false}] | -78 | CELSIUS | 0.5 | HOUR | To a solution of N-{(3R)-1-[(4-chlorophenyl)sulfonyl]piperidin-3-yl}-4-[6-(3-cyano-phenyl)imidazo[2,1-b][1,3]thiazol-5-yl]pyrimidin-2-amine (0.50 g, 0.87 mmol) in dichloromethane (DCM) (10 mL) at −78° C. was added a solution of borane tribromide (BBr3) (1.74 mL, 1.0 M in DCM). The mixture was stirred at −78° C. for 0.5... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile.Methanol | Primary amide | null | null | c1ccccc1.c1cn2ccsc2n1.c1cncnc1.C1CC[NH]CC1.c1ccccc1 | Other | ClCCl | -78 | 0.5 | CO.N#Cc1cccc(-c2nc3sccn3c2-c2ccnc(N[C@@H]3CCCN(S(=O)(=O)c4ccc(Cl)cc4)C3)n2)c1>ClCCl>NC(=O)c1cccc(-c2nc3sccn3c2-c2ccnc(N[C@@H]3CCCN(S(=O)(=O)c4ccc(Cl)cc4)C3)n2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-6a9f8a3a7f83409f943a9a3f4b8447eb | CC(C)(C)OC(=O)N1CCC[C@@H](Nc2nccc(-c3c(-c4cccc(C#N)c4)nc4sccn34)n2)C1.[OH-]>>CC(C)(C)OC(=O)N1CCC[C@@H](Nc2nccc(-c3c(-c4cccc(C(N)=O)c4)nc4sccn34)n2)C1 | C(#N)C=1C=C(C=CC1)C=1N=C2SC=CN2C1C1=NC(=NC=C1)N[C@H]1CN(CCC1)C(=O)OC(C)(C)C.[OH-].[Na+]>>C(C)(C)(C)OC(=O)N1C[C@@H](CCC1)NC1=NC=CC(=N1)C1=C(N=C2SC=CN21)C2=CC(=CC=C2)C(N)=O | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][CH2:11][C@@H:12]([NH:13][c:14]2[n:15][cH:16][cH:17][c:18](-[c:19]3[c:20](-[c:21]4[cH:22][cH:23][cH:24][c:25]([C:26]#[N:27])[cH:29]4)[n:30][c:31]4[s:32][cH:33][cH:34][n:35]34)[n:36]2)[CH2:37]1.[OH-:28]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])... | CC(C)(C)OC(=O)N1CCC[C@@H](Nc2nccc(-c3c(-c4cccc(C#N)c4)nc4sccn34)n2)C1.[OH-] | CC(C)(C)OC(=O)N1CCC[C@@H](Nc2nccc(-c3c(-c4cccc(C(N)=O)c4)nc4sccn34)n2)C1 | null | null | C(C)O | Heteroatom Alkylation and Arylation | OtherReaction | 1d1793919e847ed86dcb16487e62464531560dbf4782f9a5875bfe7e0477a3ec | d6f9d146e8ef95e62f1a3ab55a7e3b4ceec8856a5f71b6dccd4ad850f945b658 | c1ccc(-c2nc3sccn3c2-c2ccnc(N[C@@H]3CCCNC3)n2)cc1 | [N;H0;D1;+0:1]#[C;H0;D2;+0:2]-[c:3](:[c:4]):[c:5].[OH-;D0:6]>>[NH2;D1;+0:1]-[C;H0;D3;+0:2](=[O;H0;D1;+0:6])-[c:3](:[c:4]):[c:5] | 83 | [{"value": 83.0, "product": "C(C)(C)(C)OC(=O)N1C[C@@H](CCC1)NC1=NC=CC(=N1)C1=C(N=C2SC=CN21)C2=CC(=CC=C2)C(N)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 82.7, "product": "C(C)(C)(C)OC(=O)N1C[C@@H](CCC1)NC1=NC=CC(=N1)C1=C(N=C2SC=CN21)C2=CC(=CC=C2)C(N)=O", "details": "CALCULATEDPERCENTYIELD", "is_desir... | 75 | CELSIUS | null | null | To a solution of tert-butyl (3R)-3-({4-[6-(3-cyanophenyl)imidazo[2,1-b][1,3]thiazol-5-yl]pyrimidin-2-yl}amino)piperidine-1-carboxylate (0.204 g, 0.407 mmol) in ethanol (5 mL) was added 25% aqueous sodium hydroxide (0.072 mL, 0.448 mmol). The mixture was heated at 75° C. for 20 hours. Solvent was removed to dryness. Res... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile | Primary amide | null | null | C1CC[NH]CC1.c1cncnc1.c1ccccc1.c1cn2ccsc2n1 | null | C(C)O | 75 | null | CC(C)(C)OC(=O)N1CCC[C@@H](Nc2nccc(-c3c(-c4cccc(C#N)c4)nc4sccn34)n2)C1.[OH-]>C(C)O>CC(C)(C)OC(=O)N1CCC[C@@H](Nc2nccc(-c3c(-c4cccc(C(N)=O)c4)nc4sccn34)n2)C1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d1761b5fdfe44dc7a2349407925282f7 | CC(C)(C)OC(=O)N1CCC[C@@H](Nc2nccc(-c3c(-c4cccc(C(N)=O)c4)nc4sccn34)n2)C1>>NC(=O)c1cccc(-c2nc3sccn3c2-c2ccnc(N[C@@H]3CCCNC3)n2)c1 | C(C)(C)(C)OC(=O)N1C[C@@H](CCC1)NC1=NC=CC(=N1)C1=C(N=C2SC=CN21)C2=CC(=CC=C2)C(N)=O.Cl>>N1C[C@@H](CCC1)NC1=NC=CC(=N1)C1=C(N=C2SC=CN21)C=2C=C(C(=O)N)C=CC2 | CC(C)(C)OC(=O)[N:27]1[CH2:26][CH2:25][CH2:24][C@@H:23]([NH:22][c:21]2[n:20][cH:19][cH:18][c:17](-[c:16]3[c:9](-[c:8]4[cH:7][cH:6][cH:5][c:4]([C:2]([NH2:1])=[O:3])[cH:30]4)[n:10][c:11]4[s:12][cH:13][cH:14][n:15]43)[n:29]2)[CH2:28]1>>[NH2:1][C:2](=[O:3])[c:4]1[cH:5][cH:6][cH:7][c:8](-[c:9]2[n:10][c:11]3[s:12][cH:13][cH:1... | CC(C)(C)OC(=O)N1CCC[C@@H](Nc2nccc(-c3c(-c4cccc(C(N)=O)c4)nc4sccn34)n2)C1 | NC(=O)c1cccc(-c2nc3sccn3c2-c2ccnc(N[C@@H]3CCCNC3)n2)c1 | null | null | C(C)(=O)OCC | Reduction | Boc amine deprotection | bf3cd5dc3e17e694d8665c89f5d7e08e8763b18436a633eb66e9bf530b8b0316 | a94b29c7264c852156fc1cdd4a0951a4fc26c06d0edc9e50c743825dbf79e3fd | c1ccc(-c2nc3sccn3c2-c2ccnc(N[C@@H]3CCCNC3)n2)cc1 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1](-[C:2]-[C:3])-[C:4]-[C:5]>>[C:5]-[C:4]-[NH;D2;+0:1]-[C:2]-[C:3] | 107.2 | [{"value": 97.0, "product": "N1C[C@@H](CCC1)NC1=NC=CC(=N1)C1=C(N=C2SC=CN21)C=2C=C(C(=O)N)C=CC2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 107.2, "product": "N1C[C@@H](CCC1)NC1=NC=CC(=N1)C1=C(N=C2SC=CN21)C=2C=C(C(=O)N)C=CC2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | (R)-3-{4-[6-(3-carbamoyl-phenyl)-imidazo[2,1-b]thiazol-5-yl]-pyrimidin-2-ylamino}-piperidine-1-carboxylic acid tert-butyl ester (0.15 g, 0.289 mmol) was dissolved in 3 mL of ethyl acetate and treated with 3 ml of 3.0 M HCl in ethyl acetate at room temperature (RT) overnight. Solid product was filtered, washed ethyl ace... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Secondary amine | C1CC[NH]CC1 | C1CCNCC1 | c1ccccc1.c1cn2ccsc2n1.c1cncnc1.C1CCNCC1 | HO- | C(C)(=O)OCC | null | null | CC(C)(C)OC(=O)N1CCC[C@@H](Nc2nccc(-c3c(-c4cccc(C(N)=O)c4)nc4sccn34)n2)C1>C(C)(=O)OCC>NC(=O)c1cccc(-c2nc3sccn3c2-c2ccnc(N[C@@H]3CCCNC3)n2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ed0c7b9a15ff46eca7a60f23a0d386a8 | CON(C)C(=O)c1cccc(-c2nc3sccn3c2-c2ccnc(N[C@@H]3CCCN(S(=O)(=O)c4ccc(Cl)cc4)C3)n2)c1.[OH-]>>O=C(O)c1cccc(-c2nc3sccn3c2-c2ccnc(N[C@@H]3CCCN(S(=O)(=O)c4ccc(Cl)cc4)C3)n2)c1 | ClC1=CC=C(C=C1)S(=O)(=O)N1C[C@@H](CCC1)NC1=NC=CC(=N1)C1=C(N=C2SC=CN21)C=2C=C(C(=O)N(C)OC)C=CC2.[OH-].[Li+]>>ClC1=CC=C(C=C1)S(=O)(=O)N1C[C@@H](CCC1)NC1=NC=CC(=N1)C1=C(N=C2SC=CN21)C=2C=C(C(=O)O)C=CC2 | CON(C)[C:2](=[O:1])[c:4]1[cH:5][cH:6][cH:7][c:8](-[c:9]2[n:10][c:11]3[s:12][cH:13][cH:14][n:15]3[c:16]2-[c:17]2[cH:18][cH:19][n:20][c:21]([NH:22][C@@H:23]3[CH2:24][CH2:25][CH2:26][N:27]([S:28](=[O:29])(=[O:30])[c:31]4[cH:32][cH:33][c:34]([Cl:35])[cH:36][cH:37]4)[CH2:38]3)[n:39]2)[cH:40]1.[OH-:3]>>[O:1]=[C:2]([OH:3])[c:... | CON(C)C(=O)c1cccc(-c2nc3sccn3c2-c2ccnc(N[C@@H]3CCCN(S(=O)(=O)c4ccc(Cl)cc4)C3)n2)c1.[OH-] | O=C(O)c1cccc(-c2nc3sccn3c2-c2ccnc(N[C@@H]3CCCN(S(=O)(=O)c4ccc(Cl)cc4)C3)n2)c1 | null | null | O1CCCC1.O.CO | Acylation | OtherReaction | e4458a7867863c954d58565c6ddd87c2eeab98b7c07ecdd463e9753ebb748946 | c01215fbf8824351bac42d78014a20af2990d2d56c6ce8ce9b2f77fd36798755 | O=S(=O)(c1ccccc1)N1CCC[C@@H](Nc2nccc(-c3c(-c4ccccc4)nc4sccn34)n2)C1 | C-O-N(-C)-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[OH-;D0:6]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[OH;D1;+0:6])-[c:3](:[c:4]):[c:5] | null | [] | null | null | 48 | HOUR | To a solution of 3-(5-{2-[(R)-1-(4-chloro-benzenesulfonyl)-piperidin-3-ylamino]-pyrimidin-4-yl}-imidazo[2,1-b]thiazol-6-yl)-N-methoxy-N-methyl-benzamide (0.57 g, 0.089 mmol) in a mixture of methanol (1.0 mL) and tetrahydrofuran (THF) (3.0 mL) was added a solution of lithium hydroxide (0.075 g, 0.179 mmoL) in water (1.0... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide | Carboxylic acid | null | null | c1ccccc1.c1cn2ccsc2n1.c1cncnc1.C1CC[NH]CC1.c1ccccc1 | HO- | O1CCCC1.O.CO | null | 48 | CON(C)C(=O)c1cccc(-c2nc3sccn3c2-c2ccnc(N[C@@H]3CCCN(S(=O)(=O)c4ccc(Cl)cc4)C3)n2)c1.[OH-]>O1CCCC1.O.CO>O=C(O)c1cccc(-c2nc3sccn3c2-c2ccnc(N[C@@H]3CCCN(S(=O)(=O)c4ccc(Cl)cc4)C3)n2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-2f983a535bf843b38eb33d4849312b9f | CON(C)C(=O)c1cccc(-c2nc3sccn3c2-c2ccnc(N[C@@H]3CCCN(S(=O)(=O)c4ccc(Cl)cc4)C3)n2)c1>>CC(=O)c1cccc(-c2nc3sccn3c2-c2ccnc(N[C@@H]3CCCN(S(=O)(=O)c4ccc(Cl)cc4)C3)n2)c1 | ClC1=CC=C(C=C1)S(=O)(=O)N1C[C@@H](CCC1)NC1=NC=CC(=N1)C1=C(N=C2SC=CN21)C=2C=C(C(=O)N(C)OC)C=CC2.C[Mg]Cl>>ClC1=CC=C(C=C1)S(=O)(=O)N1C[C@@H](CCC1)NC1=NC=CC(=N1)C1=C(N=C2SC=CN21)C=2C=C(C=CC2)C(C)=O | CON(C)[C:2](=[O:3])[c:4]1[cH:5][cH:6][cH:7][c:8](-[c:9]2[n:10][c:11]3[s:12][cH:13][cH:14][n:15]3[c:16]2-[c:17]2[cH:18][cH:19][n:20][c:21]([NH:22][C@@H:23]3[CH2:24][CH2:25][CH2:26][N:27]([S:28](=[O:29])(=[O:30])[c:31]4[cH:32][cH:33][c:34]([Cl:35])[cH:36][cH:37]4)[CH2:38]3)[n:39]2)[cH:40]1>>[CH3:1][C:2](=[O:3])[c:4]1[cH:... | CON(C)C(=O)c1cccc(-c2nc3sccn3c2-c2ccnc(N[C@@H]3CCCN(S(=O)(=O)c4ccc(Cl)cc4)C3)n2)c1 | CC(=O)c1cccc(-c2nc3sccn3c2-c2ccnc(N[C@@H]3CCCN(S(=O)(=O)c4ccc(Cl)cc4)C3)n2)c1 | null | null | O1CCCC1 | Functional Group Interconversion | OtherReaction | 0e1b501f4aadb0e84ffc93b33216cc37dfe617cb6c3e325779c58539a7f5c4e4 | af85307a4412ed48cedcfde84079732215472ffbe274bdc1dc12e9979d5c5e06 | O=S(=O)(c1ccccc1)N1CCC[C@@H](Nc2nccc(-c3c(-c4ccccc4)nc4sccn34)n2)C1 | C-O-N(-C)-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5]>>[C;D1;H3:6]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5] | 91 | [{"value": 91.0, "product": "ClC1=CC=C(C=C1)S(=O)(=O)N1C[C@@H](CCC1)NC1=NC=CC(=N1)C1=C(N=C2SC=CN21)C=2C=C(C=CC2)C(C)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | To a solution of 3-(5-{2-[(R)-1-(4-chloro-benzenesulfonyl)-piperidin-3-ylamino]-pyrimidin-4-yl}-imidazo[2,1-b]thiazol-6-yl)-N-methoxy-N-methyl-benzamide (0.10 g, 0.157 mmol) in anhydrous tetrahydrofuran (THF) (3.0 mL) at 0° C. was added a solution of methyl magnesium chloride (3.0 M in THF) (0.523 mL, 1.57 mmoL). The m... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide | Ketone | null | null | c1ccccc1.c1cn2ccsc2n1.c1cncnc1.C1CC[NH]CC1.c1ccccc1 | HO- | O1CCCC1 | null | 3 | CON(C)C(=O)c1cccc(-c2nc3sccn3c2-c2ccnc(N[C@@H]3CCCN(S(=O)(=O)c4ccc(Cl)cc4)C3)n2)c1>O1CCCC1>CC(=O)c1cccc(-c2nc3sccn3c2-c2ccnc(N[C@@H]3CCCN(S(=O)(=O)c4ccc(Cl)cc4)C3)n2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ffc7e0f6e2c74807b834f0c1dc768f51 | CC(=O)c1cccc(-c2nc3sccn3c2-c2ccnc(N[C@@H]3CCCN(S(=O)(=O)c4ccc(Cl)cc4)C3)n2)c1.NO>>C/C(=N\O)c1cccc(-c2nc3sccn3c2-c2ccnc(N[C@@H]3CCCN(S(=O)(=O)c4ccc(Cl)cc4)C3)n2)c1 | ClC1=CC=C(C=C1)S(=O)(=O)N1C[C@@H](CCC1)NC1=NC=CC(=N1)C1=C(N=C2SC=CN21)C=2C=C(C=CC2)C(C)=O.Cl.NO.C(C)(=O)O>>ClC1=CC=C(C=C1)S(=O)(=O)N1C[C@@H](CCC1)NC1=NC=CC(=N1)C1=C(N=C2SC=CN21)C=2C=C(C=CC2)/C(/C)=N/O | O=[C:2]([CH3:1])[c:5]1[cH:6][cH:7][cH:8][c:9](-[c:10]2[n:11][c:12]3[s:13][cH:14][cH:15][n:16]3[c:17]2-[c:18]2[cH:19][cH:20][n:21][c:22]([NH:23][C@@H:24]3[CH2:25][CH2:26][CH2:27][N:28]([S:29](=[O:30])(=[O:31])[c:32]4[cH:33][cH:34][c:35]([Cl:36])[cH:37][cH:38]4)[CH2:39]3)[n:40]2)[cH:41]1.[NH2:3][OH:4]>>[CH3:1]/[C:2](=[N:... | CC(=O)c1cccc(-c2nc3sccn3c2-c2ccnc(N[C@@H]3CCCN(S(=O)(=O)c4ccc(Cl)cc4)C3)n2)c1.NO | C/C(=N\O)c1cccc(-c2nc3sccn3c2-c2ccnc(N[C@@H]3CCCN(S(=O)(=O)c4ccc(Cl)cc4)C3)n2)c1 | null | null | ClCCl.CO | Heteroatom Alkylation and Arylation | OtherReaction | b5fd91d879f097d0ef2e8e2d3ef7d2ef0195968870a9602a47b8324c601790b9 | 1a0ef15294bdb221fb8888b5d4c7fcf00473b11e53da288791d32747daa48d23 | O=S(=O)(c1ccccc1)N1CCC[C@@H](Nc2nccc(-c3c(-c4ccccc4)nc4sccn34)n2)C1 | O=[C;H0;D3;+0:1](-[C;D1;H3:2])-[c:3](:[c:4]):[c:5].[NH2;D1;+0:6]-[O;D1;H1:7]>>[C;D1;H3:2]/[C;H0;D3;+0:1](=[N;H0;D2;+0:6]\[O;D1;H1:7])-[c:3](:[c:4]):[c:5] | 67.5 | [{"value": 67.0, "product": "ClC1=CC=C(C=C1)S(=O)(=O)N1C[C@@H](CCC1)NC1=NC=CC(=N1)C1=C(N=C2SC=CN21)C=2C=C(C=CC2)/C(/C)=N/O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 67.5, "product": "ClC1=CC=C(C=C1)S(=O)(=O)N1C[C@@H](CCC1)NC1=NC=CC(=N1)C1=C(N=C2SC=CN21)C=2C=C(C=CC2)/C(/C)=N/O", "details": "CALCULATED... | 50 | CELSIUS | null | null | To a mixture of 1-(3-{5-[2-({(3R)-1-[(4-chlorophenyl)sulfonyl]piperidin-3-yl}amino)pyrimidin-4-yl]imidazo[2,1-b][1,3]thiazol-6-yl}phenyl)ethanone (0.10 g, 0.168 mmol) and hydroxylamine hydrochloride (0.0125 g, 0.188 mmoL) in methanol (2.0 mL) was added 0.2 mL of acetic acid. The mixture was heated at 50° C. for 3 hours... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Primary amine | Oxime | null | null | c1ccccc1.c1cn2ccsc2n1.c1cncnc1.C1CC[NH]CC1.c1ccccc1 | HO- | ClCCl.CO | 50 | null | CC(=O)c1cccc(-c2nc3sccn3c2-c2ccnc(N[C@@H]3CCCN(S(=O)(=O)c4ccc(Cl)cc4)C3)n2)c1.NO>ClCCl.CO>C/C(=N\O)c1cccc(-c2nc3sccn3c2-c2ccnc(N[C@@H]3CCCN(S(=O)(=O)c4ccc(Cl)cc4)C3)n2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-4778e9adea704e30a5f454fbb8db3ba5 | CON(C)C(=O)c1cccc(-c2nc3sccn3c2-c2ccnc(N[C@@H]3CCCN(S(=O)(=O)c4ccc(Cl)cc4)C3)n2)c1>>O=Cc1cccc(-c2nc3sccn3c2-c2ccnc(N[C@@H]3CCCN(S(=O)(=O)c4ccc(Cl)cc4)C3)n2)c1 | ClC1=CC=C(C=C1)S(=O)(=O)N1C[C@@H](CCC1)NC1=NC=CC(=N1)C1=C(N=C2SC=CN21)C=2C=C(C(=O)N(C)OC)C=CC2.[H-].[Al+3].[Li+].[H-].[H-].[H-]>>ClC1=CC=C(C=C1)S(=O)(=O)N1C[C@@H](CCC1)NC1=NC=CC(=N1)C1=C(N=C2SC=CN21)C=2C=C(C=O)C=CC2 | CON(C)[C:2](=[O:1])[c:3]1[cH:4][cH:5][cH:6][c:7](-[c:8]2[n:9][c:10]3[s:11][cH:12][cH:13][n:14]3[c:15]2-[c:16]2[cH:17][cH:18][n:19][c:20]([NH:21][C@@H:22]3[CH2:23][CH2:24][CH2:25][N:26]([S:27](=[O:28])(=[O:29])[c:30]4[cH:31][cH:32][c:33]([Cl:34])[cH:35][cH:36]4)[CH2:37]3)[n:38]2)[cH:39]1>>[O:1]=[CH:2][c:3]1[cH:4][cH:5][... | CON(C)C(=O)c1cccc(-c2nc3sccn3c2-c2ccnc(N[C@@H]3CCCN(S(=O)(=O)c4ccc(Cl)cc4)C3)n2)c1 | O=Cc1cccc(-c2nc3sccn3c2-c2ccnc(N[C@@H]3CCCN(S(=O)(=O)c4ccc(Cl)cc4)C3)n2)c1 | null | null | O1CCCC1 | Reduction | OtherReaction | 1ad7fd93ee9decf7147397a16abe4237898f80cc43934fb11b6a369d0f378a48 | 11e681cf0fbb4d124dda7df91cf446f896c1a2472cb9bea5b83f41b090ec7b28 | O=S(=O)(c1ccccc1)N1CCC[C@@H](Nc2nccc(-c3c(-c4ccccc4)nc4sccn34)n2)C1 | C-O-N(-C)-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5]>>[O;D1;H0:2]=[CH;D2;+0:1]-[c:3](:[c:4]):[c:5] | 73.1 | [{"value": 73.0, "product": "ClC1=CC=C(C=C1)S(=O)(=O)N1C[C@@H](CCC1)NC1=NC=CC(=N1)C1=C(N=C2SC=CN21)C=2C=C(C=O)C=CC2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 73.1, "product": "ClC1=CC=C(C=C1)S(=O)(=O)N1C[C@@H](CCC1)NC1=NC=CC(=N1)C1=C(N=C2SC=CN21)C=2C=C(C=O)C=CC2", "details": "CALCULATEDPERCENTYIELD",... | 0 | CELSIUS | 30 | MINUTE | To a solution of 3-(5-{2-[(R)-1-(4-chloro-benzenesulfonyl)-piperidin-3-ylamino]-pyrimidin-4-yl}-imidazo[2,1-b]thiazol-6-yl)-N-methoxy-N-methyl-benzamide (0.05 g, 0.078 mmol) in anhydrous tetrahydrofuran (THF) (3.0 mL) at 0° C. was added a solution of lithium aluminum hydride (LAH) (2.0 M in THF) (0.078 mL, 0.15 mmol). ... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide | Aldehyde | null | null | c1ccccc1.c1cn2ccsc2n1.c1cncnc1.C1CC[NH]CC1.c1ccccc1 | HO- | O1CCCC1 | 0 | 0.5 | CON(C)C(=O)c1cccc(-c2nc3sccn3c2-c2ccnc(N[C@@H]3CCCN(S(=O)(=O)c4ccc(Cl)cc4)C3)n2)c1>O1CCCC1>O=Cc1cccc(-c2nc3sccn3c2-c2ccnc(N[C@@H]3CCCN(S(=O)(=O)c4ccc(Cl)cc4)C3)n2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-fac448887d99423fbc37cb339ce21182 | NO.O=Cc1cccc(-c2nc3sccn3c2-c2ccnc(N[C@@H]3CCCN(S(=O)(=O)c4ccc(Cl)cc4)C3)n2)c1>>O=S(=O)(c1ccc(Cl)cc1)N1CCC[C@@H](Nc2nccc(-c3c(-c4cccc(C=NO)c4)nc4sccn34)n2)C1 | ClC1=CC=C(C=C1)S(=O)(=O)N1C[C@@H](CCC1)NC1=NC=CC(=N1)C1=C(N=C2SC=CN21)C=2C=C(C=O)C=CC2.Cl.NO.C(C)(=O)O>>ClC1=CC=C(C=C1)S(=O)(=O)N1C[C@@H](CCC1)NC1=NC=CC(=N1)C1=C(N=C2SC=CN21)C=2C=C(C=NO)C=CC2 | [NH2:30][OH:31].O=[CH:29][c:28]1[cH:27][cH:26][cH:25][c:24](-[c:23]2[c:22](-[c:21]3[cH:20][cH:19][n:18][c:17]([NH:16][C@@H:15]4[CH2:14][CH2:13][CH2:12][N:11]([S:2](=[O:1])(=[O:3])[c:4]5[cH:5][cH:6][c:7]([Cl:8])[cH:9][cH:10]5)[CH2:40]4)[n:39]3)[n:38]3[c:34]([n:33]2)[s:35][cH:36][cH:37]3)[cH:32]1>>[O:1]=[S:2](=[O:3])([c:... | NO.O=Cc1cccc(-c2nc3sccn3c2-c2ccnc(N[C@@H]3CCCN(S(=O)(=O)c4ccc(Cl)cc4)C3)n2)c1 | O=S(=O)(c1ccc(Cl)cc1)N1CCC[C@@H](Nc2nccc(-c3c(-c4cccc(C=NO)c4)nc4sccn34)n2)C1 | null | null | ClCCl.CO | Heteroatom Alkylation and Arylation | OtherReaction | 26f32c058bcc6b69b34e9c38433bccb165270e0a55ab24439c783c1aee9d8dac | 3593c4a8dedbac5f92a1a749cef37ecd686935362f91b9154f0c9930a5edea38 | O=S(=O)(c1ccccc1)N1CCC[C@@H](Nc2nccc(-c3c(-c4ccccc4)nc4sccn34)n2)C1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[NH2;D1;+0:5]-[O;D1;H1:6]>>[O;D1;H1:6]-[N;H0;D2;+0:5]=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4] | 61.3 | [{"value": 61.0, "product": "ClC1=CC=C(C=C1)S(=O)(=O)N1C[C@@H](CCC1)NC1=NC=CC(=N1)C1=C(N=C2SC=CN21)C=2C=C(C=NO)C=CC2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 61.3, "product": "ClC1=CC=C(C=C1)S(=O)(=O)N1C[C@@H](CCC1)NC1=NC=CC(=N1)C1=C(N=C2SC=CN21)C=2C=C(C=NO)C=CC2", "details": "CALCULATEDPERCENTYIELD... | 50 | CELSIUS | null | null | To a mixture 3-{5-[2-({(3R)-1-[(4-chlorophenyl)sulfonyl]piperidin-3-yl}amino)pyrimidin-4-yl]imidazo[2,1-b][1,3]thiazol-6-yl}benzaldehyde (0.81 g, 0.14 mmol) and hydroxylamine hydrochloride (0.0107 g, 0.154 mmoL) in methanol (2.0 mL) was added 0.2 mL of acetic acid. The mixture was heated at 50° C. for 2 hours. After co... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Primary amine | Oxime | null | null | c1ccccc1.C1CC[NH]CC1.c1cncnc1.c1ccccc1.c1cn2ccsc2n1 | HO- | ClCCl.CO | 50 | null | NO.O=Cc1cccc(-c2nc3sccn3c2-c2ccnc(N[C@@H]3CCCN(S(=O)(=O)c4ccc(Cl)cc4)C3)n2)c1>ClCCl.CO>O=S(=O)(c1ccc(Cl)cc1)N1CCC[C@@H](Nc2nccc(-c3c(-c4cccc(C=NO)c4)nc4sccn34)n2)C1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-cc1c0bcfdd8d4f3bba5acc4f84a0f39d | O=Cc1cccc(-c2nc3sccn3c2-c2ccnc(N[C@@H]3CCCN(S(=O)(=O)c4ccc(Cl)cc4)C3)n2)c1>>O=S(=O)(c1ccc(Cl)cc1)N1CCC[C@@H](Nc2nccc(-c3c(-c4cccc(CO)c4)nc4sccn34)n2)C1 | ClC1=CC=C(C=C1)S(=O)(=O)N1C[C@@H](CCC1)NC1=NC=CC(=N1)C1=C(N=C2SC=CN21)C=2C=C(C=O)C=CC2.[H-].[Al+3].[Li+].[H-].[H-].[H-]>>ClC1=CC=C(C=C1)S(=O)(=O)N1C[C@@H](CCC1)NC1=NC=CC(=N1)C1=C(N=C2SC=CN21)C=2C=C(C=CC2)CO | [O:1]=[S:2](=[O:3])([c:4]1[cH:5][cH:6][c:7]([Cl:8])[cH:9][cH:10]1)[N:11]1[CH2:12][CH2:13][CH2:14][C@@H:15]([NH:16][c:17]2[n:18][cH:19][cH:20][c:21](-[c:22]3[c:23](-[c:24]4[cH:25][cH:26][cH:27][c:28]([CH:29]=[O:30])[cH:31]4)[n:32][c:33]4[s:34][cH:35][cH:36][n:37]34)[n:38]2)[CH2:39]1>>[O:1]=[S:2](=[O:3])([c:4]1[cH:5][cH:... | O=Cc1cccc(-c2nc3sccn3c2-c2ccnc(N[C@@H]3CCCN(S(=O)(=O)c4ccc(Cl)cc4)C3)n2)c1 | O=S(=O)(c1ccc(Cl)cc1)N1CCC[C@@H](Nc2nccc(-c3c(-c4cccc(CO)c4)nc4sccn34)n2)C1 | null | null | O1CCCC1 | Reduction | Reduction of aldehydes and ketones to alcohols | e7895795cd3f75445716c94697823c5929dcd4b5344525875fe75d36bca2f9d7 | 21bb81d5469aaaca71ab12c186bea4016451717fad8780cf288858a7d8fbc55a | O=S(=O)(c1ccccc1)N1CCC[C@@H](Nc2nccc(-c3c(-c4ccccc4)nc4sccn34)n2)C1 | [O;H0;D1;+0:1]=[CH;D2;+0:2]-[c:3](:[c:4]):[c:5]>>[OH;D1;+0:1]-[CH2;D2;+0:2]-[c:3](:[c:4]):[c:5] | 71 | [{"value": 71.0, "product": "ClC1=CC=C(C=C1)S(=O)(=O)N1C[C@@H](CCC1)NC1=NC=CC(=N1)C1=C(N=C2SC=CN21)C=2C=C(C=CC2)CO", "details": "PERCENTYIELD", "is_desired": false}, {"value": 70.6, "product": "ClC1=CC=C(C=C1)S(=O)(=O)N1C[C@@H](CCC1)NC1=NC=CC(=N1)C1=C(N=C2SC=CN21)C=2C=C(C=CC2)CO", "details": "CALCULATEDPERCENTYIELD", "... | null | null | 1 | HOUR | To a mixture 3-{5-[2-({(3R)-1-[(4-chlorophenyl)sulfonyl]piperidin-3-yl}amino)pyrimidin-4-yl]imidazo [2,1-b][1,3]thiazol-6-yl}benzaldehyde (0.20 g, 0.346 mmol) in anhydrous tetrahydrofuran (THF) (5.0 mL) at room temperature was added a solution of lithium aluminum hydride (LAH) (2.0 M in THF) (0.346 mL, 0.692 mmol). The... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | Primary alcohol | null | null | c1ccccc1.C1CC[NH]CC1.c1cncnc1.c1ccccc1.c1cn2ccsc2n1 | null | O1CCCC1 | null | 1 | O=Cc1cccc(-c2nc3sccn3c2-c2ccnc(N[C@@H]3CCCN(S(=O)(=O)c4ccc(Cl)cc4)C3)n2)c1>O1CCCC1>O=S(=O)(c1ccc(Cl)cc1)N1CCC[C@@H](Nc2nccc(-c3c(-c4cccc(CO)c4)nc4sccn34)n2)C1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a248a620d0164213b25a65efa3042531 | Cc1nc(-c2cccc(-c3nc4sccn4c3-c3ccnc(N[C@@H]4CCCN(C(=O)OC(C)(C)C)C4)n3)c2)no1>>Cc1nc(-c2cccc(-c3nc4sccn4c3-c3ccnc(N[C@@H]4CCCNC4)n3)c2)no1 | C(C)(C)(C)OC(=O)N1C[C@@H](CCC1)NC1=NC=CC(=N1)C1=C(N=C2SC=CN21)C2=CC(=CC=C2)C2=NOC(=N2)C.Cl>>CC1=NC(=NO1)C=1C=C(C=CC1)C=1N=C2SC=CN2C1C1=NC(=NC=C1)N[C@H]1CNCCC1 | CC(C)(C)OC(=O)[N:28]1[CH2:27][CH2:26][CH2:25][C@@H:24]([NH:23][c:22]2[n:21][cH:20][cH:19][c:18](-[c:17]3[c:10](-[c:9]4[cH:8][cH:7][cH:6][c:5](-[c:4]5[n:3][c:2]([CH3:1])[o:33][n:32]5)[cH:31]4)[n:11][c:12]4[s:13][cH:14][cH:15][n:16]43)[n:30]2)[CH2:29]1>>[CH3:1][c:2]1[n:3][c:4](-[c:5]2[cH:6][cH:7][cH:8][c:9](-[c:10]3[n:11... | Cc1nc(-c2cccc(-c3nc4sccn4c3-c3ccnc(N[C@@H]4CCCN(C(=O)OC(C)(C)C)C4)n3)c2)no1 | Cc1nc(-c2cccc(-c3nc4sccn4c3-c3ccnc(N[C@@H]4CCCNC4)n3)c2)no1 | null | null | C(C)(=O)OCC | Reduction | Boc amine deprotection | bf3cd5dc3e17e694d8665c89f5d7e08e8763b18436a633eb66e9bf530b8b0316 | a94b29c7264c852156fc1cdd4a0951a4fc26c06d0edc9e50c743825dbf79e3fd | c1cc(-c2ncon2)cc(-c2nc3sccn3c2-c2ccnc(N[C@@H]3CCCNC3)n2)c1 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1](-[C:2]-[C:3])-[C:4]-[C:5]>>[C:5]-[C:4]-[NH;D2;+0:1]-[C:2]-[C:3] | 109.4 | [{"value": 100.0, "product": "CC1=NC(=NO1)C=1C=C(C=CC1)C=1N=C2SC=CN2C1C1=NC(=NC=C1)N[C@H]1CNCCC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 109.4, "product": "CC1=NC(=NO1)C=1C=C(C=CC1)C=1N=C2SC=CN2C1C1=NC(=NC=C1)N[C@H]1CNCCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | ((R)-3-(4-{6-[3-(5-Methyl-[1,2,4]oxadiazol-3-yl)-phenyl]-imidazo[2,1-b]thiazol-5-yl}-pyrimidin-2-ylamino)-piperidine-1-carboxylic acid tert-butyl ester (0.15 g, 0.269 mmol) was dissolved in 2 mL of ethyl acetate and treated with 2 ml of 3.0 M HCl in ethyl acetate at room temperature (RT) overnight. Solid product was fi... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Secondary amine | C1CC[NH]CC1 | C1CCNCC1 | c1ncon1.c1ccccc1.c1cn2ccsc2n1.c1cncnc1.C1CCNCC1 | HO- | C(C)(=O)OCC | null | null | Cc1nc(-c2cccc(-c3nc4sccn4c3-c3ccnc(N[C@@H]4CCCN(C(=O)OC(C)(C)C)C4)n3)c2)no1>C(C)(=O)OCC>Cc1nc(-c2cccc(-c3nc4sccn4c3-c3ccnc(N[C@@H]4CCCNC4)n3)c2)no1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a5f349f2bfac4e1383c3b5f581edc10e | C[C@@H](CO)NC(=O)OC(C)(C)C>>C[C@@H](C=O)NC(=O)OC(C)(C)C | C(C)(C)(C)OC(=O)N[C@H](CO)C.CC(=O)OI1(C=2C=CC=CC2C(=O)O1)(OC(=O)C)OC(=O)C.S([O-])(O)=O.