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-f5ea4275f12a4d89add6cc64e08ca0fc | CNC1CCN(C)CC1.NN.O=C(C(=C1SCS1)c1ccncc1)c1ccc(Cl)cc1>>CN1CCC(N(C)c2n[nH]c(-c3ccc(Cl)cc3)c2-c2ccncc2)CC1.O.O | NN.ClC1=CC=C(C=C1)C(C(C1=CC=NC=C1)=C1SCS1)=O.CN1CCC(CC1)NC>>O.O.ClC1=CC=C(C=C1)C1=C(C(=NN1)N(C1CCN(CC1)C)C)C1=CC=NC=C1 | [CH3:1][N:2]1[CH2:3][CH2:4][CH:5]([NH:6][CH3:7])[CH2:26][CH2:27]1.[NH2:9][NH2:10].C1S[C:8](=[C:19]([C:11]([c:12]2[cH:13][cH:14][c:15]([Cl:16])[cH:17][cH:18]2)=[O:28])[c:20]2[cH:21][cH:22][n:23][cH:24][cH:25]2)S1>>[CH3:1][N:2]1[CH2:3][CH2:4][CH:5]([N:6]([CH3:7])[c:8]2[n:9][nH:10][c:11](-[c:12]3[cH:13][cH:14][c:15]([Cl:1... | CNC1CCN(C)CC1.NN.O=C(C(=C1SCS1)c1ccncc1)c1ccc(Cl)cc1 | CN1CCC(N(C)c2n[nH]c(-c3ccc(Cl)cc3)c2-c2ccncc2)CC1.O.O | null | null | C1(=CC=CC=C1)C | Aromatic Heterocycle Formation | OtherReaction | 66668f7b040d350eff55912a616182c18833fa880914cf26d39c7fcc73985fce | 1e5f9b38d7db4fe595144f898e5235f6b6271ba8ecf3ac3e92120040e09a299c | c1ccc(-c2[nH]nc(NC3CCNCC3)c2-c2ccncc2)cc1 | [C:1]-[C:2](-[NH;D2;+0:3]-[C;D1;H3:4])-[C:5].[NH2;D1;+0:6]-[NH2;D1;+0:7].[O;H0;D1;+0:8]=[C;H0;D3;+0:9](-[C;H0;D3;+0:10](=[C;H0;D3;+0:11]1-S-C-S-1)-[c;H0;D3;+0:12]1:[c:13]:[c:14]:[#7;a:15]:[c:16]:[c:17]:1)-[c;H0;D3;+0:18](:[c:19]:[c:20]):[c:21]:[c:22]>>[C:1]-[C:2](-[N;H0;D3;+0:3](-[C;D1;H3:4])-[c;H0;D3;+0:11]1:[n;H0;D2;... | null | [] | null | null | 16 | HOUR | A solution of 1-(4-chlorophenyl)-2-(1,3-dithietan-2-ylidene)-2-(4-pyridinyl)ethanone (3.2 g, 0.01 mol; prepared as set forth in Step 1 of Example A-341) and 1-methyl-4-methylaminopiperidine (3.8 g, 0.03 mol) in 30 mL of toluene refluxed for six hours under nitrogen. The mixture was cooled and solvent was removed under ... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Ketone.Secondary amine.Monosulfide.Monosulfide | Tertiary amine | C1SCS1 | c1cn[nH]c1 | C1CC[NH]CC1.c1cn[nH]c1.c1ccccc1.c1ccncc1 | Other | C1(=CC=CC=C1)C | null | 16 | CNC1CCN(C)CC1.NN.O=C(C(=C1SCS1)c1ccncc1)c1ccc(Cl)cc1>C1(=CC=CC=C1)C>CN1CCC(N(C)c2n[nH]c(-c3ccc(Cl)cc3)c2-c2ccncc2)CC1.O.O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-a36163f273644400a750bd00a453d89a | COC(=O)c1cccc(C)c1.Cc1ccncc1>>Cc1ccccc1C(=O)Cc1ccncc1 | C([O-])(O)=O.[Na+].CC=1C=C(C(=O)OC)C=CC1.N1=CC=C(C=C1)C>>C1(=C(C=CC=C1)C(CC1=CC=NC=C1)=O)C | CO[C:8]([c:6]1[cH:5][cH:4][cH:3][c:2]([CH3:1])[cH:7]1)=[O:9].[CH3:10][c:11]1[cH:12][cH:13][n:14][cH:15][cH:16]1>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][cH:6][c:7]1[C:8](=[O:9])[CH2:10][c:11]1[cH:12][cH:13][n:14][cH:15][cH:16]1 | COC(=O)c1cccc(C)c1.Cc1ccncc1 | Cc1ccccc1C(=O)Cc1ccncc1 | null | null | O1CCCC1 | C-C Coupling | OtherReaction | f71c5083a5ac794cf8cea99a1f880de7dc082a90bfbd324fa7eea301f55849c8 | f80cbbd7f2bfc042e62829b7de30498cf0880b808f2adad888ffdfe089982722 | O=C(Cc1ccncc1)c1ccccc1 | C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c;H0;D3;+0:3]1:[c:4]:[c:5]:[c:6]:[c:7](-[C;D1;H3:8]):[cH;D2;+0:9]:1.[CH3;D1;+0:10]-[c:11]1:[c:12]:[c:13]:[#7;a:14]:[c:15]:[c:16]:1>>[C;D1;H3:8]-[c:7]1:[c:6]:[c:5]:[c:4]:[cH;D2;+0:3]:[c;H0;D3;+0:9]:1-[C;H0;D3;+0:1](=[O;D1;H0:2])-[CH2;D2;+0:10]-[c:11]1:[c:12]:[c:13]:[#7;a:14]:[c:15]:[c:1... | 67 | [{"value": 67.0, "product": "C1(=C(C=CC=C1)C(CC1=CC=NC=C1)=O)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 16 | HOUR | Methyl 3-methylbenzoate (6.0 g, 40 mmol), tetrahydrofuran (50 mL), and 4-picoline (4.1 g, 44 mmol) were stirred at −78° C. under an atmosphere of nitrogen. Sodium (bis)trimethylsilylamide 1.0 M in tetrahydrofuran (88 mL, 88 mmol) was added dropwise. The mixture was allowed to warm to room temperature, stirred for 16 ho... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Ketone | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccncc1 | HO- | O1CCCC1 | null | 16 | COC(=O)c1cccc(C)c1.Cc1ccncc1>O1CCCC1>Cc1ccccc1C(=O)Cc1ccncc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-3c2395c0b857419f92a68432f944dc02 | COC(OC)N(C)C.O=C(Cc1ccncc1)c1ccc(Cl)cc1>>CN(C)C=C(C(=O)c1ccc(Cl)cc1)c1ccncc1 | ClC1=CC=C(C=C1)C(CC1=CC=NC=C1)=O.COC(N(C)C)OC>>CN(C=C(C(=O)C1=CC=C(C=C1)Cl)C1=CC=NC=C1)C | CO[CH:4](OC)[N:2]([CH3:1])[CH3:3].[CH2:5]([C:6](=[O:7])[c:8]1[cH:9][cH:10][c:11]([Cl:12])[cH:13][cH:14]1)[c:15]1[cH:16][cH:17][n:18][cH:19][cH:20]1>>[CH3:1][N:2]([CH3:3])[CH:4]=[C:5]([C:6](=[O:7])[c:8]1[cH:9][cH:10][c:11]([Cl:12])[cH:13][cH:14]1)[c:15]1[cH:16][cH:17][n:18][cH:19][cH:20]1 | COC(OC)N(C)C.O=C(Cc1ccncc1)c1ccc(Cl)cc1 | CN(C)C=C(C(=O)c1ccc(Cl)cc1)c1ccncc1 | null | null | null | C-C Coupling | OtherReaction | 57f48fac7254684faf48980af66a0d538cb8dee0ab05f049059285d4840b8be4 | 49ae3600e90e05c7cda8811d9438748b91211f407b3eab7b1bcb51e798f4d85a | [CH]=C(C(=O)c1ccccc1)c1ccncc1 | C-O-[CH;D3;+0:1](-O-C)-[#7:2](-[C;D1;H3:3])-[C;D1;H3:4].[O;D1;H0:5]=[C:6](-[c:7])-[CH2;D2;+0:8]-[c:9]1:[c:10]:[c:11]:[#7;a:12]:[c:13]:[c:14]:1>>[C;D1;H3:3]-[#7:2](-[C;D1;H3:4])-[CH;D2;+0:1]=[C;H0;D3;+0:8](-[C:6](=[O;D1;H0:5])-[c:7])-[c:9]1:[c:10]:[c:11]:[#7;a:12]:[c:13]:[c:14]:1 | 93 | [{"value": 93.0, "product": "CN(C=C(C(=O)C1=CC=C(C=C1)Cl)C1=CC=NC=C1)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 92.0, "product": "CN(C=C(C(=O)C1=CC=C(C=C1)Cl)C1=CC=NC=C1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 4-chlorophenyl-2-(pyridin-4-yl)ethan-1-one (20.0 g, 86.4 mmol) and N,N-dimethylformamide dimethylacetal (57.6 mL, 0.43 mole) was heated at 100° C. for 3½ hours. The reaction mixture was concentrated in vacuo, and the residue crystallized from methyl butyl ether to give 3-dimethylamino-1-(4-chlorophenyl)-2... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ether.Ether | Enamine | null | null | c1ccccc1.c1ccncc1 | HO- | null | null | null | COC(OC)N(C)C.O=C(Cc1ccncc1)c1ccc(Cl)cc1>>CN(C)C=C(C(=O)c1ccc(Cl)cc1)c1ccncc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-e54c2312aec14dd88e707cc27d2a5367 | CN(C)C=C(C(=O)c1ccc(Cl)cc1)c1ccncc1.NO>>Clc1ccc(-c2oncc2-c2ccncc2)cc1 | CN(C=C(C(=O)C1=CC=C(C=C1)Cl)C1=CC=NC=C1)C.Cl.NO>>ClC1=CC=C(C=C1)C1=C(C=NO1)C1=CC=NC=C1 | CN(C)[CH:9]=[C:10]([C:6](=O)[c:5]1[cH:4][cH:3][c:2]([Cl:1])[cH:18][cH:17]1)[c:11]1[cH:12][cH:13][n:14][cH:15][cH:16]1.[OH:7][NH2:8]>>[Cl:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[o:7][n:8][cH:9][c:10]2-[c:11]2[cH:12][cH:13][n:14][cH:15][cH:16]2)[cH:17][cH:18]1 | CN(C)C=C(C(=O)c1ccc(Cl)cc1)c1ccncc1.NO | Clc1ccc(-c2oncc2-c2ccncc2)cc1 | null | null | C(C)O | Aromatic Heterocycle Formation | OtherReaction | a7518d17f0a3bf60b4868b3d11fe5be619126351e9a5ed1794e47c5ba67d9f56 | 11da551d0a7bf93f6d300d0e461ec1d4a2060497908163f95323146dc93cd499 | c1ccc(-c2oncc2-c2ccncc2)cc1 | C-N(-C)-[CH;D2;+0:1]=[C;H0;D3;+0:2](-[C;H0;D3;+0:3](=O)-[c;H0;D3;+0:4](:[c:5]:[c:6]):[c:7]:[c:8])-[c;H0;D3;+0:9]1:[c:10]:[c:11]:[#7;a:12]:[c:13]:[c:14]:1.[NH2;D1;+0:15]-[OH;D1;+0:16]>>[c:6]:[c:5]:[c;H0;D3;+0:4](-[c;H0;D3;+0:3]1:[o;H0;D2;+0:16]:[n;H0;D2;+0:15]:[cH;D2;+0:1]:[c;H0;D3;+0:2]:1-[c;H0;D3;+0:9]1:[c:10]:[c:11]:... | 100.2 | [{"value": 93.0, "product": "ClC1=CC=C(C=C1)C1=C(C=NO1)C1=CC=NC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 100.2, "product": "ClC1=CC=C(C=C1)C1=C(C=NO1)C1=CC=NC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 3-dimethylamino-1-(4-chlorophenyl)-2-(pyridin-4-yl)-2-propen-1-one (22.80 g, 79.7 mmol), hydroxylamine hydrochloride (18.01 g, 0.26 mole), and 150 mL ethanol was heated to reflux for 30 minutes. The reaction mixture was then cooled to room temperature and concentrated in vacuo. The residue was dissolved i... | 10.6084/m9.figshare.5104873.v1 | null | Enamine.Ketone.Primary amine | null | null | c1cnoc1 | c1ccccc1.c1cnoc1.c1ccncc1 | HO- | C(C)O | null | null | CN(C)C=C(C(=O)c1ccc(Cl)cc1)c1ccncc1.NO>C(C)O>Clc1ccc(-c2oncc2-c2ccncc2)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-fa98c3cbc4724ae7bf67ca62ca3a59ba | Clc1ccc(-c2oncc2-c2ccncc2)cc1>>N#CC(C(=O)c1ccc(Cl)cc1)c1ccncc1 | ClC1=CC=C(C=C1)C1=C(C=NO1)C1=CC=NC=C1.[OH-].[Na+].Cl>>ClC1=CC=C(C=C1)C(C(C#N)C1=CC=NC=C1)=O | [n:1]1[cH:2][c:3](-[c:13]2[cH:14][cH:15][n:16][cH:17][cH:18]2)[c:4](-[c:6]2[cH:7][cH:8][c:9]([Cl:10])[cH:11][cH:12]2)[o:5]1>>[N:1]#[C:2][CH:3]([C:4](=[O:5])[c:6]1[cH:7][cH:8][c:9]([Cl:10])[cH:11][cH:12]1)[c:13]1[cH:14][cH:15][n:16][cH:17][cH:18]1 | Clc1ccc(-c2oncc2-c2ccncc2)cc1 | N#CC(C(=O)c1ccc(Cl)cc1)c1ccncc1 | null | null | null | Functional Group Interconversion | OtherReaction | 988f5ecb6893138f7696b85137f70a283649704fd2748dac4566897d9fa89a3f | 094ab7cbf55168da34d8325942e7e2db7a6a5f62d13487c76c266fa6a77fadf8 | O=C(Cc1ccncc1)c1ccccc1 | [c:1]:[c:2]:[c;H0;D3;+0:3](-[c;H0;D3;+0:4]1:[o;H0;D2;+0:5]:[n;H0;D2;+0:6]:[cH;D2;+0:7]:[c;H0;D3;+0:8]:1-[c;H0;D3;+0:9]1:[c:10]:[c:11]:[#7;a:12]:[c:13]:[c:14]:1):[c:15]:[c:16]>>[N;H0;D1;+0:6]#[C;H0;D2;+0:7]-[CH;D3;+0:8](-[C;H0;D3;+0:4](=[O;H0;D1;+0:5])-[c;H0;D3;+0:3](:[c:2]:[c:1]):[c:15]:[c:16])-[c;H0;D3;+0:9]1:[c:10]:[... | 97.5 | [{"value": 97.5, "product": "ClC1=CC=C(C=C1)C(C(C#N)C1=CC=NC=C1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 5-(4-chlorophenyl)-4-(pyridin-4-yl)isoxazole (20.5 g, 79.9 mmol) and 150 mL of a 1N sodium hydroxide solution was stirred at 60° C. for 1 hour. The reaction mixture was cooled to room temperature and adjusted to pH 6 with concentrated hydrochloric acid. The precipitates were filtered, washed with water an... | 10.6084/m9.figshare.5104873.v1 | null | null | Ketone.Nitrile | c1cnoc1 | null | c1ccccc1.c1ccncc1 | null | null | null | null | Clc1ccc(-c2oncc2-c2ccncc2)cc1>>N#CC(C(=O)c1ccc(Cl)cc1)c1ccncc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-c2cfab61dacf4fe79de29a3b11fabbe1 | N#CC(C(=O)c1ccc(Cl)cc1)c1ccncc1.NN>>Nc1[nH]nc(-c2ccc(Cl)cc2)c1-c1ccncc1 | NN.ClC1=CC=C(C=C1)C(C(C#N)C1=CC=NC=C1)=O.P(Cl)(Cl)Cl>>NC1=C(C(=NN1)C1=CC=C(C=C1)Cl)C1=CC=NC=C1 | O=[C:5]([c:6]1[cH:7][cH:8][c:9]([Cl:10])[cH:11][cH:12]1)[CH:13]([C:2]#[N:1])[c:14]1[cH:15][cH:16][n:17][cH:18][cH:19]1.[NH2:3][NH2:4]>>[NH2:1][c:2]1[nH:3][n:4][c:5](-[c:6]2[cH:7][cH:8][c:9]([Cl:10])[cH:11][cH:12]2)[c:13]1-[c:14]1[cH:15][cH:16][n:17][cH:18][cH:19]1 | N#CC(C(=O)c1ccc(Cl)cc1)c1ccncc1.NN | Nc1[nH]nc(-c2ccc(Cl)cc2)c1-c1ccncc1 | null | null | C(C)#N | Aromatic Heterocycle Formation | OtherReaction | 5313ea2b547a7e97f846d9307e42ac2925475188c06332e189417467db3f09a0 | a78e9303472e036bbc8878e5b3222e30e9aba072d6de158deb64f510e46fb597 | c1ccc(-c2n[nH]cc2-c2ccncc2)cc1 | O=[C;H0;D3;+0:1](-[CH;D3;+0:2](-[C;H0;D2;+0:3]#[N;H0;D1;+0:4])-[c;H0;D3;+0:5]1:[c:6]:[c:7]:[#7;a:8]:[c:9]:[c:10]:1)-[c;H0;D3;+0:11](:[c:12]:[c:13]):[c:14]:[c:15].[NH2;D1;+0:16]-[NH2;D1;+0:17]>>[NH2;D1;+0:4]-[c;H0;D3;+0:3]1:[nH;D2;+0:16]:[n;H0;D2;+0:17]:[c;H0;D3;+0:1](-[c;H0;D3;+0:11](:[c:12]:[c:13]):[c:14]:[c:15]):[c;H... | 54.3 | [{"value": 54.0, "product": "NC1=C(C(=NN1)C1=CC=C(C=C1)Cl)C1=CC=NC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 54.3, "product": "NC1=C(C(=NN1)C1=CC=C(C=C1)Cl)C1=CC=NC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 3-(4-chlorophenyl)-3-oxo-2-(pyridin-4-yl)propanenitrile (3.50 g, 13.6 mmol) in 40 mL acetonitrile and phosphorous trichloride (14.2 ml, 163 mmol) was stirred at 100° C. for 5 hours. The reaction mixture was concentrated in vacuo, and the residue taken up in toluene and concentrated again. The residue was ... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Ketone.Nitrile | Primary amine | null | c1cn[nH]c1 | c1cn[nH]c1.c1ccccc1.c1ccncc1 | HO- | C(C)#N | null | null | N#CC(C(=O)c1ccc(Cl)cc1)c1ccncc1.NN>C(C)#N>Nc1[nH]nc(-c2ccc(Cl)cc2)c1-c1ccncc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-6a244503d35e42249897c86205157480 | CC(=O)O.O=C1C=C(Br)C(=O)O1.O=C1C=CC(=O)N1.c1cn[nH]c1>>COc1ccc(CN)c(OC)c1 | N1N=CC=C1.C1(C=CC(N1)=O)=O.[H][H].C(C)(=O)O.Br/C=1/C(=O)OC(\C1)=O>>COC1=C(CN)C=CC(=C1)OC | O=C(O)[CH3:1].O=[C:4]1O[C:9](=[O:10])[C:6](Br)=[CH:5]1.O=[C:7]1C=CC(=[O:2])[NH:8]1.n1[nH][cH:12][cH:3][cH:11]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][NH2:8])[c:9]([O:10][CH3:11])[cH:12]1 | CC(=O)O.O=C1C=C(Br)C(=O)O1.O=C1C=CC(=O)N1.c1cn[nH]c1 | COc1ccc(CN)c(OC)c1 | null | null | C(C)(=O)OC(C)=O | Heteroatom Alkylation and Arylation | OtherReaction | aa934dc3a27fded16e6e719e1a086ed9af0e6d5e4347ab13fe9409b061031e56 | 058aee31981cc2e7f5bc4f3d5e93dac606cf1b8b758c4fadbb2159f717b53416 | c1ccccc1 | Br-[C;H0;D3;+0:1]1=[CH;D2;+0:2]-[C;H0;D3;+0:3](=O)-O-[C;H0;D3;+0:4]-1=[O;H0;D1;+0:5].O-C(=O)-[CH3;D1;+0:6].O=[C;H0;D3;+0:7]1-C=C-C(=[O;H0;D1;+0:8])-[NH;D2;+0:9]-1.[cH;D2;+0:10]1:[cH;D2;+0:11]:[cH;D2;+0:12]:[nH]:n:1>>[CH3;D1;+0:10]-[O;H0;D2;+0:5]-[c;H0;D3;+0:4]1:[cH;D2;+0:12]:[c;H0;D3;+0:11](-[O;H0;D2;+0:8]-[CH3;D1;+0:6... | null | [] | null | null | null | null | Scheme C-6 illustrates the synthesis of the male imide pyrazole scaffold C-63 wherein R4 is hydrogen. The synthesis starts with the condensation reaction of bromomaleic anhydride B77 with 2,4-dimethoxybenzylamine in acetic acid and acetic anhydride, giving rise to intermediate B78. The maleimide B78 is then treated wit... | 10.6084/m9.figshare.5104873.v1 | null | Alkenyl halide.Anhydride.Carboxylic acid.Unsubstituted dicarboximide | Ether.Ether.Primary amine | C1=CCOC1.C1=CCNC1.c1cn[nH]c1 | c1ccccc1 | c1ccccc1 | Br- | C(C)(=O)OC(C)=O | null | null | CC(=O)O.O=C1C=C(Br)C(=O)O1.O=C1C=CC(=O)N1.c1cn[nH]c1>C(C)(=O)OC(C)=O>COc1ccc(CN)c(OC)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-f1994b11a73a40d4874f3873cedb76f6 | CCOC(=O)c1ccc(F)cc1.Cc1ccncc1>>O=C(Cc1ccncc1)c1ccc(F)cc1 | FC1=CC=C(C(=O)OCC)C=C1.N1=CC=C(C=C1)C.[Li+].C[Si](C)(C)[N-][Si](C)(C)C.O>>FC1=CC=C(C=C1)C(CC1=CC=NC=C1)=O | CCO[C:2](=[O:1])[c:10]1[cH:11][cH:12][c:13]([F:14])[cH:15][cH:16]1.[CH3:3][c:4]1[cH:5][cH:6][n:7][cH:8][cH:9]1>>[O:1]=[C:2]([CH2:3][c:4]1[cH:5][cH:6][n:7][cH:8][cH:9]1)[c:10]1[cH:11][cH:12][c:13]([F:14])[cH:15][cH:16]1 | CCOC(=O)c1ccc(F)cc1.Cc1ccncc1 | O=C(Cc1ccncc1)c1ccc(F)cc1 | null | null | CCCCCC.C(C)#N.O.C1CCOC1 | C-C Coupling | OtherReaction | 8ce89878f5db9b98fa4633d16adf2407dbf79d96925d930c608f1ce0756e674e | f80cbbd7f2bfc042e62829b7de30498cf0880b808f2adad888ffdfe089982722 | O=C(Cc1ccncc1)c1ccccc1 | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[CH3;D1;+0:6]-[c:7]1:[c:8]:[c:9]:[#7;a:10]:[c:11]:[c:12]:1>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[CH2;D2;+0:6]-[c:7]1:[c:8]:[c:9]:[#7;a:10]:[c:11]:[c:12]:1)-[c:3](:[c:4]):[c:5] | null | [] | null | null | 1 | HOUR | 4-picoline (40 g, 0.43 mol) was added to a LiHMDS solution (0.45 mol, 450 mL of a 1.0 M solution in THF) over 30 minutes at room temperature (a slight exotherm was observed) The resulting solution was stirred for 1 h. This solution was added to ethyl 4-fluorobenzoate (75.8 g, 0.45 mol, neat) over 1 h. The mixture was s... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Ketone | null | null | c1ccncc1.c1ccccc1 | HO- | CCCCCC.C(C)#N.O.C1CCOC1 | null | 1 | CCOC(=O)c1ccc(F)cc1.Cc1ccncc1>CCCCCC.C(C)#N.O.C1CCOC1>O=C(Cc1ccncc1)c1ccc(F)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-f0043a2def8a4d06a30359f60dfea182 | CC(C)(C)OC(=O)N1CCN(c2n[nH]c(-c3ccc(F)cc3)c2-c2ccncc2)CC1.O=C(NCC(=O)C1CC(=O)N(O)C1=O)OCc1ccccc1>>NCc1c(-c2ccncc2)c(-c2ccc(F)cc2)nn1C(=O)OCc1ccccc1 | C(C1=CC=CC=C1)OC(=O)NCC(=O)C1C(=O)N(C(C1)=O)O.C1CCOC1.O.NN.FC1=CC=C(C=C1)C1=C(C(=NN1)N1CCN(CC1)C(=O)OC(C)(C)C)C1=CC=NC=C1.C1CCOC1.CC(C)(C)[O-].[K+].CC(C)(C)O.C1CCOC1>>C(C1=CC=CC=C1)OC(=O)N1N=C(C(=C1CN)C1=CC=NC=C1)C1=CC=C(C=C1)F | CC(C)(C)OC(=O)N1CCN([c:3]2[c:4](-[c:5]3[cH:6][cH:7][n:8][cH:9][cH:10]3)[c:11](-[c:12]3[cH:13][cH:14][c:15]([F:16])[cH:17][cH:18]3)[nH:19][n:20]2)CC1.O=C1CC(C(=O)[CH2:2][NH:1][C:21](=[O:22])[O:23][CH2:24][c:25]2[cH:26][cH:27][cH:28][cH:29][cH:30]2)C(=O)N1O>>[NH2:1][CH2:2][c:3]1[c:4](-[c:5]2[cH:6][cH:7][n:8][cH:9][cH:10]... | CC(C)(C)OC(=O)N1CCN(c2n[nH]c(-c3ccc(F)cc3)c2-c2ccncc2)CC1.O=C(NCC(=O)C1CC(=O)N(O)C1=O)OCc1ccccc1 | NCc1c(-c2ccncc2)c(-c2ccc(F)cc2)nn1C(=O)OCc1ccccc1 | null | null | O.CC(=O)O.C(C)(=O)OCC | Acylation | OtherReaction | e948f38baa4a382286e7606bfdfe71cd793ef4bfed517f46ba1e9e8c82fd3aa3 | ed2040ef5e96ece2e68ddd1f63bca138356c74a198afcc01aa5dbdc6fcbebffc | O=C(OCc1ccccc1)n1cc(-c2ccncc2)c(-c2ccccc2)n1 | C-C(-C)(-C)-O-C(=O)-N1-C-C-N(-[c;H0;D3;+0:1]2:[n;H0;D2;+0:2]:[nH;D2;+0:3]:[c:4](-[c:5]):[c:6]:2-[c:7])-C-C-1.O-N1-C(=O)-C-C(-C(=O)-[CH2;D2;+0:8]-[NH;D2;+0:9]-[C;H0;D3;+0:10](=[O;D1;H0:11])-[#8:12]-[C:13])-C-1=O>>[C:13]-[#8:12]-[C;H0;D3;+0:10](=[O;D1;H0:11])-[n;H0;D3;+0:2]1:[n;H0;D2;+0:3]:[c:4](-[c:5]):[c:6](-[c:7]):[c;... | null | [] | null | null | 1 | HOUR | A 3 L round bottom flask fitted with a mechanical stirrer, N2 inlet and an addition funnel was was charged wtih 557 mL (0.56 mol) of 1 M t-BuOK in THF and 53 mL (0.56 mol) of t-BuOH. The ketone, 1 (60 g, 0.28 mol) was dissolved in 600 mL of THF and added to the stirred mixture at room temperature. A yellow precipitate ... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Carbamic ester.Ketone.Ether.Ether.Tertiary amide.Tertiary amide.Tertiary amine.Boc | Ether.Primary amine | C1CNCCN1.c1cn[nH]c1.C1CCNC1 | c1cn[nH]c1 | c1cn[nH]c1.c1ccncc1.c1ccccc1.c1ccccc1 | HO- | O.CC(=O)O.C(C)(=O)OCC | null | 1 | CC(C)(C)OC(=O)N1CCN(c2n[nH]c(-c3ccc(F)cc3)c2-c2ccncc2)CC1.O=C(NCC(=O)C1CC(=O)N(O)C1=O)OCc1ccccc1>O.CC(=O)O.C(C)(=O)OCC>NCc1c(-c2ccncc2)c(-c2ccc(F)cc2)nn1C(=O)OCc1ccccc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-20bcf6d0be51405da84d66068bf9abd6 | C=O.Clc1ccc(-c2n[nH]c(C3CCNCC3)c2-c2ccncc2)cc1>>CN1CCC(c2[nH]nc(-c3ccc(Cl)cc3)c2-c2ccncc2)CC1 | Cl.N1CCC(CC1)C1=C(C(=NN1)C1=CC=C(C=C1)Cl)C1=CC=NC=C1.C=O>>CN1CCC(CC1)C1=C(C(=NN1)C1=CC=C(C=C1)Cl)C1=CC=NC=C1 | O=[CH2:1].[NH:2]1[CH2:3][CH2:4][CH:5]([c:6]2[nH:7][n:8][c:9](-[c:10]3[cH:11][cH:12][c:13]([Cl:14])[cH:15][cH:16]3)[c:17]2-[c:18]2[cH:19][cH:20][n:21][cH:22][cH:23]2)[CH2:24][CH2:25]1>>[CH3:1][N:2]1[CH2:3][CH2:4][CH:5]([c:6]2[nH:7][n:8][c:9](-[c:10]3[cH:11][cH:12][c:13]([Cl:14])[cH:15][cH:16]3)[c:17]2-[c:18]2[cH:19][cH:... | C=O.Clc1ccc(-c2n[nH]c(C3CCNCC3)c2-c2ccncc2)cc1 | CN1CCC(c2[nH]nc(-c3ccc(Cl)cc3)c2-c2ccncc2)CC1 | null | null | C(=O)O | Heteroatom Alkylation and Arylation | Eschweiler-Clarke Secondary Amine Methylation | e23db47f33553519e7237e30c3b19a21fcbb90bde44fbb5566021920bc9b7164 | e1fdef8fde1c506d7c9deb8fd5e6f322eceea2abce3167abcf412a1fa4fd5443 | c1ccc(-c2n[nH]c(C3CCNCC3)c2-c2ccncc2)cc1 | O=[CH2;D1;+0:1].[C:2]-[C:3]-[NH;D2;+0:4]-[C:5]-[C:6]>>[C:2]-[C:3]-[N;H0;D3;+0:4](-[CH3;D1;+0:1])-[C:5]-[C:6] | null | [] | 75 | CELSIUS | 48 | HOUR | To a solution of 5-(4-piperidyl)-4-(4-pyridyl)-3-(4-chlorophenyl)pyrazole hydrochloride (Example C-74) (25 g, 61 mmol) in 140 mL of formic acid (96%) was added 50 g of formaldehyde (37%). The solution was stirred at 75° C. for 48 h and was cooled to room temperature. The excess formic acid was removed under reduced pre... | 10.6084/m9.figshare.5104873.v1 | null | Formaldehyde.Secondary amine | Tertiary amine | C1CCNCC1 | C1CC[NH]CC1 | C1CC[NH]CC1.c1cn[nH]c1.c1ccccc1.c1ccncc1 | Other | C(=O)O | 75 | 48 | C=O.Clc1ccc(-c2n[nH]c(C3CCNCC3)c2-c2ccncc2)cc1>C(=O)O>CN1CCC(c2[nH]nc(-c3ccc(Cl)cc3)c2-c2ccncc2)CC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-3c18face392345ea9efa734606e357f7 | CC(=O)Cl.Clc1ccc(-c2n[nH]c(C3CCNCC3)c2-c2ccncc2)cc1>>CC(=O)N1CCC(c2[nH]nc(-c3ccc(Cl)cc3)c2-c2ccncc2)CC1 | Cl.N1CCC(CC1)C1=C(C(=NN1)C1=CC=C(C=C1)Cl)C1=CC=NC=C1.C(C)(=O)Cl>>C(C)(=O)N1CCC(CC1)C1=C(C(=NN1)C1=CC=C(C=C1)Cl)C1=CC=NC=C1 | Cl[C:2]([CH3:1])=[O:3].[NH:4]1[CH2:5][CH2:6][CH:7]([c:8]2[nH:9][n:10][c:11](-[c:12]3[cH:13][cH:14][c:15]([Cl:16])[cH:17][cH:18]3)[c:19]2-[c:20]2[cH:21][cH:22][n:23][cH:24][cH:25]2)[CH2:26][CH2:27]1>>[CH3:1][C:2](=[O:3])[N:4]1[CH2:5][CH2:6][CH:7]([c:8]2[nH:9][n:10][c:11](-[c:12]3[cH:13][cH:14][c:15]([Cl:16])[cH:17][cH:1... | CC(=O)Cl.Clc1ccc(-c2n[nH]c(C3CCNCC3)c2-c2ccncc2)cc1 | CC(=O)N1CCC(c2[nH]nc(-c3ccc(Cl)cc3)c2-c2ccncc2)CC1 | null | CN(C1=CC=NC=C1)C | null | Acylation | N-alkylation of secondary amines with alkyl halides | aaa7c80569e6aa145ac8d7318e06893ee71aff0c965e85eca836522c948938d5 | 96cb0a2fed10552c5770a45a2d6523b47ac3e38928b4a9c698d8577451182dcd | c1ccc(-c2n[nH]c(C3CCNCC3)c2-c2ccncc2)cc1 | Cl-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[C:4]-[C:5]-[NH;D2;+0:6]-[C:7]-[C:8]>>[C:4]-[C:5]-[N;H0;D3;+0:6](-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3])-[C:7]-[C:8] | null | [] | null | null | 3 | HOUR | To a stirred suspension of 5-(4-piperidyl)-4-(4-pyridyl)-3-(4-chlorophenyl)pyrazole hydrochloride (Example C-74) (1 g, 2.4 mmol) in 24 mL of CH2Cl, was added 4-dimethylamino pyridine (0.88 g, 7.2 mmol) and acetyl chloride (0.21 g, 2.6 mmol). The solution was stirred for 3 h and the solvent was removed under reduced pre... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Secondary amine | Tertiary amide | C1CCNCC1 | C1CC[NH]CC1 | C1CC[NH]CC1.c1cn[nH]c1.c1ccccc1.c1ccncc1 | HCl | CN(C1=CC=NC=C1)C | null | 3 | CC(=O)Cl.Clc1ccc(-c2n[nH]c(C3CCNCC3)c2-c2ccncc2)cc1>CN(C1=CC=NC=C1)C>CC(=O)N1CCC(c2[nH]nc(-c3ccc(Cl)cc3)c2-c2ccncc2)CC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-97c15f2003174d97bcaaf348c665dccb | COCCBr.Clc1ccc(-c2n[nH]c(C3CCNCC3)c2-c2ccncc2)cc1>>COCCN1CCC(c2[nH]nc(-c3ccc(Cl)cc3)c2-c2ccncc2)CC1 | [OH-].[Na+].Cl.N1CCC(CC1)C1=C(C(=NN1)C1=CC=C(C=C1)Cl)C1=CC=NC=C1.CCN(C(C)C)C(C)C.COCCBr>>COCCN1CCC(CC1)C1=C(C(=NN1)C1=CC=C(C=C1)Cl)C1=CC=NC=C1 | Br[CH2:4][CH2:3][O:2][CH3:1].[NH:5]1[CH2:6][CH2:7][CH:8]([c:9]2[nH:10][n:11][c:12](-[c:13]3[cH:14][cH:15][c:16]([Cl:17])[cH:18][cH:19]3)[c:20]2-[c:21]2[cH:22][cH:23][n:24][cH:25][cH:26]2)[CH2:27][CH2:28]1>>[CH3:1][O:2][CH2:3][CH2:4][N:5]1[CH2:6][CH2:7][CH:8]([c:9]2[nH:10][n:11][c:12](-[c:13]3[cH:14][cH:15][c:16]([Cl:17... | COCCBr.Clc1ccc(-c2n[nH]c(C3CCNCC3)c2-c2ccncc2)cc1 | COCCN1CCC(c2[nH]nc(-c3ccc(Cl)cc3)c2-c2ccncc2)CC1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 0240b8450ff2c489d02f5f0d90bc953079d7a3ab239d35a03f26392fc248b4ef | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | c1ccc(-c2n[nH]c(C3CCNCC3)c2-c2ccncc2)cc1 | Br-[CH2;D2;+0:1]-[C:2]-[#8:3].[C:4]-[C:5]-[NH;D2;+0:6]-[C:7]-[C:8]>>[#8:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:6](-[C:5]-[C:4])-[C:7]-[C:8] | null | [] | null | null | 5 | DAY | To a stirred suspension of 5-(4-piperidyl)-4-(4-pyridyl)-3-(4-chlorophenyl)pyrazole hydrochloride (Example C-74) (500 mg, 1.2 mmol) in 12 mL of DMF was added Hunig's base (790 mg, 6.1 mmol) and 2-bromoethyl methyl ether (850 mg, 6.1 mmol). The solution was stirred at room temperature for 5 days. The solution was poured... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1CCNCC1 | C1CC[NH]CC1 | C1CC[NH]CC1.c1cn[nH]c1.c1ccccc1.c1ccncc1 | HBr | CN(C)C=O | null | 120 | COCCBr.Clc1ccc(-c2n[nH]c(C3CCNCC3)c2-c2ccncc2)cc1>CN(C)C=O>COCCN1CCC(c2[nH]nc(-c3ccc(Cl)cc3)c2-c2ccncc2)CC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-dced9e77dfa444e38e07a3cc1c984cdb | Clc1ccc(-c2n[nH]c(C3CCNCC3)c2-c2ccncc2)cc1.O=Cc1nccs1>>Cc1nc(N2CCC(c3[nH]nc(-c4ccc(Cl)cc4)c3-c3ccncc3)CC2)cs1 | [BH3-]C#N.[Na+].Cl.N1CCC(CC1)C1=C(C(=NN1)C1=CC=C(C=C1)Cl)C1=CC=NC=C1.C(OC)(OC)OC.S1C(=NC=C1)C=O.[OH-].[Na+]>>CC=1SC=C(N1)N1CCC(CC1)C1=C(C(=NN1)C1=CC=C(C=C1)Cl)C1=CC=NC=C1 | [NH:5]1[CH2:6][CH2:7][CH:8]([c:9]2[nH:10][n:11][c:12](-[c:13]3[cH:14][cH:15][c:16]([Cl:17])[cH:18][cH:19]3)[c:20]2-[c:21]2[cH:22][cH:23][n:24][cH:25][cH:26]2)[CH2:27][CH2:28]1.O=[CH:1][c:2]1[n:3][cH:4][cH:29][s:30]1>>[CH3:1][c:2]1[n:3][c:4]([N:5]2[CH2:6][CH2:7][CH:8]([c:9]3[nH:10][n:11][c:12](-[c:13]4[cH:14][cH:15][c:1... | Clc1ccc(-c2n[nH]c(C3CCNCC3)c2-c2ccncc2)cc1.O=Cc1nccs1 | Cc1nc(N2CCC(c3[nH]nc(-c4ccc(Cl)cc4)c3-c3ccncc3)CC2)cs1 | null | null | CO | Heteroatom Alkylation and Arylation | OtherReaction | 6ab34a471146709f1a33979f57c33225c09d5e389eff2af66114e1d73f679a9e | 2d03f38884b1fbb0c0d6e6f2de31afb25102fec87f347c3a123e064c1bfef0ad | c1ccc(-c2n[nH]c(C3CCN(c4cscn4)CC3)c2-c2ccncc2)cc1 | O=[CH;D2;+0:1]-[c:2]1:[#16;a:3]:[c:4]:[cH;D2;+0:5]:[#7;a:6]:1.[C:7]-[C:8]-[NH;D2;+0:9]-[C:10]-[C:11]>>[C:7]-[C:8]-[N;H0;D3;+0:9](-[c;H0;D3;+0:5]1:[#7;a:6]:[c:2](-[CH3;D1;+0:1]):[#16;a:3]:[c:4]:1)-[C:10]-[C:11] | null | [] | null | null | 2 | HOUR | To a suspension of 5-(4-piperidyl)-4-(4-pyridyl)-3-(4-chlorophenyl)pyrazole hydrochloride (Example C-74) in 12 mL of MeOH was added trimethyl orthoformate (2.6 g, 24.4 mmol) and 2-thiazolecarboxaldehyde (1.4 g, 12.2 mmol). The suspension was stirred at room temperature for 2 h. To this mixture was added NaCNBH3 (1.5 g,... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Secondary amine | Tertiary amine | C1CCNCC1.c1cscn1 | c1cscn1.C1CC[NH]CC1 | c1cscn1.C1CC[NH]CC1.c1cn[nH]c1.c1ccccc1.c1ccncc1 | Other | CO | null | 2 | Clc1ccc(-c2n[nH]c(C3CCNCC3)c2-c2ccncc2)cc1.O=Cc1nccs1>CO>Cc1nc(N2CCC(c3[nH]nc(-c4ccc(Cl)cc4)c3-c3ccncc3)CC2)cs1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-79735cfa6b494b23a9edd70a44272171 | CC(C)=O.FC(F)(F)c1ccc(-c2n[nH]c(C3CCNCC3)c2-c2ccncc2)cc1>>CC(C)N1CCC(c2[nH]nc(-c3ccc(C(F)(F)F)cc3)c2-c2ccncc2)CC1 | [OH-].[Na+].N1CCC(CC1)C1=C(C(=NN1)C1=CC=C(C=C1)C(F)(F)F)C1=CC=NC=C1.CC(=O)O.CC(=O)C>>CC(C)N1CCC(CC1)C1=C(C(=NN1)C1=CC=C(C=C1)C(F)(F)F)C1=CC=NC=C1 | O=[C:2]([CH3:1])[CH3:3].[NH:4]1[CH2:5][CH2:6][CH:7]([c:8]2[nH:9][n:10][c:11](-[c:12]3[cH:13][cH:14][c:15]([C:16]([F:17])([F:18])[F:19])[cH:20][cH:21]3)[c:22]2-[c:23]2[cH:24][cH:25][n:26][cH:27][cH:28]2)[CH2:29][CH2:30]1>>[CH3:1][CH:2]([CH3:3])[N:4]1[CH2:5][CH2:6][CH:7]([c:8]2[nH:9][n:10][c:11](-[c:12]3[cH:13][cH:14][c:... | CC(C)=O.FC(F)(F)c1ccc(-c2n[nH]c(C3CCNCC3)c2-c2ccncc2)cc1 | CC(C)N1CCC(c2[nH]nc(-c3ccc(C(F)(F)F)cc3)c2-c2ccncc2)CC1 | null | null | null | Heteroatom Alkylation and Arylation | reductive amination | 5b9aae81d5db6cfc5f72477ba0ee2aec96ad799a6d24e9c614e5f4b9464c670b | 99acf13bfcfe579f51ccb82c65e4ca039ee7ca9b6fcd2747a3d9a292a88e564e | c1ccc(-c2n[nH]c(C3CCNCC3)c2-c2ccncc2)cc1 | O=[C;H0;D3;+0:1](-[C;D1;H3:2])-[C;D1;H3:3].[C:4]-[C:5]-[NH;D2;+0:6]-[C:7]-[C:8]>>[C:4]-[C:5]-[N;H0;D3;+0:6](-[CH;D3;+0:1](-[C;D1;H3:2])-[C;D1;H3:3])-[C:7]-[C:8] | null | [] | null | null | 5 | DAY | To a solution of 5-(4-piperidyl)-4-(4-pyridyl)-3-(4-(trifluoromethyl)phenyl]pyrazole (Example C-83) (300 mg, 0.7 mmol) in 50 mL of acetone was added 1 mL of AcOH and NaBH(OAc), (15 g, 70.8 mmol). The mixture was warmed to reflux and was stirred for 5 days, The reaction mixture was poured onto 100 mL of 2.5 N NaOH and w... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Secondary amine | Tertiary amine | C1CCNCC1 | C1CC[NH]CC1 | C1CC[NH]CC1.c1cn[nH]c1.c1ccccc1.c1ccncc1 | Other | null | null | 120 | CC(C)=O.FC(F)(F)c1ccc(-c2n[nH]c(C3CCNCC3)c2-c2ccncc2)cc1>>CC(C)N1CCC(c2[nH]nc(-c3ccc(C(F)(F)F)cc3)c2-c2ccncc2)CC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-2689bdda56db4c80b9e66c9627ee0bc3 | NCc1[nH]nc(-c2ccc(F)cc2)c1-c1ccncc1.O=C([O-])c1ccc([N+](=O)[O-])cc1>>O=CNCc1[nH]nc(-c2ccc(F)cc2)c1-c1ccncc1 | NCC1=C(C(=NN1)C1=CC=C(C=C1)F)C1=CC=NC=C1.[N+](=O)([O-])C1=CC=C(C=C1)C(=O)[O-]>>C(=O)NCC1=C(C(=NN1)C1=CC=C(C=C1)F)C1=CC=NC=C1 | [NH2:3][CH2:4][c:5]1[nH:6][n:7][c:8](-[c:9]2[cH:10][cH:11][c:12]([F:13])[cH:14][cH:15]2)[c:16]1-[c:17]1[cH:18][cH:19][n:20][cH:21][cH:22]1.O=[N+]([O-])c1ccc([C:2]([O-])=[O:1])cc1>>[O:1]=[CH:2][NH:3][CH2:4][c:5]1[nH:6][n:7][c:8](-[c:9]2[cH:10][cH:11][c:12]([F:13])[cH:14][cH:15]2)[c:16]1-[c:17]1[cH:18][cH:19][n:20][cH:21... | NCc1[nH]nc(-c2ccc(F)cc2)c1-c1ccncc1.O=C([O-])c1ccc([N+](=O)[O-])cc1 | O=CNCc1[nH]nc(-c2ccc(F)cc2)c1-c1ccncc1 | null | null | ClCCl | Acylation | OtherReaction | 53536c10ab6fa1c783a73616ee215bbf57da847929ac526782b4b4f7b975c55e | 76d22477696609d5ed2280b234b5ae086344d95da5ff6e529c547c7b73d4f1dd | c1ccc(-c2n[nH]cc2-c2ccncc2)cc1 | O=[N+](-[O-])-c1:c:c:c(-[C;H0;D3;+0:1](-[O-])=[O;D1;H0:2]):c:c:1.[#7;a:3]:[#7;a:4]:[c:5]-[C:6]-[NH2;D1;+0:7]>>[#7;a:3]:[#7;a:4]:[c:5]-[C:6]-[NH;D2;+0:7]-[CH;D2;+0:1]=[O;D1;H0:2] | null | [] | null | null | 24 | HOUR | To a suspension of 5-aminomethyl-4-(4-pyridyl)-3-(4-fluorophenyl)pyrazole (Example C-1) (8.04 g, 30 mmol) in 120 mL dichloromethane was added p-nitrophenylformate (6.01 g, 36 mmol) as a solid. The suspension was stirred for 24 h at room temperature and the solvents removed under reduced pressure. The residue was tritur... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group.Primary amine | Secondary amide | c1ccccc1 | null | c1cn[nH]c1.c1ccccc1.c1ccncc1 | HO- | ClCCl | null | 24 | NCc1[nH]nc(-c2ccc(F)cc2)c1-c1ccncc1.O=C([O-])c1ccc([N+](=O)[O-])cc1>ClCCl>O=CNCc1[nH]nc(-c2ccc(F)cc2)c1-c1ccncc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-91d7bdcc2d4243dabeaafed2aa049044 | O=CNCc1[nH]nc(-c2ccc(F)cc2)c1-c1ccncc1>>CNCc1[nH]nc(-c2ccc(F)cc2)c1-c1ccncc1 | Cl.B.C(=O)NCC1=C(C(=NN1)C1=CC=C(C=C1)F)C1=CC=NC=C1>>CNCC1=C(C(=NN1)C1=CC=C(C=C1)F)C1=CC=NC=C1 | O=[CH:1][NH:2][CH2:3][c:4]1[nH:5][n:6][c:7](-[c:8]2[cH:9][cH:10][c:11]([F:12])[cH:13][cH:14]2)[c:15]1-[c:16]1[cH:17][cH:18][n:19][cH:20][cH:21]1>>[CH3:1][NH:2][CH2:3][c:4]1[nH:5][n:6][c:7](-[c:8]2[cH:9][cH:10][c:11]([F:12])[cH:13][cH:14]2)[c:15]1-[c:16]1[cH:17][cH:18][n:19][cH:20][cH:21]1 | O=CNCc1[nH]nc(-c2ccc(F)cc2)c1-c1ccncc1 | CNCc1[nH]nc(-c2ccc(F)cc2)c1-c1ccncc1 | null | null | O1CCCC1 | Reduction | OtherReaction | 85b757f1833edc9e5c6365ee6b904683f414e7b9a5f9bfcfd7addca401447058 | ab40188eef2f825df7003af0ffae31d0ce53d126542122535627d3d354cbc9fe | c1ccc(-c2n[nH]cc2-c2ccncc2)cc1 | O=[CH;D2;+0:1]-[#7:2]-[C:3]>>[C:3]-[#7:2]-[CH3;D1;+0:1] | null | [] | null | null | 24 | HOUR | To a suspension of 5-(N-formylaminomethyl)-4-(4-pyridyl)-3-(4-fluorophenyl)pyrazole (8.74 g, 29.5 mmol) in 90 mL anhydrous tetrahydrofuran was added a 1.0 M solution of borane in tetrahydrofuran (90 mL, 90 mmol) and the mixture was stirred at room temperature for 24 h. 1 N aqueous hydrochloric acid (100 mL) was then ad... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide | null | null | null | c1cn[nH]c1.c1ccccc1.c1ccncc1 | Other | O1CCCC1 | null | 24 | O=CNCc1[nH]nc(-c2ccc(F)cc2)c1-c1ccncc1>O1CCCC1>CNCc1[nH]nc(-c2ccc(F)cc2)c1-c1ccncc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-68e71c52b3254c508c88af67df123562 | Clc1ccc(-c2n[nH]c(C3CCNCC3)c2-c2ccncc2)cc1.Fc1ccc(-c2n[nH]c([C@H]3CCCN3)c2-c2ccncc2)cc1>>CN1CCC[C@@H]1c1[nH]nc(-c2ccc(F)cc2)c1-c1ccncc1 | N1[C@H](CCC1)C1=C(C(=NN1)C1=CC=C(C=C1)F)C1=CC=NC=C1.Cl.N1CCC(CC1)C1=C(C(=NN1)C1=CC=C(C=C1)Cl)C1=CC=NC=C1>>CN1[C@H](CCC1)C1=C(C(=NN1)C1=CC=C(C=C1)F)C1=CC=NC=C1 | Clc1ccc(-c2n[nH]c(C3CCN[CH2:1]C3)c2-c2ccncc2)cc1.[NH:2]1[CH2:3][CH2:4][CH2:5][C@@H:6]1[c:7]1[nH:8][n:9][c:10](-[c:11]2[cH:12][cH:13][c:14]([F:15])[cH:16][cH:17]2)[c:18]1-[c:19]1[cH:20][cH:21][n:22][cH:23][cH:24]1>>[CH3:1][N:2]1[CH2:3][CH2:4][CH2:5][C@@H:6]1[c:7]1[nH:8][n:9][c:10](-[c:11]2[cH:12][cH:13][c:14]([F:15])[cH... | Clc1ccc(-c2n[nH]c(C3CCNCC3)c2-c2ccncc2)cc1.Fc1ccc(-c2n[nH]c([C@H]3CCCN3)c2-c2ccncc2)cc1 | CN1CCC[C@@H]1c1[nH]nc(-c2ccc(F)cc2)c1-c1ccncc1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 433acd56bde9a044e1b491560f137a87a8aed8615a81c51e12b5227791ad18c3 | 0825728d9008e169c37027081dd8b311d6afab66bc278b37ccd7245c60572ece | c1ccc(-c2n[nH]c([C@H]3CCCN3)c2-c2ccncc2)cc1 | Cl-c1:c:c:c(-c2:n:[nH]:c(-C3-C-C-N-[CH2;D2;+0:1]-C-3):c:2-c2:c:c:n:c:c:2):c:c:1.[#7;a:2]:[#7;a:3]:[c:4]-[C:5]1-[C:6]-[C:7]-[C:8]-[NH;D2;+0:9]-1>>[#7;a:2]:[#7;a:3]:[c:4]-[C:5]1-[C:6]-[C:7]-[C:8]-[N;H0;D3;+0:9]-1-[CH3;D1;+0:1] | null | [] | null | null | null | null | By following the method of Example C-75 and substituting (R)-5-(2-pyrolidinyl)-4-(4-pyridyl)-3-(4-fluorophenyl)pyrazole Example C-125) for 5-(4-piperidyl)-4-(4-pyridyl)-3-(4-chlorophenyl)pyrazole hydrochloride (Example C-74) the title compound was prepared: MS (M+H): 323 (base peak).
Conditions: See reaction.notes.proc... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine.Secondary amine | Tertiary amine | c1ccccc1.c1cn[nH]c1.C1CCNCC1.c1ccncc1.C1CCNC1 | C1CC[NH]C1 | C1CC[NH]C1.c1cn[nH]c1.c1ccccc1.c1ccncc1 | HCl | null | null | null | Clc1ccc(-c2n[nH]c(C3CCNCC3)c2-c2ccncc2)cc1.Fc1ccc(-c2n[nH]c([C@H]3CCCN3)c2-c2ccncc2)cc1>>CN1CCC[C@@H]1c1[nH]nc(-c2ccc(F)cc2)c1-c1ccncc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-b33be114347149539f4155a63f188620 | CO.O=C(O)CCCc1[nH]nc(-c2ccc(F)cc2)c1-c1ccncc1>>COC(=O)CCCc1[nH]nc(-c2ccc(F)cc2)c1-c1ccncc1 | N1=CC=C(C=C1)C=1C(=NNC1CCCC(=O)O)C1=CC=C(C=C1)F.OS(=O)(=O)O.CO>>N1=CC=C(C=C1)C=1C(=NNC1CCCC(=O)OC)C1=CC=C(C=C1)F | [CH3:1][OH:2].O[C:3](=[O:4])[CH2:5][CH2:6][CH2:7][c:8]1[nH:9][n:10][c:11](-[c:12]2[cH:13][cH:14][c:15]([F:16])[cH:17][cH:18]2)[c:19]1-[c:20]1[cH:21][cH:22][n:23][cH:24][cH:25]1>>[CH3:1][O:2][C:3](=[O:4])[CH2:5][CH2:6][CH2:7][c:8]1[nH:9][n:10][c:11](-[c:12]2[cH:13][cH:14][c:15]([F:16])[cH:17][cH:18]2)[c:19]1-[c:20]1[cH:... | CO.O=C(O)CCCc1[nH]nc(-c2ccc(F)cc2)c1-c1ccncc1 | COC(=O)CCCc1[nH]nc(-c2ccc(F)cc2)c1-c1ccncc1 | null | null | null | Protection | Esterification of Carboxylic Acids | 9cecdbd189c6f9c3648521d17154d013842a5498de4e76e65efb1d842973340b | af0b8064f2e82ebe66c4c29d2391785ac1b993104265ccdc4d67ca79e36fa3c8 | c1ccc(-c2n[nH]cc2-c2ccncc2)cc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[C;D1;H3:5]-[OH;D1;+0:6]>>[C:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[O;H0;D2;+0:6]-[C;D1;H3:5] | null | [] | null | null | 8 | HOUR | To a solution of 4-(4-(4-pyridyl)-3-(4-fluorophenyl)pyrazolyl)butyric acid (Example C-130) (40 g, 123 mmol) in 650 mL of MeOH was added 20 mL of concentrated H2SO4. The solution was stirred overnight at room temperature. The solution was concentrated and diluted with 200 mL of water. The solution was cooled with an ice... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Methanol | Ester | null | null | c1cn[nH]c1.c1ccccc1.c1ccncc1 | HO- | null | null | 8 | CO.O=C(O)CCCc1[nH]nc(-c2ccc(F)cc2)c1-c1ccncc1>>COC(=O)CCCc1[nH]nc(-c2ccc(F)cc2)c1-c1ccncc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-25197e05dc084f9fa03ae9e4d2a04866 | COC(=O)CCCc1[nH]nc(-c2ccc(F)cc2)c1-c1ccncc1.N>>NC(=O)CCCc1[nH]nc(-c2ccc(F)cc2)c1-c1ccncc1 | N1=CC=C(C=C1)C=1C(=NNC1CCCC(=O)OC)C1=CC=C(C=C1)F.N.N>>N1=CC=C(C=C1)C=1C(=NNC1CCCC(=O)N)C1=CC=C(C=C1)F | CO[C:2](=[O:3])[CH2:4][CH2:5][CH2:6][c:7]1[nH:8][n:9][c:10](-[c:11]2[cH:12][cH:13][c:14]([F:15])[cH:16][cH:17]2)[c:18]1-[c:19]1[cH:20][cH:21][n:22][cH:23][cH:24]1.[NH3:1]>>[NH2:1][C:2](=[O:3])[CH2:4][CH2:5][CH2:6][c:7]1[nH:8][n:9][c:10](-[c:11]2[cH:12][cH:13][c:14]([F:15])[cH:16][cH:17]2)[c:18]1-[c:19]1[cH:20][cH:21][n... | COC(=O)CCCc1[nH]nc(-c2ccc(F)cc2)c1-c1ccncc1.N | NC(=O)CCCc1[nH]nc(-c2ccc(F)cc2)c1-c1ccncc1 | null | null | CCOCC.CO | Acylation | OtherReaction | d5b10d4f469e7a196a3b04a6a9e159a7d90514b6df5b50c1197d4b1b774c04e1 | adc0ef6f6c1340dd2dbab737c85bf17fc842769181c5db1a2b4f82b391b28f9f | c1ccc(-c2n[nH]cc2-c2ccncc2)cc1 | C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[NH3;D0;+0:5]>>[C:4]-[C:3]-[C;H0;D3;+0:1](-[NH2;D1;+0:5])=[O;D1;H0:2] | null | [] | null | null | null | null | A solution of methyl 4-(4-(4-pyridyl)-3-(4-fluorophenyl)pyrazolyl)butyrate (39 g, 120 mmol) in 600 mL of MeOH was saturated with NH3. The solution was periodically treated with additional NH3 over a 24 h period. The solution was degassed with a stream of nitrogen and the solution was concentrated to leave a yellow soli... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary amide | null | null | c1cn[nH]c1.c1ccccc1.c1ccncc1 | HO- | CCOCC.CO | null | null | COC(=O)CCCc1[nH]nc(-c2ccc(F)cc2)c1-c1ccncc1.N>CCOCC.CO>NC(=O)CCCc1[nH]nc(-c2ccc(F)cc2)c1-c1ccncc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-9e21a5212f064237840651a288bbb3a8 | Clc1ccc(-c2n[nH]c(C3CCNCC3)c2-c2ccncn2)cc1.O=C(O)CO>>O=C(CO)n1nc(-c2ccc(Cl)cc2)c(-c2ccncn2)c1C1CCNCC1 | C(CO)(=O)O.N1CCC(CC1)C1=C(C(=NN1)C1=CC=C(C=C1)Cl)C1=NC=NC=C1.CCN(C(C)C)C(C)C.Cl.CN(CCCN=C=NCC)C.Cl.ON1N=NC2=C1C=CC=C2.C(CO)(=O)O>>OCC(=O)N1N=C(C(=C1C1CCNCC1)C1=NC=NC=C1)C1=CC=C(C=C1)Cl | [nH:5]1[n:6][c:7](-[c:8]2[cH:9][cH:10][c:11]([Cl:12])[cH:13][cH:14]2)[c:15](-[c:16]2[cH:17][cH:18][n:19][cH:20][n:21]2)[c:22]1[CH:23]1[CH2:24][CH2:25][NH:26][CH2:27][CH2:28]1.O[C:2](=[O:1])[CH2:3][OH:4]>>[O:1]=[C:2]([CH2:3][OH:4])[n:5]1[n:6][c:7](-[c:8]2[cH:9][cH:10][c:11]([Cl:12])[cH:13][cH:14]2)[c:15](-[c:16]2[cH:17]... | Clc1ccc(-c2n[nH]c(C3CCNCC3)c2-c2ccncn2)cc1.O=C(O)CO | O=C(CO)n1nc(-c2ccc(Cl)cc2)c(-c2ccncn2)c1C1CCNCC1 | null | null | CO.C(C)#N.C(Cl)Cl.[OH-].[Na+] | Acylation | OtherReaction | 2f03974be3ec6f146d7d653aab098743bb23dc338a45170f86080e0c6ac12f4d | d6b6da3f4e6a1bff80118626f0eda39fc948645429a79c2af70ffd0ea7000442 | c1ccc(-c2n[nH]c(C3CCNCC3)c2-c2ccncn2)cc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[O;D1;H1:4].[C:5]-[c:6]1:[c:7]:[c:8]:[#7;a:9]:[nH;D2;+0:10]:1>>[C:5]-[c:6]1:[c:7]:[c:8]:[#7;a:9]:[n;H0;D3;+0:10]:1-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[O;D1;H1:4] | 77.4 | [{"value": 77.4, "product": "OCC(=O)N1N=C(C(=C1C1CCNCC1)C1=NC=NC=C1)C1=CC=C(C=C1)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | A 1 L round bottom flask was charged with 34.2 g (102 mmol) of 5-(4-piperidyl)-4-(4-pyrimidyl)-3-(4-chlorophenyl)pyrazole, 500 mL of CH2Cl2 and 26.6 mL (153 mmol) of Hunig's base. To this suspension was added 16.5 g (122 mmol) of 1-hydroxybenzotriazole and 8.1 g (106 mmol) of glycolic acid. The addition of glycolic aci... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | null | c1cn[nH]c1 | c1cn[nH]c1 | c1cn[nH]c1.c1ccccc1.c1cncnc1.C1CCNCC1 | HO- | CO.C(C)#N.C(Cl)Cl.[OH-].[Na+] | null | 8 | Clc1ccc(-c2n[nH]c(C3CCNCC3)c2-c2ccncn2)cc1.O=C(O)CO>CO.C(C)#N.C(Cl)Cl.[OH-].[Na+]>O=C(CO)n1nc(-c2ccc(Cl)cc2)c(-c2ccncn2)c1C1CCNCC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-9256389df5634aa0b6a4f269a2a5d611 | O=C(CO)n1nc(-c2ccc(Cl)cc2)c(-c2ccncn2)c1C1CCNCC1>>O=C(CO)n1nc(-c2ccc(Cl)cc2)c(-c2ccncn2)c1C1CCNCC1 | Cl.OCC(=O)N1N=C(C(=C1C1CCNCC1)C1=NC=NC=C1)C1=CC=C(C=C1)Cl>>Cl.OCC(=O)N1N=C(C(=C1C1CCNCC1)C1=NC=NC=C1)C1=CC=C(C=C1)Cl | [O:2]=[C:3]([CH2:4][OH:5])[n:6]1[n:7][c:8](-[c:9]2[cH:10][cH:11][c:12]([Cl:13])[cH:14][cH:15]2)[c:16](-[c:17]2[cH:18][cH:19][n:20][cH:21][n:22]2)[c:23]1[CH:24]1[CH2:25][CH2:26][NH:27][CH2:28][CH2:29]1>>[O:2]=[C:3]([CH2:4][OH:5])[n:6]1[n:7][c:8](-[c:9]2[cH:10][cH:11][c:12]([Cl:13])[cH:14][cH:15]2)[c:16](-[c:17]2[cH:18][... | O=C(CO)n1nc(-c2ccc(Cl)cc2)c(-c2ccncn2)c1C1CCNCC1 | O=C(CO)n1nc(-c2ccc(Cl)cc2)c(-c2ccncn2)c1C1CCNCC1 | null | null | O1CCOCC1.CCOCC | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | c1ccc(-c2n[nH]c(C3CCNCC3)c2-c2ccncn2)cc1 | null | 190.9 | [{"value": 190.9, "product": "Cl.OCC(=O)N1N=C(C(=C1C1CCNCC1)C1=NC=NC=C1)C1=CC=C(C=C1)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | A 25 mL round bottom flask was charged with 65 mg (0.164 mmol) of N-(2-hydroxyacetyl)-5-(4-piperidyl)-4-(4-pyrimidyl)-3-(4-chlorophenyl)pyrazole and 2.5 mL of dioxane. To this suspension was added 0.082 mL of 4 N HCl in dioxane. The mixture was stirred for 2 hours. The mixture was diluted with 5 mL of Et2O and filtered... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | c1cn[nH]c1.c1ccccc1.c1cncnc1.C1CCNCC1 | null | O1CCOCC1.CCOCC | null | 2 | O=C(CO)n1nc(-c2ccc(Cl)cc2)c(-c2ccncn2)c1C1CCNCC1>O1CCOCC1.CCOCC>O=C(CO)n1nc(-c2ccc(Cl)cc2)c(-c2ccncn2)c1C1CCNCC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-b94034fa01654e1fbaf9e8144889e1a6 | C=[CH][Sn]([CH2]CCC)([CH2]CCC)[CH2]CCC.CC(C)NC(=O)Cc1ccc(Br)cc1>>C=Cc1ccc(CC(=O)NC(C)C)cc1 | C(C)(C)NC(CC1=CC=C(C=C1)Br)=O.C(=C)[Sn](CCCC)(CCCC)CCCC>>C(C)(C)NC(CC1=CC=C(C=C1)C=C)=O | CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[CH:2]=[CH2:1].Br[c:3]1[cH:4][cH:5][c:6]([CH2:7][C:8](=[O:9])[NH:10][CH:11]([CH3:12])[CH3:13])[cH:14][cH:15]1>>[CH2:1]=[CH:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][C:8](=[O:9])[NH:10][CH:11]([CH3:12])[CH3:13])[cH:14][cH:15]1 | C=[CH][Sn]([CH2]CCC)([CH2]CCC)[CH2]CCC.CC(C)NC(=O)Cc1ccc(Br)cc1 | C=Cc1ccc(CC(=O)NC(C)C)cc1 | null | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1 | C1(=CC=CC=C1)C.C(C)(=O)OCC | C-C Coupling | Stille reaction_vinyl | 70c70ea31829ab76af60acb09a55c00bc191f62cf69589ba5bf99dde81769bb5 | ec03c739f58696d2a3659a73884744e1a490a20a587da6f115be382b663cf23d | c1ccccc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].C-C-C-[CH2]-[Sn](-[CH2]-C-C-C)(-[CH2]-C-C-C)-[CH;D2;+0:6]=[C;D1;H2:7]>>[C;D1;H2:7]=[CH;D2;+0:6]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5] | 72.8 | [{"value": 72.8, "product": "C(C)(C)NC(CC1=CC=C(C=C1)C=C)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | N-Isopropyl-4-bromophenylacetamide (1.0 g) and vinyltributyltin (1.4 ml) were dissolved in toluene (12 ml). After adding tetrakistriphenylphosphinepalladium (0.5 g) thereto, the resultant mixture was heated under reflux for 4 hr. Then it was allowed to cool and diluted with ethyl acetate. The resulting solid was filter... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Vinyl.Tin | Vinyl | c1ccccc1 | c1ccccc1 | c1ccccc1 | HBr.Sn | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.C1(=CC=CC=C1)C.C(C)(=O)OCC | null | null | C=[CH][Sn]([CH2]CCC)([CH2]CCC)[CH2]CCC.CC(C)NC(=O)Cc1ccc(Br)cc1>C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.C1(=CC=CC=C1)C.C(C)(=O)OCC>C=Cc1ccc(CC(=O)NC(C)C)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-37b599736875400c8225ce2333f92727 | CCOC(C)=O.O.O=Cc1ccc(CCBr)cc1>>COC(=O)Cc1ccc(CC(=O)OC)cc1 | C[Mg]Br.O.C(C)(=O)OCC.BrCCC1=CC=C(C=O)C=C1.O1CCCC1>>C1(=CC=C(C=C1)CC(=O)OC)CC(=O)OC | CC([O:2][CH2:1][CH3:16])=[O:4].[OH2:13].Br[CH2:3][CH2:5][c:6]1[cH:7][cH:8][c:10]([CH:11]=[O:12])[cH:9][cH:15]1>>[CH3:1][O:2][C:3](=[O:4])[CH2:5][c:6]1[cH:7][cH:8][c:9]([CH2:10][C:11](=[O:12])[O:13][CH3:14])[cH:15][cH:16]1 | CCOC(C)=O.O.O=Cc1ccc(CCBr)cc1 | COC(=O)Cc1ccc(CC(=O)OC)cc1 | null | null | C(C)OCC | Acylation | OtherReaction | 91372d826df6ef8e84e390feaba0a01e7f9cd143d11f5b8d973496ed8697b163 | ee7c720141e3d2b05d1e11591d31f22cffa57878fece3d64240d86b782cfabc9 | c1ccccc1 | Br-[CH2;D2;+0:1]-[C:2]-[c;H0;D3;+0:3]1:[c:4]:[cH;D2;+0:5]:[c;H0;D3;+0:6](-[CH;D2;+0:7]=[O;D1;H0:8]):[cH;D2;+0:9]:[cH;D2;+0:10]:1.C-C(=[O;H0;D1;+0:11])-[O;H0;D2;+0:12]-[CH2;D2;+0:13]-[CH3;D1;+0:14].[OH2;D0;+0:15]>>[C;D1;H3:16]-[O;H0;D2;+0:15]-[C;H0;D3;+0:7](=[O;D1;H0:8])-[CH2;D2;+0:6]-[c;H0;D3;+0:9]1:[cH;D2;+0:10]:[cH;D... | 83.8 | [{"value": 83.8, "product": "C1(=CC=C(C=C1)CC(=O)OC)CC(=O)OC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | 4-(2-Bromoethyl)benzaldehyde (3.245 g) was dissolved in tetrahydrofuran (60 ml). Under ice cooling, a 3 M solution (4.9 ml) of methylmagnesium bromide in diethyl ether was added dropwise thereinto and the resultant mixture was stirred for 1.5 hr. After adding water and ethyl acetate, the layers were separated and the o... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aldehyde.Ester | Ester.Ester | c1ccccc1 | c1ccccc1 | c1ccccc1 | HBr | C(C)OCC | null | null | CCOC(C)=O.O.O=Cc1ccc(CCBr)cc1>C(C)OCC>COC(=O)Cc1ccc(CC(=O)OC)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-9c715bb37e9649afb3d25881488e8d52 | CCOC(=O)Cc1cccnc1>>CC(O)c1cccnc1 | N1=CC(=CC=C1)CC(=O)OCC.[H-].[Al+3].[Li+].[H-].[H-].[H-].O>>N1=CC(=CC=C1)C(C)O | CCO[C:1]([CH2:2][c:4]1[cH:5][cH:6][cH:7][n:8][cH:9]1)=[O:3]>>[CH3:1][CH:2]([OH:3])[c:4]1[cH:5][cH:6][cH:7][n:8][cH:9]1 | CCOC(=O)Cc1cccnc1 | CC(O)c1cccnc1 | null | null | O1CCCC1 | Miscellaneous | OtherReaction | b70a25915ab830e521879009e29b0bac89269fd1eaa24efb2ebe13b0d4cbd6fe | 0e7855212176179ed381c5dc4edbc294ca16d80af5fce34cf8e59e7573d05d39 | c1ccncc1 | C-C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[CH2;D2;+0:3]-[c:4](:[c:5]):[c:6]:[#7;a:7]:[c:8]>>[CH3;D1;+0:1]-[CH;D3;+0:3](-[OH;D1;+0:2])-[c:4](:[c:5]):[c:6]:[#7;a:7]:[c:8] | null | [] | null | null | 30 | MINUTE | Ethyl 3-pyridylacetate (2.0 ml) was dissolved in tetrahydrofuran (66 ml). Under ice cooling, lithium aluminum hydride (0.5 g) was added thereto followed by stirring for 30 min. After adding water (0.5 ml), a 5 N aqueous solution of sodium hydroxide (0.5 ml) and further water (1.5 ml), the resulting precipitate was filt... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Secondary alcohol | null | null | c1ccncc1 | HO- | O1CCCC1 | null | 0.5 | CCOC(=O)Cc1cccnc1>O1CCCC1>CC(O)c1cccnc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-2f1de5f6f73f47e19d07246a745e2b19 | CCOCC.COc1ccc(Br)cn1>>COc1ccc(CCO)cn1 | BrC=1C=CC(=NC1)OC.C(C)OCC>>COC1=NC=C(C=C1)CCO | CC[O:9][CH2:8][CH3:7].Br[c:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[n:11][cH:10]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][CH2:8][OH:9])[cH:10][n:11]1 | CCOCC.COc1ccc(Br)cn1 | COc1ccc(CCO)cn1 | null | null | null | C-C Coupling | OtherReaction | 4335d7b99a8e8d0857328045d90e233853aadf22ad65ea572a16e1716cf0b80f | 104534dc5f965e596cd2f673f5d9f6169287a1e8ccc931bc81d74b3081323966 | c1ccncc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[c:4]:[c:5]:[c:6]:1.C-C-[O;H0;D2;+0:7]-[C:8]-[CH3;D1;+0:9]>>[OH;D1;+0:7]-[C:8]-[CH2;D2;+0:9]-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[c:4]:[c:5]:[c:6]:1 | 62.7 | [{"value": 62.7, "product": "COC1=NC=C(C=C1)CCO", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | 5-Bromo-2-methoxypyridine (2.628 g) synthesized as reported in Tetrahedron, 1373 (1985). was dissolved in diethyl ether (40 ml) and then treated as in the above Production Example 16-1 to give the title compound (1.342 g) as a pale yellow oil (yield: 62.7%).
