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-ae2bce0aa2434bbe9aa4872d5d9cafd6 | COCOc1ccc(C2(C)COc3cc(OCOC)ccc3C2(O)C#CCOc2ccc(CCCO[Si](C)(C)C(C)(C)C)cc2)cc1>>COCOc1ccc(C2(C)COc3cc(OCOC)ccc3C2C#CCOc2ccc(CCCO[Si](C)(C)C(C)(C)C)cc2)cc1 | [Si](C)(C)(C(C)(C)C)OCCCC1=CC=C(OCC#CC2(C(COC3=CC(=CC=C23)OCOC)(C)C2=CC=C(C=C2)OCOC)O)C=C1.[Si](C)(C)(C(C)(C)C)OCCCCCCCC#CC1C(CSC2=CC(=CC=C12)OC)(C)C1=CC=C(C=C1)OC>>[Si](C)(C)(C(C)(C)C)OCCCC1=CC=C(OCC#CC2C(COC3=CC(=CC=C23)OCOC)(C)C2=CC=C(C=C2)OCOC)C=C1 | O[C:23]1([C:24]#[C:25][CH2:26][O:27][c:28]2[cH:29][cH:30][c:31]([CH2:32][CH2:33][CH2:34][O:35][Si:36]([CH3:37])([CH3:38])[C:39]([CH3:40])([CH3:41])[CH3:42])[cH:43][cH:44]2)[C:9]([c:8]2[cH:7][cH:6][c:5]([O:4][CH2:3][O:2][CH3:1])[cH:46][cH:45]2)([CH3:10])[CH2:11][O:12][c:13]2[cH:14][c:15]([O:16][CH2:17][O:18][CH3:19])[cH... | COCOc1ccc(C2(C)COc3cc(OCOC)ccc3C2(O)C#CCOc2ccc(CCCO[Si](C)(C)C(C)(C)C)cc2)cc1 | COCOc1ccc(C2(C)COc3cc(OCOC)ccc3C2C#CCOc2ccc(CCCO[Si](C)(C)C(C)(C)C)cc2)cc1 | null | null | null | Reduction | OtherReaction | d9ad9de0a2df8f543d454c115f7a58d9a012b1cbcc0f40fa0bf7cc7b376ca1e8 | dfa71f841ee148297c95b5d95b7150768ab9356304fca8dbfde20c6dadd639d3 | C(#CC1c2ccccc2OCC1c1ccccc1)COc1ccccc1 | O-[C;H0;D4;+0:1]1(-[C:2]#[C:3]-[C:4])-[c:5](:[c:6]):[c:7]-[#8:8]-[C:9]-[C:10]-1(-[C;D1;H3:11])-[c:12]>>[C:4]-[C:3]#[C:2]-[CH;D3;+0:1]1-[c:5](:[c:6]):[c:7]-[#8:8]-[C:9]-[C:10]-1(-[C;D1;H3:11])-[c:12] | null | [] | null | null | null | null | The title compound was prepared from 4-{3-[4-(3-t-butyldimethylsilyloxypropyl)phenoxy]-1-propynyl}-7-methoxymethyloxy-3-(4-methoxymethyloxyphenyl)-3-methylchroman-4-ol according to the same method for the synthesis of 4-[9-(t-butyldimethylsilyloxy)-1-nonynyl]-7-methoxy-3-(4-methoxyphenyl)-3-methylthiochroman described ... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary alcohol | null | c1ccc2c(c1)CCCO2 | c1ccc2c(c1)CCCO2 | c1ccccc1.c1ccc2c(c1)CCCO2.c1ccccc1 | Other | null | null | null | COCOc1ccc(C2(C)COc3cc(OCOC)ccc3C2(O)C#CCOc2ccc(CCCO[Si](C)(C)C(C)(C)C)cc2)cc1>>COCOc1ccc(C2(C)COc3cc(OCOC)ccc3C2C#CCOc2ccc(CCCO[Si](C)(C)C(C)(C)C)cc2)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-98c2443a642f46f187349ca6df202f00 | COCOc1ccc(C2(C)COc3cc(OCOC)ccc3C2C#CCOc2ccc(CCCO[Si](C)(C)C(C)(C)C)cc2)cc1>>COCOc1ccc(C2(C)COc3cc(OCOC)ccc3C2CCCOc2ccc(CCCO[Si](C)(C)C(C)(C)C)cc2)cc1 | [Si](C)(C)(C(C)(C)C)OCCCC1=CC=C(OCC#CC2C(COC3=CC(=CC=C23)OCOC)(C)C2=CC=C(C=C2)OCOC)C=C1.[Si](C)(C)(C(C)(C)C)OCCCCCCCCCC1C(CSC2=CC(=CC=C12)OC)(C)C1=CC=C(C=C1)OC>>[Si](C)(C)(C(C)(C)C)OCCCC1=CC=C(OCCCC2C(COC3=CC(=CC=C23)OCOC)(C)C2=CC=C(C=C2)OCOC)C=C1 | [CH3:1][O:2][CH2:3][O:4][c:5]1[cH:6][cH:7][c:8]([C:9]2([CH3:10])[CH2:11][O:12][c:13]3[cH:14][c:15]([O:16][CH2:17][O:18][CH3:19])[cH:20][cH:21][c:22]3[CH:23]2[C:24]#[C:25][CH2:26][O:27][c:28]2[cH:29][cH:30][c:31]([CH2:32][CH2:33][CH2:34][O:35][Si:36]([CH3:37])([CH3:38])[C:39]([CH3:40])([CH3:41])[CH3:42])[cH:43][cH:44]2)... | COCOc1ccc(C2(C)COc3cc(OCOC)ccc3C2C#CCOc2ccc(CCCO[Si](C)(C)C(C)(C)C)cc2)cc1 | COCOc1ccc(C2(C)COc3cc(OCOC)ccc3C2CCCOc2ccc(CCCO[Si](C)(C)C(C)(C)C)cc2)cc1 | null | null | null | Reduction | OtherReaction | 2bb8d5b532a2781e0a7c069a5cd3e8a7e8d44660c0ec1d9e17c04d8ba2cb383b | 1990560e9c55934bde8ca0feaed9c61d80f37f94f0cf240a9929dc374d0a33aa | c1ccc(OCCCC2c3ccccc3OCC2c2ccccc2)cc1 | [#8:1]-[C:2]-[C;H0;D2;+0:3]#[C;H0;D2;+0:4]-[C:5](-[C:6])-[c:7]>>[#8:1]-[C:2]-[CH2;D2;+0:3]-[CH2;D2;+0:4]-[C:5](-[C:6])-[c:7] | null | [] | null | null | null | null | The title compound was prepared from 4-{3-[4-(3-t-butyldimethylsilyloxypropyl)phenoxy]-1-propynyl}-7-methoxymethyloxy-3-(4-methoxymethyloxyphenyl)-3-methylchroman according to the same method for the synthesis of 4-[9-(t-butyldimethylsilyloxy)-1-nonyl]-7-methoxy-3-(4-methoxyphenyl)-3-methylthiochroman described in Inte... | 10.6084/m9.figshare.5104873.v1 | null | Alkyne | null | null | null | c1ccccc1.c1ccc2c(c1)CCCO2.c1ccccc1 | null | null | null | null | COCOc1ccc(C2(C)COc3cc(OCOC)ccc3C2C#CCOc2ccc(CCCO[Si](C)(C)C(C)(C)C)cc2)cc1>>COCOc1ccc(C2(C)COc3cc(OCOC)ccc3C2CCCOc2ccc(CCCO[Si](C)(C)C(C)(C)C)cc2)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-6c73446eef51478ba3bef8d5670c76fa | COCOc1ccc(C2(C)COc3cc(OCOC)ccc3C2CCCOc2ccc(CCCO[Si](C)(C)C(C)(C)C)cc2)cc1>>COCOc1ccc(C2(C)COc3cc(OCOC)ccc3C2CCCOc2ccc(CCCO)cc2)cc1 | [Si](C)(C)(C(C)(C)C)OCCCC1=CC=C(OCCCC2C(COC3=CC(=CC=C23)OCOC)(C)C2=CC=C(C=C2)OCOC)C=C1.OCCCCCCCCCC1C(COC2=CC(=CC=C12)OCOC)(C)C1=CC=C(C=C1)OCOC>>OCCCC1=CC=C(OCCCC2C(COC3=CC(=CC=C23)OCOC)(C)C2=CC=C(C=C2)OCOC)C=C1 | CC(C)(C)[Si](C)(C)[O:35][CH2:34][CH2:33][CH2:32][c:31]1[cH:30][cH:29][c:28]([O:27][CH2:26][CH2:25][CH2:24][CH:23]2[C:9]([c:8]3[cH:7][cH:6][c:5]([O:4][CH2:3][O:2][CH3:1])[cH:39][cH:38]3)([CH3:10])[CH2:11][O:12][c:13]3[cH:14][c:15]([O:16][CH2:17][O:18][CH3:19])[cH:20][cH:21][c:22]32)[cH:37][cH:36]1>>[CH3:1][O:2][CH2:3][O... | COCOc1ccc(C2(C)COc3cc(OCOC)ccc3C2CCCOc2ccc(CCCO[Si](C)(C)C(C)(C)C)cc2)cc1 | COCOc1ccc(C2(C)COc3cc(OCOC)ccc3C2CCCOc2ccc(CCCO)cc2)cc1 | null | null | null | Deprotection | Alcohol deprotection from silyl ethers | 6ff8c9c41093ab5237b871dd4689ba6431022d615e227d3774901a983c846e4b | 84d9f5b4e7757c58e584c26c7d52c9a3f594fbcb0c0d22f34765a93a932fcd5b | c1ccc(OCCCC2c3ccccc3OCC2c2ccccc2)cc1 | C-C(-C)(-C)-[Si](-C)(-C)-[O;H0;D2;+0:1]-[C:2]-[C:3]>>[C:3]-[C:2]-[OH;D1;+0:1] | null | [] | null | null | null | null | The title compound was prepared from (3RS,4RS)-4-{3-[4-(3-t-butyl-dimethylsilyloxypropyl)phenoxy]-1-propyl}-7-methoxymethyloxy-3-(4-methoxymethyloxyphenyl)-3-methylchroman according to the same method for the synthesis of 4-[9-hydroxy-1-nonyl]-7-methoxymethyloxy-3-(4-methoxymethyloxyphenyl)-3-methylchroman described in... | 10.6084/m9.figshare.5104873.v1 | null | TMS ether protective group | Primary alcohol | null | null | c1ccccc1.c1ccc2c(c1)CCCO2.c1ccccc1 | Other | null | null | null | COCOc1ccc(C2(C)COc3cc(OCOC)ccc3C2CCCOc2ccc(CCCO[Si](C)(C)C(C)(C)C)cc2)cc1>>COCOc1ccc(C2(C)COc3cc(OCOC)ccc3C2CCCOc2ccc(CCCO)cc2)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-cb5613b1b5b74d26bc9c8f8102fa89da | CC(C)(C)OC(=O)CBr.COCOc1ccc(C2(C)COc3cc(OCOC)ccc3C2CCCCc2ccc(O)cc2)cc1>>COCOc1ccc(C2(C)COc3cc(OCOC)ccc3C2CCCCc2ccc(OCC(=O)OC(C)(C)C)cc2)cc1 | O.C(C)(C)(C)OC(CBr)=O.OC1=CC=C(C=C1)CCCCC1C(COC2=CC(=CC=C12)OCOC)(C)C1=CC=C(C=C1)OCOC.[H-].[Na+]>>C(C)(C)(C)OC(=O)COC1=CC=C(C=C1)CCCCC1C(COC2=CC(=CC=C12)OCOC)(C)C1=CC=C(C=C1)OCOC | Br[CH2:33][C:34](=[O:35])[O:36][C:37]([CH3:38])([CH3:39])[CH3:40].[CH3:1][O:2][CH2:3][O:4][c:5]1[cH:6][cH:7][c:8]([C:9]2([CH3:10])[CH2:11][O:12][c:13]3[cH:14][c:15]([O:16][CH2:17][O:18][CH3:19])[cH:20][cH:21][c:22]3[CH:23]2[CH2:24][CH2:25][CH2:26][CH2:27][c:28]2[cH:29][cH:30][c:31]([OH:32])[cH:41][cH:42]2)[cH:43][cH:44... | CC(C)(C)OC(=O)CBr.COCOc1ccc(C2(C)COc3cc(OCOC)ccc3C2CCCCc2ccc(O)cc2)cc1 | COCOc1ccc(C2(C)COc3cc(OCOC)ccc3C2CCCCc2ccc(OCC(=O)OC(C)(C)C)cc2)cc1 | null | null | O1CCCC1 | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 50d675b335c583a6ce22e1164b27a78b18b9ca447d45137820c344bcb6369217 | 0865de4e1853c59ac25437e36fd18b03329566cb9eff4b4f0ce70d5714692fd3 | c1ccc(CCCCC2c3ccccc3OCC2c2ccccc2)cc1 | Br-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#8:4]-[C:5](-[C;D1;H3:6])(-[C;D1;H3:7])-[C;D1;H3:8].[OH;D1;+0:9]-[c:10](:[c:11]):[c:12]>>[C;D1;H3:6]-[C:5](-[C;D1;H3:7])(-[C;D1;H3:8])-[#8:4]-[C:2](=[O;D1;H0:3])-[CH2;D2;+0:1]-[O;H0;D2;+0:9]-[c:10](:[c:11]):[c:12] | 99.5 | [{"value": 99.5, "product": "C(C)(C)(C)OC(=O)COC1=CC=C(C=C1)CCCCC1C(COC2=CC(=CC=C12)OCOC)(C)C1=CC=C(C=C1)OCOC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 20 | MINUTE | To a solution of 4-[4-(4-hydroxyphenyl)-1-butyl]-7-methoxymethyloxy-3-(4-methoxymethyloxyphenyl)-3-methylchroman (481 mg, 0.976 mmol) in dry tetrahydrofuran (8 ml) was added sodium hydride (22.7 mg, 1.418 mmol) at room temperature and stirred for 20 minutes. Bromoacetic acid tert-butylester (276.7 mg, 1.418 mmol) was a... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester.Aromatic alcohol | Ester.Ether | null | null | c1ccccc1.c1ccc2c(c1)CCCO2.c1ccccc1 | HBr | O1CCCC1 | null | 0.333333 | CC(C)(C)OC(=O)CBr.COCOc1ccc(C2(C)COc3cc(OCOC)ccc3C2CCCCc2ccc(O)cc2)cc1>O1CCCC1>COCOc1ccc(C2(C)COc3cc(OCOC)ccc3C2CCCCc2ccc(OCC(=O)OC(C)(C)C)cc2)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-d3ba945d069046049c5a08a5de0469e4 | COCOc1ccc(C2(C)COc3cc(OCOC)ccc3C2CCCCc2ccc(OCC(=O)OC(C)(C)C)cc2)cc1>>COCOc1ccc(C2(C)COc3cc(OCOC)ccc3C2CCCCc2ccc(OCCO)cc2)cc1 | C(C)(=O)OCC.[OH-].[Na+].C(C)(C)(C)OC(=O)COC1=CC=C(C=C1)CCCCC1C(COC2=CC(=CC=C12)OCOC)(C)C1=CC=C(C=C1)OCOC.[H-].[Al+3].[Li+].[H-].[H-].[H-]>>OCCOC1=CC=C(C=C1)CCCCC1C(COC2=CC(=CC=C12)OCOC)(C)C1=CC=C(C=C1)OCOC | CC(C)(C)O[C:34]([CH2:33][O:32][c:31]1[cH:30][cH:29][c:28]([CH2:27][CH2:26][CH2:25][CH2:24][CH:23]2[C:9]([c:8]3[cH:7][cH:6][c:5]([O:4][CH2:3][O:2][CH3:1])[cH:39][cH:38]3)([CH3:10])[CH2:11][O:12][c:13]3[cH:14][c:15]([O:16][CH2:17][O:18][CH3:19])[cH:20][cH:21][c:22]32)[cH:37][cH:36]1)=[O:35]>>[CH3:1][O:2][CH2:3][O:4][c:5]... | COCOc1ccc(C2(C)COc3cc(OCOC)ccc3C2CCCCc2ccc(OCC(=O)OC(C)(C)C)cc2)cc1 | COCOc1ccc(C2(C)COc3cc(OCOC)ccc3C2CCCCc2ccc(OCCO)cc2)cc1 | null | null | O1CCCC1 | Reduction | Reduction of ester to primary alcohol | 005ed55ca3498ead0a405ca36187c0e85620a6bf11f425e5d3f35c18fb5c1feb | b685880638f3f6d2edbccd81c5d4aa218aa09f2b7a06a7fe669dee5c38c3c0e3 | c1ccc(CCCCC2c3ccccc3OCC2c2ccccc2)cc1 | C-C(-C)(-C)-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[C:3]-[#8:4]>>[#8:4]-[C:3]-[CH2;D2;+0:1]-[OH;D1;+0:2] | 100 | [{"value": 100.0, "product": "OCCOC1=CC=C(C=C1)CCCCC1C(COC2=CC(=CC=C12)OCOC)(C)C1=CC=C(C=C1)OCOC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 4 | HOUR | To a solution of 4-{4-[4-(t-butoxycarbonylmethyloxy)phenyl]-1-butyl}-7-methoxymethyloxy-3-(4-methoxymethyloxyphenyl)-3-methylchroman (744 mg, 1.226 mmol) in dry tetrahydrofuran (10 mi) was added lithium aluminum hydride (71.8 mg, 1.89 mmol) at 0° C. and stirred for 4 h at the room temperature. When the reaction was com... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Boc | Primary alcohol | null | null | c1ccccc1.c1ccc2c(c1)CCCO2.c1ccccc1 | HO- | O1CCCC1 | null | 4 | COCOc1ccc(C2(C)COc3cc(OCOC)ccc3C2CCCCc2ccc(OCC(=O)OC(C)(C)C)cc2)cc1>O1CCCC1>COCOc1ccc(C2(C)COc3cc(OCOC)ccc3C2CCCCc2ccc(OCCO)cc2)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-f5535ef36f8a41b7b00ca4f5d150d61a | CC(C)(C)[Si](C)(C)OCCCCCCCCCI.COc1ccc2c(c1)OCC(C)(c1cccnc1)C2=O>>COc1ccc2c(c1)OCC(C)(c1cccnc1)C2(O)CCCCCCCCCO[Si](C)(C)C(C)(C)C | [NH4+].[Cl-].COC1=CC=C2C(C(COC2=C1)(C=1C=NC=CC1)C)=O.[Si](C)(C)(C(C)(C)C)OCCCCCCCCCI.[Li]C(C)(C)C>>[Si](C)(C)(C(C)(C)C)OCCCCCCCCCC1(C(COC2=CC(=CC=C12)OC)(C=1C=NC=CC1)C)O | I[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][O:30][Si:31]([CH3:32])([CH3:33])[C:34]([CH3:35])([CH3:36])[CH3:37].[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([cH:8]1)[O:9][CH2:10][C:11]([CH3:12])([c:13]1[cH:14][cH:15][cH:16][n:17][cH:18]1)[C:19]2=[O:20]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[c:7... | CC(C)(C)[Si](C)(C)OCCCCCCCCCI.COc1ccc2c(c1)OCC(C)(c1cccnc1)C2=O | COc1ccc2c(c1)OCC(C)(c1cccnc1)C2(O)CCCCCCCCCO[Si](C)(C)C(C)(C)C | null | null | CCCCC.C(C)OCC.C1CCOC1 | C-C Coupling | Grignard_alcohol | 3564a312877016c9d06e74226a688b803cc3abe5b2bca6c50de489b2e8dea1a8 | afe96a58b8c6ca4e103c0c96e2a417cdee8e581054f8e646150ad555cb751905 | c1cncc(C2COc3ccccc3C2)c1 | I-[CH2;D2;+0:1]-[C:2]-[C:3].[#7;a:4]:[c:5]:[c:6]-[C:7]1(-[C;D1;H3:8])-[C:9]-[#8:10]-[c:11]:[c:12](:[c:13])-[C;H0;D3;+0:14]-1=[O;H0;D1;+0:15]>>[#7;a:4]:[c:5]:[c:6]-[C:7]1(-[C;D1;H3:8])-[C:9]-[#8:10]-[c:11]:[c:12](:[c:13])-[C;H0;D4;+0:14]-1(-[OH;D1;+0:15])-[CH2;D2;+0:1]-[C:2]-[C:3] | 75.1 | [{"value": 75.0, "product": "[Si](C)(C)(C(C)(C)C)OCCCCCCCCCC1(C(COC2=CC(=CC=C12)OC)(C=1C=NC=CC1)C)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 75.1, "product": "[Si](C)(C)(C(C)(C)C)OCCCCCCCCCC1(C(COC2=CC(=CC=C12)OC)(C=1C=NC=CC1)C)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -78 | CELSIUS | 10 | MINUTE | To a solution of 9-(t-butyldimethylsilyloxy)nonyl iodide (1.05 g, 2.7 mmol) in pentane (10 ml) and diethylether (7 ml) was added at −78° C. t-BuLi (1.64M in pentane, 3.62 ml, 5.94 mmol), which was stirred for 10 minutes and then stirred for 1 h at room temperature. The mixture was cooled to −78° C. again, and a solutio... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ketone | Tertiary alcohol | c1ccc2c(c1)CCCO2 | c1ccc2c(c1)CCCO2 | c1ccc2c(c1)CCCO2.c1ccncc1 | I- | CCCCC.C(C)OCC.C1CCOC1 | -78 | 0.166667 | CC(C)(C)[Si](C)(C)OCCCCCCCCCI.COc1ccc2c(c1)OCC(C)(c1cccnc1)C2=O>CCCCC.C(C)OCC.C1CCOC1>COc1ccc2c(c1)OCC(C)(c1cccnc1)C2(O)CCCCCCCCCO[Si](C)(C)C(C)(C)C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-b681396a40da49328be1769d375a8d89 | COCOc1ccc(C2COc3cc(OCOC)ccc3C2CCCCCCCCCO)cc1.CS(=O)(=O)Cl>>COCOc1ccc(C2COc3cc(OCOC)ccc3C2CCCCCCCCCOS(C)(=O)=O)cc1 | O.OCCCCCCCCCC1C(COC2=CC(=CC=C12)OCOC)C1=CC=C(C=C1)OCOC.C(C)N(CC)CC.CS(=O)(=O)Cl>>CS(=O)(=O)OCCCCCCCCCC1C(COC2=CC(=CC=C12)OCOC)C1=CC=C(C=C1)OCOC | [CH3:1][O:2][CH2:3][O:4][c:5]1[cH:6][cH:7][c:8]([CH:9]2[CH2:10][O:11][c:12]3[cH:13][c:14]([O:15][CH2:16][O:17][CH3:18])[cH:19][cH:20][c:21]3[CH:22]2[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][OH:32])[cH:37][cH:38]1.Cl[S:33]([CH3:34])(=[O:35])=[O:36]>>[CH3:1][O:2][CH2:3][O:4][c:5]1[cH:6][cH:... | COCOc1ccc(C2COc3cc(OCOC)ccc3C2CCCCCCCCCO)cc1.CS(=O)(=O)Cl | COCOc1ccc(C2COc3cc(OCOC)ccc3C2CCCCCCCCCOS(C)(=O)=O)cc1 | null | null | C(Cl)Cl | Acylation | Formation of Sulfonic Esters | 2fa969eb2c954bb96793348a1b2335ec63fbd290dadec6e3e02295e1768e64cf | cb77b899e4adf980b1def97230ef2861660fd7f9602260ec64747d9afd3a795a | c1ccc(C2COc3ccccc3C2)cc1 | Cl-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4].[C:5]-[C:6]-[OH;D1;+0:7]>>[C:5]-[C:6]-[O;H0;D2;+0:7]-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4] | 99 | [{"value": 99.0, "product": "CS(=O)(=O)OCCCCCCCCCC1C(COC2=CC(=CC=C12)OCOC)C1=CC=C(C=C1)OCOC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 98.5, "product": "CS(=O)(=O)OCCCCCCCCCC1C(COC2=CC(=CC=C12)OCOC)C1=CC=C(C=C1)OCOC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 45 | MINUTE | To a solution of (3RS,4RS)-4-(9-hydroxynonyl)-7-methoxymethoxy-3-(4-methoxymethoxyphenyl)chroman (222 mg, 0.470 mmol) and triethylamine (0.135 ml, 0.961 mmol) in CH2Cl2 (5 ml) at 0° C. under nitrogen was added methanesulfonyl chloride (0.055 ml, 0.71 mmol). The resulting solution was stirred at 0° C. for 45 min, and th... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Sulfonyl halide | Mesylate | null | null | c1ccccc1.c1ccc2c(c1)CCCO2 | HCl | C(Cl)Cl | 0 | 0.75 | COCOc1ccc(C2COc3cc(OCOC)ccc3C2CCCCCCCCCO)cc1.CS(=O)(=O)Cl>C(Cl)Cl>COCOc1ccc(C2COc3cc(OCOC)ccc3C2CCCCCCCCCOS(C)(=O)=O)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-e8908afb197149f1a016045aa0013908 | COCOc1ccc(C2COc3cc(OCOC)ccc3C2CCCCCCCCCSCCCC(F)(F)C(F)(F)F)cc1>>Oc1ccc(C2COc3cc(O)ccc3C2CCCCCCCCCSCCCC(F)(F)C(F)(F)F)cc1 | O.COCOC1=CC=C2C(C(COC2=C1)C1=CC=C(C=C1)OCOC)CCCCCCCCCSCCCC(C(F)(F)F)(F)F.Cl>>OC1=CC=C2C(C(COC2=C1)C1=CC=C(C=C1)O)CCCCCCCCCSCCCC(C(F)(F)F)(F)F | COC[O:1][c:2]1[cH:3][cH:4][c:5]([CH:6]2[CH2:7][O:8][c:9]3[cH:10][c:11]([O:12]COC)[cH:13][cH:14][c:15]3[CH:16]2[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][S:26][CH2:27][CH2:28][CH2:29][C:30]([F:31])([F:32])[C:33]([F:34])([F:35])[F:36])[cH:37][cH:38]1>>[OH:1][c:2]1[cH:3][cH:4][c:5]([CH:6]2[CH... | COCOc1ccc(C2COc3cc(OCOC)ccc3C2CCCCCCCCCSCCCC(F)(F)C(F)(F)F)cc1 | Oc1ccc(C2COc3cc(O)ccc3C2CCCCCCCCCSCCCC(F)(F)C(F)(F)F)cc1 | null | null | CCO | Reduction | OtherReaction | ca434a15af04bd105d14de328e5decdefa40fa872c8bf2d8a06e38dd9d786610 | 9290d799ef03b273f5a33508bad8fca1206e009b9df18f946351c38e7647a04c | c1ccc(C2COc3ccccc3C2)cc1 | C-O-C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4].C-O-C-[O;H0;D2;+0:5]-[c:6](:[c:7]):[c:8]>>[OH;D1;+0:1]-[c:2](:[c:3]):[c:4].[OH;D1;+0:5]-[c:6](:[c:7]):[c:8] | 80 | [{"value": 80.0, "product": "OC1=CC=C2C(C(COC2=C1)C1=CC=C(C=C1)O)CCCCCCCCCSCCCC(C(F)(F)F)(F)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 79.5, "product": "OC1=CC=C2C(C(COC2=C1)C1=CC=C(C=C1)O)CCCCCCCCCSCCCC(C(F)(F)F)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 17 | HOUR | To a solution of (3RS,4RS)-7-methoxymethoxy-3-(4-methoxymethoxyphenyl)-4-[9-(4,4,5,5,5-pentafluoropentylthio)nonyl]chroman (204 mg, 0.314 mmol) in EtOH (2 ml) was added 6N HCl (0.2 ml, 1.2 mmol). The resulting solution was stirred between 40 and 45° C. for 17 hr, and then poured into H2O. The mixture was extracted with... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether.Ether.Ether | Aromatic alcohol.Aromatic alcohol | null | null | c1ccccc1.c1ccc2c(c1)CCCO2 | HO- | CCO | null | 17 | COCOc1ccc(C2COc3cc(OCOC)ccc3C2CCCCCCCCCSCCCC(F)(F)C(F)(F)F)cc1>CCO>Oc1ccc(C2COc3cc(O)ccc3C2CCCCCCCCCSCCCC(F)(F)C(F)(F)F)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-f9fd6cf2533f4847b46d5d3daee6cddd | Oc1ccc(C2COc3cc(O)ccc3C2CCCCCCCCCSCCCC(F)(F)C(F)(F)F)cc1>>O=S(CCCCCCCCCC1c2ccc(O)cc2OCC1c1ccc(O)cc1)CCCC(F)(F)C(F)(F)F | OC1=CC=C2C(C(COC2=C1)C1=CC=C(C=C1)O)CCCCCCCCCSCCCC(C(F)(F)F)(F)F.O.OOS(=O)[O-].[K+].O>>OC1=CC=C2C(C(COC2=C1)C1=CC=C(C=C1)O)CCCCCCCCCS(=O)CCCC(C(F)(F)F)(F)F | [S:2]([CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH:12]1[c:13]2[cH:14][cH:15][c:16]([OH:17])[cH:18][c:19]2[O:20][CH2:21][CH:22]1[c:23]1[cH:24][cH:25][c:26]([OH:27])[cH:28][cH:29]1)[CH2:30][CH2:31][CH2:32][C:33]([F:34])([F:35])[C:36]([F:37])([F:38])[F:39]>>[O:1]=[S:2]([CH2:3][CH2:4][CH2:5][CH2:6][... | Oc1ccc(C2COc3cc(O)ccc3C2CCCCCCCCCSCCCC(F)(F)C(F)(F)F)cc1 | O=S(CCCCCCCCCC1c2ccc(O)cc2OCC1c1ccc(O)cc1)CCCC(F)(F)C(F)(F)F | null | null | C1CCOC1 | Oxidation | Sulfanyl to sulfinyl | 9edfaf6d72a81452ea8e3a1cdcb10a58409fff36608e97019e7273998b3d5373 | f5f6bb6ca76a2267cd589767b4d67e7a17ab1ac383eeb6143dcd5d92e00e1b6a | c1ccc(C2COc3ccccc3C2)cc1 | [C:1]-[C:2]-[S;H0;D2;+0:3]-[C:4]-[C:5]>>[C:1]-[C:2]-[S;H0;D3;+0:3](=[O;D1;H0:6])-[C:4]-[C:5] | 73 | [{"value": 73.0, "product": "OC1=CC=C2C(C(COC2=C1)C1=CC=C(C=C1)O)CCCCCCCCCS(=O)CCCC(C(F)(F)F)(F)F", "details": "PERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 3.5 | HOUR | To a solution of (3RS,4RS)-7-hydroxy-3-(4-hydroxyphenyl)-4-[9-(4,4,5,5,5-pentafluoropentylthio)nonyl]chroman (140 mg, 0.250 mmol) and H2O (0.05 ml) in THF (1.2 ml) at 0° C. was added Oxone® (monopersulfate compound; DuPont product) (77 mg, 0.125 mmol). The resulting solution was stirred at 0° C. for 3.5 hr, and then po... | 10.6084/m9.figshare.5104873.v1 | null | Monosulfide | Sulfoxide | null | null | c1ccc2c(c1)CCCO2.c1ccccc1 | null | C1CCOC1 | 0 | 3.5 | Oc1ccc(C2COc3cc(O)ccc3C2CCCCCCCCCSCCCC(F)(F)C(F)(F)F)cc1>C1CCOC1>O=S(CCCCCCCCCC1c2ccc(O)cc2OCC1c1ccc(O)cc1)CCCC(F)(F)C(F)(F)F |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-3a47379b3ceb4d8bb2427f79f266f219 | C=CCCCCCC(=O)CC(=O)OCC.FC(F)(F)C(F)(F)CCCI>>C=CCCCCCC(=O)C(CCCC(F)(F)C(F)(F)F)C(=O)OCC | O.FC(CCCI)(C(F)(F)F)F.C(C)OC(CC(CCCCCC=C)=O)=O.CC(C)([O-])C.[K+]>>C(C)OC(C(C(CCCCCC=C)=O)CCCC(C(F)(F)F)(F)F)=O | [CH2:1]=[CH:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][C:8](=[O:9])[CH2:10][C:21](=[O:22])[O:23][CH2:24][CH3:25].I[CH2:11][CH2:12][CH2:13][C:14]([F:15])([F:16])[C:17]([F:18])([F:19])[F:20]>>[CH2:1]=[CH:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][C:8](=[O:9])[CH:10]([CH2:11][CH2:12][CH2:13][C:14]([F:15])([F:16])[C:17]([F:18])([F:1... | C=CCCCCCC(=O)CC(=O)OCC.FC(F)(F)C(F)(F)CCCI | C=CCCCCCC(=O)C(CCCC(F)(F)C(F)(F)F)C(=O)OCC | null | null | C1CCOC1 | C-C Coupling | OtherReaction | eb3faf2a43700925ab4f46cf65072b7145e4e060dba25a917e6b7428f38e349e | 61bad66347ae366bfd0a2cd3779dd3d0c29125e97564b97243e11258be3b2a9f | null | I-[CH2;D2;+0:1]-[C:2]-[C:3].