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-c3a75813d0b24864aa4f7cd526efd6aa | ord-436e57e046c14b64a8417132af3d956e | CCN.O=C(O)Cc1ccc2c(c1)N(C1CCN(CCc3ccc(F)cc3)CC1)CC2>>CCNC(=O)Cc1ccc2c(c1)N(C1CCN(CCc3ccc(F)cc3)CC1)CC2 | C(=O)(N1C=NC=C1)N1C=NC=C1.FC1=CC=C(CCN2CCC(CC2)N2CCC3=CC=C(C=C23)CC(=O)O)C=C1.C([O-])(O)=O.[Na+].Cl.C(C)N>>FC1=CC=C(CCN2CCC(CC2)N2CCC3=CC=C(C=C23)CC(NCC)=O)C=C1 | [CH3:1][CH2:2][NH2:3].O[C:4](=[O:5])[CH2:6][c:7]1[cH:8][cH:9][c:10]2[c:11]([cH:12]1)[N:13]([CH:14]1[CH2:15][CH2:16][N:17]([CH2:18][CH2:19][c:20]3[cH:21][cH:22][c:23]([F:24])[cH:25][cH:26]3)[CH2:27][CH2:28]1)[CH2:29][CH2:30]2>>[CH3:1][CH2:2][NH:3][C:4](=[O:5])[CH2:6][c:7]1[cH:8][cH:9][c:10]2[c:11]([cH:12]1)[N:13]([CH:14... | CCN.O=C(O)Cc1ccc2c(c1)N(C1CCN(CCc3ccc(F)cc3)CC1)CC2 | CCNC(=O)Cc1ccc2c(c1)N(C1CCN(CCc3ccc(F)cc3)CC1)CC2 | null | null | CN(C=O)C.C(C)(=O)OCC | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | c1ccc(CCN2CCC(N3CCc4ccccc43)CC2)cc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[c:4].[C;D1;H3:5]-[C:6]-[NH2;D1;+0:7]>>[C;D1;H3:5]-[C:6]-[NH;D2;+0:7]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[c:4] | 60.7 | [{"value": 56.0, "product": "FC1=CC=C(CCN2CCC(CC2)N2CCC3=CC=C(C=C23)CC(NCC)=O)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 60.7, "product": "FC1=CC=C(CCN2CCC(CC2)N2CCC3=CC=C(C=C23)CC(NCC)=O)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | Under ice cooling, 1,1′-carbonyldiimidazole (1.0 g) was added to a solution of 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-carboxymethylindoline (2.0 g) in dimethylformamide (40 ml). After stirring the mixture for 2 hr, ethylamine hydrochloride (0.51 g) was added thereto. Then the resultant mixture was allowed to warm to... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | C1CC[NH]CC1.c1ccccc1.c1ccc2c(c1)CC[NH]2 | HO- | CN(C=O)C.C(C)(=O)OCC | null | 2 | CCN.O=C(O)Cc1ccc2c(c1)N(C1CCN(CCc3ccc(F)cc3)CC1)CC2>CN(C=O)C.C(C)(=O)OCC>CCNC(=O)Cc1ccc2c(c1)N(C1CCN(CCc3ccc(F)cc3)CC1)CC2 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-1cb140fd327d45739df3badf916eff95 | CC(C)N.O=C(O)Cc1ccc2c(c1)N(C1CCN(CCc3ccc(F)cc3)CC1)CC2>>CC(C)NC(=O)Cc1ccc2c(c1)N(C1CCN(CCc3ccc(F)cc3)CC1)CC2 | C(C)(C)N.C(=O)(N1C=NC=C1)N1C=NC=C1.FC1=CC=C(CCN2CCC(CC2)N2CCC3=CC=C(C=C23)CC(=O)O)C=C1.C(C)(=O)OCC>>FC1=CC=C(CCN2CCC(CC2)N2CCC3=CC=C(C=C23)CC(NC(C)C)=O)C=C1 | [CH3:1][CH:2]([CH3:3])[NH2:4].O[C:5](=[O:6])[CH2:7][c:8]1[cH:9][cH:10][c:11]2[c:12]([cH:13]1)[N:14]([CH:15]1[CH2:16][CH2:17][N:18]([CH2:19][CH2:20][c:21]3[cH:22][cH:23][c:24]([F:25])[cH:26][cH:27]3)[CH2:28][CH2:29]1)[CH2:30][CH2:31]2>>[CH3:1][CH:2]([CH3:3])[NH:4][C:5](=[O:6])[CH2:7][c:8]1[cH:9][cH:10][c:11]2[c:12]([cH:... | CC(C)N.O=C(O)Cc1ccc2c(c1)N(C1CCN(CCc3ccc(F)cc3)CC1)CC2 | CC(C)NC(=O)Cc1ccc2c(c1)N(C1CCN(CCc3ccc(F)cc3)CC1)CC2 | null | null | CN(C=O)C | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | c1ccc(CCN2CCC(N3CCc4ccccc43)CC2)cc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[c:4].[C;D1;H3:5]-[C:6](-[C;D1;H3:7])-[NH2;D1;+0:8]>>[C;D1;H3:5]-[C:6](-[C;D1;H3:7])-[NH;D2;+0:8]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[c:4] | 52 | [{"value": 52.0, "product": "FC1=CC=C(CCN2CCC(CC2)N2CCC3=CC=C(C=C23)CC(NC(C)C)=O)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 51.8, "product": "FC1=CC=C(CCN2CCC(CC2)N2CCC3=CC=C(C=C23)CC(NC(C)C)=O)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | Under ice cooling, 1,1′-carbonyldimidazole (15 g) was added to a solution of 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-carboxymethylindoline (30 g) in dimethylformamide (240 ml) and the resultant mixture was stirred for 2 hr. After adding isopropylamine (5.6 g), the mixture was warmed to room temperature and then stirr... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | C1CC[NH]CC1.c1ccccc1.c1ccc2c(c1)CC[NH]2 | HO- | CN(C=O)C | null | 2 | CC(C)N.O=C(O)Cc1ccc2c(c1)N(C1CCN(CCc3ccc(F)cc3)CC1)CC2>CN(C=O)C>CC(C)NC(=O)Cc1ccc2c(c1)N(C1CCN(CCc3ccc(F)cc3)CC1)CC2 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-c4b8544b77384950aec80f4d618c1cc6 | NC1CC1.O=C(O)Cc1ccc2c(c1)N(C1CCN(CCc3ccc(F)cc3)CC1)CC2>>O=C(Cc1ccc2c(c1)N(C1CCN(CCc3ccc(F)cc3)CC1)CC2)NC1CC1 | FC1=CC=C(CCN2CCC(CC2)N2CCC3=CC=C(C=C23)CC(=O)O)C=C1.C(=O)(N1C=NC=C1)N1C=NC=C1.C1(CC1)N>>FC1=CC=C(CCN2CCC(CC2)N2CCC3=CC=C(C=C23)CC(NC2CC2)=O)C=C1 | [NH2:28][CH:29]1[CH2:30][CH2:31]1.O[C:2](=[O:1])[CH2:3][c:4]1[cH:5][cH:6][c:7]2[c:8]([cH:9]1)[N:10]([CH:11]1[CH2:12][CH2:13][N:14]([CH2:15][CH2:16][c:17]3[cH:18][cH:19][c:20]([F:21])[cH:22][cH:23]3)[CH2:24][CH2:25]1)[CH2:26][CH2:27]2>>[O:1]=[C:2]([CH2:3][c:4]1[cH:5][cH:6][c:7]2[c:8]([cH:9]1)[N:10]([CH:11]1[CH2:12][CH2:... | NC1CC1.O=C(O)Cc1ccc2c(c1)N(C1CCN(CCc3ccc(F)cc3)CC1)CC2 | O=C(Cc1ccc2c(c1)N(C1CCN(CCc3ccc(F)cc3)CC1)CC2)NC1CC1 | null | null | null | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(Cc1ccc2c(c1)N(C1CCN(CCc3ccccc3)CC1)CC2)NC1CC1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[c:4].[NH2;D1;+0:5]-[C:6]1-[C:7]-[C:8]-1>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[C:3]-[c:4])-[NH;D2;+0:5]-[C:6]1-[C:7]-[C:8]-1 | 40 | [{"value": 40.0, "product": "FC1=CC=C(CCN2CCC(CC2)N2CCC3=CC=C(C=C23)CC(NC2CC2)=O)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 39.9, "product": "FC1=CC=C(CCN2CCC(CC2)N2CCC3=CC=C(C=C23)CC(NC2CC2)=O)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 1-[1-(4-Fluorophenethyl)piperidin-4-yl]-6-carboxymethylindoline (250 mg), 1,1′-carbonyldiimidazole (130 mg) and cyclopropylamine (45 mg) were treated as in Example 151 to give the title compound (110 mg) as a white powder (yield: 40%).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | C1CC[NH]CC1.c1ccccc1.c1ccc2c(c1)CC[NH]2.C1CC1 | HO- | null | null | null | NC1CC1.O=C(O)Cc1ccc2c(c1)N(C1CCN(CCc3ccc(F)cc3)CC1)CC2>>O=C(Cc1ccc2c(c1)N(C1CCN(CCc3ccc(F)cc3)CC1)CC2)NC1CC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-e3387712dca3470db68e1f996fb9dfaf | CC(C)C(=O)Cl.NCc1ccc2c(c1)N(C1CCN(CCc3ccc(F)cc3)CC1)CC2>>CC(C)C(=O)NCc1ccc2c(c1)N(C1CCN(CCc3ccc(F)cc3)CC1)CC2 | FC1=CC=C(CCN2CCC(CC2)N2CCC3=CC=C(C=C23)CN)C=C1.C(C(C)C)(=O)Cl>>FC1=CC=C(CCN2CCC(CC2)N2CCC3=CC=C(C=C23)CNC(C(C)C)=O)C=C1 | Cl[C:4]([CH:2]([CH3:1])[CH3:3])=[O:5].[NH2:6][CH2:7][c:8]1[cH:9][cH:10][c:11]2[c:12]([cH:13]1)[N:14]([CH:15]1[CH2:16][CH2:17][N:18]([CH2:19][CH2:20][c:21]3[cH:22][cH:23][c:24]([F:25])[cH:26][cH:27]3)[CH2:28][CH2:29]1)[CH2:30][CH2:31]2>>[CH3:1][CH:2]([CH3:3])[C:4](=[O:5])[NH:6][CH2:7][c:8]1[cH:9][cH:10][c:11]2[c:12]([cH... | CC(C)C(=O)Cl.NCc1ccc2c(c1)N(C1CCN(CCc3ccc(F)cc3)CC1)CC2 | CC(C)C(=O)NCc1ccc2c(c1)N(C1CCN(CCc3ccc(F)cc3)CC1)CC2 | null | null | C(C)N(CC)CC | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | c1ccc(CCN2CCC(N3CCc4ccccc43)CC2)cc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C;D1;H3:4])-[C;D1;H3:5].[NH2;D1;+0:6]-[C:7]-[c:8]>>[C;D1;H3:4]-[C:3](-[C;D1;H3:5])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:6]-[C:7]-[c:8] | 58 | [{"value": 58.0, "product": "FC1=CC=C(CCN2CCC(CC2)N2CCC3=CC=C(C=C23)CNC(C(C)C)=O)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 55.9, "product": "FC1=CC=C(CCN2CCC(CC2)N2CCC3=CC=C(C=C23)CNC(C(C)C)=O)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 1-[1-(4-Fluorophenethyl)piperidin-4-yl]-6-aminomethylindoline (300 mg), triethylamine (80 mg) and isobutyryl chloride (90 mg) were treated as in Example 133 to give the title compound (200 mg) as white needles (yield: 58%).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | C1CC[NH]CC1.c1ccccc1.c1ccc2c(c1)CC[NH]2 | HCl | C(C)N(CC)CC | null | null | CC(C)C(=O)Cl.NCc1ccc2c(c1)N(C1CCN(CCc3ccc(F)cc3)CC1)CC2>C(C)N(CC)CC>CC(C)C(=O)NCc1ccc2c(c1)N(C1CCN(CCc3ccc(F)cc3)CC1)CC2 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-ece830a4cf254389874be2a399685014 | CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[c]1nccs1.Fc1ccc(CCN2CCC(N3CCc4ccc(Br)cc43)CC2)cc1>>Fc1ccc(CCN2CCC(N3CCc4ccc(-c5nccs5)cc43)CC2)cc1 | FC1=CC=C(CCN2CCC(CC2)N2CCC3=CC=C(C=C23)Br)C=C1.C(CCC)[Sn](C=1SC=CN1)(CCCC)CCCC>>FC1=CC=C(CCN2CCC(CC2)N2CCC3=CC=C(C=C23)C=2SC=CN2)C=C1 | CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[c:19]1[n:20][cH:21][cH:22][s:23]1.Br[c:18]1[cH:17][cH:16][c:15]2[c:25]([cH:24]1)[N:12]([CH:11]1[CH2:10][CH2:9][N:8]([CH2:7][CH2:6][c:5]3[cH:4][cH:3][c:2]([F:1])[cH:29][cH:28]3)[CH2:27][CH2:26]1)[CH2:13][CH2:14]2>>[F:1][c:2]1[cH:3][cH:4][c:5]([CH2:6][CH2:7][N:8]2[CH2:9][CH2:10][CH:11]([N... | CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[c]1nccs1.Fc1ccc(CCN2CCC(N3CCc4ccc(Br)cc43)CC2)cc1 | Fc1ccc(CCN2CCC(N3CCc4ccc(-c5nccs5)cc43)CC2)cc1 | null | null | null | C-C Coupling | Stille reaction_aryl | d445b84fa2e7a1c3a57dce74bdb6063b3f9c4ca4c327b54392c55e6c4acc2917 | db27eeefac0475c6d74fa10b3167e95a61caaae74e8bbafd45892452c0c3d4d6 | c1ccc(CCN2CCC(N3CCc4ccc(-c5nccs5)cc43)CC2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5]-[#7:6].C-C-C-[CH2]-[Sn](-[CH2]-C-C-C)(-[CH2]-C-C-C)-[c;H0;D3;+0:7]1:[#16;a:8]:[c:9]:[c:10]:[#7;a:11]:1>>[#7:6]-[c:5]:[c:4]:[c;H0;D3;+0:1](-[c;H0;D3;+0:7]1:[#16;a:8]:[c:9]:[c:10]:[#7;a:11]:1):[c:2]:[c:3] | 3 | [{"value": 3.0, "product": "FC1=CC=C(CCN2CCC(CC2)N2CCC3=CC=C(C=C23)C=2SC=CN2)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 3.0, "product": "FC1=CC=C(CCN2CCC(CC2)N2CCC3=CC=C(C=C23)C=2SC=CN2)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 1-[1-(4-Fluorophenethyl)piperidin-4-yl]-6-bromoindoline (0.56 g) and 2-tributylstannylthiazole (2.778 g) synthesized in accordance with the method described in Synthesis, 757 (1986). were treated as in Production Example 13-2 to give the title compound (0.017 g) as pale yellow crystals (yield: 3.0%).
Conditions: See re... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Tin | null | c1cscn1.c1ccc2c(c1)CC[NH]2 | c1ccc2c(c1)CC[NH]2.c1cscn1 | c1ccccc1.C1CC[NH]CC1.c1ccc2c(c1)CC[NH]2.c1cscn1 | HBr.Sn | null | null | null | CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[c]1nccs1.Fc1ccc(CCN2CCC(N3CCc4ccc(Br)cc43)CC2)cc1>>Fc1ccc(CCN2CCC(N3CCc4ccc(-c5nccs5)cc43)CC2)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-dc576177fc81464e9394638c7b608ad8 | CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[c]1cccn1C.Fc1ccc(CCN2CCC(N3CCc4ccc(Br)cc43)CC2)cc1>>Cn1cccc1-c1ccc2c(c1)N(C1CCN(CCc3ccc(F)cc3)CC1)CC2 | FC1=CC=C(CCN2CCC(CC2)N2CCC3=CC=C(C=C23)Br)C=C1.CN1C(=CC=C1)[Sn](CCCC)(CCCC)CCCC>>FC1=CC=C(CCN2CCC(CC2)N2CCC3=CC=C(C=C23)C=2N(C=CC2)C)C=C1 | CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[c:6]1[n:2]([CH3:1])[cH:3][cH:4][cH:5]1.Br[c:7]1[cH:8][cH:9][c:10]2[c:11]([cH:12]1)[N:13]([CH:14]1[CH2:15][CH2:16][N:17]([CH2:18][CH2:19][c:20]3[cH:21][cH:22][c:23]([F:24])[cH:25][cH:26]3)[CH2:27][CH2:28]1)[CH2:29][CH2:30]2>>[CH3:1][n:2]1[cH:3][cH:4][cH:5][c:6]1-[c:7]1[cH:8][cH:9][c:10]2... | CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[c]1cccn1C.Fc1ccc(CCN2CCC(N3CCc4ccc(Br)cc43)CC2)cc1 | Cn1cccc1-c1ccc2c(c1)N(C1CCN(CCc3ccc(F)cc3)CC1)CC2 | null | null | null | C-C Coupling | Stille reaction_aryl | f29f53de1f28e53ad0d85a2e1503769895e07a091150ab0667f1b9ad55740490 | db27eeefac0475c6d74fa10b3167e95a61caaae74e8bbafd45892452c0c3d4d6 | c1ccc(CCN2CCC(N3CCc4ccc(-c5ccc[nH]5)cc43)CC2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]-[#7:4]):[c:5]:[c:6].C-C-C-[CH2]-[Sn](-[CH2]-C-C-C)(-[CH2]-C-C-C)-[c;H0;D3;+0:7]1:[c:8]:[c:9]:[c:10]:[#7;a:11]:1-[C;D1;H3:12]>>[#7:4]-[c:3]:[c:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:7]1:[c:8]:[c:9]:[c:10]:[#7;a:11]:1-[C;D1;H3:12]):[c:5]:[c:6] | 16 | [{"value": 15.8, "product": "FC1=CC=C(CCN2CCC(CC2)N2CCC3=CC=C(C=C23)C=2N(C=CC2)C)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 16.0, "product": "FC1=CC=C(CCN2CCC(CC2)N2CCC3=CC=C(C=C23)C=2N(C=CC2)C)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 1-[1-(4-Fluorophenethyl)piperidin-4-yl]-6-bromoindoline (0.1 g) and 1-methyl-2-tributylstannylpyrrole (0.37 g) synthesized in accordance with the method described in Tetrahedron Lett., 4407 (1986). were treated as in Production Example 13-2 to give the title compound (0.016 g) as a yellow oil (yield: 15.8%).
Conditions... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Tin | null | c1ccc[nH]1.c1ccc2c(c1)CC[NH]2 | c1ccc[nH]1.c1ccc2c(c1)CC[NH]2 | c1ccc[nH]1.C1CC[NH]CC1.c1ccccc1.c1ccc2c(c1)CC[NH]2 | HBr.Sn | null | null | null | CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[c]1cccn1C.Fc1ccc(CCN2CCC(N3CCc4ccc(Br)cc43)CC2)cc1>>Cn1cccc1-c1ccc2c(c1)N(C1CCN(CCc3ccc(F)cc3)CC1)CC2 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-bfc0cbaab805490e9e0e6d954c03d1ab | Brc1ccccn1.O=Cc1ccc2c(c1)N(C1CCN(CCc3ccc(F)cc3)CC1)CC2>>OC(c1ccc2c(c1)N(C1CCN(CCc3ccc(F)cc3)CC1)CC2)c1ccccn1 | BrC1=NC=CC=C1.FC1=CC=C(CCN2CCC(CC2)N2CCC3=CC=C(C=C23)C=O)C=C1>>FC1=CC=C(CCN2CCC(CC2)N2CCC3=CC=C(C=C23)C(C2=NC=CC=C2)O)C=C1 | Br[c:27]1[cH:28][cH:29][cH:30][cH:31][n:32]1.[O:1]=[CH:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([cH:8]1)[N:9]([CH:10]1[CH2:11][CH2:12][N:13]([CH2:14][CH2:15][c:16]3[cH:17][cH:18][c:19]([F:20])[cH:21][cH:22]3)[CH2:23][CH2:24]1)[CH2:25][CH2:26]2>>[OH:1][CH:2]([c:3]1[cH:4][cH:5][c:6]2[c:7]([cH:8]1)[N:9]([CH:10]1[CH2:11][CH2:12][N:... | Brc1ccccn1.O=Cc1ccc2c(c1)N(C1CCN(CCc3ccc(F)cc3)CC1)CC2 | OC(c1ccc2c(c1)N(C1CCN(CCc3ccc(F)cc3)CC1)CC2)c1ccccn1 | null | null | C(C)OCC | C-C Coupling | Grignard_alcohol | b19854b2eef93f01734a1ce1e1a8bde192af0da0e7ae2b2f44efcbe0d23365f0 | 1c0bd0afc1d5e370e3c8193faf738f03752295e40fa0eb99c756011e9a4be26b | c1ccc(CCN2CCC(N3CCc4ccc(Cc5ccccn5)cc43)CC2)cc1 | Br-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5].[O;H0;D1;+0:6]=[CH;D2;+0:7]-[c:8](:[c:9]):[c:10]>>[OH;D1;+0:6]-[CH;D3;+0:7](-[c:8](:[c:9]):[c:10])-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5] | 56.1 | [{"value": 56.1, "product": "FC1=CC=C(CCN2CCC(CC2)N2CCC3=CC=C(C=C23)C(C2=NC=CC=C2)O)C=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | 2-Bromopyridine (0.16 ml), 1-[1-(4-fluorophenethyl)-piperidin-4-yl]-6-formylindoline (0.5 g) and diethyl ether employed as the solvent were treated as in Example 93 to give the title compound (0.344 g) as a yellow oil (yield: 56.1%).
Conditions: See reaction.notes.procedure_details.
Workup: were treated as in Example 9... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aldehyde | Secondary alcohol | c1ccncc1 | c1ccncc1 | C1CC[NH]CC1.c1ccccc1.c1ccc2c(c1)CC[NH]2.c1ccncc1 | Br- | C(C)OCC | null | null | Brc1ccccn1.O=Cc1ccc2c(c1)N(C1CCN(CCc3ccc(F)cc3)CC1)CC2>C(C)OCC>OC(c1ccc2c(c1)N(C1CCN(CCc3ccc(F)cc3)CC1)CC2)c1ccccn1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-d5f63a48d4ca4b87914def778f1304f4 | OC(c1ccc2c(c1)N(C1CCN(CCc3ccc(F)cc3)CC1)CC2)c1ccccn1>>Fc1ccc(CCN2CCC(N3CCc4ccc(Cc5ccccn5)cc43)CC2)cc1 | FC1=CC=C(CCN2CCC(CC2)N2CCC3=CC=C(C=C23)C(C2=NC=CC=C2)O)C=C1.Cl>>FC1=CC=C(CCN2CCC(CC2)N2CCC3=CC=C(C=C23)CC2=NC=CC=C2)C=C1 | O[CH:19]([c:18]1[cH:17][cH:16][c:15]2[c:27]([cH:26]1)[N:12]([CH:11]1[CH2:10][CH2:9][N:8]([CH2:7][CH2:6][c:5]3[cH:4][cH:3][c:2]([F:1])[cH:31][cH:30]3)[CH2:29][CH2:28]1)[CH2:13][CH2:14]2)[c:20]1[cH:21][cH:22][cH:23][cH:24][n:25]1>>[F:1][c:2]1[cH:3][cH:4][c:5]([CH2:6][CH2:7][N:8]2[CH2:9][CH2:10][CH:11]([N:12]3[CH2:13][CH2... | OC(c1ccc2c(c1)N(C1CCN(CCc3ccc(F)cc3)CC1)CC2)c1ccccn1 | Fc1ccc(CCN2CCC(N3CCc4ccc(Cc5ccccn5)cc43)CC2)cc1 | null | [C].[Pd] | C(C)O | Reduction | OtherReaction | 3c5af32aa639db2ebe4d9851942e9468e1838e06ae5b2c1669bca1d5e0922c33 | 46f8a11b80b06e754a5a34198d843342612a5e7ede950bda52ce3a500cedba0b | c1ccc(CCN2CCC(N3CCc4ccc(Cc5ccccn5)cc43)CC2)cc1 | O-[CH;D3;+0:1](-[c:2](:[c:3]):[c:4])-[c:5](:[c:6]):[#7;a:7]:[c:8]>>[c:3]:[c:2](-[CH2;D2;+0:1]-[c:5](:[c:6]):[#7;a:7]:[c:8]):[c:4] | 24.6 | [{"value": 24.6, "product": "FC1=CC=C(CCN2CCC(CC2)N2CCC3=CC=C(C=C23)CC2=NC=CC=C2)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 24.6, "product": "FC1=CC=C(CCN2CCC(CC2)N2CCC3=CC=C(C=C23)CC2=NC=CC=C2)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 1-[1-(4-Fluorophenethyl)piperidin-4-yl]-6-[1-hydroxy-1-(2-pyridyl)methyl]indoline (0.321 g) was dissolved in ethanol (86.4 ml) f ollowed by the addition of 1 N hydrochloric acid (3.7 ml) and palladium carbon. Then the resultant mixture was catalytically reduced under atmospheric pressure for 3 hr. After filtering off t... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol | null | null | null | c1ccccc1.C1CC[NH]CC1.c1ccc2c(c1)CC[NH]2.c1ccncc1 | Other | [C].[Pd].C(C)O | null | null | OC(c1ccc2c(c1)N(C1CCN(CCc3ccc(F)cc3)CC1)CC2)c1ccccn1>[C].[Pd].C(C)O>Fc1ccc(CCN2CCC(N3CCc4ccc(Cc5ccccn5)cc43)CC2)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-4682ae589ccb4eb28364b61a4dd24c1e | Brc1cccnc1.O=Cc1ccc2c(c1)N(C1CCN(CCc3ccc(F)cc3)CC1)CC2>>OC(c1cccnc1)c1ccc2c(c1)N(C1CCN(CCc3ccc(F)cc3)CC1)CC2 | BrC=1C=NC=CC1.FC1=CC=C(CCN2CCC(CC2)N2CCC3=CC=C(C=C23)C=O)C=C1>>FC1=CC=C(CCN2CCC(CC2)N2CCC3=CC=C(C=C23)C(C=2C=NC=CC2)O)C=C1 | Br[c:3]1[cH:4][cH:5][cH:6][n:7][cH:8]1.[O:1]=[CH:2][c:9]1[cH:10][cH:11][c:12]2[c:13]([cH:14]1)[N:15]([CH:16]1[CH2:17][CH2:18][N:19]([CH2:20][CH2:21][c:22]3[cH:23][cH:24][c:25]([F:26])[cH:27][cH:28]3)[CH2:29][CH2:30]1)[CH2:31][CH2:32]2>>[OH:1][CH:2]([c:3]1[cH:4][cH:5][cH:6][n:7][cH:8]1)[c:9]1[cH:10][cH:11][c:12]2[c:13](... | Brc1cccnc1.O=Cc1ccc2c(c1)N(C1CCN(CCc3ccc(F)cc3)CC1)CC2 | OC(c1cccnc1)c1ccc2c(c1)N(C1CCN(CCc3ccc(F)cc3)CC1)CC2 | null | null | C(C)OCC | C-C Coupling | Grignard_alcohol | b19854b2eef93f01734a1ce1e1a8bde192af0da0e7ae2b2f44efcbe0d23365f0 | 1c0bd0afc1d5e370e3c8193faf738f03752295e40fa0eb99c756011e9a4be26b | c1ccc(CCN2CCC(N3CCc4ccc(Cc5cccnc5)cc43)CC2)cc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[#7;a:5]:[c:6]:1.[O;H0;D1;+0:7]=[CH;D2;+0:8]-[c:9](:[c:10]):[c:11]>>[OH;D1;+0:7]-[CH;D3;+0:8](-[c:9](:[c:10]):[c:11])-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[#7;a:5]:[c:6]:1 | 68.8 | [{"value": 68.8, "product": "FC1=CC=C(CCN2CCC(CC2)N2CCC3=CC=C(C=C23)C(C=2C=NC=CC2)O)C=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | 3-Bromopyridine (0.44 ml), 1-[1-(4-fluorophenethyl)-piperidin-4-yl]-6-formylindoline (0.4 g) and diethyl ether employed as the solvent were treated as in Example 93 to give the title compound (0.337 g) as a yellow oil (yield: 68.8%).
Conditions: See reaction.notes.procedure_details.