[Na+]>>C(C)(C)(C)OC(=O)N[C@H](C=O)C | [CH3:1][C@@H:2]([CH2:3][OH:4])[NH:5][C:6](=[O:7])[O:8][C:9]([CH3:10])([CH3:11])[CH3:12]>>[CH3:1][C@@H:2]([CH:3]=[O:4])[NH:5][C:6](=[O:7])[O:8][C:9]([CH3:10])([CH3:11])[CH3:12] | C[C@@H](CO)NC(=O)OC(C)(C)C | C[C@@H](C=O)NC(=O)OC(C)(C)C | null | null | C(Cl)Cl.C(C)(=O)OCC | Oxidation | Oxidation or Dehydrogenation of Alcohols to Aldehydes and Ketones | 41bfa9deea81b465c88ad21fdfb64a2e1ba29490558cf430df132cb98b4a538b | 0a03c6724c1862e8f86d4a463afda55b8e067dc6cb42597b472eb7cabc03eda3 | null | [C;D1;H3:1]-[C:2](-[C;D1;H3:3])(-[C;D1;H3:4])-[#8:5]-[C:6](=[O;D1;H0:7])-[#7:8]-[C:9](-[C;D1;H3:10])-[CH2;D2;+0:11]-[OH;D1;+0:12]>>[C;D1;H3:1]-[C:2](-[C;D1;H3:3])(-[C;D1;H3:4])-[#8:5]-[C:6](=[O;D1;H0:7])-[#7:8]-[C:9](-[C;D1;H3:10])-[CH;D2;+0:11]=[O;H0;D1;+0:12] | 92 | [{"value": 92.0, "product": "C(C)(C)(C)OC(=O)N[C@H](C=O)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 92.0, "product": "C(C)(C)(C)OC(=O)N[C@H](C=O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | (S)-(−)-2-(tert-Butoxycarbonylamino)-1-propanol (523 mg, 2.98 mmol, 1.0 equiv.) was dissolved in 45 mL methylene chloride in a 100 mL r.b. flask with a magnetic stir bar. To this clear homogeneous solution, Dess-Martin periodinane (1.523 g, 3.591 mmol, 1.2 equiv.) was added in one portion and the cloudy white reaction ... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | Aldehyde | null | null | null | null | C(Cl)Cl.C(C)(=O)OCC | null | 2 | C[C@@H](CO)NC(=O)OC(C)(C)C>C(Cl)Cl.C(C)(=O)OCC>C[C@@H](C=O)NC(=O)OC(C)(C)C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-890e7f96539a48dfa6ab3c51f9e65ca2 | C[C@@H](CO)NC(=O)Cc1ccccc1>>C[C@@H](C=O)NC(=O)Cc1ccccc1 | C(C1=CC=CC=C1)C(=O)N[C@H](CO)C.CC(=O)OI1(C=2C=CC=CC2C(=O)O1)(OC(=O)C)OC(=O)C>>C(C1=CC=CC=C1)C(=O)N[C@H](C=O)C | [CH3:1][C@@H:2]([CH2:3][OH:4])[NH:5][C:6](=[O:7])[CH2:8][c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1>>[CH3:1][C@@H:2]([CH:3]=[O:4])[NH:5][C:6](=[O:7])[CH2:8][c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1 | C[C@@H](CO)NC(=O)Cc1ccccc1 | C[C@@H](C=O)NC(=O)Cc1ccccc1 | null | null | C(Cl)Cl | Oxidation | Oxidation or Dehydrogenation of Alcohols to Aldehydes and Ketones | 41bfa9deea81b465c88ad21fdfb64a2e1ba29490558cf430df132cb98b4a538b | 0a03c6724c1862e8f86d4a463afda55b8e067dc6cb42597b472eb7cabc03eda3 | c1ccccc1 | [C;D1;H3:1]-[C:2](-[#7:3]-[C:4]=[O;D1;H0:5])-[CH2;D2;+0:6]-[OH;D1;+0:7]>>[C;D1;H3:1]-[C:2](-[#7:3]-[C:4]=[O;D1;H0:5])-[CH;D2;+0:6]=[O;H0;D1;+0:7] | null | [] | null | null | 2 | HOUR | (S)-2-(benzylcarbonylamino)-propanol (5 g, 23.9 mmol) was dissolved in CH2Cl2 (200 mL) and treated with Dess-Martin periodinane (12.26 g, 1.1 eq). The mixture was stirred for 2 hours, then quenched with sodium thiosulphate, and the solvent removed in vacuo. The residue was then separated between sodium hydroxide (1M, 5... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | Aldehyde | null | null | c1ccccc1 | null | C(Cl)Cl | null | 2 | C[C@@H](CO)NC(=O)Cc1ccccc1>C(Cl)Cl>C[C@@H](C=O)NC(=O)Cc1ccccc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-0cd77599b927482a828e3244fc616796 | C[C@@H](CNc1ccc(OC(F)(F)F)cc1)NC(=O)OCc1ccccc1>>C[C@H](N)CNc1ccc(OC(F)(F)F)cc1 | C(C1=CC=CC=C1)OC(N[C@H](CNC1=CC=C(C=C1)OC(F)(F)F)C)=O>>FC(OC1=CC=C(C=C1)NC[C@H](C)N)(F)F | O=C(OCc1ccccc1)[NH:3][C@@H:2]([CH3:1])[CH2:4][NH:5][c:6]1[cH:7][cH:8][c:9]([O:10][C:11]([F:12])([F:13])[F:14])[cH:15][cH:16]1>>[CH3:1][C@H:2]([NH2:3])[CH2:4][NH:5][c:6]1[cH:7][cH:8][c:9]([O:10][C:11]([F:12])([F:13])[F:14])[cH:15][cH:16]1 | C[C@@H](CNc1ccc(OC(F)(F)F)cc1)NC(=O)OCc1ccccc1 | C[C@H](N)CNc1ccc(OC(F)(F)F)cc1 | null | [Pd] | C(C)O | Reduction | Hydrogenolysis of amides/imides/carbamates | 087b6600ba91d3df931fe6979f2445c192cbfd59e04fd2d8a10f7c7573ac669f | 4e549866ec1acadec4c84aaf8495992a28ec78d8ea5ef1b9f44dd843b0dcb7d4 | c1ccccc1 | O=C(-O-C-c1:c:c:c:c:c:1)-[NH;D2;+0:1]-[C:2](-[C:3])-[C;D1;H3:4]>>[C:3]-[C:2](-[C;D1;H3:4])-[NH2;D1;+0:1] | 72 | [{"value": 72.0, "product": "FC(OC1=CC=C(C=C1)NC[C@H](C)N)(F)F", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | [1-(S)-Methyl-2-(4-trifluoromethoxy-phenylamino)-ethyl]-carbamic acid benzyl ester (23.9 mmol) was dissolved in ethanol (200 mL) then placed under nitrogen. 10% Palladium on carbon was added (0.5 g) and the mixture was stirred under hydrogen (atmospheric pressure) overnight. When reaction was complete, the mixture was ... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether | Primary amine | c1ccccc1 | null | c1ccccc1 | HO- | [Pd].C(C)O | null | 8 | C[C@@H](CNc1ccc(OC(F)(F)F)cc1)NC(=O)OCc1ccccc1>[Pd].C(C)O>C[C@H](N)CNc1ccc(OC(F)(F)F)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e0900b2a0fdb44c48afe1aea2bd808ca | C=C(C)CBr.CC(C)(C)OC(=O)Nc1ccc(F)cc1>>C=C(C)Cc1cc(F)ccc1NC(=O)OC(C)(C)C | [Li]C(C)(C)C.CCCCC.C(=O)(OC(C)(C)C)NC1=CC=C(C=C1)F.C(C(C)=C)Br>>C(C)(C)(C)OC(NC1=C(C=C(C=C1)F)CC(=C)C)=O | Br[CH2:4][C:2](=[CH2:1])[CH3:3].[cH:5]1[cH:6][c:7]([F:8])[cH:9][cH:10][c:11]1[NH:12][C:13](=[O:14])[O:15][C:16]([CH3:17])([CH3:18])[CH3:19]>>[CH2:1]=[C:2]([CH3:3])[CH2:4][c:5]1[cH:6][c:7]([F:8])[cH:9][cH:10][c:11]1[NH:12][C:13](=[O:14])[O:15][C:16]([CH3:17])([CH3:18])[CH3:19] | C=C(C)CBr.CC(C)(C)OC(=O)Nc1ccc(F)cc1 | C=C(C)Cc1cc(F)ccc1NC(=O)OC(C)(C)C | null | null | C1CCOC1 | C-C Coupling | Friedel-Crafts alkylation with halide | abd82b32c15853d5913cc8f5d51923ff8cee2c9e5cfc2628ece51b84576c3f2d | f5e5e22797736d188bba28deb76a4cee8e4fee4dca04fe24f733d2ee68a23361 | c1ccccc1 | Br-[CH2;D2;+0:1]-[C:2](=[C;D1;H2:3])-[C;D1;H3:4].[C;D1;H3:5]-[C:6](-[C;D1;H3:7])(-[C;D1;H3:8])-[#8:9]-[C:10](=[O;D1;H0:11])-[#7:12]-[c:13](:[c:14]):[cH;D2;+0:15]:[c:16]:[c:17]>>[C;D1;H2:3]=[C:2](-[C;D1;H3:4])-[CH2;D2;+0:1]-[c;H0;D3;+0:15](:[c:16]:[c:17]):[c:13](-[#7:12]-[C:10](=[O;D1;H0:11])-[#8:9]-[C:6](-[C;D1;H3:5])(... | 80 | [{"value": 80.0, "product": "C(C)(C)(C)OC(NC1=C(C=C(C=C1)F)CC(=C)C)=O", "details": "PERCENTYIELD", "is_desired": false}] | -20 | CELSIUS | 2.5 | HOUR | A solution of N-Boc-4-fluoroaniline (9.02 g, 42.7 mmol) in THF (112 mL) was cooled to −60° C. using a cryocool instrument. The solution was treated with 1.7 M t-BuLi in pentane (63 mL, 106.7 mmol) dropwise. After the first equivalent of base was consumed, a yellow solution formed. The reaction was allowed to warm to −2... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1ccccc1 | c1ccccc1 | c1ccccc1 | HBr | C1CCOC1 | -20 | 2.5 | C=C(C)CBr.CC(C)(C)OC(=O)Nc1ccc(F)cc1>C1CCOC1>C=C(C)Cc1cc(F)ccc1NC(=O)OC(C)(C)C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-5c7c19b5f0cb4d9b892729fa46059a03 | C=C(C)Cc1cc(F)ccc1NC(=O)OC(C)(C)C>>CC1(C)Cc2cc(F)ccc2N1 | CS(=O)(=O)O.C(C)(C)(C)OC(NC1=C(C=C(C=C1)F)CC(=C)C)=O.C1(=CC=CC=C1)OC.FC(C(=O)O)(F)F>>CC1(NC2=CC=C(C=C2C1)F)C | CC(C)(C)OC(=O)[NH:12][c:11]1[c:5]([CH2:4][C:2](=[CH2:1])[CH3:3])[cH:6][c:7]([F:8])[cH:9][cH:10]1>>[CH3:1][C:2]1([CH3:3])[CH2:4][c:5]2[cH:6][c:7]([F:8])[cH:9][cH:10][c:11]2[NH:12]1 | C=C(C)Cc1cc(F)ccc1NC(=O)OC(C)(C)C | CC1(C)Cc2cc(F)ccc2N1 | null | null | ClCCl | Heteroatom Alkylation and Arylation | OtherReaction | b9db8b959ce76a9ce9ae402df8bd3b8657a4d8353a0f20fd79710a2c4e90449b | f4be2a1dc40806f7d87a3d054308bec820304200bc50fd9c846232e4d6353bb4 | c1ccc2c(c1)CCN2 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[c:2](:[c:3]):[c:4]-[C:5]-[C;H0;D3;+0:6](-[C;D1;H3:7])=[CH2;D1;+0:8]>>[C;D1;H3:7]-[C;H0;D4;+0:6]1(-[CH3;D1;+0:8])-[C:5]-[c:4]:[c:2](:[c:3])-[NH;D2;+0:1]-1 | 66 | [{"value": 66.0, "product": "CC1(NC2=CC=C(C=C2C1)F)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 65.8, "product": "CC1(NC2=CC=C(C=C2C1)F)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 170 | CELSIUS | 4 | HOUR | A sample of [4-Fluoro-2-(2-methyl-allyl)-phenyl]-carbamic acid tert-butyl ester (1.10 g, 4.14 mmol) was treated with anisole (5 mL), dichloromethane (5 mL) and trifluoroacetic acid (5 mL) and stirred for 4 hours. The solvent was removed and the reaction was transferred to a microwave reaction vial using methanesulfonic... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Vinyl.Boc | Secondary amine | null | c1ccc2c(c1)CCN2 | c1ccc2c(c1)CCN2 | HO- | ClCCl | 170 | 4 | C=C(C)Cc1cc(F)ccc1NC(=O)OC(C)(C)C>ClCCl>CC1(C)Cc2cc(F)ccc2N1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e1442b980ca14987bec905ca68964d5f | C=C(C)CN(C(C)=O)c1ccc(F)cc1>>CC(=O)N1CC(C)(C)c2cc(F)ccc21 | FC1=CC=C(C=C1)N(C(C)=O)CC(=C)C.[Cl-].[Cl-].[Cl-].[Al+3].O>>FC=1C=C2C(CN(C2=CC1)C(C)=O)(C)C | [CH3:1][C:2](=[O:3])[N:4]([CH2:5][C:6]([CH3:7])=[CH2:8])[c:15]1[cH:9][cH:10][c:11]([F:12])[cH:13][cH:14]1>>[CH3:1][C:2](=[O:3])[N:4]1[CH2:5][C:6]([CH3:7])([CH3:8])[c:9]2[cH:10][c:11]([F:12])[cH:13][cH:14][c:15]21 | C=C(C)CN(C(C)=O)c1ccc(F)cc1 | CC(=O)N1CC(C)(C)c2cc(F)ccc21 | null | null | C(C)(=O)OCC | C-C Coupling | OtherReaction | 4d710ad3c860e47fcf3f7015a55b39b05e571ad23da36e5437a9a2523003c972 | 48297e5b607b4624d5b08506879ba8f9dd47fb272c10888542fa01ef83829ef2 | c1ccc2c(c1)CCN2 | [C;D1;H3:1]-[C:2](=[O;D1;H0:3])-[#7:4](-[C:5]-[C;H0;D3;+0:6](-[C;D1;H3:7])=[CH2;D1;+0:8])-[c:9](:[c:10]):[cH;D2;+0:11]:[c:12]:[c:13]>>[C;D1;H3:1]-[C:2](=[O;D1;H0:3])-[#7:4]1-[C:5]-[C;H0;D4;+0:6](-[C;D1;H3:7])(-[CH3;D1;+0:8])-[c;H0;D3;+0:11](:[c:12]:[c:13]):[c:9]-1:[c:10] | null | [] | 150 | CELSIUS | null | null | According to the procedure described in S. Coulton et al. WO9925709 with the following modifications. N-(4-Fluoro-phenyl)-N-(2-methyl-allyl)-acetamide (5 grams, 24.12 mmol) was added to a microwave tube with aluminum trichloride (7 grams, 52.4 mmol). The tube was capped and heated to 150° C. for 20 minutes under microw... | 10.6084/m9.figshare.5104873.v1 | null | Vinyl | null | c1ccccc1 | c1ccc2c(c1)CC[NH]2 | c1ccc2c(c1)CC[NH]2 | null | C(C)(=O)OCC | 150 | null | C=C(C)CN(C(C)=O)c1ccc(F)cc1>C(C)(=O)OCC>CC(=O)N1CC(C)(C)c2cc(F)ccc21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-93a099c3483445ae9df313c7ccd83d5c | CC(=O)N1CC(C)(C)c2cc(F)ccc21>>CC1(C)CNc2ccc(F)cc21 | FC=1C=C2C(CN(C2=CC1)C(C)=O)(C)C>>CC1(CNC2=CC=C(C=C12)F)C | CC(=O)[N:5]1[CH2:4][C:2]([CH3:1])([CH3:3])[c:12]2[c:6]1[cH:7][cH:8][c:9]([F:10])[cH:11]2>>[CH3:1][C:2]1([CH3:3])[CH2:4][NH:5][c:6]2[cH:7][cH:8][c:9]([F:10])[cH:11][c:12]21 | CC(=O)N1CC(C)(C)c2cc(F)ccc21 | CC1(C)CNc2ccc(F)cc21 | null | null | Cl | Reduction | Hydrogenolysis of tertiary amines | 3325d321b6e740eb07332b61ecb10184cad4db5efbb86509e39d17e13b7f3d02 | 62cf08a8ae6315067a063b5b3495125ccbdaff6b2340ce1d3e1c7b6cde962ae4 | c1ccc2c(c1)CCN2 | C-C(=O)-[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 | null | [] | 200 | CELSIUS | null | null | According to the procedure described in S. Coulton et al. WO9925709 with the following modifications. N-(4-Fluoro-phenyl)-N-(2-methyl-allyl)-acetamide (5 grams, 24.12 mmol) was added to a microwave tube with aluminum trichloride (7 grams, 52.4 mmol). The tube was capped and heated to 150° C. for 20 minutes under microw... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide | Secondary amine | c1ccc2c(c1)CC[NH]2 | c1ccc2c(c1)CCN2 | c1ccc2c(c1)CCN2 | HO- | Cl | 200 | null | CC(=O)N1CC(C)(C)c2cc(F)ccc21>Cl>CC1(C)CNc2ccc(F)cc21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-4a688b44877b428d8a89c050175e0a95 | O=C(N[C@H](C(=O)O)C1CC1)OCc1ccccc1>>O=C(N[C@H](CO)C1CC1)OCc1ccccc1 | C(C1=CC=CC=C1)OC(=O)N[C@H](C(=O)O)C1CC1.Cl>>C(C1=CC=CC=C1)OC(N[C@H](CO)C1CC1)=O | O=[C:5]([C@@H:4]([NH:3][C:2](=[O:1])[O:10][CH2:11][c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1)[CH:7]1[CH2:8][CH2:9]1)[OH:6]>>[O:1]=[C:2]([NH:3][C@H:4]([CH2:5][OH:6])[CH:7]1[CH2:8][CH2:9]1)[O:10][CH2:11][c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1 | O=C(N[C@H](C(=O)O)C1CC1)OCc1ccccc1 | O=C(N[C@H](CO)C1CC1)OCc1ccccc1 | null | null | C1CCOC1 | Reduction | Reduction of carboxylic acid to primary alcohol | 0db83a5ebe1e318b78b55461cf7eb8f7c004eef0f9e3b6666d3df4c96b5f665e | 93b4621647b04d2ad2f2825215b1567f171ba61fe10d136b5db6ea0470aa4932 | O=C(NCC1CC1)OCc1ccccc1 | O=[C;H0;D3;+0:1](-[O;D1;H1:2])-[C:3](-[C:4])-[#7:5]-[C:6]=[O;D1;H0:7]>>[C:4]-[C:3](-[#7:5]-[C:6]=[O;D1;H0:7])-[CH2;D2;+0:1]-[O;D1;H1:2] | 50 | [{"value": 50.0, "product": "C(C1=CC=CC=C1)OC(N[C@H](CO)C1CC1)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 49.8, "product": "C(C1=CC=CC=C1)OC(N[C@H](CO)C1CC1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 4 | HOUR | A solution of (S)-benzyloxycarbonylamino-cyclopropyl-acetic acid (3.2 g, 12.8 mmol) in THF (20 mL) was cooled in an ice/water bath and treated with a 1 M solution of BH3 in THF (16.7 mL, 16.7 mmol). The reaction was stirred for 4 hours and then treated with 1 M HCl until the bubbling ceased. The reaction was stirred ov... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Primary alcohol | null | null | C1CC1.c1ccccc1 | Other | C1CCOC1 | null | 4 | O=C(N[C@H](C(=O)O)C1CC1)OCc1ccccc1>C1CCOC1>O=C(N[C@H](CO)C1CC1)OCc1ccccc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-fad66d30e14f4e2597d7628ec4bb0ca3 | COc1ccc(CCl)cc1.O=C1Nc2ccc(F)cc2C1=O>>COc1ccc(CN2C(=O)C(=O)c3cc(F)ccc32)cc1 | FC=1C=C2C(C(NC2=CC1)=O)=O.[H-].[Na+].COC1=CC=C(CCl)C=C1>>FC=1C=C2C(C(N(C2=CC1)CC1=CC=C(C=C1)OC)=O)=O | Cl[CH2:7][c:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:21][cH:20]1.[NH:8]1[C:9](=[O:10])[C:11](=[O:12])[c:13]2[cH:14][c:15]([F:16])[cH:17][cH:18][c:19]21>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][N:8]2[C:9](=[O:10])[C:11](=[O:12])[c:13]3[cH:14][c:15]([F:16])[cH:17][cH:18][c:19]32)[cH:20][cH:21]1 | COc1ccc(CCl)cc1.O=C1Nc2ccc(F)cc2C1=O | COc1ccc(CN2C(=O)C(=O)c3cc(F)ccc32)cc1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | c168ddb7803c893ec5334f16b8c2262b487eff0908e05ac9b9feab6bfceb9bd3 | 4a6c1e88c9e8bed487b746792f88d478ff36cc235f9a217d4632e6babdebdc9a | O=C1C(=O)N(Cc2ccccc2)c2ccccc21 | Cl-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[O;D1;H0:5]=[C:6]1-[NH;D2;+0:7]-[c:8](:[c:9]):[c:10]-[C:11]-1=[O;D1;H0:12]>>[O;D1;H0:5]=[C:6]1-[C:11](=[O;D1;H0:12])-[c:10]:[c:8](:[c:9])-[N;H0;D3;+0:7]-1-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4] | 82.4 | [{"value": 82.0, "product": "FC=1C=C2C(C(N(C2=CC1)CC1=CC=C(C=C1)OC)=O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 82.4, "product": "FC=1C=C2C(C(N(C2=CC1)CC1=CC=C(C=C1)OC)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 15 | MINUTE | A solution of 5-fluoroisatin (5 g, 30.2 mmol) in DMF (60 mL) was cooled in an ice/water bath and treated with sodium hydride (1.44 g, 60.6 mmol) portionwise. The reaction was stirred for 15 minutes after the addition of the last portion and then treated with p-methoxybenzyl chloride (5.32 g, 45.3 mmol) and allowed to s... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amide | Tertiary amide | c1ccc2c(c1)CCN2 | c1ccc2c(c1)CC[NH]2 | c1ccccc1.c1ccc2c(c1)CC[NH]2 | HCl | CN(C)C=O | null | 0.25 | COc1ccc(CCl)cc1.O=C1Nc2ccc(F)cc2C1=O>CN(C)C=O>COc1ccc(CN2C(=O)C(=O)c3cc(F)ccc32)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-90138d8dc9d84d73ad6048fe33ec7bc8 | COc1ccc(CCl)cc1.O=C1Nc2ccc(F)cc2C1=O>>COc1ccc(CN2C(=O)C(=O)c3cc(F)ccc32)cc1 | O.FC=1C=C2C(C(NC2=CC1)=O)=O.[H-].[Na+].COC1=CC=C(CCl)C=C1>>FC=1C=C2C(C(N(C2=CC1)CC1=CC=C(C=C1)OC)=O)=O | Cl[CH2:7][c:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:21][cH:20]1.[NH:8]1[C:9](=[O:10])[C:11](=[O:12])[c:13]2[cH:14][c:15]([F:16])[cH:17][cH:18][c:19]21>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][N:8]2[C:9](=[O:10])[C:11](=[O:12])[c:13]3[cH:14][c:15]([F:16])[cH:17][cH:18][c:19]32)[cH:20][cH:21]1 | COc1ccc(CCl)cc1.O=C1Nc2ccc(F)cc2C1=O | COc1ccc(CN2C(=O)C(=O)c3cc(F)ccc32)cc1 | null | null | C(C)(=O)OCC.CCCCCC.CN(C)C=O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | c168ddb7803c893ec5334f16b8c2262b487eff0908e05ac9b9feab6bfceb9bd3 | 4a6c1e88c9e8bed487b746792f88d478ff36cc235f9a217d4632e6babdebdc9a | O=C1C(=O)N(Cc2ccccc2)c2ccccc21 | Cl-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[O;D1;H0:5]=[C:6]1-[NH;D2;+0:7]-[c:8](:[c:9]):[c:10]-[C:11]-1=[O;D1;H0:12]>>[O;D1;H0:5]=[C:6]1-[C:11](=[O;D1;H0:12])-[c:10]:[c:8](:[c:9])-[N;H0;D3;+0:7]-1-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4] | 80 | [{"value": 80.0, "product": "FC=1C=C2C(C(N(C2=CC1)CC1=CC=C(C=C1)OC)=O)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 15 | MINUTE | 5-Fluoro-1H-indole-2,3-dione (956 mg, 5.79 mmol, 1 eq) was added as a solution in dry DMF to a stirred slurry of sodium hydride (278 mg, 11.6 mmol, 2 eq) in dry DMF drop wise over 15 minutes under an inert atmosphere with adequate pressure release to accommodate H2 evolution. The resulting mixture was stirred for 1 hou... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amide | Tertiary amide | c1ccc2c(c1)CCN2 | c1ccc2c(c1)CC[NH]2 | c1ccccc1.c1ccc2c(c1)CC[NH]2 | HCl | C(C)(=O)OCC.CCCCCC.CN(C)C=O | null | 0.25 | COc1ccc(CCl)cc1.O=C1Nc2ccc(F)cc2C1=O>C(C)(=O)OCC.CCCCCC.CN(C)C=O>COc1ccc(CN2C(=O)C(=O)c3cc(F)ccc32)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-3d2bf968e38a48499b840bebcf57db85 | C[C@@](O)(C(=O)O)C1CCCCC1.NCCN1CCc2cc(F)ccc21>>O=C(NCCN1CCc2cc(F)ccc21)[C@@H](O)CC1CCCCC1 | C1(CCCCC1)[C@@](C(=O)O)(O)C.FC=1C=C2CCN(C2=CC1)CCN.CN(C)C(=[N+](C)C)ON1C2=C(C=CC=N2)N=N1.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>>C1(CCCCC1)C[C@@H](C(=O)NCCN1CCC2=CC(=CC=C12)F)O | O[C:2](=[O:1])[C@:16]([OH:17])([CH3:18])[CH:19]1[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24]1.[NH2:3][CH2:4][CH2:5][N:6]1[CH2:7][CH2:8][c:9]2[cH:10][c:11]([F:12])[cH:13][cH:14][c:15]21>>[O:1]=[C:2]([NH:3][CH2:4][CH2:5][N:6]1[CH2:7][CH2:8][c:9]2[cH:10][c:11]([F:12])[cH:13][cH:14][c:15]21)[C@@H:16]([OH:17])[CH2:18][CH:19]1[C... | C[C@@](O)(C(=O)O)C1CCCCC1.NCCN1CCc2cc(F)ccc21 | O=C(NCCN1CCc2cc(F)ccc21)[C@@H](O)CC1CCCCC1 | null | null | C(Cl)Cl.C(C)(=O)OCC | Acylation | OtherReaction | 8b5cce7e7b144073d5b05dd864ab1077165b109863da7ae2850d3790f9ed42d5 | 315769563e8b03437a63a4166d6856a701ea134077d01ad7d2e966fdc1d17f39 | O=C(CCC1CCCCC1)NCCN1CCc2ccccc21 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C@@;H0;D4;+0:3](-[CH3;D1;+0:4])(-[O;D1;H1:5])-[CH;D3;+0:6](-[C:7]-[C:8])-[C:9]-[C:10].[C:11]-[C:12]-[NH2;D1;+0:13]>>[C:8]-[C:7]-[CH;D3;+0:6](-[CH2;D2;+0:4]-[C@H;D3;+0:3](-[O;D1;H1:5])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:13]-[C:12]-[C:11])-[C:9]-[C:10] | 28 | [{"value": 28.0, "product": "C1(CCCCC1)C[C@@H](C(=O)NCCN1CCC2=CC(=CC=C12)F)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a stirring suspension of (S)-cyclohexyl lactic acid (558 mg, 3.42 mmol) in CH2Cl2 was added 2-(5-fluoro-2,3-dihydro-indol-1-yl)-ethylamine (616 mg, 3.42 mmol), HATU (1.429 g, 3.76 mmol), and DIEA (1.79 mL, 10.3 mmol). The reaction mixture was stirred at room temperature for several hours until the starting material ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Tertiary alcohol.Primary amine | Secondary amide.Secondary alcohol | C1CCCCC1 | C1CCCCC1 | c1ccc2c(c1)CC[NH]2.C1CCCCC1 | HO- | C(Cl)Cl.C(C)(=O)OCC | null | null | C[C@@](O)(C(=O)O)C1CCCCC1.NCCN1CCc2cc(F)ccc21>C(Cl)Cl.C(C)(=O)OCC>O=C(NCCN1CCc2cc(F)ccc21)[C@@H](O)CC1CCCCC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-f869eb9b164c4cca94362b68c0e38e8d | COC(=O)[C@@H](CC(=O)O)CC1CCCCC1.NCCNc1ccc(F)cc1>>COC(=O)[C@@H](CC(=O)NCCNc1ccc(F)cc1)CC1CCCCC1 | COC([C@@H](CC(=O)O)CC1CCCCC1)=O.C(C)(C)N(CC)C(C)C.CN(C)C(=[N+](C)C)ON1C2=C(C=CC=N2)N=N1.F[P-](F)(F)(F)(F)F.FC1=CC=C(C=C1)NCCN>>COC([C@@H](CC(=O)NCCNC1=CC=C(C=C1)F)CC1CCCCC1)=O | O[C:7]([CH2:6][C@H:5]([C:3]([O:2][CH3:1])=[O:4])[CH2:20][CH:21]1[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26]1)=[O:8].[NH2:9][CH2:10][CH2:11][NH:12][c:13]1[cH:14][cH:15][c:16]([F:17])[cH:18][cH:19]1>>[CH3:1][O:2][C:3](=[O:4])[C@@H:5]([CH2:6][C:7](=[O:8])[NH:9][CH2:10][CH2:11][NH:12][c:13]1[cH:14][cH:15][c:16]([F:17])[cH:18]... | COC(=O)[C@@H](CC(=O)O)CC1CCCCC1.NCCNc1ccc(F)cc1 | COC(=O)[C@@H](CC(=O)NCCNc1ccc(F)cc1)CC1CCCCC1 | null | null | ClCCl | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(CCCC1CCCCC1)NCCNc1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4]-[C:5](-[#8:6])=[O;D1;H0:7].[C:8]-[C:9]-[NH2;D1;+0:10]>>[#8:6]-[C:5](=[O;D1;H0:7])-[C:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:10]-[C:9]-[C:8] | 65 | [{"value": 65.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | 5 | HOUR | (R)-2-(Cyclohexylmethyl)succinic acid-1-methyl ester (211 mg, 0.93 mmol) from Acros Organics was treated with (500 μL, 2.87 mmol, 3.1 eq.) of diisopropylethylamine, HATU (360 mg, 1.096 mmol, 1.2 eq.) and (N-(4-Fluoro-phenyl)-ethane-1,2-diamine) (210 mg, 0.93 mmol, 1 eq.). The reagents were dissolved in dry dichlorometh... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.C1CCCCC1 | HO- | ClCCl | null | 5 | COC(=O)[C@@H](CC(=O)O)CC1CCCCC1.NCCNc1ccc(F)cc1>ClCCl>COC(=O)[C@@H](CC(=O)NCCNc1ccc(F)cc1)CC1CCCCC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d0407a9318944a7e917dcccb34ff3fef | COC(=O)[C@@H](CC(=O)NCCNc1ccc(F)cc1)CC1CCCCC1>>O=C(C[C@@H](CC1CCCCC1)C(=O)O)NCCNc1ccc(F)cc1 | COC([C@@H](CC(=O)NCCNC1=CC=C(C=C1)F)CC1CCCCC1)=O.[OH-].