[C:4]-[#8:5]-[C:6](=[O;D1;H0:7])-[CH2;D2;+0:8]-[C:9](-[C:10])=[O;D1;H0:11]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[CH;D3;+0:8](-[C:6](=[O;D1;H0:7])-[#8:5]-[C:4])-[C:9](-[C:10])=[O;D1;H0:11] | 59 | [{"value": 59.0, "product": "C(C)OC(C(C(CCCCCC=C)=O)CCCC(C(F)(F)F)(F)F)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | On the other hand, to a solution of 3-oxo-dec-9-enoic acid ethyl ester (4.32 g, 20.3 mmol) in THF (15 ml) at 0° C. was added potassium tert-butoxide (2.73 g, 24.3 mmol) This resulting mixture was stirred at room temperature under nitrogen for 30 min. The mixture of 4,4,5,5,5-pentafluoro-iodopentane was added and mixtur... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ketone | Ketone.Ester | null | null | null | HI | C1CCOC1 | null | 0.5 | C=CCCCCCC(=O)CC(=O)OCC.FC(F)(F)C(F)(F)CCCI>C1CCOC1>C=CCCCCCC(=O)C(CCCC(F)(F)C(F)(F)F)C(=O)OCC |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-f7467f471bd84b2393713aa13d35d7c3 | OCCCC(F)(F)C(F)(F)F>>O=C(O)CCC(F)(F)C(F)(F)F | CC(=O)C.OS(=O)(=O)O.O=[Cr](=O)=O.FC(CCCO)(C(F)(F)F)F>>FC(CCC(=O)O)(C(F)(F)F)F | [CH2:2]([OH:3])[CH2:4][CH2:5][C:6]([F:7])([F:8])[C:9]([F:10])([F:11])[F:12]>>[O:1]=[C:2]([OH:3])[CH2:4][CH2:5][C:6]([F:7])([F:8])[C:9]([F:10])([F:11])[F:12] | OCCCC(F)(F)C(F)(F)F | O=C(O)CCC(F)(F)C(F)(F)F | null | null | CC(=O)C | Oxidation | Oxidation of alcohol to carboxylic acid | b709baac44a995a9a8f6386a6b5d87f98c32eb5a0636340abc1f778fae827230 | 4454822e22dc2dc24e7495385256bfce456e337c240bb764261f81dbeda1aaa1 | null | [C:1]-[C:2]-[CH2;D2;+0:3]-[O;D1;H1:4]>>[C:1]-[C:2]-[C;H0;D3;+0:3](=[O;D1;H0:5])-[O;D1;H1:4] | 82.1 | [{"value": 82.0, "product": "FC(CCC(=O)O)(C(F)(F)F)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 82.1, "product": "FC(CCC(=O)O)(C(F)(F)F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | To a stirred solution of Jones reagent (20 ml, 160 mmol) in acetone (20 ml), cooled in an ice bath, a solution of 4,4,5,5,5-pentafluoro-1-pentanol (7.12 g, 40 mmol) in acetone (30 ml) was added dropwise. After remaining ice bath, the mixture was stirred continuously at room temperature for 1 h. The mixture was poured i... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | Carboxylic acid | null | null | null | Other | CC(=O)C | null | 1 | OCCCC(F)(F)C(F)(F)F>CC(=O)C>O=C(O)CCC(F)(F)C(F)(F)F |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-c9a8b8dff5a04d489160160a139b1a41 | CCOC(C)=O.O=C(Cl)CCC(F)(F)C(F)(F)F>>CCOC(=O)CC(=O)CCC(F)(F)C(F)(F)F | FC(CCC(=O)Cl)(C(F)(F)F)F.C(C)(=O)OCC.C[Si]([N-][Si](C)(C)C)(C)C.[Na+]>>FC(CCC(CC(=O)OCC)=O)(C(F)(F)F)F | [CH3:1][CH2:2][O:3][C:4](=[O:5])[CH3:6].Cl[C:7](=[O:8])[CH2:9][CH2:10][C:11]([F:12])([F:13])[C:14]([F:15])([F:16])[F:17]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][C:7](=[O:8])[CH2:9][CH2:10][C:11]([F:12])([F:13])[C:14]([F:15])([F:16])[F:17] | CCOC(C)=O.O=C(Cl)CCC(F)(F)C(F)(F)F | CCOC(=O)CC(=O)CCC(F)(F)C(F)(F)F | null | null | C1CCOC1 | C-C Coupling | OtherReaction | 9c255438d8e6adeba9ee52582b8e97af5f85bef382cd416953270ac55bd10486 | 4c7bc8856483317e0c04a17d8cd6aba13cdf5ed9f64b61fe01f230a819039f82 | null | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[C:5]-[#8:6]-[C:7](-[CH3;D1;+0:8])=[O;D1;H0:9]>>[C:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[CH2;D2;+0:8]-[C:7](=[O;D1;H0:9])-[#8:6]-[C:5] | 56 | [{"value": 56.0, "product": "FC(CCC(CC(=O)OCC)=O)(C(F)(F)F)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 55.7, "product": "FC(CCC(CC(=O)OCC)=O)(C(F)(F)F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a stirred solution of ethyl acetate enolate, prepared from ethyl acetate (4.4 g, 50 mmol) and sodium hexamethyldisilazide (50 mmol) in THF at −70° C., was added neat 4,4,5,5,5-pentafluoropentanoyl chloride (2.1 g, 10 mmol) at −70° C. Cooling bath was removed and the reaction mixture was allowed to warm to room tempe... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Ester | Ketone | null | null | null | HCl | C1CCOC1 | null | null | CCOC(C)=O.O=C(Cl)CCC(F)(F)C(F)(F)F>C1CCOC1>CCOC(=O)CC(=O)CCC(F)(F)C(F)(F)F |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-8f05e99b3c1f4ee294971c754d2bc47e | C=CCCCCCCBr.[I-]>>C=CCCCCCCI | BrCCCCCCC=C.[I-].[Na+]>>ICCCCCCC=C | Br[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=[CH2:1].[I-:9]>>[CH2:1]=[CH:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][I:9] | C=CCCCCCCBr.[I-] | C=CCCCCCCI | null | null | CC(CC)=O | Functional Group Interconversion | OtherReaction | e944a2acb95a43a23818321f2ac2f96ba2f2b8d34f52c1cfd1e3802d2403177f | e2ca6f9fe1078a3836d617896a4e5cc310fb155ca459b021e2b549b3e61f1df7 | null | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[I-;H0;D0:4]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[I;H0;D1;+0:4] | null | [] | null | null | null | null | A mixture of 8-bromo-1-octene (1.34 g, 7 mmol) and sodium iodide (5.25 g, 35 mmol) in 2-butanone (15 ml) was stirred under reflux for 1 h. The mixture was concentrated in vacuo to a half of its original volume and hexane and water was added. Organic layer was washed with 5% aqueous sodium thiosulfate, saturated sodium ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | Primary halide | null | null | null | Br- | CC(CC)=O | null | null | C=CCCCCCCBr.[I-]>CC(CC)=O>C=CCCCCCCI |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-126b46c583eb4d38b98c533b7ad86f3c | C=CCCCCCCI.CCOC(=O)CC(=O)CCC(F)(F)C(F)(F)F>>C=CCCCCCCC(C(=O)CCC(F)(F)C(F)(F)F)C(=O)OCC | FC(CCC(CC(=O)OCC)=O)(C(F)(F)F)F.[O-]CCCC.ICCCCCCC=C>>FC(CCC(=O)C(C(=O)OCC)CCCCCCC=C)(C(F)(F)F)F | I[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=[CH2:1].[CH2:9]([C:10](=[O:11])[CH2:12][CH2:13][C:14]([F:15])([F:16])[C:17]([F:18])([F:19])[F:20])[C:21](=[O:22])[O:23][CH2:24][CH3:25]>>[CH2:1]=[CH:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH:9]([C:10](=[O:11])[CH2:12][CH2:13][C:14]([F:15])([F:16])[C:17]([F:18])([F... | C=CCCCCCCI.CCOC(=O)CC(=O)CCC(F)(F)C(F)(F)F | C=CCCCCCCC(C(=O)CCC(F)(F)C(F)(F)F)C(=O)OCC | null | null | [K].C1CCOC1 | C-C Coupling | OtherReaction | eb3faf2a43700925ab4f46cf65072b7145e4e060dba25a917e6b7428f38e349e | 61bad66347ae366bfd0a2cd3779dd3d0c29125e97564b97243e11258be3b2a9f | null | I-[CH2;D2;+0:1]-[C:2]-[C:3].[C:4]-[C:5](=[O;D1;H0:6])-[CH2;D2;+0:7]-[C:8](=[O;D1;H0:9])-[#8:10]-[C:11]>>[C:4]-[C:5](=[O;D1;H0:6])-[CH;D3;+0:7](-[CH2;D2;+0:1]-[C:2]-[C:3])-[C:8](=[O;D1;H0:9])-[#8:10]-[C:11] | null | [] | null | null | 30 | MINUTE | To a stirred solution of ethyl 6,6,7,7,7-pentafluoro-3-oxoheptanoate (262 mg, 1 mmol) in anhydrous THF (4 ml), potassium tret-butoxide (112 mg, 1 mmol) was added as a solid and the mixture was stirred at room temperature for 30 min. Then to a solution of 8-iodo-1-octene (357 mg, 1.5 mmol) in anhydrous THF (1 ml) was ad... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ketone | Ketone.Ester | null | null | null | HI | [K].C1CCOC1 | null | 0.5 | C=CCCCCCCI.CCOC(=O)CC(=O)CCC(F)(F)C(F)(F)F>[K].C1CCOC1>C=CCCCCCCC(C(=O)CCC(F)(F)C(F)(F)F)C(=O)OCC |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-bba4881519bd4898a0f1cb168e48df4a | CCOC(=O)C(CCCCCCCCCC1c2ccc(OCOC)cc2OCC1(C)c1ccc(OCOC)cc1)C(=O)CCC(F)(F)C(F)(F)F>>CCOC(=O)C(CCCCCCCCCC1c2ccc(O)cc2OCC1(C)c1ccc(O)cc1)C(=O)CCC(F)(F)C(F)(F)F | FC(CCC(=O)C(C(=O)OCC)CCCCCCCCCC1C(COC2=CC(=CC=C12)OCOC)(C)C1=CC=C(C=C1)OCOC)(C(F)(F)F)F>>FC(CCC(=O)C(C(=O)OCC)CCCCCCCCCC1C(COC2=CC(=CC=C12)O)(C)C1=CC=C(C=C1)O)(C(F)(F)F)F | COC[O:21][c:20]1[cH:19][cH:18][c:17]2[c:23]([cH:22]1)[O:24][CH2:25][C:26]([CH3:27])([c:28]1[cH:29][cH:30][c:31]([O:32]COC)[cH:33][cH:34]1)[CH:16]2[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[C:35](=[O:36])[CH2:37][CH2:38][C:39]([F:40])([F:41])[C:42]([F:43... | CCOC(=O)C(CCCCCCCCCC1c2ccc(OCOC)cc2OCC1(C)c1ccc(OCOC)cc1)C(=O)CCC(F)(F)C(F)(F)F | CCOC(=O)C(CCCCCCCCCC1c2ccc(O)cc2OCC1(C)c1ccc(O)cc1)C(=O)CCC(F)(F)C(F)(F)F | null | Cl | C(C)(=O)OCC.C(C)O | Reduction | OtherReaction | ca434a15af04bd105d14de328e5decdefa40fa872c8bf2d8a06e38dd9d786610 | 9290d799ef03b273f5a33508bad8fca1206e009b9df18f946351c38e7647a04c | c1ccc(C2COc3ccccc3C2)cc1 | C-O-C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4].C-O-C-[O;H0;D2;+0:5]-[c:6](:[c:7]):[c:8]>>[OH;D1;+0:1]-[c:2](:[c:3]):[c:4].[OH;D1;+0:5]-[c:6](:[c:7]):[c:8] | null | [] | null | null | 2.5 | DAY | To a stirred solution of ethyl 2-(4,4,5,5,5-pentafluoro-1-oxopentyl)-11-[(3RS,4RS)-7-methoxymethoxy-3-(4-methoxymethoxyphenyl)-3-methylchroman-4-yl]undecanoate (128 mg, 0.17 mmol) in ethyl alcohol (5 ml), was added concentrated aqueous hydrochloric acid (10 drops) at room temperature under N2 atmosphere. The mixture wa... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether.Ether.Ether | Aromatic alcohol.Aromatic alcohol | null | null | c1ccc2c(c1)CCCO2.c1ccccc1 | HO- | Cl.C(C)(=O)OCC.C(C)O | null | 60 | CCOC(=O)C(CCCCCCCCCC1c2ccc(OCOC)cc2OCC1(C)c1ccc(OCOC)cc1)C(=O)CCC(F)(F)C(F)(F)F>Cl.C(C)(=O)OCC.C(C)O>CCOC(=O)C(CCCCCCCCCC1c2ccc(O)cc2OCC1(C)c1ccc(O)cc1)C(=O)CCC(F)(F)C(F)(F)F |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-5622d29f00734a1982d17b4dcd5b87fc | CCOC(=O)/C(=C/CCC(F)(F)C(F)(F)F)CCCCCCCCCC1c2ccc(OCOC)cc2OCC1(C)c1ccc(OCOC)cc1>>COCOc1ccc(C2(C)COc3cc(OCOC)ccc3C2CCCCCCCCC/C(=C\CCC(F)(F)C(F)(F)F)C(=O)O)cc1 | FC(CC/C=C(/C(=O)OCC)\CCCCCCCCCC1C(COC2=CC(=CC=C12)OCOC)(C)C1=CC=C(C=C1)OCOC)(C(F)(F)F)F.Cl>>FC(CC/C=C(/C(=O)O)\CCCCCCCCCC1C(COC2=CC(=CC=C12)OCOC)(C)C1=CC=C(C=C1)OCOC)(C(F)(F)F)F | CC[O:46][C:44](/[C:33]([CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH:23]1[C:9]([c:8]2[cH:7][cH:6][c:5]([O:4][CH2:3][O:2][CH3:1])[cH:48][cH:47]2)([CH3:10])[CH2:11][O:12][c:13]2[cH:14][c:15]([O:16][CH2:17][O:18][CH3:19])[cH:20][cH:21][c:22]21)=[CH:34]/[CH2:35][CH2:36][C:37]([F:38])([F:39])[C... | CCOC(=O)/C(=C/CCC(F)(F)C(F)(F)F)CCCCCCCCCC1c2ccc(OCOC)cc2OCC1(C)c1ccc(OCOC)cc1 | COCOc1ccc(C2(C)COc3cc(OCOC)ccc3C2CCCCCCCCC/C(=C\CCC(F)(F)C(F)(F)F)C(=O)O)cc1 | null | null | [OH-].