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-517acf81c55344f99fba65175862b982 | ClCCCBr.Cn1c(C(O)c2ccc(Cl)cc2)cnc1S>>Cn1c(C(O)c2ccc(Cl)cc2)cnc1SCCCCl | ClC1=CC=C(C=C1)C(O)C=1N(C(=NC1)S)C.C(=O)([O-])[O-].[K+].[K+].BrCCCCl>>ClC1=CC=C(C=C1)C(O)C=1N(C(=NC1)SCCCCl)C | Br[CH2:17][CH2:18][CH2:19][Cl:20].[CH3:1][n:2]1[c:3]([CH:4]([OH:5])[c:6]2[cH:7][cH:8][c:9]([Cl:10])[cH:11][cH:12]2)[cH:13][n:14][c:15]1[SH:16]>>[CH3:1][n:2]1[c:3]([CH:4]([OH:5])[c:6]2[cH:7][cH:8][c:9]([Cl:10])[cH:11][cH:12]2)[cH:13][n:14][c:15]1[S:16][CH2:17][CH2:18][CH2:19][Cl:20] | ClCCCBr.Cn1c(C(O)c2ccc(Cl)cc2)cnc1S | Cn1c(C(O)c2ccc(Cl)cc2)cnc1SCCCCl | null | null | CC(=O)C.CN(C)C=O | Heteroatom Alkylation and Arylation | thioether_nucl_sub | 26df88c6a3f5f203c89584658be4e126cb42994c98a2e16bc812e1036cdae857 | 8b2f52296c3a93039174c980b6042ba15754e04d6892a1284c3a32985220b214 | c1ccc(Cc2cnc[nH]2)cc1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[C;D1;H3:4]-[#7;a:5]1:[c:6]:[c:7]:[#7;a:8]:[c:9]:1-[SH;D1;+0:10]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[S;H0;D2;+0:10]-[c:9]1:[#7;a:8]:[c:7]:[c:6]:[#7;a:5]:1-[C;D1;H3:4] | 69 | [{"value": 69.0, "product": "ClC1=CC=C(C=C1)C(O)C=1N(C(=NC1)SCCCCl)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 68.4, "product": "ClC1=CC=C(C=C1)C(O)C=1N(C(=NC1)SCCCCl)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 16 | HOUR | The product of Example I, Step A (0.09 g) in acetone (2 mL) and DMF (2 mL) was treated with K2CO3 (0.2 g) followed by 1-bromo-3-chloropropane (0.11 g). The mixture was allowed to stir at rt for 16 h and was then partitioned between EtOAc (50 mL) and brine (50 mL). The organic layer was separated and washed with brine (... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic thiol | Monosulfide | null | null | c1cnc[nH]1.c1ccccc1 | HBr | CC(=O)C.CN(C)C=O | null | 16 | ClCCCBr.Cn1c(C(O)c2ccc(Cl)cc2)cnc1S>CC(=O)C.CN(C)C=O>Cn1c(C(O)c2ccc(Cl)cc2)cnc1SCCCCl |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-11ad7b5b2b0443ce966e181291007d7a | Cn1c(C(=O)c2ccc(Br)cc2)cnc1SCCCN1CCCCC1>>Cn1c(C(O)c2ccc(Br)cc2)cnc1SCCCN1CCCCC1 | BrC1=CC=C(C=C1)C(=O)C=1N(C(=NC1)SCCCN1CCCCC1)C>>BrC1=CC=C(C=C1)C(O)C=1N(C(=NC1)SCCCN1CCCCC1)C | [CH3:1][n:2]1[c:3]([C:4](=[O:5])[c:6]2[cH:7][cH:8][c:9]([Br:10])[cH:11][cH:12]2)[cH:13][n:14][c:15]1[S:16][CH2:17][CH2:18][CH2:19][N:20]1[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25]1>>[CH3:1][n:2]1[c:3]([CH:4]([OH:5])[c:6]2[cH:7][cH:8][c:9]([Br:10])[cH:11][cH:12]2)[cH:13][n:14][c:15]1[S:16][CH2:17][CH2:18][CH2:19][N:20]1[C... | Cn1c(C(=O)c2ccc(Br)cc2)cnc1SCCCN1CCCCC1 | Cn1c(C(O)c2ccc(Br)cc2)cnc1SCCCN1CCCCC1 | null | O=[Mn]=O | null | Reduction | Reduction of ketone to secondary alcohol | 02790ac194d8bf7ccb13d6247c59412024d87f77d2c906ef7804f021f57d5070 | 1bd3cd74b454139c0a0068ac0135836499926b274bff569df163210c6c944a89 | c1ccc(Cc2cnc(SCCCN3CCCCC3)[nH]2)cc1 | [C;D1;H3:1]-[#7;a:2]1:[c:3]:[#7;a:4]:[c:5]:[c:6]:1-[C;H0;D3;+0:7](=[O;H0;D1;+0:8])-[c:9](:[c:10]):[c:11]>>[C;D1;H3:1]-[#7;a:2]1:[c:3]:[#7;a:4]:[c:5]:[c:6]:1-[CH;D3;+0:7](-[OH;D1;+0:8])-[c:9](:[c:10]):[c:11] | 20 | [{"value": 20.0, "product": "BrC1=CC=C(C=C1)C(O)C=1N(C(=NC1)SCCCN1CCCCC1)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The product of Example III, Step B (0.11 g) in acetone (5 mL) and DMF (5 mL) was treated with piperidine (0.22 g) and K2CO3 (1.8 g). The reaction mixture was allowed to stir for 16 h and then partitioned between EtOAc (75 mL) and aqueous (aq.) saturated (satd.) NaHCO3 (50 mL). The organic portion was washed with brine ... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Secondary alcohol | null | null | c1cnc[nH]1.c1ccccc1.C1CC[NH]CC1 | null | O=[Mn]=O | null | null | Cn1c(C(=O)c2ccc(Br)cc2)cnc1SCCCN1CCCCC1>O=[Mn]=O>Cn1c(C(O)c2ccc(Br)cc2)cnc1SCCCN1CCCCC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-7cf15beb6df540968fa3d3aaa5a6be29 | CCCBr.Cn1c(C(O)c2ccc(Cl)cc2)cnc1S>>CCCSc1ncc(C(O)c2ccc(Cl)cc2)n1C | ClC1=CC=C(C=C1)C(O)C=1N(C(=NC1)S)C.BrCCC>>ClC1=CC=C(C=C1)C(O)C=1N(C(=NC1)SCCC)C | Br[CH2:3][CH2:2][CH3:1].[SH:4][c:5]1[n:6][cH:7][c:8]([CH:9]([OH:10])[c:11]2[cH:12][cH:13][c:14]([Cl:15])[cH:16][cH:17]2)[n:18]1[CH3:19]>>[CH3:1][CH2:2][CH2:3][S:4][c:5]1[n:6][cH:7][c:8]([CH:9]([OH:10])[c:11]2[cH:12][cH:13][c:14]([Cl:15])[cH:16][cH:17]2)[n:18]1[CH3:19] | CCCBr.Cn1c(C(O)c2ccc(Cl)cc2)cnc1S | CCCSc1ncc(C(O)c2ccc(Cl)cc2)n1C | null | null | null | Heteroatom Alkylation and Arylation | thioether_nucl_sub | 26df88c6a3f5f203c89584658be4e126cb42994c98a2e16bc812e1036cdae857 | 8b2f52296c3a93039174c980b6042ba15754e04d6892a1284c3a32985220b214 | c1ccc(Cc2cnc[nH]2)cc1 | Br-[CH2;D2;+0:1]-[C:2]-[C;D1;H3:3].[C;D1;H3:4]-[#7;a:5]1:[c:6]:[c:7]:[#7;a:8]:[c:9]:1-[SH;D1;+0:10]>>[C;D1;H3:4]-[#7;a:5]1:[c:6]:[c:7]:[#7;a:8]:[c:9]:1-[S;H0;D2;+0:10]-[CH2;D2;+0:1]-[C:2]-[C;D1;H3:3] | 71 | [{"value": 71.0, "product": "ClC1=CC=C(C=C1)C(O)C=1N(C(=NC1)SCCC)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The product of Example I, Step A (3.35 g) was subjected to the same conditions as described in Example I, Step B except that bromopropane (1.4 mL) was employed as the alkylating agent to provide (4-Chlorophenyl)-(3-methyl-2-propylsulfanyl-3H-imidazol-4-yl)-methanol (2.69 g, 71%). M calc=296; M+H found=297. Calculated f... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic thiol | Monosulfide | null | null | c1c[nH]cn1.c1ccccc1 | HBr | null | null | null | CCCBr.Cn1c(C(O)c2ccc(Cl)cc2)cnc1S>>CCCSc1ncc(C(O)c2ccc(Cl)cc2)n1C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a571ddaab69d4c9f82dbb29e0efdbdb4 | CN(C)CCCSc1ncc(C(=O)c2ccc(Cl)cc2)n1C.OO>>CN(C)CCCS(=O)c1ncc(C(=O)c2ccc(Cl)cc2)n1C | [OH-].[Na+].O.ClC1=CC=C(C=C1)C(=O)C=1N(C(=NC1)SCCCN(C)C)C.OO>>ClC1=CC=C(C=C1)C(=O)C=1N(C(=NC1)S(=O)CCCN(C)C)C | [CH3:1][N:2]([CH3:3])[CH2:4][CH2:5][CH2:6][S:7][c:9]1[n:10][cH:11][c:12]([C:13](=[O:14])[c:15]2[cH:16][cH:17][c:18]([Cl:19])[cH:20][cH:21]2)[n:22]1[CH3:23].O[OH:8]>>[CH3:1][N:2]([CH3:3])[CH2:4][CH2:5][CH2:6][S:7](=[O:8])[c:9]1[n:10][cH:11][c:12]([C:13](=[O:14])[c:15]2[cH:16][cH:17][c:18]([Cl:19])[cH:20][cH:21]2)[n:22]1... | CN(C)CCCSc1ncc(C(=O)c2ccc(Cl)cc2)n1C.OO | CN(C)CCCS(=O)c1ncc(C(=O)c2ccc(Cl)cc2)n1C | null | null | C(C)(=O)O | Oxidation | Sulfanyl to sulfinyl_H2O2 | 3f94fa67dce0f9d1622f25c2f6b679e0a2528e6d5c5559b15aed37456745a4b5 | 099322fb111e24ec324e6fad75d493a762ca0cd5af0df8c6f3bfd25c910b45a8 | O=C(c1ccccc1)c1cnc[nH]1 | O-[OH;D1;+0:1].[C:2]-[C:3]-[S;H0;D2;+0:4]-[c:5]1:[#7;a:6]:[c:7]:[c:8](-[C:9]=[O;D1;H0:10]):[#7;a:11]:1-[C;D1;H3:12]>>[C:2]-[C:3]-[S;H0;D3;+0:4](=[O;H0;D1;+0:1])-[c:5]1:[#7;a:6]:[c:7]:[c:8](-[C:9]=[O;D1;H0:10]):[#7;a:11]:1-[C;D1;H3:12] | null | [] | null | null | 48 | HOUR | To a stirred solution of (4-Chloro-phenyl)-[2-(3-dimethylamino-propylsulfanyl)-3-methyl-3H-imidazol-4-yl]-methanone (135 mg) in glacial acetic acid (4.00 mL) was added at rt H2O2 (82.0 μL; 30 wt. % in water). The reaction solution was stirred for 48 h at rt, and water (10.0 mL) was added. The solution was brought to pH... | 10.6084/m9.figshare.5104873.v1 | null | Peroxide.Monosulfide | Sulfoxide | null | null | c1c[nH]cn1.c1ccccc1 | HO- | C(C)(=O)O | null | 48 | CN(C)CCCSc1ncc(C(=O)c2ccc(Cl)cc2)n1C.OO>C(C)(=O)O>CN(C)CCCS(=O)c1ncc(C(=O)c2ccc(Cl)cc2)n1C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-30840878b9f5488a905dae2b4792dd68 | CNOC.O=C(Cl)c1ccc(Cl)cc1>>CON(C)C(=O)c1ccc(Cl)cc1 | ClC1=CC=C(C(=O)Cl)C=C1.Cl.CNOC.C(C)N(CC)CC>>ClC1=CC=C(C(=O)N(C)OC)C=C1 | [CH3:1][O:2][NH:3][CH3:4].Cl[C:5](=[O:6])[c:7]1[cH:8][cH:9][c:10]([Cl:11])[cH:12][cH:13]1>>[CH3:1][O:2][N:3]([CH3:4])[C:5](=[O:6])[c:7]1[cH:8][cH:9][c:10]([Cl:11])[cH:12][cH:13]1 | CNOC.O=C(Cl)c1ccc(Cl)cc1 | CON(C)C(=O)c1ccc(Cl)cc1 | null | null | C(Cl)Cl | Acylation | N-alkylation of secondary amines with alkyl halides | b92e0bfd3d683c1f2a209adfe70a67ad7cb0d87749eb59e8fe0cf1689bc291e0 | 96cb0a2fed10552c5770a45a2d6523b47ac3e38928b4a9c698d8577451182dcd | c1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[C;D1;H3:6]-[#8:7]-[NH;D2;+0:8]-[C;D1;H3:9]>>[C;D1;H3:6]-[#8:7]-[N;H0;D3;+0:8](-[C;D1;H3:9])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5] | 92.7 | [{"value": 92.0, "product": "ClC1=CC=C(C(=O)N(C)OC)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 92.7, "product": "ClC1=CC=C(C(=O)N(C)OC)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 8 | HOUR | A 1-L, three-necked, round-bottomed flask equipped with a magnetic stirrer, nitrogen inlet and an addition funnel was charged with N,O-dimethylhydroxylamine hydrochloride (20 g, 0.20 mol) and CH2Cl2 (250 mL). The mixture was cooled to 0° C. and triethylamine (24 g, 0.20 mol) was added, followed by a solution of 4-chlor... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Secondary amine | Tertiary amide | null | null | c1ccccc1 | HCl | C(Cl)Cl | 0 | 8 | CNOC.O=C(Cl)c1ccc(Cl)cc1>C(Cl)Cl>CON(C)C(=O)c1ccc(Cl)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-33784d9269ba4120a88d59e8cd38a9a7 | CC(C)N1CCC(CO)CC1.Cn1c(C(=O)c2ccc(Cl)cc2)cnc1Cl>>CC(C)N1CCC(COc2ncc(C(=O)c3ccc(Cl)cc3)n2C)CC1 | ClC1=NC=C(N1C)C(=O)C1=CC=C(C=C1)Cl.[H-].[Na+].C(C)(C)N1CCC(CC1)CO>>ClC1=CC=C(C=C1)C(=O)C=1N(C(=NC1)OCC1CCN(CC1)C(C)C)C | [CH3:1][CH:2]([CH3:3])[N:4]1[CH2:5][CH2:6][CH:7]([CH2:8][OH:9])[CH2:25][CH2:26]1.Cl[c:10]1[n:11][cH:12][c:13]([C:14](=[O:15])[c:16]2[cH:17][cH:18][c:19]([Cl:20])[cH:21][cH:22]2)[n:23]1[CH3:24]>>[CH3:1][CH:2]([CH3:3])[N:4]1[CH2:5][CH2:6][CH:7]([CH2:8][O:9][c:10]2[n:11][cH:12][c:13]([C:14](=[O:15])[c:16]3[cH:17][cH:18][c... | CC(C)N1CCC(CO)CC1.Cn1c(C(=O)c2ccc(Cl)cc2)cnc1Cl | CC(C)N1CCC(COc2ncc(C(=O)c3ccc(Cl)cc3)n2C)CC1 | null | null | C1CCOC1 | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | dd7acae407244f874fe9cfeba5336cc9dccd653601cdd03778244273ecfb33d8 | a4cafa7bcd156e21cca6eaac1b32e28ec8540642a31181122e6957f3d7559631 | O=C(c1ccccc1)c1cnc(OCC2CCNCC2)[nH]1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4](-[C:5]=[O;D1;H0:6]):[#7;a:7]:1-[C;D1;H3:8].[C:9]-[C:10]-[OH;D1;+0:11]>>[C:9]-[C:10]-[O;H0;D2;+0:11]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4](-[C:5]=[O;D1;H0:6]):[#7;a:7]:1-[C;D1;H3:8] | 78 | [{"value": 78.0, "product": "ClC1=CC=C(C=C1)C(=O)C=1N(C(=NC1)OCC1CCN(CC1)C(C)C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 77.6, "product": "ClC1=CC=C(C=C1)C(=O)C=1N(C(=NC1)OCC1CCN(CC1)C(C)C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 2 | HOUR | To a 1-L, three-necked, round-bottomed flask equipped with a magnetic stirrer, nitrogen inlet and an addition funnel was added NaH (1.45 g, 0.061 mol) and THF (300 mL). The stirred suspension was cooled to 0° C. and (1-isopropyl-piperidin-4-yl)-methanol (9.5 g, 0.06 mol) was added. The cooling bath was removed, and the... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary alcohol | Ether | c1c[nH]cn1 | c1c[nH]cn1 | C1CC[NH]CC1.c1c[nH]cn1.c1ccccc1 | HCl | C1CCOC1 | 0 | 2 | CC(C)N1CCC(CO)CC1.Cn1c(C(=O)c2ccc(Cl)cc2)cnc1Cl>C1CCOC1>CC(C)N1CCC(COc2ncc(C(=O)c3ccc(Cl)cc3)n2C)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-162b6e4d486440c3b824c1d7e9705d69 | CN1CCC(Sc2ncc(C(O[Si](C)(C)C(C)(C)C)c3cccc(F)c3)n2C)CC1>>CN1CCC(Sc2ncc(C(O)c3cccc(F)c3)n2C)CC1 | FC=1C=C(C=CC1)C(C1=CN=C(N1C)SC1CCN(CC1)C)O[Si](C)(C)C(C)(C)C.[H-].[Na+].FC=1C=C(C=CC1)C(C1=CN=C(N1C)Cl)O[Si](C)(C)C(C)(C)C>>FC=1C=C(C=CC1)C(O)C=1N(C(=NC1)SC1CCN(CC1)C)C | CC(C)(C)[Si](C)(C)[O:12][CH:11]([c:10]1[cH:9][n:8][c:7]([S:6][CH:5]2[CH2:4][CH2:3][N:2]([CH3:1])[CH2:23][CH2:22]2)[n:20]1[CH3:21])[c:13]1[cH:14][cH:15][cH:16][c:17]([F:18])[cH:19]1>>[CH3:1][N:2]1[CH2:3][CH2:4][CH:5]([S:6][c:7]2[n:8][cH:9][c:10]([CH:11]([OH:12])[c:13]3[cH:14][cH:15][cH:16][c:17]([F:18])[cH:19]3)[n:20]2[... | CN1CCC(Sc2ncc(C(O[Si](C)(C)C(C)(C)C)c3cccc(F)c3)n2C)CC1 | CN1CCC(Sc2ncc(C(O)c3cccc(F)c3)n2C)CC1 | null | null | C1CCOC1 | Deprotection | Alcohol deprotection from silyl ethers | 050b4fb4e1e9936189860d27dded10ae70a294a642c52f800eb9d5aaef7955cc | 88623e19d23cdfe8e1a4c167fd6cfc51d774a1c784b87a7bb2df8153ee93e67a | c1ccc(Cc2cnc(SC3CCNCC3)[nH]2)cc1 | C-C(-C)(-C)-[Si](-C)(-C)-[O;H0;D2;+0:1]-[C:2](-[c:3])-[c:4](:[#7;a:5]):[c:6]:[#7;a:7]>>[#7;a:5]:[c:4](-[C:2](-[OH;D1;+0:1])-[c:3]):[c:6]:[#7;a:7] | null | [] | null | null | 30 | MINUTE | 4-{5-[(3-Fluoro-phenyl)-(tert-butyl-dimethyl-silanyloxy)-methyl]-1-methyl-1H-imidazol-2-ylsulfanyl}-1-methyl-piperidine. To a 0° C. solution of 1-methyl-piperidine-thiol (1.5 equivalents) in THF (0.2 M) is added NaH (60% dispersion in oil, 1.5 equivalents). After 30 min, 5-[(3-fluoro-phenyl)-(tert-butyl-dimethyl-silany... | 10.6084/m9.figshare.5104873.v1 | null | TMS ether protective group | Secondary alcohol | null | null | C1CC[NH]CC1.c1c[nH]cn1.c1ccccc1 | Other | C1CCOC1 | null | 0.5 | CN1CCC(Sc2ncc(C(O[Si](C)(C)C(C)(C)C)c3cccc(F)c3)n2C)CC1>C1CCOC1>CN1CCC(Sc2ncc(C(O)c3cccc(F)c3)n2C)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-1e436c8e703f4c7799339d289b3f6850 | CC(C)N1CCC(Oc2cc3cc(C(=O)O)[nH]c3cc2Br)CC1.O=S(=O)(N1CCCCC1)N1CCNCC1>>CC(C)N1CCC(Oc2cc3cc(C(=O)N4CCN(S(=O)(=O)N5CCCCC5)CC4)[nH]c3cc2Br)CC1 | Cl.BrC1=C(C=C2C=C(NC2=C1)C(=O)O)OC1CCN(CC1)C(C)C.F[B-](F)(F)F.N1(N=NC2=C1C=CC=C2)OC(=[N+](C)C)N(C)C.N1(CCCCC1)S(=O)(=O)N1CCNCC1.C(C)(C)N(C(C)C)CC.C([O-])(O)=O.[Na+]>>BrC1=C(C=C2C=C(NC2=C1)C(=O)N1CCN(CC1)S(=O)(=O)N1CCCCC1)OC1CCN(CC1)C(C)C | O[C:14]([c:13]1[cH:12][c:11]2[cH:10][c:9]([O:8][CH:7]3[CH2:6][CH2:5][N:4]([CH:2]([CH3:1])[CH3:3])[CH2:37][CH2:36]3)[c:34]([Br:35])[cH:33][c:32]2[nH:31]1)=[O:15].[NH:16]1[CH2:17][CH2:18][N:19]([S:20](=[O:21])(=[O:22])[N:23]2[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28]2)[CH2:29][CH2:30]1>>[CH3:1][CH:2]([CH3:3])[N:4]1[CH2:5][... | CC(C)N1CCC(Oc2cc3cc(C(=O)O)[nH]c3cc2Br)CC1.O=S(=O)(N1CCCCC1)N1CCNCC1 | CC(C)N1CCC(Oc2cc3cc(C(=O)N4CCN(S(=O)(=O)N5CCCCC5)CC4)[nH]c3cc2Br)CC1 | null | null | CN(C=O)C | Acylation | Acylation of Nitrogen Nucleophiles by Carboxylic Acids | ed26ef5eea92a0cc433b3f89a34f4c61724425fa15a9d0ec83a0f7a903eec831 | c5e4172490b2731ba9322b68af56376edadc31ce0bb9a3dfdea23a1817a852fd | O=C(c1cc2cc(OC3CCNCC3)ccc2[nH]1)N1CCN(S(=O)(=O)N2CCCCC2)CC1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[#7;a:5]:[c:6].[#7:7]1-[C:8]-[C:9]-[NH;D2;+0:10]-[C:11]-[C:12]-1>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[N;H0;D3;+0:10]1-[C:9]-[C:8]-[#7:7]-[C:12]-[C:11]-1)-[c:3](:[c:4]):[#7;a:5]:[c:6] | 56 | [{"value": 56.0, "product": "BrC1=C(C=C2C=C(NC2=C1)C(=O)N1CCN(CC1)S(=O)(=O)N1CCCCC1)OC1CCN(CC1)C(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 55.9, "product": "BrC1=C(C=C2C=C(NC2=C1)C(=O)N1CCN(CC1)S(=O)(=O)N1CCCCC1)OC1CCN(CC1)C(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 0.5 g (1.20 mmol) 6-bromo-5-(1-isopropyl-piperidin-4-yloxy)-1H-indole-2-carboxylic acid hydrochloride in 8 mL N,N-dimethylformamide, 0.48 g (1.50 mmol) O-(benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium tetrafluoroborate, 0.31 g (1.33 mmol) 1-(piperidin-1-yl-sulfonyl)-piperazine and 1.0 mL (0.77 g, 6.0... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | Tertiary amide | C1CNCC[NH]1 | C1C[NH]CC[NH]1 | C1CC[NH]CC1.c1ccc2[nH]ccc2c1.C1C[NH]CC[NH]1.C1CC[NH]CC1 | HO- | CN(C=O)C | null | null | CC(C)N1CCC(Oc2cc3cc(C(=O)O)[nH]c3cc2Br)CC1.O=S(=O)(N1CCCCC1)N1CCNCC1>CN(C=O)C>CC(C)N1CCC(Oc2cc3cc(C(=O)N4CCN(S(=O)(=O)N5CCCCC5)CC4)[nH]c3cc2Br)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-4b5d9e30fc7b4282b9a64386311c57ff | CC(C)N1CCC(O)CC1.CCOC(=O)c1cc2cc(O)c(Br)cc2[nH]1>>CCOC(=O)c1cc2cc(OC3CCN(C(C)C)CC3)c(Br)cc2[nH]1 | N(=NC(=O)OC(C)(C)C)C(=O)OC(C)(C)C.C(C)OC(=O)C=1NC2=CC(=C(C=C2C1)O)Br.C(C)(C)N1CCC(CC1)O.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1>>C(C)OC(=O)C=1NC2=CC(=C(C=C2C1)OC1CCN(CC1)C(C)C)Br | O[CH:12]1[CH2:13][CH2:14][N:15]([CH:16]([CH3:17])[CH3:18])[CH2:19][CH2:20]1.[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][c:8]2[cH:9][c:10]([OH:11])[c:21]([Br:22])[cH:23][c:24]2[nH:25]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][c:8]2[cH:9][c:10]([O:11][CH:12]3[CH2:13][CH2:14][N:15]([CH:16]([CH3:17])[CH3:18])[CH2:19]... | CC(C)N1CCC(O)CC1.CCOC(=O)c1cc2cc(O)c(Br)cc2[nH]1 | CCOC(=O)c1cc2cc(OC3CCN(C(C)C)CC3)c(Br)cc2[nH]1 | null | null | O1CCCC1 | Heteroatom Alkylation and Arylation | Mitsunobu aryl ether | a9e936b0e9135225700edbab1c7696738b7f1f0756494b6ceeeda63b184d572f | 776ba735002e33225fbc578943016110c2c43efefd97bfeea4ec3cc2e2e1532f | c1cc2cc(OC3CCNCC3)ccc2[nH]1 | O-[CH;D3;+0:1]1-[C:2]-[C:3]-[#7:4]-[C:5]-[C:6]-1.[OH;D1;+0:7]-[c:8](:[c:9]):[c:10]>>[c:9]:[c:8](-[O;H0;D2;+0:7]-[CH;D3;+0:1]1-[C:2]-[C:3]-[#7:4]-[C:5]-[C:6]-1):[c:10] | 76 | [{"value": 76.0, "product": "C(C)OC(=O)C=1NC2=CC(=C(C=C2C1)OC1CCN(CC1)C(C)C)Br", "details": "PERCENTYIELD", "is_desired": false}, {"value": 75.7, "product": "C(C)OC(=O)C=1NC2=CC(=C(C=C2C1)OC1CCN(CC1)C(C)C)Br", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 18 | HOUR | To a suspension of 5.7 g (20.0 mmol) 6-bromo-5-hydroxy-1H-indole-2-carboxylic acid ethyl ester in 120 mL tetrahydrofuran, 3.44 g (24.0 mmol) isopropyl-piperidin-4-ol and 6.30 g (24.0 mmol) triphenylphosphine were added. The suspension was cooled to 0° C. and 5.53 g (24.0 mmol) di-tert-butyl azodicarboxylate was added. ... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol.Aromatic alcohol | Ether | C1CC[NH]CC1 | C1CC[NH]CC1 | c1ccc2[nH]ccc2c1.C1CC[NH]CC1 | HO- | O1CCCC1 | 0 | 18 | CC(C)N1CCC(O)CC1.CCOC(=O)c1cc2cc(O)c(Br)cc2[nH]1>O1CCCC1>CCOC(=O)c1cc2cc(OC3CCN(C(C)C)CC3)c(Br)cc2[nH]1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-4dd177b61f4645da8471e1b54c07186b | CCOC(=O)c1cc2cc(OC)c(Br)cc2[nH]1>>CCOC(=O)c1cc2cc(O)c(Br)cc2[nH]1 | C(C)OC(=O)C=1NC2=CC(=C(C=C2C1)OC)Br.B(Br)(Br)Br.C([O-])(O)=O.[Na+]>>C(C)OC(=O)C=1NC2=CC(=C(C=C2C1)O)Br | C[O:11][c:10]1[cH:9][c:8]2[cH:7][c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[nH:16][c:15]2[cH:14][c:12]1[Br:13]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][c:8]2[cH:9][c:10]([OH:11])[c:12]([Br:13])[cH:14][c:15]2[nH:16]1 | CCOC(=O)c1cc2cc(OC)c(Br)cc2[nH]1 | CCOC(=O)c1cc2cc(O)c(Br)cc2[nH]1 | null | null | ClCCl | Deprotection | Cleavage of methoxy ethers to alcohols | c5320c7dfa4f544d4900efcae9b3262bf0d5286bcf39c86109232351f35b23d5 | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | c1ccc2[nH]ccc2c1 | C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[OH;D1;+0:1]-[c:2](:[c:3]):[c:4] | 72.2 | [{"value": 72.0, "product": "C(C)OC(=O)C=1NC2=CC(=C(C=C2C1)O)Br", "details": "PERCENTYIELD", "is_desired": false}, {"value": 72.2, "product": "C(C)OC(=O)C=1NC2=CC(=C(C=C2C1)O)Br", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 8.30 g (27.8 mmol) 6-bromo-5-methoxy-1H-indole-2-carboxylic acid ethyl ester (prepared according to J. Org. Chem. 1974, 39, 3580) in 160 mL dichloromethane was cooled to −78° C. At this temperature, 55.7 mL boron tribromide (55.7 mmol; 1M solution in dichloromethane) were added. The solution was allowed t... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | null | null | c1ccc2[nH]ccc2c1 | Other | ClCCl | null | null | CCOC(=O)c1cc2cc(OC)c(Br)cc2[nH]1>ClCCl>CCOC(=O)c1cc2cc(O)c(Br)cc2[nH]1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-da0d5627de604b18965097ada43a05cd | CC(C)N1CCC(Oc2cc3cc(C(=O)O)[nH]c3cc2Br)CC1.CS(=O)(=O)N1CCNCC1>>CC(C)N1CCC(Oc2cc3cc(C(=O)N4CCN(S(C)(=O)=O)CC4)[nH]c3cc2Br)CC1 | Cl.BrC1=C(C=C2C=C(NC2=C1)C(=O)O)OC1CCN(CC1)C(C)C.CS(=O)(=O)N1CCNCC1>>BrC1=C(C=C2C=C(NC2=C1)C(=O)N1CCN(CC1)S(=O)(=O)C)OC1CCN(CC1)C(C)C | O[C:14]([c:13]1[cH:12][c:11]2[cH:10][c:9]([O:8][CH:7]3[CH2:6][CH2:5][N:4]([CH:2]([CH3:1])[CH3:3])[CH2:32][CH2:31]3)[c:29]([Br:30])[cH:28][c:27]2[nH:26]1)=[O:15].[NH:16]1[CH2:17][CH2:18][N:19]([S:20]([CH3:21])(=[O:22])=[O:23])[CH2:24][CH2:25]1>>[CH3:1][CH:2]([CH3:3])[N:4]1[CH2:5][CH2:6][CH:7]([O:8][c:9]2[cH:10][c:11]3[c... | CC(C)N1CCC(Oc2cc3cc(C(=O)O)[nH]c3cc2Br)CC1.CS(=O)(=O)N1CCNCC1 | CC(C)N1CCC(Oc2cc3cc(C(=O)N4CCN(S(C)(=O)=O)CC4)[nH]c3cc2Br)CC1 | null | null | null | Acylation | Acylation of Nitrogen Nucleophiles by Carboxylic Acids | ed26ef5eea92a0cc433b3f89a34f4c61724425fa15a9d0ec83a0f7a903eec831 | c5e4172490b2731ba9322b68af56376edadc31ce0bb9a3dfdea23a1817a852fd | O=C(c1cc2cc(OC3CCNCC3)ccc2[nH]1)N1CCNCC1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[#7;a:5]:[c:6].[#7:7]1-[C:8]-[C:9]-[NH;D2;+0:10]-[C:11]-[C:12]-1>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[N;H0;D3;+0:10]1-[C:9]-[C:8]-[#7:7]-[C:12]-[C:11]-1)-[c:3](:[c:4]):[#7;a:5]:[c:6] | 45 | [{"value": 45.0, "product": "BrC1=C(C=C2C=C(NC2=C1)C(=O)N1CCN(CC1)S(=O)(=O)C)OC1CCN(CC1)C(C)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The title compound was synthesized in analogy to example 1, from 6-bromo-5-(1-isopropyl-piperidin-4-yloxy)-1H-indole-2-carboxylic acid hydrochloride (example 1, intermediate a) and 1-methylsulfonyl-piperazine to afford the title compound as a light-yellow solid (45%).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | Tertiary amide | C1CNCC[NH]1 | C1C[NH]CC[NH]1 | C1CC[NH]CC1.c1ccc2[nH]ccc2c1.C1C[NH]CC[NH]1 | HO- | null | null | null | CC(C)N1CCC(Oc2cc3cc(C(=O)O)[nH]c3cc2Br)CC1.CS(=O)(=O)N1CCNCC1>>CC(C)N1CCC(Oc2cc3cc(C(=O)N4CCN(S(C)(=O)=O)CC4)[nH]c3cc2Br)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-30cf47e103e547e6aad1f0f986f90b5c | CC(C)N1CCC(Oc2cc3cc(C(=O)N4CCN(S(=O)(=O)N5CCCCC5)CC4)[nH]c3cc2Br)CC1.CC(C)OS(C)(=O)=O>>CC(C)N1CCC(Oc2cc3cc(C(=O)N4CCN(S(=O)(=O)N5CCCCC5)CC4)n(C(C)C)c3cc2Br)CC1 | C([O-])(O)=O.[Na+].BrC1=C(C=C2C=C(NC2=C1)C(=O)N1CCN(CC1)S(=O)(=O)N1CCCCC1)OC1CCN(CC1)C(C)C.C([O-])([O-])=O.[Cs+].[Cs+].CS(=O)(=O)OC(C)C>>BrC1=C(C=C2C=C(N(C2=C1)C(C)C)C(=O)N1CCN(CC1)S(=O)(=O)N1CCCCC1)OC1CCN(CC1)C(C)C | [CH3:1][CH:2]([CH3:3])[N:4]1[CH2:5][CH2:6][CH:7]([O:8][c:9]2[cH:10][c:11]3[cH:12][c:13]([C:14](=[O:15])[N:16]4[CH2:17][CH2:18][N:19]([S:20](=[O:21])(=[O:22])[N:23]5[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28]5)[CH2:29][CH2:30]4)[nH:31][c:35]3[cH:36][c:37]2[Br:38])[CH2:39][CH2:40]1.CS(=O)(=O)O[CH:32]([CH3:33])[CH3:34]>>[CH3... | CC(C)N1CCC(Oc2cc3cc(C(=O)N4CCN(S(=O)(=O)N5CCCCC5)CC4)[nH]c3cc2Br)CC1.CC(C)OS(C)(=O)=O | CC(C)N1CCC(Oc2cc3cc(C(=O)N4CCN(S(=O)(=O)N5CCCCC5)CC4)n(C(C)C)c3cc2Br)CC1 | null | null | C(C)#N | Heteroatom Alkylation and Arylation | OtherReaction | d896e99f48a796a768d64b339abb5adbd8bc977c5bccdd47720d3a6657256b55 | 0b4f3c8c88df0a792d0db7d59004d7fe5681a61dd48ef2449ddca2d636f76ada | O=C(c1cc2cc(OC3CCNCC3)ccc2[nH]1)N1CCN(S(=O)(=O)N2CCCCC2)CC1 | C-S(=O)(=O)-O-[CH;D3;+0:1](-[C;D1;H3:2])-[C;D1;H3:3].[C:4]-[#7:5](-[C:6](=[O;D1;H0:7])-[c:8]1:[c:9]:[c:10]:[c:11](:[c:12]):[nH;D2;+0:13]:1)-[C:14]>>[C:4]-[#7:5](-[C:6](=[O;D1;H0:7])-[c:8]1:[c:9]:[c:10]:[c:11](:[c:12]):[n;H0;D3;+0:13]:1-[CH;D3;+0:1](-[C;D1;H3:2])-[C;D1;H3:3])-[C:14] | 56 | [{"value": 56.0, "product": "BrC1=C(C=C2C=C(N(C2=C1)C(C)C)C(=O)N1CCN(CC1)S(=O)(=O)N1CCCCC1)OC1CCN(CC1)C(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 55.3, "product": "BrC1=C(C=C2C=C(N(C2=C1)C(C)C)C(=O)N1CCN(CC1)S(=O)(=O)N1CCCCC1)OC1CCN(CC1)C(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": f... | null | null | null | null | To a solution of 100 mg (0.17 mmol) [6-bromo-5-(1-isopropyl-piperidin-4-yloxy)-1H-indol-2-yl]-[4-(piperidine-1-sulfonyl)-piperazin-1-yl]-methanone (example 1) in 3 mL acetonitrile were added 109 mg (0.33 mmol) cesium carbonate and 46 mg (0.33 mmol) isopropyl methanesulfonate. The reaction was stirred under reflux for 1... | 10.6084/m9.figshare.5104873.v1 | null | Mesylate | null | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1 | C1CC[NH]CC1.c1ccc2[nH]ccc2c1.C1C[NH]CC[NH]1.C1CC[NH]CC1 | MsOH.HO- | C(C)#N | null | null | CC(C)N1CCC(Oc2cc3cc(C(=O)N4CCN(S(=O)(=O)N5CCCCC5)CC4)[nH]c3cc2Br)CC1.CC(C)OS(C)(=O)=O>C(C)#N>CC(C)N1CCC(Oc2cc3cc(C(=O)N4CCN(S(=O)(=O)N5CCCCC5)CC4)n(C(C)C)c3cc2Br)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-5f491590137e407ca62e853e1fef83e6 | CC(C)N1CCC(Oc2cc3cc(C(=O)N4CCN(S(=O)(=O)N5CCCCC5)CC4)[nH]c3cc2Br)CC1.OB(O)c1ccnc(Cl)c1>>CC(C)N1CCC(Oc2cc3cc(C(=O)N4CCN(S(=O)(=O)N5CCCCC5)CC4)n(-c4ccnc(Cl)c4)c3cc2Br)CC1 | BrC1=C(C=C2C=C(NC2=C1)C(=O)N1CCN(CC1)S(=O)(=O)N1CCCCC1)OC1CCN(CC1)C(C)C.ClC1=NC=CC(=C1)B(O)O.N1=CC=CC=C1>>BrC1=C(C=C2C=C(N(C2=C1)C1=CC(=NC=C1)Cl)C(=O)N1CCN(CC1)S(=O)(=O)N1CCCCC1)OC1CCN(CC1)C(C)C | [CH3:1][CH:2]([CH3:3])[N:4]1[CH2:5][CH2:6][CH:7]([O:8][c:9]2[cH:10][c:11]3[cH:12][c:13]([C:14](=[O:15])[N:16]4[CH2:17][CH2:18][N:19]([S:20](=[O:21])(=[O:22])[N:23]5[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28]5)[CH2:29][CH2:30]4)[nH:31][c:39]3[cH:40][c:41]2[Br:42])[CH2:43][CH2:44]1.OB(O)[c:32]1[cH:33][cH:34][n:35][c:36]([Cl... | CC(C)N1CCC(Oc2cc3cc(C(=O)N4CCN(S(=O)(=O)N5CCCCC5)CC4)[nH]c3cc2Br)CC1.OB(O)c1ccnc(Cl)c1 | CC(C)N1CCC(Oc2cc3cc(C(=O)N4CCN(S(=O)(=O)N5CCCCC5)CC4)n(-c4ccnc(Cl)c4)c3cc2Br)CC1 | null | C(C)(=O)[O-].[Cu+2].C(C)(=O)[O-] | C(Cl)(Cl)Cl | Heteroatom Alkylation and Arylation | OtherReaction | bb8efea1bfa0f318149646b016b0217e3f23a7e855502149afe40216d906e877 | e0368246531386f86cd0aa9da1423eb47f529b782fb229563cefe1166d6ba4f5 | O=C(c1cc2cc(OC3CCNCC3)ccc2n1-c1ccncc1)N1CCN(S(=O)(=O)N2CCCCC2)CC1 | O-B(-O)-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[#7;a:4]:[c:5](-[Cl;D1;H0:6]):[c:7]:1.