[Li+]>>C1(CCCCC1)C[C@@H](C(=O)O)CC(=O)NCCNC1=CC=C(C=C1)F | C[O:14][C:12]([C@@H:4]([CH2:3][C:2](=[O:1])[NH:15][CH2:16][CH2:17][NH:18][c:19]1[cH:20][cH:21][c:22]([F:23])[cH:24][cH:25]1)[CH2:5][CH:6]1[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11]1)=[O:13]>>[O:1]=[C:2]([CH2:3][C@@H:4]([CH2:5][CH:6]1[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11]1)[C:12](=[O:13])[OH:14])[NH:15][CH2:16][CH2:17][NH:18]... | COC(=O)[C@@H](CC(=O)NCCNc1ccc(F)cc1)CC1CCCCC1 | O=C(C[C@@H](CC1CCCCC1)C(=O)O)NCCNc1ccc(F)cc1 | null | null | O.CO | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | O=C(CCCC1CCCCC1)NCCNc1ccccc1 | 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] | 86 | [{"value": 86.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | 23 | CELSIUS | 8 | HOUR | (R)-2-cyclohexylmethyl-N-[2-(4-fluoro-phenylamino)-ethyl]-succinamic acid methyl ester (220 mg, 0.60 mmol, 1.0 eq.) was dissolved in a mixture of MeOH (4.5 mL) and H2O (3 mL) and placed in a 0° C. ice bath. Lithium hydroxide (30 mg, 1.25 mmol, 2.1 eq.) was added in one portion and allowed to stir for 8 hours, slowly wa... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | C1CCCCC1.c1ccccc1 | Other | O.CO | 23 | 8 | COC(=O)[C@@H](CC(=O)NCCNc1ccc(F)cc1)CC1CCCCC1>O.CO>O=C(C[C@@H](CC1CCCCC1)C(=O)O)NCCNc1ccc(F)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-5577055f2f0042359bf67e6684fc6dd9 | C1COCCN1.O=C(C[C@@H](CC1CCCCC1)C(=O)O)NCCNc1ccc(F)cc1>>O=C(C[C@@H](CC1CCCCC1)C(=O)N1CCOCC1)NCCNc1ccc(F)cc1 | C(C)(C)N(CC)C(C)C.C1(CCCCC1)C[C@@H](C(=O)O)CC(=O)NCCNC1=CC=C(C=C1)F.N1CCOCC1.CN(C)C(=[N+](C)C)ON1C2=C(C=CC=N2)N=N1.F[P-](F)(F)(F)(F)F>>C1(CCCCC1)C[C@H](CC(=O)NCCNC1=CC=C(C=C1)F)C(=O)N1CCOCC1 | [NH:14]1[CH2:15][CH2:16][O:17][CH2:18][CH2:19]1.O[C:12]([C@@H:4]([CH2:3][C:2](=[O:1])[NH:20][CH2:21][CH2:22][NH:23][c:24]1[cH:25][cH:26][c:27]([F:28])[cH:29][cH:30]1)[CH2:5][CH:6]1[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11]1)=[O:13]>>[O:1]=[C:2]([CH2:3][C@@H:4]([CH2:5][CH:6]1[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11]1)[C:12](=[O:... | C1COCCN1.O=C(C[C@@H](CC1CCCCC1)C(=O)O)NCCNc1ccc(F)cc1 | O=C(C[C@@H](CC1CCCCC1)C(=O)N1CCOCC1)NCCNc1ccc(F)cc1 | null | null | ClCCl | Acylation | Acylation of Nitrogen Nucleophiles by Carboxylic Acids | 2ef483949e7ba3e5f888cf14cdce25fa611f75be09fdf1854a473be519821b59 | c5e4172490b2731ba9322b68af56376edadc31ce0bb9a3dfdea23a1817a852fd | O=C(C[C@@H](CC1CCCCC1)C(=O)N1CCOCC1)NCCNc1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[C:5]-[C:6](-[#7:7])=[O;D1;H0:8].[#8:9]1-[C:10]-[C:11]-[NH;D2;+0:12]-[C:13]-[C:14]-1>>[#7:7]-[C:6](=[O;D1;H0:8])-[C:5]-[C:3](-[C:4])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[N;H0;D3;+0:12]1-[C:11]-[C:10]-[#8:9]-[C:14]-[C:13]-1 | 48.1 | [{"value": 40.0, "product": "C1(CCCCC1)C[C@H](CC(=O)NCCNC1=CC=C(C=C1)F)C(=O)N1CCOCC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 48.1, "product": "C1(CCCCC1)C[C@H](CC(=O)NCCNC1=CC=C(C=C1)F)C(=O)N1CCOCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | (R)-2-cyclohexylmethyl-N-[2-(4-fluoro-phenylamino)-ethyl]-succinamic acid (220 mg, 0.52 mmol) was treated with morpholine (110 μL, 1.26 mmol, 2.4 eq.) and HATU (238 mg, 0.72 mmol, 1.4 eq.). The reagents were dissolved in dry dichloromethane (4 mL) and treated with diisopropylethylamine (315 μL, 1.81 mmol, 3.5 eq.). The... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | Tertiary amide | C1COCCN1 | C1COCC[NH]1 | C1CCCCC1.C1COCC[NH]1.c1ccccc1 | HO- | ClCCl | null | null | C1COCCN1.O=C(C[C@@H](CC1CCCCC1)C(=O)O)NCCNc1ccc(F)cc1>ClCCl>O=C(C[C@@H](CC1CCCCC1)C(=O)N1CCOCC1)NCCNc1ccc(F)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-6a83582ae7f04490a5d77f1c027da962 | O=C(N[C@@H](COCc1ccccc1)CN1CCc2cc(F)ccc21)O[C@@H](CC1CCCCC1)C(=O)N1CCOCC1>>O=C(N[C@@H](CO)CN1CCc2cc(F)ccc21)O[C@@H](CC1CCCCC1)C(=O)N1CCOCC1 | C1(CCCCC1)C[C@@H](C(=O)N1CCOCC1)OC(N[C@H](CN1CCC2=CC(=CC=C12)F)COCC1=CC=CC=C1)=O>>C1(CCCCC1)C[C@@H](C(=O)N1CCOCC1)OC(N[C@H](CN1CCC2=CC(=CC=C12)F)CO)=O | c1ccc(C[O:6][CH2:5][C@H:4]([NH:3][C:2](=[O:1])[O:18][C@@H:19]([CH2:20][CH:21]2[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26]2)[C:27](=[O:28])[N:29]2[CH2:30][CH2:31][O:32][CH2:33][CH2:34]2)[CH2:7][N:8]2[CH2:9][CH2:10][c:11]3[cH:12][c:13]([F:14])[cH:15][cH:16][c:17]32)cc1>>[O:1]=[C:2]([NH:3][C@@H:4]([CH2:5][OH:6])[CH2:7][N:8]1... | O=C(N[C@@H](COCc1ccccc1)CN1CCc2cc(F)ccc21)O[C@@H](CC1CCCCC1)C(=O)N1CCOCC1 | O=C(N[C@@H](CO)CN1CCc2cc(F)ccc21)O[C@@H](CC1CCCCC1)C(=O)N1CCOCC1 | null | [Pd] | CO | Deprotection | Hydroxyl benzyl deprotection | c8a6fd2e05b2d36256c76b73aaf4118f20eb14abce1c0289b554265e30b218aa | 29a81fd08d26edc3da6d72c4958026f5af2119326dc1b4714ee5be1c41835609 | O=C(NCCN1CCc2ccccc21)O[C@@H](CC1CCCCC1)C(=O)N1CCOCC1 | [C:1]-[C:2]-[O;H0;D2;+0:3]-C-c1:c:c:c:c:c:1>>[C:1]-[C:2]-[OH;D1;+0:3] | 71.4 | [{"value": 71.0, "product": "C1(CCCCC1)C[C@@H](C(=O)N1CCOCC1)OC(N[C@H](CN1CCC2=CC(=CC=C12)F)CO)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 71.4, "product": "C1(CCCCC1)C[C@@H](C(=O)N1CCOCC1)OC(N[C@H](CN1CCC2=CC(=CC=C12)F)CO)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | The title compound of Example 10 (50 mg, 0.088 mmol) was dissolved in a minimum amount of methanol (approx. 1-2 mL) and a catalytic amount of 10% Pd/C was added. Air was purged from the reaction vessel and H2 gas was introduced via a balloon. The reaction mixture was stirred for several hours under a H2 atmosphere, aft... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Primary alcohol | c1ccccc1 | null | c1ccc2c(c1)CC[NH]2.C1CCCCC1.C1COCC[NH]1 | Other | [Pd].CO | null | null | O=C(N[C@@H](COCc1ccccc1)CN1CCc2cc(F)ccc21)O[C@@H](CC1CCCCC1)C(=O)N1CCOCC1>[Pd].CO>O=C(N[C@@H](CO)CN1CCc2cc(F)ccc21)O[C@@H](CC1CCCCC1)C(=O)N1CCOCC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-51a95571010e457c8778b0219e6c730d | CC(C)(C)OC(=O)C[C@@H](CC1CCCC1)C(=O)N1C(=O)OC[C@@H]1Cc1ccccc1.OO>>CC(C)(C)OC(=O)C[C@@H](CC1CCCC1)C(=O)O | OO.[Li+].[OH-].C(C)(C)(C)OC(C[C@H](C(=O)N1C(OC[C@@H]1CC1=CC=CC=C1)=O)CC1CCCC1)=O.S(=O)([O-])[O-].[Na+].[Na+].C([O-])(O)=O.[Na+]>>C(C)(C)(C)OC(C[C@H](C(=O)O)CC1CCCC1)=O | O=C1OC[C@H](Cc2ccccc2)N1[C:16]([C@@H:9]([CH2:8][C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:10][CH:11]1[CH2:12][CH2:13][CH2:14][CH2:15]1)=[O:17].O[OH:18]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[CH2:8][C@@H:9]([CH2:10][CH:11]1[CH2:12][CH2:13][CH2:14][CH2:15]1)[C:16](=[O:17])[OH:18] | CC(C)(C)OC(=O)C[C@@H](CC1CCCC1)C(=O)N1C(=O)OC[C@@H]1Cc1ccccc1.OO | CC(C)(C)OC(=O)C[C@@H](CC1CCCC1)C(=O)O | null | null | O.C1CCOC1 | Protection | OtherReaction | 5e8d363a37fc08652d7428d883ecf869fb4ee2b7eef0b3e6daf3598f9da8bd9f | c56e1872d5846fe1c198ecc1bf4849e80e217897fb667d1c951e7cecf0d4c289 | C1CCCC1 | 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:7](-[#8:8])=[O;D1;H0:9]>>[#8:8]-[C:7](=[O;D1;H0:9])-[C:6]-[C:4](-[C:5])-[C;H0;D3;+0:2](=[O;D1;H0:3])-[OH;D1;+0:1] | 73 | [{"value": 73.0, "product": "C(C)(C)(C)OC(C[C@H](C(=O)O)CC1CCCC1)=O", "details": "PERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | null | null | 4-(4-(S)-Benzyl-2-oxo-oxazolidin-3-yl)-3-(R)-cyclopentylmethyl-4-oxo-butyric acid tert-butyl ester (620 mg, 1.49 mmol, 1.0 eq.) was dissolved in THF (35 mL) and cooled in a 0° C. ice-water bath. Hydrogen peroxide (31 w/w %) (654 μL, 5.97 mmol, 4.0 eq.) and LiOH (72 mg, 2.98 mmol, 2.0 eq.) in water (7.5 mL) was added to... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Substituted dicarboximide.Peroxide | Carboxylic acid | C1COCN1.c1ccccc1 | null | C1CCCC1 | HO- | O.C1CCOC1 | 0 | null | CC(C)(C)OC(=O)C[C@@H](CC1CCCC1)C(=O)N1C(=O)OC[C@@H]1Cc1ccccc1.OO>O.C1CCOC1>CC(C)(C)OC(=O)C[C@@H](CC1CCCC1)C(=O)O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-1cc77382802c48728c4db5a5d524e272 | C[C@H](N)CNc1ccc(OC(F)(F)F)cc1.O=C(O)[C@H](CSCc1ccccc1)NC(=O)N1CCOCC1>>C[C@@H](CNc1ccc(OC(F)(F)F)cc1)NC(=O)[C@H](CSCc1ccccc1)NC(=O)N1CCOCC1 | CCN(C(C)C)C(C)C.C(C1=CC=CC=C1)SC[C@@H](C(=O)O)NC(=O)N1CCOCC1.FC(OC1=CC=C(C=C1)NC[C@H](C)N)(F)F.CN(C)C(=[N+](C)C)ON1C2=C(C=CC=N2)N=N1.F[P-](F)(F)(F)(F)F>>C(C1=CC=CC=C1)SC[C@@H](C(N[C@H](CNC1=CC=C(C=C1)OC(F)(F)F)C)=O)NC(=O)N1CCOCC1 | [CH3:1][C@@H:2]([CH2:3][NH:4][c:5]1[cH:6][cH:7][c:8]([O:9][C:10]([F:11])([F:12])[F:13])[cH:14][cH:15]1)[NH2:16].O[C:17](=[O:18])[C@H:19]([CH2:20][S:21][CH2:22][c:23]1[cH:24][cH:25][cH:26][cH:27][cH:28]1)[NH:29][C:30](=[O:31])[N:32]1[CH2:33][CH2:34][O:35][CH2:36][CH2:37]1>>[CH3:1][C@@H:2]([CH2:3][NH:4][c:5]1[cH:6][cH:7]... | C[C@H](N)CNc1ccc(OC(F)(F)F)cc1.O=C(O)[C@H](CSCc1ccccc1)NC(=O)N1CCOCC1 | C[C@@H](CNc1ccc(OC(F)(F)F)cc1)NC(=O)[C@H](CSCc1ccccc1)NC(=O)N1CCOCC1 | null | null | C(Cl)Cl | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(NCCNc1ccccc1)[C@H](CSCc1ccccc1)NC(=O)N1CCOCC1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[#7:5]-[C:6]=[O;D1;H0:7].[C:8]-[C:9](-[C;D1;H3:10])-[NH2;D1;+0:11]>>[C:4]-[C:3](-[#7:5]-[C:6]=[O;D1;H0:7])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:11]-[C:9](-[C:8])-[C;D1;H3:10] | 6.4 | [{"value": 5.0, "product": "C(C1=CC=CC=C1)SC[C@@H](C(N[C@H](CNC1=CC=C(C=C1)OC(F)(F)F)C)=O)NC(=O)N1CCOCC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 6.4, "product": "C(C1=CC=CC=C1)SC[C@@H](C(N[C@H](CNC1=CC=C(C=C1)OC(F)(F)F)C)=O)NC(=O)N1CCOCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 3-Benzylsulfanyl-2-(R)-[(morpholine-4-carbonyl)-amino]-propionic acid (182 mg, 0.56 mmol, 1.2 eq.), N1-(4-Trifluoromethoxy-phenyl)-(S)-propane-1,2-diamine from Scheme 1a (110 mg, 0.47 mmol, 1.0 eq.), and HATU (185 mg, 0.56 mmol, 1.2 eq.) were dissolved in CH2Cl2 (2 mL) at room temperature. DIPEA (245 μL, 1.41 mmol, 3.0... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccccc1.C1COCC[NH]1 | HO- | C(Cl)Cl | null | null | C[C@H](N)CNc1ccc(OC(F)(F)F)cc1.O=C(O)[C@H](CSCc1ccccc1)NC(=O)N1CCOCC1>C(Cl)Cl>C[C@@H](CNc1ccc(OC(F)(F)F)cc1)NC(=O)[C@H](CSCc1ccccc1)NC(=O)N1CCOCC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-b03582c0106445d5969ece8a2d778f3b | C[C@H](N)CNc1ccc(OC(F)(F)F)cc1.O=C(O)[C@H](CS(=O)(=O)Cc1ccccc1)NC(=O)N1CCOCC1>>C[C@@H](CNc1ccc(OC(F)(F)F)cc1)NC(=O)[C@H](CS(=O)(=O)Cc1ccccc1)NC(=O)N1CCOCC1 | N1(CCOCC1)C(=O)N[C@H](C(=O)O)CS(=O)(=O)CC1=CC=CC=C1.FC(OC1=CC=C(C=C1)NC[C@H](C)N)(F)F.C(CCl)Cl.C=1C=CC2=C(C1)N=NN2O.CN1CCOCC1>>C[C@@H](CNC1=CC=C(C=C1)OC(F)(F)F)NC(=O)[C@H](CS(=O)(=O)CC1=CC=CC=C1)NC(=O)N1CCOCC1 | [CH3:1][C@@H:2]([CH2:3][NH:4][c:5]1[cH:6][cH:7][c:8]([O:9][C:10]([F:11])([F:12])[F:13])[cH:14][cH:15]1)[NH2:16].O[C:17](=[O:18])[C@H:19]([CH2:20][S:21](=[O:22])(=[O:23])[CH2:24][c:25]1[cH:26][cH:27][cH:28][cH:29][cH:30]1)[NH:31][C:32](=[O:33])[N:34]1[CH2:35][CH2:36][O:37][CH2:38][CH2:39]1>>[CH3:1][C@@H:2]([CH2:3][NH:4]... | C[C@H](N)CNc1ccc(OC(F)(F)F)cc1.O=C(O)[C@H](CS(=O)(=O)Cc1ccccc1)NC(=O)N1CCOCC1 | C[C@@H](CNc1ccc(OC(F)(F)F)cc1)NC(=O)[C@H](CS(=O)(=O)Cc1ccccc1)NC(=O)N1CCOCC1 | null | null | C(Cl)Cl | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(NCCNc1ccccc1)[C@H](CS(=O)(=O)Cc1ccccc1)NC(=O)N1CCOCC1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[#7:5]-[C:6]=[O;D1;H0:7].[C:8]-[C:9](-[C;D1;H3:10])-[NH2;D1;+0:11]>>[C:4]-[C:3](-[#7:5]-[C:6]=[O;D1;H0:7])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:11]-[C:9](-[C:8])-[C;D1;H3:10] | 31 | [{"value": 31.0, "product": "C[C@@H](CNC1=CC=C(C=C1)OC(F)(F)F)NC(=O)[C@H](CS(=O)(=O)CC1=CC=CC=C1)NC(=O)N1CCOCC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 28.6, "product": "C[C@@H](CNC1=CC=C(C=C1)OC(F)(F)F)NC(=O)[C@H](CS(=O)(=O)CC1=CC=CC=C1)NC(=O)N1CCOCC1", "details": "CALCULATEDPERCENTYIELD", "is_des... | null | null | null | null | 2-(R)-[(Morpholine-4-carbonyl)-amino]-3-phenylmethanesulfonyl-propionic acid (73 mg, 0.21 mmol, 1.0 eq.), N1-(4-Trifluoromethoxy-phenyl)-(S)-propane-1,2-diamine from Scheme 1a (48 mg, 0.21 mmol, 1.0 eq.), EDC (59 mg, 0.31 mmol, 1.5 eq.), and HOBT (38 mg, 0.25 mmol, 1.2 eq.) were dissolved in CH2Cl2 at room temperature.... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccccc1.C1COCC[NH]1 | HO- | C(Cl)Cl | null | null | C[C@H](N)CNc1ccc(OC(F)(F)F)cc1.O=C(O)[C@H](CS(=O)(=O)Cc1ccccc1)NC(=O)N1CCOCC1>C(Cl)Cl>C[C@@H](CNc1ccc(OC(F)(F)F)cc1)NC(=O)[C@H](CS(=O)(=O)Cc1ccccc1)NC(=O)N1CCOCC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-8d58f29af60b4591908b70035a518ec4 | CC(C)(C)OC(=O)C[C@@H](CCC1CCCCC1)C(=O)N1C(=O)OC[C@@H]1Cc1ccccc1>>O=C(O)C[C@@H](CCC1CCCCC1)C(=O)N1C(=O)OC[C@@H]1Cc1ccccc1 | C(C)(C)(C)OC(C[C@@H](CCC1CCCCC1)C(=O)N1C(OC[C@@H]1CC1=CC=CC=C1)=O)=O.C(Cl)Cl.C(=O)(C(F)(F)F)O>>C(C1=CC=CC=C1)[C@@H]1N(C(OC1)=O)C(=O)[C@@H](CC(=O)O)CCC1CCCCC1 | CC(C)(C)[O:3][C:2](=[O:1])[CH2:4][C@@H:5]([CH2:6][CH2:7][CH:8]1[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13]1)[C:14](=[O:15])[N:16]1[C:17](=[O:18])[O:19][CH2:20][C@@H:21]1[CH2:22][c:23]1[cH:24][cH:25][cH:26][cH:27][cH:28]1>>[O:1]=[C:2]([OH:3])[CH2:4][C@@H:5]([CH2:6][CH2:7][CH:8]1[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13]1)[C:14... | CC(C)(C)OC(=O)C[C@@H](CCC1CCCCC1)C(=O)N1C(=O)OC[C@@H]1Cc1ccccc1 | O=C(O)C[C@@H](CCC1CCCCC1)C(=O)N1C(=O)OC[C@@H]1Cc1ccccc1 | null | null | O | Deprotection | Deprotection of carboxylic acid | 152e5537e48c95b4a3e767536b0f9f68d1308e5f484070828ab5ed951805157a | 7f019d4cfe9b3036d0a2d3a3209aa0e1fcb05418ebee15a4be5e125d315d5f01 | O=C(CCCC1CCCCC1)N1C(=O)OC[C@@H]1Cc1ccccc1 | C-C(-C)(-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 | 3-(R)-(4-(S)-Benzyl-2-oxo-oxazolidine-3-carbonyl)-5-cyclohexyl-pentanoic acid tert-butyl ester (2.01 g, 4.53 mmol, 1.0 eq) was treated with a 45:50:5 CH2Cl2:TFA:H2O solution. The reaction was monitored by LC/MS and complete after 1 hour. The solution was evaporated and provided a quantitative yield of 3-(R)-(4-(S)-Benz... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Boc | Carboxylic acid | null | null | C1CCCCC1.C1COC[NH]1.c1ccccc1 | Other | O | null | 1 | CC(C)(C)OC(=O)C[C@@H](CCC1CCCCC1)C(=O)N1C(=O)OC[C@@H]1Cc1ccccc1>O>O=C(O)C[C@@H](CCC1CCCCC1)C(=O)N1C(=O)OC[C@@H]1Cc1ccccc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-f9dba20689f8425caa177133c2210e82 | C1COCCN1.O=C(O)C[C@@H](CCC1CCCCC1)C(=O)N1C(=O)OC[C@@H]1Cc1ccccc1>>O=C(C[C@@H](CCC1CCCCC1)C(=O)N1C(=O)OC[C@@H]1Cc1ccccc1)N1CCOCC1 | N1CCOCC1.C(C1=CC=CC=C1)[C@@H]1N(C(OC1)=O)C(=O)[C@@H](CC(=O)O)CCC1CCCCC1.CN(C)C(=[N+](C)C)ON1C2=C(C=CC=N2)N=N1.F[P-](F)(F)(F)(F)F.N1CCOCC1.CCN(C(C)C)C(C)C>>C(C1=CC=CC=C1)[C@@H]1N(C(OC1)=O)C([C@@H](CC(=O)N1CCOCC1)CCC1CCCCC1)=O | [NH:28]1[CH2:29][CH2:30][O:31][CH2:32][CH2:33]1.O[C:2](=[O:1])[CH2:3][C@@H:4]([CH2:5][CH2:6][CH:7]1[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12]1)[C:13](=[O:14])[N:15]1[C:16](=[O:17])[O:18][CH2:19][C@@H:20]1[CH2:21][c:22]1[cH:23][cH:24][cH:25][cH:26][cH:27]1>>[O:1]=[C:2]([CH2:3][C@@H:4]([CH2:5][CH2:6][CH:7]1[CH2:8][CH2:9][CH2... | C1COCCN1.O=C(O)C[C@@H](CCC1CCCCC1)C(=O)N1C(=O)OC[C@@H]1Cc1ccccc1 | O=C(C[C@@H](CCC1CCCCC1)C(=O)N1C(=O)OC[C@@H]1Cc1ccccc1)N1CCOCC1 | null | null | CN(C)C=O.C(Cl)Cl.C(C)(=O)OCC | Acylation | Acylation of Nitrogen Nucleophiles by Carboxylic Acids | 2ef483949e7ba3e5f888cf14cdce25fa611f75be09fdf1854a473be519821b59 | c5e4172490b2731ba9322b68af56376edadc31ce0bb9a3dfdea23a1817a852fd | O=C(C[C@@H](CCC1CCCCC1)C(=O)N1C(=O)OC[C@@H]1Cc1ccccc1)N1CCOCC1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4]-[C:5](-[#7:6])=[O;D1;H0:7].[#8:8]1-[C:9]-[C:10]-[NH;D2;+0:11]-[C:12]-[C:13]-1>>[#7:6]-[C:5](=[O;D1;H0:7])-[C:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[N;H0;D3;+0:11]1-[C:10]-[C:9]-[#8:8]-[C:13]-[C:12]-1 | 92.3 | [{"value": 92.0, "product": "C(C1=CC=CC=C1)[C@@H]1N(C(OC1)=O)C([C@@H](CC(=O)N1CCOCC1)CCC1CCCCC1)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 92.3, "product": "C(C1=CC=CC=C1)[C@@H]1N(C(OC1)=O)C([C@@H](CC(=O)N1CCOCC1)CCC1CCCCC1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 3-(R)-(4-(S)-Benzyl-2-oxo-oxazolidine-3-carbonyl)-5-cyclohexyl-pentanoic acid (1.76 g, 4.53 mmol, 1.0 eq.) dissolved in DMF (10 mL) and treated with HATU (1.3 g, 5.0 mmol, 1.1 eq.), morpholine (680 μL, 7.77 mmol, 1.7 eq.) and DIPEA (870 μL, 5.0 mmol, 1.1 eq.). Alternatively an additional equivalent of morpholine can be... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | Tertiary amide | C1COCCN1 | C1COCC[NH]1 | C1CCCCC1.C1COC[NH]1.c1ccccc1.C1COCC[NH]1 | HO- | CN(C)C=O.C(Cl)Cl.C(C)(=O)OCC | null | null | C1COCCN1.O=C(O)C[C@@H](CCC1CCCCC1)C(=O)N1C(=O)OC[C@@H]1Cc1ccccc1>CN(C)C=O.C(Cl)Cl.C(C)(=O)OCC>O=C(C[C@@H](CCC1CCCCC1)C(=O)N1C(=O)OC[C@@H]1Cc1ccccc1)N1CCOCC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-c73d7984a4e44da3b5dfa3e104d5e889 | C[C@H](N)CNc1ccc(OC(F)(F)F)cc1.O=C(O)[C@H](CCC1CCCCC1)CC(=O)N1CCOCC1>>C[C@@H](CNc1ccc(OC(F)(F)F)cc1)NC(=O)[C@H](CCC1CCCCC1)CC(=O)N1CCOCC1 | C1(CCCCC1)CC[C@@H](C(=O)O)CC(=O)N1CCOCC1.CN(C)C(=[N+](C)C)ON1C2=C(C=CC=N2)N=N1.F[P-](F)(F)(F)(F)F.FC(OC1=CC=C(C=C1)NC[C@H](C)N)(F)F.CCN(C(C)C)C(C)C>>C1(CCCCC1)CC[C@@H](C(=O)N[C@H](CNC1=CC=C(C=C1)OC(F)(F)F)C)CC(=O)N1CCOCC1 | [CH3:1][C@@H:2]([CH2:3][NH:4][c:5]1[cH:6][cH:7][c:8]([O:9][C:10]([F:11])([F:12])[F:13])[cH:14][cH:15]1)[NH2:16].O[C:17](=[O:18])[C@H:19]([CH2:20][CH2:21][CH:22]1[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27]1)[CH2:28][C:29](=[O:30])[N:31]1[CH2:32][CH2:33][O:34][CH2:35][CH2:36]1>>[CH3:1][C@@H:2]([CH2:3][NH:4][c:5]1[cH:6][cH:7... | C[C@H](N)CNc1ccc(OC(F)(F)F)cc1.O=C(O)[C@H](CCC1CCCCC1)CC(=O)N1CCOCC1 | C[C@@H](CNc1ccc(OC(F)(F)F)cc1)NC(=O)[C@H](CCC1CCCCC1)CC(=O)N1CCOCC1 | null | null | CN(C)C=O.C(Cl)Cl.C(C)(=O)OCC | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(NCCNc1ccccc1)[C@H](CCC1CCCCC1)CC(=O)N1CCOCC1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[C:5]-[C:6](-[#7:7])=[O;D1;H0:8].[C:9]-[C:10](-[C;D1;H3:11])-[NH2;D1;+0:12]>>[#7:7]-[C:6](=[O;D1;H0:8])-[C:5]-[C:3](-[C:4])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:12]-[C:10](-[C:9])-[C;D1;H3:11] | null | [] | null | null | null | null | 2-(R)-(2-Cyclohexyl-ethyl)-4-morpholin-4-yl-4-oxo-butyric acid (98 mg, 0.33 mmol, 1.0 eq.) dissolved in DMF (2 mL) and treated with HATU (137 mg, 0.36 mmol, 1.1 eq.), (S)—N1-(4-Trifluoromethoxy-phenyl)-propane-1,2-diamine (85 mg, 0.36 mmol, 1.1 eq.) and DIPEA (63 μL, 0.36 mmol, 1.1 eq.). Alternatively CH2Cl2 can be use... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.C1CCCCC1.C1COCC[NH]1 | HO- | CN(C)C=O.C(Cl)Cl.C(C)(=O)OCC | null | null | C[C@H](N)CNc1ccc(OC(F)(F)F)cc1.O=C(O)[C@H](CCC1CCCCC1)CC(=O)N1CCOCC1>CN(C)C=O.C(Cl)Cl.C(C)(=O)OCC>C[C@@H](CNc1ccc(OC(F)(F)F)cc1)NC(=O)[C@H](CCC1CCCCC1)CC(=O)N1CCOCC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-363979f881834f339393193845b4e342 | C=CC(=O)O.C=CCC(C)(C)C>>CC(C)(C)CC=CC(=O)O | CC(CC=C)(C)C.C(C=C)(=O)O>>CC(CC=CC(=O)O)(C)C | [CH2:6]=[CH:7][C:8](=[O:9])[OH:10].C=C[CH2:5][C:2]([CH3:1])([CH3:3])[CH3:4]>>[CH3:1][C:2]([CH3:3])([CH3:4])[CH2:5][CH:6]=[CH:7][C:8](=[O:9])[OH:10] | C=CC(=O)O.C=CCC(C)(C)C | CC(C)(C)CC=CC(=O)O | null | [Ru] | C(Cl)Cl | C-C Coupling | OtherReaction | 117d9a19ce3d25c46858e5d44570547905555fd9d79d47e129edbc20f2e9139d | 7cc827c291e2a977a7a91dfb00752230897a77bed46038b3e1551b560ca4b6fc | null | C=C-[CH2;D2;+0:1]-[C:2](-[C;D1;H3:3])(-[C;D1;H3:4])-[C;D1;H3:5].[CH2;D1;+0:6]=[C:7]-[C:8](=[O;D1;H0:9])-[O;D1;H1:10]>>[C;D1;H3:3]-[C:2](-[C;D1;H3:4])(-[C;D1;H3:5])-[CH2;D2;+0:1]-[CH;D2;+0:6]=[C:7]-[C:8](=[O;D1;H0:9])-[O;D1;H1:10] | 99 | [{"value": 99.0, "product": "CC(CC=CC(=O)O)(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 98.7, "product": "CC(CC=CC(=O)O)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 5,5-Dimethyl-hex-2-enoic acid was prepared using a modified procedure from Chatterjee, A. K. et al. J. Am. Chem. Soc. 2003, 125(37), 11360-11370. 4,4-Dimethyl-1-pentene (5.0 mL, 34.77 mmol, 1.5 eq.) and acrylic acid (1.54 mL, 22.51 mmol, 1.0 eq.) were added to a solution of ruthenium catalyst ([1,3-bis(2,4,6-trimethylp... | 10.6084/m9.figshare.5104873.v1 | null | Allyl.Vinyl | null | null | null | null | Other | [Ru].C(Cl)Cl | null | null | C=CC(=O)O.C=CCC(C)(C)C>[Ru].C(Cl)Cl>CC(C)(C)CC=CC(=O)O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-6c4ebff5f0044ba8a0948b33a77e2c07 | CC(C)(C)C=O.CCOP(=O)(CC(=O)OC)OCC>>COC(=O)C=CC(C)(C)C | O.[Li]CCCC.C(C)OP(=O)(OCC)CC(=O)OC.CC(C=O)(C)C>>COC(C=CC(C)(C)C)=O | O=[CH:6][C:7]([CH3:8])([CH3:9])[CH3:10].CCOP(=O)(OCC)[CH2:5][C:3]([O:2][CH3:1])=[O:4]>>[CH3:1][O:2][C:3](=[O:4])[CH:5]=[CH:6][C:7]([CH3:8])([CH3:9])[CH3:10] | CC(C)(C)C=O.CCOP(=O)(CC(=O)OC)OCC | COC(=O)C=CC(C)(C)C | null | null | C1CCOC1 | C-C Coupling | Wittig with Phosphonium | a86984aeb4a9963534e0b081b0ecca18455fda1775f36ce168d1ca4cf966df3e | 203dd34a20dceaf1737adbf20e01b43c2424e4e4b1722d942d1a796d895396e6 | null | C-C-O-P(=O)(-O-C-C)-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#8:4]-[C;D1;H3:5].O=[CH;D2;+0:6]-[C:7](-[C;D1;H3:8])(-[C;D1;H3:9])-[C;D1;H3:10]>>[C;D1;H3:8]-[C:7](-[C;D1;H3:9])(-[C;D1;H3:10])-[CH;D2;+0:6]=[CH;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#8:4]-[C;D1;H3:5] | null | [] | -78 | CELSIUS | 20 | MINUTE | Methyl diethylphosphonoacetate (13.35 mL, 73.6 mmol, 1.05 eq.) was dissolved in THF (30 mL) and cooled to −78° C. in an acetone-dry ice bath. n-BuLi (1.6M in hexanes) (45.8 mL, 73.2 mmol, 1.05 eq.) was added slowly over 20 min. Trimethylacetaldehyde (6.0 g, 69.6 mmol, 1.0 eq.), was added to the reaction and allowed to ... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ester | Ester | null | null | null | HO- | C1CCOC1 | -78 | 0.333333 | CC(C)(C)C=O.CCOP(=O)(CC(=O)OC)OCC>C1CCOC1>COC(=O)C=CC(C)(C)C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-2c239dc3820e416cbba4e6bf8b0413c1 | COC(=O)C=CC(C)(C)C>>COC(=O)CCC(C)(C)C | COC(C=CC(C)(C)C)=O>>COC(CCC(C)(C)C)=O | [CH3:1][O:2][C:3](=[O:4])[CH:5]=[CH:6][C:7]([CH3:8])([CH3:9])[CH3:10]>>[CH3:1][O:2][C:3](=[O:4])[CH2:5][CH2:6][C:7]([CH3:8])([CH3:9])[CH3:10] | COC(=O)C=CC(C)(C)C | COC(=O)CCC(C)(C)C | null | [Pd] | CO.C(C)(=O)OCC | Reduction | Hydrogenation (double to single) | c04c38f95d7b746e5bdb99c368a7a33956c97b95b54c7ad89be2a85526386ec9 | 9a50abf8d2e4cd9195d7a0cadbe97483a261a81cf70b653cfddd5ecf76d383a6 | null | [C;D1;H3:1]-[C:2](-[C;D1;H3:3])(-[C;D1;H3:4])-[CH;D2;+0:5]=[CH;D2;+0:6]-[C:7](=[O;D1;H0:8])-[#8:9]-[C;D1;H3:10]>>[C;D1;H3:1]-[C:2](-[C;D1;H3:3])(-[C;D1;H3:4])-[CH2;D2;+0:5]-[CH2;D2;+0:6]-[C:7](=[O;D1;H0:8])-[#8:9]-[C;D1;H3:10] | 81 | [{"value": 81.0, "product": "COC(CCC(C)(C)C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 80.8, "product": "COC(CCC(C)(C)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 12 | HOUR | 4,4-Dimethyl-pent-2-enoic acid methyl ester (8.52 g, 60.0 mmol) was dissolved in MeOH (30 mL) and ethyl acetate (30 mL). Palladium on carbon (10 wt %) (˜50 mg) was added to the reaction and was placed under a H2 balloon (1 atm). The reaction was allowed to stir for 12 hours, flushed with nitrogen and filtered over a pa... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Ester | null | null | null | null | [Pd].CO.C(C)(=O)OCC | null | 12 | COC(=O)C=CC(C)(C)C>[Pd].CO.C(C)(=O)OCC>COC(=O)CCC(C)(C)C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-0d4ea798a4f64207a19b310872483710 | COC(=O)CCC(C)(C)C>>CC(C)(C)CCC(=O)O | COC(CCC(C)(C)C)=O.[OH-].[Na+]>>CC(CCC(=O)O)(C)C | C[O:9][C:7]([CH2:6][CH2:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:8]>>[CH3:1][C:2]([CH3:3])([CH3:4])[CH2:5][CH2:6][C:7](=[O:8])[OH:9] | COC(=O)CCC(C)(C)C | CC(C)(C)CCC(=O)O | null | null | O.C(Cl)Cl | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | null | 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] | 85 | [{"value": 85.0, "product": "CC(CCC(=O)O)(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 84.7, "product": "CC(CCC(=O)O)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 4.5 | HOUR | 4,4-Dimethyl-pentanoic acid methyl ester (7.0 g, 48.5 mmol, 1.0 eq.) was treated with a solution of NaOH (4.0 g, 100 mmol, 2.1 eq.) in water (5 mL). The homogeneous solution was allowed to stir for 4-5 hours. The reaction was diluted with CH2Cl2 and the aqueous layer was extracted with CH2Cl2 (50 mL×3). The aqueous lay... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | null | Other | O.C(Cl)Cl | null | 4.5 | COC(=O)CCC(C)(C)C>O.C(Cl)Cl>CC(C)(C)CCC(=O)O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-7382ee2eb4ff48368b5a9b8708fcd1a2 | C[C@@H](CNc1ccc(OC(F)(F)F)cc1)NC(=O)[C@@H](CC(=O)N1CCSCC1)CC1CCCCC1>>C[C@@H](CNc1ccc(OC(F)(F)F)cc1)NC(=O)[C@@H](CC(=O)N1CCS(=O)(=O)CC1)CC1CCCCC1 | OOS(=O)[O-].[K+].C1(CCCCC1)C[C@@H](C(=O)N[C@H](CNC1=CC=C(C=C1)OC(F)(F)F)C)CC(N1CCSCC1)=O>>C1(CCCCC1)C[C@@H](C(=O)N[C@H](CNC1=CC=C(C=C1)OC(F)(F)F)C)CC(=O)N1CCS(CC1)(=O)=O | [CH3:1][C@@H:2]([CH2:3][NH:4][c:5]1[cH:6][cH:7][c:8]([O:9][C:10]([F:11])([F:12])[F:13])[cH:14][cH:15]1)[NH:16][C:17](=[O:18])[C@@H:19]([CH2:20][C:21](=[O:22])[N:23]1[CH2:24][CH2:25][S:26][CH2:29][CH2:30]1)[CH2:31][CH:32]1[CH2:33][CH2:34][CH2:35][CH2:36][CH2:37]1>>[CH3:1][C@@H:2]([CH2:3][NH:4][c:5]1[cH:6][cH:7][c:8]([O:... | C[C@@H](CNc1ccc(OC(F)(F)F)cc1)NC(=O)[C@@H](CC(=O)N1CCSCC1)CC1CCCCC1 | C[C@@H](CNc1ccc(OC(F)(F)F)cc1)NC(=O)[C@@H](CC(=O)N1CCS(=O)(=O)CC1)CC1CCCCC1 | null | null | null | Oxidation | OtherReaction | 4e68790434c882ffa16cbefcd9615ee85d2b208cef00d7ba37514eb822eb67a9 | 5cedc1bf0f43f21d78a249521ecfcec19fc5ac4895c41eed0e84f0c2618149fa | O=C(NCCNc1ccccc1)[C@@H](CC(=O)N1CCS(=O)(=O)CC1)CC1CCCCC1 | [#7:1]1-[C:2]-[C:3]-[S;H0;D2;+0:4]-[C:5]-[C:6]-1>>[O;D1;H0:7]=[S;H0;D4;+0:4]1(=[O;D1;H0:8])-[C:3]-[C:2]-[#7:1]-[C:6]-[C:5]-1 | null | [] | null | null | null | null | The compound was synthesized in a similar fashion to Example 6. An OXONE oxidation was employed title compound of Example 51 to furnish the sulfone. A procedure was used as described in McCarthy, J. R. et al. Org. Synth., CV9, 446. 1H NMR (CD3OD, 400 MHz) δ 0.73-0.79 (m, 2H), 1.00-1.19 (m, 7H), 1.10 (d, J=6.8 Hz), 1.34... | 10.6084/m9.figshare.5104873.v1 | null | Monosulfide | Sulfone | C1CSCC[NH]1 | C1CSCC[NH]1 | c1ccccc1.C1CSCC[NH]1.C1CCCCC1 | null | null | null | null | C[C@@H](CNc1ccc(OC(F)(F)F)cc1)NC(=O)[C@@H](CC(=O)N1CCSCC1)CC1CCCCC1>>C[C@@H](CNc1ccc(OC(F)(F)F)cc1)NC(=O)[C@@H](CC(=O)N1CCS(=O)(=O)CC1)CC1CCCCC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-982f8fedc2954565b07439f8735834fd | CC(C)[C@H](N)CO.O=C(O)[C@@H](CC(=O)N1CCOCC1)c1ccc(F)cc1>>CC(C)[C@@H](CO)NC(=O)[C@@H](CC(=O)N1CCOCC1)c1ccc(F)cc1 | C(C)(C)N(CC)C(C)C.FC1=CC=C(C=C1)[C@@H](C(=O)O)CC(=O)N1CCOCC1.N[C@H](CO)C(C)C.CN(C)C(=[N+](C)C)ON1C2=C(C=CC=N2)N=N1.F[P-](F)(F)(F)(F)F>>FC1=CC=C(C=C1)[C@@H](C(=O)N[C@@H](C(C)C)CO)CC(=O)N1CCOCC1 | [CH3:1][CH:2]([CH3:3])[C@@H:4]([CH2:5][OH:6])[NH2:7].O[C:8](=[O:9])[C@@H:10]([CH2:11][C:12](=[O:13])[N:14]1[CH2:15][CH2:16][O:17][CH2:18][CH2:19]1)[c:20]1[cH:21][cH:22][c:23]([F:24])[cH:25][cH:26]1>>[CH3:1][CH:2]([CH3:3])[C@@H:4]([CH2:5][OH:6])[NH:7][C:8](=[O:9])[C@@H:10]([CH2:11][C:12](=[O:13])[N:14]1[CH2:15][CH2:16][... | CC(C)[C@H](N)CO.O=C(O)[C@@H](CC(=O)N1CCOCC1)c1ccc(F)cc1 | CC(C)[C@@H](CO)NC(=O)[C@@H](CC(=O)N1CCOCC1)c1ccc(F)cc1 | null | null | CCCCCC.C(Cl)Cl.CCOC(=O)C | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(CCc1ccccc1)N1CCOCC1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[c:4])-[C:5]-[C:6](-[#7:7])=[O;D1;H0:8].[C:9]-[C:10](-[C:11])-[NH2;D1;+0:12]>>[#7:7]-[C:6](=[O;D1;H0:8])-[C:5]-[C:3](-[c:4])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:12]-[C:10](-[C:9])-[C:11] | 41 | [{"value": 41.0, "product": "FC1=CC=C(C=C1)[C@@H](C(=O)N[C@@H](C(C)C)CO)CC(=O)N1CCOCC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 40.6, "product": "FC1=CC=C(C=C1)[C@@H](C(=O)N[C@@H](C(C)C)CO)CC(=O)N1CCOCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 2-(S)-(4-Fluoro-phenyl)-4-morpholin-4-yl-4-oxo-butyric acid (2.00 g, 7.11 mmol, 1.0 eq.), 2-(S)-Amino-3-methyl-butan-1-ol (1.59 g, 7.33 mmol, 1.03 eq.) and HATU (2.41 g, 7.33 mmol, 1.03 mmol) were dissolved in CH2Cl2 and stirred at room temperature. Diisopropylethylamine (3.9 mL, 21.98 mmol, 3.1 eq.) was added via syri... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | C1COCC[NH]1.c1ccccc1 | HO- | CCCCCC.C(Cl)Cl.CCOC(=O)C | null | null | CC(C)[C@H](N)CO.O=C(O)[C@@H](CC(=O)N1CCOCC1)c1ccc(F)cc1>CCCCCC.C(Cl)Cl.CCOC(=O)C>CC(C)[C@@H](CO)NC(=O)[C@@H](CC(=O)N1CCOCC1)c1ccc(F)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ed10a5a388014fa48116a42541cc0bf6 | CC(C)[C@@H](CO)NC(=O)[C@@H](CC(=O)N1CCOCC1)c1ccc(F)cc1>>CC(C)[C@@H](C=O)NC(=O)[C@@H](CC(=O)N1CCOCC1)c1ccc(F)cc1 | FC1=CC=C(C=C1)[C@@H](C(=O)N[C@@H](C(C)C)CO)CC(=O)N1CCOCC1.CC(=O)OI1(C=2C=CC=CC2C(=O)O1)(OC(=O)C)OC(=O)C>>FC1=CC=C(C=C1)[C@@H](C(=O)N[C@@H](C(C)C)C=O)CC(=O)N1CCOCC1 | [CH3:1][CH:2]([CH3:3])[C@@H:4]([CH2:5][OH:6])[NH:7][C:8](=[O:9])[C@@H:10]([CH2:11][C:12](=[O:13])[N:14]1[CH2:15][CH2:16][O:17][CH2:18][CH2:19]1)[c:20]1[cH:21][cH:22][c:23]([F:24])[cH:25][cH:26]1>>[CH3:1][CH:2]([CH3:3])[C@@H:4]([CH:5]=[O:6])[NH:7][C:8](=[O:9])[C@@H:10]([CH2:11][C:12](=[O:13])[N:14]1[CH2:15][CH2:16][O:17... | CC(C)[C@@H](CO)NC(=O)[C@@H](CC(=O)N1CCOCC1)c1ccc(F)cc1 | CC(C)[C@@H](C=O)NC(=O)[C@@H](CC(=O)N1CCOCC1)c1ccc(F)cc1 | null | null | C(Cl)Cl.CCOC(=O)C | Oxidation | Oxidation or Dehydrogenation of Alcohols to Aldehydes and Ketones | 41bfa9deea81b465c88ad21fdfb64a2e1ba29490558cf430df132cb98b4a538b | 0a03c6724c1862e8f86d4a463afda55b8e067dc6cb42597b472eb7cabc03eda3 | O=C(CCc1ccccc1)N1CCOCC1 | [C:1]-[C:2](-[#7:3]-[C:4]=[O;D1;H0:5])-[CH2;D2;+0:6]-[OH;D1;+0:7]>>[C:1]-[C:2](-[#7:3]-[C:4]=[O;D1;H0:5])-[CH;D2;+0:6]=[O;H0;D1;+0:7] | 62 | [{"value": 62.0, "product": "FC1=CC=C(C=C1)[C@@H](C(=O)N[C@@H](C(C)C)C=O)CC(=O)N1CCOCC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 61.7, "product": "FC1=CC=C(C=C1)[C@@H](C(=O)N[C@@H](C(C)C)C=O)CC(=O)N1CCOCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 2-(S)-(4-Fluoro-phenyl)-N-(1-(S)-hydroxymethyl-2-methyl-propyl)-4-morpholin-4-yl-4-oxo-butyramide (2.31 g, 6.30 mmol, 1.0 eq.) was dissolved in CH2Cl2 (32 mL) and stirred at room temperature. Dess-Martin Periodinane (2.67 g, 6.30 mmol, 1.0 eq.) was added in one portion and the reaction is monitored by LC/MS and TLC. Up... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | Aldehyde | null | null | C1COCC[NH]1.c1ccccc1 | null | C(Cl)Cl.CCOC(=O)C | null | null | CC(C)[C@@H](CO)NC(=O)[C@@H](CC(=O)N1CCOCC1)c1ccc(F)cc1>C(Cl)Cl.CCOC(=O)C>CC(C)[C@@H](C=O)NC(=O)[C@@H](CC(=O)N1CCOCC1)c1ccc(F)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-950430614803451d89e67ca6730e7c21 | CC(C)[C@@H](C=O)NC(=O)[C@@H](CC(=O)N1CCOCC1)c1ccc(F)cc1.COc1ccc(N)cn1>>COc1ccc(NC[C@@H](NC(=O)[C@@H](CC(=O)N2CCOCC2)c2ccc(F)cc2)C(C)C)cn1 | C(#N)[BH3-].[Na+].FC1=CC=C(C=C1)[C@@H](C(=O)N[C@@H](C(C)C)C=O)CC(=O)N1CCOCC1.NC=1C=CC(=NC1)OC.C(C)(=O)O>>FC1=CC=C(C=C1)[C@@H](C(=O)N[C@@H](C(C)C)CNC=1C=NC(=CC1)OC)CC(=O)N1CCOCC1 | O=[CH:8][C@@H:9]([NH:10][C:11](=[O:12])[C@@H:13]([CH2:14][C:15](=[O:16])[N:17]1[CH2:18][CH2:19][O:20][CH2:21][CH2:22]1)[c:23]1[cH:24][cH:25][c:26]([F:27])[cH:28][cH:29]1)[CH:30]([CH3:31])[CH3:32].[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([NH2:7])[cH:33][n:34]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([NH:7][CH2:8][C@@H:9]([NH:10... | CC(C)[C@@H](C=O)NC(=O)[C@@H](CC(=O)N1CCOCC1)c1ccc(F)cc1.COc1ccc(N)cn1 | COc1ccc(NC[C@@H](NC(=O)[C@@H](CC(=O)N2CCOCC2)c2ccc(F)cc2)C(C)C)cn1 | null | null | CO | Heteroatom Alkylation and Arylation | Reductive amination with aldehyde | 422be648aea52bce28ccc8fb32ec3178aaa47bbd624f063874619362f075b5f2 | 7915721a3e395aed85e3c40dc4d725c571a931ac517c6a0da16f2a2b0bb5eac7 | O=C(NCCNc1cccnc1)[C@@H](CC(=O)N1CCOCC1)c1ccccc1 | O=[CH;D2;+0:1]-[C:2](-[C:3])-[#7:4]-[C:5]=[O;D1;H0:6].[NH2;D1;+0:7]-[c:8](:[c:9]):[c:10]:[#7;a:11]:[c:12]>>[C:3]-[C:2](-[#7:4]-[C:5]=[O;D1;H0:6])-[CH2;D2;+0:1]-[NH;D2;+0:7]-[c:8](:[c:9]):[c:10]:[#7;a:11]:[c:12] | null | [] | null | null | null | null | 2-(S)-(4-Fluoro-phenyl)-N-(1-(S)-formyl-2-methyl-propyl)-4-morpholin-4-yl-4-oxo-butyramide (350 mg, 0.96 mmol, 1.0 eq.) and 5-Amino-2-methoxy-pyridine (240 μL, 1.92 mmol, 2.0 eq.) dissolved in MeOH (2.5 mL) and acetic acid (106 mL, 1.92 mmol, 2.0 eq.) added via syringe at room temperature. Sodium cyanoborohydride (121 ... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Primary amine | Secondary amine | null | null | c1ccncc1.C1COCC[NH]1.c1ccccc1 | Other | CO | null | null | CC(C)[C@@H](C=O)NC(=O)[C@@H](CC(=O)N1CCOCC1)c1ccc(F)cc1.COc1ccc(N)cn1>CO>COc1ccc(NC[C@@H](NC(=O)[C@@H](CC(=O)N2CCOCC2)c2ccc(F)cc2)C(C)C)cn1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-bd9245b2f7094d11a58f50b566c68df3 | C=C1CCC(C(=O)OCC)CC1>>C=C1CCC(CO)CC1 | C(C)OC(=O)C1CCC(CC1)=C.[H-].[H-].[H-].[H-].[Li+].[Al+3]>>C=C1CCC(CC1)CO | CCO[C:6]([CH:5]1[CH2:4][CH2:3][C:2](=[CH2:1])[CH2:9][CH2:8]1)=[O:7]>>[CH2:1]=[C:2]1[CH2:3][CH2:4][CH:5]([CH2:6][OH:7])[CH2:8][CH2:9]1 | C=C1CCC(C(=O)OCC)CC1 | C=C1CCC(CO)CC1 | null | null | null | Reduction | Reduction of ester to primary alcohol | 21d61543c6ec8a8cebe1b3ef55ef3dd20acbf79a4f1c12a7fb51e32be7a3248a | 1fbcd628a0426673c5d10aa49a977cd2d1ae02a8cdf57bbb10d94aa03a94e937 | C=C1CCCCC1 | C-C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[C:3](-[C:4])-[C:5]>>[C:4]-[C:3](-[CH2;D2;+0:1]-[OH;D1;+0:2])-[C:5] | null | [] | null | null | null | null | The reduction reaction of 4-methylene-cyclohexanecarboxylic acid ethyl ester with LAH is as described in the above reference. The product was purified by distillation to provide (4-methylene-cyclohexyl)-methanol as clear oil (3.67 g, 29.09 mmol, 50% over Step A and B).
Conditions: See reaction.notes.procedure_details.
... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary alcohol | null | null | C1CCCCC1 | HO- | null | null | null | C=C1CCC(C(=O)OCC)CC1>>C=C1CCC(CO)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-98383634377349609046a0d1ae6cb608 | OCC1CCC2(CC1)CC2>>O=CC1CCC2(CC1)CC2 | C1CC12CCC(CC2)CO.[Cr](=O)(=O)([O-])O[Cr](=O)(=O)[O-].[NH+]1=CC=CC=C1.[NH+]1=CC=CC=C1>>C1CC12CCC(CC2)C=O | [OH:1][CH2:2][CH:3]1[CH2:4][CH2:5][C:6]2([CH2:7][CH2:8]1)[CH2:9][CH2:10]2>>[O:1]=[CH:2][CH:3]1[CH2:4][CH2:5][C:6]2([CH2:7][CH2:8]1)[CH2:9][CH2:10]2 | OCC1CCC2(CC1)CC2 | O=CC1CCC2(CC1)CC2 | null | null | C(Cl)Cl | Oxidation | Oxidation or Dehydrogenation of Alcohols to Aldehydes and Ketones | 41bfa9deea81b465c88ad21fdfb64a2e1ba29490558cf430df132cb98b4a538b | 0a03c6724c1862e8f86d4a463afda55b8e067dc6cb42597b472eb7cabc03eda3 | C1CCC2(CC1)CC2 | [C:1]-[C:2](-[CH2;D2;+0:3]-[OH;D1;+0:4])-[C:5]>>[C:1]-[C:2](-[CH;D2;+0:3]=[O;H0;D1;+0:4])-[C:5] | null | [] | null | null | null | null | Spiro[2.5]oct-6-yl-methanol (2.57 g, 18.3 mmol, 1.0 eq.) was dissolved in CH2Cl2 (30 mL) and placed in a ice-water bath at 0° C. Pyridinium dichromate (PCC) (7.9 g, 36.6 mmol, 2.0 eq.) was added and the reaction warmed to room temperature for 4 hours with stirring. The crude reaction was filtered through a Celite pad a... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | Aldehyde | null | null | C1CCC2(CC1)CC2 | null | C(Cl)Cl | null | null | OCC1CCC2(CC1)CC2>C(Cl)Cl>O=CC1CCC2(CC1)CC2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-da02151b449d42cbbe103aa172662fa2 | COC(=O)[C@@H](O)CSCc1ccccc1>>O=C(O)[C@@H](O)CSCc1ccccc1 | COC([C@H](CSCC1=CC=CC=C1)O)=O.[OH-].[Li+]>>C(C1=CC=CC=C1)SC[C@@H](C(=O)O)O | C[O:3][C:2](=[O:1])[C@@H:4]([OH:5])[CH2:6][S:7][CH2:8][c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1>>[O:1]=[C:2]([OH:3])[C@@H:4]([OH:5])[CH2:6][S:7][CH2:8][c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1 | COC(=O)[C@@H](O)CSCc1ccccc1 | O=C(O)[C@@H](O)CSCc1ccccc1 | null | null | null | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccccc1 | C-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4]>>[C:3]-[C:2](=[O;D1;H0:4])-[OH;D1;+0:1] | 46 | [{"value": 46.0, "product": "C(C1=CC=CC=C1)SC[C@@H](C(=O)O)O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | This reaction was performed as previously described by Deechongkit, S.; You, S.-L.; Kelly, J. W. Org. Lett. 2004, 6, 497, using (R)-3-Benzylsulfanyl-2-hydroxy-propionic acid methyl ester 110b and lithium hydroxide. (R)-3-Benzylsulfanyl-2-hydroxy-propionic acid 110c (3.08 g, 14.51 mmol, 46%) was isolated as a viscous oi... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1 | Other | null | null | null | COC(=O)[C@@H](O)CSCc1ccccc1>>O=C(O)[C@@H](O)CSCc1ccccc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-7d4f59b686e344d1bf374226933acbae | CCOC(C)=O.COc1ccc2c(c1)CCC(c1ccccc1)=C2C(O)c1ccc(OCCN2CCCC2)cc1>>COc1ccc2c(Cc3ccc(OCCN4CCCCC4)cc3)c(-c3ccccc3)ccc2c1 | C1(=CC=CC=C1)C1=C(C2=CC=C(C=C2CC1)OC)C(O)C1=CC=C(C=C1)OCCN1CCCC1.C(C)(=O)OCC.Cl.C(C)(=O)OCC>>Cl.C1(=CC=CC=C1)C1=C(C2=CC=C(C=C2C=C1)OC)CC1=CC=C(C=C1)OCCN1CCCCC1 | CC(=O)OC[CH3:19].O[CH:8]([C:7]1=[C:24]([c:25]2[cH:26][cH:27][cH:28][cH:29][cH:30]2)[CH2:31][CH2:32][c:33]2[c:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:34]2)[c:9]1[cH:10][cH:11][c:12]([O:13][CH2:14][CH2:15][N:16]2[CH2:17][CH2:18][CH2:20][CH2:21]2)[cH:22][cH:23]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([CH2:8][c:9]3[cH:10... | CCOC(C)=O.COc1ccc2c(c1)CCC(c1ccccc1)=C2C(O)c1ccc(OCCN2CCCC2)cc1 | COc1ccc2c(Cc3ccc(OCCN4CCCCC4)cc3)c(-c3ccccc3)ccc2c1 | null | null | null | C-C Coupling | OtherReaction | 2957d45d0c4fb28629395caf7bb4bede51ca9d5a4978360cfacccd6f227c82b4 | 85dc278ba9c307395886aa35ef1fcafb5013915b72e73ef6ca23953dd492bbfb | c1ccc(-c2ccc3ccccc3c2Cc2ccc(OCCN3CCCCC3)cc2)cc1 | C-C(=O)-O-C-[CH3;D1;+0:1].O-[CH;D3;+0:2](-[C;H0;D3;+0:3]1=[C;H0;D3;+0:4](-[c;H0;D3;+0:5](:[c:6]:[c:7]):[c:8]:[c:9])-[CH2;D2;+0:10]-[CH2;D2;+0:11]-[c:12](:[c:13]):[c:14]-1:[c:15])-[c:16](:[c:17]):[c:18].[C:19]-[#7:20]1-[C:21]-[CH2;D2;+0:22]-[CH2;D2;+0:23]-[C:24]-1>>[C:19]-[#7:20]1-[C:21]-[CH2;D2;+0:22]-[CH2;D2;+0:1]-[CH... | 89 | [{"value": 89.0, "product": "Cl.C1(=CC=CC=C1)C1=C(C2=CC=C(C=C2C=C1)OC)CC1=CC=C(C=C1)OCCN1CCCCC1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 0.5 | MINUTE | To a solution of the product of Example 7 (8.7 g, 18.5 mmol) stirring in ethyl acetate (100 mL) was added a saturated solution of hydrochloric acid gas in ethyl acetate (250 mL). After 0.5 min, the resulting solution was concentrated to give 8.0 g (89%) of the desired product as a white foam which was used without furt... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Secondary alcohol | null | C1=Cc2ccccc2CC1.C1CC[NH]C1 | C1CC[NH]CC1.c1ccc2ccccc2c1 | c1ccccc1.C1CC[NH]CC1.c1ccccc1.c1ccc2ccccc2c1 | HO- | null | null | 0.008333 | CCOC(C)=O.COc1ccc2c(c1)CCC(c1ccccc1)=C2C(O)c1ccc(OCCN2CCCC2)cc1>>COc1ccc2c(Cc3ccc(OCCN4CCCCC4)cc3)c(-c3ccccc3)ccc2c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e8449c6acb0f4a579849e68b76896835 | COc1ccc2c(Cc3ccc(OCCN4CCCCC4)cc3)c(-c3ccccc3)ccc2c1>>Oc1ccc2c(Cc3ccc(OCCN4CCCCC4)cc3)c(-c3ccccc3)ccc2c1 | Cl.C1(=CC=CC=C1)C1=C(C2=CC=C(C=C2C=C1)OC)CC1=CC=C(C=C1)OCCN1CCCCC1.B(Cl)(Cl)Cl.CO>>C1(=CC=CC=C1)C1=C(C2=CC=C(C=C2C=C1)O)CC1=CC=C(C=C1)OCCN1CCCCC1 | C[O:1][c:2]1[cH:3][cH:4][c:5]2[c:6]([CH2:7][c:8]3[cH:9][cH:10][c:11]([O:12][CH2:13][CH2:14][N:15]4[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20]4)[cH:21][cH:22]3)[c:23](-[c:24]3[cH:25][cH:26][cH:27][cH:28][cH:29]3)[cH:30][cH:31][c:32]2[cH:33]1>>[OH:1][c:2]1[cH:3][cH:4][c:5]2[c:6]([CH2:7][c:8]3[cH:9][cH:10][c:11]([O:12][CH2:1... | COc1ccc2c(Cc3ccc(OCCN4CCCCC4)cc3)c(-c3ccccc3)ccc2c1 | Oc1ccc2c(Cc3ccc(OCCN4CCCCC4)cc3)c(-c3ccccc3)ccc2c1 | null | null | ClCCCl | Deprotection | Cleavage of methoxy ethers to alcohols | c5320c7dfa4f544d4900efcae9b3262bf0d5286bcf39c86109232351f35b23d5 | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | c1ccc(-c2ccc3ccccc3c2Cc2ccc(OCCN3CCCCC3)cc2)cc1 | C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[OH;D1;+0:1]-[c:2](:[c:3]):[c:4] | 77.1 | [{"value": 63.0, "product": "C1(=CC=CC=C1)C1=C(C2=CC=C(C=C2C=C1)O)CC1=CC=C(C=C1)OCCN1CCCCC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 77.1, "product": "C1(=CC=CC=C1)C1=C(C2=CC=C(C=C2C=C1)O)CC1=CC=C(C=C1)OCCN1CCCCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | To a solution of the product of Example 9 (4.0 g, 8.0 mmol) stirring in 1,2-dichloroethane (50 mL) at 0° C. was added boron trichloride (10 mL, 117.0 mmol). The resulting dark purple solution was stirred at room temperature overnight in a sealed tube then cooled to 0° C. Methanol (50 mL) was carefully added dropwise ov... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | null | null | c1ccccc1.C1CC[NH]CC1.c1ccccc1.c1ccc2ccccc2c1 | Other | ClCCCl | null | 8 | COc1ccc2c(Cc3ccc(OCCN4CCCCC4)cc3)c(-c3ccccc3)ccc2c1>ClCCCl>Oc1ccc2c(Cc3ccc(OCCN4CCCCC4)cc3)c(-c3ccccc3)ccc2c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ad44e7ac7b774522b622396f93e5e114 | COc1ccc(C2=C(C(O)c3ccc(OCCN4CCCC4)cc3)c3ccccc3CC2)cc1>>COc1ccc(-c2ccc3ccccc3c2Cc2ccc(OCCN3CCCC3)cc2)cc1 | COC1=CC=C(C=C1)C1=C(C2=CC=CC=C2CC1)C(O)C1=CC=C(C=C1)OCCN1CCCC1.Cl>>Cl.COC1=CC=C(C=C1)C1=C(C2=CC=CC=C2C=C1)CC1=CC=C(C=C1)OCCN1CCCC1 | O[CH:17]([C:16]1=[C:7]([c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:33][cH:32]2)[CH2:8][CH2:9][c:10]2[cH:11][cH:12][cH:13][cH:14][c:15]21)[c:18]1[cH:19][cH:20][c:21]([O:22][CH2:23][CH2:24][N:25]2[CH2:26][CH2:27][CH2:28][CH2:29]2)[cH:30][cH:31]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][cH:9][c:10]3[cH:11][cH:12][c... | COc1ccc(C2=C(C(O)c3ccc(OCCN4CCCC4)cc3)c3ccccc3CC2)cc1 | COc1ccc(-c2ccc3ccccc3c2Cc2ccc(OCCN3CCCC3)cc2)cc1 | null | null | CO | Reduction | OtherReaction | 993798e8877653e2916ebad5ce02cd2f327385a2c7261328e2a315c7a52a0875 | 46f8a11b80b06e754a5a34198d843342612a5e7ede950bda52ce3a500cedba0b | c1ccc(-c2ccc3ccccc3c2Cc2ccc(OCCN3CCCC3)cc2)cc1 | O-[CH;D3;+0:1](-[C;H0;D3;+0:2]1=[C;H0;D3;+0:3](-[c;H0;D3;+0:4](:[c:5]:[c:6]):[c:7]:[c:8])-[CH2;D2;+0:9]-[CH2;D2;+0:10]-[c:11](:[c:12]):[c:13]-1:[c:14])-[c:15](:[c:16]):[c:17]>>[c:12]:[c:11]1:[cH;D2;+0:10]:[cH;D2;+0:9]:[c;H0;D3;+0:3](-[c;H0;D3;+0:4](:[c:5]:[c:6]):[c:7]:[c:8]):[c;H0;D3;+0:2](-[CH2;D2;+0:1]-[c:15](:[c:16]... | null | [] | -20 | CELSIUS | null | null | To a solution of the product of Example 14 (2.0 g, 4.58 mmol) stirring in methanol (50 mL) at ambient temperature was added methanolic hydrochloric acid (10 mL of a saturated solution). The reaction mixture was then concentrated to 20 mL and cooled to −20° C. for several hours. Filtration gave 0.62 g of the desired pro... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol | null | C1=Cc2ccccc2CC1 | c1ccc2ccccc2c1 | c1ccccc1.c1ccc2ccccc2c1.c1ccccc1.C1CC[NH]C1 | HO- | CO | -20 | null | COc1ccc(C2=C(C(O)c3ccc(OCCN4CCCC4)cc3)c3ccccc3CC2)cc1>CO>COc1ccc(-c2ccc3ccccc3c2Cc2ccc(OCCN3CCCC3)cc2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-9b1d83f0de6c4b3fabb8088122a431b3 | COc1ccc(-c2ccc3cc(OC)ccc3c2-c2cc(OCCN3CCCC3)ccc2C)cc1>>Cc1ccc(OCCN2CCCC2)cc1-c1c(-c2ccc(O)cc2)ccc2cc(O)ccc12 | Cl.COC1=CC=C(C=C1)C1=C(C2=CC=C(C=C2C=C1)OC)C1=C(C=CC(=C1)OCCN1CCCC1)C.B(Cl)(Cl)Cl.CO>>OC1=CC=C(C=C1)C1=C(C2=CC=C(C=C2C=C1)O)C1=C(C=CC(=C1)OCCN1CCCC1)C | C[O:22][c:21]1[cH:20][cH:19][c:18](-[c:17]2[c:16](-[c:15]3[c:2]([CH3:1])[cH:3][cH:4][c:5]([O:6][CH2:7][CH2:8][N:9]4[CH2:10][CH2:11][CH2:12][CH2:13]4)[cH:14]3)[c:33]3[c:27]([cH:26][cH:25]2)[cH:28][c:29]([O:30]C)[cH:31][cH:32]3)[cH:24][cH:23]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([O:6][CH2:7][CH2:8][N:9]2[CH2:10][CH2:11][CH2:... | COc1ccc(-c2ccc3cc(OC)ccc3c2-c2cc(OCCN3CCCC3)ccc2C)cc1 | Cc1ccc(OCCN2CCCC2)cc1-c1c(-c2ccc(O)cc2)ccc2cc(O)ccc12 | null | null | ClCCCl | Deprotection | OtherReaction | a0f05885bbc65ae2846cad0ac34029941211b2ef3a426958b0c8aa83bb16fe86 | 9df751cd682ad9d54ed75d7313aaead6a019c5d37ede15c4672866d319b900ff | c1ccc(-c2ccc3ccccc3c2-c2cccc(OCCN3CCCC3)c2)cc1 | C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4].C-[O;H0;D2;+0:5]-[c:6](:[c:7]):[c:8]>>[OH;D1;+0:1]-[c:2](:[c:3]):[c:4].[OH;D1;+0:5]-[c:6](:[c:7]):[c:8] | 29.8 | [{"value": 27.0, "product": "OC1=CC=C(C=C1)C1=C(C2=CC=C(C=C2C=C1)O)C1=C(C=CC(=C1)OCCN1CCCC1)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 29.8, "product": "OC1=CC=C(C=C1)C1=C(C2=CC=C(C=C2C=C1)O)C1=C(C=CC(=C1)OCCN1CCCC1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | To a solution of the product of Example 18 (1.61 g, 2.60 mmol) in 1.2-dichloroethane (30 mL) stirring at 0° C. was added boron trichloride (10 ml, 117 mmol). The resulting dark purple solution was stirred overnight at ambient temperature in a sealed tube. After cooling the solution to 0° C., methanol (25 mL) was carefu... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether | Aromatic alcohol.Aromatic alcohol | null | null | c1ccccc1.C1CC[NH]C1.c1ccccc1.c1ccc2ccccc2c1 | Other | ClCCCl | null | 8 | COc1ccc(-c2ccc3cc(OC)ccc3c2-c2cc(OCCN3CCCC3)ccc2C)cc1>ClCCCl>Cc1ccc(OCCN2CCCC2)cc1-c1c(-c2ccc(O)cc2)ccc2cc(O)ccc12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-dc057ad441ce406a8baaa2d771d26321 | COc1ccc(C2=C(C(O)c3ccc(OCCCN4CCCCC4)cc3)c3ccc(OC)cc3CC2)cc1>>COc1ccc(-c2ccc3cc(OC)ccc3c2Cc2ccc(OCCCN3CCCCC3)cc2)cc1 | COC1=CC=C(C=C1)C1=C(C2=CC=C(C=C2CC1)OC)C(O)C1=CC=C(C=C1)OCCCN1CCCCC1.Cl>>Cl.COC1=CC=C(C=C1)C1=C(C2=CC=C(C=C2C=C1)OC)CC1=CC=C(C=C1)OCCCN1CCCCC1 | O[CH:19]([C:18]1=[C:7]([c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:37][cH:36]2)[CH2:8][CH2:9][c:10]2[cH:11][c:12]([O:13][CH3:14])[cH:15][cH:16][c:17]21)[c:20]1[cH:21][cH:22][c:23]([O:24][CH2:25][CH2:26][CH2:27][N:28]2[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33]2)[cH:34][cH:35]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:... | COc1ccc(C2=C(C(O)c3ccc(OCCCN4CCCCC4)cc3)c3ccc(OC)cc3CC2)cc1 | COc1ccc(-c2ccc3cc(OC)ccc3c2Cc2ccc(OCCCN3CCCCC3)cc2)cc1 | null | null | C(C)(=O)OCC | Reduction | OtherReaction | 993798e8877653e2916ebad5ce02cd2f327385a2c7261328e2a315c7a52a0875 | 46f8a11b80b06e754a5a34198d843342612a5e7ede950bda52ce3a500cedba0b | c1ccc(-c2ccc3ccccc3c2Cc2ccc(OCCCN3CCCCC3)cc2)cc1 | O-[CH;D3;+0:1](-[C;H0;D3;+0:2]1=[C;H0;D3;+0:3](-[c;H0;D3;+0:4](:[c:5]:[c:6]):[c:7]:[c:8])-[CH2;D2;+0:9]-[CH2;D2;+0:10]-[c:11](:[c:12]):[c:13]-1:[c:14])-[c:15](:[c:16]):[c:17]>>[c:12]:[c:11]1:[cH;D2;+0:10]:[cH;D2;+0:9]:[c;H0;D3;+0:3](-[c;H0;D3;+0:4](:[c:5]:[c:6]):[c:7]:[c:8]):[c;H0;D3;+0:2](-[CH2;D2;+0:1]-[c:15](:[c:16]... | 97 | [{"value": 97.0, "product": "Cl.COC1=CC=C(C=C1)C1=C(C2=CC=C(C=C2C=C1)OC)CC1=CC=C(C=C1)OCCCN1CCCCC1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Reaction of the product of Example 21 (1.5 g, 2.9 mmol) with hydrochloric acid (50 mL of a saturated ethyl acetate solution) in ethyl acetate (50 mL) according to the procedure in Example 18 gave a 97% yield of the desired product: 1H-NMR (300 MHz, CDCl3) δ 7.70-7.80 (m, 2H), 7.42 (d, J=8.4 Hz, 1H), 7.15-7.30 (m, 3H), ... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol | null | C1=Cc2ccccc2CC1 | c1ccc2ccccc2c1 | c1ccccc1.c1ccc2ccccc2c1.c1ccccc1.C1CC[NH]CC1 | HO- | C(C)(=O)OCC | null | null | COc1ccc(C2=C(C(O)c3ccc(OCCCN4CCCCC4)cc3)c3ccc(OC)cc3CC2)cc1>C(C)(=O)OCC>COc1ccc(-c2ccc3cc(OC)ccc3c2Cc2ccc(OCCCN3CCCCC3)cc2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-9ef2e52800084124aa06cb2024b3092f | CC(=O)c1ccccn1.COC(=O)C(=O)[O-]>>COC(=O)C(O)=CC(=O)c1cccnc1 | Cl.C(C)(=O)C1=NC=CC=C1.C(C(=O)[O-])(=O)OC.CO.C[O-].[Na+]>>COC(C(=CC(C=1C=NC=CC1)=O)O)=O | [CH3:7][C:8](=[O:9])[c:10]1[cH:11][cH:12][cH:13][cH:15][n:14]1.[O-][C:5]([C:3]([O:2][CH3:1])=[O:4])=[O:6]>>[CH3:1][O:2][C:3](=[O:4])[C:5]([OH:6])=[CH:7][C:8](=[O:9])[c:10]1[cH:11][cH:12][cH:13][n:14][cH:15]1 | CC(=O)c1ccccn1.COC(=O)C(=O)[O-] | COC(=O)C(O)=CC(=O)c1cccnc1 | null | null | null | C-C Coupling | OtherReaction | 41ecb874d1a6123b790c013cc0681b994f2c9ce6c828e5f6f24a6cd098ee46cf | 4c8da19c226c76fb5f286d8c34536e387adc6ed030260abb13908c23f0221ea1 | c1ccncc1 | [C;D1;H3:1]-[#8:2]-[C:3](=[O;D1;H0:4])-[C;H0;D3;+0:5](-[O-])=[O;H0;D1;+0:6].[CH3;D1;+0:7]-[C:8](=[O;D1;H0:9])-[c;H0;D3;+0:10]1:[c:11]:[c:12]:[cH;D2;+0:13]:[cH;D2;+0:14]:[n;H0;D2;+0:15]:1>>[C;D1;H3:1]-[#8:2]-[C:3](=[O;D1;H0:4])-[C;H0;D3;+0:5](-[OH;D1;+0:6])=[CH;D2;+0:7]-[C:8](=[O;D1;H0:9])-[c;H0;D3;+0:10]1:[c:11]:[c:12]... | null | [] | null | null | 15 | MINUTE | Acetyl pyridine (1.81 mL, 16.5 mmol) and methyl oxalate (3.12 g, 26.4 mmol) were dissolved in MeOH (30 mL, anhydrous). Sodium methoxide (6.9 mL, 25% in MeOH) was added over 10 min. Reaction solidified and was complete after 15 minutes. The solid mass was dissolved when acidified with HCl (10%, aqueous). The pH was then... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ester | Ketone.Ester.Enol | c1ccncc1 | c1ccncc1 | c1ccncc1 | HO- | null | null | 0.25 | CC(=O)c1ccccn1.COC(=O)C(=O)[O-]>>COC(=O)C(O)=CC(=O)c1cccnc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-f5aed28b2a534cc69f7da8f20e43ea6a | COC(=O)C(O)=CC(=O)c1cccnc1.NNc1ccc(Cl)c(Cl)c1>>COC(=O)c1cc(-c2cccnc2)n(-c2ccc(Cl)c(Cl)c2)n1 | COC(C(=CC(C=1C=NC=CC1)=O)O)=O.Cl.ClC=1C=C(C=CC1Cl)NN>>Cl.COC(=O)C1=NN(C(=C1)C=1C=NC=CC1)C1=CC(=C(C=C1)Cl)Cl | O=[C:7]([CH:6]=[C:5](O)[C:3]([O:2][CH3:1])=[O:4])[c:8]1[cH:9][cH:10][cH:11][n:12][cH:13]1.[NH:14]([c:15]1[cH:16][cH:17][c:18]([Cl:19])[c:20]([Cl:21])[cH:22]1)[NH2:23]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7](-[c:8]2[cH:9][cH:10][cH:11][n:12][cH:13]2)[n:14](-[c:15]2[cH:16][cH:17][c:18]([Cl:19])[c:20]([Cl:21])[cH:22]2... | COC(=O)C(O)=CC(=O)c1cccnc1.NNc1ccc(Cl)c(Cl)c1 | COC(=O)c1cc(-c2cccnc2)n(-c2ccc(Cl)c(Cl)c2)n1 | null | null | CCO | Aromatic Heterocycle Formation | OtherReaction | 33fc2e04255bbdd64fba97753a6f26842e3fecdd69cce27401cb60480f0a7288 | bd726ca0015f6098456e848ff1ee644dfe9256f0c8347a12b063c9b5b821ebd7 | c1ccc(-n2nccc2-c2cccnc2)cc1 | O-[C;H0;D3;+0:1](=[CH;D2;+0:2]-[C;H0;D3;+0:3](=O)-[c;H0;D3;+0:4]1:[c:5]:[#7;a:6]:[c:7]:[c:8]:[c:9]:1)-[C:10](=[O;D1;H0:11])-[#8:12]-[C;D1;H3:13].[NH2;D1;+0:14]-[NH;D2;+0:15]-[c;H0;D3;+0:16](:[c:17]:[c:18]):[c:19]:[c:20]>>[C;D1;H3:13]-[#8:12]-[C:10](=[O;D1;H0:11])-[c;H0;D3;+0:1]1:[cH;D2;+0:2]:[c;H0;D3;+0:3](-[c;H0;D3;+0... | 128 | [{"value": 70.0, "product": "Cl.COC(=O)C1=NN(C(=C1)C=1C=NC=CC1)C1=CC(=C(C=C1)Cl)Cl", "details": "PERCENTYIELD", "is_desired": false}, {"value": 128.0, "product": "Cl.COC(=O)C1=NN(C(=C1)C=1C=NC=CC1)C1=CC(=C(C=C1)Cl)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | null | null | To a solution of 1 (2.90 g, 14.0 mmol) in EtOH (60 mL, anhydrous) was added 3,4-dichlorophenyl hydrazine hydrochloride (3.29 g, 15.4 mmol). The solution was heated to reflux for 30 min and then cooled to 0° C. The precipitate was collected by filtration and washed with H2O and MeOH to yield 2 (3.79 g, 70%) as an off-wh... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Ketone.Ester.Enol | Ester | null | c1cc[nH]n1 | c1cc[nH]n1.c1ccncc1.c1ccccc1 | HO- | CCO | 0 | null | COC(=O)C(O)=CC(=O)c1cccnc1.NNc1ccc(Cl)c(Cl)c1>CCO>COC(=O)c1cc(-c2cccnc2)n(-c2ccc(Cl)c(Cl)c2)n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-2b78ff2d3f9b42b2824d22f2c0de4457 | COC(=O)c1cc(-c2cccnc2)n(-c2ccc(Cl)c(Cl)c2)n1.[N-]=[N+]=NP(=O)(c1ccccc1)c1ccccc1>>[N-]=[N+]=NC(=O)c1cc(-c2cccnc2)n(-c2ccc(Cl)c(Cl)c2)n1 | C(C)N(CC)CC.Cl.COC(=O)C1=NN(C(=C1)C=1C=NC=CC1)C1=CC(=C(C=C1)Cl)Cl.C(C)(C)(C)O.C1(=CC=CC=C1)P(=O)(C1=CC=CC=C1)N=[N+]=[N-]>>ClC=1C=C(C=CC1Cl)N1N=C(C=C1C=1C=NC=CC1)C(=O)N=[N+]=[N-] | CO[C:4](=[O:5])[c:6]1[cH:7][c:8](-[c:9]2[cH:10][cH:11][cH:12][n:13][cH:14]2)[n:15](-[c:16]2[cH:17][cH:18][c:19]([Cl:20])[c:21]([Cl:22])[cH:23]2)[n:24]1.O=P(c1ccccc1)(c1ccccc1)[N:3]=[N+:2]=[N-:1]>>[N-:1]=[N+:2]=[N:3][C:4](=[O:5])[c:6]1[cH:7][c:8](-[c:9]2[cH:10][cH:11][cH:12][n:13][cH:14]2)[n:15](-[c:16]2[cH:17][cH:18][c... | COC(=O)c1cc(-c2cccnc2)n(-c2ccc(Cl)c(Cl)c2)n1.[N-]=[N+]=NP(=O)(c1ccccc1)c1ccccc1 | [N-]=[N+]=NC(=O)c1cc(-c2cccnc2)n(-c2ccc(Cl)c(Cl)c2)n1 | null | null | CN(C)C=O | Acylation | OtherReaction | 7a7fbf95c42bedc701751c2ac46610ef4946f6e1aaab767c9db970462abf9de2 | da67ad6d8377f1cd9033aeb7148ee43a2ffc587f4fbff78d156d7a1ce69356d7 | c1ccc(-n2nccc2-c2cccnc2)cc1 | C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[#7;a:4]:[#7;a:5](-[c:6]):[c:7]:[c:8]:1.O=P(-[N;H0;D2;+0:9]=[#7;+:10]=[N;-;D1;H0:11])(-c1:c:c:c:c:c:1)-c1:c:c:c:c:c:1>>[N;-;D1;H0:11]=[#7;+:10]=[N;H0;D2;+0:9]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[#7;a:4]:[#7;a:5](-[c:6]):[c:7]:[c:8]:1 | null | [] | 0 | CELSIUS | 1 | HOUR | A solution of 3 (100 mg, 0.27 mmol) and t-butyl alcohol (28.4 μL, 0.30 mmol) in DMF (5 mL, anhydrous) was cooled to 0° C. Diphenylphosphoryl azide (64 μL, 0.30 mmol) was added to the solution. Triethylamine (103 μL, 0.60 mmol) was then added over 10 min. The solution was stirred 1 h at 0° C. and allowed to warm to room... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Azide | Azide | c1ccccc1.c1ccccc1 | null | c1cc[nH]n1.c1ccncc1.c1ccccc1 | HO- | CN(C)C=O | 0 | 1 | COC(=O)c1cc(-c2cccnc2)n(-c2ccc(Cl)c(Cl)c2)n1.[N-]=[N+]=NP(=O)(c1ccccc1)c1ccccc1>CN(C)C=O>[N-]=[N+]=NC(=O)c1cc(-c2cccnc2)n(-c2ccc(Cl)c(Cl)c2)n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a14940a24cf345248637d1b5745da86a | COC(=O)Cl.Nc1ccc(F)c([N+](=O)[O-])c1>>COC(=O)Nc1ccc(F)c([N+](=O)[O-])c1 | ClC(=O)OC.FC1=C(C=C(N)C=C1)[N+](=O)[O-].CCN(C(C)C)C(C)C>>COC(NC1=CC(=C(C=C1)F)[N+](=O)[O-])=O | Cl[C:3]([O:2][CH3:1])=[O:4].[NH2:5][c:6]1[cH:7][cH:8][c:9]([F:10])[c:11]([N+:12](=[O:13])[O-:14])[cH:15]1>>[CH3:1][O:2][C:3](=[O:4])[NH:5][c:6]1[cH:7][cH:8][c:9]([F:10])[c:11]([N+:12](=[O:13])[O-:14])[cH:15]1 | COC(=O)Cl.Nc1ccc(F)c([N+](=O)[O-])c1 | COC(=O)Nc1ccc(F)c([N+](=O)[O-])c1 | null | null | ClCCl | 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;D1;H3:4].[NH2;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[C;D1;H3:4]-[#8:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:5]-[c:6](:[c:7]):[c:8] | null | [] | null | null | 8 | HOUR | Methyl chloroformate (13.2 mL, 170.2 mmol) was added dropwise to a cold (0° C.) dichloromethane (200 mL) solution of 4-fluoro-3-nitro aniline (24.15 g, 154.7 mmol) and DIPEA (35 mL, 201 mmol). The reaction mixture was stirred at rt overnight. The solution was then diluted with 200 mL of dichloromethane and washed with ... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Ether.Primary amine | Carbamic ester | null | null | c1ccccc1 | HCl | ClCCl | null | 8 | COC(=O)Cl.Nc1ccc(F)c([N+](=O)[O-])c1>ClCCl>COC(=O)Nc1ccc(F)c([N+](=O)[O-])c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-b7cdc726aa8545ffacfb760efffc8f3b | COC(=O)Nc1ccc(F)c([N+](=O)[O-])c1.NCC1CCCCC1>>COC(=O)Nc1ccc(NCC2CCCCC2)c([N+](=O)[O-])c1 | COC(NC1=CC(=C(C=C1)F)[N+](=O)[O-])=O.C1(CCCCC1)CN>>COC(NC1=CC(=C(C=C1)NCC1CCCCC1)[N+](=O)[O-])=O | F[c:9]1[cH:8][cH:7][c:6]([NH:5][C:3]([O:2][CH3:1])=[O:4])[cH:22][c:18]1[N+:19](=[O:20])[O-:21].[NH2:10][CH2:11][CH:12]1[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]1>>[CH3:1][O:2][C:3](=[O:4])[NH:5][c:6]1[cH:7][cH:8][c:9]([NH:10][CH2:11][CH:12]2[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]2)[c:18]([N+:19](=[O:20])[O-:21])[cH:22]... | COC(=O)Nc1ccc(F)c([N+](=O)[O-])c1.NCC1CCCCC1 | COC(=O)Nc1ccc(NCC2CCCCC2)c([N+](=O)[O-])c1 | null | null | CCO | Heteroatom Alkylation and Arylation | Buchwald-Hartwig/Ullmann-Goldberg/N-arylation primary amine | da9dae6a655c4bd18887b692f91621e77027436294d6e1fc7be7295afb364796 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(NCC2CCCCC2)cc1 | F-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[#7;+:5]):[c:6].[C:7]-[C:8]-[NH2;D1;+0:9]>>[#7;+:5]-[c:4](:[c:6]):[c;H0;D3;+0:1](-[NH;D2;+0:9]-[C:8]-[C:7]):[c:2]:[c:3] | null | [] | null | null | null | null | Methyl(4-fluoro-3-nitrophenyl)carbamate (1.00 g, 4.67 mmol) and cyclohexylmethyl amine (0.730 mL, 5.60 mmol) were stirred in EtOH (20 mL) containing TEA (1.0 mL, 7.00 mmol) at 75° C. for 24 h. The solvent was concentrated. The residue was dissolved in EtOAc and washed with 5% KHSO4 aqueous solution, saturated NaHCO3 aq... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccccc1 | c1ccccc1 | c1ccccc1.C1CCCCC1 | HF | CCO | null | null | COC(=O)Nc1ccc(F)c([N+](=O)[O-])c1.NCC1CCCCC1>CCO>COC(=O)Nc1ccc(NCC2CCCCC2)c([N+](=O)[O-])c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e6bcad80cf7741f689703833b32c99fb | COC(=O)Nc1ccc(NCC2CCCCC2)c([N+](=O)[O-])c1>>COC(=O)Nc1ccc(NCC2CCCCC2)c(N)c1 | C1(CCCCC1)CNC1=C(C=C(C=C1)NC(OC)=O)[N+](=O)[O-]>>NC=1C=C(C=CC1NCC1CCCCC1)NC(OC)=O | O=[N+:19]([O-])[c:18]1[c:9]([NH:10][CH2:11][CH:12]2[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]2)[cH:8][cH:7][c:6]([NH:5][C:3]([O:2][CH3:1])=[O:4])[cH:20]1>>[CH3:1][O:2][C:3](=[O:4])[NH:5][c:6]1[cH:7][cH:8][c:9]([NH:10][CH2:11][CH:12]2[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]2)[c:18]([NH2:19])[cH:20]1 | COC(=O)Nc1ccc(NCC2CCCCC2)c([N+](=O)[O-])c1 | COC(=O)Nc1ccc(NCC2CCCCC2)c(N)c1 | null | null | [Pd].CCOC(=O)C | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccc(NCC2CCCCC2)cc1 | 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 | 8 | HOUR | Methyl {4-[(cyclohexylmethyl)amino]-3-nitrophenyl}carbamate (1.05 g, 3.42 mmol) was dissolved in 30 mL of EtOAc containing a catalytic amount of 10% Pd/C. The solution was shaken in a Parr hydrogenation apparatus under H2 atmosphere (40 psi) at RT overnight The solution was filtered through Celite and the solvent was e... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1.C1CCCCC1 | Other | [Pd].CCOC(=O)C | null | 8 | COC(=O)Nc1ccc(NCC2CCCCC2)c([N+](=O)[O-])c1>[Pd].CCOC(=O)C>COC(=O)Nc1ccc(NCC2CCCCC2)c(N)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a8d54946ad3147e7b2825390666925f5 | CC(C)(C)C(=O)Cl.COC(=O)Nc1ccc(NCC2CCCCC2)c(N)c1>>COC(=O)Nc1ccc2c(c1)nc(C(C)(C)C)n2CC1CCCCC1 | NC=1C=C(C=CC1NCC1CCCCC1)NC(OC)=O.CC(C(=O)Cl)(C)C>>COC(NC1=CC2=C(N(C(=N2)C(C)(C)C)CC2CCCCC2)C=C1)=O | O=[C:13](Cl)[C:14]([CH3:15])([CH3:16])[CH3:17].[CH3:1][O:2][C:3](=[O:4])[NH:5][c:6]1[cH:7][cH:8][c:9]([NH:18][CH2:19][CH:20]2[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25]2)[c:10]([NH2:12])[cH:11]1>>[CH3:1][O:2][C:3](=[O:4])[NH:5][c:6]1[cH:7][cH:8][c:9]2[c:10]([cH:11]1)[n:12][c:13]([C:14]([CH3:15])([CH3:16])[CH3:17])[n:18]2[... | CC(C)(C)C(=O)Cl.COC(=O)Nc1ccc(NCC2CCCCC2)c(N)c1 | COC(=O)Nc1ccc2c(c1)nc(C(C)(C)C)n2CC1CCCCC1 | null | CN(C)C=1C=CN=CC1 | ClCCl | Aromatic Heterocycle Formation | OtherReaction | b48b9f848f2f637750a62e12d0a60718d527408df46b4fc5f95f8aac64874f8d | 56ef83dfadec35a1cf1db968b807e178cc4924ce15bf36d774883783cef0f450 | c1ccc2c(c1)ncn2CC1CCCCC1 | Cl-[C;H0;D3;+0:1](=O)-[C:2](-[C;D1;H3:3])(-[C;D1;H3:4])-[C;D1;H3:5].[C:6]-[C:7]-[NH;D2;+0:8]-[c:9](:[c:10]):[c:11](-[NH2;D1;+0:12]):[c:13]>>[C:6]-[C:7]-[n;H0;D3;+0:8]1:[c:9](:[c:10]):[c:11](:[c:13]):[n;H0;D2;+0:12]:[c;H0;D3;+0:1]:1-[C:2](-[C;D1;H3:3])(-[C;D1;H3:4])-[C;D1;H3:5] | null | [] | null | null | 1 | HOUR | Methyl {3-amino-4-[(cyclohexylmethyl)amino]phenyl}carbamate (950 mg, 3.43 mmol) and DMAP (100 mg, 0.858 mmol) were dissolved in 25 mL of dichloromethane. Trimethylacetyl chloride (0.460 mL, 3.77 mmol) was added dropwise and the solution stirred at RT for 1 h. The solvent was concentrated. The residue was divided in two... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine.Secondary amine | null | c1ccccc1 | c1ccc2nc[nH]c2c1 | c1ccc2nc[nH]c2c1.C1CCCCC1 | HCl | CN(C)C=1C=CN=CC1.ClCCl | null | 1 | CC(C)(C)C(=O)Cl.COC(=O)Nc1ccc(NCC2CCCCC2)c(N)c1>CN(C)C=1C=CN=CC1.ClCCl>COC(=O)Nc1ccc2c(c1)nc(C(C)(C)C)n2CC1CCCCC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d46b3c62044847c4bcb3f8670203ab74 | COC(=O)Nc1ccc2c(c1)nc(C(C)(C)C)n2CC1CCCCC1>>CNc1ccc2c(c1)nc(C(C)(C)C)n2CC1CCCCC1 | COC(NC1=CC2=C(N(C(=N2)C(C)(C)C)CC2CCCCC2)C=C1)=O.Cl.CCOCC.[H-].[H-].[H-].[H-].[Li+].[Al+3]>>C(C)(C)(C)C1=NC2=C(N1CC1CCCCC1)C=CC(=C2)NC | CO[C:1](=O)[NH:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([cH:8]1)[n:9][c:10]([C:11]([CH3:12])([CH3:13])[CH3:14])[n:15]2[CH2:16][CH:17]1[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22]1>>[CH3:1][NH:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([cH:8]1)[n:9][c:10]([C:11]([CH3:12])([CH3:13])[CH3:14])[n:15]2[CH2:16][CH:17]1[CH2:18][CH2:19][CH2:20][CH2:21... | COC(=O)Nc1ccc2c(c1)nc(C(C)(C)C)n2CC1CCCCC1 | CNc1ccc2c(c1)nc(C(C)(C)C)n2CC1CCCCC1 | null | null | C1CCOC1 | Reduction | OtherReaction | 0162385dd3f2239a186ebaf1047930f21ea49a4113c06354aed30cdbf1cd719c | f6bec327410058c9cba187636b48ed5ef90429f24bf839d7fb4e0588ab9ff83e | c1ccc2c(c1)ncn2CC1CCCCC1 | C-O-[C;H0;D3;+0:1](=O)-[#7:2]-[c:3]>>[CH3;D1;+0:1]-[#7:2]-[c:3] | null | [] | 0 | CELSIUS | 15 | MINUTE | Methyl[2-tert-butyl-1-(cyclohexylmethyl)-1H-benzimidazol-5-yl]carbamate (650 mg, 1.89 mmol) was dissolved in 20 mL of THF at 0° C. under nitrogen. 1M HCl/ether (2.65 mL, 2.65 mmol) was added dropwise and the solution stirred at 0° C. for 15 min. LiAlH4 (360 mg, 9.45 mmol) was then slowly added and the solution stirred ... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether | null | null | null | c1ccc2nc[nH]c2c1.C1CCCCC1 | Other | C1CCOC1 | 0 | 0.25 | COC(=O)Nc1ccc2c(c1)nc(C(C)(C)C)n2CC1CCCCC1>C1CCOC1>CNc1ccc2c(c1)nc(C(C)(C)C)n2CC1CCCCC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e930e5e86d4642739fcf31be87fc626e | CC(=O)OC(C)=O.Nc1ccc(F)c([N+](=O)[O-])c1>>CC(=O)Nc1ccc(F)c([N+](=O)[O-])c1 | FC1=C(C=C(N)C=C1)[N+](=O)[O-].C(C)(=O)OC(C)=O>>FC1=C(C=C(C=C1)NC(C)=O)[N+](=O)[O-] | CC(=O)O[C:2]([CH3:1])=[O:3].[NH2:4][c:5]1[cH:6][cH:7][c:8]([F:9])[c:10]([N+:11](=[O:12])[O-:13])[cH:14]1>>[CH3:1][C:2](=[O:3])[NH:4][c:5]1[cH:6][cH:7][c:8]([F:9])[c:10]([N+:11](=[O:12])[O-:13])[cH:14]1 | CC(=O)OC(C)=O.Nc1ccc(F)c([N+](=O)[O-])c1 | CC(=O)Nc1ccc(F)c([N+](=O)[O-])c1 | null | null | null | Acylation | Aminolysis of esters | 87d35e51b477fc9a658a6f307eb56d84c8879182772c9dd3a42ec0d584fd2684 | 627cbc0550c9f51ad0105d9fcf46677e8c93bed87ee95bfe69292a82550c95b7 | c1ccccc1 | C-C(=O)-O-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[NH2;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[C;D1;H3:2]-[C;H0;D3;+0:1](=[O;D1;H0:3])-[NH;D2;+0:4]-[c:5](:[c:6]):[c:7] | 70 | [{"value": 70.0, "product": "FC1=C(C=C(C=C1)NC(C)=O)[N+](=O)[O-]", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | 4-Fluoro-3-nitro-aniline (45.0 g, 288.2 mmol) was added portionwise to acetic anhydride (150 mL) at room temperature. The reaction mixture was stirred at room temperature for 2 h. The white solid was collected and dried in vacuo to give the desired title compound (42.0 g, 70%).