[K+].C(C)O | Deprotection | Ester saponification (alkyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccc(C2COc3ccccc3C2)cc1 | C-C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])/[C:4](-[C:5])=[C:6]/[C:7]>>[C:5]/[C:4](=[C:6]\[C:7])-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1] | null | [] | 70 | CELSIUS | 5 | HOUR | To a stirred solution of ethyl (E)-6,6,7,7,7-pentafluoro-2-{9-[(3RS,4RS)-7-methoxymethoxy-3-(4-methoxymethoxyphenyl)-3-methylchroman-4-yl]nonyl}-2-h eptenoate (116 mg, 0.16 mmol) in ethyl alcohol (5 ml), 5 N aqueous potassium hydroxide solution was added and the mixture was stirred under N2 atmosphere at 70° C. for 5 h... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1.c1ccc2c(c1)CCCO2 | Other | [OH-].[K+].C(C)O | 70 | 5 | CCOC(=O)/C(=C/CCC(F)(F)C(F)(F)F)CCCCCCCCCC1c2ccc(OCOC)cc2OCC1(C)c1ccc(OCOC)cc1>[OH-].[K+].C(C)O>COCOc1ccc(C2(C)COc3cc(OCOC)ccc3C2CCCCCCCCC/C(=C\CCC(F)(F)C(F)(F)F)C(=O)O)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-64820e20b2e1429798acad9ad3103b90 | COCOc1ccc(C2(C)COc3cc(OCOC)ccc3C2CCCCCCCCC/C(=C\CCC(F)(F)C(F)(F)F)C(=O)O)cc1>>CC1(c2ccc(O)cc2)COc2cc(O)ccc2C1CCCCCCCCC/C(=C\CCC(F)(F)C(F)(F)F)C(=O)O | FC(CC/C=C(/C(=O)O)\CCCCCCCCCC1C(COC2=CC(=CC=C12)OCOC)(C)C1=CC=C(C=C1)OCOC)(C(F)(F)F)F>>FC(CC/C=C(/C(=O)O)\CCCCCCCCCC1C(COC2=CC(=CC=C12)O)(C)C1=CC=C(C=C1)O)(C(F)(F)F)F | COC[O:7][c:6]1[cH:5][cH:4][c:3]([C:2]2([CH3:1])[CH2:10][O:11][c:12]3[cH:13][c:14]([O:15]COC)[cH:16][cH:17][c:18]3[CH:19]2[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28]/[C:29](=[CH:30]\[CH2:31][CH2:32][C:33]([F:34])([F:35])[C:36]([F:37])([F:38])[F:39])[C:40](=[O:41])[OH:42])[cH:9][cH:8]1>>[CH3:... | COCOc1ccc(C2(C)COc3cc(OCOC)ccc3C2CCCCCCCCC/C(=C\CCC(F)(F)C(F)(F)F)C(=O)O)cc1 | CC1(c2ccc(O)cc2)COc2cc(O)ccc2C1CCCCCCCCC/C(=C\CCC(F)(F)C(F)(F)F)C(=O)O | null | Cl | O.C(C)O | Reduction | OtherReaction | ca434a15af04bd105d14de328e5decdefa40fa872c8bf2d8a06e38dd9d786610 | 9290d799ef03b273f5a33508bad8fca1206e009b9df18f946351c38e7647a04c | c1ccc(C2COc3ccccc3C2)cc1 | C-O-C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4].C-O-C-[O;H0;D2;+0:5]-[c:6](:[c:7]):[c:8]>>[OH;D1;+0:1]-[c:2](:[c:3]):[c:4].[OH;D1;+0:5]-[c:6](:[c:7]):[c:8] | null | [] | 40 | CELSIUS | 6 | HOUR | To a stirred solution of (E)-6,6,7,7,7-pentafluoro-2-{9-[(3RS,4RS)-7-methoxymethoxy-3-(4-methoxymethoxyphenyl)-3-methylchroman-4-yl]nonyl}-2-heptenoic acid (111 mg, 0.16 mmol) in ethyl alcohol (5 ml), was added 6 N aqueous solution of hydrochloric acid (30 drops) and the reaction mixture was stirred at 40° C. for 6 h. ... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether.Ether.Ether | Aromatic alcohol.Aromatic alcohol | null | null | c1ccccc1.c1ccc2c(c1)CCCO2 | HO- | Cl.O.C(C)O | 40 | 6 | COCOc1ccc(C2(C)COc3cc(OCOC)ccc3C2CCCCCCCCC/C(=C\CCC(F)(F)C(F)(F)F)C(=O)O)cc1>Cl.O.C(C)O>CC1(c2ccc(O)cc2)COc2cc(O)ccc2C1CCCCCCCCC/C(=C\CCC(F)(F)C(F)(F)F)C(=O)O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-8a2c55af2e3b4a24ae2a63540a9262c5 | COCOc1ccc(C2(C)COc3cc(OCOC)ccc3C2CCCCCCCCCN)cc1.O=S(=O)(Cl)CCCC(F)(F)C(F)(F)F>>COCOc1ccc(C2(C)COc3cc(OCOC)ccc3C2CCCCCCCCCNCCCC(F)(F)C(F)(F)F)cc1 | NCCCCCCCCCC1C(COC2=CC(=CC=C12)OCOC)(C)C1=CC=C(C=C1)OCOC.FC(CCCS(=O)(=O)Cl)(C(F)(F)F)F.C(C)N(CC)CC>>COCOC1=CC=C2C(C(COC2=C1)(C)C1=CC=C(C=C1)OCOC)CCCCCCCCCNCCCC(C(F)(F)F)(F)F | [CH3:1][O:2][CH2:3][O:4][c:5]1[cH:6][cH:7][c:8]([C:9]2([CH3:10])[CH2:11][O:12][c:13]3[cH:14][c:15]([O:16][CH2:17][O:18][CH3:19])[cH:20][cH:21][c:22]3[CH:23]2[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][NH2:33])[cH:44][cH:45]1.O=S(=O)(Cl)[CH2:34][CH2:35][CH2:36][C:37]([F:38])([F:39])[C:40]([F... | COCOc1ccc(C2(C)COc3cc(OCOC)ccc3C2CCCCCCCCCN)cc1.O=S(=O)(Cl)CCCC(F)(F)C(F)(F)F | COCOc1ccc(C2(C)COc3cc(OCOC)ccc3C2CCCCCCCCCNCCCC(F)(F)C(F)(F)F)cc1 | null | null | C(Cl)Cl | Heteroatom Alkylation and Arylation | OtherReaction | 158f49fe57c7ac38d88fe4b2207dc19199f94508ccd68dac6442c76c103458a3 | 298452d0d798e9f10a3b6cebf52647f808001249292b5fe8eb23812442d1d9b8 | c1ccc(C2COc3ccccc3C2)cc1 | Cl-S(=O)(=O)-[CH2;D2;+0:1]-[C:2]-[C:3].[C:4]-[C:5]-[NH2;D1;+0:6]>>[C:4]-[C:5]-[NH;D2;+0:6]-[CH2;D2;+0:1]-[C:2]-[C:3] | 73.8 | [{"value": 67.0, "product": "COCOC1=CC=C2C(C(COC2=C1)(C)C1=CC=C(C=C1)OCOC)CCCCCCCCCNCCCC(C(F)(F)F)(F)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 73.8, "product": "COCOC1=CC=C2C(C(COC2=C1)(C)C1=CC=C(C=C1)OCOC)CCCCCCCCCNCCCC(C(F)(F)F)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 30 | MINUTE | 4-(9-aminononyl)-7-methoxymethoxy-3-(4-methoxymethoxyphenyl)-3-methylchroman (82.3 mg, 0.17 mmol) was dissolved in 5 ml of methylenechloride under argon atmosphere, which was then cooled down to 0° C. 4,4,5,5,5-pentafluoropentylsulfonyl chloride (110.4 mg, 0.42 mmol) in 1 ml of methylene chloride and triethylamine (0.0... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Sulfonyl halide | Secondary amine | null | null | c1ccccc1.c1ccc2c(c1)CCCO2 | HCl | C(Cl)Cl | 0 | 0.5 | COCOc1ccc(C2(C)COc3cc(OCOC)ccc3C2CCCCCCCCCN)cc1.O=S(=O)(Cl)CCCC(F)(F)C(F)(F)F>C(Cl)Cl>COCOc1ccc(C2(C)COc3cc(OCOC)ccc3C2CCCCCCCCCNCCCC(F)(F)C(F)(F)F)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-8f46b3be43a246868cb922f99a121180 | O=Cc1ccc(Br)cc1.OCCO>>Brc1ccccc1C1COCO1 | BrC1=CC=C(C=O)C=C1.C1(=CC=CC=C1)C.C(CO)O>>BrC1=C(C=CC=C1)C1OCOC1 | [Br:1][c:2]1[cH:3][cH:4][c:7]([CH:8]=[O:12])[cH:6][cH:5]1.O[CH2:11][CH2:9][OH:10]>>[Br:1][c:2]1[cH:3][cH:4][cH:5][cH:6][c:7]1[CH:8]1[CH2:9][O:10][CH2:11][O:12]1 | O=Cc1ccc(Br)cc1.OCCO | Brc1ccccc1C1COCO1 | null | C1(=CC=C(C=C1)S(=O)(=O)O)C | null | Aromatic Heterocycle Formation | OtherReaction | 76f52cb283311be0b4b9fa2854a03dd35110b89638a33866f31c5a381154af4e | 06198f7e3e166c4884409e793066a85ca1d4434fe1fe7b176f53070242819939 | c1ccc(C2COCO2)cc1 | O-[CH2;D2;+0:1]-[CH2;D2;+0:2]-[OH;D1;+0:3].[Br;D1;H0:4]-[c;H0;D3;+0:5]1:[c:6]:[cH;D2;+0:7]:[c;H0;D3;+0:8](-[CH;D2;+0:9]=[O;H0;D1;+0:10]):[c:11]:[cH;D2;+0:12]:1>>[Br;D1;H0:4]-[c;H0;D3;+0:5]1:[c:6]:[cH;D2;+0:7]:[cH;D2;+0:12]:[c:11]:[c;H0;D3;+0:8]:1-[CH;D3;+0:9]1-[CH2;D2;+0:2]-[O;H0;D2;+0:3]-[CH2;D2;+0:1]-[O;H0;D2;+0:10]-... | 89 | [{"value": 89.0, "product": "BrC1=C(C=CC=C1)C1OCOC1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | In a round-bottomed flask equipped with a Dean Stark trap and a condenser, was added a solution of p-Bromobenzaldehyde (5 g, 27 mmol) in toluene (25 mL). To this mixture were then added p-toluenesulfonic acid (50 mg, 0.26 mmol) and etylene glycol (1.84 g, 29.7 mmol). The mixture was heated to reflux under nitrogen atmo... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aldehyde.Primary alcohol.Primary alcohol | Aromatic halide.Ether.Ether | c1ccccc1 | c1ccccc1.C1COCO1 | c1ccccc1.C1COCO1 | HO- | C1(=CC=C(C=C1)S(=O)(=O)O)C | null | null | O=Cc1ccc(Br)cc1.OCCO>C1(=CC=C(C=C1)S(=O)(=O)O)C>Brc1ccccc1C1COCO1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-7696eefa70854ec68278c2cac1e07693 | CC(C)(C)[Si](C)(C)Cl.OCc1ccc(Br)cc1>>CC(C)(C)[Si](C)(C)OCc1ccc(Br)cc1 | CO.[Si](C)(C)(C(C)(C)C)Cl.BrC1=CC=C(CO)C=C1.N1C=NC=C1>>BrC1=CC=C(CO[Si](C)(C)C(C)(C)C)C=C1 | Cl[Si:5]([C:2]([CH3:1])([CH3:3])[CH3:4])([CH3:6])[CH3:7].[OH:8][CH2:9][c:10]1[cH:11][cH:12][c:13]([Br:14])[cH:15][cH:16]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[Si:5]([CH3:6])([CH3:7])[O:8][CH2:9][c:10]1[cH:11][cH:12][c:13]([Br:14])[cH:15][cH:16]1 | CC(C)(C)[Si](C)(C)Cl.OCc1ccc(Br)cc1 | CC(C)(C)[Si](C)(C)OCc1ccc(Br)cc1 | null | null | CCCCCC.CN(C)C=O.C(C)(=O)OCC | Protection | Alcohol protection with silyl ethers | 0085cd6629412592263fdf1537bdf8c19ef10dbeafe6f880807464d8107fa715 | d2a170d01b2f3ec57d6fac058519475050ba5531f5d304635fb42e153d5bb9b5 | c1ccccc1 | Cl-[Si;H0;D4;+0:1](-[C;D1;H3:2])(-[C;D1;H3:3])-[C:4](-[C;D1;H3:5])(-[C;D1;H3:6])-[C;D1;H3:7].[OH;D1;+0:8]-[C:9]-[c:10]>>[C;D1;H3:5]-[C:4](-[C;D1;H3:6])(-[C;D1;H3:7])-[Si;H0;D4;+0:1](-[C;D1;H3:2])(-[C;D1;H3:3])-[O;H0;D2;+0:8]-[C:9]-[c:10] | 91 | [{"value": 91.0, "product": "BrC1=CC=C(CO[Si](C)(C)C(C)(C)C)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 90.7, "product": "BrC1=CC=C(CO[Si](C)(C)C(C)(C)C)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of p-bromobenzyl alcohol (5.0 g, 26.7 mmol) in DMF (10 mL) was added imidazole (4.54 g, 66.7 mmol) followed by addition of tert-butyldimethylsilyl chloride (6.01 g, 40 mmol). The progress of the reaction was monitored by TLC. When the reaction was complete (about 2 h), methanol was added and diluted by 20... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Silyl protective group | TMS ether protective group | null | null | c1ccccc1 | HCl | CCCCCC.CN(C)C=O.C(C)(=O)OCC | null | null | CC(C)(C)[Si](C)(C)Cl.OCc1ccc(Br)cc1>CCCCCC.CN(C)C=O.C(C)(=O)OCC>CC(C)(C)[Si](C)(C)OCc1ccc(Br)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-b331bea50b8341399b359a762691f74c | BrBr.CN(CCO)c1ccccc1>>OCCNCc1ccc(Br)cc1 | C(C)N(CC)CC.CN(C1=CC=CC=C1)CCO.CO.BrBr.C(C)(=O)OCC.BrBr>>BrC1=CC=C(C=C1)CNCCO | Br[Br:10].[OH:1][CH2:2][CH2:3][N:4]([CH3:5])[c:6]1[cH:7][cH:8][cH:9][cH:11][cH:12]1>>[OH:1][CH2:2][CH2:3][NH:4][CH2:5][c:6]1[cH:7][cH:8][c:9]([Br:10])[cH:11][cH:12]1 | BrBr.CN(CCO)c1ccccc1 | OCCNCc1ccc(Br)cc1 | null | [Cl-].C(C)[N+](CC)(CC)CC | C(Cl)Cl | Functional Group Interconversion | OtherReaction | bffd665e61d49b1d6457692b10477c6250cf3ee2e1f8b0416172bde2b0bbdf7e | 0a260d90fde2f27bcc20d80121977fbfb547a023e71819da383ff02783b8a0ac | c1ccccc1 | Br-[Br;H0;D1;+0:1].[C:2]-[C:3]-[N;H0;D3;+0:4](-[CH3;D1;+0:5])-[c;H0;D3;+0:6]1:[c:7]:[c:8]:[cH;D2;+0:9]:[c:10]:[c:11]:1>>[Br;H0;D1;+0:1]-[c;H0;D3;+0:9]1:[c:8]:[c:7]:[c;H0;D3;+0:6](-[CH2;D2;+0:5]-[NH;D2;+0:4]-[C:3]-[C:2]):[c:11]:[c:10]:1 | 75 | [{"value": 35.