[C:8]-[#7:9](-[C:10](=[O;D1;H0:11])-[c:12]1:[c:13]:[c:14]:[c:15](:[c:16]):[nH;D2;+0:17]:1)-[C:18]>>[C:8]-[#7:9](-[C:10](=[O;D1;H0:11])-[c:12]1:[c:13]:[c:14]:[c:15](:[c:16]):[n;H0;D3;+0:17]:1-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[#7;a:4]:[c:5](-[Cl;D1;H0:6... | 47.5 | [{"value": 47.0, "product": "BrC1=C(C=C2C=C(N(C2=C1)C1=CC(=NC=C1)Cl)C(=O)N1CCN(CC1)S(=O)(=O)N1CCCCC1)OC1CCN(CC1)C(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 47.5, "product": "BrC1=C(C=C2C=C(N(C2=C1)C1=CC(=NC=C1)Cl)C(=O)N1CCN(CC1)S(=O)(=O)N1CCCCC1)OC1CCN(CC1)C(C)C", "details": "CALCULATEDPERCENTYIE... | 35 | CELSIUS | 18 | HOUR | A suspension of 0.15 g (0.25 mmol) [6-bromo-5-(1-isopropyl-piperidin-4-yloxy)-1H-indol-2-yl]-[4-(piperidine-1-sulfonyl)-piperazin-1-yl]-methanone (example 1), 119 mg (0.76 mmol) 2-chloropyridine-4-boronic acid, 91 mg (0.50 mmol) copper(II) acetate and 80 μL (78 mg, 1.0 mmol) pyridine in 4 ml chloroform was stirred 18 h... | 10.6084/m9.figshare.5104873.v1 | null | Boronic acid | null | c1ccc2[nH]ccc2c1.c1ccncc1 | c1ccc2[nH]ccc2c1.c1ccncc1 | C1CC[NH]CC1.c1ccc2[nH]ccc2c1.C1C[NH]CC[NH]1.C1CC[NH]CC1.c1ccncc1 | HO-.B | C(C)(=O)[O-].[Cu+2].C(C)(=O)[O-].C(Cl)(Cl)Cl | 35 | 18 | CC(C)N1CCC(Oc2cc3cc(C(=O)N4CCN(S(=O)(=O)N5CCCCC5)CC4)[nH]c3cc2Br)CC1.OB(O)c1ccnc(Cl)c1>C(C)(=O)[O-].[Cu+2].C(C)(=O)[O-].C(Cl)(Cl)Cl>CC(C)N1CCC(Oc2cc3cc(C(=O)N4CCN(S(=O)(=O)N5CCCCC5)CC4)n(-c4ccnc(Cl)c4)c3cc2Br)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-664e9c5a155c430cac4fb54f62b4950a | CCS(=O)(=O)N1CCN(C(=O)c2cc3cc(OC4CCN(C(C)C)CC4)c(Br)cc3[nH]2)CC1.CS(=O)(=O)OCC(F)(F)F>>CCS(=O)(=O)N1CCN(C(=O)c2cc3cc(OC4CCN(C(C)C)CC4)c(Br)cc3n2CC(F)(F)F)CC1 | O.CS(=O)(=O)OCC(F)(F)F.BrC1=C(C=C2C=C(NC2=C1)C(=O)N1CCN(CC1)S(=O)(=O)CC)OC1CCN(CC1)C(C)C.[H-].[Na+]>>BrC1=C(C=C2C=C(N(C2=C1)CC(F)(F)F)C(=O)N1CCN(CC1)S(=O)(=O)CC)OC1CCN(CC1)C(C)C | [CH3:1][CH2:2][S:3](=[O:4])(=[O:5])[N:6]1[CH2:7][CH2:8][N:9]([C:10](=[O:11])[c:12]2[cH:13][c:14]3[cH:15][c:16]([O:17][CH:18]4[CH2:19][CH2:20][N:21]([CH:22]([CH3:23])[CH3:24])[CH2:25][CH2:26]4)[c:27]([Br:28])[cH:29][c:30]3[nH:31]2)[CH2:37][CH2:38]1.CS(=O)(=O)O[CH2:32][C:33]([F:34])([F:35])[F:36]>>[CH3:1][CH2:2][S:3](=[O... | CCS(=O)(=O)N1CCN(C(=O)c2cc3cc(OC4CCN(C(C)C)CC4)c(Br)cc3[nH]2)CC1.CS(=O)(=O)OCC(F)(F)F | CCS(=O)(=O)N1CCN(C(=O)c2cc3cc(OC4CCN(C(C)C)CC4)c(Br)cc3n2CC(F)(F)F)CC1 | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | OtherReaction | d896e99f48a796a768d64b339abb5adbd8bc977c5bccdd47720d3a6657256b55 | 0b4f3c8c88df0a792d0db7d59004d7fe5681a61dd48ef2449ddca2d636f76ada | O=C(c1cc2cc(OC3CCNCC3)ccc2[nH]1)N1CCNCC1 | C-S(=O)(=O)-O-[CH2;D2;+0:1]-[C:2](-[F;D1;H0:3])(-[F;D1;H0:4])-[F;D1;H0:5].[C:6]-[#7:7](-[C:8](=[O;D1;H0:9])-[c:10]1:[c:11]:[c:12]:[c:13](:[c:14]):[nH;D2;+0:15]:1)-[C:16]>>[C:6]-[#7:7](-[C:8](=[O;D1;H0:9])-[c:10]1:[c:11]:[c:12]:[c:13](:[c:14]):[n;H0;D3;+0:15]:1-[CH2;D2;+0:1]-[C:2](-[F;D1;H0:3])(-[F;D1;H0:4])-[F;D1;H0:5]... | 53 | [{"value": 52.0, "product": "BrC1=C(C=C2C=C(N(C2=C1)CC(F)(F)F)C(=O)N1CCN(CC1)S(=O)(=O)CC)OC1CCN(CC1)C(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 53.0, "product": "BrC1=C(C=C2C=C(N(C2=C1)CC(F)(F)F)C(=O)N1CCN(CC1)S(=O)(=O)CC)OC1CCN(CC1)C(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false... | 70 | CELSIUS | 15 | MINUTE | To a solution of 144 mg (0.26 mmol) [6-bromo-5-(1-isopropyl-piperidin-4-yloxy)-1H-indol-2-yl]-(4-ethanesulfonyl-piperazin-1-yl)-methanone (example 10) in 3 mL N,N-dimethylformamide, were added 13 mg (0.29 mmol; 55% dispersion in mineral oil) sodium hydride. The reaction mixture was stirred 15 min at 70° C. 68 mg (0.29 ... | 10.6084/m9.figshare.5104873.v1 | null | Mesylate | null | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1 | C1C[NH]CC[NH]1.c1ccc2[nH]ccc2c1.C1CC[NH]CC1 | MsOH.HO- | CN(C=O)C | 70 | 0.25 | CCS(=O)(=O)N1CCN(C(=O)c2cc3cc(OC4CCN(C(C)C)CC4)c(Br)cc3[nH]2)CC1.CS(=O)(=O)OCC(F)(F)F>CN(C=O)C>CCS(=O)(=O)N1CCN(C(=O)c2cc3cc(OC4CCN(C(C)C)CC4)c(Br)cc3n2CC(F)(F)F)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-3ebb0e6b7e434129bfef22e8e0b9d4cf | CC(C)N1CCC(Oc2cc3cc(C(=O)O)[nH]c3cc2Br)CC1.O=S(=O)(N1CCNCC1)C(F)(F)F>>CC(C)N1CCC(Oc2cc3cc(C(=O)N4CCN(S(=O)(=O)C(F)(F)F)CC4)[nH]c3cc2Br)CC1 | FC(S(=O)(=O)Cl)(F)F.BrC1=C(C=C2C=C(NC2=C1)C(=O)O)OC1CCN(CC1)C(C)C.Cl.FC(S(=O)(=O)N1CCNCC1)(F)F.N1(CCNCC1)C(=O)OC(C)(C)C>>BrC1=C(C=C2C=C(NC2=C1)C(=O)N1CCN(CC1)S(=O)(=O)C(F)(F)F)OC1CCN(CC1)C(C)C | O[C:14]([c:13]1[cH:12][c:11]2[cH:10][c:9]([O:8][CH:7]3[CH2:6][CH2:5][N:4]([CH:2]([CH3:1])[CH3:3])[CH2:35][CH2:34]3)[c:32]([Br:33])[cH:31][c:30]2[nH:29]1)=[O:15].[NH:16]1[CH2:17][CH2:18][N:19]([S:20](=[O:21])(=[O:22])[C:23]([F:24])([F:25])[F:26])[CH2:27][CH2:28]1>>[CH3:1][CH:2]([CH3:3])[N:4]1[CH2:5][CH2:6][CH:7]([O:8][c... | CC(C)N1CCC(Oc2cc3cc(C(=O)O)[nH]c3cc2Br)CC1.O=S(=O)(N1CCNCC1)C(F)(F)F | CC(C)N1CCC(Oc2cc3cc(C(=O)N4CCN(S(=O)(=O)C(F)(F)F)CC4)[nH]c3cc2Br)CC1 | null | null | null | Acylation | Acylation of Nitrogen Nucleophiles by Carboxylic Acids | ed26ef5eea92a0cc433b3f89a34f4c61724425fa15a9d0ec83a0f7a903eec831 | c5e4172490b2731ba9322b68af56376edadc31ce0bb9a3dfdea23a1817a852fd | O=C(c1cc2cc(OC3CCNCC3)ccc2[nH]1)N1CCNCC1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[#7;a:5]:[c:6].[#7:7]1-[C:8]-[C:9]-[NH;D2;+0:10]-[C:11]-[C:12]-1>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[N;H0;D3;+0:10]1-[C:9]-[C:8]-[#7:7]-[C:12]-[C:11]-1)-[c:3](:[c:4]):[#7;a:5]:[c:6] | 48 | [{"value": 48.0, "product": "BrC1=C(C=C2C=C(NC2=C1)C(=O)N1CCN(CC1)S(=O)(=O)C(F)(F)F)OC1CCN(CC1)C(C)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The title compound was synthesized in analogy to example 1, from 6-bromo-5-(1-isopropyl-piperidin-4-yloxy)-1H-indole-2-carboxylic acid; hydrochloride (example 1, intermediate a) and 1-trifluoromethanesulfonyl-piperazine (prepared in analogy to International Patent Application Publ. No. WO 2003/064413 by using trifluoro... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | Tertiary amide | C1CNCC[NH]1 | C1C[NH]CC[NH]1 | C1CC[NH]CC1.c1ccc2[nH]ccc2c1.C1C[NH]CC[NH]1 | HO- | null | null | null | CC(C)N1CCC(Oc2cc3cc(C(=O)O)[nH]c3cc2Br)CC1.O=S(=O)(N1CCNCC1)C(F)(F)F>>CC(C)N1CCC(Oc2cc3cc(C(=O)N4CCN(S(=O)(=O)C(F)(F)F)CC4)[nH]c3cc2Br)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-2200d6b7e9f94cecbba6c389b32d518b | CC(C)(C)OC(=O)N1CCNCC1.CC(C)N1CCC(Oc2cc3cc(C(=O)O)[nH]c3cc2Br)CC1.O=S(=O)(Cl)C1CC1>>CC(C)N1CCC(Oc2cc3cc(C(=O)N4CCN(S(=O)(=O)C5CC5)CC4)[nH]c3cc2Br)CC1 | N1(CCNCC1)C(=O)OC(C)(C)C.Cl.BrC1=C(C=C2C=C(NC2=C1)C(=O)O)OC1CCN(CC1)C(C)C.C1(CC1)S(=O)(=O)N1CCNCC1.C1(CC1)S(=O)(=O)Cl>>BrC1=C(C=C2C=C(NC2=C1)C(=O)N1CCN(CC1)S(=O)(=O)C1CC1)OC1CCN(CC1)C(C)C | CC(C)(C)OC(=O)[N:19]1[CH2:18][CH2:17][NH:16][CH2:27][CH2:26]1.O[C:14]([c:13]1[cH:12][c:11]2[cH:10][c:9]([O:8][CH:7]3[CH2:6][CH2:5][N:4]([CH:2]([CH3:1])[CH3:3])[CH2:34][CH2:33]3)[c:31]([Br:32])[cH:30][c:29]2[nH:28]1)=[O:15].Cl[S:20](=[O:21])(=[O:22])[CH:23]1[CH2:24][CH2:25]1>>[CH3:1][CH:2]([CH3:3])[N:4]1[CH2:5][CH2:6][C... | CC(C)(C)OC(=O)N1CCNCC1.CC(C)N1CCC(Oc2cc3cc(C(=O)O)[nH]c3cc2Br)CC1.O=S(=O)(Cl)C1CC1 | CC(C)N1CCC(Oc2cc3cc(C(=O)N4CCN(S(=O)(=O)C5CC5)CC4)[nH]c3cc2Br)CC1 | null | null | null | Acylation | OtherReaction | 46aac7e0c5bae0c4b10c58b3e54bdd310ee6376094e059179d0bdbb508b434b4 | dd0d2994de79b42478fa7896ad0a1953280227920b0d81bb2d39f8ceafa61163 | O=C(c1cc2cc(OC3CCNCC3)ccc2[nH]1)N1CCN(S(=O)(=O)C2CC2)CC1 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1]1-[C:2]-[C:3]-[NH;D2;+0:4]-[C:5]-[C:6]-1.Cl-[S;H0;D4;+0:7](=[O;D1;H0:8])(=[O;D1;H0:9])-[C:10]1-[C:11]-[C:12]-1.O-[C;H0;D3;+0:13](=[O;D1;H0:14])-[c:15](:[c:16]):[#7;a:17]:[c:18]>>[O;D1;H0:14]=[C;H0;D3;+0:13](-[N;H0;D3;+0:4]1-[C:3]-[C:2]-[N;H0;D3;+0:1](-[S;H0;D4;+0:7](=[O;D1;H0:8])(=[O;D... | 62 | [{"value": 62.0, "product": "BrC1=C(C=C2C=C(NC2=C1)C(=O)N1CCN(CC1)S(=O)(=O)C1CC1)OC1CCN(CC1)C(C)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The title compound was synthesized in analogy to example 1, from 6-bromo-5-(1-isopropyl-piperidin-4-yloxy)-1H-indole-2-carboxylic acid hydrochloride (example 1, intermediate a) and cyclopropylsulfonyl-piperazine (prepared in analogy to International Patent Application Publ. No. WO 2003/064413 by using cyclopropylsulfon... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Carboxylic acid.Ether.Secondary amine.Sulfonyl halide.Boc | Tertiary amide.Tertiary amine | C1C[NH]CCN1 | C1C[NH]CC[NH]1 | C1CC[NH]CC1.c1ccc2[nH]ccc2c1.C1C[NH]CC[NH]1.C1CC1 | HCl | null | null | null | CC(C)(C)OC(=O)N1CCNCC1.CC(C)N1CCC(Oc2cc3cc(C(=O)O)[nH]c3cc2Br)CC1.O=S(=O)(Cl)C1CC1>>CC(C)N1CCC(Oc2cc3cc(C(=O)N4CCN(S(=O)(=O)C5CC5)CC4)[nH]c3cc2Br)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e69e3bf0f3a64f0d91ae797b41304377 | CC(C)N1CCC(Oc2cc3cc(C(=O)O)[nH]c3cc2Br)CC1.O=C(C1CC1)N1CCNCC1>>CC(C)N1CCC(Oc2cc3cc(C(=O)N4CCN(C(=O)C5CC5)CC4)[nH]c3cc2Br)CC1 | Cl.BrC1=C(C=C2C=C(NC2=C1)C(=O)O)OC1CCN(CC1)C(C)C.C1(CC1)C(=O)N1CCNCC1>>BrC1=C(C=C2C=C(NC2=C1)C(=O)N1CCN(CC1)C(=O)C1CC1)OC1CCN(CC1)C(C)C | O[C:14]([c:13]1[cH:12][c:11]2[cH:10][c:9]([O:8][CH:7]3[CH2:6][CH2:5][N:4]([CH:2]([CH3:1])[CH3:3])[CH2:33][CH2:32]3)[c:30]([Br:31])[cH:29][c:28]2[nH:27]1)=[O:15].[NH:16]1[CH2:17][CH2:18][N:19]([C:20](=[O:21])[CH:22]2[CH2:23][CH2:24]2)[CH2:25][CH2:26]1>>[CH3:1][CH:2]([CH3:3])[N:4]1[CH2:5][CH2:6][CH:7]([O:8][c:9]2[cH:10][... | CC(C)N1CCC(Oc2cc3cc(C(=O)O)[nH]c3cc2Br)CC1.O=C(C1CC1)N1CCNCC1 | CC(C)N1CCC(Oc2cc3cc(C(=O)N4CCN(C(=O)C5CC5)CC4)[nH]c3cc2Br)CC1 | null | null | null | Acylation | Acylation of Nitrogen Nucleophiles by Carboxylic Acids | ed26ef5eea92a0cc433b3f89a34f4c61724425fa15a9d0ec83a0f7a903eec831 | c5e4172490b2731ba9322b68af56376edadc31ce0bb9a3dfdea23a1817a852fd | O=C(c1cc2cc(OC3CCNCC3)ccc2[nH]1)N1CCN(C(=O)C2CC2)CC1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[#7;a:5]:[c:6].[#7:7]1-[C:8]-[C:9]-[NH;D2;+0:10]-[C:11]-[C:12]-1>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[N;H0;D3;+0:10]1-[C:9]-[C:8]-[#7:7]-[C:12]-[C:11]-1)-[c:3](:[c:4]):[#7;a:5]:[c:6] | 48 | [{"value": 48.0, "product": "BrC1=C(C=C2C=C(NC2=C1)C(=O)N1CCN(CC1)C(=O)C1CC1)OC1CCN(CC1)C(C)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The title compound was synthesized in analogy to example 1, from 6-bromo-5-(1-isopropyl-piperidin-4-yloxy)-1H-indole-2-carboxylic acid hydrochloride (example 1, intermediate a) and 1-(cyclopropanecarbonyl)piperazine to afford the title compound as a light-yellow foam (48%).
Conditions: See reaction.notes.procedure_deta... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | Tertiary amide | C1CNCC[NH]1 | C1C[NH]CC[NH]1 | C1CC[NH]CC1.c1ccc2[nH]ccc2c1.C1C[NH]CC[NH]1.C1CC1 | HO- | null | null | null | CC(C)N1CCC(Oc2cc3cc(C(=O)O)[nH]c3cc2Br)CC1.O=C(C1CC1)N1CCNCC1>>CC(C)N1CCC(Oc2cc3cc(C(=O)N4CCN(C(=O)C5CC5)CC4)[nH]c3cc2Br)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-3b3e5c9eadae4f55acaf58a8096343cf | CC(=O)N1CCNCC1.CC(C)N1CCC(Oc2cc3cc(C(=O)O)[nH]c3cc2Br)CC1>>CC(=O)N1CCN(C(=O)c2cc3cc(OC4CCN(C(C)C)CC4)c(Br)cc3[nH]2)CC1 | Cl.BrC1=C(C=C2C=C(NC2=C1)C(=O)O)OC1CCN(CC1)C(C)C.C(C)(=O)N1CCNCC1>>BrC1=C(C=C2C=C(NC2=C1)C(=O)N1CCN(CC1)C(C)=O)OC1CCN(CC1)C(C)C | [CH3:1][C:2](=[O:3])[N:4]1[CH2:5][CH2:6][NH:7][CH2:30][CH2:31]1.O[C:8](=[O:9])[c:10]1[cH:11][c:12]2[cH:13][c:14]([O:15][CH:16]3[CH2:17][CH2:18][N:19]([CH:20]([CH3:21])[CH3:22])[CH2:23][CH2:24]3)[c:25]([Br:26])[cH:27][c:28]2[nH:29]1>>[CH3:1][C:2](=[O:3])[N:4]1[CH2:5][CH2:6][N:7]([C:8](=[O:9])[c:10]2[cH:11][c:12]3[cH:13]... | CC(=O)N1CCNCC1.CC(C)N1CCC(Oc2cc3cc(C(=O)O)[nH]c3cc2Br)CC1 | CC(=O)N1CCN(C(=O)c2cc3cc(OC4CCN(C(C)C)CC4)c(Br)cc3[nH]2)CC1 | null | null | null | Acylation | Acylation of Nitrogen Nucleophiles by Carboxylic Acids | be4b86020a065d99e289e528d425e25dd0737bea0f2fd81bb05a4d03f92a7d75 | c5e4172490b2731ba9322b68af56376edadc31ce0bb9a3dfdea23a1817a852fd | O=C(c1cc2cc(OC3CCNCC3)ccc2[nH]1)N1CCNCC1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[#7;a:5]:[c:6].[#7:7]1-[C:8]-[C:9]-[NH;D2;+0:10]-[C:11]-[C:12]-1>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[N;H0;D3;+0:10]1-[C:9]-[C:8]-[#7:7]-[C:12]-[C:11]-1)-[c:3](:[c:4]):[#7;a:5]:[c:6] | 52 | [{"value": 52.0, "product": "BrC1=C(C=C2C=C(NC2=C1)C(=O)N1CCN(CC1)C(C)=O)OC1CCN(CC1)C(C)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The title compound was synthesized in analogy to example 1, from 6-bromo-5-(1-isopropyl-piperidin-4-yloxy)-1H-indole-2-carboxylic acid hydrochloride (example 1, intermediate a) and 1-acetylpiperazine to afford the title compound as a light-yellow foam (52%).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | Tertiary amide | C1C[NH]CCN1 | C1C[NH]CC[NH]1 | C1C[NH]CC[NH]1.c1ccc2[nH]ccc2c1.C1CC[NH]CC1 | HO- | null | null | null | CC(=O)N1CCNCC1.CC(C)N1CCC(Oc2cc3cc(C(=O)O)[nH]c3cc2Br)CC1>>CC(=O)N1CCN(C(=O)c2cc3cc(OC4CCN(C(C)C)CC4)c(Br)cc3[nH]2)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-5cd740228ca8414e86fd02cc422b5198 | CC(C)N1CCC(Oc2cc3cc(C(=O)N4CCN(S(=O)(=O)C5CC5)CC4)n(CCO[Si](C)(C)C(C)(C)C)c3cc2Br)CC1>>CC(C)N1CCC(Oc2cc3cc(C(=O)N4CCN(S(=O)(=O)C5CC5)CC4)n(CCO)c3cc2Br)CC1 | BrC1=C(C=C2C=C(N(C2=C1)CCO[Si](C)(C)C(C)(C)C)C(=O)N1CCN(CC1)S(=O)(=O)C1CC1)OC1CCN(CC1)C(C)C.FC(C(=O)O)(F)F>>BrC1=C(C=C2C=C(N(C2=C1)CCO)C(=O)N1CCN(CC1)S(=O)(=O)C1CC1)OC1CCN(CC1)C(C)C | CC(C)(C)[Si](C)(C)[O:31][CH2:30][CH2:29][n:28]1[c:13]([C:14](=[O:15])[N:16]2[CH2:17][CH2:18][N:19]([S:20](=[O:21])(=[O:22])[CH:23]3[CH2:24][CH2:25]3)[CH2:26][CH2:27]2)[cH:12][c:11]2[cH:10][c:9]([O:8][CH:7]3[CH2:6][CH2:5][N:4]([CH:2]([CH3:1])[CH3:3])[CH2:37][CH2:36]3)[c:34]([Br:35])[cH:33][c:32]21>>[CH3:1][CH:2]([CH3:3]... | CC(C)N1CCC(Oc2cc3cc(C(=O)N4CCN(S(=O)(=O)C5CC5)CC4)n(CCO[Si](C)(C)C(C)(C)C)c3cc2Br)CC1 | CC(C)N1CCC(Oc2cc3cc(C(=O)N4CCN(S(=O)(=O)C5CC5)CC4)n(CCO)c3cc2Br)CC1 | null | null | ClCCl | Deprotection | Alcohol deprotection from silyl ethers | 6ff8c9c41093ab5237b871dd4689ba6431022d615e227d3774901a983c846e4b | 84d9f5b4e7757c58e584c26c7d52c9a3f594fbcb0c0d22f34765a93a932fcd5b | O=C(c1cc2cc(OC3CCNCC3)ccc2[nH]1)N1CCN(S(=O)(=O)C2CC2)CC1 | C-C(-C)(-C)-[Si](-C)(-C)-[O;H0;D2;+0:1]-[C:2]-[C:3]>>[C:3]-[C:2]-[OH;D1;+0:1] | 99 | [{"value": 99.0, "product": "BrC1=C(C=C2C=C(N(C2=C1)CCO)C(=O)N1CCN(CC1)S(=O)(=O)C1CC1)OC1CCN(CC1)C(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 99.0, "product": "BrC1=C(C=C2C=C(N(C2=C1)CCO)C(=O)N1CCN(CC1)S(=O)(=O)C1CC1)OC1CCN(CC1)C(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | A solution of 85 mg (0.12 mmol) [6-bromo-1-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-5-(1-isopropyl-piperidin-4-yloxy)-1H-indol-2-yl]-(4-cyclopropanesulfonyl-piperazin-1-yl)-methanone in 2 mL dichloromethane was cooled to 0° C. and 1.0 mL (1.49 g, 13.1 mmol) trifluoroacetic acid were added. The cooling bath was remove... | 10.6084/m9.figshare.5104873.v1 | null | TMS ether protective group | Primary alcohol | null | null | C1CC[NH]CC1.c1ccc2[nH]ccc2c1.C1C[NH]CC[NH]1.C1CC1 | Other | ClCCl | null | 1 | CC(C)N1CCC(Oc2cc3cc(C(=O)N4CCN(S(=O)(=O)C5CC5)CC4)n(CCO[Si](C)(C)C(C)(C)C)c3cc2Br)CC1>ClCCl>CC(C)N1CCC(Oc2cc3cc(C(=O)N4CCN(S(=O)(=O)C5CC5)CC4)n(CCO)c3cc2Br)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-900d663f816341dd876527062f41434b | CC(C)(C)[Si](C)(C)OCCBr.CC(C)N1CCC(Oc2cc3cc(C(=O)N4CCN(S(=O)(=O)C5CC5)CC4)[nH]c3cc2Br)CC1>>CC(C)N1CCC(Oc2cc3cc(C(=O)N4CCN(S(=O)(=O)C5CC5)CC4)n(CCO[Si](C)(C)C(C)(C)C)c3cc2Br)CC1 | BrC1=C(C=C2C=C(NC2=C1)C(=O)N1CCN(CC1)S(=O)(=O)C1CC1)OC1CCN(CC1)C(C)C.[H-].[Na+].BrCCO[Si](C)(C)C(C)(C)C>>BrC1=C(C=C2C=C(N(C2=C1)CCO[Si](C)(C)C(C)(C)C)C(=O)N1CCN(CC1)S(=O)(=O)C1CC1)OC1CCN(CC1)C(C)C | Br[CH2:29][CH2:30][O:31][Si:32]([CH3:33])([CH3:34])[C:35]([CH3:36])([CH3:37])[CH3:38].[CH3:1][CH:2]([CH3:3])[N:4]1[CH2:5][CH2:6][CH:7]([O:8][c:9]2[cH:10][c:11]3[cH:12][c:13]([C:14](=[O:15])[N:16]4[CH2:17][CH2:18][N:19]([S:20](=[O:21])(=[O:22])[CH:23]5[CH2:24][CH2:25]5)[CH2:26][CH2:27]4)[nH:28][c:39]3[cH:40][c:41]2[Br:4... | CC(C)(C)[Si](C)(C)OCCBr.CC(C)N1CCC(Oc2cc3cc(C(=O)N4CCN(S(=O)(=O)C5CC5)CC4)[nH]c3cc2Br)CC1 | CC(C)N1CCC(Oc2cc3cc(C(=O)N4CCN(S(=O)(=O)C5CC5)CC4)n(CCO[Si](C)(C)C(C)(C)C)c3cc2Br)CC1 | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 92cc004fc3e2a92f5c9aa0385cdf93f1126e35d5aa485f4f5fe9240c9543c8fe | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | O=C(c1cc2cc(OC3CCNCC3)ccc2[nH]1)N1CCN(S(=O)(=O)C2CC2)CC1 | Br-[CH2;D2;+0:1]-[C:2]-[#8:3].[C:4]-[#7:5](-[C:6](=[O;D1;H0:7])-[c:8]1:[c:9]:[c:10]:[c:11](:[c:12]):[nH;D2;+0:13]:1)-[C:14]>>[#8:3]-[C:2]-[CH2;D2;+0:1]-[n;H0;D3;+0:13]1:[c:8](-[C:6](=[O;D1;H0:7])-[#7:5](-[C:4])-[C:14]):[c:9]:[c:10]:[c:11]:1:[c:12] | 36 | [{"value": 36.0, "product": "BrC1=C(C=C2C=C(N(C2=C1)CCO[Si](C)(C)C(C)(C)C)C(=O)N1CCN(CC1)S(=O)(=O)C1CC1)OC1CCN(CC1)C(C)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The title compound was prepared in analogy to example 12, from [6-bromo-5-(1-isopropyl-piperidin-4-yloxy)-1H-indol-2-yl]-(4-cyclopropanesulfonyl-piperazin-1-yl)-methanone (example 17), sodium hydride and (2-bromoethoxy)-tert-butyldimethylsilane in N,N-dimethylformamide, to afford the title compound as a colourless foam... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1 | C1CC[NH]CC1.c1ccc2[nH]ccc2c1.C1C[NH]CC[NH]1.C1CC1 | HBr | CN(C=O)C | null | null | CC(C)(C)[Si](C)(C)OCCBr.CC(C)N1CCC(Oc2cc3cc(C(=O)N4CCN(S(=O)(=O)C5CC5)CC4)[nH]c3cc2Br)CC1>CN(C=O)C>CC(C)N1CCC(Oc2cc3cc(C(=O)N4CCN(S(=O)(=O)C5CC5)CC4)n(CCO[Si](C)(C)C(C)(C)C)c3cc2Br)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-045bbf6a327c481b8dd1b5f284784d98 | CS(=O)(=O)N1CCNCC1.Cc1cc2[nH]c(C(=O)O)cc2cc1OC1CCN(C(C)C)CC1>>Cc1cc2[nH]c(C(=O)N3CCN(S(C)(=O)=O)CC3)cc2cc1OC1CCN(C(C)C)CC1 | Cl.C(C)(C)N1CCC(CC1)OC=1C=C2C=C(NC2=CC1C)C(=O)O.CS(=O)(=O)N1CCNCC1>>C(C)(C)N1CCC(CC1)OC=1C=C2C=C(NC2=CC1C)C(=O)N1CCN(CC1)S(=O)(=O)C | [NH:9]1[CH2:10][CH2:11][N:12]([S:13]([CH3:14])(=[O:15])=[O:16])[CH2:17][CH2:18]1.O[C:7]([c:6]1[nH:5][c:4]2[cH:3][c:2]([CH3:1])[c:22]([O:23][CH:24]3[CH2:25][CH2:26][N:27]([CH:28]([CH3:29])[CH3:30])[CH2:31][CH2:32]3)[cH:21][c:20]2[cH:19]1)=[O:8]>>[CH3:1][c:2]1[cH:3][c:4]2[nH:5][c:6]([C:7](=[O:8])[N:9]3[CH2:10][CH2:11][N:... | CS(=O)(=O)N1CCNCC1.Cc1cc2[nH]c(C(=O)O)cc2cc1OC1CCN(C(C)C)CC1 | Cc1cc2[nH]c(C(=O)N3CCN(S(C)(=O)=O)CC3)cc2cc1OC1CCN(C(C)C)CC1 | null | null | null | Acylation | Acylation of Nitrogen Nucleophiles by Carboxylic Acids | ed26ef5eea92a0cc433b3f89a34f4c61724425fa15a9d0ec83a0f7a903eec831 | c5e4172490b2731ba9322b68af56376edadc31ce0bb9a3dfdea23a1817a852fd | O=C(c1cc2cc(OC3CCNCC3)ccc2[nH]1)N1CCNCC1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[#7;a:5]:[c:6].[#7:7]1-[C:8]-[C:9]-[NH;D2;+0:10]-[C:11]-[C:12]-1>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[N;H0;D3;+0:10]1-[C:9]-[C:8]-[#7:7]-[C:12]-[C:11]-1)-[c:3](:[c:4]):[#7;a:5]:[c:6] | 49 | [{"value": 49.0, "product": "C(C)(C)N1CCC(CC1)OC=1C=C2C=C(NC2=CC1C)C(=O)N1CCN(CC1)S(=O)(=O)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The title compound was synthesized in analogy to example 1, from 5-(1-isopropyl-piperidin-4-yloxy)-6-methyl-1H-indole-2-carboxylic acid hydrochloride and 1-methanesulfonylpiperazine to afford the title compound as a light-yellow solid (49%).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | Tertiary amide | C1CNCC[NH]1 | C1C[NH]CC[NH]1 | c1ccc2[nH]ccc2c1.C1C[NH]CC[NH]1.C1CC[NH]CC1 | HO- | null | null | null | CS(=O)(=O)N1CCNCC1.Cc1cc2[nH]c(C(=O)O)cc2cc1OC1CCN(C(C)C)CC1>>Cc1cc2[nH]c(C(=O)N3CCN(S(C)(=O)=O)CC3)cc2cc1OC1CCN(C(C)C)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-bdc9eaeae824466c8063ebed2b0bdb5d | CC(C)N1CCC(O)CC1.CCOC(=O)c1cc2cc(O)c(C)cc2[nH]1>>CCOC(=O)c1cc2cc(OC3CCN(C(C)C)CC3)c(C)cc2[nH]1 | N(=NC(=O)OC(C)(C)C)C(=O)OC(C)(C)C.C(C)OC(=O)C=1NC2=CC(=C(C=C2C1)O)C.C(C)(C)N1CCC(CC1)O.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1>>C(C)OC(=O)C=1NC2=CC(=C(C=C2C1)OC1CCN(CC1)C(C)C)C | O[CH:12]1[CH2:13][CH2:14][N:15]([CH:16]([CH3:17])[CH3:18])[CH2:19][CH2:20]1.[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][c:8]2[cH:9][c:10]([OH:11])[c:21]([CH3:22])[cH:23][c:24]2[nH:25]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][c:8]2[cH:9][c:10]([O:11][CH:12]3[CH2:13][CH2:14][N:15]([CH:16]([CH3:17])[CH3:18])[CH2:19... | CC(C)N1CCC(O)CC1.CCOC(=O)c1cc2cc(O)c(C)cc2[nH]1 | CCOC(=O)c1cc2cc(OC3CCN(C(C)C)CC3)c(C)cc2[nH]1 | null | null | O1CCCC1 | Heteroatom Alkylation and Arylation | Mitsunobu aryl ether | a9e936b0e9135225700edbab1c7696738b7f1f0756494b6ceeeda63b184d572f | 776ba735002e33225fbc578943016110c2c43efefd97bfeea4ec3cc2e2e1532f | c1cc2cc(OC3CCNCC3)ccc2[nH]1 | O-[CH;D3;+0:1]1-[C:2]-[C:3]-[#7:4]-[C:5]-[C:6]-1.[OH;D1;+0:7]-[c:8](:[c:9]):[c:10]>>[c:9]:[c:8](-[O;H0;D2;+0:7]-[CH;D3;+0:1]1-[C:2]-[C:3]-[#7:4]-[C:5]-[C:6]-1):[c:10] | 38 | [{"value": 38.0, "product": "C(C)OC(=O)C=1NC2=CC(=C(C=C2C1)OC1CCN(CC1)C(C)C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 37.7, "product": "C(C)OC(=O)C=1NC2=CC(=C(C=C2C1)OC1CCN(CC1)C(C)C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 18 | HOUR | To a suspension of 0.125 g (0.57 mmol) 5-hydroxy-6-methyl-1H-indole-2-carboxylic acid ethyl ester in 3 mL tetrahydrofuran, 98 mg (0.68 mmol) 1-isopropyl-piperidin-4-ol and 0.18 g (0.68 mmol) triphenylphosphine were added. The reaction was cooled to 0° C., 0.16 g (0.68 mmol) di-tert-butyl azodicarboxylate were added and... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol.Aromatic alcohol | Ether | C1CC[NH]CC1 | C1CC[NH]CC1 | c1ccc2[nH]ccc2c1.C1CC[NH]CC1 | HO- | O1CCCC1 | 0 | 18 | CC(C)N1CCC(O)CC1.CCOC(=O)c1cc2cc(O)c(C)cc2[nH]1>O1CCCC1>CCOC(=O)c1cc2cc(OC3CCN(C(C)C)CC3)c(C)cc2[nH]1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-83b1e8e5275742b29be9677410a23816 | CCOC(=O)c1cc2cc(OC)c(C)cc2[nH]1>>CCOC(=O)c1cc2cc(O)c(C)cc2[nH]1 | C(C)OC(=O)C=1NC2=CC(=C(C=C2C1)OC)C.B(Br)(Br)Br>>C(C)OC(=O)C=1NC2=CC(=C(C=C2C1)O)C | C[O:11][c:10]1[cH:9][c:8]2[cH:7][c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[nH:16][c:15]2[cH:14][c:12]1[CH3:13]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][c:8]2[cH:9][c:10]([OH:11])[c:12]([CH3:13])[cH:14][c:15]2[nH:16]1 | CCOC(=O)c1cc2cc(OC)c(C)cc2[nH]1 | CCOC(=O)c1cc2cc(O)c(C)cc2[nH]1 | null | null | ClCCl | Deprotection | Cleavage of methoxy ethers to alcohols | c5320c7dfa4f544d4900efcae9b3262bf0d5286bcf39c86109232351f35b23d5 | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | c1ccc2[nH]ccc2c1 | C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[OH;D1;+0:1]-[c:2](:[c:3]):[c:4] | 43.2 | [{"value": 43.0, "product": "C(C)OC(=O)C=1NC2=CC(=C(C=C2C1)O)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 43.2, "product": "C(C)OC(=O)C=1NC2=CC(=C(C=C2C1)O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | A solution of 0.13 g (0.56 mmol) 5-methoxy-6-methyl-1H-indole-2-carboxylic acid ethyl ester in 3 mL dichloromethane was cooled to −78° C. 1.11 mL (1.1 mmol, 1 M solution in dichloromethane) boron tribromide were added and the cooling bath was removed. After stirring 2 h at room temperature, the solution was poured into... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | null | null | c1ccc2[nH]ccc2c1 | Other | ClCCl | null | 2 | CCOC(=O)c1cc2cc(OC)c(C)cc2[nH]1>ClCCl>CCOC(=O)c1cc2cc(O)c(C)cc2[nH]1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d044932258fe475c8040a0b2971784b8 | CCOC(=O)c1cc2cc(OC)c(C)cc2n1C(=O)OC(C)(C)C>>CCOC(=O)c1cc2cc(OC)c(C)cc2[nH]1 | CCOC(=O)C=1N(C2=CC(=C(C=C2C1)OC)C)C(=O)OC(C)(C)C.FC(C(=O)O)(F)F>>C(C)OC(=O)C=1NC2=CC(=C(C=C2C1)OC)C | CC(C)(C)OC(=O)[n:17]1[c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[cH:7][c:8]2[cH:9][c:10]([O:11][CH3:12])[c:13]([CH3:14])[cH:15][c:16]21>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][c:8]2[cH:9][c:10]([O:11][CH3:12])[c:13]([CH3:14])[cH:15][c:16]2[nH:17]1 | CCOC(=O)c1cc2cc(OC)c(C)cc2n1C(=O)OC(C)(C)C | CCOC(=O)c1cc2cc(OC)c(C)cc2[nH]1 | null | null | ClCCl | Reduction | Boc amine deprotection | 2e722145961e6ed684a4057199869eba686866962dedad6b4f68c70e9c6154ea | e1bf5a54b1f87284564f107662531aec2aff7de801e4606340967b38924afb28 | c1ccc2[nH]ccc2c1 | C-C(-C)(-C)-O-C(=O)-[n;H0;D3;+0:1]1:[c:2](:[c:3]):[c:4]:[c:5]:[c:6]:1-[C:7](=[O;D1;H0:8])-[#8:9]-[C:10]>>[C:10]-[#8:9]-[C:7](=[O;D1;H0:8])-[c:6]1:[c:5]:[c:4]:[c:2](:[c:3]):[nH;D2;+0:1]:1 | 97 | [{"value": 97.0, "product": "C(C)OC(=O)C=1NC2=CC(=C(C=C2C1)OC)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | A solution of 0.20 g (0.60 mmol) 5-methoxy-6-methyl-indole-1,2-dicarboxylic acid 1-tert-butyl ester 2-ethyl ester in 4 mL dichloromethane was cooled to 0° C. and 2 mL (3.0 g, 26.1 mmol) trifluoroacetic acid were added. The ice bath was removed and after stirring 1 h at room temperature the solution was evaporated to dr... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Boc | null | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1 | HO- | ClCCl | null | 1 | CCOC(=O)c1cc2cc(OC)c(C)cc2n1C(=O)OC(C)(C)C>ClCCl>CCOC(=O)c1cc2cc(OC)c(C)cc2[nH]1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e60f90ba2ed04fd082d42f89de8183e3 | CCOC(=O)c1cc2cc(OC)c(Br)cc2n1C(=O)OC(C)(C)C>>CCOC(=O)c1cc2cc(OC)c(C)cc2n1C(=O)OC(C)(C)C | C([O-])(O)=O.