Workup: were treated as in Example 9... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aldehyde | Secondary alcohol | c1ccncc1 | c1ccncc1 | c1ccncc1.C1CC[NH]CC1.c1ccccc1.c1ccc2c(c1)CC[NH]2 | Br- | C(C)OCC | null | null | Brc1cccnc1.O=Cc1ccc2c(c1)N(C1CCN(CCc3ccc(F)cc3)CC1)CC2>C(C)OCC>OC(c1cccnc1)c1ccc2c(c1)N(C1CCN(CCc3ccc(F)cc3)CC1)CC2 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-97473d1fff47429d99067411170032d9 | COc1ccccn1.O=Cc1ccc2c(c1)N(C1CCN(CCc3ccc(F)cc3)CC1)CC2>>COc1ncccc1C(O)c1ccc2c(c1)N(C1CCN(CCc3ccc(F)cc3)CC1)CC2 | COC1=NC=CC=C1.FC1=CC=C(CCN2CCC(CC2)N2CCC3=CC=C(C=C23)C=O)C=C1>>FC1=CC=C(CCN2CCC(CC2)N2CCC3=CC=C(C=C23)C(C=2C(=NC=CC2)OC)O)C=C1 | [CH3:1][O:2][c:3]1[n:4][cH:5][cH:6][cH:7][cH:8]1.[CH:9](=[O:10])[c:11]1[cH:12][cH:13][c:14]2[c:15]([cH:16]1)[N:17]([CH:18]1[CH2:19][CH2:20][N:21]([CH2:22][CH2:23][c:24]3[cH:25][cH:26][c:27]([F:28])[cH:29][cH:30]3)[CH2:31][CH2:32]1)[CH2:33][CH2:34]2>>[CH3:1][O:2][c:3]1[n:4][cH:5][cH:6][cH:7][c:8]1[CH:9]([OH:10])[c:11]1[... | COc1ccccn1.O=Cc1ccc2c(c1)N(C1CCN(CCc3ccc(F)cc3)CC1)CC2 | COc1ncccc1C(O)c1ccc2c(c1)N(C1CCN(CCc3ccc(F)cc3)CC1)CC2 | null | null | null | C-C Coupling | OtherReaction | 40f13612d6ac265abbd16b0b42c176684a0c57aff53dfd2bec4e4213354e09ff | a7cae52d902b2812376f5459a7a8b7ead54e8ef31fd78982d2e99bec532613ba | c1ccc(CCN2CCC(N3CCc4ccc(Cc5cccnc5)cc43)CC2)cc1 | [#8:1]-[c:2]1:[#7;a:3]:[c:4]:[c:5]:[c:6]:[cH;D2;+0:7]:1.[O;H0;D1;+0:8]=[CH;D2;+0:9]-[c:10](:[c:11]):[c:12]>>[#8:1]-[c:2]1:[#7;a:3]:[c:4]:[c:5]:[c:6]:[c;H0;D3;+0:7]:1-[CH;D3;+0:9](-[OH;D1;+0:8])-[c:10](:[c:11]):[c:12] | 75.2 | [{"value": 75.2, "product": "FC1=CC=C(CCN2CCC(CC2)N2CCC3=CC=C(C=C23)C(C=2C(=NC=CC2)OC)O)C=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | 2-Methoxypyridine (0.3 ml) and 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-formylindoline (0.5 g) were treated in accordance with the method described in J. Org. Chem., 1367 (1988). to give the title compound (0.493 g) as a pale yellow oil (yield: 75.2%).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | Secondary alcohol | c1ccncc1 | c1ccncc1 | c1ccncc1.C1CC[NH]CC1.c1ccccc1.c1ccc2c(c1)CC[NH]2 | null | null | null | null | COc1ccccn1.O=Cc1ccc2c(c1)N(C1CCN(CCc3ccc(F)cc3)CC1)CC2>>COc1ncccc1C(O)c1ccc2c(c1)N(C1CCN(CCc3ccc(F)cc3)CC1)CC2 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-72fc3fdffb15443da30650cfd877b0c3 | COc1cccc(Br)n1.O=Cc1ccc2c(c1)N(C1CCN(CCc3ccc(F)cc3)CC1)CC2>>COc1cccc(C(O)c2ccc3c(c2)N(C2CCN(CCc4ccc(F)cc4)CC2)CC3)n1 | CN(CCN(C)C)C.BrC1=CC=CC(=N1)OC.FC1=CC=C(CCN2CCC(CC2)N2CCC3=CC=C(C=C23)C=O)C=C1>>FC1=CC=C(CCN2CCC(CC2)N2CCC3=CC=C(C=C23)C(C2=CC=CC(=N2)OC)O)C=C1 | Br[c:7]1[cH:6][cH:5][cH:4][c:3]([O:2][CH3:1])[n:34]1.[CH:8](=[O:9])[c:10]1[cH:11][cH:12][c:13]2[c:14]([cH:15]1)[N:16]([CH:17]1[CH2:18][CH2:19][N:20]([CH2:21][CH2:22][c:23]3[cH:24][cH:25][c:26]([F:27])[cH:28][cH:29]3)[CH2:30][CH2:31]1)[CH2:32][CH2:33]2>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]([CH:8]([OH:9])[c:10]2[cH:... | COc1cccc(Br)n1.O=Cc1ccc2c(c1)N(C1CCN(CCc3ccc(F)cc3)CC1)CC2 | COc1cccc(C(O)c2ccc3c(c2)N(C2CCN(CCc4ccc(F)cc4)CC2)CC3)n1 | null | null | C(C)OCC | C-C Coupling | Grignard_alcohol | b19854b2eef93f01734a1ce1e1a8bde192af0da0e7ae2b2f44efcbe0d23365f0 | 1c0bd0afc1d5e370e3c8193faf738f03752295e40fa0eb99c756011e9a4be26b | c1ccc(CCN2CCC(N3CCc4ccc(Cc5ccccn5)cc43)CC2)cc1 | Br-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5].[O;H0;D1;+0:6]=[CH;D2;+0:7]-[c:8](:[c:9]):[c:10]>>[OH;D1;+0:6]-[CH;D3;+0:7](-[c:8](:[c:9]):[c:10])-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5] | 76.5 | [{"value": 76.5, "product": "FC1=CC=C(CCN2CCC(CC2)N2CCC3=CC=C(C=C23)C(C2=CC=CC(=N2)OC)O)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 76.5, "product": "FC1=CC=C(CCN2CCC(CC2)N2CCC3=CC=C(C=C23)C(C2=CC=CC(=N2)OC)O)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Tetramethylethylenediamine (0.26 ml) was added to 6-bromo-2-methoxypyridine (0.32 g) synthesized in accordance with the method described in Tetrahedron, 1373 (1985). and 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-formylindoline (0.4 g) and diethyl ether was employed as the solvent. The resultant mixture was treated as i... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aldehyde | Secondary alcohol | c1ccncc1 | c1ccncc1 | c1ccncc1.C1CC[NH]CC1.c1ccccc1.c1ccc2c(c1)CC[NH]2 | Br- | C(C)OCC | null | null | COc1cccc(Br)n1.O=Cc1ccc2c(c1)N(C1CCN(CCc3ccc(F)cc3)CC1)CC2>C(C)OCC>COc1cccc(C(O)c2ccc3c(c2)N(C2CCN(CCc4ccc(F)cc4)CC2)CC3)n1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-8ab6efd27df644d79ffb16a0c7f0a1ec | CN(C)c1ccccn1.[Br-]>>CN(C)c1ccc(Br)cn1 | CN(C1=NC=CC=C1)C.[Br-].C(CCC)[NH+](CCCC)CCCC>>BrC=1C=CC(=NC1)N(C)C | [CH3:1][N:2]([CH3:3])[c:4]1[cH:5][cH:6][cH:7][cH:9][n:10]1.[Br-:8]>>[CH3:1][N:2]([CH3:3])[c:4]1[cH:5][cH:6][c:7]([Br:8])[cH:9][n:10]1 | CN(C)c1ccccn1.[Br-] | CN(C)c1ccc(Br)cn1 | null | null | C(Cl)(Cl)Cl | Functional Group Interconversion | Bromination | 66a492ff31bfcbb52d9a760416ba269a4cf5a439a6c2ca9c2c3a3ed0a750b974 | 3c4065ab4a8681675e06a527dcad54d701c7bfdcac9f73f87773b05034108934 | c1ccncc1 | [#7;a:1]1:[c:2]:[c:3]:[c:4]:[cH;D2;+0:5]:[c:6]:1.[Br-;H0;D0:7]>>[Br;H0;D1;+0:7]-[c;H0;D3;+0:5]1:[c:4]:[c:3]:[c:2]:[#7;a:1]:[c:6]:1 | 72 | [{"value": 72.0, "product": "BrC=1C=CC(=NC1)N(C)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | 2-Dimethylaminopyridine (1.0 ml) was dissolved in chloroform (60 ml). After adding tributylammonium bromide (3.88 g) thereto, the resultant mixture was stirred for 7 min. Then the reaction solution was washed with an aqueous solution of sodium thiosulfate and water, dried over anhydrous sodium sulfate and concentrated ... | 10.6084/m9.figshare.5104873.v1 | null | null | Aromatic halide | c1ccncc1 | c1ccncc1 | c1ccncc1 | null | C(Cl)(Cl)Cl | null | null | CN(C)c1ccccn1.[Br-]>C(Cl)(Cl)Cl>CN(C)c1ccc(Br)cn1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-49f9de68a7b64bc7bd7b5b8f35d39ebd | CN(C)c1ccc(C=O)cn1.Fc1ccc(CCN2CCC(N3CCc4ccc(Br)cc43)CC2)cc1>>CN(C)c1ccc(Br)cn1 | FC1=CC=C(CCN2CCC(CC2)N2CCC3=CC=C(C=C23)Br)C=C1.CN(C1=NC=C(C=C1)C=O)C>>BrC=1C=CC(=NC1)N(C)C | O=C[c:7]1[cH:6][cH:5][c:4]([N:2]([CH3:1])[CH3:3])[n:10][cH:9]1.Fc1ccc(CCN2CCC(N3CCc4ccc([Br:8])cc43)CC2)cc1>>[CH3:1][N:2]([CH3:3])[c:4]1[cH:5][cH:6][c:7]([Br:8])[cH:9][n:10]1 | CN(C)c1ccc(C=O)cn1.Fc1ccc(CCN2CCC(N3CCc4ccc(Br)cc43)CC2)cc1 | CN(C)c1ccc(Br)cn1 | null | null | null | Functional Group Interconversion | OtherReaction | 02ca58a63354d77e55db02b58d2cf347bedc6e88e9847d092aa7ba0bc0c23e92 | 45156b9cda241d6c59413ddc136a1953db6e5eb8e5fe0466c09bc59b4fd9dc8f | c1ccncc1 | F-c1:c:c:c(-C-C-N2-C-C-C(-N3-C-C-c4:c:c:c(-[Br;H0;D1;+0:1]):c:c:4-3)-C-C-2):c:c:1.O=C-[c;H0;D3;+0:2]1:[c:3]:[c:4]:[c:5]:[#7;a:6]:[c:7]:1>>[Br;H0;D1;+0:1]-[c;H0;D3;+0:2]1:[c:3]:[c:4]:[c:5]:[#7;a:6]:[c:7]:1 | 150.9 | [{"value": 65.3, "product": "BrC=1C=CC(=NC1)N(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 150.9, "product": "BrC=1C=CC(=NC1)N(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 1-[1-(4-Fluorophenethyl)piperidin-4-yl]-6-bromoindoline (0.5 g) and 2-dimethylamino-5-formylpyridine (0.345 g) were treated as in Example 130 to give the title compound (0.376 g) as a colorless oil (yield: 65.3%).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Aldehyde.Tertiary amine.Tertiary amine | Aromatic halide | c1ccncc1.c1ccccc1.C1CCNCC1.c1ccc2c(c1)CCN2 | c1ccncc1 | c1ccncc1 | HF | null | null | null | CN(C)c1ccc(C=O)cn1.Fc1ccc(CCN2CCC(N3CCc4ccc(Br)cc43)CC2)cc1>>CN(C)c1ccc(Br)cn1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-6b87a79f9fe34323bdf1bb84914aa04a | Fc1ccc(CCN2CCC(N3CCc4ccc(Br)cc43)CC2)cc1>>Fc1ccc(CCN2CCC(n3ccc4ccc(Br)cc43)CC2)cc1 | FC1=CC=C(CCN2CCC(CC2)N2CCC3=CC=C(C=C23)Br)C=C1>>FC1=CC=C(CCN2CCC(CC2)N2C=CC3=CC=C(C=C23)Br)C=C1 | [F:1][c:2]1[cH:3][cH:4][c:5]([CH2:6][CH2:7][N:8]2[CH2:9][CH2:10][CH:11]([N:12]3[CH2:13][CH2:14][c:15]4[cH:16][cH:17][c:18]([Br:19])[cH:20][c:21]43)[CH2:22][CH2:23]2)[cH:24][cH:25]1>>[F:1][c:2]1[cH:3][cH:4][c:5]([CH2:6][CH2:7][N:8]2[CH2:9][CH2:10][CH:11]([n:12]3[cH:13][cH:14][c:15]4[cH:16][cH:17][c:18]([Br:19])[cH:20][c... | Fc1ccc(CCN2CCC(N3CCc4ccc(Br)cc43)CC2)cc1 | Fc1ccc(CCN2CCC(n3ccc4ccc(Br)cc43)CC2)cc1 | null | [O-2].[O-2].[Mn+4] | C(Cl)(Cl)Cl | Oxidation | OtherReaction | 3747aca2f1587cdf6a8e2beafaad24064251ebc55727950e633c859c42148a48 | d04c5715e362fd32bffcfe60290c32ad0adedbe2d4f79a927f35e0b5f372b098 | c1ccc(CCN2CCC(n3ccc4ccccc43)CC2)cc1 | [C:1]-[C:2](-[N;H0;D3;+0:3]1-[CH2;D2;+0:4]-[CH2;D2;+0:5]-[c:6](:[c:7]):[c:8]-1:[c:9])-[C:10]>>[C:1]-[C:2](-[n;H0;D3;+0:3]1:[cH;D2;+0:4]:[cH;D2;+0:5]:[c:6](:[c:7]):[c:8]:1:[c:9])-[C:10] | 482.4 | [{"value": 96.5, "product": "FC1=CC=C(CCN2CCC(CC2)N2C=CC3=CC=C(C=C23)Br)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 482.4, "product": "FC1=CC=C(CCN2CCC(CC2)N2C=CC3=CC=C(C=C23)Br)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 1-[1-(4-Fluorophenethyl)piperidin-4-yl]-6-bromoindoline (0.1 g) was dissolved in chloroform (27 ml). After adding manganese dioxide (2.75 g), the resultant mixture was heated under reflux for 4 hr. Then manganese dioxide was filtered off and the filtrate was concentrated under reduced pressure to give the title compoun... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amine | null | c1ccc2c(c1)CC[NH]2 | c1ccc2cc[nH]c2c1 | c1ccccc1.C1CC[NH]CC1.c1ccc2cc[nH]c2c1 | null | [O-2].[O-2].[Mn+4].C(Cl)(Cl)Cl | null | null | Fc1ccc(CCN2CCC(N3CCc4ccc(Br)cc43)CC2)cc1>[O-2].[O-2].[Mn+4].C(Cl)(Cl)Cl>Fc1ccc(CCN2CCC(n3ccc4ccc(Br)cc43)CC2)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-e9bfa336a970403eaf09ba797c0f7e1b | Fc1ccc(CCN2CCC(N3CCc4ccc(CCl)cc43)CC2)cc1.O=C1CNC(=O)N1>>O=C1CNC(=O)N1Cc1ccc2c(c1)N(C1CCN(CCc3ccc(F)cc3)CC1)CC2 | N1C(=O)NC(=O)C1.[H-].[Na+].FC1=CC=C(CCN2CCC(CC2)N2CCC3=CC=C(C=C23)CCl)C=C1>>FC1=CC=C(CCN2CCC(CC2)N2CCC3=CC=C(C=C23)CN2C(NCC2=O)=O)C=C1 | Cl[CH2:8][c:9]1[cH:10][cH:11][c:12]2[c:13]([cH:14]1)[N:15]([CH:16]1[CH2:17][CH2:18][N:19]([CH2:20][CH2:21][c:22]3[cH:23][cH:24][c:25]([F:26])[cH:27][cH:28]3)[CH2:29][CH2:30]1)[CH2:31][CH2:32]2.[O:1]=[C:2]1[CH2:3][NH:4][C:5](=[O:6])[NH:7]1>>[O:1]=[C:2]1[CH2:3][NH:4][C:5](=[O:6])[N:7]1[CH2:8][c:9]1[cH:10][cH:11][c:12]2[c... | Fc1ccc(CCN2CCC(N3CCc4ccc(CCl)cc43)CC2)cc1.O=C1CNC(=O)N1 | O=C1CNC(=O)N1Cc1ccc2c(c1)N(C1CCN(CCc3ccc(F)cc3)CC1)CC2 | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | b95c8d28fa328f4619a712cd548820bd7d4d3ed8e2de9f7467ced74f169834c4 | 71185a09698a72d85470086badab5839fe3f255541f1fa400a1649b43c12f685 | O=C1CNC(=O)N1Cc1ccc2c(c1)N(C1CCN(CCc3ccccc3)CC1)CC2 | Cl-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[O;D1;H0:5]=[C:6]1-[C:7]-[#7:8]-[C:9](=[O;D1;H0:10])-[NH;D2;+0:11]-1>>[O;D1;H0:5]=[C:6]1-[C:7]-[#7:8]-[C:9](=[O;D1;H0:10])-[N;H0;D3;+0:11]-1-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4] | 49.1 | [{"value": 49.0, "product": "FC1=CC=C(CCN2CCC(CC2)N2CCC3=CC=C(C=C23)CN2C(NCC2=O)=O)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 49.1, "product": "FC1=CC=C(CCN2CCC(CC2)N2CCC3=CC=C(C=C23)CN2C(NCC2=O)=O)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Hydantoin (130 mg), 60% sodium hydride (54 mg) and 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-chloromethylindoline (400 mg) were treated as in Example 202 to give the title compound (230 mg) as a white powder (yield: 49%).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Urea | Urea.Substituted dicarboximide | C1CNCN1 | C1CNC[NH]1 | C1CNC[NH]1.C1CC[NH]CC1.c1ccccc1.c1ccc2c(c1)CC[NH]2 | HCl | null | null | null | Fc1ccc(CCN2CCC(N3CCc4ccc(CCl)cc43)CC2)cc1.O=C1CNC(=O)N1>>O=C1CNC(=O)N1Cc1ccc2c(c1)N(C1CCN(CCc3ccc(F)cc3)CC1)CC2 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-65edfb8f85c34bfaa4e7a6c19e94c753 | CC1CNc2ccccc21.O=C1CCN(CCc2ccc(F)cc2)CC1>>CC1CN(C2CCN(CCc3ccc(F)cc3)CC2)c2ccccc21 | Cl.CC1CNC2=CC=CC=C12.FC1=CC=C(CCN2CCC(CC2)=O)C=C1>>FC1=CC=C(CCN2CCC(CC2)N2CC(C3=CC=CC=C23)C)C=C1 | [CH3:1][CH:2]1[CH2:3][NH:4][c:20]2[cH:21][cH:22][cH:23][cH:24][c:25]21.O=[C:5]1[CH2:6][CH2:7][N:8]([CH2:9][CH2:10][c:11]2[cH:12][cH:13][c:14]([F:15])[cH:16][cH:17]2)[CH2:18][CH2:19]1>>[CH3:1][CH:2]1[CH2:3][N:4]([CH:5]2[CH2:6][CH2:7][N:8]([CH2:9][CH2:10][c:11]3[cH:12][cH:13][c:14]([F:15])[cH:16][cH:17]3)[CH2:18][CH2:19]... | CC1CNc2ccccc21.O=C1CCN(CCc2ccc(F)cc2)CC1 | CC1CN(C2CCN(CCc3ccc(F)cc3)CC2)c2ccccc21 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | ed5f829465aab8e8fa321fc868dfe3231b2d42ce59513bacd6302db66ad15586 | 99acf13bfcfe579f51ccb82c65e4ca039ee7ca9b6fcd2747a3d9a292a88e564e | c1ccc(CCN2CCC(N3CCc4ccccc43)CC2)cc1 | O=[C;H0;D3;+0:1]1-[C:2]-[C:3]-[#7:4]-[C:5]-[C:6]-1.[c:7]:[c:8]1:[c:9]-[C:10]-[C:11]-[NH;D2;+0:12]-1>>[c:7]:[c:8]1:[c:9]-[C:10]-[C:11]-[N;H0;D3;+0:12]-1-[CH;D3;+0:1]1-[C:2]-[C:3]-[#7:4]-[C:5]-[C:6]-1 | 75.6 | [{"value": 75.6, "product": "FC1=CC=C(CCN2CCC(CC2)N2CC(C3=CC=CC=C23)C)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 3-Methylindoline (0.2 g) and 1-(4-fluorophenethyl)-4-piperidone (0.50 g) were treated as in Example 16 to give the title compound (0.384 g) as a pale yellow oil (yield: 7.0.7%) Next, hydrochloric acid was added thereto to give a salt followed by recrystallization from ethanol. Thus the hydrochloride (0.314 g) of the ti... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Secondary amine | Tertiary amine | c1ccc2c(c1)CCN2.C1CC[NH]CC1 | C1CC[NH]CC1.c1ccc2c(c1)CC[NH]2 | C1CC[NH]CC1.c1ccccc1.c1ccc2c(c1)CC[NH]2 | Other | null | null | null | CC1CNc2ccccc21.O=C1CCN(CCc2ccc(F)cc2)CC1>>CC1CN(C2CCN(CCc3ccc(F)cc3)CC2)c2ccccc21 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-91568a1f09ec49e28d81837910dbdcf9 | Nc1ccc2c(c1)N(C1CCN(CCc3ccc(F)cc3)CC1)CC2.O=C1CCC(=O)N1Cl>>Nc1cc2c(cc1Cl)CCN2C1CCN(CCc2ccc(F)cc2)CC1 | ClN1C(CCC1=O)=O.FC1=CC=C(CCN2CCC(CC2)N2CCC3=CC=C(C=C23)N)C=C1>>FC1=CC=C(CCN2CCC(CC2)N2CCC3=CC(=C(C=C23)N)Cl)C=C1 | [NH2:1][c:2]1[cH:3][c:4]2[c:5]([cH:6][cH:7]1)[CH2:9][CH2:10][N:11]2[CH:12]1[CH2:13][CH2:14][N:15]([CH2:16][CH2:17][c:18]2[cH:19][cH:20][c:21]([F:22])[cH:23][cH:24]2)[CH2:25][CH2:26]1.O=C1CCC(=O)N1[Cl:8]>>[NH2:1][c:2]1[cH:3][c:4]2[c:5]([cH:6][c:7]1[Cl:8])[CH2:9][CH2:10][N:11]2[CH:12]1[CH2:13][CH2:14][N:15]([CH2:16][CH2:... | Nc1ccc2c(c1)N(C1CCN(CCc3ccc(F)cc3)CC1)CC2.O=C1CCC(=O)N1Cl | Nc1cc2c(cc1Cl)CCN2C1CCN(CCc2ccc(F)cc2)CC1 | null | null | C(C)#N | Functional Group Interconversion | Chlorination | 749b7da521c36004136e7832d86baf4f17c3baa827b27171955ed680ce4b0dbd | 0e444576b73669992a4073cc3f7b10ed52cb9df09f9f8e4042e39e6a602aa390 | c1ccc(CCN2CCC(N3CCc4ccccc43)CC2)cc1 | O=C1-C-C-C(=O)-N-1-[Cl;H0;D1;+0:1].[N;D1;H2:2]-[c:3](:[c:4]):[cH;D2;+0:5]:[c:6]:[c:7]>>[Cl;H0;D1;+0:1]-[c;H0;D3;+0:5](:[c:6]:[c:7]):[c:3](-[N;D1;H2:2]):[c:4] | 34.5 | [{"value": 34.0, "product": "FC1=CC=C(CCN2CCC(CC2)N2CCC3=CC(=C(C=C23)N)Cl)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 34.5, "product": "FC1=CC=C(CCN2CCC(CC2)N2CCC3=CC(=C(C=C23)N)Cl)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | N-Chlorosuccinimide (0.24 g) was added at room temperature to a solution of 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-aminoindoline (0.5 g) in acetonitrile (50 ml) and the resultant mixture was stirred for 1 hr. Then the reaction mixture was filtered and concentrated under reduced pressure. Next, a 5 N aqueous solution... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Tertiary amide | Aromatic halide | c1ccc2c(c1)CC[NH]2.C1CCNC1 | c1ccc2c(c1)CC[NH]2 | c1ccc2c(c1)CC[NH]2.C1CC[NH]CC1.c1ccccc1 | HO- | C(C)#N | null | null | Nc1ccc2c(c1)N(C1CCN(CCc3ccc(F)cc3)CC1)CC2.O=C1CCC(=O)N1Cl>C(C)#N>Nc1cc2c(cc1Cl)CCN2C1CCN(CCc2ccc(F)cc2)CC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-918ca2d6d59f4de195adab010f5988c0 | COc1ccc2c(c1)N(C1CCN(CCc3ccc(F)cc3)CC1)CC2.O=C1CCC(=O)N1Cl>>COc1cc2c(cc1Cl)CCN2C1CCN(CCc2ccc(F)cc2)CC1 | [OH-].[Na+].C(C)(=O)OCC.ClN1C(CCC1=O)=O.FC1=CC=C(CCN2CCC(CC2)N2CCC3=CC=C(C=C23)OC)C=C1>>FC1=CC=C(CCN2CCC(CC2)N2CCC3=CC(=C(C=C23)OC)Cl)C=C1 | [CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([cH:7][cH:8]1)[CH2:10][CH2:11][N:12]2[CH:13]1[CH2:14][CH2:15][N:16]([CH2:17][CH2:18][c:19]2[cH:20][cH:21][c:22]([F:23])[cH:24][cH:25]2)[CH2:26][CH2:27]1.O=C1CCC(=O)N1[Cl:9]>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([cH:7][c:8]1[Cl:9])[CH2:10][CH2:11][N:12]2[CH:13]1[CH2:14][CH2:15][N:16]([... | COc1ccc2c(c1)N(C1CCN(CCc3ccc(F)cc3)CC1)CC2.O=C1CCC(=O)N1Cl | COc1cc2c(cc1Cl)CCN2C1CCN(CCc2ccc(F)cc2)CC1 | null | null | C(Cl)Cl | Functional Group Interconversion | Chlorination | 749b7da521c36004136e7832d86baf4f17c3baa827b27171955ed680ce4b0dbd | 0e444576b73669992a4073cc3f7b10ed52cb9df09f9f8e4042e39e6a602aa390 | c1ccc(CCN2CCC(N3CCc4ccccc43)CC2)cc1 | O=C1-C-C-C(=O)-N-1-[Cl;H0;D1;+0:1].[#8:2]-[c:3](:[c:4]):[cH;D2;+0:5]:[c:6]:[c:7]>>[#8:2]-[c:3](:[c:4]):[c;H0;D3;+0:5](-[Cl;H0;D1;+0:1]):[c:6]:[c:7] | 21 | [{"value": 21.0, "product": "FC1=CC=C(CCN2CCC(CC2)N2CCC3=CC(=C(C=C23)OC)Cl)C=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | N-Chlorosuccinimide (0.15 g) was added at room temperature to a solution of 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-methoxyindoline (0.39 g) in methylene chloride (5 ml) and the resultant mixture was stirred for 20 min. Then a 5 N aqueous solution of sodium hydroxide and ethyl acetate were added to the reaction solut... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Tertiary amide | Aromatic halide | c1ccc2c(c1)CC[NH]2.C1CCNC1 | c1ccc2c(c1)CC[NH]2 | c1ccc2c(c1)CC[NH]2.C1CC[NH]CC1.c1ccccc1 | HO- | C(Cl)Cl | null | null | COc1ccc2c(c1)N(C1CCN(CCc3ccc(F)cc3)CC1)CC2.O=C1CCC(=O)N1Cl>C(Cl)Cl>COc1cc2c(cc1Cl)CCN2C1CCN(CCc2ccc(F)cc2)CC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-232ee03a698e48479f56307e26524ce8 | Brc1ccc2c(c1)N(C1CCNCC1)CC2.Fc1ccc(CCBr)c(F)c1>>Fc1ccc(CCN2CCC(N3CCc4ccc(Br)cc43)CC2)c(F)c1 | N1CCC(CC1)N1CCC2=CC=C(C=C12)Br.FC1=C(CCBr)C=CC(=C1)F>>FC1=C(CCN2CCC(CC2)N2CCC3=CC=C(C=C23)Br)C=CC(=C1)F | [NH:8]1[CH2:9][CH2:10][CH:11]([N:12]2[CH2:13][CH2:14][c:15]3[cH:16][cH:17][c:18]([Br:19])[cH:20][c:21]32)[CH2:22][CH2:23]1.Br[CH2:7][CH2:6][c:5]1[cH:4][cH:3][c:2]([F:1])[cH:26][c:24]1[F:25]>>[F:1][c:2]1[cH:3][cH:4][c:5]([CH2:6][CH2:7][N:8]2[CH2:9][CH2:10][CH:11]([N:12]3[CH2:13][CH2:14][c:15]4[cH:16][cH:17][c:18]([Br:19... | Brc1ccc2c(c1)N(C1CCNCC1)CC2.Fc1ccc(CCBr)c(F)c1 | Fc1ccc(CCN2CCC(N3CCc4ccc(Br)cc43)CC2)c(F)c1 | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 0240b8450ff2c489d02f5f0d90bc953079d7a3ab239d35a03f26392fc248b4ef | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | c1ccc(CCN2CCC(N3CCc4ccccc43)CC2)cc1 | Br-[CH2;D2;+0:1]-[C:2]-[c:3].[C:4]-[C:5]-[NH;D2;+0:6]-[C:7]-[C:8]>>[C:4]-[C:5]-[N;H0;D3;+0:6](-[CH2;D2;+0:1]-[C:2]-[c:3])-[C:7]-[C:8] | 60.1 | [{"value": 60.0, "product": "FC1=C(CCN2CCC(CC2)N2CCC3=CC=C(C=C23)Br)C=CC(=C1)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 60.1, "product": "FC1=C(CCN2CCC(CC2)N2CCC3=CC=C(C=C23)Br)C=CC(=C1)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 1-(Piperidin-4-yl)-6-bromoindoline (3.0 g) and 2,4-difluorophenethyl bromide (3.1 g) were treated as in Example 2 to give the title compound (2.7 g) as a white powder (yield: 60%).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1CCNCC1 | C1CC[NH]CC1 | c1ccccc1.C1CC[NH]CC1.c1ccc2c(c1)CC[NH]2 | HBr | null | null | null | Brc1ccc2c(c1)N(C1CCNCC1)CC2.Fc1ccc(CCBr)c(F)c1>>Fc1ccc(CCN2CCC(N3CCc4ccc(Br)cc43)CC2)c(F)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-13a1790e7fce45129ffc70eafaf88007 | COc1ccc2c(c1)N(C1CCNCC1)CC2.NS(=O)(=O)c1ccc(CCBr)cc1>>COc1ccc2c(c1)N(C1CCN(CCc3ccc(S(N)(=O)=O)cc3)CC1)CC2 | N1CCC(CC1)N1CCC2=CC=C(C=C12)OC.S(N)(=O)(=O)C1=CC=C(CCBr)C=C1>>S(N)(=O)(=O)C1=CC=C(CCN2CCC(CC2)N2CCC3=CC=C(C=C23)OC)C=C1 | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([cH:8]1)[N:9]([CH:10]1[CH2:11][CH2:12][NH:13][CH2:26][CH2:27]1)[CH2:28][CH2:29]2.Br[CH2:14][CH2:15][c:16]1[cH:17][cH:18][c:19]([S:20]([NH2:21])(=[O:22])=[O:23])[cH:24][cH:25]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([cH:8]1)[N:9]([CH:10]1[CH2:11][CH2:12][N:13]([CH2:14][CH2:1... | COc1ccc2c(c1)N(C1CCNCC1)CC2.NS(=O)(=O)c1ccc(CCBr)cc1 | COc1ccc2c(c1)N(C1CCN(CCc3ccc(S(N)(=O)=O)cc3)CC1)CC2 | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 0240b8450ff2c489d02f5f0d90bc953079d7a3ab239d35a03f26392fc248b4ef | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | c1ccc(CCN2CCC(N3CCc4ccccc43)CC2)cc1 | Br-[CH2;D2;+0:1]-[C:2]-[c:3].[C:4]-[C:5]-[NH;D2;+0:6]-[C:7]-[C:8]>>[C:4]-[C:5]-[N;H0;D3;+0:6](-[CH2;D2;+0:1]-[C:2]-[c:3])-[C:7]-[C:8] | 13.1 | [{"value": 13.0, "product": "S(N)(=O)(=O)C1=CC=C(CCN2CCC(CC2)N2CCC3=CC=C(C=C23)OC)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 13.1, "product": "S(N)(=O)(=O)C1=CC=C(CCN2CCC(CC2)N2CCC3=CC=C(C=C23)OC)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 1-(Piperidin-4-yl)-6-methoxyindoline (350 mg) and 4-sulfamoylphenethyl bromide (340 mg) were treated as in Example 2 to give the title compound (70 mg) as a brown powder (yield: 13%).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1CCNCC1 | C1CC[NH]CC1 | C1CC[NH]CC1.c1ccccc1.c1ccc2c(c1)CC[NH]2 | HBr | null | null | null | COc1ccc2c(c1)N(C1CCNCC1)CC2.NS(=O)(=O)c1ccc(CCBr)cc1>>COc1ccc2c(c1)N(C1CCN(CCc3ccc(S(N)(=O)=O)cc3)CC1)CC2 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-d29c7b7a24244799ba89050c6599dab3 | Brc1ccc2c(c1)N(C1CCNCC1)CC2.Fc1ccc(OCCCBr)cc1>>Fc1ccc(OCCCN2CCC(N3CCc4ccc(Br)cc43)CC2)cc1 | N1CCC(CC1)N1CCC2=CC=C(C=C12)Br.FC1=CC=C(OCCCBr)C=C1>>FC1=CC=C(OCCCN2CCC(CC2)N2CCC3=CC=C(C=C23)Br)C=C1 | [NH:10]1[CH2:11][CH2:12][CH:13]([N:14]2[CH2:15][CH2:16][c:17]3[cH:18][cH:19][c:20]([Br:21])[cH:22][c:23]32)[CH2:24][CH2:25]1.Br[CH2:9][CH2:8][CH2:7][O:6][c:5]1[cH:4][cH:3][c:2]([F:1])[cH:27][cH:26]1>>[F:1][c:2]1[cH:3][cH:4][c:5]([O:6][CH2:7][CH2:8][CH2:9][N:10]2[CH2:11][CH2:12][CH:13]([N:14]3[CH2:15][CH2:16][c:17]4[cH:... | Brc1ccc2c(c1)N(C1CCNCC1)CC2.Fc1ccc(OCCCBr)cc1 | Fc1ccc(OCCCN2CCC(N3CCc4ccc(Br)cc43)CC2)cc1 | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 0240b8450ff2c489d02f5f0d90bc953079d7a3ab239d35a03f26392fc248b4ef | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | c1ccc(OCCCN2CCC(N3CCc4ccccc43)CC2)cc1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[C:4]-[C:5]-[NH;D2;+0:6]-[C:7]-[C:8]>>[C:4]-[C:5]-[N;H0;D3;+0:6](-[CH2;D2;+0:1]-[C:2]-[C:3])-[C:7]-[C:8] | 90 | [{"value": 90.0, "product": "FC1=CC=C(OCCCN2CCC(CC2)N2CCC3=CC=C(C=C23)Br)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 89.2, "product": "FC1=CC=C(OCCCN2CCC(CC2)N2CCC3=CC=C(C=C23)Br)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 1-(Piperidin-4-yl)-6-bromoindoline (1.6 g) and 4-fluorophenoxypropyl bromide (1.6 g) were treated as in Example 2 to give the title compound (2.2 g) as a white powder (yield: 90%).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1CCNCC1 | C1CC[NH]CC1 | c1ccccc1.C1CC[NH]CC1.c1ccc2c(c1)CC[NH]2 | HBr | null | null | null | Brc1ccc2c(c1)N(C1CCNCC1)CC2.Fc1ccc(OCCCBr)cc1>>Fc1ccc(OCCCN2CCC(N3CCc4ccc(Br)cc43)CC2)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-0d67a982b1734e37aa2e5417fc75c48c | BrCCc1ccc2ncsc2c1.COc1ccc2c(c1)N(C1CCNCC1)CC2>>COc1ccc2c(c1)N(C1CCN(CCc3ccc4ncsc4c3)CC1)CC2 | BrCCC1=CC2=C(N=CS2)C=C1.N1CCC(CC1)N1CCC2=CC=C(C=C12)OC>>S1C=NC2=C1C=C(C=C2)CCN2CCC(CC2)N2CCC1=CC=C(C=C21)OC | Br[CH2:14][CH2:15][c:16]1[cH:17][cH:18][c:19]2[n:20][cH:21][s:22][c:23]2[cH:24]1.[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([cH:8]1)[N:9]([CH:10]1[CH2:11][CH2:12][NH:13][CH2:25][CH2:26]1)[CH2:27][CH2:28]2>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([cH:8]1)[N:9]([CH:10]1[CH2:11][CH2:12][N:13]([CH2:14][CH2:15][c:16]3[cH:1... | BrCCc1ccc2ncsc2c1.COc1ccc2c(c1)N(C1CCNCC1)CC2 | COc1ccc2c(c1)N(C1CCN(CCc3ccc4ncsc4c3)CC1)CC2 | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 0240b8450ff2c489d02f5f0d90bc953079d7a3ab239d35a03f26392fc248b4ef | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | c1ccc2c(c1)CCN2C1CCN(CCc2ccc3ncsc3c2)CC1 | Br-[CH2;D2;+0:1]-[C:2]-[c:3].[C:4]-[C:5]-[NH;D2;+0:6]-[C:7]-[C:8]>>[C:4]-[C:5]-[N;H0;D3;+0:6](-[CH2;D2;+0:1]-[C:2]-[c:3])-[C:7]-[C:8] | 82.6 | [{"value": 81.9, "product": "S1C=NC2=C1C=C(C=C2)CCN2CCC(CC2)N2CCC1=CC=C(C=C21)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 82.6, "product": "S1C=NC2=C1C=C(C=C2)CCN2CCC(CC2)N2CCC1=CC=C(C=C21)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 6-(2-Bromoethyl)benzothiazole (0.108 g) and 1-(piperidin-4-yl)-6-methoxyindoline (0.105 g) were treated as in Example 2 to give the title compound (0.145 g) as a yellow oil (yield: 81.9%).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1CCNCC1 | C1CC[NH]CC1 | C1CC[NH]CC1.c1ccc2scnc2c1.c1ccc2c(c1)CC[NH]2 | HBr | null | null | null | BrCCc1ccc2ncsc2c1.COc1ccc2c(c1)N(C1CCNCC1)CC2>>COc1ccc2c(c1)N(C1CCN(CCc3ccc4ncsc4c3)CC1)CC2 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-5560cc829e98483ca2ad1691a83b6d91 | COc1ccc2c(c1)C(=O)CC2>>COc1ccc2c(c1)C(O)CC2 | COC1=CC=C2CCC(C2=C1)=O.[BH4-].