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-29798b13069746e68928538dfc6a166e | NN1CCc2ccccc21.O=C1CCCCN1>>c1cc2c3c(c1)c1c(n3CC2)CCNC1 | NN1CCC2=CC=CC=C12.O.Cl.N1C(CCCC1)=O>>Cl.C1=C2C3=C(N4C2=C(C=C1)CC4)CCNC3 | N[N:10]1[c:5]2[c:4]([cH:3][cH:2][cH:7][cH:6]2)[CH2:12][CH2:11]1.O=[C:9]1[CH2:13][CH2:14][CH2:8][CH2:16][NH:15]1>>[cH:2]1[cH:3][c:4]2[c:5]3[c:6]([cH:7]1)[c:8]1[c:9]([n:10]3[CH2:11][CH2:12]2)[CH2:13][CH2:14][NH:15][CH2:16]1 | NN1CCc2ccccc21.O=C1CCCCN1 | c1cc2c3c(c1)c1c(n3CC2)CCNC1 | null | null | C(C)(C)O | Aromatic Heterocycle Formation | OtherReaction | 760959f03481248931211a6b84cf479f544d92f0c2d0d969a37a26c4c6d56d46 | 6e34579e7c3b5183ec7e14a329ad8c29633fd7a6479856687342072bbb61dc3e | c1cc2c3c(c1)c1c(n3CC2)CCNC1 | N-[N;H0;D3;+0:1]1-[C:2]-[C:3]-[c:4]:[c:5]-1:[cH;D2;+0:6]:[c:7]:[c:8].O=[C;H0;D3;+0:9]1-[C:10]-[CH2;D2;+0:11]-[CH2;D2;+0:12]-[C:13]-[NH;D2;+0:14]-1>>[c:8]:[c:7]:[c;H0;D3;+0:6]1:[c:5]2:[c:4]-[C:3]-[C:2]-[n;H0;D3;+0:1]:2:[c;H0;D3;+0:9]2:[c;H0;D3;+0:12]:1-[C:13]-[NH;D2;+0:14]-[CH2;D2;+0:11]-[C:10]-2 | 74 | [{"value": 74.0, "product": "Cl.C1=C2C3=C(N4C2=C(C=C1)CC4)CCNC3", "details": "PERCENTYIELD", "is_desired": false}, {"value": 72.9, "product": "Cl.C1=C2C3=C(N4C2=C(C=C1)CC4)CCNC3", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 1-amino-2,3-dihydroindole (1.0 g, 5.9 mmol), piperidone hydrochloride monohydrate (0.91 g, 5.9 mmol) and isopropanol (29 mL) was brought to reflux for 4 hours. The resulting brown solid was filtered and washed with cold diethylether (20 mL) and dried under vacuum, affording the title compound (1.01 g, 74%)... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Secondary amide | Secondary amine | c1ccc2c(c1)CC[NH]2.C1CCNCC1 | c1cc2c3c(c1)c1c(n3CC2)CCNC1 | c1cc2c3c(c1)c1c(n3CC2)CCNC1 | HO- | C(C)(C)O | null | null | NN1CCc2ccccc21.O=C1CCCCN1>C(C)(C)O>c1cc2c3c(c1)c1c(n3CC2)CCNC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-93fca1292e0c4e7b86d98b4c879fe397 | c1cc2c3c(c1)c1c(n3CC2)CCNC1>>c1cc2c3c(c1)[C@H]1CNCC[C@H]1N3CC2 | Cl.C1=C2C3=C(N4C2=C(C=C1)CC4)CCNC3.[BH4-].[Na+].[OH-].[Na+]>>C1=C2[C@@H]3[C@H](N4C2=C(C=C1)CC4)CCNC3 | [cH:1]1[cH:2][c:3]2[c:4]3[c:5]([cH:6]1)[c:7]1[c:12]([n:13]3[CH2:14][CH2:15]2)[CH2:11][CH2:10][NH:9][CH2:8]1>>[cH:1]1[cH:2][c:3]2[c:4]3[c:5]([cH:6]1)[C@H:7]1[CH2:8][NH:9][CH2:10][CH2:11][C@H:12]1[N:13]3[CH2:14][CH2:15]2 | c1cc2c3c(c1)c1c(n3CC2)CCNC1 | c1cc2c3c(c1)[C@H]1CNCC[C@H]1N3CC2 | null | null | C(=O)(C(F)(F)F)O | Reduction | OtherReaction | d0d96f14a9a4072129c67110acde8d3ebeb8849f98af7a534ef431ed714cf537 | 3f9bd1254c561719832bd71149feb4e99c5764db1feb47bf9fbdfb1c414d602b | c1cc2c3c(c1)[C@H]1CNCC[C@H]1N3CC2 | [c:1]:[c:2]1:[c:3]2:[c:4]-[C:5]-[C:6]-[n;H0;D3;+0:7]:2:[c;H0;D3;+0:8]2:[c;H0;D3;+0:9]:1-[C:10]-[#7:11]-[C:12]-[C:13]-2>>[c:1]:[c:2]1:[c:3]2:[c:4]-[C:5]-[C:6]-[N;H0;D3;+0:7]-2-[C@@H;D3;+0:8]2-[C:13]-[C:12]-[#7:11]-[C:10]-[C@@H;D3;+0:9]-2-1 | 100 | [{"value": 100.0, "product": "C1=C2[C@@H]3[C@H](N4C2=C(C=C1)CC4)CCNC3", "details": "PERCENTYIELD", "is_desired": false}, {"value": 98.0, "product": "C1=C2[C@@H]3[C@H](N4C2=C(C=C1)CC4)CCNC3", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | 4,5,7,8,9,10-Hexahydropyrido[4,3-b]pyrrolo[3,2,1-hi]indole from Example 1 (0.50 g, 2.14 mmol) was stirred under N2 in TFA (15.5 mL) at 0° C. for 10 minutes. NaBH4 (0.44 g, 6.4 mmol) was added slowly keeping the temperature below 2° C. The reaction was allowed to warm to room temperature and stirred overnight. Ice chips... | 10.6084/m9.figshare.5104873.v1 | null | null | Tertiary amine | c1cc2c3c(c1)c1c(n3CC2)CCNC1 | c1cc2c3c(c1)[C@H]1CNCC[C@H]1N3CC2 | c1cc2c3c(c1)[C@H]1CNCC[C@H]1N3CC2 | null | C(=O)(C(F)(F)F)O | null | 8 | c1cc2c3c(c1)c1c(n3CC2)CCNC1>C(=O)(C(F)(F)F)O>c1cc2c3c(c1)[C@H]1CNCC[C@H]1N3CC2 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-ec8b60df59774f4f9d28c88a2a48cdfb | c1ccc2c(c1)CCCN2>>O=NN1CCCc2ccccc21 | CCOC(=O)C.N1CCCC2=CC=CC=C12.N(=O)[O-].[Na+]>>N(=O)N1CCCC2=CC=CC=C12 | [NH:3]1[CH2:4][CH2:5][CH2:6][c:7]2[cH:8][cH:9][cH:10][cH:11][c:12]21>>[O:1]=[N:2][N:3]1[CH2:4][CH2:5][CH2:6][c:7]2[cH:8][cH:9][cH:10][cH:11][c:12]21 | c1ccc2c(c1)CCCN2 | O=NN1CCCc2ccccc21 | null | null | O.CC(=O)O | Miscellaneous | OtherReaction | 78e2eaea30d28819774379a568fededf03f4bede0421cd46a2ea6f8133749482 | 797765290ff12ff8fc5d8a85352c4763898223fe8d7887a890f0208d031bd39f | c1ccc2c(c1)CCCN2 | [C:1]-[C:2]-[NH;D2;+0:3]-[c:4](:[c:5]):[c:6]>>[C:1]-[C:2]-[N;H0;D3;+0:3](-[#7:7]=[O;D1;H0:8])-[c:4](:[c:5]):[c:6] | 96.2 | [{"value": 96.0, "product": "N(=O)N1CCCC2=CC=CC=C12", "details": "PERCENTYIELD", "is_desired": false}, {"value": 96.2, "product": "N(=O)N1CCCC2=CC=CC=C12", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 2 | HOUR | 1,2,3,4-Tetrahydroquinoline (2.12 g, 15.9 mmol) was dissolved in AcOH (30 mL) and water (10 mL). The solution was cooled to 0° C. An aqueous solution of NaNO2 (1.20 g, 17.5 mmol in 3 mL water) was added dropwise. The reaction was warmed to RT and stirred 2 hrs. Water (20 mL) and EtOAc (20 mL) were added. The layers wer... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amine | Hydrazone | c1ccc2c(c1)CCCN2 | c1ccc2c(c1)CCC[NH]2 | c1ccc2c(c1)CCC[NH]2 | Other | O.CC(=O)O | 0 | 2 | c1ccc2c(c1)CCCN2>O.CC(=O)O>O=NN1CCCc2ccccc21 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-d720ac6124f142d381892dd0b19c51e1 | O=C1CCNCC1>>c1cc2c3c(c1)c1c(n3CCC2)CCNC1 | Cl.O.N1CCC(CC1)=O.Cl>>C1=CC=C2CCCN3C2=C1C1=C3CCNC1 | O=[C:12]1[CH2:3][CH2:1][NH:9][CH2:10][CH2:11]1>>[cH:1]1[cH:2][c:3]2[c:4]3[c:5]([cH:6]1)[c:7]1[c:8]([n:9]3[CH2:10][CH2:11][CH2:12]2)[CH2:13][CH2:14][NH:15][CH2:16]1 | O=C1CCNCC1 | c1cc2c3c(c1)c1c(n3CCC2)CCNC1 | null | null | CCO | Aromatic Heterocycle Formation | OtherReaction | bf232c412dcbe6340f75eabe1d590616105d2fd84204d4b0990215eac50d1560 | 486badbd7ace67904e8acbed00015464e693d4794c7e264b31386cfaaeca9f82 | c1cc2c3c(c1)c1c(n3CCC2)CCNC1 | O=[C;H0;D3;+0:1]1-[C:2]-[C:3]-[NH;D2;+0:4]-[CH2;D2;+0:5]-[CH2;D2;+0:6]-1>>[C:7]-[c:8]1:[c:9]:[c:10]2:[c:11]:[cH;D2;+0:5]:[c:12]:[c;H0;D3;+0:6]3:[c:13]:2:[n;H0;D3;+0:4]:1-[C:3]-[C:2]-[CH2;D2;+0:1]-3 | 298.5 | [{"value": 85.0, "product": "C1=CC=C2CCCN3C2=C1C1=C3CCNC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 298.5, "product": "C1=CC=C2CCCN3C2=C1C1=C3CCNC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 1,2,3,4-Tetrahydroquinoylamine (0.925 g, 6.25 mmol) and 4-piperidone monohydrate hydrochloride (0.960 g, 6.25 mmol) were dissolved in EtOH (15 mL). Conc. HCl (0.52 mL, 6.25 mmol) was added. The reaction was refluxed for 3 hrs and then cooled to RT. The precipitate was collected by vacuum filtration. The residue was was... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Secondary amine | Secondary amine | C1CCNCC1 | c1cc2c3c(c1)c1c(n3CCC2)CCNC1 | c1cc2c3c(c1)c1c(n3CCC2)CCNC1 | null | CCO | null | null | O=C1CCNCC1>CCO>c1cc2c3c(c1)c1c(n3CCC2)CCNC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-ad93a196bbba455eba00aba647b9d54a | c1cc2c3c(c1)c1c(n3CCC2)CCNC1>>c1cc2c3c(c1)[C@H]1CNCC[C@H]1N3CCC2 | O.[BH3-]C#N.[Na+].C1=CC=C2CCCN3C2=C1C1=C3CCNC1.[OH-].[Na+]>>C1=CC=C2CCCN3C2=C1[C@@H]1[C@H]3CCNC1 | [cH:1]1[cH:2][c:3]2[c:4]3[c:5]([cH:6]1)[c:7]1[c:12]([n:13]3[CH2:14][CH2:15][CH2:16]2)[CH2:11][CH2:10][NH:9][CH2:8]1>>[cH:1]1[cH:2][c:3]2[c:4]3[c:5]([cH:6]1)[C@H:7]1[CH2:8][NH:9][CH2:10][CH2:11][C@H:12]1[N:13]3[CH2:14][CH2:15][CH2:16]2 | c1cc2c3c(c1)c1c(n3CCC2)CCNC1 | c1cc2c3c(c1)[C@H]1CNCC[C@H]1N3CCC2 | null | null | C(=O)(C(F)(F)F)O | Reduction | OtherReaction | e93ed48611c781d977a85b53e67f2518501053b203225c38439aea6cc36c8223 | 3f9bd1254c561719832bd71149feb4e99c5764db1feb47bf9fbdfb1c414d602b | c1cc2c3c(c1)[C@H]1CNCC[C@H]1N3CCC2 | [C:1]-[C:2]-[n;H0;D3;+0:3]1:[c:4](:[c:5]):[c:6](:[c:7]):[c;H0;D3;+0:8]2:[c;H0;D3;+0:9]:1-[C:10]-[C:11]-[#7:12]-[C:13]-2>>[C:1]-[C:2]-[N;H0;D3;+0:3]1-[C@@H;D3;+0:9]2-[C:10]-[C:11]-[#7:12]-[C:13]-[C@@H;D3;+0:8]-2-[c:6](:[c:7]):[c:4]-1:[c:5] | 68.4 | [{"value": 68.0, "product": "C1=CC=C2CCCN3C2=C1[C@@H]1[C@H]3CCNC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 68.4, "product": "C1=CC=C2CCCN3C2=C1[C@@H]1[C@H]3CCNC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 2 | HOUR | 5,6,8,9,10,11-Hexahydro-4H-pyrido[3′,4′:4,5]pyrrolo[3,2,1-ij]quinoline (2.84 g, 11.4 mmol) was dissolved in TFA (35 mL). The reaction was cooled to 0° C. NaCNBH3(2.15 g, 34.27 mmol) was added in small portions over 30 min, keeping the temperature less than 5° C. The reaction was stirred at 0° C. for 2 h. Ice was added ... | 10.6084/m9.figshare.5104873.v1 | null | null | Tertiary amine | c1cc2c3c(c1)c1c(n3CCC2)CCNC1 | c1cc2c3c(c1)[C@H]1CNCC[C@H]1N3CCC2 | c1cc2c3c(c1)[C@H]1CNCC[C@H]1N3CCC2 | null | C(=O)(C(F)(F)F)O | 0 | 2 | c1cc2c3c(c1)c1c(n3CCC2)CCNC1>C(=O)(C(F)(F)F)O>c1cc2c3c(c1)[C@H]1CNCC[C@H]1N3CCC2 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-bcf0727f4d4244db8a03bf9cd2c4f315 | O=C(Cl)C1CC1.c1cc2c3c(c1)[C@H]1CNCC[C@H]1N3CC2>>O=C(C1CC1)N1CC[C@@H]2[C@H](C1)c1cccc3c1N2CC3 | C1=C2[C@@H]3[C@H](N4C2=C(C=C1)CC4)CCNC3.C1(CC1)C(=O)Cl>>C1(CC1)C(=O)N1C[C@H]2[C@H](N3C4=C(C=CC=C24)CC3)CC1 | Cl[C:2](=[O:1])[CH:3]1[CH2:4][CH2:5]1.[NH:6]1[CH2:7][CH2:8][C@@H:9]2[C@H:10]([CH2:11]1)[c:12]1[cH:13][cH:14][cH:15][c:16]3[c:17]1[N:18]2[CH2:19][CH2:20]3>>[O:1]=[C:2]([CH:3]1[CH2:4][CH2:5]1)[N:6]1[CH2:7][CH2:8][C@@H:9]2[C@H:10]([CH2:11]1)[c:12]1[cH:13][cH:14][cH:15][c:16]3[c:17]1[N:18]2[CH2:19][CH2:20]3 | O=C(Cl)C1CC1.c1cc2c3c(c1)[C@H]1CNCC[C@H]1N3CC2 | O=C(C1CC1)N1CC[C@@H]2[C@H](C1)c1cccc3c1N2CC3 | null | null | CCN(CC)CC.C(Cl)Cl | Acylation | N-alkylation of secondary amines with alkyl halides | b69c69e2effa328df67c7a674399cb51b723e4a94e119ef8771c688311a9ff8e | 96cb0a2fed10552c5770a45a2d6523b47ac3e38928b4a9c698d8577451182dcd | O=C(C1CC1)N1CC[C@@H]2[C@H](C1)c1cccc3c1N2CC3 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]1-[C:4]-[C:5]-1.[C:6]-[C:7]-[NH;D2;+0:8]-[C:9]-[C:10]>>[C:6]-[C:7]-[N;H0;D3;+0:8](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]1-[C:4]-[C:5]-1)-[C:9]-[C:10] | 65 | [{"value": 65.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 1 | HOUR | (±)-cis-4,5,6a,7,8,9,10,10a-octahydropyrido[4,3-b]pyrrolo[3,2,1-hi]indole from Example 3 (0.050 g, 0.25 mmol) was dissolved in CH2Cl2 (5 mL) with Et3N (0.75 mL) and cooled to 0° C. The cyclopropanecarbonyl chloride (0.026 g, 0.26 mmol) was then added dropwise. The solution was stirred at 0° C. for 1 h and then warmed t... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Secondary amine | Tertiary amide | c1cc2c3c(c1)[C@H]1CNCC[C@H]1N3CC2 | c1cc2c3c(c1)[C@H]1C[NH]CC[C@H]1N3CC2 | C1CC1.c1cc2c3c(c1)[C@H]1C[NH]CC[C@H]1N3CC2 | HCl | CCN(CC)CC.C(Cl)Cl | 0 | 1 | O=C(Cl)C1CC1.c1cc2c3c(c1)[C@H]1CNCC[C@H]1N3CC2>CCN(CC)CC.C(Cl)Cl>O=C(C1CC1)N1CC[C@@H]2[C@H](C1)c1cccc3c1N2CC3 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-f9f9519cd30a466ab13a20855785bd63 | CC(C)(C)OC(=O)N1CC[C@@H]2[C@H](C1)c1cccc3c1N2CC3.O=C1CCC(=O)N1Br>>CC(C)(C)OC(=O)N1CC[C@@H]2[C@H](C1)c1cc(Br)cc3c1N2CC3 | C1=C2[C@@H]3[C@H](N4C2=C(C=C1)CC4)CCN(C3)C(=O)OC(C)(C)C.C1CC(=O)N(C1=O)Br.O.CCOC(=O)C>>BrC=1C=C2[C@@H]3[C@H](N4C2=C(C1)CC4)CCN(C3)C(=O)OC(C)(C)C | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][C@@H:11]2[C@H:12]([CH2:13]1)[c:14]1[cH:15][cH:16][cH:18][c:19]3[c:20]1[N:21]2[CH2:22][CH2:23]3.O=C1CCC(=O)N1[Br:17]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][C@@H:11]2[C@H:12]([CH2:13]1)[c:14]1[cH:15][c:16]([Br:17])[cH:18... | CC(C)(C)OC(=O)N1CC[C@@H]2[C@H](C1)c1cccc3c1N2CC3.O=C1CCC(=O)N1Br | CC(C)(C)OC(=O)N1CC[C@@H]2[C@H](C1)c1cc(Br)cc3c1N2CC3 | null | null | CN(C)C=O | Functional Group Interconversion | Bromination | a0dde386d0832f42a55399bdd848c1ee88eaedfefee707d608d9d8092e68c714 | 0e444576b73669992a4073cc3f7b10ed52cb9df09f9f8e4042e39e6a602aa390 | c1cc2c3c(c1)[C@H]1CNCC[C@H]1N3CC2 | O=C1-C-C-C(=O)-N-1-[Br;H0;D1;+0:1].[c:2]:[c:3]:[cH;D2;+0:4]:[c:5]:[c:6]>>[Br;H0;D1;+0:1]-[c;H0;D3;+0:4](:[c:3]:[c:2]):[c:5]:[c:6] | 75.5 | [{"value": 75.0, "product": "BrC=1C=C2[C@@H]3[C@H](N4C2=C(C1)CC4)CCN(C3)C(=O)OC(C)(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 75.5, "product": "BrC=1C=C2[C@@H]3[C@H](N4C2=C(C1)CC4)CCN(C3)C(=O)OC(C)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 20 | MINUTE | To a solution of tert-butyl(±)-cis-4,5,7,8,10,10a-hexahydropyrido[4,3-b]pyrrolo[3,2,1-hi]indole-9(6aH)-carboxylate (0.576 g, 1.92 mmol) in DMF (4 mL) at 0° C., freshly recrystalized NBS (0.375 g, 2.1 mmol) was added as a solution in DMF (4 mL). The reaction was stirred at 0° C. for 20 min, after which it was warmed to ... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Tertiary amide | Aromatic halide | c1cc2c3c(c1)[C@H]1C[NH]CC[C@H]1N3CC2.C1CCNC1 | c1cc2c3c(c1)[C@H]1C[NH]CC[C@H]1N3CC2 | c1cc2c3c(c1)[C@H]1C[NH]CC[C@H]1N3CC2 | HO- | CN(C)C=O | 0 | 0.333333 | CC(C)(C)OC(=O)N1CC[C@@H]2[C@H](C1)c1cccc3c1N2CC3.O=C1CCC(=O)N1Br>CN(C)C=O>CC(C)(C)OC(=O)N1CC[C@@H]2[C@H](C1)c1cc(Br)cc3c1N2CC3 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-3906d4768b0348d3bb01ecfa3913aa58 | CC(C)(C)OC(=O)N1CC[C@@H]2[C@H](C1)c1cc(Br)cc3c1N2CC3.OB(O)c1ccc(Cl)cc1Cl>>CC(C)(C)OC(=O)N1CC[C@@H]2[C@H](C1)c1cc(-c3ccc(Cl)cc3Cl)cc3c1N2CC3 | BrC=1C=C2[C@@H]3[C@H](N4C2=C(C1)CC4)CCN(C3)C(=O)OC(C)(C)C.ClC1=C(C=CC(=C1)Cl)B(O)O.N>>ClC1=C(C=CC(=C1)Cl)C=1C=C2[C@@H]3[C@H](N4C2=C(C1)CC4)CCN(C3)C(=O)OC(C)(C)C | Br[c:16]1[cH:15][c:14]2[c:27]3[c:26]([cH:25]1)[CH2:30][CH2:29][N:28]3[C@@H:11]1[CH2:10][CH2:9][N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:13][C@@H:12]12.OB(O)[c:17]1[cH:18][cH:19][c:20]([Cl:21])[cH:22][c:23]1[Cl:24]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][C@@H:11]2[C@H:12]... | CC(C)(C)OC(=O)N1CC[C@@H]2[C@H](C1)c1cc(Br)cc3c1N2CC3.OB(O)c1ccc(Cl)cc1Cl | CC(C)(C)OC(=O)N1CC[C@@H]2[C@H](C1)c1cc(-c3ccc(Cl)cc3Cl)cc3c1N2CC3 | null | null | null | C-C Coupling | Suzuki coupling with boronic acids | ed2b77f726df32e6b1df0a3837264eae44b8abe085baac431ef84ba0347767fb | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(-c2cc3c4c(c2)[C@H]2CNCC[C@H]2N4CC3)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].O-B(-O)-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9](-[Cl;D1;H0:10]):[c:11]>>[Cl;D1;H0:10]-[c:9](:[c:11]):[c;H0;D3;+0:6](-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5]):[c:7]:[c:8] | 50.2 | [{"value": 50.0, "product": "ClC1=C(C=CC(=C1)Cl)C=1C=C2[C@@H]3[C@H](N4C2=C(C1)CC4)CCN(C3)C(=O)OC(C)(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 50.2, "product": "ClC1=C(C=CC(=C1)Cl)C=1C=C2[C@@H]3[C@H](N4C2=C(C1)CC4)CCN(C3)C(=O)OC(C)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | The title compound (55.9 mg, 50%) was prepared by the method of Example 89 Step C from tert-butyl(±)-cis-2-bromo-4,5,7,8,10,10a-hexahydropyrido[4,3-b]pyrrolo[3,2,1-hi]indole-9(6aH)-carboxylate (94 mg, 0.25 mmol) and 2,4-dichlorophenylboronic acid (95 mg, 0.5 mmol) as a white amorphous solid. MS (CI, NH3): 445 (base, M+... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1cc2c3c(c1)[C@H]1C[NH]CC[C@H]1N3CC2.c1ccccc1 | c1ccccc1.c1cc2c3c(c1)[C@H]1C[NH]CC[C@H]1N3CC2 | c1ccccc1.c1cc2c3c(c1)[C@H]1C[NH]CC[C@H]1N3CC2 | HBr.B | null | null | null | CC(C)(C)OC(=O)N1CC[C@@H]2[C@H](C1)c1cc(Br)cc3c1N2CC3.OB(O)c1ccc(Cl)cc1Cl>>CC(C)(C)OC(=O)N1CC[C@@H]2[C@H](C1)c1cc(-c3ccc(Cl)cc3Cl)cc3c1N2CC3 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-006a9ad2ef534819abaed28d73a1b715 | CC(C)(C)OC(=O)N1CC[C@@H]2[C@H](C1)c1cc(Br)cc3c1N2CC3.OB(O)c1cccc(Cl)c1Cl>>CC(C)(C)OC(=O)N1CC[C@@H]2[C@H](C1)c1cc(-c3cccc(Cl)c3Cl)cc3c1N2CC3 | BrC=1C=C2[C@@H]3[C@H](N4C2=C(C1)CC4)CCN(C3)C(=O)OC(C)(C)C.ClC1=C(C=CC=C1Cl)B(O)O>>ClC1=C(C=CC=C1Cl)C=1C=C2[C@@H]3[C@H](N4C2=C(C1)CC4)CCN(C3)C(=O)OC(C)(C)C | Br[c:16]1[cH:15][c:14]2[c:27]3[c:26]([cH:25]1)[CH2:30][CH2:29][N:28]3[C@@H:11]1[CH2:10][CH2:9][N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:13][C@@H:12]12.OB(O)[c:17]1[cH:18][cH:19][cH:20][c:21]([Cl:22])[c:23]1[Cl:24]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][C@@H:11]2[C@H:12]... | CC(C)(C)OC(=O)N1CC[C@@H]2[C@H](C1)c1cc(Br)cc3c1N2CC3.OB(O)c1cccc(Cl)c1Cl | CC(C)(C)OC(=O)N1CC[C@@H]2[C@H](C1)c1cc(-c3cccc(Cl)c3Cl)cc3c1N2CC3 | null | null | null | C-C Coupling | Suzuki coupling with boronic acids | ed2b77f726df32e6b1df0a3837264eae44b8abe085baac431ef84ba0347767fb | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(-c2cc3c4c(c2)[C@H]2CNCC[C@H]2N4CC3)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].O-B(-O)-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9](-[Cl;D1;H0:10]):[c:11]>>[Cl;D1;H0:10]-[c:9](:[c:11]):[c;H0;D3;+0:6](-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5]):[c:7]:[c:8] | null | [] | null | null | null | null | The title compound was prepared by the method of Example 90 from tert-butyl(±)-cis-2-bromo-4,5,7,8,10,10a-hexahydropyrido[4,3-b]pyrrolo[3,2,1-hi]indole-9(6aH)-carboxylate (124 mg, 0.27 mmol) and corresponding 2,3-dichlorophenylboronic acid (104 mg, 0.54 mmol), to afford after chromatographic purification the title comp... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1cc2c3c(c1)[C@H]1C[NH]CC[C@H]1N3CC2.c1ccccc1 | c1ccccc1.c1cc2c3c(c1)[C@H]1C[NH]CC[C@H]1N3CC2 | c1ccccc1.c1cc2c3c(c1)[C@H]1C[NH]CC[C@H]1N3CC2 | HBr.B | null | null | null | CC(C)(C)OC(=O)N1CC[C@@H]2[C@H](C1)c1cc(Br)cc3c1N2CC3.OB(O)c1cccc(Cl)c1Cl>>CC(C)(C)OC(=O)N1CC[C@@H]2[C@H](C1)c1cc(-c3cccc(Cl)c3Cl)cc3c1N2CC3 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-5c5d21136bfc45f999a5600509ba5edf | CC(C)(C)OC(=O)N1CC[C@@H]2[C@H](C1)c1cc(Br)cc3c1N2CC3.OB(O)c1ccc(C(F)(F)F)cc1Cl>>CC(C)(C)OC(=O)N1CC[C@@H]2[C@H](C1)c1cc(-c3ccc(C(F)(F)F)cc3Cl)cc3c1N2CC3 | BrC=1C=C2[C@@H]3[C@H](N4C2=C(C1)CC4)CCN(C3)C(=O)OC(C)(C)C.ClC1=C(C=CC(=C1)C(F)(F)F)B(O)O>>ClC1=C(C=CC(=C1)C(F)(F)F)C=1C=C2[C@@H]3[C@H](N4C2=C(C1)CC4)CCN(C3)C(=O)OC(C)(C)C | Br[c:16]1[cH:15][c:14]2[c:30]3[c:29]([cH:28]1)[CH2:33][CH2:32][N:31]3[C@@H:11]1[CH2:10][CH2:9][N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:13][C@@H:12]12.OB(O)[c:17]1[cH:18][cH:19][c:20]([C:21]([F:22])([F:23])[F:24])[cH:25][c:26]1[Cl:27]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:... | CC(C)(C)OC(=O)N1CC[C@@H]2[C@H](C1)c1cc(Br)cc3c1N2CC3.OB(O)c1ccc(C(F)(F)F)cc1Cl | CC(C)(C)OC(=O)N1CC[C@@H]2[C@H](C1)c1cc(-c3ccc(C(F)(F)F)cc3Cl)cc3c1N2CC3 | null | null | null | C-C Coupling | Suzuki coupling with boronic acids | ed2b77f726df32e6b1df0a3837264eae44b8abe085baac431ef84ba0347767fb | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(-c2cc3c4c(c2)[C@H]2CNCC[C@H]2N4CC3)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].O-B(-O)-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9](-[Cl;D1;H0:10]):[c:11]>>[Cl;D1;H0:10]-[c:9](:[c:11]):[c;H0;D3;+0:6](-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5]):[c:7]:[c:8] | null | [] | null | null | null | null | The title compound was prepared by the method of Example 90 from tert-butyl(±)-cis-2-bromo-4,5,7,8,10,10a-hexahydropyrido[4,3-b]pyrrolo[3,2,1-hi]indole-9(6aH)-carboxylate (136 mg, 0.30 mmol) and corresponding 2-chloro-4-trifluoromethylphenylboronic acid (128 mg, 0.60 mmol), to afford after chromatographic purification ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1cc2c3c(c1)[C@H]1C[NH]CC[C@H]1N3CC2.c1ccccc1 | c1ccccc1.c1cc2c3c(c1)[C@H]1C[NH]CC[C@H]1N3CC2 | c1ccccc1.c1cc2c3c(c1)[C@H]1C[NH]CC[C@H]1N3CC2 | HBr.B | null | null | null | CC(C)(C)OC(=O)N1CC[C@@H]2[C@H](C1)c1cc(Br)cc3c1N2CC3.OB(O)c1ccc(C(F)(F)F)cc1Cl>>CC(C)(C)OC(=O)N1CC[C@@H]2[C@H](C1)c1cc(-c3ccc(C(F)(F)F)cc3Cl)cc3c1N2CC3 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-154ecb8e1c894206b5a5d454de97b946 | CC(C)(C)OC(=O)N1CC[C@@H]2[C@H](C1)c1cc(Br)cc3c1N2CC3.COc1ccc(B(O)O)c(Cl)c1>>COc1ccc(-c2cc3c4c(c2)[C@H]2CN(C(=O)OC(C)(C)C)CC[C@H]2N4CC3)c(Cl)c1 | BrC=1C=C2[C@@H]3[C@H](N4C2=C(C1)CC4)CCN(C3)C(=O)OC(C)(C)C.ClC1=C(C=CC(=C1)OC)B(O)O>>ClC1=C(C=CC(=C1)OC)C=1C=C2[C@@H]3[C@H](N4C2=C(C1)CC4)CCN(C3)C(=O)OC(C)(C)C | Br[c:7]1[cH:8][c:9]2[c:10]3[c:11]([cH:12]1)[C@H:13]1[CH2:14][N:15]([C:16](=[O:17])[O:18][C:19]([CH3:20])([CH3:21])[CH3:22])[CH2:23][CH2:24][C@H:25]1[N:26]3[CH2:27][CH2:28]2.OB(O)[c:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:31][c:29]1[Cl:30]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][c:9]3[c:10]4[c:11]([cH:12]2)[C@H... | CC(C)(C)OC(=O)N1CC[C@@H]2[C@H](C1)c1cc(Br)cc3c1N2CC3.COc1ccc(B(O)O)c(Cl)c1 | COc1ccc(-c2cc3c4c(c2)[C@H]2CN(C(=O)OC(C)(C)C)CC[C@H]2N4CC3)c(Cl)c1 | null | null | null | C-C Coupling | Suzuki coupling with boronic acids | ed2b77f726df32e6b1df0a3837264eae44b8abe085baac431ef84ba0347767fb | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(-c2cc3c4c(c2)[C@H]2CNCC[C@H]2N4CC3)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].O-B(-O)-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9](-[Cl;D1;H0:10]):[c:11]>>[Cl;D1;H0:10]-[c:9](:[c:11]):[c;H0;D3;+0:6](-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5]):[c:7]:[c:8] | null | [] | null | null | null | null | The title compound was prepared by the method of Example 90 from tert-butyl(±)-cis-2-bromo-4,5,7,8,10,10a-hexahydropyrido[4,3-b]pyrrolo[3,2,1-hi]indole-9(6aH)-carboxylate (121 mg, 0.27 mmol) and corresponding 2-chloro-4-methoxyphenylboronic acid (100 mg, 0.54 mmol), to afford after chromatographic purification the titl... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1cc2c3c(c1)[C@H]1C[NH]CC[C@H]1N3CC2.c1ccccc1 | c1ccccc1.c1cc2c3c(c1)[C@H]1C[NH]CC[C@H]1N3CC2 | c1ccccc1.c1cc2c3c(c1)[C@H]1C[NH]CC[C@H]1N3CC2 | HBr.B | null | null | null | CC(C)(C)OC(=O)N1CC[C@@H]2[C@H](C1)c1cc(Br)cc3c1N2CC3.COc1ccc(B(O)O)c(Cl)c1>>COc1ccc(-c2cc3c4c(c2)[C@H]2CN(C(=O)OC(C)(C)C)CC[C@H]2N4CC3)c(Cl)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-dd0f1c75d20d4befbe6e6e272e80c78f | CC(C)(C)OC(=O)N1CC[C@@H]2[C@H](C1)c1cc(Br)cc3c1N2CC3.OB(O)c1cccc(F)c1>>CC(C)(C)OC(=O)N1CC[C@@H]2[C@H](C1)c1cc(-c3cccc(F)c3)cc3c1N2CC3 | BrC=1C=C2[C@@H]3[C@H](N4C2=C(C1)CC4)CCN(C3)C(=O)OC(C)(C)C.FC=1C=C(C=CC1)B(O)O>>FC=1C=C(C=CC1)C=1C=C2[C@@H]3[C@H](N4C2=C(C1)CC4)CCN(C3)C(=O)OC(C)(C)C | Br[c:16]1[cH:15][c:14]2[c:26]3[c:25]([cH:24]1)[CH2:29][CH2:28][N:27]3[C@@H:11]1[CH2:10][CH2:9][N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:13][C@@H:12]12.OB(O)[c:17]1[cH:18][cH:19][cH:20][c:21]([F:22])[cH:23]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][C@@H:11]2[C@H:12]([CH2:1... | CC(C)(C)OC(=O)N1CC[C@@H]2[C@H](C1)c1cc(Br)cc3c1N2CC3.OB(O)c1cccc(F)c1 | CC(C)(C)OC(=O)N1CC[C@@H]2[C@H](C1)c1cc(-c3cccc(F)c3)cc3c1N2CC3 | null | null | null | C-C Coupling | Suzuki coupling with boronic acids | ed2b77f726df32e6b1df0a3837264eae44b8abe085baac431ef84ba0347767fb | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(-c2cc3c4c(c2)[C@H]2CNCC[C@H]2N4CC3)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].O-B(-O)-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]>>[c:3]:[c:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]):[c:4]:[c:5] | null | [] | null | null | null | null | The title compound was prepared by the method of Example 90 tert-butyl(±)-cis-2-bromo-4,5,7,8,10,10a-hexahydropyrido[4,3-b]pyrrolo[3,2,1-hi]indole-9(6aH)-carboxylate (125 mg, 0.28 mmol) and corresponding 3-fluorophenylboronic acid (77 mg, 0.56 mmol), to afford after chromatographic purification the title compound (48 m... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1cc2c3c(c1)[C@H]1C[NH]CC[C@H]1N3CC2.c1ccccc1 | c1ccccc1.c1cc2c3c(c1)[C@H]1C[NH]CC[C@H]1N3CC2 | c1ccccc1.c1cc2c3c(c1)[C@H]1C[NH]CC[C@H]1N3CC2 | HBr.B | null | null | null | CC(C)(C)OC(=O)N1CC[C@@H]2[C@H](C1)c1cc(Br)cc3c1N2CC3.OB(O)c1cccc(F)c1>>CC(C)(C)OC(=O)N1CC[C@@H]2[C@H](C1)c1cc(-c3cccc(F)c3)cc3c1N2CC3 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-f7fcff5daf294dd6b4259549728818f5 | CC(C)(C)OC(=O)N1CC[C@@H]2[C@H](C1)c1cc(Br)cc3c1N2CC3.COc1ccc(B(O)O)c(OC)c1>>COc1ccc(-c2cc3c4c(c2)[C@H]2CN(C(=O)OC(C)(C)C)CC[C@H]2N4CC3)c(OC)c1 | BrC=1C=C2[C@@H]3[C@H](N4C2=C(C1)CC4)CCN(C3)C(=O)OC(C)(C)C.COC1=C(C=CC(=C1)OC)B(O)O>>COC1=C(C=CC(=C1)OC)C=1C=C2[C@@H]3[C@H](N4C2=C(C1)CC4)CCN(C3)C(=O)OC(C)(C)C | Br[c:7]1[cH:8][c:9]2[c:10]3[c:11]([cH:12]1)[C@H:13]1[CH2:14][N:15]([C:16](=[O:17])[O:18][C:19]([CH3:20])([CH3:21])[CH3:22])[CH2:23][CH2:24][C@H:25]1[N:26]3[CH2:27][CH2:28]2.OB(O)[c:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:32][c:29]1[O:30][CH3:31]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][c:9]3[c:10]4[c:11]([cH:12... | CC(C)(C)OC(=O)N1CC[C@@H]2[C@H](C1)c1cc(Br)cc3c1N2CC3.COc1ccc(B(O)O)c(OC)c1 | COc1ccc(-c2cc3c4c(c2)[C@H]2CN(C(=O)OC(C)(C)C)CC[C@H]2N4CC3)c(OC)c1 | null | null | null | C-C Coupling | Suzuki coupling with boronic acids | ed2b77f726df32e6b1df0a3837264eae44b8abe085baac431ef84ba0347767fb | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(-c2cc3c4c(c2)[C@H]2CNCC[C@H]2N4CC3)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].O-B(-O)-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9](-[#8:10]):[c:11]>>[#8:10]-[c:9](:[c:11]):[c;H0;D3;+0:6](-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5]):[c:7]:[c:8] | null | [] | null | null | null | null | The title compound was prepared by the method of Example 90 from tert-butyl(±)-cis-2-bromo-4,5,7,8,10,10a-hexahydropyrido[4,3-b]pyrrolo[3,2,1-hi]indole-9(6aH)-carboxylate (143 mg, 0.32 mmol) and corresponding 2,4-dimethoxyphenylboronic acid (115 mg, 0.63 mmol), to afford after chromatographic purification the title com... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1cc2c3c(c1)[C@H]1C[NH]CC[C@H]1N3CC2.c1ccccc1 | c1ccccc1.c1cc2c3c(c1)[C@H]1C[NH]CC[C@H]1N3CC2 | c1ccccc1.c1cc2c3c(c1)[C@H]1C[NH]CC[C@H]1N3CC2 | HBr.B | null | null | null | CC(C)(C)OC(=O)N1CC[C@@H]2[C@H](C1)c1cc(Br)cc3c1N2CC3.COc1ccc(B(O)O)c(OC)c1>>COc1ccc(-c2cc3c4c(c2)[C@H]2CN(C(=O)OC(C)(C)C)CC[C@H]2N4CC3)c(OC)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-1a8fadb98ed54f06abd147d5f908a6c3 | CC(C)(C)OC(=O)N1CC[C@@H]2[C@H](C1)c1cc(-c3ccccc3Cl)cc3c1N2CC3>>Clc1ccccc1-c1cc2c3c(c1)[C@H]1CNCC[C@H]1N3CC2 | ClC1=C(C=CC=C1)C=1C=C2[C@@H]3[C@H](N4C2=C(C1)CC4)CCN(C3)C(=O)OC(C)(C)C.[OH-].