[Na+].CCOC(=O)C=1N(C2=CC(=C(C=C2C1)OC)Br)C(=O)OC(C)(C)C.CB1OB(OB(O1)C)C.C([O-])([O-])=O.[Na+].[Na+]>>CCOC(=O)C=1N(C2=CC(=C(C=C2C1)OC)C)C(=O)OC(C)(C)C | Br[c:13]1[c:10]([O:11][CH3:12])[cH:9][c:8]2[cH:7][c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[n:17]([C:18](=[O:19])[O:20][C:21]([CH3:22])([CH3:23])[CH3:24])[c:16]2[cH:15]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][c:8]2[cH:9][c:10]([O:11][CH3:12])[c:13]([CH3:14])[cH:15][c:16]2[n:17]1[C:18](=[O:19])[O:20][C:21]([CH3:22])... | CCOC(=O)c1cc2cc(OC)c(Br)cc2n1C(=O)OC(C)(C)C | CCOC(=O)c1cc2cc(OC)c(C)cc2n1C(=O)OC(C)(C)C | 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 | O.COCCOC.C(C)(=O)OCC | Functional Group Interconversion | OtherReaction | dbd18d2678064f1f36b138b22466f91ec2b8ad6433b033470409c1d945c1e16a | 56de34d4a44cb25d9380269ee5e138b0f24b40a3a0db22c5508049dc775a861f | c1ccc2[nH]ccc2c1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3](:[c:4]:[c:5]:[c:6]:1-[#8:7]):[#7;a:8](-[C:9](-[#8:10])=[O;D1;H0:11]):[c:12]-[C:13](-[#8:14])=[O;D1;H0:15]>>[#8:7]-[c:6]1:[c:5]:[c:4]:[c:3](:[c:2]:[c;H0;D3;+0:1]:1-[C;D1;H3:16]):[#7;a:8](-[C:9](-[#8:10])=[O;D1;H0:11]):[c:12]-[C:13](-[#8:14])=[O;D1;H0:15] | 57 | [{"value": 57.0, "product": "CCOC(=O)C=1N(C2=CC(=C(C=C2C1)OC)C)C(=O)OC(C)(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 57.0, "product": "CCOC(=O)C=1N(C2=CC(=C(C=C2C1)OC)C)C(=O)OC(C)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | To a solution of 0.20 g (0.50 mmol) 6-bromo-5-methoxy-indole-1,2-dicarboxylic acid 1-tert-butyl ester 2-ethyl ester in 8 mL 1,2-dimethoxyethane were added 58 μg (0.050 mmol) tetrakis(triphenylphosphine)palladium(0). After stirring 30 min at room temperature, 76 μg (0.60 mmol) trimethylboroxine and 0.16 g (1.50 mmol) so... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | null | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1 | 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.O.COCCOC.C(C)(=O)OCC | null | 0.5 | CCOC(=O)c1cc2cc(OC)c(Br)cc2n1C(=O)OC(C)(C)C>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.O.COCCOC.C(C)(=O)OCC>CCOC(=O)c1cc2cc(OC)c(C)cc2n1C(=O)OC(C)(C)C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-dd0394a8216149ca803701f59b103fc6 | CCOC(=O)N1CCNCC1.Cc1cc2[nH]c(C(=O)O)cc2cc1OC1CCN(C(C)C)CC1>>CCOC(=O)N1CCN(C(=O)c2cc3cc(OC4CCN(C(C)C)CC4)c(C)cc3[nH]2)CC1 | Cl.C(C)(C)N1CCC(CC1)OC=1C=C2C=C(NC2=CC1C)C(=O)O.C(C)OC(=O)N1CCNCC1>>C(C)OC(=O)N1CCN(CC1)C(=O)C=1NC2=CC(=C(C=C2C1)OC1CCN(CC1)C(C)C)C | [CH3:1][CH2:2][O:3][C:4](=[O:5])[N:6]1[CH2:7][CH2:8][NH:9][CH2:32][CH2:33]1.O[C:10](=[O:11])[c:12]1[cH:13][c:14]2[cH:15][c:16]([O:17][CH:18]3[CH2:19][CH2:20][N:21]([CH:22]([CH3:23])[CH3:24])[CH2:25][CH2:26]3)[c:27]([CH3:28])[cH:29][c:30]2[nH:31]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[N:6]1[CH2:7][CH2:8][N:9]([C:10](=[O:11]... | CCOC(=O)N1CCNCC1.Cc1cc2[nH]c(C(=O)O)cc2cc1OC1CCN(C(C)C)CC1 | CCOC(=O)N1CCN(C(=O)c2cc3cc(OC4CCN(C(C)C)CC4)c(C)cc3[nH]2)CC1 | null | null | null | Acylation | Acylation of Nitrogen Nucleophiles by Carboxylic Acids | be4b86020a065d99e289e528d425e25dd0737bea0f2fd81bb05a4d03f92a7d75 | c5e4172490b2731ba9322b68af56376edadc31ce0bb9a3dfdea23a1817a852fd | O=C(c1cc2cc(OC3CCNCC3)ccc2[nH]1)N1CCNCC1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[#7;a:5]:[c:6].[#7:7]1-[C:8]-[C:9]-[NH;D2;+0:10]-[C:11]-[C:12]-1>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[N;H0;D3;+0:10]1-[C:9]-[C:8]-[#7:7]-[C:12]-[C:11]-1)-[c:3](:[c:4]):[#7;a:5]:[c:6] | 65 | [{"value": 65.0, "product": "C(C)OC(=O)N1CCN(CC1)C(=O)C=1NC2=CC(=C(C=C2C1)OC1CCN(CC1)C(C)C)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The title compound was synthesized in analogy to example 1, from 5-(1-isopropyl-piperidin-4-yloxy)-6-methyl-1H-indole-2-carboxylic acid hydrochloride and 1-ethoxycarbonylpiperazine to afford the title compound as a light-yellow foam (65%).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | Tertiary amide | C1C[NH]CCN1 | C1C[NH]CC[NH]1 | C1C[NH]CC[NH]1.c1ccc2[nH]ccc2c1.C1CC[NH]CC1 | HO- | null | null | null | CCOC(=O)N1CCNCC1.Cc1cc2[nH]c(C(=O)O)cc2cc1OC1CCN(C(C)C)CC1>>CCOC(=O)N1CCN(C(=O)c2cc3cc(OC4CCN(C(C)C)CC4)c(C)cc3[nH]2)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-9f84cf9092984fa5987f0277e691be2b | Cc1cc2[nH]c(C(=O)O)cc2cc1OC1CCN(C(C)C)CC1.O=C(C1CC1)N1CCNCC1>>Cc1cc2[nH]c(C(=O)N3CCN(C(=O)C4CC4)CC3)cc2cc1OC1CCN(C(C)C)CC1 | Cl.C(C)(C)N1CCC(CC1)OC=1C=C2C=C(NC2=CC1C)C(=O)O.C1(CC1)C(=O)N1CCNCC1>>C1(CC1)C(=O)N1CCN(CC1)C(=O)C=1NC2=CC(=C(C=C2C1)OC1CCN(CC1)C(C)C)C | O[C:7]([c:6]1[nH:5][c:4]2[cH:3][c:2]([CH3:1])[c:23]([O:24][CH:25]3[CH2:26][CH2:27][N:28]([CH:29]([CH3:30])[CH3:31])[CH2:32][CH2:33]3)[cH:22][c:21]2[cH:20]1)=[O:8].[NH:9]1[CH2:10][CH2:11][N:12]([C:13](=[O:14])[CH:15]2[CH2:16][CH2:17]2)[CH2:18][CH2:19]1>>[CH3:1][c:2]1[cH:3][c:4]2[nH:5][c:6]([C:7](=[O:8])[N:9]3[CH2:10][CH... | Cc1cc2[nH]c(C(=O)O)cc2cc1OC1CCN(C(C)C)CC1.O=C(C1CC1)N1CCNCC1 | Cc1cc2[nH]c(C(=O)N3CCN(C(=O)C4CC4)CC3)cc2cc1OC1CCN(C(C)C)CC1 | null | null | null | Acylation | Acylation of Nitrogen Nucleophiles by Carboxylic Acids | ed26ef5eea92a0cc433b3f89a34f4c61724425fa15a9d0ec83a0f7a903eec831 | c5e4172490b2731ba9322b68af56376edadc31ce0bb9a3dfdea23a1817a852fd | O=C(c1cc2cc(OC3CCNCC3)ccc2[nH]1)N1CCN(C(=O)C2CC2)CC1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[#7;a:5]:[c:6].[#7:7]1-[C:8]-[C:9]-[NH;D2;+0:10]-[C:11]-[C:12]-1>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[N;H0;D3;+0:10]1-[C:9]-[C:8]-[#7:7]-[C:12]-[C:11]-1)-[c:3](:[c:4]):[#7;a:5]:[c:6] | 56 | [{"value": 56.0, "product": "C1(CC1)C(=O)N1CCN(CC1)C(=O)C=1NC2=CC(=C(C=C2C1)OC1CCN(CC1)C(C)C)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The title compound was synthesized in analogy to example 1, from 5-(1-isopropyl-piperidin-4-yloxy)-6-methyl-1H-indole-2-carboxylic acid hydrochloride and 1-(cyclopropanecarbonyl)piperazine to afford the title compound as a light-yellow foam (56%).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | Tertiary amide | C1CNCC[NH]1 | C1C[NH]CC[NH]1 | c1ccc2[nH]ccc2c1.C1C[NH]CC[NH]1.C1CC1.C1CC[NH]CC1 | HO- | null | null | null | Cc1cc2[nH]c(C(=O)O)cc2cc1OC1CCN(C(C)C)CC1.O=C(C1CC1)N1CCNCC1>>Cc1cc2[nH]c(C(=O)N3CCN(C(=O)C4CC4)CC3)cc2cc1OC1CCN(C(C)C)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-181aad76998c4b76a9cc21cbd335fd4f | CC(C)OS(C)(=O)=O.Cc1cc2[nH]c(C(=O)N3CCN(S(C)(=O)=O)CC3)cc2cc1OC1CCN(C(C)C)CC1>>Cc1cc2c(cc1OC1CCN(C(C)C)CC1)cc(C(=O)N1CCN(S(C)(=O)=O)CC1)n2C(C)C | C(C)(C)N1CCC(CC1)OC=1C=C2C=C(NC2=CC1C)C(=O)N1CCN(CC1)S(=O)(=O)C.C([O-])([O-])=O.[Cs+].[Cs+].CS(=O)(=O)OC(C)C>>C(C)(C)N1C(=CC2=CC(=C(C=C12)C)OC1CCN(CC1)C(C)C)C(=O)N1CCN(CC1)S(=O)(=O)C | CS(=O)(=O)O[CH:33]([CH3:34])[CH3:35].[CH3:1][c:2]1[cH:3][c:4]2[c:5]([cH:6][c:7]1[O:8][CH:9]1[CH2:10][CH2:11][N:12]([CH:13]([CH3:14])[CH3:15])[CH2:16][CH2:17]1)[cH:18][c:19]([C:20](=[O:21])[N:22]1[CH2:23][CH2:24][N:25]([S:26]([CH3:27])(=[O:28])=[O:29])[CH2:30][CH2:31]1)[nH:32]2>>[CH3:1][c:2]1[cH:3][c:4]2[c:5]([cH:6][c:7... | CC(C)OS(C)(=O)=O.Cc1cc2[nH]c(C(=O)N3CCN(S(C)(=O)=O)CC3)cc2cc1OC1CCN(C(C)C)CC1 | Cc1cc2c(cc1OC1CCN(C(C)C)CC1)cc(C(=O)N1CCN(S(C)(=O)=O)CC1)n2C(C)C | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | d896e99f48a796a768d64b339abb5adbd8bc977c5bccdd47720d3a6657256b55 | 0b4f3c8c88df0a792d0db7d59004d7fe5681a61dd48ef2449ddca2d636f76ada | O=C(c1cc2cc(OC3CCNCC3)ccc2[nH]1)N1CCNCC1 | C-S(=O)(=O)-O-[CH;D3;+0:1](-[C;D1;H3:2])-[C;D1;H3:3].[C:4]-[#7:5](-[C:6](=[O;D1;H0:7])-[c:8]1:[c:9]:[c:10]:[c:11](:[c:12]):[nH;D2;+0:13]:1)-[C:14]>>[C:4]-[#7:5](-[C:6](=[O;D1;H0:7])-[c:8]1:[c:9]:[c:10]:[c:11](:[c:12]):[n;H0;D3;+0:13]:1-[CH;D3;+0:1](-[C;D1;H3:2])-[C;D1;H3:3])-[C:14] | 9 | [{"value": 9.0, "product": "C(C)(C)N1C(=CC2=CC(=C(C=C12)C)OC1CCN(CC1)C(C)C)C(=O)N1CCN(CC1)S(=O)(=O)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The title compound was synthesized in analogy to example 4, from [5-(1-isopropyl-piperidin-4-yloxy)-6-methyl-1H-indol-2-yl]-(4-methanesulfonyl-piperazin-1-yl)-methanone (example 29), cesium carbonate and isopropyl methanesulfonate, to afford the title compound as a light-yellow oil (9%).
Conditions: See reaction.notes.... | 10.6084/m9.figshare.5104873.v1 | null | Mesylate | null | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1 | C1CC[NH]CC1.c1ccc2[nH]ccc2c1.C1C[NH]CC[NH]1 | MsOH.HO- | null | null | null | CC(C)OS(C)(=O)=O.Cc1cc2[nH]c(C(=O)N3CCN(S(C)(=O)=O)CC3)cc2cc1OC1CCN(C(C)C)CC1>>Cc1cc2c(cc1OC1CCN(C(C)C)CC1)cc(C(=O)N1CCN(S(C)(=O)=O)CC1)n2C(C)C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-738d11a3f8a34cebbe5ca2ff2b99cedf | CC(C)(C)OC(=O)N1CCNCC1.CC(C)N1CCC(Oc2cc3cc(C(=O)O)[nH]c3cc2Cl)CC1>>CC(C)N1CCC(Oc2cc3cc(C(=O)N4CCN(C(=O)OC(C)(C)C)CC4)[nH]c3cc2Cl)CC1 | Cl.ClC1=C(C=C2C=C(NC2=C1)C(=O)O)OC1CCN(CC1)C(C)C.[Cl-].[Li+].C(C)(C)(C)OC(=O)N1CCNCC1.F[B-](F)(F)F.N1(N=NC2=C1C=CC=C2)OC(=[N+](C)C)N(C)C.C(C)(C)N(C(C)C)CC>>C(C)(C)(C)OC(=O)N1CCN(CC1)C(=O)C=1NC2=CC(=C(C=C2C1)OC1CCN(CC1)C(C)C)Cl | [NH:16]1[CH2:17][CH2:18][N:19]([C:20](=[O:21])[O:22][C:23]([CH3:24])([CH3:25])[CH3:26])[CH2:27][CH2:28]1.O[C:14]([c:13]1[cH:12][c:11]2[cH:10][c:9]([O:8][CH:7]3[CH2:6][CH2:5][N:4]([CH:2]([CH3:1])[CH3:3])[CH2:35][CH2:34]3)[c:32]([Cl:33])[cH:31][c:30]2[nH:29]1)=[O:15]>>[CH3:1][CH:2]([CH3:3])[N:4]1[CH2:5][CH2:6][CH:7]([O:8... | CC(C)(C)OC(=O)N1CCNCC1.CC(C)N1CCC(Oc2cc3cc(C(=O)O)[nH]c3cc2Cl)CC1 | CC(C)N1CCC(Oc2cc3cc(C(=O)N4CCN(C(=O)OC(C)(C)C)CC4)[nH]c3cc2Cl)CC1 | null | null | CN(C=O)C | Acylation | Acylation of Nitrogen Nucleophiles by Carboxylic Acids | ed26ef5eea92a0cc433b3f89a34f4c61724425fa15a9d0ec83a0f7a903eec831 | c5e4172490b2731ba9322b68af56376edadc31ce0bb9a3dfdea23a1817a852fd | O=C(c1cc2cc(OC3CCNCC3)ccc2[nH]1)N1CCNCC1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[#7;a:5]:[c:6].[#7:7]1-[C:8]-[C:9]-[NH;D2;+0:10]-[C:11]-[C:12]-1>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[N;H0;D3;+0:10]1-[C:9]-[C:8]-[#7:7]-[C:12]-[C:11]-1)-[c:3](:[c:4]):[#7;a:5]:[c:6] | 57 | [{"value": 57.0, "product": "C(C)(C)(C)OC(=O)N1CCN(CC1)C(=O)C=1NC2=CC(=C(C=C2C1)OC1CCN(CC1)C(C)C)Cl", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 20 | HOUR | A mixture of 6-chloro-5-(1-isopropyl-piperidin-4-yloxy)-1H-indole-2-carboxylic acid hydrochloride salt with 1 eq. lithium chloride (760 mg, 1.0 eq.), tert-butyl-1-piperazinecarboxylate (467 mg, 1.25 eq.), O-(benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium tetrafluoroborate (838 mg, 1.25 eq.) and N,N-diisopropylethylami... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | Tertiary amide | C1CNCC[NH]1 | C1C[NH]CC[NH]1 | C1CC[NH]CC1.c1ccc2[nH]ccc2c1.C1C[NH]CC[NH]1 | HO- | CN(C=O)C | null | 20 | CC(C)(C)OC(=O)N1CCNCC1.CC(C)N1CCC(Oc2cc3cc(C(=O)O)[nH]c3cc2Cl)CC1>CN(C=O)C>CC(C)N1CCC(Oc2cc3cc(C(=O)N4CCN(C(=O)OC(C)(C)C)CC4)[nH]c3cc2Cl)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-3bc6f73e9bb3468996e0477624b39e75 | CC(C)N1CCC(O)CC1.CCOC(=O)c1cc2cc(O)c(Cl)cc2[nH]1>>CCOC(=O)c1cc2cc(OC3CCN(C(C)C)CC3)c(Cl)cc2[nH]1 | C(C)OC(=O)C=1NC2=CC(=C(C=C2C1)O)Cl.C(C)(C)N1CCC(CC1)O.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.CC(C)(C)OC(=O)/N=N/C(=O)OC(C)(C)C>>C(C)OC(=O)C=1NC2=CC(=C(C=C2C1)OC1CCN(CC1)C(C)C)Cl | O[CH:12]1[CH2:13][CH2:14][N:15]([CH:16]([CH3:17])[CH3:18])[CH2:19][CH2:20]1.[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][c:8]2[cH:9][c:10]([OH:11])[c:21]([Cl:22])[cH:23][c:24]2[nH:25]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][c:8]2[cH:9][c:10]([O:11][CH:12]3[CH2:13][CH2:14][N:15]([CH:16]([CH3:17])[CH3:18])[CH2:19]... | CC(C)N1CCC(O)CC1.CCOC(=O)c1cc2cc(O)c(Cl)cc2[nH]1 | CCOC(=O)c1cc2cc(OC3CCN(C(C)C)CC3)c(Cl)cc2[nH]1 | null | null | O1CCCC1 | Heteroatom Alkylation and Arylation | Mitsunobu aryl ether | a9e936b0e9135225700edbab1c7696738b7f1f0756494b6ceeeda63b184d572f | 776ba735002e33225fbc578943016110c2c43efefd97bfeea4ec3cc2e2e1532f | c1cc2cc(OC3CCNCC3)ccc2[nH]1 | O-[CH;D3;+0:1]1-[C:2]-[C:3]-[#7:4]-[C:5]-[C:6]-1.[OH;D1;+0:7]-[c:8](:[c:9]):[c:10]>>[c:9]:[c:8](-[O;H0;D2;+0:7]-[CH;D3;+0:1]1-[C:2]-[C:3]-[#7:4]-[C:5]-[C:6]-1):[c:10] | 67 | [{"value": 67.0, "product": "C(C)OC(=O)C=1NC2=CC(=C(C=C2C1)OC1CCN(CC1)C(C)C)Cl", "details": "PERCENTYIELD", "is_desired": false}, {"value": 66.7, "product": "C(C)OC(=O)C=1NC2=CC(=C(C=C2C1)OC1CCN(CC1)C(C)C)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 20 | HOUR | To a cold (0° C.) mixture of 6-chloro-5-hydroxy-1H-indole-2-carboxylic acid ethyl ester (625 mg, 1.0 eq.), 1-Isopropyl-piperidin-4-ol (448 mg, 1.2 eq.) and triphenylphosphine (846 mg, 1.2 eq.) in tetrahydrofuran (8 mL) was added dropwise a solution of di-tert-butylazodicarboxylate (725 mg, 1.2 eq.) in tetrahydrofuran (... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol.Aromatic alcohol | Ether | C1CC[NH]CC1 | C1CC[NH]CC1 | c1ccc2[nH]ccc2c1.C1CC[NH]CC1 | HO- | O1CCCC1 | null | 20 | CC(C)N1CCC(O)CC1.CCOC(=O)c1cc2cc(O)c(Cl)cc2[nH]1>O1CCCC1>CCOC(=O)c1cc2cc(OC3CCN(C(C)C)CC3)c(Cl)cc2[nH]1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-2fa291c04abe4df0ac9941ccc6fda1bc | CCOC(=O)c1cc2cc(OC)c(Cl)cc2[nH]1>>CCOC(=O)c1cc2cc(O)c(Cl)cc2[nH]1 | B(Br)(Br)Br.C(C)OC(=O)C=1NC2=CC(=C(C=C2C1)OC)Cl>>C(C)OC(=O)C=1NC2=CC(=C(C=C2C1)O)Cl | C[O:11][c:10]1[cH:9][c:8]2[cH:7][c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[nH:16][c:15]2[cH:14][c:12]1[Cl:13]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][c:8]2[cH:9][c:10]([OH:11])[c:12]([Cl:13])[cH:14][c:15]2[nH:16]1 | CCOC(=O)c1cc2cc(OC)c(Cl)cc2[nH]1 | CCOC(=O)c1cc2cc(O)c(Cl)cc2[nH]1 | null | null | ClCCl | Deprotection | Cleavage of methoxy ethers to alcohols | c5320c7dfa4f544d4900efcae9b3262bf0d5286bcf39c86109232351f35b23d5 | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | c1ccc2[nH]ccc2c1 | C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[OH;D1;+0:1]-[c:2](:[c:3]):[c:4] | 74.6 | [{"value": 74.0, "product": "C(C)OC(=O)C=1NC2=CC(=C(C=C2C1)O)Cl", "details": "PERCENTYIELD", "is_desired": false}, {"value": 74.6, "product": "C(C)OC(=O)C=1NC2=CC(=C(C=C2C1)O)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | To a cooled (−78° C.) solution of 6-chloro-5-methoxy-1H-indole-2-carboxylic acid ethyl ester (930 mg, 1.0 eq.) in dichloromethane (20 mL), was slowly added a 1M solution of boron tribromide in dichloromethane (7.33 mL, 2.0 eq.). The mixture was stirred at room temperature for 1 h, partitioned between ethyl acetate and ... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | null | null | c1ccc2[nH]ccc2c1 | Other | ClCCl | null | 1 | CCOC(=O)c1cc2cc(OC)c(Cl)cc2[nH]1>ClCCl>CCOC(=O)c1cc2cc(O)c(Cl)cc2[nH]1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-04b9f57d0cd4482a9aa02d8215ee1801 | CC(C)N1CCC(Oc2cc3cc(C(=O)N4CCN(C(=O)OC(C)(C)C)CC4)[nH]c3cc2Cl)CC1>>CC(C)N1CCC(Oc2cc3cc(C(=O)N4CCNCC4)[nH]c3cc2Cl)CC1 | C(C)(C)(C)OC(=O)N1CCN(CC1)C(=O)C=1NC2=CC(=C(C=C2C1)OC1CCN(CC1)C(C)C)Cl.FC(C(=O)O)(F)F>>ClC1=C(C=C2C=C(NC2=C1)C(=O)N1CCNCC1)OC1CCN(CC1)C(C)C | CC(C)(C)OC(=O)[N:19]1[CH2:18][CH2:17][N:16]([C:14]([c:13]2[cH:12][c:11]3[cH:10][c:9]([O:8][CH:7]4[CH2:6][CH2:5][N:4]([CH:2]([CH3:1])[CH3:3])[CH2:28][CH2:27]4)[c:25]([Cl:26])[cH:24][c:23]3[nH:22]2)=[O:15])[CH2:21][CH2:20]1>>[CH3:1][CH:2]([CH3:3])[N:4]1[CH2:5][CH2:6][CH:7]([O:8][c:9]2[cH:10][c:11]3[cH:12][c:13]([C:14](=[... | CC(C)N1CCC(Oc2cc3cc(C(=O)N4CCN(C(=O)OC(C)(C)C)CC4)[nH]c3cc2Cl)CC1 | CC(C)N1CCC(Oc2cc3cc(C(=O)N4CCNCC4)[nH]c3cc2Cl)CC1 | null | null | ClCCl | Reduction | Boc amine deprotection | 2c25e19aee181a3c5131cfdfda27035fd54d4379a11d745dfb75d386bacfd500 | a94b29c7264c852156fc1cdd4a0951a4fc26c06d0edc9e50c743825dbf79e3fd | O=C(c1cc2cc(OC3CCNCC3)ccc2[nH]1)N1CCNCC1 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1]1-[C:2]-[C:3]-[#7:4]-[C:5]-[C:6]-1>>[#7:4]1-[C:3]-[C:2]-[NH;D2;+0:1]-[C:6]-[C:5]-1 | 94.2 | [{"value": 94.0, "product": "ClC1=C(C=C2C=C(NC2=C1)C(=O)N1CCNCC1)OC1CCN(CC1)C(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 94.2, "product": "ClC1=C(C=C2C=C(NC2=C1)C(=O)N1CCNCC1)OC1CCN(CC1)C(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | To a cold (0° C.) solution of 4-[6-chloro-5-(1-isopropyl-piperidin-4-yloxy)-1H-indole-2-carbonyl]-piperazine-1-carboxylic acid tert-butyl ester (example 3, 547 mg, 1.0 eq.) in dichloromethane was added trifluoroacetic acid (1.23 mL, 10 eq.) dropwise. The reaction mixture was stirred 3 h at room temperature. The mixture... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Secondary amine | C1C[NH]CC[NH]1 | C1C[NH]CCN1 | C1CC[NH]CC1.c1ccc2[nH]ccc2c1.C1C[NH]CCN1 | HO- | ClCCl | null | 3 | CC(C)N1CCC(Oc2cc3cc(C(=O)N4CCN(C(=O)OC(C)(C)C)CC4)[nH]c3cc2Cl)CC1>ClCCl>CC(C)N1CCC(Oc2cc3cc(C(=O)N4CCNCC4)[nH]c3cc2Cl)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-74d069b74f2c4196b99f3e8b80128187 | CC(C)N1CCC(Oc2cc3cc(C(=O)N4CCNCC4)[nH]c3cc2Cl)CC1.O=C(Cl)C1CC1>>CC(C)N1CCC(Oc2cc3cc(C(=O)N4CCN(C(=O)C5CC5)CC4)[nH]c3cc2Cl)CC1 | ClC1=C(C=C2C=C(NC2=C1)C(=O)N1CCNCC1)OC1CCN(CC1)C(C)C.C([O-])([O-])=O.[Cs+].[Cs+].C1(CC1)C(=O)Cl>>ClC1=C(C=C2C=C(NC2=C1)C(=O)N1CCN(CC1)C(=O)C1CC1)OC1CCN(CC1)C(C)C | [CH3:1][CH:2]([CH3:3])[N:4]1[CH2:5][CH2:6][CH:7]([O:8][c:9]2[cH:10][c:11]3[cH:12][c:13]([C:14](=[O:15])[N:16]4[CH2:17][CH2:18][NH:19][CH2:25][CH2:26]4)[nH:27][c:28]3[cH:29][c:30]2[Cl:31])[CH2:32][CH2:33]1.Cl[C:20](=[O:21])[CH:22]1[CH2:23][CH2:24]1>>[CH3:1][CH:2]([CH3:3])[N:4]1[CH2:5][CH2:6][CH:7]([O:8][c:9]2[cH:10][c:1... | CC(C)N1CCC(Oc2cc3cc(C(=O)N4CCNCC4)[nH]c3cc2Cl)CC1.O=C(Cl)C1CC1 | CC(C)N1CCC(Oc2cc3cc(C(=O)N4CCN(C(=O)C5CC5)CC4)[nH]c3cc2Cl)CC1 | null | null | C(C)#N | Acylation | N-alkylation of secondary amines with alkyl halides | 008ee4368afbd52034630a2410a1738f53049b314574435184e4e0be81b96642 | 96cb0a2fed10552c5770a45a2d6523b47ac3e38928b4a9c698d8577451182dcd | O=C(c1cc2cc(OC3CCNCC3)ccc2[nH]1)N1CCN(C(=O)C2CC2)CC1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]1-[C:4]-[C:5]-1.[#7:6]1-[C:7]-[C:8]-[NH;D2;+0:9]-[C:10]-[C:11]-1>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[C:3]1-[C:4]-[C:5]-1)-[N;H0;D3;+0:9]1-[C:8]-[C:7]-[#7:6]-[C:11]-[C:10]-1 | 46 | [{"value": 46.0, "product": "ClC1=C(C=C2C=C(NC2=C1)C(=O)N1CCN(CC1)C(=O)C1CC1)OC1CCN(CC1)C(C)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | To a mixture of [6-chloro-5-(1-isopropyl-piperidin-4-yloxy)-1H-indol-2-yl]-piperazin-1-yl-methanone (example 36, 150 mg, 1.0 eq.) and cesium carbonate (243 mg, 2.0 eq.) in acetonitrile (8 mL) was added cyclopropane carbonylchloride. The reaction mixture was refluxed 4 h. The reaction mixture was concentrated in vacuo a... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Secondary amine | Tertiary amide | C1C[NH]CCN1 | C1C[NH]CC[NH]1 | C1CC[NH]CC1.c1ccc2[nH]ccc2c1.C1C[NH]CC[NH]1.C1CC1 | HCl | C(C)#N | null | null | CC(C)N1CCC(Oc2cc3cc(C(=O)N4CCNCC4)[nH]c3cc2Cl)CC1.O=C(Cl)C1CC1>C(C)#N>CC(C)N1CCC(Oc2cc3cc(C(=O)N4CCN(C(=O)C5CC5)CC4)[nH]c3cc2Cl)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-4737d552c37844098816d5044b23a439 | CC(C)N1CCC(Oc2cc3cc(C(=O)N4CCNCC4)[nH]c3cc2Cl)CC1.CN(C)C(=O)Cl>>CC(C)N1CCC(Oc2cc3cc(C(=O)N4CCN(C(=O)N(C)C)CC4)[nH]c3cc2Cl)CC1 | ClC1=C(C=C2C=C(NC2=C1)C(=O)N1CCNCC1)OC1CCN(CC1)C(C)C.CN(C(=O)Cl)C>>CN(C(=O)N1CCN(CC1)C(=O)C=1NC2=CC(=C(C=C2C1)OC1CCN(CC1)C(C)C)Cl)C | [CH3:1][CH:2]([CH3:3])[N:4]1[CH2:5][CH2:6][CH:7]([O:8][c:9]2[cH:10][c:11]3[cH:12][c:13]([C:14](=[O:15])[N:16]4[CH2:17][CH2:18][NH:19][CH2:25][CH2:26]4)[nH:27][c:28]3[cH:29][c:30]2[Cl:31])[CH2:32][CH2:33]1.Cl[C:20](=[O:21])[N:22]([CH3:23])[CH3:24]>>[CH3:1][CH:2]([CH3:3])[N:4]1[CH2:5][CH2:6][CH:7]([O:8][c:9]2[cH:10][c:11... | CC(C)N1CCC(Oc2cc3cc(C(=O)N4CCNCC4)[nH]c3cc2Cl)CC1.CN(C)C(=O)Cl | CC(C)N1CCC(Oc2cc3cc(C(=O)N4CCN(C(=O)N(C)C)CC4)[nH]c3cc2Cl)CC1 | null | null | null | Acylation | N-alkylation of secondary amines with alkyl halides | dcfba2aa7ca13a6ccdf0aa9e5554d01dee20f5aad8e3132e302a663220e425bb | 353c6e1db25433862a8bcf26ca332f6abeb45cb685806584bc65f8cfcb712540 | O=C(c1cc2cc(OC3CCNCC3)ccc2[nH]1)N1CCNCC1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#7:3](-[C;D1;H3:4])-[C;D1;H3:5].[#7:6]1-[C:7]-[C:8]-[NH;D2;+0:9]-[C:10]-[C:11]-1>>[C;D1;H3:4]-[#7:3](-[C;D1;H3:5])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[N;H0;D3;+0:9]1-[C:8]-[C:7]-[#7:6]-[C:11]-[C:10]-1 | 62 | [{"value": 62.0, "product": "CN(C(=O)N1CCN(CC1)C(=O)C=1NC2=CC(=C(C=C2C1)OC1CCN(CC1)C(C)C)Cl)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The title compound was synthesized in analogy to example 37, from [6-chloro-5-(1-isopropyl-piperidin-4-yloxy)-1H-indol-2-yl]-piperazin-1-yl-methanone (example 36), and dimethylcarbamoyl chloride, to afford the title compound as a light-yellow solid (62%).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Tertiary amide.Secondary amine | Urea | C1C[NH]CCN1 | C1C[NH]CC[NH]1 | C1CC[NH]CC1.c1ccc2[nH]ccc2c1.C1C[NH]CC[NH]1 | HCl | null | null | null | CC(C)N1CCC(Oc2cc3cc(C(=O)N4CCNCC4)[nH]c3cc2Cl)CC1.CN(C)C(=O)Cl>>CC(C)N1CCC(Oc2cc3cc(C(=O)N4CCN(C(=O)N(C)C)CC4)[nH]c3cc2Cl)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-7a69c1e2624c4d73a131dc376e992407 | CC(C)N1CCC(Oc2cc3cc(C(=O)N4CCNCC4)[nH]c3cc2Cl)CC1.CS(=O)(=O)Cl>>CC(C)N1CCC(Oc2cc3cc(C(=O)N4CCN(S(C)(=O)=O)CC4)[nH]c3cc2Cl)CC1 | ClC1=C(C=C2C=C(NC2=C1)C(=O)N1CCNCC1)OC1CCN(CC1)C(C)C.CS(=O)(=O)Cl>>ClC1=C(C=C2C=C(NC2=C1)C(=O)N1CCN(CC1)S(=O)(=O)C)OC1CCN(CC1)C(C)C | [CH3:1][CH:2]([CH3:3])[N:4]1[CH2:5][CH2:6][CH:7]([O:8][c:9]2[cH:10][c:11]3[cH:12][c:13]([C:14](=[O:15])[N:16]4[CH2:17][CH2:18][NH:19][CH2:24][CH2:25]4)[nH:26][c:27]3[cH:28][c:29]2[Cl:30])[CH2:31][CH2:32]1.Cl[S:20]([CH3:21])(=[O:22])=[O:23]>>[CH3:1][CH:2]([CH3:3])[N:4]1[CH2:5][CH2:6][CH:7]([O:8][c:9]2[cH:10][c:11]3[cH:1... | CC(C)N1CCC(Oc2cc3cc(C(=O)N4CCNCC4)[nH]c3cc2Cl)CC1.CS(=O)(=O)Cl | CC(C)N1CCC(Oc2cc3cc(C(=O)N4CCN(S(C)(=O)=O)CC4)[nH]c3cc2Cl)CC1 | null | null | null | Acylation | Sulfonamide synthesis (Schotten-Baumann) secondary amine | c6a995ab9be6571957febbe378833244177e30fd671e64e4e1ffe6f50345cf56 | b7aca5a5d690b0846685a854bc946849e1041bfc3965161290b5ffb2821af09e | O=C(c1cc2cc(OC3CCNCC3)ccc2[nH]1)N1CCNCC1 | Cl-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4].[#7:5]1-[C:6]-[C:7]-[NH;D2;+0:8]-[C:9]-[C:10]-1>>[C;D1;H3:2]-[S;H0;D4;+0:1](=[O;D1;H0:3])(=[O;D1;H0:4])-[N;H0;D3;+0:8]1-[C:7]-[C:6]-[#7:5]-[C:10]-[C:9]-1 | 72 | [{"value": 72.0, "product": "ClC1=C(C=C2C=C(NC2=C1)C(=O)N1CCN(CC1)S(=O)(=O)C)OC1CCN(CC1)C(C)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The title compound was synthesized in analogy to example 37, from [6-chloro-5-(1-isopropyl-piperidin-4-yloxy)-1H-indol-2-yl]-piperazin-1-yl-methanone (example 36), and methanesulfonyl chloride, to afford the title compound as an off-white solid (72%).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Secondary amine.Sulfonyl halide | Tertiary amine | C1C[NH]CCN1 | C1C[NH]CC[NH]1 | C1CC[NH]CC1.c1ccc2[nH]ccc2c1.C1C[NH]CC[NH]1 | HCl | null | null | null | CC(C)N1CCC(Oc2cc3cc(C(=O)N4CCNCC4)[nH]c3cc2Cl)CC1.CS(=O)(=O)Cl>>CC(C)N1CCC(Oc2cc3cc(C(=O)N4CCN(S(C)(=O)=O)CC4)[nH]c3cc2Cl)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-1c31bd3c5b534ffe8922bc3315a8f7d6 | CC(C)(C)OC(=O)N1CCNCC1.O=S(=O)(Cl)c1ccc(C(F)(F)F)cc1>>Cl.O=S(=O)(c1ccc(C(F)(F)F)cc1)N1CCNCC1 | C(C)(C)(C)OC(=O)N1CCNCC1.C(C)N(CC)CC.FC(C1=CC=C(C=C1)S(=O)(=O)Cl)(F)F>>Cl.FC(C1=CC=C(C=C1)S(=O)(=O)N1CCNCC1)(F)F | CC(C)(C)OC(=O)[N:15]1[CH2:16][CH2:17][NH:18][CH2:19][CH2:20]1.[Cl:1][S:3](=[O:2])(=[O:4])[c:5]1[cH:6][cH:7][c:8]([C:9]([F:10])([F:11])[F:12])[cH:13][cH:14]1>>[ClH:1].[O:2]=[S:3](=[O:4])([c:5]1[cH:6][cH:7][c:8]([C:9]([F:10])([F:11])[F:12])[cH:13][cH:14]1)[N:15]1[CH2:16][CH2:17][NH:18][CH2:19][CH2:20]1 | CC(C)(C)OC(=O)N1CCNCC1.O=S(=O)(Cl)c1ccc(C(F)(F)F)cc1 | Cl.O=S(=O)(c1ccc(C(F)(F)F)cc1)N1CCNCC1 | null | null | ClCCl | Acylation | OtherReaction | fe80f4ba0030540fe0dd5c07c99df28cb9dc1f06dbe0a7382338f606945d5f85 | 705725ff5b1b5bdebe12db390e8895152ae89941b9a07e00716e981f5b25c654 | O=S(=O)(c1ccccc1)N1CCNCC1 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1]1-[C:2]-[C:3]-[#7:4]-[C:5]-[C:6]-1.[Cl;H0;D1;+0:7]-[S;H0;D4;+0:8](=[O;D1;H0:9])(=[O;D1;H0:10])-[c:11](:[c:12]):[c:13]>>[ClH;D0;+0:7].[O;D1;H0:9]=[S;H0;D4;+0:8](=[O;D1;H0:10])(-[N;H0;D3;+0:1]1-[C:2]-[C:3]-[#7:4]-[C:5]-[C:6]-1)-[c:11](:[c:12]):[c:13] | 31.4 | [{"value": 31.0, "product": "Cl.FC(C1=CC=C(C=C1)S(=O)(=O)N1CCNCC1)(F)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 31.4, "product": "Cl.FC(C1=CC=C(C=C1)S(=O)(=O)N1CCNCC1)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | To a solution of N-tert-butyloxycarbonylpiperazine (1.00 g, 5.37 mmol) in dichloromethane were added triethylamine (1.05 eq, 0.78 ml) and 4-(trifluoromethyl)-benzenesulfonyl chloride (1.02 eq, 1.345 g). The mixture was stirred overnight at room temperature, diluted with dichloromethane, washed with aqueous sodium bicar... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Sulfonyl halide.Boc | Tertiary amine | C1C[NH]CCN1 | C1C[NH]CCN1 | c1ccccc1.C1C[NH]CCN1 | HO- | ClCCl | null | 8 | CC(C)(C)OC(=O)N1CCNCC1.O=S(=O)(Cl)c1ccc(C(F)(F)F)cc1>ClCCl>Cl.O=S(=O)(c1ccc(C(F)(F)F)cc1)N1CCNCC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-2328382c02c04eac95bd1adb49588ef6 | CC(C)(C)OC(=O)N1CCNCC1.CC(C)N1CCC(Oc2ccc3[nH]c(C(=O)O)cc3c2)CC1>>CC(C)N1CCC(Oc2ccc3[nH]c(C(=O)N4CCN(C(=O)OC(C)(C)C)CC4)cc3c2)CC1 | CC(C)N1CCC(CC1)OC=1C=C2C=C(NC2=CC1)C(=O)O.C(C)(C)(C)OC(=O)N1CCNCC1>>C(C)(C)(C)OC(=O)N1CCN(CC1)C(=O)C=1NC2=CC=C(C=C2C1)OC1CCN(CC1)C(C)C | [NH:17]1[CH2:18][CH2:19][N:20]([C:21](=[O:22])[O:23][C:24]([CH3:25])([CH3:26])[CH3:27])[CH2:28][CH2:29]1.O[C:15]([c:14]1[nH:13][c:12]2[cH:11][cH:10][c:9]([O:8][CH:7]3[CH2:6][CH2:5][N:4]([CH:2]([CH3:1])[CH3:3])[CH2:34][CH2:33]3)[cH:32][c:31]2[cH:30]1)=[O:16]>>[CH3:1][CH:2]([CH3:3])[N:4]1[CH2:5][CH2:6][CH:7]([O:8][c:9]2[... | CC(C)(C)OC(=O)N1CCNCC1.CC(C)N1CCC(Oc2ccc3[nH]c(C(=O)O)cc3c2)CC1 | CC(C)N1CCC(Oc2ccc3[nH]c(C(=O)N4CCN(C(=O)OC(C)(C)C)CC4)cc3c2)CC1 | null | null | null | Acylation | Acylation of Nitrogen Nucleophiles by Carboxylic Acids | ed26ef5eea92a0cc433b3f89a34f4c61724425fa15a9d0ec83a0f7a903eec831 | c5e4172490b2731ba9322b68af56376edadc31ce0bb9a3dfdea23a1817a852fd | O=C(c1cc2cc(OC3CCNCC3)ccc2[nH]1)N1CCNCC1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[#7;a:5]:[c:6].[#7:7]1-[C:8]-[C:9]-[NH;D2;+0:10]-[C:11]-[C:12]-1>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[N;H0;D3;+0:10]1-[C:9]-[C:8]-[#7:7]-[C:12]-[C:11]-1)-[c:3](:[c:4]):[#7;a:5]:[c:6] | null | [] | null | null | null | null | The title compound was prepared in analogy to example 40b), from 5-[[1-(1-methylethyl)-4-piperidinyl]oxy]-1H-Indole-2-carboxylic acid and 1-(tert-butoxycarbonyl)piperazine. Light-yellow solid. MS (m/z): 471.1 (M+H)+.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | Tertiary amide | C1CNCC[NH]1 | C1C[NH]CC[NH]1 | C1CC[NH]CC1.c1ccc2[nH]ccc2c1.C1C[NH]CC[NH]1 | HO- | null | null | null | CC(C)(C)OC(=O)N1CCNCC1.CC(C)N1CCC(Oc2ccc3[nH]c(C(=O)O)cc3c2)CC1>>CC(C)N1CCC(Oc2ccc3[nH]c(C(=O)N4CCN(C(=O)OC(C)(C)C)CC4)cc3c2)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-adfe3d9336b84d1ba1667c8e82b797e0 | CC(C)N1CCC(Oc2ccc3[nH]c(C(=O)N4CCNCC4)cc3c2)CC1.CS(=O)(=O)Cl>>CC(C)N1CCC(Oc2ccc3[nH]c(C(=O)N4CCN(S(C)(=O)=O)CC4)cc3c2)CC1 | Cl.Cl.C(C)(C)N1CCC(CC1)OC=1C=C2C=C(NC2=CC1)C(=O)N1CCNCC1.C(C)N(CC)CC.CS(=O)(=O)Cl>>C(C)(C)N1CCC(CC1)OC=1C=C2C=C(NC2=CC1)C(=O)N1CCN(CC1)S(=O)(=O)C | [CH3:1][CH:2]([CH3:3])[N:4]1[CH2:5][CH2:6][CH:7]([O:8][c:9]2[cH:10][cH:11][c:12]3[nH:13][c:14]([C:15](=[O:16])[N:17]4[CH2:18][CH2:19][NH:20][CH2:25][CH2:26]4)[cH:27][c:28]3[cH:29]2)[CH2:30][CH2:31]1.Cl[S:21]([CH3:22])(=[O:23])=[O:24]>>[CH3:1][CH:2]([CH3:3])[N:4]1[CH2:5][CH2:6][CH:7]([O:8][c:9]2[cH:10][cH:11][c:12]3[nH:... | CC(C)N1CCC(Oc2ccc3[nH]c(C(=O)N4CCNCC4)cc3c2)CC1.CS(=O)(=O)Cl | CC(C)N1CCC(Oc2ccc3[nH]c(C(=O)N4CCN(S(C)(=O)=O)CC4)cc3c2)CC1 | null | null | ClCCl | Acylation | Sulfonamide synthesis (Schotten-Baumann) secondary amine | c6a995ab9be6571957febbe378833244177e30fd671e64e4e1ffe6f50345cf56 | b7aca5a5d690b0846685a854bc946849e1041bfc3965161290b5ffb2821af09e | O=C(c1cc2cc(OC3CCNCC3)ccc2[nH]1)N1CCNCC1 | Cl-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4].[#7:5]1-[C:6]-[C:7]-[NH;D2;+0:8]-[C:9]-[C:10]-1>>[C;D1;H3:2]-[S;H0;D4;+0:1](=[O;D1;H0:3])(=[O;D1;H0:4])-[N;H0;D3;+0:8]1-[C:7]-[C:6]-[#7:5]-[C:10]-[C:9]-1 | null | [] | null | null | 8 | HOUR | To a solution of [5-(1-isopropyl-piperidin-4-yloxy)-1H-indol-2-yl]-piperazin-1-yl-methanone dihydrochloride (82 mg, 0.22 mmol) in dichloromethane (2 ml) were added triethylamine (4.2 eq, 0.13 ml) and methanesulfonyl chloride (1.4 eq, 0.02 ml). The mixture was stirred overnight, diluted with dichloromethane and washed w... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amine.Sulfonyl halide | Tertiary amine | C1C[NH]CCN1 | C1C[NH]CC[NH]1 | C1CC[NH]CC1.c1ccc2[nH]ccc2c1.C1C[NH]CC[NH]1 | HCl | ClCCl | null | 8 | CC(C)N1CCC(Oc2ccc3[nH]c(C(=O)N4CCNCC4)cc3c2)CC1.CS(=O)(=O)Cl>ClCCl>CC(C)N1CCC(Oc2ccc3[nH]c(C(=O)N4CCN(S(C)(=O)=O)CC4)cc3c2)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-15d79e8205704d0b8c8c4122d786cc89 | CC(C)N1CCC(Oc2ccc3[nH]c(C(=O)N4CCN(C(=O)OC(C)(C)C)CC4)cc3c2)CC1>>CC(C)N1CCC(Oc2ccc3[nH]c(C(=O)N4CCNCC4)cc3c2)CC1.Cl | C(C)OCC.C(C)(C)(C)OC(=O)N1CCN(CC1)C(=O)C=1NC2=CC=C(C=C2C1)OC1CCN(CC1)C(C)C.Cl>>Cl.Cl.C(C)(C)N1CCC(CC1)OC=1C=C2C=C(NC2=CC1)C(=O)N1CCNCC1 | CC(C)(C)OC(=O)[N:20]1[CH2:19][CH2:18][N:17]([C:15]([c:14]2[nH:13][c:12]3[cH:11][cH:10][c:9]([O:8][CH:7]4[CH2:6][CH2:5][N:4]([CH:2]([CH3:1])[CH3:3])[CH2:27][CH2:26]4)[cH:25][c:24]3[cH:23]2)=[O:16])[CH2:22][CH2:21]1>>[CH3:1][CH:2]([CH3:3])[N:4]1[CH2:5][CH2:6][CH:7]([O:8][c:9]2[cH:10][cH:11][c:12]3[nH:13][c:14]([C:15](=[O... | CC(C)N1CCC(Oc2ccc3[nH]c(C(=O)N4CCN(C(=O)OC(C)(C)C)CC4)cc3c2)CC1 | CC(C)N1CCC(Oc2ccc3[nH]c(C(=O)N4CCNCC4)cc3c2)CC1.Cl | null | null | C(C)(=O)OCC | Miscellaneous | Boc amine deprotection | ca9288c3be1743ea424604bf62770990eec893f8f7f07c612f680fef8b15531e | c95e79e18f8ea11cf22745e0eab38cab98566b1b63e7d80ee200f4cb4f94f00c | O=C(c1cc2cc(OC3CCNCC3)ccc2[nH]1)N1CCNCC1 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1]1-[C:2]-[C:3]-[#7:4]-[C:5]-[C:6]-1>>[#7:4]1-[C:3]-[C:2]-[NH;D2;+0:1]-[C:6]-[C:5]-1 | null | [] | null | null | 72 | HOUR | A solution of 4-[5-(1-isopropyl-piperidin-4-yloxy)-1H-indole-2-carbonyl]-piperazine-1-carboxylic acid tert-butyl ester (800 mg, 1.7 mmol) in ethyl acetate (25 ml) was treated with hydrogen chloride (5M in ethyl acetate, 12 ml) and the mixture stirred 72 h at room temperature. The resulting suspension was cooled to 0° C... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Secondary amine | C1C[NH]CC[NH]1 | C1C[NH]CCN1 | C1CC[NH]CC1.c1ccc2[nH]ccc2c1.C1C[NH]CCN1 | HO- | C(C)(=O)OCC | null | 72 | CC(C)N1CCC(Oc2ccc3[nH]c(C(=O)N4CCN(C(=O)OC(C)(C)C)CC4)cc3c2)CC1>C(C)(=O)OCC>CC(C)N1CCC(Oc2ccc3[nH]c(C(=O)N4CCNCC4)cc3c2)CC1.Cl |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-71678daf03d8463199b3144676ffabcb | CC(C)N1CCC(Oc2ccc3[nH]c(C(=O)N4CCN(C(=O)OC(C)(C)C)CC4)cc3c2)CC1.CC(C)OS(C)(=O)=O>>CC(C)N1CCC(Oc2ccc3c(c2)cc(C(=O)N2CCN(C(=O)OC(C)(C)C)CC2)n3C(C)C)CC1 | C(C)(C)(C)OC(=O)N1CCN(CC1)C(=O)C=1NC2=CC=C(C=C2C1)OC1CCN(CC1)C(C)C.CS(=O)(=O)OC(C)C>>C(C)(C)(C)OC(=O)N1CCN(CC1)C(=O)C=1N(C2=CC=C(C=C2C1)OC1CCN(CC1)C(C)C)C(C)C | [CH3:1][CH:2]([CH3:3])[N:4]1[CH2:5][CH2:6][CH:7]([O:8][c:9]2[cH:10][cH:11][c:12]3[c:13]([cH:14]2)[cH:15][c:16]([C:17](=[O:18])[N:19]2[CH2:20][CH2:21][N:22]([C:23](=[O:24])[O:25][C:26]([CH3:27])([CH3:28])[CH3:29])[CH2:30][CH2:31]2)[nH:32]3)[CH2:36][CH2:37]1.CS(=O)(=O)O[CH:33]([CH3:34])[CH3:35]>>[CH3:1][CH:2]([CH3:3])[N:... | CC(C)N1CCC(Oc2ccc3[nH]c(C(=O)N4CCN(C(=O)OC(C)(C)C)CC4)cc3c2)CC1.CC(C)OS(C)(=O)=O | CC(C)N1CCC(Oc2ccc3c(c2)cc(C(=O)N2CCN(C(=O)OC(C)(C)C)CC2)n3C(C)C)CC1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | d896e99f48a796a768d64b339abb5adbd8bc977c5bccdd47720d3a6657256b55 | 0b4f3c8c88df0a792d0db7d59004d7fe5681a61dd48ef2449ddca2d636f76ada | O=C(c1cc2cc(OC3CCNCC3)ccc2[nH]1)N1CCNCC1 | C-S(=O)(=O)-O-[CH;D3;+0:1](-[C;D1;H3:2])-[C;D1;H3:3].[C:4]-[#7:5](-[C:6](=[O;D1;H0:7])-[c:8]1:[c:9]:[c:10]:[c:11](:[c:12]):[nH;D2;+0:13]:1)-[C:14]>>[C:4]-[#7:5](-[C:6](=[O;D1;H0:7])-[c:8]1:[c:9]:[c:10]:[c:11](:[c:12]):[n;H0;D3;+0:13]:1-[CH;D3;+0:1](-[C;D1;H3:2])-[C;D1;H3:3])-[C:14] | null | [] | null | null | null | null | The title compound was prepared in analogy to example 40a), from 4-[5-(1-isopropyl-piperidin-4-yloxy)-1H-indole-2-carbonyl]-piperazine-1-carboxylic acid tert-butyl ester and isopropyl methanesulfonate. Light-yellow foam. MS (m/z): 513.4 (M+H)+.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Mesylate | null | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1 | C1CC[NH]CC1.c1ccc2[nH]ccc2c1.C1C[NH]CC[NH]1 | MsOH.HO- | null | null | null | CC(C)N1CCC(Oc2ccc3[nH]c(C(=O)N4CCN(C(=O)OC(C)(C)C)CC4)cc3c2)CC1.CC(C)OS(C)(=O)=O>>CC(C)N1CCC(Oc2ccc3c(c2)cc(C(=O)N2CCN(C(=O)OC(C)(C)C)CC2)n3C(C)C)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-7c40ff5412994e82a0aa5a5d188694f7 | CC(C)N1CCC(Oc2ccc3c(c2)cc(C(=O)N2CCNCC2)n3C(C)C)CC1.CS(=O)(=O)Cl>>CC(C)N1CCC(Oc2ccc3c(c2)cc(C(=O)N2CCN(S(C)(=O)=O)CC2)n3C(C)C)CC1 | Cl.C(C)(C)N1C(=CC2=CC(=CC=C12)OC1CCN(CC1)C(C)C)C(=O)N1CCNCC1.CS(=O)(=O)Cl>>C(C)(C)N1C(=CC2=CC(=CC=C12)OC1CCN(CC1)C(C)C)C(=O)N1CCN(CC1)S(=O)(=O)C | [CH3:1][CH:2]([CH3:3])[N:4]1[CH2:5][CH2:6][CH:7]([O:8][c:9]2[cH:10][cH:11][c:12]3[c:13]([cH:14]2)[cH:15][c:16]([C:17](=[O:18])[N:19]2[CH2:20][CH2:21][NH:22][CH2:27][CH2:28]2)[n:29]3[CH:30]([CH3:31])[CH3:32])[CH2:33][CH2:34]1.Cl[S:23]([CH3:24])(=[O:25])=[O:26]>>[CH3:1][CH:2]([CH3:3])[N:4]1[CH2:5][CH2:6][CH:7]([O:8][c:9]... | CC(C)N1CCC(Oc2ccc3c(c2)cc(C(=O)N2CCNCC2)n3C(C)C)CC1.CS(=O)(=O)Cl | CC(C)N1CCC(Oc2ccc3c(c2)cc(C(=O)N2CCN(S(C)(=O)=O)CC2)n3C(C)C)CC1 | null | null | null | Acylation | Sulfonamide synthesis (Schotten-Baumann) secondary amine | c6a995ab9be6571957febbe378833244177e30fd671e64e4e1ffe6f50345cf56 | b7aca5a5d690b0846685a854bc946849e1041bfc3965161290b5ffb2821af09e | O=C(c1cc2cc(OC3CCNCC3)ccc2[nH]1)N1CCNCC1 | Cl-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4].[#7:5]1-[C:6]-[C:7]-[NH;D2;+0:8]-[C:9]-[C:10]-1>>[C;D1;H3:2]-[S;H0;D4;+0:1](=[O;D1;H0:3])(=[O;D1;H0:4])-[N;H0;D3;+0:8]1-[C:7]-[C:6]-[#7:5]-[C:10]-[C:9]-1 | null | [] | null | null | null | null | The title compound was prepared in analogy to example 51, from [1-isopropyl-5-(1-isopropyl-piperidin-4-yloxy)-1H-indol-2-yl]-piperazin-1-yl-methanone hydrochloride and methanesulfonyl chloride. Light-yellow foam. MS (m/z): 491.2 (M+H)+.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Secondary amine.Sulfonyl halide | Tertiary amine | C1C[NH]CCN1 | C1C[NH]CC[NH]1 | C1CC[NH]CC1.c1ccc2[nH]ccc2c1.C1C[NH]CC[NH]1 | HCl | null | null | null | CC(C)N1CCC(Oc2ccc3c(c2)cc(C(=O)N2CCNCC2)n3C(C)C)CC1.CS(=O)(=O)Cl>>CC(C)N1CCC(Oc2ccc3c(c2)cc(C(=O)N2CCN(S(C)(=O)=O)CC2)n3C(C)C)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-3918b6de77a64d928bc11431137fefad | CC(C)N1CCC(Oc2ccc3[nH]c(C(=O)N4CCN(C(=O)OC(C)(C)C)CC4)cc3c2)CC1.O=S(=O)(OCC(F)F)C(F)(F)F>>CC(C)N1CCC(Oc2ccc3c(c2)cc(C(=O)N2CCN(C(=O)OC(C)(C)C)CC2)n3CC(F)F)CC1 | C(C)(C)(C)OC(=O)N1CCN(CC1)C(=O)C=1NC2=CC=C(C=C2C1)OC1CCN(CC1)C(C)C.FC(S(=O)(=O)OCC(F)F)(F)F>>C(C)(C)(C)OC(=O)N1CCN(CC1)C(=O)C=1N(C2=CC=C(C=C2C1)OC1CCN(CC1)C(C)C)CC(F)F | [CH3:1][CH:2]([CH3:3])[N:4]1[CH2:5][CH2:6][CH:7]([O:8][c:9]2[cH:10][cH:11][c:12]3[c:13]([cH:14]2)[cH:15][c:16]([C:17](=[O:18])[N:19]2[CH2:20][CH2:21][N:22]([C:23](=[O:24])[O:25][C:26]([CH3:27])([CH3:28])[CH3:29])[CH2:30][CH2:31]2)[nH:32]3)[CH2:37][CH2:38]1.O=S(=O)(O[CH2:33][CH:34]([F:35])[F:36])C(F)(F)F>>[CH3:1][CH:2](... | CC(C)N1CCC(Oc2ccc3[nH]c(C(=O)N4CCN(C(=O)OC(C)(C)C)CC4)cc3c2)CC1.O=S(=O)(OCC(F)F)C(F)(F)F | CC(C)N1CCC(Oc2ccc3c(c2)cc(C(=O)N2CCN(C(=O)OC(C)(C)C)CC2)n3CC(F)F)CC1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 2385db9083aeddeec4cb75186a671c6c56d0b264d04bfd83b44fc14a91b1ba5c | edca11cebc61d00890fbfd7dabc6d5d646a584b4ea075d24940b00f620ebabf2 | O=C(c1cc2cc(OC3CCNCC3)ccc2[nH]1)N1CCNCC1 | F-C(-F)(-F)-S(=O)(=O)-O-[CH2;D2;+0:1]-[C:2](-[F;D1;H0:3])-[F;D1;H0:4].[C:5]-[#7:6](-[C:7](=[O;D1;H0:8])-[c:9]1:[c:10]:[c:11]:[c:12](:[c:13]):[nH;D2;+0:14]:1)-[C:15]>>[C:5]-[#7:6](-[C:7](=[O;D1;H0:8])-[c:9]1:[c:10]:[c:11]:[c:12](:[c:13]):[n;H0;D3;+0:14]:1-[CH2;D2;+0:1]-[C:2](-[F;D1;H0:3])-[F;D1;H0:4])-[C:15] | null | [] | null | null | null | null | The title compound was prepared in analogy to example 40a), from 4-[5-(1-isopropyl-piperidin-4-yloxy)-1H-indole-2-carbonyl]-piperazine-1-carboxylic acid tert-butyl ester and 2,2-difluoroethyl trifluoromethanesulfonate. Off-white solid. MS (m/z): 535.5 (M+H)+.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Triflate | null | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1 | C1CC[NH]CC1.c1ccc2[nH]ccc2c1.C1C[NH]CC[NH]1 | TfOH.HO- | null | null | null | CC(C)N1CCC(Oc2ccc3[nH]c(C(=O)N4CCN(C(=O)OC(C)(C)C)CC4)cc3c2)CC1.O=S(=O)(OCC(F)F)C(F)(F)F>>CC(C)N1CCC(Oc2ccc3c(c2)cc(C(=O)N2CCN(C(=O)OC(C)(C)C)CC2)n3CC(F)F)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-1040b731e88d4417a47ee661f952515d | CC(C)N1CCC(Oc2ccc3c(c2)cc(C(=O)N2CCNCC2)n3CC(F)F)CC1.CS(=O)(=O)Cl>>CC(C)N1CCC(Oc2ccc3c(c2)cc(C(=O)N2CCN(S(C)(=O)=O)CC2)n3CC(F)F)CC1 | Cl.FC(CN1C(=CC2=CC(=CC=C12)OC1CCN(CC1)C(C)C)C(=O)N1CCNCC1)F.CS(=O)(=O)Cl>>FC(CN1C(=CC2=CC(=CC=C12)OC1CCN(CC1)C(C)C)C(=O)N1CCN(CC1)S(=O)(=O)C)F | [CH3:1][CH:2]([CH3:3])[N:4]1[CH2:5][CH2:6][CH:7]([O:8][c:9]2[cH:10][cH:11][c:12]3[c:13]([cH:14]2)[cH:15][c:16]([C:17](=[O:18])[N:19]2[CH2:20][CH2:21][NH:22][CH2:27][CH2:28]2)[n:29]3[CH2:30][CH:31]([F:32])[F:33])[CH2:34][CH2:35]1.Cl[S:23]([CH3:24])(=[O:25])=[O:26]>>[CH3:1][CH:2]([CH3:3])[N:4]1[CH2:5][CH2:6][CH:7]([O:8][... | CC(C)N1CCC(Oc2ccc3c(c2)cc(C(=O)N2CCNCC2)n3CC(F)F)CC1.CS(=O)(=O)Cl | CC(C)N1CCC(Oc2ccc3c(c2)cc(C(=O)N2CCN(S(C)(=O)=O)CC2)n3CC(F)F)CC1 | null | null | null | Acylation | Sulfonamide synthesis (Schotten-Baumann) secondary amine | c6a995ab9be6571957febbe378833244177e30fd671e64e4e1ffe6f50345cf56 | b7aca5a5d690b0846685a854bc946849e1041bfc3965161290b5ffb2821af09e | O=C(c1cc2cc(OC3CCNCC3)ccc2[nH]1)N1CCNCC1 | Cl-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4].[#7:5]1-[C:6]-[C:7]-[NH;D2;+0:8]-[C:9]-[C:10]-1>>[C;D1;H3:2]-[S;H0;D4;+0:1](=[O;D1;H0:3])(=[O;D1;H0:4])-[N;H0;D3;+0:8]1-[C:7]-[C:6]-[#7:5]-[C:10]-[C:9]-1 | null | [] | null | null | null | null | The title compound was prepared in analogy to example 51, from [1-(2,2-difluoro-ethyl)-5-(1-isopropyl-piperidin-4-yloxy)-1H-indol-2-yl]-piperazin-1-yl-methanone hydrochloride and methanesulfonyl chloride. Light-yellow foam. MS (m/z): 513.4 (M+H)+.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Secondary amine.Sulfonyl halide | Tertiary amine | C1C[NH]CCN1 | C1C[NH]CC[NH]1 | C1CC[NH]CC1.c1ccc2[nH]ccc2c1.C1C[NH]CC[NH]1 | HCl | null | null | null | CC(C)N1CCC(Oc2ccc3c(c2)cc(C(=O)N2CCNCC2)n3CC(F)F)CC1.CS(=O)(=O)Cl>>CC(C)N1CCC(Oc2ccc3c(c2)cc(C(=O)N2CCN(S(C)(=O)=O)CC2)n3CC(F)F)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-19388a128301464e8ee3d867e2e59cb2 | CC(=O)Cl.CC(C)N1CCC(Oc2ccc3c(c2)cc(C(=O)N2CCNCC2)n3C(C)C)CC1>>CC(=O)N1CCN(C(=O)c2cc3cc(OC4CCN(C(C)C)CC4)ccc3n2C(C)C)CC1 | Cl.C(C)(C)N1C(=CC2=CC(=CC=C12)OC1CCN(CC1)C(C)C)C(=O)N1CCNCC1.C(C)(=O)Cl>>C(C)(C)N1C(=CC2=CC(=CC=C12)OC1CCN(CC1)C(C)C)C(=O)N1CCN(CC1)C(C)=O | Cl[C:2]([CH3:1])=[O:3].[NH:4]1[CH2:5][CH2:6][N:7]([C:8](=[O:9])[c:10]2[cH:11][c:12]3[cH:13][c:14]([O:15][CH:16]4[CH2:17][CH2:18][N:19]([CH:20]([CH3:21])[CH3:22])[CH2:23][CH2:24]4)[cH:25][cH:26][c:27]3[n:28]2[CH:29]([CH3:30])[CH3:31])[CH2:32][CH2:33]1>>[CH3:1][C:2](=[O:3])[N:4]1[CH2:5][CH2:6][N:7]([C:8](=[O:9])[c:10]2[c... | CC(=O)Cl.CC(C)N1CCC(Oc2ccc3c(c2)cc(C(=O)N2CCNCC2)n3C(C)C)CC1 | CC(=O)N1CCN(C(=O)c2cc3cc(OC4CCN(C(C)C)CC4)ccc3n2C(C)C)CC1 | null | null | null | Acylation | N-alkylation of secondary amines with alkyl halides | 6dd420fad17fb719b6bd840e8952a8d7b2fb24721f86f8b8f9c697a36eb97ec3 | 96cb0a2fed10552c5770a45a2d6523b47ac3e38928b4a9c698d8577451182dcd | O=C(c1cc2cc(OC3CCNCC3)ccc2[nH]1)N1CCNCC1 | Cl-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[#7:4]1-[C:5]-[C:6]-[NH;D2;+0:7]-[C:8]-[C:9]-1>>[C;D1;H3:2]-[C;H0;D3;+0:1](=[O;D1;H0:3])-[N;H0;D3;+0:7]1-[C:6]-[C:5]-[#7:4]-[C:9]-[C:8]-1 | null | [] | null | null | null | null | The title compound was prepared in analogy to example 51, from [1-isopropyl-5-(1-isopropyl-piperidin-4-yloxy)-1H-indol-2-yl]-piperazin-1-yl-methanone hydrochloride and acetyl chloride. Light-yellow foam. MS (m/z): 455.5 (M+H)+.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Secondary amine | Tertiary amide | C1CNCC[NH]1 | C1C[NH]CC[NH]1 | C1C[NH]CC[NH]1.c1ccc2[nH]ccc2c1.C1CC[NH]CC1 | HCl | null | null | null | CC(=O)Cl.CC(C)N1CCC(Oc2ccc3c(c2)cc(C(=O)N2CCNCC2)n3C(C)C)CC1>>CC(=O)N1CCN(C(=O)c2cc3cc(OC4CCN(C(C)C)CC4)ccc3n2C(C)C)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-c0ac151c3c9346e78b992cda606a1a94 | CC(C)N1CCC(Oc2ccc3[nH]c(C(=O)N4CCNCC4)cc3c2)CC1.O=S(=O)(Cl)CC(F)(F)F>>CC(C)N1CCC(Oc2ccc3[nH]c(C(=O)N4CCN(S(=O)(=O)CC(F)(F)F)CC4)cc3c2)CC1 | Cl.Cl.C(C)(C)N1CCC(CC1)OC=1C=C2C=C(NC2=CC1)C(=O)N1CCNCC1.FC(CS(=O)(=O)Cl)(F)F>>C(C)(C)N1CCC(CC1)OC=1C=C2C=C(NC2=CC1)C(=O)N1CCN(CC1)S(=O)(=O)CC(F)(F)F | [CH3:1][CH:2]([CH3:3])[N:4]1[CH2:5][CH2:6][CH:7]([O:8][c:9]2[cH:10][cH:11][c:12]3[nH:13][c:14]([C:15](=[O:16])[N:17]4[CH2:18][CH2:19][NH:20][CH2:29][CH2:30]4)[cH:31][c:32]3[cH:33]2)[CH2:34][CH2:35]1.Cl[S:21](=[O:22])(=[O:23])[CH2:24][C:25]([F:26])([F:27])[F:28]>>[CH3:1][CH:2]([CH3:3])[N:4]1[CH2:5][CH2:6][CH:7]([O:8][c:... | CC(C)N1CCC(Oc2ccc3[nH]c(C(=O)N4CCNCC4)cc3c2)CC1.O=S(=O)(Cl)CC(F)(F)F | CC(C)N1CCC(Oc2ccc3[nH]c(C(=O)N4CCN(S(=O)(=O)CC(F)(F)F)CC4)cc3c2)CC1 | null | null | null | Acylation | Sulfonamide synthesis (Schotten-Baumann) secondary amine | c6a995ab9be6571957febbe378833244177e30fd671e64e4e1ffe6f50345cf56 | b7aca5a5d690b0846685a854bc946849e1041bfc3965161290b5ffb2821af09e | O=C(c1cc2cc(OC3CCNCC3)ccc2[nH]1)N1CCNCC1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[C:4]-[C:5](-[F;D1;H0:6])(-[F;D1;H0:7])-[F;D1;H0:8].[#7:9]1-[C:10]-[C:11]-[NH;D2;+0:12]-[C:13]-[C:14]-1>>[F;D1;H0:6]-[C:5](-[F;D1;H0:7])(-[F;D1;H0:8])-[C:4]-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[N;H0;D3;+0:12]1-[C:11]-[C:10]-[#7:9]-[C:14]-[C:13]-1 | null | [] | null | null | null | null | The title compound was prepared in analogy to example 51, from [5-(1-isopropyl-piperidin-4-yloxy)-1H-indol-2-yl]-piperazin-1-yl-methanone dihydrochloride and 2,2,2-trifluoro-ethanesulfonyl chloride. Off-white solid. MS (m/z): 517.3 (M+H)+.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Secondary amine.Sulfonyl halide | Tertiary amine | C1C[NH]CCN1 | C1C[NH]CC[NH]1 | C1CC[NH]CC1.c1ccc2[nH]ccc2c1.C1C[NH]CC[NH]1 | HCl | null | null | null | CC(C)N1CCC(Oc2ccc3[nH]c(C(=O)N4CCNCC4)cc3c2)CC1.O=S(=O)(Cl)CC(F)(F)F>>CC(C)N1CCC(Oc2ccc3[nH]c(C(=O)N4CCN(S(=O)(=O)CC(F)(F)F)CC4)cc3c2)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-382105d56dcf4436bc52eca81bd4e6b4 | CC(C)N1CCC(Oc2ccc3[nH]c(C(=O)N4CCNCC4)cc3c2)CC1.O=C(Cl)C1CC1>>CC(C)N1CCC(Oc2ccc3[nH]c(C(=O)N4CCN(C(=O)C5CC5)CC4)cc3c2)CC1 | Cl.Cl.C(C)(C)N1CCC(CC1)OC=1C=C2C=C(NC2=CC1)C(=O)N1CCNCC1.C1(CC1)C(=O)Cl>>C1(CC1)C(=O)N1CCN(CC1)C(=O)C=1NC2=CC=C(C=C2C1)OC1CCN(CC1)C(C)C | [CH3:1][CH:2]([CH3:3])[N:4]1[CH2:5][CH2:6][CH:7]([O:8][c:9]2[cH:10][cH:11][c:12]3[nH:13][c:14]([C:15](=[O:16])[N:17]4[CH2:18][CH2:19][NH:20][CH2:26][CH2:27]4)[cH:28][c:29]3[cH:30]2)[CH2:31][CH2:32]1.Cl[C:21](=[O:22])[CH:23]1[CH2:24][CH2:25]1>>[CH3:1][CH:2]([CH3:3])[N:4]1[CH2:5][CH2:6][CH:7]([O:8][c:9]2[cH:10][cH:11][c:... | CC(C)N1CCC(Oc2ccc3[nH]c(C(=O)N4CCNCC4)cc3c2)CC1.O=C(Cl)C1CC1 | CC(C)N1CCC(Oc2ccc3[nH]c(C(=O)N4CCN(C(=O)C5CC5)CC4)cc3c2)CC1 | null | null | null | Acylation | N-alkylation of secondary amines with alkyl halides | 008ee4368afbd52034630a2410a1738f53049b314574435184e4e0be81b96642 | 96cb0a2fed10552c5770a45a2d6523b47ac3e38928b4a9c698d8577451182dcd | O=C(c1cc2cc(OC3CCNCC3)ccc2[nH]1)N1CCN(C(=O)C2CC2)CC1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]1-[C:4]-[C:5]-1.[#7:6]1-[C:7]-[C:8]-[NH;D2;+0:9]-[C:10]-[C:11]-1>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[C:3]1-[C:4]-[C:5]-1)-[N;H0;D3;+0:9]1-[C:8]-[C:7]-[#7:6]-[C:11]-[C:10]-1 | null | [] | null | null | null | null | The title compound was prepared in analogy to example 51, from [5-(1-isopropyl-piperidin-4-yloxy)-1H-indol-2-yl]-piperazin-1-yl-methanone dihydrochloride and cyclopropanoyl chloride. Light-yellow solid. MS (m/z): 439.5 (M+H)+.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Secondary amine | Tertiary amide | C1C[NH]CCN1 | C1C[NH]CC[NH]1 | C1CC[NH]CC1.c1ccc2[nH]ccc2c1.C1C[NH]CC[NH]1.C1CC1 | HCl | null | null | null | CC(C)N1CCC(Oc2ccc3[nH]c(C(=O)N4CCNCC4)cc3c2)CC1.O=C(Cl)C1CC1>>CC(C)N1CCC(Oc2ccc3[nH]c(C(=O)N4CCN(C(=O)C5CC5)CC4)cc3c2)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-87f57e94d60c439abf48c98e8adc4d43 | CC(C)N1CCC(Oc2ccc3[nH]c(C(=O)N4CCNCC4)cc3c2)CC1.COC(=O)Cl>>COC(=O)N1CCN(C(=O)c2cc3cc(OC4CCN(C(C)C)CC4)ccc3[nH]2)CC1 | Cl.Cl.C(C)(C)N1CCC(CC1)OC=1C=C2C=C(NC2=CC1)C(=O)N1CCNCC1.ClC(=O)OC>>COC(=O)N1CCN(CC1)C(=O)C=1NC2=CC=C(C=C2C1)OC1CCN(CC1)C(C)C | [NH:5]1[CH2:6][CH2:7][N:8]([C:9](=[O:10])[c:11]2[cH:12][c:13]3[cH:14][c:15]([O:16][CH:17]4[CH2:18][CH2:19][N:20]([CH:21]([CH3:22])[CH3:23])[CH2:24][CH2:25]4)[cH:26][cH:27][c:28]3[nH:29]2)[CH2:30][CH2:31]1.Cl[C:3]([O:2][CH3:1])=[O:4]>>[CH3:1][O:2][C:3](=[O:4])[N:5]1[CH2:6][CH2:7][N:8]([C:9](=[O:10])[c:11]2[cH:12][c:13]3... | CC(C)N1CCC(Oc2ccc3[nH]c(C(=O)N4CCNCC4)cc3c2)CC1.COC(=O)Cl | COC(=O)N1CCN(C(=O)c2cc3cc(OC4CCN(C(C)C)CC4)ccc3[nH]2)CC1 | null | null | null | Protection | N-alkylation of secondary amines with alkyl halides | 98754a5b02829fe15e66bc7afa63abfcc67bc327dedcd37a6b6b54543d6e3170 | d86dc1e6d0e089b3444b62ddfcf4c4822bdac4b60e628553036562518c29adcd | O=C(c1cc2cc(OC3CCNCC3)ccc2[nH]1)N1CCNCC1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C;D1;H3:4].[#7:5]1-[C:6]-[C:7]-[NH;D2;+0:8]-[C:9]-[C:10]-1>>[C;D1;H3:4]-[#8:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[N;H0;D3;+0:8]1-[C:7]-[C:6]-[#7:5]-[C:10]-[C:9]-1 | null | [] | null | null | null | null | The title compound was prepared in analogy to example 51, from [5-(1-isopropyl-piperidin-4-yloxy)-1H-indol-2-yl]-piperazin-1-yl-methanone dihydrochloride and methyl chloroformate. Light-yellow solid. MS (m/z): 429.3 (M+H)+.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Ether.Secondary amine | Carbamic ester | C1CNCC[NH]1 | C1C[NH]CC[NH]1 | C1C[NH]CC[NH]1.c1ccc2[nH]ccc2c1.C1CC[NH]CC1 | HCl | null | null | null | CC(C)N1CCC(Oc2ccc3[nH]c(C(=O)N4CCNCC4)cc3c2)CC1.COC(=O)Cl>>COC(=O)N1CCN(C(=O)c2cc3cc(OC4CCN(C(C)C)CC4)ccc3[nH]2)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-f7af323561ac40bd8dbd777457b6dda2 | CC(C)N1CCC(Oc2ccc3[nH]c(C(=O)N4CCNCC4)cc3c2)CC1.CN(C)C(=O)Cl>>CC(C)N1CCC(Oc2ccc3[nH]c(C(=O)N4CCN(C(=O)N(C)C)CC4)cc3c2)CC1 | Cl.Cl.C(C)(C)N1CCC(CC1)OC=1C=C2C=C(NC2=CC1)C(=O)N1CCNCC1.CN(C(=O)Cl)C>>CN(C(=O)N1CCN(CC1)C(=O)C=1NC2=CC=C(C=C2C1)OC1CCN(CC1)C(C)C)C | [CH3:1][CH:2]([CH3:3])[N:4]1[CH2:5][CH2:6][CH:7]([O:8][c:9]2[cH:10][cH:11][c:12]3[nH:13][c:14]([C:15](=[O:16])[N:17]4[CH2:18][CH2:19][NH:20][CH2:26][CH2:27]4)[cH:28][c:29]3[cH:30]2)[CH2:31][CH2:32]1.Cl[C:21](=[O:22])[N:23]([CH3:24])[CH3:25]>>[CH3:1][CH:2]([CH3:3])[N:4]1[CH2:5][CH2:6][CH:7]([O:8][c:9]2[cH:10][cH:11][c:1... | CC(C)N1CCC(Oc2ccc3[nH]c(C(=O)N4CCNCC4)cc3c2)CC1.CN(C)C(=O)Cl | CC(C)N1CCC(Oc2ccc3[nH]c(C(=O)N4CCN(C(=O)N(C)C)CC4)cc3c2)CC1 | null | null | null | Acylation | N-alkylation of secondary amines with alkyl halides | dcfba2aa7ca13a6ccdf0aa9e5554d01dee20f5aad8e3132e302a663220e425bb | 353c6e1db25433862a8bcf26ca332f6abeb45cb685806584bc65f8cfcb712540 | O=C(c1cc2cc(OC3CCNCC3)ccc2[nH]1)N1CCNCC1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#7:3](-[C;D1;H3:4])-[C;D1;H3:5].[#7:6]1-[C:7]-[C:8]-[NH;D2;+0:9]-[C:10]-[C:11]-1>>[C;D1;H3:4]-[#7:3](-[C;D1;H3:5])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[N;H0;D3;+0:9]1-[C:8]-[C:7]-[#7:6]-[C:11]-[C:10]-1 | null | [] | null | null | null | null | The title compound was prepared in analogy to example 51, from [5-(1-isopropyl-piperidin-4-yloxy)-1H-indol-2-yl]-piperazin-1-yl-methanone dihydrochloride and N,N-dimethylcarbamoyl chloride. Off-white solid. MS (m/z): 442.3 (M+H)+.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Tertiary amide.Secondary amine | Urea | C1C[NH]CCN1 | C1C[NH]CC[NH]1 | C1CC[NH]CC1.c1ccc2[nH]ccc2c1.C1C[NH]CC[NH]1 | HCl | null | null | null | CC(C)N1CCC(Oc2ccc3[nH]c(C(=O)N4CCNCC4)cc3c2)CC1.CN(C)C(=O)Cl>>CC(C)N1CCC(Oc2ccc3[nH]c(C(=O)N4CCN(C(=O)N(C)C)CC4)cc3c2)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-bb9d5cfda14c4a06994d7933fceb2b78 | CC(C)N1CCC(Oc2ccc3[nH]c(C(=O)N4CCNCC4)cc3c2)CC1.CCN(CC)C(=O)Cl>>CCN(CC)C(=O)N1CCN(C(=O)c2cc3cc(OC4CCN(C(C)C)CC4)ccc3[nH]2)CC1 | Cl.Cl.C(C)(C)N1CCC(CC1)OC=1C=C2C=C(NC2=CC1)C(=O)N1CCNCC1.C(C)N(C(=O)Cl)CC>>C(C)N(C(=O)N1CCN(CC1)C(=O)C=1NC2=CC=C(C=C2C1)OC1CCN(CC1)C(C)C)CC | [NH:8]1[CH2:9][CH2:10][N:11]([C:12](=[O:13])[c:14]2[cH:15][c:16]3[cH:17][c:18]([O:19][CH:20]4[CH2:21][CH2:22][N:23]([CH:24]([CH3:25])[CH3:26])[CH2:27][CH2:28]4)[cH:29][cH:30][c:31]3[nH:32]2)[CH2:33][CH2:34]1.Cl[C:6]([N:3]([CH2:2][CH3:1])[CH2:4][CH3:5])=[O:7]>>[CH3:1][CH2:2][N:3]([CH2:4][CH3:5])[C:6](=[O:7])[N:8]1[CH2:9... | CC(C)N1CCC(Oc2ccc3[nH]c(C(=O)N4CCNCC4)cc3c2)CC1.CCN(CC)C(=O)Cl | CCN(CC)C(=O)N1CCN(C(=O)c2cc3cc(OC4CCN(C(C)C)CC4)ccc3[nH]2)CC1 | null | null | null | Acylation | N-alkylation of secondary amines with alkyl halides | 9f480cf7d56f704fd9b7f19410e93a0b335ca09273ad87dbe310c5462f719bdc | 353c6e1db25433862a8bcf26ca332f6abeb45cb685806584bc65f8cfcb712540 | O=C(c1cc2cc(OC3CCNCC3)ccc2[nH]1)N1CCNCC1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#7:3](-[C:4])-[C:5].