[Na+]>>COC1=CC=C2CCC(C2=C1)O | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([cH:8]1)[C:9](=[O:10])[CH2:11][CH2:12]2>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([cH:8]1)[CH:9]([OH:10])[CH2:11][CH2:12]2 | COc1ccc2c(c1)C(=O)CC2 | COc1ccc2c(c1)C(O)CC2 | null | null | CO | Reduction | Reduction of ketone to secondary alcohol | 0a3f398c63bd0c6cfcdf56758ab675b7848fb8b1a73b3840e22b4343df98b04f | 1bd3cd74b454139c0a0068ac0135836499926b274bff569df163210c6c944a89 | c1ccc2c(c1)CCC2 | [O;H0;D1;+0:1]=[C;H0;D3;+0:2]1-[C:3]-[C:4]-[c:5]:[c:6]-1:[c:7]>>[OH;D1;+0:1]-[CH;D3;+0:2]1-[C:3]-[C:4]-[c:5]:[c:6]-1:[c:7] | 100.7 | [{"value": 100.7, "product": "COC1=CC=C2CCC(C2=C1)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 6-Methoxyindan-1-one (5.0 g) was dissolved in methanol (50 ml). Next, sodium tetrahydroborate (1.41 g) was added thereto at 0° C., and the resultant mixture was reacted at room temperature for 5 hr. The reaction solution was concentrated under reduced pressure and the residue was partitioned between ethyl acetate and w... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Secondary alcohol | c1ccc2c(c1)CCC2 | c1ccc2c(c1)CCC2 | c1ccc2c(c1)CCC2 | null | CO | null | null | COc1ccc2c(c1)C(=O)CC2>CO>COc1ccc2c(c1)C(O)CC2 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-311cddd1fa984dd99906ab4142f8c75b | COc1ccc2c(c1)C(N1CCN(C(C)=O)CC1)CC2>>CCN1CCN(C2CCc3ccc(OC)cc32)CC1 | C(C)(=O)N1CCN(CC1)C1CCC2=CC=C(C=C12)OC.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+].O>>C(C)N1CCN(CC1)C1CCC2=CC=C(C=C12)OC | O=[C:2]([CH3:1])[N:3]1[CH2:4][CH2:5][N:6]([CH:7]2[CH2:8][CH2:9][c:10]3[cH:11][cH:12][c:13]([O:14][CH3:15])[cH:16][c:17]32)[CH2:18][CH2:19]1>>[CH3:1][CH2:2][N:3]1[CH2:4][CH2:5][N:6]([CH:7]2[CH2:8][CH2:9][c:10]3[cH:11][cH:12][c:13]([O:14][CH3:15])[cH:16][c:17]32)[CH2:18][CH2:19]1 | COc1ccc2c(c1)C(N1CCN(C(C)=O)CC1)CC2 | CCN1CCN(C2CCc3ccc(OC)cc32)CC1 | null | null | C1CCOC1 | Reduction | Reduction of tertiary amides to amines | f74c5a050b269ec4da3871c266f01344b7447381f47cda744f8b1e9c225ae62d | c8f3c617792f7a4fae96b8a97dc0ce23461ab85d8a738fe6caacff776ef51ffa | c1ccc2c(c1)CCC2N1CCNCC1 | O=[C;H0;D3;+0:1](-[C;D1;H3:2])-[#7:3](-[C:4])-[C:5]>>[C:4]-[#7:3](-[CH2;D2;+0:1]-[C;D1;H3:2])-[C:5] | 63.2 | [{"value": 63.0, "product": "C(C)N1CCN(CC1)C1CCC2=CC=C(C=C12)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 63.2, "product": "C(C)N1CCN(CC1)C1CCC2=CC=C(C=C12)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | Lithium aluminum hydride (0.14 g) was suspended in THF. Into the resultant suspension was added dropwise a solution of 1-(4-acetylpiperazin-1-yl)-6-methoxyindan (0.50 g) in THF and the reaction mixture was heated under reflux while monitoring the reaction by TLC. Then the reaction solution was ice cooled and water (0.1... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide | null | null | null | C1C[NH]CC[NH]1.c1ccc2c(c1)CCC2 | Other | C1CCOC1 | null | 1 | COc1ccc2c(c1)C(N1CCN(C(C)=O)CC1)CC2>C1CCOC1>CCN1CCN(C2CCc3ccc(OC)cc32)CC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-1d981b97ad054fe78432ba569c0c0283 | Clc1ccc2c(n1)N(C1CCNCC1)CC2.Fc1ccc(CCBr)c(F)c1>>Fc1ccc(CCN2CCC(N3CCc4ccc(Cl)nc43)CC2)c(F)c1 | N1CCC(CC1)N1CCC2=CC=C(N=C12)Cl.FC1=C(CCBr)C=CC(=C1)F>>FC1=C(CCN2CCC(CC2)N2CCC3=CC=C(N=C23)Cl)C=CC(=C1)F | [NH:8]1[CH2:9][CH2:10][CH:11]([N:12]2[CH2:13][CH2:14][c:15]3[cH:16][cH:17][c:18]([Cl:19])[n:20][c:21]32)[CH2:22][CH2:23]1.Br[CH2:7][CH2:6][c:5]1[cH:4][cH:3][c:2]([F:1])[cH:26][c:24]1[F:25]>>[F:1][c:2]1[cH:3][cH:4][c:5]([CH2:6][CH2:7][N:8]2[CH2:9][CH2:10][CH:11]([N:12]3[CH2:13][CH2:14][c:15]4[cH:16][cH:17][c:18]([Cl:19]... | Clc1ccc2c(n1)N(C1CCNCC1)CC2.Fc1ccc(CCBr)c(F)c1 | Fc1ccc(CCN2CCC(N3CCc4ccc(Cl)nc43)CC2)c(F)c1 | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 0240b8450ff2c489d02f5f0d90bc953079d7a3ab239d35a03f26392fc248b4ef | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | c1ccc(CCN2CCC(N3CCc4cccnc43)CC2)cc1 | Br-[CH2;D2;+0:1]-[C:2]-[c:3].[C:4]-[C:5]-[NH;D2;+0:6]-[C:7]-[C:8]>>[C:4]-[C:5]-[N;H0;D3;+0:6](-[CH2;D2;+0:1]-[C:2]-[c:3])-[C:7]-[C:8] | 7.8 | [{"value": 7.8, "product": "FC1=C(CCN2CCC(CC2)N2CCC3=CC=C(N=C23)Cl)C=CC(=C1)F", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | 1-(Piperidin-4-yl)-6-chloro-7-azaindoline (0.5 g) and 2,4-difluorophenethyl bromide (0.43 g) were treated as in Example 2 to give the hydrochloride (74 mg) of the title compound as a brown powder (yield: 7.8%).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1CCNCC1 | C1CC[NH]CC1 | c1ccccc1.C1CC[NH]CC1.c1cnc2c(c1)CC[NH]2 | HBr | null | null | null | Clc1ccc2c(n1)N(C1CCNCC1)CC2.Fc1ccc(CCBr)c(F)c1>>Fc1ccc(CCN2CCC(N3CCc4ccc(Cl)nc43)CC2)c(F)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-ae8a87a35cf14a7cb905b3da0891fd3a | COc1ccc(CCBr)cc1.Clc1ccc2c(n1)N(C1CCNCC1)CC2>>COc1ccc(CCN2CCC(N3CCc4ccc(Cl)nc43)CC2)cc1 | N1CCC(CC1)N1CCC2=CC=C(N=C12)Cl.COC1=CC=C(CCBr)C=C1>>COC1=CC=C(CCN2CCC(CC2)N2CCC3=CC=C(N=C23)Cl)C=C1 | Br[CH2:8][CH2:7][c:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:26][cH:25]1.[NH:9]1[CH2:10][CH2:11][CH:12]([N:13]2[CH2:14][CH2:15][c:16]3[cH:17][cH:18][c:19]([Cl:20])[n:21][c:22]32)[CH2:23][CH2:24]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][CH2:8][N:9]2[CH2:10][CH2:11][CH:12]([N:13]3[CH2:14][CH2:15][c:16]4[cH:17][cH:18][c:... | COc1ccc(CCBr)cc1.Clc1ccc2c(n1)N(C1CCNCC1)CC2 | COc1ccc(CCN2CCC(N3CCc4ccc(Cl)nc43)CC2)cc1 | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 0240b8450ff2c489d02f5f0d90bc953079d7a3ab239d35a03f26392fc248b4ef | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | c1ccc(CCN2CCC(N3CCc4cccnc43)CC2)cc1 | Br-[CH2;D2;+0:1]-[C:2]-[c:3].[C:4]-[C:5]-[NH;D2;+0:6]-[C:7]-[C:8]>>[C:4]-[C:5]-[N;H0;D3;+0:6](-[CH2;D2;+0:1]-[C:2]-[c:3])-[C:7]-[C:8] | 16 | [{"value": 16.0, "product": "COC1=CC=C(CCN2CCC(CC2)N2CCC3=CC=C(N=C23)Cl)C=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | 1-(Piperidin-4-yl)-6-chloro-7-azaindoline (0.8 g) and 4-methoxyphenethyl bromide (0.72 g) were treated as in Example 2 to give the hydrochloride (220 mg) of the title compound as a pale yellow powder (yield: 16%).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1CCNCC1 | C1CC[NH]CC1 | c1ccccc1.C1CC[NH]CC1.c1cnc2c(c1)CC[NH]2 | HBr | null | null | null | COc1ccc(CCBr)cc1.Clc1ccc2c(n1)N(C1CCNCC1)CC2>>COc1ccc(CCN2CCC(N3CCc4ccc(Cl)nc43)CC2)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-5c575ef3b5e34900bff568b0f0856dbc | COc1ccc(CCBr)cc1.COc1ccc2c(c1)N(C1CCNCC1)CCC2>>COc1ccc(CCN2CCC(N3CCCc4ccc(OC)cc43)CC2)cc1 | O.N1CCC(CC1)N1CCCC2=CC=C(C=C12)OC.COC1=CC=C(C=C1)CCBr.C(C)(C)N(CC)C(C)C>>COC1=CC=C(C=C1)CCN1CCC(CC1)N1CCCC2=CC=C(C=C12)OC | Br[CH2:8][CH2:7][c:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:28][cH:27]1.[NH:9]1[CH2:10][CH2:11][CH:12]([N:13]2[CH2:14][CH2:15][CH2:16][c:17]3[cH:18][cH:19][c:20]([O:21][CH3:22])[cH:23][c:24]32)[CH2:25][CH2:26]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][CH2:8][N:9]2[CH2:10][CH2:11][CH:12]([N:13]3[CH2:14][CH2:15][CH2:16]... | COc1ccc(CCBr)cc1.COc1ccc2c(c1)N(C1CCNCC1)CCC2 | COc1ccc(CCN2CCC(N3CCCc4ccc(OC)cc43)CC2)cc1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 0240b8450ff2c489d02f5f0d90bc953079d7a3ab239d35a03f26392fc248b4ef | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | c1ccc(CCN2CCC(N3CCCc4ccccc43)CC2)cc1 | Br-[CH2;D2;+0:1]-[C:2]-[c:3].[C:4]-[C:5]-[NH;D2;+0:6]-[C:7]-[C:8]>>[C:4]-[C:5]-[N;H0;D3;+0:6](-[CH2;D2;+0:1]-[C:2]-[c:3])-[C:7]-[C:8] | null | [] | null | null | null | null | A solution of 1-(4-piperidinyl)-7-methoxy-1,2,3,4-tetrahydroquinoline (250 mg), 2-(4-methoxyphenyl)ethyl bromide (260 mg) and diisopropylethylamine (270 mg) in DMF (5 ml) was heated at 60° C. for 12 hr under stirring. After the completion of the reaction, the reaction solution was cooled to room temperature and water w... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1CCNCC1 | C1CC[NH]CC1 | c1ccccc1.C1CC[NH]CC1.c1ccc2c(c1)CCC[NH]2 | HBr | CN(C)C=O | null | null | COc1ccc(CCBr)cc1.COc1ccc2c(c1)N(C1CCNCC1)CCC2>CN(C)C=O>COc1ccc(CCN2CCC(N3CCCc4ccc(OC)cc43)CC2)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-4e1a5fcd05574f2a867f7e9123218cf9 | COc1ccc2c(c1)N(C1CCN(CC(=O)c3ccc(F)cc3)CC1)CCC2>>COc1ccc2c(c1)N(C1CCN(CC(O)c3ccc(F)cc3)CC1)CCC2 | O.[BH4-].[Na+].FC1=CC=C(C=C1)C(CN1CCC(CC1)N1CCCC2=CC=C(C=C12)OC)=O>>FC1=CC=C(C=C1)C(CN1CCC(CC1)N1CCCC2=CC=C(C=C12)OC)O | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([cH:8]1)[N:9]([CH:10]1[CH2:11][CH2:12][N:13]([CH2:14][C:15](=[O:16])[c:17]3[cH:18][cH:19][c:20]([F:21])[cH:22][cH:23]3)[CH2:24][CH2:25]1)[CH2:26][CH2:27][CH2:28]2>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([cH:8]1)[N:9]([CH:10]1[CH2:11][CH2:12][N:13]([CH2:14][CH:15]([OH:16])[c:... | COc1ccc2c(c1)N(C1CCN(CC(=O)c3ccc(F)cc3)CC1)CCC2 | COc1ccc2c(c1)N(C1CCN(CC(O)c3ccc(F)cc3)CC1)CCC2 | null | null | CO | Reduction | Reduction of ketone to secondary alcohol | 02790ac194d8bf7ccb13d6247c59412024d87f77d2c906ef7804f021f57d5070 | 1bd3cd74b454139c0a0068ac0135836499926b274bff569df163210c6c944a89 | c1ccc(CCN2CCC(N3CCCc4ccccc43)CC2)cc1 | [#7:1]-[C:2]-[C;H0;D3;+0:3](=[O;H0;D1;+0:4])-[c:5](:[c:6]):[c:7]>>[#7:1]-[C:2]-[CH;D3;+0:3](-[OH;D1;+0:4])-[c:5](:[c:6]):[c:7] | null | [] | null | null | 1 | HOUR | Sodium borohydride (73 mg) was added at 0° C. to a solution of 1-{1-[2-(4-fluorophenyl)-2-oxoethyl]piperidin-4-yl}-7-methoxy-1,2,3,4-tetrahydroquinoline (400 mg) in methanol (10 ml). The resultant mixture was stirred at the same temperature for 1 hr and then at room temperature for 1 hr. After the completion of the rea... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Secondary alcohol | null | null | C1CC[NH]CC1.c1ccccc1.c1ccc2c(c1)CCC[NH]2 | null | CO | null | 1 | COc1ccc2c(c1)N(C1CCN(CC(=O)c3ccc(F)cc3)CC1)CCC2>CO>COc1ccc2c(c1)N(C1CCN(CC(O)c3ccc(F)cc3)CC1)CCC2 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-6ebdcd3a48c84691bfcbe0f713571386 | CCN(CC)S(F)(F)F.COc1ccc2c(c1)N(C1CCN(CC(O)c3ccc(F)cc3)CC1)CCC2>>COc1ccc2c(c1)N(C1CCN(CC(F)c3ccc(F)cc3)CC1)CCC2 | FC1=CC=C(C=C1)C(CN1CCC(CC1)N1CCCC2=CC=C(C=C12)OC)O.C(C)N(CC)S(F)(F)F.C([O-])(O)=O.[Na+]>>FC1=CC=C(C=C1)C(CN1CCC(CC1)N1CCCC2=CC=C(C=C12)OC)F | CCN(CC)S(F)(F)[F:16].O[CH:15]([CH2:14][N:13]1[CH2:12][CH2:11][CH:10]([N:9]2[c:7]3[c:6]([cH:5][cH:4][c:3]([O:2][CH3:1])[cH:8]3)[CH2:28][CH2:27][CH2:26]2)[CH2:25][CH2:24]1)[c:17]1[cH:18][cH:19][c:20]([F:21])[cH:22][cH:23]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([cH:8]1)[N:9]([CH:10]1[CH2:11][CH2:12][N:13]([CH2:14][CH... | CCN(CC)S(F)(F)F.COc1ccc2c(c1)N(C1CCN(CC(O)c3ccc(F)cc3)CC1)CCC2 | COc1ccc2c(c1)N(C1CCN(CC(F)c3ccc(F)cc3)CC1)CCC2 | null | null | C(Cl)Cl | Functional Group Interconversion | OtherReaction | e80a7bea016c089beee31f9388d37df2ce7869af28d2e334bc331140a77cbc56 | 2e01f8a2520bb2c01521f4c10ab406a1b29fe14554ff1fda976238a9b96e671b | c1ccc(CCN2CCC(N3CCCc4ccccc43)CC2)cc1 | C-C-N(-C-C)-S(-F)(-F)-[F;H0;D1;+0:1].O-[CH;D3;+0:2](-[C:3]-[#7:4])-[c:5](:[c:6]):[c:7]>>[#7:4]-[C:3]-[CH;D3;+0:2](-[F;H0;D1;+0:1])-[c:5](:[c:6]):[c:7] | null | [] | null | null | 45 | MINUTE | A solution of 1-{1-[2-(4-fluorophenyl)-2-hydroxyethyl]piperidin-4-yl}-7-methoxy-1,2,3,4-tetrahydroquinoline (250 mg) in methylene chloride (5 ml) was cooled to −78° C. and diethylaminosulfur trifluoride (DAST, 0.1 ml) was added thereto. Then the reaction solution was stirred at the same temperature for 45 min. After th... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol.Tertiary amine | Secondary halide | null | null | C1CC[NH]CC1.c1ccccc1.c1ccc2c(c1)CCC[NH]2 | HF | C(Cl)Cl | null | 0.75 | CCN(CC)S(F)(F)F.COc1ccc2c(c1)N(C1CCN(CC(O)c3ccc(F)cc3)CC1)CCC2>C(Cl)Cl>COc1ccc2c(c1)N(C1CCN(CC(F)c3ccc(F)cc3)CC1)CCC2 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-d653e8801eb0417599bfb129e924602d | COc1ccc2c(c1)CCCC2C1CCN(CCc2ccc(F)cc2)CC1>>Oc1ccc2c(c1)CCCC2C1CCN(CCc2ccc(F)cc2)CC1 | C(C)(=O)O.Br.FC1=CC=C(C=C1)CCN1CCC(CC1)C1CCCC2=CC(=CC=C12)OC>>FC1=CC=C(C=C1)CCN1CCC(CC1)C1CCCC2=CC(=CC=C12)O | C[O:1][c:2]1[cH:3][cH:4][c:5]2[c:6]([cH:7]1)[CH2:8][CH2:9][CH2:10][CH:11]2[CH:12]1[CH2:13][CH2:14][N:15]([CH2:16][CH2:17][c:18]2[cH:19][cH:20][c:21]([F:22])[cH:23][cH:24]2)[CH2:25][CH2:26]1>>[OH:1][c:2]1[cH:3][cH:4][c:5]2[c:6]([cH:7]1)[CH2:8][CH2:9][CH2:10][CH:11]2[CH:12]1[CH2:13][CH2:14][N:15]([CH2:16][CH2:17][c:18]2[... | COc1ccc2c(c1)CCCC2C1CCN(CCc2ccc(F)cc2)CC1 | Oc1ccc2c(c1)CCCC2C1CCN(CCc2ccc(F)cc2)CC1 | null | null | O | Deprotection | Cleavage of methoxy ethers to alcohols | c5320c7dfa4f544d4900efcae9b3262bf0d5286bcf39c86109232351f35b23d5 | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | c1ccc(CCN2CCC(C3CCCc4ccccc43)CC2)cc1 | C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[OH;D1;+0:1]-[c:2](:[c:3]):[c:4] | 76.4 | [{"value": 76.4, "product": "FC1=CC=C(C=C1)CCN1CCC(CC1)C1CCCC2=CC(=CC=C12)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 76.4, "product": "FC1=CC=C(C=C1)CCN1CCC(CC1)C1CCCC2=CC(=CC=C12)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 47% hydrobromic acid (45 ml) was added to 1-[2-(4-fluorophenyl)ethyl]-4-(6-methoxy-1,2,3,4-tetrahydronaphthalen-1-yl)piperidine (2.718 g, 7.57 mmol) and the resultant mixture was heated under reflux for 1 hr. After adding glacial acetic acid (20 ml), the resultant mixture was heated under reflux for additional 1.5 hr. ... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | null | null | c1ccc2c(c1)CCCC2.C1CC[NH]CC1.c1ccccc1 | Other | O | null | null | COc1ccc2c(c1)CCCC2C1CCN(CCc2ccc(F)cc2)CC1>O>Oc1ccc2c(c1)CCCC2C1CCN(CCc2ccc(F)cc2)CC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-f37e7763df2441269aa380f4b809c0ab | COc1ccc2c(c1)C(=O)CCC2>>COc1ccc2c(c1)C(O)CCC2 | COC1=CC=C2CCCC(C2=C1)=O.[BH4-].[Na+]>>OC1CCCC2=CC=C(C=C12)OC | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([cH:8]1)[C:9](=[O:10])[CH2:11][CH2:12][CH2:13]2>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([cH:8]1)[CH:9]([OH:10])[CH2:11][CH2:12][CH2:13]2 | COc1ccc2c(c1)C(=O)CCC2 | COc1ccc2c(c1)C(O)CCC2 | null | null | CO | Reduction | Reduction of ketone to secondary alcohol | 3712a1f2cb52729543ec421b1a5b2fd3f779bad4223604244414834ade516040 | 1bd3cd74b454139c0a0068ac0135836499926b274bff569df163210c6c944a89 | c1ccc2c(c1)CCCC2 | [C:1]-[C:2]-[C;H0;D3;+0:3](=[O;H0;D1;+0:4])-[c:5](:[c:6]):[c:7]>>[C:1]-[C:2]-[CH;D3;+0:3](-[OH;D1;+0:4])-[c:5](:[c:6]):[c:7] | 102.6 | [{"value": 102.6, "product": "OC1CCCC2=CC=C(C=C12)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | 7-Methoxy-1,2,3,4-tetrahydronaphthalen-1-one (5 g) was dissolved in methanol and sodium tetrahydroborate (1.3 g) was added thereto at 0° C. After reacting at room temperature for 2 hr, the reaction solution was partitioned between ethyl acetate and water. The ethyl acetate layer was washed with water, dried and concent... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Secondary alcohol | c1ccc2c(c1)CCCC2 | c1ccc2c(c1)CCCC2 | c1ccc2c(c1)CCCC2 | null | CO | null | 2 | COc1ccc2c(c1)C(=O)CCC2>CO>COc1ccc2c(c1)C(O)CCC2 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-8b1f5308b3b2444d885fbe8797a034d2 | COc1ccc2c(c1)C(N1CCN(C(C)=O)CC1)CCC2.[OH-]>>COc1ccc2c(c1)C(O)CCC2 | C(C)(=O)N1CCN(CC1)C1CCCC2=CC=C(C=C12)OC.[OH-].[Na+]>>OC1CCCC2=CC=C(C=C12)OC | CC(=O)N1CCN([CH:9]2[c:7]3[c:6]([cH:5][cH:4][c:3]([O:2][CH3:1])[cH:8]3)[CH2:13][CH2:12][CH2:11]2)CC1.[OH-:10]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([cH:8]1)[CH:9]([OH:10])[CH2:11][CH2:12][CH2:13]2 | COc1ccc2c(c1)C(N1CCN(C(C)=O)CC1)CCC2.[OH-] | COc1ccc2c(c1)C(O)CCC2 | null | null | C(C)O | Heteroatom Alkylation and Arylation | OtherReaction | c10fc4fbcd058391030c8a136d8d0c2a4adda73035268778db1d11e3518911a8 | 8017998924666b0c77c2c1cc75f8dff887ee6beea8f0aa45174353903e6ea4f9 | c1ccc2c(c1)CCCC2 | C-C(=O)-N1-C-C-N(-[CH;D3;+0:1](-[C:2]-[C:3])-[c:4](:[c:5]):[c:6])-C-C-1.[OH-;D0:7]>>[C:3]-[C:2]-[CH;D3;+0:1](-[OH;D1;+0:7])-[c:4](:[c:5]):[c:6] | null | [] | null | null | null | null | 1-(4-Acetylpiperazin-1-yl)-7-methoxy-1,2,3,4-tetrahydronaphthalene (0.85 g) was dis solved in ethanol (10 ml). After adding an 8 N aqueous solution (3 ml) of sodium hydroxide, the resultant mixture was heated under reflux for 3 hr. Then the liquid reaction mixture was concentrated under reduced pressure and the residue... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Tertiary amine | Secondary alcohol | C1CNCCN1.c1ccc2c(c1)CCCC2 | c1ccc2c(c1)CCCC2 | c1ccc2c(c1)CCCC2 | HO- | C(C)O | null | null | COc1ccc2c(c1)C(N1CCN(C(C)=O)CC1)CCC2.[OH-]>C(C)O>COc1ccc2c(c1)C(O)CCC2 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-ad822638d79f4e5b8be7ef4382902fdb | COc1ccc2c(c1)C(N1CCNCC1)CCC2.O=C(O)Cc1ccc(F)cc1>>COc1ccc2c(c1)C(O)CCC2 | FC1=CC=C(C=C1)CC(=O)O.S(=O)(Cl)Cl.COC1=CC=C2CCCC(C2=C1)N1CCNCC1>>OC1CCCC2=CC=C(C=C12)OC | C1CN([CH:9]2[c:7]3[c:6]([cH:5][cH:4][c:3]([O:2][CH3:1])[cH:8]3)[CH2:13][CH2:12][CH2:11]2)CCN1.OC(Cc1ccc(F)cc1)=[O:10]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([cH:8]1)[CH:9]([OH:10])[CH2:11][CH2:12][CH2:13]2 | COc1ccc2c(c1)C(N1CCNCC1)CCC2.O=C(O)Cc1ccc(F)cc1 | COc1ccc2c(c1)C(O)CCC2 | null | null | C(Cl)Cl | Heteroatom Alkylation and Arylation | OtherReaction | 2961cf827bb1ea49fca957afda11c5a0620619da2bdb83166c2193644481e6bd | de100094ba82befe71404cd4e538be3f54561a34b86a6393e5a09380bb15f1f3 | c1ccc2c(c1)CCCC2 | F-c1:c:c:c(-C-C(-O)=[O;H0;D1;+0:1]):c:c:1.[C:2]-[C:3]-[CH;D3;+0:4](-N1-C-C-N-C-C-1)-[c:5](:[c:6]):[c:7]>>[C:2]-[C:3]-[CH;D3;+0:4](-[OH;D1;+0:1])-[c:5](:[c:6]):[c:7] | 129 | [{"value": 129.0, "product": "OC1CCCC2=CC=C(C=C12)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 7-Methoxy-1-(piperazin-1-yl)-1,2,3,4-tetrahydronaphthalene (0.6 g) was reacted in methylene chloride for 2 hr with an acid chloride prepared from 4-fluorophenylacetic acid (0.44 g) and thionyl chloride (0.21 ml) Then the liquid reaction mixture was partitioned between methylene chloride and water, extracted with methyl... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Carboxylic acid.Secondary amine.Tertiary amine | Secondary alcohol | C1CNCCN1.c1ccc2c(c1)CCCC2.c1ccccc1 | c1ccc2c(c1)CCCC2 | c1ccc2c(c1)CCCC2 | HF | C(Cl)Cl | null | null | COc1ccc2c(c1)C(N1CCNCC1)CCC2.O=C(O)Cc1ccc(F)cc1>C(Cl)Cl>COc1ccc2c(c1)C(O)CCC2 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-efa657249b23494891be2e7eafdbf131 | COc1ccc2c(c1)C(N1CCN(C(=O)Cc3ccc(F)cc3)CC1)CCC2.O>>COc1ccc2c(c1)C(O)CCC2 | O.[OH-].[Na+].O.FC1=CC=C(C=C1)CC(=O)N1CCN(CC1)C1CCCC2=CC=C(C=C12)OC.[H-].[Al+3].[Li+].[H-].[H-].[H-]>>OC1CCCC2=CC=C(C=C12)OC | O=C(Cc1ccc(F)cc1)N1CCN([CH:9]2[c:7]3[c:6]([cH:5][cH:4][c:3]([O:2][CH3:1])[cH:8]3)[CH2:13][CH2:12][CH2:11]2)CC1.[OH2:10]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([cH:8]1)[CH:9]([OH:10])[CH2:11][CH2:12][CH2:13]2 | COc1ccc2c(c1)C(N1CCN(C(=O)Cc3ccc(F)cc3)CC1)CCC2.O | COc1ccc2c(c1)C(O)CCC2 | null | null | C1CCOC1 | Heteroatom Alkylation and Arylation | OtherReaction | a9971ef609225c82a1da634a1e1de2cb7f1ad51599dee03470daa8e39e57cdfc | 90c04b8595a667c001655d9ce8acc23ea919c06a61e880ef9be496b39ffd5f39 | c1ccc2c(c1)CCCC2 | F-c1:c:c:c(-C-C(=O)-N2-C-C-N(-[CH;D3;+0:1](-[C:2]-[C:3])-[c:4](:[c:5]):[c:6])-C-C-2):c:c:1.[OH2;D0;+0:7]>>[C:3]-[C:2]-[CH;D3;+0:1](-[OH;D1;+0:7])-[c:4](:[c:5]):[c:6] | null | [] | null | null | null | null | 1-[4-(4-Fluorophenylacetyl)piperazin-1-yl]-7-methoxy-1,2,3,4-tetrahydronaphthalene (0.41 g) and lithium aluminum hydride (0.05 g) were heated under reflux in THF (15 ml) for 6 hr. Next, the reaction solution was cooled and water (50 ml) a 5 N aqueous solution (50 ml) of sodium hydroxide and further water (150 ml) were ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Tertiary amide.Tertiary amine | Secondary alcohol | c1ccccc1.C1CNCCN1.c1ccc2c(c1)CCCC2 | c1ccc2c(c1)CCCC2 | c1ccc2c(c1)CCCC2 | HF | C1CCOC1 | null | null | COc1ccc2c(c1)C(N1CCN(C(=O)Cc3ccc(F)cc3)CC1)CCC2.O>C1CCOC1>COc1ccc2c(c1)C(O)CCC2 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-aeeb489cee824a02859ed9c14567ecc3 | c1cc2c(cn1)CCCC2>>[O-][n+]1ccc2c(c1)CCCC2 | C([O-])([O-])=O.[Na+].[Na+].ClC1=CC(=CC=C1)C(=O)OO.C1=NC=CC=2CCCCC12>>C1=[N+](C=CC=2CCCCC12)[O-] | [n:2]1[cH:3][cH:4][c:5]2[c:6]([cH:7]1)[CH2:8][CH2:9][CH2:10][CH2:11]2>>[O-:1][n+:2]1[cH:3][cH:4][c:5]2[c:6]([cH:7]1)[CH2:8][CH2:9][CH2:10][CH2:11]2 | c1cc2c(cn1)CCCC2 | [O-][n+]1ccc2c(c1)CCCC2 | null | null | C(Cl)Cl | Functional Group Interconversion | OtherReaction | 7c9e96ff1cec817e9c8ada9984173273c7f378d7d9cf98f4ea6cadccedc7ba1d | f1bbf9aa3c82f5e49be9f6d53533b6bb152f359232b6d32090c168949766aa71 | c1cc2c(c[nH+]1)CCCC2 | [c:1]:[c:2]:[n;H0;D2;+0:3]:[c:4]:[c:5]>>[O;-;D1;H0:6]-[n+;H0;D3:3](:[c:2]:[c:1]):[c:4]:[c:5] | null | [] | null | null | null | null | 5,6,7,8-Tetrahydroisoquinoline (10 g) was added to methylene chloride (100 ml) and a 10% aqueous solution (100 ml) of sodium carbonate. Under vigorous stirring, a 70% solution of m-chloroperbenzoic acid (20 g) in methylene chloride (100 ml) was dropped thereinto at 0° C. Then the reaction solution was extracted with me... | 10.6084/m9.figshare.5104873.v1 | null | null | null | c1cc2c(cn1)CCCC2 | C1=[NH+]C=C2CCCCC2=C1 | C1=[NH+]C=C2CCCCC2=C1 | null | C(Cl)Cl | null | null | c1cc2c(cn1)CCCC2>C(Cl)Cl>[O-][n+]1ccc2c(c1)CCCC2 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-e0463063f5d14fa394ec031932afb9ba | CC(=O)NCc1ccc2c(c1)N(C1CCN(CCc3ccc(F)cc3)CC1)CC2>>CC(=O)NCc1ccc2ccn(C3CCN(CCc4ccc(F)cc4)CC3)c2c1 | FC1=CC=C(CCN2CCC(CC2)N2CCC3=CC=C(C=C23)CNC(C)=O)C=C1>>FC1=CC=C(CCN2CCC(CC2)N2C=CC3=CC=C(C=C23)CNC(C)=O)C=C1 | [CH3:1][C:2](=[O:3])[NH:4][CH2:5][c:6]1[cH:7][cH:8][c:9]2[c:28]([cH:29]1)[N:12]([CH:13]1[CH2:14][CH2:15][N:16]([CH2:17][CH2:18][c:19]3[cH:20][cH:21][c:22]([F:23])[cH:24][cH:25]3)[CH2:26][CH2:27]1)[CH2:11][CH2:10]2>>[CH3:1][C:2](=[O:3])[NH:4][CH2:5][c:6]1[cH:7][cH:8][c:9]2[cH:10][cH:11][n:12]([CH:13]3[CH2:14][CH2:15][N:... | CC(=O)NCc1ccc2c(c1)N(C1CCN(CCc3ccc(F)cc3)CC1)CC2 | CC(=O)NCc1ccc2ccn(C3CCN(CCc4ccc(F)cc4)CC3)c2c1 | null | [O-2].[O-2].[Mn+4] | CC(=O)C | Oxidation | OtherReaction | 3747aca2f1587cdf6a8e2beafaad24064251ebc55727950e633c859c42148a48 | d04c5715e362fd32bffcfe60290c32ad0adedbe2d4f79a927f35e0b5f372b098 | c1ccc(CCN2CCC(n3ccc4ccccc43)CC2)cc1 | [C:1]-[C:2](-[N;H0;D3;+0:3]1-[CH2;D2;+0:4]-[CH2;D2;+0:5]-[c:6](:[c:7]):[c:8]-1:[c:9])-[C:10]>>[C:1]-[C:2](-[n;H0;D3;+0:3]1:[cH;D2;+0:4]:[cH;D2;+0:5]:[c:6](:[c:7]):[c:8]:1:[c:9])-[C:10] | 56.3 | [{"value": 56.3, "product": "FC1=CC=C(CCN2CCC(CC2)N2C=CC3=CC=C(C=C23)CNC(C)=O)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}, {"value": 56.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | 1-[1-(4-Fluorophenethyl)piperidin-4-yl]-6-acetamidomethylindoline (7.5 g) obtained in Example 133 was dissolved in acetone (500 ml) at 50° C. To the resultant solution was added active manganese dioxide (35.6 g) in portions under stirring. The resulting suspension was heated under reflux for 1.5 hr, then filtered throu... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amine | null | c1ccc2c(c1)CC[NH]2 | c1ccc2cc[nH]c2c1 | c1ccc2cc[nH]c2c1.C1CC[NH]CC1.c1ccccc1 | null | [O-2].[O-2].[Mn+4].CC(=O)C | null | null | CC(=O)NCc1ccc2c(c1)N(C1CCN(CCc3ccc(F)cc3)CC1)CC2>[O-2].[O-2].[Mn+4].CC(=O)C>CC(=O)NCc1ccc2ccn(C3CCN(CCc4ccc(F)cc4)CC3)c2c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-9dc8408c89a94e299be6d35e8736e5aa | Cn1cccc1.Fc1ccc(CCN2CCC(n3ccc4ccc(Br)cc43)CC2)cc1>>Cn1cccc1-c1ccc2ccn(C3CCN(CCc4ccc(F)cc4)CC3)c2c1 | FC1=CC=C(CCN2CCC(CC2)N2C=CC3=CC=C(C=C23)Br)C=C1.CN1C(=CC=C1)[Sn](CCCC)(CCCC)CCCC.CN1C=CC=C1.[Cl-]>>FC1=CC=C(CCN2CCC(CC2)N2C=CC3=CC=C(C=C23)C=2N(C=CC2)C)C=C1 | [CH3:1][n:2]1[cH:3][cH:4][cH:5][cH:6]1.Br[c:7]1[cH:8][cH:9][c:10]2[cH:11][cH:12][n:13]([CH:14]3[CH2:15][CH2:16][N:17]([CH2:18][CH2:19][c:20]4[cH:21][cH:22][c:23]([F:24])[cH:25][cH:26]4)[CH2:27][CH2:28]3)[c:29]2[cH:30]1>>[CH3:1][n:2]1[cH:3][cH:4][cH:5][c:6]1-[c:7]1[cH:8][cH:9][c:10]2[cH:11][cH:12][n:13]([CH:14]3[CH2:15]... | Cn1cccc1.Fc1ccc(CCN2CCC(n3ccc4ccc(Br)cc43)CC2)cc1 | Cn1cccc1-c1ccc2ccn(C3CCN(CCc4ccc(F)cc4)CC3)c2c1 | null | null | C1(=CC=CC=C1)C.C(C)(=O)OCC | C-C Coupling | OtherReaction | 7267135040d9f66f22c4f91254139efd57637f3666b718d86edf8912e9f53490 | 48892094855745f5c51f8910c27ce7c101e08ad3f9da2a58d5512e3d9c1b432f | c1ccc(CCN2CCC(n3ccc4ccc(-c5ccc[nH]5)cc43)CC2)cc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3](:[c:4]:[c:5]:[c:6]:1):[#7;a:7](-[C:8]):[c:9].[C;D1;H3:10]-[#7;a:11]1:[c:12]:[c:13]:[c:14]:[cH;D2;+0:15]:1>>[C:8]-[#7;a:7](:[c:9]):[c:3]1:[c:4]:[c:5]:[c:6]:[c;H0;D3;+0:1](-[c;H0;D3;+0:15]2:[c:14]:[c:13]:[c:12]:[#7;a:11]:2-[C;D1;H3:10]):[c:2]:1 | 57.5 | [{"value": 57.28, "product": "FC1=CC=C(CCN2CCC(CC2)N2C=CC3=CC=C(C=C23)C=2N(C=CC2)C)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 57.5, "product": "FC1=CC=C(CCN2CCC(CC2)N2C=CC3=CC=C(C=C23)C=2N(C=CC2)C)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 1-[1-(4-Fluorophenethyl)piperidin-4-yl]-6-bromoindole (0.2 g) was dissolved in toluene (2.50 ml). Next, 1-methyl-2-tributylstannylpyrrole (1.44 g) synthesized in accordance with the method described in Tetrahedron Lett., 4407 (1986). with the use of 1-methylpyrrole and tributylthin chloride was added thereto and the re... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | null | c1cc[nH]c1.c1ccc2cc[nH]c2c1 | c1ccc[nH]1.c1ccc2cc[nH]c2c1 | c1ccc[nH]1.c1ccc2cc[nH]c2c1.C1CC[NH]CC1.c1ccccc1 | HBr | C1(=CC=CC=C1)C.C(C)(=O)OCC | null | null | Cn1cccc1.Fc1ccc(CCN2CCC(n3ccc4ccc(Br)cc43)CC2)cc1>C1(=CC=CC=C1)C.C(C)(=O)OCC>Cn1cccc1-c1ccc2ccn(C3CCN(CCc4ccc(F)cc4)CC3)c2c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-2189746554ae41daa699e07252619468 | CC(=O)NCc1ccc(CCN2CCC(N3CCc4ccccc43)CC2)cc1>>CC(=O)NCc1ccc(CCN2CCC(n3ccc4ccccc43)CC2)cc1 | C(C)(=O)NCC1=CC=C(CCN2CCC(CC2)N2CCC3=CC=CC=C23)C=C1>>C(C)(=O)NCC1=CC=C(CCN2CCC(CC2)N2C=CC3=CC=CC=C23)C=C1 | [CH3:1][C:2](=[O:3])[NH:4][CH2:5][c:6]1[cH:7][cH:8][c:9]([CH2:10][CH2:11][N:12]2[CH2:13][CH2:14][CH:15]([N:16]3[CH2:17][CH2:18][c:19]4[cH:20][cH:21][cH:22][cH:23][c:24]43)[CH2:25][CH2:26]2)[cH:27][cH:28]1>>[CH3:1][C:2](=[O:3])[NH:4][CH2:5][c:6]1[cH:7][cH:8][c:9]([CH2:10][CH2:11][N:12]2[CH2:13][CH2:14][CH:15]([n:16]3[cH... | CC(=O)NCc1ccc(CCN2CCC(N3CCc4ccccc43)CC2)cc1 | CC(=O)NCc1ccc(CCN2CCC(n3ccc4ccccc43)CC2)cc1 | null | [O-2].[O-2].[Mn+4] | C(Cl)(Cl)Cl | Oxidation | OtherReaction | e52f71b450655496f3d86d95ebb6e98299f0cbbc99b337ca618ec98c1c63efaa | d04c5715e362fd32bffcfe60290c32ad0adedbe2d4f79a927f35e0b5f372b098 | c1ccc(CCN2CCC(n3ccc4ccccc43)CC2)cc1 | [C:1]-[C:2](-[N;H0;D3;+0:3]1-[CH2;D2;+0:4]-[CH2;D2;+0:5]-[c:6](:[c:7]):[c:8]-1:[c:9])-[C:10]>>[C:1]-[C:2](-[n;H0;D3;+0:3]1:[cH;D2;+0:4]:[cH;D2;+0:5]:[c:6](:[c:7]):[c:8]:1:[c:9])-[C:10] | 80.4 | [{"value": 80.4, "product": "C(C)(=O)NCC1=CC=C(CCN2CCC(CC2)N2C=CC3=CC=CC=C23)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 80.4, "product": "C(C)(=O)NCC1=CC=C(CCN2CCC(CC2)N2C=CC3=CC=CC=C23)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A suspension of 1-[1-(4-acetamidomethylphenethyl)piperidin-4-yl]indoline (0.80 g) obtained in Example 36 and active manganese dioxide (1.32 g) in chloroform (30 ml) was heated under reflux for 6 hr with vigorous stirring. Then the reaction mixtures were filtered through celite and the residue was washed with chloroform... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amine | null | c1ccc2c(c1)CC[NH]2 | c1ccc2[nH]ccc2c1 | c1ccccc1.C1CC[NH]CC1.c1ccc2[nH]ccc2c1 | null | [O-2].[O-2].[Mn+4].C(Cl)(Cl)Cl | null | null | CC(=O)NCc1ccc(CCN2CCC(N3CCc4ccccc43)CC2)cc1>[O-2].[O-2].[Mn+4].C(Cl)(Cl)Cl>CC(=O)NCc1ccc(CCN2CCC(n3ccc4ccccc43)CC2)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-6ced43dfa1b9493f945103a2c061ea56 | N#Cc1ccc2c(c1)N(C1CCN(CCc3ccc(F)cc3)CC1)CC2>>N#Cc1ccc2ccn(C3CCN(CCc4ccc(F)cc4)CC3)c2c1 | FC1=CC=C(CCN2CCC(CC2)N2CCC3=CC=C(C=C23)C#N)C=C1>>FC1=CC=C(CCN2CCC(CC2)N2C=CC3=CC=C(C=C23)C#N)C=C1 | [N:1]#[C:2][c:3]1[cH:4][cH:5][c:6]2[c:25]([cH:26]1)[N:9]([CH:10]1[CH2:11][CH2:12][N:13]([CH2:14][CH2:15][c:16]3[cH:17][cH:18][c:19]([F:20])[cH:21][cH:22]3)[CH2:23][CH2:24]1)[CH2:8][CH2:7]2>>[N:1]#[C:2][c:3]1[cH:4][cH:5][c:6]2[cH:7][cH:8][n:9]([CH:10]3[CH2:11][CH2:12][N:13]([CH2:14][CH2:15][c:16]4[cH:17][cH:18][c:19]([F... | N#Cc1ccc2c(c1)N(C1CCN(CCc3ccc(F)cc3)CC1)CC2 | N#Cc1ccc2ccn(C3CCN(CCc4ccc(F)cc4)CC3)c2c1 | null | [O-2].[O-2].[Mn+4] | null | Oxidation | OtherReaction | 3747aca2f1587cdf6a8e2beafaad24064251ebc55727950e633c859c42148a48 | d04c5715e362fd32bffcfe60290c32ad0adedbe2d4f79a927f35e0b5f372b098 | c1ccc(CCN2CCC(n3ccc4ccccc43)CC2)cc1 | [C:1]-[C:2](-[N;H0;D3;+0:3]1-[CH2;D2;+0:4]-[CH2;D2;+0:5]-[c:6](:[c:7]):[c:8]-1:[c:9])-[C:10]>>[C:1]-[C:2](-[n;H0;D3;+0:3]1:[cH;D2;+0:4]:[cH;D2;+0:5]:[c:6](:[c:7]):[c:8]:1:[c:9])-[C:10] | 84.5 | [{"value": 83.8, "product": "FC1=CC=C(CCN2CCC(CC2)N2C=CC3=CC=C(C=C23)C#N)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 84.5, "product": "FC1=CC=C(CCN2CCC(CC2)N2C=CC3=CC=C(C=C23)C#N)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 1-[1-(4-Fluorophenethyl)piperidin-4-yl]-6-cyanoindoline (0.50 g) obtained in Example 124 and active manganese dioxide (1.00 g) were treated as in Example 288 to give the title compound (0.42 g) as a white powder (yield: 83.8%).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amine | null | c1ccc2c(c1)CC[NH]2 | c1ccc2cc[nH]c2c1 | c1ccc2cc[nH]c2c1.C1CC[NH]CC1.c1ccccc1 | null | [O-2].[O-2].[Mn+4] | null | null | N#Cc1ccc2c(c1)N(C1CCN(CCc3ccc(F)cc3)CC1)CC2>[O-2].[O-2].[Mn+4]>N#Cc1ccc2ccn(C3CCN(CCc4ccc(F)cc4)CC3)c2c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-34eee7181b7f4acfbea646de6deb5eee | COc1ccc2c(c1)N(C1CCCN(CCc3ccc(F)cc3)CC1)C(=O)C2=O>>COc1ccc2ccn(C3CCCN(CCc4ccc(F)cc4)CC3)c2c1 | FC1=CC=C(CCN2CCC(CCC2)N2C(=O)C(=O)C3=CC=C(C=C23)OC)C=C1.O>>FC1=CC=C(CCN2CCC(CCC2)N2C=CC3=CC=C(C=C23)OC)C=C1 | O=[C:7]1[c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:27][c:26]2[N:9]([CH:10]2[CH2:11][CH2:12][CH2:13][N:14]([CH2:15][CH2:16][c:17]3[cH:18][cH:19][c:20]([F:21])[cH:22][cH:23]3)[CH2:24][CH2:25]2)[C:8]1=O>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[cH:7][cH:8][n:9]([CH:10]3[CH2:11][CH2:12][CH2:13][N:14]([CH2:15][CH2:16][c:17]4[cH:1... | COc1ccc2c(c1)N(C1CCCN(CCc3ccc(F)cc3)CC1)C(=O)C2=O | COc1ccc2ccn(C3CCCN(CCc4ccc(F)cc4)CC3)c2c1 | null | null | O1CCCC1 | Miscellaneous | OtherReaction | a84df4c7a05734d228fad41600e582f9472ec1c255198b83853f95abef8b9e31 | 859a0edf2382a200eae53621e7a1399268b892a729d9a6df2ea708544919156d | c1ccc(CCN2CCCC(n3ccc4ccccc43)CC2)cc1 | O=[C;H0;D3;+0:1]1-[C;H0;D3;+0:2](=O)-[N;H0;D3;+0:3](-[C:4](-[C:5])-[C:6])-[c:7](:[c:8]):[c:9]-1:[c:10]>>[C:5]-[C:4](-[n;H0;D3;+0:3]1:[cH;D2;+0:2]:[cH;D2;+0:1]:[c:9](:[c:10]):[c:7]:1:[c:8])-[C:6] | null | [] | null | null | 11 | HOUR | 1-(4-Fluorophenethyl)-4-(6-methoxyisatin-1-yl)homopiperidine (0.4 g) was dissolved in tetrahydrofuran (1.0 ml). Under nitrogen atmosphere, a 2.0 M solution (4.0 ml) of borane-tetrahydrofuran complex in tetrahydrofuran was added dropwise thereinto in a water bath followed by heating under reflux for 3 hr. The reaction s... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Tertiary amide | null | c1ccc2c(c1)CC[NH]2 | c1ccc2cc[nH]c2c1 | c1ccc2cc[nH]c2c1.C1CCC[NH]CC1.c1ccccc1 | Other | O1CCCC1 | null | 11 | COc1ccc2c(c1)N(C1CCCN(CCc3ccc(F)cc3)CC1)C(=O)C2=O>O1CCCC1>COc1ccc2ccn(C3CCCN(CCc4ccc(F)cc4)CC3)c2c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-f23be0e308a34927aa7afcab7bc48bcb | CC1(C)CNc2cc(Br)ccc21.O=C1CCN(CCc2ccc(F)cc2)CC1>>CC1(C)C(=O)Nc2cc(Br)ccc21 | CC1(CNC2=CC(=CC=C12)Br)C.FC1=CC=C(C=C1)CCN1CCC(CC1)=O>>CC1(C(NC2=CC(=CC=C12)Br)=O)C | [CH3:1][C:2]1([CH3:3])[CH2:4][NH:6][c:7]2[cH:8][c:9]([Br:10])[cH:11][cH:12][c:13]21.Fc1ccc(CCN2CCC(=[O:5])CC2)cc1>>[CH3:1][C:2]1([CH3:3])[C:4](=[O:5])[NH:6][c:7]2[cH:8][c:9]([Br:10])[cH:11][cH:12][c:13]21 | CC1(C)CNc2cc(Br)ccc21.O=C1CCN(CCc2ccc(F)cc2)CC1 | CC1(C)C(=O)Nc2cc(Br)ccc21 | null | null | null | Miscellaneous | OtherReaction | a0ab259c8e08925af3f2c3e849ddf4e3c495b90aab9bf96ee5f3f2b5ffd3a3da | b5dc52667a844a76b4e953a6ce3aa5722e87f51ef6c3a43f3eaad3b88955cabe | O=C1Cc2ccccc2N1 | F-c1:c:c:c(-C-C-N2-C-C-C(=[O;H0;D1;+0:1])-C-C-2):c:c:1.[C;D1;H3:2]-[C:3]1(-[C;D1;H3:4])-[CH2;D2;+0:5]-[#7:6]-[c:7]:[c:8]-1>>[C;D1;H3:2]-[C:3]1(-[C;D1;H3:4])-[c:8]:[c:7]-[#7:6]-[C;H0;D3;+0:5]-1=[O;H0;D1;+0:1] | 89.2 | [{"value": 89.2, "product": "CC1(C(NC2=CC(=CC=C12)Br)=O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}, {"value": 49.8, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | 3,3-Dimethyl-6-bromoindoline (3.10 g), 1-[2-(4-fluorophenyl)ethyl]-4-piperidone (2.81 g) and triacetoxylated sodium borohydride (5.70 g) were treated as in Example 16 to give the title compound (2.72 g) as a white amorphous solid (yield: 49.8%).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ketone.Tertiary amine | Secondary amide | c1ccc2c(c1)CCN2.c1ccccc1.C1CCNCC1 | c1ccc2c(c1)CCN2 | c1ccc2c(c1)CCN2 | HF | null | null | null | CC1(C)CNc2cc(Br)ccc21.O=C1CCN(CCc2ccc(F)cc2)CC1>>CC1(C)C(=O)Nc2cc(Br)ccc21 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-3bef6cddcc8f432a9aade264ee0bee09 | CCNC(=O)Cc1ccc2c(c1)N(C1CCN(CCc3ccc(F)cc3)CC1)CC2>>CCNC(=O)Cc1ccc2ccn(C3CCN(CCc4ccc(F)cc4)CC3)c2c1 | FC1=CC=C(CCN2CCC(CC2)N2CCC3=CC=C(C=C23)CC(NCC)=O)C=C1>>FC1=CC=C(CCN2CCC(CC2)N2C=CC3=CC=C(C=C23)CC(NCC)=O)C=C1 | [CH3:1][CH2:2][NH:3][C:4](=[O:5])[CH2:6][c:7]1[cH:8][cH:9][c:10]2[c:29]([cH:30]1)[N:13]([CH:14]1[CH2:15][CH2:16][N:17]([CH2:18][CH2:19][c:20]3[cH:21][cH:22][c:23]([F:24])[cH:25][cH:26]3)[CH2:27][CH2:28]1)[CH2:12][CH2:11]2>>[CH3:1][CH2:2][NH:3][C:4](=[O:5])[CH2:6][c:7]1[cH:8][cH:9][c:10]2[cH:11][cH:12][n:13]([CH:14]3[CH... | CCNC(=O)Cc1ccc2c(c1)N(C1CCN(CCc3ccc(F)cc3)CC1)CC2 | CCNC(=O)Cc1ccc2ccn(C3CCN(CCc4ccc(F)cc4)CC3)c2c1 | null | [O-2].[O-2].[Mn+4] | C(Cl)(Cl)Cl | Oxidation | OtherReaction | 3747aca2f1587cdf6a8e2beafaad24064251ebc55727950e633c859c42148a48 | d04c5715e362fd32bffcfe60290c32ad0adedbe2d4f79a927f35e0b5f372b098 | c1ccc(CCN2CCC(n3ccc4ccccc43)CC2)cc1 | [C:1]-[C:2](-[N;H0;D3;+0:3]1-[CH2;D2;+0:4]-[CH2;D2;+0:5]-[c:6](:[c:7]):[c:8]-1:[c:9])-[C:10]>>[C:1]-[C:2](-[n;H0;D3;+0:3]1:[cH;D2;+0:4]:[cH;D2;+0:5]:[c:6](:[c:7]):[c:8]:1:[c:9])-[C:10] | 89.5 | [{"value": 89.5, "product": "FC1=CC=C(CCN2CCC(CC2)N2C=CC3=CC=C(C=C23)CC(NCC)=O)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 80.9, "product": "FC1=CC=C(CCN2CCC(CC2)N2C=CC3=CC=C(C=C23)CC(NCC)=O)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 50 | CELSIUS | 6 | HOUR | A suspension of 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-(ethylcarbamoylmethyl)indoline (0.41 g) obtained in Example 149 and active manganese dioxide (0.40 g) in chloroform (30 ml) was vigorously stirred at 50° C. for 6 hr. Then the reaction mixtures were filtered through celite and the residue was washed with chlorof... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amine | null | c1ccc2c(c1)CC[NH]2 | c1ccc2cc[nH]c2c1 | c1ccc2cc[nH]c2c1.C1CC[NH]CC1.c1ccccc1 | null | [O-2].[O-2].[Mn+4].C(Cl)(Cl)Cl | 50 | 6 | CCNC(=O)Cc1ccc2c(c1)N(C1CCN(CCc3ccc(F)cc3)CC1)CC2>[O-2].[O-2].[Mn+4].C(Cl)(Cl)Cl>CCNC(=O)Cc1ccc2ccn(C3CCN(CCc4ccc(F)cc4)CC3)c2c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-16fb0e97fa884abab3ac689844bcc368 | O=C(Cc1ccc2c(c1)N(C1CCN(CCc3ccc(F)cc3)CC1)CC2)NC1CC1>>CCNC(=O)Cc1ccc2ccn(C3CCN(CCc4ccc(F)cc4)CC3)c2c1 | FC1=CC=C(CCN2CCC(CC2)N2CCC3=CC=C(C=C23)CC(NC2CC2)=O)C=C1>>FC1=CC=C(CCN2CCC(CC2)N2C=CC3=CC=C(C=C23)CC(NCC)=O)C=C1 | C1[CH2:1][CH:2]1[NH:3][C:4](=[O:5])[CH2:6][c:7]1[cH:8][cH:9][c:10]2[c:29]([cH:30]1)[N:13]([CH:14]1[CH2:15][CH2:16][N:17]([CH2:18][CH2:19][c:20]3[cH:21][cH:22][c:23]([F:24])[cH:25][cH:26]3)[CH2:27][CH2:28]1)[CH2:12][CH2:11]2>>[CH3:1][CH2:2][NH:3][C:4](=[O:5])[CH2:6][c:7]1[cH:8][cH:9][c:10]2[cH:11][cH:12][n:13]([CH:14]3[... | O=C(Cc1ccc2c(c1)N(C1CCN(CCc3ccc(F)cc3)CC1)CC2)NC1CC1 | CCNC(=O)Cc1ccc2ccn(C3CCN(CCc4ccc(F)cc4)CC3)c2c1 | null | [O-2].[O-2].[Mn+4] | C(Cl)(Cl)Cl | Miscellaneous | OtherReaction | dc2f58da7e8b471311a622bc90fd0f7ae2d5b855bff6075cfd262edc10e73794 | e0e88c13ed23bc13580ea72b7622523bab16ba5707a3942cafb26e1a1fd53aa9 | c1ccc(CCN2CCC(n3ccc4ccccc43)CC2)cc1 | [C:1]-[C:2](-[N;H0;D3;+0:3]1-[CH2;D2;+0:4]-[CH2;D2;+0:5]-[c:6](:[c:7]):[c:8]-1:[c:9])-[C:10].[C:11]-[C:12](=[O;D1;H0:13])-[#7:14]-[CH;D3;+0:15]1-C-[CH2;D2;+0:16]-1>>[C:1]-[C:2](-[n;H0;D3;+0:3]1:[cH;D2;+0:4]:[cH;D2;+0:5]:[c:6](:[c:7]):[c:8]:1:[c:9])-[C:10].[C:11]-[C:12](=[O;D1;H0:13])-[#7:14]-[CH2;D2;+0:15]-[CH3;D1;+0:1... | 81.9 | [{"value": 81.9, "product": "FC1=CC=C(CCN2CCC(CC2)N2C=CC3=CC=C(C=C23)CC(NCC)=O)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 77.6, "product": "FC1=CC=C(CCN2CCC(CC2)N2C=CC3=CC=C(C=C23)CC(NCC)=O)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 50 | CELSIUS | 10 | HOUR | A suspension of 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-[(cyclopropylcarbamoyl)methyl]indoline (0.04 g) obtained in Example 154 and active manganese dioxide (0.04 g) in chloroform (30 ml) was vigorously stirred at 50° C. for 10 hr. Then the reaction mixtures were filtered through celite and the residue was washed wit... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amine | null | C1CC1.c1ccc2c(c1)CC[NH]2 | c1ccc2cc[nH]c2c1 | c1ccc2cc[nH]c2c1.C1CC[NH]CC1.c1ccccc1 | Other | [O-2].[O-2].[Mn+4].C(Cl)(Cl)Cl | 50 | 10 | O=C(Cc1ccc2c(c1)N(C1CCN(CCc3ccc(F)cc3)CC1)CC2)NC1CC1>[O-2].[O-2].[Mn+4].C(Cl)(Cl)Cl>CCNC(=O)Cc1ccc2ccn(C3CCN(CCc4ccc(F)cc4)CC3)c2c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-7ba06a0745eb45d59643d5c89d39e192 | CC(C)CNC(=O)Cc1ccc2c(c1)N(C1CCN(CCc3ccc(F)cc3)CC1)CC2>>CCNC(=O)Cc1ccc2ccn(C3CCN(CCc4ccc(F)cc4)CC3)c2c1 | FC1=CC=C(CCN2CCC(CC2)N2CCC3=CC=C(C=C23)CC(NCC(C)C)=O)C=C1>>FC1=CC=C(CCN2CCC(CC2)N2C=CC3=CC=C(C=C23)CC(NCC)=O)C=C1 | C[CH:1](C)[CH2:2][NH:3][C:4](=[O:5])[CH2:6][c:7]1[cH:8][cH:9][c:10]2[c:29]([cH:30]1)[N:13]([CH:14]1[CH2:15][CH2:16][N:17]([CH2:18][CH2:19][c:20]3[cH:21][cH:22][c:23]([F:24])[cH:25][cH:26]3)[CH2:27][CH2:28]1)[CH2:12][CH2:11]2>>[CH3:1][CH2:2][NH:3][C:4](=[O:5])[CH2:6][c:7]1[cH:8][cH:9][c:10]2[cH:11][cH:12][n:13]([CH:14]3... | CC(C)CNC(=O)Cc1ccc2c(c1)N(C1CCN(CCc3ccc(F)cc3)CC1)CC2 | CCNC(=O)Cc1ccc2ccn(C3CCN(CCc4ccc(F)cc4)CC3)c2c1 | null | [O-2].[O-2].[Mn+4] | C(Cl)(Cl)Cl | Miscellaneous | OtherReaction | db6a953d59beb719e5fffcfea545638d02f19b11979a682bb66f41f488175488 | e0e88c13ed23bc13580ea72b7622523bab16ba5707a3942cafb26e1a1fd53aa9 | c1ccc(CCN2CCC(n3ccc4ccccc43)CC2)cc1 | C-[CH;D3;+0:1](-C)-[C:2]-[#7:3]-[C:4]=[O;D1;H0:5].[C:6]-[C:7](-[N;H0;D3;+0:8]1-[CH2;D2;+0:9]-[CH2;D2;+0:10]-[c:11](:[c:12]):[c:13]-1:[c:14])-[C:15]>>[CH3;D1;+0:1]-[C:2]-[#7:3]-[C:4]=[O;D1;H0:5].[C:6]-[C:7](-[n;H0;D3;+0:8]1:[cH;D2;+0:9]:[cH;D2;+0:10]:[c:11](:[c:12]):[c:13]:1:[c:14])-[C:15] | 76.7 | [{"value": 70.0, "product": "FC1=CC=C(CCN2CCC(CC2)N2C=CC3=CC=C(C=C23)CC(NCC)=O)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 76.7, "product": "FC1=CC=C(CCN2CCC(CC2)N2C=CC3=CC=C(C=C23)CC(NCC)=O)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 50 | CELSIUS | 8 | HOUR | A suspension of 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-[(isobutylcarbamoyl)methyl]indoline (0.07 g) obtained in Example 152 and active manganese dioxide (0.07 g) in chloroform (30 ml) was vigorously stirred at 50° C. overnight. Then the reaction mixtures were filtered through celite and the residue was washed with c... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amine | null | c1ccc2c(c1)CC[NH]2 | c1ccc2cc[nH]c2c1 | c1ccc2cc[nH]c2c1.C1CC[NH]CC1.c1ccccc1 | Other | [O-2].[O-2].[Mn+4].C(Cl)(Cl)Cl | 50 | 8 | CC(C)CNC(=O)Cc1ccc2c(c1)N(C1CCN(CCc3ccc(F)cc3)CC1)CC2>[O-2].[O-2].[Mn+4].C(Cl)(Cl)Cl>CCNC(=O)Cc1ccc2ccn(C3CCN(CCc4ccc(F)cc4)CC3)c2c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-7997046f50a54e64aea1dc32d4734df7 | CCCNC(=O)Cc1ccc2c(c1)N(C1CCN(CCc3ccc(F)cc3)CC1)CC2>>CCNC(=O)Cc1ccc2ccn(C3CCN(CCc4ccc(F)cc4)CC3)c2c1 | FC1=CC=C(CCN2CCC(CC2)N2CCC3=CC=C(C=C23)CC(NCCC)=O)C=C1>>FC1=CC=C(CCN2CCC(CC2)N2C=CC3=CC=C(C=C23)CC(NCC)=O)C=C1 | C[CH2:1][CH2:2][NH:3][C:4](=[O:5])[CH2:6][c:7]1[cH:8][cH:9][c:10]2[c:29]([cH:30]1)[N:13]([CH:14]1[CH2:15][CH2:16][N:17]([CH2:18][CH2:19][c:20]3[cH:21][cH:22][c:23]([F:24])[cH:25][cH:26]3)[CH2:27][CH2:28]1)[CH2:12][CH2:11]2>>[CH3:1][CH2:2][NH:3][C:4](=[O:5])[CH2:6][c:7]1[cH:8][cH:9][c:10]2[cH:11][cH:12][n:13]([CH:14]3[C... | CCCNC(=O)Cc1ccc2c(c1)N(C1CCN(CCc3ccc(F)cc3)CC1)CC2 | CCNC(=O)Cc1ccc2ccn(C3CCN(CCc4ccc(F)cc4)CC3)c2c1 | null | [O-2].[O-2].[Mn+4] | C(Cl)(Cl)Cl | Miscellaneous | OtherReaction | db6a953d59beb719e5fffcfea545638d02f19b11979a682bb66f41f488175488 | e0e88c13ed23bc13580ea72b7622523bab16ba5707a3942cafb26e1a1fd53aa9 | c1ccc(CCN2CCC(n3ccc4ccccc43)CC2)cc1 | C-[CH2;D2;+0:1]-[C:2]-[#7:3]-[C:4]=[O;D1;H0:5].[C:6]-[C:7](-[N;H0;D3;+0:8]1-[CH2;D2;+0:9]-[CH2;D2;+0:10]-[c:11](:[c:12]):[c:13]-1:[c:14])-[C:15]>>[CH3;D1;+0:1]-[C:2]-[#7:3]-[C:4]=[O;D1;H0:5].[C:6]-[C:7](-[n;H0;D3;+0:8]1:[cH;D2;+0:9]:[cH;D2;+0:10]:[c:11](:[c:12]):[c:13]:1:[c:14])-[C:15] | 84.6 | [{"value": 84.6, "product": "FC1=CC=C(CCN2CCC(CC2)N2C=CC3=CC=C(C=C23)CC(NCC)=O)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 78.0, "product": "FC1=CC=C(CCN2CCC(CC2)N2C=CC3=CC=C(C=C23)CC(NCC)=O)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 50 | CELSIUS | 8 | HOUR | A suspension of 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-[(n-propylcarbamoyl)methyl]indoline (0.04 g) obtained in Example 150 and active manganese dioxide (0.08 g) in chloroform (30 ml) was vigorously stirred at 50° C. overnight. Then the reaction mixtures were filtered through celite and the residue was washed with c... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amine | null | c1ccc2c(c1)CC[NH]2 | c1ccc2cc[nH]c2c1 | c1ccc2cc[nH]c2c1.C1CC[NH]CC1.c1ccccc1 | Other | [O-2].[O-2].[Mn+4].C(Cl)(Cl)Cl | 50 | 8 | CCCNC(=O)Cc1ccc2c(c1)N(C1CCN(CCc3ccc(F)cc3)CC1)CC2>[O-2].[O-2].[Mn+4].C(Cl)(Cl)Cl>CCNC(=O)Cc1ccc2ccn(C3CCN(CCc4ccc(F)cc4)CC3)c2c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-73405c1cfbe74fcaa850e38e2982bcb1 | CC(=O)N1CCC(CN)CC1>>CCN1CCC(CN)CC1 | [H-].[Al+3].[Li+].[H-].[H-].[H-].C(C)(=O)N1CCC(CC1)CN.O.[OH-].[Na+].O>>C(C)N1CCC(CC1)CN | O=[C:2]([CH3:1])[N:3]1[CH2:4][CH2:5][CH:6]([CH2:7][NH2:8])[CH2:9][CH2:10]1>>[CH3:1][CH2:2][N:3]1[CH2:4][CH2:5][CH:6]([CH2:7][NH2:8])[CH2:9][CH2:10]1 | CC(=O)N1CCC(CN)CC1 | CCN1CCC(CN)CC1 | null | null | O1CCCC1.C(C)(=O)OCC | Reduction | Reduction of tertiary amides to amines | f74c5a050b269ec4da3871c266f01344b7447381f47cda744f8b1e9c225ae62d | c8f3c617792f7a4fae96b8a97dc0ce23461ab85d8a738fe6caacff776ef51ffa | C1CCNCC1 | O=[C;H0;D3;+0:1](-[C;D1;H3:2])-[#7:3](-[C:4])-[C:5]>>[C:4]-[#7:3](-[CH2;D2;+0:1]-[C;D1;H3:2])-[C:5] | 83.6 | [{"value": 83.6, "product": "C(C)N1CCC(CC1)CN", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Lithium aluminum hydride (1.06 g) was suspended in tetrahydrofuran (70 ml) and the resultant suspension was stirred under nitrogen atmosphere under ice cooling. Next, 1-acetyl-4-aminomethylpiperidine (4.14 g). dissolved in tetrahydrofuran (30 ml) was added thereto and the resultant mixture was stirred at room temperatu... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide | null | null | null | C1CC[NH]CC1 | Other | O1CCCC1.C(C)(=O)OCC | null | null | CC(=O)N1CCC(CN)CC1>O1CCCC1.C(C)(=O)OCC>CCN1CCC(CN)CC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-40652b9569aa48bbac61ef803c67c712 | Brc1ccc2c(c1)NCC2.O=C1CCN(CCc2ccccc2F)CC1>>Fc1ccccc1CCN1CCC(N2CCc3ccc(Br)cc32)CC1 | BrC1=CC=C2CCNC2=C1.FC1=C(CCN2CCC(CC2)=O)C=CC=C1.C(C)(=O)O.[OH-].[Na+]>>FC1=C(CCN2CCC(CC2)N2CCC3=CC=C(C=C23)Br)C=CC=C1 | [NH:14]1[CH2:15][CH2:16][c:17]2[cH:18][cH:19][c:20]([Br:21])[cH:22][c:23]21.O=[C:13]1[CH2:12][CH2:11][N:10]([CH2:9][CH2:8][c:7]2[c:2]([F:1])[cH:3][cH:4][cH:5][cH:6]2)[CH2:25][CH2:24]1>>[F:1][c:2]1[cH:3][cH:4][cH:5][cH:6][c:7]1[CH2:8][CH2:9][N:10]1[CH2:11][CH2:12][CH:13]([N:14]2[CH2:15][CH2:16][c:17]3[cH:18][cH:19][c:20... | Brc1ccc2c(c1)NCC2.O=C1CCN(CCc2ccccc2F)CC1 | Fc1ccccc1CCN1CCC(N2CCc3ccc(Br)cc32)CC1 | null | null | ClCCCl.C(C)(=O)OCC | Heteroatom Alkylation and Arylation | OtherReaction | ed5f829465aab8e8fa321fc868dfe3231b2d42ce59513bacd6302db66ad15586 | 99acf13bfcfe579f51ccb82c65e4ca039ee7ca9b6fcd2747a3d9a292a88e564e | c1ccc(CCN2CCC(N3CCc4ccccc43)CC2)cc1 | O=[C;H0;D3;+0:1]1-[C:2]-[C:3]-[#7:4]-[C:5]-[C:6]-1.[c:7]:[c:8]1:[c:9]-[C:10]-[C:11]-[NH;D2;+0:12]-1>>[c:7]:[c:8]1:[c:9]-[C:10]-[C:11]-[N;H0;D3;+0:12]-1-[CH;D3;+0:1]1-[C:2]-[C:3]-[#7:4]-[C:5]-[C:6]-1 | 66.6 | [{"value": 66.6, "product": "FC1=C(CCN2CCC(CC2)N2CCC3=CC=C(C=C23)Br)C=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 66.6, "product": "FC1=C(CCN2CCC(CC2)N2CCC3=CC=C(C=C23)Br)C=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | Triacetoxylated sodium borohydride (15.0 g) was added under ice cooling to a liquid mixture of 6-bromoindoline (9.0 g), 1-(2-fluorophenethyl)piperidin-4-one (11.0 g) and acetic acid (12.5 ml) in 1,2-dichloroethane (140 ml). Then the reaction mixtures were stirred at room temperature overnight. The reaction mixtures wer... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Secondary amine | Tertiary amine | c1ccc2c(c1)CCN2.C1CC[NH]CC1 | C1CC[NH]CC1.c1ccc2c(c1)CC[NH]2 | c1ccccc1.C1CC[NH]CC1.c1ccc2c(c1)CC[NH]2 | Other | ClCCCl.C(C)(=O)OCC | null | 8 | Brc1ccc2c(c1)NCC2.O=C1CCN(CCc2ccccc2F)CC1>ClCCCl.C(C)(=O)OCC>Fc1ccccc1CCN1CCC(N2CCc3ccc(Br)cc32)CC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-286c2e757c554ba2b8f51cc0a8f53262 | CN(C)C=O.Fc1ccccc1CCN1CCC(N2CCc3ccc(Br)cc32)CC1>>O=Cc1ccc2c(c1)N(C1CCN(CCc3ccccc3F)CC1)CC2 | CN(C=O)C.[Cl-].[NH4+].C(C)(=O)OCC.FC1=C(CCN2CCC(CC2)N2CCC3=CC=C(C=C23)Br)C=CC=C1>>FC1=C(CCN2CCC(CC2)N2CCC3=CC=C(C=C23)C=O)C=CC=C1 | CN(C)[CH:2]=[O:1].Br[c:3]1[cH:4][cH:5][c:6]2[c:7]([cH:8]1)[N:9]([CH:10]1[CH2:11][CH2:12][N:13]([CH2:14][CH2:15][c:16]3[cH:17][cH:18][cH:19][cH:20][c:21]3[F:22])[CH2:23][CH2:24]1)[CH2:25][CH2:26]2>>[O:1]=[CH:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([cH:8]1)[N:9]([CH:10]1[CH2:11][CH2:12][N:13]([CH2:14][CH2:15][c:16]3[cH:17][cH:18... | CN(C)C=O.Fc1ccccc1CCN1CCC(N2CCc3ccc(Br)cc32)CC1 | O=Cc1ccc2c(c1)N(C1CCN(CCc3ccccc3F)CC1)CC2 | null | null | O1CCCC1.CCCCCC | C-C Coupling | Bouveault aldehyde synthesis | b0efeb5180af9fbef285e253c0928a97b026f034c600036c105952925053abc3 | afd09ced98f25d311f21cc04ba6a50fe7e5516de47e17484683ded13d323b1b2 | c1ccc(CCN2CCC(N3CCc4ccccc43)CC2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5]-[#7:6].C-N(-C)-[CH;D2;+0:7]=[O;D1;H0:8]>>[#7:6]-[c:5]:[c:4]:[c;H0;D3;+0:1](-[CH;D2;+0:7]=[O;D1;H0:8]):[c:2]:[c:3] | 91.5 | [{"value": 91.5, "product": "FC1=C(CCN2CCC(CC2)N2CCC3=CC=C(C=C23)C=O)C=CC=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 10 | MINUTE | A 1.6 M solution (24 ml) of n-(butyllithium) in hexane was added dropwise at −78° C. over 10 min into a solution of 1-[1-(2-fluorophenethyl)piperidin-4-yl]-6-bromoindoline (12 g) obtained in Example 348-2) in tetrahydrofuran (200 ml). After 10 min, dimethylformamide (3.5 ml) was added thereto and the resultant mixture ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Tertiary amide | Aldehyde | c1ccc2c(c1)CC[NH]2 | c1ccc2c(c1)CC[NH]2 | C1CC[NH]CC1.c1ccccc1.c1ccc2c(c1)CC[NH]2 | HBr | O1CCCC1.CCCCCC | null | 0.166667 | CN(C)C=O.Fc1ccccc1CCN1CCC(N2CCc3ccc(Br)cc32)CC1>O1CCCC1.CCCCCC>O=Cc1ccc2c(c1)N(C1CCN(CCc3ccccc3F)CC1)CC2 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-3ebb3a470de94017a092fdbf3885cf0a | O=Cc1ccc2c(c1)N(C1CCN(CCc3ccccc3F)CC1)CC2>>O=Cc1ccc2ccn(C3CCN(CCc4ccccc4F)CC3)c2c1 | FC1=C(CCN2CCC(CC2)N2CCC3=CC=C(C=C23)C=O)C=CC=C1>>FC1=C(CCN2CCC(CC2)N2C=CC3=CC=C(C=C23)C=O)C=CC=C1 | [O:1]=[CH:2][c:3]1[cH:4][cH:5][c:6]2[c:25]([cH:26]1)[N:9]([CH:10]1[CH2:11][CH2:12][N:13]([CH2:14][CH2:15][c:16]3[cH:17][cH:18][cH:19][cH:20][c:21]3[F:22])[CH2:23][CH2:24]1)[CH2:8][CH2:7]2>>[O:1]=[CH:2][c:3]1[cH:4][cH:5][c:6]2[cH:7][cH:8][n:9]([CH:10]3[CH2:11][CH2:12][N:13]([CH2:14][CH2:15][c:16]4[cH:17][cH:18][cH:19][c... | O=Cc1ccc2c(c1)N(C1CCN(CCc3ccccc3F)CC1)CC2 | O=Cc1ccc2ccn(C3CCN(CCc4ccccc4F)CC3)c2c1 | null | [O-2].[O-2].[Mn+4].[O-2].[O-2].[Mn+4] | C(Cl)(Cl)Cl | Oxidation | OtherReaction | 3747aca2f1587cdf6a8e2beafaad24064251ebc55727950e633c859c42148a48 | d04c5715e362fd32bffcfe60290c32ad0adedbe2d4f79a927f35e0b5f372b098 | c1ccc(CCN2CCC(n3ccc4ccccc43)CC2)cc1 | [C:1]-[C:2](-[N;H0;D3;+0:3]1-[CH2;D2;+0:4]-[CH2;D2;+0:5]-[c:6](:[c:7]):[c:8]-1:[c:9])-[C:10]>>[C:1]-[C:2](-[n;H0;D3;+0:3]1:[cH;D2;+0:4]:[cH;D2;+0:5]:[c:6](:[c:7]):[c:8]:1:[c:9])-[C:10] | 78 | [{"value": 78.0, "product": "FC1=C(CCN2CCC(CC2)N2C=CC3=CC=C(C=C23)C=O)C=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 78.0, "product": "FC1=C(CCN2CCC(CC2)N2C=CC3=CC=C(C=C23)C=O)C=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A suspension of 1-[1-(2-fluorophenethyl)piperidin-4-yl]-6-formylindoline (2.50 g) obtained in Example 348-3) and activated manganese dioxide (5.0 g) in chloroform (100 ml) was heated under reflux for 4 hr under vigorous stirring. Further, activated manganese dioxide (5.0 g×1, 2.5 g×2) was added to the reaction mixture ... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amine | null | c1ccc2c(c1)CC[NH]2 | c1ccc2cc[nH]c2c1 | c1ccc2cc[nH]c2c1.C1CC[NH]CC1.c1ccccc1 | null | [O-2].[O-2].[Mn+4].[O-2].[O-2].[Mn+4].C(Cl)(Cl)Cl | null | null | O=Cc1ccc2c(c1)N(C1CCN(CCc3ccccc3F)CC1)CC2>[O-2].[O-2].[Mn+4].[O-2].[O-2].[Mn+4].C(Cl)(Cl)Cl>O=Cc1ccc2ccn(C3CCN(CCc4ccccc4F)CC3)c2c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-a03bc70265cb4b258a82aa2264d0ca35 | NO.O=Cc1ccc2ccn(C3CCN(CCc4ccccc4F)CC3)c2c1>>ON=Cc1ccc2ccn(C3CCN(CCc4ccccc4F)CC3)c2c1 | FC1=C(CCN2CCC(CC2)N2C=CC3=CC=C(C=C23)C=O)C=CC=C1.Cl.NO.C(C)(=O)[O-].[Na+]>>FC1=C(CCN2CCC(CC2)N2C=CC3=CC=C(C=C23)C=NO)C=CC=C1 | [OH:1][NH2:2].O=[CH:3][c:4]1[cH:5][cH:6][c:7]2[cH:8][cH:9][n:10]([CH:11]3[CH2:12][CH2:13][N:14]([CH2:15][CH2:16][c:17]4[cH:18][cH:19][cH:20][cH:21][c:22]4[F:23])[CH2:24][CH2:25]3)[c:26]2[cH:27]1>>[OH:1][N:2]=[CH:3][c:4]1[cH:5][cH:6][c:7]2[cH:8][cH:9][n:10]([CH:11]3[CH2:12][CH2:13][N:14]([CH2:15][CH2:16][c:17]4[cH:18][c... | NO.O=Cc1ccc2ccn(C3CCN(CCc4ccccc4F)CC3)c2c1 | ON=Cc1ccc2ccn(C3CCN(CCc4ccccc4F)CC3)c2c1 | null | null | CO | Heteroatom Alkylation and Arylation | OtherReaction | 26f32c058bcc6b69b34e9c38433bccb165270e0a55ab24439c783c1aee9d8dac | 3593c4a8dedbac5f92a1a749cef37ecd686935362f91b9154f0c9930a5edea38 | c1ccc(CCN2CCC(n3ccc4ccccc43)CC2)cc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4]:[c:5]:[#7;a:6].