Conditions: See reaction.notes.procedure_details.
Workup: tre... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ether | Primary alcohol | c1ccncc1 | c1ccncc1 | c1ccncc1 | HBr | null | null | null | CCOCC.COc1ccc(Br)cn1>>COc1ccc(CCO)cn1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-0eb8fe3008554cb3accdfc6fce7a461a | N#Cc1ccc(CCOC(c2ccccc2)(c2ccccc2)c2ccccc2)c[n+]1[O-]>>OCCc1cccnc1 | C(#N)C1=[N+](C=C(C=C1)CCOC(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)[O-].C[Si](C)(C)C#N>>N1=CC(=CC=C1)CCO | N#C[c:7]1[cH:6][cH:5][c:4]([CH2:3][CH2:2][O:1]C(c2ccccc2)(c2ccccc2)c2ccccc2)[cH:9][n+:8]1[O-]>>[OH:1][CH2:2][CH2:3][c:4]1[cH:5][cH:6][cH:7][n:8][cH:9]1 | N#Cc1ccc(CCOC(c2ccccc2)(c2ccccc2)c2ccccc2)c[n+]1[O-] | OCCc1cccnc1 | null | null | null | Reduction | OtherReaction | 336f236b49fe2497c1860950ceb3e7718504814ba7e004a6d7c59f78665a4794 | e7ed5c7790f7855e803a32103e97202001b7555dbdc8fddac3bcf89221606e30 | c1ccncc1 | N#C-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4](-[C:5]-[C:6]-[O;H0;D2;+0:7]-C(-c2:c:c:c:c:c:2)(-c2:c:c:c:c:c:2)-c2:c:c:c:c:c:2):[c:8]:[n+;H0;D3:9]:1-[O-]>>[OH;D1;+0:7]-[C:6]-[C:5]-[c:4]1:[c:3]:[c:2]:[cH;D2;+0:1]:[n;H0;D2;+0:9]:[c:8]:1 | 116.8 | [{"value": 30.0, "product": "N1=CC(=CC=C1)CCO", "details": "PERCENTYIELD", "is_desired": false}, {"value": 116.8, "product": "N1=CC(=CC=C1)CCO", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 2-Cyano-5-(2-triphenylmethyloxyethyl)pyridine N-oxide (8.0 g) and trimethylsilyl cyanide (11.2 ml) were treated as reported in Synthesis, 314 (1983). to give the title compound (2.831 g) as a pale yellow oil (yield: 30.0%).
Conditions: See reaction.notes.procedure_details.
Workup: as reported in Synthesis, 314 (1983) | 10.6084/m9.figshare.5104873.v1 | null | Ether.Nitrile | Primary alcohol | C1=CC=[NH+]C=C1.c1ccccc1.c1ccccc1.c1ccccc1 | c1ccncc1 | c1ccncc1 | HO- | null | null | null | N#Cc1ccc(CCOC(c2ccccc2)(c2ccccc2)c2ccccc2)c[n+]1[O-]>>OCCc1cccnc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-42889450e9f34e979c25d8a8947167fd | N#Cc1ccc(CCOC(c2ccccc2)(c2ccccc2)c2ccccc2)cn1>>OCCc1cccnc1 | C(#N)C1=NC=C(C=C1)CCOC(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1>>N1=CC(=CC=C1)CCO | N#C[c:7]1[cH:6][cH:5][c:4]([CH2:3][CH2:2][O:1]C(c2ccccc2)(c2ccccc2)c2ccccc2)[cH:9][n:8]1>>[OH:1][CH2:2][CH2:3][c:4]1[cH:5][cH:6][cH:7][n:8][cH:9]1 | N#Cc1ccc(CCOC(c2ccccc2)(c2ccccc2)c2ccccc2)cn1 | OCCc1cccnc1 | null | null | C(=O)O | Deprotection | OtherReaction | 9496045898f34840fa5324637239850b021e715dfbceabfc7ff0d393e90d1a6d | 06b692100416cba83613541103a19415adced64a28d012e6abb45a866a9e6777 | c1ccncc1 | N#C-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5].[C:6]-[C:7]-[O;H0;D2;+0:8]-C(-c1:c:c:c:c:c:1)(-c1:c:c:c:c:c:1)-c1:c:c:c:c:c:1>>[C:6]-[C:7]-[OH;D1;+0:8].[c:5]:[c:4]:[cH;D2;+0:1]:[#7;a:2]:[c:3] | 54.8 | [{"value": 45.7, "product": "N1=CC(=CC=C1)CCO", "details": "PERCENTYIELD", "is_desired": false}, {"value": 54.8, "product": "N1=CC(=CC=C1)CCO", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 2-(2-Cyanopyridin-5-yl)-1-triphenylmethyloxyethane (2.631 g) and formic acid (38.0 ml) were treated as reported in Tetrahedron Lett., 579 (1986). to give the title compound (0.455 g) as colorless crystals (yield: 45.7%).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Ether.Nitrile | Primary alcohol | c1ccncc1.c1ccccc1.c1ccccc1.c1ccccc1 | c1ccncc1 | c1ccncc1 | Other | C(=O)O | null | null | N#Cc1ccc(CCOC(c2ccccc2)(c2ccccc2)c2ccccc2)cn1>C(=O)O>OCCc1cccnc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-b40d176e5f5443f48ab327e972bbd53b | CO.O=C(O)c1cncc(Br)c1>>COC(=O)c1cncc(Br)c1 | BrC=1C=NC=C(C(=O)O)C1.CO>>BrC=1C=NC=C(C(=O)OC)C1 | [CH3:1][OH:2].O[C:3](=[O:4])[c:5]1[cH:6][n:7][cH:8][c:9]([Br:10])[cH:11]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][n:7][cH:8][c:9]([Br:10])[cH:11]1 | CO.O=C(O)c1cncc(Br)c1 | COC(=O)c1cncc(Br)c1 | null | null | null | Protection | Esterification of Carboxylic Acids | 9cecdbd189c6f9c3648521d17154d013842a5498de4e76e65efb1d842973340b | af0b8064f2e82ebe66c4c29d2391785ac1b993104265ccdc4d67ca79e36fa3c8 | c1ccncc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5]:[#7;a:6]:[c:7].[C;D1;H3:8]-[OH;D1;+0:9]>>[C;D1;H3:8]-[O;H0;D2;+0:9]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5]:[#7;a:6]:[c:7] | 94 | [{"value": 94.0, "product": "BrC=1C=NC=C(C(=O)OC)C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | 5-Bromonicotinic acid (10 g) and methanol were treated as in the above Production Example 3-3 to give the title compound (10.052 g) as colorless crystals (yield: 94.0%).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Methanol | Ester | null | null | c1ccncc1 | HO- | null | null | null | CO.O=C(O)c1cncc(Br)c1>>COC(=O)c1cncc(Br)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-a6a5d351b07140b0b4919059e391a22c | CN(C)C=O.OCc1cncc(Br)c1>>COC(=O)c1cncc(Br)c1 | BrC=1C=C(C=NC1)CO.N1C=NC=C1.C(C)(C)(C)[Si](Cl)(C)C.CN(C=O)C>>BrC=1C=NC=C(C(=O)OC)C1 | CN(C)C=[O:4].[OH:2][CH2:3][c:5]1[cH:6][n:7][cH:8][c:9]([Br:10])[cH:11]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][n:7][cH:8][c:9]([Br:10])[cH:11]1 | CN(C)C=O.OCc1cncc(Br)c1 | COC(=O)c1cncc(Br)c1 | null | null | null | Protection | OtherReaction | 06dc996fb3fe2bcea328b641847e642fa2940555e7ca92d695cfcafec5970be2 | 07d18d4f792992ec34c2b3f151928349dd3e0afbfc89ffe2f57a55f68b97f12a | c1ccncc1 | C-N(-C)-C=[O;H0;D1;+0:1].[OH;D1;+0:2]-[CH2;D2;+0:3]-[c:4](:[c:5]):[c:6]:[#7;a:7]:[c:8]>>[C;D1;H3:9]-[O;H0;D2;+0:2]-[C;H0;D3;+0:3](=[O;H0;D1;+0:1])-[c:4](:[c:5]):[c:6]:[#7;a:7]:[c:8] | null | [] | null | null | null | null | 5-Bromo-3-hydroxymethylpyridine (3.41 g), imidazole (13.33 g), t-butyldimethylchlorosilane (13.57 g) and N,N-dimethylformamide (63 ml) were treated as reported in J. Am. Chem. Soc., 6190 (1972) to give the title compound (5.605 g) as a yellow oil (yield: quantitative).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Primary alcohol | Ester | null | null | c1ccncc1 | Other | null | null | null | CN(C)C=O.OCc1cncc(Br)c1>>COC(=O)c1cncc(Br)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-95b25d98d1334363b00baa78d11a4e52 | CCOC(=O)Cc1ccc(N)cc1.CCSC#N>>CCOC(=O)Cc1ccc2nc(N)sc2c1 | BrBr.[OH-].[Na+].C(C)SC#N.NC1=CC=C(C=C1)CC(=O)OCC>>NC=1SC2=C(N1)C=CC(=C2)CC(=O)OCC | [CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][c:7]1[cH:8][cH:9][c:10]([NH2:11])[cH:15][cH:16]1.CC[S:14][C:12]#[N:13]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][c:7]1[cH:8][cH:9][c:10]2[n:11][c:12]([NH2:13])[s:14][c:15]2[cH:16]1 | CCOC(=O)Cc1ccc(N)cc1.CCSC#N | CCOC(=O)Cc1ccc2nc(N)sc2c1 | null | null | C(C)(=O)O | Aromatic Heterocycle Formation | OtherReaction | 85f69cbc20429aad3e79d5a7a8b787980a48bae7c033b89ff8c975cc58fe128c | 9fbec7eeeb0442c48365bff18f49e58d0e0f8879723efdf31a5c9792fec6f5c5 | c1ccc2scnc2c1 | C-C-[S;H0;D2;+0:1]-[C;H0;D2;+0:2]#[N;H0;D1;+0:3].[NH2;D1;+0:4]-[c:5](:[c:6]):[cH;D2;+0:7]:[c:8]:[c:9]>>[NH2;D1;+0:3]-[c;H0;D3;+0:2]1:[n;H0;D2;+0:4]:[c:5](:[c:6]):[c;H0;D3;+0:7](:[c:8]:[c:9]):[s;H0;D2;+0:1]:1 | 93.7 | [{"value": 93.66, "product": "NC=1SC2=C(N1)C=CC(=C2)CC(=O)OCC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 93.7, "product": "NC=1SC2=C(N1)C=CC(=C2)CC(=O)OCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 10 | CELSIUS | 2 | HOUR | Ethyl 4-aminophenylacetate (18 g) was dissolved in acetic acid (120 ml) and ethyl thiocyanate (29.3 g) was added thereto. Under ice cooling, bromine (6.2 ml) was added dropwise thereinto over 45 minutes while maintaining the reaction temperature at about 10° C. After the completion of the addition, the resultant mixtur... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile.Primary amine.Monosulfide | Primary amine | c1ccccc1 | c1ccc2scnc2c1 | c1ccc2scnc2c1 | Other | C(C)(=O)O | 10 | 2 | CCOC(=O)Cc1ccc(N)cc1.CCSC#N>C(C)(=O)O>CCOC(=O)Cc1ccc2nc(N)sc2c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-de08c7219f4c4d2fa1af9c4b77153c15 | Brc1cnn(CCOCc2ccccc2)c1>>OCCn1cc(Br)cn1 | C(C1=CC=CC=C1)OCCN1N=CC(=C1)Br.Cl>>OCCN1N=CC(=C1)Br | c1ccc(C[O:1][CH2:2][CH2:3][n:4]2[cH:5][c:6]([Br:7])[cH:8][n:9]2)cc1>>[OH:1][CH2:2][CH2:3][n:4]1[cH:5][c:6]([Br:7])[cH:8][n:9]1 | Brc1cnn(CCOCc2ccccc2)c1 | OCCn1cc(Br)cn1 | null | null | C(C)O | Deprotection | Hydroxyl benzyl deprotection | c8a6fd2e05b2d36256c76b73aaf4118f20eb14abce1c0289b554265e30b218aa | 29a81fd08d26edc3da6d72c4958026f5af2119326dc1b4714ee5be1c41835609 | c1cn[nH]c1 | [C:1]-[C:2]-[O;H0;D2;+0:3]-C-c1:c:c:c:c:c:1>>[C:1]-[C:2]-[OH;D1;+0:3] | 71.7 | [{"value": 71.0, "product": "OCCN1N=CC(=C1)Br", "details": "PERCENTYIELD", "is_desired": false}, {"value": 71.7, "product": "OCCN1N=CC(=C1)Br", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 1-(2-Benzyloxyethyl)-4-bromopyrazole (1.078 g) was dissolved in ethanol (20 ml). After adding conc. hydrochloric acid (15 ml), the resultant mixture was stirred at 80° C. for 10 hr. After allowing to cool, it was concentrated under reduced pressure followed by the addition of a saturated aqueous solution of sodium bica... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Primary alcohol | c1ccccc1 | null | c1cn[nH]c1 | Other | C(C)O | null | null | Brc1cnn(CCOCc2ccccc2)c1>C(C)O>OCCn1cc(Br)cn1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-e80df2f9f4ce49b5bd2ee745e5f5299b | OCCOCc1ccccc1>>BrCCOCc1ccccc1 | BrC=1C=NNC1.[H-].[Na+].C(C1=CC=CC=C1)OCCO>>BrCCOCC1=CC=CC=C1 | O[CH2:2][CH2:3][O:4][CH2:5][c:6]1[cH:7][cH:8][cH:9][cH:10][cH:11]1>>[Br:1][CH2:2][CH2:3][O:4][CH2:5][c:6]1[cH:7][cH:8][cH:9][cH:10][cH:11]1 | OCCOCc1ccccc1 | BrCCOCc1ccccc1 | null | null | O1CCCC1 | Functional Group Interconversion | Alkyl bromides from alcohols | bb752b9027dc4488ba075e5955118a819f80cabd751a7497b67c2eeb1db6b071 | cbf41c7cf9fe6b47a243b1674d74ed5bf46a151f7f3a71d206e23176e158facf | c1ccccc1 | O-[CH2;D2;+0:1]-[C:2]-[#8:3]>>[#8:3]-[C:2]-[CH2;D2;+0:1]-[Br;D1;H0:4] | null | [] | null | null | 30 | MINUTE | 4-Bromopyrazole (2.205 g) was dissolved in tetrahydrofuran (20 ml). Under ice cooling, 60% sodium hydride (625 mg) was added thereto followed by stirring. After 30 min, benzyl 2-bromoethyl ether (3.872 g) obtained from 2-benzyloxyethanol in the same manner as the one of Production Example 1 was added thereto and the re... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | Primary halide | null | null | c1ccccc1 | null | O1CCCC1 | null | 0.5 | OCCOCc1ccccc1>O1CCCC1>BrCCOCc1ccccc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-bf9294382bd446e1829cddfe2bb7bdae | CCOC(=O)CC(=O)OCC.O=[N+]([O-])c1cc(Br)ccc1Br>>O=C1Cc2ccc(Br)cc2N1 | BrC1=C(C=C(C=C1)Br)[N+](=O)[O-].C(C)(=O)OCC.C(CC(=O)OCC)(=O)OCC.[H-].[Na+]>>C1C2=C(C=C(C=C2)Br)NC1=O | CCOC(=O)[CH2:3][C:2](OCC)=[O:1].O=[N+:11]([O-])[c:10]1[c:4](Br)[cH:5][cH:6][c:7]([Br:8])[cH:9]1>>[O:1]=[C:2]1[CH2:3][c:4]2[cH:5][cH:6][c:7]([Br:8])[cH:9][c:10]2[NH:11]1 | CCOC(=O)CC(=O)OCC.O=[N+]([O-])c1cc(Br)ccc1Br | O=C1Cc2ccc(Br)cc2N1 | null | null | CS(=O)C | Acylation | OtherReaction | 7812a18a05bcb61caefa1d2b62d6992a9d3874183ff1a2443f248216abca3ecf | acd64d9346102b8ce061b258d498e378eb7903c6e686fb1c688fca298a28a8a6 | O=C1Cc2ccccc2N1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[N+;H0;D3:5](=O)-[O-]):[c:6].C-C-O-C(=O)-[CH2;D2;+0:7]-[C;H0;D3;+0:8](=[O;D1;H0:9])-O-C-C>>[O;D1;H0:9]=[C;H0;D3;+0:8]1-[CH2;D2;+0:7]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](:[c:6])-[NH;D2;+0:5]-1 | 85 | [{"value": 84.0, "product": "C1C2=C(C=C(C=C2)Br)NC1=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 85.0, "product": "C1C2=C(C=C(C=C2)Br)NC1=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Under ice cooling, diethyl malonate (500 g) was added dropwise into a suspension of sodium hydride (125 g) in dimethyl sulfoxide (800 ml). After the solution became homogeneous, the resultant mixture was heated to 100° C. and a solution of 2,5-dibromonitrobenzene (500 g) in dimethyl sulfoxide (400 ml) was added dropwis... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ester.Ester.Nitro group | Secondary amide | c1ccccc1 | c1ccc2c(c1)CCN2 | c1ccc2c(c1)CCN2 | HBr | CS(=O)C | null | null | CCOC(=O)CC(=O)OCC.O=[N+]([O-])c1cc(Br)ccc1Br>CS(=O)C>O=C1Cc2ccc(Br)cc2N1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-fd3a79c807b24a9bac9ef75d5fd516a0 | CC#N.CC(=O)Cl.CCN(CC)CC.CCOC(C)=O>>CC(=O)N1CCc2ccc(N)cc21 | C(C)(=O)Cl.C(C)N(CC)CC.C(C)#N.C([O-])(O)=O.[Na+].C(C)(=O)OCC>>C(C)(=O)N1CCC2=CC=C(C=C12)N | [CH3:9][C:10]#[N:11].Cl[C:2]([CH3:1])=[O:3].CC[N:4]([CH2:5][CH3:6])[CH2:12][CH3:13].CC(=O)O[CH2:8][CH3:7]>>[CH3:1][C:2](=[O:3])[N:4]1[CH2:5][CH2:6][c:7]2[cH:8][cH:9][c:10]([NH2:11])[cH:12][c:13]21 | CC#N.CC(=O)Cl.CCN(CC)CC.CCOC(C)=O | CC(=O)N1CCc2ccc(N)cc21 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | c74c2224b3c9f1acae9ef2aeed9798dfee194491a22e56a695c36e962f186a27 | a7bbb55f69883e6751623dea2d61b75565029d877195d93d695e616e279967b8 | c1ccc2c(c1)CCN2 | C-C(=O)-O-[CH2;D2;+0:1]-[CH3;D1;+0:2].C-C-[N;H0;D3;+0:3](-[C:4]-[CH3;D1;+0:5])-[CH2;D2;+0:6]-[CH3;D1;+0:7].Cl-[C;H0;D3;+0:8](-[C;D1;H3:9])=[O;D1;H0:10].[CH3;D1;+0:11]-[C;H0;D2;+0:12]#[N;H0;D1;+0:13]>>[C;D1;H3:9]-[C;H0;D3;+0:8](=[O;D1;H0:10])-[N;H0;D3;+0:3]1-[C:4]-[CH2;D2;+0:5]-[c;H0;D3;+0:2]2:[cH;D2;+0:1]:[cH;D2;+0:11]... | 58 | [{"value": 58.0, "product": "C(C)(=O)N1CCC2=CC=C(C=C12)N", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | Under ice cooling, acetyl chloride (1.7 ml) was added dropwise into a solution of 1-[1-(4-t-butoxycarbonyl)piperidin-4-yl]-6-aminomethylindoline (8.3 g) and triethylamine (2.4 g) in acetonitrile (150 ml) followed by stirring the resultant mixture at room temperature for 1 hr. To the liquid reaction mixture were added a... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Ester.Nitrile.Tertiary amine | Tertiary amide.Primary amine | null | c1ccc2c(c1)CC[NH]2 | c1ccc2c(c1)CC[NH]2 | HCl | null | null | 2 | CC#N.CC(=O)Cl.CCN(CC)CC.CCOC(C)=O>>CC(=O)N1CCc2ccc(N)cc21 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-addcacbb6213493293811ebb667a59e9 | Brc1ccc2c(c1)NCC2.CC(C)(C)OC(=O)OC(C)(C)C>>CC(C)(C)OC(=O)N1CCc2ccc(Br)cc21 | O.C(OC(C)(C)C)(OC(C)(C)C)=O.BrC1=CC=C2CCNC2=C1.C(C)N(CC)CC>>C(C)(C)(C)OC(=O)N1CCC2=CC=C(C=C12)Br | [NH:8]1[CH2:9][CH2:10][c:11]2[cH:12][cH:13][c:14]([Br:15])[cH:16][c:17]21.CC(C)(C)O[C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][c:11]2[cH:12][cH:13][c:14]([Br:15])[cH:16][c:17]21 | Brc1ccc2c(c1)NCC2.CC(C)(C)OC(=O)OC(C)(C)C | CC(C)(C)OC(=O)N1CCc2ccc(Br)cc21 | null | null | O1CCCC1.C(C)(=O)OCC | Protection | Boc amine protection of secondary amine | 048899db12914f45fba7596a782894641fa55a9880f800c2edbc02cfd88d0358 | f0869a0b34976f381b42755ff52efacfde708ff6f8d3c39d434136b4f68fd40e | c1ccc2c(c1)CCN2 | C-C(-C)(-C)-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C:4](-[C;D1;H3:5])(-[C;D1;H3:6])-[C;D1;H3:7].[c:8]:[c:9]1:[c:10]-[C:11]-[C:12]-[NH;D2;+0:13]-1>>[C;D1;H3:5]-[C:4](-[C;D1;H3:6])(-[C;D1;H3:7])-[#8:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[N;H0;D3;+0:13]1-[C:12]-[C:11]-[c:10]:[c:9]-1:[c:8] | 71.6 | [{"value": 71.0, "product": "C(C)(C)(C)OC(=O)N1CCC2=CC=C(C=C12)Br", "details": "PERCENTYIELD", "is_desired": false}, {"value": 71.6, "product": "C(C)(C)(C)OC(=O)N1CCC2=CC=C(C=C12)Br", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Di-t-butyl carbonate (6.7 g) was added to a solution of 6-bromoindoline (5.1 g) and triethylamine (3.1 g) in tetrahydrofuran (50 ml) followed by stirring the resultant mixture at room temperature overnight. After adding water and ethyl acetate thereto, the layers were separated and the organic layer was washed with bri... | 10.6084/m9.figshare.5104873.v1 | null | Carbonic Ester.Secondary amine.Boc.Boc | Carbamic ester | c1ccc2c(c1)CCN2 | c1ccc2c(c1)CC[NH]2 | c1ccc2c(c1)CC[NH]2 | HO- | O1CCCC1.C(C)(=O)OCC | null | null | Brc1ccc2c(c1)NCC2.CC(C)(C)OC(=O)OC(C)(C)C>O1CCCC1.C(C)(=O)OCC>CC(C)(C)OC(=O)N1CCc2ccc(Br)cc21 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-c9e0bf59611b4d53886e3cc23206e4cf | CC(C)(C)OC(=O)n1cc(-c2ccc(F)cc2)c2ccccc21.O=C(O)C(F)(F)F>>CC(C)(C)OC(=O)Nc1ccccc1CO | C(C)(C)(C)OC(=O)N1C=C(C2=CC=CC=C12)C1=CC=C(C=C1)F.FC(C(=O)O)(F)F>>C(C)(C)(C)OC(=O)NC1=C(CO)C=CC=C1 | Fc1ccc(-[c:15]2c[n:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[c:9]3[cH:10][cH:11][cH:12][cH:13][c:14]32)cc1.OC(C(F)(F)F)=[O:16]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][c:9]1[cH:10][cH:11][cH:12][cH:13][c:14]1[CH2:15][OH:16] | CC(C)(C)OC(=O)n1cc(-c2ccc(F)cc2)c2ccccc21.O=C(O)C(F)(F)F | CC(C)(C)OC(=O)Nc1ccccc1CO | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | cc36ea434fa74b93744a84f49ec363b9ace40aa6f22516381cbe890b8932c0dd | 8349b314e8068b03c861d620b54478afeafc95b01a300461efcecc492db205e9 | c1ccccc1 | F-C(-F)(-F)-C(-O)=[O;H0;D1;+0:1].F-c1:c:c:c(-[c;H0;D3;+0:2]2:c:[n;H0;D3;+0:3](-[C:4](=[O;D1;H0:5])-[#8:6]-[C:7](-[C;D1;H3:8])(-[C;D1;H3:9])-[C;D1;H3:10]):[c:11](:[c:12]):[c:13]:2:[c:14]):c:c:1>>[C;D1;H3:8]-[C:7](-[C;D1;H3:9])(-[C;D1;H3:10])-[#8:6]-[C:4](=[O;D1;H0:5])-[NH;D2;+0:3]-[c:11](:[c:12]):[c:13](-[CH2;D2;+0:2]-[... | 79 | [{"value": 79.0, "product": "C(C)(C)(C)OC(=O)NC1=C(CO)C=CC=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | 1-(t-Butoxy)carbonyl-3-(4-fluorophenyl)indole (0.340 g) was freed from the protecting group with the use of trifluoroacetic acid and then treated as in the above Production Example 54 to give the title compound (0.184 g) as a pale yellow oil (yield: 79.0%).
Conditions: See reaction.notes.procedure_details.