[Na+]>>ClC1=C(C=CC=C1)C=1C=C2[C@@H]3[C@H](N4C2=C(C1)CC4)CCNC3 | CC(C)(C)OC(=O)[N:16]1[CH2:15][C@@H:14]2[c:12]3[c:11]4[c:10]([cH:9][c:8](-[c:7]5[c:2]([Cl:1])[cH:3][cH:4][cH:5][cH:6]5)[cH:13]3)[CH2:22][CH2:21][N:20]4[C@@H:19]2[CH2:18][CH2:17]1>>[Cl:1][c:2]1[cH:3][cH:4][cH:5][cH:6][c:7]1-[c:8]1[cH:9][c:10]2[c:11]3[c:12]([cH:13]1)[C@H:14]1[CH2:15][NH:16][CH2:17][CH2:18][C@H:19]1[N:20]3... | CC(C)(C)OC(=O)N1CC[C@@H]2[C@H](C1)c1cc(-c3ccccc3Cl)cc3c1N2CC3 | Clc1ccccc1-c1cc2c3c(c1)[C@H]1CNCC[C@H]1N3CC2 | null | null | C(Cl)Cl.C(=O)(C(F)(F)F)O | Reduction | Boc amine deprotection | ee769ca14b92540b0ddcc4bba2d8947e6ea5d86cb05efe4f19d41715bb15ba45 | a94b29c7264c852156fc1cdd4a0951a4fc26c06d0edc9e50c743825dbf79e3fd | c1ccc(-c2cc3c4c(c2)[C@H]2CNCC[C@H]2N4CC3)cc1 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1](-[C:2]-[C:3])-[C:4]-[C:5]>>[C:3]-[C:2]-[NH;D2;+0:1]-[C:4]-[C:5] | 86 | [{"value": 86.0, "product": "ClC1=C(C=CC=C1)C=1C=C2[C@@H]3[C@H](N4C2=C(C1)CC4)CCNC3", "details": "PERCENTYIELD", "is_desired": false}, {"value": 85.7, "product": "ClC1=C(C=CC=C1)C=1C=C2[C@@H]3[C@H](N4C2=C(C1)CC4)CCNC3", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | Tert-butyl(±)-cis-2-(2-chlorophenyl)-4,5,7,8,10,10a-hexahydropyrido[4,3-b]pyrrolo[3,2,1-hi]indole-9(6aH)-carboxylate (45.1 mg, 0.11 mmol) was dissolved in 20% TFA in methylene chloride (4 mL) and was stirred at RT for 2 h. The reaction was solution was cooled to 0° C. and basified with 1M NaOH until pH>14. The layers w... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Secondary amine | c1cc2c3c(c1)[C@H]1C[NH]CC[C@H]1N3CC2 | c1cc2c3c(c1)[C@H]1CNCC[C@H]1N3CC2 | c1ccccc1.c1cc2c3c(c1)[C@H]1CNCC[C@H]1N3CC2 | HO- | C(Cl)Cl.C(=O)(C(F)(F)F)O | null | 2 | CC(C)(C)OC(=O)N1CC[C@@H]2[C@H](C1)c1cc(-c3ccccc3Cl)cc3c1N2CC3>C(Cl)Cl.C(=O)(C(F)(F)F)O>Clc1ccccc1-c1cc2c3c(c1)[C@H]1CNCC[C@H]1N3CC2 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-99baa614f1b346b58617c2caccb86746 | CC(C)(C)OC(=O)N1CC[C@@H]2[C@H](C1)c1cc(Br)cc3c1N2CCC3.OB(O)c1cccc(Cl)c1Cl>>CC(C)(C)OC(=O)N1CC[C@@H]2[C@H](C1)c1cc(-c3cccc(Cl)c3Cl)cc3c1N2CCC3 | P(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1.C([O-])([O-])=O.[Na+].[Na+].BrC=1C=C2CCCN3C2=C(C1)[C@@H]1[C@H]3CCN(C1)C(=O)OC(C)(C)C.ClC1=C(C=CC=C1Cl)B(O)O>>ClC1=C(C=CC=C1Cl)C=1C=C2CCCN3C2=C(C1)[C@@H]1[C@H]3CCN(C1)C(=O)OC(C)(C)C | Br[c:16]1[cH:15][c:14]2[c:27]3[c:26]([cH:25]1)[CH2:31][CH2:30][CH2:29][N:28]3[C@@H:11]1[CH2:10][CH2:9][N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:13][C@@H:12]12.OB(O)[c:17]1[cH:18][cH:19][cH:20][c:21]([Cl:22])[c:23]1[Cl:24]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][C@@H:11]2... | CC(C)(C)OC(=O)N1CC[C@@H]2[C@H](C1)c1cc(Br)cc3c1N2CCC3.OB(O)c1cccc(Cl)c1Cl | CC(C)(C)OC(=O)N1CC[C@@H]2[C@H](C1)c1cc(-c3cccc(Cl)c3Cl)cc3c1N2CCC3 | null | C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd] | COCCOC | C-C Coupling | Suzuki coupling with boronic acids | 64efaa37abe437fdebb17d9d55e8daecf2c7995b4abc7efe8c3132530542b64e | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(-c2cc3c4c(c2)[C@H]2CNCC[C@H]2N4CCC3)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].O-B(-O)-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9](-[Cl;D1;H0:10]):[c:11]>>[Cl;D1;H0:10]-[c:9](:[c:11]):[c;H0;D3;+0:6](-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5]):[c:7]:[c:8] | 125.9 | [{"value": 125.9, "product": "ClC1=C(C=CC=C1Cl)C=1C=C2CCCN3C2=C(C1)[C@@H]1[C@H]3CCN(C1)C(=O)OC(C)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Tert-butyl(±)-cis-2-bromo-5,6,8,9,11,11a-hexahydro-4H-pyrido[3′,4′:4,5]pyrrolo[3,2,1-ij]quinoline-10(7aH)-carboxylate (110 mg, 0.28 mmol) was dissolved in DME (4 mL). 2M aqueous sodium carbonate (0.75 ml) was added. 2,3-Dichlorophenylboronic acid (107 mg, 0.56 mmol) was added, followed by Pd2(dba)3(14.5 mg, 0.014 mmol)... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1cc2c3c(c1)[C@H]1C[NH]CC[C@H]1N3CCC2.c1ccccc1 | c1ccccc1.c1cc2c3c(c1)[C@H]1C[NH]CC[C@H]1N3CCC2 | c1ccccc1.c1cc2c3c(c1)[C@H]1C[NH]CC[C@H]1N3CCC2 | HBr.B | C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].COCCOC | null | null | CC(C)(C)OC(=O)N1CC[C@@H]2[C@H](C1)c1cc(Br)cc3c1N2CCC3.OB(O)c1cccc(Cl)c1Cl>C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].COCCOC>CC(C)(C)OC(=O)N1CC[C@@H]2[C@H](C1)c1cc(-c3cccc(Cl)c3Cl)cc3c1N2CCC3 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-5cbecf69a45d417b9fbfbe01898e22af | CC(C)(C)OC(=O)N1CC[C@@H]2[C@H](C1)c1cc(Br)cc3c1N2CCC3.OB(O)c1ccc(Cl)c(Cl)c1>>CC(C)(C)OC(=O)N1CC[C@@H]2[C@H](C1)c1cc(-c3ccc(Cl)c(Cl)c3)cc3c1N2CCC3 | BrC=1C=C2CCCN3C2=C(C1)[C@@H]1[C@H]3CCN(C1)C(=O)OC(C)(C)C.ClC=1C=C(C=CC1Cl)B(O)O>>ClC=1C=C(C=CC1Cl)C=1C=C2CCCN3C2=C(C1)[C@@H]1[C@H]3CCN(C1)C(=O)OC(C)(C)C | Br[c:16]1[cH:15][c:14]2[c:27]3[c:26]([cH:25]1)[CH2:31][CH2:30][CH2:29][N:28]3[C@@H:11]1[CH2:10][CH2:9][N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:13][C@@H:12]12.OB(O)[c:17]1[cH:18][cH:19][c:20]([Cl:21])[c:22]([Cl:23])[cH:24]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][C@@H:11... | CC(C)(C)OC(=O)N1CC[C@@H]2[C@H](C1)c1cc(Br)cc3c1N2CCC3.OB(O)c1ccc(Cl)c(Cl)c1 | CC(C)(C)OC(=O)N1CC[C@@H]2[C@H](C1)c1cc(-c3ccc(Cl)c(Cl)c3)cc3c1N2CCC3 | null | null | null | C-C Coupling | Suzuki coupling with boronic acids | 64efaa37abe437fdebb17d9d55e8daecf2c7995b4abc7efe8c3132530542b64e | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(-c2cc3c4c(c2)[C@H]2CNCC[C@H]2N4CCC3)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].O-B(-O)-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]>>[c:3]:[c:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]):[c:4]:[c:5] | null | [] | null | null | null | null | The title compound was prepared by the method of Example 109 from tert-butyl(±)-cis-2-bromo-5,6,8,9,11,11a-hexahydro-4H-pyrido[3′,4′:4,5]pyrrolo[3,2,1-ij]quinoline-10(7aH)-carboxylate (101.7 mg, 0.26 mmol) and 3,4-dichlorophenylboronic acid (97 mg, 0.52 mmol), after chromatographic purification (91.6 mg, 77%) as a whit... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1cc2c3c(c1)[C@H]1C[NH]CC[C@H]1N3CCC2.c1ccccc1 | c1ccccc1.c1cc2c3c(c1)[C@H]1C[NH]CC[C@H]1N3CCC2 | c1ccccc1.c1cc2c3c(c1)[C@H]1C[NH]CC[C@H]1N3CCC2 | HBr.B | null | null | null | CC(C)(C)OC(=O)N1CC[C@@H]2[C@H](C1)c1cc(Br)cc3c1N2CCC3.OB(O)c1ccc(Cl)c(Cl)c1>>CC(C)(C)OC(=O)N1CC[C@@H]2[C@H](C1)c1cc(-c3ccc(Cl)c(Cl)c3)cc3c1N2CCC3 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-cde78338b29647a1b343726363c1567c | CC(C)(C)OC(=O)N1CC[C@@H]2[C@H](C1)c1cc(Br)cc3c1N2CCC3.OB(O)c1ccc(C(F)(F)F)cc1Cl>>CC(C)(C)OC(=O)N1CC[C@@H]2[C@H](C1)c1cc(-c3ccc(C(F)(F)F)cc3Cl)cc3c1N2CCC3 | BrC=1C=C2CCCN3C2=C(C1)[C@@H]1[C@H]3CCN(C1)C(=O)OC(C)(C)C.ClC1=C(C=CC(=C1)C(F)(F)F)B(O)O>>ClC1=C(C=CC(=C1)C(F)(F)F)C=1C=C2CCCN3C2=C(C1)[C@@H]1[C@H]3CCN(C1)C(=O)OC(C)(C)C | Br[c:16]1[cH:15][c:14]2[c:30]3[c:29]([cH:28]1)[CH2:34][CH2:33][CH2:32][N:31]3[C@@H:11]1[CH2:10][CH2:9][N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:13][C@@H:12]12.OB(O)[c:17]1[cH:18][cH:19][c:20]([C:21]([F:22])([F:23])[F:24])[cH:25][c:26]1[Cl:27]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2... | CC(C)(C)OC(=O)N1CC[C@@H]2[C@H](C1)c1cc(Br)cc3c1N2CCC3.OB(O)c1ccc(C(F)(F)F)cc1Cl | CC(C)(C)OC(=O)N1CC[C@@H]2[C@H](C1)c1cc(-c3ccc(C(F)(F)F)cc3Cl)cc3c1N2CCC3 | null | null | null | C-C Coupling | Suzuki coupling with boronic acids | 64efaa37abe437fdebb17d9d55e8daecf2c7995b4abc7efe8c3132530542b64e | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(-c2cc3c4c(c2)[C@H]2CNCC[C@H]2N4CCC3)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].O-B(-O)-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9](-[Cl;D1;H0:10]):[c:11]>>[Cl;D1;H0:10]-[c:9](:[c:11]):[c;H0;D3;+0:6](-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5]):[c:7]:[c:8] | null | [] | null | null | null | null | The title compound was prepared by the method of Example 109 from tert-butyl(±)-cis-2-bromo-5,6,8,9,11,11a-hexahydro-4H-pyrido[3′,4′:4,5]pyrrolo[3,2,1-ij]quinoline-10(7aH)-carboxylate (63 mg, 0.16 mmol) and 2-chloro-4-(trifluoromethyl)phenylboronic acid (69 mg, 0.32 mmol), after chromatographic purification (35.9 mg, 4... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1cc2c3c(c1)[C@H]1C[NH]CC[C@H]1N3CCC2.c1ccccc1 | c1ccccc1.c1cc2c3c(c1)[C@H]1C[NH]CC[C@H]1N3CCC2 | c1ccccc1.c1cc2c3c(c1)[C@H]1C[NH]CC[C@H]1N3CCC2 | HBr.B | null | null | null | CC(C)(C)OC(=O)N1CC[C@@H]2[C@H](C1)c1cc(Br)cc3c1N2CCC3.OB(O)c1ccc(C(F)(F)F)cc1Cl>>CC(C)(C)OC(=O)N1CC[C@@H]2[C@H](C1)c1cc(-c3ccc(C(F)(F)F)cc3Cl)cc3c1N2CCC3 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-f2f53524841043028a6893ebb456e1bd | CC(C)(C)OC(=O)N1CC[C@@H]2[C@H](C1)c1cc(-c3cccc(Cl)c3Cl)cc3c1N2CCC3>>Clc1cccc(-c2cc3c4c(c2)[C@H]2CNCC[C@H]2N4CCC3)c1Cl | ClC1=C(C=CC=C1Cl)C=1C=C2CCCN3C2=C(C1)[C@@H]1[C@H]3CCN(C1)C(=O)OC(C)(C)C.[OH-].[Na+]>>ClC1=C(C=CC=C1Cl)C=1C=C2CCCN3C2=C(C1)[C@@H]1[C@H]3CCNC1 | CC(C)(C)OC(=O)[N:15]1[CH2:14][C@@H:13]2[c:11]3[c:10]4[c:9]([cH:8][c:7](-[c:6]5[cH:5][cH:4][cH:3][c:2]([Cl:1])[c:23]5[Cl:24])[cH:12]3)[CH2:22][CH2:21][CH2:20][N:19]4[C@@H:18]2[CH2:17][CH2:16]1>>[Cl:1][c:2]1[cH:3][cH:4][cH:5][c:6](-[c:7]2[cH:8][c:9]3[c:10]4[c:11]([cH:12]2)[C@H:13]2[CH2:14][NH:15][CH2:16][CH2:17][C@H:18]2... | CC(C)(C)OC(=O)N1CC[C@@H]2[C@H](C1)c1cc(-c3cccc(Cl)c3Cl)cc3c1N2CCC3 | Clc1cccc(-c2cc3c4c(c2)[C@H]2CNCC[C@H]2N4CCC3)c1Cl | null | null | C(Cl)Cl.C(=O)(C(F)(F)F)O | Reduction | Boc amine deprotection | 67aa5993ca12a9de3aab20b7fbe3684abc85bd36d1019a23212e08cda316e299 | a94b29c7264c852156fc1cdd4a0951a4fc26c06d0edc9e50c743825dbf79e3fd | c1ccc(-c2cc3c4c(c2)[C@H]2CNCC[C@H]2N4CCC3)cc1 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1](-[C:2]-[C:3])-[C:4]-[C:5]>>[C:3]-[C:2]-[NH;D2;+0:1]-[C:4]-[C:5] | 100 | [{"value": 100.0, "product": "ClC1=C(C=CC=C1Cl)C=1C=C2CCCN3C2=C(C1)[C@@H]1[C@H]3CCNC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 99.7, "product": "ClC1=C(C=CC=C1Cl)C=1C=C2CCCN3C2=C(C1)[C@@H]1[C@H]3CCNC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | Tert-butyl(±)-cis-2-(2,3-dichlorophenyl)-5,6,8,9,11,11a-hexahydro-4H-pyrido[3′,4′:4,5]pyrrolo[3,2,1-ij]quinoline-10(7aH)-carboxylate (55 mg, 0.12 mmol) was dissolved in 20% TFA in methylene chloride (4 mL) and was stirred at RT for 2 h. The reaction was solution was cooled to 0° C. and basified with 1 M NaOH until pH >... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Secondary amine | c1cc2c3c(c1)[C@H]1C[NH]CC[C@H]1N3CCC2 | c1cc2c3c(c1)[C@H]1CNCC[C@H]1N3CCC2 | c1ccccc1.c1cc2c3c(c1)[C@H]1CNCC[C@H]1N3CCC2 | HO- | C(Cl)Cl.C(=O)(C(F)(F)F)O | null | 2 | CC(C)(C)OC(=O)N1CC[C@@H]2[C@H](C1)c1cc(-c3cccc(Cl)c3Cl)cc3c1N2CCC3>C(Cl)Cl.C(=O)(C(F)(F)F)O>Clc1cccc(-c2cc3c4c(c2)[C@H]2CNCC[C@H]2N4CCC3)c1Cl |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-d7822d0a67454690a831684dfa227ebd | CC(C)(C)OC(=O)N1CC[C@@H]2[C@H](C1)c1cc(-c3ccc(Cl)c(Cl)c3)cc3c1N2CCC3>>Clc1ccc(-c2cc3c4c(c2)[C@H]2CNCC[C@H]2N4CCC3)cc1Cl | N.ClC=1C=C(C=CC1Cl)C=1C=C2CCCN3C2=C(C1)[C@@H]1[C@H]3CCN(C1)C(=O)OC(C)(C)C>>ClC=1C=C(C=CC1Cl)C=1C=C2CCCN3C2=C(C1)[C@@H]1[C@H]3CCNC1 | CC(C)(C)OC(=O)[N:14]1[CH2:13][C@@H:12]2[c:10]3[c:9]4[c:8]([cH:7][c:6](-[c:5]5[cH:4][cH:3][c:2]([Cl:1])[c:23]([Cl:24])[cH:22]5)[cH:11]3)[CH2:21][CH2:20][CH2:19][N:18]4[C@@H:17]2[CH2:16][CH2:15]1>>[Cl:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[cH:7][c:8]3[c:9]4[c:10]([cH:11]2)[C@H:12]2[CH2:13][NH:14][CH2:15][CH2:16][C@H:17]2[N:18... | CC(C)(C)OC(=O)N1CC[C@@H]2[C@H](C1)c1cc(-c3ccc(Cl)c(Cl)c3)cc3c1N2CCC3 | Clc1ccc(-c2cc3c4c(c2)[C@H]2CNCC[C@H]2N4CCC3)cc1Cl | null | null | null | Reduction | Boc amine deprotection | 67aa5993ca12a9de3aab20b7fbe3684abc85bd36d1019a23212e08cda316e299 | a94b29c7264c852156fc1cdd4a0951a4fc26c06d0edc9e50c743825dbf79e3fd | c1ccc(-c2cc3c4c(c2)[C@H]2CNCC[C@H]2N4CCC3)cc1 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1](-[C:2]-[C:3])-[C:4]-[C:5]>>[C:3]-[C:2]-[NH;D2;+0:1]-[C:4]-[C:5] | 101 | [{"value": 100.0, "product": "ClC=1C=C(C=CC1Cl)C=1C=C2CCCN3C2=C(C1)[C@@H]1[C@H]3CCNC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 101.0, "product": "ClC=1C=C(C=CC1Cl)C=1C=C2CCCN3C2=C(C1)[C@@H]1[C@H]3CCNC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | The title compound (72.6 mg, 100%) was prepared by the method of Example 112 from tert-butyl(±)-cis-2-(3,4-dichlorophenyl)-5,6,8,9,11,11a-hexahydro-4H-pyrido[3′,4′:4,5]pyrrolo[3,2,1-ij]quinoline-10(7aH)-carboxylate (90 mg, 0.20 mmol) as pale yellow amorphous solid. 1H NMR (CDCl3, 300 MHz) δ 7.58 (d, 1H, J=2.2 Hz), 7.41... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Secondary amine | c1cc2c3c(c1)[C@H]1C[NH]CC[C@H]1N3CCC2 | c1cc2c3c(c1)[C@H]1CNCC[C@H]1N3CCC2 | c1ccccc1.c1cc2c3c(c1)[C@H]1CNCC[C@H]1N3CCC2 | HO- | null | null | null | CC(C)(C)OC(=O)N1CC[C@@H]2[C@H](C1)c1cc(-c3ccc(Cl)c(Cl)c3)cc3c1N2CCC3>>Clc1ccc(-c2cc3c4c(c2)[C@H]2CNCC[C@H]2N4CCC3)cc1Cl |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-491f219a4f8548c29a74b377196d1254 | Clc1ccccc1-c1cc2c3c(c1)[C@H]1CNCC[C@H]1N3CC2.O=C(CCCCl)c1ccc(F)cc1>>O=C(CCCN1CC[C@@H]2[C@H](C1)c1cc(-c3ccccc3Cl)cc3c1N2CC3)c1ccc(F)cc1 | ClC1=C(C=CC=C1)C=1C=C2[C@@H]3[C@H](N4C2=C(C1)CC4)CCNC3.C(=O)([O-])[O-].[K+].[K+].ClCCCC(=O)C1=CC=C(C=C1)F>>ClC1=C(C=CC=C1)C=1C=C2[C@@H]3[C@H](N4C2=C(C1)CC4)CCN(C3)CCCC(=O)C3=CC=C(C=C3)F | [NH:6]1[CH2:7][CH2:8][C@@H:9]2[C@H:10]([CH2:11]1)[c:12]1[cH:13][c:14](-[c:15]3[cH:16][cH:17][cH:18][cH:19][c:20]3[Cl:21])[cH:22][c:23]3[c:24]1[N:25]2[CH2:26][CH2:27]3.Cl[CH2:5][CH2:4][CH2:3][C:2](=[O:1])[c:28]1[cH:29][cH:30][c:31]([F:32])[cH:33][cH:34]1>>[O:1]=[C:2]([CH2:3][CH2:4][CH2:5][N:6]1[CH2:7][CH2:8][C@@H:9]2[C@... | Clc1ccccc1-c1cc2c3c(c1)[C@H]1CNCC[C@H]1N3CC2.O=C(CCCCl)c1ccc(F)cc1 | O=C(CCCN1CC[C@@H]2[C@H](C1)c1cc(-c3ccccc3Cl)cc3c1N2CC3)c1ccc(F)cc1 | null | null | CCC(=O)C | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 02f6a6f6bb970189d263cd7369423e1c4bdccfb16a159809ae4cf630d5db8e3f | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | O=C(CCCN1CC[C@@H]2[C@H](C1)c1cc(-c3ccccc3)cc3c1N2CC3)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] | 47 | [{"value": 47.0, "product": "ClC1=C(C=CC=C1)C=1C=C2[C@@H]3[C@H](N4C2=C(C1)CC4)CCN(C3)CCCC(=O)C3=CC=C(C=C3)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 46.6, "product": "ClC1=C(C=CC=C1)C=1C=C2[C@@H]3[C@H](N4C2=C(C1)CC4)CCN(C3)CCCC(=O)C3=CC=C(C=C3)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": f... | null | null | null | null | (±)-Cis-2-(2-chlorophenyl)-4,5,6a,7,8,9,10,10a-octahydropyrido[4,3-b]pyrrolo[3,2,1-hi]indole (26.4 mg, 0.085 mmol) 0.7 ml of MEK. KI (14 mg, 0.085 mmol) and K2CO3(22 mg, 0.26 mmol), and 4-chloro-4′-fluorobutyrophenone (22.2 mg, 0.11 mmol) were added. The suspension was refluxed for 48 h and then cooled to rt. The suspe... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | c1cc2c3c(c1)[C@H]1CNCC[C@H]1N3CC2 | c1cc2c3c(c1)[C@H]1C[NH]CC[C@H]1N3CC2 | c1ccccc1.c1ccccc1.c1cc2c3c(c1)[C@H]1C[NH]CC[C@H]1N3CC2 | HCl | CCC(=O)C | null | null | Clc1ccccc1-c1cc2c3c(c1)[C@H]1CNCC[C@H]1N3CC2.O=C(CCCCl)c1ccc(F)cc1>CCC(=O)C>O=C(CCCN1CC[C@@H]2[C@H](C1)c1cc(-c3ccccc3Cl)cc3c1N2CC3)c1ccc(F)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-975b907ba58e4c0ab0dc0d163168e0df | Clc1ccc(-c2cc3c4c(c2)[C@H]2CNCC[C@H]2N4CC3)c(Cl)c1.O=C(CCCCl)c1ccc(F)cc1>>O=C(CCCN1CC[C@@H]2[C@H](C1)c1cc(-c3ccc(Cl)cc3Cl)cc3c1N2CC3)c1ccc(F)cc1 | ClC1=C(C=CC(=C1)Cl)C=1C=C2[C@@H]3[C@H](N4C2=C(C1)CC4)CCNC3.ClCCCC(=O)C1=CC=C(C=C1)F.C(=O)([O-])[O-].[K+].[K+]>>ClC1=C(C=CC(=C1)Cl)C=1C=C2[C@@H]3[C@H](N4C2=C(C1)CC4)CCN(C3)CCCC(=O)C3=CC=C(C=C3)F | [NH:6]1[CH2:7][CH2:8][C@@H:9]2[C@H:10]([CH2:11]1)[c:12]1[cH:13][c:14](-[c:15]3[cH:16][cH:17][c:18]([Cl:19])[cH:20][c:21]3[Cl:22])[cH:23][c:24]3[c:25]1[N:26]2[CH2:27][CH2:28]3.Cl[CH2:5][CH2:4][CH2:3][C:2](=[O:1])[c:29]1[cH:30][cH:31][c:32]([F:33])[cH:34][cH:35]1>>[O:1]=[C:2]([CH2:3][CH2:4][CH2:5][N:6]1[CH2:7][CH2:8][C@@... | Clc1ccc(-c2cc3c4c(c2)[C@H]2CNCC[C@H]2N4CC3)c(Cl)c1.O=C(CCCCl)c1ccc(F)cc1 | O=C(CCCN1CC[C@@H]2[C@H](C1)c1cc(-c3ccc(Cl)cc3Cl)cc3c1N2CC3)c1ccc(F)cc1 | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 02f6a6f6bb970189d263cd7369423e1c4bdccfb16a159809ae4cf630d5db8e3f | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | O=C(CCCN1CC[C@@H]2[C@H](C1)c1cc(-c3ccccc3)cc3c1N2CC3)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] | 37.2 | [{"value": 37.0, "product": "ClC1=C(C=CC(=C1)Cl)C=1C=C2[C@@H]3[C@H](N4C2=C(C1)CC4)CCN(C3)CCCC(=O)C3=CC=C(C=C3)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 37.2, "product": "ClC1=C(C=CC(=C1)Cl)C=1C=C2[C@@H]3[C@H](N4C2=C(C1)CC4)CCN(C3)CCCC(=O)C3=CC=C(C=C3)F", "details": "CALCULATEDPERCENTYIELD", "is_des... | null | null | null | null | The title compound (36 mg, 37%) was prepared by the method of Example 189 from (±)-cis-2-(2,4-dichlorophenyl)-4,5,6a,7,8,9,10,10a-octahydropyrido[4,3-b]pyrrolo[3,2,1-hi]indole (65.8 mg, 0.19 mmol), 4-chloro-4′-fluorobutyrophenone (50.0 mg, 0.25 mmol), KI (31.5 mg, 0.19 mmol), and K2CO3(50.0 mg, 0.57 mmol) after chromat... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | c1cc2c3c(c1)[C@H]1CNCC[C@H]1N3CC2 | c1cc2c3c(c1)[C@H]1C[NH]CC[C@H]1N3CC2 | c1ccccc1.c1ccccc1.c1cc2c3c(c1)[C@H]1C[NH]CC[C@H]1N3CC2 | HCl | null | null | null | Clc1ccc(-c2cc3c4c(c2)[C@H]2CNCC[C@H]2N4CC3)c(Cl)c1.O=C(CCCCl)c1ccc(F)cc1>>O=C(CCCN1CC[C@@H]2[C@H](C1)c1cc(-c3ccc(Cl)cc3Cl)cc3c1N2CC3)c1ccc(F)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-3ad15b70f5594f3b9ff9d040c233224a | O=C(CCCCl)c1ccc(F)cc1.c1cc2c3c(c1)[C@H]1CNCC[C@H]1N3CC2>>O=C(CCCN1CC[C@@H]2[C@H](C1)c1cccc3c1N2CC3)c1ccc(F)cc1 | C1=C2[C@@H]3[C@H](N4C2=C(C=C1)CC4)CCNC3.ClCCCC(=O)C1=CC=C(C=C1)F.C(C)N(CC)CC.O1CCOCC1>>C1=C2[C@@H]3[C@H](N4C2=C(C=C1)CC4)CCN(C3)CCCC(=O)C3=CC=C(C=C3)F | 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][C@@H:9]2[C@H:10]([CH2:11]1)[c:12]1[cH:13][cH:14][cH:15][c:16]3[c:17]1[N:18]2[CH2:19][CH2:20]3>>[O:1]=[C:2]([CH2:3][CH2:4][CH2:5][N:6]1[CH2:7][CH2:8][C@@H:9]2[C@H:10]([CH2:11]1)[c:12]1[cH:13][cH:14][cH:15][c:16]3... | O=C(CCCCl)c1ccc(F)cc1.c1cc2c3c(c1)[C@H]1CNCC[C@H]1N3CC2 | O=C(CCCN1CC[C@@H]2[C@H](C1)c1cccc3c1N2CC3)c1ccc(F)cc1 | null | null | C1(=CC=CC=C1)C | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 02f6a6f6bb970189d263cd7369423e1c4bdccfb16a159809ae4cf630d5db8e3f | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | O=C(CCCN1CC[C@@H]2[C@H](C1)c1cccc3c1N2CC3)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] | 65 | [{"value": 65.0, "product": "C1=C2[C@@H]3[C@H](N4C2=C(C=C1)CC4)CCN(C3)CCCC(=O)C3=CC=C(C=C3)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 64.7, "product": "C1=C2[C@@H]3[C@H](N4C2=C(C=C1)CC4)CCN(C3)CCCC(=O)C3=CC=C(C=C3)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of (±)-cis-4,5,6a,7,8,9,10,10a-octahydropyrido[4.3-b]pyrrolo[3,2,1-hi]indole (2.8 g, 14 mmol), 4-chloro-4′-fluorobutyrophenone (4.21 g, 21 mmol), triethylamine (3 mL), KI (3.48 g, 21 mmol), dioxane (25 mL), and toluene (25 mL) was stirred and refluxed for 15 h under an atmosphere of nitrogen and then evaporat... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | c1cc2c3c(c1)[C@H]1CNCC[C@H]1N3CC2 | c1cc2c3c(c1)[C@H]1C[NH]CC[C@H]1N3CC2 | c1ccccc1.c1cc2c3c(c1)[C@H]1C[NH]CC[C@H]1N3CC2 | HCl | C1(=CC=CC=C1)C | null | null | O=C(CCCCl)c1ccc(F)cc1.c1cc2c3c(c1)[C@H]1CNCC[C@H]1N3CC2>C1(=CC=CC=C1)C>O=C(CCCN1CC[C@@H]2[C@H](C1)c1cccc3c1N2CC3)c1ccc(F)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-c6582830226047c181cb50d2e39a90aa | CC(C)(C)OC(=O)N1CC[C@H]2[C@@H](C1)c1cc(Br)cc3c1N2CC3.COc1ccc(B(O)O)c(F)c1>>COc1ccc(-c2cc3c4c(c2)[C@@H]2CN(C(=O)OC(C)(C)C)CC[C@@H]2N4CC3)c(F)c1 | BrC=1C=C2[C@H]3[C@@H](N4C2=C(C1)CC4)CCN(C3)C(=O)OC(C)(C)C.FC1=C(C=CC(=C1)OC)B(O)O>>FC1=C(C=CC(=C1)OC)C=1C=C2[C@H]3[C@@H](N4C2=C(C1)CC4)CCN(C3)C(=O)OC(C)(C)C | Br[c:7]1[cH:8][c:9]2[c:10]3[c:11]([cH:12]1)[C@@H:13]1[CH2:14][N:15]([C:16](=[O:17])[O:18][C:19]([CH3:20])([CH3:21])[CH3:22])[CH2:23][CH2:24][C@@H:25]1[N:26]3[CH2:27][CH2:28]2.OB(O)[c:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:31][c:29]1[F:30]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][c:9]3[c:10]4[c:11]([cH:12]2)[C@... | CC(C)(C)OC(=O)N1CC[C@H]2[C@@H](C1)c1cc(Br)cc3c1N2CC3.COc1ccc(B(O)O)c(F)c1 | COc1ccc(-c2cc3c4c(c2)[C@@H]2CN(C(=O)OC(C)(C)C)CC[C@@H]2N4CC3)c(F)c1 | null | null | null | C-C Coupling | Suzuki coupling with boronic acids | 9de9ab65f6e2a1708d752f9805ab4397c406115bb682ed6a843a36653cbfe352 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(-c2cc3c4c(c2)[C@@H]2CNCC[C@@H]2N4CC3)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].O-B(-O)-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9](-[F;D1;H0:10]):[c:11]>>[F;D1;H0:10]-[c:9](:[c:11]):[c;H0;D3;+0:6](-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5]):[c:7]:[c:8] | 55 | [{"value": 55.0, "product": "FC1=C(C=CC(=C1)OC)C=1C=C2[C@H]3[C@@H](N4C2=C(C1)CC4)CCN(C3)C(=O)OC(C)(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 54.7, "product": "FC1=C(C=CC(=C1)OC)C=1C=C2[C@H]3[C@@H](N4C2=C(C1)CC4)CCN(C3)C(=O)OC(C)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Tert-butyl(6aS,10aR)-2-(2-fluoro-4-methoxyphenyl)-4,5,7,8,10,10a-hexahydropyrido[4,3-b]pyrrolo[3,2,1-hi]indole-9(6aH)-carboxylate (116 mg, 55%) was prepared by the method of Example 89 step C from tert-butyl(6aS,10aR)-2-bromo-4,5,7,8,10,10a-hexahydropyrido[4,3-b]pyrrolo[3,2,1-hi]indole-9(6aH)-carboxylate (189 mg, 0.5 m... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1cc2c3c(c1)[C@@H]1C[NH]CC[C@@H]1N3CC2.c1ccccc1 | c1ccccc1.c1cc2c3c(c1)[C@@H]1C[NH]CC[C@@H]1N3CC2 | c1ccccc1.c1cc2c3c(c1)[C@@H]1C[NH]CC[C@@H]1N3CC2 | HBr.B | null | null | null | CC(C)(C)OC(=O)N1CC[C@H]2[C@@H](C1)c1cc(Br)cc3c1N2CC3.COc1ccc(B(O)O)c(F)c1>>COc1ccc(-c2cc3c4c(c2)[C@@H]2CN(C(=O)OC(C)(C)C)CC[C@@H]2N4CC3)c(F)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-9e135e9c0edb4f25b9b636576e3b6856 | CC(C)(C)OC(=O)N1CC[C@H]2[C@@H](C1)c1cc(Br)cc3c1N2CC3.CCOc1ccc(B(O)O)c(C(F)(F)F)c1>>CCOc1ccc(-c2cc3c4c(c2)[C@@H]2CN(C(=O)OC(C)(C)C)CC[C@@H]2N4CC3)c(C(F)(F)F)c1 | BrC=1C=C2[C@H]3[C@@H](N4C2=C(C1)CC4)CCN(C3)C(=O)OC(C)(C)C.C(C)OC1=CC(=C(C=C1)B(O)O)C(F)(F)F>>C(C)OC1=CC(=C(C=C1)C=1C=C2[C@H]3[C@@H](N4C2=C(C1)CC4)CCN(C3)C(=O)OC(C)(C)C)C(F)(F)F | Br[c:8]1[cH:9][c:10]2[c:11]3[c:12]([cH:13]1)[C@@H:14]1[CH2:15][N:16]([C:17](=[O:18])[O:19][C:20]([CH3:21])([CH3:22])[CH3:23])[CH2:24][CH2:25][C@@H:26]1[N:27]3[CH2:28][CH2:29]2.OB(O)[c:7]1[cH:6][cH:5][c:4]([O:3][CH2:2][CH3:1])[cH:35][c:30]1[C:31]([F:32])([F:33])[F:34]>>[CH3:1][CH2:2][O:3][c:4]1[cH:5][cH:6][c:7](-[c:8]2[... | CC(C)(C)OC(=O)N1CC[C@H]2[C@@H](C1)c1cc(Br)cc3c1N2CC3.CCOc1ccc(B(O)O)c(C(F)(F)F)c1 | CCOc1ccc(-c2cc3c4c(c2)[C@@H]2CN(C(=O)OC(C)(C)C)CC[C@@H]2N4CC3)c(C(F)(F)F)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 | O.COCCOC | C-C Coupling | Suzuki coupling with boronic acids | 9de9ab65f6e2a1708d752f9805ab4397c406115bb682ed6a843a36653cbfe352 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(-c2cc3c4c(c2)[C@@H]2CNCC[C@@H]2N4CC3)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].O-B(-O)-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9](-[C:10](-[F;D1;H0:11])(-[F;D1;H0:12])-[F;D1;H0:13]):[c:14]>>[F;D1;H0:11]-[C:10](-[F;D1;H0:12])(-[F;D1;H0:13])-[c:9](:[c:14]):[c;H0;D3;+0:6](-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5]):[c:7]:[c:8] | 57.3 | [{"value": 57.0, "product": "C(C)OC1=CC(=C(C=C1)C=1C=C2[C@H]3[C@@H](N4C2=C(C1)CC4)CCN(C3)C(=O)OC(C)(C)C)C(F)(F)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 57.3, "product": "C(C)OC1=CC(=C(C=C1)C=1C=C2[C@H]3[C@@H](N4C2=C(C1)CC4)CCN(C3)C(=O)OC(C)(C)C)C(F)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_d... | null | null | null | null | Tert-butyl(6aS,10aR)-2-bromo-4,5,7,8,10,10a-hexahydropyrido[4,3-b]pyrrolo[3,2,1-hi]indole-9(6aH)carboxylate (189 mg, 0.5 mmol) was dissolved in DME (7.8 mL). Ba(OH)2 8H2O (236.6 mg, 0.75 mmol) in H2O (2.6 mL) was added. 4-ethoxy-2-trifluoromethylphenyl boronic acid (140 mg, 0.6 mmol) was added followed by Pd(PPh3)4 (12... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1cc2c3c(c1)[C@@H]1C[NH]CC[C@@H]1N3CC2.c1ccccc1 | c1ccccc1.c1cc2c3c(c1)[C@@H]1C[NH]CC[C@@H]1N3CC2 | c1ccccc1.c1cc2c3c(c1)[C@@H]1C[NH]CC[C@@H]1N3CC2 | HBr.B | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.O.COCCOC | null | null | CC(C)(C)OC(=O)N1CC[C@H]2[C@@H](C1)c1cc(Br)cc3c1N2CC3.CCOc1ccc(B(O)O)c(C(F)(F)F)c1>C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.O.COCCOC>CCOc1ccc(-c2cc3c4c(c2)[C@@H]2CN(C(=O)OC(C)(C)C)CC[C@@H]2N4... |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-08262f82779f438787f0bb2dc905239e | CC(C)(C)OC(=O)N1CC[C@H]2[C@@H](C1)c1cc(Br)cc3c1N2CC3.OB(O)c1ccc(Cl)cc1F>>CC(C)(C)OC(=O)N1CC[C@H]2[C@@H](C1)c1cc(-c3ccc(Cl)cc3F)cc3c1N2CC3 | BrC=1C=C2[C@H]3[C@@H](N4C2=C(C1)CC4)CCN(C3)C(=O)OC(C)(C)C.ClC1=CC(=C(C=C1)B(O)O)F>>ClC1=CC(=C(C=C1)C=1C=C2[C@H]3[C@@H](N4C2=C(C1)CC4)CCN(C3)C(=O)OC(C)(C)C)F | Br[c:16]1[cH:15][c:14]2[c:27]3[c:26]([cH:25]1)[CH2:30][CH2:29][N:28]3[C@H:11]1[CH2:10][CH2:9][N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:13][C@H:12]12.OB(O)[c:17]1[cH:18][cH:19][c:20]([Cl:21])[cH:22][c:23]1[F:24]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][C@H:11]2[C@@H:12]([C... | CC(C)(C)OC(=O)N1CC[C@H]2[C@@H](C1)c1cc(Br)cc3c1N2CC3.OB(O)c1ccc(Cl)cc1F | CC(C)(C)OC(=O)N1CC[C@H]2[C@@H](C1)c1cc(-c3ccc(Cl)cc3F)cc3c1N2CC3 | null | null | null | C-C Coupling | Suzuki coupling with boronic acids | 9de9ab65f6e2a1708d752f9805ab4397c406115bb682ed6a843a36653cbfe352 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(-c2cc3c4c(c2)[C@@H]2CNCC[C@@H]2N4CC3)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].O-B(-O)-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9](-[F;D1;H0:10]):[c:11]>>[F;D1;H0:10]-[c:9](:[c:11]):[c;H0;D3;+0:6](-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5]):[c:7]:[c:8] | null | [] | null | null | null | null | The title compound was prepared by the method of Example 89 step C from tert-butyl(6aS,10aR)-2-bromo-4,5,7,8,10,10a-hexahydropyrido[4,3-b]pyrrolo[3,2,1-hi]indole-9(6aH)carboxylate (189 mg, 0.5 mmol) and corresponding 4-chloro-2-fluorophenyl boronic acid (175 mg, 1.0 mmol) to afford after chromatographic purification th... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1cc2c3c(c1)[C@@H]1C[NH]CC[C@@H]1N3CC2.c1ccccc1 | c1ccccc1.c1cc2c3c(c1)[C@@H]1C[NH]CC[C@@H]1N3CC2 | c1ccccc1.c1cc2c3c(c1)[C@@H]1C[NH]CC[C@@H]1N3CC2 | HBr.B | null | null | null | CC(C)(C)OC(=O)N1CC[C@H]2[C@@H](C1)c1cc(Br)cc3c1N2CC3.OB(O)c1ccc(Cl)cc1F>>CC(C)(C)OC(=O)N1CC[C@H]2[C@@H](C1)c1cc(-c3ccc(Cl)cc3F)cc3c1N2CC3 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-297cbd9a04dc4be484764040c2f509eb | CC(C)(C)OC(=O)N1CC[C@H]2[C@@H](C1)c1cc(Br)cc3c1N2CC3.CC(C)Oc1ccc(B(O)O)c(C(F)(F)F)c1>>CC(C)Oc1ccc(-c2cc3c4c(c2)[C@@H]2CN(C(=O)OC(C)(C)C)CC[C@@H]2N4CC3)c(C(F)(F)F)c1 | BrC=1C=C2[C@H]3[C@@H](N4C2=C(C1)CC4)CCN(C3)C(=O)OC(C)(C)C.C(C)(C)OC1=CC(=C(C=C1)B(O)O)C(F)(F)F>>C(C)(C)OC1=CC(=C(C=C1)C=1C=C2[C@H]3[C@@H](N4C2=C(C1)CC4)CCN(C3)C(=O)OC(C)(C)C)C(F)(F)F | Br[c:9]1[cH:10][c:11]2[c:12]3[c:13]([cH:14]1)[C@@H:15]1[CH2:16][N:17]([C:18](=[O:19])[O:20][C:21]([CH3:22])([CH3:23])[CH3:24])[CH2:25][CH2:26][C@@H:27]1[N:28]3[CH2:29][CH2:30]2.OB(O)[c:8]1[cH:7][cH:6][c:5]([O:4][CH:2]([CH3:1])[CH3:3])[cH:36][c:31]1[C:32]([F:33])([F:34])[F:35]>>[CH3:1][CH:2]([CH3:3])[O:4][c:5]1[cH:6][cH... | CC(C)(C)OC(=O)N1CC[C@H]2[C@@H](C1)c1cc(Br)cc3c1N2CC3.CC(C)Oc1ccc(B(O)O)c(C(F)(F)F)c1 | CC(C)Oc1ccc(-c2cc3c4c(c2)[C@@H]2CN(C(=O)OC(C)(C)C)CC[C@@H]2N4CC3)c(C(F)(F)F)c1 | null | null | null | C-C Coupling | Suzuki coupling with boronic acids | 9de9ab65f6e2a1708d752f9805ab4397c406115bb682ed6a843a36653cbfe352 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(-c2cc3c4c(c2)[C@@H]2CNCC[C@@H]2N4CC3)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].O-B(-O)-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9](-[C:10](-[F;D1;H0:11])(-[F;D1;H0:12])-[F;D1;H0:13]):[c:14]>>[F;D1;H0:11]-[C:10](-[F;D1;H0:12])(-[F;D1;H0:13])-[c:9](:[c:14]):[c;H0;D3;+0:6](-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5]):[c:7]:[c:8] | null | [] | null | null | null | null | The title compound was prepared by the method of Example 89 step C from tert-butyl(6aS,10aR)-2-bromo-4,5,7,8,10,10a-hexahydropyrido[4,3-b]pyrrolo[3,2,1-hi]indole-9(6aH)carboxylate (189 mg, 0.5 mmol) and 4-isopropoxy-2-(trifluoromethyl)phenylboronic acid (248 mg, 1.0 mmol) to afford after chromatographic purification th... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1cc2c3c(c1)[C@@H]1C[NH]CC[C@@H]1N3CC2.c1ccccc1 | c1ccccc1.c1cc2c3c(c1)[C@@H]1C[NH]CC[C@@H]1N3CC2 | c1ccccc1.c1cc2c3c(c1)[C@@H]1C[NH]CC[C@@H]1N3CC2 | HBr.B | null | null | null | CC(C)(C)OC(=O)N1CC[C@H]2[C@@H](C1)c1cc(Br)cc3c1N2CC3.CC(C)Oc1ccc(B(O)O)c(C(F)(F)F)c1>>CC(C)Oc1ccc(-c2cc3c4c(c2)[C@@H]2CN(C(=O)OC(C)(C)C)CC[C@@H]2N4CC3)c(C(F)(F)F)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-c1727a635a0746349e92cbf7f5793a38 | CC(C)(C)OC(=O)N1CC[C@H]2[C@@H](C1)c1cc(Br)cc3c1N2CC3.COc1ccc(B(O)O)c(C(F)(F)F)c1>>COc1ccc(-c2cc3c4c(c2)[C@@H]2CN(C(=O)OC(C)(C)C)CC[C@@H]2N4CC3)c(C(F)(F)F)c1 | BrC=1C=C2[C@H]3[C@@H](N4C2=C(C1)CC4)CCN(C3)C(=O)OC(C)(C)C.COC1=CC(=C(C=C1)B(O)O)C(F)(F)F>>COC1=CC(=C(C=C1)C=1C=C2[C@H]3[C@@H](N4C2=C(C1)CC4)CCN(C3)C(=O)OC(C)(C)C)C(F)(F)F | Br[c:7]1[cH:8][c:9]2[c:10]3[c:11]([cH:12]1)[C@@H:13]1[CH2:14][N:15]([C:16](=[O:17])[O:18][C:19]([CH3:20])([CH3:21])[CH3:22])[CH2:23][CH2:24][C@@H:25]1[N:26]3[CH2:27][CH2:28]2.OB(O)[c:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:34][c:29]1[C:30]([F:31])([F:32])[F:33]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][c:9]3[c:1... | CC(C)(C)OC(=O)N1CC[C@H]2[C@@H](C1)c1cc(Br)cc3c1N2CC3.COc1ccc(B(O)O)c(C(F)(F)F)c1 | COc1ccc(-c2cc3c4c(c2)[C@@H]2CN(C(=O)OC(C)(C)C)CC[C@@H]2N4CC3)c(C(F)(F)F)c1 | null | null | null | C-C Coupling | Suzuki coupling with boronic acids | 9de9ab65f6e2a1708d752f9805ab4397c406115bb682ed6a843a36653cbfe352 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(-c2cc3c4c(c2)[C@@H]2CNCC[C@@H]2N4CC3)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].O-B(-O)-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9](-[C:10](-[F;D1;H0:11])(-[F;D1;H0:12])-[F;D1;H0:13]):[c:14]>>[F;D1;H0:11]-[C:10](-[F;D1;H0:12])(-[F;D1;H0:13])-[c:9](:[c:14]):[c;H0;D3;+0:6](-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5]):[c:7]:[c:8] | null | [] | null | null | null | null | The title compound was prepared by the method of Example 89 step C from tert-butyl(6aS,10aR)-2-bromo-4,5,7,8,10,10a-hexahydropyrido[4,3-b]pyrrolo[3,2,1-hi]indole-9(6aH)carboxylate (189 mg, 0.5 mmol) and 4-methoxy-2-(trifluoromethyl)phenylboronic acid (248 mg, 1.0 mmol) to afford after chromatographic purification the t... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1cc2c3c(c1)[C@@H]1C[NH]CC[C@@H]1N3CC2.c1ccccc1 | c1ccccc1.c1cc2c3c(c1)[C@@H]1C[NH]CC[C@@H]1N3CC2 | c1ccccc1.c1cc2c3c(c1)[C@@H]1C[NH]CC[C@@H]1N3CC2 | HBr.B | null | null | null | CC(C)(C)OC(=O)N1CC[C@H]2[C@@H](C1)c1cc(Br)cc3c1N2CC3.COc1ccc(B(O)O)c(C(F)(F)F)c1>>COc1ccc(-c2cc3c4c(c2)[C@@H]2CN(C(=O)OC(C)(C)C)CC[C@@H]2N4CC3)c(C(F)(F)F)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-9a44b35cc9334b798c7b489d1bb9df08 | CC(C)(C)OC(=O)N1CC[C@H]2[C@@H](C1)c1cc(Br)cc3c1N2CC3.OB(O)c1ccccc1>>CC(C)(C)OC(=O)N1CC[C@H]2[C@@H](C1)c1cc(-c3ccccc3)cc3c1N2CC3 | BrC=1C=C2[C@H]3[C@@H](N4C2=C(C1)CC4)CCN(C3)C(=O)OC(C)(C)C.C1(=CC=CC=C1)B(O)O>>C1(=CC=CC=C1)C=1C=C2[C@H]3[C@@H](N4C2=C(C1)CC4)CCN(C3)C(=O)OC(C)(C)C | Br[c:16]1[cH:15][c:14]2[c:25]3[c:24]([cH:23]1)[CH2:28][CH2:27][N:26]3[C@H:11]1[CH2:10][CH2:9][N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:13][C@H:12]12.OB(O)[c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][C@H:11]2[C@@H:12]([CH2:13]1)[c:14... | CC(C)(C)OC(=O)N1CC[C@H]2[C@@H](C1)c1cc(Br)cc3c1N2CC3.OB(O)c1ccccc1 | CC(C)(C)OC(=O)N1CC[C@H]2[C@@H](C1)c1cc(-c3ccccc3)cc3c1N2CC3 | null | null | null | C-C Coupling | Suzuki coupling with boronic acids | 9de9ab65f6e2a1708d752f9805ab4397c406115bb682ed6a843a36653cbfe352 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(-c2cc3c4c(c2)[C@@H]2CNCC[C@@H]2N4CC3)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].O-B(-O)-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]>>[c:3]:[c:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]):[c:4]:[c:5] | null | [] | null | null | null | null | The title compound was prepared by the method of Example 89 step C from tert-butyl(6aS,10aR)-2-bromo-4,5,7,8,10,10a-hexahydropyrido[4,3-b]pyrrolo[3,2,1-hi]indole-9(6aH)carboxylate (189 mg, 0.5 mmol) and phenylboronic acid (122 mg, 1.0 mmol) to afford after chromatographic purification the title compound (74 mg, 20%).
C... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1cc2c3c(c1)[C@@H]1C[NH]CC[C@@H]1N3CC2.c1ccccc1 | c1ccccc1.c1cc2c3c(c1)[C@@H]1C[NH]CC[C@@H]1N3CC2 | c1ccccc1.c1cc2c3c(c1)[C@@H]1C[NH]CC[C@@H]1N3CC2 | HBr.B | null | null | null | CC(C)(C)OC(=O)N1CC[C@H]2[C@@H](C1)c1cc(Br)cc3c1N2CC3.OB(O)c1ccccc1>>CC(C)(C)OC(=O)N1CC[C@H]2[C@@H](C1)c1cc(-c3ccccc3)cc3c1N2CC3 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-ec3b2caddea8466ab51f310c8e87217b | CC(C)(C)OC(=O)N1CC[C@H]2[C@@H](C1)c1cc(Br)cc3c1N2CC3.Cc1ccccc1B(O)O>>Cc1ccccc1-c1cc2c3c(c1)[C@@H]1CN(C(=O)OC(C)(C)C)CC[C@@H]1N3CC2 | BrC=1C=C2[C@H]3[C@@H](N4C2=C(C1)CC4)CCN(C3)C(=O)OC(C)(C)C.CC1=C(C=CC=C1)B(O)O>>CC1=C(C=CC=C1)C=1C=C2[C@H]3[C@@H](N4C2=C(C1)CC4)CCN(C3)C(=O)OC(C)(C)C | Br[c:8]1[cH:9][c:10]2[c:11]3[c:12]([cH:13]1)[C@@H:14]1[CH2:15][N:16]([C:17](=[O:18])[O:19][C:20]([CH3:21])([CH3:22])[CH3:23])[CH2:24][CH2:25][C@@H:26]1[N:27]3[CH2:28][CH2:29]2.OB(O)[c:7]1[c:2]([CH3:1])[cH:3][cH:4][cH:5][cH:6]1>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][cH:6][c:7]1-[c:8]1[cH:9][c:10]2[c:11]3[c:12]([cH:13]1)[C@@H:... | CC(C)(C)OC(=O)N1CC[C@H]2[C@@H](C1)c1cc(Br)cc3c1N2CC3.Cc1ccccc1B(O)O | Cc1ccccc1-c1cc2c3c(c1)[C@@H]1CN(C(=O)OC(C)(C)C)CC[C@@H]1N3CC2 | null | null | null | C-C Coupling | Suzuki coupling with boronic acids | 9de9ab65f6e2a1708d752f9805ab4397c406115bb682ed6a843a36653cbfe352 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(-c2cc3c4c(c2)[C@@H]2CNCC[C@@H]2N4CC3)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].O-B(-O)-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9](-[C;D1;H3:10]):[c:11]>>[C;D1;H3:10]-[c:9](:[c:11]):[c;H0;D3;+0:6](-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5]):[c:7]:[c:8] | null | [] | null | null | null | null | The title compound was prepared by the method of Example 89 step C from tert-butyl(6aS,10aR)-2-bromo-4,5,7,8,10,10a-hexahydropyrido[4,3-b]pyrrolo[3,2,1-hi]indole-9(6aH)carboxylate (189 mg, 0.5 mmol) and 2-methylphenylboronic acid (136 mg, 1.0 mmol) to afford after chromatographic purification the title compound (90 mg,... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1cc2c3c(c1)[C@@H]1C[NH]CC[C@@H]1N3CC2.c1ccccc1 | c1ccccc1.c1cc2c3c(c1)[C@@H]1C[NH]CC[C@@H]1N3CC2 | c1ccccc1.c1cc2c3c(c1)[C@@H]1C[NH]CC[C@@H]1N3CC2 | HBr.B | null | null | null | CC(C)(C)OC(=O)N1CC[C@H]2[C@@H](C1)c1cc(Br)cc3c1N2CC3.Cc1ccccc1B(O)O>>Cc1ccccc1-c1cc2c3c(c1)[C@@H]1CN(C(=O)OC(C)(C)C)CC[C@@H]1N3CC2 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-29c1fe2e500a42fe8058fd53cc60cf68 | CC(C)(C)OC(=O)N1CC[C@H]2[C@@H](C1)c1cc(Br)cc3c1N2CC3.OB(O)c1ccccc1C(F)(F)F>>CC(C)(C)OC(=O)N1CC[C@H]2[C@@H](C1)c1cc(-c3ccccc3C(F)(F)F)cc3c1N2CC3 | BrC=1C=C2[C@H]3[C@@H](N4C2=C(C1)CC4)CCN(C3)C(=O)OC(C)(C)C.FC(C1=C(C=CC=C1)B(O)O)(F)F>>FC(C1=C(C=CC=C1)C=1C=C2[C@H]3[C@@H](N4C2=C(C1)CC4)CCN(C3)C(=O)OC(C)(C)C)(F)F | Br[c:16]1[cH:15][c:14]2[c:29]3[c:28]([cH:27]1)[CH2:32][CH2:31][N:30]3[C@H:11]1[CH2:10][CH2:9][N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:13][C@H:12]12.OB(O)[c:17]1[cH:18][cH:19][cH:20][cH:21][c:22]1[C:23]([F:24])([F:25])[F:26]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][C@H:11... | CC(C)(C)OC(=O)N1CC[C@H]2[C@@H](C1)c1cc(Br)cc3c1N2CC3.OB(O)c1ccccc1C(F)(F)F | CC(C)(C)OC(=O)N1CC[C@H]2[C@@H](C1)c1cc(-c3ccccc3C(F)(F)F)cc3c1N2CC3 | null | null | null | C-C Coupling | Suzuki coupling with boronic acids | 9de9ab65f6e2a1708d752f9805ab4397c406115bb682ed6a843a36653cbfe352 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(-c2cc3c4c(c2)[C@@H]2CNCC[C@@H]2N4CC3)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].O-B(-O)-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9](-[C:10](-[F;D1;H0:11])(-[F;D1;H0:12])-[F;D1;H0:13]):[c:14]>>[F;D1;H0:11]-[C:10](-[F;D1;H0:12])(-[F;D1;H0:13])-[c:9](:[c:14]):[c;H0;D3;+0:6](-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5]):[c:7]:[c:8] | null | [] | null | null | null | null | The title compound was prepared by the method of Example 89 step C from tert-butyl(6aS,10aR)-2-bromo-4,5,7,8,10,10a-hexahydropyrido[4,3-b]pyrrolo[3,2,1-hi]indole-9(6aH)carboxylate (189 mg, 0.5 mmol) and 2-(trifluoromethyl)phenylboronic acid (190 mg, 1.0 mmol) to afford after chromatographic purification the title compo... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1cc2c3c(c1)[C@@H]1C[NH]CC[C@@H]1N3CC2.c1ccccc1 | c1ccccc1.c1cc2c3c(c1)[C@@H]1C[NH]CC[C@@H]1N3CC2 | c1ccccc1.c1cc2c3c(c1)[C@@H]1C[NH]CC[C@@H]1N3CC2 | HBr.B | null | null | null | CC(C)(C)OC(=O)N1CC[C@H]2[C@@H](C1)c1cc(Br)cc3c1N2CC3.OB(O)c1ccccc1C(F)(F)F>>CC(C)(C)OC(=O)N1CC[C@H]2[C@@H](C1)c1cc(-c3ccccc3C(F)(F)F)cc3c1N2CC3 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-9243ede4e3bc485695ab85173606d66b | CC(C)(C)OC(=O)N1CC[C@H]2[C@@H](C1)c1cc(Br)cc3c1N2CC3.COc1ccc(B(O)O)cc1OC>>COc1ccc(-c2cc3c4c(c2)[C@@H]2CN(C(=O)OC(C)(C)C)CC[C@@H]2N4CC3)cc1OC | BrC=1C=C2[C@H]3[C@@H](N4C2=C(C1)CC4)CCN(C3)C(=O)OC(C)(C)C.COC=1C=C(C=CC1OC)B(O)O>>COC=1C=C(C=CC1OC)C=1C=C2[C@H]3[C@@H](N4C2=C(C1)CC4)CCN(C3)C(=O)OC(C)(C)C | Br[c:7]1[cH:8][c:9]2[c:10]3[c:11]([cH:12]1)[C@@H:13]1[CH2:14][N:15]([C:16](=[O:17])[O:18][C:19]([CH3:20])([CH3:21])[CH3:22])[CH2:23][CH2:24][C@@H:25]1[N:26]3[CH2:27][CH2:28]2.OB(O)[c:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[c:30]([O:31][CH3:32])[cH:29]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][c:9]3[c:10]4[c:11]([c... | CC(C)(C)OC(=O)N1CC[C@H]2[C@@H](C1)c1cc(Br)cc3c1N2CC3.COc1ccc(B(O)O)cc1OC | COc1ccc(-c2cc3c4c(c2)[C@@H]2CN(C(=O)OC(C)(C)C)CC[C@@H]2N4CC3)cc1OC | null | null | null | C-C Coupling | Suzuki coupling with boronic acids | 9de9ab65f6e2a1708d752f9805ab4397c406115bb682ed6a843a36653cbfe352 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(-c2cc3c4c(c2)[C@@H]2CNCC[C@@H]2N4CC3)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].O-B(-O)-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]>>[c:3]:[c:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]):[c:4]:[c:5] | null | [] | null | null | null | null | The title compound was prepared by the method of Example 89 step C from tert-butyl(6aS,10aR)-2-bromo-4,5,7,8,10,10a-hexahydropyrido[4,3-b]pyrrolo[3,2,1-hi]indole-9(6aH)carboxylate (189 mg, 0.5 mmol) and corresponding 3,4-dimethoxyphenyl boronic acid (182 mg, 1.0 mmol) to afford after chromatographic purification the ti... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1cc2c3c(c1)[C@@H]1C[NH]CC[C@@H]1N3CC2.c1ccccc1 | c1ccccc1.c1cc2c3c(c1)[C@@H]1C[NH]CC[C@@H]1N3CC2 | c1ccccc1.c1cc2c3c(c1)[C@@H]1C[NH]CC[C@@H]1N3CC2 | HBr.B | null | null | null | CC(C)(C)OC(=O)N1CC[C@H]2[C@@H](C1)c1cc(Br)cc3c1N2CC3.COc1ccc(B(O)O)cc1OC>>COc1ccc(-c2cc3c4c(c2)[C@@H]2CN(C(=O)OC(C)(C)C)CC[C@@H]2N4CC3)cc1OC |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-105d7f2965fb4eb6baa12e99d277fb6e | CC(C)(C)OC(=O)N1CC[C@H]2[C@@H](C1)c1cc(Br)cc3c1N2CC3.OB(O)c1cc(Cl)ccc1Cl>>CC(C)(C)OC(=O)N1CC[C@H]2[C@@H](C1)c1cc(-c3cc(Cl)ccc3Cl)cc3c1N2CC3 | BrC=1C=C2[C@H]3[C@@H](N4C2=C(C1)CC4)CCN(C3)C(=O)OC(C)(C)C.ClC1=C(C=C(C=C1)Cl)B(O)O>>ClC1=C(C=C(C=C1)Cl)C=1C=C2[C@H]3[C@@H](N4C2=C(C1)CC4)CCN(C3)C(=O)OC(C)(C)C | Br[c:16]1[cH:15][c:14]2[c:27]3[c:26]([cH:25]1)[CH2:30][CH2:29][N:28]3[C@H:11]1[CH2:10][CH2:9][N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:13][C@H:12]12.OB(O)[c:17]1[cH:18][c:19]([Cl:20])[cH:21][cH:22][c:23]1[Cl:24]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][C@H:11]2[C@@H:12]([... | CC(C)(C)OC(=O)N1CC[C@H]2[C@@H](C1)c1cc(Br)cc3c1N2CC3.OB(O)c1cc(Cl)ccc1Cl | CC(C)(C)OC(=O)N1CC[C@H]2[C@@H](C1)c1cc(-c3cc(Cl)ccc3Cl)cc3c1N2CC3 | null | null | null | C-C Coupling | Suzuki coupling with boronic acids | 9de9ab65f6e2a1708d752f9805ab4397c406115bb682ed6a843a36653cbfe352 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(-c2cc3c4c(c2)[C@@H]2CNCC[C@@H]2N4CC3)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].O-B(-O)-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9](-[Cl;D1;H0:10]):[c:11]>>[Cl;D1;H0:10]-[c:9](:[c:11]):[c;H0;D3;+0:6](-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5]):[c:7]:[c:8] | null | [] | null | null | null | null | The title compound was prepared by the method of Example 89 step C from tert-butyl(6aS,10aR)-2-bromo-4,5,7,8,10,10a-hexahydropyrido[4,3-b]pyrrolo[3,2,1-hi]indole-9(6aH)carboxylate (189 mg, 0.5 mmol) and 2,5-dichlorophenylboronic acid (191 mg, 1.0 mmol) to afford after chromatographic purification the title compound (10... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1cc2c3c(c1)[C@@H]1C[NH]CC[C@@H]1N3CC2.c1ccccc1 | c1ccccc1.c1cc2c3c(c1)[C@@H]1C[NH]CC[C@@H]1N3CC2 | c1ccccc1.c1cc2c3c(c1)[C@@H]1C[NH]CC[C@@H]1N3CC2 | HBr.B | null | null | null | CC(C)(C)OC(=O)N1CC[C@H]2[C@@H](C1)c1cc(Br)cc3c1N2CC3.OB(O)c1cc(Cl)ccc1Cl>>CC(C)(C)OC(=O)N1CC[C@H]2[C@@H](C1)c1cc(-c3cc(Cl)ccc3Cl)cc3c1N2CC3 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-ce5e509b1c2544f5ad3c691b29c8d57e | CC(C)(C)OC(=O)N1CC[C@H]2[C@@H](C1)c1cc(Br)cc3c1N2CC3.OB(O)c1cc(Cl)cc(Cl)c1>>CC(C)(C)OC(=O)N1CC[C@H]2[C@@H](C1)c1cc(-c3cc(Cl)cc(Cl)c3)cc3c1N2CC3 | BrC=1C=C2[C@H]3[C@@H](N4C2=C(C1)CC4)CCN(C3)C(=O)OC(C)(C)C.ClC=1C=C(C=C(C1)Cl)B(O)O>>ClC=1C=C(C=C(C1)Cl)C=1C=C2[C@H]3[C@@H](N4C2=C(C1)CC4)CCN(C3)C(=O)OC(C)(C)C | Br[c:16]1[cH:15][c:14]2[c:27]3[c:26]([cH:25]1)[CH2:30][CH2:29][N:28]3[C@H:11]1[CH2:10][CH2:9][N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:13][C@H:12]12.OB(O)[c:17]1[cH:18][c:19]([Cl:20])[cH:21][c:22]([Cl:23])[cH:24]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][C@H:11]2[C@@H:12]... | CC(C)(C)OC(=O)N1CC[C@H]2[C@@H](C1)c1cc(Br)cc3c1N2CC3.OB(O)c1cc(Cl)cc(Cl)c1 | CC(C)(C)OC(=O)N1CC[C@H]2[C@@H](C1)c1cc(-c3cc(Cl)cc(Cl)c3)cc3c1N2CC3 | null | null | null | C-C Coupling | Suzuki coupling with boronic acids | 9de9ab65f6e2a1708d752f9805ab4397c406115bb682ed6a843a36653cbfe352 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(-c2cc3c4c(c2)[C@@H]2CNCC[C@@H]2N4CC3)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].O-B(-O)-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]>>[c:3]:[c:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]):[c:4]:[c:5] | null | [] | null | null | null | null | The title compound was prepared by the method of Example 89 step C from tert-butyl(6aS,10aR)-2-bromo-4,5,7,8,10,10a-hexahydropyrido[4,3-b]pyrrolo[3,2,1-hi]indole-9(6aH)carboxylate (189 mg, 0.5 mmol) and 3,5-dichlorophenylboronic acid (191 mg, 1.0 mmol) to afford after chromatographic purification the title compound (85... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1cc2c3c(c1)[C@@H]1C[NH]CC[C@@H]1N3CC2.c1ccccc1 | c1ccccc1.c1cc2c3c(c1)[C@@H]1C[NH]CC[C@@H]1N3CC2 | c1ccccc1.c1cc2c3c(c1)[C@@H]1C[NH]CC[C@@H]1N3CC2 | HBr.B | null | null | null | CC(C)(C)OC(=O)N1CC[C@H]2[C@@H](C1)c1cc(Br)cc3c1N2CC3.OB(O)c1cc(Cl)cc(Cl)c1>>CC(C)(C)OC(=O)N1CC[C@H]2[C@@H](C1)c1cc(-c3cc(Cl)cc(Cl)c3)cc3c1N2CC3 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-7c89020e55a54e6f82b3630ecff61c78 | CC(C)(C)OC(=O)N1CC[C@H]2[C@@H](C1)c1cc(Br)cc3c1N2CC3.COc1ccc(B(O)O)c(C(C)C)c1>>COc1ccc(-c2cc3c4c(c2)[C@@H]2CN(C(=O)OC(C)(C)C)CC[C@@H]2N4CC3)c(C(C)C)c1 | BrC=1C=C2[C@H]3[C@@H](N4C2=C(C1)CC4)CCN(C3)C(=O)OC(C)(C)C.C(C)(C)C1=C(C=CC(=C1)OC)B(O)O>>C(C)(C)C1=C(C=CC(=C1)OC)C=1C=C2[C@H]3[C@@H](N4C2=C(C1)CC4)CCN(C3)C(=O)OC(C)(C)C | Br[c:7]1[cH:8][c:9]2[c:10]3[c:11]([cH:12]1)[C@@H:13]1[CH2:14][N:15]([C:16](=[O:17])[O:18][C:19]([CH3:20])([CH3:21])[CH3:22])[CH2:23][CH2:24][C@@H:25]1[N:26]3[CH2:27][CH2:28]2.OB(O)[c:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:33][c:29]1[CH:30]([CH3:31])[CH3:32]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][c:9]3[c:10]4... | CC(C)(C)OC(=O)N1CC[C@H]2[C@@H](C1)c1cc(Br)cc3c1N2CC3.COc1ccc(B(O)O)c(C(C)C)c1 | COc1ccc(-c2cc3c4c(c2)[C@@H]2CN(C(=O)OC(C)(C)C)CC[C@@H]2N4CC3)c(C(C)C)c1 | null | null | null | C-C Coupling | Suzuki coupling with boronic acids | 9de9ab65f6e2a1708d752f9805ab4397c406115bb682ed6a843a36653cbfe352 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(-c2cc3c4c(c2)[C@@H]2CNCC[C@@H]2N4CC3)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].O-B(-O)-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9](-[C:10]):[c:11]>>[C:10]-[c:9](:[c:11]):[c;H0;D3;+0:6](-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5]):[c:7]:[c:8] | null | [] | null | null | null | null | The title compound was prepared by the method of Example 89 step C from tert-butyl(6aS,10aR)-2-bromo-4,5,7,8,10,10a-hexahydropyrido[4,3-b]pyrrolo[3,2,1-hi]indole-9(6aH)carboxylate (189 mg, 0.5 mmol) and corresponding 2-isopropyl-4-methoxyphenyl boronic acid (178 mg, 1.0 mmol) to afford after chromatographic purificatio... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1cc2c3c(c1)[C@@H]1C[NH]CC[C@@H]1N3CC2.c1ccccc1 | c1ccccc1.c1cc2c3c(c1)[C@@H]1C[NH]CC[C@@H]1N3CC2 | c1ccccc1.c1cc2c3c(c1)[C@@H]1C[NH]CC[C@@H]1N3CC2 | HBr.B | null | null | null | CC(C)(C)OC(=O)N1CC[C@H]2[C@@H](C1)c1cc(Br)cc3c1N2CC3.COc1ccc(B(O)O)c(C(C)C)c1>>COc1ccc(-c2cc3c4c(c2)[C@@H]2CN(C(=O)OC(C)(C)C)CC[C@@H]2N4CC3)c(C(C)C)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-25dbdaf9e53e41af861698b0feeb9f7f | CC(C)(C)OC(=O)N1CC[C@H]2[C@@H](C1)c1cc(Br)cc3c1N2CC3.COc1cc(C)c(B(O)O)cc1F>>COc1cc(C)c(-c2cc3c4c(c2)[C@@H]2CN(C(=O)OC(C)(C)C)CC[C@@H]2N4CC3)cc1F | BrC=1C=C2[C@H]3[C@@H](N4C2=C(C1)CC4)CCN(C3)C(=O)OC(C)(C)C.FC=1C(=CC(=C(C1)B(O)O)C)OC>>FC=1C(=CC(=C(C1)C=1C=C2[C@H]3[C@@H](N4C2=C(C1)CC4)CCN(C3)C(=O)OC(C)(C)C)C)OC | Br[c:8]1[cH:9][c:10]2[c:11]3[c:12]([cH:13]1)[C@@H:14]1[CH2:15][N:16]([C:17](=[O:18])[O:19][C:20]([CH3:21])([CH3:22])[CH3:23])[CH2:24][CH2:25][C@@H:26]1[N:27]3[CH2:28][CH2:29]2.OB(O)[c:7]1[c:5]([CH3:6])[cH:4][c:3]([O:2][CH3:1])[c:31]([F:32])[cH:30]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([CH3:6])[c:7](-[c:8]2[cH:9][c:10]3[c:11]... | CC(C)(C)OC(=O)N1CC[C@H]2[C@@H](C1)c1cc(Br)cc3c1N2CC3.COc1cc(C)c(B(O)O)cc1F | COc1cc(C)c(-c2cc3c4c(c2)[C@@H]2CN(C(=O)OC(C)(C)C)CC[C@@H]2N4CC3)cc1F | null | null | null | C-C Coupling | Suzuki coupling with boronic acids | 9de9ab65f6e2a1708d752f9805ab4397c406115bb682ed6a843a36653cbfe352 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(-c2cc3c4c(c2)[C@@H]2CNCC[C@@H]2N4CC3)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].O-B(-O)-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9](-[C;D1;H3:10]):[c:11]>>[C;D1;H3:10]-[c:9](:[c:11]):[c;H0;D3;+0:6](-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5]):[c:7]:[c:8] | null | [] | null | null | null | null | The title compound was prepared by the method of Example 89 step C from tert-butyl(6aS,10aR)-2-bromo-4,5,7,8,10,10a-hexahydropyrido[4,3-b]pyrrolo[3,2,1-hi]indole-9(6aH)carboxylate (189 mg, 0.5 mmol) and corresponding 5-fluoro-4-methoxy-2-methylphenyl boronic acid (184 mg, 1.0 mmol) to afford after chromatographic purif... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1cc2c3c(c1)[C@@H]1C[NH]CC[C@@H]1N3CC2.c1ccccc1 | c1ccccc1.c1cc2c3c(c1)[C@@H]1C[NH]CC[C@@H]1N3CC2 | c1ccccc1.c1cc2c3c(c1)[C@@H]1C[NH]CC[C@@H]1N3CC2 | HBr.B | null | null | null | CC(C)(C)OC(=O)N1CC[C@H]2[C@@H](C1)c1cc(Br)cc3c1N2CC3.COc1cc(C)c(B(O)O)cc1F>>COc1cc(C)c(-c2cc3c4c(c2)[C@@H]2CN(C(=O)OC(C)(C)C)CC[C@@H]2N4CC3)cc1F |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-47e7bb46feb7451abcba296bb9c3d703 | CC(C)(C)OC(=O)N1CC[C@H]2[C@@H](C1)c1cc(Br)cc3c1N2CC3.COc1ccc(B(O)O)c(C)c1>>COc1ccc(-c2cc3c4c(c2)[C@@H]2CN(C(=O)OC(C)(C)C)CC[C@@H]2N4CC3)c(C)c1 | BrC=1C=C2[C@H]3[C@@H](N4C2=C(C1)CC4)CCN(C3)C(=O)OC(C)(C)C.COC1=CC(=C(C=C1)B(O)O)C>>COC1=CC(=C(C=C1)C=1C=C2[C@H]3[C@@H](N4C2=C(C1)CC4)CCN(C3)C(=O)OC(C)(C)C)C | Br[c:7]1[cH:8][c:9]2[c:10]3[c:11]([cH:12]1)[C@@H:13]1[CH2:14][N:15]([C:16](=[O:17])[O:18][C:19]([CH3:20])([CH3:21])[CH3:22])[CH2:23][CH2:24][C@@H:25]1[N:26]3[CH2:27][CH2:28]2.OB(O)[c:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:31][c:29]1[CH3:30]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][c:9]3[c:10]4[c:11]([cH:12]2)[... | CC(C)(C)OC(=O)N1CC[C@H]2[C@@H](C1)c1cc(Br)cc3c1N2CC3.COc1ccc(B(O)O)c(C)c1 | COc1ccc(-c2cc3c4c(c2)[C@@H]2CN(C(=O)OC(C)(C)C)CC[C@@H]2N4CC3)c(C)c1 | null | null | null | C-C Coupling | Suzuki coupling with boronic acids | 9de9ab65f6e2a1708d752f9805ab4397c406115bb682ed6a843a36653cbfe352 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(-c2cc3c4c(c2)[C@@H]2CNCC[C@@H]2N4CC3)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].O-B(-O)-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9](-[C;D1;H3:10]):[c:11]>>[C;D1;H3:10]-[c:9](:[c:11]):[c;H0;D3;+0:6](-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5]):[c:7]:[c:8] | null | [] | null | null | null | null | The title compound was prepared by the method of Example 89 step C from tert-butyl(6aS,10aR)-2-bromo-4,5,7,8,10,10a-hexahydropyrido[4,3-b]pyrrolo[3,2,1-hi]indole-9(6aH)carboxylate (189 mg, 0.5 mmol) and 4-methoxy-2-methylphenylboronic acid (166 mg, 1.0 mmol) to afford after chromatographic purification the title compou... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1cc2c3c(c1)[C@@H]1C[NH]CC[C@@H]1N3CC2.c1ccccc1 | c1ccccc1.c1cc2c3c(c1)[C@@H]1C[NH]CC[C@@H]1N3CC2 | c1ccccc1.c1cc2c3c(c1)[C@@H]1C[NH]CC[C@@H]1N3CC2 | HBr.B | null | null | null | CC(C)(C)OC(=O)N1CC[C@H]2[C@@H](C1)c1cc(Br)cc3c1N2CC3.COc1ccc(B(O)O)c(C)c1>>COc1ccc(-c2cc3c4c(c2)[C@@H]2CN(C(=O)OC(C)(C)C)CC[C@@H]2N4CC3)c(C)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-3519d8ef042e4a8fa97f530a2b98d6d9 | CC(C)(C)OC(=O)N1CC[C@H]2[C@@H](C1)c1cc(Br)cc3c1N2CC3.COc1ccc(B(O)O)c(Cl)c1>>COc1ccc(-c2cc3c4c(c2)[C@@H]2CN(C(=O)OC(C)(C)C)CC[C@@H]2N4CC3)c(Cl)c1 | BrC=1C=C2[C@H]3[C@@H](N4C2=C(C1)CC4)CCN(C3)C(=O)OC(C)(C)C.ClC1=C(C=CC(=C1)OC)B(O)O>>ClC1=C(C=CC(=C1)OC)C=1C=C2[C@H]3[C@@H](N4C2=C(C1)CC4)CCN(C3)C(=O)OC(C)(C)C | Br[c:7]1[cH:8][c:9]2[c:10]3[c:11]([cH:12]1)[C@@H:13]1[CH2:14][N:15]([C:16](=[O:17])[O:18][C:19]([CH3:20])([CH3:21])[CH3:22])[CH2:23][CH2:24][C@@H:25]1[N:26]3[CH2:27][CH2:28]2.OB(O)[c:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:31][c:29]1[Cl:30]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][c:9]3[c:10]4[c:11]([cH:12]2)[C... | CC(C)(C)OC(=O)N1CC[C@H]2[C@@H](C1)c1cc(Br)cc3c1N2CC3.COc1ccc(B(O)O)c(Cl)c1 | COc1ccc(-c2cc3c4c(c2)[C@@H]2CN(C(=O)OC(C)(C)C)CC[C@@H]2N4CC3)c(Cl)c1 | null | null | null | C-C Coupling | Suzuki coupling with boronic acids | 9de9ab65f6e2a1708d752f9805ab4397c406115bb682ed6a843a36653cbfe352 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(-c2cc3c4c(c2)[C@@H]2CNCC[C@@H]2N4CC3)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].O-B(-O)-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9](-[Cl;D1;H0:10]):[c:11]>>[Cl;D1;H0:10]-[c:9](:[c:11]):[c;H0;D3;+0:6](-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5]):[c:7]:[c:8] | null | [] | null | null | null | null | The title compound was prepared by the method of Example 89 step C from tert-butyl(6aS,10aR)-2-bromo-4,5,7,8,10,10a-hexahydropyrido[4,3-b]pyrrolo[3,2,1-hi]indole-9(6aH)carboxylate (189 mg, 0.5 mmol) and 2-chloro-4-methoxyphenylboronic acid (187 mg, 1.0 mmol) to afford after chromatographic purification the title compou... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1cc2c3c(c1)[C@@H]1C[NH]CC[C@@H]1N3CC2.c1ccccc1 | c1ccccc1.c1cc2c3c(c1)[C@@H]1C[NH]CC[C@@H]1N3CC2 | c1ccccc1.c1cc2c3c(c1)[C@@H]1C[NH]CC[C@@H]1N3CC2 | HBr.B | null | null | null | CC(C)(C)OC(=O)N1CC[C@H]2[C@@H](C1)c1cc(Br)cc3c1N2CC3.COc1ccc(B(O)O)c(Cl)c1>>COc1ccc(-c2cc3c4c(c2)[C@@H]2CN(C(=O)OC(C)(C)C)CC[C@@H]2N4CC3)c(Cl)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-4df852e04e714000900922b518961fec | CC(C)(C)OC(=O)N1CC[C@H]2[C@@H](C1)c1cc(Br)cc3c1N2CC3.Cc1c(Cl)cccc1B(O)O>>Cc1c(Cl)cccc1-c1cc2c3c(c1)[C@@H]1CN(C(=O)OC(C)(C)C)CC[C@@H]1N3CC2 | BrC=1C=C2[C@H]3[C@@H](N4C2=C(C1)CC4)CCN(C3)C(=O)OC(C)(C)C.ClC=1C(=C(C=CC1)B(O)O)C>>ClC=1C(=C(C=CC1)C=1C=C2[C@H]3[C@@H](N4C2=C(C1)CC4)CCN(C3)C(=O)OC(C)(C)C)C | Br[c:9]1[cH:10][c:11]2[c:12]3[c:13]([cH:14]1)[C@@H:15]1[CH2:16][N:17]([C:18](=[O:19])[O:20][C:21]([CH3:22])([CH3:23])[CH3:24])[CH2:25][CH2:26][C@@H:27]1[N:28]3[CH2:29][CH2:30]2.OB(O)[c:8]1[c:2]([CH3:1])[c:3]([Cl:4])[cH:5][cH:6][cH:7]1>>[CH3:1][c:2]1[c:3]([Cl:4])[cH:5][cH:6][cH:7][c:8]1-[c:9]1[cH:10][c:11]2[c:12]3[c:13]... | CC(C)(C)OC(=O)N1CC[C@H]2[C@@H](C1)c1cc(Br)cc3c1N2CC3.Cc1c(Cl)cccc1B(O)O | Cc1c(Cl)cccc1-c1cc2c3c(c1)[C@@H]1CN(C(=O)OC(C)(C)C)CC[C@@H]1N3CC2 | null | null | null | C-C Coupling | Suzuki coupling with boronic acids | 9de9ab65f6e2a1708d752f9805ab4397c406115bb682ed6a843a36653cbfe352 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(-c2cc3c4c(c2)[C@@H]2CNCC[C@@H]2N4CC3)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].O-B(-O)-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9](-[C;D1;H3:10]):[c:11]>>[C;D1;H3:10]-[c:9](:[c:11]):[c;H0;D3;+0:6](-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5]):[c:7]:[c:8] | null | [] | null | null | null | null | The title compound was prepared by the method of Example 89 step C from tert-butyl(6aS,10aR)-2-bromo-4,5,7,8,10,10a-hexahydropyrido[4,3-b]pyrrolo[3,2,1-hi]indole-9(6aH)carboxylate (189 mg, 0.5 mmol) and 3-chloro-2-methylphenylboronic acid (140 mg, 1.0 mmol) to afford after chromatographic purification the title compoun... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1cc2c3c(c1)[C@@H]1C[NH]CC[C@@H]1N3CC2.c1ccccc1 | c1ccccc1.c1cc2c3c(c1)[C@@H]1C[NH]CC[C@@H]1N3CC2 | c1ccccc1.c1cc2c3c(c1)[C@@H]1C[NH]CC[C@@H]1N3CC2 | HBr.B | null | null | null | CC(C)(C)OC(=O)N1CC[C@H]2[C@@H](C1)c1cc(Br)cc3c1N2CC3.Cc1c(Cl)cccc1B(O)O>>Cc1c(Cl)cccc1-c1cc2c3c(c1)[C@@H]1CN(C(=O)OC(C)(C)C)CC[C@@H]1N3CC2 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-5936044beb9042d19c3e6b105ec7b8d2 | CC(C)(C)OC(=O)N1CC[C@H]2[C@@H](C1)c1cc(Br)cc3c1N2CC3.COc1ccc(B(O)O)c(C=O)c1>>COc1ccc(-c2cc3c4c(c2)[C@@H]2CN(C(=O)OC(C)(C)C)CC[C@@H]2N4CC3)c(C=O)c1 | BrC=1C=C2[C@H]3[C@@H](N4C2=C(C1)CC4)CCN(C3)C(=O)OC(C)(C)C.C(=O)C1=C(C=CC(=C1)OC)B(O)O.O.O.O.O.O.O.O.O.[OH-].[Ba+2].[OH-]>>C(=O)C1=C(C=CC(=C1)OC)C=1C=C2[C@H]3[C@@H](N4C2=C(C1)CC4)CCN(C3)C(=O)OC(C)(C)C | Br[c:7]1[cH:8][c:9]2[c:10]3[c:11]([cH:12]1)[C@@H:13]1[CH2:14][N:15]([C:16](=[O:17])[O:18][C:19]([CH3:20])([CH3:21])[CH3:22])[CH2:23][CH2:24][C@@H:25]1[N:26]3[CH2:27][CH2:28]2.OB(O)[c:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:32][c:29]1[CH:30]=[O:31]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][c:9]3[c:10]4[c:11]([cH:... | CC(C)(C)OC(=O)N1CC[C@H]2[C@@H](C1)c1cc(Br)cc3c1N2CC3.COc1ccc(B(O)O)c(C=O)c1 | COc1ccc(-c2cc3c4c(c2)[C@@H]2CN(C(=O)OC(C)(C)C)CC[C@@H]2N4CC3)c(C=O)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 | O.COCCOC | C-C Coupling | Suzuki coupling with boronic acids | 9de9ab65f6e2a1708d752f9805ab4397c406115bb682ed6a843a36653cbfe352 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(-c2cc3c4c(c2)[C@@H]2CNCC[C@@H]2N4CC3)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].O-B(-O)-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9](-[C:10]=[O;D1;H0:11]):[c:12]>>[O;D1;H0:11]=[C:10]-[c:9](:[c:12]):[c;H0;D3;+0:6](-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5]):[c:7]:[c:8] | 41 | [{"value": 41.0, "product": "C(=O)C1=C(C=CC(=C1)OC)C=1C=C2[C@H]3[C@@H](N4C2=C(C1)CC4)CCN(C3)C(=O)OC(C)(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 40.5, "product": "C(=O)C1=C(C=CC(=C1)OC)C=1C=C2[C@H]3[C@@H](N4C2=C(C1)CC4)CCN(C3)C(=O)OC(C)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": fal... | null | null | null | null | To a solution of tert-butyl(6aS,10aR)-2-bromo-4,5,7,8,10,10a-hexahydropyrido[4,3-b]pyrrolo[3,2,1-hi]indole-9(6aH)-carboxylate (0.600 g, 1.59 mmol) in DME (35 mL) was added 2-formyl-4-methoxybenzeneboronic acid (0.344 g, 1.91 mmol), tetrakis(triphenylphosphine)palladium(0) (0.110 g), barium hydroxide octahydrate (0.753 ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1cc2c3c(c1)[C@@H]1C[NH]CC[C@@H]1N3CC2.c1ccccc1 | c1ccccc1.c1cc2c3c(c1)[C@@H]1C[NH]CC[C@@H]1N3CC2 | c1ccccc1.c1cc2c3c(c1)[C@@H]1C[NH]CC[C@@H]1N3CC2 | HBr.B | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.O.COCCOC | null | null | CC(C)(C)OC(=O)N1CC[C@H]2[C@@H](C1)c1cc(Br)cc3c1N2CC3.COc1ccc(B(O)O)c(C=O)c1>C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.O.COCCOC>COc1ccc(-c2cc3c4c(c2)[C@@H]2CN(C(=O)OC(C)(C)C)CC[C@@H]2N4CC3)c(C... |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-48c9169ce4d940d288c2655906432df4 | CC(C)(C)OC(=O)N1CC[C@H]2[C@@H](C1)c1cc(Br)cc3c1N2CC3.OB(O)c1c(Cl)cccc1Cl>>Clc1cccc(Cl)c1-c1cc2c3c(c1)[C@@H]1CNCC[C@@H]1N3CC2 | ClC1=C(C(=CC=C1)Cl)B(O)O.BrC=1C=C2[C@H]3[C@@H](N4C2=C(C1)CC4)CCN(C3)C(=O)OC(C)(C)C>>ClC1=C(C(=CC=C1)Cl)C=1C=C2[C@H]3[C@@H](N4C2=C(C1)CC4)CCNC3 | CC(C)(C)OC(=O)[N:17]1[CH2:16][C@H:15]2[c:13]3[c:12]4[c:11]([cH:10][c:9](Br)[cH:14]3)[CH2:23][CH2:22][N:21]4[C@H:20]2[CH2:19][CH2:18]1.OB(O)[c:8]1[c:2]([Cl:1])[cH:3][cH:4][cH:5][c:6]1[Cl:7]>>[Cl:1][c:2]1[cH:3][cH:4][cH:5][c:6]([Cl:7])[c:8]1-[c:9]1[cH:10][c:11]2[c:12]3[c:13]([cH:14]1)[C@@H:15]1[CH2:16][NH:17][CH2:18][CH2... | CC(C)(C)OC(=O)N1CC[C@H]2[C@@H](C1)c1cc(Br)cc3c1N2CC3.OB(O)c1c(Cl)cccc1Cl | Clc1cccc(Cl)c1-c1cc2c3c(c1)[C@@H]1CNCC[C@@H]1N3CC2 | null | null | null | C-C Coupling | OtherReaction | 4fd7937c40041ab27d7e09bfa587c77b26a85702b24a197091bdcd0db3a36bac | f8bc7d7af72f3dcb1d8785ac96c7aaf97c54842222d3f4332a40344844fc1d1c | c1ccc(-c2cc3c4c(c2)[C@@H]2CNCC[C@@H]2N4CC3)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5]-[C:6]-[C:7]-[N;H0;D3;+0:8](-C(=O)-O-C(-C)(-C)-C)-[C:9]-[C:10].O-B(-O)-[c;H0;D3;+0:11](:[c:12](-[Cl;D1;H0:13]):[c:14]):[c:15](-[Cl;D1;H0:16]):[c:17]>>[C:10]-[C:9]-[NH;D2;+0:8]-[C:7]-[C:6]-[c:5]:[c:4]:[c;H0;D3;+0:1](-[c;H0;D3;+0:11](:[c:12](-[Cl;D1;H0:13]):[c:14]):[c:15](-[Cl;D... | null | [] | null | null | null | null | The title compound was prepared by Example 305, Step A, from tert-butyl(6aS,10aR)-2-bromo-4,5,7,8,10,10a-hexahydropyrido[4,3-b]pyrrolo[3,2,1-hi]indole-9(6aH)-carboxylate and the corresponding 2,6-dichlorobenzeneboronic acid followed by hydrolysis of the resultant BOC protected amine adduct by the procedure of Example 3... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Carbamic ester.Ether.Boronic acid.Boc | Secondary amine | c1cc2c3c(c1)[C@@H]1C[NH]CC[C@@H]1N3CC2.c1ccccc1 | c1ccccc1.c1cc2c3c(c1)[C@@H]1CNCC[C@@H]1N3CC2 | c1ccccc1.c1cc2c3c(c1)[C@@H]1CNCC[C@@H]1N3CC2 | HBr.B | null | null | null | CC(C)(C)OC(=O)N1CC[C@H]2[C@@H](C1)c1cc(Br)cc3c1N2CC3.OB(O)c1c(Cl)cccc1Cl>>Clc1cccc(Cl)c1-c1cc2c3c(c1)[C@@H]1CNCC[C@@H]1N3CC2 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-71def1db07184e0f912f7ce4d7369e42 | O=C1CC=Cc2ccccc21>>O=C1CCCc2ccccc2N1 | [OH-].[Na+].[N-]=[N+]=[N-].[Na+].C1(CC=CC2=CC=CC=C12)=O>>N1C(CCCC2=C1C=CC=C2)=O | [O:1]=[C:2]1[CH2:3][CH:4]=[CH:5][c:6]2[cH:7][cH:8][cH:9][cH:10][c:11]21>>[O:1]=[C:2]1[CH2:3][CH2:4][CH2:5][c:6]2[cH:7][cH:8][cH:9][cH:10][c:11]2[NH:12]1 | O=C1CC=Cc2ccccc21 | O=C1CCCc2ccccc2N1 | null | null | CS(=O)(=O)O | Functional Group Interconversion | OtherReaction | 5744b8823dc6f6ee1544715b9ead4b13b96b0da801b8a71168afe1c8b4401835 | 0ee35a9373b7d3eb80fc427dac719078cff31f9432b48900d8d35fce64dcdf83 | O=C1CCCc2ccccc2N1 | [O;D1;H0:1]=[C;H0;D3;+0:2]1-[C:3]-[CH;D2;+0:4]=[CH;D2;+0:5]-[c:6](:[c:7]):[c;H0;D3;+0:8]-1:[c:9]:[c:10]>>[O;D1;H0:1]=[C;H0;D3;+0:2]1-[#7:11]-[c;H0;D3;+0:8](:[c:9]:[c:10]):[c:6](:[c:7])-[CH2;D2;+0:5]-[CH2;D2;+0:4]-[C:3]-1 | 85 | [{"value": 85.0, "product": "N1C(CCCC2=C1C=CC=C2)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 84.1, "product": "N1C(CCCC2=C1C=CC=C2)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 1 | HOUR | Sodium azide (1.95 g, 30 mmol) was added in small portions to a solution of 3,4-dihydro-[(2H)-naphthalenone (2.92 g, 20 mmol) in CH3SO3H (50 mL) at 0° C. The mixture was stirred at 0° C. for 15 min, 1 hr at room temperature, poured into ice (400 mL), basified until pH>8 with 1N NaOH at 0° C. and extracted with ether (3... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Secondary amide | C1=Cc2ccccc2CC1 | c1ccc2c(c1)CCCCN2 | c1ccc2c(c1)CCCCN2 | Other | CS(=O)(=O)O | 0 | 1 | O=C1CC=Cc2ccccc21>CS(=O)(=O)O>O=C1CCCc2ccccc2N1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-6e01e8843e3e4e8cb5ca3e3fd9f2faca | O=C1CCCc2ccccc2N1>>c1ccc2c(c1)CCCCN2 | N1C(CCCC2=C1C=CC=C2)=O.[H-].[H-].[H-].[H-].[Li+].[Al+3].[C@@H]([C@H](C(=O)[O-])O)(C(=O)[O-])O.[Na+].[K+]>>N1CCCCC2=C1C=CC=C2 | O=[C:10]1[CH2:9][CH2:8][CH2:7][c:5]2[c:4]([cH:3][cH:2][cH:1][cH:6]2)[NH:11]1>>[cH:1]1[cH:2][cH:3][c:4]2[c:5]([cH:6]1)[CH2:7][CH2:8][CH2:9][CH2:10][NH:11]2 | O=C1CCCc2ccccc2N1 | c1ccc2c(c1)CCCCN2 | null | null | CCOCC.C1CCOC1 | Reduction | Reduction of secondary amides to amines | 03aa0b4e274bbc77e41c2b841353748b318e281ae4a91883373ad63bbabd4706 | ab40188eef2f825df7003af0ffae31d0ce53d126542122535627d3d354cbc9fe | c1ccc2c(c1)CCCCN2 | O=[C;H0;D3;+0:1](-[#7:2]-[c:3])-[C:4]-[C:5]>>[C:5]-[C:4]-[CH2;D2;+0:1]-[#7:2]-[c:3] | 98 | [{"value": 98.0, "product": "N1CCCCC2=C1C=CC=C2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 97.6, "product": "N1CCCCC2=C1C=CC=C2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | A solution of 1,3,4,5-tetrahydro-2H-1-benzazepin-2-one (2.71 g, 16.7 mmol) in THF (40 mL) was added dropwise to a suspension of LAH (1.27 g, 33.4 mmol) in ether (150 mL) at room temperature. The mixture was refluxed for 16 h. Saturated Rochelle's salt solution (15 mL) was added to the mixture cooled with an ice-water b... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide | null | c1ccc2c(c1)CCCCN2 | c1ccc2c(c1)CCCCN2 | c1ccc2c(c1)CCCCN2 | Other | CCOCC.C1CCOC1 | null | 2 | O=C1CCCc2ccccc2N1>CCOCC.C1CCOC1>c1ccc2c(c1)CCCCN2 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-abf1cef320334136908bfe3eab72b74d | c1ccc2c(c1)CCCCN2>>O=NN1CCCCc2ccccc21 | N(=O)[O-].[Na+].N1CCCCC2=C1C=CC=C2>>N(=O)N1CCCCC2=C1C=CC=C2 | [NH:3]1[CH2:4][CH2:5][CH2:6][CH2:7][c:8]2[cH:9][cH:10][cH:11][cH:12][c:13]21>>[O:1]=[N:2][N:3]1[CH2:4][CH2:5][CH2:6][CH2:7][c:8]2[cH:9][cH:10][cH:11][cH:12][c:13]21 | c1ccc2c(c1)CCCCN2 | O=NN1CCCCc2ccccc21 | null | null | O.CC(=O)O | Miscellaneous | OtherReaction | 62c0fc011852f73fce68cdef4477aecb694ec5a81d663346b5ccc31bb897d3f3 | 797765290ff12ff8fc5d8a85352c4763898223fe8d7887a890f0208d031bd39f | c1ccc2c(c1)CCCCN2 | [C:1]-[C:2]-[NH;D2;+0:3]-[c:4](:[c:5]):[c:6]>>[C:1]-[C:2]-[N;H0;D3;+0:3](-[#7:7]=[O;D1;H0:8])-[c:4](:[c:5]):[c:6] | 91 | [{"value": 91.0, "product": "N(=O)N1CCCCC2=C1C=CC=C2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 90.5, "product": "N(=O)N1CCCCC2=C1C=CC=C2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 5 | CELSIUS | 1 | HOUR | A solution of sodium nitrite (1.35 g, 19.6 mmol) in water (4.0 mL) was added dropwise to a solution of 2,3,4,5-tetrahydro-1H-1-benzazepine (2.40 g, 16.3 mmol) in AcOH (10 mL) at 0–10° C. The mixture was stirred at 5° C. for 10 min, room temperature for 1 h and extracted with CH2Cl2 (3×20 mL). The organic layer was drie... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amine | Hydrazone | c1ccc2c(c1)CCCCN2 | c1ccc2c(c1)CCCC[NH]2 | c1ccc2c(c1)CCCC[NH]2 | Other | O.CC(=O)O | 5 | 1 | c1ccc2c(c1)CCCCN2>O.CC(=O)O>O=NN1CCCCc2ccccc21 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-d681d7d13a2748a08aa1f01f45d2bcd7 | O=NN1CCCCc2ccccc21>>NN1CCCCc2ccccc21 | N(=O)N1CCCCC2=C1C=CC=C2.[H-].[H-].[H-].[H-].[Li+].[Al+3]>>N1(CCCCC2=C1C=CC=C2)N | O=[N:1][N:2]1[CH2:3][CH2:4][CH2:5][CH2:6][c:7]2[cH:8][cH:9][cH:10][cH:11][c:12]21>>[NH2:1][N:2]1[CH2:3][CH2:4][CH2:5][CH2:6][c:7]2[cH:8][cH:9][cH:10][cH:11][c:12]21 | O=NN1CCCCc2ccccc21 | NN1CCCCc2ccccc21 | null | null | C1CCOC1 | Reduction | OtherReaction | 5407f493a1ccf8dd5d07d54ae38e6a10270ea7ce5de5a6b7714c1deac546b85e | e98fc89254846fe35f9c53f13405831fb1e12dbc5358868ae840bffa7ffc2275 | c1ccc2c(c1)CCCCN2 | O=[N;H0;D2;+0:1]-[#7:2](-[C:3])-[c:4]>>[C:3]-[#7:2](-[NH2;D1;+0:1])-[c:4] | 68.3 | [{"value": 68.0, "product": "N1(CCCCC2=C1C=CC=C2)N", "details": "PERCENTYIELD", "is_desired": false}, {"value": 68.3, "product": "N1(CCCCC2=C1C=CC=C2)N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | A solution of 1-nitroso-2,3,4,5-tetrahydro-1H-1-benzazepine (2.60 g, 14.7 mmol) in THF (40 mL) was added dropwise under N2 to a suspension of LAH (0.56 g, 14.7 mmol) in THF (10 mL) cooled with an ice-bath such that the temperature did not rise above 15° C. The mixture was stirred at room temperature for 1 h, quenched w... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazone | Hydrazine | null | null | c1ccc2c(c1)CCCC[NH]2 | Other | C1CCOC1 | null | 1 | O=NN1CCCCc2ccccc21>C1CCOC1>NN1CCCCc2ccccc21 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-007a9a5192894f03969611e783cbe004 | C=O.Fc1cccc(F)c1-c1cc2c3c(c1)[C@@H]1CNCC[C@@H]1N3CCC2>>CN1CC[C@H]2[C@@H](C1)c1cc(-c3c(F)cccc3F)cc3c1N2CCC3 | C(=O)([O-])[O-].[Na+].[Na+].FC1=C(C(=CC=C1)F)C=1C=C2CCCN3C2=C(C1)[C@H]1[C@@H]3CCNC1.C=O.C(=O)O>>FC1=C(C(=CC=C1)F)C=1C=C2CCCN3C2=C(C1)[C@H]1[C@@H]3CCN(C1)C | O=[CH2:1].[NH:2]1[CH2:3][CH2:4][C@H:5]2[C@@H:6]([CH2:7]1)[c:8]1[cH:9][c:10](-[c:11]3[c:12]([F:13])[cH:14][cH:15][cH:16][c:17]3[F:18])[cH:19][c:20]3[c:21]1[N:22]2[CH2:23][CH2:24][CH2:25]3>>[CH3:1][N:2]1[CH2:3][CH2:4][C@H:5]2[C@@H:6]([CH2:7]1)[c:8]1[cH:9][c:10](-[c:11]3[c:12]([F:13])[cH:14][cH:15][cH:16][c:17]3[F:18])[cH... | C=O.Fc1cccc(F)c1-c1cc2c3c(c1)[C@@H]1CNCC[C@@H]1N3CCC2 | CN1CC[C@H]2[C@@H](C1)c1cc(-c3c(F)cccc3F)cc3c1N2CCC3 | null | null | O | Heteroatom Alkylation and Arylation | Eschweiler-Clarke Secondary Amine Methylation | 419d70e0d7031ec711a5194b6d9536e75babf7ae3bd52b617806c468acfd2675 | e1fdef8fde1c506d7c9deb8fd5e6f322eceea2abce3167abcf412a1fa4fd5443 | c1ccc(-c2cc3c4c(c2)[C@@H]2CNCC[C@@H]2N4CCC3)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] | 62.7 | [{"value": 62.0, "product": "FC1=C(C(=CC=C1)F)C=1C=C2CCCN3C2=C(C1)[C@H]1[C@@H]3CCN(C1)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 62.7, "product": "FC1=C(C(=CC=C1)F)C=1C=C2CCCN3C2=C(C1)[C@H]1[C@@H]3CCN(C1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | null | null | A mixture of (7aS,11aR)-2-(2,6-difluorophenyl)-5,6,7a,8,9,10,11,11a-octahydro-4H-pyrido[3′,4′:4,5]pyrrolo[3,2,1-ij]quinoline (0.050, 0.15 mmol), HCHO (0.20 mL, 2.9 mmol) and formic acid (1.0 mL, 2.9 mmol) was heated at 80° C. for 4 h and cooled to room temperature. Water (5.0 mL) was added and the solution was basified... | 10.6084/m9.figshare.5104873.v1 | null | Formaldehyde.Secondary amine | Tertiary amine | c1cc2c3c(c1)[C@@H]1CNCC[C@@H]1N3CCC2 | c1cc2c3c(c1)[C@@H]1C[NH]CC[C@@H]1N3CCC2 | c1ccccc1.c1cc2c3c(c1)[C@@H]1C[NH]CC[C@@H]1N3CCC2 | Other | O | 80 | null | C=O.Fc1cccc(F)c1-c1cc2c3c(c1)[C@@H]1CNCC[C@@H]1N3CCC2>O>CN1CC[C@H]2[C@@H](C1)c1cc(-c3c(F)cccc3F)cc3c1N2CCC3 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-42f2c69cc2e347b7aa69be5da13d5d9b | COc1ccc(-c2cc3c4c(c2)C2CN(C(=O)OC(C)(C)C)CCC2N4CCC3)c(C(F)(F)F)c1>>COc1ccc(-c2cc3c4c(c2)c2c(n4CCC3)CCNC2)c(C(F)(F)F)c1 | COC1=CC(=C(C=C1)C=1C=C2CCCN3C2=C(C1)C1C3CCN(C1)C(=O)OC(C)(C)C)C(F)(F)F>>COC1=CC(=C(C=C1)C=1C=C2CCCN3C2=C(C1)C1=C3CCNC1)C(F)(F)F | CC(C)(C)OC(=O)[N:21]1[CH2:20][CH2:19][CH:14]2[CH:13]([c:11]3[c:10]4[c:9]([cH:8][c:7](-[c:6]5[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:28][c:23]5[C:24]([F:25])([F:26])[F:27])[cH:12]3)[CH2:18][CH2:17][CH2:16][N:15]42)[CH2:22]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][c:9]3[c:10]4[c:11]([cH:12]2)[c:13]2[c:14]([n:15]4[C... | COc1ccc(-c2cc3c4c(c2)C2CN(C(=O)OC(C)(C)C)CCC2N4CCC3)c(C(F)(F)F)c1 | COc1ccc(-c2cc3c4c(c2)c2c(n4CCC3)CCNC2)c(C(F)(F)F)c1 | null | null | CC#N | Functional Group Interconversion | OtherReaction | 7e306258bbcbfc13cb6c1338ca9083281d3d6d948db1bae0fa5b43b60b6c1083 | 65c568d8f93b9d8871db2da78879ef389c05e5aea6986548c5a68a5410e59727 | c1ccc(-c2cc3c4c(c2)c2c(n4CCC3)CCNC2)cc1 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1]1-[C:2]-[C:3]-[CH;D3;+0:4]2-[CH;D3;+0:5](-[C:6]-1)-[c:7](:[c:8]):[c:9](:[c:10])-[N;H0;D3;+0:11]-2-[C:12]-[C:13]>>[C:13]-[C:12]-[n;H0;D3;+0:11]1:[c:9](:[c:10]):[c:7](:[c:8]):[c;H0;D3;+0:5]2:[c;H0;D3;+0:4]:1-[C:3]-[C:2]-[NH;D2;+0:1]-[C:6]-2 | 98 | [{"value": 98.0, "product": "COC1=CC(=C(C=C1)C=1C=C2CCCN3C2=C(C1)C1=C3CCNC1)C(F)(F)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 97.0, "product": "COC1=CC(=C(C=C1)C=1C=C2CCCN3C2=C(C1)C1=C3CCNC1)C(F)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | The title compound (0.60 g, 98%) was prepared by the general method of Example 312, step B from tert-butyl 2-[4-methoxy-2-(trifluoromethyl)phenyl]-5,6,8,9,10,11-hexahydro-4H-pyrido[3′,4′:4,5]pyrrolo[3,2,1-ij]quinoline-10(7aH)-carboxylate (0.78 g, 1.6 mmol) as a white foam. 1H NMR (CDCl3, 300 MHz) δ 2.20–2.30 (m, 2H), 2... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Tertiary amine.Boc | Secondary amine | c1cc2c3c(c1)C1C[NH]CCC1N3CCC2 | c1cc2c3c(c1)c1c(n3CCC2)CCNC1 | c1ccccc1.c1cc2c3c(c1)c1c(n3CCC2)CCNC1 | HO- | CC#N | null | null | COc1ccc(-c2cc3c4c(c2)C2CN(C(=O)OC(C)(C)C)CCC2N4CCC3)c(C(F)(F)F)c1>CC#N>COc1ccc(-c2cc3c4c(c2)c2c(n4CCC3)CCNC2)c(C(F)(F)F)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-8d1331317aa541ccb4ec4bba3244996b | CCCBr.Clc1cccc(-c2cc3c4c(c2)[C@H]2CNCC[C@H]2N4CCC3)c1Cl>>CCCN1CC[C@@H]2[C@H](C1)c1cc(-c3cccc(Cl)c3Cl)cc3c1N2CCC3 | ClC1=C(C=CC=C1Cl)C=1C=C2CCCN3C2=C(C1)[C@@H]1[C@H]3CCNC1.C(C)(C)N(C(C)C)CC.BrCCC>>ClC1=C(C=CC=C1Cl)C=1C=C2CCCN3C2=C(C1)[C@@H]1[C@H]3CCN(C1)CCC | Br[CH2:3][CH2:2][CH3:1].[NH:4]1[CH2:5][CH2:6][C@@H:7]2[C@H:8]([CH2:9]1)[c:10]1[cH:11][c:12](-[c:13]3[cH:14][cH:15][cH:16][c:17]([Cl:18])[c:19]3[Cl:20])[cH:21][c:22]3[c:23]1[N:24]2[CH2:25][CH2:26][CH2:27]3>>[CH3:1][CH2:2][CH2:3][N:4]1[CH2:5][CH2:6][C@@H:7]2[C@H:8]([CH2:9]1)[c:10]1[cH:11][c:12](-[c:13]3[cH:14][cH:15][cH:... | CCCBr.Clc1cccc(-c2cc3c4c(c2)[C@H]2CNCC[C@H]2N4CCC3)c1Cl | CCCN1CC[C@@H]2[C@H](C1)c1cc(-c3cccc(Cl)c3Cl)cc3c1N2CCC3 | null | null | O1CCOCC1 | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 14635250736ebb1f0e2e07dcba66a1eac5a18ac7f42f8c572369b3c0ad2d9436 | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | c1ccc(-c2cc3c4c(c2)[C@H]2CNCC[C@H]2N4CCC3)cc1 | Br-[CH2;D2;+0:1]-[C: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](-[CH2;D2;+0:1]-[C:2]-[C;D1;H3:3])-[C:7]-[C:8] | 82 | [{"value": 82.0, "product": "ClC1=C(C=CC=C1Cl)C=1C=C2CCCN3C2=C(C1)[C@@H]1[C@H]3CCN(C1)CCC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 81.0, "product": "ClC1=C(C=CC=C1Cl)C=1C=C2CCCN3C2=C(C1)[C@@H]1[C@H]3CCN(C1)CCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | null | null | To a solution of (±)-cis-2-(2,3-dichlorophenyl)-5,6,7a,8,9,10,11,11a-octahydro-4H-pyrido[3′,4′:4,5]pyrrolo[3,2,1-ij]quinoline (30 mg, 0.083 mmol) in 1,4-dioxane (0.5 mL) and N,N-diisopropylethylamine (108 mg, 0.83 mmol) were added 1-bromopropane (21 mg, 0.17 mmol) and KI (catalytic amount). The reaction mixture was hea... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | c1cc2c3c(c1)[C@H]1CNCC[C@H]1N3CCC2 | c1cc2c3c(c1)[C@H]1C[NH]CC[C@H]1N3CCC2 | c1ccccc1.c1cc2c3c(c1)[C@H]1C[NH]CC[C@H]1N3CCC2 | HBr | O1CCOCC1 | 100 | null | CCCBr.Clc1cccc(-c2cc3c4c(c2)[C@H]2CNCC[C@H]2N4CCC3)c1Cl>O1CCOCC1>CCCN1CC[C@@H]2[C@H](C1)c1cc(-c3cccc(Cl)c3Cl)cc3c1N2CCC3 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-7e75ff769dcb4b9b8d4a4227233d78d3 | CCCCBr.Clc1cccc(-c2cc3c4c(c2)[C@H]2CNCC[C@H]2N4CCC3)c1Cl>>CCCCN1CC[C@@H]2[C@H](C1)c1cc(-c3cccc(Cl)c3Cl)cc3c1N2CCC3 | ClC1=C(C=CC=C1Cl)C=1C=C2CCCN3C2=C(C1)[C@@H]1[C@H]3CCNC1.BrCCCC>>C(CCC)N1C[C@H]2[C@H](N3CCCC4=CC(=CC2=C34)C3=C(C(=CC=C3)Cl)Cl)CC1 | Br[CH2:4][CH2:3][CH2:2][CH3:1].[NH:5]1[CH2:6][CH2:7][C@@H:8]2[C@H:9]([CH2:10]1)[c:11]1[cH:12][c:13](-[c:14]3[cH:15][cH:16][cH:17][c:18]([Cl:19])[c:20]3[Cl:21])[cH:22][c:23]3[c:24]1[N:25]2[CH2:26][CH2:27][CH2:28]3>>[CH3:1][CH2:2][CH2:3][CH2:4][N:5]1[CH2:6][CH2:7][C@@H:8]2[C@H:9]([CH2:10]1)[c:11]1[cH:12][c:13](-[c:14]3[c... | CCCCBr.Clc1cccc(-c2cc3c4c(c2)[C@H]2CNCC[C@H]2N4CCC3)c1Cl | CCCCN1CC[C@@H]2[C@H](C1)c1cc(-c3cccc(Cl)c3Cl)cc3c1N2CCC3 | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 14635250736ebb1f0e2e07dcba66a1eac5a18ac7f42f8c572369b3c0ad2d9436 | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | c1ccc(-c2cc3c4c(c2)[C@H]2CNCC[C@H]2N4CCC3)cc1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[C:4]-[C:5]-[NH;D2;+0:6]-[C:7]-[C:8]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:6](-[C:7]-[C:8])-[C:5]-[C:4] | null | [] | null | null | null | null | The title compound was prepared by the method of Example 382 as a yellow oil (28 mg, 82%) from (±)-cis-2-(2,3-dichlorophenyl)-5,6,7a,8,9,10,11,11a-octahydro-4H-pyrido[3′,4′:4,5]pyrrolo[3,2,1-ij]quinoline (30 mg, 0.083 mmol) and 1-bromobutane (23 mg, 0.17 mmol). 1H NMR (CDCl3, 300 MHz) δ 0.92(t, J=7.3 Hz, 3H), 1.32 (se,... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | c1cc2c3c(c1)[C@H]1CNCC[C@H]1N3CCC2 | c1cc2c3c(c1)[C@H]1C[NH]CC[C@H]1N3CCC2 | c1ccccc1.c1cc2c3c(c1)[C@H]1C[NH]CC[C@H]1N3CCC2 | HBr | null | null | null | CCCCBr.Clc1cccc(-c2cc3c4c(c2)[C@H]2CNCC[C@H]2N4CCC3)c1Cl>>CCCCN1CC[C@@H]2[C@H](C1)c1cc(-c3cccc(Cl)c3Cl)cc3c1N2CCC3 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-b63d964556924fbdb248d8f38dad41b6 | Clc1cccc(-c2cc3c4c(c2)[C@@H]2CNCC[C@@H]2N4CCC3)c1Cl>>CCCCN1CC[C@H]2[C@@H](C1)c1cc(-c3cccc(Cl)c3Cl)cc3c1N2CCC3 | ClC1=C(C=CC=C1Cl)C=1C=C2CCCN3C2=C(C1)[C@H]1[C@@H]3CCNC1.N>>C(CCC)N1C[C@@H]2[C@@H](N3CCCC4=CC(=CC2=C34)C3=C(C(=CC=C3)Cl)Cl)CC1 | [cH:1]1[cH:15][c:14](-[c:13]2[cH:12][c:11]3[c:24]4[c:23]([cH:22]2)[CH2:28][CH2:27][CH2:26][N:25]4[C@H:8]2[CH2:7][CH2:6][NH:5][CH2:10][C@H:9]23)[c:20]([Cl:21])[c:18]([Cl:19])[cH:17]1>>[CH3:1][CH2:2][CH2:3][CH2:4][N:5]1[CH2:6][CH2:7][C@H:8]2[C@@H:9]([CH2:10]1)[c:11]1[cH:12][c:13](-[c:14]3[cH:15][cH:16][cH:17][c:18]([Cl:1... | Clc1cccc(-c2cc3c4c(c2)[C@@H]2CNCC[C@@H]2N4CCC3)c1Cl | CCCCN1CC[C@H]2[C@@H](C1)c1cc(-c3cccc(Cl)c3Cl)cc3c1N2CCC3 | null | null | null | Miscellaneous | OtherReaction | 198d041acdfcd05f2ce9f78baa8bf9c2fbc1afc7d8ff4f8ddee920fbfd131534 | 06e4cfdff0e70e885199cc5de7382cc871277954ed1dd9750edc3ce3b12c44bd | c1ccc(-c2cc3c4c(c2)[C@@H]2CNCC[C@@H]2N4CCC3)cc1 | [C:1]-[C:2]-[NH;D2;+0:3]-[C:4]-[C:5].[Cl;D1;H0:6]-[c:7]1:[c:8]:[c:9](-[c:10]):[cH;D2;+0:11]:[cH;D2;+0:12]:[cH;D2;+0:13]:1>>[C:1]-[C:2]-[N;H0;D3;+0:3](-[C:14]-[C:15]-[C:16]-[CH3;D1;+0:12])-[C:4]-[C:5].[Cl;D1;H0:6]-[c:7]1:[c:8]:[c:9](-[c:10]):[cH;D2;+0:11]:[c:17]:[cH;D2;+0:13]:1 | null | [] | null | null | null | null | The title compound was prepared by the method of Example 382 as a yellow oil (23 mg, 62%) from (7aS,11aR)-2-(2,3-dichlorophenyl)-5,6,7a,8,9,10,11,11a-octahydro-4H-pyrido[3′,4′:4,5]pyrrolo[3,2,1-ij]quinoline (30 mg, 0.083 mmol). The title compound was spectroscopically identical to Example 384. MS (CI, NH3): 415.1 (base... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amine | Tertiary amine | c1ccccc1.c1cc2c3c(c1)[C@@H]1CNCC[C@@H]1N3CCC2 | c1ccccc1.c1cc2c3c(c1)[C@@H]1C[NH]CC[C@@H]1N3CCC2 | c1ccccc1.c1cc2c3c(c1)[C@@H]1C[NH]CC[C@@H]1N3CCC2 | Other | null | null | null | Clc1cccc(-c2cc3c4c(c2)[C@@H]2CNCC[C@@H]2N4CCC3)c1Cl>>CCCCN1CC[C@H]2[C@@H](C1)c1cc(-c3cccc(Cl)c3Cl)cc3c1N2CCC3 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-ef5abb8dd2e24110a885b643ecab8627 | C=CCCCBr.Clc1cccc(-c2cc3c4c(c2)[C@@H]2CNCC[C@@H]2N4CCC3)c1Cl>>C=CCCCN1CC[C@H]2[C@@H](C1)c1cc(-c3cccc(Cl)c3Cl)cc3c1N2CCC3 | ClC1=C(C=CC=C1Cl)C=1C=C2CCCN3C2=C(C1)[C@H]1[C@@H]3CCNC1.BrCCCC=C.N>>ClC1=C(C=CC=C1Cl)C=1C=C2CCCN3C2=C(C1)[C@H]1[C@@H]3CCN(C1)CCCC=C | Br[CH2:5][CH2:4][CH2:3][CH:2]=[CH2:1].[NH:6]1[CH2:7][CH2:8][C@H:9]2[C@@H:10]([CH2:11]1)[c:12]1[cH:13][c:14](-[c:15]3[cH:16][cH:17][cH:18][c:19]([Cl:20])[c:21]3[Cl:22])[cH:23][c:24]3[c:25]1[N:26]2[CH2:27][CH2:28][CH2:29]3>>[CH2:1]=[CH:2][CH2:3][CH2:4][CH2:5][N:6]1[CH2:7][CH2:8][C@H:9]2[C@@H:10]([CH2:11]1)[c:12]1[cH:13][... | C=CCCCBr.Clc1cccc(-c2cc3c4c(c2)[C@@H]2CNCC[C@@H]2N4CCC3)c1Cl | C=CCCCN1CC[C@H]2[C@@H](C1)c1cc(-c3cccc(Cl)c3Cl)cc3c1N2CCC3 | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 156e57521f17e5fff63c4f7b30e3a65e7ad32d15778d94884e7e127a119f08c7 | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | c1ccc(-c2cc3c4c(c2)[C@@H]2CNCC[C@@H]2N4CCC3)cc1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3]-[C:4]=[C;D1;H2:5].[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]=[C;D1;H2:5])-[C:9]-[C:10] | null | [] | null | null | null | null | The title compound was prepared by the method of Example 382 as a yellow oil (22 mg, 62%) from (7aS,11aR)-2-(2,3-dichlorophenyl)-5,6,7a,8,9,10,11,11a-octahydro-4H-pyrido[3′,4′:4,5]pyrrolo[3,2,1-ij]quinoline (30 mg, 0.083 mmol) and 5-bromo-1-pentene (25 mg, 0.17 mmol). 1H NMR (CDCl3, 300 MHz) δ 1.62–1.75 (br, 2H), 2.01–... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | c1cc2c3c(c1)[C@@H]1CNCC[C@@H]1N3CCC2 | c1cc2c3c(c1)[C@@H]1C[NH]CC[C@@H]1N3CCC2 | c1ccccc1.c1cc2c3c(c1)[C@@H]1C[NH]CC[C@@H]1N3CCC2 | HBr | null | null | null | C=CCCCBr.Clc1cccc(-c2cc3c4c(c2)[C@@H]2CNCC[C@@H]2N4CCC3)c1Cl>>C=CCCCN1CC[C@H]2[C@@H](C1)c1cc(-c3cccc(Cl)c3Cl)cc3c1N2CCC3 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-f37eb5744a4046c2a5a5aa3ccb7fb21b | CC(C)=CCBr.Clc1cccc(-c2cc3c4c(c2)[C@@H]2CNCC[C@@H]2N4CCC3)c1Cl>>CC(C)=CCN1CC[C@H]2[C@@H](C1)c1cc(-c3cccc(Cl)c3Cl)cc3c1N2CCC3 | ClC1=C(C=CC=C1Cl)C=1C=C2CCCN3C2=C(C1)[C@H]1[C@@H]3CCNC1.BrCC=C(C)C.N>>ClC1=C(C=CC=C1Cl)C=1C=C2CCCN3C2=C(C1)[C@H]1[C@@H]3CCN(C1)CC=C(C)C | Br[CH2:5][CH:4]=[C:2]([CH3:1])[CH3:3].[NH:6]1[CH2:7][CH2:8][C@H:9]2[C@@H:10]([CH2:11]1)[c:12]1[cH:13][c:14](-[c:15]3[cH:16][cH:17][cH:18][c:19]([Cl:20])[c:21]3[Cl:22])[cH:23][c:24]3[c:25]1[N:26]2[CH2:27][CH2:28][CH2:29]3>>[CH3:1][C:2]([CH3:3])=[CH:4][CH2:5][N:6]1[CH2:7][CH2:8][C@H:9]2[C@@H:10]([CH2:11]1)[c:12]1[cH:13][... | CC(C)=CCBr.Clc1cccc(-c2cc3c4c(c2)[C@@H]2CNCC[C@@H]2N4CCC3)c1Cl | CC(C)=CCN1CC[C@H]2[C@@H](C1)c1cc(-c3cccc(Cl)c3Cl)cc3c1N2CCC3 | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 156e57521f17e5fff63c4f7b30e3a65e7ad32d15778d94884e7e127a119f08c7 | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | c1ccc(-c2cc3c4c(c2)[C@@H]2CNCC[C@@H]2N4CCC3)cc1 | Br-[CH2;D2;+0:1]-[C:2]=[C:3](-[C;D1;H3:4])-[C;D1;H3:5].[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;D1;H3:4])-[C;D1;H3:5])-[C:9]-[C:10] | null | [] | null | null | null | null | The title compound was prepared by the method of Example 382 as a yellow oil (27 mg, 76%) from (7aS,11aR)-2-(2,3-dichlorophenyl)-5,6,7a,8,9,10,11,11a-octahydro-4H-pyrido[3′,4′:4,5]pyrrolo[3,2,1-ij]quinoline (30 mg, 0.083 mmol) and 4-bromo-2-methyl-2-butene (25 mg, 0.17 mmol). MS (CI, NH3): 427.1 (base, M+H).