[NH2;D1;+0:7]-[O;D1;H1:8]>>[#7;a:6]:[c:5]:[c:4]:[c:2](-[CH;D2;+0:1]=[N;H0;D2;+0:7]-[O;D1;H1:8]):[c:3] | 96.9 | [{"value": 96.8, "product": "FC1=C(CCN2CCC(CC2)N2C=CC3=CC=C(C=C23)C=NO)C=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 96.9, "product": "FC1=C(CCN2CCC(CC2)N2C=CC3=CC=C(C=C23)C=NO)C=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | A mixture of 1-[1-(2-fluorophenethyl)piperidin-4-yl]-6-formylindole (1.94 g) obtained in Example 348-4), hydroxylamine hydrochloride (0.5 g) and anhydrous sodium acetate (0.55 g) in methanol (60 ml) was stirred at room temperature for 1 hr. Then the reaction mixtures were concentrated and the residue was partitioned be... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Primary amine | Oxime | null | null | c1ccc2cc[nH]c2c1.C1CC[NH]CC1.c1ccccc1 | HO- | CO | null | 1 | NO.O=Cc1ccc2ccn(C3CCN(CCc4ccccc4F)CC3)c2c1>CO>ON=Cc1ccc2ccn(C3CCN(CCc4ccccc4F)CC3)c2c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-07b3222edee24a299a40596e3bee1cb6 | ON=Cc1ccc2ccn(C3CCN(CCc4ccccc4F)CC3)c2c1>>O=Cc1ccc2ccn(C3CCN(CCc4ccccc4F)CC3)c2c1 | O.[OH-].[Na+].O.[H-].[Al+3].[Li+].[H-].[H-].[H-].FC1=C(CCN2CCC(CC2)N2C=CC3=CC=C(C=C23)C=NO)C=CC=C1>>FC1=C(CCN2CCC(CC2)N2C=CC3=CC=C(C=C23)C=O)C=CC=C1 | N([OH:1])=[CH:2][c:3]1[cH:4][cH:5][c:6]2[cH:7][cH:8][n:9]([CH:10]3[CH2:11][CH2:12][N:13]([CH2:14][CH2:15][c:16]4[cH:17][cH:18][cH:19][cH:20][c:21]4[F:22])[CH2:23][CH2:24]3)[c:25]2[cH:26]1>>[O:1]=[CH:2][c:3]1[cH:4][cH:5][c:6]2[cH:7][cH:8][n:9]([CH:10]3[CH2:11][CH2:12][N:13]([CH2:14][CH2:15][c:16]4[cH:17][cH:18][cH:19][c... | ON=Cc1ccc2ccn(C3CCN(CCc4ccccc4F)CC3)c2c1 | O=Cc1ccc2ccn(C3CCN(CCc4ccccc4F)CC3)c2c1 | null | null | O1CCCC1 | Reduction | OtherReaction | ba44a29b6bc3f2668228fb57b1c547775f6abf612dbaf99b39892bc5da64260c | b1fa90f32bf8c94e331ae277d083a92aaa9c2433a5ae262fd8b19e6e3c16205b | c1ccc(CCN2CCC(n3ccc4ccccc43)CC2)cc1 | [#7;a:1]:[c:2]:[c:3]:[c:4](-[CH;D2;+0:5]=N-[OH;D1;+0:6]):[c:7]>>[#7;a:1]:[c:2]:[c:3]:[c:4](-[CH;D2;+0:5]=[O;H0;D1;+0:6]):[c:7] | 49.1 | [{"value": 49.1, "product": "FC1=C(CCN2CCC(CC2)N2C=CC3=CC=C(C=C23)C=O)C=CC=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 1-[1-(2-fluorophenethyl)piperidin-4-yl]-6-hydroxyiminomethylindole (1.95 g) in tetrahydrofuran (50 ml) was added dropwise at room temperature under ice cooling and stirring into a suspension of lithium aluminum hydride (0.4 g) in tetrahydrofuran (100 ml). Then the resultant mixture was heated under reflux... | 10.6084/m9.figshare.5104873.v1 | null | Oxime | Aldehyde | null | null | c1ccc2cc[nH]c2c1.C1CC[NH]CC1.c1ccccc1 | Other | O1CCCC1 | null | null | ON=Cc1ccc2ccn(C3CCN(CCc4ccccc4F)CC3)c2c1>O1CCCC1>O=Cc1ccc2ccn(C3CCN(CCc4ccccc4F)CC3)c2c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-6772ea0dbccd44d99c7354c0a50d109a | O=C1CCCN1Cc1ccc2c(c1)N(C1CCN(CCc3ccc(F)cc3)CC1)CC2>>O=C1CCCN1Cc1ccc2ccn(C3CCN(CCc4ccc(F)cc4)CC3)c2c1 | FC1=CC=C(CCN2CCC(CC2)N2CCC3=CC=C(C=C23)CN2C(CCC2)=O)C=C1>>FC1=CC=C(CCN2CCC(CC2)N2C=CC3=CC=C(C=C23)CN2C(CCC2)=O)C=C1 | [O:1]=[C:2]1[CH2:3][CH2:4][CH2:5][N:6]1[CH2:7][c:8]1[cH:9][cH:10][c:11]2[c:30]([cH:31]1)[N:14]([CH:15]1[CH2:16][CH2:17][N:18]([CH2:19][CH2:20][c:21]3[cH:22][cH:23][c:24]([F:25])[cH:26][cH:27]3)[CH2:28][CH2:29]1)[CH2:13][CH2:12]2>>[O:1]=[C:2]1[CH2:3][CH2:4][CH2:5][N:6]1[CH2:7][c:8]1[cH:9][cH:10][c:11]2[cH:12][cH:13][n:1... | O=C1CCCN1Cc1ccc2c(c1)N(C1CCN(CCc3ccc(F)cc3)CC1)CC2 | O=C1CCCN1Cc1ccc2ccn(C3CCN(CCc4ccc(F)cc4)CC3)c2c1 | null | [O-2].[O-2].[Mn+4] | C(Cl)(Cl)Cl | Oxidation | OtherReaction | 3747aca2f1587cdf6a8e2beafaad24064251ebc55727950e633c859c42148a48 | d04c5715e362fd32bffcfe60290c32ad0adedbe2d4f79a927f35e0b5f372b098 | O=C1CCCN1Cc1ccc2ccn(C3CCN(CCc4ccccc4)CC3)c2c1 | [C:1]-[C:2](-[N;H0;D3;+0:3]1-[CH2;D2;+0:4]-[CH2;D2;+0:5]-[c:6](:[c:7]):[c:8]-1:[c:9])-[C:10]>>[C:1]-[C:2](-[n;H0;D3;+0:3]1:[cH;D2;+0:4]:[cH;D2;+0:5]:[c:6](:[c:7]):[c:8]:1:[c:9])-[C:10] | 86.7 | [{"value": 86.7, "product": "FC1=CC=C(CCN2CCC(CC2)N2C=CC3=CC=C(C=C23)CN2C(CCC2)=O)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 1-[1-(4-Fluorophenethyl)piperidin-4-yl]-6-(2-pyrrolidon-1-yl) methylindoline (80 mg) obtained in Example 202, activated manganese dioxide (400 mg) and chloroform (10 ml) were treated as in Example 285 to give the title compound (69 mg) as an oil. This oil was then crystallized from ethyl acetate by using oxalic acid (1... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amine | null | c1ccc2c(c1)CC[NH]2 | c1ccc2cc[nH]c2c1 | C1CC[NH]C1.c1ccc2cc[nH]c2c1.C1CC[NH]CC1.c1ccccc1 | null | [O-2].[O-2].[Mn+4].C(Cl)(Cl)Cl | null | null | O=C1CCCN1Cc1ccc2c(c1)N(C1CCN(CCc3ccc(F)cc3)CC1)CC2>[O-2].[O-2].[Mn+4].C(Cl)(Cl)Cl>O=C1CCCN1Cc1ccc2ccn(C3CCN(CCc4ccc(F)cc4)CC3)c2c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-db6f415e7e084b09b44668299b1aca5c | CC(Cl)Cl.CN.O=Cc1ccc2ccn(C3CCN(CCc4ccc(F)cc4)CC3)c2c1>>O=C1CCCN1Cc1ccc2ccn(C3CCN(CCc4ccc(F)cc4)CC3)c2c1 | FC1=CC=C(CCN2CCC(CC2)N2C=CC3=CC=C(C=C23)C=O)C=C1.Cl.CN.C(C)(=O)O[BH-](OC(C)=O)OC(C)=O.[Na+].ClC(C)Cl.C([O-])(O)=O.[Na+]>>FC1=CC=C(CCN2CCC(CC2)N2C=CC3=CC=C(C=C23)CN2C(CCC2)=O)C=C1 | Cl[CH:3](Cl)[CH3:4].[CH3:5][NH2:6].O=[CH:7][c:8]1[cH:9][cH:10][c:11]2[cH:12][cH:13][n:14]([CH:15]3[CH2:16][CH2:17][N:18]([CH2:19][CH2:20][c:21]4[cH:22][cH:23][c:24]([F:25])[cH:26][cH:27]4)[CH2:28][CH2:29]3)[c:30]2[cH:31]1>>[O:1]=[C:2]1[CH2:3][CH2:4][CH2:5][N:6]1[CH2:7][c:8]1[cH:9][cH:10][c:11]2[cH:12][cH:13][n:14]([CH:... | CC(Cl)Cl.CN.O=Cc1ccc2ccn(C3CCN(CCc4ccc(F)cc4)CC3)c2c1 | O=C1CCCN1Cc1ccc2ccn(C3CCN(CCc4ccc(F)cc4)CC3)c2c1 | null | null | C(C)(=O)O.C(C)(=O)OCC | Acylation | OtherReaction | c3d273483bdc1c80bdf4a28b829aa8c64d5898ae22f2b876d986c1179f06ad15 | 205c1fa4447bed2b537702cdbc8aa8d791601a402143e1139924efd3dc98eb56 | O=C1CCCN1Cc1ccc2ccn(C3CCN(CCc4ccccc4)CC3)c2c1 | Cl-[CH;D3;+0:1](-Cl)-[CH3;D1;+0:2].O=[CH;D2;+0:3]-[c:4](:[c:5]):[c:6]:[c:7]:[#7;a:8].[CH3;D1;+0:9]-[NH2;D1;+0:10]>>[#7;a:8]:[c:7]:[c:6]:[c:4](-[CH2;D2;+0:3]-[N;H0;D3;+0:10]1-[CH2;D2;+0:9]-[CH2;D2;+0:2]-[CH2;D2;+0:1]-[C:11]-1=[O;D1;H0:12]):[c:5] | null | [] | null | null | 2 | DAY | A mixture of 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-formylindole (400 mg) obtained in Example 130, methylamine hydrochloride (150 mg), sodium triacetoxyborohydride (480 mg), acetic acid (300 mg) and dichioroethane (10 ml) was stirred at room temperature for 2 days. Then a saturated aqueous solution of sodium bicarbo... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Secondary halide.Aldehyde.Primary amine | Tertiary amide | null | C1CC[NH]C1 | C1CC[NH]C1.c1ccc2cc[nH]c2c1.C1CC[NH]CC1.c1ccccc1 | HCl | C(C)(=O)O.C(C)(=O)OCC | null | 48 | CC(Cl)Cl.CN.O=Cc1ccc2ccn(C3CCN(CCc4ccc(F)cc4)CC3)c2c1>C(C)(=O)O.C(C)(=O)OCC>O=C1CCCN1Cc1ccc2ccn(C3CCN(CCc4ccc(F)cc4)CC3)c2c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-17193e9c904847d4a6ef03b9c60e57d7 | O=C(NCc1ccc2c(c1)N(C1CCN(CCc3ccc(F)cc3)CC1)CC2)C1CC1>>O=C1CCCN1Cc1ccc2ccn(C3CCN(CCc4ccc(F)cc4)CC3)c2c1 | FC1=CC=C(CCN2CCC(CC2)N2CCC3=CC=C(C=C23)CNC(=O)C2CC2)C=C1>>FC1=CC=C(CCN2CCC(CC2)N2C=CC3=CC=C(C=C23)CN2C(CCC2)=O)C=C1 | [O:1]=[C:2]([CH:3]1[CH2:4][CH2:5]1)[NH:6][CH2:7][c:8]1[cH:9][cH:10][c:11]2[c:30]([cH:31]1)[N:14]([CH:15]1[CH2:16][CH2:17][N:18]([CH2:19][CH2:20][c:21]3[cH:22][cH:23][c:24]([F:25])[cH:26][cH:27]3)[CH2:28][CH2:29]1)[CH2:13][CH2:12]2>>[O:1]=[C:2]1[CH2:3][CH2:4][CH2:5][N:6]1[CH2:7][c:8]1[cH:9][cH:10][c:11]2[cH:12][cH:13][n... | O=C(NCc1ccc2c(c1)N(C1CCN(CCc3ccc(F)cc3)CC1)CC2)C1CC1 | O=C1CCCN1Cc1ccc2ccn(C3CCN(CCc4ccc(F)cc4)CC3)c2c1 | null | [O-2].[O-2].[Mn+4] | C(Cl)(Cl)Cl | Miscellaneous | OtherReaction | 66850a32e37ee5813d16e24cd20b14324da672a3b8d8e2a657cf9bfb7d8a37f4 | e7d6a75f40cfa8c95cbb193a8ee54f6367f9aecbd6c08252ab8e7ea94bf0e325 | O=C1CCCN1Cc1ccc2ccn(C3CCN(CCc4ccccc4)CC3)c2c1 | [C:1]-[C:2](-[N;H0;D3;+0:3]1-[CH2;D2;+0:4]-[CH2;D2;+0:5]-[c:6](:[c:7]):[c:8]-1:[c:9]:[c:10]-[C:11]-[NH;D2;+0:12]-[C:13](=[O;D1;H0:14])-[CH;D3;+0:15]1-[C:16]-[CH2;D2;+0:17]-1)-[C:18]>>[C:1]-[C:2](-[n;H0;D3;+0:3]1:[cH;D2;+0:4]:[cH;D2;+0:5]:[c:6](:[c:7]):[c:8]:1:[c:9]:[c:10]-[C:11]-[N;H0;D3;+0:12]1-[CH2;D2;+0:17]-[C:16]-[... | 73 | [{"value": 73.0, "product": "FC1=CC=C(CCN2CCC(CC2)N2C=CC3=CC=C(C=C23)CN2C(CCC2)=O)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 67.0, "product": "FC1=CC=C(CCN2CCC(CC2)N2C=CC3=CC=C(C=C23)CN2C(CCC2)=O)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 1-[1-(4-Fluorophenethyl)piperidin-4-yl]-6-cyclopropanecarboxamidomethylindoline (90 mg) obtained in Example 159, activated manganese dioxide (450 mg) and chloroform (10 ml) were treated as in Example 285 to give the title compound (60 mg) as a white powder (yield: 73%).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide.Tertiary amine | Tertiary amide | C1CC1.c1ccc2c(c1)CC[NH]2 | C1CC[NH]C1.c1ccc2cc[nH]c2c1 | C1CC[NH]C1.c1ccc2cc[nH]c2c1.C1CC[NH]CC1.c1ccccc1 | null | [O-2].[O-2].[Mn+4].C(Cl)(Cl)Cl | null | null | O=C(NCc1ccc2c(c1)N(C1CCN(CCc3ccc(F)cc3)CC1)CC2)C1CC1>[O-2].[O-2].[Mn+4].C(Cl)(Cl)Cl>O=C1CCCN1Cc1ccc2ccn(C3CCN(CCc4ccc(F)cc4)CC3)c2c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-f6008e2deae94d1d9608c4cff099a8cd | CC(=O)OCC(=O)Cl.NCc1ccc2ccn(C3CCN(CCc4ccc(F)cc4)CC3)c2c1>>O=C1CCCN1Cc1ccc2ccn(C3CCN(CCc4ccc(F)cc4)CC3)c2c1 | FC1=CC=C(CCN2CCC(CC2)N2C=CC3=CC=C(C=C23)CN)C=C1.C(C)(=O)OCC(=O)Cl.N1=CC=CC=C1.O1CCCC1>>FC1=CC=C(CCN2CCC(CC2)N2C=CC3=CC=C(C=C23)CN2C(CCC2)=O)C=C1 | CC(=O)O[CH2:3][C:2](Cl)=[O:1].[NH2:6][CH2:7][c:8]1[cH:9][cH:10][c:11]2[cH:12][cH:13][n:14]([CH:15]3[CH2:16][CH2:17][N:18]([CH2:19][CH2:20][c:21]4[cH:22][cH:23][c:24]([F:25])[cH:26][cH:27]4)[CH2:28][CH2:29]3)[c:30]2[cH:31]1>>[O:1]=[C:2]1[CH2:3][CH2:4][CH2:5][N:6]1[CH2:7][c:8]1[cH:9][cH:10][c:11]2[cH:12][cH:13][n:14]([CH... | CC(=O)OCC(=O)Cl.NCc1ccc2ccn(C3CCN(CCc4ccc(F)cc4)CC3)c2c1 | O=C1CCCN1Cc1ccc2ccn(C3CCN(CCc4ccc(F)cc4)CC3)c2c1 | null | null | C(C)(=O)OCC | Acylation | OtherReaction | d3152cb18340aec4b17ebcd05c87360eff3e4bf32ea4fdc330b006fde23aabb1 | 3617c40794de267638fa47b80bd41c84cb8b3ee6ac22db6cf047ce280090a7a9 | O=C1CCCN1Cc1ccc2ccn(C3CCN(CCc4ccccc4)CC3)c2c1 | C-C(=O)-O-[CH2;D2;+0:1]-[C;H0;D3;+0:2](-Cl)=[O;D1;H0:3].[NH2;D1;+0:4]-[C:5]-[c:6]>>[O;D1;H0:3]=[C;H0;D3;+0:2]1-[CH2;D2;+0:1]-[C:7]-[C:8]-[N;H0;D3;+0:4]-1-[C:5]-[c:6] | 80 | [{"value": 80.0, "product": "FC1=CC=C(CCN2CCC(CC2)N2C=CC3=CC=C(C=C23)CN2C(CCC2)=O)C=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | A mixture of 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-aminomethylindole (150 mg) obtained in Example 322-3), acetoxyacetyl chloride (64 mg), pyridine (3 ml) and tetrahydrofuran (5 ml) was stirred under ice cooling for 30 min. Then ice water and ethyl acetate were added to the reaction mixtures. The organic layer was s... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Ester.Primary amine | Tertiary amide | null | C1CC[NH]C1 | C1CC[NH]C1.c1ccc2cc[nH]c2c1.C1CC[NH]CC1.c1ccccc1 | HCl | C(C)(=O)OCC | null | 0.5 | CC(=O)OCC(=O)Cl.NCc1ccc2ccn(C3CCN(CCc4ccc(F)cc4)CC3)c2c1>C(C)(=O)OCC>O=C1CCCN1Cc1ccc2ccn(C3CCN(CCc4ccc(F)cc4)CC3)c2c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-5878ea9430eb41c6b46a4d9002ff9adc | CCOC(C)=O.NCc1ccc2ccn(C3CCN(CCc4ccc(F)cc4)CC3)c2c1>>O=C1CCCN1Cc1ccc2ccn(C3CCN(CCc4ccc(F)cc4)CC3)c2c1 | C([O-])(O)=O.[Na+].C(C)(=O)OCC.FC1=CC=C(CCN2CCC(CC2)N2C=CC3=CC=C(C=C23)CN)C=C1.FC(C(=O)O)F>>FC1=CC=C(CCN2CCC(CC2)N2C=CC3=CC=C(C=C23)CN2C(CCC2)=O)C=C1 | O([C:2](=[O:1])[CH3:3])[CH2:5][CH3:4].[NH2:6][CH2:7][c:8]1[cH:9][cH:10][c:11]2[cH:12][cH:13][n:14]([CH:15]3[CH2:16][CH2:17][N:18]([CH2:19][CH2:20][c:21]4[cH:22][cH:23][c:24]([F:25])[cH:26][cH:27]4)[CH2:28][CH2:29]3)[c:30]2[cH:31]1>>[O:1]=[C:2]1[CH2:3][CH2:4][CH2:5][N:6]1[CH2:7][c:8]1[cH:9][cH:10][c:11]2[cH:12][cH:13][n... | CCOC(C)=O.NCc1ccc2ccn(C3CCN(CCc4ccc(F)cc4)CC3)c2c1 | O=C1CCCN1Cc1ccc2ccn(C3CCN(CCc4ccc(F)cc4)CC3)c2c1 | null | null | CN(C=O)C | Acylation | OtherReaction | 6a777f65a1ac1032c5787496e625dfb6cb6ea5d3df685c86c910aacc375a16d1 | ab33057bb8fb2c9dad5b018a4f87637d8c1c3babde576dc33e825e140481b8d2 | O=C1CCCN1Cc1ccc2ccn(C3CCN(CCc4ccccc4)CC3)c2c1 | [CH3;D1;+0:1]-[C;H0;D3;+0:2](=[O;D1;H0:3])-O-[CH2;D2;+0:4]-[CH3;D1;+0:5].[NH2;D1;+0:6]-[C:7]-[c:8]>>[O;D1;H0:3]=[C;H0;D3;+0:2]1-[CH2;D2;+0:1]-[CH2;D2;+0:5]-[CH2;D2;+0:4]-[N;H0;D3;+0:6]-1-[C:7]-[c:8] | 65 | [{"value": 65.0, "product": "FC1=CC=C(CCN2CCC(CC2)N2C=CC3=CC=C(C=C23)CN2C(CCC2)=O)C=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Under ice cooling, N,N′-carbonyldiimidazole (160 mg) was added to a solution of difluoroacetic acid (96 mg) in dimethylformamide (5 ml) and the resultant mixture was stirred for 30 min. Next, a solution of 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-aminomethylindole (150 mg) obtained in Example 322-3) in dimethylformami... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Primary amine | Tertiary amide | null | C1CC[NH]C1 | C1CC[NH]C1.c1ccc2cc[nH]c2c1.C1CC[NH]CC1.c1ccccc1 | HO- | CN(C=O)C | null | null | CCOC(C)=O.NCc1ccc2ccn(C3CCN(CCc4ccc(F)cc4)CC3)c2c1>CN(C=O)C>O=C1CCCN1Cc1ccc2ccn(C3CCN(CCc4ccc(F)cc4)CC3)c2c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-1f6edfbacefb473bb7c0f45c91590ff7 | CCOC(=O)Cl.NCc1ccc2ccn(C3CCN(CCc4ccc(F)cc4)CC3)c2c1>>O=C1CCCN1Cc1ccc2ccn(C3CCN(CCc4ccc(F)cc4)CC3)c2c1 | FC1=CC=C(CCN2CCC(CC2)N2C=CC3=CC=C(C=C23)CN)C=C1.C(OCC)(=O)Cl.FCC(=O)[O-].[Na+].C([O-])(O)=O.[Na+]>>FC1=CC=C(CCN2CCC(CC2)N2C=CC3=CC=C(C=C23)CN2C(CCC2)=O)C=C1 | Cl[C:2](O[CH2:5][CH3:4])=[O:1].[NH2:6][CH2:7][c:8]1[cH:9][cH:10][c:11]2[cH:12][cH:13][n:14]([CH:15]3[CH2:16][CH2:17][N:18]([CH2:19][CH2:20][c:21]4[cH:22][cH:23][c:24]([F:25])[cH:26][cH:27]4)[CH2:28][CH2:29]3)[c:30]2[cH:31]1>>[O:1]=[C:2]1[CH2:3][CH2:4][CH2:5][N:6]1[CH2:7][c:8]1[cH:9][cH:10][c:11]2[cH:12][cH:13][n:14]([C... | CCOC(=O)Cl.NCc1ccc2ccn(C3CCN(CCc4ccc(F)cc4)CC3)c2c1 | O=C1CCCN1Cc1ccc2ccn(C3CCN(CCc4ccc(F)cc4)CC3)c2c1 | null | null | CN(C=O)C.C(C)(=O)OCC | Acylation | OtherReaction | 812d6a9403bf429fb4a08f4c5bb34171f771f8903f0e40a7e992d11e4f1d938b | 43226331ece5df825bd4d10a4bf9a63611e15f024f26fb5d3fabc263c42282e6 | O=C1CCCN1Cc1ccc2ccn(C3CCN(CCc4ccccc4)CC3)c2c1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-O-[CH2;D2;+0:3]-[CH3;D1;+0:4].[NH2;D1;+0:5]-[C:6]-[c:7]>>[O;D1;H0:2]=[C;H0;D3;+0:1]1-[C:8]-[CH2;D2;+0:4]-[CH2;D2;+0:3]-[N;H0;D3;+0:5]-1-[C:6]-[c:7] | 57 | [{"value": 57.0, "product": "FC1=CC=C(CCN2CCC(CC2)N2C=CC3=CC=C(C=C23)CN2C(CCC2)=O)C=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Under ice cooling, ethyl chlorocarbonate (96 μl) was added to a suspension of sodium fluoroacetate (100 mg) in dimethylformamide (5 ml) and the resultant mixture was stirred for 20 min. Next, a solution of 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-aminomethylindole (150 mg) obtainedinExample 322-3) indimethylformamide ... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Ether.Primary amine | Tertiary amide | null | C1CC[NH]C1 | C1CC[NH]C1.c1ccc2cc[nH]c2c1.C1CC[NH]CC1.c1ccccc1 | HCl | CN(C=O)C.C(C)(=O)OCC | null | null | CCOC(=O)Cl.NCc1ccc2ccn(C3CCN(CCc4ccc(F)cc4)CC3)c2c1>CN(C=O)C.C(C)(=O)OCC>O=C1CCCN1Cc1ccc2ccn(C3CCN(CCc4ccc(F)cc4)CC3)c2c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-0381ca1bede240ecb8f1d620b37bcd2a | NCc1ccc2ccn(C3CCN(CCc4ccc(F)cc4)CC3)c2c1.O=C(Cl)CCCl>>O=C1CCCN1Cc1ccc2ccn(C3CCN(CCc4ccc(F)cc4)CC3)c2c1 | FC1=CC=C(CCN2CCC(CC2)N2C=CC3=CC=C(C=C23)CN)C=C1.ClCCC(=O)Cl.N1=CC=CC=C1.C([O-])(O)=O.[Na+]>>FC1=CC=C(CCN2CCC(CC2)N2C=CC3=CC=C(C=C23)CN2C(CCC2)=O)C=C1 | [NH2:6][CH2:7][c:8]1[cH:9][cH:10][c:11]2[cH:12][cH:13][n:14]([CH:15]3[CH2:16][CH2:17][N:18]([CH2:19][CH2:20][c:21]4[cH:22][cH:23][c:24]([F:25])[cH:26][cH:27]4)[CH2:28][CH2:29]3)[c:30]2[cH:31]1.Cl[C:2](=[O:1])[CH2:3][CH2:4]Cl>>[O:1]=[C:2]1[CH2:3][CH2:4][CH2:5][N:6]1[CH2:7][c:8]1[cH:9][cH:10][c:11]2[cH:12][cH:13][n:14]([... | NCc1ccc2ccn(C3CCN(CCc4ccc(F)cc4)CC3)c2c1.O=C(Cl)CCCl | O=C1CCCN1Cc1ccc2ccn(C3CCN(CCc4ccc(F)cc4)CC3)c2c1 | null | null | C(C)(=O)OCC | Acylation | OtherReaction | 7505e341c7bb64a4572500d1a99ce3a100c2f492bf864f977df7b850a072f2f5 | 8b35e8410bcf3c8bdff4698b3ea59db09850817ec720e2e45b797eaef876f90e | O=C1CCCN1Cc1ccc2ccn(C3CCN(CCc4ccccc4)CC3)c2c1 | Cl-[CH2;D2;+0:1]-[C:2]-[C;H0;D3;+0:3](-Cl)=[O;D1;H0:4].[NH2;D1;+0:5]-[C:6]-[c:7]>>[O;D1;H0:4]=[C;H0;D3;+0:3]1-[C:2]-[CH2;D2;+0:1]-[C:8]-[N;H0;D3;+0:5]-1-[C:6]-[c:7] | 16 | [{"value": 16.0, "product": "FC1=CC=C(CCN2CCC(CC2)N2C=CC3=CC=C(C=C23)CN2C(CCC2)=O)C=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | Under ice cooling, a mixture of 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-aminomethylindole (150 mg) obtained in Example 322-3), 3-chloropropionyl chloride (70 mg) and pyridine (5 ml) was stirred for 2 hr. Then a saturated aqueous solution of sodium bicarbonate and ethyl acetate were added to the reaction mixtures. The... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary halide.Primary amine | Tertiary amide | null | C1CC[NH]C1 | C1CC[NH]C1.c1ccc2cc[nH]c2c1.C1CC[NH]CC1.c1ccccc1 | Other | C(C)(=O)OCC | null | 2 | NCc1ccc2ccn(C3CCN(CCc4ccc(F)cc4)CC3)c2c1.O=C(Cl)CCCl>C(C)(=O)OCC>O=C1CCCN1Cc1ccc2ccn(C3CCN(CCc4ccc(F)cc4)CC3)c2c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-a8efe9a858a94d8dab5828dd295f7317 | CCOC(C)=O.NCc1ccc2ccn(C3CCN(CCc4ccc(F)cc4)CC3)c2c1>>O=C1CCCN1Cc1ccc2ccn(C3CCN(CCc4ccc(F)cc4)CC3)c2c1 | FC1=CC=C(CCN2CCC(CC2)N2C=CC3=CC=C(C=C23)CN)C=C1.CN(C=O)C.C(C)(=O)OCC>>FC1=CC=C(CCN2CCC(CC2)N2C=CC3=CC=C(C=C23)CN2C(CCC2)=O)C=C1 | O([C:2](=[O:1])[CH3:3])[CH2:5][CH3:4].[NH2:6][CH2:7][c:8]1[cH:9][cH:10][c:11]2[cH:12][cH:13][n:14]([CH:15]3[CH2:16][CH2:17][N:18]([CH2:19][CH2:20][c:21]4[cH:22][cH:23][c:24]([F:25])[cH:26][cH:27]4)[CH2:28][CH2:29]3)[c:30]2[cH:31]1>>[O:1]=[C:2]1[CH2:3][CH2:4][CH2:5][N:6]1[CH2:7][c:8]1[cH:9][cH:10][c:11]2[cH:12][cH:13][n... | CCOC(C)=O.NCc1ccc2ccn(C3CCN(CCc4ccc(F)cc4)CC3)c2c1 | O=C1CCCN1Cc1ccc2ccn(C3CCN(CCc4ccc(F)cc4)CC3)c2c1 | null | null | null | Acylation | OtherReaction | 6a777f65a1ac1032c5787496e625dfb6cb6ea5d3df685c86c910aacc375a16d1 | ab33057bb8fb2c9dad5b018a4f87637d8c1c3babde576dc33e825e140481b8d2 | O=C1CCCN1Cc1ccc2ccn(C3CCN(CCc4ccccc4)CC3)c2c1 | [CH3;D1;+0:1]-[C;H0;D3;+0:2](=[O;D1;H0:3])-O-[CH2;D2;+0:4]-[CH3;D1;+0:5].[NH2;D1;+0:6]-[C:7]-[c:8]>>[O;D1;H0:3]=[C;H0;D3;+0:2]1-[CH2;D2;+0:1]-[CH2;D2;+0:5]-[CH2;D2;+0:4]-[N;H0;D3;+0:6]-1-[C:7]-[c:8] | null | [] | null | null | null | null | Under ice cooling, N,N′-carbonyldiimidazole (160 mg) was added to a solution of 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-aminomethylindole (150 mg) obtained in Example 322-3) in dimethylformamide (5 ml) and the resultant mixture was stirred for 30 min. Then ice water and ethyl acetate were added to the reaction mixtur... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Primary amine | Tertiary amide | null | C1CC[NH]C1 | C1CC[NH]C1.c1ccc2cc[nH]c2c1.C1CC[NH]CC1.c1ccccc1 | HO- | null | null | null | CCOC(C)=O.NCc1ccc2ccn(C3CCN(CCc4ccc(F)cc4)CC3)c2c1>>O=C1CCCN1Cc1ccc2ccn(C3CCN(CCc4ccc(F)cc4)CC3)c2c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-72804b42f5bf48d8ac80aeeca9d0c7a5 | NCc1ccc2ccn(C3CCN(CCc4ccc(F)cc4)CC3)c2c1.O=C1CCO1>>O=C1CCCN1Cc1ccc2ccn(C3CCN(CCc4ccc(F)cc4)CC3)c2c1 | FC1=CC=C(CCN2CCC(CC2)N2C=CC3=CC=C(C=C23)CN)C=C1.C1(CCO1)=O.C1(=CC=CC=C1)C>>FC1=CC=C(CCN2CCC(CC2)N2C=CC3=CC=C(C=C23)CN2C(CCC2)=O)C=C1 | [NH2:6][CH2:7][c:8]1[cH:9][cH:10][c:11]2[cH:12][cH:13][n:14]([CH:15]3[CH2:16][CH2:17][N:18]([CH2:19][CH2:20][c:21]4[cH:22][cH:23][c:24]([F:25])[cH:26][cH:27]4)[CH2:28][CH2:29]3)[c:30]2[cH:31]1.O1[C:2](=[O:1])[CH2:3][CH2:4]1>>[O:1]=[C:2]1[CH2:3][CH2:4][CH2:5][N:6]1[CH2:7][c:8]1[cH:9][cH:10][c:11]2[cH:12][cH:13][n:14]([C... | NCc1ccc2ccn(C3CCN(CCc4ccc(F)cc4)CC3)c2c1.O=C1CCO1 | O=C1CCCN1Cc1ccc2ccn(C3CCN(CCc4ccc(F)cc4)CC3)c2c1 | null | null | null | Acylation | OtherReaction | 5a985e732d926ab881ce0a3f2162e71474b657433f917b7601ce70bfbb848e1a | ab33057bb8fb2c9dad5b018a4f87637d8c1c3babde576dc33e825e140481b8d2 | O=C1CCCN1Cc1ccc2ccn(C3CCN(CCc4ccccc4)CC3)c2c1 | [NH2;D1;+0:1]-[C:2]-[c:3].[O;D1;H0:4]=[C;H0;D3;+0:5]1-O-[CH2;D2;+0:6]-[C:7]-1>>[O;D1;H0:4]=[C;H0;D3;+0:5]1-[C:7]-[CH2;D2;+0:6]-[C:8]-[N;H0;D3;+0:1]-1-[C:2]-[c:3] | 45 | [{"value": 45.0, "product": "FC1=CC=C(CCN2CCC(CC2)N2C=CC3=CC=C(C=C23)CN2C(CCC2)=O)C=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-aminomethylindole (150 mg) obtained in Example 322-3), propiolactone (30 mg) and toluene (10 ml) was heated under reflux for 2 hr. Then the reaction solution was concentrated under reduced pressure and the residue was purified by silica gel column chromatography (e... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Primary amine | Tertiary amide | C1COC1 | C1CC[NH]C1 | C1CC[NH]C1.c1ccc2cc[nH]c2c1.C1CC[NH]CC1.c1ccccc1 | null | null | null | null | NCc1ccc2ccn(C3CCN(CCc4ccc(F)cc4)CC3)c2c1.O=C1CCO1>>O=C1CCCN1Cc1ccc2ccn(C3CCN(CCc4ccc(F)cc4)CC3)c2c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-9d1a8770810041799eef5f2768e408fc | CC(=O)NCc1ccc2c(C=O)cn(C3CCN(CCc4ccc(F)cc4)CC3)c2c1>>O=C1CCCN1Cc1ccc2ccn(C3CCN(CCc4ccc(F)cc4)CC3)c2c1 | FC1=CC=C(CCN2CCC(CC2)N2C=C(C3=CC=C(C=C23)CNC(C)=O)C=O)C=C1.Cl.NO.C(C)(=O)[O-].[Na+]>>FC1=CC=C(CCN2CCC(CC2)N2C=CC3=CC=C(C=C23)CN2C(CCC2)=O)C=C1 | O=[CH:5][c:12]1[c:11]2[cH:10][cH:9][c:8]([CH2:7][NH:6][C:2](=[O:1])[CH3:3])[cH:31][c:30]2[n:14]([CH:15]2[CH2:16][CH2:17][N:18]([CH2:19][CH2:20][c:21]3[cH:22][cH:23][c:24]([F:25])[cH:26][cH:27]3)[CH2:28][CH2:29]2)[cH:13]1>>[O:1]=[C:2]1[CH2:3][CH2:4][CH2:5][N:6]1[CH2:7][c:8]1[cH:9][cH:10][c:11]2[cH:12][cH:13][n:14]([CH:1... | CC(=O)NCc1ccc2c(C=O)cn(C3CCN(CCc4ccc(F)cc4)CC3)c2c1 | O=C1CCCN1Cc1ccc2ccn(C3CCN(CCc4ccc(F)cc4)CC3)c2c1 | null | null | CO | Heteroatom Alkylation and Arylation | OtherReaction | 7c37826c527ab703cd7a978ed429192f573e7cccdad5cc582bacd3bd5a5ab4e4 | 6f84bf7988e8ac4f6bd3ebf120d06640da1903a6aa109e14d174066ac037ad57 | O=C1CCCN1Cc1ccc2ccn(C3CCN(CCc4ccccc4)CC3)c2c1 | O=[CH;D2;+0:1]-[c;H0;D3;+0:2]1:[c:3]:[#7;a:4](-[C:5]):[c:6](:[c:7]:[c:8]-[C:9]-[NH;D2;+0:10]-[C:11](-[CH3;D1;+0:12])=[O;D1;H0:13]):[c:14]:1:[c:15]>>[C:5]-[#7;a:4]1:[c:3]:[cH;D2;+0:2]:[c:14](:[c:15]):[c:6]:1:[c:7]:[c:8]-[C:9]-[N;H0;D3;+0:10]1-[CH2;D2;+0:1]-[C:16]-[CH2;D2;+0:12]-[C:11]-1=[O;D1;H0:13] | 89.3 | [{"value": 88.5, "product": "FC1=CC=C(CCN2CCC(CC2)N2C=CC3=CC=C(C=C23)CN2C(CCC2)=O)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 89.3, "product": "FC1=CC=C(CCN2CCC(CC2)N2C=CC3=CC=C(C=C23)CN2C(CCC2)=O)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | A liquid mixture of 1-[1-(4-fluorophenethyl)piperidin-4-yl]-3-formyl-6-acetamidomethylindole (0.09 g) obtained in Example 370, hydroxylamine hydrochloride (0.02 g) and anhydrous sodium acetate (0.03 g) in methanol (10 ml) was stirred at room temperature for 1 hr. Then the reaction mixtures were concentrated and the res... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Secondary amide | Tertiary amide | c1ccc2cc[nH]c2c1 | C1CC[NH]C1.c1ccc2cc[nH]c2c1 | C1CC[NH]C1.c1ccc2cc[nH]c2c1.C1CC[NH]CC1.c1ccccc1 | null | CO | null | 1 | CC(=O)NCc1ccc2c(C=O)cn(C3CCN(CCc4ccc(F)cc4)CC3)c2c1>CO>O=C1CCCN1Cc1ccc2ccn(C3CCN(CCc4ccc(F)cc4)CC3)c2c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-2d73e15d03a34a1d801a6b2b29e3d121 | CCN(CC)CC.NCc1ccc2ccn(C3CCN(CCc4ccc(F)cc4)CC3)c2c1>>O=C1CCCN1Cc1ccc2ccn(C3CCN(CCc4ccc(F)cc4)CC3)c2c1 | FC1=CC=C(CCN2CCC(CC2)N2C=CC3=CC=C(C=C23)CN)C=C1.ClCC(=O)Cl.C(C)N(CC)CC.C([O-])(O)=O.[Na+]>>FC1=CC=C(CCN2CCC(CC2)N2C=CC3=CC=C(C=C23)CN2C(CCC2)=O)C=C1 | CCN(CC)[CH2:5][CH3:4].[NH2:6][CH2:7][c:8]1[cH:9][cH:10][c:11]2[cH:12][cH:13][n:14]([CH:15]3[CH2:16][CH2:17][N:18]([CH2:19][CH2:20][c:21]4[cH:22][cH:23][c:24]([F:25])[cH:26][cH:27]4)[CH2:28][CH2:29]3)[c:30]2[cH:31]1>>[O:1]=[C:2]1[CH2:3][CH2:4][CH2:5][N:6]1[CH2:7][c:8]1[cH:9][cH:10][c:11]2[cH:12][cH:13][n:14]([CH:15]3[CH... | CCN(CC)CC.NCc1ccc2ccn(C3CCN(CCc4ccc(F)cc4)CC3)c2c1 | O=C1CCCN1Cc1ccc2ccn(C3CCN(CCc4ccc(F)cc4)CC3)c2c1 | null | null | C(C)#N.C(C)(=O)OCC | Acylation | OtherReaction | 8630767fe74897b03d4bf8643ff130bc86c63bed739dd79676a35b3a79ab25d9 | 12b46cc5ae9451c48715a4d8ca226c6f99fd913678f6b19ad1ad4c6d041a3310 | O=C1CCCN1Cc1ccc2ccn(C3CCN(CCc4ccccc4)CC3)c2c1 | C-C-N(-C-C)-[CH2;D2;+0:1]-[CH3;D1;+0:2].[NH2;D1;+0:3]-[C:4]-[c:5]>>[O;D1;H0:6]=[C:7]1-[C:8]-[CH2;D2;+0:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:3]-1-[C:4]-[c:5] | 50.3 | [{"value": 49.0, "product": "FC1=CC=C(CCN2CCC(CC2)N2C=CC3=CC=C(C=C23)CN2C(CCC2)=O)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 50.3, "product": "FC1=CC=C(CCN2CCC(CC2)N2C=CC3=CC=C(C=C23)CN2C(CCC2)=O)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | A mixture of 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-aminomethylindole (150 mg) obtained in Example 322-3), chloroacetyl chloride (60 mg), triethylamine (50 mg) and acetonitrile (5 ml) was stirred under ice cooling for 2 hr. Then a saturated aqueous solution of sodium bicarbonate and ethyl acetate were added to the r... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Tertiary amine | Tertiary amide | null | C1CC[NH]C1 | C1CC[NH]C1.c1ccc2cc[nH]c2c1.C1CC[NH]CC1.c1ccccc1 | Other | C(C)#N.C(C)(=O)OCC | null | 2 | CCN(CC)CC.NCc1ccc2ccn(C3CCN(CCc4ccc(F)cc4)CC3)c2c1>C(C)#N.C(C)(=O)OCC>O=C1CCCN1Cc1ccc2ccn(C3CCN(CCc4ccc(F)cc4)CC3)c2c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-45ed6580381c44b894859e9fd18c3406 | CCN(CC)CC.NCc1ccc2ccn(C3CCN(CCc4ccc(F)cc4)CC3)c2c1>>O=C1CCCN1Cc1ccc2ccn(C3CCN(CCc4ccc(F)cc4)CC3)c2c1 | FC1=CC=C(CCN2CCC(CC2)N2C=CC3=CC=C(C=C23)CN)C=C1.BrCC(=O)Cl.C(C)N(CC)CC>>FC1=CC=C(CCN2CCC(CC2)N2C=CC3=CC=C(C=C23)CN2C(CCC2)=O)C=C1 | CCN(CC)[CH2:5][CH3:4].