[#7:6]1-[C:7]-[C:8]-[NH;D2;+0:9]-[C:10]-[C:11]-1>>[C:4]-[#7:3](-[C:5])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[N;H0;D3;+0:9]1-[C:10]-[C:11]-[#7:6]-[C:7]-[C:8]-1 | null | [] | null | null | null | null | The title compound was prepared in analogy to example 51, from [5-(1-isopropyl-piperidin-4-yloxy)-1H-indol-2-yl]-piperazin-1-yl-methanone dihydrochloride and N,N-diethylcarbamoyl chloride. Off-white solid. MS (m/z): 470.6 (M+H)+.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Tertiary amide.Secondary amine | Urea | C1CNCC[NH]1 | C1C[NH]CC[NH]1 | C1C[NH]CC[NH]1.c1ccc2[nH]ccc2c1.C1CC[NH]CC1 | HCl | null | null | null | CC(C)N1CCC(Oc2ccc3[nH]c(C(=O)N4CCNCC4)cc3c2)CC1.CCN(CC)C(=O)Cl>>CCN(CC)C(=O)N1CCN(C(=O)c2cc3cc(OC4CCN(C(C)C)CC4)ccc3[nH]2)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-cfb1338ead364847928af1d93d45ec38 | CC(C)N1CCC(Oc2ccc3c(c2)cc(C(=O)N2CCNCC2)n3CC(F)F)CC1.CC(C)S(=O)(=O)Cl>>CC(C)N1CCC(Oc2ccc3c(c2)cc(C(=O)N2CCN(S(=O)(=O)C(C)C)CC2)n3CC(F)F)CC1 | Cl.FC(CN1C(=CC2=CC(=CC=C12)OC1CCN(CC1)C(C)C)C(=O)N1CCNCC1)F.CC(C)S(=O)(=O)Cl>>FC(CN1C(=CC2=CC(=CC=C12)OC1CCN(CC1)C(C)C)C(=O)N1CCN(CC1)S(=O)(=O)C(C)C)F | [CH3:1][CH:2]([CH3:3])[N:4]1[CH2:5][CH2:6][CH:7]([O:8][c:9]2[cH:10][cH:11][c:12]3[c:13]([cH:14]2)[cH:15][c:16]([C:17](=[O:18])[N:19]2[CH2:20][CH2:21][NH:22][CH2:29][CH2:30]2)[n:31]3[CH2:32][CH:33]([F:34])[F:35])[CH2:36][CH2:37]1.Cl[S:23](=[O:24])(=[O:25])[CH:26]([CH3:27])[CH3:28]>>[CH3:1][CH:2]([CH3:3])[N:4]1[CH2:5][CH... | CC(C)N1CCC(Oc2ccc3c(c2)cc(C(=O)N2CCNCC2)n3CC(F)F)CC1.CC(C)S(=O)(=O)Cl | CC(C)N1CCC(Oc2ccc3c(c2)cc(C(=O)N2CCN(S(=O)(=O)C(C)C)CC2)n3CC(F)F)CC1 | null | null | null | Acylation | Sulfonamide synthesis (Schotten-Baumann) secondary amine | c6a995ab9be6571957febbe378833244177e30fd671e64e4e1ffe6f50345cf56 | b7aca5a5d690b0846685a854bc946849e1041bfc3965161290b5ffb2821af09e | O=C(c1cc2cc(OC3CCNCC3)ccc2[nH]1)N1CCNCC1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[C:4](-[C;D1;H3:5])-[C;D1;H3:6].[#7:7]1-[C:8]-[C:9]-[NH;D2;+0:10]-[C:11]-[C:12]-1>>[C;D1;H3:5]-[C:4](-[C;D1;H3:6])-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[N;H0;D3;+0:10]1-[C:9]-[C:8]-[#7:7]-[C:12]-[C:11]-1 | null | [] | null | null | null | null | The title compound was prepared in analogy to example 51, from [1-(2,2-difluoro-ethyl)-5-(1-isopropyl-piperidin-4-yloxy)-1H-indol-2-yl]-piperazin-1-yl-methanone hydrochloride and 2-propanesulfonyl chloride. Light-yellow solid. MS (m/z): 541.3 (M+H)+.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Secondary amine.Sulfonyl halide | Tertiary amine | C1C[NH]CCN1 | C1C[NH]CC[NH]1 | C1CC[NH]CC1.c1ccc2[nH]ccc2c1.C1C[NH]CC[NH]1 | HCl | null | null | null | CC(C)N1CCC(Oc2ccc3c(c2)cc(C(=O)N2CCNCC2)n3CC(F)F)CC1.CC(C)S(=O)(=O)Cl>>CC(C)N1CCC(Oc2ccc3c(c2)cc(C(=O)N2CCN(S(=O)(=O)C(C)C)CC2)n3CC(F)F)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ed6980d1808a40398d906655820e2cf6 | CC(C)N1CCC(Oc2ccc3c(c2)cc(C(=O)N2CCNCC2)n3CC(F)F)CC1.O=C(Cl)C1CC1>>CC(C)N1CCC(Oc2ccc3c(c2)cc(C(=O)N2CCN(C(=O)C4CC4)CC2)n3CC(F)F)CC1 | Cl.FC(CN1C(=CC2=CC(=CC=C12)OC1CCN(CC1)C(C)C)C(=O)N1CCNCC1)F.C1(CC1)C(=O)Cl>>C1(CC1)C(=O)N1CCN(CC1)C(=O)C=1N(C2=CC=C(C=C2C1)OC1CCN(CC1)C(C)C)CC(F)F | [CH3:1][CH:2]([CH3:3])[N:4]1[CH2:5][CH2:6][CH:7]([O:8][c:9]2[cH:10][cH:11][c:12]3[c:13]([cH:14]2)[cH:15][c:16]([C:17](=[O:18])[N:19]2[CH2:20][CH2:21][NH:22][CH2:28][CH2:29]2)[n:30]3[CH2:31][CH:32]([F:33])[F:34])[CH2:35][CH2:36]1.Cl[C:23](=[O:24])[CH:25]1[CH2:26][CH2:27]1>>[CH3:1][CH:2]([CH3:3])[N:4]1[CH2:5][CH2:6][CH:7... | CC(C)N1CCC(Oc2ccc3c(c2)cc(C(=O)N2CCNCC2)n3CC(F)F)CC1.O=C(Cl)C1CC1 | CC(C)N1CCC(Oc2ccc3c(c2)cc(C(=O)N2CCN(C(=O)C4CC4)CC2)n3CC(F)F)CC1 | null | null | null | Acylation | N-alkylation of secondary amines with alkyl halides | 008ee4368afbd52034630a2410a1738f53049b314574435184e4e0be81b96642 | 96cb0a2fed10552c5770a45a2d6523b47ac3e38928b4a9c698d8577451182dcd | O=C(c1cc2cc(OC3CCNCC3)ccc2[nH]1)N1CCN(C(=O)C2CC2)CC1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]1-[C:4]-[C:5]-1.[#7:6]1-[C:7]-[C:8]-[NH;D2;+0:9]-[C:10]-[C:11]-1>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[C:3]1-[C:4]-[C:5]-1)-[N;H0;D3;+0:9]1-[C:8]-[C:7]-[#7:6]-[C:11]-[C:10]-1 | null | [] | null | null | null | null | The title compound was prepared in analogy to example 51, from [1-(2,2-difluoro-ethyl)-5-(1-isopropyl-piperidin-4-yloxy)-1H-indol-2-yl]-piperazin-1-yl-methanone hydrochloride and cyclopropanoyl chloride. Off-white solid. MS (m/z): 503.2 (M+H)+.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Secondary amine | Tertiary amide | C1C[NH]CCN1 | C1C[NH]CC[NH]1 | C1CC[NH]CC1.c1ccc2[nH]ccc2c1.C1C[NH]CC[NH]1.C1CC1 | HCl | null | null | null | CC(C)N1CCC(Oc2ccc3c(c2)cc(C(=O)N2CCNCC2)n3CC(F)F)CC1.O=C(Cl)C1CC1>>CC(C)N1CCC(Oc2ccc3c(c2)cc(C(=O)N2CCN(C(=O)C4CC4)CC2)n3CC(F)F)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-7d9c0a156feb4065a98cadd44a99b88a | CC(C)N1CCC(Oc2ccc3c(c2)cc(C(=O)N2CCNCC2)n3CC(F)F)CC1.O=S(=O)(Cl)CC(F)(F)F>>CC(C)N1CCC(Oc2ccc3c(c2)cc(C(=O)N2CCN(S(=O)(=O)CC(F)(F)F)CC2)n3CC(F)F)CC1 | Cl.FC(CN1C(=CC2=CC(=CC=C12)OC1CCN(CC1)C(C)C)C(=O)N1CCNCC1)F.FC(CS(=O)(=O)Cl)(F)F>>FC(CN1C(=CC2=CC(=CC=C12)OC1CCN(CC1)C(C)C)C(=O)N1CCN(CC1)S(=O)(=O)CC(F)(F)F)F | [CH3:1][CH:2]([CH3:3])[N:4]1[CH2:5][CH2:6][CH:7]([O:8][c:9]2[cH:10][cH:11][c:12]3[c:13]([cH:14]2)[cH:15][c:16]([C:17](=[O:18])[N:19]2[CH2:20][CH2:21][NH:22][CH2:31][CH2:32]2)[n:33]3[CH2:34][CH:35]([F:36])[F:37])[CH2:38][CH2:39]1.Cl[S:23](=[O:24])(=[O:25])[CH2:26][C:27]([F:28])([F:29])[F:30]>>[CH3:1][CH:2]([CH3:3])[N:4]... | CC(C)N1CCC(Oc2ccc3c(c2)cc(C(=O)N2CCNCC2)n3CC(F)F)CC1.O=S(=O)(Cl)CC(F)(F)F | CC(C)N1CCC(Oc2ccc3c(c2)cc(C(=O)N2CCN(S(=O)(=O)CC(F)(F)F)CC2)n3CC(F)F)CC1 | null | null | null | Acylation | Sulfonamide synthesis (Schotten-Baumann) secondary amine | c6a995ab9be6571957febbe378833244177e30fd671e64e4e1ffe6f50345cf56 | b7aca5a5d690b0846685a854bc946849e1041bfc3965161290b5ffb2821af09e | O=C(c1cc2cc(OC3CCNCC3)ccc2[nH]1)N1CCNCC1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[C:4]-[C:5](-[F;D1;H0:6])(-[F;D1;H0:7])-[F;D1;H0:8].[#7:9]1-[C:10]-[C:11]-[NH;D2;+0:12]-[C:13]-[C:14]-1>>[F;D1;H0:6]-[C:5](-[F;D1;H0:7])(-[F;D1;H0:8])-[C:4]-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[N;H0;D3;+0:12]1-[C:11]-[C:10]-[#7:9]-[C:14]-[C:13]-1 | null | [] | null | null | null | null | The title compound was prepared in analogy to example 51, from [1-(2,2-difluoro-ethyl)-5-(1-isopropyl-piperidin-4-yloxy)-1H-indol-2-yl]-piperazin-1-yl-methanone hydrochloride and 2,2,2-trifluoro-ethanesulfonyl chloride. Light-yellow solid. MS (m/z): 581.3 (M+H)+.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Secondary amine.Sulfonyl halide | Tertiary amine | C1C[NH]CCN1 | C1C[NH]CC[NH]1 | C1CC[NH]CC1.c1ccc2[nH]ccc2c1.C1C[NH]CC[NH]1 | HCl | null | null | null | CC(C)N1CCC(Oc2ccc3c(c2)cc(C(=O)N2CCNCC2)n3CC(F)F)CC1.O=S(=O)(Cl)CC(F)(F)F>>CC(C)N1CCC(Oc2ccc3c(c2)cc(C(=O)N2CCN(S(=O)(=O)CC(F)(F)F)CC2)n3CC(F)F)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e7b6fac5fd3942649843ebfb88f09278 | CC(C)N1CCC(Oc2ccc3c(c2)cc(C(=O)N2CCNCC2)n3CC(F)F)CC1.COC(=O)Cl>>COC(=O)N1CCN(C(=O)c2cc3cc(OC4CCN(C(C)C)CC4)ccc3n2CC(F)F)CC1 | Cl.FC(CN1C(=CC2=CC(=CC=C12)OC1CCN(CC1)C(C)C)C(=O)N1CCNCC1)F.ClC(=O)OC>>COC(=O)N1CCN(CC1)C(=O)C=1N(C2=CC=C(C=C2C1)OC1CCN(CC1)C(C)C)CC(F)F | [NH:5]1[CH2:6][CH2:7][N:8]([C:9](=[O:10])[c:11]2[cH:12][c:13]3[cH:14][c:15]([O:16][CH:17]4[CH2:18][CH2:19][N:20]([CH:21]([CH3:22])[CH3:23])[CH2:24][CH2:25]4)[cH:26][cH:27][c:28]3[n:29]2[CH2:30][CH:31]([F:32])[F:33])[CH2:34][CH2:35]1.Cl[C:3]([O:2][CH3:1])=[O:4]>>[CH3:1][O:2][C:3](=[O:4])[N:5]1[CH2:6][CH2:7][N:8]([C:9](=... | CC(C)N1CCC(Oc2ccc3c(c2)cc(C(=O)N2CCNCC2)n3CC(F)F)CC1.COC(=O)Cl | COC(=O)N1CCN(C(=O)c2cc3cc(OC4CCN(C(C)C)CC4)ccc3n2CC(F)F)CC1 | null | null | null | Protection | N-alkylation of secondary amines with alkyl halides | 98754a5b02829fe15e66bc7afa63abfcc67bc327dedcd37a6b6b54543d6e3170 | d86dc1e6d0e089b3444b62ddfcf4c4822bdac4b60e628553036562518c29adcd | O=C(c1cc2cc(OC3CCNCC3)ccc2[nH]1)N1CCNCC1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C;D1;H3:4].[#7:5]1-[C:6]-[C:7]-[NH;D2;+0:8]-[C:9]-[C:10]-1>>[C;D1;H3:4]-[#8:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[N;H0;D3;+0:8]1-[C:7]-[C:6]-[#7:5]-[C:10]-[C:9]-1 | null | [] | null | null | null | null | The title compound was prepared in analogy to example 51, from [1-(2,2-difluoro-ethyl)-5-(1-isopropyl-piperidin-4-yloxy)-1H-indol-2-yl]-piperazin-1-yl-methanone hydrochloride and methyl chloroformate. Light-yellow solid. MS (m/z): 493.2 (M+H)+.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Ether.Secondary amine | Carbamic ester | C1CNCC[NH]1 | C1C[NH]CC[NH]1 | C1C[NH]CC[NH]1.c1ccc2[nH]ccc2c1.C1CC[NH]CC1 | HCl | null | null | null | CC(C)N1CCC(Oc2ccc3c(c2)cc(C(=O)N2CCNCC2)n3CC(F)F)CC1.COC(=O)Cl>>COC(=O)N1CCN(C(=O)c2cc3cc(OC4CCN(C(C)C)CC4)ccc3n2CC(F)F)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-4b36ce3541724bef9408a57b3288fb20 | CC(C)N1CCC(Oc2ccc3c(c2)cc(C(=O)N2CCNCC2)n3CC(F)F)CC1.CN(C)C(=O)Cl>>CC(C)N1CCC(Oc2ccc3c(c2)cc(C(=O)N2CCN(C(=O)N(C)C)CC2)n3CC(F)F)CC1 | Cl.FC(CN1C(=CC2=CC(=CC=C12)OC1CCN(CC1)C(C)C)C(=O)N1CCNCC1)F.CN(C(=O)Cl)C>>CN(C(=O)N1CCN(CC1)C(=O)C=1N(C2=CC=C(C=C2C1)OC1CCN(CC1)C(C)C)CC(F)F)C | [CH3:1][CH:2]([CH3:3])[N:4]1[CH2:5][CH2:6][CH:7]([O:8][c:9]2[cH:10][cH:11][c:12]3[c:13]([cH:14]2)[cH:15][c:16]([C:17](=[O:18])[N:19]2[CH2:20][CH2:21][NH:22][CH2:28][CH2:29]2)[n:30]3[CH2:31][CH:32]([F:33])[F:34])[CH2:35][CH2:36]1.Cl[C:23](=[O:24])[N:25]([CH3:26])[CH3:27]>>[CH3:1][CH:2]([CH3:3])[N:4]1[CH2:5][CH2:6][CH:7]... | CC(C)N1CCC(Oc2ccc3c(c2)cc(C(=O)N2CCNCC2)n3CC(F)F)CC1.CN(C)C(=O)Cl | CC(C)N1CCC(Oc2ccc3c(c2)cc(C(=O)N2CCN(C(=O)N(C)C)CC2)n3CC(F)F)CC1 | null | null | null | Acylation | N-alkylation of secondary amines with alkyl halides | dcfba2aa7ca13a6ccdf0aa9e5554d01dee20f5aad8e3132e302a663220e425bb | 353c6e1db25433862a8bcf26ca332f6abeb45cb685806584bc65f8cfcb712540 | O=C(c1cc2cc(OC3CCNCC3)ccc2[nH]1)N1CCNCC1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#7:3](-[C;D1;H3:4])-[C;D1;H3:5].[#7:6]1-[C:7]-[C:8]-[NH;D2;+0:9]-[C:10]-[C:11]-1>>[C;D1;H3:4]-[#7:3](-[C;D1;H3:5])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[N;H0;D3;+0:9]1-[C:8]-[C:7]-[#7:6]-[C:11]-[C:10]-1 | null | [] | null | null | null | null | The title compound was prepared in analogy to example 51, from [1-(2,2-difluoro-ethyl)-5-(1-isopropyl-piperidin-4-yloxy)-1H-indol-2-yl]-piperazin-1-yl-methanone hydrochloride and N,N-dimethylcarbamoyl chloride. Off-white solid. MS (m/z): 506.4 (M+H)+.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Tertiary amide.Secondary amine | Urea | C1C[NH]CCN1 | C1C[NH]CC[NH]1 | C1CC[NH]CC1.c1ccc2[nH]ccc2c1.C1C[NH]CC[NH]1 | HCl | null | null | null | CC(C)N1CCC(Oc2ccc3c(c2)cc(C(=O)N2CCNCC2)n3CC(F)F)CC1.CN(C)C(=O)Cl>>CC(C)N1CCC(Oc2ccc3c(c2)cc(C(=O)N2CCN(C(=O)N(C)C)CC2)n3CC(F)F)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-404c8fffa7124c2dbf7089c2aded08e2 | CC(C)N1CCC(Oc2ccc3c(c2)cc(C(=O)N2CCNCC2)n3CC(F)F)CC1.CCN(CC)C(=O)Cl>>CCN(CC)C(=O)N1CCN(C(=O)c2cc3cc(OC4CCN(C(C)C)CC4)ccc3n2CC(F)F)CC1 | Cl.FC(CN1C(=CC2=CC(=CC=C12)OC1CCN(CC1)C(C)C)C(=O)N1CCNCC1)F.C(C)N(C(=O)Cl)CC>>C(C)N(C(=O)N1CCN(CC1)C(=O)C=1N(C2=CC=C(C=C2C1)OC1CCN(CC1)C(C)C)CC(F)F)CC | [NH:8]1[CH2:9][CH2:10][N:11]([C:12](=[O:13])[c:14]2[cH:15][c:16]3[cH:17][c:18]([O:19][CH:20]4[CH2:21][CH2:22][N:23]([CH:24]([CH3:25])[CH3:26])[CH2:27][CH2:28]4)[cH:29][cH:30][c:31]3[n:32]2[CH2:33][CH:34]([F:35])[F:36])[CH2:37][CH2:38]1.Cl[C:6]([N:3]([CH2:2][CH3:1])[CH2:4][CH3:5])=[O:7]>>[CH3:1][CH2:2][N:3]([CH2:4][CH3:... | CC(C)N1CCC(Oc2ccc3c(c2)cc(C(=O)N2CCNCC2)n3CC(F)F)CC1.CCN(CC)C(=O)Cl | CCN(CC)C(=O)N1CCN(C(=O)c2cc3cc(OC4CCN(C(C)C)CC4)ccc3n2CC(F)F)CC1 | null | null | null | Acylation | N-alkylation of secondary amines with alkyl halides | 9f480cf7d56f704fd9b7f19410e93a0b335ca09273ad87dbe310c5462f719bdc | 353c6e1db25433862a8bcf26ca332f6abeb45cb685806584bc65f8cfcb712540 | O=C(c1cc2cc(OC3CCNCC3)ccc2[nH]1)N1CCNCC1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#7:3](-[C:4])-[C:5].[#7:6]1-[C:7]-[C:8]-[NH;D2;+0:9]-[C:10]-[C:11]-1>>[C:4]-[#7:3](-[C:5])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[N;H0;D3;+0:9]1-[C:10]-[C:11]-[#7:6]-[C:7]-[C:8]-1 | null | [] | null | null | null | null | The title compound was prepared in analogy to example 51, from [1-(2,2-difluoro-ethyl)-5-(1-isopropyl-piperidin-4-yloxy)-1H-indol-2-yl]-piperazin-1-yl-methanone hydrochloride and N,N-diethylcarbamoyl chloride. Off-white solid. MS (m/z): 534.3 (M+H)+.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Tertiary amide.Secondary amine | Urea | C1CNCC[NH]1 | C1C[NH]CC[NH]1 | C1C[NH]CC[NH]1.c1ccc2[nH]ccc2c1.C1CC[NH]CC1 | HCl | null | null | null | CC(C)N1CCC(Oc2ccc3c(c2)cc(C(=O)N2CCNCC2)n3CC(F)F)CC1.CCN(CC)C(=O)Cl>>CCN(CC)C(=O)N1CCN(C(=O)c2cc3cc(OC4CCN(C(C)C)CC4)ccc3n2CC(F)F)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-3159aa5af3f9439fad1f68b2b64e444b | CC(C)N1CCC(Oc2ccc3c(c2)cc(C(=O)N2CCNCC2)n3CC(F)F)CC1.CN(C)S(=O)(=O)Cl>>CC(C)N1CCC(Oc2ccc3c(c2)cc(C(=O)N2CCN(S(=O)(=O)N(C)C)CC2)n3CC(F)F)CC1 | Cl.FC(CN1C(=CC2=CC(=CC=C12)OC1CCN(CC1)C(C)C)C(=O)N1CCNCC1)F.CN(S(=O)(=O)Cl)C>>CN(S(=O)(=O)N1CCN(CC1)C(=O)C=1N(C2=CC=C(C=C2C1)OC1CCN(CC1)C(C)C)CC(F)F)C | [CH3:1][CH:2]([CH3:3])[N:4]1[CH2:5][CH2:6][CH:7]([O:8][c:9]2[cH:10][cH:11][c:12]3[c:13]([cH:14]2)[cH:15][c:16]([C:17](=[O:18])[N:19]2[CH2:20][CH2:21][NH:22][CH2:29][CH2:30]2)[n:31]3[CH2:32][CH:33]([F:34])[F:35])[CH2:36][CH2:37]1.Cl[S:23](=[O:24])(=[O:25])[N:26]([CH3:27])[CH3:28]>>[CH3:1][CH:2]([CH3:3])[N:4]1[CH2:5][CH2... | CC(C)N1CCC(Oc2ccc3c(c2)cc(C(=O)N2CCNCC2)n3CC(F)F)CC1.CN(C)S(=O)(=O)Cl | CC(C)N1CCC(Oc2ccc3c(c2)cc(C(=O)N2CCN(S(=O)(=O)N(C)C)CC2)n3CC(F)F)CC1 | null | null | null | Acylation | Sulfonamide synthesis (Schotten-Baumann) secondary amine | 9472b3d472badfbf976c26bebba6611bda86b371cf2a2283d41c5954a87661db | 6c2a4c35ccae10843ff928afe56a8d3bc92b152c9bcc4d800e2ad816b6c86d86 | O=C(c1cc2cc(OC3CCNCC3)ccc2[nH]1)N1CCNCC1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[#7:4](-[C;D1;H3:5])-[C;D1;H3:6].[#7:7]1-[C:8]-[C:9]-[NH;D2;+0:10]-[C:11]-[C:12]-1>>[C;D1;H3:5]-[#7:4](-[C;D1;H3:6])-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[N;H0;D3;+0:10]1-[C:9]-[C:8]-[#7:7]-[C:12]-[C:11]-1 | null | [] | null | null | null | null | The title compound was prepared in analogy to example 51, from [1-(2,2-difluoro-ethyl)-5-(1-isopropyl-piperidin-4-yloxy)-1H-indol-2-yl]-piperazin-1-yl-methanone hydrochloride and dimethylsulfamoyl chloride. Light-yellow solid. MS (m/z): 542.3 (M+H)+.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Secondary amine | Tertiary amine | C1C[NH]CCN1 | C1C[NH]CC[NH]1 | C1CC[NH]CC1.c1ccc2[nH]ccc2c1.C1C[NH]CC[NH]1 | HCl | null | null | null | CC(C)N1CCC(Oc2ccc3c(c2)cc(C(=O)N2CCNCC2)n3CC(F)F)CC1.CN(C)S(=O)(=O)Cl>>CC(C)N1CCC(Oc2ccc3c(c2)cc(C(=O)N2CCN(S(=O)(=O)N(C)C)CC2)n3CC(F)F)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-5120230619c8480f96c7be153d77ec80 | CC(C)N1CCC(Oc2ccc3c(c2)cc(C(=O)N2CCNCC2)n3C(C)C)CC1.CC(C)S(=O)(=O)Cl>>CC(C)N1CCC(Oc2ccc3c(c2)cc(C(=O)N2CCN(S(=O)(=O)C(C)C)CC2)n3C(C)C)CC1 | Cl.C(C)(C)N1C(=CC2=CC(=CC=C12)OC1CCN(CC1)C(C)C)C(=O)N1CCNCC1.CC(C)S(=O)(=O)Cl>>C(C)(C)N1C(=CC2=CC(=CC=C12)OC1CCN(CC1)C(C)C)C(=O)N1CCN(CC1)S(=O)(=O)C(C)C | [CH3:1][CH:2]([CH3:3])[N:4]1[CH2:5][CH2:6][CH:7]([O:8][c:9]2[cH:10][cH:11][c:12]3[c:13]([cH:14]2)[cH:15][c:16]([C:17](=[O:18])[N:19]2[CH2:20][CH2:21][NH:22][CH2:29][CH2:30]2)[n:31]3[CH:32]([CH3:33])[CH3:34])[CH2:35][CH2:36]1.Cl[S:23](=[O:24])(=[O:25])[CH:26]([CH3:27])[CH3:28]>>[CH3:1][CH:2]([CH3:3])[N:4]1[CH2:5][CH2:6]... | CC(C)N1CCC(Oc2ccc3c(c2)cc(C(=O)N2CCNCC2)n3C(C)C)CC1.CC(C)S(=O)(=O)Cl | CC(C)N1CCC(Oc2ccc3c(c2)cc(C(=O)N2CCN(S(=O)(=O)C(C)C)CC2)n3C(C)C)CC1 | null | null | null | Acylation | Sulfonamide synthesis (Schotten-Baumann) secondary amine | c6a995ab9be6571957febbe378833244177e30fd671e64e4e1ffe6f50345cf56 | b7aca5a5d690b0846685a854bc946849e1041bfc3965161290b5ffb2821af09e | O=C(c1cc2cc(OC3CCNCC3)ccc2[nH]1)N1CCNCC1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[C:4](-[C;D1;H3:5])-[C;D1;H3:6].[#7:7]1-[C:8]-[C:9]-[NH;D2;+0:10]-[C:11]-[C:12]-1>>[C;D1;H3:5]-[C:4](-[C;D1;H3:6])-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[N;H0;D3;+0:10]1-[C:9]-[C:8]-[#7:7]-[C:12]-[C:11]-1 | null | [] | null | null | null | null | The title compound was prepared in analogy to example 51, from [1-isopropyl-5-(1-isopropyl-piperidin-4-yloxy)-1H-indol-2-yl]-piperazin-1-yl-methanone hydrochloride and 2-propanesulfonyl chloride. Off-white solid. MS (m/z): 519.3 (M+H)+.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Secondary amine.Sulfonyl halide | Tertiary amine | C1C[NH]CCN1 | C1C[NH]CC[NH]1 | C1CC[NH]CC1.c1ccc2[nH]ccc2c1.C1C[NH]CC[NH]1 | HCl | null | null | null | CC(C)N1CCC(Oc2ccc3c(c2)cc(C(=O)N2CCNCC2)n3C(C)C)CC1.CC(C)S(=O)(=O)Cl>>CC(C)N1CCC(Oc2ccc3c(c2)cc(C(=O)N2CCN(S(=O)(=O)C(C)C)CC2)n3C(C)C)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-eb1cc6f7607f4d44ac6677ec2084b722 | CC(C)N1CCC(Oc2ccc3c(c2)cc(C(=O)N2CCNCC2)n3C(C)C)CC1.O=C(Cl)C1CC1>>CC(C)N1CCC(Oc2ccc3c(c2)cc(C(=O)N2CCN(C(=O)C4CC4)CC2)n3C(C)C)CC1 | Cl.C(C)(C)N1C(=CC2=CC(=CC=C12)OC1CCN(CC1)C(C)C)C(=O)N1CCNCC1.C1(CC1)C(=O)Cl>>C1(CC1)C(=O)N1CCN(CC1)C(=O)C=1N(C2=CC=C(C=C2C1)OC1CCN(CC1)C(C)C)C(C)C | [CH3:1][CH:2]([CH3:3])[N:4]1[CH2:5][CH2:6][CH:7]([O:8][c:9]2[cH:10][cH:11][c:12]3[c:13]([cH:14]2)[cH:15][c:16]([C:17](=[O:18])[N:19]2[CH2:20][CH2:21][NH:22][CH2:28][CH2:29]2)[n:30]3[CH:31]([CH3:32])[CH3:33])[CH2:34][CH2:35]1.Cl[C:23](=[O:24])[CH:25]1[CH2:26][CH2:27]1>>[CH3:1][CH:2]([CH3:3])[N:4]1[CH2:5][CH2:6][CH:7]([O... | CC(C)N1CCC(Oc2ccc3c(c2)cc(C(=O)N2CCNCC2)n3C(C)C)CC1.O=C(Cl)C1CC1 | CC(C)N1CCC(Oc2ccc3c(c2)cc(C(=O)N2CCN(C(=O)C4CC4)CC2)n3C(C)C)CC1 | null | null | null | Acylation | N-alkylation of secondary amines with alkyl halides | 008ee4368afbd52034630a2410a1738f53049b314574435184e4e0be81b96642 | 96cb0a2fed10552c5770a45a2d6523b47ac3e38928b4a9c698d8577451182dcd | O=C(c1cc2cc(OC3CCNCC3)ccc2[nH]1)N1CCN(C(=O)C2CC2)CC1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]1-[C:4]-[C:5]-1.[#7:6]1-[C:7]-[C:8]-[NH;D2;+0:9]-[C:10]-[C:11]-1>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[C:3]1-[C:4]-[C:5]-1)-[N;H0;D3;+0:9]1-[C:8]-[C:7]-[#7:6]-[C:11]-[C:10]-1 | null | [] | null | null | null | null | The title compound was prepared in analogy to example 51, from [1-isopropyl-5-(1-isopropyl-piperidin-4-yloxy)-1H-indol-2-yl]-piperazin-1-yl-methanone hydrochloride and cyclopropanoyl chloride. Light-yellow solid. MS (m/z): 481.5 (M+H)+.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Secondary amine | Tertiary amide | C1C[NH]CCN1 | C1C[NH]CC[NH]1 | C1CC[NH]CC1.c1ccc2[nH]ccc2c1.C1C[NH]CC[NH]1.C1CC1 | HCl | null | null | null | CC(C)N1CCC(Oc2ccc3c(c2)cc(C(=O)N2CCNCC2)n3C(C)C)CC1.O=C(Cl)C1CC1>>CC(C)N1CCC(Oc2ccc3c(c2)cc(C(=O)N2CCN(C(=O)C4CC4)CC2)n3C(C)C)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-5dd32515a0e04f91ae30da32c08171de | CC(C)N1CCC(Oc2ccc3c(c2)cc(C(=O)N2CCNCC2)n3C(C)C)CC1.O=S(=O)(Cl)CC(F)(F)F>>CC(C)N1CCC(Oc2ccc3c(c2)cc(C(=O)N2CCN(S(=O)(=O)CC(F)(F)F)CC2)n3C(C)C)CC1 | Cl.C(C)(C)N1C(=CC2=CC(=CC=C12)OC1CCN(CC1)C(C)C)C(=O)N1CCNCC1.FC(CS(=O)(=O)Cl)(F)F>>C(C)(C)N1C(=CC2=CC(=CC=C12)OC1CCN(CC1)C(C)C)C(=O)N1CCN(CC1)S(=O)(=O)CC(F)(F)F | [CH3:1][CH:2]([CH3:3])[N:4]1[CH2:5][CH2:6][CH:7]([O:8][c:9]2[cH:10][cH:11][c:12]3[c:13]([cH:14]2)[cH:15][c:16]([C:17](=[O:18])[N:19]2[CH2:20][CH2:21][NH:22][CH2:31][CH2:32]2)[n:33]3[CH:34]([CH3:35])[CH3:36])[CH2:37][CH2:38]1.Cl[S:23](=[O:24])(=[O:25])[CH2:26][C:27]([F:28])([F:29])[F:30]>>[CH3:1][CH:2]([CH3:3])[N:4]1[CH... | CC(C)N1CCC(Oc2ccc3c(c2)cc(C(=O)N2CCNCC2)n3C(C)C)CC1.O=S(=O)(Cl)CC(F)(F)F | CC(C)N1CCC(Oc2ccc3c(c2)cc(C(=O)N2CCN(S(=O)(=O)CC(F)(F)F)CC2)n3C(C)C)CC1 | null | null | null | Acylation | Sulfonamide synthesis (Schotten-Baumann) secondary amine | c6a995ab9be6571957febbe378833244177e30fd671e64e4e1ffe6f50345cf56 | b7aca5a5d690b0846685a854bc946849e1041bfc3965161290b5ffb2821af09e | O=C(c1cc2cc(OC3CCNCC3)ccc2[nH]1)N1CCNCC1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[C:4]-[C:5](-[F;D1;H0:6])(-[F;D1;H0:7])-[F;D1;H0:8].[#7:9]1-[C:10]-[C:11]-[NH;D2;+0:12]-[C:13]-[C:14]-1>>[F;D1;H0:6]-[C:5](-[F;D1;H0:7])(-[F;D1;H0:8])-[C:4]-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[N;H0;D3;+0:12]1-[C:11]-[C:10]-[#7:9]-[C:14]-[C:13]-1 | null | [] | null | null | null | null | The title compound was prepared in analogy to example 51, from [1-isopropyl-5-(1-isopropyl-piperidin-4-yloxy)-1H-indol-2-yl]-piperazin-1-yl-methanone hydrochloride and 2,2,2-trifluoro-ethanesulfonyl chloride. Off-white solid. MS (m/z): 559.4 (M+H)+.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Secondary amine.Sulfonyl halide | Tertiary amine | C1C[NH]CCN1 | C1C[NH]CC[NH]1 | C1CC[NH]CC1.c1ccc2[nH]ccc2c1.C1C[NH]CC[NH]1 | HCl | null | null | null | CC(C)N1CCC(Oc2ccc3c(c2)cc(C(=O)N2CCNCC2)n3C(C)C)CC1.O=S(=O)(Cl)CC(F)(F)F>>CC(C)N1CCC(Oc2ccc3c(c2)cc(C(=O)N2CCN(S(=O)(=O)CC(F)(F)F)CC2)n3C(C)C)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-eb3407d9cc5248b692d8d413b2487919 | CC(C)N1CCC(Oc2ccc3c(c2)cc(C(=O)N2CCNCC2)n3C(C)C)CC1.COC(=O)Cl>>COC(=O)N1CCN(C(=O)c2cc3cc(OC4CCN(C(C)C)CC4)ccc3n2C(C)C)CC1 | Cl.C(C)(C)N1C(=CC2=CC(=CC=C12)OC1CCN(CC1)C(C)C)C(=O)N1CCNCC1.ClC(=O)OC>>COC(=O)N1CCN(CC1)C(=O)C=1N(C2=CC=C(C=C2C1)OC1CCN(CC1)C(C)C)C(C)C | [NH:5]1[CH2:6][CH2:7][N:8]([C:9](=[O:10])[c:11]2[cH:12][c:13]3[cH:14][c:15]([O:16][CH:17]4[CH2:18][CH2:19][N:20]([CH:21]([CH3:22])[CH3:23])[CH2:24][CH2:25]4)[cH:26][cH:27][c:28]3[n:29]2[CH:30]([CH3:31])[CH3:32])[CH2:33][CH2:34]1.Cl[C:3]([O:2][CH3:1])=[O:4]>>[CH3:1][O:2][C:3](=[O:4])[N:5]1[CH2:6][CH2:7][N:8]([C:9](=[O:1... | CC(C)N1CCC(Oc2ccc3c(c2)cc(C(=O)N2CCNCC2)n3C(C)C)CC1.COC(=O)Cl | COC(=O)N1CCN(C(=O)c2cc3cc(OC4CCN(C(C)C)CC4)ccc3n2C(C)C)CC1 | null | null | null | Protection | N-alkylation of secondary amines with alkyl halides | 98754a5b02829fe15e66bc7afa63abfcc67bc327dedcd37a6b6b54543d6e3170 | d86dc1e6d0e089b3444b62ddfcf4c4822bdac4b60e628553036562518c29adcd | O=C(c1cc2cc(OC3CCNCC3)ccc2[nH]1)N1CCNCC1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C;D1;H3:4].[#7:5]1-[C:6]-[C:7]-[NH;D2;+0:8]-[C:9]-[C:10]-1>>[C;D1;H3:4]-[#8:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[N;H0;D3;+0:8]1-[C:7]-[C:6]-[#7:5]-[C:10]-[C:9]-1 | null | [] | null | null | null | null | The title compound was prepared in analogy to example 51, from [1-isopropyl-5-(1-isopropyl-piperidin-4-yloxy)-1H-indol-2-yl]-piperazin-1-yl-methanone hydrochloride and methyl chloroformate. Light-yellow solid. MS (m/z): 471.3 (M+H)+.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Ether.Secondary amine | Carbamic ester | C1CNCC[NH]1 | C1C[NH]CC[NH]1 | C1C[NH]CC[NH]1.c1ccc2[nH]ccc2c1.C1CC[NH]CC1 | HCl | null | null | null | CC(C)N1CCC(Oc2ccc3c(c2)cc(C(=O)N2CCNCC2)n3C(C)C)CC1.COC(=O)Cl>>COC(=O)N1CCN(C(=O)c2cc3cc(OC4CCN(C(C)C)CC4)ccc3n2C(C)C)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-b553fe7f352442599fb3f72a1466f5d7 | CC(C)N1CCC(Oc2ccc3c(c2)cc(C(=O)N2CCNCC2)n3C(C)C)CC1.CN(C)C(=O)Cl>>CC(C)N1CCC(Oc2ccc3c(c2)cc(C(=O)N2CCN(C(=O)N(C)C)CC2)n3C(C)C)CC1 | Cl.C(C)(C)N1C(=CC2=CC(=CC=C12)OC1CCN(CC1)C(C)C)C(=O)N1CCNCC1.CN(C(=O)Cl)C>>CN(C(=O)N1CCN(CC1)C(=O)C=1N(C2=CC=C(C=C2C1)OC1CCN(CC1)C(C)C)C(C)C)C | [CH3:1][CH:2]([CH3:3])[N:4]1[CH2:5][CH2:6][CH:7]([O:8][c:9]2[cH:10][cH:11][c:12]3[c:13]([cH:14]2)[cH:15][c:16]([C:17](=[O:18])[N:19]2[CH2:20][CH2:21][NH:22][CH2:28][CH2:29]2)[n:30]3[CH:31]([CH3:32])[CH3:33])[CH2:34][CH2:35]1.Cl[C:23](=[O:24])[N:25]([CH3:26])[CH3:27]>>[CH3:1][CH:2]([CH3:3])[N:4]1[CH2:5][CH2:6][CH:7]([O:... | CC(C)N1CCC(Oc2ccc3c(c2)cc(C(=O)N2CCNCC2)n3C(C)C)CC1.CN(C)C(=O)Cl | CC(C)N1CCC(Oc2ccc3c(c2)cc(C(=O)N2CCN(C(=O)N(C)C)CC2)n3C(C)C)CC1 | null | null | null | Acylation | N-alkylation of secondary amines with alkyl halides | dcfba2aa7ca13a6ccdf0aa9e5554d01dee20f5aad8e3132e302a663220e425bb | 353c6e1db25433862a8bcf26ca332f6abeb45cb685806584bc65f8cfcb712540 | O=C(c1cc2cc(OC3CCNCC3)ccc2[nH]1)N1CCNCC1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#7:3](-[C;D1;H3:4])-[C;D1;H3:5].[#7:6]1-[C:7]-[C:8]-[NH;D2;+0:9]-[C:10]-[C:11]-1>>[C;D1;H3:4]-[#7:3](-[C;D1;H3:5])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[N;H0;D3;+0:9]1-[C:8]-[C:7]-[#7:6]-[C:11]-[C:10]-1 | null | [] | null | null | null | null | The title compound was prepared in analogy to example 51, from [1-isopropyl-5-(1-isopropyl-piperidin-4-yloxy)-1H-indol-2-yl]-piperazin-1-yl-methanone hydrochloride and N,N-dimethylcarbamoyl chloride. Off-white solid. MS (m/z): 484.4 (M+H)+.