Conditions: See reaction.notes.procedure_... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Primary amine | Secondary amide | null | null | c1ccccc1 | HO- | null | null | 2 | CC(=O)OC(C)=O.Nc1ccc(F)c([N+](=O)[O-])c1>>CC(=O)Nc1ccc(F)c([N+](=O)[O-])c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-34443b7ffb7e4235aaf40ecc280e5e45 | CC(=O)Nc1ccc(F)c([N+](=O)[O-])c1.NCC1CCCCC1>>CC(=O)Nc1ccc(NCC2CCCCC2)c([N+](=O)[O-])c1 | C1(CCCCC1)CN.FC1=C(C=C(C=C1)NC(C)=O)[N+](=O)[O-].C([O-])([O-])=O.[Na+].[Na+]>>C1(CCCCC1)CNC1=C(C=C(C=C1)NC(C)=O)[N+](=O)[O-] | F[c:8]1[cH:7][cH:6][c:5]([NH:4][C:2]([CH3:1])=[O:3])[cH:21][c:17]1[N+:18](=[O:19])[O-:20].[NH2:9][CH2:10][CH:11]1[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]1>>[CH3:1][C:2](=[O:3])[NH:4][c:5]1[cH:6][cH:7][c:8]([NH:9][CH2:10][CH:11]2[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]2)[c:17]([N+:18](=[O:19])[O-:20])[cH:21]1 | CC(=O)Nc1ccc(F)c([N+](=O)[O-])c1.NCC1CCCCC1 | CC(=O)Nc1ccc(NCC2CCCCC2)c([N+](=O)[O-])c1 | null | null | O.CCO | Heteroatom Alkylation and Arylation | Buchwald-Hartwig/Ullmann-Goldberg/N-arylation primary amine | da9dae6a655c4bd18887b692f91621e77027436294d6e1fc7be7295afb364796 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(NCC2CCCCC2)cc1 | F-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[#7;+:5]):[c:6].[C:7]-[C:8]-[NH2;D1;+0:9]>>[#7;+:5]-[c:4](:[c:6]):[c;H0;D3;+0:1](-[NH;D2;+0:9]-[C:8]-[C:7]):[c:2]:[c:3] | 113.3 | [{"value": 100.0, "product": "C1(CCCCC1)CNC1=C(C=C(C=C1)NC(C)=O)[N+](=O)[O-]", "details": "PERCENTYIELD", "is_desired": false}, {"value": 113.3, "product": "C1(CCCCC1)CNC1=C(C=C(C=C1)NC(C)=O)[N+](=O)[O-]", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | null | null | Cyclohexylmethylamine (2.86 mL, 2.49 g, 22.0 mmol) was added to a mixture of N-(4-fluoro-3-nitrophenyl)acetamide (3.96 g, 20.0 mmol) and sodium carbonate (4.66 g, 44 mmol) in EtOH (50 mL) at room temperature. The reaction mixture was heated for 48 h at 60° C., and diluted with H2O (800 mL). The orange solid was precipi... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccccc1 | c1ccccc1 | c1ccccc1.C1CCCCC1 | HF | O.CCO | 60 | null | CC(=O)Nc1ccc(F)c([N+](=O)[O-])c1.NCC1CCCCC1>O.CCO>CC(=O)Nc1ccc(NCC2CCCCC2)c([N+](=O)[O-])c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-b6c975447a644a87a3fb29bfe2e09877 | CCC(C)(C)c1nc2cc(NC(C)=O)ccc2n1CC1CCCCC1>>CCC(C)(C)c1nc2cc(N)ccc2n1CC1CCCCC1 | C1(CCCCC1)CN1C(=NC2=C1C=CC(=C2)NC(C)=O)C(CC)(C)C.Cl>>C1(CCCCC1)CN1C(=NC2=C1C=CC(=C2)N)C(CC)(C)C | CC(=O)[NH:11][c:10]1[cH:9][c:8]2[n:7][c:6]([C:3]([CH2:2][CH3:1])([CH3:4])[CH3:5])[n:15]([CH2:16][CH:17]3[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22]3)[c:14]2[cH:13][cH:12]1>>[CH3:1][CH2:2][C:3]([CH3:4])([CH3:5])[c:6]1[n:7][c:8]2[cH:9][c:10]([NH2:11])[cH:12][cH:13][c:14]2[n:15]1[CH2:16][CH:17]1[CH2:18][CH2:19][CH2:20][CH2:2... | CCC(C)(C)c1nc2cc(NC(C)=O)ccc2n1CC1CCCCC1 | CCC(C)(C)c1nc2cc(N)ccc2n1CC1CCCCC1 | null | null | C(C)O | Reduction | Hydrogenolysis of amides/imides/carbamates | 755df58c254dea764fdda078ffd678ec540bba057c83683be04c253f1270ac7b | 025f7cefe51e71668ad5d09fca32df168e9b538347403e4d5c1748073e538adc | c1ccc2c(c1)ncn2CC1CCCCC1 | C-C(=O)-[NH;D2;+0:1]-[c:2](:[c:3]):[c:4]:[c:5]:[#7;a:6]>>[#7;a:6]:[c:5]:[c:4]:[c:2](-[NH2;D1;+0:1]):[c:3] | 127.3 | [{"value": 100.0, "product": "C1(CCCCC1)CN1C(=NC2=C1C=CC(=C2)N)C(CC)(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 127.3, "product": "C1(CCCCC1)CN1C(=NC2=C1C=CC(=C2)N)C(CC)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | N-[1-(Cyclohexylmethyl)-2-(1,1-dimethylpropyl)-1H-benzimidazol-5-yl]acetamide (105.4 mg, 0.309 mmol) was dissolved in ethanol (3 mL) and 2N HCl aqueous solution (2 mL) in a Teflon-capped test tube. The vessel was irradiated by microwave for 45 min. at 120° C. After evaporation and drying in vacuo, 117.8 mg (100%) of th... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide | Primary amine | null | null | c1ccc2nc[nH]c2c1.C1CCCCC1 | HO- | C(C)O | null | null | CCC(C)(C)c1nc2cc(NC(C)=O)ccc2n1CC1CCCCC1>C(C)O>CCC(C)(C)c1nc2cc(N)ccc2n1CC1CCCCC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-aba0c9350b3d445eba5866611aea8a27 | CCC(C)(C)C(=O)Cl.CCC(C)(C)c1nc2cc(N)ccc2n1CC1CCCCC1>>CCC(C)(C)C(=O)Nc1ccc2c(c1)nc(C(C)(C)CC)n2CC1CCCCC1 | CC(C(=O)Cl)(CC)C.Cl.C1(CCCCC1)CN1C(=NC2=C1C=CC(=C2)N)C(CC)(C)C>>C1(CCCCC1)CN1C(=NC2=C1C=CC(=C2)NC(C(CC)(C)C)=O)C(CC)(C)C | Cl[C:6]([C:3]([CH2:2][CH3:1])([CH3:4])[CH3:5])=[O:7].[NH2:8][c:9]1[cH:10][cH:11][c:12]2[c:13]([cH:14]1)[n:15][c:16]([C:17]([CH3:18])([CH3:19])[CH2:20][CH3:21])[n:22]2[CH2:23][CH:24]1[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29]1>>[CH3:1][CH2:2][C:3]([CH3:4])([CH3:5])[C:6](=[O:7])[NH:8][c:9]1[cH:10][cH:11][c:12]2[c:13]([cH:1... | CCC(C)(C)C(=O)Cl.CCC(C)(C)c1nc2cc(N)ccc2n1CC1CCCCC1 | CCC(C)(C)C(=O)Nc1ccc2c(c1)nc(C(C)(C)CC)n2CC1CCCCC1 | null | CN(C)C=1C=CN=CC1 | C(C)#N.CCOC(=O)C | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | c1ccc2c(c1)ncn2CC1CCCCC1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])(-[C;D1;H3:5])-[C;D1;H3:6].[#7;a:7]:[c:8]:[c:9]:[c:10](-[NH2;D1;+0:11]):[c:12]>>[#7;a:7]:[c:8]:[c:9]:[c:10](-[NH;D2;+0:11]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])(-[C;D1;H3:5])-[C;D1;H3:6]):[c:12] | 87 | [{"value": 87.0, "product": "C1(CCCCC1)CN1C(=NC2=C1C=CC(=C2)NC(C(CC)(C)C)=O)C(CC)(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 86.5, "product": "C1(CCCCC1)CN1C(=NC2=C1C=CC(=C2)NC(C(CC)(C)C)=O)C(CC)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 6 | HOUR | 2,2-Dimethylbutyryl chloride (24.6 mg, 0.18 mmol) was added to a mixture of 1-(cyclohexylmethyl)-2-(1,1-dimethylpropyl)-1H-benzimidazol-5-amine hydrochloride (65.0 mg, 0.15 mmol) (for preparation see in Example 7, step B) and DMAP (73.3 mg, 0.60 mmol) in acetonitrile (5 mL) at 0° C. The mixture was stirred for 6 h at r... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccc2nc[nH]c2c1.C1CCCCC1 | HCl | CN(C)C=1C=CN=CC1.C(C)#N.CCOC(=O)C | null | 6 | CCC(C)(C)C(=O)Cl.CCC(C)(C)c1nc2cc(N)ccc2n1CC1CCCCC1>CN(C)C=1C=CN=CC1.C(C)#N.CCOC(=O)C>CCC(C)(C)C(=O)Nc1ccc2c(c1)nc(C(C)(C)CC)n2CC1CCCCC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d51432f38f2c4258983d49f9195f03f3 | CC(=O)Nc1ccc(NCC2CCCCC2)c(N)c1.CC(C)(C)C(=O)Cl>>CC(=O)Nc1ccc2c(c1)nc(C(C)(C)C)n2CC1CCCCC1 | NC=1C=C(C=CC1NCC1CCCCC1)NC(C)=O.CC(C(=O)Cl)(C)C>>C(C)(C)(C)C1=NC2=C(N1CC1CCCCC1)C=CC(=C2)NC(C)=O | [CH3:1][C:2](=[O:3])[NH:4][c:5]1[cH:6][cH:7][c:8]([NH:17][CH2:18][CH:19]2[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24]2)[c:9]([NH2:11])[cH:10]1.O=[C:12](Cl)[C:13]([CH3:14])([CH3:15])[CH3:16]>>[CH3:1][C:2](=[O:3])[NH:4][c:5]1[cH:6][cH:7][c:8]2[c:9]([cH:10]1)[n:11][c:12]([C:13]([CH3:14])([CH3:15])[CH3:16])[n:17]2[CH2:18][CH:1... | CC(=O)Nc1ccc(NCC2CCCCC2)c(N)c1.CC(C)(C)C(=O)Cl | CC(=O)Nc1ccc2c(c1)nc(C(C)(C)C)n2CC1CCCCC1 | null | CN(C)C=1C=CN=CC1 | ClCCl | Aromatic Heterocycle Formation | OtherReaction | b48b9f848f2f637750a62e12d0a60718d527408df46b4fc5f95f8aac64874f8d | 56ef83dfadec35a1cf1db968b807e178cc4924ce15bf36d774883783cef0f450 | c1ccc2c(c1)ncn2CC1CCCCC1 | Cl-[C;H0;D3;+0:1](=O)-[C:2](-[C;D1;H3:3])(-[C;D1;H3:4])-[C;D1;H3:5].[C:6]-[C:7]-[NH;D2;+0:8]-[c:9](:[c:10]):[c:11](-[NH2;D1;+0:12]):[c:13]>>[C:6]-[C:7]-[n;H0;D3;+0:8]1:[c:9](:[c:10]):[c:11](:[c:13]):[n;H0;D2;+0:12]:[c;H0;D3;+0:1]:1-[C:2](-[C;D1;H3:3])(-[C;D1;H3:4])-[C;D1;H3:5] | 72 | [{"value": 72.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the same procedure of Example 6, a mixture of N-{3-amino-4-[(cyclohexylmethyl)amino]phenyl}acetamide (1.57 g, 6.0 mmol) (for preparation see in Example 6, step D) and DMAP (0.15 g, 1.2 mmol) in dichloromethane (70 mL) was treated with trimethylacetyl choride (0.83 g, 6.6 mmol) at −10° C. After evaporation of ... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine.Secondary amine | null | c1ccccc1 | c1ccc2nc[nH]c2c1 | c1ccc2nc[nH]c2c1.C1CCCCC1 | HCl | CN(C)C=1C=CN=CC1.ClCCl | null | null | CC(=O)Nc1ccc(NCC2CCCCC2)c(N)c1.CC(C)(C)C(=O)Cl>CN(C)C=1C=CN=CC1.ClCCl>CC(=O)Nc1ccc2c(c1)nc(C(C)(C)C)n2CC1CCCCC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-5ee226211554458a9e908dd0753bfaf1 | CC(=O)Nc1ccc2c(c1)nc(C(C)(C)C)n2CC1CCCCC1.CI>>CC(=O)N(C)c1ccc2c(c1)nc(C(C)(C)C)n2CC1CCCCC1 | [H-].[Na+].C(C)(C)(C)C1=NC2=C(N1CC1CCCCC1)C=CC(=C2)NC(C)=O.IC>>C(C)(C)(C)C1=NC2=C(N1CC1CCCCC1)C=CC(=C2)N(C(C)=O)C | [CH3:1][C:2](=[O:3])[NH:4][c:6]1[cH:7][cH:8][c:9]2[c:10]([cH:11]1)[n:12][c:13]([C:14]([CH3:15])([CH3:16])[CH3:17])[n:18]2[CH2:19][CH:20]1[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25]1.I[CH3:5]>>[CH3:1][C:2](=[O:3])[N:4]([CH3:5])[c:6]1[cH:7][cH:8][c:9]2[c:10]([cH:11]1)[n:12][c:13]([C:14]([CH3:15])([CH3:16])[CH3:17])[n:18]2[C... | CC(=O)Nc1ccc2c(c1)nc(C(C)(C)C)n2CC1CCCCC1.CI | CC(=O)N(C)c1ccc2c(c1)nc(C(C)(C)C)n2CC1CCCCC1 | null | null | C1CCOC1 | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 780d850c4b8333c4b07101ff526eea0725c627f5cbcabe141bddc514762f1fac | 0a16658309ac5595448433dd7ef49294830b145345df0b202ccd54727262e629 | c1ccc2c(c1)ncn2CC1CCCCC1 | I-[CH3;D1;+0:1].[#7;a:2]:[c:3]:[c:4]:[c:5](-[NH;D2;+0:6]-[C:7](-[C;D1;H3:8])=[O;D1;H0:9]):[c:10]>>[#7;a:2]:[c:3]:[c:4]:[c:5](-[N;H0;D3;+0:6](-[CH3;D1;+0:1])-[C:7](-[C;D1;H3:8])=[O;D1;H0:9]):[c:10] | 100 | [{"value": 100.0, "product": "C(C)(C)(C)C1=NC2=C(N1CC1CCCCC1)C=CC(=C2)N(C(C)=O)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | Sodium hydride (201.5 mg, 5.04 mmol) was added to a solution of N-[2-tert-butyl-1-(cyclohexylmethyl)-1H-benzimidazol-5-yl]acetamide (549.8 mg, 1.68 mmol) (for preparation see in Example 9) in THF (50 mL) at 0° C. Stirring for 30 min., iodomethane was added. The resulting mixture was stirred overnight at room temperatur... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide | Tertiary amide | null | null | c1ccc2nc[nH]c2c1.C1CCCCC1 | HI | C1CCOC1 | null | 0.5 | CC(=O)Nc1ccc2c(c1)nc(C(C)(C)C)n2CC1CCCCC1.CI>C1CCOC1>CC(=O)N(C)c1ccc2c(c1)nc(C(C)(C)C)n2CC1CCCCC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-6e11388875cb4d1e9dd3d37e11d95193 | CC(C)(C)C(=O)Cl.Nc1ccc(F)c([N+](=O)[O-])c1>>CC(C)(C)C(=O)Nc1ccc(F)c([N+](=O)[O-])c1 | FC1=C(C=C(N)C=C1)[N+](=O)[O-].CC(C(=O)Cl)(C)C>>FC1=C(C=C(C=C1)NC(C(C)(C)C)=O)[N+](=O)[O-] | Cl[C:5]([C:2]([CH3:1])([CH3:3])[CH3:4])=[O:6].[NH2:7][c:8]1[cH:9][cH:10][c:11]([F:12])[c:13]([N+:14](=[O:15])[O-:16])[cH:17]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[C:5](=[O:6])[NH:7][c:8]1[cH:9][cH:10][c:11]([F:12])[c:13]([N+:14](=[O:15])[O-:16])[cH:17]1 | CC(C)(C)C(=O)Cl.Nc1ccc(F)c([N+](=O)[O-])c1 | CC(C)(C)C(=O)Nc1ccc(F)c([N+](=O)[O-])c1 | null | CN(C)C=1C=CN=CC1 | C(Cl)Cl | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | c1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C;D1;H3:4])(-[C;D1;H3:5])-[C;D1;H3:6].[NH2;D1;+0:7]-[c:8](:[c:9]):[c:10]>>[C;D1;H3:4]-[C:3](-[C;D1;H3:5])(-[C;D1;H3:6])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:7]-[c:8](:[c:9]):[c:10] | null | [] | null | null | 3 | HOUR | 4-Fluoro-3-nitroaniline (500 mg, 3.20 mmol) and DMAP (586 mg, 4.80 mmol) were dissolved in 25 mL of DCM. Trimethylacetyl chloride (0.587 mL, 4.80 mmol) was added dropwise and the solution was stirred at rt for 3 h. The solution was washed with 5% KHSO4 solution, saturated NaHCO3 solution, brine and dried over anhydrous... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccccc1 | HCl | CN(C)C=1C=CN=CC1.C(Cl)Cl | null | 3 | CC(C)(C)C(=O)Cl.Nc1ccc(F)c([N+](=O)[O-])c1>CN(C)C=1C=CN=CC1.C(Cl)Cl>CC(C)(C)C(=O)Nc1ccc(F)c([N+](=O)[O-])c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-473ac90a2b0d4fa7a2f6d8d1489c704b | CC(C)(C)C(=O)Nc1ccc(F)c([N+](=O)[O-])c1.NCC1CCCCC1>>CC(C)(C)C(=O)Nc1ccc(NCC2CCCCC2)c([N+](=O)[O-])c1 | FC1=C(C=C(C=C1)NC(C(C)(C)C)=O)[N+](=O)[O-].C1(CCCCC1)CN.C(C)N(CC)CC>>C1(CCCCC1)CNC1=C(C=C(C=C1)NC(C(C)(C)C)=O)[N+](=O)[O-] | F[c:11]1[cH:10][cH:9][c:8]([NH:7][C:5]([C:2]([CH3:1])([CH3:3])[CH3:4])=[O:6])[cH:24][c:20]1[N+:21](=[O:22])[O-:23].[NH2:12][CH2:13][CH:14]1[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[C:5](=[O:6])[NH:7][c:8]1[cH:9][cH:10][c:11]([NH:12][CH2:13][CH:14]2[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]... | CC(C)(C)C(=O)Nc1ccc(F)c([N+](=O)[O-])c1.NCC1CCCCC1 | CC(C)(C)C(=O)Nc1ccc(NCC2CCCCC2)c([N+](=O)[O-])c1 | null | null | CCO | Heteroatom Alkylation and Arylation | Buchwald-Hartwig/Ullmann-Goldberg/N-arylation primary amine | da9dae6a655c4bd18887b692f91621e77027436294d6e1fc7be7295afb364796 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(NCC2CCCCC2)cc1 | F-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[#7;+:5]):[c:6].[C:7]-[C:8]-[NH2;D1;+0:9]>>[#7;+:5]-[c:4](:[c:6]):[c;H0;D3;+0:1](-[NH;D2;+0:9]-[C:8]-[C:7]):[c:2]:[c:3] | null | [] | null | null | null | null | N-(4-Fluoro-3-nitrophenyl)-2,2-dimethylpropanamide (158 mg, 0.658 mmol) and cyclohexylmethylamine (0.100 mL, 0.790 mmol) were stirred in 3 mL of EtOH containing triethylamine (0.140 mL, 0.987 mmol) at 75° C. for 24 h. The solvent was evaporated. The residue was dissolved in EtOAc and washed with 5% KHSO4 solution, satu... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccccc1 | c1ccccc1 | c1ccccc1.C1CCCCC1 | HF | CCO | null | null | CC(C)(C)C(=O)Nc1ccc(F)c([N+](=O)[O-])c1.NCC1CCCCC1>CCO>CC(C)(C)C(=O)Nc1ccc(NCC2CCCCC2)c([N+](=O)[O-])c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-618390cab0f248739bb4b9165dc5860d | CC(C)(C)C(=O)Nc1ccc(NCC2CCCCC2)c([N+](=O)[O-])c1>>CC(C)(C)C(=O)Nc1ccc(NCC2CCCCC2)c(N)c1 | C1(CCCCC1)CNC1=C(C=C(C=C1)NC(C(C)(C)C)=O)[N+](=O)[O-]>>NC=1C=C(C=CC1NCC1CCCCC1)NC(C(C)(C)C)=O | O=[N+:21]([O-])[c:20]1[c:11]([NH:12][CH2:13][CH:14]2[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]2)[cH:10][cH:9][c:8]([NH:7][C:5]([C:2]([CH3:1])([CH3:3])[CH3:4])=[O:6])[cH:22]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[C:5](=[O:6])[NH:7][c:8]1[cH:9][cH:10][c:11]([NH:12][CH2:13][CH:14]2[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]2)[c:20](... | CC(C)(C)C(=O)Nc1ccc(NCC2CCCCC2)c([N+](=O)[O-])c1 | CC(C)(C)C(=O)Nc1ccc(NCC2CCCCC2)c(N)c1 | null | null | [Pd].CCOC(=O)C | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccc(NCC2CCCCC2)cc1 | 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 | 24 | HOUR | N-{4-[(Cyclohexylmethyl)amino]-3-nitrophenyl}-2,2-dimethylpropanamide (215 mg, 0.645 mmol) was dissolved in 20 mL of EtOAc containing a catalytic amount of 10% Pd/C. The solution was shaken in a Parr hydrogenation apparatus under H2 atmosphere (45 psi) at RT for 24 h. The solution was filtered through Celite and the so... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1.C1CCCCC1 | Other | [Pd].CCOC(=O)C | null | 24 | CC(C)(C)C(=O)Nc1ccc(NCC2CCCCC2)c([N+](=O)[O-])c1>[Pd].CCOC(=O)C>CC(C)(C)C(=O)Nc1ccc(NCC2CCCCC2)c(N)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-6e348835439b42cf93ab335a3b32cf69 | CCCc1nc2c(C)cc(-c3nc4ccccc4n3C)cc2[nH]1.O=C(O)c1ccccc1-c1ccc(CBr)cc1>>CCCc1nc2c(C)cc(-c3nc4ccccc4n3C)cc2n1Cc1ccc(-c2ccccc2C(=O)OC)cc1 | BrCC1=CC=C(C=C1)C=1C(=CC=CC1)C(=O)O.CN1C(=NC2=C1C=CC=C2)C2=CC1=C(N=C(N1)CCC)C(=C2)C.C(=O)([O-])[O-].[K+].[K+]>>CCCC1=NC2=C(C=C(C=C2N1CC3=CC=C(C=C3)C4=CC=CC=C4C(=O)OC)C5=NC6=CC=CC=C6N5C)C | [CH3:1][CH2:2][CH2:3][c:4]1[n:5][c:6]2[c:7]([CH3:8])[cH:9][c:10](-[c:11]3[n:12][c:13]4[cH:14][cH:15][cH:16][cH:17][c:18]4[n:19]3[CH3:20])[cH:21][c:22]2[nH:23]1.Br[CH2:24][c:25]1[cH:26][cH:27][c:28](-[c:29]2[cH:30][cH:31][cH:32][cH:33][c:34]2[C:35](=[O:36])[OH:37])[cH:39][cH:40]1>>[CH3:1][CH2:2][CH2:3][c:4]1[n:5][c:6]2[... | CCCc1nc2c(C)cc(-c3nc4ccccc4n3C)cc2[nH]1.O=C(O)c1ccccc1-c1ccc(CBr)cc1 | CCCc1nc2c(C)cc(-c3nc4ccccc4n3C)cc2n1Cc1ccc(-c2ccccc2C(=O)OC)cc1 | null | [Cl-].C[N+](CCCC)(CCCC)CCCC | C1(=CC=CC=C1)C | Heteroatom Alkylation and Arylation | OtherReaction | 1695564f165c55ad3fbe70715b473f448c2f40815bd3cea3555039072c26d832 | 8446834f0edd1e71a2dcaffc09b80c7367abf3407263a8998354a2d20c1766bb | c1ccc(-c2ccc(Cn3cnc4ccc(-c5nc6ccccc6[nH]5)cc43)cc2)cc1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[O;D1;H0:5]=[C:6](-[OH;D1;+0:7])-[c:8].[C:9]-[c:10]1:[#7;a:11]:[c:12](:[c:13]):[c:14](:[c:15]):[nH;D2;+0:16]:1>>[C;D1;H3:17]-[O;H0;D2;+0:7]-[C:6](=[O;D1;H0:5])-[c:8].[C:9]-[c:10]1:[#7;a:11]:[c:12](:[c:13]):[c:14](:[c:15]):[n;H0;D3;+0:16]:1-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4] | 72.3 | [{"value": 69.0, "product": "CCCC1=NC2=C(C=C(C=C2N1CC3=CC=C(C=C3)C4=CC=CC=C4C(=O)OC)C5=NC6=CC=CC=C6N5C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 72.3, "product": "CCCC1=NC2=C(C=C(C=C2N1CC3=CC=C(C=C3)C4=CC=CC=C4C(=O)OC)C5=NC6=CC=CC=C6N5C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 87.5 | CELSIUS | 6 | HOUR | 1,7′-dimethyl-2′-propyl-1H,3′H-[2,5′]bibenzoimidazolyl (BIM) (4 g), Aliquat® 175 (1.36 ml), K2CO3 (8.19 g), and toluene (50 ml) were added to a 250 ml round bottom flask equipped with a magnetic stirring bar and reflux condenser. The mixture was heated to reflux (about 85-90° C.) until a clear brown organic solution wa... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Carboxylic acid | Ester | c1ccc2[nH]cnc2c1 | c1ccc2[nH]cnc2c1 | c1ccc2[nH]cnc2c1.c1nc2ccccc2[nH]1.c1ccccc1.c1ccccc1 | null | [Cl-].C[N+](CCCC)(CCCC)CCCC.C1(=CC=CC=C1)C | 87.5 | 6 | CCCc1nc2c(C)cc(-c3nc4ccccc4n3C)cc2[nH]1.O=C(O)c1ccccc1-c1ccc(CBr)cc1>[Cl-].C[N+](CCCC)(CCCC)CCCC.C1(=CC=CC=C1)C>CCCc1nc2c(C)cc(-c3nc4ccccc4n3C)cc2n1Cc1ccc(-c2ccccc2C(=O)OC)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-03e184bd9fb4474c9d96946be137c486 | CC(C)(C)OC(=O)Nc1ccccc1N.COC(=O)c1ccc(C(=O)O)s1>>COC(=O)c1ccc(C(=O)Nc2ccccc2NC(=O)OC(C)(C)C)s1 | C(=O)(N1C=NC=C1)N1C=NC=C1.COC(=O)C=1SC(=CC1)C(=O)O.C(C)(C)(C)OC(NC1=C(C=CC=C1)N)=O>>COC(=O)C=1SC(=CC1)C(NC1=C(C=CC=C1)NC(=O)OC(C)(C)C)=O | [NH2:11][c:12]1[cH:13][cH:14][cH:15][cH:16][c:17]1[NH:18][C:19](=[O:20])[O:21][C:22]([CH3:23])([CH3:24])[CH3:25].O[C:9]([c:8]1[cH:7][cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[s:26]1)=[O:10]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([C:9](=[O:10])[NH:11][c:12]2[cH:13][cH:14][cH:15][cH:16][c:17]2[NH:18][C:19](=[O:20]... | CC(C)(C)OC(=O)Nc1ccccc1N.COC(=O)c1ccc(C(=O)O)s1 | COC(=O)c1ccc(C(=O)Nc2ccccc2NC(=O)OC(C)(C)C)s1 | null | null | C1CCOC1 | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(Nc1ccccc1)c1cccs1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[#16;a:5]:[c:6]-[C:7](-[#8:8])=[O;D1;H0:9].[NH2;D1;+0:10]-[c:11](:[c:12]):[c:13]>>[#8:8]-[C:7](=[O;D1;H0:9])-[c:6]:[#16;a:5]:[c:3](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:10]-[c:11](:[c:12]):[c:13]):[c:4] | 80.2 | [{"value": 80.2, "product": "COC(=O)C=1SC(=CC1)C(NC1=C(C=CC=C1)NC(=O)OC(C)(C)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 4 | HOUR | Under an argon atmosphere 21.0 g (129 mmol) carbonyldiimidazol was added to a solution of 24.1 g (129 mmol) thiophene-2,5-dicarboxylic acid monomethyl ester in 600 ml THF. After 2 h at rt 26.9 g (129 mmol) (2-amino-phenyl)-carbamic acid tert-butyl ester were added and the reaction mixture was stirred for further 4 h at... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccsc1.c1ccccc1 | HO- | C1CCOC1 | null | 4 | CC(C)(C)OC(=O)Nc1ccccc1N.COC(=O)c1ccc(C(=O)O)s1>C1CCOC1>COC(=O)c1ccc(C(=O)Nc2ccccc2NC(=O)OC(C)(C)C)s1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-b033aa5185934b6fbcdd9dcb079a7e3e | COC(=O)c1ccc(C(=O)Nc2ccccc2NC(=O)OC(C)(C)C)s1>>CC(C)(C)OC(=O)Nc1ccccc1NC(=O)c1ccc(C(=O)O)s1 | COC(=O)C=1SC(=CC1)C(NC1=C(C=CC=C1)NC(=O)OC(C)(C)C)=O.[OH-].[K+]>>C(C)(C)(C)OC(=O)NC1=C(C=CC=C1)NC(=O)C1=CC=C(S1)C(=O)O | C[O:24][C:22]([c:21]1[cH:20][cH:19][c:18]([C:16]([NH:15][c:14]2[c:9]([NH:8][C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[cH:10][cH:11][cH:12][cH:13]2)=[O:17])[s:25]1)=[O:23]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][c:9]1[cH:10][cH:11][cH:12][cH:13][c:14]1[NH:15][C:16](=[O:17])[c:18]1[cH:19][cH:20][c:... | COC(=O)c1ccc(C(=O)Nc2ccccc2NC(=O)OC(C)(C)C)s1 | CC(C)(C)OC(=O)Nc1ccccc1NC(=O)c1ccc(C(=O)O)s1 | null | null | O.CO | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | O=C(Nc1ccccc1)c1cccs1 | 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] | 80 | [{"value": 80.0, "product": "C(C)(C)(C)OC(=O)NC1=C(C=CC=C1)NC(=O)C1=CC=C(S1)C(=O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | DAY | To a suspension of 18.5 g (50 mmol) 5-(2-tert-Butoxycarbonylamino-phenyl-carbamoyl)-thiophene-2-carboxylic acid methyl ester in 500 ml MeOH was added within 20 minutes a solution of 5.6 g (100 mmol) potassium hydroxide in 100 ml water. The reaction mixture was stirred at room temperature for 2 d. The MeOH was evaporate... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1.c1ccsc1 | Other | O.CO | null | 48 | COC(=O)c1ccc(C(=O)Nc2ccccc2NC(=O)OC(C)(C)C)s1>O.CO>CC(C)(C)OC(=O)Nc1ccccc1NC(=O)c1ccc(C(=O)O)s1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-b076af4194334424a356e8ccd3dc643f | CC(C)(C)OC(=O)Nc1ccccc1NC(=O)c1ccc(C(=O)O)s1.CCCC(C)N>>CCCC(C)NC(=O)c1ccc(C(=O)Nc2ccccc2NC(=O)OC(C)(C)C)s1 | CC(CCC)N.C(C)(C)(C)OC(=O)NC1=C(C=CC=C1)NC(=O)C1=CC=C(S1)C(=O)O.C(=O)(N1C=NC=C1)N1C=NC=C1>>C(C)(C)(C)OC(NC1=C(C=CC=C1)NC(=O)C=1SC(=CC1)C(NC(CCC)C)=O)=O | O[C:7](=[O:8])[c:9]1[cH:10][cH:11][c:12]([C:13](=[O:14])[NH:15][c:16]2[cH:17][cH:18][cH:19][cH:20][c:21]2[NH:22][C:23](=[O:24])[O:25][C:26]([CH3:27])([CH3:28])[CH3:29])[s:30]1.[CH3:1][CH2:2][CH2:3][CH:4]([CH3:5])[NH2:6]>>[CH3:1][CH2:2][CH2:3][CH:4]([CH3:5])[NH:6][C:7](=[O:8])[c:9]1[cH:10][cH:11][c:12]([C:13](=[O:14])[N... | CC(C)(C)OC(=O)Nc1ccccc1NC(=O)c1ccc(C(=O)O)s1.CCCC(C)N | CCCC(C)NC(=O)c1ccc(C(=O)Nc2ccccc2NC(=O)OC(C)(C)C)s1 | null | null | C1CCOC1 | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(Nc1ccccc1)c1cccs1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[#16;a:5]:[c:6]-[C:7](-[#7:8])=[O;D1;H0:9].[C:10]-[C:11](-[C;D1;H3:12])-[NH2;D1;+0:13]>>[#7:8]-[C:7](=[O;D1;H0:9])-[c:6]:[#16;a:5]:[c:3](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:13]-[C:11](-[C:10])-[C;D1;H3:12]):[c:4] | null | [] | 45 | CELSIUS | 1 | HOUR | To a solution of 4.4 g (12.1 mmol) 5-(2-tert-butoxycarbonylamino-phenylcarbamoyl)-thiophene-2-carboxylic acid in 80 ml THF were added 2.2 g (13.6 mmol) carbonyldiimidazol. The reaction mixture was stirred at 45° C. for 1 h and then cooled to rt. After addition of 1.05 g (12 mmol) 2-pentylamine the reaction mixture was ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccsc1.c1ccccc1 | HO- | C1CCOC1 | 45 | 1 | CC(C)(C)OC(=O)Nc1ccccc1NC(=O)c1ccc(C(=O)O)s1.CCCC(C)N>C1CCOC1>CCCC(C)NC(=O)c1ccc(C(=O)Nc2ccccc2NC(=O)OC(C)(C)C)s1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-555416858ee142e9b821a504eebd6180 | CC(C)N(CCN)C(C)C.COC(=O)c1ccc(C(=O)[O-])nc1>>COC(=O)c1ccc(C(=O)NCCN(C(C)C)C(C)C)nc1 | COC(=O)C=1C=CC(=NC1)C(=O)[O-].[K+].S(=O)(Cl)Cl.C(C)(C)N(CCN)C(C)C.C(C)N(CC)CC>>COC(C1=CN=C(C=C1)C(NCCN(C(C)C)C(C)C)=O)=O | [NH2:11][CH2:12][CH2:13][N:14]([CH:15]([CH3:16])[CH3:17])[CH:18]([CH3:19])[CH3:20].[O-][C:9]([c:8]1[cH:7][cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[cH:22][n:21]1)=[O:10]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([C:9](=[O:10])[NH:11][CH2:12][CH2:13][N:14]([CH:15]([CH3:16])[CH3:17])[CH:18]([CH3:19])[CH3:20])[n:21][c... | CC(C)N(CCN)C(C)C.COC(=O)c1ccc(C(=O)[O-])nc1 | COC(=O)c1ccc(C(=O)NCCN(C(C)C)C(C)C)nc1 | null | null | ClC(C)Cl.C(Cl)Cl.CN(C)C=O | Acylation | OtherReaction | 01b411aa709aa72475efefee2037796aeb41c60940ddba8e15aefc45a95317a8 | 45ca336cc0b18cf59a837ab710e8845f67d23306b24bf1f37b36a34a2de4779a | c1ccncc1 | [C:1]-[C:2]-[NH2;D1;+0:3].