[NH2:6][CH2:7][c:8]1[cH:9][cH:10][c:11]2[cH:12][cH:13][n:14]([CH:15]3[CH2:16][CH2:17][N:18]([CH2:19][CH2:20][c:21]4[cH:22][cH:23][c:24]([F:25])[cH:26][cH:27]4)[CH2:28][CH2:29]3)[c:30]2[cH:31]1>>[O:1]=[C:2]1[CH2:3][CH2:4][CH2:5][N:6]1[CH2:7][c:8]1[cH:9][cH:10][c:11]2[cH:12][cH:13][n:14]([CH:15]3[CH... | CCN(CC)CC.NCc1ccc2ccn(C3CCN(CCc4ccc(F)cc4)CC3)c2c1 | O=C1CCCN1Cc1ccc2ccn(C3CCN(CCc4ccc(F)cc4)CC3)c2c1 | null | null | C(C)#N | Acylation | OtherReaction | 8630767fe74897b03d4bf8643ff130bc86c63bed739dd79676a35b3a79ab25d9 | 12b46cc5ae9451c48715a4d8ca226c6f99fd913678f6b19ad1ad4c6d041a3310 | O=C1CCCN1Cc1ccc2ccn(C3CCN(CCc4ccccc4)CC3)c2c1 | C-C-N(-C-C)-[CH2;D2;+0:1]-[CH3;D1;+0:2].[NH2;D1;+0:3]-[C:4]-[c:5]>>[O;D1;H0:6]=[C:7]1-[C:8]-[CH2;D2;+0:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:3]-1-[C:4]-[c:5] | 72.5 | [{"value": 65.0, "product": "FC1=CC=C(CCN2CCC(CC2)N2C=CC3=CC=C(C=C23)CN2C(CCC2)=O)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 72.5, "product": "FC1=CC=C(CCN2CCC(CC2)N2C=CC3=CC=C(C=C23)CN2C(CCC2)=O)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 1-[1-(4-Fluorophenethyl)piperidin-4-yl]-6-aminomethylindole (370 mg) obtained in Example 322-3), bromoacetyl chloride (220 mg), triethylamine (140 mg) and acetonitrile (10 ml) were treated as in Example 373 to give the title compound (320 mg) as an oil (yield: 65%).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Tertiary amine | Tertiary amide | null | C1CC[NH]C1 | C1CC[NH]C1.c1ccc2cc[nH]c2c1.C1CC[NH]CC1.c1ccccc1 | Other | C(C)#N | null | null | CCN(CC)CC.NCc1ccc2ccn(C3CCN(CCc4ccc(F)cc4)CC3)c2c1>C(C)#N>O=C1CCCN1Cc1ccc2ccn(C3CCN(CCc4ccc(F)cc4)CC3)c2c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-41c8a63353404d65814532fb7150e4d9 | CCOC(C)=O.CNC.O=C(CBr)NCc1ccc2ccn(C3CCN(CCc4ccc(F)cc4)CC3)c2c1>>O=C1CCCN1Cc1ccc2ccn(C3CCN(CCc4ccc(F)cc4)CC3)c2c1 | CNC.FC1=CC=C(CCN2CCC(CC2)N2C=CC3=CC=C(C=C23)CNC(CBr)=O)C=C1.O.C(C)(=O)OCC>>FC1=CC=C(CCN2CCC(CC2)N2C=CC3=CC=C(C=C23)CN2C(CCC2)=O)C=C1 | CC(=O)OC[CH3:4].CN[CH3:5].Br[CH2:3][C:2](=[O:1])[NH:6][CH2:7][c:8]1[cH:9][cH:10][c:11]2[cH:12][cH:13][n:14]([CH:15]3[CH2:16][CH2:17][N:18]([CH2:19][CH2:20][c:21]4[cH:22][cH:23][c:24]([F:25])[cH:26][cH:27]4)[CH2:28][CH2:29]3)[c:30]2[cH:31]1>>[O:1]=[C:2]1[CH2:3][CH2:4][CH2:5][N:6]1[CH2:7][c:8]1[cH:9][cH:10][c:11]2[cH:12]... | CCOC(C)=O.CNC.O=C(CBr)NCc1ccc2ccn(C3CCN(CCc4ccc(F)cc4)CC3)c2c1 | O=C1CCCN1Cc1ccc2ccn(C3CCN(CCc4ccc(F)cc4)CC3)c2c1 | null | null | O1CCCC1.CN(C=O)C | Heteroatom Alkylation and Arylation | OtherReaction | fbbd98fa64b303b28dc73e6b7954f1784ae319e3d62de46585dbf633748f036f | 2c16b065d05b73991fcbfc222d2054ef55cbb94588ca61a6d9beb53c16f6f062 | O=C1CCCN1Cc1ccc2ccn(C3CCN(CCc4ccccc4)CC3)c2c1 | Br-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[NH;D2;+0:4]-[C:5]-[c:6].C-C(=O)-O-C-[CH3;D1;+0:7].C-N-[CH3;D1;+0:8]>>[O;D1;H0:3]=[C:2]1-[CH2;D2;+0:1]-[CH2;D2;+0:7]-[CH2;D2;+0:8]-[N;H0;D3;+0:4]-1-[C:5]-[c:6] | null | [] | null | null | null | null | A mixture of 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-bromoacetamidomethylindole (170 mg) obtained in Example 374, a 2 M solution (2.2 ml) of dimethylamine in tetrahydrofuran and dimethylformamide (5 ml) was stirred at room temperature for 2 hr. Then water and ethyl acetate were added to the reaction solution. The org... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester.Secondary amide.Secondary amine | Tertiary amide | null | C1CC[NH]C1 | C1CC[NH]C1.c1ccc2cc[nH]c2c1.C1CC[NH]CC1.c1ccccc1 | HBr | O1CCCC1.CN(C=O)C | null | null | CCOC(C)=O.CNC.O=C(CBr)NCc1ccc2ccn(C3CCN(CCc4ccc(F)cc4)CC3)c2c1>O1CCCC1.CN(C=O)C>O=C1CCCN1Cc1ccc2ccn(C3CCN(CCc4ccc(F)cc4)CC3)c2c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-3f70d9f9b5254fe589885b6e3d06d864 | NCc1ccc2ccn(C3CCN(CCc4ccc(F)cc4)CC3)c2c1.O=C(CCBr)NCc1ccc2ccn(C3CCN(CCc4ccc(F)cc4)CC3)c2c1.O=C(Cl)CCBr>>O=C1CCCN1Cc1ccc2ccn(C3CCN(CCc4ccc(F)cc4)CC3)c2c1 | FC1=CC=C(CCN2CCC(CC2)N2C=CC3=CC=C(C=C23)CN)C=C1.FC1=CC=C(CCN2CCC(CC2)N2C=CC3=CC=C(C=C23)CNC(CCBr)=O)C=C1.BrCCC(=O)Cl.C(C)N(CC)CC>>FC1=CC=C(CCN2CCC(CC2)N2C=CC3=CC=C(C=C23)CN2C(CCC2)=O)C=C1 | [NH2:6][CH2:7][c:8]1[cH:9][cH:10][c:11]2[cH:12][cH:13][n:14]([CH:15]3[CH2:16][CH2:17][N:18]([CH2:19][CH2:20][c:21]4[cH:22][cH:23][c:24]([F:25])[cH:26][cH:27]4)[CH2:28][CH2:29]3)[c:30]2[cH:31]1.O=C(C[CH2:5]Br)NCc1ccc2ccn(C3CCN(CCc4ccc(F)cc4)CC3)c2c1.Cl[C:2](=[O:1])[CH2:3][CH2:4]Br>>[O:1]=[C:2]1[CH2:3][CH2:4][CH2:5][N:6]... | NCc1ccc2ccn(C3CCN(CCc4ccc(F)cc4)CC3)c2c1.O=C(CCBr)NCc1ccc2ccn(C3CCN(CCc4ccc(F)cc4)CC3)c2c1.O=C(Cl)CCBr | O=C1CCCN1Cc1ccc2ccn(C3CCN(CCc4ccc(F)cc4)CC3)c2c1 | null | null | C(C)#N | Acylation | OtherReaction | 99d0aabdaf7812e93b630556ec32331de0f6dfe81cd524de3a82060712565495 | 3e377fb2c9f706ed2dd47664a82f1154017bd790cac7fb9960b18b79a1956278 | O=C1CCCN1Cc1ccc2ccn(C3CCN(CCc4ccccc4)CC3)c2c1 | Br-[CH2;D2;+0:1]-C-C(=O)-N-C-c1:c:c:c2:c:c:n(-C3-C-C-N(-C-C-c4:c:c:c(-F):c:c:4)-C-C-3):c:2:c:1.Br-[CH2;D2;+0:2]-[C:3]-[C;H0;D3;+0:4](-Cl)=[O;D1;H0:5].[NH2;D1;+0:6]-[C:7]-[c:8]>>[O;D1;H0:5]=[C;H0;D3;+0:4]1-[C:3]-[CH2;D2;+0:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:6]-1-[C:7]-[c:8] | 156.5 | [{"value": 57.0, "product": "FC1=CC=C(CCN2CCC(CC2)N2C=CC3=CC=C(C=C23)CN2C(CCC2)=O)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 156.5, "product": "FC1=CC=C(CCN2CCC(CC2)N2C=CC3=CC=C(C=C23)CN2C(CCC2)=O)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 1H-NMR(400 MHz,DMSO-d6); δ(ppm) 1.40-1.50(2H,m), 1.60-1.71(4H,m), 2.00-2.08(2H,m), 2.12-2.26(2H,m), 2.37-2.52(2H,m), 2.70-3.10(8H,m), 3.39-3.49(2H,m), 3.52-3.63(2H,m), 4.42(2H,d,J=6.0 Hz), 4.45-4.58(1H,m), 6.43(1H,d,J=3.2 Hz), 6.96(1H,d,J=8.0 Hz), 7.10-7.19(2H,m), 7.26-7.34(2H,m), 7.44(1H,d,J=3.2 Hz), 7.47(1H,s), 7.49(... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Aromatic halide.Primary halide.Primary halide.Secondary amide.Primary amine.Tertiary amine | Tertiary amide | c1ccc2[nH]ccc2c1.C1CCNCC1.c1ccccc1 | C1CC[NH]C1 | C1CC[NH]C1.c1ccc2cc[nH]c2c1.C1CC[NH]CC1.c1ccccc1 | HF.Br- | C(C)#N | null | null | NCc1ccc2ccn(C3CCN(CCc4ccc(F)cc4)CC3)c2c1.O=C(CCBr)NCc1ccc2ccn(C3CCN(CCc4ccc(F)cc4)CC3)c2c1.O=C(Cl)CCBr>C(C)#N>O=C1CCCN1Cc1ccc2ccn(C3CCN(CCc4ccc(F)cc4)CC3)c2c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-167e085545df4b919f7bdf06c1160f76 | CNC.O=C(CCBr)NCc1ccc2ccn(C3CCN(CCc4ccc(F)cc4)CC3)c2c1>>O=C1CCCN1Cc1ccc2ccn(C3CCN(CCc4ccc(F)cc4)CC3)c2c1 | CNC.FC1=CC=C(CCN2CCC(CC2)N2C=CC3=CC=C(C=C23)CNC(CCBr)=O)C=C1.O.C(C)(=O)OCC>>FC1=CC=C(CCN2CCC(CC2)N2C=CC3=CC=C(C=C23)CN2C(CCC2)=O)C=C1 | CN[CH3:5].Br[CH2:4][CH2:3][C:2](=[O:1])[NH:6][CH2:7][c:8]1[cH:9][cH:10][c:11]2[cH:12][cH:13][n:14]([CH:15]3[CH2:16][CH2:17][N:18]([CH2:19][CH2:20][c:21]4[cH:22][cH:23][c:24]([F:25])[cH:26][cH:27]4)[CH2:28][CH2:29]3)[c:30]2[cH:31]1>>[O:1]=[C:2]1[CH2:3][CH2:4][CH2:5][N:6]1[CH2:7][c:8]1[cH:9][cH:10][c:11]2[cH:12][cH:13][n... | CNC.O=C(CCBr)NCc1ccc2ccn(C3CCN(CCc4ccc(F)cc4)CC3)c2c1 | O=C1CCCN1Cc1ccc2ccn(C3CCN(CCc4ccc(F)cc4)CC3)c2c1 | null | null | O1CCCC1.C1(=CC=CC=C1)C | Heteroatom Alkylation and Arylation | OtherReaction | a8ab73d8d7c3232f11625d3aa72560c0b8a2cd204db5646afd7663b12078d394 | 6c7943849849a233dbab56f467881d43a6d8f821d0ecc7a6ed000a2d9ef4cdda | O=C1CCCN1Cc1ccc2ccn(C3CCN(CCc4ccccc4)CC3)c2c1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3](=[O;D1;H0:4])-[NH;D2;+0:5]-[C:6]-[c:7].C-N-[CH3;D1;+0:8]>>[O;D1;H0:4]=[C:3]1-[C:2]-[CH2;D2;+0:1]-[CH2;D2;+0:8]-[N;H0;D3;+0:5]-1-[C:6]-[c:7] | null | [] | null | null | null | null | A mixture of 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-(3-bromopropionylamino)methylindole (150 mg) obtained in Example 377, a 2 M solution (5.0 ml) of dimethylamine in tetrahydrofuran and toluene (5 ml) was heated at 80 to 90° C. for 1.5 days. Then water and ethyl acetate were added to the reaction mixtures. The organ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amide.Secondary amine | Tertiary amide | null | C1CC[NH]C1 | C1CC[NH]C1.c1ccc2cc[nH]c2c1.C1CC[NH]CC1.c1ccccc1 | HBr | O1CCCC1.C1(=CC=CC=C1)C | null | null | CNC.O=C(CCBr)NCc1ccc2ccn(C3CCN(CCc4ccc(F)cc4)CC3)c2c1>O1CCCC1.C1(=CC=CC=C1)C>O=C1CCCN1Cc1ccc2ccn(C3CCN(CCc4ccc(F)cc4)CC3)c2c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-1fe013e97fc84e1abb5208dc998a674b | CCN(CC)CC.CN(C)C(=O)Cl.NCc1ccc2ccn(C3CCN(CCc4ccc(F)cc4)CC3)c2c1>>O=C1CCCN1Cc1ccc2ccn(C3CCN(CCc4ccc(F)cc4)CC3)c2c1 | FC1=CC=C(CCN2CCC(CC2)N2C=CC3=CC=C(C=C23)CN)C=C1.CN(C(=O)Cl)C.C(C)N(CC)CC>>FC1=CC=C(CCN2CCC(CC2)N2C=CC3=CC=C(C=C23)CN2C(CCC2)=O)C=C1 | CCN(CC)[CH2:5][CH3:4].CN([C:2](Cl)=[O:1])[CH3:3].[NH2:6][CH2:7][c:8]1[cH:9][cH:10][c:11]2[cH:12][cH:13][n:14]([CH:15]3[CH2:16][CH2:17][N:18]([CH2:19][CH2:20][c:21]4[cH:22][cH:23][c:24]([F:25])[cH:26][cH:27]4)[CH2:28][CH2:29]3)[c:30]2[cH:31]1>>[O:1]=[C:2]1[CH2:3][CH2:4][CH2:5][N:6]1[CH2:7][c:8]1[cH:9][cH:10][c:11]2[cH:1... | CCN(CC)CC.CN(C)C(=O)Cl.NCc1ccc2ccn(C3CCN(CCc4ccc(F)cc4)CC3)c2c1 | O=C1CCCN1Cc1ccc2ccn(C3CCN(CCc4ccc(F)cc4)CC3)c2c1 | null | null | C(C)#N | Acylation | OtherReaction | 2a3982fd3c9accc14a00a89619a997ed70a2e3c17f26f229c0a0da86ab24c301 | fa69b1530fccecfcd3137ea8e390fe87d722b3dd5537b1423f681eb7cf4280c5 | O=C1CCCN1Cc1ccc2ccn(C3CCN(CCc4ccccc4)CC3)c2c1 | C-C-N(-C-C)-[CH2;D2;+0:1]-[CH3;D1;+0:2].C-N(-[CH3;D1;+0:3])-[C;H0;D3;+0:4](-Cl)=[O;D1;H0:5].[NH2;D1;+0:6]-[C:7]-[c:8]>>[O;D1;H0:5]=[C;H0;D3;+0:4]1-[CH2;D2;+0:3]-[CH2;D2;+0:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:6]-1-[C:7]-[c:8] | 72.6 | [{"value": 72.0, "product": "FC1=CC=C(CCN2CCC(CC2)N2C=CC3=CC=C(C=C23)CN2C(CCC2)=O)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 72.6, "product": "FC1=CC=C(CCN2CCC(CC2)N2C=CC3=CC=C(C=C23)CN2C(CCC2)=O)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 1-[1-(4-Fluorophenethyl)piperidin-4-yl]-6-aminomethylindole (150 mg) obtained in Example 322-3), dimethylcarbamyl chloride (54 mg), triethylamine (50 mg) and acetonitrile (5 ml) were treated as in Example 373 to give the title compound (130 mg) as a white powder (yield: 72%).
Conditions: See reaction.notes.procedure_de... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Tertiary amide.Primary amine.Tertiary amine | Tertiary amide | null | C1CC[NH]C1 | C1CC[NH]C1.c1ccc2cc[nH]c2c1.C1CC[NH]CC1.c1ccccc1 | HCl | C(C)#N | null | null | CCN(CC)CC.CN(C)C(=O)Cl.NCc1ccc2ccn(C3CCN(CCc4ccc(F)cc4)CC3)c2c1>C(C)#N>O=C1CCCN1Cc1ccc2ccn(C3CCN(CCc4ccc(F)cc4)CC3)c2c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-11e78a2fcddc4818bf1574250803ddad | BrCCc1cccnc1.CC(=O)NCc1ccc2ccn(C3CCNCC3)c2c1>>CC(=O)NCc1ccc2ccn(C3CCN(CCc4cccnc4)CC3)c2c1 | C([O-])([O-])=O.[K+].[K+].N1CCC(CC1)N1C=CC2=CC=C(C=C12)CNC(C)=O.BrCCC=1C=NC=CC1>>N1=CC(=CC=C1)CCN1CCC(CC1)N1C=CC2=CC=C(C=C12)CNC(C)=O | Br[CH2:17][CH2:18][c:19]1[cH:20][cH:21][cH:22][n:23][cH:24]1.[CH3:1][C:2](=[O:3])[NH:4][CH2:5][c:6]1[cH:7][cH:8][c:9]2[cH:10][cH:11][n:12]([CH:13]3[CH2:14][CH2:15][NH:16][CH2:25][CH2:26]3)[c:27]2[cH:28]1>>[CH3:1][C:2](=[O:3])[NH:4][CH2:5][c:6]1[cH:7][cH:8][c:9]2[cH:10][cH:11][n:12]([CH:13]3[CH2:14][CH2:15][N:16]([CH2:1... | BrCCc1cccnc1.CC(=O)NCc1ccc2ccn(C3CCNCC3)c2c1 | CC(=O)NCc1ccc2ccn(C3CCN(CCc4cccnc4)CC3)c2c1 | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 0240b8450ff2c489d02f5f0d90bc953079d7a3ab239d35a03f26392fc248b4ef | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | c1cncc(CCN2CCC(n3ccc4ccccc43)CC2)c1 | Br-[CH2;D2;+0:1]-[C:2]-[c:3]:[c:4]:[#7;a:5].[C:6]-[C:7]-[NH;D2;+0:8]-[C:9]-[C:10]>>[#7;a:5]:[c:4]:[c:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:8](-[C:7]-[C:6])-[C:9]-[C:10] | 75.5 | [{"value": 75.5, "product": "N1=CC(=CC=C1)CCN1CCC(CC1)N1C=CC2=CC=C(C=C12)CNC(C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 43.2, "product": "N1=CC(=CC=C1)CCN1CCC(CC1)N1C=CC2=CC=C(C=C12)CNC(C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Potassium carbonate (0.5 g) was added to a solution of 1-(piperidin-4-yl)-6-acetamidomethylindole (0.10 g) obtained in Example 386-1) and 3-(2-bromoethyl)pyridine (0.07 g) obtained in Production Example 26-2 in N,N-dimethylformamide (5 ml) and the resultant mixture was stirred at 70° C. for 6 hr. Then the reaction mixt... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1CCNCC1 | C1CC[NH]CC1 | c1ccc2cc[nH]c2c1.C1CC[NH]CC1.c1ccncc1 | HBr | CN(C=O)C | null | null | BrCCc1cccnc1.CC(=O)NCc1ccc2ccn(C3CCNCC3)c2c1>CN(C=O)C>CC(=O)NCc1ccc2ccn(C3CCN(CCc4cccnc4)CC3)c2c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-e15c3dfc89994171b108cb79c4a78f5e | CC(=O)NCc1ccc2ccn(C3CCNCC3)c2c1.CC(O)c1ccc(CCBr)cc1>>CC(=O)NCc1ccc2ccn(C3(C(Cc4ccccc4)C(C)O)CCNCC3)c2c1 | C([O-])([O-])=O.[K+].[K+].N1CCC(CC1)N1C=CC2=CC=C(C=C12)CNC(C)=O.OC(C)C1=CC=C(CCBr)C=C1.CN(C=O)C>>OC(C)C(CC1=CC=CC=C1)C1(CCNCC1)N1C=CC2=CC=C(C=C12)CNC(C)=O | [CH3:1][C:2](=[O:3])[NH:4][CH2:5][c:6]1[cH:7][cH:8][c:9]2[cH:10][cH:11][n:12]([CH:13]3[CH2:25][CH2:26][NH:27][CH2:28][CH2:29]3)[c:30]2[cH:31]1.Br[CH2:14][CH2:15][c:16]1[cH:17][cH:18][c:19]([CH:22]([CH3:23])[OH:24])[cH:20][cH:21]1>>[CH3:1][C:2](=[O:3])[NH:4][CH2:5][c:6]1[cH:7][cH:8][c:9]2[cH:10][cH:11][n:12]([C:13]3([CH... | CC(=O)NCc1ccc2ccn(C3CCNCC3)c2c1.CC(O)c1ccc(CCBr)cc1 | CC(=O)NCc1ccc2ccn(C3(C(Cc4ccccc4)C(C)O)CCNCC3)c2c1 | null | null | null | C-C Coupling | OtherReaction | 74cab9211349dbe72611321e090a9a69e2245e8e8a001e202d3823d9c8d34329 | 70285494c8a6a84990fb103b229428eafa9b6c119bc126c6371d15cb1bcd1236 | c1ccc(CCC2(n3ccc4ccccc43)CCNCC2)cc1 | Br-[CH2;D2;+0:1]-[C:2]-[c:3]1:[c:4]:[c:5]:[c;H0;D3;+0:6](-[CH;D3;+0:7](-[C;D1;H3:8])-[O;D1;H1:9]):[c:10]:[c:11]:1.[c:12]:[#7;a:13](-[CH;D3;+0:14]1-[C:15]-[C:16]-[#7:17]-[C:18]-[C:19]-1):[c:20]>>[C;D1;H3:8]-[CH;D3;+0:7](-[O;D1;H1:9])-[CH;D3;+0:1](-[C:2]-[c:3]1:[c:4]:[c:5]:[cH;D2;+0:6]:[c:10]:[c:11]:1)-[C;H0;D4;+0:14]1(-... | 45.3 | [{"value": 45.3, "product": "OC(C)C(CC1=CC=CC=C1)C1(CCNCC1)N1C=CC2=CC=C(C=C12)CNC(C)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Potassium carbonate (0.5 g) was added to a solution of 1-(piperidin-4-yl)-6-acetamidomethylindole (0.10 g) obtained in Example 386-1) and 4-(1-hydroxyethyl)phenethyl bromide (0.07 g) obtained in Production Example 19 in N,N-dimethylformamide (5 ml) and the resultant mixture was stirred at 70° C. for 6 hr. Then the reac... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary alcohol | Secondary alcohol | C1CCNCC1.c1ccccc1 | c1ccccc1.C1CCNCC1 | c1ccc2cc[nH]c2c1.c1ccccc1.C1CCNCC1 | HBr | null | null | null | CC(=O)NCc1ccc2ccn(C3CCNCC3)c2c1.CC(O)c1ccc(CCBr)cc1>>CC(=O)NCc1ccc2ccn(C3(C(Cc4ccccc4)C(C)O)CCNCC3)c2c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-5af42bbbaf3f46088edb01a641e798f2 | CCOC(C)=O.O.O=Cc1ccc2c(c1)N(C1CCN(CCc3ccc(F)cc3)CC1)CC2>>CC(O)c1ccc2ccn(C3CCN(CCc4ccc(F)cc4)CC3)c2c1.O=C(O)C(=O)O | [Cl-].[NH4+].O.C(C)(=O)OCC.C[Mg]Br.FC1=CC=C(CCN2CCC(CC2)N2CCC3=CC=C(C=C23)C=O)C=C1>>C(C(=O)O)(=O)O.FC1=CC=C(CCN2CCC(CC2)N2C=CC3=CC=C(C=C23)C(C)O)C=C1 | CC[O:33][C:31]([CH3:29])=[O:32].[OH2:28].[CH:2](=[O:3])[c:4]1[cH:5][cH:6][c:7]2[c:26]([cH:27]1)[N:10]([CH:11]1[CH2:12][CH2:13][N:14]([CH2:15][CH2:16][c:17]3[cH:18][cH:19][c:20]([F:21])[cH:22][cH:23]3)[CH2:24][CH2:25]1)[CH2:9][CH2:8]2>>[CH3:1][CH:2]([OH:3])[c:4]1[cH:5][cH:6][c:7]2[cH:8][cH:9][n:10]([CH:11]3[CH2:12][CH2:... | CCOC(C)=O.O.O=Cc1ccc2c(c1)N(C1CCN(CCc3ccc(F)cc3)CC1)CC2 | CC(O)c1ccc2ccn(C3CCN(CCc4ccc(F)cc4)CC3)c2c1.O=C(O)C(=O)O | null | null | O1CCCC1.CCOCC | Acylation | OtherReaction | d6d7bbcaaf60e31456dd453134a47911963e7c19670d7e0c40e92762ee9e6979 | a2492da4c3c82546086c7343be26c10bb8d72162fc917198cf7e834d9d8c6a50 | c1ccc(CCN2CCC(n3ccc4ccccc43)CC2)cc1 | C-C-[O;H0;D2;+0:1]-[C:2](-[CH3;D1;+0:3])=[O;D1;H0:4].[C:5]-[C:6](-[N;H0;D3;+0:7]1-[CH2;D2;+0:8]-[CH2;D2;+0:9]-[c:10]2:[c:11]:[c:12]:[c:13](-[CH;D2;+0:14]=[O;H0;D1;+0:15]):[c:16]:[c:17]:2-1)-[C:18].[OH2;D0;+0:19]>>[C:5]-[C:6](-[n;H0;D3;+0:7]1:[cH;D2;+0:8]:[cH;D2;+0:9]:[c:10]2:[c:11]:[c:12]:[c:13](-[CH;D3;+0:14](-[C;D1;H... | null | [] | null | null | null | null | 1-[1-(4-Fluorophenethyl)piperidin-4-yl]-6-formylindoline (0.15 g) obtained in Example 130 was dissolved in tetrahydrofuran (5 ml) and stirred under ice cooling. To the resultant solution was added a 1.0 M solution (0.5 ml) of methylmagnesium bromide in ether and the mixture was stirred for 30 min. Then a saturated aque... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ester.Tertiary amine | Carboxylic acid.Carboxylic acid.Secondary alcohol | c1ccc2c(c1)CC[NH]2 | c1ccc2cc[nH]c2c1 | c1ccc2cc[nH]c2c1.C1CC[NH]CC1.c1ccccc1 | null | O1CCCC1.CCOCC | null | null | CCOC(C)=O.O.O=Cc1ccc2c(c1)N(C1CCN(CCc3ccc(F)cc3)CC1)CC2>O1CCCC1.CCOCC>CC(O)c1ccc2ccn(C3CCN(CCc4ccc(F)cc4)CC3)c2c1.O=C(O)C(=O)O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-271189629c0649539b8aa11b42376277 | CC(=O)Cl.CC1(C)CN(C2CCN(CCc3ccc(F)cc3)CC2)c2cc(CN)ccc21>>CC(=O)NCc1ccc2c(c1)N(C1CCN(CCc3ccc(F)cc3)CC1)CC2(C)C | [OH-].[Na+].C(C)N(CC)CC.C(C)(=O)Cl.CC1(CN(C2=CC(=CC=C12)CN)C1CCN(CC1)CCC1=CC=C(C=C1)F)C>>CC1(CN(C2=CC(=CC=C12)CNC(C)=O)C1CCN(CC1)CCC1=CC=C(C=C1)F)C | Cl[C:2]([CH3:1])=[O:3].[NH2:4][CH2:5][c:6]1[cH:7][cH:8][c:9]2[c:10]([cH:11]1)[N:12]([CH:13]1[CH2:14][CH2:15][N:16]([CH2:17][CH2:18][c:19]3[cH:20][cH:21][c:22]([F:23])[cH:24][cH:25]3)[CH2:26][CH2:27]1)[CH2:28][C:29]2([CH3:30])[CH3:31]>>[CH3:1][C:2](=[O:3])[NH:4][CH2:5][c:6]1[cH:7][cH:8][c:9]2[c:10]([cH:11]1)[N:12]([CH:1... | CC(=O)Cl.CC1(C)CN(C2CCN(CCc3ccc(F)cc3)CC2)c2cc(CN)ccc21 | CC(=O)NCc1ccc2c(c1)N(C1CCN(CCc3ccc(F)cc3)CC1)CC2(C)C | null | null | O1CCCC1.O | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | c1ccc(CCN2CCC(N3CCc4ccccc43)CC2)cc1 | Cl-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[NH2;D1;+0:4]-[C:5]-[c:6]>>[C;D1;H3:2]-[C;H0;D3;+0:1](=[O;D1;H0:3])-[NH;D2;+0:4]-[C:5]-[c:6] | 73.7 | [{"value": 73.7, "product": "CC1(CN(C2=CC(=CC=C12)CNC(C)=O)C1CCN(CC1)CCC1=CC=C(C=C1)F)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Under ice cooling, acetyl chloride (0.05 ml) was added dropwise into a solution of 3,3-dimethyl-1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-aminomethylindoline (0.22 g) obtained above and triethylamine (0.5 ml) in tetrahydrofuran (10 ml) and the resultant mixture was stirred at room temperature for 1 hr. Then a 1 N aqueo... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | C1CC[NH]CC1.c1ccccc1.c1ccc2c(c1)CC[NH]2 | HCl | O1CCCC1.O | null | null | CC(=O)Cl.CC1(C)CN(C2CCN(CCc3ccc(F)cc3)CC2)c2cc(CN)ccc21>O1CCCC1.O>CC(=O)NCc1ccc2c(c1)N(C1CCN(CCc3ccc(F)cc3)CC1)CC2(C)C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-41acfd82f73d47af87ceb039e051c050 | CC(=O)N1CCC(=O)CC1.COc1cccc(N)c1>>COc1cccc(NC2CCN(C(C)=O)CC2)c1 | C(C)(=O)O[BH-](OC(C)=O)OC(C)=O.[Na+].COC1=CC(=CC=C1)N.C(C)(=O)N1CCC(CC1)=O.[OH-].[Na+]>>C(C)(=O)N1CCC(CC1)NC1=CC(=CC=C1)OC | O=[C:9]1[CH2:10][CH2:11][N:12]([C:13]([CH3:14])=[O:15])[CH2:16][CH2:17]1.[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]([NH2:8])[cH:18]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]([NH:8][CH:9]2[CH2:10][CH2:11][N:12]([C:13]([CH3:14])=[O:15])[CH2:16][CH2:17]2)[cH:18]1 | CC(=O)N1CCC(=O)CC1.COc1cccc(N)c1 | COc1cccc(NC2CCN(C(C)=O)CC2)c1 | null | null | ClC(C)Cl.C(C)(=O)O.C(C)(=O)OCC | Heteroatom Alkylation and Arylation | Reductive amination with ketone | 42e9e55fb09951ae64da272b20a0fe6708e6155493933c6a5b57bd203fbe3626 | 07faf85ffe990e88a1de7fd04a339bf226f78d8bfae9712ea59eebd76bb54b9f | c1ccc(NC2CCNCC2)cc1 | O=[C;H0;D3;+0:1]1-[C:2]-[C:3]-[#7:4]-[C:5]-[C:6]-1.[NH2;D1;+0:7]-[c:8](:[c:9]):[c:10]>>[c:9]:[c:8](-[NH;D2;+0:7]-[CH;D3;+0:1]1-[C:2]-[C:3]-[#7:4]-[C:5]-[C:6]-1):[c:10] | 88.7 | [{"value": 87.9, "product": "C(C)(=O)N1CCC(CC1)NC1=CC(=CC=C1)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 88.7, "product": "C(C)(=O)N1CCC(CC1)NC1=CC(=CC=C1)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | Under ice cooling, sodium triacetoxyborohydride (12.0 g) was added to a liquid mixture of m-anisidine (4.40 g), 1-acetylpiperidin-4-one (5.0 g) and acetic acid (8 ml) in dichloroethane (80 ml). Then the reaction mixtures were stirred at room temperature overnight. The reaction mixtures were diluted with ethyl acetate (... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Primary amine | Secondary amine | C1CC[NH]CC1 | C1CC[NH]CC1 | c1ccccc1.C1CC[NH]CC1 | Other | ClC(C)Cl.C(C)(=O)O.C(C)(=O)OCC | null | 8 | CC(=O)N1CCC(=O)CC1.COc1cccc(N)c1>ClC(C)Cl.C(C)(=O)O.C(C)(=O)OCC>COc1cccc(NC2CCN(C(C)=O)CC2)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-8523842c5ee249419d04ca9122dbe120 | C=C(C)CCl.COc1cccc(NC2CCN(C(C)=O)CC2)c1>>C=C(C)CN(c1cccc(OC)c1)C1CCN(C(C)=O)CC1 | C(C)(=O)N1CCC(CC1)NC1=CC(=CC=C1)OC.ClCC(=C)C.C([O-])([O-])=O.[K+].[K+]>>C(C)(=O)N1CCC(CC1)N(C1=CC(=CC=C1)OC)CC(=C)C | Cl[CH2:4][C:2](=[CH2:1])[CH3:3].[NH:5]([c:6]1[cH:7][cH:8][cH:9][c:10]([O:11][CH3:12])[cH:13]1)[CH:14]1[CH2:15][CH2:16][N:17]([C:18]([CH3:19])=[O:20])[CH2:21][CH2:22]1>>[CH2:1]=[C:2]([CH3:3])[CH2:4][N:5]([c:6]1[cH:7][cH:8][cH:9][c:10]([O:11][CH3:12])[cH:13]1)[CH:14]1[CH2:15][CH2:16][N:17]([C:18]([CH3:19])=[O:20])[CH2:21... | C=C(C)CCl.COc1cccc(NC2CCN(C(C)=O)CC2)c1 | C=C(C)CN(c1cccc(OC)c1)C1CCN(C(C)=O)CC1 | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 6d58cac08ccced0a33ed16fbca180bc12aa011288d6476106d98a7b2cbc3d709 | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | c1ccc(NC2CCNCC2)cc1 | Cl-[CH2;D2;+0:1]-[C:2](=[C;D1;H2:3])-[C;D1;H3:4].[C:5]-[C:6](-[NH;D2;+0:7]-[c:8](:[c:9]):[c:10])-[C:11]>>[C:5]-[C:6](-[N;H0;D3;+0:7](-[CH2;D2;+0:1]-[C:2](=[C;D1;H2:3])-[C;D1;H3:4])-[c:8](:[c:9]):[c:10])-[C:11] | 63.6 | [{"value": 63.6, "product": "C(C)(=O)N1CCC(CC1)N(C1=CC(=CC=C1)OC)CC(=C)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of N-(l-acetylpiperidin-4-yl)-3-methoxyaniline (2.0 g), 3-chloro-2-methylpropene (10 ml) and potassium carbonate (5.0 g) in dimethylformamide (50 ml) was reacted at 80° C. for 6 hr. Then the reaction mixtures were concentrated under reduced pressure and partitioned between ethyl acetate and water. The ethyl a... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | null | null | c1ccccc1.C1CC[NH]CC1 | HCl | CN(C=O)C | null | null | C=C(C)CCl.COc1cccc(NC2CCN(C(C)=O)CC2)c1>CN(C=O)C>C=C(C)CN(c1cccc(OC)c1)C1CCN(C(C)=O)CC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-179e002ccc924b4486694817bb5e0033 | CN=C=O.NCc1ccc2c(c1)N(C1CCN(CCc3ccc(F)cc3)CC1)CC2>>CNC(=O)NCc1ccc2ccn(C3CCN(CCc4ccc(F)cc4)CC3)c2c1 | CN=C=O.FC1=CC=C(CCN2CCC(CC2)N2CCC3=CC=C(C=C23)CN)C=C1>>FC1=CC=C(CCN2CCC(CC2)N2C=CC3=CC=C(C=C23)CNC(=O)NC)C=C1 | [CH3:1][N:2]=[C:3]=[O:4].[NH2:5][CH2:6][c:7]1[cH:8][cH:9][c:10]2[c:29]([cH:30]1)[N:13]([CH:14]1[CH2:15][CH2:16][N:17]([CH2:18][CH2:19][c:20]3[cH:21][cH:22][c:23]([F:24])[cH:25][cH:26]3)[CH2:27][CH2:28]1)[CH2:12][CH2:11]2>>[CH3:1][NH:2][C:3](=[O:4])[NH:5][CH2:6][c:7]1[cH:8][cH:9][c:10]2[cH:11][cH:12][n:13]([CH:14]3[CH2:... | CN=C=O.NCc1ccc2c(c1)N(C1CCN(CCc3ccc(F)cc3)CC1)CC2 | CNC(=O)NCc1ccc2ccn(C3CCN(CCc4ccc(F)cc4)CC3)c2c1 | null | null | C(C)(=O)OCC | Acylation | OtherReaction | 2fc640272b578c5277cf09e910fd3523485a0ee28f89f555762214f3b5bf663c | ae0ea28c076c051064f412db80e76c29cc0f43a270e5900b0a789606b8f5ee28 | c1ccc(CCN2CCC(n3ccc4ccccc43)CC2)cc1 | [C;D1;H3:1]-[N;H0;D2;+0:2]=[C;H0;D2;+0:3]=[O;D1;H0:4].[C:5]-[C:6](-[N;H0;D3;+0:7]1-[CH2;D2;+0:8]-[CH2;D2;+0:9]-[c:10](:[c:11]):[c:12]-1:[c:13]:[c:14]-[C:15]-[NH2;D1;+0:16])-[C:17]>>[C:5]-[C:6](-[n;H0;D3;+0:7]1:[cH;D2;+0:8]:[cH;D2;+0:9]:[c:10](:[c:11]):[c:12]:1:[c:13]:[c:14]-[C:15]-[NH;D2;+0:16]-[C;H0;D3;+0:3](=[O;D1;H0... | 67.3 | [{"value": 67.0, "product": "FC1=CC=C(CCN2CCC(CC2)N2C=CC3=CC=C(C=C23)CNC(=O)NC)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 67.3, "product": "FC1=CC=C(CCN2CCC(CC2)N2C=CC3=CC=C(C=C23)CNC(=O)NC)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Under ice cooling, methyl isocyanate (0.02 g) was added dropwise into a solution of 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-aminomethylindoline (0.09 g) obtained in Example 132 in ethyl acetate (10 ml) and the resultant mixture was stirred at room temperature for 1 hr. The resulting precipitate was collected by filtr... | 10.6084/m9.figshare.5104873.v1 | null | Isocyanate.Primary amine.Tertiary amine | Urea | c1ccc2c(c1)CC[NH]2 | c1ccc2cc[nH]c2c1 | c1ccc2cc[nH]c2c1.C1CC[NH]CC1.c1ccccc1 | null | C(C)(=O)OCC | null | null | CN=C=O.NCc1ccc2c(c1)N(C1CCN(CCc3ccc(F)cc3)CC1)CC2>C(C)(=O)OCC>CNC(=O)NCc1ccc2ccn(C3CCN(CCc4ccc(F)cc4)CC3)c2c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-1fa6841080d844fb9d031972cc00f02e | Cl>>Cl | CC(C)CC(C1(CCC1)C=2C=CC(=CC2)Cl)N(C)C.Cl>>CC(C)CC(C1(CCC1)C=2C=CC(=CC2)Cl)N(C)C.Cl | [ClH:20]>>[ClH:20] | Cl | Cl | null | null | CC(C)(C)OC.C(C)OCC | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | null | null | null | [] | null | null | 30 | MINUTE | Sibutramine free base (2.25 g) was dissolved in MTBE (20 mL) and that solution was added to 20 mL 1M HCl in diethyl ether. The reaction mixture was stirred for 30 minutes, and the solid was collected by filtration to give 1.73 g after drying. The product was characterized by 1H NMR.