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Tertiary amide.Secondary amine | Urea | C1C[NH]CCN1 | C1C[NH]CC[NH]1 | C1CC[NH]CC1.c1ccc2[nH]ccc2c1.C1C[NH]CC[NH]1 | HCl | null | null | null | CC(C)N1CCC(Oc2ccc3c(c2)cc(C(=O)N2CCNCC2)n3C(C)C)CC1.CN(C)C(=O)Cl>>CC(C)N1CCC(Oc2ccc3c(c2)cc(C(=O)N2CCN(C(=O)N(C)C)CC2)n3C(C)C)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-437296a80f494ff988b45523fbb7fb55 | CC(C)N1CCC(Oc2ccc3c(c2)cc(C(=O)N2CCNCC2)n3C(C)C)CC1.CCN(CC)C(=O)Cl>>CCN(CC)C(=O)N1CCN(C(=O)c2cc3cc(OC4CCN(C(C)C)CC4)ccc3n2C(C)C)CC1 | Cl.C(C)(C)N1C(=CC2=CC(=CC=C12)OC1CCN(CC1)C(C)C)C(=O)N1CCNCC1.C(C)N(C(=O)Cl)CC>>C(C)N(C(=O)N1CCN(CC1)C(=O)C=1N(C2=CC=C(C=C2C1)OC1CCN(CC1)C(C)C)C(C)C)CC | [NH:8]1[CH2:9][CH2:10][N:11]([C:12](=[O:13])[c:14]2[cH:15][c:16]3[cH:17][c:18]([O:19][CH:20]4[CH2:21][CH2:22][N:23]([CH:24]([CH3:25])[CH3:26])[CH2:27][CH2:28]4)[cH:29][cH:30][c:31]3[n:32]2[CH:33]([CH3:34])[CH3:35])[CH2:36][CH2:37]1.Cl[C:6]([N:3]([CH2:2][CH3:1])[CH2:4][CH3:5])=[O:7]>>[CH3:1][CH2:2][N:3]([CH2:4][CH3:5])[... | CC(C)N1CCC(Oc2ccc3c(c2)cc(C(=O)N2CCNCC2)n3C(C)C)CC1.CCN(CC)C(=O)Cl | CCN(CC)C(=O)N1CCN(C(=O)c2cc3cc(OC4CCN(C(C)C)CC4)ccc3n2C(C)C)CC1 | null | null | null | Acylation | N-alkylation of secondary amines with alkyl halides | 9f480cf7d56f704fd9b7f19410e93a0b335ca09273ad87dbe310c5462f719bdc | 353c6e1db25433862a8bcf26ca332f6abeb45cb685806584bc65f8cfcb712540 | O=C(c1cc2cc(OC3CCNCC3)ccc2[nH]1)N1CCNCC1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#7:3](-[C:4])-[C:5].[#7:6]1-[C:7]-[C:8]-[NH;D2;+0:9]-[C:10]-[C:11]-1>>[C:4]-[#7:3](-[C:5])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[N;H0;D3;+0:9]1-[C:10]-[C:11]-[#7:6]-[C:7]-[C:8]-1 | null | [] | null | null | null | null | The title compound was prepared in analogy to example 51, from [1-isopropyl-5-(1-isopropyl-piperidin-4-yloxy)-1H-indol-2-yl]-piperazin-1-yl-methanone hydrochloride and N,N-diethylcarbamoyl chloride. Off-white solid. MS (m/z): 512.5 (M+H)+.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Tertiary amide.Secondary amine | Urea | C1CNCC[NH]1 | C1C[NH]CC[NH]1 | C1C[NH]CC[NH]1.c1ccc2[nH]ccc2c1.C1CC[NH]CC1 | HCl | null | null | null | CC(C)N1CCC(Oc2ccc3c(c2)cc(C(=O)N2CCNCC2)n3C(C)C)CC1.CCN(CC)C(=O)Cl>>CCN(CC)C(=O)N1CCN(C(=O)c2cc3cc(OC4CCN(C(C)C)CC4)ccc3n2C(C)C)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-07a967d2170243e8be4f2abc93e1bedd | CC(C)N1CCC(Oc2ccc3c(c2)cc(C(=O)N2CCNCC2)n3C(C)C)CC1.O=S(=O)(Cl)C(F)(F)F>>CC(C)N1CCC(Oc2ccc3c(c2)cc(C(=O)N2CCN(S(=O)(=O)C(F)(F)F)CC2)n3C(C)C)CC1 | Cl.C(C)(C)N1C(=CC2=CC(=CC=C12)OC1CCN(CC1)C(C)C)C(=O)N1CCNCC1.FC(S(=O)(=O)Cl)(F)F>>C(C)(C)N1C(=CC2=CC(=CC=C12)OC1CCN(CC1)C(C)C)C(=O)N1CCN(CC1)S(=O)(=O)C(F)(F)F | [CH3:1][CH:2]([CH3:3])[N:4]1[CH2:5][CH2:6][CH:7]([O:8][c:9]2[cH:10][cH:11][c:12]3[c:13]([cH:14]2)[cH:15][c:16]([C:17](=[O:18])[N:19]2[CH2:20][CH2:21][NH:22][CH2:30][CH2:31]2)[n:32]3[CH:33]([CH3:34])[CH3:35])[CH2:36][CH2:37]1.Cl[S:23](=[O:24])(=[O:25])[C:26]([F:27])([F:28])[F:29]>>[CH3:1][CH:2]([CH3:3])[N:4]1[CH2:5][CH2... | CC(C)N1CCC(Oc2ccc3c(c2)cc(C(=O)N2CCNCC2)n3C(C)C)CC1.O=S(=O)(Cl)C(F)(F)F | CC(C)N1CCC(Oc2ccc3c(c2)cc(C(=O)N2CCN(S(=O)(=O)C(F)(F)F)CC2)n3C(C)C)CC1 | null | null | null | Acylation | Sulfonamide synthesis (Schotten-Baumann) secondary amine | c6a995ab9be6571957febbe378833244177e30fd671e64e4e1ffe6f50345cf56 | b7aca5a5d690b0846685a854bc946849e1041bfc3965161290b5ffb2821af09e | O=C(c1cc2cc(OC3CCNCC3)ccc2[nH]1)N1CCNCC1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[C:4](-[F;D1;H0:5])(-[F;D1;H0:6])-[F;D1;H0:7].[#7:8]1-[C:9]-[C:10]-[NH;D2;+0:11]-[C:12]-[C:13]-1>>[F;D1;H0:5]-[C:4](-[F;D1;H0:6])(-[F;D1;H0:7])-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[N;H0;D3;+0:11]1-[C:10]-[C:9]-[#7:8]-[C:13]-[C:12]-1 | null | [] | null | null | null | null | The title compound was prepared in analogy to example 51, from [1-isopropyl-5-(1-isopropyl-piperidin-4-yloxy)-1H-indol-2-yl]-piperazin-1-yl-methanone hydrochloride and trifluoromethanesulfonyl chloride. Light-yellow solid. MS (m/z): 545.3 (M+H)+.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Secondary amine.Sulfonyl halide | Tertiary amine | C1C[NH]CCN1 | C1C[NH]CC[NH]1 | C1CC[NH]CC1.c1ccc2[nH]ccc2c1.C1C[NH]CC[NH]1 | HCl | null | null | null | CC(C)N1CCC(Oc2ccc3c(c2)cc(C(=O)N2CCNCC2)n3C(C)C)CC1.O=S(=O)(Cl)C(F)(F)F>>CC(C)N1CCC(Oc2ccc3c(c2)cc(C(=O)N2CCN(S(=O)(=O)C(F)(F)F)CC2)n3C(C)C)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-c7201a39bff44238a0369f8fa7b950e0 | CC(C)N1CCC(Oc2ccc3c(c2)cc(C(=O)N2CCNCC2)n3C(C)C)CC1.CN(C)S(=O)(=O)Cl>>CC(C)N1CCC(Oc2ccc3c(c2)cc(C(=O)N2CCN(S(=O)(=O)N(C)C)CC2)n3C(C)C)CC1 | Cl.C(C)(C)N1C(=CC2=CC(=CC=C12)OC1CCN(CC1)C(C)C)C(=O)N1CCNCC1.CN(S(=O)(=O)Cl)C>>CN(S(=O)(=O)N1CCN(CC1)C(=O)C=1N(C2=CC=C(C=C2C1)OC1CCN(CC1)C(C)C)C(C)C)C | [CH3:1][CH:2]([CH3:3])[N:4]1[CH2:5][CH2:6][CH:7]([O:8][c:9]2[cH:10][cH:11][c:12]3[c:13]([cH:14]2)[cH:15][c:16]([C:17](=[O:18])[N:19]2[CH2:20][CH2:21][NH:22][CH2:29][CH2:30]2)[n:31]3[CH:32]([CH3:33])[CH3:34])[CH2:35][CH2:36]1.Cl[S:23](=[O:24])(=[O:25])[N:26]([CH3:27])[CH3:28]>>[CH3:1][CH:2]([CH3:3])[N:4]1[CH2:5][CH2:6][... | CC(C)N1CCC(Oc2ccc3c(c2)cc(C(=O)N2CCNCC2)n3C(C)C)CC1.CN(C)S(=O)(=O)Cl | CC(C)N1CCC(Oc2ccc3c(c2)cc(C(=O)N2CCN(S(=O)(=O)N(C)C)CC2)n3C(C)C)CC1 | null | null | null | Acylation | Sulfonamide synthesis (Schotten-Baumann) secondary amine | 9472b3d472badfbf976c26bebba6611bda86b371cf2a2283d41c5954a87661db | 6c2a4c35ccae10843ff928afe56a8d3bc92b152c9bcc4d800e2ad816b6c86d86 | O=C(c1cc2cc(OC3CCNCC3)ccc2[nH]1)N1CCNCC1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[#7:4](-[C;D1;H3:5])-[C;D1;H3:6].[#7:7]1-[C:8]-[C:9]-[NH;D2;+0:10]-[C:11]-[C:12]-1>>[C;D1;H3:5]-[#7:4](-[C;D1;H3:6])-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[N;H0;D3;+0:10]1-[C:9]-[C:8]-[#7:7]-[C:12]-[C:11]-1 | null | [] | null | null | null | null | The title compound was prepared in analogy to example 51, from [1-isopropyl-5-(1-isopropyl-piperidin-4-yloxy)-1H-indol-2-yl]-piperazin-1-yl-methanone hydrochloride and dimethylsulfamoyl chloride. Light-yellow foam. MS (m/z): 520.2 (M+H)+.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Secondary amine | Tertiary amine | C1C[NH]CCN1 | C1C[NH]CC[NH]1 | C1CC[NH]CC1.c1ccc2[nH]ccc2c1.C1C[NH]CC[NH]1 | HCl | null | null | null | CC(C)N1CCC(Oc2ccc3c(c2)cc(C(=O)N2CCNCC2)n3C(C)C)CC1.CN(C)S(=O)(=O)Cl>>CC(C)N1CCC(Oc2ccc3c(c2)cc(C(=O)N2CCN(S(=O)(=O)N(C)C)CC2)n3C(C)C)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-63c3ca63d3ed41baa0d4b9fe576da2ca | COC(=O)N1CCNCC1.O=C(O)c1cc2cc(OC3CCN(CC(F)(F)F)CC3)ccc2[nH]1>>COC(=O)N1CCN(C(=O)c2cc3cc(OC4CCN(CC(F)(F)F)CC4)ccc3[nH]2)CC1 | FC(CN1CCC(CC1)OC=1C=C2C=C(NC2=CC1)C(=O)O)(F)F.N1(CCNCC1)C(=O)OC>>COC(=O)N1CCN(CC1)C(=O)C=1NC2=CC=C(C=C2C1)OC1CCN(CC1)CC(F)(F)F | [CH3:1][O:2][C:3](=[O:4])[N:5]1[CH2:6][CH2:7][NH:8][CH2:32][CH2:33]1.O[C:9](=[O:10])[c:11]1[cH:12][c:13]2[cH:14][c:15]([O:16][CH:17]3[CH2:18][CH2:19][N:20]([CH2:21][C:22]([F:23])([F:24])[F:25])[CH2:26][CH2:27]3)[cH:28][cH:29][c:30]2[nH:31]1>>[CH3:1][O:2][C:3](=[O:4])[N:5]1[CH2:6][CH2:7][N:8]([C:9](=[O:10])[c:11]2[cH:12... | COC(=O)N1CCNCC1.O=C(O)c1cc2cc(OC3CCN(CC(F)(F)F)CC3)ccc2[nH]1 | COC(=O)N1CCN(C(=O)c2cc3cc(OC4CCN(CC(F)(F)F)CC4)ccc3[nH]2)CC1 | null | null | null | Acylation | Acylation of Nitrogen Nucleophiles by Carboxylic Acids | be4b86020a065d99e289e528d425e25dd0737bea0f2fd81bb05a4d03f92a7d75 | c5e4172490b2731ba9322b68af56376edadc31ce0bb9a3dfdea23a1817a852fd | O=C(c1cc2cc(OC3CCNCC3)ccc2[nH]1)N1CCNCC1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[#7;a:5]:[c:6].[#7:7]1-[C:8]-[C:9]-[NH;D2;+0:10]-[C:11]-[C:12]-1>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[N;H0;D3;+0:10]1-[C:9]-[C:8]-[#7:7]-[C:12]-[C:11]-1)-[c:3](:[c:4]):[#7;a:5]:[c:6] | null | [] | null | null | null | null | The title compound was prepared in analogy to example 40b), from 5-[1-(2,2,2-trifluoro-ethyl)-piperidin-4-yloxy]-1H-indole-2-carboxylic acid and methyl piperazine-1-carboxylate. Light yellow solid. MS (m/z): 469.3 (M+H)+.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | Tertiary amide | C1C[NH]CCN1 | C1C[NH]CC[NH]1 | C1C[NH]CC[NH]1.c1ccc2[nH]ccc2c1.C1CC[NH]CC1 | HO- | null | null | null | COC(=O)N1CCNCC1.O=C(O)c1cc2cc(OC3CCN(CC(F)(F)F)CC3)ccc2[nH]1>>COC(=O)N1CCN(C(=O)c2cc3cc(OC4CCN(CC(F)(F)F)CC4)ccc3[nH]2)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-678c86ed5e184ea29bab85536d9aef8e | CCOC(=O)c1cc2cc(O)ccc2[nH]1.OC1CCN(CC(F)(F)F)CC1>>CCOC(=O)c1cc2cc(OC3CCN(CC(F)(F)F)CC3)ccc2[nH]1 | OC=1C=C2C=C(NC2=CC1)C(=O)OCC.FC(CN1CCC(CC1)O)(F)F.N(=NC(=O)OC(C)C)C(=O)OC(C)C>>FC(CN1CCC(CC1)OC=1C=C2C=C(NC2=CC1)C(=O)OCC)(F)F | [CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][c:8]2[cH:9][c:10]([OH:11])[cH:23][cH:24][c:25]2[nH:26]1.O[CH:12]1[CH2:13][CH2:14][N:15]([CH2:16][C:17]([F:18])([F:19])[F:20])[CH2:21][CH2:22]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][c:8]2[cH:9][c:10]([O:11][CH:12]3[CH2:13][CH2:14][N:15]([CH2:16][C:17]([F:18])([F:19])[... | CCOC(=O)c1cc2cc(O)ccc2[nH]1.OC1CCN(CC(F)(F)F)CC1 | CCOC(=O)c1cc2cc(OC3CCN(CC(F)(F)F)CC3)ccc2[nH]1 | null | null | null | Heteroatom Alkylation and Arylation | Mitsunobu aryl ether | a9e936b0e9135225700edbab1c7696738b7f1f0756494b6ceeeda63b184d572f | 776ba735002e33225fbc578943016110c2c43efefd97bfeea4ec3cc2e2e1532f | c1cc2cc(OC3CCNCC3)ccc2[nH]1 | O-[CH;D3;+0:1]1-[C:2]-[C:3]-[#7:4]-[C:5]-[C:6]-1.[OH;D1;+0:7]-[c:8](:[c:9]):[c:10]>>[c:9]:[c:8](-[O;H0;D2;+0:7]-[CH;D3;+0:1]1-[C:2]-[C:3]-[#7:4]-[C:5]-[C:6]-1):[c:10] | null | [] | null | null | null | null | The title compound was prepared in analogy to example 40d), from ethyl 5-hydroxyindole-2-carboxylate and 1-(2,2,2-trifluoro-ethyl)piperidin-4-ol, using diisopropyl azodicarboxylate instead of diethyl azodicarboxylate. Off-white solid. MS (m/z): 371.2 (M+H)+.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol.Aromatic alcohol | Ether | C1CC[NH]CC1 | C1CC[NH]CC1 | c1ccc2[nH]ccc2c1.C1CC[NH]CC1 | HO- | null | null | null | CCOC(=O)c1cc2cc(O)ccc2[nH]1.OC1CCN(CC(F)(F)F)CC1>>CCOC(=O)c1cc2cc(OC3CCN(CC(F)(F)F)CC3)ccc2[nH]1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-fbec5948a29a4f66ba74d90f261126e9 | CN(C)C1(c2ccccc2)CCC(C=O)CC1.Fc1ccc(C[P+](c2ccccc2)(c2ccccc2)c2ccccc2)cc1.[Cl-]>>CN(C)C1(c2ccccc2)CCC(C=Cc2ccc(F)cc2)CC1.Cl | CN(C1(CCC(CC1)C=O)C1=CC=CC=C1)C.[Cl-].FC1=CC=C(C[P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.[K].C(C)(C)(C)[O-]>>Cl.FC1=CC=C(C=C1)C=CC1CCC(CC1)(C1=CC=CC=C1)N(C)C | O=[CH:14][CH:13]1[CH2:12][CH2:11][C:4]([N:2]([CH3:1])[CH3:3])([c:5]2[cH:6][cH:7][cH:8][cH:9][cH:10]2)[CH2:24][CH2:23]1.c1ccc([P+](c2ccccc2)(c2ccccc2)[CH2:15][c:16]2[cH:17][cH:18][c:19]([F:20])[cH:21][cH:22]2)cc1.[Cl-:25]>>[CH3:1][N:2]([CH3:3])[C:4]1([c:5]2[cH:6][cH:7][cH:8][cH:9][cH:10]2)[CH2:11][CH2:12][CH:13]([CH:14]... | CN(C)C1(c2ccccc2)CCC(C=O)CC1.Fc1ccc(C[P+](c2ccccc2)(c2ccccc2)c2ccccc2)cc1.[Cl-] | CN(C)C1(c2ccccc2)CCC(C=Cc2ccc(F)cc2)CC1.Cl | null | null | C1CCOC1 | C-C Coupling | OtherReaction | cb5f277ac55a0e763ef643becc05f1522019cc4161daceb249ed2d634b78153b | cedc9d4b791e43eacf8e7ecfa6a98d1dc0438794e96e4f1c4bef436b78f82bd8 | C(=CC1CCC(c2ccccc2)CC1)c1ccccc1 | O=[CH;D2;+0:1]-[C:2](-[C:3])-[C:4].[Cl-;H0;D0:5].[c:6]:[c:7](-[CH2;D2;+0:8]-[P+](-c1:c:c:c:c:c:1)(-c1:c:c:c:c:c:1)-c1:c:c:c:c:c:1):[c:9]>>[C:3]-[C:2](-[CH;D2;+0:1]=[CH;D2;+0:8]-[c:7](:[c:6]):[c:9])-[C:4].[ClH;D0;+0:5] | null | [] | null | null | 30 | MINUTE | 4-fluorobenzyltriphenyl phosphonium chloride (1.22 g, 3 mmole) was suspended under argon in abs. THF (15 ml) and cooled to −5° C. Potassium-tert-butanolate (337 mg, 3 mmole) dissolved in THF (14 ml) was added dropwise and the mixture post-stirred for 30 min at <0°. 4-dimethylamino-4-phenylcyclohexane carbaldehyde (467 ... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | null | c1ccccc1.c1ccccc1.c1ccccc1 | null | c1ccccc1.C1CCCCC1.c1ccccc1 | HO- | C1CCOC1 | null | 0.5 | CN(C)C1(c2ccccc2)CCC(C=O)CC1.Fc1ccc(C[P+](c2ccccc2)(c2ccccc2)c2ccccc2)cc1.[Cl-]>C1CCOC1>CN(C)C1(c2ccccc2)CCC(C=Cc2ccc(F)cc2)CC1.Cl |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-b9baa8b938bb4678b620f56fdeca6529 | CN(C)C1(c2ccccc2)CCC(C=Cc2ccc(F)cc2)CC1>>CN(C)C1(c2ccccc2)CCC(C=Cc2ccc(F)cc2)CC1.CN(C)C1(c2ccccc2)CCC(C=Cc2ccc(F)cc2)CC1 | Cl.FC1=CC=C(C=C1)C=CC1CCC(CC1)(C1=CC=CC=C1)N(C)C>>Cl.FC1=CC=C(C=C1)C=CC1CCC(CC1)(C1=CC=CC=C1)N(C)C.FC1=CC=C(C=C1)C=CC1CCC(CC1)(C1=CC=CC=C1)N(C)C | [CH3:1][N:2]([C:4]1([c:5]2[cH:6][cH:7][cH:8][cH:9][cH:10]2)[CH2:35][CH2:36][CH:37]([CH:38]=[CH:39][c:40]2[cH:22][cH:21][c:19]([F:20])[cH:18][cH:41]2)[CH2:45][CH2:46]1)[CH3:29]>>[CH3:1][N:2]([CH3:3])[C:4]1([c:5]2[cH:6][cH:7][cH:8][cH:9][cH:10]2)[CH2:11][CH2:12][CH:13]([CH:14]=[CH:15][c:16]2[cH:17][cH:18][c:19]([F:20])[c... | CN(C)C1(c2ccccc2)CCC(C=Cc2ccc(F)cc2)CC1 | CN(C)C1(c2ccccc2)CCC(C=Cc2ccc(F)cc2)CC1.CN(C)C1(c2ccccc2)CCC(C=Cc2ccc(F)cc2)CC1 | null | null | CC(CC)=O | Aromatic Heterocycle Formation | OtherReaction | 08a033d2514c88484b05c94ceb1115d3c299505ec196d8cd87e779e6e35794dd | 7709ea319235d24cfb5c0056ba368e49dcaf4917f91bb00220f500abe1e9be2a | C(=CC1CCC(c2ccccc2)CC1)c1ccccc1.C(=CC1CCC(c2ccccc2)CC1)c1ccccc1 | [C;D1;H3:1]-[N;H0;D3;+0:2](-[CH3;D1;+0:3])-[C;H0;D4;+0:4]1(-[c:5](:[c:6]):[c:7])-[CH2;D2;+0:8]-[C:9]-[CH;D3;+0:10](-[C:11]=[C:12]-[c;H0;D3;+0:13]2:[cH;D2;+0:14]:[c:15]:[c:16](-[F;D1;H0:17]):[cH;D2;+0:18]:[cH;D2;+0:19]:2)-[CH2;D2;+0:20]-[CH2;D2;+0:21]-1>>[#7:22]-[C:23]1(-[c;H0;D3;+0:3](:[c:24]:[c:25]):[c:26]:[c:27])-[C:... | null | [] | null | null | 2 | HOUR | As described for Example 5, 69 mg of the second most polar diastereoisomer of {4-[2-(4-fluorophenyl)vinyl]-1-phenylcyclohexyl}dimethylamine were also obtained (yellow oil) which were dissolved in 2-butanone (1.5 ml), and subsequently 3.3M ethanolic HCl (194 μl, 0.6 mmole) was added and the mixture stirred for 2 h. Afte... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amine | Aromatic halide.Tertiary amine.Tertiary amine | C1CCCCC1.c1ccccc1 | C1CCCCC1.c1ccccc1.c1ccccc1.C1CCCCC1.c1ccccc1 | c1ccccc1.C1CCCCC1.c1ccccc1.c1ccccc1.C1CCCCC1.c1ccccc1 | Other | CC(CC)=O | null | 2 | CN(C)C1(c2ccccc2)CCC(C=Cc2ccc(F)cc2)CC1>CC(CC)=O>CN(C)C1(c2ccccc2)CCC(C=Cc2ccc(F)cc2)CC1.CN(C)C1(c2ccccc2)CCC(C=Cc2ccc(F)cc2)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-b389fc697dc240099ed29c4eb07b7eba | Cl>>Cl | C(C)OCC.Cl.N1C=C(C2=CC=CC=C12)CC=CC1CCC(CC1)(C1=CC=CC=C1)N(C)C.N1C=C(C2=CC=CC=C12)CC=CC1CCC(CC1)(C1=CC=CC=C1)N(C)C.Cl[Si](C)(C)C>>Cl.N1C=C(C2=CC=CC=C12)CC=CC1CCC(CC1)(C1=CC=CC=C1)N(C)C | [ClH:28]>>[ClH:28] | Cl | Cl | null | null | CC(CC)=O | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | null | null | null | [] | null | null | null | null | As described for Example 8, less polar diastereoisomers of {4-[3-(1H-indol-3-yl)-propenyl]-1-phenylcyclohexyl}dimethylamine were not obtained cleanly. For purification, 750 mg non-polar crude product were suspended in 95 ml water and 1 ml 85% by weight phosphoric acid. The suspension was shaken with diethyl ether (3×20... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | null | null | CC(CC)=O | null | null | Cl>CC(CC)=O>Cl |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-b451d5cf75864953be053b6145451a1d | BrC(Br)(Br)Br.CC(C)(C)OC(=O)n1cc(C=O)c2ccccc21>>CC(C)(C)OC(=O)n1cc(C=C(Br)Br)c2ccccc21 | CCCCCC.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C(C)(C)(C)OC(=O)N1C=C(C2=CC=CC=C12)C=O.BrC(Br)(Br)Br>>C(C)(C)(C)OC(=O)N1C=C(C2=CC=CC=C12)C=C(Br)Br | Br[C:12](Br)([Br:13])[Br:14].O=[CH:11][c:10]1[cH:9][n:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[c:20]2[c:15]1[cH:16][cH:17][cH:18][cH:19]2>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[n:8]1[cH:9][c:10]([CH:11]=[C:12]([Br:13])[Br:14])[c:15]2[cH:16][cH:17][cH:18][cH:19][c:20]12 | BrC(Br)(Br)Br.CC(C)(C)OC(=O)n1cc(C=O)c2ccccc21 | CC(C)(C)OC(=O)n1cc(C=C(Br)Br)c2ccccc21 | null | null | C(Cl)Cl | C-C Coupling | OtherReaction | b27e55226bb2edd452ae488b95081b2b03421ee27be6c3935dbea4c7a5eeb5f6 | 695d5d1b30a064e72a7d907baf677e910730421b6580cc4e59d378cd6f0be898 | c1ccc2[nH]ccc2c1 | Br-[C;H0;D4;+0:1](-Br)(-[Br;D1;H0:2])-[Br;D1;H0:3].O=[CH;D2;+0:4]-[c:5]1:[c:6]:[c:7]:[#7;a:8](-[C:9](-[#8:10])=[O;D1;H0:11]):[c:12]:1>>[#8:10]-[C:9](=[O;D1;H0:11])-[#7;a:8]1:[c:7]:[c:6]:[c:5](-[CH;D2;+0:4]=[C;H0;D3;+0:1](-[Br;D1;H0:2])-[Br;D1;H0:3]):[c:12]:1 | 95.2 | [{"value": 95.2, "product": "C(C)(C)(C)OC(=O)N1C=C(C2=CC=CC=C12)C=C(Br)Br", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 1 | HOUR | Triphenylphosphane (17.2 g, 65.5 mmole) was added in portions at 0° C., while stirring and within 60 min to a solution of tetrabromocarbon (10.9 g, 32.7 mmole) in DCM (120 ml) and post-stirred for 1 h at 0° C. 3-formyl-indole-1-carboxylic acid-tert-butylester (4 g, 16.4 mmole) dissolved in DCM (30 ml) was subsequently ... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary halide.Tertiary halide.Tertiary halide.Tertiary halide.Aldehyde | Alkenyl halide.Alkenyl halide | null | null | c1c[nH]c2ccccc12 | Br- | C(Cl)Cl | 0 | 1 | BrC(Br)(Br)Br.CC(C)(C)OC(=O)n1cc(C=O)c2ccccc21>C(Cl)Cl>CC(C)(C)OC(=O)n1cc(C=C(Br)Br)c2ccccc21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-1b6e7812a3de42a88c5b16d0566d6771 | CC(=O)Nc1cccc2c1C(=O)OC2=O.CCOc1cc(C(N)CS(C)(=O)=O)ccc1OC>>CCOc1cc(C(CS(C)(=O)=O)N2C(=O)c3cccc(NC(C)=O)c3C2=O)ccc1OC | C(C)OC=1C=C(C=CC1OC)C(CS(=O)(=O)C)N.C(C)(=O)NC1=C2C(C(=O)OC2=O)=CC=C1>>C(C)OC=1C=C(C=CC1OC)C(CS(=O)(=O)C)N1C(C2=CC=CC(=C2C1=O)NC(C)=O)=O | O1[C:14](=[O:15])[c:16]2[cH:17][cH:18][cH:19][c:20]([NH:21][C:22]([CH3:23])=[O:24])[c:25]2[C:26]1=[O:27].[CH3:1][CH2:2][O:3][c:4]1[cH:5][c:6]([CH:7]([CH2:8][S:9]([CH3:10])(=[O:11])=[O:12])[NH2:13])[cH:28][cH:29][c:30]1[O:31][CH3:32]>>[CH3:1][CH2:2][O:3][c:4]1[cH:5][c:6]([CH:7]([CH2:8][S:9]([CH3:10])(=[O:11])=[O:12])[N:... | CC(=O)Nc1cccc2c1C(=O)OC2=O.CCOc1cc(C(N)CS(C)(=O)=O)ccc1OC | CCOc1cc(C(CS(C)(=O)=O)N2C(=O)c3cccc(NC(C)=O)c3C2=O)ccc1OC | null | null | C(C)(=O)O | Acylation | Phthalic anhydride to phthalimide | c3c986d6e09320348d40a4a59ca107882ce771f249842049dc55e55f334c675b | 2bbbf7b24648445e31d33a2a26f8618c2067bd23957587cc459f3c45a03ed48a | O=C1c2ccccc2C(=O)N1Cc1ccccc1 | [C:1]-[C:2](-[NH2;D1;+0:3])-[c:4].[O;D1;H0:5]=[C;H0;D3;+0:6]1-O-[C;H0;D3;+0:7](=[O;D1;H0:8])-[c:9](:[c:10]):[c:11]-1:[c:12]>>[C:1]-[C:2](-[c:4])-[N;H0;D3;+0:3]1-[C;H0;D3;+0:6](=[O;D1;H0:5])-[c:11](:[c:12]):[c:9](:[c:10])-[C;H0;D3;+0:7]-1=[O;D1;H0:8] | 59.3 | [{"value": 59.0, "product": "C(C)OC=1C=C(C=CC1OC)C(CS(=O)(=O)C)N1C(C2=CC=CC(=C2C1=O)NC(C)=O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 59.3, "product": "C(C)OC=1C=C(C=CC1OC)C(CS(=O)(=O)C)N1C(C2=CC=CC(=C2C1=O)NC(C)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A stirred solution of 1-(3-ethoxy-4-methoxyphenyl)-2-methylsulfonylethylamine (1.0 g, 3.7 mmol) and 3-acetamidophthalic anhydride (751 mg, 3.66 mmol) in acetic acid (20 mL) was heated at reflux for 15 h. The solvent was removed in vacuo to yield an oil. Chromatography of the resulting oil yielded the product as a yello... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Ester.Ester.Primary amine | Substituted dicarboximide | c1ccc2c(c1)COC2 | c1ccc2c(c1)C[NH]C2 | c1ccccc1.c1ccc2c(c1)C[NH]C2 | HO- | C(C)(=O)O | null | null | CC(=O)Nc1cccc2c1C(=O)OC2=O.CCOc1cc(C(N)CS(C)(=O)=O)ccc1OC>C(C)(=O)O>CCOc1cc(C(CS(C)(=O)=O)N2C(=O)c3cccc(NC(C)=O)c3C2=O)ccc1OC |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-22faef66200548b3880e574be715cd13 | O=C(O)c1cccc([N+](=O)[O-])c1C(=O)O>>Nc1cccc(C(=O)O)c1C(=O)O | [H][H].[H][H].[N+](=O)([O-])C1=C(C(C(=O)O)=CC=C1)C(=O)O.[H][H]>>NC1=C(C(C(=O)O)=CC=C1)C(=O)O | O=[N+:1]([O-])[c:2]1[cH:3][cH:4][cH:5][c:6]([C:7](=[O:8])[OH:9])[c:10]1[C:11](=[O:12])[OH:13]>>[NH2:1][c:2]1[cH:3][cH:4][cH:5][c:6]([C:7](=[O:8])[OH:9])[c:10]1[C:11](=[O:12])[OH:13] | O=C(O)c1cccc([N+](=O)[O-])c1C(=O)O | Nc1cccc(C(=O)O)c1C(=O)O | null | [Pd] | C(C)O | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccccc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]-[C:5](=[O;D1;H0:6])-[O;D1;H1:7]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4]-[C:5](=[O;D1;H0:6])-[O;D1;H1:7] | 84 | [{"value": 84.0, "product": "NC1=C(C(C(=O)O)=CC=C1)C(=O)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 84.0, "product": "NC1=C(C(C(=O)O)=CC=C1)C(=O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 13 | HOUR | 10% Pd/C (2.5 g), 3-nitrophthalic acid (75.0 g, 355 mmol) and ethanol (1.5 L) were charged to a 2.5 L Parr hydrogenator, under a nitrogen atmosphere. Hydrogen was charged to the reaction vessel for up to 55 psi. The mixture was shaken for 13 hours, maintaining hydrogen pressure between 50 and 55 psi. Hydrogen was relea... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1 | Other | [Pd].C(C)O | null | 13 | O=C(O)c1cccc([N+](=O)[O-])c1C(=O)O>[Pd].C(C)O>Nc1cccc(C(=O)O)c1C(=O)O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-84a7a6b4fbab40d78942753c14739e12 | CC(=O)OC(C)=O.Nc1cccc(C(=O)O)c1C(=O)O>>CC(=O)Nc1cccc2c1C(=O)OC2=O | NC1=C(C(C(=O)O)=CC=C1)C(=O)O.C(C)(=O)OC(C)=O>>C(C)(=O)NC1=C2C(C(=O)OC2=O)=CC=C1 | CC(=O)O[C:2]([CH3:1])=[O:3].O[C:14]([c:9]1[cH:8][cH:7][cH:6][c:5]([NH2:4])[c:10]1[C:11](=[O:12])[OH:13])=[O:15]>>[CH3:1][C:2](=[O:3])[NH:4][c:5]1[cH:6][cH:7][cH:8][c:9]2[c:10]1[C:11](=[O:12])[O:13][C:14]2=[O:15] | CC(=O)OC(C)=O.Nc1cccc(C(=O)O)c1C(=O)O | CC(=O)Nc1cccc2c1C(=O)OC2=O | null | null | null | Acylation | OtherReaction | 617c13c0fd0733e95edf575c7a45ee818629fb61a4451b32cd2addac5c310e5b | ffc045ed8a9408524e8f5f9dc2e099a8f11ba6601fd402a08d042de24191cf1d | O=C1OC(=O)c2ccccc21 | C-C(=O)-O-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].O-[C;H0;D3;+0:4](=[O;D1;H0:5])-[c:6](:[c:7]):[c:8](-[C:9](=[O;D1;H0:10])-[OH;D1;+0:11]):[c:12](-[NH2;D1;+0:13]):[c:14]>>[C;D1;H3:2]-[C;H0;D3;+0:1](=[O;D1;H0:3])-[NH;D2;+0:13]-[c:12](:[c:14]):[c:8]1:[c:6](:[c:7])-[C;H0;D3;+0:4](=[O;D1;H0:5])-[O;H0;D2;+0:11]-[C:9]-1=[O;D... | 61 | [{"value": 61.0, "product": "C(C)(=O)NC1=C2C(C(=O)OC2=O)=CC=C1", "details": "PERCENTYIELD", "is_desired": false}] | 2.5 | CELSIUS | null | null | A 1 L 3-necked round bottom flask was equipped with a mechanical stirrer, thermometer, and condenser and charged with 3-aminophthalic acid (108 g, 596 mmol) and acetic anhydride (550 mL). The reaction mixture was heated to reflux for 3 hours and cooled to ambient temperature and further to 0-5° C. for another 1 hour. T... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Carboxylic acid.Carboxylic acid.Primary amine | Anhydride.Ester.Ester.Secondary amide | null | c1ccc2c(c1)COC2 | c1ccc2c(c1)COC2 | HO- | null | 2.5 | null | CC(=O)OC(C)=O.Nc1cccc(C(=O)O)c1C(=O)O>>CC(=O)Nc1cccc2c1C(=O)OC2=O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-bc03aed0730246ecae54382a543353ca | CCOc1cc(C(N)CS(C)(=O)=O)ccc1OC>>CCOc1cc([C@H](N)CS(C)(=O)=O)ccc1OC | C(C)OC=1C=C(C=CC1OC)C(CS(=O)(=O)C)N.C(C)(=O)N[C@@H](CC(C)C)C(=O)O>>C(C)(=O)N[C@@H](CC(C)C)C(=O)O.C(C)OC=1C=C(C=CC1OC)[C@@H](CS(=O)(=O)C)N | [CH3:13][CH2:14][O:15][c:16]1[cH:17][c:18]([CH:19]([NH2:20])[CH2:21][S:22]([CH3:23])(=[O:24])=[O:25])[cH:26][cH:27][c:28]1[O:29][CH3:30]>>[CH3:13][CH2:14][O:15][c:16]1[cH:17][c:18]([C@H:19]([NH2:20])[CH2:21][S:22]([CH3:23])(=[O:24])=[O:25])[cH:26][cH:27][c:28]1[O:29][CH3:30] | CCOc1cc(C(N)CS(C)(=O)=O)ccc1OC | CCOc1cc([C@H](N)CS(C)(=O)=O)ccc1OC | null | null | CO | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | c1ccccc1 | null | 90 | [{"value": 90.0, "product": "C(C)(=O)N[C@@H](CC(C)C)C(=O)O.C(C)OC=1C=C(C=CC1OC)[C@@H](CS(=O)(=O)C)N", "details": "PERCENTYIELD", "is_desired": false}, {"value": 37.0, "product": "C(C)(=O)N[C@@H](CC(C)C)C(=O)O.C(C)OC=1C=C(C=CC1OC)[C@@H](CS(=O)(=O)C)N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | A 3 L 3-necked round bottom flask was equipped with a mechanical stirrer, thermometer, and condenser and charged with 2-(3-ethoxy-4-methoxyphenyl)-1-(methylsulphonyl)-eth-2-ylamine (137.0 g, 500 mmol), N-acetyl-L-leucine (52 g, 300 mmol), and methanol (1.0 L). The stirred slurry was heated to reflux for 1 hour. The sti... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | c1ccccc1 | null | CO | null | 3 | CCOc1cc(C(N)CS(C)(=O)=O)ccc1OC>CO>CCOc1cc([C@H](N)CS(C)(=O)=O)ccc1OC |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a99944e743914f408ab0c52108d16f81 | CC(=O)Nc1cccc2c1C(=O)OC2=O.CCOc1cc([C@H](N)CS(C)(=O)=O)ccc1OC>>CCOc1cc(C(CS(C)(=O)=O)N2C(=O)c3cccc(N)c3C2=O)ccc1OC | C(C)(=O)N[C@@H](CC(C)C)C(=O)O.C(C)OC=1C=C(C=CC1OC)[C@@H](CS(=O)(=O)C)N.C(C)(=O)NC1=C2C(C(=O)OC2=O)=CC=C1>>C(C)OC=1C=C(C=CC1OC)C(CS(=O)(=O)C)N1C(C2=CC=CC(=C2C1=O)N)=O | CC(=O)[NH:21][c:20]1[cH:19][cH:18][cH:17][c:16]2[c:22]1[C:23](=[O:24])O[C:14]2=[O:15].[CH3:1][CH2:2][O:3][c:4]1[cH:5][c:6]([C@@H:7]([CH2:8][S:9]([CH3:10])(=[O:11])=[O:12])[NH2:13])[cH:25][cH:26][c:27]1[O:28][CH3:29]>>[CH3:1][CH2:2][O:3][c:4]1[cH:5][c:6]([CH:7]([CH2:8][S:9]([CH3:10])(=[O:11])=[O:12])[N:13]2[C:14](=[O:15... | CC(=O)Nc1cccc2c1C(=O)OC2=O.CCOc1cc([C@H](N)CS(C)(=O)=O)ccc1OC | CCOc1cc(C(CS(C)(=O)=O)N2C(=O)c3cccc(N)c3C2=O)ccc1OC | null | null | C(C)(=O)O | Acylation | OtherReaction | 3fcce89fe65d3a59d909d36c6ff10c55d9a99436771d834354e62b57b35184a8 | 0a142f4ab6dc4e530e33b11a80b96ebde5221dc70ae5f3a91acd13dfc0df8a03 | O=C1c2ccccc2C(=O)N1Cc1ccccc1 | C-C(=O)-[NH;D2;+0:1]-[c:2](:[c:3]):[c:4]1:[c:5](:[c:6])-[C;H0;D3;+0:7](=[O;D1;H0:8])-O-[C;H0;D3;+0:9]-1=[O;D1;H0:10].