Workup: trea... | 10.6084/m9.figshare.5104873.v1 | null | Trifluoro group.Aromatic halide.Carboxylic acid | Carbamic ester.Primary alcohol | c1ccccc1.c1c[nH]c2ccccc12 | c1ccccc1 | c1ccccc1 | HF | null | null | null | CC(C)(C)OC(=O)n1cc(-c2ccc(F)cc2)c2ccccc21.O=C(O)C(F)(F)F>>CC(C)(C)OC(=O)Nc1ccccc1CO |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-64f40cb0f4e94dffa304fb3cc84114ca | CCN(CC)C(=O)n1cc(C=O)c2ccccc21.COc1cccc(C[P+](c2ccccc2)(c2ccccc2)c2ccccc2)c1>>CCN(CC)C(=O)n1cc(C=Cc2cccc(OC)c2)c2ccccc21 | [Cl-].COC=1C=C(C[P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=CC1.C(C)N(C(=O)N1C=C(C2=CC=CC=C12)C=O)CC>>C(C)N(C(=O)N1C=C(C2=CC=CC=C12)C=CC1=CC(=CC=C1)OC)CC | O=[CH:11][c:10]1[cH:9][n:8]([C:6]([N:3]([CH2:2][CH3:1])[CH2:4][CH3:5])=[O:7])[c:26]2[c:21]1[cH:22][cH:23][cH:24][cH:25]2.c1ccc([P+](c2ccccc2)(c2ccccc2)[CH2:12][c:13]2[cH:14][cH:15][cH:16][c:17]([O:18][CH3:19])[cH:20]2)cc1>>[CH3:1][CH2:2][N:3]([CH2:4][CH3:5])[C:6](=[O:7])[n:8]1[cH:9][c:10]([CH:11]=[CH:12][c:13]2[cH:14][... | CCN(CC)C(=O)n1cc(C=O)c2ccccc21.COc1cccc(C[P+](c2ccccc2)(c2ccccc2)c2ccccc2)c1 | CCN(CC)C(=O)n1cc(C=Cc2cccc(OC)c2)c2ccccc21 | null | null | O1CCCC1 | C-C Coupling | Wittig with Phosphonium | cb5f277ac55a0e763ef643becc05f1522019cc4161daceb249ed2d634b78153b | cedc9d4b791e43eacf8e7ecfa6a98d1dc0438794e96e4f1c4bef436b78f82bd8 | C(=Cc1c[nH]c2ccccc12)c1ccccc1 | O=[CH;D2;+0:1]-[c:2]1:[c:3]:[c:4]:[#7;a:5](-[C:6](-[#7:7])=[O;D1;H0:8]):[c:9]:1.[c:10]:[c:11](-[CH2;D2;+0:12]-[P+](-c1:c:c:c:c:c:1)(-c1:c:c:c:c:c:1)-c1:c:c:c:c:c:1):[c:13]>>[#7:7]-[C:6](=[O;D1;H0:8])-[#7;a:5]1:[c:4]:[c:3]:[c:2](-[CH;D2;+0:1]=[CH;D2;+0:12]-[c:11](:[c:10]):[c:13]):[c:9]:1 | 59.2 | [{"value": 59.1, "product": "C(C)N(C(=O)N1C=C(C2=CC=CC=C12)C=CC1=CC(=CC=C1)OC)CC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 59.2, "product": "C(C)N(C(=O)N1C=C(C2=CC=CC=C12)C=CC1=CC(=CC=C1)OC)CC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 3-Methoxybenzyltriphenylphosphonium chloride (1.71 g) and 1-diethylcarbamoyl-3-formylindole (1.71 g), which had been synthesized according to the method of Tetrahedron Lett., 1869 (1986)., were reacted in tetrahydrofuran (5 ml) as in the above Production Example 41-1 to give the title compound (0.842 g) as a brown oil ... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | null | c1ccccc1.c1ccccc1.c1ccccc1 | null | c1ccccc1.c1c[nH]c2ccccc12 | HO- | O1CCCC1 | null | null | CCN(CC)C(=O)n1cc(C=O)c2ccccc21.COc1cccc(C[P+](c2ccccc2)(c2ccccc2)c2ccccc2)c1>O1CCCC1>CCN(CC)C(=O)n1cc(C=Cc2cccc(OC)c2)c2ccccc21 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-c567076c452241ecb7e57b0176766525 | Fc1cccc(C[PH3+])c1.O=Cc1c[nH]c2ccccc12>>Fc1cccc(C=Cc2c[nH]c3ccccc23)c1 | C(=O)C1=CNC2=CC=CC=C12.[Cl-].FC=1C=C(C[PH3+])C=CC1>>FC=1C=C(C=CC1)C=CC1=CNC2=CC=CC=C12 | [PH3+][CH2:7][c:6]1[cH:5][cH:4][cH:3][c:2]([F:1])[cH:18]1.O=[CH:8][c:9]1[cH:10][nH:11][c:12]2[cH:13][cH:14][cH:15][cH:16][c:17]12>>[F:1][c:2]1[cH:3][cH:4][cH:5][c:6]([CH:7]=[CH:8][c:9]2[cH:10][nH:11][c:12]3[cH:13][cH:14][cH:15][cH:16][c:17]23)[cH:18]1 | Fc1cccc(C[PH3+])c1.O=Cc1c[nH]c2ccccc12 | Fc1cccc(C=Cc2c[nH]c3ccccc23)c1 | null | null | null | C-C Coupling | Wittig with Phosphonium | 43d4e2f03e758941ee99f59641d5d56e6475fe935434d251d75d5cdebbe19869 | cedc9d4b791e43eacf8e7ecfa6a98d1dc0438794e96e4f1c4bef436b78f82bd8 | C(=Cc1c[nH]c2ccccc12)c1ccccc1 | O=[CH;D2;+0:1]-[c:2]1:[c:3]:[#7;a:4]:[c:5]:[c:6]:1.[PH3+]-[CH2;D2;+0:7]-[c:8](:[c:9]):[c:10]>>[c:9]:[c:8](-[CH;D2;+0:7]=[CH;D2;+0:1]-[c:2]1:[c:3]:[#7;a:4]:[c:5]:[c:6]:1):[c:10] | 73.1 | [{"value": 73.1, "product": "FC=1C=C(C=CC1)C=CC1=CNC2=CC=CC=C12", "details": "PERCENTYIELD", "is_desired": false}, {"value": 36.6, "product": "FC=1C=C(C=CC1)C=CC1=CNC2=CC=CC=C12", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 3-Formylindole (1.0 g) and 3-fluorobenzylphosphonium chloride (2.8 g) were treated as in the above Production Example 41-1 to give the title compound (0.598 g) as colorless crystals (yield: 73.1%).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | null | null | null | c1ccccc1.c1ccc2[nH]ccc2c1 | HO- | null | null | null | Fc1cccc(C[PH3+])c1.O=Cc1c[nH]c2ccccc12>>Fc1cccc(C=Cc2c[nH]c3ccccc23)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-6aca4d9405034a5ebf05bb0ae75cb5b8 | Brc1cccc2[nH]ccc12.OB(O)c1ccc(F)cc1>>Fc1cccc(C=Cc2c[nH]c3ccccc23)c1 | BrC1=C2C=CNC2=CC=C1.FC1=CC=C(C=C1)B(O)O.C([O-])([O-])=O.[Na+].[Na+].C1(=CC=CC=C1)C>>FC=1C=C(C=CC1)C=CC1=CNC2=CC=CC=C12 | Br[c:16]1[cH:15][cH:14][cH:13][c:12]2[nH:11][cH:10][cH:9][c:17]21.OB(O)[c:5]1[cH:4][cH:3][c:2]([F:1])[cH:18][cH:6]1>>[F:1][c:2]1[cH:3][cH:4][cH:5][c:6]([CH:7]=[CH:8][c:9]2[cH:10][nH:11][c:12]3[cH:13][cH:14][cH:15][cH:16][c:17]23)[cH:18]1 | Brc1cccc2[nH]ccc12.OB(O)c1ccc(F)cc1 | Fc1cccc(C=Cc2c[nH]c3ccccc23)c1 | null | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1 | C(C)(=O)OCC | C-C Coupling | OtherReaction | 42e21206f0250bb469664981cf521bd21ce6ff7bf8a8e9271f94397f7d3b79cb | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | C(=Cc1c[nH]c2ccccc12)c1ccccc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[c:5]2:[#7;a:6]:[c:7]:[cH;D2;+0:8]:[c:9]:2:1.O-B(-O)-[c;H0;D3;+0:10]1:[c:11]:[c:12]:[c:13]:[c:14]:[cH;D2;+0:15]:1>>[#7;a:6]1:[c:7]:[c;H0;D3;+0:8](-[C:16]=[C:17]-[c;H0;D3;+0:15]2:[c:14]:[c:13]:[c:12]:[c:11]:[cH;D2;+0:10]:2):[c:9]2:[cH;D2;+0:1]:[c:2]:[c:3]:[c:4]:[c:5]:1:2 | 46 | [{"value": 46.0, "product": "FC=1C=C(C=CC1)C=CC1=CNC2=CC=CC=C12", "details": "PERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 1 | HOUR | A mixture of 4-bromoindole (1.0 g), which had been synthesized according to the method of J. Org. Chem. (1986, Vol. 5, No. 26, p. 5106.), 4-fluorophenylboronic acid (1.1 g), tetrakis(triphenylphosphine)palladium (0.24 g), a 10% aqueous solution (10 ml) of sodium carbonate and toluene (20 ml) was heated under reflux for... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccc2[nH]ccc2c1.c1ccccc1 | c1ccccc1.c1ccc2[nH]ccc2c1 | c1ccccc1.c1ccc2[nH]ccc2c1 | Br-.B | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.C(C)(=O)OCC | 0 | 1 | Brc1cccc2[nH]ccc12.OB(O)c1ccc(F)cc1>C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.C(C)(=O)OCC>Fc1cccc(C=Cc2c[nH]c3ccccc23)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-d14dd00914d64c3b9ce4a6f342d4f9c1 | CC(=O)N1CCc2ccc(N)cc21.O=S(=O)(Cl)c1ccc(F)cc1>>Fc1cccc(C=Cc2c[nH]c3ccccc23)c1 | FC1=CC=C(C=C1)S(=O)(=O)Cl.C(C)(=O)N1CCC2=CC=C(C=C12)N.N1=CC=CC=C1>>FC=1C=C(C=CC1)C=CC1=CNC2=CC=CC=C12 | CC(=O)[N:11]1[CH2:10][CH2:9][c:17]2[c:12]1[cH:13][c:14](N)[cH:15][cH:16]2.O=S(=O)(Cl)[c:5]1[cH:4][cH:3][c:2]([F:1])[cH:18][cH:6]1>>[F:1][c:2]1[cH:3][cH:4][cH:5][c:6]([CH:7]=[CH:8][c:9]2[cH:10][nH:11][c:12]3[cH:13][cH:14][cH:15][cH:16][c:17]23)[cH:18]1 | CC(=O)N1CCc2ccc(N)cc21.O=S(=O)(Cl)c1ccc(F)cc1 | Fc1cccc(C=Cc2c[nH]c3ccccc23)c1 | null | null | null | C-C Coupling | OtherReaction | 016c635e44be3cbff54a0d86e8f700e0da6cd97710e1dfbf24307817d04d7407 | f004724b4dca50351cfa6c50f100ac1c467927a8d677ae7e3c255f61491e8973 | C(=Cc1c[nH]c2ccccc12)c1ccccc1 | C-C(=O)-[N;H0;D3;+0:1]1-[CH2;D2;+0:2]-[CH2;D2;+0:3]-[c:4]2:[c:5]:[c:6]:[c;H0;D3;+0:7](-N):[c:8]:[c:9]:2-1.Cl-S(=O)(=O)-[c;H0;D3;+0:10]1:[c:11]:[c:12]:[c:13]:[c:14]:[cH;D2;+0:15]:1>>[C:16](=[C:17]-[c;H0;D3;+0:3]1:[cH;D2;+0:2]:[nH;D2;+0:1]:[c:9]2:[c:8]:[cH;D2;+0:7]:[c:6]:[c:5]:[c:4]:2:1)-[c;H0;D3;+0:15]1:[c:14]:[c:13]:[c... | 82 | [{"value": 82.0, "product": "FC=1C=C(C=CC1)C=CC1=CNC2=CC=CC=C12", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Under ice cooling, 4-fluorobenzenesulfonyl chloride (1.4 g) was added dropwise into a solution (10 ml) of 1-acetyl-6-aminoindoline (1.0 g) in pyridine followed by stirring the resultant mixture for 30 min. After concentrating it under reduced pressure, 5 N hydrochloric acid was added thereto and the resultant mixture w... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Primary amine.Sulfonyl halide | null | c1ccc2c(c1)CC[NH]2.c1ccccc1 | c1ccccc1.c1ccc2[nH]ccc2c1 | c1ccccc1.c1ccc2[nH]ccc2c1 | HCl | null | null | null | CC(=O)N1CCc2ccc(N)cc21.O=S(=O)(Cl)c1ccc(F)cc1>>Fc1cccc(C=Cc2c[nH]c3ccccc23)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-d26a1681126c47aaacdd07b2c0719e47 | O=C1CCN(c2ccc(F)cc2)CC1.c1ccc2c(c1)CCN2>>Fc1ccc(N2CCC(N3CCc4ccccc43)CC2)cc1 | N1CCC2=CC=CC=C12.FC1=CC=C(C=C1)N1CCC(CC1)=O.C(C)(=O)O.ClC(C)Cl>>FC1=CC=C(C=C1)N1CCC(CC1)N1CCC2=CC=CC=C12 | O=[C:9]1[CH2:8][CH2:7][N:6]([c:5]2[cH:4][cH:3][c:2]([F:1])[cH:22][cH:21]2)[CH2:20][CH2:19]1.[NH:10]1[CH2:11][CH2:12][c:13]2[cH:14][cH:15][cH:16][cH:17][c:18]21>>[F:1][c:2]1[cH:3][cH:4][c:5]([N:6]2[CH2:7][CH2:8][CH:9]([N:10]3[CH2:11][CH2:12][c:13]4[cH:14][cH:15][cH:16][cH:17][c:18]43)[CH2:19][CH2:20]2)[cH:21][cH:22]1 | O=C1CCN(c2ccc(F)cc2)CC1.c1ccc2c(c1)CCN2 | Fc1ccc(N2CCC(N3CCc4ccccc43)CC2)cc1 | null | null | C(C)(=O)OCC | Heteroatom Alkylation and Arylation | OtherReaction | ed5f829465aab8e8fa321fc868dfe3231b2d42ce59513bacd6302db66ad15586 | 99acf13bfcfe579f51ccb82c65e4ca039ee7ca9b6fcd2747a3d9a292a88e564e | c1ccc(N2CCC(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 | 63 | [{"value": 63.0, "product": "FC1=CC=C(C=C1)N1CCC(CC1)N1CCC2=CC=CC=C12", "details": "PERCENTYIELD", "is_desired": false}, {"value": 63.0, "product": "FC1=CC=C(C=C1)N1CCC(CC1)N1CCC2=CC=CC=C12", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | Triacetoxylated sodium borohydride (760 mg) was added to a mixture of indoline (300 mg), 1-(4-fluorophenyl)-4-piperidone (580 mg), acetic acid (650 mg) and dichloroethane (30 ml), and the mixture was stirred for 2 hr. The obtained reaction solution was mixed with ethyl acetate and a saturated aqueous solution of sodium... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Secondary amine | Tertiary amine | C1CC[NH]CC1.c1ccc2c(c1)CCN2 | C1CC[NH]CC1.c1ccc2c(c1)CC[NH]2 | c1ccccc1.C1CC[NH]CC1.c1ccc2c(c1)CC[NH]2 | Other | C(C)(=O)OCC | null | 2 | O=C1CCN(c2ccc(F)cc2)CC1.c1ccc2c(c1)CCN2>C(C)(=O)OCC>Fc1ccc(N2CCC(N3CCc4ccccc43)CC2)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-208f2bf09efd4eea8e8df35499530e4a | O=C(O)Cc1ccc(F)c(F)c1.c1ccc2c(c1)CCN2C1CCNCC1>>Fc1ccc(CCN2CCC(N3CCc4ccccc43)CC2)cc1F | [OH-].[Na+].N1CCC(CC1)N1CCC2=CC=CC=C12.[H-].[Al+3].[Li+].[H-].[H-].[H-].FC=1C=C(C=CC1F)CC(=O)O>>FC=1C=C(CCN2CCC(CC2)N2CCC3=CC=CC=C23)C=CC1F | O=[C:7](O)[CH2:6][c:5]1[cH:4][cH:3][c:2]([F:1])[c:24]([F:25])[cH:23]1.[NH:8]1[CH2:9][CH2:10][CH:11]([N:12]2[CH2:13][CH2:14][c:15]3[cH:16][cH:17][cH:18][cH:19][c:20]32)[CH2:21][CH2:22]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][CH2:14][c:15]4[cH:16][cH:17][cH:18][cH:19][c:2... | O=C(O)Cc1ccc(F)c(F)c1.c1ccc2c(c1)CCN2C1CCNCC1 | Fc1ccc(CCN2CCC(N3CCc4ccccc43)CC2)cc1F | null | null | O1CCCC1.O.C(C)(=O)OCC | Heteroatom Alkylation and Arylation | OtherReaction | 975a081594f7f4a257607ac3cd18fdcd01393be8c2b2c02c5180311115b3d5fa | 5fb52ddc67e52a472f28d69e60f3ac94989e70b5307ac3fa95fe53e87c1d2696 | c1ccc(CCN2CCC(N3CCc4ccccc43)CC2)cc1 | O-[C;H0;D3;+0:1](=O)-[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] | 112.2 | [{"value": 112.2, "product": "FC=1C=C(CCN2CCC(CC2)N2CCC3=CC=CC=C23)C=CC1F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | 3,4-Difluorophenylacetic acid (0.095 g) was dissolved in tetrahydrofuran (5.0 ml). After adding 1,1-carbonyldiimidazole (0.089 g) to the resultant solution, the resultant mixture was stirred at room temperature for 15 min followedbytheadditionof 1-(piperidin-4-yl)indoline (0.1 g). After stirring at room temperature ove... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | Tertiary amine | C1CCNCC1 | C1CC[NH]CC1 | c1ccccc1.C1CC[NH]CC1.c1ccc2c(c1)CC[NH]2 | Other | O1CCCC1.O.C(C)(=O)OCC | null | 8 | O=C(O)Cc1ccc(F)c(F)c1.c1ccc2c(c1)CCN2C1CCNCC1>O1CCCC1.O.C(C)(=O)OCC>Fc1ccc(CCN2CCC(N3CCc4ccccc43)CC2)cc1F |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-592c2ccfeb014b6889583b5bbbafa3fb | CC(CBr)c1ccc(F)cc1.CN(C)C=O.c1ccc2c(c1)CCN2N1CCNCC1>>CC(CN1CCC(N2CCc3ccccc32)CC1)c1ccc(F)cc1 | N1CCN(CC1)N1CCC2=CC=CC=C12.CN(C=O)C.O.BrCC(C)C1=CC=C(C=C1)F.C(C)N(CC)CC>>FC1=CC=C(C=C1)C(CN1CCC(CC1)N1CCC2=CC=CC=C12)C | Br[CH2:3][CH:2]([CH3:1])[c:19]1[cH:20][cH:21][c:22]([F:23])[cH:24][cH:25]1.CN(C=O)[CH3:7].N1([N:8]2[CH2:9][CH2:10][c:11]3[cH:12][cH:13][cH:14][cH:15][c:16]32)[CH2:6][CH2:5][NH:4][CH2:18][CH2:17]1>>[CH3:1][CH:2]([CH2:3][N:4]1[CH2:5][CH2:6][CH:7]([N:8]2[CH2:9][CH2:10][c:11]3[cH:12][cH:13][cH:14][cH:15][c:16]32)[CH2:17][C... | CC(CBr)c1ccc(F)cc1.CN(C)C=O.c1ccc2c(c1)CCN2N1CCNCC1 | CC(CN1CCC(N2CCc3ccccc32)CC1)c1ccc(F)cc1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | b37082be9999d78e926181ae12b7211259545977a49ceae9dfb7fe9bdd60616e | 820ce533be53ecf6f8e00a40de3563b07515a2706cd963a657028835e321f8a6 | c1ccc(CCN2CCC(N3CCc4ccccc43)CC2)cc1 | Br-[CH2;D2;+0:1]-[C:2](-[C;D1;H3:3])-[c:4].C-N(-[CH3;D1;+0:5])-C=O.[c:6]:[c:7]1:[c:8]-[C:9]-[C:10]-[N;H0;D3;+0:11]-1-N1-[CH2;D2;+0:12]-[C:13]-[NH;D2;+0:14]-[C:15]-[CH2;D2;+0:16]-1>>[C;D1;H3:3]-[C:2](-[c:4])-[CH2;D2;+0:1]-[N;H0;D3;+0:14]1-[C:13]-[CH2;D2;+0:12]-[CH;D3;+0:5](-[N;H0;D3;+0:11]2-[C:10]-[C:9]-[c:8]:[c:7]-2:[c... | null | [] | 60 | CELSIUS | 8 | HOUR | 1-(4-Piperazinyl)indoline (0.20 g) was dissolved in dimethylformamide (3 ml) and 4-(2-bromo-1-methylethyl)fluorobenzene (10.0 g) and triethylamine (0.14 ml) were added to the resultant solution followed by stirring at 60° C. overnight. After adding water, the liquid reaction mixture was extracted with ethyl acetate. Th... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Primary halide.Tertiary amide.Secondary amine | Tertiary amine.Tertiary amine | c1ccc2c(c1)CC[NH]2.C1CNCCN1 | C1CC[NH]CC1.c1ccc2c(c1)CC[NH]2 | C1CC[NH]CC1.c1ccc2c(c1)CC[NH]2.c1ccccc1 | HBr | null | 60 | 8 | CC(CBr)c1ccc(F)cc1.CN(C)C=O.c1ccc2c(c1)CCN2N1CCNCC1>>CC(CN1CCC(N2CCc3ccccc32)CC1)c1ccc(F)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-2fc0163eedf04b9084ed4dbc0ab44981 | COc1ccc(CCN2CCC(N3CCc4ccccc43)CC2)cc1>>Oc1ccc(CCN2CCC(N3CCc4ccccc43)CC2)cc1 | COC1=CC=C(CCN2CCC(CC2)N2CCC3=CC=CC=C23)C=C1.C([O-])(O)=O.[Na+]>>OC1=CC=C(CCN2CCC(CC2)N2CCC3=CC=CC=C23)C=C1 | C[O: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][cH:18][cH:19][c:20]43)[CH2:21][CH2:22]2)[cH:23][cH:24]1>>[OH: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][cH:18][cH:19][c:20]43)[CH2:... | COc1ccc(CCN2CCC(N3CCc4ccccc43)CC2)cc1 | Oc1ccc(CCN2CCC(N3CCc4ccccc43)CC2)cc1 | null | null | Br | Deprotection | Cleavage of methoxy ethers to alcohols | c5320c7dfa4f544d4900efcae9b3262bf0d5286bcf39c86109232351f35b23d5 | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | c1ccc(CCN2CCC(N3CCc4ccccc43)CC2)cc1 | C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[OH;D1;+0:1]-[c:2](:[c:3]):[c:4] | 75.7 | [{"value": 75.7, "product": "OC1=CC=C(CCN2CCC(CC2)N2CCC3=CC=CC=C23)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 51.3, "product": "OC1=CC=C(CCN2CCC(CC2)N2CCC3=CC=CC=C23)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 1-[1-(4-Methoxyphenethyl)piperidin-4-yl]indoline (0.23 g) was dissolved in a 47% aqueous solution (5 ml) of hydrobromic acid and the resultant solution was heated under reflux for 90 min. After allowing to cool, the resultant mixture was poured into a saturated aqueous solution of sodium bicarbonate (pH 9-10), extracte... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | null | null | c1ccccc1.C1CC[NH]CC1.c1ccc2c(c1)CC[NH]2 | Other | Br | null | null | COc1ccc(CCN2CCC(N3CCc4ccccc43)CC2)cc1>Br>Oc1ccc(CCN2CCC(N3CCc4ccccc43)CC2)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-a960bfee6eb84d98a502de7b889a1a4c | ON=Cc1ccc(CCN2CCC(N3CCc4ccccc43)CC2)cc1>>N#Cc1ccc(CCN2CCC(N3CCc4ccccc43)CC2)cc1 | ON=CC1=CC=C(CCN2CCC(CC2)N2CCC3=CC=CC=C23)C=C1.C(C)N(CC)CC.FC(C(=O)OC(C(F)(F)F)=O)(F)F.C([O-])(O)=O.[Na+]>>C(#N)C1=CC=C(CCN2CCC(CC2)N2CCC3=CC=CC=C23)C=C1 | O[N:1]=[CH: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][cH:19][cH:20][c:21]43)[CH2:22][CH2:23]2)[cH:24][cH:25]1>>[N:1]#[C: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][cH:19][cH:20]... | ON=Cc1ccc(CCN2CCC(N3CCc4ccccc43)CC2)cc1 | N#Cc1ccc(CCN2CCC(N3CCc4ccccc43)CC2)cc1 | null | null | C(Cl)Cl | Functional Group Interconversion | OtherReaction | 17f476cc256704e312f02cdb730538a4d2e78e129aaed9ef4aa555a9b052c890 | 9ad4e779dba60265752423413bc1b61ff9562539f91b24f3b3d9205e4bb46232 | c1ccc(CCN2CCC(N3CCc4ccccc43)CC2)cc1 | O-[N;H0;D2;+0:1]=[CH;D2;+0:2]-[c:3](:[c:4]):[c:5]>>[N;H0;D1;+0:1]#[C;H0;D2;+0:2]-[c:3](:[c:4]):[c:5] | 28.9 | [{"value": 28.9, "product": "C(#N)C1=CC=C(CCN2CCC(CC2)N2CCC3=CC=CC=C23)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 28.5, "product": "C(#N)C1=CC=C(CCN2CCC(CC2)N2CCC3=CC=CC=C23)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | 1-[1-(4-Hydroxyiminomethylphenethyl)piperidin-4-yl]indoline (0.466 g) was dissolved in methylene chloride (6.5 ml) and triethylamine (0.35 ml) was added thereto. In a nitrogen atmosphere at −78° C., trifluoroacetic anhydride (0.14 ml) was added dropwise into the resultant solution followed by stirring for 3 hr. After a... | 10.6084/m9.figshare.5104873.v1 | null | Oxime | Nitrile | null | null | c1ccccc1.C1CC[NH]CC1.c1ccc2c(c1)CC[NH]2 | HO- | C(Cl)Cl | null | 3 | ON=Cc1ccc(CCN2CCC(N3CCc4ccccc43)CC2)cc1>C(Cl)Cl>N#Cc1ccc(CCN2CCC(N3CCc4ccccc43)CC2)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-ad20e0323510435ca07d8ef1ac76a650 | CN(C)C=O.Oc1ccc(CCN2CCC(N3CCc4ccccc43)CC2)cc1>>OCCOc1ccc(CCN2CCC(N3CCc4ccccc43)CC2)cc1 | [F-].C(CCC)[N+](CCCC)(CCCC)CCCC.CN(C=O)C.OC1=CC=C(CCN2CCC(CC2)N2CCC3=CC=CC=C23)C=C1.C([O-])([O-])=O.[K+].[K+]>>OCCOC1=CC=C(CCN2CCC(CC2)N2CCC3=CC=CC=C23)C=C1 | CN(C)[CH:2]=[O:1].[OH:4][c:5]1[cH:6][cH:7][c:8]([CH2:9][CH2:10][N:11]2[CH2:12][CH2:13][CH:14]([N:15]3[CH2:16][CH2:17][c:18]4[cH:19][cH:20][cH:21][cH:22][c:23]43)[CH2:24][CH2:25]2)[cH:26][cH:27]1>>[OH:1][CH2:2][CH2:3][O:4][c:5]1[cH:6][cH:7][c:8]([CH2:9][CH2:10][N:11]2[CH2:12][CH2:13][CH:14]([N:15]3[CH2:16][CH2:17][c:18]... | CN(C)C=O.Oc1ccc(CCN2CCC(N3CCc4ccccc43)CC2)cc1 | OCCOc1ccc(CCN2CCC(N3CCc4ccccc43)CC2)cc1 | null | null | O1CCCC1 | Heteroatom Alkylation and Arylation | OtherReaction | bcf9fd981fd2040cd6d8220c5c5519db7d44191b04393e05f3bd9366deb5fa31 | be844049e57b80b3886f8f5940a33c5bdd841a7aa6ac8ef048df5c8a542461b5 | c1ccc(CCN2CCC(N3CCc4ccccc43)CC2)cc1 | C-N(-C)-[CH;D2;+0:1]=[O;H0;D1;+0:2].[OH;D1;+0:3]-[c:4](:[c:5]):[c:6]>>[OH;D1;+0:2]-[CH2;D2;+0:1]-[C:7]-[O;H0;D2;+0:3]-[c:4](:[c:5]):[c:6] | 69 | [{"value": 69.0, "product": "OCCOC1=CC=C(CCN2CCC(CC2)N2CCC3=CC=CC=C23)C=C1", "details": "PERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | 28 | HOUR | N,N-Dimethylformamide (2.5 ml) was added to 1-[1-(4-hydroxyphenethyl)piperidin-4-yl]indoline (0.1 g), potassium carbonate (0.081 g) and 1-bromo-2-di(t-butyl)dimethylsilyloxyethane (0.20 g) and the resultant mixture was heated and stirred at 80° C. for 28 hr. After allowing to cool, it was extracted with ethyl acetate (... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Aromatic alcohol | Ether.Primary alcohol | null | null | c1ccccc1.C1CC[NH]CC1.c1ccc2c(c1)CC[NH]2 | Other | O1CCCC1 | 80 | 28 | CN(C)C=O.Oc1ccc(CCN2CCC(N3CCc4ccccc43)CC2)cc1>O1CCCC1>OCCOc1ccc(CCN2CCC(N3CCc4ccccc43)CC2)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-956123743f00448098c5eda3eb046329 | CS(=O)(=O)c1ccc(CCBr)cc1.c1ccc2c(c1)CCN2C1CCNCC1>>CS(=O)(=O)c1ccc(CCN2CCC(N3CCc4ccccc43)CC2)cc1 | N1CCC(CC1)N1CCC2=CC=CC=C12.CS(=O)(=O)C1=CC=C(CCBr)C=C1>>CS(=O)(=O)C1=CC=C(CCN2CCC(CC2)N2CCC3=CC=CC=C23)C=C1 | Br[CH2:10][CH2:9][c:8]1[cH:7][cH:6][c:5]([S:2]([CH3:1])(=[O:3])=[O:4])[cH:27][cH:26]1.[NH:11]1[CH2:12][CH2:13][CH:14]([N:15]2[CH2:16][CH2:17][c:18]3[cH:19][cH:20][cH:21][cH:22][c:23]32)[CH2:24][CH2:25]1>>[CH3:1][S:2](=[O:3])(=[O:4])[c:5]1[cH:6][cH:7][c:8]([CH2:9][CH2:10][N:11]2[CH2:12][CH2:13][CH:14]([N:15]3[CH2:16][CH... | CS(=O)(=O)c1ccc(CCBr)cc1.c1ccc2c(c1)CCN2C1CCNCC1 | CS(=O)(=O)c1ccc(CCN2CCC(N3CCc4ccccc43)CC2)cc1 | 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] | 47.3 | [{"value": 43.0, "product": "CS(=O)(=O)C1=CC=C(CCN2CCC(CC2)N2CCC3=CC=CC=C23)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 47.3, "product": "CS(=O)(=O)C1=CC=C(CCN2CCC(CC2)N2CCC3=CC=CC=C23)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 1-(Piperidin-4-yl)indoline (200 mg) and 4-methane-sulfonylphenethyl bromide (290 mg) were treated as in Example 2 to give the title compound (180 mg) as a white powder (yield: 43%).