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}, {"value": 75.0, "product": "BrC1=CC=C(C=C1)CNCCO", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 2-(N-methylanilino)ethanol (0.76 g, 5 mmol) in methylene chloride (5 mL) were added tetraethylammonium chloride (83.0 mg, 0.5 mmol) and 0.1 mL of methanol. While stirring, a solution of bromine (0.8 g, 5 mmol) in methylene chloride (5 mL) was added slowly in a period of 5 minutes. When the color of the... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amine | Aromatic halide.Secondary amine | c1ccccc1 | c1ccccc1 | c1ccccc1 | HBr | [Cl-].C(C)[N+](CC)(CC)CC.C(Cl)Cl | null | null | BrBr.CN(CCO)c1ccccc1>[Cl-].C(C)[N+](CC)(CC)CC.C(Cl)Cl>OCCNCc1ccc(Br)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-93791a264422479192af704bf0566f67 | COCOc1ccc(C2(C)COc3cc(OCOC)ccc3C2c2ccc(O[Si](C)(C)C(C)(C)C)cc2)cc1>>COCOc1ccc(C2(C)COc3cc(OCOC)ccc3C2c2ccc(O)cc2)cc1 | [Si](C)(C)(C(C)(C)C)OC1=CC=C(C=C1)C1C(COC2=CC(=CC=C12)OCOC)(C)C1=CC=C(C=C1)OCOC.O>>OC1=CC=C(C=C1)C1C(COC2=CC(=CC=C12)OCOC)(C)C1=CC=C(C=C1)OCOC | CC(C)(C)[Si](C)(C)[O:28][c:27]1[cH:26][cH:25][c:24]([CH:23]2[C:9]([c:8]3[cH:7][cH:6][c:5]([O:4][CH2:3][O:2][CH3:1])[cH:32][cH:31]3)([CH3:10])[CH2:11][O:12][c:13]3[cH:14][c:15]([O:16][CH2:17][O:18][CH3:19])[cH:20][cH:21][c:22]32)[cH:30][cH:29]1>>[CH3:1][O:2][CH2:3][O:4][c:5]1[cH:6][cH:7][c:8]([C:9]2([CH3:10])[CH2:11][O:... | COCOc1ccc(C2(C)COc3cc(OCOC)ccc3C2c2ccc(O[Si](C)(C)C(C)(C)C)cc2)cc1 | COCOc1ccc(C2(C)COc3cc(OCOC)ccc3C2c2ccc(O)cc2)cc1 | null | null | O1CCCC1 | Deprotection | Alcohol deprotection from silyl ethers | e70131badc7d7d580ed75b2dfb3ce6df2a5f496b2119611cf5354e1267babe73 | b09ece7bccc3ff762f4ff5407ad846fffba6d6a63735853c86a86d29904f54ed | c1ccc(C2COc3ccccc3C2c2ccccc2)cc1 | C-C(-C)(-C)-[Si](-C)(-C)-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[OH;D1;+0:1]-[c:2](:[c:3]):[c:4] | 96.7 | [{"value": 96.4, "product": "OC1=CC=C(C=C1)C1C(COC2=CC(=CC=C12)OCOC)(C)C1=CC=C(C=C1)OCOC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 96.7, "product": "OC1=CC=C(C=C1)C1C(COC2=CC(=CC=C12)OCOC)(C)C1=CC=C(C=C1)OCOC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | To a solution of (3RS,4RS)-4-[4-(t-butyldimethylsilyloxy)phenyl]-7-(methoxymethoxy)-3-[4-(methoxymethoxy)phenyl]-3-methylchroman (1.1 g, 1.99 mmol) in tetrabydrofuran (10 ml) was added 1N-tetrabutylainmoniumfluoride (3.99 ml, 3.99 mmol) in tetrahydrofuran and stirred at room temperature for 1 hour. After the reaction w... | 10.6084/m9.figshare.5104873.v1 | null | TMS ether protective group | Aromatic alcohol | null | null | c1ccccc1.c1ccc2c(c1)CCCO2.c1ccccc1 | Other | O1CCCC1 | null | 1 | COCOc1ccc(C2(C)COc3cc(OCOC)ccc3C2c2ccc(O[Si](C)(C)C(C)(C)C)cc2)cc1>O1CCCC1>COCOc1ccc(C2(C)COc3cc(OCOC)ccc3C2c2ccc(O)cc2)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-f4d215045ecf4defbe0bf8cdee4ae013 | CCOC(=O)C(CCCCOc1ccc(C2c3ccc(OCOC)cc3OCC2(C)c2ccc(OCOC)cc2)cc1)(CCCC(F)(F)C(F)(F)F)C(=O)OCC>>CC1(c2ccc(O)cc2)COc2cc(O)ccc2C1c1ccc(OCCCCC(CCCC(F)(F)C(F)(F)F)C(=O)O)cc1 | FC(CCCC(C(=O)OCC)(C(=O)OCC)CCCCOC1=CC=C(C=C1)C1C(COC2=CC(=CC=C12)OCOC)(C1=CC=C(C=C1)OCOC)C)(C(F)(F)F)F.[OH-].[K+].Cl>>OC1=CC=C2C(C(COC2=C1)(C)C1=CC=C(C=C1)O)C1=CC=C(OCCCCC(C(=O)O)CCCC(C(F)(F)F)(F)F)C=C1 | CCOC(=O)[C:29]([CH2:28][CH2:27][CH2:26][CH2:25][O:24][c:23]1[cH:22][cH:21][c:20]([CH:19]2[C:2]([CH3:1])([c:3]3[cH:4][cH:5][c:6]([O:7]COC)[cH:8][cH:9]3)[CH2:10][O:11][c:12]3[cH:13][c:14]([O:15]COC)[cH:16][cH:17][c:18]32)[cH:44][cH:43]1)([CH2:30][CH2:31][CH2:32][C:33]([F:34])([F:35])[C:36]([F:37])([F:38])[F:39])[C:40](=[... | CCOC(=O)C(CCCCOc1ccc(C2c3ccc(OCOC)cc3OCC2(C)c2ccc(OCOC)cc2)cc1)(CCCC(F)(F)C(F)(F)F)C(=O)OCC | CC1(c2ccc(O)cc2)COc2cc(O)ccc2C1c1ccc(OCCCCC(CCCC(F)(F)C(F)(F)F)C(=O)O)cc1 | null | null | O.C(C)O | Reduction | OtherReaction | 6fc58f7e34786a8c30482cd79af46100cfd1f07d1d5b945a432845d8fef6bcea | 12f44de4c575550003c50f0c8cf10614449e1119b65f0c51a60883df20a320e1 | c1ccc(C2COc3ccccc3C2c2ccccc2)cc1 | C-C-O-C(=O)-[C;H0;D4;+0:1](-[C:2]-[C:3])(-[C:4]-[C:5])-[C:6](=[O;D1;H0:7])-[O;H0;D2;+0:8]-C-C.C-O-C-[O;H0;D2;+0:9]-[c:10](:[c:11]):[c:12].C-O-C-[O;H0;D2;+0:13]-[c:14](:[c:15]):[c:16]>>[C:3]-[C:2]-[CH;D3;+0:1](-[C:4]-[C:5])-[C:6](=[O;D1;H0:7])-[OH;D1;+0:8].[OH;D1;+0:9]-[c:10](:[c:11]):[c:12].[OH;D1;+0:13]-[c:14](:[c:15]... | 121.2 | [{"value": 121.2, "product": "OC1=CC=C2C(C(COC2=C1)(C)C1=CC=C(C=C1)O)C1=CC=C(OCCCCC(C(=O)O)CCCC(C(F)(F)F)(F)F)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of diethyl 2-(4,4,5,5,5-pentafluoropentyl)-2-(4-((3RS,4RS)-4-(3-methyl-7-(methyloxymethyloxy)-3-(4-(methyloxymethyloxy)phenyl)chroman-4-yl)phenyloxy)butyl)propane-1,3-dioate (0.552 g, 0.68 mmol) in ethanol (10 ml) was added the solution of potassium hydroxide (1.53 g, 27.23 mmol) in water (5 ml) and the m... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester.Ether.Ether.Ether.Ether | Carboxylic acid.Aromatic alcohol.Aromatic alcohol | null | null | c1ccccc1.c1ccc2c(c1)CCCO2.c1ccccc1 | HO- | O.C(C)O | null | null | CCOC(=O)C(CCCCOc1ccc(C2c3ccc(OCOC)cc3OCC2(C)c2ccc(OCOC)cc2)cc1)(CCCC(F)(F)C(F)(F)F)C(=O)OCC>O.C(C)O>CC1(c2ccc(O)cc2)COc2cc(O)ccc2C1c1ccc(OCCCCC(CCCC(F)(F)C(F)(F)F)C(=O)O)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-92e5dcd1589c4ee4b4d85ade5225b0e3 | CC1(c2ccc(O)cc2)COc2cc(O)ccc2C1c1ccc(OCCCCC(CCCC(F)(F)C(F)(F)F)(C(=O)O)C(=O)O)cc1>>CC1(c2ccc(O)cc2)COc2cc(O)ccc2C1c1ccc(OCCCCC(CCCC(F)(F)C(F)(F)F)C(=O)O)cc1 | FC(CCCC(C(=O)O)(C(=O)O)CCCCOC1=CC=C(C=C1)C1C(COC2=CC(=CC=C12)O)(C)C1=CC=C(C=C1)O)(C(F)(F)F)F.[Na+].[Cl-]>>OC1=CC=C2C(C(COC2=C1)(C)C1=CC=C(C=C1)O)C1=CC=C(OCCCCC(C(=O)O)CCCC(C(F)(F)F)(F)F)C=C1 | O=C(O)[C:29]([CH2:28][CH2:27][CH2:26][CH2:25][O:24][c:23]1[cH:22][cH:21][c:20]([CH:19]2[C:2]([CH3:1])([c:3]3[cH:4][cH:5][c:6]([OH:7])[cH:8][cH:9]3)[CH2:10][O:11][c:12]3[cH:13][c:14]([OH:15])[cH:16][cH:17][c:18]32)[cH:44][cH:43]1)([CH2:30][CH2:31][CH2:32][C:33]([F:34])([F:35])[C:36]([F:37])([F:38])[F:39])[C:40](=[O:41])... | CC1(c2ccc(O)cc2)COc2cc(O)ccc2C1c1ccc(OCCCCC(CCCC(F)(F)C(F)(F)F)(C(=O)O)C(=O)O)cc1 | CC1(c2ccc(O)cc2)COc2cc(O)ccc2C1c1ccc(OCCCCC(CCCC(F)(F)C(F)(F)F)C(=O)O)cc1 | null | null | CS(=O)C | Reduction | OtherReaction | 1dcdb0afd061fc08423f0103da81d9d30c22c6dc8004c40ee82cae1f931e4d18 | 292164ffdf89eeb341ee9424f24084b252a703a26bb77721b558b0f8a8528c45 | c1ccc(C2COc3ccccc3C2c2ccccc2)cc1 | O-C(=O)-[C;H0;D4;+0:1](-[C:2]-[C:3])(-[C:4]-[C:5])-[C:6](=[O;D1;H0:7])-[O;D1;H1:8]>>[C:3]-[C:2]-[CH;D3;+0:1](-[C:4]-[C:5])-[C:6](=[O;D1;H0:7])-[O;D1;H1:8] | 67.6 | [{"value": 67.6, "product": "OC1=CC=C2C(C(COC2=C1)(C)C1=CC=C(C=C1)O)C1=CC=C(OCCCCC(C(=O)O)CCCC(C(F)(F)F)(F)F)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 67.6, "product": "OC1=CC=C2C(C(COC2=C1)(C)C1=CC=C(C=C1)O)C1=CC=C(OCCCCC(C(=O)O)CCCC(C(F)(F)F)(F)F)C=C1", "details": "CALCULATEDPERCENTYIELD", "is... | null | null | null | null | A solution of (4,4,5,5,5-pentafluoropentyl)(4-(4-(7-hydroxy-3-(4-hydroxyphenyl)-3-methylchroman-4-yl)phenyloxy)butyl)methane-1,1-dicarboxylic acid (0.19 g, 0.285 mmol) in dimethylsulfoxide (7.6 ml) was stirred at 125° C. for 3 hours. After the reaction was completed, the reaction mixture was treated with saturated NaCl... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | null | null | null | c1ccccc1.c1ccc2c(c1)CCCO2.c1ccccc1 | Other | CS(=O)C | null | null | CC1(c2ccc(O)cc2)COc2cc(O)ccc2C1c1ccc(OCCCCC(CCCC(F)(F)C(F)(F)F)(C(=O)O)C(=O)O)cc1>CS(=O)C>CC1(c2ccc(O)cc2)COc2cc(O)ccc2C1c1ccc(OCCCCC(CCCC(F)(F)C(F)(F)F)C(=O)O)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-147e45d0a1ff43f18315a65df564fe69 | CC(C)(C)[Si](C)(C)Cl.OCCCCCCCBr>>CC(C)(C)[Si](C)(C)OCCCCCCCBr | O.BrCCCCCCCO.N1C=NC=C1.[Si](C)(C)(C(C)(C)C)Cl>>[Si](C)(C)(C(C)(C)C)OCCCCCCCBr | Cl[Si:5]([C:2]([CH3:1])([CH3:3])[CH3:4])([CH3:6])[CH3:7].[OH:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][Br:16]>>[CH3:1][C:2]([CH3:3])([CH3:4])[Si:5]([CH3:6])([CH3:7])[O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][Br:16] | CC(C)(C)[Si](C)(C)Cl.OCCCCCCCBr | CC(C)(C)[Si](C)(C)OCCCCCCCBr | null | null | O1CCCC1 | Protection | Alcohol protection with silyl ethers | 0085cd6629412592263fdf1537bdf8c19ef10dbeafe6f880807464d8107fa715 | d2a170d01b2f3ec57d6fac058519475050ba5531f5d304635fb42e153d5bb9b5 | null | Cl-[Si;H0;D4;+0:1](-[C;D1;H3:2])(-[C;D1;H3:3])-[C:4](-[C;D1;H3:5])(-[C;D1;H3:6])-[C;D1;H3:7].[C:8]-[C:9]-[OH;D1;+0:10]>>[C:8]-[C:9]-[O;H0;D2;+0:10]-[Si;H0;D4;+0:1](-[C;D1;H3:2])(-[C;D1;H3:3])-[C:4](-[C;D1;H3:5])(-[C;D1;H3:6])-[C;D1;H3:7] | 72 | [{"value": 72.0, "product": "[Si](C)(C)(C(C)(C)C)OCCCCCCCBr", "details": "PERCENTYIELD", "is_desired": false}, {"value": 72.0, "product": "[Si](C)(C)(C(C)(C)C)OCCCCCCCBr", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | To a solution of 7-bromoheptanol (50 g, 25.6 mmole) and imidazole (4.2 g, 61.5 mmole) in dry tetrahydrofuran (80 ml) was added t-butyldimethylsilyl chloride (4.6 g, 30.8 mmole) dropwise during 1 hour at room temperature. Then the reaction mixture was stirred overnight at room temperature. When the reaction was complete... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Silyl protective group | TMS ether protective group | null | null | null | HCl | O1CCCC1 | null | 8 | CC(C)(C)[Si](C)(C)Cl.OCCCCCCCBr>O1CCCC1>CC(C)(C)[Si](C)(C)OCCCCCCCBr |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-09abb0bcc34b4aab8e6936789d4ceded | CCOC(=O)C(CCCC(F)(F)C(F)(F)F)C(=O)OCC.ClCCCCCCBr>>CCOC(=O)C(CCCCCCCl)(CCCC(F)(F)C(F)(F)F)C(=O)OCC | O.BrCCCCCCCl.C(C)OC(C(C(=O)OCC)CCCC(C(F)(F)F)(F)F)=O.[H-].