[#16:11]-[C:12]-[C@@H;D3;+0:13](-[NH2;D1;+0:14])-[c:15](:[c:16]):[c:17]>>[#16:11]-[C:12]-[CH;D3;+0:13](-[N;H0;D3;+0:14]1-[C;H0;D3;+0:7](=[O;D1;H0:8])-[c:5](:[c:6]):[c:4](:[c:2](-[NH2;D1;+0:1]):[c:3])-[C;... | 82.8 | [{"value": 75.0, "product": "C(C)OC=1C=C(C=CC1OC)C(CS(=O)(=O)C)N1C(C2=CC=CC(=C2C1=O)N)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 82.8, "product": "C(C)OC=1C=C(C=CC1OC)C(CS(=O)(=O)C)N1C(C2=CC=CC(=C2C1=O)N)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A 500 mL 3-necked round bottom flask was equipped with a mechanical stirrer, thermometer, and condenser. The reaction vessel was charged with (S)-2-(3-ethoxy-4-methoxyphenyl)-1-(methylsulphonyl)-eth-2-yl amine N-acetyl-L-leucine salt (25 g, 56 mmol, 98% ee), 3-acetamidophthalic anhydride (12.1 g 58.8 mmol), and glacial... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Ester.Ester.Secondary amide.Primary amine | Substituted dicarboximide.Primary amine | c1ccc2c(c1)COC2 | c1ccc2c(c1)C[NH]C2 | c1ccccc1.c1ccc2c(c1)C[NH]C2 | HO- | C(C)(=O)O | null | null | CC(=O)Nc1cccc2c1C(=O)OC2=O.CCOc1cc([C@H](N)CS(C)(=O)=O)ccc1OC>C(C)(=O)O>CCOc1cc(C(CS(C)(=O)=O)N2C(=O)c3cccc(N)c3C2=O)ccc1OC |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-25375e3403b849d89b8e5f17ac754ba2 | CC(=O)OC(C)=O.Oc1cccc(Cl)c1>>CC(=O)Oc1cccc(Cl)c1 | ClC=1C=C(C=CC1)O.C(C)(=O)OC(C)=O.[Na]>>C(C)(=O)OC1=CC(=CC=C1)Cl | CC(=O)O[C:2]([CH3:1])=[O:3].[OH:4][c:5]1[cH:6][cH:7][cH:8][c:9]([Cl:10])[cH:11]1>>[CH3:1][C:2](=[O:3])[O:4][c:5]1[cH:6][cH:7][cH:8][c:9]([Cl:10])[cH:11]1 | CC(=O)OC(C)=O.Oc1cccc(Cl)c1 | CC(=O)Oc1cccc(Cl)c1 | null | S(O)(O)(=O)=O | null | Acylation | Acetic anhydride and alcohol to ester | 55f321cc520ab80a97c517ea4db1ffe6ba0ea312e2db70f74b0966421bec0a44 | 96218bff9f96200922f4dff3481116557fe6986cba41ef7bff8cc8a0b43bd224 | c1ccccc1 | C-C(=O)-O-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[OH;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[C;D1;H3:2]-[C;H0;D3;+0:1](=[O;D1;H0:3])-[O;H0;D2;+0:4]-[c:5](:[c:6]):[c:7] | null | [] | 120 | CELSIUS | 45 | MINUTE | 3-Chlorophenol (100 g, 0.78 mol) was dissolved in acetic anhydride (75 mL, 0.8 mol). Upon addition of 1 drop of concentrated sulfuric acid, the temperature raised to 120° C. After 45 minutes, the mixture was cooled and poured into a solution of sodium hydrogenocarbonate (8 g in 1 L of water) and extracted with diethyle... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Aromatic alcohol | Ester | null | null | c1ccccc1 | HO- | S(O)(O)(=O)=O | 120 | 0.75 | CC(=O)OC(C)=O.Oc1cccc(Cl)c1>S(O)(O)(=O)=O>CC(=O)Oc1cccc(Cl)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-4d56cf976bb44648b361f8bf4ea541af | CC(=O)c1ccc(Cl)cc1O.CC(C)=O>>CC1(C)CC(=O)c2ccc(Cl)cc2O1 | CC(=O)C1=C(C=C(C=C1)Cl)O.CC(=O)C.N1CCCC1>>ClC1=CC2=C(C(CC(O2)(C)C)=O)C=C1 | [CH3:4][C:5](=[O:6])[c:7]1[cH:8][cH:9][c:10]([Cl:11])[cH:12][c:13]1[OH:14].O=[C:2]([CH3:1])[CH3:3]>>[CH3:1][C:2]1([CH3:3])[CH2:4][C:5](=[O:6])[c:7]2[cH:8][cH:9][c:10]([Cl:11])[cH:12][c:13]2[O:14]1 | CC(=O)c1ccc(Cl)cc1O.CC(C)=O | CC1(C)CC(=O)c2ccc(Cl)cc2O1 | null | null | CO | Heteroatom Alkylation and Arylation | OtherReaction | 177c53c6f229e3255e30105214dd5c7935fd1f18d03e441505a34379447ca7ce | 2b19ddad93f276f7cba72518a5f5b44fb4fd6e49b358f1173e7b2c08a31b3f60 | O=C1CCOc2ccccc21 | O=[C;H0;D3;+0:1](-[C;D1;H3:2])-[C;D1;H3:3].[CH3;D1;+0:4]-[C:5](=[O;D1;H0:6])-[c:7]:[c:8](-[OH;D1;+0:9]):[c:10]>>[C;D1;H3:2]-[C;H0;D4;+0:1]1(-[C;D1;H3:3])-[CH2;D2;+0:4]-[C:5](=[O;D1;H0:6])-[c:7]:[c:8](:[c:10])-[O;H0;D2;+0:9]-1 | null | [] | null | null | null | null | A solution of 4-chloro-2-hydroxyacetophenone (20 g, 0.1176 mol), acetone (13.3 mL, 0.1811 mol) and pyrrolidine (15 mL, 0.18 mol) in methanol (475 mL) was stirred at 25° C. overnight. The mixture was then concentrated to a red oil. Water was added and the solution was adjusted to pH 1 with concentrated hydrochloric acid... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ketone.Aromatic alcohol | Ketone.Ether | null | c1ccc2c(c1)CCCO2 | c1ccc2c(c1)CCCO2 | HO- | CO | null | null | CC(=O)c1ccc(Cl)cc1O.CC(C)=O>CO>CC1(C)CC(=O)c2ccc(Cl)cc2O1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-acf9316207ca49a4b73f93a9e869c50a | CC(=O)c1cc(Br)ccc1O.O=C1CCCC1>>O=C1CC2(CCCC2)Oc2ccc(Br)cc21 | CC(=O)C1=C(C=CC(=C1)Br)O.C1(CCCC1)=O.N1CCCC1>>BrC=1C=CC2=C(C(CC3(CCCC3)O2)=O)C1 | [O:1]=[C:2]([CH3:3])[c:16]1[c:10]([OH:9])[cH:11][cH:12][c:13]([Br:14])[cH:15]1.O=[C:4]1[CH2:5][CH2:6][CH2:7][CH2:8]1>>[O:1]=[C:2]1[CH2:3][C:4]2([CH2:5][CH2:6][CH2:7][CH2:8]2)[O:9][c:10]2[cH:11][cH:12][c:13]([Br:14])[cH:15][c:16]21 | CC(=O)c1cc(Br)ccc1O.O=C1CCCC1 | O=C1CC2(CCCC2)Oc2ccc(Br)cc21 | null | null | CO | Heteroatom Alkylation and Arylation | OtherReaction | 54f8457e0ef414d7ecba4bad766f9e864aebfcb56b4f48ae0699e350957831b7 | 2b19ddad93f276f7cba72518a5f5b44fb4fd6e49b358f1173e7b2c08a31b3f60 | O=C1CC2(CCCC2)Oc2ccccc21 | O=[C;H0;D3;+0:1]1-[C:2]-[C:3]-[C:4]-[C:5]-1.[CH3;D1;+0:6]-[C:7](=[O;D1;H0:8])-[c:9]:[c:10](-[OH;D1;+0:11]):[c:12]>>[O;D1;H0:8]=[C:7]1-[CH2;D2;+0:6]-[C;H0;D4;+0:1]2(-[C:2]-[C:3]-[C:4]-[C:5]-2)-[O;H0;D2;+0:11]-[c:10](:[c:12]):[c:9]-1 | null | [] | null | null | null | null | A solution of 5-bromo-2-hydroxyacetophenone (31.6 g, 0.1477 mol), cyclopentanone (26 mL, 0.2939 mol) and pyrrolidine (24 mL, 0.288 mol) in methanol (600 mL) was stirred at 25° C. overnight. The mixture was then concentrated to a red oil. Water was added and the solution was adjusted to pH 1 with concentrated hydrochlor... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ketone.Aromatic alcohol | Ketone.Ether | C1CCCC1 | c1ccc2c(c1)CCC1(CCCC1)O2 | c1ccc2c(c1)CCC1(CCCC1)O2 | HO- | CO | null | null | CC(=O)c1cc(Br)ccc1O.O=C1CCCC1>CO>O=C1CC2(CCCC2)Oc2ccc(Br)cc21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-f0f4ba2f76c247f393accfad4465076f | O=C1CC2(CCCC2)Oc2ccc(Br)cc21>>OC1CC2(CCCC2)Oc2ccc(Br)cc21 | [BH4-].[Na+].BrC=1C=CC2=C(C(CC3(CCCC3)O2)=O)C1.Cl>>BrC=1C=CC2=C(C(CC3(CCCC3)O2)O)C1 | [O:1]=[C:2]1[CH2:3][C:4]2([CH2:5][CH2:6][CH2:7][CH2:8]2)[O:9][c:10]2[cH:11][cH:12][c:13]([Br:14])[cH:15][c:16]21>>[OH:1][CH:2]1[CH2:3][C:4]2([CH2:5][CH2:6][CH2:7][CH2:8]2)[O:9][c:10]2[cH:11][cH:12][c:13]([Br:14])[cH:15][c:16]21 | O=C1CC2(CCCC2)Oc2ccc(Br)cc21 | OC1CC2(CCCC2)Oc2ccc(Br)cc21 | null | null | CO | Reduction | Reduction of ketone to secondary alcohol | eb0e0d46e51393c1b1c6557345907d37c04068e329616b7f9cbfe08d8cc38897 | 1bd3cd74b454139c0a0068ac0135836499926b274bff569df163210c6c944a89 | c1ccc2c(c1)CCC1(CCCC1)O2 | [O;H0;D1;+0:1]=[C;H0;D3;+0:2]1-[C:3]-[C:4]-[#8:5]-[c:6]:[c:7]-1:[c:8]>>[OH;D1;+0:1]-[CH;D3;+0:2]1-[C:3]-[C:4]-[#8:5]-[c:6]:[c:7]-1:[c:8] | null | [] | null | null | 30 | MINUTE | Sodium borohydride (4.65 g, 0.123 mol) was added to a stirred suspension of 6-bromo-3,4-dihydro-spiro[2H-1-benzopyran-2,1′-cyclopentan]-4-one (31.83 g, 0.1137 mol) in methanol (650 mL) at 0° C. and the mixture was maintained at this temperature for a further 30 minutes. After stirring for an additional 30 minutes at ro... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Secondary alcohol | c1ccc2c(c1)CCC1(CCCC1)O2 | c1ccc2c(c1)CCC1(CCCC1)O2 | c1ccc2c(c1)CCC1(CCCC1)O2 | null | CO | null | 0.5 | O=C1CC2(CCCC2)Oc2ccc(Br)cc21>CO>OC1CC2(CCCC2)Oc2ccc(Br)cc21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e1920ef2f02749dd94be0827329a4137 | CN(C)c1cccc(O)c1.N#CCC#N.O=Cc1ccc2c(c1)OCO2>>CN(C)c1ccc2c(c1)OC(N)=C(C#N)C2c1ccc2c(c1)OCO2 | N1CCCCC1.CN(C=1C=C(C=CC1)O)C.C1=CC2=C(C=C1C=O)OCO2.C(CC#N)#N>>NC=1OC2=CC(=CC=C2C(C1C#N)C1=CC2=C(C=C1)OCO2)N(C)C | [CH3:1][N:2]([CH3:3])[c:4]1[cH:5][cH:6][cH:7][c:8]([OH:10])[cH:9]1.[C:11](#[N:12])[CH2:13][C:14]#[N:15].O=[CH:16][c:17]1[cH:18][cH:19][c:20]2[c:21]([cH:22]1)[O:23][CH2:24][O:25]2>>[CH3:1][N:2]([CH3:3])[c:4]1[cH:5][cH:6][c:7]2[c:8]([cH:9]1)[O:10][C:11]([NH2:12])=[C:13]([C:14]#[N:15])[CH:16]2[c:17]1[cH:18][cH:19][c:20]2[... | CN(C)c1cccc(O)c1.N#CCC#N.O=Cc1ccc2c(c1)OCO2 | CN(C)c1ccc2c(c1)OC(N)=C(C#N)C2c1ccc2c(c1)OCO2 | null | null | C(C)O | Acylation | OtherReaction | 49e188f97b5969b9740a7436492b0baaa1bf2e17f3288b4209ac7db1391444e0 | b60f684fc894decc11bc6e0a45d6754f936c8349174c81d94024a37d26dffaa5 | C1=CC(c2ccc3c(c2)OCO3)c2ccccc2O1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[N;D1;H0:5]#[C:6]-[CH2;D2;+0:7]-[C;H0;D2;+0:8]#[N;H0;D1;+0:9].[OH;D1;+0:10]-[c:11](:[c:12]):[cH;D2;+0:13]:[c:14]:[c:15]>>[N;D1;H0:5]#[C:6]-[C;H0;D3;+0:7]1=[C;H0;D3;+0:8](-[NH2;D1;+0:9])-[O;H0;D2;+0:10]-[c:11](:[c:12]):[c;H0;D3;+0:13](:[c:14]:[c:15])-[CH;D3;+0:1]-1-[c:2](:[c:3]):[c:4] | 79.3 | [{"value": 79.0, "product": "NC=1OC2=CC(=CC=C2C(C1C#N)C1=CC2=C(C=C1)OCO2)N(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 79.3, "product": "NC=1OC2=CC(=CC=C2C(C1C#N)C1=CC2=C(C=C1)OCO2)N(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | To a mixture of 3-dimethylaminophenol (489 mg, 3.56 mmol), piperonal (535 mg, 3.56 mmol), and malononitrile (233 mg, 3.53 mmol) in ethanol (20 ml) was added piperidine (0.70 ml, 7.1 mmol). The mixture was stirred at room temperature for 2 h and the resulting solid was collected by filtration, washed with methanol and d... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Nitrile.Aromatic alcohol | Enamine.Ether | c1ccccc1 | C1=COc2ccccc2C1 | C1=COc2ccccc2C1.c1ccc2c(c1)OCO2 | HO- | C(C)O | null | 2 | CN(C)c1cccc(O)c1.N#CCC#N.O=Cc1ccc2c(c1)OCO2>C(C)O>CN(C)c1ccc2c(c1)OC(N)=C(C#N)C2c1ccc2c(c1)OCO2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e966886be5474db9aad6c3016524dfe8 | CCC(=O)Cl.CN(C)c1ccc2c(c1)OC(N)=C(C#N)C2c1ccc2c(c1)OCO2>>CCC(=O)NC1=C(C#N)C(c2ccc3c(c2)OCO3)c2ccc(N(C)C)cc2O1 | C(CC)(=O)Cl.NC=1OC2=CC(=CC=C2C(C1C#N)C1=CC2=C(C=C1)OCO2)N(C)C.N1=CC=CC=C1>>C(#N)C1=C(OC2=CC(=CC=C2C1C1=CC2=C(C=C1)OCO2)N(C)C)NC(CC)=O | Cl[C:3]([CH2:2][CH3:1])=[O:4].[NH2:5][C:6]1=[C:7]([C:8]#[N:9])[CH:10]([c:11]2[cH:12][cH:13][c:14]3[c:15]([cH:16]2)[O:17][CH2:18][O:19]3)[c:20]2[cH:21][cH:22][c:23]([N:24]([CH3:25])[CH3:26])[cH:27][c:28]2[O:29]1>>[CH3:1][CH2:2][C:3](=[O:4])[NH:5][C:6]1=[C:7]([C:8]#[N:9])[CH:10]([c:11]2[cH:12][cH:13][c:14]3[c:15]([cH:16]... | CCC(=O)Cl.CN(C)c1ccc2c(c1)OC(N)=C(C#N)C2c1ccc2c(c1)OCO2 | CCC(=O)NC1=C(C#N)C(c2ccc3c(c2)OCO3)c2ccc(N(C)C)cc2O1 | null | null | ClCCl.CCCCCC.CCOC(=O)C | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 67a4a916abe1047968b46c9f8f63822c89bf28a1a4f499fb1f5fb567edb4070f | 178c607e9acb60b2ba315fc0f5a1f8155b3bc47827f60f3f62cd4667d5360363 | C1=CC(c2ccc3c(c2)OCO3)c2ccccc2O1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C;D1;H3:4].[C:5]-[C:6](-[C:7]#[N;D1;H0:8])=[C:9](-[NH2;D1;+0:10])-[#8:11]-[c:12]>>[C:5]-[C:6](-[C:7]#[N;D1;H0:8])=[C:9](-[NH;D2;+0:10]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C;D1;H3:4])-[#8:11]-[c:12] | 14 | [{"value": 14.0, "product": "C(#N)C1=C(OC2=CC(=CC=C2C1C1=CC2=C(C=C1)OCO2)N(C)C)NC(CC)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 4 | HOUR | To a solution of 2-amino-3-cyano-7-dimethylamino-4-(3,4-methylenedioxyphenyl)-4H-chromene (102 mg, 0.30 mmol) in dichloromethane (5 ml) was added pyridine (0.7 ml) at 0° C., followed by propionyl chloride (0.3 ml). The mixture was then stirred at room temperature for 4 h, diluted with 1:1 hexane/EtOAc (80 ml), washed w... | 10.6084/m9.figshare.5104873.v1 | null | Enamine.Acyl halide | Enamine.Secondary amide | null | null | c1ccc2c(c1)OCO2.C1=COc2ccccc2C1 | HCl | ClCCl.CCCCCC.CCOC(=O)C | null | 4 | CCC(=O)Cl.CN(C)c1ccc2c(c1)OC(N)=C(C#N)C2c1ccc2c(c1)OCO2>ClCCl.CCCCCC.CCOC(=O)C>CCC(=O)NC1=C(C#N)C(c2ccc3c(c2)OCO3)c2ccc(N(C)C)cc2O1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-b317cfc19b124188b1c578197f6f698d | COc1cc(C2c3ccc(N(C)C)cc3OC(=N)C2C(=O)c2ccccc2)cc2c1OCO2>>COc1cc(C2C(C(=O)c3ccccc3)=C(N)Oc3cc(N(C)C)ccc32)cc2c1OCO2 | N=C1OC2=CC(=CC=C2C(C1C(C1=CC=CC=C1)=O)C1=CC(=C2C(=C1)OCO2)OC)N(C)C.C(C)N(CC)CC>>NC=1OC2=CC(=CC=C2C(C1C(C1=CC=CC=C1)=O)C1=CC(=C2C(=C1)OCO2)OC)N(C)C | [CH3:1][O:2][c:3]1[cH:4][c:5]([CH:6]2[CH:7]([C:8](=[O:9])[c:10]3[cH:11][cH:12][cH:13][cH:14][cH:15]3)[C:16](=[NH:17])[O:18][c:19]3[cH:20][c:21]([N:22]([CH3:23])[CH3:24])[cH:25][cH:26][c:27]32)[cH:28][c:29]2[c:30]1[O:31][CH2:32][O:33]2>>[CH3:1][O:2][c:3]1[cH:4][c:5]([CH:6]2[C:7]([C:8](=[O:9])[c:10]3[cH:11][cH:12][cH:13]... | COc1cc(C2c3ccc(N(C)C)cc3OC(=N)C2C(=O)c2ccccc2)cc2c1OCO2 | COc1cc(C2C(C(=O)c3ccccc3)=C(N)Oc3cc(N(C)C)ccc32)cc2c1OCO2 | null | null | C(C)O | Miscellaneous | OtherReaction | 45ba87f560add860ec82d3f9c1a75167fdb400737f2ecedb227dc87b5a69340d | bf7f1a19d2e8b1324c5e79c8242a88993bcd0e4d5a562c8fd4c9cc645aa5a46d | O=C(C1=COc2ccccc2C1c1ccc2c(c1)OCO2)c1ccccc1 | [NH;D1;+0:1]=[C;H0;D3;+0:2]1-[#8:3]-[c:4]:[c:5]-[C:6](-[c:7])-[CH;D3;+0:8]-1-[C:9](=[O;D1;H0:10])-[c:11]>>[NH2;D1;+0:1]-[C;H0;D3;+0:2]1=[C;H0;D3;+0:8](-[C:9](=[O;D1;H0:10])-[c:11])-[C:6](-[c:7])-[c:5]:[c:4]-[#8:3]-1 | 72 | [{"value": 72.0, "product": "NC=1OC2=CC(=CC=C2C(C1C(C1=CC=CC=C1)=O)C1=CC(=C2C(=C1)OCO2)OC)N(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 68.6, "product": "NC=1OC2=CC(=CC=C2C(C1C(C1=CC=CC=C1)=O)C1=CC(=C2C(=C1)OCO2)OC)N(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 2-imino-3-benzoyl-7-dimethylamino-4-(3-methoxy-4,5-methylenedioxyphenyl)-chromane (26 mg, 0.059 mmol) and triethylamine (0.1 ml) in ethanol (5 ml) was refluxed for 12 h. It was concentrated, and the residue was purified by column chromatography (silica gel, EtOAc/Hexane=1:5) to give 18 mg (72%) of the tit... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ether | Enamine | c1ccc2c(c1)CCCO2 | C1=COc2ccccc2C1 | c1ccccc1.C1=COc2ccccc2C1.c1ccc2c(c1)OCO2 | null | C(C)O | null | null | COc1cc(C2c3ccc(N(C)C)cc3OC(=N)C2C(=O)c2ccccc2)cc2c1OCO2>C(C)O>COc1cc(C2C(C(=O)c3ccccc3)=C(N)Oc3cc(N(C)C)ccc32)cc2c1OCO2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d27353f34a1b4168a72fadcaff16e6f7 | CC(=O)OC(C)=O.CN(C)c1ccc2c(c1)OC(c1cc3c(c(C#N)c1N)OCO3)=CC2>>CC(=O)Nc1c(C2=CCc3ccc(N(C)C)cc3O2)cc2c(c1C#N)OCO2 | NC1=C(C=C2C(=C1C#N)OCO2)C=2OC1=CC(=CC=C1CC2)N(C)C.C(C)(=O)OC(C)=O>>C(C)(=O)NC1=C(C=C2C(=C1C#N)OCO2)C=2OC1=CC(=CC=C1CC2)N(C)C | CC(=O)O[C:2]([CH3:1])=[O:3].[NH2:4][c:5]1[c:6]([C:7]2=[CH:8][CH2:9][c:10]3[cH:11][cH:12][c:13]([N:14]([CH3:15])[CH3:16])[cH:17][c:18]3[O:19]2)[cH:20][c:21]2[c:22]([c:23]1[C:24]#[N:25])[O:26][CH2:27][O:28]2>>[CH3:1][C:2](=[O:3])[NH:4][c:5]1[c:6]([C:7]2=[CH:8][CH2:9][c:10]3[cH:11][cH:12][c:13]([N:14]([CH3:15])[CH3:16])[c... | CC(=O)OC(C)=O.CN(C)c1ccc2c(c1)OC(c1cc3c(c(C#N)c1N)OCO3)=CC2 | CC(=O)Nc1c(C2=CCc3ccc(N(C)C)cc3O2)cc2c(c1C#N)OCO2 | null | null | N1=CC=CC=C1.CCCCCC.CCOC(=O)C | Acylation | Aminolysis of esters | 87d35e51b477fc9a658a6f307eb56d84c8879182772c9dd3a42ec0d584fd2684 | 627cbc0550c9f51ad0105d9fcf46677e8c93bed87ee95bfe69292a82550c95b7 | C1=C(c2ccc3c(c2)OCO3)Oc2ccccc2C1 | C-C(=O)-O-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[C:4]=[C:5]-[c:6]:[c:7](-[NH2;D1;+0:8]):[c:9]>>[C:4]=[C:5]-[c:6]:[c:7](-[NH;D2;+0:8]-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3]):[c:9] | 8.2 | [{"value": 8.0, "product": "C(C)(=O)NC1=C(C=C2C(=C1C#N)OCO2)C=2OC1=CC(=CC=C1CC2)N(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 8.2, "product": "C(C)(=O)NC1=C(C=C2C(=C1C#N)OCO2)C=2OC1=CC(=CC=C1CC2)N(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | DAY | To a solution of 2-amino-3-cyano-7-dimethylamino-4-(methylenedioxy)phenyl-4H-chromene (43 mg, 0.13 mmol) in pyridine (1 ml) was added acetic anhydride (0.25 ml, 2.6 mmol) at room temperature. The mixture was stirred at room temperature for 3 days, then diluted with 1:1 hexane/EtOAc (40 ml), washed with water, 2N HCl, w... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Primary amine | Secondary amide | null | null | C1=COc2ccccc2C1.c1ccc2c(c1)OCO2 | HO- | N1=CC=CC=C1.CCCCCC.CCOC(=O)C | null | 72 | CC(=O)OC(C)=O.CN(C)c1ccc2c(c1)OC(c1cc3c(c(C#N)c1N)OCO3)=CC2>N1=CC=CC=C1.CCCCCC.CCOC(=O)C>CC(=O)Nc1c(C2=CCc3ccc(N(C)C)cc3O2)cc2c(c1C#N)OCO2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-c18e14163bca4fb3aaa3287112574a66 | CCOC(=O)Cl.CCOC(C)=O.CN(C)c1ccc2c(c1)OC(c1cc3c(c(C#N)c1N)OCO3)=CC2>>CCOC(=O)N(C(=O)OCC)c1c(C2=CCc3ccc(N(C)C)cc3O2)cc2c(c1C#N)OCO2 | CCCCCC.CCOC(=O)C.C(C)OC(=O)Cl.NC1=C(C=C2C(=C1C#N)OCO2)C=2OC1=CC(=CC=C1CC2)N(C)C.N1=CC=CC=C1>>C(#N)C=1C(=C(C=C2C1OCO2)C=2OC1=CC(=CC=C1CC2)N(C)C)N(C(=O)OCC)C(=O)OCC | Cl[C:7](=[O:8])[O:9][CH2:10][CH3:11].C[C:4]([O:3][CH2:2][CH3:1])=[O:5].[NH2:6][c:12]1[c:13]([C:14]2=[CH:15][CH2:16][c:17]3[cH:18][cH:19][c:20]([N:21]([CH3:22])[CH3:23])[cH:24][c:25]3[O:26]2)[cH:27][c:28]2[c:29]([c:30]1[C:31]#[N:32])[O:33][CH2:34][O:35]2>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[N:6]([C:7](=[O:8])[O:9][CH2:10][... | CCOC(=O)Cl.CCOC(C)=O.CN(C)c1ccc2c(c1)OC(c1cc3c(c(C#N)c1N)OCO3)=CC2 | CCOC(=O)N(C(=O)OCC)c1c(C2=CCc3ccc(N(C)C)cc3O2)cc2c(c1C#N)OCO2 | null | null | C(Cl)Cl | Protection | OtherReaction | 45ee5455fcf11e0be4df85e6b2593ba4e1756b905b15ea854e46ef15b9f113b6 | 35252a2ab228bb8b20a4165ea934452c8cf7700f54d1d2284f6502617da964aa | C1=C(c2ccc3c(c2)OCO3)Oc2ccccc2C1 | C-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C:4].Cl-[C;H0;D3;+0:5](=[O;D1;H0:6])-[#8:7]-[C:8].[C:9]=[C:10]-[c:11]:[c:12](-[NH2;D1;+0:13]):[c:14]>>[C:8]-[#8:7]-[C;H0;D3;+0:5](=[O;D1;H0:6])-[N;H0;D3;+0:13](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C:4])-[c:12](:[c:14]):[c:11]-[C:10]=[C:9] | 7 | [{"value": 7.0, "product": "C(#N)C=1C(=C(C=C2C1OCO2)C=2OC1=CC(=CC=C1CC2)N(C)C)N(C(=O)OCC)C(=O)OCC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | To a solution of 2-amino-3-cyano-7-dimethylamino-4-(methylenedioxy)phenyl-4H-chromene (53 mg, 0.16 mmol) in methylenechloride (3 ml) was added pyridine (0.06 ml, 0.74 mmol), followed by ethylchloroformate (0.045 ml, 0.47 mmol). The mixture was stirred at room temperature overnight, then diluted with 1:1 hexane/EtOAc (4... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Ester.Ether.Primary amine | Carbamic ester.Carbamic ester | null | null | C1=COc2ccccc2C1.c1ccc2c(c1)OCO2 | HCl | C(Cl)Cl | null | 8 | CCOC(=O)Cl.CCOC(C)=O.CN(C)c1ccc2c(c1)OC(c1cc3c(c(C#N)c1N)OCO3)=CC2>C(Cl)Cl>CCOC(=O)N(C(=O)OCC)c1c(C2=CCc3ccc(N(C)C)cc3O2)cc2c(c1C#N)OCO2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-201c08821a414945bd087660652d455b | COc1cc(C2C(C#N)=C(N)Oc3cc(N)ccc32)cc(Br)c1OC.O=C(Cl)CCl>>COc1cc(C2C(C#N)=C(N)Oc3cc(NC(=O)CCl)ccc32)cc(Br)c1OC | ClCC(=O)Cl.NC=1OC2=CC(=CC=C2C(C1C#N)C1=CC(=C(C(=C1)OC)OC)Br)N.C(C)(C)N(C(C)C)CC>>NC=1OC2=CC(=CC=C2C(C1C#N)C1=CC(=C(C(=C1)OC)OC)Br)NC(CCl)=O | [CH3:1][O:2][c:3]1[cH:4][c:5]([CH:6]2[C:7]([C:8]#[N:9])=[C:10]([NH2:11])[O:12][c:13]3[cH:14][c:15]([NH2:16])[cH:21][cH:22][c:23]32)[cH:24][c:25]([Br:26])[c:27]1[O:28][CH3:29].Cl[C:17](=[O:18])[CH2:19][Cl:20]>>[CH3:1][O:2][c:3]1[cH:4][c:5]([CH:6]2[C:7]([C:8]#[N:9])=[C:10]([NH2:11])[O:12][c:13]3[cH:14][c:15]([NH:16][C:17... | COc1cc(C2C(C#N)=C(N)Oc3cc(N)ccc32)cc(Br)c1OC.O=C(Cl)CCl | COc1cc(C2C(C#N)=C(N)Oc3cc(NC(=O)CCl)ccc32)cc(Br)c1OC | null | null | ClCCl.O.C(C)(=O)OCC | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | C1=CC(c2ccccc2)c2ccccc2O1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[Cl;D1;H0:4].[NH2;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[Cl;D1;H0:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:5]-[c:6](:[c:7]):[c:8] | 24 | [{"value": 24.0, "product": "NC=1OC2=CC(=CC=C2C(C1C#N)C1=CC(=C(C(=C1)OC)OC)Br)NC(CCl)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | To a solution of 2,7-diamino-3-cyano-4-(3-bromo-4,5-dimethoxy phenyl)-4H-chromene (50 mg, 0.124 mmol) in dichloromethane (2 ml) was added N,N-diisopropylethylamine (0.043 ml, 0.247 mmol). The flask was cooled in iced water and a solution of chloroacetyl chloride (14 mg, 0.124 mmol) in dichloromethane (1 ml) was added d... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccccc1.C1=COc2ccccc2C1 | HCl | ClCCl.O.C(C)(=O)OCC | null | 3 | COc1cc(C2C(C#N)=C(N)Oc3cc(N)ccc32)cc(Br)c1OC.O=C(Cl)CCl>ClCCl.O.C(C)(=O)OCC>COc1cc(C2C(C#N)=C(N)Oc3cc(NC(=O)CCl)ccc32)cc(Br)c1OC |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-2ff9eab2003048e3b6321905acbed681 | COc1cc(C2C(C#N)=C(N)Oc3cc(N(C)C)ccc32)cc(Br)c1OC.O=C(Cl)CCl>>COc1cc(C2C(C#N)=C(NC(=O)CCl)Oc3cc(N(C)C)ccc32)cc(Br)c1OC | NC=1OC2=CC(=CC=C2C(C1C#N)C1=CC(=C(C(=C1)OC)OC)Br)N(C)C.ClCC(=O)Cl>>ClCC(=O)NC=1OC2=CC(=CC=C2C(C1C#N)C1=CC(=C(C(=C1)OC)OC)Br)N(C)C | [CH3:1][O:2][c:3]1[cH:4][c:5]([CH:6]2[C:7]([C:8]#[N:9])=[C:10]([NH2:11])[O:16][c:17]3[cH:18][c:19]([N:20]([CH3:21])[CH3:22])[cH:23][cH:24][c:25]32)[cH:26][c:27]([Br:28])[c:29]1[O:30][CH3:31].Cl[C:12](=[O:13])[CH2:14][Cl:15]>>[CH3:1][O:2][c:3]1[cH:4][c:5]([CH:6]2[C:7]([C:8]#[N:9])=[C:10]([NH:11][C:12](=[O:13])[CH2:14][C... | COc1cc(C2C(C#N)=C(N)Oc3cc(N(C)C)ccc32)cc(Br)c1OC.O=C(Cl)CCl | COc1cc(C2C(C#N)=C(NC(=O)CCl)Oc3cc(N(C)C)ccc32)cc(Br)c1OC | null | null | null | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 67a4a916abe1047968b46c9f8f63822c89bf28a1a4f499fb1f5fb567edb4070f | 178c607e9acb60b2ba315fc0f5a1f8155b3bc47827f60f3f62cd4667d5360363 | C1=CC(c2ccccc2)c2ccccc2O1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[Cl;D1;H0:4].[C:5]-[C:6](-[C:7]#[N;D1;H0:8])=[C:9](-[NH2;D1;+0:10])-[#8:11]-[c:12]>>[C:5]-[C:6](-[C:7]#[N;D1;H0:8])=[C:9](-[NH;D2;+0:10]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[Cl;D1;H0:4])-[#8:11]-[c:12] | null | [] | null | null | null | null | The title compound was prepared from 2-amino-3-cyano-7-dimethylamino-4-(3-bromo-4,5-dimethoxyphenyl)-4H-chromene and chloroacetyl chloride as a yellow solid by a procedure similar to that described for Example 80. 1H NMR (CDCl3): 8.26 (s, 1H), 6.97-6.80 (m, 3H), 6.50-6.46 (m, 1H), 6.33 (d, J=2.4, 1H), 4.73 (s, 3H), 4.2... | 10.6084/m9.figshare.5104873.v1 | null | Enamine.Acyl halide | Enamine.Secondary amide | null | null | c1ccccc1.C1=COc2ccccc2C1 | HCl | null | null | null | COc1cc(C2C(C#N)=C(N)Oc3cc(N(C)C)ccc32)cc(Br)c1OC.O=C(Cl)CCl>>COc1cc(C2C(C#N)=C(NC(=O)CCl)Oc3cc(N(C)C)ccc32)cc(Br)c1OC |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-562ff9997ada41358d60dd652982a399 | C=CC(=O)Cl.COc1cc(C2C(C#N)=C(N)Oc3cc(N(C)C)ccc32)cc(Br)c1OC>>C=CC(=O)NC1=C(C#N)C(c2cc(Br)c(OC)c(OC)c2)c2ccc(N(C)C)cc2O1 | NC=1OC2=CC(=CC=C2C(C1C#N)C1=CC(=C(C(=C1)OC)OC)Br)N(C)C.C(C=C)(=O)Cl>>C(C=C)(=O)NC=1OC2=CC(=CC=C2C(C1C#N)C1=CC(=C(C(=C1)OC)OC)Br)N(C)C | Cl[C:3]([CH:2]=[CH2:1])=[O:4].[NH2:5][C:6]1=[C:7]([C:8]#[N:9])[CH:10]([c:11]2[cH:12][c:13]([Br:14])[c:15]([O:16][CH3:17])[c:18]([O:19][CH3:20])[cH:21]2)[c:22]2[cH:23][cH:24][c:25]([N:26]([CH3:27])[CH3:28])[cH:29][c:30]2[O:31]1>>[CH2:1]=[CH:2][C:3](=[O:4])[NH:5][C:6]1=[C:7]([C:8]#[N:9])[CH:10]([c:11]2[cH:12][c:13]([Br:1... | C=CC(=O)Cl.COc1cc(C2C(C#N)=C(N)Oc3cc(N(C)C)ccc32)cc(Br)c1OC | C=CC(=O)NC1=C(C#N)C(c2cc(Br)c(OC)c(OC)c2)c2ccc(N(C)C)cc2O1 | null | null | null | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 67a4a916abe1047968b46c9f8f63822c89bf28a1a4f499fb1f5fb567edb4070f | 178c607e9acb60b2ba315fc0f5a1f8155b3bc47827f60f3f62cd4667d5360363 | C1=CC(c2ccccc2)c2ccccc2O1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]=[C;D1;H2:4].[C:5]-[C:6](-[C:7]#[N;D1;H0:8])=[C:9](-[NH2;D1;+0:10])-[#8:11]-[c:12]>>[C:5]-[C:6](-[C:7]#[N;D1;H0:8])=[C:9](-[NH;D2;+0:10]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]=[C;D1;H2:4])-[#8:11]-[c:12] | null | [] | null | null | null | null | The title compound was prepared from 2-amino-3-cyano-7-dimethylamino-4-(3-bromo-4,5-dimethoxyphenyl)-4H-chromene and acryloyl chloride as a yellow solid by a procedure similar to that described for Example 80. 1H NMR (CDCl3): 6.96-6.23 (m, 7H), 5.92 (d, J=10.2, 1H), 4.73 (s, 1H), 3.87 (s, 3H), 3.85 (s, 3H), 2.96 (s, 6H... | 10.6084/m9.figshare.5104873.v1 | null | Enamine.Acyl halide | Enamine.Secondary amide | null | null | c1ccccc1.C1=COc2ccccc2C1 | HCl | null | null | null | C=CC(=O)Cl.COc1cc(C2C(C#N)=C(N)Oc3cc(N(C)C)ccc32)cc(Br)c1OC>>C=CC(=O)NC1=C(C#N)C(c2cc(Br)c(OC)c(OC)c2)c2ccc(N(C)C)cc2O1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-58f8c0ca330b4f2b9b5a9aebfe77c59f | COc1cc(C2C(C#N)=C(N)Oc3cc(N(C)C)ccc32)cc(Br)c1OC.O=C(Cl)CCC(=O)Cl>>COc1cc(C2C(C#N)=C(N3C(=O)CCC3=O)Oc3cc(N(C)C)ccc32)cc(Br)c1OC | NC=1OC2=CC(=CC=C2C(C1C#N)C1=CC(=C(C(=C1)OC)OC)Br)N(C)C.C(CCC(=O)Cl)(=O)Cl>>C(#N)C1=C(OC2=CC(=CC=C2C1C1=CC(=C(C(=C1)OC)OC)Br)N(C)C)N1C(CCC1=O)=O | [CH3:1][O:2][c:3]1[cH:4][c:5]([CH:6]2[C:7]([C:8]#[N:9])=[C:10]([NH2:11])[O:18][c:19]3[cH:20][c:21]([N:22]([CH3:23])[CH3:24])[cH:25][cH:26][c:27]32)[cH:28][c:29]([Br:30])[c:31]1[O:32][CH3:33].Cl[C:12](=[O:13])[CH2:14][CH2:15][C:16](Cl)=[O:17]>>[CH3:1][O:2][c:3]1[cH:4][c:5]([CH:6]2[C:7]([C:8]#[N:9])=[C:10]([N:11]3[C:12](... | COc1cc(C2C(C#N)=C(N)Oc3cc(N(C)C)ccc32)cc(Br)c1OC.O=C(Cl)CCC(=O)Cl | COc1cc(C2C(C#N)=C(N3C(=O)CCC3=O)Oc3cc(N(C)C)ccc32)cc(Br)c1OC | null | null | null | Acylation | OtherReaction | 7d15395d78c281a9616558a40d468741555ea5d9291ddf4bae6f7b5a6f8a00d6 | 29157ec0c8fd9dbe195d2dcc3b2fc6ab025cc069cbb3df87e2beb54a124ad28f | O=C1CCC(=O)N1C1=CC(c2ccccc2)c2ccccc2O1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4]-[C;H0;D3;+0:5](-Cl)=[O;D1;H0:6].