[O-]-[C;H0;D3;+0:4](=[O;D1;H0:5])-[c:6](:[c:7]):[#7;a:8]:[c:9]>>[C:1]-[C:2]-[NH;D2;+0:3]-[C;H0;D3;+0:4](=[O;D1;H0:5])-[c:6](:[c:7]):[#7;a:8]:[c:9] | 74 | [{"value": 74.0, "product": "COC(C1=CN=C(C=C1)C(NCCN(C(C)C)C(C)C)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 12 | HOUR | A suspension of 1.1 g (5 mmol) potassium 5-methoxycarbonyl-pyridine-2-carboxylate, 0.9 ml (12 mmol) thionyl chloride and 0.1 ml DMF in 5 ml dichloroethane was heated at reflux for 2 h. To the reaction mixture 5 ml CH2Cl2 were added and the solvent was evaporated. This procedure was repeated three times. The residue was... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | Secondary amide | null | null | c1ccncc1 | HO- | ClC(C)Cl.C(Cl)Cl.CN(C)C=O | null | 12 | CC(C)N(CCN)C(C)C.COC(=O)c1ccc(C(=O)[O-])nc1>ClC(C)Cl.C(Cl)Cl.CN(C)C=O>COC(=O)c1ccc(C(=O)NCCN(C(C)C)C(C)C)nc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d4f71ddca79f434ca74141127ac04f8c | COC(=O)c1ccc(C(=O)NCCN(C(C)C)C(C)C)nc1>>CC(C)N(CCNC(=O)c1ccc(C(=O)O)cn1)C(C)C | COC(C1=CN=C(C=C1)C(NCCN(C(C)C)C(C)C)=O)=O.[OH-].[Na+]>>C(C)(C)N(CCNC(=O)C1=NC=C(C(=O)O)C=C1)C(C)C | C[O:16][C:14]([c:13]1[cH:12][cH:11][c:10]([C:8]([NH:7][CH2:6][CH2:5][N:4]([CH:2]([CH3:1])[CH3:3])[CH:19]([CH3:20])[CH3:21])=[O:9])[n:18][cH:17]1)=[O:15]>>[CH3:1][CH:2]([CH3:3])[N:4]([CH2:5][CH2:6][NH:7][C:8](=[O:9])[c:10]1[cH:11][cH:12][c:13]([C:14](=[O:15])[OH:16])[cH:17][n:18]1)[CH:19]([CH3:20])[CH3:21] | COC(=O)c1ccc(C(=O)NCCN(C(C)C)C(C)C)nc1 | CC(C)N(CCNC(=O)c1ccc(C(=O)O)cn1)C(C)C | null | null | CO.C1CCOC1 | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccncc1 | C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]:[c:5]:[#7;a:6]>>[#7;a:6]:[c:5]:[c:4]-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1] | 88.9 | [{"value": 88.9, "product": "C(C)(C)N(CCNC(=O)C1=NC=C(C(=O)O)C=C1)C(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 1100 mg (3.6 mmol) 6-(2-diisopropylamino-ethylcarbamoyl)-nicotinic acid methyl ester in 10 ml THF and 3.0 ml MeOH was added 3.6 ml of an 2N aqueous NaOH solution. After 4 h at rt the solvent was evaporated. The residue was acidified with 1N HCl, filtered off and washed with water to give 936 mg (3.2 mm... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccncc1 | Other | CO.C1CCOC1 | null | null | COC(=O)c1ccc(C(=O)NCCN(C(C)C)C(C)C)nc1>CO.C1CCOC1>CC(C)N(CCNC(=O)c1ccc(C(=O)O)cn1)C(C)C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-6580ca4d42294055a46fcc7aa014cfdd | COC(=O)OC.O=C1CCc2cc(F)ccc2C1>>COC(=O)C1=C(O)CCc2cc(F)ccc21 | C(C)(=O)O.[H-].[Na+].C(OC)(OC)=O.FC=1C=C2CCC(CC2=CC1)=O>>FC=1C=C2CCC(=C(C2=CC1)C(=O)OC)O | CO[C:3]([O:2][CH3:1])=[O:4].[CH2:5]1[C:6](=[O:7])[CH2:8][CH2:9][c:10]2[cH:11][c:12]([F:13])[cH:14][cH:15][c:16]21>>[CH3:1][O:2][C:3](=[O:4])[C:5]1=[C:6]([OH:7])[CH2:8][CH2:9][c:10]2[cH:11][c:12]([F:13])[cH:14][cH:15][c:16]21 | COC(=O)OC.O=C1CCc2cc(F)ccc2C1 | COC(=O)C1=C(O)CCc2cc(F)ccc21 | null | null | O.C1(=CC=CC=C1)C | Acylation | OtherReaction | 5d9c81ecf4037759bc3774402d21bcd515500b9416fbff21a1b406ba2c541e6c | a17e333db4ac4c45047cd486becf44e6d06842c4a345b2a174026b25ac18fe66 | C1=Cc2ccccc2CC1 | C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C;D1;H3:4].[O;H0;D1;+0:5]=[C;H0;D3;+0:6]1-[C:7]-[C:8]-[c:9]:[c:10](:[c:11])-[CH2;D2;+0:12]-1>>[C;D1;H3:4]-[#8:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C;H0;D3;+0:12]1=[C;H0;D3;+0:6](-[OH;D1;+0:5])-[C:7]-[C:8]-[c:9]:[c:10]-1:[c:11] | 102.1 | [{"value": 102.1, "product": "FC=1C=C2CCC(=C(C2=CC1)C(=O)OC)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | null | null | 12.66 g (316 mmol) of 60% sodium hydride in oil, 900 ml of toluene and 17.69 ml (210 mmol) of dimethyl carbonate are introduced into a 2 l reactor. The reaction mixture is stirred at reflux for 1 h. A solution of 19 g (115 mmol) of 6-fluoro-3,4-dihydro-1H-naphthalen-2-one in 350 ml of toluene is subsequently added. The... | 10.6084/m9.figshare.5104873.v1 | null | Carbonic Ester.Ketone | Ester.Enol | c1ccc2c(c1)CCCC2 | C1=Cc2ccccc2CC1 | C1=Cc2ccccc2CC1 | HO- | O.C1(=CC=CC=C1)C | 0 | null | COC(=O)OC.O=C1CCc2cc(F)ccc2C1>O.C1(=CC=CC=C1)C>COC(=O)C1=C(O)CCc2cc(F)ccc21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-36ae9e63c57349b388155145f013119f | COC(=O)OC.O=C1CCc2cc(Cl)ccc2C1>>COC(=O)C1=C(O)CCc2cc(Cl)ccc21 | C(C)(=O)O.[H-].[Na+].C(OC)(OC)=O.ClC=1C=C2CCC(CC2=CC1)=O>>ClC=1C=C2CCC(=C(C2=CC1)C(=O)OC)O | CO[C:3]([O:2][CH3:1])=[O:4].[CH2:5]1[C:6](=[O:7])[CH2:8][CH2:9][c:10]2[cH:11][c:12]([Cl:13])[cH:14][cH:15][c:16]21>>[CH3:1][O:2][C:3](=[O:4])[C:5]1=[C:6]([OH:7])[CH2:8][CH2:9][c:10]2[cH:11][c:12]([Cl:13])[cH:14][cH:15][c:16]21 | COC(=O)OC.O=C1CCc2cc(Cl)ccc2C1 | COC(=O)C1=C(O)CCc2cc(Cl)ccc21 | null | null | O.C1(=CC=CC=C1)C | Acylation | OtherReaction | 5d9c81ecf4037759bc3774402d21bcd515500b9416fbff21a1b406ba2c541e6c | a17e333db4ac4c45047cd486becf44e6d06842c4a345b2a174026b25ac18fe66 | C1=Cc2ccccc2CC1 | C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C;D1;H3:4].[O;H0;D1;+0:5]=[C;H0;D3;+0:6]1-[C:7]-[C:8]-[c:9]:[c:10](:[c:11])-[CH2;D2;+0:12]-1>>[C;D1;H3:4]-[#8:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C;H0;D3;+0:12]1=[C;H0;D3;+0:6](-[OH;D1;+0:5])-[C:7]-[C:8]-[c:9]:[c:10]-1:[c:11] | 63.8 | [{"value": 63.8, "product": "ClC=1C=C2CCC(=C(C2=CC1)C(=O)OC)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | null | null | 10.1 g (252 mmol) of 60% sodium hydride in oil, 621 ml of toluene and 14.18 ml (163 mmol) of dimethyl carbonate are introduced into a 2 l reactor. The reaction mixture is stirred at reflux for 1 h. A solution of 15.2 g (84 mmol) of 6-chloro-3,4-dihydro-1H-naphthalen-2-one in 268 ml of toluene is subsequently added. The... | 10.6084/m9.figshare.5104873.v1 | null | Carbonic Ester.Ketone | Ester.Enol | c1ccc2c(c1)CCCC2 | C1=Cc2ccccc2CC1 | C1=Cc2ccccc2CC1 | HO- | O.C1(=CC=CC=C1)C | 0 | null | COC(=O)OC.O=C1CCc2cc(Cl)ccc2C1>O.C1(=CC=CC=C1)C>COC(=O)C1=C(O)CCc2cc(Cl)ccc21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-593b8763859d48099f2fdd0590072d81 | COC(=O)OC.COc1ccc2c(c1)CC(=O)CC2>>COC(=O)C1=C(O)CCc2cc(OC)ccc21 | C(C)(=O)O.[H-].[Na+].C(OC)(OC)=O.COC1=CC=C2CCC(CC2=C1)=O>>COC=1C=C2CCC(=C(C2=CC1)C(=O)OC)O | CO[C:3]([O:2][CH3:1])=[O:4].[CH2:5]1[C:6](=[O:7])[CH2:8][CH2:9][c:17]2[c:10]1[cH:11][c:12]([O:13][CH3:14])[cH:15][cH:16]2>>[CH3:1][O:2][C:3](=[O:4])[C:5]1=[C:6]([OH:7])[CH2:8][CH2:9][c:10]2[cH:11][c:12]([O:13][CH3:14])[cH:15][cH:16][c:17]21 | COC(=O)OC.COc1ccc2c(c1)CC(=O)CC2 | COC(=O)C1=C(O)CCc2cc(OC)ccc21 | null | null | O.C1(=CC=CC=C1)C.C(Cl)Cl.CCCCCCC | Acylation | OtherReaction | 5d9c81ecf4037759bc3774402d21bcd515500b9416fbff21a1b406ba2c541e6c | a17e333db4ac4c45047cd486becf44e6d06842c4a345b2a174026b25ac18fe66 | C1=Cc2ccccc2CC1 | C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C;D1;H3:4].[O;H0;D1;+0:5]=[C;H0;D3;+0:6]1-[C:7]-[CH2;D2;+0:8]-[c;H0;D3;+0:9]2:[c:10]:[c:11]:[c:12]:[c:13]:[c;H0;D3;+0:14]:2-[CH2;D2;+0:15]-1>>[C;D1;H3:4]-[#8:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C;H0;D3;+0:15]1=[C;H0;D3;+0:6](-[OH;D1;+0:5])-[C:7]-[CH2;D2;+0:8]-[c;H0;D3;+0:14]2:[c:13... | null | [] | 0 | CELSIUS | null | null | 3.4 g (85.12 mmol) of 60% sodium hydride in oil, 180 ml of toluene and 4.78 ml (56.75 mmol) of dimethyl carbonate are introduced into a 1 l reactor. The reaction mixture is stirred at reflux for 1 h. A solution of 5 g (28.37 mmol) of 7-methoxy-3,4-dihydro-1H-naphthalen-2-one in 100 ml of toluene is subsequently added. ... | 10.6084/m9.figshare.5104873.v1 | null | Carbonic Ester.Ketone | Ester.Enol | c1ccc2c(c1)CCCC2 | C1=Cc2ccccc2CC1 | C1=Cc2ccccc2CC1 | HO- | O.C1(=CC=CC=C1)C.C(Cl)Cl.CCCCCCC | 0 | null | COC(=O)OC.COc1ccc2c(c1)CC(=O)CC2>O.C1(=CC=CC=C1)C.C(Cl)Cl.CCCCCCC>COC(=O)C1=C(O)CCc2cc(OC)ccc21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-5adedddb5d9c4d5195e95bda36137964 | CC(C)N(C(=O)Oc1nn(-c2ccncc2)c2c1-c1ccc(Cl)cc1CC2)C(C)C>>CC(C)N(C(=O)Oc1nn(-c2ccncc2)c2ccc3cc(Cl)ccc3c12)C(C)C.Cl | C(C)(C)N(C(OC1=NN(C=2CCC3=C(C12)C=CC(=C3)Cl)C3=CC=NC=C3)=O)C(C)C.BrN1C(CCC1=O)=O.N(=NC(C#N)(C)C)C(C#N)(C)C>>Cl.C(C)(C)N(C(OC1=NN(C=2C=CC3=C(C12)C=CC(=C3)Cl)C3=CC=NC=C3)=O)C(C)C | [CH3:1][CH:2]([CH3:3])[N:4]([C:5](=[O:6])[O:7][c:8]1[n:9][n:10](-[c:11]2[cH:12][cH:13][n:14][cH:15][cH:16]2)[c:17]2[c:27]1-[c:26]1[c:20]([cH:21][c:22]([Cl:23])[cH:24][cH:25]1)[CH2:19][CH2:18]2)[CH:28]([CH3:29])[CH3:30]>>[CH3:1][CH:2]([CH3:3])[N:4]([C:5](=[O:6])[O:7][c:8]1[n:9][n:10](-[c:11]2[cH:12][cH:13][n:14][cH:15][... | CC(C)N(C(=O)Oc1nn(-c2ccncc2)c2c1-c1ccc(Cl)cc1CC2)C(C)C | CC(C)N(C(=O)Oc1nn(-c2ccncc2)c2ccc3cc(Cl)ccc3c12)C(C)C.Cl | null | null | Cl.C(C)(C)O.C(Cl)(Cl)(Cl)Cl | Miscellaneous | OtherReaction | 090fe45c3b84079cbdfd7b82e205a304c6ad82109b20fd38e0a4c736d914bfda | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | c1ccc2c(c1)ccc1c2cnn1-c1ccncc1 | [#7:1]-[C:2](=[O;D1;H0:3])-[#8:4]-[c:5]1:[#7;a:6]:[#7;a:7](-[c:8]):[c:9]2:[c;H0;D3;+0:10]:1-[c;H0;D3;+0:11](:[c:12]:[c:13]):[c:14](:[c:15])-[CH2;D2;+0:16]-[CH2;D2;+0:17]-2>>[#7:1]-[C:2](=[O;D1;H0:3])-[#8:4]-[c:5]1:[#7;a:6]:[#7;a:7](-[c:8]):[c:9]2:[cH;D2;+0:17]:[cH;D2;+0:16]:[c:14](:[c:15]):[c;H0;D3;+0:11](:[c:12]:[c:13... | 153.8 | [{"value": 153.8, "product": "Cl.C(C)(C)N(C(OC1=NN(C=2C=CC3=C(C12)C=CC(=C3)Cl)C3=CC=NC=C3)=O)C(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 1.65 g (3.38 mmol) of 7-chloro-4,5-dihydro-3-(pyrid-4-yl)-3H-benzo[e]indazol-1-yl N,N-diisopropylcarbamate, prepared according to the method described in Example 5, 1.105 g (6.21 mmol) of N-bromosuccinimide and 0.127 g (0.78 mmol) of 2,2′-azobis(2-methylpropionitrile) are added to a 100 ml reactor. The mixture, dissolv... | 10.6084/m9.figshare.5104873.v1 | null | null | null | c1ccc2c(c1)CCc1n[nH]cc12 | c1ccc2c(c1)ccc1n[nH]cc12 | c1ccncc1.c1ccc2c(c1)ccc1n[nH]cc12 | Other | Cl.C(C)(C)O.C(Cl)(Cl)(Cl)Cl | null | null | CC(C)N(C(=O)Oc1nn(-c2ccncc2)c2c1-c1ccc(Cl)cc1CC2)C(C)C>Cl.C(C)(C)O.C(Cl)(Cl)(Cl)Cl>CC(C)N(C(=O)Oc1nn(-c2ccncc2)c2ccc3cc(Cl)ccc3c12)C(C)C.Cl |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-3654749bd2124ffea1d495cab9ceb180 | CN(CCO)Cc1ccccc1>>CN(CC=O)Cc1ccccc1 | N1=CC=CC=C1.S(=O)(=O)=O.C(C1=CC=CC=C1)N(CCO)C.CCN(C(C)C)C(C)C.CS(=O)C>>C(C1=CC=CC=C1)N(C)CC=O | [CH3:1][N:2]([CH2:3][CH2:4][OH:5])[CH2:6][c:7]1[cH:8][cH:9][cH:10][cH:11][cH:12]1>>[CH3:1][N:2]([CH2:3][CH:4]=[O:5])[CH2:6][c:7]1[cH:8][cH:9][cH:10][cH:11][cH:12]1 | CN(CCO)Cc1ccccc1 | CN(CC=O)Cc1ccccc1 | null | null | C(Cl)Cl | Oxidation | Oxidation or Dehydrogenation of Alcohols to Aldehydes and Ketones | 41bfa9deea81b465c88ad21fdfb64a2e1ba29490558cf430df132cb98b4a538b | 0a03c6724c1862e8f86d4a463afda55b8e067dc6cb42597b472eb7cabc03eda3 | c1ccccc1 | [#7:1]-[C:2]-[CH2;D2;+0:3]-[OH;D1;+0:4]>>[#7:1]-[C:2]-[CH;D2;+0:3]=[O;H0;D1;+0:4] | null | [] | -10 | CELSIUS | 2 | HOUR | To a 3-necked 2-L flask was added N-benzyl-N-methylethanolamine (30.5 g, 0.182 mol), DCM (0.5 L), DIPEA (95 mL, 0.546 mol) and DMSO (41 mL, 0.728 mol). Using an ice bath, the mixture was cooled to about −10° C. and sulfur trioxide pyridine-complex (87 g, 0.546 mol) was added in 4 portions over 5 minute intervals. The r... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | Aldehyde | null | null | c1ccccc1 | null | C(Cl)Cl | -10 | 2 | CN(CCO)Cc1ccccc1>C(Cl)Cl>CN(CC=O)Cc1ccccc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-835950a0473148e2ba014fda33faac7f | COC(OC)N(C)C.Nc1nc(Br)cnc1Br>>CN(C)C=Nc1nc(Br)cnc1Br | BrC=1C(=NC(=CN1)Br)N.COC(N(C)C)OC>>BrC=1C(=NC(=CN1)Br)N=CN(C)C | CO[CH:4](OC)[N:2]([CH3:1])[CH3:3].[NH2:5][c:6]1[n:7][c:8]([Br:9])[cH:10][n:11][c:12]1[Br:13]>>[CH3:1][N:2]([CH3:3])[CH:4]=[N:5][c:6]1[n:7][c:8]([Br:9])[cH:10][n:11][c:12]1[Br:13] | COC(OC)N(C)C.Nc1nc(Br)cnc1Br | CN(C)C=Nc1nc(Br)cnc1Br | null | null | C(C)O | Heteroatom Alkylation and Arylation | OtherReaction | 0d701f00585e4f39a6a7fc9a495a6e4c12bb39eb0ddc06ef90888eddc323e4b7 | e5ad6b21478dc075562b413728aa025da8232f58653a7afd9501cb514659723b | c1cnccn1 | C-O-[CH;D3;+0:1](-O-C)-[#7:2](-[C;D1;H3:3])-[C;D1;H3:4].[Br;D1;H0:5]-[c:6]1:[#7;a:7]:[c:8]:[c:9]:[#7;a:10]:[c:11]:1-[NH2;D1;+0:12]>>[Br;D1;H0:5]-[c:6]1:[#7;a:7]:[c:8]:[c:9]:[#7;a:10]:[c:11]:1-[N;H0;D2;+0:12]=[CH;D2;+0:1]-[#7:2](-[C;D1;H3:3])-[C;D1;H3:4] | 99.3 | [{"value": 99.3, "product": "BrC=1C(=NC(=CN1)Br)N=CN(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 3,6-dibromo-pyrazin-2-ylamine (15.37 g, 60.80 mmol) and N,N-dimethylformamide dimethyl acetal (10.1 mL, 76.00 mmol), suspended in ethanol (150 mL), is refluxed for 2 hours. The reaction mixture is evaporated in vacuo affording the title compound (18.6 g). 1H-NMR (400 MHz, CDCl3) δ(ppm) 3.20 (s, 3H), 3.21 (... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether.Primary amine | null | null | null | c1cnccn1 | HO- | C(C)O | null | null | COC(OC)N(C)C.Nc1nc(Br)cnc1Br>C(C)O>CN(C)C=Nc1nc(Br)cnc1Br |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-1e737b89f157485b802b28ad6ae009a4 | CN(C)C=Nc1nc(Br)cnc1Br.NO>>ON=CNc1nc(Br)cnc1Br | BrC=1C(=NC(=CN1)Br)N=CN(C)C.Cl.NO>>BrC=1C(=NC(=CN1)Br)NC=NO | CN(C)[CH:3]=[N:4][c:5]1[n:6][c:7]([Br:8])[cH:9][n:10][c:11]1[Br:12].[OH:1][NH2:2]>>[OH:1][N:2]=[CH:3][NH:4][c:5]1[n:6][c:7]([Br:8])[cH:9][n:10][c:11]1[Br:12] | CN(C)C=Nc1nc(Br)cnc1Br.NO | ON=CNc1nc(Br)cnc1Br | null | null | CO | Heteroatom Alkylation and Arylation | OtherReaction | 9c6166fd7e5a817bf213fd9daccfae72f646d2b10a52b5122c4c1be4856f9ac0 | ecd935dc844075fc6e2817ede9c8c1363134a018b1e26143e72f4dc910dff438 | c1cnccn1 | C-N(-C)-[CH;D2;+0:1]=[N;H0;D2;+0:2]-[c:3]1:[#7;a:4]:[c:5]:[c:6]:[#7;a:7]:[c:8]:1-[Br;D1;H0:9].[NH2;D1;+0:10]-[O;D1;H1:11]>>[Br;D1;H0:9]-[c:8]1:[#7;a:7]:[c:6]:[c:5]:[#7;a:4]:[c:3]:1-[NH;D2;+0:2]-[CH;D2;+0:1]=[N;H0;D2;+0:10]-[O;D1;H1:11] | 97 | [{"value": 97.0, "product": "BrC=1C(=NC(=CN1)Br)NC=NO", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 16 | HOUR | To a solution of N′-(3,6-dibromo-pyrazin-2-yl)-N,N-dimethylformamidine (18.6 g, 60.80 mmol) in methanol (200 mL) is added hydroxylamine hydrochloride (5.91 g, 85.12 mmol) in one portion. The reaction is stirred at room temperature for 16 hours. The solvent is evaporated and the solid residue is treated with cold (ice c... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Tertiary amine | Secondary amine.Oxime | null | null | c1cnccn1 | Other | CO | null | 16 | CN(C)C=Nc1nc(Br)cnc1Br.NO>CO>ON=CNc1nc(Br)cnc1Br |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-8435ddd943c94774ab8a007e9038c22c | ON=CNc1nc(Br)cnc1Br>>Brc1ncc(Br)n2ncnc12 | BrC=1C(=NC(=CN1)Br)NC=NO.C(=O)(O)[O-].[Na+]>>BrC1=CN=C(C=2N1N=CN2)Br | O[N:8]=[CH:9][NH:10][c:11]1[c:2]([Br:1])[n:3][cH:4][c:5]([Br:6])[n:7]1>>[Br:1][c:2]1[n:3][cH:4][c:5]([Br:6])[n:7]2[n:8][cH:9][n:10][c:11]12 | ON=CNc1nc(Br)cnc1Br | Brc1ncc(Br)n2ncnc12 | null | null | O | Aromatic Heterocycle Formation | OtherReaction | 1fa44d6fb59f874198f0796e8eb1848cb936176048c11601bbc53c105abaffc3 | c1d239b36a16d8c63e1df13f889e3523ec358c146b56c8c2a09aa8afeeaad4d2 | c1cn2ncnc2cn1 | O-[N;H0;D2;+0:1]=[CH;D2;+0:2]-[NH;D2;+0:3]-[c:4]1:[n;H0;D2;+0:5]:[c:6](-[Br;D1;H0:7]):[c:8]:[#7;a:9]:[c:10]:1-[Br;D1;H0:11]>>[Br;D1;H0:11]-[c:10]1:[#7;a:9]:[c:8]:[c:6](-[Br;D1;H0:7]):[n;H0;D3;+0:5]2:[n;H0;D2;+0:1]:[cH;D2;+0:2]:[n;H0;D2;+0:3]:[c:4]:1:2 | 62.1 | [{"value": 62.1, "product": "BrC1=CN=C(C=2N1N=CN2)Br", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1.75 | HOUR | N-(3,6-dibromo-pyrazin-2-yl)-N′-hydroxyformamidine (17.4 mg, 58.80 mmol) is treated with polyphosphoric acid (150 g) for one hour at 50° C. and then for 1.75 hours at 70° C. After cooling to room temperature, water is added to the reaction mixture. The resultant suspension is brought to pH 8 by careful addition of soli... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amine.Oxime | null | c1cnccn1 | c1cn2ncnc2cn1 | c1cn2ncnc2cn1 | HO- | O | null | 1.75 | ON=CNc1nc(Br)cnc1Br>O>Brc1ncc(Br)n2ncnc12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-3027a9cb758e4615b7dfccaa86d4073f | Brc1ncc(Br)n2ncnc12.Nc1ccc(N2CCOCC2)cc1>>Brc1cnc(Nc2ccc(N3CCOCC3)cc2)c2ncnn12 | BrC1=CN=C(C=2N1N=CN2)Br.C1COCCN1C2=CC=C(C=C2)N.C(C)N(C(C)C)C(C)C>>BrC1=CN=C(C=2N1N=CN2)NC2=CC=C(C=C2)N2CCOCC2 | Br[c:5]1[n:4][cH:3][c:2]([Br:1])[n:23]2[c:19]1[n:20][cH:21][n:22]2.[NH2:6][c:7]1[cH:8][cH:9][c:10]([N:11]2[CH2:12][CH2:13][O:14][CH2:15][CH2:16]2)[cH:17][cH:18]1>>[Br:1][c:2]1[cH:3][n:4][c:5]([NH:6][c:7]2[cH:8][cH:9][c:10]([N:11]3[CH2:12][CH2:13][O:14][CH2:15][CH2:16]3)[cH:17][cH:18]2)[c:19]2[n:20][cH:21][n:22][n:23]12 | Brc1ncc(Br)n2ncnc12.Nc1ccc(N2CCOCC2)cc1 | Brc1cnc(Nc2ccc(N3CCOCC3)cc2)c2ncnn12 | null | null | CC(C)O | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | aecfb0ede2c5d7901fea69101287828edf21f7a6e48b6ff83fe43de0688f1ef1 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1cn2ncnc2c(Nc2ccc(N3CCOCC3)cc2)n1 | Br-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]:[#7;a:5]2:[#7;a:6]:[c:7]:[#7;a:8]:[c:9]:2:1.[NH2;D1;+0:10]-[c:11](:[c:12]):[c:13]>>[c:12]:[c:11](-[NH;D2;+0:10]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]:[#7;a:5]2:[#7;a:6]:[c:7]:[#7;a:8]:[c:9]:2:1):[c:13] | 94 | [{"value": 94.0, "product": "BrC1=CN=C(C=2N1N=CN2)NC2=CC=C(C=C2)N2CCOCC2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 93.8, "product": "BrC1=CN=C(C=2N1N=CN2)NC2=CC=C(C=C2)N2CCOCC2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 5,8-dibromo-[1,2,4]triazolo[1,5-a]pyrazine (123 mg, 443 μmol), 4-(4-morpholino)aniline (118 mg. 0.664 mmol) and N-ethyldiisopropylamine (116 mL, 0.664 mmol) is heated at reflux in 2-propanol (3 mL) for 4.5 hours. The reaction mixture is evaporated to dryness and the residue partitioned between dichlorometh... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cn2ncnc2cn1 | c1cn2ncnc2cn1 | c1ccccc1.C1COCC[NH]1.c1cn2ncnc2cn1 | HBr | CC(C)O | null | null | Brc1ncc(Br)n2ncnc12.Nc1ccc(N2CCOCC2)cc1>CC(C)O>Brc1cnc(Nc2ccc(N3CCOCC3)cc2)c2ncnn12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-36290199d22b4ef481537591340ea0ba | CN1CCN(c2ccc(Nc3ncc(Br)n4ncnc34)cc2)CC1.COc1cc(B(O)O)ccn1>>COc1cc(-c2cnc(Nc3ccc(N4CCN(C)CC4)cc3)c3ncnn23)ccn1 | C(=O)([O-])[O-].[Na+].[Na+].BrC1=CN=C(C=2N1N=CN2)NC2=CC=C(C=C2)N2CCN(CC2)C.COC1=NC=CC(=C1)B(O)O>>COC1=NC=CC(=C1)C1=CN=C(C=2N1N=CN2)NC2=CC=C(C=C2)N2CCN(CC2)C | Br[c:6]1[cH:7][n:8][c:9]([NH:10][c:11]2[cH:12][cH:13][c:14]([N:15]3[CH2:16][CH2:17][N:18]([CH3:19])[CH2:20][CH2:21]3)[cH:22][cH:23]2)[c:24]2[n:25][cH:26][n:27][n:28]12.OB(O)[c:5]1[cH:4][c:3]([O:2][CH3:1])[n:31][cH:30][cH:29]1>>[CH3:1][O:2][c:3]1[cH:4][c:5](-[c:6]2[cH:7][n:8][c:9]([NH:10][c:11]3[cH:12][cH:13][c:14]([N:1... | CN1CCN(c2ccc(Nc3ncc(Br)n4ncnc34)cc2)CC1.COc1cc(B(O)O)ccn1 | COc1cc(-c2cnc(Nc3ccc(N4CCN(C)CC4)cc3)c3ncnn23)ccn1 | 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 | CN(C)C=O.O1CCOCC1 | C-C Coupling | Suzuki coupling with boronic acids | 5d08686f43da8e30538f859764d1c446b3e676ebc229f2d3adde0518ff14c3b0 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1cc(-c2cnc(Nc3ccc(N4CCNCC4)cc3)c3ncnn23)ccn1 | Br-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[c:4]:[c:5]2:[#7;a:6]:[c:7]:[#7;a:8]:[#7;a:9]:2:1.O-B(-O)-[c;H0;D3;+0:10]1:[c:11]:[c:12]:[#7;a:13]:[c:14](-[#8:15]):[c:16]:1>>[#8:15]-[c:14]1:[#7;a:13]:[c:12]:[c:11]:[c;H0;D3;+0:10](-[c;H0;D3;+0:1]2:[c:2]:[#7;a:3]:[c:4]:[c:5]3:[#7;a:6]:[c:7]:[#7;a:8]:[#7;a:9]:3:2):[c:16]:1 | 47 | [{"value": 47.0, "product": "COC1=NC=CC(=C1)C1=CN=C(C=2N1N=CN2)NC2=CC=C(C=C2)N2CCN(CC2)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 46.6, "product": "COC1=NC=CC(=C1)C1=CN=C(C=2N1N=CN2)NC2=CC=C(C=C2)N2CCN(CC2)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | This compound may be prepared using methods as described for Compound 6, step 4 using (5-bromo-[1,2,4]triazolo[1,5-a]pyrazin-8-yl)-[4-(4-methyl-piperazin-1-yl)-phenyl]-amine (80 mg, 0.206 mmol), 2-methoxypyridine-4-boronic acid (63 mg, 0.412 mmol), Pd(PPh3)4 (0.052 mmol) and 1.5N Na2CO3 (1.1 mL, 1.65 mmol) in 2:1 DMF/d... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1cn2ncnc2cn1.c1ccncc1 | c1ccncc1.c1cn2ncnc2cn1 | c1ccncc1.c1ccccc1.C1C[NH]CC[NH]1.c1cn2ncnc2cn1 | HBr.B | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.CN(C)C=O.O1CCOCC1 | null | null | CN1CCN(c2ccc(Nc3ncc(Br)n4ncnc34)cc2)CC1.COc1cc(B(O)O)ccn1>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.CN(C)C=O.O1CCOCC1>COc1cc(-c2cnc(Nc3ccc(N4CCN(C)CC4)cc3)c3ncnn23)ccn1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-142319d9b5d94c9b8cb3e693faf50430 | Brc1ncc(Br)n2ncnc12.CN1CCN(c2ccc(N)cc2)CC1>>CN1CCN(c2ccc(Nc3ncc(Br)n4ncnc34)cc2)CC1 | BrC1=CN=C(C=2N1N=CN2)Br.CN1CCN(CC1)C1=CC=C(C=C1)N.C(C)N(C(C)C)C(C)C>>BrC1=CN=C(C=2N1N=CN2)NC2=CC=C(C=C2)N2CCN(CC2)C | Br[c:11]1[n:12][cH:13][c:14]([Br:15])[n:16]2[n:17][cH:18][n:19][c:20]12.[CH3:1][N:2]1[CH2:3][CH2:4][N:5]([c:6]2[cH:7][cH:8][c:9]([NH2:10])[cH:21][cH:22]2)[CH2:23][CH2:24]1>>[CH3:1][N:2]1[CH2:3][CH2:4][N:5]([c:6]2[cH:7][cH:8][c:9]([NH:10][c:11]3[n:12][cH:13][c:14]([Br:15])[n:16]4[n:17][cH:18][n:19][c:20]34)[cH:21][cH:22... | Brc1ncc(Br)n2ncnc12.CN1CCN(c2ccc(N)cc2)CC1 | CN1CCN(c2ccc(Nc3ncc(Br)n4ncnc34)cc2)CC1 | null | null | CC(C)O | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | aecfb0ede2c5d7901fea69101287828edf21f7a6e48b6ff83fe43de0688f1ef1 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1cn2ncnc2c(Nc2ccc(N3CCNCC3)cc2)n1 | Br-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]:[#7;a:5]2:[#7;a:6]:[c:7]:[#7;a:8]:[c:9]:2:1.