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 | CS(=O)(=O)c1ccc(CCBr)cc1.c1ccc2c(c1)CCN2C1CCNCC1>>CS(=O)(=O)c1ccc(CCN2CCC(N3CCc4ccccc43)CC2)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-3368bc5eb73f47f98ef2b13d0303d0e8 | O=[N+]([O-])c1ccc(CCBr)cc1.c1ccc2c(c1)CCN2N1CCNCC1>>O=[N+]([O-])c1ccc(CCN2CCC(N3CCc4ccccc43)CC2)cc1 | BrCCC1=CC=C(C=C1)[N+](=O)[O-].C(C)N(CC)CC.N1CCN(CC1)N1CCC2=CC=CC=C12.CN(C=O)C.O>>[N+](=O)([O-])C1=CC=C(CCN2CCC(CC2)N2CCC3=CC=CC=C23)C=C1 | Br[CH2:9][CH2:8][c:7]1[cH:6][cH:5][c:4]([N+:2](=[O:1])[O-:3])[cH:26][cH:25]1.N1([N:14]2[CH2:15][CH2:16][c:17]3[cH:18][cH:19][cH:20][cH:21][c:22]32)[CH2:12][CH2:11][NH:10][CH2:24][CH2:23]1>>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][cH:6][c: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:18][cH:1... | O=[N+]([O-])c1ccc(CCBr)cc1.c1ccc2c(c1)CCN2N1CCNCC1 | O=[N+]([O-])c1ccc(CCN2CCC(N3CCc4ccccc43)CC2)cc1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 677dc689e2186ab56c65d8a206f7b8ddb6ff34ff7b3272fd1d7c0e08eb66cf1f | 9360613445906e489a694b835bc83d77c0f0bce85fb9916039db4e34a3991950 | c1ccc(CCN2CCC(N3CCc4ccccc43)CC2)cc1 | Br-[CH2;D2;+0:1]-[C:2]-[c:3].[c:4]:[c:5]1:[c:6]-[C:7]-[C:8]-[N;H0;D3;+0:9]-1-N1-[CH2;D2;+0:10]-[C:11]-[NH;D2;+0:12]-[C:13]-[CH2;D2;+0:14]-1>>[c:4]:[c:5]1:[c:6]-[C:7]-[C:8]-[N;H0;D3;+0:9]-1-[C:15]1-[CH2;D2;+0:10]-[C:11]-[N;H0;D3;+0:12](-[CH2;D2;+0:1]-[C:2]-[c:3])-[C:13]-[CH2;D2;+0:14]-1 | null | [] | null | null | null | null | 1-(Piperazin-4-yl)indoline (2.00 g) was dissolved in dimethylformamide (20 ml) and 4-(2-bromoethyl)nitrobenzene (10.0 g) and triethylamine (2.9 ml) were added thereto followed by stirring the resultant mixture at 100° C. overnight. After adding water to the reaction solution, extracted with ethyl acetate, the organic l... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Primary halide.Secondary amine | Tertiary amine.Tertiary amine | c1ccc2c(c1)CC[NH]2.C1CNCCN1 | C1CC[NH]CC1.c1ccc2c(c1)CC[NH]2 | c1ccccc1.C1CC[NH]CC1.c1ccc2c(c1)CC[NH]2 | Br- | null | null | null | O=[N+]([O-])c1ccc(CCBr)cc1.c1ccc2c(c1)CCN2N1CCNCC1>>O=[N+]([O-])c1ccc(CCN2CCC(N3CCc4ccccc43)CC2)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-dd5bb6d2163d4851b2305b4614d03792 | O=[N+]([O-])c1ccc(CCN2CCC(N3CCc4ccccc43)CC2)cc1>>Nc1ccc(CCN2CCC(N3CCc4ccccc43)CC2)cc1 | Cl.[N+](=O)([O-])C1=CC=C(CCN2CCC(CC2)N2CCC3=CC=CC=C23)C=C1>>NC1=CC=C(CCN2CCC(CC2)N2CCC3=CC=CC=C23)C=C1 | O=[N+:1]([O-])[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][cH:18][cH:19][c:20]43)[CH2:21][CH2:22]2)[cH:23][cH:24]1>>[NH2:1][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][cH:18][cH:19][c:20... | O=[N+]([O-])c1ccc(CCN2CCC(N3CCc4ccccc43)CC2)cc1 | Nc1ccc(CCN2CCC(N3CCc4ccccc43)CC2)cc1 | null | [Pd] | CO | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccc(CCN2CCC(N3CCc4ccccc43)CC2)cc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | 0.1 | [{"value": 0.1, "product": "NC1=CC=C(CCN2CCC(CC2)N2CCC3=CC=CC=C23)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 1-[1-(4-Nitrophenethyl)piperidin-4-yl]indoline (780 g) was dissolved in methanol (7 ml) and conc. hydrochloric acid (0.5 ml) was added dropwise into the resultant solution. Subsequently, the resultant mixture was catalytically reduced under atmospheric pressure in the presence of a palladium catalyst. After filtering o... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1.C1CC[NH]CC1.c1ccc2c(c1)CC[NH]2 | Other | [Pd].CO | null | null | O=[N+]([O-])c1ccc(CCN2CCC(N3CCc4ccccc43)CC2)cc1>[Pd].CO>Nc1ccc(CCN2CCC(N3CCc4ccccc43)CC2)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-de6d8003fadc47fbb3111aa40970f83a | CC(=O)Cl.Nc1ccc(CCN2CCC(N3CCc4ccccc43)CC2)cc1>>CC(=O)Nc1ccc(CCN2CCC(N3CCc4ccccc43)CC2)cc1 | C(C)(=O)Cl.NC1=CC=C(CCN2CCC(CC2)N2CCC3=CC=CC=C23)C=C1.C([O-])([O-])=O.[K+].[K+]>>C(C)(=O)NC1=CC=C(CCN2CCC(CC2)N2CCC3=CC=CC=C23)C=C1 | Cl[C:2]([CH3:1])=[O:3].[NH2:4][c:5]1[cH:6][cH:7][c:8]([CH2:9][CH2:10][N:11]2[CH2:12][CH2:13][CH:14]([N:15]3[CH2:16][CH2:17][c:18]4[cH:19][cH:20][cH:21][cH:22][c:23]43)[CH2:24][CH2:25]2)[cH:26][cH:27]1>>[CH3:1][C:2](=[O:3])[NH:4][c:5]1[cH:6][cH:7][c:8]([CH2:9][CH2:10][N:11]2[CH2:12][CH2:13][CH:14]([N:15]3[CH2:16][CH2:17... | CC(=O)Cl.Nc1ccc(CCN2CCC(N3CCc4ccccc43)CC2)cc1 | CC(=O)Nc1ccc(CCN2CCC(N3CCc4ccccc43)CC2)cc1 | null | null | C(Cl)Cl | 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:7]>>[C;D1;H3:2]-[C;H0;D3;+0:1](=[O;D1;H0:3])-[NH;D2;+0:4]-[c:5](:[c:6]):[c:7] | null | [] | null | null | 45 | MINUTE | 1-[1-(4-Aminophenethyl)piperidin-4-yl]indoline (310 mg) was dissolved in methylene chloride (3 ml). Under ice cooling, acetyl chloride (0.103 ml) was added to the resultant solution followed by stirring the obtained mixture for 45 min. After adding a 10% aqueous solution of potassium carbonate, the reaction solution wa... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccccc1.C1CC[NH]CC1.c1ccc2c(c1)CC[NH]2 | HCl | C(Cl)Cl | null | 0.75 | CC(=O)Cl.Nc1ccc(CCN2CCC(N3CCc4ccccc43)CC2)cc1>C(Cl)Cl>CC(=O)Nc1ccc(CCN2CCC(N3CCc4ccccc43)CC2)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-92e4dcda843b4be29dd3f2eee44ed090 | CC(=O)Nc1ccc(CCN2CCC(N3CCc4ccccc43)CC2)cc1>>CCNc1ccc(CCN2CCC(N3CCc4ccccc43)CC2)cc1 | O.[H-].[Al+3].[Li+].[H-].[H-].[H-].N(C(=O)C)C1=CC=C(CCN2CCC(CC2)N2CCC3=CC=CC=C23)C=C1>>C(C)NC1=CC=C(CCN2CCC(CC2)N2CCC3=CC=CC=C23)C=C1 | O=[C:2]([CH3:1])[NH:3][c:4]1[cH:5][cH:6][c: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:18][cH:19][cH:20][cH:21][c:22]43)[CH2:23][CH2:24]2)[cH:25][cH:26]1>>[CH3:1][CH2:2][NH:3][c:4]1[cH:5][cH:6][c: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:18][... | CC(=O)Nc1ccc(CCN2CCC(N3CCc4ccccc43)CC2)cc1 | CCNc1ccc(CCN2CCC(N3CCc4ccccc43)CC2)cc1 | null | null | O1CCCC1 | Reduction | Reduction of secondary amides to amines | 85b757f1833edc9e5c6365ee6b904683f414e7b9a5f9bfcfd7addca401447058 | ab40188eef2f825df7003af0ffae31d0ce53d126542122535627d3d354cbc9fe | c1ccc(CCN2CCC(N3CCc4ccccc43)CC2)cc1 | O=[C;H0;D3;+0:1](-[C;D1;H3:2])-[#7:3]-[c:4]>>[C;D1;H3:2]-[CH2;D2;+0:1]-[#7:3]-[c:4] | 30.8 | [{"value": 30.8, "product": "C(C)NC1=CC=C(CCN2CCC(CC2)N2CCC3=CC=CC=C23)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 1-[1-(4-Acetaminophenethyl)piperidin-4-yl]indoline (135 mg) was dissolved in tetrahydrofuran (5 ml). After adding lithium aluminum hydride (28 mg) at room temperature, the resultant mixture was heated under reflux for 2 hr. After adding water, the reaction solution was extracted with ethyl acetate. Then the organic lay... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide | null | null | null | c1ccccc1.C1CC[NH]CC1.c1ccc2c(c1)CC[NH]2 | Other | O1CCCC1 | null | null | CC(=O)Nc1ccc(CCN2CCC(N3CCc4ccccc43)CC2)cc1>O1CCCC1>CCNc1ccc(CCN2CCC(N3CCc4ccccc43)CC2)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-98ebcd9e97ca4f119dabd45ea7c19bd3 | ON=Cc1ccc(CCN2CCC(N3CCc4ccccc43)CC2)cc1>>NCc1ccc(CCN2CCC(N3CCc4ccccc43)CC2)cc1 | O.[OH-].[Na+].O.[H-].[Al+3].[Li+].[H-].[H-].[H-].ON=CC1=CC=C(CCN2CCC(CC2)N2CCC3=CC=CC=C23)C=C1>>NCC1=CC=C(CCN2CCC(CC2)N2CCC3=CC=CC=C23)C=C1 | O[N:1]=[CH: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][cH:19][cH:20][c:21]43)[CH2:22][CH2:23]2)[cH:24][cH:25]1>>[NH2:1][CH2:2][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][cH:19][cH:... | ON=Cc1ccc(CCN2CCC(N3CCc4ccccc43)CC2)cc1 | NCc1ccc(CCN2CCC(N3CCc4ccccc43)CC2)cc1 | null | null | O1CCCC1 | Reduction | OtherReaction | 2911de7676f9c054838849cab652dcb324de4944866edb887235c5bf7854a715 | 4a7bf747f64425b21ceaa04fbc4c046ccf522c774aa5649ec92eba03e46bfee5 | c1ccc(CCN2CCC(N3CCc4ccccc43)CC2)cc1 | O-[N;H0;D2;+0:1]=[CH;D2;+0:2]-[c:3](:[c:4]):[c:5]>>[NH2;D1;+0:1]-[CH2;D2;+0:2]-[c:3](:[c:4]):[c:5] | 56.2 | [{"value": 56.2, "product": "NCC1=CC=C(CCN2CCC(CC2)N2CCC3=CC=CC=C23)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 56.2, "product": "NCC1=CC=C(CCN2CCC(CC2)N2CCC3=CC=CC=C23)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 1-[1-(4-Hydroxyiminomethylphenethyl)piperidin-4-yl]indoline (2.71 g) was dissolved in tetrahydrofuran (40 ml). Under ice cooling, lithium aluminum hydride (0.59 g) was added thereto and the resultant mixture was heated under reflux for 2 hr. Then the reaction mixture was ice cooled again followed by the addition of wat... | 10.6084/m9.figshare.5104873.v1 | null | Oxime | Primary amine | null | null | c1ccccc1.C1CC[NH]CC1.c1ccc2c(c1)CC[NH]2 | Other | O1CCCC1 | null | null | ON=Cc1ccc(CCN2CCC(N3CCc4ccccc43)CC2)cc1>O1CCCC1>NCc1ccc(CCN2CCC(N3CCc4ccccc43)CC2)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-c4d8ab43de154be5b60ed348ae175194 | CC(=O)Cl.NCc1ccc(CCN2CCC(N3CCc4ccccc43)CC2)cc1>>CC(=O)NCc1ccc(CCN2CCC(N3CCc4ccccc43)CC2)cc1 | C([O-])(O)=O.[Na+].C(C)(=O)Cl.NCC1=CC=C(CCN2CCC(CC2)N2CCC3=CC=CC=C23)C=C1>>C(C)(=O)NCC1=CC=C(CCN2CCC(CC2)N2CCC3=CC=CC=C23)C=C1 | Cl[C:2]([CH3:1])=[O:3].[NH2:4][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]... | CC(=O)Cl.NCc1ccc(CCN2CCC(N3CCc4ccccc43)CC2)cc1 | CC(=O)NCc1ccc(CCN2CCC(N3CCc4ccccc43)CC2)cc1 | null | null | O1CCCC1 | 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] | 79.2 | [{"value": 79.2, "product": "C(C)(=O)NCC1=CC=C(CCN2CCC(CC2)N2CCC3=CC=CC=C23)C=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | 1-[1-(4-Aminomethylphenethyl)piperidin-4-yl]indoline (0.6 g) was dissolved in tetrahydrofuran (9.0 ml). Under ice cooling, acetyl chloride (0.14 ml) was added dropwise thereinto and the resultant mixture was stirred for 2 hr. After adding a saturated aqueous solution of sodium bicarbonate, the mixture was extracted wit... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccccc1.C1CC[NH]CC1.c1ccc2c(c1)CC[NH]2 | HCl | O1CCCC1 | null | null | CC(=O)Cl.NCc1ccc(CCN2CCC(N3CCc4ccccc43)CC2)cc1>O1CCCC1>CC(=O)NCc1ccc(CCN2CCC(N3CCc4ccccc43)CC2)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-c405968da8c749ae9db01908a1174187 | NCc1ccc(CCN2CCC(N3CCc4ccccc43)CC2)cc1.O=C(Cl)CCl>>O=C(CCl)NCc1ccc(CCN2CCC(N3CCc4ccccc43)CC2)cc1 | NCC1=CC=C(CCN2CCC(CC2)N2CCC3=CC=CC=C23)C=C1.ClCC(=O)Cl>>ClCC(=O)NCC1=CC=C(CCN2CCC(CC2)N2CCC3=CC=CC=C23)C=C1 | [NH2:5][CH2:6][c:7]1[cH:8][cH:9][c:10]([CH2:11][CH2:12][N:13]2[CH2:14][CH2:15][CH:16]([N:17]3[CH2:18][CH2:19][c:20]4[cH:21][cH:22][cH:23][cH:24][c:25]43)[CH2:26][CH2:27]2)[cH:28][cH:29]1.Cl[C:2](=[O:1])[CH2:3][Cl:4]>>[O:1]=[C:2]([CH2:3][Cl:4])[NH:5][CH2:6][c:7]1[cH:8][cH:9][c:10]([CH2:11][CH2:12][N:13]2[CH2:14][CH2:15]... | NCc1ccc(CCN2CCC(N3CCc4ccccc43)CC2)cc1.O=C(Cl)CCl | O=C(CCl)NCc1ccc(CCN2CCC(N3CCc4ccccc43)CC2)cc1 | null | null | null | 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]-[Cl;D1;H0:4].[NH2;D1;+0:5]-[C:6]-[c:7]>>[Cl;D1;H0:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:5]-[C:6]-[c:7] | 62.1 | [{"value": 62.1, "product": "ClCC(=O)NCC1=CC=C(CCN2CCC(CC2)N2CCC3=CC=CC=C23)C=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | 1-[1-(4-Aminomethylphenethyl)piperidin-4-yl]indoline (0.1 g) and chloroacetyl chloride (0.026 ml) were treated as in Example 36 to give the title compound (0.074 g) as a pale yellow oil (yield: 62.1%).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccccc1.C1CC[NH]CC1.c1ccc2c(c1)CC[NH]2 | HCl | null | null | null | NCc1ccc(CCN2CCC(N3CCc4ccccc43)CC2)cc1.O=C(Cl)CCl>>O=C(CCl)NCc1ccc(CCN2CCC(N3CCc4ccccc43)CC2)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-61788ba822c24d7a88900203c3ff9301 | CS(=O)(=O)Cl.NCc1ccc(CCN2CCC(N3CCc4ccccc43)CC2)cc1>>CS(=O)(=O)NCc1ccc(CCN2CCC(N3CCc4ccccc43)CC2)cc1 | NCC1=CC=C(CCN2CCC(CC2)N2CCC3=CC=CC=C23)C=C1.CS(=O)(=O)Cl>>CS(=O)(=O)NCC1=CC=C(CCN2CCC(CC2)N2CCC3=CC=CC=C23)C=C1 | Cl[S:2]([CH3:1])(=[O:3])=[O:4].[NH2:5][CH2:6][c:7]1[cH:8][cH:9][c:10]([CH2:11][CH2:12][N:13]2[CH2:14][CH2:15][CH:16]([N:17]3[CH2:18][CH2:19][c:20]4[cH:21][cH:22][cH:23][cH:24][c:25]43)[CH2:26][CH2:27]2)[cH:28][cH:29]1>>[CH3:1][S:2](=[O:3])(=[O:4])[NH:5][CH2:6][c:7]1[cH:8][cH:9][c:10]([CH2:11][CH2:12][N:13]2[CH2:14][CH2... | CS(=O)(=O)Cl.NCc1ccc(CCN2CCC(N3CCc4ccccc43)CC2)cc1 | CS(=O)(=O)NCc1ccc(CCN2CCC(N3CCc4ccccc43)CC2)cc1 | null | null | null | Miscellaneous | Sulfonamide synthesis (Schotten-Baumann) primary amine | a86b0632821e188c0a5dc5a5a2aac298ab3eccaee8a52ba46078c3d5975a290d | 50f8fbf3d327483c3eeff8f6cbd4065e4c7600bb501fbe08958a5c79a0926428 | c1ccc(CCN2CCC(N3CCc4ccccc43)CC2)cc1 | Cl-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4].[NH2;D1;+0:5]-[C:6]-[c:7]>>[C;D1;H3:2]-[S;H0;D4;+0:1](=[O;D1;H0:3])(=[O;D1;H0:4])-[NH;D2;+0:5]-[C:6]-[c:7] | 54.5 | [{"value": 54.5, "product": "CS(=O)(=O)NCC1=CC=C(CCN2CCC(CC2)N2CCC3=CC=CC=C23)C=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | 1-[1-(4-Aminomethylphenethyl)piperidin-4-yl]indoline (0.120 g) and methanesulfonyl chloride (0.030 ml) were treated as in Example 36 to give the title compound (0.078 g) as a pale yel low oil (yield: 54.5%).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Sulfonyl halide | Sulfonamide | null | null | c1ccccc1.C1CC[NH]CC1.c1ccc2c(c1)CC[NH]2 | HCl | null | null | null | CS(=O)(=O)Cl.NCc1ccc(CCN2CCC(N3CCc4ccccc43)CC2)cc1>>CS(=O)(=O)NCc1ccc(CCN2CCC(N3CCc4ccccc43)CC2)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-1a7c18596ed54aedaf32d9601c726b6d | CC1CN(C2CCN(CCc3ccc(CN)cc3)CC2)c2ccccc21.CCC(=O)Cl>>CCC(=O)NCc1ccc(CCN2CCC(N3CC(C)c4ccccc43)CC2)cc1 | NCC1=CC=C(CCN2CCC(CC2)N2CC(C3=CC=CC=C23)C)C=C1.C(CC)(=O)Cl>>C(CC)(=O)NCC1=CC=C(CCN2CCC(CC2)N2CC(C3=CC=CC=C23)C)C=C1 | [NH2:5][CH2:6][c:7]1[cH:8][cH:9][c:10]([CH2:11][CH2:12][N:13]2[CH2:14][CH2:15][CH:16]([N:17]3[CH2:18][CH:19]([CH3:20])[c:21]4[cH:22][cH:23][cH:24][cH:25][c:26]43)[CH2:27][CH2:28]2)[cH:29][cH:30]1.Cl[C:3]([CH2:2][CH3:1])=[O:4]>>[CH3:1][CH2:2][C:3](=[O:4])[NH:5][CH2:6][c:7]1[cH:8][cH:9][c:10]([CH2:11][CH2:12][N:13]2[CH2:... | CC1CN(C2CCN(CCc3ccc(CN)cc3)CC2)c2ccccc21.CCC(=O)Cl | CCC(=O)NCc1ccc(CCN2CCC(N3CC(C)c4ccccc43)CC2)cc1 | null | null | null | 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].[NH2;D1;+0:5]-[C:6]-[c:7]>>[C;D1;H3:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:5]-[C:6]-[c:7] | null | [] | null | null | null | null | 1-[1-(4-Aminomethylphenethyl)piperidin-4-yl]-3-methylindoline (0.1 g) and propionyl chloride (0.028 ml) were treated as in Example 36 to give the title compound (0.122 g) as a pale yellow oil (yield: quantitative).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccccc1.C1CC[NH]CC1.c1ccc2c(c1)CC[NH]2 | HCl | null | null | null | CC1CN(C2CCN(CCc3ccc(CN)cc3)CC2)c2ccccc21.CCC(=O)Cl>>CCC(=O)NCc1ccc(CCN2CCC(N3CC(C)c4ccccc43)CC2)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-58b15d9f5d06430c8c06f339cd5d714b | NS(=O)(=O)c1ccc(CCBr)cc1.c1ccc2c(c1)CCN2C1CCNCC1>>NS(=O)(=O)c1ccc(CCN2CCC(N3CCc4ccccc43)CC2)cc1 | N1CCC(CC1)N1CCC2=CC=CC=C12.S(N)(=O)(=O)C1=CC=C(CCBr)C=C1>>S(N)(=O)(=O)C1=CC=C(CCN2CCC(CC2)N2CCC3=CC=CC=C23)C=C1 | Br[CH2:10][CH2:9][c:8]1[cH:7][cH:6][c:5]([S:2]([NH2:1])(=[O:3])=[O:4])[cH:27][cH:26]1.[NH:11]1[CH2:12][CH2:13][CH:14]([N:15]2[CH2:16][CH2:17][c:18]3[cH:19][cH:20][cH:21][cH:22][c:23]32)[CH2:24][CH2:25]1>>[NH2:1][S:2](=[O:3])(=[O:4])[c:5]1[cH:6][cH:7][c:8]([CH2:9][CH2:10][N:11]2[CH2:12][CH2:13][CH:14]([N:15]3[CH2:16][CH... | NS(=O)(=O)c1ccc(CCBr)cc1.c1ccc2c(c1)CCN2C1CCNCC1 | NS(=O)(=O)c1ccc(CCN2CCC(N3CCc4ccccc43)CC2)cc1 | 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] | 10.5 | [{"value": 10.0, "product": "S(N)(=O)(=O)C1=CC=C(CCN2CCC(CC2)N2CCC3=CC=CC=C23)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 10.5, "product": "S(N)(=O)(=O)C1=CC=C(CCN2CCC(CC2)N2CCC3=CC=CC=C23)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 1-(Piperidin-4-yl)indoline (300 mg) and 4-sulfamoylphenethyl bromide (400 mg) were treated as in Example 2 to give the title compound (60 mg) as a pale yellow powder (yield: 10%).
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 | NS(=O)(=O)c1ccc(CCBr)cc1.c1ccc2c(c1)CCN2C1CCNCC1>>NS(=O)(=O)c1ccc(CCN2CCC(N3CCc4ccccc43)CC2)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-cdc91ced91d74f89b74f555814d0e4b3 | CN(C)CCCl.Oc1ccc(CCN2CCC(N3CCc4ccccc43)CC2)cc1>>CN(C)CCOc1ccc(CCN2CCC(N3CCc4ccccc43)CC2)cc1 | CN(C=O)C.OC1=CC=C(CCN2CCC(CC2)N2CCC3=CC=CC=C23)C=C1.C([O-])([O-])=O.[K+].[K+].Cl.CN(CCCl)C>>CN(CCOC1=CC=C(CCN2CCC(CC2)N2CCC3=CC=CC=C23)C=C1)C | Cl[CH2:5][CH2:4][N:2]([CH3:1])[CH3:3].[OH:6][c:7]1[cH:8][cH:9][c:10]([CH2:11][CH2:12][N:13]2[CH2:14][CH2:15][CH:16]([N:17]3[CH2:18][CH2:19][c:20]4[cH:21][cH:22][cH:23][cH:24][c:25]43)[CH2:26][CH2:27]2)[cH:28][cH:29]1>>[CH3:1][N:2]([CH3:3])[CH2:4][CH2:5][O:6][c:7]1[cH:8][cH:9][c:10]([CH2:11][CH2:12][N:13]2[CH2:14][CH2:1... | CN(C)CCCl.Oc1ccc(CCN2CCC(N3CCc4ccccc43)CC2)cc1 | CN(C)CCOc1ccc(CCN2CCC(N3CCc4ccccc43)CC2)cc1 | null | null | C(C)(=O)OCC | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | c1ccc(CCN2CCC(N3CCc4ccccc43)CC2)cc1 | Cl-[CH2;D2;+0:1]-[C:2]-[#7:3].[OH;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[#7:3]-[C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:4]-[c:5](:[c:6]):[c:7] | 42.6 | [{"value": 27.0, "product": "CN(CCOC1=CC=C(CCN2CCC(CC2)N2CCC3=CC=CC=C23)C=C1)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 42.6, "product": "CN(CCOC1=CC=C(CCN2CCC(CC2)N2CCC3=CC=CC=C23)C=C1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | 12 | HOUR | N,N-Dimethylformamide (2.5 ml) was added to 1-[1-(4-hydroxyphenethyl)piperidin-4-yl]indoline (0.1 g), potassium carbonate (0.081 g) and 2-dimethylaminoethyl chloride hydrochloride (0.078 g) followed by stirring at 80° C. overnight (12 hr). After allowing to cool, the resultant mixture was mixed with ethyl acetate (200 ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccccc1.C1CC[NH]CC1.c1ccc2c(c1)CC[NH]2 | HCl | C(C)(=O)OCC | 80 | 12 | CN(C)CCCl.Oc1ccc(CCN2CCC(N3CCc4ccccc43)CC2)cc1>C(C)(=O)OCC>CN(C)CCOc1ccc(CCN2CCC(N3CCc4ccccc43)CC2)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-0f91c50ccd684cd2b7b7bf9f1aa760b3 | NCCN1CCC(N2CCc3ccccc32)CC1.O=S(=O)(Cl)c1ccc(Cl)cc1>>O=S(=O)(NCCN1CCC(N2CCc3ccccc32)CC1)c1ccc(Cl)cc1 | O.ClC1=CC=C(C=C1)S(=O)(=O)Cl.NCCN1CCC(CC1)N1CCC2=CC=CC=C12>>ClC1=CC=C(C=C1)S(=O)(=O)NCCN1CCC(CC1)N1CCC2=CC=CC=C12 | [NH2:4][CH2:5][CH2:6][N:7]1[CH2:8][CH2:9][CH:10]([N:11]2[CH2:12][CH2:13][c:14]3[cH:15][cH:16][cH:17][cH:18][c:19]32)[CH2:20][CH2:21]1.Cl[S:2](=[O:1])(=[O:3])[c:22]1[cH:23][cH:24][c:25]([Cl:26])[cH:27][cH:28]1>>[O:1]=[S:2](=[O:3])([NH:4][CH2:5][CH2:6][N:7]1[CH2:8][CH2:9][CH:10]([N:11]2[CH2:12][CH2:13][c:14]3[cH:15][cH:1... | NCCN1CCC(N2CCc3ccccc32)CC1.O=S(=O)(Cl)c1ccc(Cl)cc1 | O=S(=O)(NCCN1CCC(N2CCc3ccccc32)CC1)c1ccc(Cl)cc1 | null | null | C(Cl)(Cl)Cl | Miscellaneous | Sulfonamide synthesis (Schotten-Baumann) primary amine | a86b0632821e188c0a5dc5a5a2aac298ab3eccaee8a52ba46078c3d5975a290d | 50f8fbf3d327483c3eeff8f6cbd4065e4c7600bb501fbe08958a5c79a0926428 | O=S(=O)(NCCN1CCC(N2CCc3ccccc32)CC1)c1ccccc1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6].[C:7]-[C:8]-[NH2;D1;+0:9]>>[C:7]-[C:8]-[NH;D2;+0:9]-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6] | 69.4 | [{"value": 69.4, "product": "ClC1=CC=C(C=C1)S(=O)(=O)NCCN1CCC(CC1)N1CCC2=CC=CC=C12", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 1-[1-(2-Aminoethyl)piperidin-4-yl]indoline (113 mg) was dissolved in chloroform (3 ml). Under ice cooling, 4-chlorobenzenesulfonyl chloride (97 mg) was added thereto and the resultant mixture was stirred for 6 hr. After adding water, the reaction solution was extracted with chloroform. The organic layer was washed with... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Sulfonyl halide | Sulfonamide | null | null | C1CC[NH]CC1.c1ccc2c(c1)CC[NH]2.c1ccccc1 | HCl | C(Cl)(Cl)Cl | null | null | NCCN1CCC(N2CCc3ccccc32)CC1.O=S(=O)(Cl)c1ccc(Cl)cc1>C(Cl)(Cl)Cl>O=S(=O)(NCCN1CCC(N2CCc3ccccc32)CC1)c1ccc(Cl)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-2ba0c1ebc6474761a4ac0aa9a5bce8d5 | COc1ccc(S(=O)(=O)Cl)cc1.NCCN1CCC(N2CCc3ccccc32)CC1>>COc1ccc(S(=O)(=O)NCCN2CCC(N3CCc4ccccc43)CC2)cc1 | O.COC1=CC=C(C=C1)S(=O)(=O)Cl.NCCN1CCC(CC1)N1CCC2=CC=CC=C12>>COC1=CC=C(C=C1)S(=O)(=O)NCCN1CCC(CC1)N1CCC2=CC=CC=C12 | Cl[S:7]([c:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:29][cH:28]1)(=[O:8])=[O:9].[NH2:10][CH2:11][CH2:12][N:13]1[CH2:14][CH2:15][CH:16]([N:17]2[CH2:18][CH2:19][c:20]3[cH:21][cH:22][cH:23][cH:24][c:25]32)[CH2:26][CH2:27]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([S:7](=[O:8])(=[O:9])[NH:10][CH2:11][CH2:12][N:13]2[CH2:14][CH2:15]... | COc1ccc(S(=O)(=O)Cl)cc1.NCCN1CCC(N2CCc3ccccc32)CC1 | COc1ccc(S(=O)(=O)NCCN2CCC(N3CCc4ccccc43)CC2)cc1 | null | null | C(Cl)(Cl)Cl | Acylation | Sulfonamide synthesis (Schotten-Baumann) primary amine | 4c44ef6d7646f6ef25dd125d2c32c713d8dcae7c603407faa5f0fb810631670e | 8fce8115d8a725afa92eb3910ded29d4c852e5133eba78a425054f41f7142603 | O=S(=O)(NCCN1CCC(N2CCc3ccccc32)CC1)c1ccccc1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6].[C:7]-[C:8]-[NH2;D1;+0:9]>>[C:7]-[C:8]-[NH;D2;+0:9]-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6] | 23.6 | [{"value": 23.6, "product": "COC1=CC=C(C=C1)S(=O)(=O)NCCN1CCC(CC1)N1CCC2=CC=CC=C12", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 1-[1-(2-Aminoethyl)piperidin-4-yl]indoline (113 mg) was dissolved in chloroform (3 ml). Under ice cooling, 4-methoxybenzenesulfonyl chloride (95 mg) was added thereto and the resultant mixture was stirred at room temperature overnight. After adding water, the reaction solution was extracted with chloroform. The organic... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Sulfonyl halide | Sulfonamide | null | null | c1ccccc1.C1CC[NH]CC1.c1ccc2c(c1)CC[NH]2 | HCl | C(Cl)(Cl)Cl | null | null | COc1ccc(S(=O)(=O)Cl)cc1.NCCN1CCC(N2CCc3ccccc32)CC1>C(Cl)(Cl)Cl>COc1ccc(S(=O)(=O)NCCN2CCC(N3CCc4ccccc43)CC2)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-2bb1e17f0a3f4e93b14ba3e801491e35 | C=Cc1ccncc1.c1ccc2c(c1)CCN2C1CCNCC1>>c1ccc2c(c1)CCN2C1CCN(CCc2ccncc2)CC1 | N1CCC(CC1)N1CCC2=CC=CC=C12.C(=C)C1=CC=NC=C1>>N1=CC=C(C=C1)CCN1CCC(CC1)N1CCC2=CC=CC=C12 | [CH2:14]=[CH:15][c:16]1[cH:17][cH:18][n:19][cH:20][cH:21]1.[cH:1]1[cH:2][cH:3][c:4]2[c:5]([cH:6]1)[CH2:7][CH2:8][N:9]2[CH:10]1[CH2:11][CH2:12][NH:13][CH2:22][CH2:23]1>>[cH:1]1[cH:2][cH:3][c:4]2[c:5]([cH:6]1)[CH2:7][CH2:8][N:9]2[CH:10]1[CH2:11][CH2:12][N:13]([CH2:14][CH2:15][c:16]2[cH:17][cH:18][n:19][cH:20][cH:21]2)[CH... | C=Cc1ccncc1.c1ccc2c(c1)CCN2C1CCNCC1 | c1ccc2c(c1)CCN2C1CCN(CCc2ccncc2)CC1 | null | null | C(C)O | Heteroatom Alkylation and Arylation | aza-Michael addition secondary | d3e8cc768c824777b70742851768dcb27bf5f461c310912ac3f5a7abd08f6975 | 828fcbb87adfef9f22c9a1e52b43c3df76cb2e49bfe62b57e8b79965772a2bed | c1ccc2c(c1)CCN2C1CCN(CCc2ccncc2)CC1 | [CH2;D1;+0:1]=[CH;D2;+0:2]-[c:3]1:[c:4]:[c:5]:[#7;a:6]:[c:7]:[c:8]:1.[C:9]-[C:10]-[NH;D2;+0:11]-[C:12]-[C:13]>>[C:9]-[C:10]-[N;H0;D3;+0:11](-[CH2;D2;+0:1]-[CH2;D2;+0:2]-[c:3]1:[c:4]:[c:5]:[#7;a:6]:[c:7]:[c:8]:1)-[C:12]-[C:13] | 42.5 | [{"value": 42.5, "product": "N1=CC=C(C=C1)CCN1CCC(CC1)N1CCC2=CC=CC=C12", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | 1-(4-Piperidyl)indoline (0.1 g) was dissolved in ethanol (5 ml). After adding 4-vinylpyridine (0.16 ml), the resultant mixture was heated under reflux in a nitrogen atmosphere for 12 hr. Then the reaction solution was concentrated under reduced pressure and purified by silica gel column chromatography (toluene/acetone ... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amine.Vinyl | Tertiary amine | C1CCNCC1 | C1CC[NH]CC1 | c1ccc2c(c1)CC[NH]2.C1CC[NH]CC1.c1ccncc1 | null | C(C)O | null | null | C=Cc1ccncc1.c1ccc2c(c1)CCN2C1CCNCC1>C(C)O>c1ccc2c(c1)CCN2C1CCN(CCc2ccncc2)CC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-bb11cc6880ba4d5fa5d7545a818fa5e0 | N#Cc1ccc(CCN2CCC(N3CCc4ccccc43)CC2)cn1.[OH-]>>OCc1ccc(CCN2CCC(N3CCc4ccccc43)CC2)cn1 | [H-].C(C(C)C)[Al+]CC(C)C.[OH-].[Na+].S(O)(O)(=O)=O.C(#N)C1=NC=C(C=C1)CCN1CCC(CC1)N1CCC2=CC=CC=C12>>OCC1=NC=C(C=C1)CCN1CCC(CC1)N1CCC2=CC=CC=C12 | N#[C: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][cH:19][cH:20][c:21]43)[CH2:22][CH2:23]2)[cH:24][n:25]1.[OH-:1]>>[OH:1][CH2:2][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][cH:19][cH:... | N#Cc1ccc(CCN2CCC(N3CCc4ccccc43)CC2)cn1.[OH-] | OCc1ccc(CCN2CCC(N3CCc4ccccc43)CC2)cn1 | null | null | C1(=CC=CC=C1)C.C(C)OCC | Heteroatom Alkylation and Arylation | OtherReaction | de8451f7accf081f64d60bd8bcf02c61258886de72b58dc9936a5f7169bb9351 | eedcb470bce1034787f09ffbed71b4db95dde0db3dc2ac4fbd696e8c31768261 | c1cncc(CCN2CCC(N3CCc4ccccc43)CC2)c1 | N#[C;H0;D2;+0:1]-[c:2](:[c:3]):[#7;a:4]:[c:5].[OH-;D0:6]>>[OH;D1;+0:6]-[CH2;D2;+0:1]-[c:2](:[c:3]):[#7;a:4]:[c:5] | 64.5 | [{"value": 64.5, "product": "OCC1=NC=C(C=C1)CCN1CCC(CC1)N1CCC2=CC=CC=C12", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | 1-{1-[2-(2-Cyanopyridin-5-yl)ethyl]piperidin-4-yl}indoline (0.103 g) was dissolved in toluene (1.5 ml). In a nitrogen atmosphere at −78° C., a 1.5 M solution (0.44 ml) of diisobutylaluminum hydride in toluene was added thereto and the resultant mixture was stirred under the same conditions for 1 hr. Then the reaction s... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile | Primary alcohol | null | null | c1ccncc1.C1CC[NH]CC1.c1ccc2c(c1)CC[NH]2 | Other | C1(=CC=CC=C1)C.C(C)OCC | null | null | N#Cc1ccc(CCN2CCC(N3CCc4ccccc43)CC2)cn1.[OH-]>C1(=CC=CC=C1)C.C(C)OCC>OCc1ccc(CCN2CCC(N3CCc4ccccc43)CC2)cn1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-b76d243ab5e244ce93d72c604ae26413 | OCc1ccc(OCCCBr)cc1.c1ccc2c(c1)CCN2C1CCNCC1>>OCc1ccc(OCCCN2CCC(N3CCc4ccccc43)CC2)cc1 | N1CCC(CC1)N1CCC2=CC=CC=C12.BrCCCOC1=CC=C(CO)C=C1>>OCC1=CC=C(OCCCN2CCC(CC2)N2CCC3=CC=CC=C23)C=C1 | Br[CH2:10][CH2:9][CH2:8][O:7][c:6]1[cH:5][cH:4][c:3]([CH2:2][OH:1])[cH:27][cH:26]1.[NH:11]1[CH2:12][CH2:13][CH:14]([N:15]2[CH2:16][CH2:17][c:18]3[cH:19][cH:20][cH:21][cH:22][c:23]32)[CH2:24][CH2:25]1>>[OH:1][CH2:2][c:3]1[cH:4][cH:5][c:6]([O:7][CH2:8][CH2:9][CH2:10][N:11]2[CH2:12][CH2:13][CH:14]([N:15]3[CH2:16][CH2:17][... | OCc1ccc(OCCCBr)cc1.c1ccc2c(c1)CCN2C1CCNCC1 | OCc1ccc(OCCCN2CCC(N3CCc4ccccc43)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] | 92 | [{"value": 92.0, "product": "OCC1=CC=C(OCCCN2CCC(CC2)N2CCC3=CC=CC=C23)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 88.6, "product": "OCC1=CC=C(OCCCN2CCC(CC2)N2CCC3=CC=CC=C23)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 1-(4-Piperidyl)indoline (263 mg) and 4-(3-bromopropoxy)benzyl alcohol (389 mg) were treated as in Example 2 to give the title compound (422 mg) as a pale orange amorphous solid (yield: 92%).