Conditions... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | c1cc2c3c(c1)[C@@H]1CNCC[C@@H]1N3CCC2 | c1cc2c3c(c1)[C@@H]1C[NH]CC[C@@H]1N3CCC2 | c1ccccc1.c1cc2c3c(c1)[C@@H]1C[NH]CC[C@@H]1N3CCC2 | HBr | null | null | null | CC(C)=CCBr.Clc1cccc(-c2cc3c4c(c2)[C@@H]2CNCC[C@@H]2N4CCC3)c1Cl>>CC(C)=CCN1CC[C@H]2[C@@H](C1)c1cc(-c3cccc(Cl)c3Cl)cc3c1N2CCC3 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-1f1f0cdd4be94721ae13beccfbc3b458 | CCCBr.Clc1ccc(-c2cc3c4c(c2)[C@@H]2CNCC[C@@H]2N4CCC3)c(Cl)c1>>CCCN1CC[C@H]2[C@@H](C1)c1cc(-c3ccc(Cl)cc3Cl)cc3c1N2CCC3 | ClC1=C(C=CC(=C1)Cl)C=1C=C2CCCN3C2=C(C1)[C@H]1[C@@H]3CCNC1.BrCCC.N>>ClC1=C(C=CC(=C1)Cl)C=1C=C2CCCN3C2=C(C1)[C@H]1[C@@H]3CCN(C1)CCC | Br[CH2:3][CH2:2][CH3:1].[NH:4]1[CH2:5][CH2:6][C@H:7]2[C@@H:8]([CH2:9]1)[c:10]1[cH:11][c:12](-[c:13]3[cH:14][cH:15][c:16]([Cl:17])[cH:18][c:19]3[Cl:20])[cH:21][c:22]3[c:23]1[N:24]2[CH2:25][CH2:26][CH2:27]3>>[CH3:1][CH2:2][CH2:3][N:4]1[CH2:5][CH2:6][C@H:7]2[C@@H:8]([CH2:9]1)[c:10]1[cH:11][c:12](-[c:13]3[cH:14][cH:15][c:1... | CCCBr.Clc1ccc(-c2cc3c4c(c2)[C@@H]2CNCC[C@@H]2N4CCC3)c(Cl)c1 | CCCN1CC[C@H]2[C@@H](C1)c1cc(-c3ccc(Cl)cc3Cl)cc3c1N2CCC3 | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 156e57521f17e5fff63c4f7b30e3a65e7ad32d15778d94884e7e127a119f08c7 | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | c1ccc(-c2cc3c4c(c2)[C@@H]2CNCC[C@@H]2N4CCC3)cc1 | Br-[CH2;D2;+0:1]-[C: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](-[CH2;D2;+0:1]-[C:2]-[C;D1;H3:3])-[C:7]-[C:8] | null | [] | null | null | null | null | The title compound was prepared by the method of Example 382 as a yellow oil (21 mg, 65%) from (7aS,11aR)-2-(2,4-dichlorophenyl)-5,6,7a,8,9,10,11,11a-octahydro-4H-pyrido[3′,4′:4,5]pyrrolo[3,2,1-ij]quinoline (30 mg, 0.083 mmol) and 1-bromopropane (30 mg, 0.24 mmol). 1H NMR (CDCl3, 300 MHz) δ 0.92 (t, J=7.3 Hz, 3H), 1.61... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | c1cc2c3c(c1)[C@@H]1CNCC[C@@H]1N3CCC2 | c1cc2c3c(c1)[C@@H]1C[NH]CC[C@@H]1N3CCC2 | c1ccccc1.c1cc2c3c(c1)[C@@H]1C[NH]CC[C@@H]1N3CCC2 | HBr | null | null | null | CCCBr.Clc1ccc(-c2cc3c4c(c2)[C@@H]2CNCC[C@@H]2N4CCC3)c(Cl)c1>>CCCN1CC[C@H]2[C@@H](C1)c1cc(-c3ccc(Cl)cc3Cl)cc3c1N2CCC3 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-c59f42d892b249838ff953619909281e | CCCCBr.Clc1ccc(-c2cc3c4c(c2)[C@@H]2CNCC[C@@H]2N4CCC3)c(Cl)c1>>CCCCN1CC[C@H]2[C@@H](C1)c1cc(-c3ccc(Cl)cc3Cl)cc3c1N2CCC3 | ClC1=C(C=CC(=C1)Cl)C=1C=C2CCCN3C2=C(C1)[C@H]1[C@@H]3CCNC1.BrCCCC.N>>C(CCC)N1C[C@@H]2[C@@H](N3CCCC4=CC(=CC2=C34)C3=C(C=C(C=C3)Cl)Cl)CC1 | Br[CH2:4][CH2:3][CH2:2][CH3:1].[NH:5]1[CH2:6][CH2:7][C@H:8]2[C@@H:9]([CH2:10]1)[c:11]1[cH:12][c:13](-[c:14]3[cH:15][cH:16][c:17]([Cl:18])[cH:19][c:20]3[Cl:21])[cH:22][c:23]3[c:24]1[N:25]2[CH2:26][CH2:27][CH2:28]3>>[CH3:1][CH2:2][CH2:3][CH2:4][N:5]1[CH2:6][CH2:7][C@H:8]2[C@@H:9]([CH2:10]1)[c:11]1[cH:12][c:13](-[c:14]3[c... | CCCCBr.Clc1ccc(-c2cc3c4c(c2)[C@@H]2CNCC[C@@H]2N4CCC3)c(Cl)c1 | CCCCN1CC[C@H]2[C@@H](C1)c1cc(-c3ccc(Cl)cc3Cl)cc3c1N2CCC3 | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 156e57521f17e5fff63c4f7b30e3a65e7ad32d15778d94884e7e127a119f08c7 | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | c1ccc(-c2cc3c4c(c2)[C@@H]2CNCC[C@@H]2N4CCC3)cc1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[C:4]-[C:5]-[NH;D2;+0:6]-[C:7]-[C:8]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:6](-[C:7]-[C:8])-[C:5]-[C:4] | null | [] | null | null | null | null | The title compound was prepared by the method of Example 382 as a yellow oil (21 mg, 61%) from (7aS,11aR)-2-(2,4-dichlorophenyl)-5,6,7a,8,9,10,11,11a-octahydro-4H-pyrido[3′,4′:4,5]pyrrolo[3,2,1-ij]quinoline (30 mg, 0.083 mmol) and 1-bromobutane (23 mg, 0.17 mmol). MS (CI, NH3): 415.1 (base, M+H).
Conditions: See reacti... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | c1cc2c3c(c1)[C@@H]1CNCC[C@@H]1N3CCC2 | c1cc2c3c(c1)[C@@H]1C[NH]CC[C@@H]1N3CCC2 | c1ccccc1.c1cc2c3c(c1)[C@@H]1C[NH]CC[C@@H]1N3CCC2 | HBr | null | null | null | CCCCBr.Clc1ccc(-c2cc3c4c(c2)[C@@H]2CNCC[C@@H]2N4CCC3)c(Cl)c1>>CCCCN1CC[C@H]2[C@@H](C1)c1cc(-c3ccc(Cl)cc3Cl)cc3c1N2CCC3 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-33c64ac96fcc4760bb40c1d56201cd4b | C=CCCCBr.Clc1ccc(-c2cc3c4c(c2)[C@@H]2CNCC[C@@H]2N4CCC3)c(Cl)c1>>C=CCCCN1CC[C@H]2[C@@H](C1)c1cc(-c3ccc(Cl)cc3Cl)cc3c1N2CCC3 | ClC1=C(C=CC(=C1)Cl)C=1C=C2CCCN3C2=C(C1)[C@H]1[C@@H]3CCNC1.BrCCCC=C.N>>ClC1=C(C=CC(=C1)Cl)C=1C=C2CCCN3C2=C(C1)[C@H]1[C@@H]3CCN(C1)CCCC=C | Br[CH2:5][CH2:4][CH2:3][CH:2]=[CH2:1].[NH:6]1[CH2:7][CH2:8][C@H:9]2[C@@H:10]([CH2:11]1)[c:12]1[cH:13][c:14](-[c:15]3[cH:16][cH:17][c:18]([Cl:19])[cH:20][c:21]3[Cl:22])[cH:23][c:24]3[c:25]1[N:26]2[CH2:27][CH2:28][CH2:29]3>>[CH2:1]=[CH:2][CH2:3][CH2:4][CH2:5][N:6]1[CH2:7][CH2:8][C@H:9]2[C@@H:10]([CH2:11]1)[c:12]1[cH:13][... | C=CCCCBr.Clc1ccc(-c2cc3c4c(c2)[C@@H]2CNCC[C@@H]2N4CCC3)c(Cl)c1 | C=CCCCN1CC[C@H]2[C@@H](C1)c1cc(-c3ccc(Cl)cc3Cl)cc3c1N2CCC3 | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 156e57521f17e5fff63c4f7b30e3a65e7ad32d15778d94884e7e127a119f08c7 | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | c1ccc(-c2cc3c4c(c2)[C@@H]2CNCC[C@@H]2N4CCC3)cc1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3]-[C:4]=[C;D1;H2:5].[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]=[C;D1;H2:5])-[C:9]-[C:10] | null | [] | null | null | null | null | The title compound was prepared by the method of Example 382 as a yellow oil (23 mg, 67%) from (7aS,11aR)-2-(2,4-dichlorophenyl)-5,6,7a,8,9,10,11,11a-octahydro-4H-pyrido[3′,4′:4,5]pyrrolo[3,2,1-ij]quinoline (30 mg, 0.083 mmol) and 5-bromo-1-pentene (25 mg, 0.16 mmol). MS (CI, NH3): 427.1 (base, M+H).
Conditions: See re... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | c1cc2c3c(c1)[C@@H]1CNCC[C@@H]1N3CCC2 | c1cc2c3c(c1)[C@@H]1C[NH]CC[C@@H]1N3CCC2 | c1ccccc1.c1cc2c3c(c1)[C@@H]1C[NH]CC[C@@H]1N3CCC2 | HBr | null | null | null | C=CCCCBr.Clc1ccc(-c2cc3c4c(c2)[C@@H]2CNCC[C@@H]2N4CCC3)c(Cl)c1>>C=CCCCN1CC[C@H]2[C@@H](C1)c1cc(-c3ccc(Cl)cc3Cl)cc3c1N2CCC3 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-8981e0181aee476d83d906edd7021bd3 | CC(C)=CCBr.Clc1ccc(-c2cc3c4c(c2)[C@@H]2CNCC[C@@H]2N4CCC3)c(Cl)c1>>CC(C)=CCN1CC[C@H]2[C@@H](C1)c1cc(-c3ccc(Cl)cc3Cl)cc3c1N2CCC3 | ClC1=C(C=CC(=C1)Cl)C=1C=C2CCCN3C2=C(C1)[C@H]1[C@@H]3CCNC1.BrCC=C(C)C.N>>ClC1=C(C=CC(=C1)Cl)C=1C=C2CCCN3C2=C(C1)[C@H]1[C@@H]3CCN(C1)CC=C(C)C | Br[CH2:5][CH:4]=[C:2]([CH3:1])[CH3:3].[NH:6]1[CH2:7][CH2:8][C@H:9]2[C@@H:10]([CH2:11]1)[c:12]1[cH:13][c:14](-[c:15]3[cH:16][cH:17][c:18]([Cl:19])[cH:20][c:21]3[Cl:22])[cH:23][c:24]3[c:25]1[N:26]2[CH2:27][CH2:28][CH2:29]3>>[CH3:1][C:2]([CH3:3])=[CH:4][CH2:5][N:6]1[CH2:7][CH2:8][C@H:9]2[C@@H:10]([CH2:11]1)[c:12]1[cH:13][... | CC(C)=CCBr.Clc1ccc(-c2cc3c4c(c2)[C@@H]2CNCC[C@@H]2N4CCC3)c(Cl)c1 | CC(C)=CCN1CC[C@H]2[C@@H](C1)c1cc(-c3ccc(Cl)cc3Cl)cc3c1N2CCC3 | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 156e57521f17e5fff63c4f7b30e3a65e7ad32d15778d94884e7e127a119f08c7 | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | c1ccc(-c2cc3c4c(c2)[C@@H]2CNCC[C@@H]2N4CCC3)cc1 | Br-[CH2;D2;+0:1]-[C:2]=[C:3](-[C;D1;H3:4])-[C;D1;H3:5].[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;D1;H3:4])-[C;D1;H3:5])-[C:9]-[C:10] | null | [] | null | null | null | null | The title compound was prepared by the method of Example 382 as a yellow oil (26 mg, 76%) from (7aS,11aR)-2-(2,4-dichlorophenyl)-5,6,7a,8,9,10,11,11a-octahydro-4H-pyrido[3′,4′:4,5]pyrrolo[3,2,1-ij]quinoline (30 mg, 0.083 mmol) and 4-bromo-2-methyl-2-butene (25 mg, 0.16 mmol). 1H NMR (CDCl3, 300 MHz) δ 1.68 (s, 3H), 1.8... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | c1cc2c3c(c1)[C@@H]1CNCC[C@@H]1N3CCC2 | c1cc2c3c(c1)[C@@H]1C[NH]CC[C@@H]1N3CCC2 | c1ccccc1.c1cc2c3c(c1)[C@@H]1C[NH]CC[C@@H]1N3CCC2 | HBr | null | null | null | CC(C)=CCBr.Clc1ccc(-c2cc3c4c(c2)[C@@H]2CNCC[C@@H]2N4CCC3)c(Cl)c1>>CC(C)=CCN1CC[C@H]2[C@@H](C1)c1cc(-c3ccc(Cl)cc3Cl)cc3c1N2CCC3 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-83e41d3c9d1f4cad91ad58eed1d68f76 | CC(=O)O.COc1ccc(-c2cc3c4c(c2)[C@@H]2CNCC[C@@H]2N4CCC3)c(C(F)(F)F)c1>>CCN1CC[C@H]2[C@@H](C1)c1cc(-c3ccc(OC)cc3C(F)(F)F)cc3c1N2CCC3 | COC1=CC(=C(C=C1)C=1C=C2CCCN3C2=C(C1)[C@H]1[C@@H]3CCNC1)C(F)(F)F.C(C)(=O)O>>C(C)N1C[C@@H]2[C@@H](N3CCCC4=CC(=CC2=C34)C3=C(C=C(C=C3)OC)C(F)(F)F)CC1 | O=[C:2](O)[CH3:1].[NH:3]1[CH2:4][CH2:5][C@H:6]2[C@@H:7]([CH2:8]1)[c:9]1[cH:10][c:11](-[c:12]3[cH:13][cH:14][c:15]([O:16][CH3:17])[cH:18][c:19]3[C:20]([F:21])([F:22])[F:23])[cH:24][c:25]3[c:26]1[N:27]2[CH2:28][CH2:29][CH2:30]3>>[CH3:1][CH2:2][N:3]1[CH2:4][CH2:5][C@H:6]2[C@@H:7]([CH2:8]1)[c:9]1[cH:10][c:11](-[c:12]3[cH:1... | CC(=O)O.COc1ccc(-c2cc3c4c(c2)[C@@H]2CNCC[C@@H]2N4CCC3)c(C(F)(F)F)c1 | CCN1CC[C@H]2[C@@H](C1)c1cc(-c3ccc(OC)cc3C(F)(F)F)cc3c1N2CCC3 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | e0e7ebd8b7c9a80b7d0d9109dbd6f95a4e158c7ec6e82a0ee064d106aacb775d | 5fb52ddc67e52a472f28d69e60f3ac94989e70b5307ac3fa95fe53e87c1d2696 | c1ccc(-c2cc3c4c(c2)[C@@H]2CNCC[C@@H]2N4CCC3)cc1 | O-[C;H0;D3;+0:1](=O)-[C;D1;H3:2].[C:3]-[C:4]-[NH;D2;+0:5]-[C:6]-[C:7]>>[C:3]-[C:4]-[N;H0;D3;+0:5](-[CH2;D2;+0:1]-[C;D1;H3:2])-[C:6]-[C:7] | 81 | [{"value": 81.0, "product": "C(C)N1C[C@@H]2[C@@H](N3CCCC4=CC(=CC2=C34)C3=C(C=C(C=C3)OC)C(F)(F)F)CC1", "details": "PERCENTYIELD", "is_desired": false}] | 55 | CELSIUS | 15 | HOUR | To a solution of (7aS,11aR)-2-[4-methoxy-2-(trifluoromethyl)phenyl]-5,6,7a,8,9,10,11,11a-octahydro-4H-pyrido[3′,4′:4,5]pyrrolo[3,2,1-ij]quinoline (30 mg, 0.077 mmol) in acetic acid (0.28 mL) was added NaBH (30 mg, 0.80 mmol) in 2 portion in 10 min interval at 55° C. The reaction mixture was stirred for 15 h at 55° C. t... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | Tertiary amine | c1cc2c3c(c1)[C@@H]1CNCC[C@@H]1N3CCC2 | c1cc2c3c(c1)[C@@H]1C[NH]CC[C@@H]1N3CCC2 | c1ccccc1.c1cc2c3c(c1)[C@@H]1C[NH]CC[C@@H]1N3CCC2 | Other | null | 55 | 15 | CC(=O)O.COc1ccc(-c2cc3c4c(c2)[C@@H]2CNCC[C@@H]2N4CCC3)c(C(F)(F)F)c1>>CCN1CC[C@H]2[C@@H](C1)c1cc(-c3ccc(OC)cc3C(F)(F)F)cc3c1N2CCC3 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-019691de00ee4d9790b1345f07ffa579 | CCCBr.COc1ccc(-c2cc3c4c(c2)[C@@H]2CNCC[C@@H]2N4CCC3)c(C(F)(F)F)c1>>CCCN1CC[C@H]2[C@@H](C1)c1cc(-c3ccc(OC)cc3C(F)(F)F)cc3c1N2CCC3 | COC1=CC(=C(C=C1)C=1C=C2CCCN3C2=C(C1)[C@H]1[C@@H]3CCNC1)C(F)(F)F.BrCCC.N>>COC1=CC(=C(C=C1)C=1C=C2CCCN3C2=C(C1)[C@H]1[C@@H]3CCN(C1)CCC)C(F)(F)F | Br[CH2:3][CH2:2][CH3:1].[NH:4]1[CH2:5][CH2:6][C@H:7]2[C@@H:8]([CH2:9]1)[c:10]1[cH:11][c:12](-[c:13]3[cH:14][cH:15][c:16]([O:17][CH3:18])[cH:19][c:20]3[C:21]([F:22])([F:23])[F:24])[cH:25][c:26]3[c:27]1[N:28]2[CH2:29][CH2:30][CH2:31]3>>[CH3:1][CH2:2][CH2:3][N:4]1[CH2:5][CH2:6][C@H:7]2[C@@H:8]([CH2:9]1)[c:10]1[cH:11][c:12... | CCCBr.COc1ccc(-c2cc3c4c(c2)[C@@H]2CNCC[C@@H]2N4CCC3)c(C(F)(F)F)c1 | CCCN1CC[C@H]2[C@@H](C1)c1cc(-c3ccc(OC)cc3C(F)(F)F)cc3c1N2CCC3 | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 156e57521f17e5fff63c4f7b30e3a65e7ad32d15778d94884e7e127a119f08c7 | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | c1ccc(-c2cc3c4c(c2)[C@@H]2CNCC[C@@H]2N4CCC3)cc1 | Br-[CH2;D2;+0:1]-[C: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](-[CH2;D2;+0:1]-[C:2]-[C;D1;H3:3])-[C:7]-[C:8] | null | [] | null | null | null | null | The title compound was prepared by the method of Example 382 as a yellow oil (23 mg, 69%) from (7aS,11aR)-2-[4-methoxy-2-(trifluoromethyl)phenyl]-5,6,7a,8,9,10,11,11a-octahydro-4H-pyrido[3′,4′:4,5]pyrrolo[3,2,1-ij]quinoline (30 mg, 0.077 mmol) and 1-bromopropane (20 mg, 0.15 mmol). 1H NMR (CDCl3, 300 MHz) δ 0.98 (t, J=... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | c1cc2c3c(c1)[C@@H]1CNCC[C@@H]1N3CCC2 | c1cc2c3c(c1)[C@@H]1C[NH]CC[C@@H]1N3CCC2 | c1ccccc1.c1cc2c3c(c1)[C@@H]1C[NH]CC[C@@H]1N3CCC2 | HBr | null | null | null | CCCBr.COc1ccc(-c2cc3c4c(c2)[C@@H]2CNCC[C@@H]2N4CCC3)c(C(F)(F)F)c1>>CCCN1CC[C@H]2[C@@H](C1)c1cc(-c3ccc(OC)cc3C(F)(F)F)cc3c1N2CCC3 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-7731258d52554c538766be4be2588ee7 | C=CCCCBr.COc1ccc(-c2cc3c4c(c2)[C@@H]2CNCC[C@@H]2N4CCC3)c(C(F)(F)F)c1>>C=CCCCN1CC[C@H]2[C@@H](C1)c1cc(-c3ccc(OC)cc3C(F)(F)F)cc3c1N2CCC3 | COC1=CC(=C(C=C1)C=1C=C2CCCN3C2=C(C1)[C@H]1[C@@H]3CCNC1)C(F)(F)F.BrCCCC=C.N>>COC1=CC(=C(C=C1)C=1C=C2CCCN3C2=C(C1)[C@H]1[C@@H]3CCN(C1)CCCC=C)C(F)(F)F | Br[CH2:5][CH2:4][CH2:3][CH:2]=[CH2:1].[NH:6]1[CH2:7][CH2:8][C@H:9]2[C@@H:10]([CH2:11]1)[c:12]1[cH:13][c:14](-[c:15]3[cH:16][cH:17][c:18]([O:19][CH3:20])[cH:21][c:22]3[C:23]([F:24])([F:25])[F:26])[cH:27][c:28]3[c:29]1[N:30]2[CH2:31][CH2:32][CH2:33]3>>[CH2:1]=[CH:2][CH2:3][CH2:4][CH2:5][N:6]1[CH2:7][CH2:8][C@H:9]2[C@@H:1... | C=CCCCBr.COc1ccc(-c2cc3c4c(c2)[C@@H]2CNCC[C@@H]2N4CCC3)c(C(F)(F)F)c1 | C=CCCCN1CC[C@H]2[C@@H](C1)c1cc(-c3ccc(OC)cc3C(F)(F)F)cc3c1N2CCC3 | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 156e57521f17e5fff63c4f7b30e3a65e7ad32d15778d94884e7e127a119f08c7 | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | c1ccc(-c2cc3c4c(c2)[C@@H]2CNCC[C@@H]2N4CCC3)cc1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3]-[C:4]=[C;D1;H2:5].[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]=[C;D1;H2:5])-[C:9]-[C:10] | null | [] | null | null | null | null | The title compound was prepared by the method of Example 382 as a yellow oil (22 mg, 63%) from (7aS,11aR)-2-[4-methoxy-2-(trifluoromethyl)phenyl]-5,6,7a,8,9,10,11,11a-octahydro-4H-pyrido[3′,4′:4,5]pyrrolo[3,2,1-ij]quinoline (30 mg, 0.077 mmol) and 5-bromo-1-pentene (23 mg, 0.15 mmol). 1H NMR (CDCl3, 300 MHz) δ 1.68–1.7... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | c1cc2c3c(c1)[C@@H]1CNCC[C@@H]1N3CCC2 | c1cc2c3c(c1)[C@@H]1C[NH]CC[C@@H]1N3CCC2 | c1ccccc1.c1cc2c3c(c1)[C@@H]1C[NH]CC[C@@H]1N3CCC2 | HBr | null | null | null | C=CCCCBr.COc1ccc(-c2cc3c4c(c2)[C@@H]2CNCC[C@@H]2N4CCC3)c(C(F)(F)F)c1>>C=CCCCN1CC[C@H]2[C@@H](C1)c1cc(-c3ccc(OC)cc3C(F)(F)F)cc3c1N2CCC3 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-be84112bc56d4414a3b53e853ae54309 | CC(C)=CCBr.COc1ccc(-c2cc3c4c(c2)[C@@H]2CNCC[C@@H]2N4CCC3)c(C(F)(F)F)c1>>COc1ccc(-c2cc3c4c(c2)[C@@H]2CN(CC=C(C)C)CC[C@@H]2N4CCC3)c(C(F)(F)F)c1 | COC1=CC(=C(C=C1)C=1C=C2CCCN3C2=C(C1)[C@H]1[C@@H]3CCNC1)C(F)(F)F.BrCC=C(C)C.N>>COC1=CC(=C(C=C1)C=1C=C2CCCN3C2=C(C1)[C@H]1[C@@H]3CCN(C1)CC=C(C)C)C(F)(F)F | Br[CH2:16][CH:17]=[C:18]([CH3:19])[CH3:20].[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][c:9]3[c:10]4[c:11]([cH:12]2)[C@@H:13]2[CH2:14][NH:15][CH2:21][CH2:22][C@@H:23]2[N:24]4[CH2:25][CH2:26][CH2:27]3)[c:28]([C:29]([F:30])([F:31])[F:32])[cH:33]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][c:9]3[c:10]4[c:11](... | CC(C)=CCBr.COc1ccc(-c2cc3c4c(c2)[C@@H]2CNCC[C@@H]2N4CCC3)c(C(F)(F)F)c1 | COc1ccc(-c2cc3c4c(c2)[C@@H]2CN(CC=C(C)C)CC[C@@H]2N4CCC3)c(C(F)(F)F)c1 | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 156e57521f17e5fff63c4f7b30e3a65e7ad32d15778d94884e7e127a119f08c7 | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | c1ccc(-c2cc3c4c(c2)[C@@H]2CNCC[C@@H]2N4CCC3)cc1 | Br-[CH2;D2;+0:1]-[C:2]=[C:3](-[C;D1;H3:4])-[C;D1;H3:5].[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;D1;H3:4])-[C;D1;H3:5])-[C:9]-[C:10] | null | [] | null | null | null | null | The title compound was prepared by the method of Example 382 as a yellow oil (25 mg, 71%) from (7aS,11aR)-2-[4-methoxy-2-(trifluoromethyl)phenyl]-5,6,7a,8,9,10,11,11a-octahydro-4H-pyrido[3′,4′:4,5]pyrrolo[3,2,1-ij]quinoline (30 mg, 0.077 mmol) and 4-bromo-2-methyl-2-butene (23 mg, 0.15 mmol). 1H NMR (CDCl3, 300 MHz) δ ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | c1cc2c3c(c1)[C@@H]1CNCC[C@@H]1N3CCC2 | c1cc2c3c(c1)[C@@H]1C[NH]CC[C@@H]1N3CCC2 | c1ccccc1.c1cc2c3c(c1)[C@@H]1C[NH]CC[C@@H]1N3CCC2 | HBr | null | null | null | CC(C)=CCBr.COc1ccc(-c2cc3c4c(c2)[C@@H]2CNCC[C@@H]2N4CCC3)c(C(F)(F)F)c1>>COc1ccc(-c2cc3c4c(c2)[C@@H]2CN(CC=C(C)C)CC[C@@H]2N4CCC3)c(C(F)(F)F)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-6e128f1b10e14991a701ea8344cb1b66 | COc1ccc(-c2cc3c4c(c2)[C@@H]2CNCC[C@@H]2N4CCC3)c(C(F)(F)F)c1.FC(F)CBr>>COc1ccc(-c2cc3c4c(c2)[C@@H]2CN(CC(F)F)CC[C@@H]2N4CCC3)c(C(F)(F)F)c1 | COC1=CC(=C(C=C1)C=1C=C2CCCN3C2=C(C1)[C@H]1[C@@H]3CCNC1)C(F)(F)F.BrCC(F)F.N>>FC(CN1C[C@@H]2[C@@H](N3CCCC4=CC(=CC2=C34)C3=C(C=C(C=C3)OC)C(F)(F)F)CC1)F | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][c:9]3[c:10]4[c:11]([cH:12]2)[C@@H:13]2[CH2:14][NH:15][CH2:20][CH2:21][C@@H:22]2[N:23]4[CH2:24][CH2:25][CH2:26]3)[c:27]([C:28]([F:29])([F:30])[F:31])[cH:32]1.Br[CH2:16][CH:17]([F:18])[F:19]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][c:9]3[c:10]4[c:11]([cH:12]2)[C... | COc1ccc(-c2cc3c4c(c2)[C@@H]2CNCC[C@@H]2N4CCC3)c(C(F)(F)F)c1.FC(F)CBr | COc1ccc(-c2cc3c4c(c2)[C@@H]2CN(CC(F)F)CC[C@@H]2N4CCC3)c(C(F)(F)F)c1 | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 156e57521f17e5fff63c4f7b30e3a65e7ad32d15778d94884e7e127a119f08c7 | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | c1ccc(-c2cc3c4c(c2)[C@@H]2CNCC[C@@H]2N4CCC3)cc1 | Br-[CH2;D2;+0:1]-[C:2](-[F;D1;H0:3])-[F;D1;H0:4].[C:5]-[C:6]-[NH;D2;+0:7]-[C:8]-[C:9]>>[C:5]-[C:6]-[N;H0;D3;+0:7](-[CH2;D2;+0:1]-[C:2](-[F;D1;H0:3])-[F;D1;H0:4])-[C:8]-[C:9] | null | [] | null | null | null | null | The title compound was prepared by the method of Example 382 as a yellow oil (27 mg, 77%) from (7aS,11aR)-2-[4-methoxy-2-(trifluoromethyl)phenyl]-5,6,7a,8,9,10,11,11a-octahydro-4H-pyrido[3′,4′:4,5]pyrrolo[3,2,1-ij]quinoline (30 mg, 0.077 mmol) and 2-bromo-1,1-difluoroethane (35 mg, 0.23 mmol). MS (C1, NH3): 453.1 (base... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | c1cc2c3c(c1)[C@@H]1CNCC[C@@H]1N3CCC2 | c1cc2c3c(c1)[C@@H]1C[NH]CC[C@@H]1N3CCC2 | c1ccccc1.c1cc2c3c(c1)[C@@H]1C[NH]CC[C@@H]1N3CCC2 | HBr | null | null | null | COc1ccc(-c2cc3c4c(c2)[C@@H]2CNCC[C@@H]2N4CCC3)c(C(F)(F)F)c1.FC(F)CBr>>COc1ccc(-c2cc3c4c(c2)[C@@H]2CN(CC(F)F)CC[C@@H]2N4CCC3)c(C(F)(F)F)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-0bfe6daad78c40cdacb575412bab00f5 | O=C(CCCCl)c1ccc(F)cc1.c1cc2c3c(c1)[C@@H]1CNCC[C@@H]1N3CCC2>>O=C(CCCN1CC[C@H]2[C@@H](C1)c1cccc3c1N2CCC3)c1ccc(F)cc1 | C1=CC=C2CCCN3C2=C1[C@H]1[C@@H]3CCNC1.ClCCCC(=O)C1=CC=C(C=C1)F.C(=O)([O-])[O-].[K+].[K+]>>C1=CC=C2CCCN3C2=C1[C@H]1[C@@H]3CCN(C1)CCCC(=O)C1=CC=C(C=C1)F | Cl[CH2:5][CH2:4][CH2:3][C:2](=[O:1])[c:22]1[cH:23][cH:24][c:25]([F:26])[cH:27][cH:28]1.[NH:6]1[CH2:7][CH2:8][C@H:9]2[C@@H:10]([CH2:11]1)[c:12]1[cH:13][cH:14][cH:15][c:16]3[c:17]1[N:18]2[CH2:19][CH2:20][CH2:21]3>>[O:1]=[C:2]([CH2:3][CH2:4][CH2:5][N:6]1[CH2:7][CH2:8][C@H:9]2[C@@H:10]([CH2:11]1)[c:12]1[cH:13][cH:14][cH:15... | O=C(CCCCl)c1ccc(F)cc1.c1cc2c3c(c1)[C@@H]1CNCC[C@@H]1N3CCC2 | O=C(CCCN1CC[C@H]2[C@@H](C1)c1cccc3c1N2CCC3)c1ccc(F)cc1 | null | null | O1CCOCC1.C(Cl)(Cl)Cl | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 156e57521f17e5fff63c4f7b30e3a65e7ad32d15778d94884e7e127a119f08c7 | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | O=C(CCCN1CC[C@H]2[C@@H](C1)c1cccc3c1N2CCC3)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] | 58.1 | [{"value": 58.0, "product": "C1=CC=C2CCCN3C2=C1[C@H]1[C@@H]3CCN(C1)CCCC(=O)C1=CC=C(C=C1)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 58.1, "product": "C1=CC=C2CCCN3C2=C1[C@H]1[C@@H]3CCN(C1)CCCC(=O)C1=CC=C(C=C1)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | null | null | To a solution of (7aS,11aR)-5,6,7a, 8,9,10,11,11a-octahydro-4H-pyrido[3′,4′:4,5]pyrrolo[3,2,1-ij]quinoline (0.21 g, 1.0 mmol)) in 1,4-dioxane (7.0 mL) were added 4-chloro-4′-fluorobutyrophenone (0.40 g, 2.0 mmol), KI (catalytic amount) and K2CO3(0.28 g, 2.0 mmol). The reaction mixture was heated at 100° C. for 48 h. Th... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | c1cc2c3c(c1)[C@@H]1CNCC[C@@H]1N3CCC2 | c1cc2c3c(c1)[C@@H]1C[NH]CC[C@@H]1N3CCC2 | c1ccccc1.c1cc2c3c(c1)[C@@H]1C[NH]CC[C@@H]1N3CCC2 | HCl | O1CCOCC1.C(Cl)(Cl)Cl | 100 | null | O=C(CCCCl)c1ccc(F)cc1.c1cc2c3c(c1)[C@@H]1CNCC[C@@H]1N3CCC2>O1CCOCC1.C(Cl)(Cl)Cl>O=C(CCCN1CC[C@H]2[C@@H](C1)c1cccc3c1N2CCC3)c1ccc(F)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-95d94df1e86b4f8f9ce0b368d3acebc4 | Nc1ccccc1C(=O)CCCCl.c1cc2c3c(c1)[C@@H]1CNCC[C@@H]1N3CCC2>>Nc1ccccc1C(=O)CCCN1CC[C@H]2[C@@H](C1)c1cccc3c1N2CCC3 | C1=CC=C2CCCN3C2=C1[C@H]1[C@@H]3CCNC1.ClCCCC(=O)C1=C(C=CC=C1)N.C(=O)([O-])[O-].[K+].[K+]>>C1=CC=C2CCCN3C2=C1[C@H]1[C@@H]3CCN(C1)CCCC(=O)C1=C(C=CC=C1)N | Cl[CH2:12][CH2:11][CH2:10][C:8]([c:7]1[c:2]([NH2:1])[cH:3][cH:4][cH:5][cH:6]1)=[O:9].[NH:13]1[CH2:14][CH2:15][C@H:16]2[C@@H:17]([CH2:18]1)[c:19]1[cH:20][cH:21][cH:22][c:23]3[c:24]1[N:25]2[CH2:26][CH2:27][CH2:28]3>>[NH2:1][c:2]1[cH:3][cH:4][cH:5][cH:6][c:7]1[C:8](=[O:9])[CH2:10][CH2:11][CH2:12][N:13]1[CH2:14][CH2:15][C@... | Nc1ccccc1C(=O)CCCCl.c1cc2c3c(c1)[C@@H]1CNCC[C@@H]1N3CCC2 | Nc1ccccc1C(=O)CCCN1CC[C@H]2[C@@H](C1)c1cccc3c1N2CCC3 | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 156e57521f17e5fff63c4f7b30e3a65e7ad32d15778d94884e7e127a119f08c7 | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | O=C(CCCN1CC[C@H]2[C@@H](C1)c1cccc3c1N2CCC3)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] | 16.5 | [{"value": 16.0, "product": "C1=CC=C2CCCN3C2=C1[C@H]1[C@@H]3CCN(C1)CCCC(=O)C1=C(C=CC=C1)N", "details": "PERCENTYIELD", "is_desired": false}, {"value": 16.5, "product": "C1=CC=C2CCCN3C2=C1[C@H]1[C@@H]3CCN(C1)CCCC(=O)C1=C(C=CC=C1)N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | The title compound (0.031 g, 16%) was prepared by the general method of Example 402 from (7aS,11aR)-5,6,7a,8,9,10,11,11a-octahydro-4H-pyrido[3′,4′:4,5]pyrrolo[3,2,1-ij]quinoline (0.11 g, 0.50 mmol), 4-chloro-2′-aminobutyrophenone (0.20 g, 1.0 mmol), KI (catalytic) and K2CO3(0.14 g, 1.0 mmol) after chromatographic purif... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | c1cc2c3c(c1)[C@@H]1CNCC[C@@H]1N3CCC2 | c1cc2c3c(c1)[C@@H]1C[NH]CC[C@@H]1N3CCC2 | c1ccccc1.c1cc2c3c(c1)[C@@H]1C[NH]CC[C@@H]1N3CCC2 | HCl | null | null | null | Nc1ccccc1C(=O)CCCCl.c1cc2c3c(c1)[C@@H]1CNCC[C@@H]1N3CCC2>>Nc1ccccc1C(=O)CCCN1CC[C@H]2[C@@H](C1)c1cccc3c1N2CCC3 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-dc60dc5225a44bfe9f24a2c40f4c49b7 | Nc1ccccc1C(=O)CCCCl.c1cc2c3c(c1)[C@H]1CNCC[C@H]1N3CCC2>>Nc1ccccc1C(=O)CCCN1CC[C@@H]2[C@H](C1)c1cccc3c1N2CCC3 | C1=CC=C2CCCN3C2=C1[C@@H]1[C@H]3CCNC1.ClCCCC(=O)C1=C(C=CC=C1)N.C(=O)([O-])[O-].[K+].[K+]>>C1=CC=C2CCCN3C2=C1[C@@H]1[C@H]3CCN(C1)CCCC(=O)C1=C(C=CC=C1)N | Cl[CH2:12][CH2:11][CH2:10][C:8]([c:7]1[c:2]([NH2:1])[cH:3][cH:4][cH:5][cH:6]1)=[O:9].[NH:13]1[CH2:14][CH2:15][C@@H:16]2[C@H:17]([CH2:18]1)[c:19]1[cH:20][cH:21][cH:22][c:23]3[c:24]1[N:25]2[CH2:26][CH2:27][CH2:28]3>>[NH2:1][c:2]1[cH:3][cH:4][cH:5][cH:6][c:7]1[C:8](=[O:9])[CH2:10][CH2:11][CH2:12][N:13]1[CH2:14][CH2:15][C@... | Nc1ccccc1C(=O)CCCCl.c1cc2c3c(c1)[C@H]1CNCC[C@H]1N3CCC2 | Nc1ccccc1C(=O)CCCN1CC[C@@H]2[C@H](C1)c1cccc3c1N2CCC3 | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 14635250736ebb1f0e2e07dcba66a1eac5a18ac7f42f8c572369b3c0ad2d9436 | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | O=C(CCCN1CC[C@@H]2[C@H](C1)c1cccc3c1N2CCC3)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] | 42.6 | [{"value": 42.0, "product": "C1=CC=C2CCCN3C2=C1[C@@H]1[C@H]3CCN(C1)CCCC(=O)C1=C(C=CC=C1)N", "details": "PERCENTYIELD", "is_desired": false}, {"value": 42.6, "product": "C1=CC=C2CCCN3C2=C1[C@@H]1[C@H]3CCN(C1)CCCC(=O)C1=C(C=CC=C1)N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | The title compound (0.080 g, 42%) was prepared by the general method of Example 402 from (7aR,11aS)-5,6,7a,8,9,10,11,11a-octahydro-4H-pyrido[3′,4′:4,5]pyrrolo[3,2,1-ij]quinoline (0.11 g, 0.50 mmol), 4-chloro-2′-aminobutyrophenone (0.20 g, 1.0 mmol), KI (catalytic) and K2CO3(0.14 g, 1.0 mmol) after chromatographic purif... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | c1cc2c3c(c1)[C@H]1CNCC[C@H]1N3CCC2 | c1cc2c3c(c1)[C@H]1C[NH]CC[C@H]1N3CCC2 | c1ccccc1.c1cc2c3c(c1)[C@H]1C[NH]CC[C@H]1N3CCC2 | HCl | null | null | null | Nc1ccccc1C(=O)CCCCl.c1cc2c3c(c1)[C@H]1CNCC[C@H]1N3CCC2>>Nc1ccccc1C(=O)CCCN1CC[C@@H]2[C@H](C1)c1cccc3c1N2CCC3 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-90614dcdadaa449b92372b398361fb07 | Fc1ccc(OCCCCl)cc1.c1cc2c3c(c1)[C@H]1CNCC[C@H]1N3CCC2>>Fc1ccc(OCCCN2CC[C@@H]3[C@H](C2)c2cccc4c2N3CCC4)cc1 | C1=CC=C2CCCN3C2=C1[C@@H]1[C@H]3CCNC1.ClCCCOC1=CC=C(C=C1)F.C(=O)([O-])[O-].[K+].[K+]>>FC1=CC=C(C=C1)OCCCN1C[C@H]2[C@H](N3CCCC4=CC=CC2=C34)CC1 | Cl[CH2:9][CH2:8][CH2:7][O:6][c:5]1[cH:4][cH:3][c:2]([F:1])[cH:27][cH:26]1.[NH:10]1[CH2:11][CH2:12][C@@H:13]2[C@H:14]([CH2:15]1)[c:16]1[cH:17][cH:18][cH:19][c:20]3[c:21]1[N:22]2[CH2:23][CH2:24][CH2:25]3>>[F:1][c:2]1[cH:3][cH:4][c:5]([O:6][CH2:7][CH2:8][CH2:9][N:10]2[CH2:11][CH2:12][C@@H:13]3[C@H:14]([CH2:15]2)[c:16]2[cH... | Fc1ccc(OCCCCl)cc1.c1cc2c3c(c1)[C@H]1CNCC[C@H]1N3CCC2 | Fc1ccc(OCCCN2CC[C@@H]3[C@H](C2)c2cccc4c2N3CCC4)cc1 | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 14635250736ebb1f0e2e07dcba66a1eac5a18ac7f42f8c572369b3c0ad2d9436 | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | c1ccc(OCCCN2CC[C@@H]3[C@H](C2)c2cccc4c2N3CCC4)cc1 | Cl-[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] | 32 | [{"value": 32.0, "product": "FC1=CC=C(C=C1)OCCCN1C[C@H]2[C@H](N3CCCC4=CC=CC2=C34)CC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 31.8, "product": "FC1=CC=C(C=C1)OCCCN1C[C@H]2[C@H](N3CCCC4=CC=CC2=C34)CC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | The title compound (0.14 g, 32%) was prepared by the general method of Example 402 from (±)-cis-5,6,7a,8,9,10,11,11a-octahydro-4H-pyrido[3′,4′:4,5]pyrrolo[3,2,1-ij]quinoline (0.25 g, 1.2 mmol), 1-(3-chloropropoxy)-4-fluorobezene (0.37 g, 2.0 mmol), KI (catalytic) and K2CO3(0.28 g, 2.0 mmol) after chromatographic purifi... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | c1cc2c3c(c1)[C@H]1CNCC[C@H]1N3CCC2 | c1cc2c3c(c1)[C@H]1C[NH]CC[C@H]1N3CCC2 | c1ccccc1.c1cc2c3c(c1)[C@H]1C[NH]CC[C@H]1N3CCC2 | HCl | null | null | null | Fc1ccc(OCCCCl)cc1.c1cc2c3c(c1)[C@H]1CNCC[C@H]1N3CCC2>>Fc1ccc(OCCCN2CC[C@@H]3[C@H](C2)c2cccc4c2N3CCC4)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-957a5c4b9c7a472cbf657a9c8162b1bc | Fc1ccc2c(CCCCl)noc2c1.c1cc2c3c(c1)[C@H]1CNCC[C@H]1N3CCC2>>Fc1ccc2c(CCCN3CC[C@@H]4[C@H](C3)c3cccc5c3N4CCC5)noc2c1 | C1=CC=C2CCCN3C2=C1[C@@H]1[C@H]3CCNC1.ClCCCC1=NOC2=C1C=CC(=C2)F.C(=O)([O-])[O-].[K+].[K+]>>FC1=CC2=C(C(=NO2)CCCN2C[C@H]3[C@H](N4CCCC5=CC=CC3=C45)CC2)C=C1 | Cl[CH2:9][CH2:8][CH2:7][c:6]1[c:5]2[cH:4][cH:3][c:2]([F:1])[cH:29][c:28]2[o:27][n:26]1.[NH:10]1[CH2:11][CH2:12][C@@H:13]2[C@H:14]([CH2:15]1)[c:16]1[cH:17][cH:18][cH:19][c:20]3[c:21]1[N:22]2[CH2:23][CH2:24][CH2:25]3>>[F:1][c:2]1[cH:3][cH:4][c:5]2[c:6]([CH2:7][CH2:8][CH2:9][N:10]3[CH2:11][CH2:12][C@@H:13]4[C@H:14]([CH2:1... | Fc1ccc2c(CCCCl)noc2c1.c1cc2c3c(c1)[C@H]1CNCC[C@H]1N3CCC2 | Fc1ccc2c(CCCN3CC[C@@H]4[C@H](C3)c3cccc5c3N4CCC5)noc2c1 | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 14635250736ebb1f0e2e07dcba66a1eac5a18ac7f42f8c572369b3c0ad2d9436 | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | c1cc2c3c(c1)[C@H]1CN(CCCc4noc5ccccc45)CC[C@H]1N3CCC2 | Cl-[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] | 32 | [{"value": 32.0, "product": "FC1=CC2=C(C(=NO2)CCCN2C[C@H]3[C@H](N4CCCC5=CC=CC3=C45)CC2)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 31.9, "product": "FC1=CC2=C(C(=NO2)CCCN2C[C@H]3[C@H](N4CCCC5=CC=CC3=C45)CC2)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | The title compound (0.15 g, 32%) was prepared by the general method of Example 402 from (±)-cis-5,6,7a,8,9,10,11,11a-octahydro-4H-pyrido[3′,4′:4,5]pyrrolo[3,2,1-ij]quinoline (0.25 g, 1.2 mmol), 3-(3-chloropropyl)-6-fluoro-1,2-benzisoxazole (0.43 g, 2.0 mmol), KI (catalytic) and K2CO3(0.28 g, 2.0 mmol) after chromatogra... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | c1cc2c3c(c1)[C@H]1CNCC[C@H]1N3CCC2 | c1cc2c3c(c1)[C@H]1C[NH]CC[C@H]1N3CCC2 | c1ccc2oncc2c1.c1cc2c3c(c1)[C@H]1C[NH]CC[C@H]1N3CCC2 | HCl | null | null | null | Fc1ccc2c(CCCCl)noc2c1.c1cc2c3c(c1)[C@H]1CNCC[C@H]1N3CCC2>>Fc1ccc2c(CCCN3CC[C@@H]4[C@H](C3)c3cccc5c3N4CCC5)noc2c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-2f60ee695f98447898537ff670b3426c | C1=NCc2c(n3c4c(cccc24)CCC3)C1.O=C(CCCCl)c1ccc(F)cc1>>O=C(CCCN1CCc2c(c3cccc4c3n2CCC4)C1)c1ccc(F)cc1 | C1=CC=C2CCCN3C2=C1C1=C3CC=NC1.ClCCCC(=O)C1=CC=C(C=C1)F.C(=O)([O-])[O-].[K+].[K+]>>FC1=CC=C(C=C1)C(CCCN1CC2=C(N3CCCC4=CC=CC2=C34)CC1)=O | [N:6]1=[CH:7][CH2:8][c:9]2[c:10]([c:11]3[cH:12][cH:13][cH:14][c:15]4[c:16]3[n:17]2[CH2:18][CH2:19][CH2:20]4)[CH2:21]1.Cl[CH2:5][CH2:4][CH2:3][C:2](=[O:1])[c:22]1[cH:23][cH:24][c:25]([F:26])[cH:27][cH:28]1>>[O:1]=[C:2]([CH2:3][CH2:4][CH2:5][N:6]1[CH2:7][CH2:8][c:9]2[c:10]([c:11]3[cH:12][cH:13][cH:14][c:15]4[c:16]3[n:17]... | C1=NCc2c(n3c4c(cccc24)CCC3)C1.O=C(CCCCl)c1ccc(F)cc1 | O=C(CCCN1CCc2c(c3cccc4c3n2CCC4)C1)c1ccc(F)cc1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 20c678aa68223531a61f0d459d61e7c095f8d41d138260befa8347a01d746931 | 7bfceca4e5a6a17e9237a714f96d9b2ea66f2cd9b0dc410b3b326e85455fe161 | O=C(CCCN1CCc2c(c3cccc4c3n2CCC4)C1)c1ccccc1 | Cl-[CH2;D2;+0:1]-[C:2]-[C:3]-[C:4]=[O;D1;H0:5].[#7;a:6]:[c:7]1:[c:8]-[C:9]-[N;H0;D2;+0:10]=[CH;D2;+0:11]-[C:12]-1>>[#7;a:6]:[c:7]1:[c:8]-[C:9]-[N;H0;D3;+0:10](-[CH2;D2;+0:1]-[C:2]-[C:3]-[C:4]=[O;D1;H0:5])-[CH2;D2;+0:11]-[C:12]-1 | 28 | [{"value": 28.0, "product": "FC1=CC=C(C=C1)C(CCCN1CC2=C(N3CCCC4=CC=CC2=C34)CC1)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 28.0, "product": "FC1=CC=C(C=C1)C(CCCN1CC2=C(N3CCCC4=CC=CC2=C34)CC1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | The title compound (0.060 g, 28%) was prepared by the general method of Example 402 from 5,6,8,11-tetrahydro-4H-pyrido[3′,4′:4,5]pyrrolo[3,2,1-ij]quinoline (0.12 g, 0.57 mmol), 4-chloro-4′-fluorobutyrophenone (0.40 g, 2.0 mmol), KI (catalytic) and K2CO3(0.28 g, 2.0 mmol) after chromatographic purification as a white am... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Substituted imine | Tertiary amine | C1=NCc2c(n3c4c(cccc24)CCC3)C1 | c1cc2c3c(c1)c1c(n3CCC2)CC[NH]C1 | c1ccccc1.c1cc2c3c(c1)c1c(n3CCC2)CC[NH]C1 | Other | null | null | null | C1=NCc2c(n3c4c(cccc24)CCC3)C1.O=C(CCCCl)c1ccc(F)cc1>>O=C(CCCN1CCc2c(c3cccc4c3n2CCC4)C1)c1ccc(F)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-df5c7077024449179fdde45e96083de1 | Nc1cc(F)ccc1C(=O)CCCCl.c1cc2c3c(c1)[C@H]1CNCC[C@H]1N3CCC2>>Nc1cc(F)ccc1C(=O)CCCN1CC[C@@H]2[C@H](C1)c1cccc3c1N2CCC3 | C1=CC=C2CCCN3C2=C1[C@@H]1[C@H]3CCNC1.NC1=C(C=CC(=C1)F)C(CCCCl)=O>>C1=CC=C2CCCN3C2=C1[C@@H]1[C@H]3CCN(C1)CCCC(=O)C1=C(C=C(C=C1)F)N | Cl[CH2:13][CH2:12][CH2:11][C:9]([c:8]1[c:2]([NH2:1])[cH:3][c:4]([F:5])[cH:6][cH:7]1)=[O:10].[NH:14]1[CH2:15][CH2:16][C@@H:17]2[C@H:18]([CH2:19]1)[c:20]1[cH:21][cH:22][cH:23][c:24]3[c:25]1[N:26]2[CH2:27][CH2:28][CH2:29]3>>[NH2:1][c:2]1[cH:3][c:4]([F:5])[cH:6][cH:7][c:8]1[C:9](=[O:10])[CH2:11][CH2:12][CH2:13][N:14]1[CH2:... | Nc1cc(F)ccc1C(=O)CCCCl.c1cc2c3c(c1)[C@H]1CNCC[C@H]1N3CCC2 | Nc1cc(F)ccc1C(=O)CCCN1CC[C@@H]2[C@H](C1)c1cccc3c1N2CCC3 | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 14635250736ebb1f0e2e07dcba66a1eac5a18ac7f42f8c572369b3c0ad2d9436 | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | O=C(CCCN1CC[C@@H]2[C@H](C1)c1cccc3c1N2CCC3)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] | null | [] | null | null | null | null | The title compound was prepared by the method of Example 402 as a red oil (99 mg, 54%) from (±)-cis-5,6,7a,8,9,10,11,11a-octahydro-4H-pyrido[3′,4′:4,5]pyrrolo[3,2,1-ij]quinoline (100 mg, 0.47 mmol) and 1-(2-amino-4-fluorophenyl)-4-chloro-1-butanone (152 mg, 0.70 mmol). 1H NMR (CDCl3, 300 MHz) δ 1.95–2.15 (m, 7H), 2.37–... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | c1cc2c3c(c1)[C@H]1CNCC[C@H]1N3CCC2 | c1cc2c3c(c1)[C@H]1C[NH]CC[C@H]1N3CCC2 | c1ccccc1.c1cc2c3c(c1)[C@H]1C[NH]CC[C@H]1N3CCC2 | HCl | null | null | null | Nc1cc(F)ccc1C(=O)CCCCl.c1cc2c3c(c1)[C@H]1CNCC[C@H]1N3CCC2>>Nc1cc(F)ccc1C(=O)CCCN1CC[C@@H]2[C@H](C1)c1cccc3c1N2CCC3 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-b47e8604729d4430800ac336b08336ba | Nc1cc(F)ccc1C(=O)CCCCl.c1cc2c3c(c1)[C@@H]1CNCC[C@@H]1N3CCC2>>Nc1cc(F)ccc1C(=O)CCCN1CC[C@H]2[C@@H](C1)c1cccc3c1N2CCC3 | C1=CC=C2CCCN3C2=C1[C@H]1[C@@H]3CCNC1.NC1=C(C=CC(=C1)F)C(CCCCl)=O>>C1=CC=C2CCCN3C2=C1[C@H]1[C@@H]3CCN(C1)CCCC(=O)C1=C(C=C(C=C1)F)N | Cl[CH2:13][CH2:12][CH2:11][C:9]([c:8]1[c:2]([NH2:1])[cH:3][c:4]([F:5])[cH:6][cH:7]1)=[O:10].[NH:14]1[CH2:15][CH2:16][C@H:17]2[C@@H:18]([CH2:19]1)[c:20]1[cH:21][cH:22][cH:23][c:24]3[c:25]1[N:26]2[CH2:27][CH2:28][CH2:29]3>>[NH2:1][c:2]1[cH:3][c:4]([F:5])[cH:6][cH:7][c:8]1[C:9](=[O:10])[CH2:11][CH2:12][CH2:13][N:14]1[CH2:... | Nc1cc(F)ccc1C(=O)CCCCl.c1cc2c3c(c1)[C@@H]1CNCC[C@@H]1N3CCC2 | Nc1cc(F)ccc1C(=O)CCCN1CC[C@H]2[C@@H](C1)c1cccc3c1N2CCC3 | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 156e57521f17e5fff63c4f7b30e3a65e7ad32d15778d94884e7e127a119f08c7 | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | O=C(CCCN1CC[C@H]2[C@@H](C1)c1cccc3c1N2CCC3)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] | null | [] | null | null | null | null | The title compound was prepared by the method of Example 402 as a yellow oil (35 mg, 20%) from (7aS,11aR)-5,6,7a,8,9,10,11,11a-octahydro-4H-pyrido[3′,4′:4,5]pyrrolo[3,2,1-ij]quinoline (100 mg, 0.47 mmol) and 1-(2-amino-4-fluorophenyl)-4-chloro-1-butanone (202 mg, 0.93 mmol). The title compound was spectroscopically ide... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | c1cc2c3c(c1)[C@@H]1CNCC[C@@H]1N3CCC2 | c1cc2c3c(c1)[C@@H]1C[NH]CC[C@@H]1N3CCC2 | c1ccccc1.c1cc2c3c(c1)[C@@H]1C[NH]CC[C@@H]1N3CCC2 | HCl | null | null | null | Nc1cc(F)ccc1C(=O)CCCCl.c1cc2c3c(c1)[C@@H]1CNCC[C@@H]1N3CCC2>>Nc1cc(F)ccc1C(=O)CCCN1CC[C@H]2[C@@H](C1)c1cccc3c1N2CCC3 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-c632375c8b934537a2b2dd3bb2e1ae7b | Nc1cc(F)ccc1C(=O)CCCCl.c1cc2c3c(c1)[C@H]1CNCC[C@H]1N3CCC2>>Nc1cc(F)ccc1C(=O)CCCN1CC[C@@H]2[C@H](C1)c1cccc3c1N2CCC3 | C1=CC=C2CCCN3C2=C1[C@@H]1[C@H]3CCNC1.NC1=C(C=CC(=C1)F)C(CCCCl)=O>>C1=CC=C2CCCN3C2=C1[C@@H]1[C@H]3CCN(C1)CCCC(=O)C1=C(C=C(C=C1)F)N | Cl[CH2:13][CH2:12][CH2:11][C:9]([c:8]1[c:2]([NH2:1])[cH:3][c:4]([F:5])[cH:6][cH:7]1)=[O:10].[NH:14]1[CH2:15][CH2:16][C@@H:17]2[C@H:18]([CH2:19]1)[c:20]1[cH:21][cH:22][cH:23][c:24]3[c:25]1[N:26]2[CH2:27][CH2:28][CH2:29]3>>[NH2:1][c:2]1[cH:3][c:4]([F:5])[cH:6][cH:7][c:8]1[C:9](=[O:10])[CH2:11][CH2:12][CH2:13][N:14]1[CH2:... | Nc1cc(F)ccc1C(=O)CCCCl.c1cc2c3c(c1)[C@H]1CNCC[C@H]1N3CCC2 | Nc1cc(F)ccc1C(=O)CCCN1CC[C@@H]2[C@H](C1)c1cccc3c1N2CCC3 | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 14635250736ebb1f0e2e07dcba66a1eac5a18ac7f42f8c572369b3c0ad2d9436 | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | O=C(CCCN1CC[C@@H]2[C@H](C1)c1cccc3c1N2CCC3)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] | null | [] | null | null | null | null | The title compound was prepared by the method of Example 402 as a yellow oil (95 mg, 34%) from (7aR,11aS)-5,6,7a,8,9,10,11,11a-octahydro-4H-pyrido[3′,4′:4,5]pyrrolo[3,2,1-ij]quinoline (150 mg, 0.70 mmol) and 1-(2-amino-4-fluorophenyl)-4-chloro-1-butanone (303 mg, 1.40 mmol). The title compound was spectroscopically ide... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | c1cc2c3c(c1)[C@H]1CNCC[C@H]1N3CCC2 | c1cc2c3c(c1)[C@H]1C[NH]CC[C@H]1N3CCC2 | c1ccccc1.c1cc2c3c(c1)[C@H]1C[NH]CC[C@H]1N3CCC2 | HCl | null | null | null | Nc1cc(F)ccc1C(=O)CCCCl.c1cc2c3c(c1)[C@H]1CNCC[C@H]1N3CCC2>>Nc1cc(F)ccc1C(=O)CCCN1CC[C@@H]2[C@H](C1)c1cccc3c1N2CCC3 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-655e5c57ab72416783a7fb8d2b3be283 | NC1C=Cc2ccccc2N1.O=C1CCCNCC1>>c1cc2c3c(c1)c1c(n3CCC2)CCNCC1 | N1C(C=CC2=CC=CC=C12)N.Cl.N1CCC(CCC1)=O.Cl>>C1=CC=C2CCCN3C2=C1C1=C3CCNCC1 | N[CH:10]1[NH:9][c:4]2[c:3]([cH:2][cH:1][cH:6][cH:5]2)[CH:12]=[CH:11]1.O=[C:7]1[CH2:8][CH2:13][CH2:14][NH:15][CH2:16][CH2:17]1>>[cH:1]1[cH:2][c:3]2[c:4]3[c:5]([cH:6]1)[c:7]1[c:8]([n:9]3[CH2:10][CH2:11][CH2:12]2)[CH2:13][CH2:14][NH:15][CH2:16][CH2:17]1 | NC1C=Cc2ccccc2N1.O=C1CCCNCC1 | c1cc2c3c(c1)c1c(n3CCC2)CCNCC1 | null | null | CCO | Aromatic Heterocycle Formation | OtherReaction | cefa10b74758fd3e31c781d8a1f04de194cbac8be5243f0c931657062ee4d1a6 | fa378c03d4ddd7d70ab7aa9f3d6eed55b9b2769c0b0df538cbca5bebab4230d9 | c1cc2c3c(c1)c1c(n3CCC2)CCNCC1 | N-[CH;D3;+0:1]1-[CH;D2;+0:2]=[CH;D2;+0:3]-[c:4]2:[c:5]:[c:6]:[c:7]:[cH;D2;+0:8]:[c:9]:2-[NH;D2;+0:10]-1.O=[C;H0;D3;+0:11]1-[C:12]-[C:13]-[#7:14]-[C:15]-[C:16]-[CH2;D2;+0:17]-1>>[#7:14]1-[C:15]-[C:16]-[c;H0;D3;+0:17]2:[c;H0;D3;+0:11](:[c;H0;D3;+0:8]3:[c:7]:[c:6]:[c:5]:[c:4]4:[c:9]:3:[n;H0;D3;+0:10]:2-[CH2;D2;+0:1]-[CH2;... | 45 | [{"value": 45.0, "product": "C1=CC=C2CCCN3C2=C1C1=C3CCNCC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 25.2, "product": "C1=CC=C2CCCN3C2=C1C1=C3CCNCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 20 | CELSIUS | null | null | To a solution of 3,4-dihydro-[(2H)-quinolinamine (1.0 g, 14 mmol) and hexahydro-4H-azepin-4-one hydrochloride (1.0 g, 14 mmol) in EtOH (13 mL) was added concentrated HCl (1.2 mL). The reaction was stirred at reflux for 14 h, then cooled to 20° C. A brown precipitate was filtered from the reaction mixture, affording the... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Primary amine.Secondary amine | null | C1=Cc2ccccc2NC1.C1CCCNCC1 | c1cc2c3c(c1)c1c(n3CCC2)CCNCC1 | c1cc2c3c(c1)c1c(n3CCC2)CCNCC1 | HO- | CCO | 20 | null | NC1C=Cc2ccccc2N1.O=C1CCCNCC1>CCO>c1cc2c3c(c1)c1c(n3CCC2)CCNCC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-108005c9cfc147bc98fde0f344854524 | CC(C)(C)OC(=O)N1CCC2c3cccc4c3N(CCC4)C2CC1>>c1cc2c3c(c1)C1CCNCCC1N3CCC2 | C1=CC=C2CCCN3C2=C1C1C3CCN(CC1)C(=O)OC(C)(C)C.C(=O)(C(F)(F)F)O>>C1=CC=C2CCCN3C2=C1C1C3CCNCC1 | CC(C)(C)OC(=O)[N:10]1[CH2:9][CH2:8][CH:7]2[c:5]3[c:4]4[c:3]([cH:2][cH:1][cH:6]3)[CH2:17][CH2:16][CH2:15][N:14]4[CH:13]2[CH2:12][CH2:11]1>>[cH:1]1[cH:2][c:3]2[c:4]3[c:5]([cH:6]1)[CH:7]1[CH2:8][CH2:9][NH:10][CH2:11][CH2:12][CH:13]1[N:14]3[CH2:15][CH2:16][CH2:17]2 | CC(C)(C)OC(=O)N1CCC2c3cccc4c3N(CCC4)C2CC1 | c1cc2c3c(c1)C1CCNCCC1N3CCC2 | null | null | C(Cl)Cl | Reduction | Boc amine deprotection | ed18f9d2bcd6f23ef2c17006684e02f77b03ee947f51a20f1cf8e4e6e5eb1b55 | a94b29c7264c852156fc1cdd4a0951a4fc26c06d0edc9e50c743825dbf79e3fd | c1cc2c3c(c1)C1CCNCCC1N3CCC2 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1](-[C:2]-[C:3])-[C:4]-[C:5]>>[C:3]-[C:2]-[NH;D2;+0:1]-[C:4]-[C:5] | 59 | [{"value": 59.0, "product": "C1=CC=C2CCCN3C2=C1C1C3CCNCC1", "details": "PERCENTYIELD", "is_desired": false}] | 20 | CELSIUS | 3 | HOUR | To a solution of tert-butyl(±)-5,6,8,9,10,11,12,12a-octahydro-4H,7aH-azepino[4′,5′:4,5]pyrrolo[3,2,1-ij]quinoline-10-carboxylate in CH2Cl2 (2.4 mL) was added TFA (0.6 mL). This was stirred at 20° C. for 3 h. The reaction mixture was diluted with CH2Cl2 (50 mL) and washed with saturated NaHCO3(50 mL) and brine (50 mL), ... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Secondary amine | c1cc2c3c(c1)C1CC[NH]CCC1N3CCC2 | c1cc2c3c(c1)C1CCNCCC1N3CCC2 | c1cc2c3c(c1)C1CCNCCC1N3CCC2 | HO- | C(Cl)Cl | 20 | 3 | CC(C)(C)OC(=O)N1CCC2c3cccc4c3N(CCC4)C2CC1>C(Cl)Cl>c1cc2c3c(c1)C1CCNCCC1N3CCC2 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-427f376eea2545d9bee460fe1511bd36 | OC1=CC(=NN2CCCc3ccccc32)CCC1>>O=C1CCCc2c1c1cccc3c1n2CCC3 | Cl.N1(CCCC2=CC=CC=C12)N=C1C=C(CCC1)O.Cl.CC(=O)O>>C1=C2C=3C(CCCC3N3C2=C(C=C1)CCC3)=O | N(=[C:6]1[CH2:5][CH2:4][CH2:3][C:2]([OH:1])=[CH:7]1)[N:14]1[c:13]2[cH:8][cH:9][cH:10][cH:11][c:12]2[CH2:17][CH2:16][CH2:15]1>>[O:1]=[C:2]1[CH2:3][CH2:4][CH2:5][c:6]2[c:7]1[c:8]1[cH:9][cH:10][cH:11][c:12]3[c:13]1[n:14]2[CH2:15][CH2:16][CH2:17]3 | OC1=CC(=NN2CCCc3ccccc32)CCC1 | O=C1CCCc2c1c1cccc3c1n2CCC3 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | d238eac31464d48b17d6f43a7fd12bf21b29cd4caac6bf00518c532357a618e5 | e5aae0c145089bb22154f16396b35a40de983fc3158851adcbc7922cfa892651 | O=C1CCCc2c1c1cccc3c1n2CCC3 | [C:1]-[C:2]-[N;H0;D3;+0:3](-N=[C;H0;D3;+0:4]1-[C:5]-[C:6]-[C:7]-[C;H0;D3;+0:8](-[OH;D1;+0:9])=[CH;D2;+0:10]-1)-[c:11](:[c:12]):[cH;D2;+0:13]:[c:14]:[c:15]>>[C:1]-[C:2]-[n;H0;D3;+0:3]1:[c:11](:[c:12]):[c;H0;D3;+0:13](:[c:14]:[c:15]):[c;H0;D3;+0:10]2:[c;H0;D3;+0:4]:1-[C:5]-[C:6]-[C:7]-[C;H0;D3;+0:8]-2=[O;H0;D1;+0:9] | 33 | [{"value": 33.0, "product": "C1=C2C=3C(CCCC3N3C2=C(C=C1)CCC3)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | 3-(3,4-Dihydro-1-(2H)-quinolinylimino)-1-cyclohexen-1-ol hydrochloride (4.78 g, 17 mmol) was mixed with AcOH (37 mL) and conc. HCl (6.1 mL). The reaction mixture was refluxed for 1 h and cooled to RT. The reaction mixture was concentrated in vacuo then the residue was dissolved in CH2Cl2. The organic solution was washe... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazone.Enol | Ketone | C1=CCCCC1.c1ccc2c(c1)CCC[NH]2 | c1cc2c3c(c1)c1c(n3CCC2)CCCC1 | c1cc2c3c(c1)c1c(n3CCC2)CCCC1 | Other | null | null | null | OC1=CC(=NN2CCCc3ccccc32)CCC1>>O=C1CCCc2c1c1cccc3c1n2CCC3 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-1681b8dee83b4d608a01bebe5de466d7 | O=C1NCCCc2c1c1cccc3c1n2CCC3>>c1cc2c3c(c1)c1c(n3CCC2)CCCNC1 | O.[OH-].[Na+].O.[H-].[H-].[H-].[H-].[Li+].[Al+3].C1=CC=C2CCCN3C2=C1C1=C3CCCNC1=O>>C1=CC=C2CCCN3C2=C1C1=C3CCCNC1 | O=[C:17]1[c:7]2[c:5]3[c:4]4[c:3]([cH:2][cH:1][cH:6]3)[CH2:12][CH2:11][CH2:10][n:9]4[c:8]2[CH2:13][CH2:14][CH2:15][NH:16]1>>[cH:1]1[cH:2][c:3]2[c:4]3[c:5]([cH:6]1)[c:7]1[c:8]([n:9]3[CH2:10][CH2:11][CH2:12]2)[CH2:13][CH2:14][CH2:15][NH:16][CH2:17]1 | O=C1NCCCc2c1c1cccc3c1n2CCC3 | c1cc2c3c(c1)c1c(n3CCC2)CCCNC1 | null | null | O1CCOCC1 | Reduction | Reduction of secondary amides to amines | efd37a789229e86b41925d2d4c91a8da1659447e20c9e1fc1fbe74e18fbb0408 | ab40188eef2f825df7003af0ffae31d0ce53d126542122535627d3d354cbc9fe | c1cc2c3c(c1)c1c(n3CCC2)CCCNC1 | O=[C;H0;D3;+0:1](-[#7:2]-[C:3])-[c:4]1:[c:5]:[c:6]:[#7;a:7](:[c:8]:1-[C:9])-[C:10]>>[C:10]-[#7;a:7]1:[c:6]:[c:5]:[c:4](:[c:8]:1-[C:9])-[CH2;D2;+0:1]-[#7:2]-[C:3] | 95.4 | [{"value": 95.0, "product": "C1=CC=C2CCCN3C2=C1C1=C3CCCNC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 95.4, "product": "C1=CC=C2CCCN3C2=C1C1=C3CCCNC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 20 | CELSIUS | 1 | HOUR | To a suspension of LiAlH4 in 1,4-dioxane (26 mL) was added 5,6,8,9,10,11-hexahydro-4H,12H-azepino[3′,4′:4,5]pyrrolo[3,2,1-ij]quinolin-12-one (300 mg, 1.25 mmol) under N2 at 20° C. The reaction mixture was refluxed for 15 h. The reaction mixture was cooled in an ice bath and added successively with H2O (0.3 mL), 15% NaO... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide | null | c1cc2c3c(c1)c1c(n3CCC2)CCCNC1 | c1cc2c3c(c1)c1c(n3CCC2)CCCNC1 | c1cc2c3c(c1)c1c(n3CCC2)CCCNC1 | Other | O1CCOCC1 | 20 | 1 | O=C1NCCCc2c1c1cccc3c1n2CCC3>O1CCOCC1>c1cc2c3c(c1)c1c(n3CCC2)CCCNC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-84928b4c96ed4056a17c8bb993abb6b0 | c1cc2c3c(c1)c1c(n3CCC2)CCCNC1>>c1cc2c3c(c1)[C@H]1CNCCC[C@H]1N3CCC2 | C1=CC=C2CCCN3C2=C1C1=C3CCCNC1.[SiH](CC)(CC)CC>>C1=CC=C2CCCN3C2=C1[C@@H]1[C@H]3CCCNC1 | [cH:1]1[cH:2][c:3]2[c:4]3[c:5]([cH:6]1)[c:7]1[c:13]([n:14]3[CH2:15][CH2:16][CH2:17]2)[CH2:12][CH2:11][CH2:10][NH:9][CH2:8]1>>[cH:1]1[cH:2][c:3]2[c:4]3[c:5]([cH:6]1)[C@H:7]1[CH2:8][NH:9][CH2:10][CH2:11][CH2:12][C@H:13]1[N:14]3[CH2:15][CH2:16][CH2:17]2 | c1cc2c3c(c1)c1c(n3CCC2)CCCNC1 | c1cc2c3c(c1)[C@H]1CNCCC[C@H]1N3CCC2 | null | null | C(=O)(C(F)(F)F)O | Reduction | OtherReaction | 9dc9992145bee012e8fe9e726e1767f90d76d71d767a9341efd7fca7f34e28d2 | 3f9bd1254c561719832bd71149feb4e99c5764db1feb47bf9fbdfb1c414d602b | c1cc2c3c(c1)[C@H]1CNCCC[C@H]1N3CCC2 | [C:1]-[C:2]-[n;H0;D3;+0:3]1:[c:4](:[c:5]):[c:6](:[c:7]):[c;H0;D3;+0:8]2:[c;H0;D3;+0:9]:1-[C:10]-[C:11]-[C:12]-[#7:13]-[C:14]-2>>[C:1]-[C:2]-[N;H0;D3;+0:3]1-[C@@H;D3;+0:9]2-[C:10]-[C:11]-[C:12]-[#7:13]-[C:14]-[C@@H;D3;+0:8]-2-[c:6](:[c:7]):[c:4]-1:[c:5] | 83 | [{"value": 83.0, "product": "C1=CC=C2CCCN3C2=C1[C@@H]1[C@H]3CCCNC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 82.6, "product": "C1=CC=C2CCCN3C2=C1[C@@H]1[C@H]3CCCNC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | DAY | To a solution of 5,6,9,10,11,12-hexahydro-4H,8H-azepino[3′,4′:4,5]pyrrolo[3,2,1-ij]quinoline (240 mg, 1.06 mmol) in TFA (4.0 ML) was added Et3SiH (2.0 mL). The mixture was stirred for 3 days then concentrated in vacuo. The residue was dissolved in dilute AcOH and washed with Et2O. The aqueous solution was basified with... | 10.6084/m9.figshare.5104873.v1 | null | null | Tertiary amine | c1cc2c3c(c1)c1c(n3CCC2)CCCNC1 | c1cc2c3c(c1)[C@H]1CNCCC[C@H]1N3CCC2 | c1cc2c3c(c1)[C@H]1CNCCC[C@H]1N3CCC2 | null | C(=O)(C(F)(F)F)O | null | 72 | c1cc2c3c(c1)c1c(n3CCC2)CCCNC1>C(=O)(C(F)(F)F)O>c1cc2c3c(c1)[C@H]1CNCCC[C@H]1N3CCC2 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-1b37376a3bc2410d98d86cf23efb5d5a | CC(C)(C)OC(=O)N1CCC[C@@H]2[C@H](C1)c1cc(Br)cc3c1N2CCC3.COc1ccc(B(O)O)c(C(F)(F)F)c1>>COc1ccc(-c2cc3c4c(c2)[C@H]2CN(C(=O)OC(C)(C)C)CCC[C@H]2N4CCC3)c(C(F)(F)F)c1 | BrC=1C=C2CCCN3C2=C(C1)[C@@H]1[C@H]3CCCN(C1)C(=O)OC(C)(C)C.COC1=CC(=C(C=C1)B(O)O)C(F)(F)F>>COC1=CC(=C(C=C1)C=1C=C2CCCN3C2=C(C1)[C@@H]1[C@H]3CCCN(C1)C(=O)OC(C)(C)C)C(F)(F)F | Br[c:7]1[cH:8][c:9]2[c:10]3[c:11]([cH:12]1)[C@H:13]1[CH2:14][N:15]([C:16](=[O:17])[O:18][C:19]([CH3:20])([CH3:21])[CH3:22])[CH2:23][CH2:24][CH2:25][C@H:26]1[N:27]3[CH2:28][CH2:29][CH2:30]2.OB(O)[c:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:36][c:31]1[C:32]([F:33])([F:34])[F:35]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[c... | CC(C)(C)OC(=O)N1CCC[C@@H]2[C@H](C1)c1cc(Br)cc3c1N2CCC3.COc1ccc(B(O)O)c(C(F)(F)F)c1 | COc1ccc(-c2cc3c4c(c2)[C@H]2CN(C(=O)OC(C)(C)C)CCC[C@H]2N4CCC3)c(C(F)(F)F)c1 | null | null | null | C-C Coupling | Suzuki coupling with boronic acids | 6ece39ec942ede915c0bde2dc32721d005f83859b9575210631872d90958e172 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(-c2cc3c4c(c2)[C@H]2CNCCC[C@H]2N4CCC3)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].O-B(-O)-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9](-[C:10](-[F;D1;H0:11])(-[F;D1;H0:12])-[F;D1;H0:13]):[c:14]>>[F;D1;H0:11]-[C:10](-[F;D1;H0:12])(-[F;D1;H0:13])-[c:9](:[c:14]):[c;H0;D3;+0:6](-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5]):[c:7]:[c:8] | 92.9 | [{"value": 91.0, "product": "COC1=CC(=C(C=C1)C=1C=C2CCCN3C2=C(C1)[C@@H]1[C@H]3CCCN(C1)C(=O)OC(C)(C)C)C(F)(F)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 92.9, "product": "COC1=CC(=C(C=C1)C=1C=C2CCCN3C2=C(C1)[C@@H]1[C@H]3CCCN(C1)C(=O)OC(C)(C)C)C(F)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired... | null | null | null | null | Tert-butyl(±)-cis-2-[4-methoxy-2-(trifluoromethyl)phenyl]-5,6,8,9,10,11,12,12a-octahydro-4H,7aH-azepino[3′,4′:4,5]pyrrolo[3,2,1-ij]quinoline-11-carboxylate (56 mg, 91%) was prepared by the general method of Example 319, step A from tert-butyl(±)-cis-2-bromo-5,6,8,9,10,11,12,12a-octahydro-4H,7aH-azepino[3′,4′:4,5]pyrrol... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1cc2c3c(c1)[C@H]1C[NH]CCC[C@H]1N3CCC2.c1ccccc1 | c1ccccc1.c1cc2c3c(c1)[C@H]1C[NH]CCC[C@H]1N3CCC2 | c1ccccc1.c1cc2c3c(c1)[C@H]1C[NH]CCC[C@H]1N3CCC2 | HBr.B | null | null | null | CC(C)(C)OC(=O)N1CCC[C@@H]2[C@H](C1)c1cc(Br)cc3c1N2CCC3.COc1ccc(B(O)O)c(C(F)(F)F)c1>>COc1ccc(-c2cc3c4c(c2)[C@H]2CN(C(=O)OC(C)(C)C)CCC[C@H]2N4CCC3)c(C(F)(F)F)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-a12787f32a5943e39172e13a95b10ffd | OB(O)c1cccs1.OCCc1cccc(Br)c1>>OCC(c1ccccc1)c1cccs1 | BrC=1C=C(CCO)C=CC1.S1C(=CC=C1)B(O)O.C(=O)(O)[O-].[Na+]>>S1C(=CC=C1)C(CO)C1=CC=CC=C1 | OB(O)[c:10]1[cH:11][cH:12][cH:13][s:14]1.Br[c:8]1[cH:7][cH:6][cH:5][c:4]([CH2:3][CH2:2][OH:1])[cH:9]1>>[OH:1][CH2:2][CH:3]([c:4]1[cH:5][cH:6][cH:7][cH:8][cH:9]1)[c:10]1[cH:11][cH:12][cH:13][s:14]1 | OB(O)c1cccs1.OCCc1cccc(Br)c1 | OCC(c1ccccc1)c1cccs1 | null | null | COCCOC | C-C Coupling | OtherReaction | a9e750b5cb26673fc488a731642519fa5963d6a2e4d2eeb976470c7f17606def | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(Cc2cccs2)cc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[c:5](-[CH2;D2;+0:6]-[C:7]-[O;D1;H1:8]):[c:9]:1.O-B(-O)-[c;H0;D3;+0:10]1:[#16;a:11]:[c:12]:[c:13]:[c:14]:1>>[O;D1;H1:8]-[C:7]-[CH;D3;+0:6](-[c:5]1:[c:4]:[c:3]:[c:2]:[cH;D2;+0:1]:[c:9]:1)-[c;H0;D3;+0:10]1:[#16;a:11]:[c:12]:[c:13]:[c:14]:1 | null | [] | null | null | null | null | 3-Bromophenethyl alcohol (4 ml, 29.8 mmol) was dissolved in 1,2-dimethoxyethane (225 mL) and mixed with tetrakistriphenylphosphine palladium[0] (2.6 g, 2.25 mmol) at room temperature. The reaction mixture was then added to a solution of 2-thienyl-boronic acid (12.6 g, 99 mmol) and 1 N NaHCO3 (90 mL). The reaction mixtu... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccsc1.c1ccccc1 | c1ccccc1.c1ccsc1 | c1ccccc1.c1ccsc1 | HBr.B | COCCOC | null | null | OB(O)c1cccs1.OCCc1cccc(Br)c1>COCCOC>OCC(c1ccccc1)c1cccs1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-f2b5fb9d76734f329f88f2840c6c43b0 | BrP(Br)Br.OC1Cc2cccc3cccc1c23>>BrC1Cc2cccc3cccc1c23 | C1(CC2=CC=CC3=CC=CC1=C23)O.P(Br)(Br)Br>>BrC1CC2=CC=CC3=CC=CC1=C23 | BrP(Br)[Br:1].O[CH:2]1[CH2:3][c:4]2[cH:5][cH:6][cH:7][c:8]3[cH:9][cH:10][cH:11][c:12]1[c:13]23>>[Br:1][CH:2]1[CH2:3][c:4]2[cH:5][cH:6][cH:7][c:8]3[cH:9][cH:10][cH:11][c:12]1[c:13]23 | BrP(Br)Br.OC1Cc2cccc3cccc1c23 | BrC1Cc2cccc3cccc1c23 | null | null | C(C)OCC | Functional Group Interconversion | OtherReaction | 964348a893fb0ea0b71fe0bfa849bf397e64006f1f9448180e34b372fc69c7ec | 495868b18ac37eabad313a8861412e57f019fb3569a2b2e50afa3ee29413ec02 | c1cc2c3c(cccc3c1)CC2 | Br-P(-Br)-[Br;H0;D1;+0:1].O-[CH;D3;+0:2]1-[C:3]-[c:4]:[c:5]:[c:6]-1:[c:7]>>[Br;H0;D1;+0:1]-[CH;D3;+0:2]1-[C:3]-[c:4]:[c:5]:[c:6]-1:[c:7] | null | [] | 0 | CELSIUS | 30 | MINUTE | Acenaphthen-1-ol (88 mol) was dissolved in diethyl ether (150 mL) and cooled down to 0° C. Phosphorous tribromide (3.2 mL, 35 mmol) was then added slowly under nitrogen atmosphere. The reaction mixture was stirred for 30 minutes at room temperature and cooled to 0° C. The reaction mixture was partitioned with water and... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol | Secondary halide | c1cc2c3c(cccc3c1)CC2 | c1cc2c3c(cccc3c1)CC2 | c1cc2c3c(cccc3c1)CC2 | HBr | C(C)OCC | 0 | 0.5 | BrP(Br)Br.OC1Cc2cccc3cccc1c23>C(C)OCC>BrC1Cc2cccc3cccc1c23 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-231dfdd907524f57b25cca4f12bbebc1 | Cc1cccc2cccc(C)c12.O=C1CCC(=O)N1Br>>Cc1cccc2cccc(CBr)c12 | CC1=CC=CC2=CC=CC(=C12)C.BrN1C(CCC1=O)=O.C(C1=CC=CC=C1)(=O)OOC(C1=CC=CC=C1)=O>>BrCC1=CC=CC2=CC=CC(=C12)C | [CH3:1][c:2]1[cH:3][cH:4][cH:5][c:6]2[cH:7][cH:8][cH:9][c:10]([CH3:11])[c:13]12.O=C1CCC(=O)N1[Br:12]>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][c:6]2[cH:7][cH:8][cH:9][c:10]([CH2:11][Br:12])[c:13]12 | Cc1cccc2cccc(C)c12.O=C1CCC(=O)N1Br | Cc1cccc2cccc(CBr)c12 | null | null | C(Cl)(Cl)(Cl)Cl | Functional Group Interconversion | Wohl-Ziegler bromination benzyl primary | 45c0aca0d63a96f0092e6dded9c888827eaf6379dac179e1cefc99293896300a | 08f5e7e34d3f321cce3e85421b38226d6240cca0939494ae61032d4f8405cf22 | c1ccc2ccccc2c1 | O=C1-C-C-C(=O)-N-1-[Br;H0;D1;+0:1].[CH3;D1;+0:2]-[c:3](:[c:4]):[c:5]>>[Br;H0;D1;+0:1]-[CH2;D2;+0:2]-[c:3](:[c:4]):[c:5] | null | [] | null | null | null | null | 1,8-Dimethyl-naphthalene (1.30 g, 8.32 mmol) was dissolved in dry carbon tetrachloride (80 mL). To the reaction mixture was added N-bromosuccinimide (1.39 g, 7.82 mmol), dibenzoyl peroxide (6 mg, catalyst) and the reaction mixture was refluxing for 6 hours under nitrogen atmosphere. The reaction mixture was cooled to r... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Tertiary amide | Primary halide | C1CCNC1 | null | c1ccc2ccccc2c1 | HO- | C(Cl)(Cl)(Cl)Cl | null | null | Cc1cccc2cccc(C)c12.O=C1CCC(=O)N1Br>C(Cl)(Cl)(Cl)Cl>Cc1cccc2cccc(CBr)c12 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-75b5c83e857d41b9bef97714e1eb5bd8 | Cc1cccc2c1C(C(=O)O)CCC2>>Cc1cccc2c1C(CO)CCC2 | CC=1C=CC=C2CCCC(C12)C(=O)O.ClCCl>>CC=1C=CC=C2CCCC(C12)CO | O=[C:9]([CH:8]1[c:7]2[c:2]([CH3:1])[cH:3][cH:4][cH:5][c:6]2[CH2:13][CH2:12][CH2:11]1)[OH:10]>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][c:6]2[c:7]1[CH:8]([CH2:9][OH:10])[CH2:11][CH2:12][CH2:13]2 | Cc1cccc2c1C(C(=O)O)CCC2 | Cc1cccc2c1C(CO)CCC2 | null | null | O1CCCC1 | Reduction | Reduction of carboxylic acid to primary alcohol | 0db83a5ebe1e318b78b55461cf7eb8f7c004eef0f9e3b6666d3df4c96b5f665e | 93b4621647b04d2ad2f2825215b1567f171ba61fe10d136b5db6ea0470aa4932 | c1ccc2c(c1)CCCC2 | O=[C;H0;D3;+0:1](-[O;D1;H1:2])-[C:3](-[C:4])-[c:5]>>[C:4]-[C:3](-[CH2;D2;+0:1]-[O;D1;H1:2])-[c:5] | null | [] | null | null | 15 | MINUTE | 8-Methyl-1,2,3,4-tetrahydro-naphthalene-1-carboxylic acid (J. Org. Chem. 1982, 47, 2590–2593) (0.066 g, 0.34 mmol) was dissolved in tetrahydrofuran (3 mL). To the solution was then added at 0° C. a 1.0M solution of borane-methyl sulfide complex in dichloromethane (0.7 mL, 0.69 mmol). The reaction mixture was stirred at... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Primary alcohol | null | null | c1ccc2c(c1)CCCC2 | Other | O1CCCC1 | null | 0.25 | Cc1cccc2c1C(C(=O)O)CCC2>O1CCCC1>Cc1cccc2c1C(CO)CCC2 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-e50bc815ce264a92a4f7c341ff683809 | Cc1cccc2c1C(CO)CCC2>>Cc1cccc2c1C(C=O)CCC2 | CC=1C=CC=C2CCCC(C12)CO.CC(=O)OI1(C2=CC=CC=C2C(=O)O1)(OC(=O)C)OC(=O)C.CC(=O)OI1(C=2C=CC=CC2C(=O)O1)(OC(=O)C)OC(=O)C>>CC=1C=CC=C2CCCC(C12)C=O | [CH3:1][c:2]1[cH:3][cH:4][cH:5][c:6]2[c:7]1[CH:8]([CH2:9][OH:10])[CH2:11][CH2:12][CH2:13]2>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][c:6]2[c:7]1[CH:8]([CH:9]=[O:10])[CH2:11][CH2:12][CH2:13]2 | Cc1cccc2c1C(CO)CCC2 | Cc1cccc2c1C(C=O)CCC2 | null | null | ClCCl | Oxidation | Oxidation or Dehydrogenation of Alcohols to Aldehydes and Ketones | 41bfa9deea81b465c88ad21fdfb64a2e1ba29490558cf430df132cb98b4a538b | 0a03c6724c1862e8f86d4a463afda55b8e067dc6cb42597b472eb7cabc03eda3 | c1ccc2c(c1)CCCC2 | [C:1]-[C:2](-[CH2;D2;+0:3]-[OH;D1;+0:4])-[c:5]>>[C:1]-[C:2](-[CH;D2;+0:3]=[O;H0;D1;+0:4])-[c:5] | null | [] | null | null | 2 | HOUR | (8-Methyl-1,2,3,4-tetrahydro-naphthalen-1-yl)-methanol (0.03 g, 0.17 mmol) was dissolved in dichloromethane (0.5 mL). To the solution was then added 1,1,1-triacetoxy-1,1-dihydro-1,2-benziodoxol-3 (1H)-one, also known as Dess-Martin periodinane (0.087 g, 0.20 mmol). The reaction mixture was stirred for 2 hrs then partit... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | Aldehyde | null | null | c1ccc2c(c1)CCCC2 | null | ClCCl | null | 2 | Cc1cccc2c1C(CO)CCC2>ClCCl>Cc1cccc2c1C(C=O)CCC2 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-72af2a30687844fa9df2bfb9b8bbf530 | CC(C)(C)[SiH2]OC(C)(C)c1cccc2cccc(CO)c12>>CC(C)(C)[SiH2]OC(C)(C)c1cccc2cccc(C=O)c12 | C(C)(C)(C)[SiH2]OC(C=1C=CC=C2C=CC=C(C12)CO)(C)C.CC(=O)OI1(C2=CC=CC=C2C(=O)O1)(OC(=O)C)OC(=O)C.CC(=O)OI1(C=2C=CC=CC2C(=O)O1)(OC(=O)C)OC(=O)C>>C(C)(C)(C)[SiH2]OC(C=1C=CC=C2C=CC=C(C12)C=O)(C)C | [CH3:1][C:2]([CH3:3])([CH3:4])[SiH2:5][O:6][C:7]([CH3:8])([CH3:9])[c:10]1[cH:11][cH:12][cH:13][c:14]2[cH:15][cH:16][cH:17][c:18]([CH2:19][OH:20])[c:21]12>>[CH3:1][C:2]([CH3:3])([CH3:4])[SiH2:5][O:6][C:7]([CH3:8])([CH3:9])[c:10]1[cH:11][cH:12][cH:13][c:14]2[cH:15][cH:16][cH:17][c:18]([CH:19]=[O:20])[c:21]12 | CC(C)(C)[SiH2]OC(C)(C)c1cccc2cccc(CO)c12 | CC(C)(C)[SiH2]OC(C)(C)c1cccc2cccc(C=O)c12 | null | null | ClCCl | Oxidation | Oxidation or Dehydrogenation of Alcohols to Aldehydes and Ketones | 41bfa9deea81b465c88ad21fdfb64a2e1ba29490558cf430df132cb98b4a538b | 0a03c6724c1862e8f86d4a463afda55b8e067dc6cb42597b472eb7cabc03eda3 | c1ccc2ccccc2c1 | [OH;D1;+0:1]-[CH2;D2;+0:2]-[c:3](:[c:4]):[c:5]>>[O;H0;D1;+0:1]=[CH;D2;+0:2]-[c:3](:[c:4]):[c:5] | null | [] | null | null | 1 | HOUR | [8-(tert-Butyl-dimethyl-silanyloxymethyl)-naphthalen-1-yl]-methanol (Aust. J. Chem. 1996, 49, 793–800) (0.2 g, 0.66 mmol) was dissolved in dichloromethane (8 mL). To the solution was then added 1,1,1-triacetoxy-1,1-dihydro-1,2-benziodoxol-3 (1H)-one, also known as Dess-Martin periodinane (0.56 g, 1.32 mmol). The reacti... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | Aldehyde | null | null | c1ccc2ccccc2c1 | null | ClCCl | null | 1 | CC(C)(C)[SiH2]OC(C)(C)c1cccc2cccc(CO)c12>ClCCl>CC(C)(C)[SiH2]OC(C)(C)c1cccc2cccc(C=O)c12 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-4df3871460894af1b8b3d6aebbe29cb1 | CC(C)(C)[SiH2]OC(C)(C)c1cccc2cccc(C=O)c12.O=C1NCN(c2ccc(F)cc2)C12CCNCC2>>CC(C)(C)[SiH2]OC(C)(C)c1cccc2cccc(CN3CCC4(CC3)C(=O)NCN4c3ccc(F)cc3)c12 | C(C)(=O)O.FC1=CC=C(C=C1)N1CNC(C12CCNCC2)=O.C(C)(C)(C)[SiH2]OC(C=1C=CC=C2C=CC=C(C12)C=O)(C)C.C(C)(=O)O[BH-](OC(C)=O)OC(C)=O.[Na+]>>C(C)(C)(C)[SiH2]OC(C=1C=CC=C2C=CC=C(C12)CN1CCC2(C(NCN2C2=CC=C(C=C2)F)=O)CC1)(C)C | O=[CH:19][c:18]1[cH:17][cH:16][cH:15][c:14]2[cH:13][cH:12][cH:11][c:10]([C:7]([O:6][SiH2:5][C:2]([CH3:1])([CH3:3])[CH3:4])([CH3:8])[CH3:9])[c:38]21.[NH:20]1[CH2:21][CH2:22][C:23]2([CH2:24][CH2:25]1)[C:26](=[O:27])[NH:28][CH2:29][N:30]2[c:31]1[cH:32][cH:33][c:34]([F:35])[cH:36][cH:37]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[Si... | CC(C)(C)[SiH2]OC(C)(C)c1cccc2cccc(C=O)c12.O=C1NCN(c2ccc(F)cc2)C12CCNCC2 | CC(C)(C)[SiH2]OC(C)(C)c1cccc2cccc(CN3CCC4(CC3)C(=O)NCN4c3ccc(F)cc3)c12 | null | null | ClCCCl | Heteroatom Alkylation and Arylation | reductive amination | ae053ab422a821c7351275e61e26e76c3d705adc6ecc2d9eb9b7d77f1bd32ce0 | 2d03f38884b1fbb0c0d6e6f2de31afb25102fec87f347c3a123e064c1bfef0ad | O=C1NCN(c2ccccc2)C12CCN(Cc1cccc3ccccc13)CC2 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[C:5]-[C:6]-[NH;D2;+0:7]-[C:8]-[C:9]>>[C:5]-[C:6]-[N;H0;D3;+0:7](-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4])-[C:8]-[C:9] | null | [] | null | null | 1 | HOUR | 1-(4-Fluoro-phenyl)-1,3,8-triaza-spiro[4.5]decan-4-one (0.056 g, 0.22 mmol) and 8-(tert-butyl-dimethyl-silanyloxymethyl)-naphthalene-1-carbaldehyde (0.067 g, 0.22 mmol) were dissolved in dry 1,2-dichloroethane (5 mL). To the reaction mixture was added crashed 4A Molecular Sieve (0.028 g), a catalytic amount of glacial ... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Secondary amine | Tertiary amine | C1CC2(CCN1)CNC[NH]2 | C1CC2(CC[NH]1)CNC[NH]2 | c1ccc2ccccc2c1.C1CC2(CC[NH]1)CNC[NH]2.c1ccccc1 | Other | ClCCCl | null | 1 | CC(C)(C)[SiH2]OC(C)(C)c1cccc2cccc(C=O)c12.O=C1NCN(c2ccc(F)cc2)C12CCNCC2>ClCCCl>CC(C)(C)[SiH2]OC(C)(C)c1cccc2cccc(CN3CCC4(CC3)C(=O)NCN4c3ccc(F)cc3)c12 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-a25636b5b72c4cfea13c1a333bb2a9e0 | COCc1cccc2cccc(CO)c12>>COCc1cccc2cccc(C=O)c12 | COCC=1C=CC=C2C=CC=C(C12)CO.CC(=O)OI1(C2=CC=CC=C2C(=O)O1)(OC(=O)C)OC(=O)C.CC(=O)OI1(C=2C=CC=CC2C(=O)O1)(OC(=O)C)OC(=O)C>>COCC=1C=CC=C2C=CC=C(C12)C=O | [CH3:1][O:2][CH2:3][c:4]1[cH:5][cH:6][cH:7][c:8]2[cH:9][cH:10][cH:11][c:12]([CH2:13][OH:14])[c:15]12>>[CH3:1][O:2][CH2:3][c:4]1[cH:5][cH:6][cH:7][c:8]2[cH:9][cH:10][cH:11][c:12]([CH:13]=[O:14])[c:15]12 | COCc1cccc2cccc(CO)c12 | COCc1cccc2cccc(C=O)c12 | null | null | ClCCl | Oxidation | Oxidation or Dehydrogenation of Alcohols to Aldehydes and Ketones | 41bfa9deea81b465c88ad21fdfb64a2e1ba29490558cf430df132cb98b4a538b | 0a03c6724c1862e8f86d4a463afda55b8e067dc6cb42597b472eb7cabc03eda3 | c1ccc2ccccc2c1 | [OH;D1;+0:1]-[CH2;D2;+0:2]-[c:3](:[c:4]):[c:5]>>[O;H0;D1;+0:1]=[CH;D2;+0:2]-[c:3](:[c:4]):[c:5] | null | [] | null | null | 1 | HOUR | (8-Methoxymethyl-naphthalen-1-yl)-methanol (Tetrahedron Lett. 1997; 38, 8161–8164) (0.36 g, 1.8 mmol) was dissolved in dichloromethane (10 mL). To the solution was then added 1,1,1-triacetoxy-1,1-dihydro-1,2-benziodoxol-3 (1H)-one, also known as Dess-Martin periodinane (1.5 g, 3.6 mmol). The reaction mixture was stirre... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | Aldehyde | null | null | c1ccc2ccccc2c1 | null | ClCCl | null | 1 | COCc1cccc2cccc(CO)c12>ClCCl>COCc1cccc2cccc(C=O)c12 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-3879087fbd464ccaa8a46e159e6bd089 | O=C1OC(=O)c2cccc3cccc1c23>>OCc1cccc2cccc(CO)c12 | Cl.C=1C=C2C=CC=C3C2=C(C1)C(=O)OC3=O.CC(C)C[AlH]CC(C)C>>OCC=1C=CC=C2C=CC=C(C12)CO | O=[C:12]1[c:11]2[cH:10][cH:9][cH:8][c:7]3[cH:6][cH:5][cH:4][c:3]([c:14]32)[C:2](=[O:1])[O:13]1>>[OH:1][CH2:2][c:3]1[cH:4][cH:5][cH:6][c:7]2[cH:8][cH:9][cH:10][c:11]([CH2:12][OH:13])[c:14]12 | O=C1OC(=O)c2cccc3cccc1c23 | OCc1cccc2cccc(CO)c12 | null | null | O.C1(=CC=CC=C1)C.C(C)(=O)OCC | Reduction | OtherReaction | e4e58a08265f9c16a69d1fb6912296c64045b780aca9ff6b0a473b1affc07f8c | 62efeb05e7838a098a8a3af9d4f83fa4539c6fc2ad44bda3a588044dee3bd05e | c1ccc2ccccc2c1 | O=[C;H0;D3;+0:1]1-[O;H0;D2;+0:2]-[C;H0;D3;+0:3](=[O;H0;D1;+0:4])-[c:5](:[c:6]):[c:7]:[c:8]-1:[c:9]>>[OH;D1;+0:2]-[CH2;D2;+0:1]-[c:8](:[c:9]):[c:7]:[c:5](-[CH2;D2;+0:3]-[OH;D1;+0:4]):[c:6] | null | [] | 95 | CELSIUS | null | null | A 12-L 4-neck flask equipped with a thermocouple, an overhead stirrer, a 2-L addition funnel, and a condenser under N2 was charged with 1,8-naphthalic anhydride (200 g, 1.0 mol) in toluene (2.5 L) at room temperature. The reaction mixture was agitated while adding DIBAL-H (1.5 M in toluene, 2.664 L, 4 mol) via the addi... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride | Primary alcohol.Primary alcohol | c1cc2c3c(cccc3c1)COC2 | null | c1ccc2ccccc2c1 | Other | O.C1(=CC=CC=C1)C.C(C)(=O)OCC | 95 | null | O=C1OC(=O)c2cccc3cccc1c23>O.C1(=CC=CC=C1)C.C(C)(=O)OCC>OCc1cccc2cccc(CO)c12 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-8e79b6a113824593bb16a770d256b969 | OCc1cccc2cccc(CO)c12>>c1cc2c3c(cccc3c1)COC2 | OCC=1C=CC=C2C=CC=C(C12)CO.P(O)(O)(O)=O.O>>C1OCC2=C3C(C=CC=C13)=CC=C2 | O[CH2:11][c:5]1[c:4]2[c:3]([CH2:13][OH:12])[cH:2][cH:1][cH:10][c:9]2[cH:8][cH:7][cH:6]1>>[cH:1]1[cH:2][c:3]2[c:4]3[c:5]([cH:6][cH:7][cH:8][c:9]3[cH:10]1)[CH2:11][O:12][CH2:13]2 | OCc1cccc2cccc(CO)c12 | c1cc2c3c(cccc3c1)COC2 | null | null | C(Cl)Cl | Heteroatom Alkylation and Arylation | OtherReaction | 7a022ee7575095b658f46c33cf58e3e7745d5ae26a68e2a0aeff243326c547ba | 31a44c623e879cda50fc3ef399266dde4d5f7d364c38209e2960d8959326fbb0 | c1cc2c3c(cccc3c1)COC2 | O-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4]:[c:5]-[C:6]-[OH;D1;+0:7]>>[c:3]:[c:2]1:[c:4]:[c:5]-[C:6]-[O;H0;D2;+0:7]-[CH2;D2;+0:1]-1 | null | [] | 140 | CELSIUS | 3 | HOUR | A 1-L 3-neck flask equipped with an overhead stirrer, a condenser, and a thermocouple was charged with (8-hydroxymethyl-naphthalen-1-yl)-methanol (33.0 g, 0.175 mol), concentrated phosphoric acid (225 mL), and water (5 mL). The reaction mixture was stirred at 140° C. for 3 h, cooled to room temperature, diluted with CH... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Primary alcohol | Ether | null | c1cc2c3c(cccc3c1)COC2 | c1cc2c3c(cccc3c1)COC2 | HO- | C(Cl)Cl | 140 | 3 | OCc1cccc2cccc(CO)c12>C(Cl)Cl>c1cc2c3c(cccc3c1)COC2 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-b4c42341490541d690b7fc9727fdba94 | c1cc2c3c(cccc3c1)COC2>>Cc1cccc2cccc(CO)c12 | C1OCC2=C3C(C=CC=C13)=CC=C2.[K].C1=CC=CC2=CC=CC=C12>>CC=1C=CC=C2C=CC=C(C12)CO | [CH2:1]1[c:2]2[cH:3][cH:4][cH:5][c:6]3[cH:7][cH:8][cH:9][c:10]([c:13]23)[CH2:11][O:12]1>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][c:6]2[cH:7][cH:8][cH:9][c:10]([CH2:11][OH:12])[c:13]12 | c1cc2c3c(cccc3c1)COC2 | Cc1cccc2cccc(CO)c12 | null | null | C1CCOC1 | Reduction | OtherReaction | 9e7aa4e2310d8cf889e024142a126a965e7d80af2bbbb851508b0e8df6b1ab6f | f3c13c34886a9ee39fc7fda8af9901946f6871b5562065675a15384eea5a8281 | c1ccc2ccccc2c1 | [c:1]:[c:2]1:[c:3]:[c:4]-[C:5]-[O;H0;D2;+0:6]-[CH2;D2;+0:7]-1>>[CH3;D1;+0:7]-[c:2](:[c:1]):[c:3]:[c:4]-[C:5]-[OH;D1;+0:6] | null | [] | 60 | CELSIUS | 20 | MINUTE | A 3-L 4-neck flask equipped with an overhead stirrer, a thermocouple, a condenser, a nitrogen inlet, and a 1-L addition funnel was charged with potassium (30 g, 0.764 mol) and THF (1 L). The metal suspension was heated to 60° C. for 30 min and then stirred to room temperature. To the reaction mixture was then added nap... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Primary alcohol | c1cc2c3c(cccc3c1)COC2 | null | c1ccc2ccccc2c1 | null | C1CCOC1 | 60 | 0.333333 | c1cc2c3c(cccc3c1)COC2>C1CCOC1>Cc1cccc2cccc(CO)c12 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-e10bac357a914c2cbd3244584d019b6c | Cc1cccc2cccc(CO)c12>>Cc1cccc2cccc(C=O)c12 | CC=1C=CC=C2C=CC=C(C12)CO>>CC=1C=CC=C2C=CC=C(C12)C=O | [CH3:1][c:2]1[cH:3][cH:4][cH:5][c:6]2[cH:7][cH:8][cH:9][c:10]([CH2:11][OH:12])[c:13]12>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][c:6]2[cH:7][cH:8][cH:9][c:10]([CH:11]=[O:12])[c:13]12 | Cc1cccc2cccc(CO)c12 | Cc1cccc2cccc(C=O)c12 | null | null | C(Cl)Cl | Oxidation | Oxidation or Dehydrogenation of Alcohols to Aldehydes and Ketones | 41bfa9deea81b465c88ad21fdfb64a2e1ba29490558cf430df132cb98b4a538b | 0a03c6724c1862e8f86d4a463afda55b8e067dc6cb42597b472eb7cabc03eda3 | c1ccc2ccccc2c1 | [OH;D1;+0:1]-[CH2;D2;+0:2]-[c:3](:[c:4]):[c:5]>>[O;H0;D1;+0:1]=[CH;D2;+0:2]-[c:3](:[c:4]):[c:5] | null | [] | null | null | 6 | HOUR | A 1-L 4-neck equipped with an overhead stirrer, a condenser and a thermocouple was charged with 8-methyl-1-napthalenemethanol (18.5 g, 0.107 mol) in CH2Cl2 (500 mL) and stirred at room temperature under N2. Solid Mn(IV)O2 (61 g, 0.7 mol) was carefully added and the reaction was stirred at room temperature for 3 h, then... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | Aldehyde | null | null | c1ccc2ccccc2c1 | null | C(Cl)Cl | null | 6 | Cc1cccc2cccc(CO)c12>C(Cl)Cl>Cc1cccc2cccc(C=O)c12 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-6b636811dd8747e0bcf5a55f27875bcb | Cc1cccc2cccc(C=O)c12.O=C1NCN(c2ccc(F)cc2)C12CCNCC2>>Cc1cccc2cccc(CN3CCC4(CC3)C(=O)NCN4c3ccc(F)cc3)c12 | [OH-].[Na+].CC=1C=CC=C2C=CC=C(C12)C=O.FC1=CC=C(C=C1)N1CNC(C12CCNCC2)=O.[BH-](OC(=O)C)(OC(=O)C)OC(=O)C.[Na+]>>FC1=CC=C(C=C1)N1CNC(C12CCN(CC2)CC2=CC=CC1=CC=CC(=C21)C)=O | O=[CH:11][c:10]1[cH:9][cH:8][cH:7][c:6]2[cH:5][cH:4][cH:3][c:2]([CH3:1])[c:30]21.[NH:12]1[CH2:13][CH2:14][C:15]2([CH2:16][CH2:17]1)[C:18](=[O:19])[NH:20][CH2:21][N:22]2[c:23]1[cH:24][cH:25][c:26]([F:27])[cH:28][cH:29]1>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][c:6]2[cH:7][cH:8][cH:9][c:10]([CH2:11][N:12]3[CH2:13][CH2:14][C:15]4... | Cc1cccc2cccc(C=O)c12.O=C1NCN(c2ccc(F)cc2)C12CCNCC2 | Cc1cccc2cccc(CN3CCC4(CC3)C(=O)NCN4c3ccc(F)cc3)c12 | null | null | CC(=O)O.C(Cl)Cl.C(C)OCC | Heteroatom Alkylation and Arylation | reductive amination | ae053ab422a821c7351275e61e26e76c3d705adc6ecc2d9eb9b7d77f1bd32ce0 | 2d03f38884b1fbb0c0d6e6f2de31afb25102fec87f347c3a123e064c1bfef0ad | O=C1NCN(c2ccccc2)C12CCN(Cc1cccc3ccccc13)CC2 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[C:5]-[C:6]-[NH;D2;+0:7]-[C:8]-[C:9]>>[C:5]-[C:6]-[N;H0;D3;+0:7](-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4])-[C:8]-[C:9] | null | [] | 50 | CELSIUS | 20 | MINUTE | A 1-L 3-neck flask equipped with an overhead stirrer and a thermocouple was charged with 8-methyl-naphthalene-1-carbaldehyde (13.75 g, 0.08 mol) and 1-(4-fluoro-phenyl)-1,3,8-triaza-spiro[4.5]decan-4-one (21.5 g, 0.085 mol) under N2 in CH2Cl2 (500 mL). After stirring for 20 min, HOAc (1 mL) was added followed by carefu... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Secondary amine | Tertiary amine | C1CC2(CCN1)CNC[NH]2 | C1CC2(CC[NH]1)CNC[NH]2 | c1ccc2ccccc2c1.C1CC2(CC[NH]1)CNC[NH]2.c1ccccc1 | Other | CC(=O)O.C(Cl)Cl.C(C)OCC | 50 | 0.333333 | Cc1cccc2cccc(C=O)c12.O=C1NCN(c2ccc(F)cc2)C12CCNCC2>CC(=O)O.C(Cl)Cl.C(C)OCC>Cc1cccc2cccc(CN3CCC4(CC3)C(=O)NCN4c3ccc(F)cc3)c12 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-546acd1575ad4076993b2c6ec03af105 | COC(=O)[C@H]1[C@@H](c2ccc(F)cc2)C[C@@H]2CC[C@H]1N2C.Cl>>Clc1ccc(C23CNCC2C3)cc1Cl | Cl.Cl.FC1=CC=C(C=C1)C(OCCN1CCN(CC1)CCCC1=CC=CC=C1)C1=CC=C(C=C1)F.C1CN(CCN1CCCC2=CC=CC=C2)CCOC(C3=CC=C(C=C3)F)C4=CC=C(C=C4)F.NCCC1=CC(O)=C(O)C=C1.CN1[C@H]2CC[C@@H]1[C@H]([C@H](C2)C3=CC=C(C=C3)F)C(=O)OC.NCCC1=CC(O)=C(O)C=C1>>Cl.ClC=1C=C(C=CC1Cl)C12CNCC2C1 | COC(=O)[C@@H:8]1[C@H]2C[CH2:10][C@H:11](N2C)[CH2:12][C@@H:7]1[c:6]1[cH:5][cH:4][c:3](F)[cH:14][cH:13]1.[ClH:15]>>[Cl:2][c:3]1[cH:4][cH:5][c:6]([C:7]23[CH2:8][NH:9][CH2:10][CH:11]2[CH2:12]3)[cH:13][c:14]1[Cl:15] | COC(=O)[C@H]1[C@@H](c2ccc(F)cc2)C[C@@H]2CC[C@H]1N2C.Cl | Clc1ccc(C23CNCC2C3)cc1Cl | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 7fd43b7a431fbe87e25671e3bad8b4d727dd63fee79d5ea69cd18958ba2bd4d8 | 7ead3674a3a97c765db7a7f941d33bc50c45ce420e8e0212173f30bd8cd7673d | c1ccc(C23CNCC2C3)cc1 | null | null | [] | null | null | null | null | The dopamine uptake transporter binding assay was performed according to the methods described in Madras et al., 1989, Mol. Pharmacol. 36(4):518–524 and Javitch et al., 1984, Mol. Pharmacol. 26(1):35–44. The receptor source was guinea pig striatal membranes; the radioligand was [3H]WIN 35,428 (DuPont-NEN, Boston, Mass.... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ester.Tertiary amine | Aromatic halide.Aromatic halide.Secondary amine | C1C[C@@H]2CC[C@H](C1)N2.c1ccccc1 | c1ccccc1.C1NCC2CC12 | c1ccccc1.C1NCC2CC12 | HF | null | null | null | COC(=O)[C@H]1[C@@H](c2ccc(F)cc2)C[C@@H]2CC[C@H]1N2C.Cl>>Clc1ccc(C23CNCC2C3)cc1Cl |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-09fb40855c5646c49cc533afa783da8e | CCO.O=C(O)c1c[nH]c2ccccc12>>CCOC(=O)c1c[nH]c2ccccc12 | N1C=C(C2=CC=CC=C12)C(=O)O.C(C)O>>C(C)OC(=O)C1=CNC2=CC=CC=C12 | [CH3:1][CH2:2][OH:3].O[C:4](=[O:5])[c:6]1[cH:7][nH:8][c:9]2[cH:10][cH:11][cH:12][cH:13][c:14]12>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][nH:8][c:9]2[cH:10][cH:11][cH:12][cH:13][c:14]12 | CCO.O=C(O)c1c[nH]c2ccccc12 | CCOC(=O)c1c[nH]c2ccccc12 | null | null | null | Protection | Esterification of Carboxylic Acids | 070670f68a20c1021da94fabee54def4688122fb721af5f52cd5a03630845d0e | 0d8a72b7375d91aa7263e766e03a3cb7c4fa91e27abcd590409ff03b98eed690 | c1ccc2[nH]ccc2c1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[c:4]:[c:5]:[#7;a:6]:[c:7]:1.