Conditions: See reaction.notes.proce... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | null | null | CC(C)(C)OC.C(C)OCC | null | 0.5 | Cl>CC(C)(C)OC.C(C)OCC>Cl |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-17bfc81018684969b5db50f881bf3c10 | COC(=O)c1cc(C=O)cc(OC)c1OC.N#Cc1ccc(N)cc1.[C-]#[N+]Cc1ccccc1>>COC(=O)c1cc(C(Nc2ccc(C#N)cc2)C(=O)OC)cc(OC)c1OC | C(=O)C=1C=C(C(=C(C(=O)OC)C1)OC)OC.NC1=CC=C(C#N)C=C1.C(C1=CC=CC=C1)[N+]#[C-]>>C(#N)C1=CC=C(C=C1)NC(C=1C=C(C(=C(C(=O)OC)C1)OC)OC)C(=O)OC | [CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([CH:8]=[O:19])[cH:22][c:23]([O:24][CH3:25])[c:26]1[O:27][CH3:28].[NH2:9][c:10]1[cH:11][cH:12][c:13]([C:14]#[N:15])[cH:16][cH:17]1.c1ccc([CH2:18][N+]#[C-:21])cc1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([CH:8]([NH:9][c:10]2[cH:11][cH:12][c:13]([C:14]#[N:15])[cH:16][cH:17]2)[... | COC(=O)c1cc(C=O)cc(OC)c1OC.N#Cc1ccc(N)cc1.[C-]#[N+]Cc1ccccc1 | COC(=O)c1cc(C(Nc2ccc(C#N)cc2)C(=O)OC)cc(OC)c1OC | null | null | null | Acylation | OtherReaction | f47e35587b108d05f20011e35418ae3bbac52cc18b48092e1f6a3934b462af2a | ccdd12dc1fe6d9fc366671da76e2604d95a8657e060905968474cf190e0408d0 | c1ccc(CNc2ccccc2)cc1 | [C-;H0;D1:1]#[N+]-[CH2;D2;+0:2]-c1:c:c:c:c:c:1.[NH2;D1;+0:3]-[c:4](:[c:5]):[c:6].[O;H0;D1;+0:7]=[CH;D2;+0:8]-[c:9](:[c:10]):[c:11]>>[CH3;D1;+0:1]-[#8:12]-[C;H0;D3;+0:2](=[O;H0;D1;+0:7])-[CH;D3;+0:8](-[NH;D2;+0:3]-[c:4](:[c:5]):[c:6])-[c:9](:[c:10]):[c:11] | null | [] | null | null | null | null | In analogy to Example 1.1, methyl 5-formyl-2,3-dimethoxy-benzoate (F. Y. Wu, D. L. b rink, J. Agric. Food Chem. (1977) 25 692) was reacted with 4-aminobenzonitrile and benzyl isonitrile to give methyl (RS)-5-[(4-cyano-phenylamino)-methoxycarbonyl-methyl]-2,3-dimethoxy-benzoate.
Conditions: See reaction.notes.procedure_... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Isocyanide.Primary amine | Ester.Secondary amine | c1ccccc1 | null | c1ccccc1.c1ccccc1 | Other | null | null | null | COC(=O)c1cc(C=O)cc(OC)c1OC.N#Cc1ccc(N)cc1.[C-]#[N+]Cc1ccccc1>>COC(=O)c1cc(C(Nc2ccc(C#N)cc2)C(=O)OC)cc(OC)c1OC |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-fd352fe73f91463cad095e459fd55d63 | CCOC(=O)CBr.Cc1cc(O)c(C=O)cc1C>>CCOC(=O)COc1cc(C)c(C)cc1C=O | BrCC(=O)OCC.C([O-])([O-])=O.[K+].[K+].OC1=C(C=O)C=C(C(=C1)C)C>>C(=O)C1=C(OCC(=O)OCC)C=C(C(=C1)C)C | Br[CH2:6][C:4]([O:3][CH2:2][CH3:1])=[O:5].[OH:7][c:8]1[cH:9][c:10]([CH3:11])[c:12]([CH3:13])[cH:14][c:15]1[CH:16]=[O:17]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][O:7][c:8]1[cH:9][c:10]([CH3:11])[c:12]([CH3:13])[cH:14][c:15]1[CH:16]=[O:17] | CCOC(=O)CBr.Cc1cc(O)c(C=O)cc1C | CCOC(=O)COc1cc(C)c(C)cc1C=O | null | null | CC(=O)C | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 50d675b335c583a6ce22e1164b27a78b18b9ca447d45137820c344bcb6369217 | 0865de4e1853c59ac25437e36fd18b03329566cb9eff4b4f0ce70d5714692fd3 | c1ccccc1 | Br-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#8:4]-[C:5].[O;D1;H0:6]=[C:7]-[c:8]:[c:9](-[OH;D1;+0:10]):[c:11]>>[C:5]-[#8:4]-[C:2](=[O;D1;H0:3])-[CH2;D2;+0:1]-[O;H0;D2;+0:10]-[c:9](:[c:11]):[c:8]-[C:7]=[O;D1;H0:6] | null | [] | null | null | null | null | 0.808 ml of ethyl bromoacetate and 1 g of potassium carbonate were added to a solution of 838 mg of 2-hydroxy-4,5-dimethylbenzaldehyde (J. Chem. Soc. (1953) 820) in 150 ml of acetone. The suspension obtained was heated to reflux overnight and then filtered. The filtrate was concentrated. The crude product was isolated ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester.Aromatic alcohol | Ester.Ether | null | null | c1ccccc1 | HBr | CC(=O)C | null | null | CCOC(=O)CBr.Cc1cc(O)c(C=O)cc1C>CC(=O)C>CCOC(=O)COc1cc(C)c(C)cc1C=O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-b97b8eefbfc7419ab5eba8df0265952e | C=CC(=O)OC.COc1cc(Br)c(C=O)cc1OC>>COC(=O)/C=C/c1cc(OC)c(OC)cc1C=O | C(C=C)(=O)OC.C(C)N(CC)CC.C1(=C(C=CC=C1)P(C1=C(C=CC=C1)C)C1=C(C=CC=C1)C)C.BrC1=CC(=C(C=C1C=O)OC)OC>>C(=O)C1=C(C=C(C(=C1)OC)OC)/C=C/C(=O)OC | [CH3:1][O:2][C:3](=[O:4])[CH:5]=[CH2:6].Br[c:7]1[cH:8][c:9]([O:10][CH3:11])[c:12]([O:13][CH3:14])[cH:15][c:16]1[CH:17]=[O:18]>>[CH3:1][O:2][C:3](=[O:4])/[CH:5]=[CH:6]/[c:7]1[cH:8][c:9]([O:10][CH3:11])[c:12]([O:13][CH3:14])[cH:15][c:16]1[CH:17]=[O:18] | C=CC(=O)OC.COc1cc(Br)c(C=O)cc1OC | COC(=O)/C=C/c1cc(OC)c(OC)cc1C=O | null | CC(=O)[O-].CC(=O)[O-].[Pd+2] | O.CC(=O)N(C)C.C(C)(=O)OCC | C-C Coupling | Heck terminal vinyl | 55becfded1a3842d5a03bbf3e1610411c659aff0806930400c4db2ef61f9c87f | 4b186811a4930853b446d93d9faa39b267bddb9ce0b8021bda5c5a3b2bc69f0b | c1ccccc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[C:5]=[O;D1;H0:6]):[c:7].[C;D1;H3:8]-[#8:9]-[C:10](=[O;D1;H0:11])-[C:12]=[CH2;D1;+0:13]>>[C;D1;H3:8]-[#8:9]-[C:10](=[O;D1;H0:11])/[C:12]=[CH;D2;+0:13]/[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[C:5]=[O;D1;H0:6]):[c:7] | null | [] | null | null | null | null | 6.2 ml of methyl acrylate, 25 ml of triethylamine, 270 mg of Pd(OAc)2 and 1.5 g of tri-(o-tolyl)-phosphine were added to a solution of 14.7 g of 6-bromoveratraldehyde in 100 ml of dimethylacetamide. The reaction mixture was heated for 4 hours to 110° C., then left to cool to room temperature and poured into a mixture o... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Vinyl | null | c1ccccc1 | c1ccccc1 | c1ccccc1 | HBr | CC(=O)[O-].CC(=O)[O-].[Pd+2].O.CC(=O)N(C)C.C(C)(=O)OCC | null | null | C=CC(=O)OC.COc1cc(Br)c(C=O)cc1OC>CC(=O)[O-].CC(=O)[O-].[Pd+2].O.CC(=O)N(C)C.C(C)(=O)OCC>COC(=O)/C=C/c1cc(OC)c(OC)cc1C=O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-baa0c40687454d8bb60075d881da00b7 | CCOC(=O)c1cc(CO)cc(C(C)(C)O[SiH2]C(C)(C)C)c1>>CCOC(=O)c1cc(C=O)cc(C(C)(C)O[SiH2]C(C)(C)C)c1 | C(C)N(CC)CC.C(C(=O)Cl)(=O)Cl.CS(=O)C.C(C)(C)(C)[SiH2]OC(C=1C=C(C(=O)OCC)C=C(C1)CO)(C)C>>C(C)(C)(C)[SiH2]OC(C=1C=C(C(=O)OCC)C=C(C1)C=O)(C)C | [CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][c:8]([CH2:9][OH:10])[cH:11][c:12]([C:13]([CH3:14])([CH3:15])[O:16][SiH2:17][C:18]([CH3:19])([CH3:20])[CH3:21])[cH:22]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][c:8]([CH:9]=[O:10])[cH:11][c:12]([C:13]([CH3:14])([CH3:15])[O:16][SiH2:17][C:18]([CH3:19])([CH3:20])[CH3:21])[... | CCOC(=O)c1cc(CO)cc(C(C)(C)O[SiH2]C(C)(C)C)c1 | CCOC(=O)c1cc(C=O)cc(C(C)(C)O[SiH2]C(C)(C)C)c1 | null | null | C(Cl)Cl | Oxidation | Oxidation or Dehydrogenation of Alcohols to Aldehydes and Ketones | 41bfa9deea81b465c88ad21fdfb64a2e1ba29490558cf430df132cb98b4a538b | 0a03c6724c1862e8f86d4a463afda55b8e067dc6cb42597b472eb7cabc03eda3 | c1ccccc1 | [OH;D1;+0:1]-[CH2;D2;+0:2]-[c:3](:[c:4]):[c:5]>>[O;H0;D1;+0:1]=[CH;D2;+0:2]-[c:3](:[c:4]):[c:5] | 100.6 | [{"value": 100.6, "product": "C(C)(C)(C)[SiH2]OC(C=1C=C(C(=O)OCC)C=C(C1)C=O)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 0.64 ml of oxalyl chloride was added at −60° C. to a solution of 0.76 ml of dimethyl sulphoxide in 10 ml of CH2Cl2. After 5 minutes 2 g of ethyl 3-(tert-butyl-dimethyl-silanyloxymethyl)-5-hydroxymethyl-benzoate (Example 31.1) in 20 ml of CH2Cl2 were added over 5 minutes in a manner such that the temperature did not exc... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | Aldehyde | null | null | c1ccccc1 | null | C(Cl)Cl | null | null | CCOC(=O)c1cc(CO)cc(C(C)(C)O[SiH2]C(C)(C)C)c1>C(Cl)Cl>CCOC(=O)c1cc(C=O)cc(C(C)(C)O[SiH2]C(C)(C)C)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-ef8f8e2abfad4a5192c207ac03e17018 | CC(C)(C)OC(=O)/N=C(\NC(=O)OC(C)(C)C)c1ccc(NC(C(=O)[O-])c2cccc(OCc3ccccc3)c2)cc1>>COC(=O)C(Nc1ccc(C(=N)N)cc1)c1cccc(OCc2ccccc2)c1 | C(C1=CC=CC=C1)OC=1C=C(C=CC1)C(C(=O)[O-])NC1=CC=C(C=C1)/C(=N/C(=O)OC(C)(C)C)/NC(=O)OC(C)(C)C.FC(C(=O)O)(F)F>>FC(C(=O)O)(F)F.C(C1=CC=CC=C1)OC=1C=C(C=CC1)C(C(=O)OC)NC1=CC=C(C=C1)C(N)=N | CC(C)(C)OC(=O)[NH:13]/[C:11]([c:10]1[cH:9][cH:8][c:7]([NH:6][CH:5]([C:3]([O-:2])=[O:4])[c:16]2[cH:17][cH:18][cH:19][c:20]([O:21][CH2:22][c:23]3[cH:24][cH:25][cH:26][cH:27][cH:28]3)[cH:29]2)[cH:15][cH:14]1)=[N:12]\[C:1](=O)OC(C)(C)C>>[CH3:1][O:2][C:3](=[O:4])[CH:5]([NH:6][c:7]1[cH:8][cH:9][c:10]([C:11](=[NH:12])[NH2:13]... | CC(C)(C)OC(=O)/N=C(\NC(=O)OC(C)(C)C)c1ccc(NC(C(=O)[O-])c2cccc(OCc3ccccc3)c2)cc1 | COC(=O)C(Nc1ccc(C(=N)N)cc1)c1cccc(OCc2ccccc2)c1 | null | null | C(Cl)Cl | Miscellaneous | OtherReaction | 5431a1578af2dff9c4ff352eb6b473e28f26aeee029277f131a427a08a118c93 | e57094758b6659504a00db5afda3b231965ea2fa57a86e6fa4aa6a6bccf5bbb0 | c1ccc(COc2cccc(CNc3ccccc3)c2)cc1 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]/[C:2](-[c:3])=[N;H0;D2;+0:4]\[C;H0;D3;+0:5](=O)-O-C(-C)(-C)-C.[C:6]-[C:7](-[O-;H0;D1:8])=[O;D1;H0:9]>>[C:6]-[C:7](=[O;D1;H0:9])-[O;H0;D2;+0:8]-[CH3;D1;+0:5].[NH2;D1;+0:1]-[C:2](=[NH;D1;+0:4])-[c:3] | null | [] | null | null | 50 | MINUTE | 655 mg of methyl (E)/(Z)-(RS)-(3-benzyloxy-phenyl)-[4-(tert-butoxycarbonylamino-tert-butoxycarbonylimino-methyl)-phenylamino]-acetate were treated in 3 ml of methylene chloride with 3 ml of trifluoroacetic acid and left to stand for 50 min. at room temperature. The solution was evaporated in a vacuum and the residue wa... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Ether.Boc.Boc | Ester.Primary amine | null | null | c1ccccc1.c1ccccc1.c1ccccc1 | HO- | C(Cl)Cl | null | 0.833333 | CC(C)(C)OC(=O)/N=C(\NC(=O)OC(C)(C)C)c1ccc(NC(C(=O)[O-])c2cccc(OCc3ccccc3)c2)cc1>C(Cl)Cl>COC(=O)C(Nc1ccc(C(=N)N)cc1)c1cccc(OCc2ccccc2)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-23e181aa40de4f3d9632fd447aad400c | CCOC(=O)COc1ccccc1C(Nc1ccc(C(=N)NC(=O)OC(C)(C)C)cc1)C(=O)OCC>>N=C(N)c1ccc(NC(C(=O)O)c2ccccc2OCC(=O)O)cc1 | C(C)(C)(C)OC(=O)NC(C1=CC=C(C=C1)NC(C(=O)OCC)C1=C(C=CC=C1)OCC(=O)OCC)=N.[Li+].[OH-]>>C(N)(=N)C1=CC=C(C=C1)NC(C(=O)O)C1=C(C=CC=C1)OCC(=O)O | CC[O:12][C:10]([CH:9]([NH:8][c:7]1[cH:6][cH:5][c:4]([C:2]([NH:1]C(=O)OC(C)(C)C)=[NH:3])[cH:25][cH:24]1)[c:13]1[cH:14][cH:15][cH:16][cH:17][c:18]1[O:19][CH2:20][C:21](=[O:22])[O:23]CC)=[O:11]>>[NH:1]=[C:2]([NH2:3])[c:4]1[cH:5][cH:6][c:7]([NH:8][CH:9]([C:10](=[O:11])[OH:12])[c:13]2[cH:14][cH:15][cH:16][cH:17][c:18]2[O:19... | CCOC(=O)COc1ccccc1C(Nc1ccc(C(=N)NC(=O)OC(C)(C)C)cc1)C(=O)OCC | N=C(N)c1ccc(NC(C(=O)O)c2ccccc2OCC(=O)O)cc1 | null | null | C1CCOC1 | Miscellaneous | OtherReaction | 647f9a5870bd6337349c6d06f6210da5832381490688e1d2d52e78299c303821 | 7ff63e5d030f4410ccbe34bde826d5b8e9027a8f941c35c3f4fa9048b784b240 | c1ccc(CNc2ccccc2)cc1 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[C;H0;D3;+0:2](=[NH;D1;+0:3])-[c:4](:[c:5]):[c:6].C-C-[O;H0;D2;+0:7]-[C:8](-[C:9])=[O;D1;H0:10].C-C-[O;H0;D2;+0:11]-[C:12](-[C:13])=[O;D1;H0:14]>>[C:13]-[C:12](=[O;D1;H0:14])-[OH;D1;+0:11].[C:9]-[C:8](=[O;D1;H0:10])-[OH;D1;+0:7].[NH2;D1;+0:3]-[C;H0;D3;+0:2](=[NH;D1;+0:1])-[c:4](:[c:5]):... | 53.1 | [{"value": 53.1, "product": "C(N)(=N)C1=CC=C(C=C1)NC(C(=O)O)C1=C(C=CC=C1)OCC(=O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 4 | HOUR | 499 mg of ethyl (RS)-[4-(tert-butoxycarbonylamino-imino-methyl)-phenylamino]-(2-ethoxycarbonylmethoxy-phenyl)-acetate were treated in 14 ml of THF with 2 ml of 1N LiOH, adjusted to pH 4 after 4 hrs. with 2 ml of 1N HCl and evaporated in a vacuum. From acetonitrile-water there were obtained 182 mg of (RS)-(4-carbamimido... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ester.Ester.Ether.Boc | Carboxylic acid.Carboxylic acid.Primary amine | null | null | c1ccccc1.c1ccccc1 | HO- | C1CCOC1 | null | 4 | CCOC(=O)COc1ccccc1C(Nc1ccc(C(=N)NC(=O)OC(C)(C)C)cc1)C(=O)OCC>C1CCOC1>N=C(N)c1ccc(NC(C(=O)O)c2ccccc2OCC(=O)O)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-04746fadfa9e4bddbb619165a355184c | [H]/N=C(\NO)c1ccc(NC(C(=O)O)c2cc(OC)ccc2OC)cc1>>COc1ccc(OC)c(C(Nc2ccc(C(=N)N)cc2)C(=O)O)c1 | COC1=C(C=C(C=C1)OC)C(C(=O)O)NC1=CC=C(C=C1)/C(/NO)=N/[H].O>>C(N)(=N)C1=CC=C(C=C1)NC(C(=O)O)C1=C(C=CC(=C1)OC)OC | [H]/[N:18]=[C:16](/[c:15]1[cH:14][cH:13][c:12]([NH:11][CH:10]([c:9]2[c:6]([O:7][CH3:8])[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:24]2)[C:21](=[O:22])[OH:23])[cH:20][cH:19]1)[NH:17]O>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([O:7][CH3:8])[c:9]([CH:10]([NH:11][c:12]2[cH:13][cH:14][c:15]([C:16](=[NH:17])[NH2:18])[cH:19][cH:20]2)[C:21... | [H]/N=C(\NO)c1ccc(NC(C(=O)O)c2cc(OC)ccc2OC)cc1 | COc1ccc(OC)c(C(Nc2ccc(C(=N)N)cc2)C(=O)O)c1 | null | [Ni] | C(C)(=O)O | Miscellaneous | OtherReaction | 16a8af26e651f18d3f377c424332b1cb6f241cbeed04815d9849f17f17011d79 | 9e4acd19c4d8d44390dc672a44f6364a57c3a30bfe0036124e313667cbc7e8d9 | c1ccc(CNc2ccccc2)cc1 | O-[NH;D2;+0:1]/[C;H0;D3;+0:2](=[N;H0;D2;+0:3]\[H])-[c:4](:[c:5]):[c:6]>>[NH2;D1;+0:3]-[C;H0;D3;+0:2](=[NH;D1;+0:1])-[c:4](:[c:5]):[c:6] | 76.3 | [{"value": 76.3, "product": "C(N)(=N)C1=CC=C(C=C1)NC(C(=O)O)C1=C(C=CC(=C1)OC)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 555 mg of (Z)-(RS)-(2,5-dimethoxy-phenyl)-[4-(N-hydroxycarbamimidoyl)-phenylamino]-acetic acid were stirred under hydrogen in 8 ml of acetic acid and 16 ml of water in the presence of Raney-nickel. After the addition 13 ml of acetic acid the solution was filtered clear and evaporated in a vacuum. The residue was tritur... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amine | Primary amine | null | null | c1ccccc1.c1ccccc1 | Other | [Ni].C(C)(=O)O | null | null | [H]/N=C(\NO)c1ccc(NC(C(=O)O)c2cc(OC)ccc2OC)cc1>[Ni].C(C)(=O)O>COc1ccc(OC)c(C(Nc2ccc(C(=N)N)cc2)C(=O)O)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-355c78732744411cbcbcd0a78914fe00 | CCOC(=O)COc1ccc(OCc2ccccc2)cc1C(Nc1ccc(C#N)cc1)C(=O)OCC>>CCOC(=O)COc1ccc(OCc2ccccc2)cc1C(Nc1ccc(C(N)=S)cc1)C(=O)OCC | C(C1=CC=CC=C1)OC=1C=CC(=C(C1)C(C(=O)OCC)NC1=CC=C(C=C1)C#N)OCC(=O)OCC.P(=S)(SCC)(OCC)[O-].C(C)O>>C(C1=CC=CC=C1)OC=1C=CC(=C(C1)C(C(=O)OCC)NC1=CC=C(C=C1)C(N)=S)OCC(=O)OCC | [CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][O:7][c:8]1[cH:9][cH:10][c:11]([O:12][CH2:13][c:14]2[cH:15][cH:16][cH:17][cH:18][cH:19]2)[cH:20][c:21]1[CH:22]([NH:23][c:24]1[cH:25][cH:26][c:27]([C:28]#[N:29])[cH:31][cH:32]1)[C:33](=[O:34])[O:35][CH2:36][CH3:37]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][O:7][c:8]1[cH:9][cH:10][c:... | CCOC(=O)COc1ccc(OCc2ccccc2)cc1C(Nc1ccc(C#N)cc1)C(=O)OCC | CCOC(=O)COc1ccc(OCc2ccccc2)cc1C(Nc1ccc(C(N)=S)cc1)C(=O)OCC | null | null | C(C)(=O)OCC | Functional Group Addition | OtherReaction | 8bd1997ca69ee7332804bccbc3bd24c7b4e53460dd9092ae4bba96e531e7f422 | e4db13eae38cbdaef260d1f9800aaa52b1b91c5b72abf8089250e7d1f1121d9a | c1ccc(COc2cccc(CNc3ccccc3)c2)cc1 | [N;H0;D1;+0:1]#[C;H0;D2;+0:2]-[c:3](:[c:4]):[c:5]>>[NH2;D1;+0:1]-[C;H0;D3;+0:2](=[S;D1;H0:6])-[c:3](:[c:4]):[c:5] | null | [] | null | null | null | null | 1.7 g of ethyl (RS)-(5-benzyloxy-2-ethoxycarbonylmethoxy-phenyl)-(4-cyano-phenylamino)-acetate, 1.13 ml of diethyl dithiophosphate and 4 ml of ethanol were heated for 2 hrs. to 60° C. The reaction mixture was diluted with ethyl acetate, washed with saturated sodium hydrogen carbonate solution, water and saturated sodiu... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile | Thioamide | null | null | c1ccccc1.c1ccccc1.c1ccccc1 | Other | C(C)(=O)OCC | null | null | CCOC(=O)COc1ccc(OCc2ccccc2)cc1C(Nc1ccc(C#N)cc1)C(=O)OCC>C(C)(=O)OCC>CCOC(=O)COc1ccc(OCc2ccccc2)cc1C(Nc1ccc(C(N)=S)cc1)C(=O)OCC |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-9037f5f224e44f06a1a39c64bbbd4f5d | COc1ccc(OCC(=O)O)c(C(Nc2ccc(C(=N)NC(=O)OC(C)(C)C)cc2)C(=O)O)c1>>COc1ccc(OCC(=O)O)c(C(Nc2ccc(C(=N)N)cc2)C(=O)O)c1 | C(C)(C)(C)OC(=O)NC(C1=CC=C(C=C1)NC(C(=O)O)C1=C(C=CC(=C1)OC)OCC(=O)O)=N.C(=O)(C(F)(F)F)O>>C(N)(=N)C1=CC=C(C=C1)NC(C(=O)O)C1=C(C=CC(=C1)OC)OCC(=O)O | CC(C)(C)OC(=O)[NH:21][C:19]([c:18]1[cH:17][cH:16][c:15]([NH:14][CH:13]([c:12]2[c:6]([O:7][CH2:8][C:9](=[O:10])[OH:11])[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:27]2)[C:24](=[O:25])[OH:26])[cH:23][cH:22]1)=[NH:20]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([O:7][CH2:8][C:9](=[O:10])[OH:11])[c:12]([CH:13]([NH:14][c:15]2[cH:16][cH:17]... | COc1ccc(OCC(=O)O)c(C(Nc2ccc(C(=N)NC(=O)OC(C)(C)C)cc2)C(=O)O)c1 | COc1ccc(OCC(=O)O)c(C(Nc2ccc(C(=N)N)cc2)C(=O)O)c1 | null | null | C(Cl)Cl | Reduction | Hydrogenolysis of amides/imides/carbamates | 3c33dd2a2d355ee5ba0287367e209aa147a39aa00607f0c95fb2bf1ade45d014 | c5b5dffe7dd8beebdc1baa8b5b05300a9f7079e65dcfd42ade6f8a77ff09537d | c1ccc(CNc2ccccc2)cc1 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[C:2](=[N;D1;H1:3])-[c:4]>>[N;D1;H1:3]=[C:2](-[NH2;D1;+0:1])-[c:4] | null | [] | null | null | null | null | 356 mg of (RS)-[4-(tert-butoxy carbonylamino-imino-methyl)-phenylamino]-(2-carboxymethoxy-5-methoxy-phenyl)-acetic acid were stirred in 3.7 ml of methylene chloride and 3.7 ml of TFA for one hour. The reaction mixture was evaporated in a vacuum and the residue was chromatographed on silica gel with ethyl acetate-aceton... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Primary amine | null | null | c1ccccc1.c1ccccc1 | HO- | C(Cl)Cl | null | null | COc1ccc(OCC(=O)O)c(C(Nc2ccc(C(=N)NC(=O)OC(C)(C)C)cc2)C(=O)O)c1>C(Cl)Cl>COc1ccc(OCC(=O)O)c(C(Nc2ccc(C(=N)N)cc2)C(=O)O)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-a2eb71f613a744499ce0869e752a2ba4 | CCOC(=O)CCCCBr.CCOc1ccc(O)c(C=O)c1>>CCOC(=O)CCCCOc1ccc(OCC)cc1C=O | C(C)OC=1C=CC(=C(C=O)C1)O.BrCCCCC(=O)OCC.C(=O)([O-])[O-].[K+].[K+]>>C(C)OC1=CC(=C(OCCCCC(=O)OCC)C=C1)C=O | Br[CH2:9][CH2:8][CH2:7][CH2:6][C:4]([O:3][CH2:2][CH3:1])=[O:5].[OH:10][c:11]1[cH:12][cH:13][c:14]([O:15][CH2:16][CH3:17])[cH:18][c:19]1[CH:20]=[O:21]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][CH2:7][CH2:8][CH2:9][O:10][c:11]1[cH:12][cH:13][c:14]([O:15][CH2:16][CH3:17])[cH:18][c:19]1[CH:20]=[O:21] | CCOC(=O)CCCCBr.CCOc1ccc(O)c(C=O)c1 | CCOC(=O)CCCCOc1ccc(OCC)cc1C=O | null | null | CS(=O)C | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | c1ccccc1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[O;D1;H0:4]=[C:5]-[c:6]:[c:7](-[OH;D1;+0:8]):[c:9]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:8]-[c:7](:[c:9]):[c:6]-[C:5]=[O;D1;H0:4] | null | [] | null | null | null | null | 2.49 g of 5-ethoxy-2-hydroxy-benzaldehyde, 2.7 ml of ethyl 5-bromovalerate, 15 ml of DMSO, 3.1 g of K2CO3 and 75 mg of KI were stirred for 2.5 hrs. at 55° C. After working up and chromatography on silica gel there were obtained 4.7 g of ethyl 5-(4-ethoxy-2-formyl-phenoxy)-pentanoate. MS: 294 (M)+.