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 | OCc1ccc(OCCCBr)cc1.c1ccc2c(c1)CCN2C1CCNCC1>>OCc1ccc(OCCCN2CCC(N3CCc4ccccc43)CC2)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-3c49fb2daed44571ab4925b6595dac42 | O=C(CCCCl)c1ccc(F)cc1.c1ccc2c(c1)CCN2C1CCNCC1>>O=C(CCCN1CCC(N2CCc3ccccc32)CC1)c1ccc(F)cc1 | N1CCC(CC1)N1CCC2=CC=CC=C12.ClCCCC(=O)C1=CC=C(C=C1)F>>FC1=CC=C(C=C1)C(CCCN1CCC(CC1)N1CCC2=CC=CC=C12)=O | Cl[CH2:5][CH2:4][CH2:3][C:2](=[O:1])[c:21]1[cH:22][cH:23][c:24]([F:25])[cH:26][cH:27]1.[NH:6]1[CH2:7][CH2:8][CH:9]([N:10]2[CH2:11][CH2:12][c:13]3[cH:14][cH:15][cH:16][cH:17][c:18]32)[CH2:19][CH2:20]1>>[O:1]=[C:2]([CH2:3][CH2:4][CH2:5][N:6]1[CH2:7][CH2:8][CH:9]([N:10]2[CH2:11][CH2:12][c:13]3[cH:14][cH:15][cH:16][cH:17][... | O=C(CCCCl)c1ccc(F)cc1.c1ccc2c(c1)CCN2C1CCNCC1 | O=C(CCCN1CCC(N2CCc3ccccc32)CC1)c1ccc(F)cc1 | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 0240b8450ff2c489d02f5f0d90bc953079d7a3ab239d35a03f26392fc248b4ef | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | O=C(CCCN1CCC(N2CCc3ccccc32)CC1)c1ccccc1 | Cl-[CH2;D2;+0:1]-[C:2]-[C:3]-[C:4]=[O;D1;H0:5].[C:6]-[C:7]-[NH;D2;+0:8]-[C:9]-[C:10]>>[C:6]-[C:7]-[N;H0;D3;+0:8](-[CH2;D2;+0:1]-[C:2]-[C:3]-[C:4]=[O;D1;H0:5])-[C:9]-[C:10] | 27.6 | [{"value": 27.0, "product": "FC1=CC=C(C=C1)C(CCCN1CCC(CC1)N1CCC2=CC=CC=C12)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 27.6, "product": "FC1=CC=C(C=C1)C(CCCN1CCC(CC1)N1CCC2=CC=CC=C12)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 1-(Piperidin-4-yl)indoline (1.0 g) and 4-chloro-1-(4-fluorophenyl)-1-butanone (1.1 g) were treated as in Example 2 to give the title compound (0.5 g) (yield: 27%).
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.c1ccc2c(c1)CC[NH]2.c1ccccc1 | HCl | null | null | null | O=C(CCCCl)c1ccc(F)cc1.c1ccc2c(c1)CCN2C1CCNCC1>>O=C(CCCN1CCC(N2CCc3ccccc32)CC1)c1ccc(F)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-d3ee222fd0f34ea4b9b1ada4fc613bdb | CCOC(=O)C1CN(Cc2ccccc2)CCC1=O.OCCO>>CCOC(=O)C1CN(Cc2ccccc2)CCC12OCCO2 | C(CO)O.C([O-])(O)=O.[Na+].O.C1(=CC=C(C=C1)S(=O)(=O)O)C.C(C1=CC=CC=C1)N1CC(C(CC1)=O)C(=O)OCC>>C(C1=CC=CC=C1)N1CC(C2(CC1)OCCO2)C(=O)OCC | [CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]1[CH2:7][N:8]([CH2:9][c:10]2[cH:11][cH:12][cH:13][cH:14][cH:15]2)[CH2:16][CH2:17][C:18]1=[O:19].O[CH2:20][CH2:21][OH:22]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]1[CH2:7][N:8]([CH2:9][c:10]2[cH:11][cH:12][cH:13][cH:14][cH:15]2)[CH2:16][CH2:17][C:18]12[O:19][CH2:20][CH2:21][O:22]2 | CCOC(=O)C1CN(Cc2ccccc2)CCC1=O.OCCO | CCOC(=O)C1CN(Cc2ccccc2)CCC12OCCO2 | null | null | C1(=CC=CC=C1)C | Heteroatom Alkylation and Arylation | OtherReaction | 8837aae4b2af99c66f81e15dbb86b5cc26349851d4056388a7d764086a8d3d5d | f8121a7732f8ef583111433d2b2d82886bf3a134c51dc6363d813c8cbf4e36f5 | c1ccc(CN2CCC3(CC2)OCCO3)cc1 | O-[CH2;D2;+0:1]-[C:2]-[OH;D1;+0:3].[C:4]-[#8:5]-[C:6](=[O;D1;H0:7])-[C:8]1-[C:9]-[#7:10]-[C:11]-[C:12]-[C;H0;D3;+0:13]-1=[O;H0;D1;+0:14]>>[C:4]-[#8:5]-[C:6](=[O;D1;H0:7])-[C:8]1-[C:9]-[#7:10]-[C:11]-[C:12]-[C;H0;D4;+0:13]-12-[O;H0;D2;+0:14]-[CH2;D2;+0:1]-[C:2]-[O;H0;D2;+0:3]-2 | 66 | [{"value": 66.0, "product": "C(C1=CC=CC=C1)N1CC(C2(CC1)OCCO2)C(=O)OCC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | p-Toluenesulfonic acid monohydrate (1.5 g) was added to a solution (600 ml) of ethyl 1-benzyl-4-oxo-3-piperidinecarboxylate (CAS Registry No. 1454-53-1, 44.7 g) and ethylene glycol (100 ml) in toluene and the resultant mixture was heated under reflux overnight. After cooling the mixture to room temperature, ice water (... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Primary alcohol.Primary alcohol | Ether.Ether | C1CC[NH]CC1 | C1CC2(CC[NH]1)OCCO2 | c1ccccc1.C1CC2(CC[NH]1)OCCO2 | HO- | C1(=CC=CC=C1)C | null | null | CCOC(=O)C1CN(Cc2ccccc2)CCC1=O.OCCO>C1(=CC=CC=C1)C>CCOC(=O)C1CN(Cc2ccccc2)CCC12OCCO2 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-5bf9346edb7047869aa6abab44bb6ed5 | CC(=O)OC[C@@H]1CNCC[C@@H]1N1CCc2ccccc21.Fc1ccc(CCBr)cc1>>CC(=O)OC[C@@H]1CN(CCc2ccc(F)cc2)CC[C@@H]1N1CCc2ccccc21 | C(C)(=O)OC[C@@H]1CNCC[C@@H]1N1CCC2=CC=CC=C12.O.C(C)N(CC)CC.FC1=CC=C(CCBr)C=C1>>FC1=CC=C(CCN2C[C@H]([C@H](CC2)N2CCC3=CC=CC=C23)COC(C)=O)C=C1 | [CH3:1][C:2](=[O:3])[O:4][CH2:5][C@@H:6]1[CH2:7][NH:8][CH2:18][CH2:19][C@@H:20]1[N:21]1[CH2:22][CH2:23][c:24]2[cH:25][cH:26][cH:27][cH:28][c:29]21.Br[CH2:9][CH2:10][c:11]1[cH:12][cH:13][c:14]([F:15])[cH:16][cH:17]1>>[CH3:1][C:2](=[O:3])[O:4][CH2:5][C@@H:6]1[CH2:7][N:8]([CH2:9][CH2:10][c:11]2[cH:12][cH:13][c:14]([F:15])... | CC(=O)OC[C@@H]1CNCC[C@@H]1N1CCc2ccccc21.Fc1ccc(CCBr)cc1 | CC(=O)OC[C@@H]1CN(CCc2ccc(F)cc2)CC[C@@H]1N1CCc2ccccc21 | null | null | CN(C=O)C.CO | 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] | 28 | [{"value": 28.0, "product": "FC1=CC=C(CCN2C[C@H]([C@H](CC2)N2CCC3=CC=CC=C23)COC(C)=O)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 24.7, "product": "FC1=CC=C(CCN2C[C@H]([C@H](CC2)N2CCC3=CC=CC=C23)COC(C)=O)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 50 | CELSIUS | 2 | HOUR | cis-1-(3-Acetoxymethylpiperidin-4-yl)indoline (280 mg) was dissolved in dimethylformamide (4 ml) and methanol (1 ml). To the resultant solution were added triethylamine (222 mg) and 4-fluorophenethyl bromide (285 mg) followed by stirring at 50° C. for 2 hr. Then the reaction mixture was cooled and water (50 ml) was add... | 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 | CN(C=O)C.CO | 50 | 2 | CC(=O)OC[C@@H]1CNCC[C@@H]1N1CCc2ccccc21.Fc1ccc(CCBr)cc1>CN(C=O)C.CO>CC(=O)OC[C@@H]1CN(CCc2ccc(F)cc2)CC[C@@H]1N1CCc2ccccc21 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-a6f9dfc9446d4a34ad9dc802fdee3ced | CCOC(=O)[C@@H]1CN(C(C)=O)CC[C@H]1N1CCc2ccccc21>>CC(=O)N1CC[C@@H](N2CCc3ccccc32)[C@H](CO)C1 | C(C)(=O)OCC.O.C(C)(=O)N1C[C@H]([C@@H](CC1)N1CCC2=CC=CC=C12)C(=O)OCC.[BH4-].[Na+].[BH4-].[Na+]>>C(C)(=O)N1C[C@H]([C@@H](CC1)N1CCC2=CC=CC=C12)CO | CCO[C:18]([C@H:17]1[C@H:7]([N:8]2[CH2:9][CH2:10][c:11]3[cH:12][cH:13][cH:14][cH:15][c:16]32)[CH2:6][CH2:5][N:4]([C:2]([CH3:1])=[O:3])[CH2:20]1)=[O:19]>>[CH3:1][C:2](=[O:3])[N:4]1[CH2:5][CH2:6][C@@H:7]([N:8]2[CH2:9][CH2:10][c:11]3[cH:12][cH:13][cH:14][cH:15][c:16]32)[C@H:17]([CH2:18][OH:19])[CH2:20]1 | CCOC(=O)[C@@H]1CN(C(C)=O)CC[C@H]1N1CCc2ccccc21 | CC(=O)N1CC[C@@H](N2CCc3ccccc32)[C@H](CO)C1 | null | null | C(C)O | Reduction | Reduction of ester to primary alcohol | 21d61543c6ec8a8cebe1b3ef55ef3dd20acbf79a4f1c12a7fb51e32be7a3248a | 1fbcd628a0426673c5d10aa49a977cd2d1ae02a8cdf57bbb10d94aa03a94e937 | c1ccc2c(c1)CCN2C1CCNCC1 | C-C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[C:3](-[C:4])-[C:5]-[#7:6]>>[#7:6]-[C:5]-[C:3](-[CH2;D2;+0:1]-[OH;D1;+0:2])-[C:4] | 39 | [{"value": 39.0, "product": "C(C)(=O)N1C[C@H]([C@@H](CC1)N1CCC2=CC=CC=C12)CO", "details": "PERCENTYIELD", "is_desired": false}, {"value": 37.0, "product": "C(C)(=O)N1C[C@H]([C@@H](CC1)N1CCC2=CC=CC=C12)CO", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | To a solution of trans-1-(1-acetyl-3-ethoxycarbonyl-piperidin-4-yl)indoline (780 mg) in ethanol (40 ml) was added sodium borohydride (5.7 g) in 3 portions at 30 min. intervals. After stirring at room temperature overnight, sodium borohydride (3.3 g) was added thereto and the resultant mixture was stirred for additional... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary alcohol | null | null | C1CC[NH]CC1.c1ccc2c(c1)CC[NH]2 | HO- | C(C)O | null | 8 | CCOC(=O)[C@@H]1CN(C(C)=O)CC[C@H]1N1CCc2ccccc21>C(C)O>CC(=O)N1CC[C@@H](N2CCc3ccccc32)[C@H](CO)C1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-7f1244c632724b3dab3c580dc4dc560a | CCN1CC[C@H](N2CCc3ccccc32)[C@H](CO)C1.Oc1ccc(F)cc1>>CCN1CC[C@H](N2CCc3ccccc32)[C@H](COc2ccc(F)cc2)C1 | FC1=CC=C(C=C1)O.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C(C)N1C[C@H]([C@H](CC1)N1CCC2=CC=CC=C12)CO.N(=NC(=O)OCC)C(=O)OCC>>C(C)N1C[C@H]([C@H](CC1)N1CCC2=CC=CC=C12)COC1=CC=C(C=C1)F | O[CH2:17][C@H:16]1[C@@H:6]([N:7]2[CH2:8][CH2:9][c:10]3[cH:11][cH:12][cH:13][cH:14][c:15]32)[CH2:5][CH2:4][N:3]([CH2:2][CH3:1])[CH2:26]1.[OH:18][c:19]1[cH:20][cH:21][c:22]([F:23])[cH:24][cH:25]1>>[CH3:1][CH2:2][N:3]1[CH2:4][CH2:5][C@H:6]([N:7]2[CH2:8][CH2:9][c:10]3[cH:11][cH:12][cH:13][cH:14][c:15]32)[C@H:16]([CH2:17][O... | CCN1CC[C@H](N2CCc3ccccc32)[C@H](CO)C1.Oc1ccc(F)cc1 | CCN1CC[C@H](N2CCc3ccccc32)[C@H](COc2ccc(F)cc2)C1 | null | null | O1CCCC1.O | Heteroatom Alkylation and Arylation | Mitsunobu aryl ether | 86bfb73617450d22f9456ed5ce4d96a73f1f8fc0c016bebae57fda68e2da86a2 | 2258bd14c3b5449b92dc09cf9fa522f88d5071b4af20f7e968b60aa1ae6db0cf | c1ccc(OC[C@@H]2CNCC[C@@H]2N2CCc3ccccc32)cc1 | O-[CH2;D2;+0:1]-[C:2](-[C:3])-[C:4]-[#7:5].[OH;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[#7:5]-[C:4]-[C:2](-[CH2;D2;+0:1]-[O;H0;D2;+0:6]-[c:7](:[c:8]):[c:9])-[C:3] | 25 | [{"value": 25.0, "product": "C(C)N1C[C@H]([C@H](CC1)N1CCC2=CC=CC=C12)COC1=CC=C(C=C1)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 24.5, "product": "C(C)N1C[C@H]([C@H](CC1)N1CCC2=CC=CC=C12)COC1=CC=C(C=C1)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | Under a nitrogen gas stream, 4-fluorophenol (168 mg) and triphenyiphosphine (420 mg) were added to a solution of cis-1-(1-ethyl-3-hydroxymethylpiperidin-4-yl)indoline (300 mg) in tetrahydrofuran (4 ml). After cooling the resultant mixture to −10° C., diethyl azodicarboxylate (278 mg) was gradually added dropwise therei... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Aromatic alcohol | Ether | null | null | C1CC[NH]CC1.c1ccc2c(c1)CC[NH]2.c1ccccc1 | HO- | O1CCCC1.O | null | 8 | CCN1CC[C@H](N2CCc3ccccc32)[C@H](CO)C1.Oc1ccc(F)cc1>O1CCCC1.O>CCN1CC[C@H](N2CCc3ccccc32)[C@H](COc2ccc(F)cc2)C1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-bdc10942f9644763a2671ea8333cb2cf | CCOC(=O)C1CN(Cc2ccccc2)CCC1=O>>CCOC(=O)C1CNCCC1=O | Cl.C(C1=CC=CC=C1)N1CC(C(CC1)=O)C(=O)OCC>>Cl.O=C1C(CNCC1)C(=O)OCC | c1ccc(C[N:8]2[CH2:7][CH:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[C:11](=[O:12])[CH2:10][CH2:9]2)cc1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]1[CH2:7][NH:8][CH2:9][CH2:10][C:11]1=[O:12] | CCOC(=O)C1CN(Cc2ccccc2)CCC1=O | CCOC(=O)C1CNCCC1=O | null | [Pd] | CO | Deprotection | Hydrogenolysis of tertiary amines | cd3c1aa319cad45f383f17cc0b8bfc8337d7078d779f654933f9a447e64292a5 | 1c99dd446c0bf4ae872cd8df8de34955be195747c234e9f3c49f46d1de614f66 | O=C1CCNCC1 | [#8:1]-[C:2](=[O;D1;H0:3])-[C:4]1-[C:5]-[N;H0;D3;+0:6](-C-c2:c:c:c:c:c:2)-[C:7]-[C:8]-[C:9]-1=[O;D1;H0:10]>>[#8:1]-[C:2](=[O;D1;H0:3])-[C:4]1-[C:5]-[NH;D2;+0:6]-[C:7]-[C:8]-[C:9]-1=[O;D1;H0:10] | 97 | [{"value": 97.0, "product": "Cl.O=C1C(CNCC1)C(=O)OCC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 95.6, "product": "Cl.O=C1C(CNCC1)C(=O)OCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 10% palladium/active carbon (2 g) was added to a solution of ethyl 1-benzyl-4-oxo-3-piperidinecarboxylate hydrochloride (30 g) in methanol (500 ml) and the resultant mixture was stirred at room temperature under hydrogen atmosphere for a day. After filtering the reaction mixture through celite, the filtrate was concent... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amine | Secondary amine | c1ccccc1.C1CC[NH]CC1 | C1CCNCC1 | C1CCNCC1 | Other | [Pd].CO | null | null | CCOC(=O)C1CN(Cc2ccccc2)CCC1=O>[Pd].CO>CCOC(=O)C1CNCCC1=O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-feb2337b8d0f47378f7cf0a77a12479f | CCOC(=O)C1CN(C(C)=O)CCC1=O.c1ccc2c(c1)CCN2>>CCOC(=O)[C@@H]1CN(C(C)=O)CC[C@@H]1N1CCc2ccccc21 | N1CCC2=CC=CC=C12.C(C)(=O)N1CC(C(CC1)=O)C(=O)OCC>>C(C)(=O)N1C[C@H]([C@H](CC1)N1CCC2=CC=CC=C12)C(=O)OCC | O=[C:14]1[CH:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[CH2:7][N:8]([C:9]([CH3:10])=[O:11])[CH2:12][CH2:13]1.[NH:15]1[CH2:16][CH2:17][c:18]2[cH:19][cH:20][cH:21][cH:22][c:23]21>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[C@@H:6]1[CH2:7][N:8]([C:9]([CH3:10])=[O:11])[CH2:12][CH2:13][C@@H:14]1[N:15]1[CH2:16][CH2:17][c:18]2[cH:19][cH:20][... | CCOC(=O)C1CN(C(C)=O)CCC1=O.c1ccc2c(c1)CCN2 | CCOC(=O)[C@@H]1CN(C(C)=O)CC[C@@H]1N1CCc2ccccc21 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | ed5f829465aab8e8fa321fc868dfe3231b2d42ce59513bacd6302db66ad15586 | 99acf13bfcfe579f51ccb82c65e4ca039ee7ca9b6fcd2747a3d9a292a88e564e | c1ccc2c(c1)CCN2C1CCNCC1 | O=[C;H0;D3;+0:1]1-[C:2]-[C:3]-[#7:4](-[C:5](-[C;D1;H3:6])=[O;D1;H0:7])-[C:8]-[CH;D3;+0:9]-1-[C:10](=[O;D1;H0:11])-[#8:12]-[C:13].[c:14]:[c:15]1:[c:16]-[C:17]-[C:18]-[NH;D2;+0:19]-1>>[C:13]-[#8:12]-[C:10](=[O;D1;H0:11])-[C@@H;D3;+0:9]1-[C:8]-[#7:4](-[C:5](-[C;D1;H3:6])=[O;D1;H0:7])-[C:3]-[C:2]-[C@@H;D3;+0:1]-1-[N;H0;D3;... | 22 | [{"value": 22.0, "product": "C(C)(=O)N1C[C@H]([C@H](CC1)N1CCC2=CC=CC=C12)C(=O)OCC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 21.5, "product": "C(C)(=O)N1C[C@H]([C@H](CC1)N1CCC2=CC=CC=C12)C(=O)OCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Indoline (12.5 g), ethyl 1-acetyl-4-oxo-3-piperidinecarboxylate (22.3 g) and triacetoxylated sodium borohydride (48.7 g) were treated as in Example 1 to give the title compound (7.12 g) as a pale yellow powder (yield: 22%).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Secondary amine | Tertiary amine | C1CC[NH]CC1.c1ccc2c(c1)CCN2 | C1CC[NH]CC1.c1ccc2c(c1)CC[NH]2 | C1CC[NH]CC1.c1ccc2c(c1)CC[NH]2 | Other | null | null | null | CCOC(=O)C1CN(C(C)=O)CCC1=O.c1ccc2c(c1)CCN2>>CCOC(=O)[C@@H]1CN(C(C)=O)CC[C@@H]1N1CCc2ccccc21 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-85ab805df84f412a9fe3c4095e8a3069 | CCOC(=O)[C@@H]1CN(C(C)=O)CC[C@H]1N1CCc2ccccc21>>CCN1CC[C@@H](N2CCc3ccccc32)[C@H](CO)C1 | C(C)(=O)N1C[C@H]([C@@H](CC1)N1CCC2=CC=CC=C12)C(=O)OCC.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+].O>>C(C)N1C[C@H]([C@@H](CC1)N1CCC2=CC=CC=C12)CO | CCO[C:17]([C@H:16]1[C@H:6]([N:7]2[CH2:8][CH2:9][c:10]3[cH:11][cH:12][cH:13][cH:14][c:15]32)[CH2:5][CH2:4][N:3]([C:2](=O)[CH3:1])[CH2:19]1)=[O:18]>>[CH3:1][CH2:2][N:3]1[CH2:4][CH2:5][C@@H:6]([N:7]2[CH2:8][CH2:9][c:10]3[cH:11][cH:12][cH:13][cH:14][c:15]32)[C@H:16]([CH2:17][OH:18])[CH2:19]1 | CCOC(=O)[C@@H]1CN(C(C)=O)CC[C@H]1N1CCc2ccccc21 | CCN1CC[C@@H](N2CCc3ccccc32)[C@H](CO)C1 | null | null | O1CCCC1.C(C)(=O)OCC | Reduction | OtherReaction | c69e55c870fca7a48716cf1a13d3b1c66b1429a862fb2c663e47b4c648179c46 | a65143cb02ef97811e30a8153880ab0c649a356c31e2df2bd3a78b2a9b48cbfc | c1ccc2c(c1)CCN2C1CCNCC1 | C-C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[C:3](-[C:4])-[C:5]-[#7:6](-[C;H0;D3;+0:7](=O)-[C;D1;H3:8])-[C:9]>>[C:9]-[#7:6](-[CH2;D2;+0:7]-[C;D1;H3:8])-[C:5]-[C:3](-[CH2;D2;+0:1]-[OH;D1;+0:2])-[C:4] | 49 | [{"value": 49.0, "product": "C(C)N1C[C@H]([C@@H](CC1)N1CCC2=CC=CC=C12)CO", "details": "PERCENTYIELD", "is_desired": false}, {"value": 48.6, "product": "C(C)N1C[C@H]([C@@H](CC1)N1CCC2=CC=CC=C12)CO", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 8 | HOUR | In a stream of nitrogen, lithium aluminum hydride (133 mg) was carefully added to dry tetrahydrofuran (5 ml) under ice cooling. To the resultant mixture was gradually added a solution of trans-1-(1-acetyl-3-ethoxycarbonylpiperidin-4-yl)indoline (850 mg) in dry tetrahydrofuran (5 ml) and the resulting mixture was stirre... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Tertiary amide | Primary alcohol | null | null | C1CC[NH]CC1.c1ccc2c(c1)CC[NH]2 | Other | O1CCCC1.C(C)(=O)OCC | 0 | 8 | CCOC(=O)[C@@H]1CN(C(C)=O)CC[C@H]1N1CCc2ccccc21>O1CCCC1.C(C)(=O)OCC>CCN1CC[C@@H](N2CCc3ccccc32)[C@H](CO)C1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-ccb9223705f34e2f950d70ce02420337 | CC(=O)N1CCC(=O)CC1.c1ccc2c(c1)CCN2>>CC(=O)N1CCC(N2CCc3ccccc32)CC1 | N1CCC2=CC=CC=C12.C(C)(=O)N1CCC(CC1)=O.C(C)(=O)O>>C(C)(=O)N1CCC(CC1)N1CCC2=CC=CC=C12 | O=[C:7]1[CH2:6][CH2:5][N:4]([C:2]([CH3:1])=[O:3])[CH2:18][CH2:17]1.[NH:8]1[CH2:9][CH2:10][c:11]2[cH:12][cH:13][cH:14][cH:15][c:16]21>>[CH3:1][C:2](=[O:3])[N:4]1[CH2:5][CH2:6][CH:7]([N:8]2[CH2:9][CH2:10][c:11]3[cH:12][cH:13][cH:14][cH:15][c:16]32)[CH2:17][CH2:18]1 | CC(=O)N1CCC(=O)CC1.c1ccc2c(c1)CCN2 | CC(=O)N1CCC(N2CCc3ccccc32)CC1 | null | [C].[Pd] | CO | Heteroatom Alkylation and Arylation | OtherReaction | ed5f829465aab8e8fa321fc868dfe3231b2d42ce59513bacd6302db66ad15586 | 99acf13bfcfe579f51ccb82c65e4ca039ee7ca9b6fcd2747a3d9a292a88e564e | c1ccc2c(c1)CCN2C1CCNCC1 | 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 | 82.2 | [{"value": 82.2, "product": "C(C)(=O)N1CCC(CC1)N1CCC2=CC=CC=C12", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Indoline (25 ml), 1-acetyl-4-piperidone (25 g) and glacial acetic acid (20 ml) were dissolved in methanol (300 ml). After adding 10% palladium carbon (1.0 g) thereto, catalytic reduction was carried out under atmospheric pressure. After the completion of the reaction, the reaction solution was filtered through celite, ... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Secondary amine | Tertiary amine | C1CC[NH]CC1.c1ccc2c(c1)CCN2 | C1CC[NH]CC1.c1ccc2c(c1)CC[NH]2 | C1CC[NH]CC1.c1ccc2c(c1)CC[NH]2 | Other | [C].[Pd].CO | null | null | CC(=O)N1CCC(=O)CC1.c1ccc2c(c1)CCN2>[C].[Pd].CO>CC(=O)N1CCC(N2CCc3ccccc32)CC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-2a3e382943c5490cadfd94645bfca5a0 | Brc1ccc2c(c1)NCC2.CC(C)(C)OC(=O)N1CCC(=O)CC1>>CC(C)(C)OC(=O)N1CCC(N2CCc3ccc(Br)cc32)CC1 | ClC(C)Cl.BrC1=CC=C2CCNC2=C1.C(C)(C)(C)OC(=O)N1CCC(CC1)=O>>C(C)(C)(C)OC(=O)N1CCC(CC1)N1CCC2=CC=C(C=C12)Br | [NH:12]1[CH2:13][CH2:14][c:15]2[cH:16][cH:17][c:18]([Br:19])[cH:20][c:21]21.O=[C:11]1[CH2:10][CH2:9][N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:23][CH2:22]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N: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:... | Brc1ccc2c(c1)NCC2.CC(C)(C)OC(=O)N1CCC(=O)CC1 | CC(C)(C)OC(=O)N1CCC(N2CCc3ccc(Br)cc32)CC1 | null | null | C(C)(=O)O | Heteroatom Alkylation and Arylation | OtherReaction | ed5f829465aab8e8fa321fc868dfe3231b2d42ce59513bacd6302db66ad15586 | 99acf13bfcfe579f51ccb82c65e4ca039ee7ca9b6fcd2747a3d9a292a88e564e | c1ccc2c(c1)CCN2C1CCNCC1 | 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 | 64 | [{"value": 64.0, "product": "C(C)(C)(C)OC(=O)N1CCC(CC1)N1CCC2=CC=C(C=C12)Br", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | Triacetoxylated sodium borohydride (11.7 g) was added to a mixture of 6- bromoindoline (8.3 g), 1-(t-butoxycarbonyl)-4-piperidone (10 g, [CAS Registry No. 7909-07-3]), acetic acid (14.9 g) and dichloroethane (200 ml) followed by stirring overnight. Then the reaction solution was concentrated under reduced pressure, and... | 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.c1ccc2c(c1)CC[NH]2 | Other | C(C)(=O)O | null | 8 | Brc1ccc2c(c1)NCC2.CC(C)(C)OC(=O)N1CCC(=O)CC1>C(C)(=O)O>CC(C)(C)OC(=O)N1CCC(N2CCc3ccc(Br)cc32)CC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-7d9016fa0d5b4078bf455b179cad85f1 | CC(C)(C)OC(=O)N1CCC(N2CCc3ccc(Br)cc32)CC1.CN(C)C=O>>CC(C)(C)OC(=O)N1CCC(N2CCc3ccc(CO)cc32)CC1 | CN(C=O)C.C(CCC)[Li].C(C)(C)(C)OC(=O)N1CCC(CC1)N1CCC2=CC=C(C=C12)Br.[Cl-].[NH4+]>>C(C)(C)(C)OC(=O)N1CCC(CC1)N1CCC2=CC=C(C=C12)CO | Br[c:18]1[cH:17][cH:16][c:15]2[c:22]([cH:21]1)[N:12]([CH:11]1[CH2:10][CH2:9][N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:24][CH2:23]1)[CH2:13][CH2:14]2.CN(C)[CH:19]=[O:20]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][CH:11]([N:12]2[CH2:13][CH2:14][c:15]3[cH:16][cH:17][c:18]([CH2... | CC(C)(C)OC(=O)N1CCC(N2CCc3ccc(Br)cc32)CC1.CN(C)C=O | CC(C)(C)OC(=O)N1CCC(N2CCc3ccc(CO)cc32)CC1 | null | null | O1CCCC1.CCCCCC.C(C)(=O)OCC | C-C Coupling | OtherReaction | a566eec5596c9d667a6958558ee72eeb1b632cb6f31de3019d9e5d0a3a12f7c7 | 970d2c669f12a11dd05b27d160ae86c4d1d2ef9cf45eec6ba4632daedfc92cdb | c1ccc2c(c1)CCN2C1CCNCC1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5]-[#7:6].C-N(-C)-[CH;D2;+0:7]=[O;H0;D1;+0:8]>>[#7:6]-[c:5]:[c:4]:[c;H0;D3;+0:1](-[CH2;D2;+0:7]-[OH;D1;+0:8]):[c:2]:[c:3] | 91 | [{"value": 91.0, "product": "C(C)(C)(C)OC(=O)N1CCC(CC1)N1CCC2=CC=C(C=C12)CO", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A 2.5 M solution (16 ml) of n-butyllithium in hexane was added dropwise at ±78° C. into a solution of 1-[1-(t-butoxycarbonyl)piperidin-4-yl]-6-bromoindoline (10 g) in tetrahydrofuran (250 ml) over 5 mm. After 10 mm, dimethylformamide (3.0 ml) was added and the resultant mixture was allowed to warm to room temperature. ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Tertiary amide | Primary alcohol | c1ccc2c(c1)CC[NH]2 | c1ccc2c(c1)CC[NH]2 | C1CC[NH]CC1.c1ccc2c(c1)CC[NH]2 | HBr | O1CCCC1.CCCCCC.C(C)(=O)OCC | null | null | CC(C)(C)OC(=O)N1CCC(N2CCc3ccc(Br)cc32)CC1.CN(C)C=O>O1CCCC1.CCCCCC.C(C)(=O)OCC>CC(C)(C)OC(=O)N1CCC(N2CCc3ccc(CO)cc32)CC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-f74630e205be4e358ba34415d369db12 | CC(C)(C)OC(=O)N1CCC(N2CCc3ccc(CO)cc32)CC1.O=C1NC(=O)c2ccccc21>>CC(C)(C)OC(=O)N1CCC(N2CCc3ccc(CN)cc32)CC1 | N(=NC(=O)OCC)C(=O)OCC.C(C)(C)(C)OC(=O)N1CCC(CC1)N1CCC2=CC=C(C=C12)CO.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(C=2C(C(N1)=O)=CC=CC2)=O>>C(C)(C)(C)OC(=O)N1CCC(CC1)N1CCC2=CC=C(C=C12)CN | O[CH2:19][c:18]1[cH:17][cH:16][c:15]2[c:22]([cH:21]1)[N:12]([CH:11]1[CH2:10][CH2:9][N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:24][CH2:23]1)[CH2:13][CH2:14]2.O=C1c2ccccc2C(=O)[NH:20]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][CH:11]([N:12]2[CH2:13][CH2:14][c:15]3[cH:16][cH:1... | CC(C)(C)OC(=O)N1CCC(N2CCc3ccc(CO)cc32)CC1.O=C1NC(=O)c2ccccc21 | CC(C)(C)OC(=O)N1CCC(N2CCc3ccc(CN)cc32)CC1 | null | null | O1CCCC1 | Heteroatom Alkylation and Arylation | OtherReaction | 01a9fc9e46a0f4b1dde1c9fae31d864cb253836f6f5b51c8c8f29d6f5c731156 | 6579eb1fe34d0c886a93f8997f9204f864cfc5defef576f26b88aabe6eddf99c | c1ccc2c(c1)CCN2C1CCNCC1 | O-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].O=C1-[NH;D2;+0:5]-C(=O)-c2:c:c:c:c:c:2-1>>[NH2;D1;+0:5]-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4] | 105.4 | [{"value": 105.4, "product": "C(C)(C)(C)OC(=O)N1CCC(CC1)N1CCC2=CC=C(C=C12)CN", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Under ice cooling, a solution of diethyl azodicarboxylate (4.6 g) in tetrahydrofuran (20 ml) was added dropwise into a solution of 1-[1-(t-butoxycarbonyl)piperidin-4-yl]-6-hydroxymethylindoline (7.9 g), triphenylphosphine (6.9 g) and phthalimide (3.9 g) in tetrahydrofuran (250 ml) and the resultant mixture was stirred ... | 10.6084/m9.figshare.5104873.v1 | null | Unsubstituted dicarboximide.Primary alcohol | Primary amine | c1ccc2c(c1)CNC2 | null | C1CC[NH]CC1.c1ccc2c(c1)CC[NH]2 | HO- | O1CCCC1 | null | null | CC(C)(C)OC(=O)N1CCC(N2CCc3ccc(CO)cc32)CC1.O=C1NC(=O)c2ccccc21>O1CCCC1>CC(C)(C)OC(=O)N1CCC(N2CCc3ccc(CN)cc32)CC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-cfd9ed927294493280549e069f5a78b4 | CC(=O)NCc1ccc2c(c1)N(C1CCNCC1)CC2.COc1ccc(CCBr)cc1>>COc1ccc(CCN2CCC(N3CCc4ccc(CNC(C)=O)cc43)CC2)cc1 | N1CCC(CC1)N1CCC2=CC=C(C=C12)CNC(C)=O.COC1=CC=C(CCBr)C=C1>>COC1=CC=C(CCN2CCC(CC2)N2CCC3=CC=C(C=C23)CNC(C)=O)C=C1 | [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]([CH2:20][NH:21][C:22]([CH3:23])=[O:24])[cH:25][c:26]32)[CH2:27][CH2:28]1.Br[CH2:8][CH2:7][c:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:30][cH:29]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]... | CC(=O)NCc1ccc2c(c1)N(C1CCNCC1)CC2.COc1ccc(CCBr)cc1 | COc1ccc(CCN2CCC(N3CCc4ccc(CNC(C)=O)cc43)CC2)cc1 | 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] | 53.7 | [{"value": 53.0, "product": "COC1=CC=C(CCN2CCC(CC2)N2CCC3=CC=C(C=C23)CNC(C)=O)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 53.7, "product": "COC1=CC=C(CCN2CCC(CC2)N2CCC3=CC=C(C=C23)CNC(C)=O)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 1-(Piperidin-4-yl)-6-acetamidomethylindoline (250 mg) and 4-methoxyphenethyl bromide (240 mg) were treated as in Example 2 to give the title compound (200 mg) as a white powder (yield: 53%).