[C;D1;H3:8]-[C:9]-[OH;D1;+0:10]>>[C;D1;H3:8]-[C:9]-[O;H0;D2;+0:10]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[c:4]:[c:5]:[#7;a:6]:[c:7]:1 | null | [] | null | null | null | null | The title compound is prepared starting from indole-3-carboxylic acid (commercially available from Aldrich) by esterification with ethanol using standard methods of organic synthesis (e.g. J. March, Advanced Organic Chemistry, Reactions, Mechanisms and Structure (1992, 4th edition) 393–394 (Wiley interscience, New York... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary alcohol | Ester | null | null | c1ccc2[nH]ccc2c1 | HO- | null | null | null | CCO.O=C(O)c1c[nH]c2ccccc12>>CCOC(=O)c1c[nH]c2ccccc12 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-534f9192c0244256a60b0050c0f98bee | O=C1Nc2ccccc2C1=O.OB(O)c1ccsc1>>O=C1C(=O)N(c2ccsc2)c2ccccc21 | C(C)N(CC)CC.N1C(C(C2=CC=CC=C12)=O)=O.S1C=C(C=C1)B(O)O>>S1C=C(C=C1)N1C(C(C2=CC=CC=C12)=O)=O | [O:1]=[C:2]1[C:3](=[O:4])[NH:5][c:11]2[cH:12][cH:13][cH:14][cH:15][c:16]21.OB(O)[c:6]1[cH:7][cH:8][s:9][cH:10]1>>[O:1]=[C:2]1[C:3](=[O:4])[N:5]([c:6]2[cH:7][cH:8][s:9][cH:10]2)[c:11]2[cH:12][cH:13][cH:14][cH:15][c:16]21 | O=C1Nc2ccccc2C1=O.OB(O)c1ccsc1 | O=C1C(=O)N(c2ccsc2)c2ccccc21 | null | C(C)(=O)[O-].[Cu+2].C(C)(=O)[O-] | C(Cl)Cl | Heteroatom Alkylation and Arylation | Petasis reaction with amines and boronic acids | be3d88681ac45276609ee88d2d0617d0b24c7e5449c029bdbdb9b91a4d91e9d8 | d8988f95994c3a53b8581714df91fdcf58fce7c875a9f3af0fd1011694639d17 | O=C1C(=O)N(c2ccsc2)c2ccccc21 | O-B(-O)-[c;H0;D3;+0:1]1:[c:2]:[#16;a:3]:[c:4]:[c:5]:1.[O;D1;H0:6]=[C:7]1-[c:8]:[c:9](:[c:10])-[NH;D2;+0:11]-[C:12]-1=[O;D1;H0:13]>>[O;D1;H0:6]=[C:7]1-[c:8]:[c:9](:[c:10])-[N;H0;D3;+0:11](-[c;H0;D3;+0:1]2:[c:2]:[#16;a:3]:[c:4]:[c:5]:2)-[C:12]-1=[O;D1;H0:13] | 50 | [{"value": 50.0, "product": "S1C=C(C=C1)N1C(C(C2=CC=CC=C12)=O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 4.7, "product": "S1C=C(C=C1)N1C(C(C2=CC=CC=C12)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | Triethylamine (56.9 mL, 0.408 mol), was added to a mixture of 1H-indole-2,3-dione (15.0 g, 0.102 mol), copper (II) acetate (46.0 g, 0.255 mol), and 3-thienylboronic acid (19.6 g, 0.153 mol) in CH2Cl2 (500 mL). The reaction mixture was stirred overnight, filtered through Celite, rinsed with EtOAc/hexane (1:1, 300 mL), a... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide.Boronic acid | Tertiary amide | c1ccc2c(c1)CCN2.c1ccsc1 | c1ccsc1.c1ccc2c(c1)CC[NH]2 | c1ccsc1.c1ccc2c(c1)CC[NH]2 | HO-.B | C(C)(=O)[O-].[Cu+2].C(C)(=O)[O-].C(Cl)Cl | null | 8 | O=C1Nc2ccccc2C1=O.OB(O)c1ccsc1>C(C)(=O)[O-].[Cu+2].C(C)(=O)[O-].C(Cl)Cl>O=C1C(=O)N(c2ccsc2)c2ccccc21 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-b3bd69e1cfda432c9a2febc7a47dc33c | Cc1ccc(N)cc1.O=C1C(=O)N(c2ccsc2)c2ccccc21>>Cc1ccc(/N=C2/C(=O)N(c3ccsc3)c3ccccc32)cc1 | S1C=C(C=C1)N1C(C(C2=CC=CC=C12)=O)=O.NC1=CC=C(C=C1)C>>CC1=CC=C(C=C1)\N=C/1\C(N(C2=CC=CC=C12)C1=CSC=C1)=O | [CH3:1][c:2]1[cH:3][cH:4][c:5]([NH2:6])[cH:22][cH:23]1.O=[C:7]1[C:8](=[O:9])[N:10]([c:11]2[cH:12][cH:13][s:14][cH:15]2)[c:16]2[cH:17][cH:18][cH:19][cH:20][c:21]21>>[CH3:1][c:2]1[cH:3][cH:4][c:5](/[N:6]=[C:7]2/[C:8](=[O:9])[N:10]([c:11]3[cH:12][cH:13][s:14][cH:15]3)[c:16]3[cH:17][cH:18][cH:19][cH:20][c:21]32)[cH:22][cH:... | Cc1ccc(N)cc1.O=C1C(=O)N(c2ccsc2)c2ccccc21 | Cc1ccc(/N=C2/C(=O)N(c3ccsc3)c3ccccc32)cc1 | null | null | CC(=O)O.CO | Heteroatom Alkylation and Arylation | Addition of primary amines to ketones/thiocarbonyls | 561e2daf1aa504fe4e7a04c4a24377b070a888e3731bdc015219988535a1cb4e | 009cc6a97ebe0dc96c669f0ef59b95bcc20de7cae20b1b648ce8f8fa82309e57 | O=C1/C(=N/c2ccccc2)c2ccccc2N1c1ccsc1 | O=[C;H0;D3;+0:1]1-[C:2](=[O;D1;H0:3])-[#7:4](-[c:5]:[c:6]:[#16;a:7])-[c:8]:[c:9]-1:[c:10].[NH2;D1;+0:11]-[c:12](:[c:13]):[c:14]>>[#16;a:7]:[c:6]:[c:5]-[#7:4]1-[c:8]:[c:9](:[c:10])/[C;H0;D3;+0:1](=[N;H0;D2;+0:11]\[c:12](:[c:13]):[c:14])-[C:2]-1=[O;D1;H0:3] | 50.5 | [{"value": 50.0, "product": "CC1=CC=C(C=C1)\\N=C/1\\C(N(C2=CC=CC=C12)C1=CSC=C1)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 50.5, "product": "CC1=CC=C(C=C1)\\N=C/1\\C(N(C2=CC=CC=C12)C1=CSC=C1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 12 | HOUR | A solution of 1-(3-Thienyl)-1H-indole-2,3-dione (20 mg, 0.087 mmol) in 1% HOAc/MeOH (8 mL) was added to a solution of p-toluidine (19 mg, 0.18 mmol) in 1% HOAc/MeOH (8 mL). The reaction mixture was stirred for 12 h at room temperature, heated at 50° C. for 1 h, and concentrated in vacuo. The residue was purified by pre... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Primary amine | Substituted imine | c1ccc2c(c1)CC[NH]2 | c1ccc2c(c1)CC[NH]2 | c1ccccc1.c1ccsc1.c1ccc2c(c1)CC[NH]2 | HO- | CC(=O)O.CO | null | 12 | Cc1ccc(N)cc1.O=C1C(=O)N(c2ccsc2)c2ccccc21>CC(=O)O.CO>Cc1ccc(/N=C2/C(=O)N(c3ccsc3)c3ccccc32)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-13a748ea89544f7e966aecd26c9bb618 | O=C1/C(=N\c2ccc(Br)cc2)c2ccccc2N1c1ccccc1.OB(O)c1ccsc1>>O=C1/C(=N\c2ccc(-c3ccsc3)cc2)c2ccccc2N1c1ccccc1 | BrC1=CC=C(C=C1)\N=C\1/C(N(C2=CC=CC=C12)C1=CC=CC=C1)=O.S1C=C(C=C1)B(O)O.C(=O)([O-])[O-].[Na+].[Na+]>>C1(=CC=CC=C1)N1C(\C(\C2=CC=CC=C12)=N/C1=CC=C(C=C1)C1=CSC=C1)=O | Br[c:8]1[cH:7][cH:6][c:5](/[N:4]=[C:3]2\[C:2](=[O:1])[N:22]([c:23]3[cH:24][cH:25][cH:26][cH:27][cH:28]3)[c:21]3[c:16]2[cH:17][cH:18][cH:19][cH:20]3)[cH:15][cH:14]1.OB(O)[c:9]1[cH:10][cH:11][s:12][cH:13]1>>[O:1]=[C:2]1/[C:3](=[N:4]\[c:5]2[cH:6][cH:7][c:8](-[c:9]3[cH:10][cH:11][s:12][cH:13]3)[cH:14][cH:15]2)[c:16]2[cH:17... | O=C1/C(=N\c2ccc(Br)cc2)c2ccccc2N1c1ccccc1.OB(O)c1ccsc1 | O=C1/C(=N\c2ccc(-c3ccsc3)cc2)c2ccccc2N1c1ccccc1 | 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 | C1CCOC1 | C-C Coupling | Suzuki coupling with boronic acids | a9e750b5cb26673fc488a731642519fa5963d6a2e4d2eeb976470c7f17606def | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | O=C1/C(=N\c2ccc(-c3ccsc3)cc2)c2ccccc2N1c1ccccc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].O-B(-O)-[c;H0;D3;+0:6]1:[c:7]:[c:8]:[#16;a:9]:[c:10]:1>>[c:3]:[c:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:6]1:[c:7]:[c:8]:[#16;a:9]:[c:10]:1):[c:4]:[c:5] | 35.6 | [{"value": 35.0, "product": "C1(=CC=CC=C1)N1C(\\C(\\C2=CC=CC=C12)=N/C1=CC=C(C=C1)C1=CSC=C1)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 35.6, "product": "C1(=CC=CC=C1)N1C(\\C(\\C2=CC=CC=C12)=N/C1=CC=C(C=C1)C1=CSC=C1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of (3Z)-3-[(4-bromophenyl)imino]-1-phenyl-1,3-dihydro-2H-indol-2-one (50.0 mg, 0.133 mmol), thiophene-3-boronic acid (26.0 mg, 0.199 mmol), tetrakis(triphenylphosphine)palladium(0) (31.0 mg, 0.0268 mmol in THF (5 mL), and aqueous Na2CO3 (2M, 100 μL) was heated at 67° C. for 24 h. The crude product was concent... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccccc1.c1ccsc1 | c1ccccc1.c1ccsc1 | c1ccccc1.c1ccsc1.c1ccc2c(c1)CC[NH]2.c1ccccc1 | HBr.B | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.C1CCOC1 | null | null | O=C1/C(=N\c2ccc(Br)cc2)c2ccccc2N1c1ccccc1.OB(O)c1ccsc1>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.C1CCOC1>O=C1/C(=N\c2ccc(-c3ccsc3)cc2)c2ccccc2N1c1ccccc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-c998e9f185cc4e6cb70325548c13fc31 | Nc1cccc(C(F)(F)F)c1.O=C1Nc2ccc(Br)cc2C1=O>>O=C1Nc2ccc(Br)cc2/C1=N/c1cccc(C(F)(F)F)c1 | BrC=1C=C2C(C(NC2=CC1)=O)=O.FC(C=1C=C(N)C=CC1)(F)F.C(C)(=O)O>>BrC=1C=C2/C(/C(NC2=CC1)=O)=N/C1=CC(=CC=C1)C(F)(F)F | [NH2:12][c:13]1[cH:14][cH:15][cH:16][c:17]([C:18]([F:19])([F:20])[F:21])[cH:22]1.O=[C:11]1[C:2](=[O:1])[NH:3][c:4]2[cH:5][cH:6][c:7]([Br:8])[cH:9][c:10]21>>[O:1]=[C:2]1[NH:3][c:4]2[cH:5][cH:6][c:7]([Br:8])[cH:9][c:10]2/[C:11]1=[N:12]/[c:13]1[cH:14][cH:15][cH:16][c:17]([C:18]([F:19])([F:20])[F:21])[cH:22]1 | Nc1cccc(C(F)(F)F)c1.O=C1Nc2ccc(Br)cc2C1=O | O=C1Nc2ccc(Br)cc2/C1=N/c1cccc(C(F)(F)F)c1 | null | null | CO | Heteroatom Alkylation and Arylation | Addition of primary amines to ketones/thiocarbonyls | 4bfb2d13f747833357b7c6041ae6574aa9266b585017c0b5867f288cad7cdf61 | 009cc6a97ebe0dc96c669f0ef59b95bcc20de7cae20b1b648ce8f8fa82309e57 | O=C1Nc2ccccc2/C1=N/c1ccccc1 | O=[C;H0;D3;+0:1]1-[C:2](=[O;D1;H0:3])-[#7:4]-[c:5]:[c:6]-1:[c:7].[NH2;D1;+0:8]-[c:9](:[c:10]):[c:11]>>[O;D1;H0:3]=[C:2]1-[#7:4]-[c:5]:[c:6](:[c:7])/[C;H0;D3;+0:1]-1=[N;H0;D2;+0:8]/[c:9](:[c:10]):[c:11] | 392.3 | [{"value": 40.0, "product": "BrC=1C=C2/C(/C(NC2=CC1)=O)=N/C1=CC(=CC=C1)C(F)(F)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 392.3, "product": "BrC=1C=C2/C(/C(NC2=CC1)=O)=N/C1=CC(=CC=C1)C(F)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 50 | CELSIUS | 12 | HOUR | A mixture of 5-bromo-1H-indole-2,3-dione (1.0 g, 0.442 mmol) and 3-trifluoromethylaniline (0.993 g, 6.2 mmol) in a solution of 1% acetic acid in methanol was stirred at 50° C. for 12 h. The crude product was concentrated in vacuo, giving the desired crude product (640 mg, 40%).
Conditions: See reaction.notes.procedure_... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Primary amine | Substituted imine | c1ccc2c(c1)CCN2 | c1ccc2c(c1)CCN2 | c1ccc2c(c1)CCN2.c1ccccc1 | HO- | CO | 50 | 12 | Nc1cccc(C(F)(F)F)c1.O=C1Nc2ccc(Br)cc2C1=O>CO>O=C1Nc2ccc(Br)cc2/C1=N/c1cccc(C(F)(F)F)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-fd5616a14b0c4fb7b191c5db3918eeb2 | O=C1Nc2ccc(Br)cc2/C1=N/c1cccc(C(F)(F)F)c1.OB(O)c1ccccc1>>O=C1/C(=N\c2cccc(C(F)(F)F)c2)c2cc(Br)ccc2N1c1ccccc1 | BrC=1C=C2/C(/C(NC2=CC1)=O)=N/C1=CC(=CC=C1)C(F)(F)F.C(C)N(CC)CC.C1(=CC=CC=C1)B(O)O>>BrC=1C=C2/C(/C(N(C2=CC1)C1=CC=CC=C1)=O)=N/C1=CC(=CC=C1)C(F)(F)F | [O:1]=[C:2]1/[C:3](=[N:4]\[c:5]2[cH:6][cH:7][cH:8][c:9]([C:10]([F:11])([F:12])[F:13])[cH:14]2)[c:15]2[cH:16][c:17]([Br:18])[cH:19][cH:20][c:21]2[NH:22]1.OB(O)[c:23]1[cH:24][cH:25][cH:26][cH:27][cH:28]1>>[O:1]=[C:2]1/[C:3](=[N:4]\[c:5]2[cH:6][cH:7][cH:8][c:9]([C:10]([F:11])([F:12])[F:13])[cH:14]2)[c:15]2[cH:16][c:17]([B... | O=C1Nc2ccc(Br)cc2/C1=N/c1cccc(C(F)(F)F)c1.OB(O)c1ccccc1 | O=C1/C(=N\c2cccc(C(F)(F)F)c2)c2cc(Br)ccc2N1c1ccccc1 | null | C(C)(=O)[O-].[Cu+2].C(C)(=O)[O-] | C(Cl)Cl | Heteroatom Alkylation and Arylation | Petasis reaction with amines and boronic acids | 7d50cd3130b5c4a1ba2100ed241ee573a7c045be5ef047e05c10679ee3f81d2a | d8988f95994c3a53b8581714df91fdcf58fce7c875a9f3af0fd1011694639d17 | O=C1/C(=N\c2ccccc2)c2ccccc2N1c1ccccc1 | O-B(-O)-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[#7:6]=[C:7]1/[c:8]:[c:9](:[c:10])-[NH;D2;+0:11]-[C:12]-1=[O;D1;H0:13]>>[#7:6]=[C:7]1/[c:8]:[c:9](:[c:10])-[N;H0;D3;+0:11](-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5])-[C:12]-1=[O;D1;H0:13] | 20 | [{"value": 20.0, "product": "BrC=1C=C2/C(/C(N(C2=CC1)C1=CC=CC=C1)=O)=N/C1=CC(=CC=C1)C(F)(F)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 18.2, "product": "BrC=1C=C2/C(/C(N(C2=CC1)C1=CC=CC=C1)=O)=N/C1=CC(=CC=C1)C(F)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 12 | HOUR | A mixture of (3z)-5-bromo-3-{[3-(trifluoromethyl)phenyl]imino}-1,3-dihydro-2h-indol-2-one (100 mg, 0.272 mmol), copper (II) acetate (54 mg, 0.33 mmol), triethylamine (82.8 mg, 0.817 mmol), and benzene boronic acid (40 mg, 0.325 mmol) in 5 mL of CH2Cl2 was stirred at room temperature for 12 h. The crude mixture was conc... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide.Boronic acid | Tertiary amide | c1ccc2c(c1)CCN2.c1ccccc1 | c1ccc2c(c1)CC[NH]2.c1ccccc1 | c1ccccc1.c1ccc2c(c1)CC[NH]2.c1ccccc1 | HO-.B | C(C)(=O)[O-].[Cu+2].C(C)(=O)[O-].C(Cl)Cl | null | 12 | O=C1Nc2ccc(Br)cc2/C1=N/c1cccc(C(F)(F)F)c1.OB(O)c1ccccc1>C(C)(=O)[O-].[Cu+2].C(C)(=O)[O-].C(Cl)Cl>O=C1/C(=N\c2cccc(C(F)(F)F)c2)c2cc(Br)ccc2N1c1ccccc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-d46320bdbf2d4cf3bd047b878bf1dd82 | O=C1/C(=N\c2cccc(C(F)(F)F)c2)c2cc(Br)ccc2N1c1ccccc1.OB(O)c1ccccc1>>O=C1/C(=N\c2cccc(C(F)(F)F)c2)c2cc(-c3ccccc3)ccc2N1c1ccccc1 | BrC=1C=C2/C(/C(N(C2=CC1)C1=CC=CC=C1)=O)=N/C1=CC(=CC=C1)C(F)(F)F.C1(=CC=CC=C1)B(O)O.C(=O)([O-])[O-].[Na+].[Na+]>>C1(=CC=CC=C1)N1C(\C(\C2=CC(=CC=C12)C1=CC=CC=C1)=N/C1=CC(=CC=C1)C(F)(F)F)=O | Br[c:17]1[cH:16][c:15]2[c:26]([cH:25][cH:24]1)[N:27]([c:28]1[cH:29][cH:30][cH:31][cH:32][cH:33]1)[C:2](=[O:1])/[C:3]2=[N:4]\[c:5]1[cH:6][cH:7][cH:8][c:9]([C:10]([F:11])([F:12])[F:13])[cH:14]1.OB(O)[c:18]1[cH:19][cH:20][cH:21][cH:22][cH:23]1>>[O:1]=[C:2]1/[C:3](=[N:4]\[c:5]2[cH:6][cH:7][cH:8][c:9]([C:10]([F:11])([F:12])... | O=C1/C(=N\c2cccc(C(F)(F)F)c2)c2cc(Br)ccc2N1c1ccccc1.OB(O)c1ccccc1 | O=C1/C(=N\c2cccc(C(F)(F)F)c2)c2cc(-c3ccccc3)ccc2N1c1ccccc1 | 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 | C1CCOC1 | C-C Coupling | Suzuki coupling with boronic acids | 230d216bd15e8f05452eb03e7fbfe4df8d73bb6c1b59a26bce79f50e659677d0 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | O=C1/C(=N\c2ccccc2)c2cc(-c3ccccc3)ccc2N1c1ccccc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].O-B(-O)-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]>>[c:3]:[c:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]):[c:4]:[c:5] | 18.1 | [{"value": 18.0, "product": "C1(=CC=CC=C1)N1C(\\C(\\C2=CC(=CC=C12)C1=CC=CC=C1)=N/C1=CC(=CC=C1)C(F)(F)F)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 18.1, "product": "C1(=CC=CC=C1)N1C(\\C(\\C2=CC(=CC=C12)C1=CC=CC=C1)=N/C1=CC(=CC=C1)C(F)(F)F)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false... | 67 | CELSIUS | null | null | A mixture of (3z)-5-bromo-1-phenyl-3-{[3-(trifluoromethyl)phenyl]imino}-1,3-dihydro-2H-indol-2-one (22 mg, 0.05 mmol), tetrakis(triphenylphosphine)palladium(0) (12.0 mg, 0.01 mmol), benzene boronic acid (10 mg, 0.08 mmol) in THF (5 mL), and aqueous Na2CO3 (2M, 100 μL) was heated at 67° C. for 24 h. The crude product wa... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccc2c(c1)CC[NH]2.c1ccccc1 | c1ccc2c(c1)CC[NH]2.c1ccccc1 | c1ccccc1.c1ccc2c(c1)CC[NH]2.c1ccccc1.c1ccccc1 | HBr.B | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.C1CCOC1 | 67 | null | O=C1/C(=N\c2cccc(C(F)(F)F)c2)c2cc(Br)ccc2N1c1ccccc1.OB(O)c1ccccc1>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.C1CCOC1>O=C1/C(=N\c2cccc(C(F)(F)F)c2)c2cc(-c3ccccc3)ccc2N1c1ccccc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-268356a64b264db1a90cb36dc8e4239e | CCOC(=O)c1ccc(CN2C(=O)C(=O)c3ccccc32)o1.Nc1cccc(C(F)(F)F)c1>>CCOC(=O)c1ccc(CN2C(=O)/C(=N\c3cccc(C(F)(F)F)c3)c3ccccc32)o1 | O=C1N(C2=CC=CC=C2C1=O)CC1=CC=C(O1)C(=O)OCC.FC(C=1C=C(N)C=CC1)(F)F>>O=C\1N(C2=CC=CC=C2/C1=N/C1=CC(=CC=C1)C(F)(F)F)CC1=CC=C(O1)C(=O)OCC | O=[C:14]1[C:12](=[O:13])[N:11]([CH2:10][c:9]2[cH:8][cH:7][c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[o:32]2)[c:31]2[c:26]1[cH:27][cH:28][cH:29][cH:30]2.[NH2:15][c:16]1[cH:17][cH:18][cH:19][c:20]([C:21]([F:22])([F:23])[F:24])[cH:25]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][c:9]([CH2:10][N:11]2[C:12](=[O:13])/[C:... | CCOC(=O)c1ccc(CN2C(=O)C(=O)c3ccccc32)o1.Nc1cccc(C(F)(F)F)c1 | CCOC(=O)c1ccc(CN2C(=O)/C(=N\c3cccc(C(F)(F)F)c3)c3ccccc32)o1 | null | null | C(Cl)(Cl)Cl | Heteroatom Alkylation and Arylation | Addition of primary amines to ketones/thiocarbonyls | 561e2daf1aa504fe4e7a04c4a24377b070a888e3731bdc015219988535a1cb4e | 009cc6a97ebe0dc96c669f0ef59b95bcc20de7cae20b1b648ce8f8fa82309e57 | O=C1/C(=N\c2ccccc2)c2ccccc2N1Cc1ccco1 | O=[C;H0;D3;+0:1]1-[C:2](=[O;D1;H0:3])-[#7:4](-[C:5])-[c:6]:[c:7]-1:[c:8].[NH2;D1;+0:9]-[c:10](:[c:11]):[c:12]>>[C:5]-[#7:4]1-[c:6]:[c:7](:[c:8])/[C;H0;D3;+0:1](=[N;H0;D2;+0:9]/[c:10](:[c:11]):[c:12])-[C:2]-1=[O;D1;H0:3] | 23 | [{"value": 23.0, "product": "O=C\\1N(C2=CC=CC=C2/C1=N/C1=CC(=CC=C1)C(F)(F)F)CC1=CC=C(O1)C(=O)OCC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 22.6, "product": "O=C\\1N(C2=CC=CC=C2/C1=N/C1=CC(=CC=C1)C(F)(F)F)CC1=CC=C(O1)C(=O)OCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 140 | CELSIUS | null | null | A mixture of ethyl 5-[(2,3-dioxo-2,3-dihydro-1H-indol-1-yl)methyl]-2-furoate (60 mg, 0.200 mmol) and 3-trifluromethylaniline (32 mg, 0.200 mmol) was heated at 140° C. for 2 h. The residue was dissolved in CHCl3 (1 mL) and purified by preparative TLC using EtOAc/hexane 6:4), giving the desired product (20 mg, 23%)
Condi... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Primary amine | Substituted imine | c1ccc2c(c1)CC[NH]2 | c1ccc2c(c1)CC[NH]2 | c1ccoc1.c1ccccc1.c1ccc2c(c1)CC[NH]2 | HO- | C(Cl)(Cl)Cl | 140 | null | CCOC(=O)c1ccc(CN2C(=O)C(=O)c3ccccc32)o1.Nc1cccc(C(F)(F)F)c1>C(Cl)(Cl)Cl>CCOC(=O)c1ccc(CN2C(=O)/C(=N\c3cccc(C(F)(F)F)c3)c3ccccc32)o1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-7d22e1f6b3ff4c17bdbdbfc64e1a4348 | O=C1Nc2ccccc2/C1=N/c1cccc(C(F)(F)F)c1.OB(O)c1ccc(Br)cc1>>O=C1/C(=N\c2cccc(C(F)(F)F)c2)c2ccccc2N1c1ccc(Br)cc1 | FC(C=1C=C(C=CC1)\N=C\1/C(NC2=CC=CC=C12)=O)(F)F.C(C)N(CC)CC.BrC1=CC=C(C=C1)B(O)O>>BrC1=CC=C(C=C1)N1C(\C(\C2=CC=CC=C12)=N/C1=CC(=CC=C1)C(F)(F)F)=O | [O:1]=[C:2]1/[C:3](=[N:4]\[c:5]2[cH:6][cH:7][cH:8][c:9]([C:10]([F:11])([F:12])[F:13])[cH:14]2)[c:15]2[cH:16][cH:17][cH:18][cH:19][c:20]2[NH:21]1.OB(O)[c:22]1[cH:23][cH:24][c:25]([Br:26])[cH:27][cH:28]1>>[O:1]=[C:2]1/[C:3](=[N:4]\[c:5]2[cH:6][cH:7][cH:8][c:9]([C:10]([F:11])([F:12])[F:13])[cH:14]2)[c:15]2[cH:16][cH:17][c... | O=C1Nc2ccccc2/C1=N/c1cccc(C(F)(F)F)c1.OB(O)c1ccc(Br)cc1 | O=C1/C(=N\c2cccc(C(F)(F)F)c2)c2ccccc2N1c1ccc(Br)cc1 | null | C(C)(=O)[O-].[Cu+2].C(C)(=O)[O-] | C(Cl)Cl | Heteroatom Alkylation and Arylation | Petasis reaction with amines and boronic acids | 7d50cd3130b5c4a1ba2100ed241ee573a7c045be5ef047e05c10679ee3f81d2a | d8988f95994c3a53b8581714df91fdcf58fce7c875a9f3af0fd1011694639d17 | O=C1/C(=N\c2ccccc2)c2ccccc2N1c1ccccc1 | O-B(-O)-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[#7:6]=[C:7]1/[c:8]:[c:9](:[c:10])-[NH;D2;+0:11]-[C:12]-1=[O;D1;H0:13]>>[#7:6]=[C:7]1/[c:8]:[c:9](:[c:10])-[N;H0;D3;+0:11](-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5])-[C:12]-1=[O;D1;H0:13] | 42.4 | [{"value": 42.0, "product": "BrC1=CC=C(C=C1)N1C(\\C(\\C2=CC=CC=C12)=N/C1=CC(=CC=C1)C(F)(F)F)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 42.4, "product": "BrC1=CC=C(C=C1)N1C(\\C(\\C2=CC=CC=C12)=N/C1=CC(=CC=C1)C(F)(F)F)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of (3Z)-3-{[3-(trifluoromethyl)phenyl]imino}-1,3-dihydro-2H-indol-2-one (100 mg, 0.344 mmol), copper (II) acetate (93 mg, 0.516 mmol), triethylamine (105 mg, 1.03 mmol), and 4-bromobenzene boronic acid (104 mg, 0.516 mmol) in 5 mL of CH2Cl2 was stirred at room temperature for 12 h. The crude mixture was conc... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide.Boronic acid | Tertiary amide | c1ccc2c(c1)CCN2.c1ccccc1 | c1ccc2c(c1)CC[NH]2.c1ccccc1 | c1ccccc1.c1ccc2c(c1)CC[NH]2.c1ccccc1 | HO-.B | C(C)(=O)[O-].[Cu+2].C(C)(=O)[O-].C(Cl)Cl | null | null | O=C1Nc2ccccc2/C1=N/c1cccc(C(F)(F)F)c1.OB(O)c1ccc(Br)cc1>C(C)(=O)[O-].[Cu+2].C(C)(=O)[O-].C(Cl)Cl>O=C1/C(=N\c2cccc(C(F)(F)F)c2)c2ccccc2N1c1ccc(Br)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-c9cd8e20b5c343e987e06cd2189b8dec | Nc1cccc(C(F)(F)F)c1.O=C1C(=O)N(Cc2ccc(Cl)s2)c2ccccc21>>O=C1C(=Nc2cccc(C(F)(F)F)c2)c2ccccc2N1Cc1ccc(Cl)s1 | ClC1=CC=C(S1)CN1C(C(C2=CC=CC=C12)=O)=O.FC(C=1C=C(N)C=CC1)(F)F>>ClC1=CC=C(S1)CN1C(C(C2=CC=CC=C12)=NC1=CC(=CC=C1)C(F)(F)F)=O | [NH2:4][c:5]1[cH:6][cH:7][cH:8][c:9]([C:10]([F:11])([F:12])[F:13])[cH:14]1.O=[C:3]1[C:2](=[O:1])[N:21]([CH2:22][c:23]2[cH:24][cH:25][c:26]([Cl:27])[s:28]2)[c:20]2[c:15]1[cH:16][cH:17][cH:18][cH:19]2>>[O:1]=[C:2]1[C:3](=[N:4][c:5]2[cH:6][cH:7][cH:8][c:9]([C:10]([F:11])([F:12])[F:13])[cH:14]2)[c:15]2[cH:16][cH:17][cH:18]... | Nc1cccc(C(F)(F)F)c1.O=C1C(=O)N(Cc2ccc(Cl)s2)c2ccccc21 | O=C1C(=Nc2cccc(C(F)(F)F)c2)c2ccccc2N1Cc1ccc(Cl)s1 | null | null | null | Heteroatom Alkylation and Arylation | Addition of primary amines to ketones/thiocarbonyls | 561e2daf1aa504fe4e7a04c4a24377b070a888e3731bdc015219988535a1cb4e | 009cc6a97ebe0dc96c669f0ef59b95bcc20de7cae20b1b648ce8f8fa82309e57 | O=C1C(=Nc2ccccc2)c2ccccc2N1Cc1cccs1 | O=[C;H0;D3;+0:1]1-[C:2](=[O;D1;H0:3])-[#7:4](-[C:5])-[c:6]:[c:7]-1:[c:8].[NH2;D1;+0:9]-[c:10](:[c:11]):[c:12]>>[C:5]-[#7:4]1-[c:6]:[c:7](:[c:8])-[C;H0;D3;+0:1](=[N;H0;D2;+0:9]-[c:10](:[c:11]):[c:12])-[C:2]-1=[O;D1;H0:3] | 61 | [{"value": 61.0, "product": "ClC1=CC=C(S1)CN1C(C(C2=CC=CC=C12)=NC1=CC(=CC=C1)C(F)(F)F)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 55.6, "product": "ClC1=CC=C(S1)CN1C(C(C2=CC=CC=C12)=NC1=CC(=CC=C1)C(F)(F)F)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 140 | CELSIUS | null | null | A mixture of 1-[(5-chloro-2-thienyl)methyl]-2H-indole-2,3-dione (25 mg, 0.09 mmol) (prepared as described below) and 3-trifluoromethylaniline (11.3 μL, 0.09 mmol) was heated neat at 140° C. for 2 h. The crude material was purified by preparative TLC using a mixture of 3:7 ethyl acetate in hexane as the eluent, giving t... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Primary amine | Substituted imine | c1ccc2c(c1)CC[NH]2 | c1ccc2c(c1)CC[NH]2 | c1ccccc1.c1ccc2c(c1)CC[NH]2.c1ccsc1 | HO- | null | 140 | null | Nc1cccc(C(F)(F)F)c1.O=C1C(=O)N(Cc2ccc(Cl)s2)c2ccccc21>>O=C1C(=Nc2cccc(C(F)(F)F)c2)c2ccccc2N1Cc1ccc(Cl)s1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-d1d6786b0e10444cac3e9491ea0af702 | ClCc1ccc(Cl)s1.O=C1Nc2ccccc2C1=O>>O=C1C(=O)N(Cc2ccc(Cl)s2)c2ccccc21 | N1C(=O)C(=O)C2=CC=CC=C12.[H-].[Na+].ClC=1SC(=CC1)CCl>>ClC1=CC=C(S1)CN1C(C(C2=CC=CC=C12)=O)=O | Cl[CH2:6][c:7]1[cH:8][cH:9][c:10]([Cl:11])[s:12]1.[O:1]=[C:2]1[C:3](=[O:4])[NH:5][c:13]2[cH:14][cH:15][cH:16][cH:17][c:18]21>>[O:1]=[C:2]1[C:3](=[O:4])[N:5]([CH2:6][c:7]2[cH:8][cH:9][c:10]([Cl:11])[s:12]2)[c:13]2[cH:14][cH:15][cH:16][cH:17][c:18]21 | ClCc1ccc(Cl)s1.O=C1Nc2ccccc2C1=O | O=C1C(=O)N(Cc2ccc(Cl)s2)c2ccccc21 | null | null | O1CCOCC1 | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | c168ddb7803c893ec5334f16b8c2262b487eff0908e05ac9b9feab6bfceb9bd3 | 4a6c1e88c9e8bed487b746792f88d478ff36cc235f9a217d4632e6babdebdc9a | O=C1C(=O)N(Cc2cccs2)c2ccccc21 | Cl-[CH2;D2;+0:1]-[c:2](:[c:3]):[#16;a:4]:[c:5].[O;D1;H0:6]=[C:7]1-[c:8]:[c:9](:[c:10])-[NH;D2;+0:11]-[C:12]-1=[O;D1;H0:13]>>[O;D1;H0:6]=[C:7]1-[c:8]:[c:9](:[c:10])-[N;H0;D3;+0:11](-[CH2;D2;+0:1]-[c:2](:[c:3]):[#16;a:4]:[c:5])-[C:12]-1=[O;D1;H0:13] | 22.4 | [{"value": 22.0, "product": "ClC1=CC=C(S1)CN1C(C(C2=CC=CC=C12)=O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 22.4, "product": "ClC1=CC=C(S1)CN1C(C(C2=CC=CC=C12)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 5 | MINUTE | A solution of isatin (125 mg, 0.85 mmol) in anhydrous dioxane (10 mL) was added dropwise to a solution of sodium hydride (60% dispersion in mineral oil, 24 mg, 0.62 mmol) in anhydrous dioxane (10 mL) at 0° C. under argon. The mixture was allowed to stir for 5 minutes and then 2-chloro-5-(chloromethyl)thiophene (0.12 mL... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amide | Tertiary amide | c1ccc2c(c1)CCN2 | c1ccc2c(c1)CC[NH]2 | c1ccsc1.c1ccc2c(c1)CC[NH]2 | HCl | O1CCOCC1 | null | 0.083333 | ClCc1ccc(Cl)s1.O=C1Nc2ccccc2C1=O>O1CCOCC1>O=C1C(=O)N(Cc2ccc(Cl)s2)c2ccccc21 |
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