Conditions: See react... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccccc1 | HBr | CS(=O)C | null | null | CCOC(=O)CCCCBr.CCOc1ccc(O)c(C=O)c1>CS(=O)C>CCOC(=O)CCCCOc1ccc(OCC)cc1C=O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-3073f82253ee49d7a6edcb9ca4401b21 | [H]/N=C(\NO)c1ccc(NC(C(=O)OCC)c2cc(OCC)ccc2OCC(N)=O)cc1>>CCOc1ccc(OCC(N)=O)c(C(Nc2ccc(C(=N)N)cc2)C(=O)OC)c1 | C(N)(=O)COC1=C(C=C(C=C1)OCC)C(C(=O)OCC)NC1=CC=C(C=C1)/C(/NO)=N/[H]>>C(N)(=N)C1=CC=C(C=C1)NC(C(=O)OC)C1=C(C=CC(=C1)OCC)OCC(N)=O | [H]/[N:22]=[C:20](/[c:19]1[cH:18][cH:17][c:16]([NH:15][CH:14]([c:13]2[c:7]([O:8][CH2:9][C:10]([NH2:11])=[O:12])[cH:6][cH:5][c:4]([O:3][CH2:2][CH3:1])[cH:29]2)[C:25](=[O:26])[O:27][CH2:28]C)[cH:24][cH:23]1)[NH:21]O>>[CH3:1][CH2:2][O:3][c:4]1[cH:5][cH:6][c:7]([O:8][CH2:9][C:10]([NH2:11])=[O:12])[c:13]([CH:14]([NH:15][c:1... | [H]/N=C(\NO)c1ccc(NC(C(=O)OCC)c2cc(OCC)ccc2OCC(N)=O)cc1 | CCOc1ccc(OCC(N)=O)c(C(Nc2ccc(C(=N)N)cc2)C(=O)OC)c1 | null | [Ni] | CO.C(C)(=O)O | Miscellaneous | OtherReaction | dcc5ee52d81033e5b9742805182f0ff51187fe3c31968b8b08f3ee7c2e5ac6a5 | cdc6da687ac2ce49ab2aa65caa571f4243cf5107722e2106cff9c71428fdf8c9 | c1ccc(CNc2ccccc2)cc1 | C-[CH2;D2;+0:1]-[#8:2]-[C:3](-[C:4])=[O;D1;H0:5].O-[NH;D2;+0:6]/[C;H0;D3;+0:7](=[N;H0;D2;+0:8]\[H])-[c:9](:[c:10]):[c:11]>>[C:4]-[C:3](=[O;D1;H0:5])-[#8:2]-[CH3;D1;+0:1].[NH2;D1;+0:8]-[C;H0;D3;+0:7](=[NH;D1;+0:6])-[c:9](:[c:10]):[c:11] | 93.4 | [{"value": 93.4, "product": "C(N)(=N)C1=CC=C(C=C1)NC(C(=O)OC)C1=C(C=CC(=C1)OCC)OCC(N)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 305 mg of ethyl (Z)-(RS)-(2-carbamoylmethoxy-5-ethoxy-phenyl)-[4-(N-hydroxy-carbamimidoyl)-phenylamino]-acetate were treated in 8 ml of methanol-acetic acid (1:1) with Raney-nickel and stirred under hydrogen. The reaction mixture was filtered, evaporated in a vacuum and, for purification, the residue was triturated in ... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Secondary amine | Ester.Primary amine | null | null | c1ccccc1.c1ccccc1 | HO- | [Ni].CO.C(C)(=O)O | null | null | [H]/N=C(\NO)c1ccc(NC(C(=O)OCC)c2cc(OCC)ccc2OCC(N)=O)cc1>[Ni].CO.C(C)(=O)O>CCOc1ccc(OCC(N)=O)c(C(Nc2ccc(C(=N)N)cc2)C(=O)OC)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-caf06e2106ea4040ad96d94341f3d01b | CCOc1ccc(OCC(N)=O)c(C(Nc2ccc(C(=N)N)cc2)C(=O)OC)c1>>CCOc1ccc(OCC(N)=O)c(C(Nc2ccc(C(=N)N)cc2)C(=O)O)c1 | C(N)(=N)C1=CC=C(C=C1)NC(C(=O)OC)C1=C(C=CC(=C1)OCC)OCC(N)=O.[Li+].[OH-]>>C(N)(=N)C1=CC=C(C=C1)NC(C(=O)O)C1=C(C=CC(=C1)OCC)OCC(N)=O | C[O:27][C:25]([CH:14]([c:13]1[c:7]([O:8][CH2:9][C:10]([NH2:11])=[O:12])[cH:6][cH:5][c:4]([O:3][CH2:2][CH3:1])[cH:28]1)[NH:15][c:16]1[cH:17][cH:18][c:19]([C:20](=[NH:21])[NH2:22])[cH:23][cH:24]1)=[O:26]>>[CH3:1][CH2:2][O:3][c:4]1[cH:5][cH:6][c:7]([O:8][CH2:9][C:10]([NH2:11])=[O:12])[c:13]([CH:14]([NH:15][c:16]2[cH:17][c... | CCOc1ccc(OCC(N)=O)c(C(Nc2ccc(C(=N)N)cc2)C(=O)OC)c1 | CCOc1ccc(OCC(N)=O)c(C(Nc2ccc(C(=N)N)cc2)C(=O)O)c1 | null | null | C1CCOC1 | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccc(CNc2ccccc2)cc1 | C-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4]>>[C:3]-[C:2](=[O;D1;H0:4])-[OH;D1;+0:1] | null | [] | null | null | null | null | The methyl (RS)-(4-carbamimidoyl-phenylamino)-(2-carbamoylmethoxy-5-ethoxy-phenyl)-acetate was saponified in THF with 1N LiOH to give (RS)-(4-carbamimidoyl-phenylamino)-(2-carbamoylmethoxy-5-ethoxy-phenyl)-acetic acid and purified by trituration in water and dilute ammonia; m.p. 266° C., MS: 387 (M+H)+.
Conditions: See... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1.c1ccccc1 | Other | C1CCOC1 | null | null | CCOc1ccc(OCC(N)=O)c(C(Nc2ccc(C(=N)N)cc2)C(=O)OC)c1>C1CCOC1>CCOc1ccc(OCC(N)=O)c(C(Nc2ccc(C(=N)N)cc2)C(=O)O)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-e050d09ad6fd44e2867e7ef533b45e48 | CC(O)Cl.COc1ccc(C=O)c(O)c1>>COc1ccc(C=O)c(OCCO)c1 | OC1=C(C=O)C=CC(=C1)OC.C(=O)([O-])[O-].[K+].[K+].ClC(C)O>>OCCOC1=C(C=O)C=CC(=C1)OC | Cl[CH:12]([CH3:11])[OH:13].[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH:7]=[O:8])[c:9]([OH:10])[cH:14]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH:7]=[O:8])[c:9]([O:10][CH2:11][CH2:12][OH:13])[cH:14]1 | CC(O)Cl.COc1ccc(C=O)c(O)c1 | COc1ccc(C=O)c(OCCO)c1 | null | null | CS(=O)C | Heteroatom Alkylation and Arylation | OtherReaction | 2a9380ebb68334989924756cf01b7949046a4f7a65a764f1d76e39ed500565f9 | 2786f500c47f12973cdffc6c715f1d0ddaf160e62af6ac2ce87986b5e7d6597e | c1ccccc1 | Cl-[CH;D3;+0:1](-[CH3;D1;+0:2])-[O;D1;H1:3].[O;D1;H0:4]=[C:5]-[c:6]:[c:7](-[OH;D1;+0:8]):[c:9]>>[O;D1;H0:4]=[C:5]-[c:6]:[c:7](-[O;H0;D2;+0:8]-[CH2;D2;+0:2]-[CH2;D2;+0:1]-[O;D1;H1:3]):[c:9] | null | [] | null | null | null | null | 2.5 g of 2-hydroxy-4-methoxybenzaldehyde, 6.8 g of K2CO3, 3.3 ml of chloroethanol and 33 ml of DMSO were heated for 8 hrs. to 80° C. Extraction with ethyl acetate and chromatography on silica gel with methylene chloride-acetone gave 2.1 g of 2-(2-hydroxy-ethoxy)-4-methoxy-benzaldehyde, m.p. 94° C., MS: 196 (M)+.
Condit... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Secondary alcohol.Aromatic alcohol | Ether.Primary alcohol | null | null | c1ccccc1 | HCl | CS(=O)C | null | null | CC(O)Cl.COc1ccc(C=O)c(O)c1>CS(=O)C>COc1ccc(C=O)c(OCCO)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-066c90e585734d8794466e96dcddc3e2 | CCCc1ccc(O)c(C)c1.O=C(O)C(F)(F)F>>CCCc1cc(C)c(O)c(C=O)c1 | C1N2CN3CN1CN(C2)C3.CC1=C(C=CC(=C1)CCC)O.FC(C(=O)O)(F)F.Cl>>OC1=C(C=O)C=C(C=C1C)CCC | [CH3:1][CH2:2][CH2:3][c:4]1[cH:5][c:6]([CH3:7])[c:8]([OH:9])[cH:10][cH:13]1.O[C:11](C(F)(F)F)=[O:12]>>[CH3:1][CH2:2][CH2:3][c:4]1[cH:5][c:6]([CH3:7])[c:8]([OH:9])[c:10]([CH:11]=[O:12])[cH:13]1 | CCCc1ccc(O)c(C)c1.O=C(O)C(F)(F)F | CCCc1cc(C)c(O)c(C=O)c1 | null | null | C(C)(=O)OCC | C-C Coupling | OtherReaction | 90f745ece0b80581a2adb80202cff13794970e7773efa9f99af5aee9558e7702 | 926b2e005c3200dff13912ddbfc878368a562a8e6eabbdd8fa25db32ad9e0671 | c1ccccc1 | F-C(-F)(-F)-[C;H0;D3;+0:1](-O)=[O;D1;H0:2].[O;D1;H1:3]-[c:4](:[c:5]):[cH;D2;+0:6]:[c:7]:[c:8]>>[O;D1;H0:2]=[CH;D2;+0:1]-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:4](-[O;D1;H1:3]):[c:5] | null | [] | null | null | 1 | HOUR | 4.2 g of hexamethylenetetramine were cautiously added to 1.5 g of 2-methyl-4-propyl-phenol in 11 ml of trifluoroacetic acid and the mixture was heated for 5 hrs. to 120° C. After the addition of 11 ml of 1N hydrochloric acid the mixture was stirred for 1 hr. at 107° C. The mixture was cooled to room temperature, dilute... | 10.6084/m9.figshare.5104873.v1 | null | Trifluoro group.Carboxylic acid | Aldehyde | c1ccccc1 | c1ccccc1 | c1ccccc1 | HF | C(C)(=O)OCC | null | 1 | CCCc1ccc(O)c(C)c1.O=C(O)C(F)(F)F>C(C)(=O)OCC>CCCc1cc(C)c(O)c(C=O)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-0baaad83b32b4bc39b88f19861cabf4c | CCOc1cc(C=O)ccc1O.OCCBr>>CCOc1cc(C=O)ccc1OCCO | BrCCO.C([O-])([O-])=O.[K+].[K+].C(C)OC=1C=C(C=O)C=CC1O>>C(C)OC=1C=C(C=O)C=CC1OCCO | [CH3:1][CH2:2][O:3][c:4]1[cH:5][c:6]([CH:7]=[O:8])[cH:9][cH:10][c:11]1[OH:12].Br[CH2:13][CH2:14][OH:15]>>[CH3:1][CH2:2][O:3][c:4]1[cH:5][c:6]([CH:7]=[O:8])[cH:9][cH:10][c:11]1[O:12][CH2:13][CH2:14][OH:15] | CCOc1cc(C=O)ccc1O.OCCBr | CCOc1cc(C=O)ccc1OCCO | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | c1ccccc1 | Br-[CH2;D2;+0:1]-[C:2]-[O;D1;H1:3].[OH;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[O;D1;H1:3]-[C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:4]-[c:5](:[c:6]):[c:7] | null | [] | 120 | CELSIUS | null | null | 2.76 ml of 2-bromoethanol and 5.40 g of potassium carbonate were added to a solution of 5 g of 3-ethoxy-4-hydroxybenzaldehyde in 150 ml of DMF. The reaction mixture was heated to 70° C. overnight and subsequently to 120° C. for a further 4 hrs. Then, the mixture was left to cool to room temperature, filtered and concen... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccccc1 | HBr | CN(C)C=O | 120 | null | CCOc1cc(C=O)ccc1O.OCCBr>CN(C)C=O>CCOc1cc(C=O)ccc1OCCO |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-8bad292a7e054daab3cb6369aa944890 | CC(C)Oc1ccc(C=O)cc1OCCO>>CC(C)Oc1ccc(C=O)cc1O | BrCCO.OCCOC=1C=C(C=O)C=CC1OC(C)C>>OC=1C=C(C=O)C=CC1OC(C)C | OCC[O:13][c:12]1[c:5]([O:4][CH:2]([CH3:1])[CH3:3])[cH:6][cH:7][c:8]([CH:9]=[O:10])[cH:11]1>>[CH3:1][CH:2]([CH3:3])[O:4][c:5]1[cH:6][cH:7][c:8]([CH:9]=[O:10])[cH:11][c:12]1[OH:13] | CC(C)Oc1ccc(C=O)cc1OCCO | CC(C)Oc1ccc(C=O)cc1O | null | null | null | Reduction | OtherReaction | 4a66bcf82a2b9b4fffef5c6b6c007d1d0481718dd10228721dcf3aa4deefb7f2 | f78fa56f31fe176e07ba04b30637e2c1222d7496d48126ef057f127f14b0ebb7 | c1ccccc1 | O-C-C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[OH;D1;+0:1]-[c:2](:[c:3]):[c:4] | 75 | [{"value": 75.0, "product": "OC=1C=C(C=O)C=CC1OC(C)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | from 3-hydroxy-4-isopropoxybenzaldehyde (prepared in 75% yield by monoalkylation of 3,4-dihydroxybenzaldehyde with isopropyl bromide and K2CO3 in DMF) and 2-bromo-ethanol there was obtained 3-(2-hydroxy-ethoxy)-4-isopropoxy-benzaldehyde, which was subsequently converted by reaction with 4-aminobenzonitrile and toluene-... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Primary alcohol | Aromatic alcohol | null | null | c1ccccc1 | HO- | null | null | null | CC(C)Oc1ccc(C=O)cc1OCCO>>CC(C)Oc1ccc(C=O)cc1O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-2063ef9bf60b47c195f8389bf096c4d4 | COC(=O)C(Nc1ccc(C#N)cc1)c1ccc(OC)c(N)c1.O=C1CCCC(=O)O1>>COC(=O)C(Nc1ccc(C#N)cc1)c1ccc(OC)c(NC(=O)CCCC(=O)O)c1 | NC=1C=C(C=CC1OC)C(C(=O)OC)NC1=CC=C(C=C1)C#N.C1(CCCC(=O)O1)=O.CCN(C(C)C)C(C)C>>C(#N)C1=CC=C(C=C1)NC(C=1C=CC(=C(C1)NC(=O)CCCC(=O)O)OC)C(=O)OC | [CH3:1][O:2][C:3](=[O:4])[CH:5]([NH:6][c:7]1[cH:8][cH:9][c:10]([C:11]#[N:12])[cH:13][cH:14]1)[c:15]1[cH:16][cH:17][c:18]([O:19][CH3:20])[c:21]([NH2:22])[cH:31]1.[C:23]1(=[O:24])[CH2:25][CH2:26][CH2:27][C:28](=[O:29])[O:30]1>>[CH3:1][O:2][C:3](=[O:4])[CH:5]([NH:6][c:7]1[cH:8][cH:9][c:10]([C:11]#[N:12])[cH:13][cH:14]1)[c... | COC(=O)C(Nc1ccc(C#N)cc1)c1ccc(OC)c(N)c1.O=C1CCCC(=O)O1 | COC(=O)C(Nc1ccc(C#N)cc1)c1ccc(OC)c(NC(=O)CCCC(=O)O)c1 | null | null | CN(C)C=O | Protection | OtherReaction | f6be9d499b924ab549bee67179c1b1cd0c968ccc4bcf3fa6e4d0ec37226c4fbe | d83a5fe7c1575bfa4f6a9dc1cf7406e299c5c7ecfc75f13bc6d348857a70653f | c1ccc(CNc2ccccc2)cc1 | [NH2;D1;+0:1]-[c:2](:[c:3]):[c:4].[O;D1;H0:5]=[C;H0;D3;+0:6]1-[C:7]-[C:8]-[C:9]-[C:10](=[O;D1;H0:11])-[O;H0;D2;+0:12]-1>>[O;D1;H0:5]=[C;H0;D3;+0:6](-[C:7]-[C:8]-[C:9]-[C:10](=[O;D1;H0:11])-[OH;D1;+0:12])-[NH;D2;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | null | null | In analogy to Example 70.4–6, from the methyl (RS)-(3-amino-4-methoxy-phenyl)-(4-cyano-phenylamino)-acetate described in Example 70.3, glutaric anhydride and Hünig's base in DMF there was obtained (RS)-4-{5-[(4-cyano-phenylamino)-methoxycarbonyl-methyl]-2-methoxy-phenylcarbamoyl}-butyric acid, which was subsequently co... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Primary amine | Carboxylic acid.Secondary amide | C1CCOCC1 | null | c1ccccc1.c1ccccc1 | null | CN(C)C=O | null | null | COC(=O)C(Nc1ccc(C#N)cc1)c1ccc(OC)c(N)c1.O=C1CCCC(=O)O1>CN(C)C=O>COC(=O)C(Nc1ccc(C#N)cc1)c1ccc(OC)c(NC(=O)CCCC(=O)O)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-bf09a1dc06e4487f919dbbc9a6f83e7d | COC(=O)C(Nc1ccc(C#N)cc1)c1ccc(OC)c(NC(=O)CCCC(=O)O)c1.O=C1CCC(=O)O1>>CCN(C(C)C)C(C)C.COC(=O)C(Nc1ccc(C#N)cc1)c1ccc(OC)c(NC(=O)CCC(=O)O)c1 | C(#N)C1=CC=C(C=C1)NC(C=1C=CC(=C(C1)NC(=O)CCCC(=O)O)OC)C(=O)OC.C1(CCC(=O)O1)=O>>CCN(C(C)C)C(C)C.C(#N)C1=CC=C(C=C1)NC(C=1C=CC(=C(C1)NC(CCC(=O)O)=O)OC)C(=O)OC | [CH2:1]([CH2:5][C:32]([NH:15][c:30]1[c:27]([O:28][CH3:29])[cH:26][cH:25][c:24]([CH:14]([NH:3][c:16]2[cH:17][cH:18][c:19]([C:20]#[N:21])[cH:22][cH:23]2)[C:12]([O:11][CH3:10])=[O:13])[cH:39]1)=[O:33])[CH2:35][C:36](=[O:37])[OH:38].O=[C:4]1O[C:7](=O)[CH2:8][CH2:6]1>>[CH3:1][CH2:2][N:3]([CH:4]([CH3:5])[CH3:6])[CH:7]([CH3:8... | COC(=O)C(Nc1ccc(C#N)cc1)c1ccc(OC)c(NC(=O)CCCC(=O)O)c1.O=C1CCC(=O)O1 | CCN(C(C)C)C(C)C.COC(=O)C(Nc1ccc(C#N)cc1)c1ccc(OC)c(NC(=O)CCC(=O)O)c1 | null | null | null | C-C Coupling | OtherReaction | e384b2844334f0aa6f0f3515e166c00e9c45c18f25b67b1260278e31d6a5338d | a8e33a85a7b4837b798665ef6050f0ffbf1b03358012185df5d47635f6f56996 | c1ccc(CNc2ccccc2)cc1 | O=[C;H0;D3;+0:1]1-O-[C;H0;D3;+0:2](=O)-[CH2;D2;+0:3]-[CH2;D2;+0:4]-1.[#8:5]-[c:6]1:[c:7]:[c:8]:[c:9](-[CH;D3;+0:10](-[NH;D2;+0:11]-[c;H0;D3;+0:12](:[c:13]:[c:14]):[c:15]:[c:16])-[C:17](=[O;D1;H0:18])-[#8:19]-[C;D1;H3:20]):[c:21]:[c;H0;D3;+0:22]:1-[NH;D2;+0:23]-[C;H0;D3;+0:24](=[O;D1;H0:25])-[CH2;D2;+0:26]-[CH2;D2;+0:27... | null | [] | null | null | null | null | In analogy to Example 70.4–6, from the methyl (RS)-(3-amino-4-methoxy-phenyl)-(4-cyano-phenylamino)-acetate described in Example 70.3, succinic anhydride and Hünig's base there was obtained (RS)-N-{5-[(4-cyano-phenylamino)-methoxycarbonyl-methyl]-2-methoxy-phenyl}-succinamidic acid, which was subsequently converted via... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Ester.Secondary amide.Secondary amine | Ester.Secondary amide.Secondary amine.Tertiary amine | c1ccccc1.c1ccccc1.C1CCOC1 | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | null | null | null | null | COC(=O)C(Nc1ccc(C#N)cc1)c1ccc(OC)c(NC(=O)CCCC(=O)O)c1.O=C1CCC(=O)O1>>CCN(C(C)C)C(C)C.COC(=O)C(Nc1ccc(C#N)cc1)c1ccc(OC)c(NC(=O)CCC(=O)O)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-b756258db26b4c7393b28ec15c898830 | COC(=O)c1cc(I)cc(C(=O)OC)c1>>OCc1cc(I)cc(CO)c1 | Cl.[BH4-].[Na+].COC(C1=CC(C(=O)OC)=CC(=C1)I)=O>>OCC=1C=C(C=C(C1)I)CO | CO[C:2](=[O:1])[c:3]1[cH:4][c:5]([I:6])[cH:7][c:8]([C:9](OC)=[O:10])[cH:11]1>>[OH:1][CH2:2][c:3]1[cH:4][c:5]([I:6])[cH:7][c:8]([CH2:9][OH:10])[cH:11]1 | COC(=O)c1cc(I)cc(C(=O)OC)c1 | OCc1cc(I)cc(CO)c1 | null | null | O.C1CCOC1 | Reduction | OtherReaction | 8eb0b0948ba02d6bff2e6dcc47886480a262869f201923801796429d5f921f16 | 3906c52a610c5241bd14656b0a46d01a4c70864c3b16d9b6e34a49708e61df8d | c1ccccc1 | C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[c:3](:[c:4]):[c:5]:[c:6](-[C;H0;D3;+0:7](=[O;H0;D1;+0:8])-O-C):[c:9]>>[OH;D1;+0:8]-[CH2;D2;+0:7]-[c:6](:[c:9]):[c:5]:[c:3](-[CH2;D2;+0:1]-[OH;D1;+0:2]):[c:4] | null | [] | null | null | 1 | DAY | A solution of dimethyl-5-iodisophthalate in 800 ml of THF was treated with with 22.2 g of CaCI2. Then, 15.2 g of NaBH4 were added portionwise. The mixture was stirred for one day at room temperature. Then, the mixture was acidified with 250 ml of 3N HCl and diluted with 2 l of H2O. The crude product was isolated by ext... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester | Primary alcohol.Primary alcohol | null | null | c1ccccc1 | Other | O.C1CCOC1 | null | 24 | COC(=O)c1cc(I)cc(C(=O)OC)c1>O.C1CCOC1>OCc1cc(I)cc(CO)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-9908b37de9214e75a9b350b7380e92d7 | COC(=O)C(Nc1ccc(C#N)cc1)c1cc(C=O)cc(C=O)c1>>C=Cc1cc(C=O)cc(C(Nc2ccc(C#N)cc2)C(=O)OC)c1 | C(#N)C1=CC=C(C=C1)NC(C(=O)OC)C1=CC(=CC(=C1)C=O)C=O.C([O-])([O-])=O.[K+].[K+]>>C(#N)C1=CC=C(C=C1)NC(C(=O)OC)C1=CC(=CC(=C1)C=C)C=O | O=[CH:2][c:3]1[cH:4][c:5]([CH:6]=[O:7])[cH:8][c:9]([CH:10]([NH:11][c:12]2[cH:13][cH:14][c:15]([C:16]#[N:17])[cH:18][cH:19]2)[C:20](=[O:21])[O:22][CH3:23])[cH:24]1>>[CH2:1]=[CH:2][c:3]1[cH:4][c:5]([CH:6]=[O:7])[cH:8][c:9]([CH:10]([NH:11][c:12]2[cH:13][cH:14][c:15]([C:16]#[N:17])[cH:18][cH:19]2)[C:20](=[O:21])[O:22][CH3:... | COC(=O)C(Nc1ccc(C#N)cc1)c1cc(C=O)cc(C=O)c1 | C=Cc1cc(C=O)cc(C(Nc2ccc(C#N)cc2)C(=O)OC)c1 | null | [Br-].C[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1 | O1CCOCC1.CN(C)C=O | Functional Group Interconversion | OtherReaction | dd6fb167b4e71f3ea190d18ad4e87d18c641d879b83b47beb9dc06bc791584b1 | 6b3ec9b506a5bb4882685e77a1e07fcb518f891061dfbc2d36767289330c841e | c1ccc(CNc2ccccc2)cc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[C;D1;H2:5]=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4] | 45.9 | [{"value": 45.9, "product": "C(#N)C1=CC=C(C=C1)NC(C(=O)OC)C1=CC(=CC(=C1)C=C)C=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 2.87 g of methyl (RS)-(4-cyano-phenylamino)-(3,5-diformyl-phenyl)-acetate in 20 ml of dioxan and 1.3 ml of DMF was treated with 3.18 g of methyltriphenylphosphonium bromid and 1.84 g of potassium carbonate. The suspension was heated for 3 days to 100° C. It was left to cool to room temperature, filtered a... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | Vinyl | null | null | c1ccccc1.c1ccccc1 | null | [Br-].C[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1.O1CCOCC1.CN(C)C=O | null | null | COC(=O)C(Nc1ccc(C#N)cc1)c1cc(C=O)cc(C=O)c1>[Br-].C[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1.O1CCOCC1.CN(C)C=O>C=Cc1cc(C=O)cc(C(Nc2ccc(C#N)cc2)C(=O)OC)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-2c3e8dd25a97498fa7f2918b43c0afd0 | C1CCNC1.C=Cc1cc(C=O)cc(C(Nc2ccc(C#N)cc2)C(=O)OC)c1>>C=Cc1cc(CN2CCCC2)cc(C(Nc2ccc(C#N)cc2)C(=O)OC)c1 | Cl.C(#N)C1=CC=C(C=C1)NC(C(=O)OC)C1=CC(=CC(=C1)C=C)C=O.N1CCCC1.[Na]>>C(#N)C1=CC=C(C=C1)NC(C(=O)OC)C1=CC(=CC(=C1)C=C)CN1CCCC1 | [NH:7]1[CH2:8][CH2:9][CH2:10][CH2:11]1.O=[CH:6][c:5]1[cH:4][c:3]([CH:2]=[CH2:1])[cH:28][c:13]([CH:14]([NH:15][c:16]2[cH:17][cH:18][c:19]([C:20]#[N:21])[cH:22][cH:23]2)[C:24](=[O:25])[O:26][CH3:27])[cH:12]1>>[CH2:1]=[CH:2][c:3]1[cH:4][c:5]([CH2:6][N:7]2[CH2:8][CH2:9][CH2:10][CH2:11]2)[cH:12][c:13]([CH:14]([NH:15][c:16]2... | C1CCNC1.C=Cc1cc(C=O)cc(C(Nc2ccc(C#N)cc2)C(=O)OC)c1 | C=Cc1cc(CN2CCCC2)cc(C(Nc2ccc(C#N)cc2)C(=O)OC)c1 | null | null | C(C)(=O)O.CO | Heteroatom Alkylation and Arylation | reductive amination | f320c54beea598cd731a01400cf9495fa26416685f3307ec69cb487e38cf79c3 | 2d03f38884b1fbb0c0d6e6f2de31afb25102fec87f347c3a123e064c1bfef0ad | c1ccc(NCc2cccc(CN3CCCC3)c2)cc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[C:5]1-[C:6]-[NH;D2;+0:7]-[C:8]-[C:9]-1>>[c:3]:[c:2](-[CH2;D2;+0:1]-[N;H0;D3;+0:7]1-[C:6]-[C:5]-[C:9]-[C:8]-1):[c:4] | null | [] | null | null | 8 | HOUR | Eine suspension von 200 mg of the aldehyde described in Example 80.1 and 0.062 ml of pyrrolidine in 2 ml of MeOH was adjusted to pH 6 by the dropwise addition of acetic acid. Then, 46 mg of sodium cyanoborhydride were added and the mixture was stirred overnight at room temperature. It was acidified to pH 3 with 1N HCl ... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Secondary amine | Tertiary amine | C1CCNC1 | C1CC[NH]C1 | c1ccccc1.C1CC[NH]C1.c1ccccc1 | Other | C(C)(=O)O.CO | null | 8 | C1CCNC1.C=Cc1cc(C=O)cc(C(Nc2ccc(C#N)cc2)C(=O)OC)c1>C(C)(=O)O.CO>C=Cc1cc(CN2CCCC2)cc(C(Nc2ccc(C#N)cc2)C(=O)OC)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-22162707b9e04266845c1816e90d3c06 | C1N2CN3CN1CN(C2)C3.CCc1ccc(O)cc1.O>>CCc1ccc(O)c(C=O)c1 | C1N2CN3CN1CN(C2)C3.C(C)C1=CC=C(C=C1)O.O.Cl>>C(C)C=1C=CC(=C(C=O)C1)O | C1N2CN3CN1CN(C2)[CH2:9]3.[CH3:1][CH2:2][c:3]1[cH:4][cH:5][c:6]([OH:7])[cH:8][cH:11]1.[OH2:10]>>[CH3:1][CH2:2][c:3]1[cH:4][cH:5][c:6]([OH:7])[c:8]([CH:9]=[O:10])[cH:11]1 | C1N2CN3CN1CN(C2)C3.CCc1ccc(O)cc1.O | CCc1ccc(O)c(C=O)c1 | null | null | CC(=O)O.C(C)OCC | Heteroatom Alkylation and Arylation | OtherReaction | 98d7ac5b3983168fb9ed670a6d6243789108504bf9b3fe21aa37d25ce36a0563 | ddcb0f373c34c33f09380f6f3c17bae455c33e7b8311682c33023bb3f450b77f | c1ccccc1 | C1-N2-C-N3-C-N-1-C-N(-C-2)-[CH2;D2;+0:1]-3.[O;D1;H1:2]-[c:3](:[c:4]):[cH;D2;+0:5]:[c:6]:[c:7].[OH2;D0;+0:8]>>[O;D1;H1:2]-[c:3](:[c:4]):[c;H0;D3;+0:5](-[CH;D2;+0:1]=[O;H0;D1;+0:8]):[c:6]:[c:7] | null | [] | null | null | 5 | HOUR | 114 g of hexamethylenetetramine were added to a solution of 20 g of 4-ethylphenol in 400 ml of AcOH. The reaction solution was stirred for 5 hrs. at 100° C. Then, 150 ml of H2O and 150 ml of 25% HCl solution were added. The mixture was stirred for 1 hr. at 100° C. Then, it was left to cool to room temperature. The crud... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amine.Tertiary amine.Tertiary amine.Tertiary amine | Aldehyde | c1ccccc1.C1N2CN3CN1CN(C2)C3 | c1ccccc1 | c1ccccc1 | Other | CC(=O)O.C(C)OCC | null | 5 | C1N2CN3CN1CN(C2)C3.CCc1ccc(O)cc1.O>CC(=O)O.C(C)OCC>CCc1ccc(O)c(C=O)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-555f353c0dd84093b0ef48f51cd08b7f | CCC(=O)c1ccc(O)cc1.O>>CCC(=O)c1ccc(O)c(C=O)c1 | Cl.O.C(Cl)(Cl)Cl.CCC(=O)C1=CC=C(C=C1)O.[OH-].[Na+].C(Cl)(Cl)Cl>>OC1=C(C=O)C=C(C=C1)C(CC)=O | [CH3:1][CH2:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([OH:9])[cH:10][cH:13]1.[OH2:12]>>[CH3:1][CH2:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([OH:9])[c:10]([CH:11]=[O:12])[cH:13]1 | CCC(=O)c1ccc(O)cc1.O | CCC(=O)c1ccc(O)c(C=O)c1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | e3eb3563143a436a1b6dd1eadac83913d5a87e712b8ad652ab28367873285db5 | be117abed4a0a0378ea43d3a5c1ccf903b86823ade7e92fcb09d68743e45d19a | c1ccccc1 | [O;D1;H0:1]=[C:2]-[c:3]:[c:4]:[cH;D2;+0:5]:[c:6](-[O;D1;H1:7]):[c:8].[OH2;D0;+0:9]>>[O;D1;H0:1]=[C:2]-[c:3]:[c:4]:[c;H0;D3;+0:5](-[C:10]=[O;H0;D1;+0:9]):[c:6](-[O;D1;H1:7]):[c:8] | null | [] | null | null | 5 | HOUR | 21 ml of CHCl3 were added dropwise within 30 minutes to a suspension, heated to 55° C., of 20 g of 4-hydroxypropiophenone in 95 ml of 28% NaOH. The yellow suspension was heated for 1.5 hrs. to 55° C. Then, a further 5 ml of CHCl3 were added dropwise. After a further 5 hours at 60° C. the mixture was left to cool to roo... | 10.6084/m9.figshare.5104873.v1 | null | null | Aldehyde | c1ccccc1 | c1ccccc1 | c1ccccc1 | Other | null | null | 5 | CCC(=O)c1ccc(O)cc1.O>>CCC(=O)c1ccc(O)c(C=O)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-b966adeec5a648ae97ec3fc6acffb13d | CCOc1ccc(C=O)cc1OCC.O=[N+]([O-])O>>CCOc1cc(C=O)c([N+](=O)[O-])cc1OCC | [N+](=O)(O)[O-].C(C)OC=1C=C(C=O)C=CC1OCC>>C(C)OC1=CC(=C(C=O)C=C1OCC)[N+](=O)[O-] | [CH3:1][CH2:2][O:3][c:4]1[cH:5][cH:6][c:9]([CH:7]=[O:8])[cH:13][c:14]1[O:15][CH2:16][CH3:17].O[N+:10](=[O:11])[O-:12]>>[CH3:1][CH2:2][O:3][c:4]1[cH:5][c:6]([CH:7]=[O:8])[c:9]([N+:10](=[O:11])[O-:12])[cH:13][c:14]1[O:15][CH2:16][CH3:17] | CCOc1ccc(C=O)cc1OCC.O=[N+]([O-])O | CCOc1cc(C=O)c([N+](=O)[O-])cc1OCC | null | null | ClCCCl | Functional Group Addition | Aromatic nitration with HNO3 | ba69704fd3b997e3e689ef12d366ef8a72a7280cad9edbd0ec40fe273d882ebd | e8f2d48f0735c41a2e2e297558a82e57e6bd4104e0ea84db8bd38839e2328cb4 | c1ccccc1 | O-[N+;H0;D3:1](-[O;-;D1;H0:2])=[O;D1;H0:3].[O;D1;H0:4]=[CH;D2;+0:5]-[c;H0;D3;+0:6]1:[c:7]:[c:8]:[c:9]:[c:10]:[cH;D2;+0:11]:1>>[O;-;D1;H0:2]-[N+;H0;D3:1](=[O;D1;H0:3])-[c;H0;D3;+0:6]1:[c:7]:[c:8]:[c:9]:[c:10]:[c;H0;D3;+0:11]:1-[CH;D2;+0:5]=[O;D1;H0:4] | null | [] | 0 | CELSIUS | null | null | 2.13 ml of fuming nitric acid were added within 30 minutes to a solution, cooled to −30° C. of 10 g of 3,4-diethoxybenzaldehyde in 185 ml of 1,2-dichloroethane. Subsequently, the reaction mixture was left to warm to 0° C. and was poured on to ice. The product was isolated by extraction. There were obtained 12.06 g of 4... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Nitrate | Aldehyde.Nitro group | c1ccccc1 | c1ccccc1 | c1ccccc1 | HO- | ClCCCl | 0 | null | CCOc1ccc(C=O)cc1OCC.O=[N+]([O-])O>ClCCCl>CCOc1cc(C=O)c([N+](=O)[O-])cc1OCC |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-c8f31cbe78c94129b2d06d5f9fafd1fc | Cc1ccc(CO)cc1C.II>>Cc1cc(I)c(CO)cc1C | CC=1C=C(CO)C=CC1C.CN(CCN(C)C)C.II.S(O)(O)(=O)=O.C(CCC)[Li]>>IC1=C(C=C(C(=C1)C)C)CO | [CH3:1][c:2]1[cH:3][cH:4][c:6]([CH2:7][OH:8])[cH:9][c:10]1[CH3:11].I[I:5]>>[CH3:1][c:2]1[cH:3][c:4]([I:5])[c:6]([CH2:7][OH:8])[cH:9][c:10]1[CH3:11] | Cc1ccc(CO)cc1C.II | Cc1cc(I)c(CO)cc1C | null | null | CCCCC.C1CCOC1 | Functional Group Interconversion | OtherReaction | f6effe61353895b318215d8bd9b6bb1105cafbf7be8c217d748df587260b32c3 | 3c4065ab4a8681675e06a527dcad54d701c7bfdcac9f73f87773b05034108934 | c1ccccc1 | I-[I;H0;D1;+0:1].[C:2]-[c:3](:[c:4]):[cH;D2;+0:5]:[c:6]:[c:7]>>[C:2]-[c:3](:[c:4]):[c;H0;D3;+0:5](-[I;H0;D1;+0:1]):[c:6]:[c:7] | 22.5 | [{"value": 22.5, "product": "IC1=C(C=C(C(=C1)C)C)CO", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -30 | CELSIUS | 15 | MINUTE | A solution, cooled to 0° C., of 6.81 g of 3,4-dimethylbenzyl alcohol and 11.62 ml of N,N,N′,N′-tetramethyl-ethylenediamine in 150 ml of pentane was treated with 62.5 ml of n-butyllithium solution (1.6M in hexane). The reaction mixture was boiled at reflux for 11 hrs. Then, 12.69 g of iodine in 50 ml of THF were added d... | 10.6084/m9.figshare.5104873.v1 | null | null | Aromatic halide | c1ccccc1 | c1ccccc1 | c1ccccc1 | HI | CCCCC.C1CCOC1 | -30 | 0.25 | Cc1ccc(CO)cc1C.II>CCCCC.C1CCOC1>Cc1cc(I)c(CO)cc1C |
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