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 | CC(=O)NCc1ccc2c(c1)N(C1CCNCC1)CC2.COc1ccc(CCBr)cc1>>COc1ccc(CCN2CCC(N3CCc4ccc(CNC(C)=O)cc43)CC2)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-2572e495efd94b7a846d1b4132a3a55c | CC(=O)NCc1ccc2c(c1)N(C1CCNCC1)CC2.Clc1ccc(CCBr)cc1>>CC(=O)NCc1ccc2c(c1)N(C1CCN(CCc3ccc(Cl)cc3)CC1)CC2 | N1CCC(CC1)N1CCC2=CC=C(C=C12)CNC(C)=O.ClC1=CC=C(CCBr)C=C1>>ClC1=CC=C(CCN2CCC(CC2)N2CCC3=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:10]([cH:11]1)[N:12]([CH:13]1[CH2:14][CH2:15][NH:16][CH2:26][CH2:27]1)[CH2:28][CH2:29]2.Br[CH2:17][CH2:18][c:19]1[cH:20][cH:21][c:22]([Cl:23])[cH:24][cH:25]1>>[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:13]1[CH2:14][CH2:1... | CC(=O)NCc1ccc2c(c1)N(C1CCNCC1)CC2.Clc1ccc(CCBr)cc1 | CC(=O)NCc1ccc2c(c1)N(C1CCN(CCc3ccc(Cl)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] | 63.7 | [{"value": 63.7, "product": "ClC1=CC=C(CCN2CCC(CC2)N2CCC3=CC=C(C=C23)CNC(C)=O)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}, {"value": 63.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | 1-(Piperidin-4-yl)-6-acetamidomethylindoline (250 mg) and 4-chlorophenethyl bromide (240 mg) were treated as in Example 2 to give the title compound (240 mg) as white scaly crystals (yield: 63%).
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 | CC(=O)NCc1ccc2c(c1)N(C1CCNCC1)CC2.Clc1ccc(CCBr)cc1>>CC(=O)NCc1ccc2c(c1)N(C1CCN(CCc3ccc(Cl)cc3)CC1)CC2 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-1e67596720d74f23a89845765389e7b4 | O=C1C(=O)N(C2CCN(CCc3ccc(F)cc3)CC2)c2cc(Br)ccc21>>Fc1ccc(CCN2CCC(Nc3cccc(Br)c3)CC2)cc1 | FC1=CC=C(CCN2CCC(CC2)N2C(C(C3=CC=C(C=C23)Br)=O)=O)C=C1.C(C)(=O)OCC.C([O-])(O)=O.[Na+]>>FC1=CC=C(CCN2CCC(CC2)NC2=CC(=CC=C2)Br)C=C1 | O=C1C(=O)[c:14]2[c:13]([cH:19][c:17]([Br:18])[cH:16][cH:15]2)[N:12]1[CH:11]1[CH2:10][CH2:9][N:8]([CH2:7][CH2:6][c:5]2[cH:4][cH:3][c:2]([F:1])[cH:23][cH:22]2)[CH2:21][CH2:20]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]([NH:12][c:13]3[cH:14][cH:15][cH:16][c:17]([Br:18])[cH:19]3)[CH2:20][CH2:... | O=C1C(=O)N(C2CCN(CCc3ccc(F)cc3)CC2)c2cc(Br)ccc21 | Fc1ccc(CCN2CCC(Nc3cccc(Br)c3)CC2)cc1 | null | null | O1CCCC1 | Reduction | OtherReaction | b9c8320677b34658dd8572519ee4c194caff359ad11fda4a89bb2f58ba9c2076 | a015d11427a53681cda20e7b24639c6813016c95c68c508a68a86bf2eacf68b9 | c1ccc(CCN2CCC(Nc3ccccc3)CC2)cc1 | O=C1-C(=O)-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](:[c:5])-[N;H0;D3;+0:6]-1-[C:7](-[C:8])-[C:9]>>[C:8]-[C:7](-[NH;D2;+0:6]-[c:4](:[c:5]):[cH;D2;+0:1]:[c:2]:[c:3])-[C:9] | 60.2 | [{"value": 57.0, "product": "FC1=CC=C(CCN2CCC(CC2)NC2=CC(=CC=C2)Br)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 60.2, "product": "FC1=CC=C(CCN2CCC(CC2)NC2=CC(=CC=C2)Br)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | Under ice cooling, a 1 M solution (69 ml) of a borane/tetrahydrofuran complex in tetrahydrofuran was added dropwise into a solution of 1-[1-(4-fluorophenethyl)-piperidin-4-yl]-2,3-dioxo-6-bromoindoline (7.4 g) in tetrahydrofuran (150 ml) followed by stirring at room temperature overnight and heating under reflux for 3 ... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Tertiary amide | Secondary amine | c1ccc2c(c1)CC[NH]2 | c1ccccc1 | c1ccccc1.C1CC[NH]CC1.c1ccccc1 | Other | O1CCCC1 | null | 8 | O=C1C(=O)N(C2CCN(CCc3ccc(F)cc3)CC2)c2cc(Br)ccc21>O1CCCC1>Fc1ccc(CCN2CCC(Nc3cccc(Br)c3)CC2)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-c939434da50a4458820aa9fba936657c | Fc1ccc(CCN2CCC(n3ccc4ccc(Br)cc43)CC2)cc1>>Fc1ccc(CCN2CCC(Nc3cccc(Br)c3)CC2)cc1 | FC1=CC=C(CCN2CCC(CC2)N2C=CC3=CC=C(C=C23)Br)C=C1.O>>FC1=CC=C(CCN2CCC(CC2)NC2=CC(=CC=C2)Br)C=C1 | c1c[c:14]2[c:13]([n:12]1[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:23][cH:22]3)[CH2:21][CH2:20]1)[cH:19][c:17]([Br:18])[cH:16][cH:15]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]([NH:12][c:13]3[cH:14][cH:15][cH:16][c:17]([Br:18])[cH:19]3)[CH2:20][CH2:21]2)[... | Fc1ccc(CCN2CCC(n3ccc4ccc(Br)cc43)CC2)cc1 | Fc1ccc(CCN2CCC(Nc3cccc(Br)c3)CC2)cc1 | null | null | O1CCCC1.FC(C(=O)O)(F)F | Miscellaneous | OtherReaction | 4920e2124f418bc362123ca4f7f50ea177f7cc060edca484b788b44801301525 | e3fff3959aaf1f1f768c1d470ac1a5edda16cd88af5e820de158d44d48f28485 | c1ccc(CCN2CCC(Nc3ccccc3)CC2)cc1 | [C:1]-[C:2](-[n;H0;D3;+0:3]1:c:c:[c;H0;D3;+0:4](:[c:5]:[c:6]):[c:7]:1:[c:8])-[C:9]>>[C:1]-[C:2](-[NH;D2;+0:3]-[c:7](:[c:8]):[cH;D2;+0:4]:[c:5]:[c:6])-[C:9] | 54.5 | [{"value": 51.0, "product": "FC1=CC=C(CCN2CCC(CC2)NC2=CC(=CC=C2)Br)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 54.5, "product": "FC1=CC=C(CCN2CCC(CC2)NC2=CC(=CC=C2)Br)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | Under ice cooling, a 1 M solution (20 ml) of a borane/tetrahydrofuran complex in tetrahydrofuran was added dropwise into a solution of 1-[1-(4-fluorophenethyl)-piperidin-4-yl]-6-bromoindole (3.9 g) in trifluoroacetic acid (50 ml) followed by stirring for 3 hr. After adding water thereto and concentrating under reduced ... | 10.6084/m9.figshare.5104873.v1 | null | null | Secondary amine | c1ccc2cc[nH]c2c1 | c1ccccc1 | c1ccccc1.C1CC[NH]CC1.c1ccccc1 | Other | O1CCCC1.FC(C(=O)O)(F)F | null | 3 | Fc1ccc(CCN2CCC(n3ccc4ccc(Br)cc43)CC2)cc1>O1CCCC1.FC(C(=O)O)(F)F>Fc1ccc(CCN2CCC(Nc3cccc(Br)c3)CC2)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-b859a7b4953a47449466d6cd502ab05c | Brc1ccc2c(c1)NCC2.O=C1CCN(CCc2ccc(F)cc2)CC1>>Fc1ccc(CCN2CCC(N3CCc4ccc(Br)cc43)CC2)cc1 | BrC1=CC=C2CCNC2=C1.FC1=CC=C(CCN2CCC(CC2)=O)C=C1.ClC(C)Cl>>FC1=CC=C(CCN2CCC(CC2)N2CCC3=CC=C(C=C23)Br)C=C1 | [NH:12]1[CH2:13][CH2:14][c:15]2[cH:16][cH:17][c:18]([Br:19])[cH:20][c:21]21.O=[C:11]1[CH2:10][CH2:9][N:8]([CH2:7][CH2:6][c:5]2[cH:4][cH:3][c:2]([F:1])[cH:25][cH:24]2)[CH2:23][CH2:22]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][CH2:14][c:15]4[cH:16][cH:17][c:18]([Br:19])[cH:... | Brc1ccc2c(c1)NCC2.O=C1CCN(CCc2ccc(F)cc2)CC1 | Fc1ccc(CCN2CCC(N3CCc4ccc(Br)cc43)CC2)cc1 | null | null | C(C)(=O)O | 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 | 58 | [{"value": 58.0, "product": "FC1=CC=C(CCN2CCC(CC2)N2CCC3=CC=C(C=C23)Br)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 58.0, "product": "FC1=CC=C(CCN2CCC(CC2)N2CCC3=CC=C(C=C23)Br)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | Triacetoxylated sodium borohydride (298 g) was added over 30 min to a mixture of 6-bromoindoline (175 g), 1-(4-fluorophenethyl)-4-piperidone (194 g), acetic acid (250 ml) and dichloroethane (2.5 l) followed by stirring 2 hr. Then the reaction solution was concentrated under reduced pressure, diluted with ethyl acetate ... | 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 | C(C)(=O)O | null | 2 | Brc1ccc2c(c1)NCC2.O=C1CCN(CCc2ccc(F)cc2)CC1>C(C)(=O)O>Fc1ccc(CCN2CCC(N3CCc4ccc(Br)cc43)CC2)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-e7d4cd65b46a418e97851547d9f306ea | COc1cccc(NC2CCN(Cc3ccccc3)CC2)c1.O=C(Cl)C(=O)Cl>>COc1ccc2c(c1)N(C1CCN(Cc3ccccc3)CC1)C(=O)C2=O | C([O-])(O)=O.[Na+].C(C1=CC=CC=C1)N1CCC(CC1)NC1=CC(=CC=C1)OC.C(C(=O)Cl)(=O)Cl>>C(C1=CC=CC=C1)N1CCC(CC1)N1C(C(C2=CC=C(C=C12)OC)=O)=O | [CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]([NH:9][CH:10]2[CH2:11][CH2:12][N:13]([CH2:14][c:15]3[cH:16][cH:17][cH:18][cH:19][cH:20]3)[CH2:21][CH2:22]2)[cH:8]1.Cl[C:23](=[O:24])[C:25](Cl)=[O:26]>>[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]3[cH:16][cH:17][cH:18][cH:... | COc1cccc(NC2CCN(Cc3ccccc3)CC2)c1.O=C(Cl)C(=O)Cl | COc1ccc2c(c1)N(C1CCN(Cc3ccccc3)CC1)C(=O)C2=O | null | null | CCOCC | C-C Coupling | OtherReaction | 6a10097f4225ba13178890c174513a7b86a4b892858a159598fe0b919b5b7f4c | 0af6e381714f2bbb9141db62725e8f568d93f0a4df11cc8f8187f633769f627c | O=C1C(=O)N(C2CCN(Cc3ccccc3)CC2)c2ccccc21 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C;H0;D3;+0:3](-Cl)=[O;D1;H0:4].[C:5]-[C:6](-[NH;D2;+0:7]-[c:8](:[c:9]):[cH;D2;+0:10]:[c:11]:[c:12])-[C:13]>>[C:5]-[C:6](-[N;H0;D3;+0:7]1-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C;H0;D3;+0:3](=[O;D1;H0:4])-[c;H0;D3;+0:10](:[c:11]:[c:12]):[c:8]-1:[c:9])-[C:13] | 73.3 | [{"value": 73.0, "product": "C(C1=CC=CC=C1)N1CCC(CC1)N1C(C(C2=CC=C(C=C12)OC)=O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 73.3, "product": "C(C1=CC=CC=C1)N1CCC(CC1)N1C(C(C2=CC=C(C=C12)OC)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1.5 | HOUR | 1-Benzyl-4-(3-methoxyphenyl)aminopiperidine (1.88 g) synthesized in accordance with the method of Referential Example 1 of JP-B 40-6347 was dissolved in ether (38 ml). Into the resultant solution was added dropwise oxalyl chlori de (1.62 g) over 30 min at room temperature followed by heating under reflux for 3.5 hr. Af... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Acyl halide.Secondary amine | Ketone.Tertiary amide | c1ccccc1 | c1ccc2c(c1)CC[NH]2 | C1CC[NH]CC1.c1ccccc1.c1ccc2c(c1)CC[NH]2 | HCl | CCOCC | null | 1.5 | COc1cccc(NC2CCN(Cc3ccccc3)CC2)c1.O=C(Cl)C(=O)Cl>CCOCC>COc1ccc2c(c1)N(C1CCN(Cc3ccccc3)CC1)C(=O)C2=O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-264b00879f70421db4e632e523b628a0 | COc1ccc2c(c1)N(C1CCN(Cc3ccccc3)CC1)C(=O)C2=O>>COc1ccc2ccn(C3CCN(Cc4ccccc4)CC3)c2c1 | C(C1=CC=CC=C1)N1CCC(CC1)N1C(C(C2=CC=C(C=C12)OC)=O)=O.C([O-])(O)=O.[Na+]>>C(C1=CC=CC=C1)N1CCC(CC1)N1C=CC2=CC=C(C=C12)OC | O=[C:7]1[c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:24][c:23]2[N:9]([CH:10]2[CH2:11][CH2:12][N:13]([CH2:14][c:15]3[cH:16][cH:17][cH:18][cH:19][cH:20]3)[CH2:21][CH2:22]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][N:13]([CH2:14][c:15]4[cH:16][cH:17][cH:18][cH:19][cH:20]4)[CH2:21... | COc1ccc2c(c1)N(C1CCN(Cc3ccccc3)CC1)C(=O)C2=O | COc1ccc2ccn(C3CCN(Cc4ccccc4)CC3)c2c1 | null | null | O1CCCC1 | Miscellaneous | OtherReaction | a84df4c7a05734d228fad41600e582f9472ec1c255198b83853f95abef8b9e31 | 859a0edf2382a200eae53621e7a1399268b892a729d9a6df2ea708544919156d | c1ccc(CN2CCC(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] | 28 | [{"value": 28.0, "product": "C(C1=CC=CC=C1)N1CCC(CC1)N1C=CC2=CC=C(C=C12)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 27.8, "product": "C(C1=CC=CC=C1)N1CCC(CC1)N1C=CC2=CC=C(C=C12)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | A 2 M solution (0.47 ml) of a diborane/dimethyl sulfide complex in tetrahydrofuran was added to a solution of 1-(1-benzylpiperidin-4-yl)-6-methoxyindoline-2,3-dione (110 mg) in tetrahydrofuran (2 ml) followed by stirring for 1 hr and then heating under reflux for 4.5 hr. After the completion of the reaction, an aqueous... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Tertiary amide | null | c1ccc2c(c1)CC[NH]2 | c1ccc2cc[nH]c2c1 | c1ccc2cc[nH]c2c1.C1CC[NH]CC1.c1ccccc1 | Other | O1CCCC1 | null | 1 | COc1ccc2c(c1)N(C1CCN(Cc3ccccc3)CC1)C(=O)C2=O>O1CCCC1>COc1ccc2ccn(C3CCN(Cc4ccccc4)CC3)c2c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-a3024f37927f46e597f945009b3e32ef | COc1ccc2ccn(C3CCN(CCc4ccc(F)cc4)CC3)c2c1>>COc1ccc2c(c1)NCC2 | FC1=CC=C(CCN2CCC(CC2)N2C=CC3=CC=C(C=C23)OC)C=C1.O>>COC1=CC=C2CCNC2=C1 | Fc1ccc(CCN2CCC([n:9]3[c:7]4[c:6]([cH:5][cH:4][c:3]([O:2][CH3:1])[cH:8]4)[cH:11][cH:10]3)CC2)cc1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([cH:8]1)[NH:9][CH2:10][CH2:11]2 | COc1ccc2ccn(C3CCN(CCc4ccc(F)cc4)CC3)c2c1 | COc1ccc2c(c1)NCC2 | null | null | FC(C(=O)O)(F)F | Deprotection | OtherReaction | d98c55e7aec242ac1a50cc6c7603625dcdf76ee23c114a48cbf5bb94a03bbd49 | 1c2495fab43afd53fc03b1098e2211ccfcbe4ad2bea8ca5d2b8fbd53e59ff1e2 | c1ccc2c(c1)CCN2 | F-c1:c:c:c(-C-C-N2-C-C-C(-[n;H0;D3;+0:1]3:[cH;D2;+0:2]:[cH;D2;+0:3]:[c:4](:[c:5]):[c:6]:3:[c:7])-C-C-2):c:c:1>>[c:5]:[c:4]1:[c:6](:[c:7])-[NH;D2;+0:1]-[CH2;D2;+0:2]-[CH2;D2;+0:3]-1 | 98.4 | [{"value": 35.0, "product": "COC1=CC=C2CCNC2=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 98.4, "product": "COC1=CC=C2CCNC2=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 30 | MINUTE | A 1 M solution (0.18 ml) of a borane/tetrahydrofuran complex was added dropwise at 0° C. into a solution of 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-methoxyindole (24 mg) in trifluoroacetic acid (1 ml) over 2 min followed by stirring at 0° C. for 30 min. Af ter the completion of the reaction, water (0.1 ml) was added ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Tertiary amine | Secondary amine | c1ccccc1.C1CCNCC1.c1ccc2cc[nH]c2c1 | c1ccc2c(c1)CCN2 | c1ccc2c(c1)CCN2 | HF | FC(C(=O)O)(F)F | 0 | 0.5 | COc1ccc2ccn(C3CCN(CCc4ccc(F)cc4)CC3)c2c1>FC(C(=O)O)(F)F>COc1ccc2c(c1)NCC2 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-8b3e73ec0c7140a8b321f36640b8abab | Fc1ccc(CCBr)cc1.O=[N+]([O-])c1ccc2c(c1)N(C1CCNCC1)CC2>>O=[N+]([O-])c1ccc2c(c1)N(C1CCN(CCc3ccc(F)cc3)CC1)CC2 | N1CCC(CC1)N1CCC2=CC=C(C=C12)[N+](=O)[O-].FC1=CC=C(CCBr)C=C1>>FC1=CC=C(CCN2CCC(CC2)N2CCC3=CC=C(C=C23)[N+](=O)[O-])C=C1 | Br[CH2:15][CH2:16][c:17]1[cH:18][cH:19][c:20]([F:21])[cH:22][cH:23]1.[O:1]=[N+:2]([O-: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][NH:14][CH2:24][CH2:25]1)[CH2:26][CH2:27]2>>[O:1]=[N+:2]([O-: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]... | Fc1ccc(CCBr)cc1.O=[N+]([O-])c1ccc2c(c1)N(C1CCNCC1)CC2 | O=[N+]([O-])c1ccc2c(c1)N(C1CCN(CCc3ccc(F)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] | 97.5 | [{"value": 81.0, "product": "FC1=CC=C(CCN2CCC(CC2)N2CCC3=CC=C(C=C23)[N+](=O)[O-])C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 97.5, "product": "FC1=CC=C(CCN2CCC(CC2)N2CCC3=CC=C(C=C23)[N+](=O)[O-])C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 1-(Piperidin-4-yl)-6-nitroindoline (3.5 g) and 4-fluorophenethyl bromide (4.1 g) were treated as in Example 2 to give the title compound (5.1 g) as apaleyellowpowder (yield: 81%).