[NH2;D1;+0:10]-[c:11](:[c:12]):[c:13]>>[c:12]:[c:11](-[NH;D2;+0:10]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]:[#7;a:5]2:[#7;a:6]:[c:7]:[#7;a:8]:[c:9]:2:1):[c:13] | 50.4 | [{"value": 50.4, "product": "BrC1=CN=C(C=2N1N=CN2)NC2=CC=C(C=C2)N2CCN(CC2)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 5,8-dibromo-[1,2,4]triazolo[1,5-a]pyrazine (2 g, 7.20 mmol), 4-(4-methyl-piperazin-1-yl)-phenylamine (1.65 g, 8.64 mmol) and N-ethyldiisopropyl-amine (1.5 mL, 8.64 mmol) is heated at 80° C. in 2-propanol (50 mL) for 8 hours. The reaction mixture is evaporated to dryness and the residue partitioned between ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cn2ncnc2cn1 | c1cn2ncnc2cn1 | C1C[NH]CC[NH]1.c1ccccc1.c1cn2ncnc2cn1 | HBr | CC(C)O | null | null | Brc1ncc(Br)n2ncnc12.CN1CCN(c2ccc(N)cc2)CC1>CC(C)O>CN1CCN(c2ccc(Nc3ncc(Br)n4ncnc34)cc2)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-bf0b15a623a643ca8612d5bf1a657bbb | O=C(O)c1sccc1Br>>NC(=O)c1cc(Br)cs1 | BrC1=C(SC=C1)C(=O)O.Cl.C(C)N=C=NCCCN(C)C.O.ON1N=NC2=C1C=CC=C2.O>>BrC=1C=C(SC1)C(=O)N | O[C:2](=[O:3])[c:4]1[c:6]([Br:7])[cH:5][cH:8][s:9]1>>[NH2:1][C:2](=[O:3])[c:4]1[cH:5][c:6]([Br:7])[cH:8][s:9]1 | O=C(O)c1sccc1Br | NC(=O)c1cc(Br)cs1 | null | null | CN(C)C=O | Functional Group Interconversion | OtherReaction | 88c98fffcc34d527a612bb0d59e9cb29f690664f80d146dcce3712eb24cd731f | 5714ff853ee51aa1194ed7b37a31c645a0cb082d2b538f94dd2497088a2eecf7 | c1ccsc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c;H0;D3;+0:3]1:[#16;a:4]:[cH;D2;+0:5]:[cH;D2;+0:6]:[c;H0;D3;+0:7]:1-[Br;D1;H0:8]>>[Br;D1;H0:8]-[c;H0;D3;+0:7]1:[cH;D2;+0:6]:[c;H0;D3;+0:3](-[C;H0;D3;+0:1](-[N;D1;H2:9])=[O;D1;H0:2]):[#16;a:4]:[cH;D2;+0:5]:1 | 78 | [{"value": 78.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 5 | HOUR | A solution of 4 bromo-thiophene-2-carboxylic acid (2.0 g, 9.66 mmol), 1-ethyl-3-(3′-dimethylaminopropyl)carbodiimide hydrochloride (2.04 g, 10.63 mmol) and 1-hydroxybenzotriazole hydrate (1.44 g, 10.63 mmol) in DMF (20 mL) is stirred at room temperature for 2 hours. The reaction mixture is then cooled to 0° C. and aq. ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Carboxylic acid | Aromatic halide.Primary amide | c1ccsc1 | c1ccsc1 | c1ccsc1 | null | CN(C)C=O | 0 | 5 | O=C(O)c1sccc1Br>CN(C)C=O>NC(=O)c1cc(Br)cs1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-44cfe51f98c9404a98626aa029bb074a | N.O=C(O)c1ccc(Br)s1>>NC(=O)c1ccc(Br)s1 | N.BrC1=CC=C(S1)C(=O)O.O.ON1N=NC2=C1C=CC=C2.C(C)N=C=NCCCN(C)C>>BrC1=CC=C(S1)C(=O)N | [NH3:1].O[C:2](=[O:3])[c:4]1[cH:5][cH:6][c:7]([Br:8])[s:9]1>>[NH2:1][C:2](=[O:3])[c:4]1[cH:5][cH:6][c:7]([Br:8])[s:9]1 | N.O=C(O)c1ccc(Br)s1 | NC(=O)c1ccc(Br)s1 | null | null | CN(C)C=O | Acylation | Carboxylic acid to amide conversion | 1283aef55d7ee699f097a8e5267689198c76ba671644401547f902657820236d | cb0a71c3fb37a76e96fbd81aae6f95a28398a03d1ad2c8e877085e735efb98f1 | c1ccsc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[#16;a:5]:[c:6].[NH3;D0;+0:7]>>[NH2;D1;+0:7]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[#16;a:5]:[c:6] | 84.2 | [{"value": 84.0, "product": "BrC1=CC=C(S1)C(=O)N", "details": "PERCENTYIELD", "is_desired": false}, {"value": 84.2, "product": "BrC1=CC=C(S1)C(=O)N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 8 | HOUR | A solution of 5-bromo-thiophene-2-carboxylic acid (4.51 g, 21.78 mmol), 3-hydroxybenzotriazole hydrate (3.24 g, 23.96 mmol), 1-ethyl-3-(3′-dimethylaminopropyl)carbodiimide (4.6 g, 23.96 mmol) in DMF (70 mL) is stirred at room temperature for 2 hours. The reaction mixture is then cooled to 0° C. and aq. 35% NH3 (2.2 mL)... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Primary amide | null | null | c1ccsc1 | HO- | CN(C)C=O | 0 | 8 | N.O=C(O)c1ccc(Br)s1>CN(C)C=O>NC(=O)c1ccc(Br)s1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-27d59b0c73f54c99a026e5b3704acb56 | CC1(C)OB(c2ccc(C(N)=O)s2)OC1(C)C.CN1CCN(c2ccc(Nc3ncc(-c4csc(C(N)=O)c4)n4ncnc34)cc2)CC1>>CN1CCN(c2ccc(Nc3ncc(-c4ccc(C(N)=O)s4)n4ncnc34)cc2)CC1.N | CC1(OB(OC1(C)C)C1=CC=C(S1)C(=O)N)C.CN1CCN(CC1)C1=CC=C(C=C1)NC=1C=2N(C(=CN1)C=1C=C(SC1)C(=O)N)N=CN2.C(=O)([O-])[O-].[Na+].[Na+].CN1CCN(CC1)C1=CC=C(C=C1)N>>N.CN1CCN(CC1)C1=CC=C(C=C1)NC=1C=2N(C(=CN1)C1=CC=C(S1)C(=O)N)N=CN2 | CC1(C)OB(c2[cH:16][cH:17][c:18]([C:19]([NH2:20])=[O:21])[s:22]2)OC1(C)C.O=C(c1c[c:15](-[c:14]2[cH:13][n:12][c:11]([NH:10][c:9]3[cH:8][cH:7][c:6]([N:5]4[CH2:4][CH2:3][N:2]([CH3:1])[CH2:31][CH2:30]4)[cH:29][cH:28]3)[c:27]3[n:23]2[n:24][cH:25][n:26]3)cs1)[NH2:32]>>[CH3:1][N:2]1[CH2:3][CH2:4][N:5]([c:6]2[cH:7][cH:8][c:9]([... | CC1(C)OB(c2ccc(C(N)=O)s2)OC1(C)C.CN1CCN(c2ccc(Nc3ncc(-c4csc(C(N)=O)c4)n4ncnc34)cc2)CC1 | CN1CCN(c2ccc(Nc3ncc(-c4ccc(C(N)=O)s4)n4ncnc34)cc2)CC1.N | 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 | Miscellaneous | OtherReaction | 7c91011d7ca932b4650404ee0f5c9c5b345e30ce123b75474c550eb6fcfd4df2 | f3f7f26bbd316ddb41ef1d9256d6e3eab68cee0318289c68e4524d92797ff759 | c1csc(-c2cnc(Nc3ccc(N4CCNCC4)cc3)c3ncnn23)c1 | C-C1(-C)-O-B(-c2:[cH;D2;+0:1]:[c:2]:[c:3](-[C:4](-[N;D1;H2:5])=[O;D1;H0:6]):[s;H0;D2;+0:7]:2)-O-C-1(-C)-C.O=C(-[NH2;D1;+0:8])-c1:c:[c;H0;D3;+0:9](-[c:10]2:[c:11]:[#7;a:12]:[c:13]:[c:14]3:[#7;a:15]:[c:16]:[#7;a:17]:[#7;a:18]:2:3):c:s:1>>[N;D1;H2:5]-[C:4](=[O;D1;H0:6])-[c:3]1:[c:2]:[cH;D2;+0:1]:[c;H0;D3;+0:9](-[c:10]2:[c... | 21 | [{"value": 21.0, "product": "CN1CCN(CC1)C1=CC=C(C=C1)NC=1C=2N(C(=CN1)C1=CC=C(S1)C(=O)N)N=CN2", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | This compound may be prepared using methods as described for Compound 6, step 4 using 5-bromo-[1,2,4]triazolo[1,5-a]pyrazin-8-yl)-[4-(4-methyl-piperazin-1-yl)-phenyl]-amine (100 mg, 0.258 mmol), 5-(4,4,5,5-tetramethyl-[1,3,2]dioxa-borolan-2-yl)-thiophene-2-carboxylic acid amide (130 mg, 0.516 mmol) and Pd(PPh3)4 (74 mg... | 10.6084/m9.figshare.5104873.v1 | null | Primary amide.Boronic ester | null | B1OCCO1.c1ccsc1.c1ccsc1 | c1ccsc1 | C1C[NH]CC[NH]1.c1ccccc1.c1ccsc1.c1cn2ncnc2cn1 | 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 | null | null | CC1(C)OB(c2ccc(C(N)=O)s2)OC1(C)C.CN1CCN(c2ccc(Nc3ncc(-c4csc(C(N)=O)c4)n4ncnc34)cc2)CC1>C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.O1CCOCC1>CN1CCN(c2ccc(Nc3ncc(-c4ccc(C(N)=O)s4)n4ncnc34)cc2)CC1... |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-1be6752f028e44bf8d127f68b503efe8 | Brc1cnc(Nc2ccc(N3CCOCC3)cc2)c2ncnn12.CN1CCN(c2ccc(Nc3ncc(-c4csc(C(N)=O)c4)n4ncnc34)cc2)CC1.Cc1[nH]ncc1B1OC(C)(C)C(C)(C)O1>>Cc1[nH]ncc1-c1cnc(Nc2ccc(N3CCOCC3)cc2)c2ncnn12.N | CC1=C(C=NN1)B1OC(C(O1)(C)C)(C)C.CN1CCN(CC1)C1=CC=C(C=C1)NC=1C=2N(C(=CN1)C=1C=C(SC1)C(=O)N)N=CN2.C(=O)([O-])[O-].[Na+].[Na+].BrC1=CN=C(C=2N1N=CN2)NC2=CC=C(C=C2)N2CCOCC2>>N.CC1=C(C=NN1)C1=CN=C(C=2N1N=CN2)NC2=CC=C(C=C2)N2CCOCC2 | Br[c:7]1[cH:8][n:9][c:10]([NH:11][c:12]2[cH:13][cH:14][c:15]([N:16]3[CH2:17][CH2:18][O:19][CH2:20][CH2:21]3)[cH:22][cH:23]2)[c:24]2[n:25][cH:26][n:27][n:28]12.CN1CCN(c2ccc(Nc3ncc(-c4csc(C(=O)[NH2:29])c4)n4ncnc34)cc2)CC1.CC1(C)OB([c:6]2[c:2]([CH3:1])[nH:3][n:4][cH:5]2)OC1(C)C>>[CH3:1][c:2]1[nH:3][n:4][cH:5][c:6]1-[c:7]1... | Brc1cnc(Nc2ccc(N3CCOCC3)cc2)c2ncnn12.CN1CCN(c2ccc(Nc3ncc(-c4csc(C(N)=O)c4)n4ncnc34)cc2)CC1.Cc1[nH]ncc1B1OC(C)(C)C(C)(C)O1 | Cc1[nH]ncc1-c1cnc(Nc2ccc(N3CCOCC3)cc2)c2ncnn12.N | 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 | OtherReaction | 5450a2db6e7305c45383870e931e62f9935b44015cf383067240af8b2a416783 | 96e5f3628c1bd4659dd3e9821904115decf673d0e8e42bb7900b7f521b084c51 | c1nc2c(Nc3ccc(N4CCOCC4)cc3)ncc(-c3cn[nH]c3)n2n1 | Br-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[c:4]:[c:5]2:[#7;a:6]:[c:7]:[#7;a:8]:[#7;a:9]:2:1.C-C1(-C)-O-B(-[c;H0;D3;+0:10]2:[c:11]:[#7;a:12]:[#7;a:13]:[c:14]:2-[C;D1;H3:15])-O-C-1(-C)-C.C-N1-C-C-N(-c2:c:c:c(-N-c3:n:c:c(-c4:c:s:c(-C(=O)-[NH2;D1;+0:16]):c:4):n4:n:c:n:c:3:4):c:c:2)-C-C-1>>[C;D1;H3:15]-[c:14]1:[#7;a:13]:[#7;a:12]:[... | 7.5 | [{"value": 7.5, "product": "CC1=C(C=NN1)C1=CN=C(C=2N1N=CN2)NC2=CC=C(C=C2)N2CCOCC2", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | This compound may be prepared using methods as described for Compound 6, step 4 using (5-bromo-[1,2,4]triazolo[1,5-a]pyrazin-8-yl)-(4-morpholin-4-yl-phenyl)-amine (0.2 g, 0.53 mmol), 5-methyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrazole (222 mg, 1.06 mmol), and Pd(PPh3)4 (0.154 mg, 0.134 mmol) in 1.5M N... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amide.Secondary amine.Tertiary amine.Tertiary amine.Boronic ester | null | c1cn2ncnc2cn1.C1CNCCN1.c1ccccc1.c1ccsc1.c1cn2ncnc2cn1.B1OCCO1.c1cn[nH]c1 | c1cn[nH]c1.c1cn2ncnc2cn1 | c1cn[nH]c1.c1ccccc1.C1COCC[NH]1.c1cn2ncnc2cn1 | HBr.B | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.O1CCOCC1 | null | null | Brc1cnc(Nc2ccc(N3CCOCC3)cc2)c2ncnn12.CN1CCN(c2ccc(Nc3ncc(-c4csc(C(N)=O)c4)n4ncnc34)cc2)CC1.Cc1[nH]ncc1B1OC(C)(C)C(C)(C)O1>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>Cc1[nH]ncc1-c1cnc(... |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e824f0d68eec45008eaf33f03d3aea81 | Brc1cnc(Nc2ccc(N3CCOCC3)cc2)c2ncnn12.CN1CCN(c2ccc(Nc3ncc(-c4csc(C(N)=O)c4)n4ncnc34)cc2)CC1>>NC(=O)c1cc(-c2cnc(Nc3ccc(N4CCOCC4)cc3)c3ncnn23)cs1 | C(=O)([O-])[O-].[Na+].[Na+].CN1CCN(CC1)C1=CC=C(C=C1)NC=1C=2N(C(=CN1)C=1C=C(SC1)C(=O)N)N=CN2.BrC1=CN=C(C=2N1N=CN2)NC2=CC=C(C=C2)N2CCOCC2.CC1(OB(OC1(C)C)C=1C=C(SC1)C(=O)N)C>>N1(CCOCC1)C1=CC=C(C=C1)NC=1C=2N(C(=CN1)C=1C=C(SC1)C(=O)N)N=CN2 | Br[c:7]1[cH:8][n:9][c:10]([NH:11][c:12]2[cH:13][cH:14][c:15]([N:16]3[CH2:17][CH2:18][O:19][CH2:20][CH2:21]3)[cH:22][cH:23]2)[c:24]2[n:25][cH:26][n:27][n:28]12.CN1CCN(c2ccc(Nc3ncc(-[c:6]4[cH:5][c:4]([C:2]([NH2:1])=[O:3])[s:30][cH:29]4)n4ncnc34)cc2)CC1>>[NH2:1][C:2](=[O:3])[c:4]1[cH:5][c:6](-[c:7]2[cH:8][n:9][c:10]([NH:1... | Brc1cnc(Nc2ccc(N3CCOCC3)cc2)c2ncnn12.CN1CCN(c2ccc(Nc3ncc(-c4csc(C(N)=O)c4)n4ncnc34)cc2)CC1 | NC(=O)c1cc(-c2cnc(Nc3ccc(N4CCOCC4)cc3)c3ncnn23)cs1 | 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 | OtherReaction | 611105c70cffe68ca772f63b3c7585081a4d3c0cedb754af02c62b3e48eb31ea | 29d6ca637af3bedb92e90114efa267a3e4e226d46d2cbc04aef1a3fdafc7a7e3 | c1nc2c(Nc3ccc(N4CCOCC4)cc3)ncc(-c3ccsc3)n2n1 | Br-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[c:4]:[c:5]2:[#7;a:6]:[c:7]:[#7;a:8]:[#7;a:9]:2:1.C-N1-C-C-N(-c2:c:c:c(-N-c3:n:c:c(-[c;H0;D3;+0:10]4:[c:11]:[#16;a:12]:[c:13](-[C:14](-[N;D1;H2:15])=[O;D1;H0:16]):[c:17]:4):n4:n:c:n:c:3:4):c:c:2)-C-C-1>>[N;D1;H2:15]-[C:14](=[O;D1;H0:16])-[c:13]1:[#16;a:12]:[c:11]:[c;H0;D3;+0:10](-[c;H0... | 37.4 | [{"value": 37.4, "product": "N1(CCOCC1)C1=CC=C(C=C1)NC=1C=2N(C(=CN1)C=1C=C(SC1)C(=O)N)N=CN2", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | This compound may be prepared using methods as described for Compound 6, step 4 using (5-bromo-[1,2,4]triazolo[1,5-a]pyrazin-8-yl)-(4-morpholin-4-yl-phenyl)-amine (0.2 g, 0.53 mmol), 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-thiophene-2-carboxylic acid amide (0.27 mg, 1.06 mmol), and Pd(PPh3)4 (0.15 mg, 0.133 mm... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine.Tertiary amine.Tertiary amine | null | c1cn2ncnc2cn1.C1CNCCN1.c1ccccc1.c1ccsc1.c1cn2ncnc2cn1 | c1ccsc1.c1cn2ncnc2cn1 | c1ccsc1.c1ccccc1.C1COCC[NH]1.c1cn2ncnc2cn1 | HBr | 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 | null | null | Brc1cnc(Nc2ccc(N3CCOCC3)cc2)c2ncnn12.CN1CCN(c2ccc(Nc3ncc(-c4csc(C(N)=O)c4)n4ncnc34)cc2)CC1>C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.O1CCOCC1>NC(=O)c1cc(-c2cnc(Nc3ccc(N4CCOCC4)cc3)c3ncnn23)cs... |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-f0e66e2bb47948cd888b49e707892845 | CN1CCN(c2ccc(Nc3ncc(Br)n4ncnc34)cc2)CC1.Cc1[nH]ncc1B1OC(C)(C)C(C)(C)O1>>Cc1[nH]ncc1-c1cnc(Nc2ccc(N3CCN(C)CC3)cc2)c2ncnn12 | C(=O)([O-])[O-].[Na+].[Na+].CN1CCN(CC1)C1=CC=C(C=C1)NC=1C=2N(C(=CN1)C=1C=C(SC1)C(=O)N)N=CN2.BrC1=CN=C(C=2N1N=CN2)NC2=CC=C(C=C2)N2CCN(CC2)C.CC1=C(C=NN1)B1OC(C(O1)(C)C)(C)C>>CC1=C(C=NN1)C1=CN=C(C=2N1N=CN2)NC2=CC=C(C=C2)N2CCN(CC2)C | Br[c:7]1[cH:8][n:9][c:10]([NH:11][c:12]2[cH:13][cH:14][c:15]([N:16]3[CH2:17][CH2:18][N:19]([CH3:20])[CH2:21][CH2:22]3)[cH:23][cH:24]2)[c:25]2[n:26][cH:27][n:28][n:29]12.CC1(C)OB([c:6]2[c:2]([CH3:1])[nH:3][n:4][cH:5]2)OC1(C)C>>[CH3:1][c:2]1[nH:3][n:4][cH:5][c:6]1-[c:7]1[cH:8][n:9][c:10]([NH:11][c:12]2[cH:13][cH:14][c:15... | CN1CCN(c2ccc(Nc3ncc(Br)n4ncnc34)cc2)CC1.Cc1[nH]ncc1B1OC(C)(C)C(C)(C)O1 | Cc1[nH]ncc1-c1cnc(Nc2ccc(N3CCN(C)CC3)cc2)c2ncnn12 | 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 esters | 3b077e58a8068174133a7eecad35957570f9290725408c31a955826b02d2e470 | b42efb3b6a7742d5af594c6a3031e487327e58e9f8c2f428ee68996c98377910 | c1nc2c(Nc3ccc(N4CCNCC4)cc3)ncc(-c3cn[nH]c3)n2n1 | Br-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[c:4]:[c:5]2:[#7;a:6]:[c:7]:[#7;a:8]:[#7;a:9]:2:1.C-C1(-C)-O-B(-[c;H0;D3;+0:10]2:[c:11]:[#7;a:12]:[#7;a:13]:[c:14]:2-[C;D1;H3:15])-O-C-1(-C)-C>>[C;D1;H3:15]-[c:14]1:[#7;a:13]:[#7;a:12]:[c:11]:[c;H0;D3;+0:10]:1-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[c:4]:[c:5]2:[#7;a:6]:[c:7]:[#7;a:8]:[#7;a:9]... | 7 | [{"value": 7.0, "product": "CC1=C(C=NN1)C1=CN=C(C=2N1N=CN2)NC2=CC=C(C=C2)N2CCN(CC2)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | This compound may be prepared using methods as described for Compound 6, step 4 using (5-bromo-[1,2,4]triazolo[1,5-a]pyrazin-8-yl)-[4-(4-methyl-piperazin-1-yl)-phenyl]-amine (132 mg, 0.340 mmol), 5-methyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrazole (141 mg, 0.68 mmol), Pd(PPh3)4 (98 mg, 0.085 mmol) and... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic ester | null | c1cn2ncnc2cn1.B1OCCO1.c1cn[nH]c1 | c1cn[nH]c1.c1cn2ncnc2cn1 | c1cn[nH]c1.c1ccccc1.C1C[NH]CC[NH]1.c1cn2ncnc2cn1 | HBr.B | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.O1CCOCC1 | null | null | CN1CCN(c2ccc(Nc3ncc(Br)n4ncnc34)cc2)CC1.Cc1[nH]ncc1B1OC(C)(C)C(C)(C)O1>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>Cc1[nH]ncc1-c1cnc(Nc2ccc(N3CCN(C)CC3)cc2)c2ncnn12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-785ca2cd5f0f4662b415f70122108024 | Brc1ncc(Br)n2ncnc12.Nc1ccc(N2CCOCC2)c(F)c1>>Fc1cc(Nc2ncc(Br)n3ncnc23)ccc1N1CCOCC1 | CCN(C(C)C)C(C)C.CN1CCN(CC1)C1=CC=C(C=C1)NC=1C=2N(C(=CN1)C=1C=C(SC1)C(=O)N)N=CN2.BrC1=CN=C(C=2N1N=CN2)Br.FC=1C=C(C=CC1N1CCOCC1)N>>BrC1=CN=C(C=2N1N=CN2)NC2=CC(=C(C=C2)N2CCOCC2)F | Br[c:6]1[n:7][cH:8][c:9]([Br:10])[n:11]2[n:12][cH:13][n:14][c:15]12.[F:1][c:2]1[cH:3][c:4]([NH2:5])[cH:16][cH:17][c:18]1[N:19]1[CH2:20][CH2:21][O:22][CH2:23][CH2:24]1>>[F:1][c:2]1[cH:3][c:4]([NH:5][c:6]2[n:7][cH:8][c:9]([Br:10])[n:11]3[n:12][cH:13][n:14][c:15]23)[cH:16][cH:17][c:18]1[N:19]1[CH2:20][CH2:21][O:22][CH2:23... | Brc1ncc(Br)n2ncnc12.Nc1ccc(N2CCOCC2)c(F)c1 | Fc1cc(Nc2ncc(Br)n3ncnc23)ccc1N1CCOCC1 | null | null | CC(C)O | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | aecfb0ede2c5d7901fea69101287828edf21f7a6e48b6ff83fe43de0688f1ef1 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1cn2ncnc2c(Nc2ccc(N3CCOCC3)cc2)n1 | Br-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]:[#7;a:5]2:[#7;a:6]:[c:7]:[#7;a:8]:[c:9]:2:1.[NH2;D1;+0:10]-[c:11](:[c:12]):[c:13]>>[c:12]:[c:11](-[NH;D2;+0:10]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]:[#7;a:5]2:[#7;a:6]:[c:7]:[#7;a:8]:[c:9]:2:1):[c:13] | 98.5 | [{"value": 98.0, "product": "BrC1=CN=C(C=2N1N=CN2)NC2=CC(=C(C=C2)N2CCOCC2)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 98.5, "product": "BrC1=CN=C(C=2N1N=CN2)NC2=CC(=C(C=C2)N2CCOCC2)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | This compound may be prepared using methods as described for Compound 6, step 1 using 5,8-dibromo-[1,2,4]triazolo[1,5-a]pyrazine (0.5 g, 1.799 mmol), 3-fluoro-4-morpholin-4-yl-phenylamine (0.53 g, 2.70 mmol), and DIPEA (0.470 mL, 2.70 mmol) in 2-propanol (6 mL). The reaction mixture is partitioned between 10% citric ac... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cn2ncnc2cn1 | c1cn2ncnc2cn1 | c1ccccc1.c1cn2ncnc2cn1.C1COCC[NH]1 | HBr | CC(C)O | null | null | Brc1ncc(Br)n2ncnc12.Nc1ccc(N2CCOCC2)c(F)c1>CC(C)O>Fc1cc(Nc2ncc(Br)n3ncnc23)ccc1N1CCOCC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-abcfc0fd01024e77a4fdc5b5948e1eb0 | Brc1ncc(Br)n2ncnc12.CC(C)O.CN1CCN(c2ccc(Nc3ncc(-c4csc(C(N)=O)c4)n4ncnc34)cc2)CC1>>NC(=O)c1cc(Nc2ncc(Br)n3ncnc23)ccc1N1CCOCC1 | CN1CCN(CC1)C1=CC=C(C=C1)NC=1C=2N(C(=CN1)C=1C=C(SC1)C(=O)N)N=CN2.BrC1=CN=C(C=2N1N=CN2)Br.CCOCC.CC(C)O.CC(C)O.C(C)(C)N(C(C)C)CC>>BrC1=CN=C(C=2N1N=CN2)NC=2C=CC(=C(C(=O)N)C2)N2CCOCC2 | Br[c:8]1[n:9][cH:10][c:11]([Br:12])[n:13]2[n:14][cH:15][n:16][c:17]12.CC(C)[OH:24].CN1[CH2:23][CH2:22][N:21]([c:20]2cc[c:6]([NH:7]c3ncc(-c4cs[c:4]([C:2]([NH2:1])=[O:3])[cH:5]4)n4ncnc34)[cH:18][cH:19]2)[CH2:26][CH2:25]1>>[NH2:1][C:2](=[O:3])[c:4]1[cH:5][c:6]([NH:7][c:8]2[n:9][cH:10][c:11]([Br:12])[n:13]3[n:14][cH:15][n:... | Brc1ncc(Br)n2ncnc12.CC(C)O.CN1CCN(c2ccc(Nc3ncc(-c4csc(C(N)=O)c4)n4ncnc34)cc2)CC1 | NC(=O)c1cc(Nc2ncc(Br)n3ncnc23)ccc1N1CCOCC1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | f24be8ea534e9125d766fcfc3db0d39d1570189087ed9b240d08fee6ed445d29 | 93b1adaa9fdf847e37e9437ec2849798bd990e21a9ad5ba2bd6bd1346eaa708d | c1cn2ncnc2c(Nc2ccc(N3CCOCC3)cc2)n1 | Br-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]:[#7;a:5]2:[#7;a:6]:[c:7]:[#7;a:8]:[c:9]:2:1.C-C(-C)-[OH;D1;+0:10].C-N1-[CH2;D2;+0:11]-[C:12]-[#7:13](-[c;H0;D3;+0:14]2:[c:15]:[c:16]:[c;H0;D3;+0:17](-[NH;D2;+0:18]-c3:n:c:c(-c4:[cH;D2;+0:19]:[c;H0;D3;+0:20](-[C:21](-[N;D1;H2:22])=[O;D1;H0:23]):s:c:4):n4:n:c:n:c:3:4):c:c:2)-[C:24]... | 73 | [{"value": 73.0, "product": "BrC1=CN=C(C=2N1N=CN2)NC=2C=CC(=C(C(=O)N)C2)N2CCOCC2", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | This compound may be prepared using methods as described for Compound 6, step 1 using 5,8-dibromo-[1,2,4]triazolo[1,5-a]pyrazine (250 mg, 0.90 mmol) 5-amino-2-morpholin-4-yl benzamide (299 mg, 1.35 mmol) and N,N-diisopropylethylamine (0.24 mL, 1.35 mmol) in 2-propanol (7 mL). Trituration with iPrOH and Et2O affords the... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary alcohol.Secondary amine.Tertiary amine | Ether.Secondary amine | c1cn2ncnc2cn1.C1CNCC[NH]1.c1ccccc1.c1ccsc1.c1cn2ncnc2cn1 | c1ccccc1.c1cn2ncnc2cn1.C1COCC[NH]1 | c1ccccc1.c1cn2ncnc2cn1.C1COCC[NH]1 | HBr | null | null | null | Brc1ncc(Br)n2ncnc12.CC(C)O.CN1CCN(c2ccc(Nc3ncc(-c4csc(C(N)=O)c4)n4ncnc34)cc2)CC1>>NC(=O)c1cc(Nc2ncc(Br)n3ncnc23)ccc1N1CCOCC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-6c6efd22323b4263a477df3bd1120f0d | CC1(C)OB(c2cn[nH]c2)OC1(C)C.CN1CCN(c2ccc(Nc3ncc(-c4csc(C(N)=O)c4)n4ncnc34)cc2)CC1.NC(=O)c1cc(Nc2ncc(Br)n3ncnc23)ccc1N1CCOCC1>>N.NC(=O)c1cc(Nc2ncc(-c3cn[nH]c3)n3ncnc23)ccc1N1CCOCC1 | CC1(OB(OC1(C)C)C=1C=NNC1)C.CN1CCN(CC1)C1=CC=C(C=C1)NC=1C=2N(C(=CN1)C=1C=C(SC1)C(=O)N)N=CN2.BrC1=CN=C(C=2N1N=CN2)NC=2C=CC(=C(C(=O)N)C2)N2CCOCC2>>N.N1N=CC(=C1)C1=CN=C(C=2N1N=CN2)NC=2C=CC(=C(C(=O)N)C2)N2CCOCC2 | CC1(C)OB([c:13]2[cH:14][n:15][nH:16][cH:17]2)OC1(C)C.CN1CCN(c2ccc(Nc3ncc(-c4csc(C(=O)[NH2:1])c4)n4ncnc34)cc2)CC1.Br[c:12]1[cH:11][n:10][c:9]([NH:8][c:7]2[cH:6][c:5]([C:3]([NH2:2])=[O:4])[c:25]([N:26]3[CH2:27][CH2:28][O:29][CH2:30][CH2:31]3)[cH:24][cH:23]2)[c:22]2[n:18]1[n:19][cH:20][n:21]2>>[NH3:1].[NH2:2][C:3](=[O:4])... | CC1(C)OB(c2cn[nH]c2)OC1(C)C.CN1CCN(c2ccc(Nc3ncc(-c4csc(C(N)=O)c4)n4ncnc34)cc2)CC1.NC(=O)c1cc(Nc2ncc(Br)n3ncnc23)ccc1N1CCOCC1 | N.NC(=O)c1cc(Nc2ncc(-c3cn[nH]c3)n3ncnc23)ccc1N1CCOCC1 | 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(=O)([O-])[O-].[K+].[K+] | C-C Coupling | OtherReaction | 5450a2db6e7305c45383870e931e62f9935b44015cf383067240af8b2a416783 | 96e5f3628c1bd4659dd3e9821904115decf673d0e8e42bb7900b7f521b084c51 | c1nc2c(Nc3ccc(N4CCOCC4)cc3)ncc(-c3cn[nH]c3)n2n1 | Br-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[c:4]:[c:5]2:[#7;a:6]:[c:7]:[#7;a:8]:[#7;a:9]:2:1.C-C1(-C)-O-B(-[c;H0;D3;+0:10]2:[c:11]:[#7;a:12]:[#7;a:13]:[c:14]:2)-O-C-1(-C)-C.C-N1-C-C-N(-c2:c:c:c(-N-c3:n:c:c(-c4:c:s:c(-C(=O)-[NH2;D1;+0:15]):c:4):n4:n:c:n:c:3:4):c:c:2)-C-C-1>>[#7;a:3]1:[c:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:10]2:[c:11]... | 30 | [{"value": 30.0, "product": "N1N=CC(=C1)C1=CN=C(C=2N1N=CN2)NC=2C=CC(=C(C(=O)N)C2)N2CCOCC2", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | This compound may be prepared using methods as described for Compound 6, step 4 using 5-(5-bromo-[1,2,4]triazolo[1,5-a]pyrazin-8-ylamino)-2-morpholin-4-yl-benzamide (140 mg, 0.33 mmol), 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrazole (130 mg, 0.67 mmol) and Pd(PPh3)4 (96 mg, 0.083 mmol) in 1.5M K2CO3 (aq) ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amide.Secondary amine.Tertiary amine.Tertiary amine.Boronic ester | null | B1OCCO1.c1cn[nH]c1.C1CNCCN1.c1ccccc1.c1ccsc1.c1cn2ncnc2cn1.c1cn2ncnc2cn1 | c1cn[nH]c1.c1cn2ncnc2cn1 | c1ccccc1.c1cn[nH]c1.c1cn2ncnc2cn1.C1COCC[NH]1 | HBr.B | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.O1CCOCC1.C(=O)([O-])[O-].[K+].[K+] | null | null | CC1(C)OB(c2cn[nH]c2)OC1(C)C.CN1CCN(c2ccc(Nc3ncc(-c4csc(C(N)=O)c4)n4ncnc34)cc2)CC1.NC(=O)c1cc(Nc2ncc(Br)n3ncnc23)ccc1N1CCOCC1>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(=O)([O-])[O-]... |
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