[C:7]-[C:8](-[C:9]#[N;D1;H0:10])=[C:11](-[NH2;D1;+0:12])-[#8:13]-[c:14]>>[C:7]-[C:8](-[C:9]#[N;D1;H0:10])=[C:11](-[N;H0;D3;+0:12]1-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4]-[C;H0;D3;+0:5]-1=[O;D1;H0:6])-[#8:13]-[c:14] | null | [] | null | null | null | null | The title compound was prepared from 2-amino-3-cyano-7-dimethylamino-4-(3-bromo-4,5-dimethoxyphenyl)-4H-chromene and succinyl chloride as a yellow solid by a procedure similar to that described for Example 80. 1H NMR (CDCl3): 7.12 (d, J=1.8, 1H), 6.89-6.85 (m, 2H), 6.47 (m, 1H), 6.26 (d, J=2.7, 1H), 4.79 (s, 1H), 3.87 ... | 10.6084/m9.figshare.5104873.v1 | null | Enamine.Acyl halide.Acyl halide | Enamine.Substituted dicarboximide | null | C1CC[NH]C1 | c1ccccc1.C1CC[NH]C1.C1=COc2ccccc2C1 | HCl | null | null | null | COc1cc(C2C(C#N)=C(N)Oc3cc(N(C)C)ccc32)cc(Br)c1OC.O=C(Cl)CCC(=O)Cl>>COc1cc(C2C(C#N)=C(N3C(=O)CCC3=O)Oc3cc(N(C)C)ccc32)cc(Br)c1OC |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d9a3a53e3d734a35b41bdca07ea9ab63 | COc1cc(C=O)cc(Br)c1OC.N#CCC#N.Oc1cccc2ncccc12>>COc1cc(C2C(C#N)=C(N)Oc3c2ccc2ncccc32)cc(Br)c1OC | BrC=1C(=C(C=C(C=O)C1)OC)OC.C(CC#N)#N.N1CCCCC1.OC1=C2C=CC=NC2=CC=C1.N1CCCCC1>>NC1=C(C(C2=C(O1)C=1C=CC=NC1C=C2)C2=CC(=C(C(=C2)OC)OC)Br)C#N | O=[CH:6][c:5]1[cH:4][c:3]([O:2][CH3:1])[c:26]([O:27][CH3:28])[c:24]([Br:25])[cH:23]1.[CH2:7]([C:8]#[N:9])[C:10]#[N:11].[OH:12][c:13]1[cH:14][cH:15][cH:16][c:17]2[n:18][cH:19][cH:20][cH:21][c:22]12>>[CH3:1][O:2][c:3]1[cH:4][c:5]([CH:6]2[C:7]([C:8]#[N:9])=[C:10]([NH2:11])[O:12][c:13]3[c:14]2[cH:15][cH:16][c:17]2[n:18][cH... | COc1cc(C=O)cc(Br)c1OC.N#CCC#N.Oc1cccc2ncccc12 | COc1cc(C2C(C#N)=C(N)Oc3c2ccc2ncccc32)cc(Br)c1OC | null | null | C(C)O | Acylation | OtherReaction | 8feabb3dfb0e416e3ac80df630c2adede4d565a7eb79cb5cd201fcb8127fa80c | b60f684fc894decc11bc6e0a45d6754f936c8349174c81d94024a37d26dffaa5 | C1=CC(c2ccccc2)c2ccc3ncccc3c2O1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[#7;a:5]:[c:6]1:[c:7]:[c:8]:[cH;D2;+0:9]:[c:10](-[OH;D1;+0:11]):[c:12]:1.[N;D1;H0:13]#[C:14]-[CH2;D2;+0:15]-[C;H0;D2;+0:16]#[N;H0;D1;+0:17]>>[#7;a:5]:[c:6]1:[c:7]:[c:8]:[c;H0;D3;+0:9]2:[c:10](:[c:12]:1)-[O;H0;D2;+0:11]-[C;H0;D3;+0:16](-[NH2;D1;+0:17])=[C;H0;D3;+0:15](-[C:14]#[N;D1;H0:... | 11.4 | [{"value": 11.0, "product": "NC1=C(C(C2=C(O1)C=1C=CC=NC1C=C2)C2=CC(=C(C(=C2)OC)OC)Br)C#N", "details": "PERCENTYIELD", "is_desired": false}, {"value": 11.4, "product": "NC1=C(C(C2=C(O1)C=1C=CC=NC1C=C2)C2=CC(=C(C(=C2)OC)OC)Br)C#N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 15 | MINUTE | To a mixture of 5-bromoveratraldehyde (245 mg, 1 mmol) and malononitrile (66 mg, 1 mmol) in ethanol (2 ml) was added piperidine (0.1 ml, 1 mmol). The mixture was stirred at room temperature for 15 min, then refluxed for 1 h, and cooled to room temperature. To the mixture was added piperidine (0.1 ml, 1 mmol) and 5-hydr... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Nitrile.Aromatic alcohol | Enamine.Ether | c1ccc2ncccc2c1 | C1=COc2c(ccc3ncccc23)C1 | c1ccccc1.C1=COc2c(ccc3ncccc23)C1 | HO- | C(C)O | null | 0.25 | COc1cc(C=O)cc(Br)c1OC.N#CCC#N.Oc1cccc2ncccc12>C(C)O>COc1cc(C2C(C#N)=C(N)Oc3c2ccc2ncccc32)cc(Br)c1OC |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-b282559e2fdd442e84eef5ad9ae52f05 | CCOc1cccc(O)c1.COc1cc(C=O)cc(Br)c1OC.N#CCC#N>>CCOc1ccc2c(c1)OC(N)=C(C#N)C2c1cc(Br)c(OC)c(OC)c1 | C(C)OC=1C=C(C=CC1)O.BrC=1C(=C(C=C(C=O)C1)OC)OC.C(CC#N)#N.N1CCCCC1>>NC=1OC2=CC(=CC=C2C(C1C#N)C1=CC(=C(C(=C1)OC)OC)Br)OCC | [CH3:1][CH2:2][O:3][c:4]1[cH:5][cH:6][cH:7][c:8]([OH:10])[cH:9]1.O=[CH:16][c:17]1[cH:18][c:19]([Br:20])[c:21]([O:22][CH3:23])[c:24]([O:25][CH3:26])[cH:27]1.[C:11](#[N:12])[CH2:13][C:14]#[N:15]>>[CH3:1][CH2:2][O:3][c:4]1[cH:5][cH:6][c:7]2[c:8]([cH:9]1)[O:10][C:11]([NH2:12])=[C:13]([C:14]#[N:15])[CH:16]2[c:17]1[cH:18][c:... | CCOc1cccc(O)c1.COc1cc(C=O)cc(Br)c1OC.N#CCC#N | CCOc1ccc2c(c1)OC(N)=C(C#N)C2c1cc(Br)c(OC)c(OC)c1 | null | null | C(C)O | Acylation | OtherReaction | 49e188f97b5969b9740a7436492b0baaa1bf2e17f3288b4209ac7db1391444e0 | b60f684fc894decc11bc6e0a45d6754f936c8349174c81d94024a37d26dffaa5 | C1=CC(c2ccccc2)c2ccccc2O1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[N;D1;H0:5]#[C:6]-[CH2;D2;+0:7]-[C;H0;D2;+0:8]#[N;H0;D1;+0:9].[OH;D1;+0:10]-[c:11](:[c:12]):[cH;D2;+0:13]:[c:14]:[c:15]>>[N;D1;H0:5]#[C:6]-[C;H0;D3;+0:7]1=[C;H0;D3;+0:8](-[NH2;D1;+0:9])-[O;H0;D2;+0:10]-[c:11](:[c:12]):[c;H0;D3;+0:13](:[c:14]:[c:15])-[CH;D3;+0:1]-1-[c:2](:[c:3]):[c:4] | null | [] | null | null | 15 | MINUTE | To a mixture of 5-bromoveratraldehyde (245 mg, 1 mmol) and malononitrile (66 mg, 1 mmol) in ethanol (2 ml) was added piperidine (0.1 ml, 1 mmol). The mixture was stirred at room temperature for 15 min, then 3-ethoxyphenol (138 mg, 1 mmol) was added and it was stirred overnight. The solvent was evaporated and the residu... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Nitrile.Aromatic alcohol | Enamine.Ether | c1ccccc1 | C1=COc2ccccc2C1 | C1=COc2ccccc2C1.c1ccccc1 | HO- | C(C)O | null | 0.25 | CCOc1cccc(O)c1.COc1cc(C=O)cc(Br)c1OC.N#CCC#N>C(C)O>CCOc1ccc2c(c1)OC(N)=C(C#N)C2c1cc(Br)c(OC)c(OC)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a074e92f266541c7b358a10c1af19b40 | COc1cc(C=O)cc(Br)c1OC.N#CCC#N>>COc1cc(C=C(C#N)C#N)cc(Br)c1OC | BrC=1C(=C(C=C(C=O)C1)OC)OC.C(CC#N)#N.N1CCCCC1>>COC=1C=C(C=C(C#N)C#N)C=C(C1OC)Br | O=[CH:6][c:5]1[cH:4][c:3]([O:2][CH3:1])[c:15]([O:16][CH3:17])[c:13]([Br:14])[cH:12]1.[CH2:7]([C:8]#[N:9])[C:10]#[N:11]>>[CH3:1][O:2][c:3]1[cH:4][c:5]([CH:6]=[C:7]([C:8]#[N:9])[C:10]#[N:11])[cH:12][c:13]([Br:14])[c:15]1[O:16][CH3:17] | COc1cc(C=O)cc(Br)c1OC.N#CCC#N | COc1cc(C=C(C#N)C#N)cc(Br)c1OC | null | null | C(C)O | C-C Coupling | Knoevenagel Condensation | 43d4e2f03e758941ee99f59641d5d56e6475fe935434d251d75d5cdebbe19869 | cedc9d4b791e43eacf8e7ecfa6a98d1dc0438794e96e4f1c4bef436b78f82bd8 | c1ccccc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[N;D1;H0:5]#[C:6]-[CH2;D2;+0:7]-[C:8]#[N;D1;H0:9]>>[N;D1;H0:5]#[C:6]-[C;H0;D3;+0:7](-[C:8]#[N;D1;H0:9])=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | 15 | MINUTE | To a mixture of 5-bromoveratraldehyde (245 mg, 1 mmol) and malononitrile (66 mg, 1 mmol) in ethanol was added piperidine (0.1 ml, 1 mmol). The mixture was stirred at room temperature for 15 min to give the product 3,4-dimethoxy-5-bromobenzylidenemalononitrile as a yellow precipitate.
Conditions: See reaction.notes.proc... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | null | null | null | c1ccccc1 | HO- | C(C)O | null | 0.25 | COc1cc(C=O)cc(Br)c1OC.N#CCC#N>C(C)O>COc1cc(C=C(C#N)C#N)cc(Br)c1OC |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-38a4490365184c17bf9ebd83390c64c8 | COc1cc(C=C(C#N)C#N)cc(Br)c1OC.Oc1cccc2c1CCCC2>>COc1cc(C2C(C#N)=C(N)Oc3c2ccc2c3CCCC2)cc(Br)c1OC | COC=1C=C(C=C(C#N)C#N)C=C(C1OC)Br.C1(=CC=CC=2CCCCC12)O.N1CCCCC1>>NC1=C(C(C2=C(O1)C=1CCCCC1C=C2)C2=CC(=C(C(=C2)OC)OC)Br)C#N | [CH3:1][O:2][c:3]1[cH:4][c:5]([CH:6]=[C:7]([C:8]#[N:9])[C:10]#[N:11])[cH:23][c:24]([Br:25])[c:26]1[O:27][CH3:28].[OH:12][c:13]1[cH:14][cH:15][cH:16][c:17]2[c:18]1[CH2:19][CH2:20][CH2:21][CH2:22]2>>[CH3:1][O:2][c:3]1[cH:4][c:5]([CH:6]2[C:7]([C:8]#[N:9])=[C:10]([NH2:11])[O:12][c:13]3[c:14]2[cH:15][cH:16][c:17]2[c:18]3[CH... | COc1cc(C=C(C#N)C#N)cc(Br)c1OC.Oc1cccc2c1CCCC2 | COc1cc(C2C(C#N)=C(N)Oc3c2ccc2c3CCCC2)cc(Br)c1OC | null | null | C(C)O | Acylation | OtherReaction | a94361ed2aa33ffb583f60fe41e504a358046c07f64e58249dd1f70a86e8505d | ddf492156ebbbd95b0675ccdaeb616c1c2acd58502f5ae6be273b2a40457d4ef | C1=CC(c2ccccc2)c2ccc3c(c2O1)CCCC3 | [N;D1;H0:1]#[C:2]-[C;H0;D3;+0:3](-[C;H0;D2;+0:4]#[N;H0;D1;+0:5])=[CH;D2;+0:6]-[c:7](:[c:8]):[c:9].[OH;D1;+0:10]-[c:11](:[c:12]):[cH;D2;+0:13]:[c:14]:[c:15]>>[N;D1;H0:1]#[C:2]-[C;H0;D3;+0:3]1=[C;H0;D3;+0:4](-[NH2;D1;+0:5])-[O;H0;D2;+0:10]-[c:11](:[c:12]):[c;H0;D3;+0:13](:[c:14]:[c:15])-[CH;D3;+0:6]-1-[c:7](:[c:8]):[c:9] | 1.4 | [{"value": 1.4, "product": "NC1=C(C(C2=C(O1)C=1CCCCC1C=C2)C2=CC(=C(C(=C2)OC)OC)Br)C#N", "details": "PERCENTYIELD", "is_desired": false}, {"value": 1.4, "product": "NC1=C(C(C2=C(O1)C=1CCCCC1C=C2)C2=CC(=C(C(=C2)OC)OC)Br)C#N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a stirred suspension of 3,4-dimethoxy-5-bromobenzylidenemalononitrile (293 mg, 1 mmol) and 5,6,7,8-Tetrahydro-1-naphthol (148 mg, 1 mmol) in ethanol (4 ml) was added piperidine (0.1 ml, 1 mmol), and the mixture was refluxed for 2 h. The solvent was evaporated and the residue was purified by column chromatography (Et... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile.Aromatic alcohol | Enamine.Ether | c1ccc2c(c1)CCCC2 | C1=COc2c(ccc3c2CCCC3)C1 | c1ccccc1.C1=COc2c(ccc3c2CCCC3)C1 | null | C(C)O | null | null | COc1cc(C=C(C#N)C#N)cc(Br)c1OC.Oc1cccc2c1CCCC2>C(C)O>COc1cc(C2C(C#N)=C(N)Oc3c2ccc2c3CCCC2)cc(Br)c1OC |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a7e5b2eb35eb40ad98877d39ad88aeca | COc1cc(C=C(C#N)C#N)cc(OC)c1OC.Oc1cccc2ncccc12>>COc1cc(C2C(C#N)=C(N)Oc3c2ccc2ncccc32)cc(OC)c1OC | COC=1C=C(C=C(C#N)C#N)C=C(C1OC)OC.OC1=C2C=CC=NC2=CC=C1>>NC1=C(C(C2=C(O1)C=1C=CC=NC1C=C2)C2=CC(=C(C(=C2)OC)OC)OC)C#N | [CH3:1][O:2][c:3]1[cH:4][c:5]([CH:6]=[C:7]([C:8]#[N:9])[C:10]#[N:11])[cH:23][c:24]([O:25][CH3:26])[c:27]1[O:28][CH3:29].[OH:12][c:13]1[cH:14][cH:15][cH:16][c:17]2[n:18][cH:19][cH:20][cH:21][c:22]12>>[CH3:1][O:2][c:3]1[cH:4][c:5]([CH:6]2[C:7]([C:8]#[N:9])=[C:10]([NH2:11])[O:12][c:13]3[c:14]2[cH:15][cH:16][c:17]2[n:18][c... | COc1cc(C=C(C#N)C#N)cc(OC)c1OC.Oc1cccc2ncccc12 | COc1cc(C2C(C#N)=C(N)Oc3c2ccc2ncccc32)cc(OC)c1OC | null | null | null | Acylation | OtherReaction | ea8195ef7b92aa5adf18836e24efa2282d12f28bca1973edef107593961550ee | ddf492156ebbbd95b0675ccdaeb616c1c2acd58502f5ae6be273b2a40457d4ef | C1=CC(c2ccccc2)c2ccc3ncccc3c2O1 | [#7;a:1]:[c:2]1:[c:3]:[c:4]:[cH;D2;+0:5]:[c:6](-[OH;D1;+0:7]):[c:8]:1.[N;D1;H0:9]#[C:10]-[C;H0;D3;+0:11](-[C;H0;D2;+0:12]#[N;H0;D1;+0:13])=[CH;D2;+0:14]-[c:15](:[c:16]):[c:17]>>[#7;a:1]:[c:2]1:[c:3]:[c:4]:[c;H0;D3;+0:5]2:[c:6](:[c:8]:1)-[O;H0;D2;+0:7]-[C;H0;D3;+0:12](-[NH2;D1;+0:13])=[C;H0;D3;+0:11](-[C:10]#[N;D1;H0:9]... | null | [] | null | null | null | null | The title compound was prepared from 3,4,5-trimethoxybenzylidenemalononitrile (244 mg, 1 mmol) and 5-hydroxyquinoline by a procedure similar to that described for Example 145.11H NMR (CDCl3): 8.96 (m, 1H), 8.52 (d, J=8.7, 1H), 7.82 (d, J=9.0, 1H), 7.52 (m, 1H), 7.33 (d, J=8.7, 1H), 6.43 (s, 2H), 4.83 (m, 3H), 3.83 (s, ... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile.Aromatic alcohol | Enamine.Ether | c1ccc2ncccc2c1 | C1=COc2c(ccc3ncccc23)C1 | c1ccccc1.C1=COc2c(ccc3ncccc23)C1 | null | null | null | null | COc1cc(C=C(C#N)C#N)cc(OC)c1OC.Oc1cccc2ncccc12>>COc1cc(C2C(C#N)=C(N)Oc3c2ccc2ncccc32)cc(OC)c1OC |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-dc32dab8144d4f6a9059963a3961787d | CN(C(=O)CCCCC(c1ccc(F)cc1)c1ccc(F)cc1)C1CCN(C(=O)c2ccccc2)C1>>CN(C(=O)CCCCC(c1ccc(F)cc1)c1ccc(F)cc1)[C@@H]1CCNC1 | C(C1=CC=CC=C1)(=O)N1CC(CC1)N(C(CCCCC(C1=CC=C(C=C1)F)C1=CC=C(C=C1)F)=O)C>>CN(C(CCCCC(C1=CC=C(C=C1)F)C1=CC=C(C=C1)F)=O)[C@H]1CNCC1 | O=C(c1ccccc1)[N:27]1[CH2:26][CH2:25][CH:24]([N:2]([CH3:1])[C:3](=[O:4])[CH2:5][CH2:6][CH2:7][CH2:8][CH:9]([c:10]2[cH:11][cH:12][c:13]([F:14])[cH:15][cH:16]2)[c:17]2[cH:18][cH:19][c:20]([F:21])[cH:22][cH:23]2)[CH2:28]1>>[CH3:1][N:2]([C:3](=[O:4])[CH2:5][CH2:6][CH2:7][CH2:8][CH:9]([c:10]1[cH:11][cH:12][c:13]([F:14])[cH:1... | CN(C(=O)CCCCC(c1ccc(F)cc1)c1ccc(F)cc1)C1CCN(C(=O)c2ccccc2)C1 | CN(C(=O)CCCCC(c1ccc(F)cc1)c1ccc(F)cc1)[C@@H]1CCNC1 | null | [Pd] | CO | Reduction | Hydrogenolysis of tertiary amines | f31a24fac1247652ffb9d16bd05f6451f460ef232d259564a837b8998ec61ef8 | 62cf08a8ae6315067a063b5b3495125ccbdaff6b2340ce1d3e1c7b6cde962ae4 | O=C(CCCCC(c1ccccc1)c1ccccc1)N[C@@H]1CCNC1 | O=C(-[N;H0;D3;+0:1]1-[C:2]-[C:3]-[C:4]-[C:5]-1)-c1:c:c:c:c:c:1>>[C:4]1-[C:3]-[C:2]-[NH;D2;+0:1]-[C:5]-1 | null | [] | null | null | 24 | HOUR | To a solution of 6,6-Bis-(4-fluoro-phenyl)-hexanoic acid(1-benzoyl-pyrrolidin-3-yl)-methyl amide(1.0 g, 2.1 mmol in CH3OH (50 ml) was added Pd/C 20% (250 mg). The resulting slurry was hydrogenated at 50 psi for 24 hours. The catalyst was filtered through Celite and filtrate evaporated under reduced pressure to give 0.7... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide | Secondary amine | c1ccccc1.C1CC[NH]C1 | C1CCNC1 | c1ccccc1.c1ccccc1.C1CCNC1 | HO- | [Pd].CO | null | 24 | CN(C(=O)CCCCC(c1ccc(F)cc1)c1ccc(F)cc1)C1CCN(C(=O)c2ccccc2)C1>[Pd].CO>CN(C(=O)CCCCC(c1ccc(F)cc1)c1ccc(F)cc1)[C@@H]1CCNC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-f5d8b6a413cc454b9f8f119c04545da2 | CN(C(=O)CCCCC(c1ccc(F)cc1)c1ccc(F)cc1)[C@@H]1CCNC1.COc1c(C(C)(C)C)cc(C(=O)O)cc1C(C)(C)C>>COc1c(C(C)(C)C)cc(C(=O)N2CC[C@@H](N(C)C(=O)CCCCC(c3ccc(F)cc3)c3ccc(F)cc3)C2)cc1C(C)(C)C | C(CCl)Cl.CN(C(CCCCC(C1=CC=C(C=C1)F)C1=CC=C(C=C1)F)=O)[C@H]1CNCC1.C(C)(C)(C)C=1C=C(C(=O)O)C=C(C1OC)C(C)(C)C>>C(C)(C)(C)C=1C=C(C(=O)N2C[C@@H](CC2)N(C(CCCCC(C2=CC=C(C=C2)F)C2=CC=C(C=C2)F)=O)C)C=C(C1OC)C(C)(C)C | [NH:13]1[CH2:14][CH2:15][C@@H:16]([N:17]([CH3:18])[C:19](=[O:20])[CH2:21][CH2:22][CH2:23][CH2:24][CH:25]([c:26]2[cH:27][cH:28][c:29]([F:30])[cH:31][cH:32]2)[c:33]2[cH:34][cH:35][c:36]([F:37])[cH:38][cH:39]2)[CH2:40]1.O[C:11]([c:10]1[cH:9][c:4]([C:5]([CH3:6])([CH3:7])[CH3:8])[c:3]([O:2][CH3:1])[c:42]([C:43]([CH3:44])([C... | CN(C(=O)CCCCC(c1ccc(F)cc1)c1ccc(F)cc1)[C@@H]1CCNC1.COc1c(C(C)(C)C)cc(C(=O)O)cc1C(C)(C)C | COc1c(C(C)(C)C)cc(C(=O)N2CC[C@@H](N(C)C(=O)CCCCC(c3ccc(F)cc3)c3ccc(F)cc3)C2)cc1C(C)(C)C | null | CN(C)C=1C=CN=CC1 | C(Cl)Cl | Acylation | Acylation of Nitrogen Nucleophiles by Carboxylic Acids | a590d96426a2fbaed42913d9daf8a16471a16de4978200f1d35a30a10009ebe7 | c5e4172490b2731ba9322b68af56376edadc31ce0bb9a3dfdea23a1817a852fd | O=C(CCCCC(c1ccccc1)c1ccccc1)N[C@@H]1CCN(C(=O)c2ccccc2)C1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[C:6]1-[C:7]-[C:8]-[C:9]-[NH;D2;+0:10]-1>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[N;H0;D3;+0:10]1-[C:6]-[C:7]-[C:8]-[C:9]-1)-[c:3](:[c:4]):[c:5] | 86.1 | [{"value": 86.1, "product": "C(C)(C)(C)C=1C=C(C(=O)N2C[C@@H](CC2)N(C(CCCCC(C2=CC=C(C=C2)F)C2=CC=C(C=C2)F)=O)C)C=C(C1OC)C(C)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | To a solution of (R)-6,6-Bis-(4-fluoro-phenyl)-hexanoic acid methyl-pyrrolidin-3-yl-amide (0.78 g, 2.02 mmol) in dry CH2Cl2 (30 ml) was added 3,5-di-tert-butyl-4-methoxy benzoic acid (0.53 g, 2.02 mmol) under nitrogen. To the reaction was added EDC (0.77 g, 4.04 mmol) and DMAP (cat) and the reaction mixture stirred und... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | Tertiary amide | C1CCNC1 | C1CC[NH]C1 | c1ccccc1.C1CC[NH]C1.c1ccccc1.c1ccccc1 | HO- | CN(C)C=1C=CN=CC1.C(Cl)Cl | null | 8 | CN(C(=O)CCCCC(c1ccc(F)cc1)c1ccc(F)cc1)[C@@H]1CCNC1.COc1c(C(C)(C)C)cc(C(=O)O)cc1C(C)(C)C>CN(C)C=1C=CN=CC1.C(Cl)Cl>COc1c(C(C)(C)C)cc(C(=O)N2CC[C@@H](N(C)C(=O)CCCCC(c3ccc(F)cc3)c3ccc(F)cc3)C2)cc1C(C)(C)C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a3bd9ab8933c44248386fa66145baa8d | CN(C(=O)CC(c1ccccc1)c1ccccc1)C1CCNC1.O=Cc1ccncc1>>CN(C(=O)CC(c1ccccc1)c1ccccc1)[C@@H]1CCN(Cc2ccncc2)C1 | CN(C(CC(C1=CC=CC=C1)C1=CC=CC=C1)=O)C1CNCC1.N1=CC=C(C=C1)C=O.C(C)(=O)O[BH-](OC(C)=O)OC(C)=O.[Na+]>>CN(C(CC(C1=CC=CC=C1)C1=CC=CC=C1)=O)[C@H]1CN(CC1)CC1=CC=NC=C1 | [CH3:1][N:2]([C:3](=[O:4])[CH2:5][CH:6]([c:7]1[cH:8][cH:9][cH:10][cH:11][cH:12]1)[c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1)[CH:19]1[CH2:20][CH2:21][NH:22][CH2:30]1.O=[CH:23][c:24]1[cH:25][cH:26][n:27][cH:28][cH:29]1>>[CH3:1][N:2]([C:3](=[O:4])[CH2:5][CH:6]([c:7]1[cH:8][cH:9][cH:10][cH:11][cH:12]1)[c:13]1[cH:14][cH:15... | CN(C(=O)CC(c1ccccc1)c1ccccc1)C1CCNC1.O=Cc1ccncc1 | CN(C(=O)CC(c1ccccc1)c1ccccc1)[C@@H]1CCN(Cc2ccncc2)C1 | null | null | C(Cl)Cl | Heteroatom Alkylation and Arylation | reductive amination | f320c54beea598cd731a01400cf9495fa26416685f3307ec69cb487e38cf79c3 | 2d03f38884b1fbb0c0d6e6f2de31afb25102fec87f347c3a123e064c1bfef0ad | O=C(CC(c1ccccc1)c1ccccc1)N[C@@H]1CCN(Cc2ccncc2)C1 | O=[CH;D2;+0:1]-[c:2]1:[c:3]:[c:4]:[#7;a:5]:[c:6]:[c:7]:1.[C:8]1-[C:9]-[C:10]-[NH;D2;+0:11]-[C:12]-1>>[#7;a:5]1:[c:4]:[c:3]:[c:2](-[CH2;D2;+0:1]-[N;H0;D3;+0:11]2-[C:10]-[C:9]-[C:8]-[C:12]-2):[c:7]:[c:6]:1 | null | [] | null | null | 8 | HOUR | To a solution of N-methyl-3,3-diphenyl-N-pyrrolidin-3-yl-propionamide(0.45 g, 1.46 mmol) in CH2Cl2 (10 ml) was added 4-pyridinecarboxaldehyde(0.14 ml, 1.46 mmol), sodium triacetoxyborohydride(0.4 g, 1.89 mmol) and ACOH (0.17 ml, 2.92 mmol). The resulting solution was stirred at room temperature under nitrogen overnight... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Secondary amine | Tertiary amine | C1CCNC1 | C1CC[NH]C1 | c1ccccc1.c1ccccc1.C1CC[NH]C1.c1ccncc1 | Other | C(Cl)Cl | null | 8 | CN(C(=O)CC(c1ccccc1)c1ccccc1)C1CCNC1.O=Cc1ccncc1>C(Cl)Cl>CN(C(=O)CC(c1ccccc1)c1ccccc1)[C@@H]1CCN(Cc2ccncc2)C1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-4b9b104873a24f28b297fe2e3acb4c52 | CN[C@@H]1CCN(C(=O)c2ccccc2)C1.O=C=NC(c1ccccc1)c1ccccc1>>CN(C(=O)NC(c1ccccc1)c1ccccc1)[C@@H]1CCN(Cc2ccccc2)C1 | C(C1=CC=CC=C1)(=O)N1C[C@@H](CC1)NC.C1(=CC=CC=C1)C(C1=CC=CC=C1)N=C=O>>C(C1=CC=CC=C1)(C1=CC=CC=C1)NC(N(C)[C@H]1CN(CC1)CC1=CC=CC=C1)=O | O=[C:23]([N:22]1[CH2:21][CH2:20][C@@H:19]([NH:2][CH3:1])[CH2:30]1)[c:24]1[cH:25][cH:26][cH:27][cH:28][cH:29]1.[C:3](=[O:4])=[N:5][CH:6]([c:7]1[cH:8][cH:9][cH:10][cH:11][cH:12]1)[c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1>>[CH3:1][N:2]([C:3](=[O:4])[NH:5][CH:6]([c:7]1[cH:8][cH:9][cH:10][cH:11][cH:12]1)[c:13]1[cH:14][cH:... | CN[C@@H]1CCN(C(=O)c2ccccc2)C1.O=C=NC(c1ccccc1)c1ccccc1 | CN(C(=O)NC(c1ccccc1)c1ccccc1)[C@@H]1CCN(Cc2ccccc2)C1 | null | null | C(Cl)Cl | Acylation | OtherReaction | 74260046603649fc395e9d3c55a57d192ab3ac71476c8cd70621864058712e96 | 626f1d479955946092959f41e51d9bd68cb2ca1088930412532e655b2a1d7d80 | O=C(NC(c1ccccc1)c1ccccc1)N[C@@H]1CCN(Cc2ccccc2)C1 | O=[C;H0;D3;+0:1](-[#7:2]1-[C:3]-[C:4]-[C:5](-[NH;D2;+0:6]-[C;D1;H3:7])-[C:8]-1)-[c:9](:[c:10]):[c:11].[O;D1;H0:12]=[C;H0;D2;+0:13]=[N;H0;D2;+0:14]-[C:15](-[c:16])-[c:17]>>[C;D1;H3:7]-[N;H0;D3;+0:6](-[C:5]1-[C:4]-[C:3]-[#7:2](-[CH2;D2;+0:1]-[c:9](:[c:10]):[c:11])-[C:8]-1)-[C;H0;D3;+0:13](=[O;D1;H0:12])-[NH;D2;+0:14]-[C:... | 96.8 | [{"value": 96.8, "product": "C(C1=CC=CC=C1)(C1=CC=CC=C1)NC(N(C)[C@H]1CN(CC1)CC1=CC=CC=C1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | To a solution of (R)-(1-benzoyl-pyrrolidin-3-yl)-methyl-amine(0.32 g, 1.68 mmol) in dry CH2Cl2 (5 ml) was added diphenylmethyl isocyanate(0.32 ml, 1.68 mmol) dropwise under nitrogen. The resulting mixture was stirred at room temperature overnight. Removal of solvent under reduced pressure followed by column chromatogra... | 10.6084/m9.figshare.5104873.v1 | null | Isocyanate.Tertiary amide.Secondary amine | Urea | null | null | c1ccccc1.c1ccccc1.C1CC[NH]C1.c1ccccc1 | Other | C(Cl)Cl | null | 8 | CN[C@@H]1CCN(C(=O)c2ccccc2)C1.O=C=NC(c1ccccc1)c1ccccc1>C(Cl)Cl>CN(C(=O)NC(c1ccccc1)c1ccccc1)[C@@H]1CCN(Cc2ccccc2)C1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-189f5f3cf8bb43dca2e6b5ca20960bd3 | CN(C(=O)NC(c1ccccc1)c1ccccc1)C1CCN(C(=O)c2ccccc2)C1>>CN(C(=O)NC(c1ccccc1)c1ccccc1)[C@@H]1CCNC1 | C(C1=CC=CC=C1)(C1=CC=CC=C1)NC(N(C)C1CN(CC1)C(C1=CC=CC=C1)=O)=O>>C(C1=CC=CC=C1)(C1=CC=CC=C1)NC(N([C@H]1CNCC1)C)=O | O=C(c1ccccc1)[N:22]1[CH2:21][CH2:20][CH:19]([N:2]([CH3:1])[C:3](=[O:4])[NH:5][CH:6]([c:7]2[cH:8][cH:9][cH:10][cH:11][cH:12]2)[c:13]2[cH:14][cH:15][cH:16][cH:17][cH:18]2)[CH2:23]1>>[CH3:1][N:2]([C:3](=[O:4])[NH:5][CH:6]([c:7]1[cH:8][cH:9][cH:10][cH:11][cH:12]1)[c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1)[C@@H:19]1[CH2:2... | CN(C(=O)NC(c1ccccc1)c1ccccc1)C1CCN(C(=O)c2ccccc2)C1 | CN(C(=O)NC(c1ccccc1)c1ccccc1)[C@@H]1CCNC1 | null | [Pd] | CO | Reduction | Hydrogenolysis of tertiary amines | f31a24fac1247652ffb9d16bd05f6451f460ef232d259564a837b8998ec61ef8 | 62cf08a8ae6315067a063b5b3495125ccbdaff6b2340ce1d3e1c7b6cde962ae4 | O=C(NC(c1ccccc1)c1ccccc1)N[C@@H]1CCNC1 | O=C(-[N;H0;D3;+0:1]1-[C:2]-[C:3]-[C:4]-[C:5]-1)-c1:c:c:c:c:c:1>>[C:4]1-[C:3]-[C:2]-[NH;D2;+0:1]-[C:5]-1 | 116.4 | [{"value": 116.4, "product": "C(C1=CC=CC=C1)(C1=CC=CC=C1)NC(N([C@H]1CNCC1)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 24 | HOUR | To a solution of 3-benzhydryl-1-(1-benzoyl-pyrrolidin-3-yl)-1-methyl-urea (0.7 g, 1.75 mmol) in CH3OH (25 ml) was added Pd/C 20% (175 mg). The resulting slurry was hydrogenated at 50 psi for 24 hours. The catalyst was filtered through Celite and filtrate evaporated under reduced pressure to, give 0.63 g of desired prod... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide | Secondary amine | c1ccccc1.C1CC[NH]C1 | C1CCNC1 | c1ccccc1.c1ccccc1.C1CCNC1 | HO- | [Pd].CO | null | 24 | CN(C(=O)NC(c1ccccc1)c1ccccc1)C1CCN(C(=O)c2ccccc2)C1>[Pd].CO>CN(C(=O)NC(c1ccccc1)c1ccccc1)[C@@H]1CCNC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-64ad327fd7e5418c8db679f5c0b209c6 | BrC(c1ccccc1)c1ccccc1.CN(C(=O)NC(c1ccccc1)c1ccccc1)C1CCNC1>>CN(C(=O)NC(c1ccccc1)c1ccccc1)[C@@H]1CCN(C(c2ccccc2)c2ccccc2)C1 | BrC(C1=CC=CC=C1)C1=CC=CC=C1.C(C1=CC=CC=C1)(C1=CC=CC=C1)NC(N(C1CNCC1)C)=O.C(=O)([O-])[O-].[K+].[K+]>>C(C1=CC=CC=C1)(C1=CC=CC=C1)NC(N(C)[C@H]1CN(CC1)C(C1=CC=CC=C1)C1=CC=CC=C1)=O | Br[CH:23]([c:24]1[cH:25][cH:26][cH:27][cH:28][cH:29]1)[c:30]1[cH:31][cH:32][cH:33][cH:34][cH:35]1.[CH3:1][N:2]([C:3](=[O:4])[NH:5][CH:6]([c:7]1[cH:8][cH:9][cH:10][cH:11][cH:12]1)[c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1)[CH:19]1[CH2:20][CH2:21][NH:22][CH2:36]1>>[CH3:1][N:2]([C:3](=[O:4])[NH:5][CH:6]([c:7]1[cH:8][cH:9... | BrC(c1ccccc1)c1ccccc1.CN(C(=O)NC(c1ccccc1)c1ccccc1)C1CCNC1 | CN(C(=O)NC(c1ccccc1)c1ccccc1)[C@@H]1CCN(C(c2ccccc2)c2ccccc2)C1 | null | null | CC(CC)=O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 10cc789bcfe0ae11c7b2b474c79d3cdda850354ad720004a77dedb66c0fbd515 | fb63ba09935e18320be03869002f6d5d0f0321fe7dbcd94a5ae956c3effd182d | O=C(NC(c1ccccc1)c1ccccc1)N[C@@H]1CCN(C(c2ccccc2)c2ccccc2)C1 | Br-[CH;D3;+0:1](-[c:2](:[c:3]):[c:4])-[c:5](:[c:6]):[c:7].[C:8]1-[C:9]-[C:10]-[NH;D2;+0:11]-[C:12]-1>>[c:3]:[c:2](-[CH;D3;+0:1](-[N;H0;D3;+0:11]1-[C:10]-[C:9]-[C:8]-[C:12]-1)-[c:5](:[c:6]):[c:7]):[c:4] | null | [] | null | null | null | null | To a solution of bromodiphenylmethane (0.43 g, 1.75 mmol) in butanone (10 ml) was added 3-benzhydryl-1-methyl-1-pyrrolidin-3-yl-urea(0.65 g, 2.1 mmol), K2CO3 (0.24, 1.75 mmol) and KI (0.29 g, 1.75 mmol). The mixture was heated under reflux for 18 hours, then filtered and the solvent was removed in vacuo. The residue wa... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Secondary amine | Tertiary amine | C1CCNC1 | C1CC[NH]C1 | c1ccccc1.c1ccccc1.C1CC[NH]C1.c1ccccc1.c1ccccc1 | HBr | CC(CC)=O | null | null | BrC(c1ccccc1)c1ccccc1.CN(C(=O)NC(c1ccccc1)c1ccccc1)C1CCNC1>CC(CC)=O>CN(C(=O)NC(c1ccccc1)c1ccccc1)[C@@H]1CCN(C(c2ccccc2)c2ccccc2)C1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-fa9c619af59e4c759fc0932583cffe39 | CN[C@@H]1CCN(C(=O)c2ccccc2)C1.O=C(O)CN(c1ccccc1)c1ccccc1>>CN(C(=O)CN(c1ccccc1)c1ccccc1)[C@@H]1CCN(Cc2ccccc2)C1 | C(CCl)Cl.C(C1=CC=CC=C1)(=O)N1C[C@@H](CC1)NC.C1(=CC=CC=C1)N(C1=CC=CC=C1)CC(=O)O>>C(C1=CC=CC=C1)N1C[C@@H](CC1)N(C(CN(C1=CC=CC=C1)C1=CC=CC=C1)=O)C | O=[C:23]([N:22]1[CH2:21][CH2:20][C@@H:19]([NH:2][CH3:1])[CH2:30]1)[c:24]1[cH:25][cH:26][cH:27][cH:28][cH:29]1.O[C:3](=[O:4])[CH2:5][N:6]([c:7]1[cH:8][cH:9][cH:10][cH:11][cH:12]1)[c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1>>[CH3:1][N:2]([C:3](=[O:4])[CH2:5][N:6]([c:7]1[cH:8][cH:9][cH:10][cH:11][cH:12]1)[c:13]1[cH:14][cH... | CN[C@@H]1CCN(C(=O)c2ccccc2)C1.O=C(O)CN(c1ccccc1)c1ccccc1 | CN(C(=O)CN(c1ccccc1)c1ccccc1)[C@@H]1CCN(Cc2ccccc2)C1 | null | CN(C)C=1C=CN=CC1 | C(Cl)Cl | Acylation | OtherReaction | 54b269d0f28fb1926d29899001218d7b6cda7f176425e41c60d8cf23ca5b9e74 | 66c584447dc5daff0aa8fe93aecae17349beecb2ac876e4bae5adb72d01b4bc0 | O=C(CN(c1ccccc1)c1ccccc1)N[C@@H]1CCN(Cc2ccccc2)C1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[#7:4].O=[C;H0;D3;+0:5](-[#7:6]1-[C:7]-[C:8]-[C:9](-[NH;D2;+0:10]-[C;D1;H3:11])-[C:12]-1)-[c:13](:[c:14]):[c:15]>>[#7:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[N;H0;D3;+0:10](-[C;D1;H3:11])-[C:9]1-[C:8]-[C:7]-[#7:6](-[CH2;D2;+0:5]-[c:13](:[c:14]):[c:15])-[C:12]-1 | 101.3 | [{"value": 101.3, "product": "C(C1=CC=CC=C1)N1C[C@@H](CC1)N(C(CN(C1=CC=CC=C1)C1=CC=CC=C1)=O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | To a solution of (R)-(1-benzoyl-pyrrolidin-3-yl)-methyl-amine(0.32 g, 1.68 mmol) in dry CH2Cl2 (20 ml) was added diphenylaminoacetic acid (0.38 g, 1.68 mmol) under nitrogen. To the reaction was added EDC (0.65 g, 3.36 mmol) and DMAP (cat) and the reaction mixture stirred under nitrogen at room temperature overnight. Th... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Tertiary amide.Secondary amine | Tertiary amide | null | null | c1ccccc1.c1ccccc1.C1CC[NH]C1.c1ccccc1 | Other | CN(C)C=1C=CN=CC1.C(Cl)Cl | null | 8 | CN[C@@H]1CCN(C(=O)c2ccccc2)C1.O=C(O)CN(c1ccccc1)c1ccccc1>CN(C)C=1C=CN=CC1.C(Cl)Cl>CN(C(=O)CN(c1ccccc1)c1ccccc1)[C@@H]1CCN(Cc2ccccc2)C1 |
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