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 | Fc1ccc(CCBr)cc1.O=[N+]([O-])c1ccc2c(c1)N(C1CCNCC1)CC2>>O=[N+]([O-])c1ccc2c(c1)N(C1CCN(CCc3ccc(F)cc3)CC1)CC2 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-381d0a18accf4c868236c3a8c20fa098 | CC(=O)OC(C)=O.Nc1ccc2c(c1)N(C1CCN(CCc3ccc(F)cc3)CC1)CC2>>CC(=O)Nc1ccc2c(c1)N(C1CCN(CCc3ccc(F)cc3)CC1)CC2 | FC1=CC=C(CCN2CCC(CC2)N2CCC3=CC=C(C=C23)N)C=C1.C(C)(=O)OC(C)=O>>FC1=CC=C(CCN2CCC(CC2)N2CCC3=CC=C(C=C23)NC(C)=O)C=C1 | CC(=O)O[C:2]([CH3:1])=[O:3].[NH2:4][c:5]1[cH:6][cH:7][c:8]2[c:9]([cH:10]1)[N:11]([CH:12]1[CH2:13][CH2:14][N:15]([CH2:16][CH2:17][c:18]3[cH:19][cH:20][c:21]([F:22])[cH:23][cH:24]3)[CH2:25][CH2:26]1)[CH2:27][CH2:28]2>>[CH3:1][C:2](=[O:3])[NH:4][c:5]1[cH:6][cH:7][c:8]2[c:9]([cH:10]1)[N:11]([CH:12]1[CH2:13][CH2:14][N:15]([... | CC(=O)OC(C)=O.Nc1ccc2c(c1)N(C1CCN(CCc3ccc(F)cc3)CC1)CC2 | CC(=O)Nc1ccc2c(c1)N(C1CCN(CCc3ccc(F)cc3)CC1)CC2 | null | null | null | Acylation | Aminolysis of esters | 87d35e51b477fc9a658a6f307eb56d84c8879182772c9dd3a42ec0d584fd2684 | 627cbc0550c9f51ad0105d9fcf46677e8c93bed87ee95bfe69292a82550c95b7 | c1ccc(CCN2CCC(N3CCc4ccccc43)CC2)cc1 | C-C(=O)-O-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[NH2;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[C;D1;H3:2]-[C;H0;D3;+0:1](=[O;D1;H0:3])-[NH;D2;+0:4]-[c:5](:[c:6]):[c:7] | 41 | [{"value": 41.0, "product": "FC1=CC=C(CCN2CCC(CC2)N2CCC3=CC=C(C=C23)NC(C)=O)C=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | 1-[1-(4-Fluorophenethyl)piperidin-4-yl]-6-aminoindoline (1.0 g) and acetic anhydride (1 ml) were treated as in Example 133 to give the title compound (450 mg) as a pale yellow powder (yield: 41%).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Primary amine | Secondary amide | null | null | C1CC[NH]CC1.c1ccccc1.c1ccc2c(c1)CC[NH]2 | HO- | null | null | null | CC(=O)OC(C)=O.Nc1ccc2c(c1)N(C1CCN(CCc3ccc(F)cc3)CC1)CC2>>CC(=O)Nc1ccc2c(c1)N(C1CCN(CCc3ccc(F)cc3)CC1)CC2 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-939df83e61034b7fb3378a75d1b9faaf | ON=Cc1ccc2c(c1)N(C1CCN(CCc3ccc(F)cc3)CC1)CC2>>N#Cc1ccc2c(c1)N(C1CCN(CCc3ccc(F)cc3)CC1)CC2 | C([O-])(O)=O.[Na+].FC(S(=O)(=O)OS(=O)(=O)C(F)(F)F)(F)F.FC1=CC=C(CCN2CCC(CC2)N2CCC3=CC=C(C=C23)C=NO)C=C1.C(C)N(CC)CC>>FC1=CC=C(CCN2CCC(CC2)N2CCC3=CC=C(C=C23)C#N)C=C1 | O[N: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>>[N:1]#[C: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... | ON=Cc1ccc2c(c1)N(C1CCN(CCc3ccc(F)cc3)CC1)CC2 | N#Cc1ccc2c(c1)N(C1CCN(CCc3ccc(F)cc3)CC1)CC2 | null | null | C(Cl)(Cl)Cl.C(Cl)Cl | Functional Group Interconversion | OtherReaction | 17f476cc256704e312f02cdb730538a4d2e78e129aaed9ef4aa555a9b052c890 | 9ad4e779dba60265752423413bc1b61ff9562539f91b24f3b3d9205e4bb46232 | c1ccc(CCN2CCC(N3CCc4ccccc43)CC2)cc1 | O-[N;H0;D2;+0:1]=[CH;D2;+0:2]-[c:3](:[c:4]):[c:5]>>[N;H0;D1;+0:1]#[C;H0;D2;+0:2]-[c:3](:[c:4]):[c:5] | 70.1 | [{"value": 67.0, "product": "FC1=CC=C(CCN2CCC(CC2)N2CCC3=CC=C(C=C23)C#N)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 70.1, "product": "FC1=CC=C(CCN2CCC(CC2)N2CCC3=CC=C(C=C23)C#N)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Trifluoromethanesulfonic anhydride (0.72 ml) was added dropwise at −78° C. into a solution of 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-hydroxyiminomethylindoline (1.5 g) and triethylamine (1.2 ml) in methylene chloride (1 l) and the resultant mixture was warmed to room temperature. Next, a saturated aqueous solution o... | 10.6084/m9.figshare.5104873.v1 | null | Oxime | Nitrile | null | null | C1CC[NH]CC1.c1ccccc1.c1ccc2c(c1)CC[NH]2 | HO- | C(Cl)(Cl)Cl.C(Cl)Cl | null | null | ON=Cc1ccc2c(c1)N(C1CCN(CCc3ccc(F)cc3)CC1)CC2>C(Cl)(Cl)Cl.C(Cl)Cl>N#Cc1ccc2c(c1)N(C1CCN(CCc3ccc(F)cc3)CC1)CC2 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-9fd986be4eff4eae98c09c670616dbc9 | CCOC(C)=O.N#Cc1ccc2c(c1)N(C1CCN(CCc3ccc(F)cc3)CC1)CC2>>NC(=O)c1ccc2c(c1)N(C1CCN(CCc3ccc(F)cc3)CC1)CC2 | FC1=CC=C(CCN2CCC(CC2)N2CCC3=CC=C(C=C23)C#N)C=C1.[OH-].[Na+].C(C)(=O)OCC>>FC1=CC=C(CCN2CCC(CC2)N2CCC3=CC=C(C=C23)C(N)=O)C=C1 | CCOC(C)=[O:3].[N:1]#[C:2][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>>[NH2:1][C:2](=[O: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:... | CCOC(C)=O.N#Cc1ccc2c(c1)N(C1CCN(CCc3ccc(F)cc3)CC1)CC2 | NC(=O)c1ccc2c(c1)N(C1CCN(CCc3ccc(F)cc3)CC1)CC2 | null | null | S(O)(O)(=O)=O | Miscellaneous | OtherReaction | f6f311902008ea50ca03769c972f0e9ad0ad2128a6d56657bb512d769c46ee05 | 6db77340885b60424131a70cbbe01b9cccb1071b967c44700e27103926a14e67 | c1ccc(CCN2CCC(N3CCc4ccccc43)CC2)cc1 | C-C-O-C(-C)=[O;H0;D1;+0:1].[N;H0;D1;+0:2]#[C;H0;D2;+0:3]-[c:4](:[c:5]):[c:6]>>[NH2;D1;+0:2]-[C;H0;D3;+0:3](=[O;H0;D1;+0:1])-[c:4](:[c:5]):[c:6] | 77 | [{"value": 77.0, "product": "FC1=CC=C(CCN2CCC(CC2)N2CCC3=CC=C(C=C23)C(N)=O)C=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-cyanoindoline (1.0 g) in conc. sulfuric acid (1 l) was heated at 50° C. for 2 hr. After diluting with ice water, the reaction solution was basified with a conc. aqueous solution of sodium hydroxide. Then ethyl acetate was added thereto and the layers were separate... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Nitrile | Primary amide | null | null | C1CC[NH]CC1.c1ccccc1.c1ccc2c(c1)CC[NH]2 | HO- | S(O)(O)(=O)=O | null | null | CCOC(C)=O.N#Cc1ccc2c(c1)N(C1CCN(CCc3ccc(F)cc3)CC1)CC2>S(O)(O)(=O)=O>NC(=O)c1ccc2c(c1)N(C1CCN(CCc3ccc(F)cc3)CC1)CC2 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-e3eec821340f44e9a277867fc7a6326b | CC(=O)N(C)C.Fc1ccc(CCN2CCC(N3CCc4ccc(Br)cc43)CC2)cc1>>CC(=O)c1ccc2c(c1)N(C1CCN(CCc3ccc(F)cc3)CC1)CC2 | CC(=O)N(C)C.C(CCC)[Li].FC1=CC=C(CCN2CCC(CC2)N2CCC3=CC=C(C=C23)Br)C=C1.[Cl-].[NH4+]>>FC1=CC=C(CCN2CCC(CC2)N2CCC3=CC=C(C=C23)C(C)=O)C=C1 | CN(C)[C:2]([CH3:1])=[O:3].Br[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>>[CH3:1][C:2](=[O: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]... | CC(=O)N(C)C.Fc1ccc(CCN2CCC(N3CCc4ccc(Br)cc43)CC2)cc1 | CC(=O)c1ccc2c(c1)N(C1CCN(CCc3ccc(F)cc3)CC1)CC2 | null | null | O1CCCC1.CCCCCC.C(C)(=O)OCC | C-C Coupling | Asymmetric ketones from N,N-dimethylamides | 22a19df05bda2b6ee7d13c32784a53c0d7bb790621ad97066e2818815b4722ee | 7d9aa59f8ecc532475d910f9ab122332ecbb7f9444a37371b7c1bac80798d342 | c1ccc(CCN2CCC(N3CCc4ccccc43)CC2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5]-[#7:6].C-N(-C)-[C;H0;D3;+0:7](-[C;D1;H3:8])=[O;D1;H0:9]>>[#7:6]-[c:5]:[c:4]:[c;H0;D3;+0:1](-[C;H0;D3;+0:7](-[C;D1;H3:8])=[O;D1;H0:9]):[c:2]:[c:3] | 27 | [{"value": 27.0, "product": "FC1=CC=C(CCN2CCC(CC2)N2CCC3=CC=C(C=C23)C(C)=O)C=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 10 | MINUTE | A 2.5 M solution (1.5 ml) of n-butyllithium in hexane was added dropwise at −78° C. into a solution (30 ml) of 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-bromoindoline (1.0 g) in tetrahydrofuran over 5 min. After 10 min, dimethylacetamide (0.34 ml) was added thereto and the resultant mixture was warmed to room temperatu... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Tertiary amide | Ketone | c1ccc2c(c1)CC[NH]2 | c1ccc2c(c1)CC[NH]2 | C1CC[NH]CC1.c1ccccc1.c1ccc2c(c1)CC[NH]2 | HBr | O1CCCC1.CCCCCC.C(C)(=O)OCC | null | 0.166667 | CC(=O)N(C)C.Fc1ccc(CCN2CCC(N3CCc4ccc(Br)cc43)CC2)cc1>O1CCCC1.CCCCCC.C(C)(=O)OCC>CC(=O)c1ccc2c(c1)N(C1CCN(CCc3ccc(F)cc3)CC1)CC2 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-c538c94a90844577a538f940baee3bfb | CN(C)C=O.Fc1ccc(CCN2CCC(N3CCc4ccc(Br)cc43)CC2)cc1>>O=Cc1ccc2c(c1)N(C1CCN(CCc3ccc(F)cc3)CC1)CC2 | CN(C=O)C.C(CCC)[Li].FC1=CC=C(CCN2CCC(CC2)N2CCC3=CC=C(C=C23)Br)C=C1.[Cl-].[NH4+]>>FC1=CC=C(CCN2CCC(CC2)N2CCC3=CC=C(C=C23)C=O)C=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][c:19]([F:20])[cH:21][cH:22]3)[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:... | CN(C)C=O.Fc1ccc(CCN2CCC(N3CCc4ccc(Br)cc43)CC2)cc1 | O=Cc1ccc2c(c1)N(C1CCN(CCc3ccc(F)cc3)CC1)CC2 | null | null | O1CCCC1.CCCCCC.C(C)(=O)OCC | 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] | null | [] | null | null | 10 | MINUTE | A 2.5 M solution (50 ml) of n-butyllithium in hexane was added dropwise at −78° C. into a solution of 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-bromoindoline (40 g) in tetrahydrofuran (1 l) over 10 min. After 10 min, dimethylformamide (11.6 ml) was added thereto and the resultant mixture was warmed to room temperature.... | 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.C(C)(=O)OCC | null | 0.166667 | CN(C)C=O.Fc1ccc(CCN2CCC(N3CCc4ccc(Br)cc43)CC2)cc1>O1CCCC1.CCCCCC.C(C)(=O)OCC>O=Cc1ccc2c(c1)N(C1CCN(CCc3ccc(F)cc3)CC1)CC2 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-bac566a5a11f4e82b6bb453578a6c236 | O=Cc1ccc2c(c1)N(C1CCN(CCc3ccc(F)cc3)CC1)CC2.[NH3+]O>>ON=Cc1ccc2c(c1)N(C1CCN(CCc3ccc(F)cc3)CC1)CC2 | FC1=CC=C(CCN2CCC(CC2)N2CCC3=CC=C(C=C23)C=O)C=C1.[Cl-].O[NH3+].C(C)(=O)[O-].[Na+]>>FC1=CC=C(CCN2CCC(CC2)N2CCC3=CC=C(C=C23)C=NO)C=C1 | O=[CH: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.[OH:1][NH3+:2]>>[OH:1][N:2]=[CH: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... | O=Cc1ccc2c(c1)N(C1CCN(CCc3ccc(F)cc3)CC1)CC2.[NH3+]O | ON=Cc1ccc2c(c1)N(C1CCN(CCc3ccc(F)cc3)CC1)CC2 | null | null | C(C)O | Functional Group Interconversion | OtherReaction | 9575b3f7e9975c02abe24e99b2681a2813f6f73af9b27467491bf10c6c26ae48 | 5ddad3e703fe819c706f37fb03eddf29d0a60c973b030a231bcdc1b66cd51b53 | c1ccc(CCN2CCC(N3CCc4ccccc43)CC2)cc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[NH3+;D1:5]-[O;D1;H1:6]>>[O;D1;H1:6]-[N;H0;D2;+0:5]=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4] | 85 | [{"value": 85.0, "product": "FC1=CC=C(CCN2CCC(CC2)N2CCC3=CC=C(C=C23)C=NO)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 85.0, "product": "FC1=CC=C(CCN2CCC(CC2)N2CCC3=CC=C(C=C23)C=NO)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A suspension of crude 1-[1-(4-fluorophenethyl)-piperidin-4-yl]-6-formylindoline (35 g), hydroxylammonium chloride (10.4 g) and anhydrous sodium acetate (12.3 g) in ethanol (400 ml) was stirred at room temperature for a day. Then the reaction solution was concentrated under reduced pressure, diluted with ethyl acetate (... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | Oxime | null | null | C1CC[NH]CC1.c1ccccc1.c1ccc2c(c1)CC[NH]2 | HO- | C(C)O | null | null | O=Cc1ccc2c(c1)N(C1CCN(CCc3ccc(F)cc3)CC1)CC2.[NH3+]O>C(C)O>ON=Cc1ccc2c(c1)N(C1CCN(CCc3ccc(F)cc3)CC1)CC2 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-f67998969c9543d6b23fd1c0c58706c3 | ON=Cc1ccc2c(c1)N(C1CCN(CCc3ccc(F)cc3)CC1)CC2>>NCc1ccc2c(c1)N(C1CCN(CCc3ccc(F)cc3)CC1)CC2 | FC1=CC=C(CCN2CCC(CC2)N2CCC3=CC=C(C=C23)C=NO)C=C1.[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+].O.O>>FC1=CC=C(CCN2CCC(CC2)N2CCC3=CC=C(C=C23)CN)C=C1 | O[N: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>>[NH2:1][CH2:2][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... | ON=Cc1ccc2c(c1)N(C1CCN(CCc3ccc(F)cc3)CC1)CC2 | NCc1ccc2c(c1)N(C1CCN(CCc3ccc(F)cc3)CC1)CC2 | null | null | O1CCCC1 | Reduction | OtherReaction | 2911de7676f9c054838849cab652dcb324de4944866edb887235c5bf7854a715 | 4a7bf747f64425b21ceaa04fbc4c046ccf522c774aa5649ec92eba03e46bfee5 | c1ccc(CCN2CCC(N3CCc4ccccc43)CC2)cc1 | O-[N;H0;D2;+0:1]=[CH;D2;+0:2]-[c:3](:[c:4]):[c:5]>>[NH2;D1;+0:1]-[CH2;D2;+0:2]-[c:3](:[c:4]):[c:5] | null | [] | null | null | null | null | Under ice cooling and stirring, 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-hydroxyiminomethylindoline (31 g) was added in portions to a suspension of lithium aluminum hydride (8.0 g) in tetrahydrofuran (500 ml) and then the resultant mixture was heated under reflux for 3 hr. Under cooling with ice water, water (8 ml), a... | 10.6084/m9.figshare.5104873.v1 | null | Oxime | Primary amine | null | null | C1CC[NH]CC1.c1ccccc1.c1ccc2c(c1)CC[NH]2 | Other | O1CCCC1 | null | null | ON=Cc1ccc2c(c1)N(C1CCN(CCc3ccc(F)cc3)CC1)CC2>O1CCCC1>NCc1ccc2c(c1)N(C1CCN(CCc3ccc(F)cc3)CC1)CC2 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-6456d55eb9c6470e9ebbb30f543165a7 | CC(=O)Cl.NCc1ccc2c(c1)N(C1CCN(CCc3ccc(F)cc3)CC1)CC2>>CC(=O)NCc1ccc2c(c1)N(C1CCN(CCc3ccc(F)cc3)CC1)CC2 | [OH-].[Na+].C(C)N(CC)CC.C(C)(=O)Cl.FC1=CC=C(CCN2CCC(CC2)N2CCC3=CC=C(C=C23)CN)C=C1>>FC1=CC=C(CCN2CCC(CC2)N2CCC3=CC=C(C=C23)CNC(C)=O)C=C1 | 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][CH2:29]2>>[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:13]1[CH2:14][CH2:... | CC(=O)Cl.NCc1ccc2c(c1)N(C1CCN(CCc3ccc(F)cc3)CC1)CC2 | CC(=O)NCc1ccc2c(c1)N(C1CCN(CCc3ccc(F)cc3)CC1)CC2 | null | null | O.C(C)#N | 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] | 54 | [{"value": 54.0, "product": "FC1=CC=C(CCN2CCC(CC2)N2CCC3=CC=C(C=C23)CNC(C)=O)C=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Under ice cooling, acetyl chloride (6.6 ml) was added dropwise into a solution of 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-aminomethylindoline (30 g) obtained above and triethylamine (9.4 g) in acetonitrile (500 ml) and the resultant mixture was stirred at room temperature for 1 hr. After adding a 5 N aqueous solution... | 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 | O.C(C)#N | null | null | CC(=O)Cl.NCc1ccc2c(c1)N(C1CCN(CCc3ccc(F)cc3)CC1)CC2>O.C(C)#N>CC(=O)NCc1ccc2c(c1)N(C1CCN(CCc3ccc(F)cc3)CC1)CC2 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-d10a9493fdcc4556bbcc37962679dd8c | CC(=O)NCc1ccc2c(c1)N(C1CCNCC1)CC2.Fc1ccccc1CCBr>>CC(=O)NCc1ccc2c(c1)N(C1CCN(CCc3ccccc3F)CC1)CC2 | N1CCC(CC1)N1CCC2=CC=C(C=C12)CNC(C)=O.FC1=C(CCBr)C=CC=C1>>FC1=C(CCN2CCC(CC2)N2CCC3=CC=C(C=C23)CNC(C)=O)C=CC=C1 | [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:13]1[CH2:14][CH2:15][NH:16][CH2:26][CH2:27]1)[CH2:28][CH2:29]2.Br[CH2:17][CH2:18][c:19]1[cH:20][cH:21][cH:22][cH:23][c:24]1[F:25]>>[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:13]1[CH2:14][CH2:15][... | CC(=O)NCc1ccc2c(c1)N(C1CCNCC1)CC2.Fc1ccccc1CCBr | CC(=O)NCc1ccc2c(c1)N(C1CCN(CCc3ccccc3F)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] | 52.5 | [{"value": 52.0, "product": "FC1=C(CCN2CCC(CC2)N2CCC3=CC=C(C=C23)CNC(C)=O)C=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 52.5, "product": "FC1=C(CCN2CCC(CC2)N2CCC3=CC=C(C=C23)CNC(C)=O)C=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 1-(Piperidin-4-yl)-6-acetamidomethylindoline (250 mg) and 2-fluorophenethyl bromide (220 mg) were treated as in Example 2 to give the title compound (190 mg) as a whitepowder (yield: 52%).
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 | CC(=O)NCc1ccc2c(c1)N(C1CCNCC1)CC2.Fc1ccccc1CCBr>>CC(=O)NCc1ccc2c(c1)N(C1CCN(CCc3ccccc3F)CC1)CC2 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-838fbd70a9434ecf819bd5f2549b97b6 | CC(=O)NCc1ccc2c(c1)N(C1CCNCC1)CC2.Fc1cccc(CCBr)c1>>CC(=O)NCc1ccc2c(c1)N(C1CCN(CCc3cccc(F)c3)CC1)CC2 | N1CCC(CC1)N1CCC2=CC=C(C=C12)CNC(C)=O.FC=1C=C(CCBr)C=CC1>>FC=1C=C(CCN2CCC(CC2)N2CCC3=CC=C(C=C23)CNC(C)=O)C=CC1 | [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:13]1[CH2:14][CH2:15][NH:16][CH2:26][CH2:27]1)[CH2:28][CH2:29]2.Br[CH2:17][CH2:18][c:19]1[cH:20][cH:21][cH:22][c:23]([F:24])[cH:25]1>>[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:13]1[CH2:14][CH2:15... | CC(=O)NCc1ccc2c(c1)N(C1CCNCC1)CC2.Fc1cccc(CCBr)c1 | CC(=O)NCc1ccc2c(c1)N(C1CCN(CCc3cccc(F)c3)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] | 58.1 | [{"value": 58.0, "product": "FC=1C=C(CCN2CCC(CC2)N2CCC3=CC=C(C=C23)CNC(C)=O)C=CC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 58.1, "product": "FC=1C=C(CCN2CCC(CC2)N2CCC3=CC=C(C=C23)CNC(C)=O)C=CC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 1-(Piperidin-4-yl)-6-acetamidomethylindoline (250 mg) and 3-fluorophenethyl bromide (220 mg) were treated as in Example 2 to give the title compound (210 mg) as white needles (yield: 58%).
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 | CC(=O)NCc1ccc2c(c1)N(C1CCNCC1)CC2.Fc1cccc(CCBr)c1>>CC(=O)NCc1ccc2c(c1)N(C1CCN(CCc3cccc(F)c3)CC1)CC2 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-0e74d73763f4442bb6e38f8eb19be79d | CN(C)C=O.Fc1ccc(CCN2CCC(N3CCc4ccc(Br)cc43)CC2)cc1>>OCc1ccc2c(c1)N(C1CCN(CCc3ccc(F)cc3)CC1)CC2 | CN(C=O)C.C(CCC)[Li].FC1=CC=C(CCN2CCC(CC2)N2CCC3=CC=C(C=C23)Br)C=C1.[Cl-].[NH4+]>>FC1=CC=C(CCN2CCC(CC2)N2CCC3=CC=C(C=C23)CO)C=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][c:19]([F:20])[cH:21][cH:22]3)[CH2:23][CH2:24]1)[CH2:25][CH2:26]2>>[OH:1][CH2:2][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... | CN(C)C=O.Fc1ccc(CCN2CCC(N3CCc4ccc(Br)cc43)CC2)cc1 | OCc1ccc2c(c1)N(C1CCN(CCc3ccc(F)cc3)CC1)CC2 | null | null | O1CCCC1.CCCCCC.C(C)(=O)OCC | C-C Coupling | OtherReaction | a566eec5596c9d667a6958558ee72eeb1b632cb6f31de3019d9e5d0a3a12f7c7 | 970d2c669f12a11dd05b27d160ae86c4d1d2ef9cf45eec6ba4632daedfc92cdb | 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;H0;D1;+0:8]>>[#7:6]-[c:5]:[c:4]:[c;H0;D3;+0:1](-[CH2;D2;+0:7]-[OH;D1;+0:8]):[c:2]:[c:3] | null | [] | null | null | 10 | MINUTE | A 2.5 M solution (100 ml) of n-butyllithium in hexane was added dropwise at −78° C. into a solution (2 l) of 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-bromoindoline (80 g) in tetrahydrofuran over 15 min. After 10 min, dimethylformamide (23.2 ml) was added thereto and the resultant mixture was warmed to room temperature... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Tertiary amide | Primary alcohol | c1ccc2c(c1)CC[NH]2 | c1ccc2c(c1)CC[NH]2 | C1CC[NH]CC1.c1ccccc1.c1ccc2c(c1)CC[NH]2 | HBr | O1CCCC1.CCCCCC.C(C)(=O)OCC | null | 0.166667 | CN(C)C=O.Fc1ccc(CCN2CCC(N3CCc4ccc(Br)cc43)CC2)cc1>O1CCCC1.CCCCCC.C(C)(=O)OCC>OCc1ccc2c(c1)N(C1CCN(CCc3ccc(F)cc3)CC1)CC2 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-5934a8dc59a344e399a8ff0010ae2aa2 | CC(=O)c1ccc2c(c1)N(C1CCN(CCc3ccc(F)cc3)CC1)CC2>>CC(O)c1ccc2c(c1)N(C1CCN(CCc3ccc(F)cc3)CC1)CC2 | [BH4-].[Na+].FC1=CC=C(CCN2CCC(CC2)N2CCC3=CC=C(C=C23)C(C)=O)C=C1.C(C)(=O)OCC.O>>FC1=CC=C(CCN2CCC(CC2)N2CCC3=CC=C(C=C23)C(C)O)C=C1 | [CH3:1][C:2](=[O: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>>[CH3:1][CH:2]([OH: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... | CC(=O)c1ccc2c(c1)N(C1CCN(CCc3ccc(F)cc3)CC1)CC2 | CC(O)c1ccc2c(c1)N(C1CCN(CCc3ccc(F)cc3)CC1)CC2 | null | null | C(C)O | Reduction | Reduction of ketone to secondary alcohol | 02790ac194d8bf7ccb13d6247c59412024d87f77d2c906ef7804f021f57d5070 | 1bd3cd74b454139c0a0068ac0135836499926b274bff569df163210c6c944a89 | c1ccc(CCN2CCC(N3CCc4ccccc43)CC2)cc1 | [C;D1;H3:1]-[C;H0;D3;+0:2](=[O;H0;D1;+0:3])-[c:4](:[c:5]):[c:6]>>[C;D1;H3:1]-[CH;D3;+0:2](-[OH;D1;+0:3])-[c:4](:[c:5]):[c:6] | 89 | [{"value": 89.0, "product": "FC1=CC=C(CCN2CCC(CC2)N2CCC3=CC=C(C=C23)C(C)O)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 87.8, "product": "FC1=CC=C(CCN2CCC(CC2)N2CCC3=CC=C(C=C23)C(C)O)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Sodium borohydride (0.03 g) was added to a solution (5 ml) of 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-acetylindoline (0.17 g) in ethanol and the resultant mixture was stirred at room temperature overnight. Then ethyl acetate and water were added to the reaction solution and the layers were separated. The organic laye... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Secondary alcohol | null | null | C1CC[NH]CC1.c1ccccc1.c1ccc2c(c1)CC[NH]2 | null | C(C)O | null | null | CC(=O)c1ccc2c(c1)N(C1CCN(CCc3ccc(F)cc3)CC1)CC2>C(C)O>CC(O)c1ccc2c(c1)N(C1CCN(CCc3ccc(F)cc3)CC1)CC2 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-f901dcfdd1f5429a82c4808f6b54f730 | O=Cc1ccc2c(c1)N(C1CCN(CCc3ccc(F)cc3)CC1)CC2>>CCC(O)c1ccc2c(c1)N(C1CCN(CCc3ccc(F)cc3)CC1)CC2 | C(C)[Mg].FC1=CC=C(CCN2CCC(CC2)N2CCC3=CC=C(C=C23)C=O)C=C1.[Cl-].[NH4+].C(C)(=O)OCC>>FC1=CC=C(CCN2CCC(CC2)N2CCC3=CC=C(C=C23)C(CC)O)C=C1 | [CH:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]2[c:9]([cH:10]1)[N:11]([CH:12]1[CH2:13][CH2:14][N:15]([CH2:16][CH2:17][c:18]3[cH:19][cH:20][c:21]([F:22])[cH:23][cH:24]3)[CH2:25][CH2:26]1)[CH2:27][CH2:28]2>>[CH3:1][CH2:2][CH:3]([OH:4])[c:5]1[cH:6][cH:7][c:8]2[c:9]([cH:10]1)[N:11]([CH:12]1[CH2:13][CH2:14][N:15]([CH2:16][CH2:17][c:1... | O=Cc1ccc2c(c1)N(C1CCN(CCc3ccc(F)cc3)CC1)CC2 | CCC(O)c1ccc2c(c1)N(C1CCN(CCc3ccc(F)cc3)CC1)CC2 | null | null | O1CCCC1.CCOCC | Miscellaneous | OtherReaction | 1ffaf80f172e20da969364a5d2977299bc51b204f2262675c45c8ec58ff36ac0 | e005d650d08e61fc67b766830eb53235a9bc084cc3667d2f8a73c2fb8bb34277 | c1ccc(CCN2CCC(N3CCc4ccccc43)CC2)cc1 | [O;H0;D1;+0:1]=[CH;D2;+0:2]-[c:3](:[c:4]):[c:5]>>[C;D1;H3:6]-[C:7]-[CH;D3;+0:2](-[OH;D1;+0:1])-[c:3](:[c:4]):[c:5] | 66 | [{"value": 66.0, "product": "FC1=CC=C(CCN2CCC(CC2)N2CCC3=CC=C(C=C23)C(CC)O)C=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A 3 M solution (1.4 ml) of ethylmagnesium in ether was added dropwise at −78° C. into a solution of 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-formylindoline (1.0 g) in tetrahydrofuran (30 ml) and the resultant mixture was allowed to warm to room temperature. Then a saturated aqueous solution of ammonium chloride and et... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | Secondary alcohol | null | null | C1CC[NH]CC1.c1ccccc1.c1ccc2c(c1)CC[NH]2 | Other | O1CCCC1.CCOCC | null | null | O=Cc1ccc2c(c1)N(C1CCN(CCc3ccc(F)cc3)CC1)CC2>O1CCCC1.CCOCC>CCC(O)c1ccc2c(c1)N(C1CCN(CCc3ccc(F)cc3)CC1)CC2 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-7b4a5ba2bb0948feb754fedc653f46cb | Cl.OCc1ccc2c(c1)N(C1CCN(CCc3ccc(F)cc3)CC1)CC2>>Fc1ccc(CCN2CCC(N3CCc4ccc(CCl)cc43)CC2)cc1 | [OH-].[Na+].Cl.FC1=CC=C(CCN2CCC(CC2)N2CCC3=CC=C(C=C23)CO)C=C1>>FC1=CC=C(CCN2CCC(CC2)N2CCC3=CC=C(C=C23)CCl)C=C1 | [ClH:20].O[CH2:19][c:18]1[cH:17][cH:16][c:15]2[c:22]([cH:21]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:26][cH:25]3)[CH2:24][CH2:23]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:12]3[CH2:13][CH2:14][c:15]4[cH:16][cH:17][c:18]([C... | Cl.OCc1ccc2c(c1)N(C1CCN(CCc3ccc(F)cc3)CC1)CC2 | Fc1ccc(CCN2CCC(N3CCc4ccc(CCl)cc43)CC2)cc1 | null | null | C(C)(=O)OCC | Miscellaneous | Alcohol to chloride_HCl | cd3478bc4d4e901afd9352e983cdb4ff4c2fc601772cf0af2f0553c983f9121c | 9b4091cd4cf205a0767d592c748f58d9aed076d9567056ed2bfdc4af71bd7267 | c1ccc(CCN2CCC(N3CCc4ccccc43)CC2)cc1 | O-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[ClH;D0;+0:5]>>[Cl;H0;D1;+0:5]-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4] | 94 | [{"value": 94.0, "product": "FC1=CC=C(CCN2CCC(CC2)N2CCC3=CC=C(C=C23)CCl)C=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Conc. hydrochloric acid (280 ml) was added to 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-hydroxymethylindoline (about 70 g) and the resultant mixture was stirred at 80° C. for a day. Under ice cooling, the reaction solution was neutralized with a conc. aqueous solution of sodium hydroxide followed by addition of ethyl a... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | Primary halide | null | null | c1ccccc1.C1CC[NH]CC1.c1ccc2c(c1)CC[NH]2 | HO- | C(C)(=O)OCC | null | null | Cl.OCc1ccc2c(c1)N(C1CCN(CCc3ccc(F)cc3)CC1)CC2>C(C)(=O)OCC>Fc1ccc(CCN2CCC(N3CCc4ccc(CCl)cc43)CC2)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-dbe8ac018eab4f28a8567ad116fe05d1 | OCc1ccc2c(c1)N(C1CCN(CCc3ccc(F)cc3)CC1)CC2.[Cl-]>>Fc1ccc(CCN2CCC(N3CCc4ccc(CCl)cc43)CC2)cc1 | CCN(CC)S(F)(F)F.FC1=CC=C(CCN2CCC(CC2)N2CCC3=CC=C(C=C23)CO)C=C1.[Cl-].C([O-])(O)=O.[Na+]>>FC1=CC=C(CCN2CCC(CC2)N2CCC3=CC=C(C=C23)CCl)C=C1 | O[CH2:19][c:18]1[cH:17][cH:16][c:15]2[c:22]([cH:21]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:26][cH:25]3)[CH2:24][CH2:23]1)[CH2:13][CH2:14]2.[Cl-:20]>>[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]([C... | OCc1ccc2c(c1)N(C1CCN(CCc3ccc(F)cc3)CC1)CC2.[Cl-] | Fc1ccc(CCN2CCC(N3CCc4ccc(CCl)cc43)CC2)cc1 | null | null | C(C)(=O)OCC | Functional Group Interconversion | Alcohol to chloride_Salt | bb752b9027dc4488ba075e5955118a819f80cabd751a7497b67c2eeb1db6b071 | cbf41c7cf9fe6b47a243b1674d74ed5bf46a151f7f3a71d206e23176e158facf | c1ccc(CCN2CCC(N3CCc4ccccc43)CC2)cc1 | O-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[Cl-;H0;D0:5]>>[Cl;H0;D1;+0:5]-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4] | 30 | [{"value": 30.0, "product": "FC1=CC=C(CCN2CCC(CC2)N2CCC3=CC=C(C=C23)CCl)C=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Diethylaminosulfatrifluoride (DAST, 160 mg) was added dropwise at −78° C. into a solution of 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-hydroxymethylindoline (300 mg) inmethylene chloride (10 ml) and the resultant mixture was stirred for 1 hr. Then a saturated aqueous solution of sodium bicarbonate and ethyl acetate wer... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | Primary halide | null | null | c1ccccc1.C1CC[NH]CC1.c1ccc2c(c1)CC[NH]2 | HO- | C(C)(=O)OCC | null | null | OCc1ccc2c(c1)N(C1CCN(CCc3ccc(F)cc3)CC1)CC2.[Cl-]>C(C)(=O)OCC>Fc1ccc(CCN2CCC(N3CCc4ccc(CCl)cc43)CC2)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-b2e13b913e8d4084bce170b6149d6a66 | Fc1ccc(CCN2CCC(N3CCc4ccc(CCl)cc43)CC2)cc1.[C-]#N>>N#CCc1ccc2c(c1)N(C1CCN(CCc3ccc(F)cc3)CC1)CC2 | [C-]#N.[Na+].FC1=CC=C(CCN2CCC(CC2)N2CCC3=CC=C(C=C23)CCl)C=C1>>FC1=CC=C(CCN2CCC(CC2)N2CCC3=CC=C(C=C23)CC#N)C=C1 | Cl[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.[N:1]#[C-:2]>>[N: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][CH2:13][N:14]([CH2:15][CH2:16][c:17]3[... | Fc1ccc(CCN2CCC(N3CCc4ccc(CCl)cc43)CC2)cc1.[C-]#N | N#CCc1ccc2c(c1)N(C1CCN(CCc3ccc(F)cc3)CC1)CC2 | null | null | CS(=O)C | C-C Coupling | OtherReaction | 347b040e695b34bb71d78d55beea9c7162795a061d052426f1f803b52c4cbe4d | 1dbefa1fc17e03074aa3f6619987f71dfa9a1cb0d61de142a880cd3f05e4f004 | c1ccc(CCN2CCC(N3CCc4ccccc43)CC2)cc1 | Cl-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[C-;H0;D1:5]#[N;D1;H0:6]>>[N;D1;H0:6]#[C;H0;D2;+0:5]-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4] | 98.2 | [{"value": 93.0, "product": "FC1=CC=C(CCN2CCC(CC2)N2CCC3=CC=C(C=C23)CC#N)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 98.2, "product": "FC1=CC=C(CCN2CCC(CC2)N2CCC3=CC=C(C=C23)CC#N)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Dimethyl sulfoxide (500 ml) and sodium cyanide (9.8 g) were added to 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-chloromethylindoline (about 70 g) and the resultant mixture was stirred at 50° C. for 2 hr. Next, ice water (500 ml) was added to the reaction solution followed by vigorously stirring. The resulting crystals w... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | Nitrile | null | null | C1CC[NH]CC1.c1ccccc1.c1ccc2c(c1)CC[NH]2 | Other | CS(=O)C | null | null | Fc1ccc(CCN2CCC(N3CCc4ccc(CCl)cc43)CC2)cc1.[C-]#N>CS(=O)C>N#CCc1ccc2c(c1)N(C1CCN(CCc3ccc(F)cc3)CC1)CC2 |
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