[Na+]>>C(C)OC(C(C(=O)OCC)(CCCC(C(F)(F)F)(F)F)CCCCCCCl)=O | [CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([CH2:14][CH2:15][CH2:16][C:17]([F:18])([F:19])[C:20]([F:21])([F:22])[F:23])[C:24](=[O:25])[O:26][CH2:27][CH3:28].Br[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][Cl:13]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6]([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][Cl:13])([CH2:14][CH2:15][CH2... | CCOC(=O)C(CCCC(F)(F)C(F)(F)F)C(=O)OCC.ClCCCCCCBr | CCOC(=O)C(CCCCCCCl)(CCCC(F)(F)C(F)(F)F)C(=O)OCC | null | null | O1CCCC1 | C-C Coupling | OtherReaction | 8175b6573d6439ec7ccc45bf6b48843ab56b46dccfc6504384c4766d09f35cc7 | d1817e44576d3a158547867a56245217a593d4f828a6d6dfaa8ed11276894e44 | null | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[C:4]-[C:5]-[CH;D3;+0:6](-[C:7](=[O;D1;H0:8])-[#8:9]-[C:10])-[C:11](=[O;D1;H0:12])-[#8:13]-[C:14]>>[C:4]-[C:5]-[C;H0;D4;+0:6](-[CH2;D2;+0:1]-[C:2]-[C:3])(-[C:7](=[O;D1;H0:8])-[#8:9]-[C:10])-[C:11](=[O;D1;H0:12])-[#8:13]-[C:14] | 56 | [{"value": 56.0, "product": "C(C)OC(C(C(=O)OCC)(CCCC(C(F)(F)F)(F)F)CCCCCCCl)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 55.5, "product": "C(C)OC(C(C(=O)OCC)(CCCC(C(F)(F)F)(F)F)CCCCCCCl)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | To a solution of (4,4,5,5,5-pentafluoropentyl)malonic acid diethyl ester (1 g, 3.12 mmol) in tetrahydrofuran (15 ml) was added sodium hydride (175 mg, 4.37 mmol), which was then stirred for 30 min at rt. 1-Bromo-6-chlorohexane (0.7 ml, 4.68 mmol) was added to this reaction mixture and the reaction mixture was refluxed ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester.Ester | Ester.Ester | null | null | null | HBr | O1CCCC1 | null | 0.5 | CCOC(=O)C(CCCC(F)(F)C(F)(F)F)C(=O)OCC.ClCCCCCCBr>O1CCCC1>CCOC(=O)C(CCCCCCCl)(CCCC(F)(F)C(F)(F)F)C(=O)OCC |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-7d17d3645d6548c9873294a02e062c24 | CCOC(=O)C(CCCCCCCl)(CCCC(F)(F)C(F)(F)F)C(=O)OCC.[I-]>>CCOC(=O)C(CCCCCCI)(CCCC(F)(F)C(F)(F)F)C(=O)OCC | O.C(C)OC(C(C(=O)OCC)(CCCC(C(F)(F)F)(F)F)CCCCCCCl)=O.[I-].[Na+]>>C(C)OC(C(C(=O)OCC)(CCCC(C(F)(F)F)(F)F)CCCCCCI)=O | Cl[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][C:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])([CH2:14][CH2:15][CH2:16][C:17]([F:18])([F:19])[C:20]([F:21])([F:22])[F:23])[C:24](=[O:25])[O:26][CH2:27][CH3:28].[I-:13]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6]([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][I:13])([CH2:14][CH2:15][CH2... | CCOC(=O)C(CCCCCCCl)(CCCC(F)(F)C(F)(F)F)C(=O)OCC.[I-] | CCOC(=O)C(CCCCCCI)(CCCC(F)(F)C(F)(F)F)C(=O)OCC | null | null | CC(=O)C | Functional Group Interconversion | OtherReaction | e944a2acb95a43a23818321f2ac2f96ba2f2b8d34f52c1cfd1e3802d2403177f | e2ca6f9fe1078a3836d617896a4e5cc310fb155ca459b021e2b549b3e61f1df7 | null | Cl-[CH2;D2;+0:1]-[C:2]-[C:3].[I-;H0;D0:4]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[I;H0;D1;+0:4] | 89.4 | [{"value": 89.0, "product": "C(C)OC(C(C(=O)OCC)(CCCC(C(F)(F)F)(F)F)CCCCCCI)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 89.4, "product": "C(C)OC(C(C(=O)OCC)(CCCC(C(F)(F)F)(F)F)CCCCCCI)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 6-chlorohexyl-(4,4,5,5,5-pentafluoropentyl)malonic acid diethyl ester (743 mg, 1.69 mmol) in acetone (5 ml) was added sodium iodide (761 mg, 5.08 mmol), which was then refluxed for 4 h. When the reaction was completed, water was added to the reaction mixture and extracted with ethyl acetate. Then, the ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | Primary halide | null | null | null | Other | CC(=O)C | null | null | CCOC(=O)C(CCCCCCCl)(CCCC(F)(F)C(F)(F)F)C(=O)OCC.[I-]>CC(=O)C>CCOC(=O)C(CCCCCCI)(CCCC(F)(F)C(F)(F)F)C(=O)OCC |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-f80513410356425d8f6b7c43ded5850e | CC(C)OB(OC(C)C)OC(C)C.Fc1ccc(-c2nn(C(c3ccccc3)(c3ccccc3)c3ccccc3)cc2Br)cc1>>OB(O)c1cn(C(c2ccccc2)(c2ccccc2)c2ccccc2)nc1-c1ccc(F)cc1 | B(OC(C)C)(OC(C)C)OC(C)C.C(CCC)[Li].BrC=1C(=NN(C1)C(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)C1=CC=C(C=C1)F.[Cl-].[NH4+]>>FC1=CC=C(C=C1)C1=NN(C=C1B(O)O)C(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1 | CC(C)O[B:2]([O:1]C(C)C)[O:3]C(C)C.Br[c:4]1[cH:5][n:6]([C:7]([c:8]2[cH:9][cH:10][cH:11][cH:12][cH:13]2)([c:14]2[cH:15][cH:16][cH:17][cH:18][cH:19]2)[c:20]2[cH:21][cH:22][cH:23][cH:24][cH:25]2)[n:26][c:27]1-[c:28]1[cH:29][cH:30][c:31]([F:32])[cH:33][cH:34]1>>[OH:1][B:2]([OH:3])[c:4]1[cH:5][n:6]([C:7]([c:8]2[cH:9][cH:10][... | CC(C)OB(OC(C)C)OC(C)C.Fc1ccc(-c2nn(C(c3ccccc3)(c3ccccc3)c3ccccc3)cc2Br)cc1 | OB(O)c1cn(C(c2ccccc2)(c2ccccc2)c2ccccc2)nc1-c1ccc(F)cc1 | null | null | O1CCCC1.O.CCCCCC | Miscellaneous | Preparation of boronic acids | 3844510e1842c6edc8fafe6b1abc924cfc5e60e61202cd5af68f36b3305fbec1 | dafd25fbe01879c365f8c874026e570f49824f4bb82016b29d0c5d21aeb58ca3 | c1ccc(-c2ccn(C(c3ccccc3)(c3ccccc3)c3ccccc3)n2)cc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3](-[C:4]):[#7;a:5]:[c:6]:1-[c:7].C-C(-C)-O-[B;H0;D3;+0:8](-[O;H0;D2;+0:9]-C(-C)-C)-[O;H0;D2;+0:10]-C(-C)-C>>[C:4]-[#7;a:3]1:[#7;a:5]:[c:6](-[c:7]):[c;H0;D3;+0:1](-[B;H0;D3;+0:8](-[OH;D1;+0:9])-[OH;D1;+0:10]):[c:2]:1 | null | [] | 0 | CELSIUS | 30 | MINUTE | 47.5 g 4-bromo-3-(4-fluorophenyl)-1-trityl-1H-pyrazole was dissolved in 400 mL anhydrous tetrahydrofuran, and then 40.7 mL solution of 1.6 M n-butyl lithium in hexane was added dropwise thereto at −70° C. The mixture was stirred for 30 minutes, 17.2 mL triisopropyl borate was added dropwise thereto, and the mixture was... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | Boronic acid | c1cn[nH]c1 | c1cn[nH]c1 | c1cn[nH]c1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | HBr | O1CCCC1.O.CCCCCC | 0 | 0.5 | CC(C)OB(OC(C)C)OC(C)C.Fc1ccc(-c2nn(C(c3ccccc3)(c3ccccc3)c3ccccc3)cc2Br)cc1>O1CCCC1.O.CCCCCC>OB(O)c1cn(C(c2ccccc2)(c2ccccc2)c2ccccc2)nc1-c1ccc(F)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-e067988a14f641bf928dd0855ddf7da7 | CC(C)OB(OC(C)C)OC(C)C.N#Cc1ccc(-c2nn(C(c3ccccc3)(c3ccccc3)c3ccccc3)cc2I)cc1>>N#Cc1ccc(-c2nn(C(c3ccccc3)(c3ccccc3)c3ccccc3)cc2B(O)O)cc1 | [Cl-].[NH4+].C(C)(C)[Mg]Br.IC=1C(=NN(C1)C(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)C1=CC=C(C#N)C=C1.B(OC(C)C)(OC(C)C)OC(C)C>>C(#N)C1=CC=C(C=C1)C1=NN(C=C1B(O)O)C(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1 | CC(C)O[B:31]([O:32]C(C)C)[O:33]C(C)C.I[c:30]1[c:7](-[c:6]2[cH:5][cH:4][c:3]([C:2]#[N:1])[cH:35][cH:34]2)[n:8][n:9]([C:10]([c:11]2[cH:12][cH:13][cH:14][cH:15][cH:16]2)([c:17]2[cH:18][cH:19][cH:20][cH:21][cH:22]2)[c:23]2[cH:24][cH:25][cH:26][cH:27][cH:28]2)[cH:29]1>>[N:1]#[C:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[n:8][n:9]([C... | CC(C)OB(OC(C)C)OC(C)C.N#Cc1ccc(-c2nn(C(c3ccccc3)(c3ccccc3)c3ccccc3)cc2I)cc1 | N#Cc1ccc(-c2nn(C(c3ccccc3)(c3ccccc3)c3ccccc3)cc2B(O)O)cc1 | null | null | O1CCCC1 | Miscellaneous | OtherReaction | 976aa5a00df0539fe32ca1f676305423435df099e4ae744398549c49ada58b5c | dafd25fbe01879c365f8c874026e570f49824f4bb82016b29d0c5d21aeb58ca3 | c1ccc(-c2ccn(C(c3ccccc3)(c3ccccc3)c3ccccc3)n2)cc1 | C-C(-C)-O-[B;H0;D3;+0:1](-[O;H0;D2;+0:2]-C(-C)-C)-[O;H0;D2;+0:3]-C(-C)-C.I-[c;H0;D3;+0:4]1:[c:5]:[#7;a:6](-[C:7]):[#7;a:8]:[c:9]:1-[c:10]>>[C:7]-[#7;a:6]1:[#7;a:8]:[c:9](-[c:10]):[c;H0;D3;+0:4](-[B;H0;D3;+0:1](-[OH;D1;+0:2])-[OH;D1;+0:3]):[c:5]:1 | null | [] | null | null | 30 | MINUTE | 17.2 mL of 0.75 M isopropyl magnesium bromide was added dropwise at −40° C. into a solution of 6 g 4-(4-iodo-1-trityl-1H-3-pyrazolyl)benzonitrile in tetrahydrofuran, and the mixture was stirred for 30 minutes. Subsequently, 3.3 mL triisopropyl borate was added dropwise thereto at −40° C. ad stirred at −10° C. for 2 hou... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | Boronic acid | c1c[nH]nc1 | c1c[nH]nc1 | c1ccccc1.c1c[nH]nc1.c1ccccc1.c1ccccc1.c1ccccc1 | HI | O1CCCC1 | null | 0.5 | CC(C)OB(OC(C)C)OC(C)C.N#Cc1ccc(-c2nn(C(c3ccccc3)(c3ccccc3)c3ccccc3)cc2I)cc1>O1CCCC1>N#Cc1ccc(-c2nn(C(c3ccccc3)(c3ccccc3)c3ccccc3)cc2B(O)O)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-11e0cb72b6b940c093fc6fa91043590f | Brc1ccc2nccn2c1.OB(O)c1cn(C(c2ccccc2)(c2ccccc2)c2ccccc2)nc1-c1ccc(F)cc1>>Fc1ccc(-c2nn(C(c3ccccc3)(c3ccccc3)c3ccccc3)cc2-c2ccc3nccn3c2)cc1 | BrC=1C=CC=2N(C1)C=CN2.FC1=CC=C(C=C1)C1=NN(C=C1B(O)O)C(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1.C(C)O.C([O-])([O-])=O.[Na+].[Na+]>>FC1=CC=C(C=C1)C1=NN(C=C1C=1C=CC=2N(C1)C=CN2)C(C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2 | Br[c:30]1[cH:31][cH:32][c:33]2[n:34][cH:35][cH:36][n:37]2[cH:38]1.OB(O)[c:29]1[c:6](-[c:5]2[cH:4][cH:3][c:2]([F:1])[cH:40][cH:39]2)[n:7][n:8]([C:9]([c:10]2[cH:11][cH:12][cH:13][cH:14][cH:15]2)([c:16]2[cH:17][cH:18][cH:19][cH:20][cH:21]2)[c:22]2[cH:23][cH:24][cH:25][cH:26][cH:27]2)[cH:28]1>>[F:1][c:2]1[cH:3][cH:4][c:5](... | Brc1ccc2nccn2c1.OB(O)c1cn(C(c2ccccc2)(c2ccccc2)c2ccccc2)nc1-c1ccc(F)cc1 | Fc1ccc(-c2nn(C(c3ccccc3)(c3ccccc3)c3ccccc3)cc2-c2ccc3nccn3c2)cc1 | null | null | C1(=CC=CC=C1)C.C(C)(=O)OCC | C-C Coupling | Suzuki coupling with boronic acids | 608f2ba96b58fcb8873cdb9afc2c5161844f5a23b41ffec02067329cf10e0c19 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(-c2nn(C(c3ccccc3)(c3ccccc3)c3ccccc3)cc2-c2ccc3nccn3c2)cc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]2:[#7;a:5]:[c:6]:[c:7]:[#7;a:8]:2:[c:9]:1.O-B(-O)-[c;H0;D3;+0:10]1:[c:11]:[#7;a:12](-[C:13]):[#7;a:14]:[c:15]:1-[c:16]>>[C:13]-[#7;a:12]1:[#7;a:14]:[c:15](-[c:16]):[c;H0;D3;+0:10](-[c;H0;D3;+0:1]2:[c:2]:[c:3]:[c:4]3:[#7;a:5]:[c:6]:[c:7]:[#7;a:8]:3:[c:9]:2):[c:11]:1 | 80 | [{"value": 80.0, "product": "FC1=CC=C(C=C1)C1=NN(C=C1C=1C=CC=2N(C1)C=CN2)C(C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 2.2 g 6-bromoimidazo[1,2-a]pyridine, 6 g 3-(4-fluorophenyl)-1-trityl-1H-4-pyrazolylboronic acid (compound in Production Example 25), and 647 mg tetrakistriphenyl phosphine palladium were heated in a solution mixture of 30 mL ethanol, 30 mL toluene and 17 mL of 2 N aqueous sodium carbonate at 80° C. for 2 hours in a str... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccn2ccnc2c1.c1c[nH]nc1 | c1c[nH]nc1.c1ccn2ccnc2c1 | c1ccccc1.c1c[nH]nc1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccn2ccnc2c1 | HBr.B | C1(=CC=CC=C1)C.C(C)(=O)OCC | null | null | Brc1ccc2nccn2c1.OB(O)c1cn(C(c2ccccc2)(c2ccccc2)c2ccccc2)nc1-c1ccc(F)cc1>C1(=CC=CC=C1)C.C(C)(=O)OCC>Fc1ccc(-c2nn(C(c3ccccc3)(c3ccccc3)c3ccccc3)cc2-c2ccc3nccn3c2)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-0e4d0ba3a8134211880ae0d64a80913e | CSc1ccc(-c2nn(C(c3ccccc3)(c3ccccc3)c3ccccc3)cc2-c2ccc3ncc(I)n3c2)cc1>>CS(=O)(=O)c1ccc(-c2nn(C(c3ccccc3)(c3ccccc3)c3ccccc3)cc2-c2ccc3ncc(I)n3c2)cc1 | O.IC1=CN=C2N1C=C(C=C2)C=2C(=NN(C2)C(C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C2=CC=C(C=C2)SC.OOS(=O)[O-].[K+]>>IC1=CN=C2N1C=C(C=C2)C=2C(=NN(C2)C(C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C2=CC=C(C=C2)S(=O)(=O)C | [CH3:1][S:2][c:5]1[cH:6][cH:7][c:8](-[c:9]2[n:10][n:11]([C:12]([c:13]3[cH:14][cH:15][cH:16][cH:17][cH:18]3)([c:19]3[cH:20][cH:21][cH:22][cH:23][cH:24]3)[c:25]3[cH:26][cH:27][cH:28][cH:29][cH:30]3)[cH:31][c:32]2-[c:33]2[cH:34][cH:35][c:36]3[n:37][cH:38][c:39]([I:40])[n:41]3[cH:42]2)[cH:43][cH:44]1>>[CH3:1][S:2](=[O:3])(... | CSc1ccc(-c2nn(C(c3ccccc3)(c3ccccc3)c3ccccc3)cc2-c2ccc3ncc(I)n3c2)cc1 | CS(=O)(=O)c1ccc(-c2nn(C(c3ccccc3)(c3ccccc3)c3ccccc3)cc2-c2ccc3ncc(I)n3c2)cc1 | null | null | O1CCCC1.CO | Oxidation | OtherReaction | 20dd6d48007b4fe7cd760226f21413eb5e71e6468db112596c2e7ea4858c8ac1 | 5cedc1bf0f43f21d78a249521ecfcec19fc5ac4895c41eed0e84f0c2618149fa | c1ccc(-c2nn(C(c3ccccc3)(c3ccccc3)c3ccccc3)cc2-c2ccc3nccn3c2)cc1 | [C;D1;H3:1]-[S;H0;D2;+0:2]-[c:3](:[c:4]):[c:5]>>[C;D1;H3:1]-[S;H0;D4;+0:2](=[O;D1;H0:6])(=[O;D1;H0:7])-[c:3](:[c:4]):[c:5] | null | [] | null | null | 2 | HOUR | 1.7 g 3-iodo-6-{3-[4-(methylsulfanyl)phenyl]-1-trityl-1H-4-pyrazolyl}imidazo[1,2-a]pyridine obtained in Example 42 was dissolved in a solvent mixture of 30 mL tetrahydrofuran and 30 mL methanol, and then 20 mL aqueous solution of 3.1 g oxone was added in divided portions thereto. The mixture was stirred at room tempera... | 10.6084/m9.figshare.5104873.v1 | null | Monosulfide | Sulfone | null | null | c1ccccc1.c1c[nH]nc1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccn2ccnc2c1 | null | O1CCCC1.CO | null | 2 | CSc1ccc(-c2nn(C(c3ccccc3)(c3ccccc3)c3ccccc3)cc2-c2ccc3ncc(I)n3c2)cc1>O1CCCC1.CO>CS(=O)(=O)c1ccc(-c2nn(C(c3ccccc3)(c3ccccc3)c3ccccc3)cc2-c2ccc3ncc(I)n3c2)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-91676370c4b44065a709dbf40d068486 | Brc1ccc2nccn2c1.O=C1CCC(=O)N1I>>Brc1ccc2ncc(I)n2c1 | S(=S)(=O)([O-])[O-].[Na+].[Na+].IN1C(CCC1=O)=O.BrC=1C=CC=2N(C1)C=CN2.O>>BrC=1C=CC=2N(C1)C(=CN2)I | [Br:1][c:2]1[cH:3][cH:4][c:5]2[n:6][cH:7][cH:8][n:10]2[cH:11]1.O=C1CCC(=O)N1[I:9]>>[Br:1][c:2]1[cH:3][cH:4][c:5]2[n:6][cH:7][c:8]([I:9])[n:10]2[cH:11]1 | Brc1ccc2nccn2c1.O=C1CCC(=O)N1I | Brc1ccc2ncc(I)n2c1 | null | null | CN(C=O)C | Functional Group Interconversion | OtherReaction | 4574e733f80d194ce9380df52b6f0165984d072a1369f9c636a5ef16f4be8d67 | 0e444576b73669992a4073cc3f7b10ed52cb9df09f9f8e4042e39e6a602aa390 | c1ccn2ccnc2c1 | O=C1-C-C-C(=O)-N-1-[I;H0;D1;+0:1].[c:2]:[#7;a:3]1:[cH;D2;+0:4]:[c:5]:[#7;a:6]:[c:7]:1:[c:8]>>[I;H0;D1;+0:1]-[c;H0;D3;+0:4]1:[c:5]:[#7;a:6]:[c:7](:[c:8]):[#7;a:3]:1:[c:2] | 91.5 | [{"value": 91.5, "product": "BrC=1C=CC=2N(C1)C(=CN2)I", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | 10.7 g N-iodosuccinimide was added in divided portions to 100 mL solution of 9 g 6-bromoimidazo[1,2-a]pyridine in N,N-dimethylformamide, and the mixture was stirred for 2 hours. An aqueous sodium thiosulfate solution was added thereto and stirred for 1 hour, water was added thereto, and the formed crystals were collect... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Tertiary amide | Aromatic halide | c1ccn2ccnc2c1.C1CCNC1 | c1ccn2ccnc2c1 | c1ccn2ccnc2c1 | HO- | CN(C=O)C | null | 2 | Brc1ccc2nccn2c1.O=C1CCC(=O)N1I>CN(C=O)C>Brc1ccc2ncc(I)n2c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-bdd0da86c2d84590b4e49a37136c4830 | Brc1ccc2ncc(I)n2c1.COc1ccc(B(O)O)cc1>>COc1ccc(-c2cnc3ccc(Br)cn23)cc1 | C(CCO)O.COC1=CC=C(C=C1)B(O)O.BrC=1C=CC=2N(C1)C(=CN2)I.P(=O)([O-])([O-])[O-].[K+].[K+].[K+]>>BrC=1C=CC=2N(C1)C(=CN2)C2=CC=C(C=C2)OC | I[c:7]1[cH:8][n:9][c:10]2[cH:11][cH:12][c:13]([Br:14])[cH:15][n:16]12.OB(O)[c:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:18][cH:17]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][n:9][c:10]3[cH:11][cH:12][c:13]([Br:14])[cH:15][n:16]23)[cH:17][cH:18]1 | Brc1ccc2ncc(I)n2c1.COc1ccc(B(O)O)cc1 | COc1ccc(-c2cnc3ccc(Br)cn23)cc1 | null | null | CN(C=O)C.C(C)OCC | C-C Coupling | Suzuki coupling with boronic acids | 6d2f92e38cbc7faf246cda8a4b8669001b5c18f23ff87160bd75535916dab019 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(-c2cnc3ccccn23)cc1 | I-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[c:4](:[c:5]):[#7;a:6]:1:[c:7].O-B(-O)-[c;H0;D3;+0:8](:[c:9]:[c:10]):[c:11]:[c:12]>>[c:5]:[c:4]1:[#7;a:3]:[c:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:8](:[c:9]:[c:10]):[c:11]:[c:12]):[#7;a:6]:1:[c:7] | 78.9 | [{"value": 78.9, "product": "BrC=1C=CC=2N(C1)C(=CN2)C2=CC=C(C=C2)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | 0.81 mL 1,3-propane diol was added to a suspension of 1.69 g 4-methoxyphenylboronic acid in 15 mL diethyl ether, and the mixture was stirred a room temperature for 1 hour. Formed water was removed, and the organic solvent was evaporated, whereby an oil was obtained. 2.7 g 6-bromo-3-iodoimidazo[1,2-a]pyridine (compound ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccn2ccnc2c1.c1ccccc1 | c1ccccc1.c1ccn2ccnc2c1 | c1ccccc1.c1ccn2ccnc2c1 | HI.B | CN(C=O)C.C(C)OCC | null | 1 | Brc1ccc2ncc(I)n2c1.COc1ccc(B(O)O)cc1>CN(C=O)C.C(C)OCC>COc1ccc(-c2cnc3ccc(Br)cn23)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-87ea1ccdc5514c38a6a2a4a05e08cb86 | Brc1ccc2ncc(I)n2c1.COC(=O)c1ccc(B2OC(C)(C)C(C)(C)O2)cc1>>COC(=O)c1ccc(-c2cnc3ccc(Br)cn23)cc1 | BrC=1C=CC=2N(C1)C(=CN2)I.P(=O)([O-])([O-])[O-].[K+].[K+].[K+].CC1(OB(OC1(C)C)C1=CC=C(C(=O)OC)C=C1)C>>BrC=1C=CC=2N(C1)C(=CN2)C2=CC=C(C(=O)OC)C=C2 | I[c:9]1[cH:10][n:11][c:12]2[cH:13][cH:14][c:15]([Br:16])[cH:17][n:18]12.CC1(C)OB([c:8]2[cH:7][cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[cH:20][cH:19]2)OC1(C)C>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8](-[c:9]2[cH:10][n:11][c:12]3[cH:13][cH:14][c:15]([Br:16])[cH:17][n:18]23)[cH:19][cH:20]1 | Brc1ccc2ncc(I)n2c1.COC(=O)c1ccc(B2OC(C)(C)C(C)(C)O2)cc1 | COC(=O)c1ccc(-c2cnc3ccc(Br)cn23)cc1 | null | null | CN(C=O)C | C-C Coupling | Suzuki coupling with boronic esters | dcda447711556696a2b0cc312b40d9049503597a5d54a34fea6736b791985a24 | b42efb3b6a7742d5af594c6a3031e487327e58e9f8c2f428ee68996c98377910 | c1ccc(-c2cnc3ccccn23)cc1 | C-C1(-C)-O-B(-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5])-O-C-1(-C)-C.I-[c;H0;D3;+0:6]1:[c:7]:[#7;a:8]:[c:9](:[c:10]):[#7;a:11]:1:[c:12]>>[c:10]:[c:9]1:[#7;a:8]:[c:7]:[c;H0;D3;+0:6](-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5]):[#7;a:11]:1:[c:12] | 67.8 | [{"value": 67.8, "product": "BrC=1C=CC=2N(C1)C(=CN2)C2=CC=C(C(=O)OC)C=C2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 2.3 g methyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate prepared according to T. Ishiyama et al., J. Org. Chem., 60, 7508 (1995), 2.0 g 6-bromo-3-iodoimidazo[1,2-a]pyridine (compound in Production Example 49), 2.5 g potassium phosphate, 360 mg tetrakistriphenyl phosphine palladium and 30 mL N,N-dimethylfor... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic ester | null | c1ccn2ccnc2c1.B1OCCO1.c1ccccc1 | c1ccccc1.c1ccn2ccnc2c1 | c1ccccc1.c1ccn2ccnc2c1 | HI.B | CN(C=O)C | null | null | Brc1ccc2ncc(I)n2c1.COC(=O)c1ccc(B2OC(C)(C)C(C)(C)O2)cc1>CN(C=O)C>COC(=O)c1ccc(-c2cnc3ccc(Br)cn23)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-0ca7047a8a154fe59d87a77e0f61519f | Nc1cc(Br)ccc1[N+](=O)[O-].S=C=S>>Sc1nc2ccc(Br)cc2[nH]1 | BrC=1C=CC(=C(N)C1)[N+](=O)[O-].C(=S)=S.[OH-].[K+].O>>BrC=1C=CC2=C(NC(=N2)S)C1 | O=[N+:3]([O-])[c:4]1[cH:5][cH:6][c:7]([Br:8])[cH:9][c:10]1[NH2:11].S=[C:2]=[S:1]>>[SH:1][c:2]1[n:3][c:4]2[cH:5][cH:6][c:7]([Br:8])[cH:9][c:10]2[nH:11]1 | Nc1cc(Br)ccc1[N+](=O)[O-].S=C=S | Sc1nc2ccc(Br)cc2[nH]1 | null | null | C(C)(=O)O.CO.C(C)O | Aromatic Heterocycle Formation | OtherReaction | c2c29974f4b5be07c21486a5b198dab3d77dbe80b212fcca89a8c66a9fb55acd | ecf3fe2b0af561b8897dfd28d098c701162f656ce0345b917de68408521bab59 | c1ccc2[nH]cnc2c1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4](-[NH2;D1;+0:5]):[c:6].S=[C;H0;D2;+0:7]=[S;H0;D1;+0:8]>>[SH;D1;+0:8]-[c;H0;D3;+0:7]1:[n;H0;D2;+0:1]:[c:2](:[c:3]):[c:4](:[c:6]):[nH;D2;+0:5]:1 | null | [] | null | null | null | null | 6.7 g of 4-bromo-1,2-benzenediamine obtained by reducing 5-bromo-2-nitroaniline was dissolved in 50 mL methanol, then 4.4 mL carbon disulfide was added thereto, a solution of 1.3 g potassium hydroxide in 40 mL ethanol was added little by little thereto, and the mixture was heated for 3.5 hours under reflux. The reactio... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group.Primary amine | Aromatic thiol | c1ccccc1 | c1ccc2[nH]cnc2c1 | c1ccc2[nH]cnc2c1 | Other | C(C)(=O)O.CO.C(C)O | null | null | Nc1cc(Br)ccc1[N+](=O)[O-].S=C=S>C(C)(=O)O.CO.C(C)O>Sc1nc2ccc(Br)cc2[nH]1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-6487d75bc2b74dfa990fbea3b98399e4 | CCSc1nc2ccc(Br)cc2n1COC(=O)C(C)(C)C>>CCSc1nc2ccc(Br)cc2[nH]1 | C(C(C)(C)C)(=O)OCN1C(=NC2=C1C=C(C=C2)Br)SCC.C(C(C)(C)C)(=O)OCN1C(=NC2=C1C=CC(=C2)Br)SCC>>BrC=1C=CC2=C(NC(=N2)SCC)C1 | CC(C)(C)C(=O)OC[n:13]1[c:4]([S:3][CH2:2][CH3:1])[n:5][c:6]2[cH:7][cH:8][c:9]([Br:10])[cH:11][c:12]21>>[CH3:1][CH2:2][S:3][c:4]1[n:5][c:6]2[cH:7][cH:8][c:9]([Br:10])[cH:11][c:12]2[nH:13]1 | CCSc1nc2ccc(Br)cc2n1COC(=O)C(C)(C)C | CCSc1nc2ccc(Br)cc2[nH]1 | null | null | null | Reduction | OtherReaction | 5e0e8f5be04754a5d1256a4b21b46ea8a49e71232936a58e92fcccb42ba1ebb2 | b8e5da8ea19c403a2e974791a9cf591400749acb6b71151717aaece4f3b22bef | c1ccc2[nH]cnc2c1 | C-C(-C)(-C)-C(=O)-O-C-[n;H0;D3;+0:1]1:[c:2](:[c:3]):[c:4](:[c:5]):[#7;a:6]:[c:7]:1-[#16:8]>>[#16:8]-[c:7]1:[#7;a:6]:[c:4](:[c:5]):[c:2](:[c:3]):[nH;D2;+0:1]:1 | null | [] | null | null | null | null | 11.8 g mixture of [6-bromo-2-(ethylsulfanyl)-1H-benzo[d]imidazol-1-yl]methyl pivalate and [5-bromo-2-(ethylsulfanyl)-1H-benzo[d]imidazol-1-yl]methyl pivalate in a ratio of 1:1 was obtained as pale yellow solid by the same method as in Production Example 64 from 8.1 g 6-bromo-2-(ethylsulfanyl)-1H-benzo[d]imidazole obtai... | 10.6084/m9.figshare.5104873.v1 | null | Ester | null | c1ccc2nc[nH]c2c1 | c1ccc2[nH]cnc2c1 | c1ccc2[nH]cnc2c1 | HO- | null | null | null | CCSc1nc2ccc(Br)cc2n1COC(=O)C(C)(C)C>>CCSc1nc2ccc(Br)cc2[nH]1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-826001f3bb384ba3ae1349f678af87ac | CN1CCNCC1.Clc1ccnc2ccc(Br)cc12>>CN1CCN(c2ccnc3ccc(Br)cc23)CC1 | BrC=1C=C2C(=CC=NC2=CC1)Cl.CN1CCNCC1.C([O-])([O-])=O.[K+].[K+].CN(C=O)C>>BrC=1C=C2C(=CC=NC2=CC1)N1CCN(CC1)C | [CH3:1][N:2]1[CH2:3][CH2:4][NH:5][CH2:17][CH2:18]1.Cl[c:6]1[cH:7][cH:8][n:9][c:10]2[cH:11][cH:12][c:13]([Br:14])[cH:15][c:16]12>>[CH3:1][N:2]1[CH2:3][CH2:4][N:5]([c:6]2[cH:7][cH:8][n:9][c:10]3[cH:11][cH:12][c:13]([Br:14])[cH:15][c:16]23)[CH2:17][CH2:18]1 | CN1CCNCC1.Clc1ccnc2ccc(Br)cc12 | CN1CCN(c2ccnc3ccc(Br)cc23)CC1 | null | null | O.C(C)(=O)OCC | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | 9f69c5c4a4ea31f8d76ec3987be7bd40b9cb34092e5d3f4fe2f7075ca0afa5f4 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc2c(N3CCNCC3)ccnc2c1 | Cl-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8].[#7:9]1-[C:10]-[C:11]-[NH;D2;+0:12]-[C:13]-[C:14]-1>>[c:6]:[c:5]1:[#7;a:4]:[c:3]:[c:2]:[c;H0;D3;+0:1](-[N;H0;D3;+0:12]2-[C:11]-[C:10]-[#7:9]-[C:14]-[C:13]-2):[c:7]:1:[c:8] | null | [] | 130 | CELSIUS | 8 | HOUR | A mixture of 485 mg 6-bromo-4-chloroquinoline, 1.1 mL N-methyl piperazine, 415 mg potassium carbonate and 10 mL N,N-dimethylformamide was stirred at 130° C. for 8 hours. Ethyl acetate and water were added to the reaction solution, and the organic layer was separated. The organic layer was washed with water and brine an... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | C1C[NH]CCN1.c1ccc2ncccc2c1 | C1C[NH]CC[NH]1.c1ccc2ncccc2c1 | C1C[NH]CC[NH]1.c1ccc2ncccc2c1 | HCl | O.C(C)(=O)OCC | 130 | 8 | CN1CCNCC1.Clc1ccnc2ccc(Br)cc12>O.C(C)(=O)OCC>CN1CCN(c2ccnc3ccc(Br)cc23)CC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-a1988d1ba7504d79b97782eddbccf622 | C1COCCN1.Clc1ccnc2ccc(Br)cc12>>Brc1ccc2nccc(N3CCOCC3)c2c1 | BrC=1C=C2C(=CC=NC2=CC1)Cl.N1CCOCC1>>BrC=1C=C2C(=CC=NC2=CC1)N1CCOCC1 | [NH:10]1[CH2:11][CH2:12][O:13][CH2:14][CH2:15]1.Cl[c:9]1[cH:8][cH:7][n:6][c:5]2[cH:4][cH:3][c:2]([Br:1])[cH:17][c:16]21>>[Br:1][c:2]1[cH:3][cH:4][c:5]2[n:6][cH:7][cH:8][c:9]([N:10]3[CH2:11][CH2:12][O:13][CH2:14][CH2:15]3)[c:16]2[cH:17]1 | C1COCCN1.Clc1ccnc2ccc(Br)cc12 | Brc1ccc2nccc(N3CCOCC3)c2c1 | null | null | null | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | 7aa932588efc8aa136efe0e43f3ce3bc189e51460b145a5586838f54c5c09e43 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc2c(N3CCOCC3)ccnc2c1 | Cl-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8].[#8:9]1-[C:10]-[C:11]-[NH;D2;+0:12]-[C:13]-[C:14]-1>>[c:8]:[c:7]1:[c:5](:[c:6]):[#7;a:4]:[c:3]:[c:2]:[c;H0;D3;+0:1]:1-[N;H0;D3;+0:12]1-[C:11]-[C:10]-[#8:9]-[C:14]-[C:13]-1 | null | [] | null | null | null | null | 122 mg 6-bromo-4-chloroquinoline and 0.13 mL morpholine were reacted by the same method as in Production Example 74 to give 68 mg of the title compound as a colorless oil.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | C1COCCN1.c1ccc2ncccc2c1 | c1ccc2ncccc2c1.C1COCC[NH]1 | c1ccc2ncccc2c1.C1COCC[NH]1 | HCl | null | null | null | C1COCCN1.Clc1ccnc2ccc(Br)cc12>>Brc1ccc2nccc(N3CCOCC3)c2c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-9f5c47e6abf24ea29759758b6122ce6b | Clc1ccnc2ccc(Br)cc12.c1ccc(N2CCNCC2)nc1>>Brc1ccc2nccc(N3CCN(c4ccccn4)CC3)c2c1 | BrC=1C=C2C(=CC=NC2=CC1)Cl.N1=C(C=CC=C1)N1CCNCC1>>BrC=1C=C2C(=CC=NC2=CC1)N1CCN(CC1)C1=NC=CC=C1 | Cl[c:9]1[cH:8][cH:7][n:6][c:5]2[cH:4][cH:3][c:2]([Br:1])[cH:23][c:22]21.[NH:10]1[CH2:11][CH2:12][N:13]([c:14]2[cH:15][cH:16][cH:17][cH:18][n:19]2)[CH2:20][CH2:21]1>>[Br:1][c:2]1[cH:3][cH:4][c:5]2[n:6][cH:7][cH:8][c:9]([N:10]3[CH2:11][CH2:12][N:13]([c:14]4[cH:15][cH:16][cH:17][cH:18][n:19]4)[CH2:20][CH2:21]3)[c:22]2[cH:... | Clc1ccnc2ccc(Br)cc12.c1ccc(N2CCNCC2)nc1 | Brc1ccc2nccc(N3CCN(c4ccccn4)CC3)c2c1 | null | null | null | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | 98c8ae975f310a76e6895ad2c03786dcf0895f15908d93475fb9e11cf83466fa | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc(N2CCN(c3ccnc4ccccc34)CC2)nc1 | Cl-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8].[#7:9]1-[C:10]-[C:11]-[NH;D2;+0:12]-[C:13]-[C:14]-1>>[c:8]:[c:7]1:[c:5](:[c:6]):[#7;a:4]:[c:3]:[c:2]:[c;H0;D3;+0:1]:1-[N;H0;D3;+0:12]1-[C:11]-[C:10]-[#7:9]-[C:14]-[C:13]-1 | null | [] | null | null | null | null | 291 mg 6-bromo-4-chloroquinoline and 0.91 mL 4-(2-pyridyl)piperazine were reacted by the same method as in Production Example 74 to give 373 mg of the title compound as a colorless oil.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | c1ccc2ncccc2c1.C1CNCC[NH]1 | c1ccc2ncccc2c1.C1C[NH]CC[NH]1 | c1ccc2ncccc2c1.C1C[NH]CC[NH]1.c1ccncc1 | HCl | null | null | null | Clc1ccnc2ccc(Br)cc12.c1ccc(N2CCNCC2)nc1>>Brc1ccc2nccc(N3CCN(c4ccccn4)CC3)c2c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-27070b7657314989abb352220f1b84f4 | CC(C)(C)OC(=O)N1CCNCC1.Clc1ccnc2ccc(Br)cc12>>CC(C)(C)OC(=O)N1CCN(c2ccnc3ccc(Br)cc23)CC1 | BrC=1C=C2C(=CC=NC2=CC1)Cl.N1(CCNCC1)C(=O)OC(C)(C)C.C(C)N(CC)CC.CS(=O)C>>BrC=1C=C2C(=CC=NC2=CC1)N1CCN(CC1)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][NH:11][CH2:23][CH2:24]1.Cl[c:12]1[cH:13][cH:14][n:15][c:16]2[cH:17][cH:18][c:19]([Br:20])[cH:21][c:22]12>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][N:11]([c:12]2[cH:13][cH:14][n:15][c:16]3[cH:17][cH:18][c:19]([Br:20])[cH:2... | CC(C)(C)OC(=O)N1CCNCC1.Clc1ccnc2ccc(Br)cc12 | CC(C)(C)OC(=O)N1CCN(c2ccnc3ccc(Br)cc23)CC1 | null | null | O.C(C)(=O)OCC | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | 9f69c5c4a4ea31f8d76ec3987be7bd40b9cb34092e5d3f4fe2f7075ca0afa5f4 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc2c(N3CCNCC3)ccnc2c1 | Cl-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8].[#7:9]1-[C:10]-[C:11]-[NH;D2;+0:12]-[C:13]-[C:14]-1>>[c:6]:[c:5]1:[#7;a:4]:[c:3]:[c:2]:[c;H0;D3;+0:1](-[N;H0;D3;+0:12]2-[C:13]-[C:14]-[#7:9]-[C:10]-[C:11]-2):[c:7]:1:[c:8] | 71.7 | [{"value": 71.7, "product": "BrC=1C=C2C(=CC=NC2=CC1)N1CCN(CC1)C(=O)OC(C)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | 8 | HOUR | A mixture of 243 mg 6-bromo-4-chloroquinoline, 373 mg t-butyl 1-piperazine carboxylate, 0.28 mL triethylamine and 10 mL dimethyl sulfoxide was stirred at 80° C. overnight. Ethyl acetate and water were added to the reaction solution, and the organic layer was separated, washed twice with water and then with brine and dr... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | C1C[NH]CCN1.c1ccc2ncccc2c1 | C1C[NH]CC[NH]1.c1ccc2ncccc2c1 | C1C[NH]CC[NH]1.c1ccc2ncccc2c1 | HCl | O.C(C)(=O)OCC | 80 | 8 | CC(C)(C)OC(=O)N1CCNCC1.Clc1ccnc2ccc(Br)cc12>O.C(C)(=O)OCC>CC(C)(C)OC(=O)N1CCN(c2ccnc3ccc(Br)cc23)CC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-81d64fbcd2ec4401aa24fe933c90a8e1 | COC1CCNCC1.Clc1ccnc2ccc(Br)cc12>>COC1CCN(c2ccnc3ccc(Br)cc23)CC1 | BrC=1C=C2C(=CC=NC2=CC1)Cl.Cl.COC1CCNCC1.C(C)N(CC)CC.CN(C=O)C>>COC1CCN(CC1)C1=CC=NC2=CC=C(C=C12)Br | [CH3:1][O:2][CH:3]1[CH2:4][CH2:5][NH:6][CH2:18][CH2:19]1.Cl[c:7]1[cH:8][cH:9][n:10][c:11]2[cH:12][cH:13][c:14]([Br:15])[cH:16][c:17]12>>[CH3:1][O:2][CH:3]1[CH2:4][CH2:5][N:6]([c:7]2[cH:8][cH:9][n:10][c:11]3[cH:12][cH:13][c:14]([Br:15])[cH:16][c:17]23)[CH2:18][CH2:19]1 | COC1CCNCC1.Clc1ccnc2ccc(Br)cc12 | COC1CCN(c2ccnc3ccc(Br)cc23)CC1 | null | null | O.C(C)(=O)OCC | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | 6ca896bdf5cf17e98a9402041cc62e117ebb3e6ff582ec413fbc5219ab9874c5 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc2c(N3CCCCC3)ccnc2c1 | Cl-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8].[C:9]-[C:10]-[NH;D2;+0:11]-[C:12]-[C:13]>>[C:9]-[C:10]-[N;H0;D3;+0:11](-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8])-[C:12]-[C:13] | 77.9 | [{"value": 77.9, "product": "COC1CCN(CC1)C1=CC=NC2=CC=C(C=C12)Br", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 130 | CELSIUS | 8 | HOUR | A mixture of 500 mg 6-bromo-4-chloroquinoline, 330 mg 4-methoxypiperidine monohydrochloride, 0.57 mL triethylamine and 10 mL N,N-dimethylformamide was stirred at 130° C. for 8 hours. Ethyl acetate and water were added to the reaction solution, and the organic layer was separated. The organic layer was washed with water... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | C1CCNCC1.c1ccc2ncccc2c1 | C1CC[NH]CC1.c1ccc2ncccc2c1 | C1CC[NH]CC1.c1ccc2ncccc2c1 | HCl | O.C(C)(=O)OCC | 130 | 8 | COC1CCNCC1.Clc1ccnc2ccc(Br)cc12>O.C(C)(=O)OCC>COC1CCN(c2ccnc3ccc(Br)cc23)CC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-89fd9da20ba146b4ac2f3d471bf591bc | CO[C@H]1CNC[C@@H]1OC.Clc1ccnc2ccc(Br)cc12>>CO[C@H]1CN(c2ccnc3ccc(Br)cc23)C[C@@H]1OC | BrC=1C=C2C(=CC=NC2=CC1)Cl.Cl.CO[C@H]1CNC[C@@H]1OC>>BrC=1C=C2C(=CC=NC2=CC1)N1C[C@@H]([C@H](C1)OC)OC | [CH3:1][O:2][C@H:3]1[CH2:4][NH:5][CH2:17][C@@H:18]1[O:19][CH3:20].Cl[c:6]1[cH:7][cH:8][n:9][c:10]2[cH:11][cH:12][c:13]([Br:14])[cH:15][c:16]12>>[CH3:1][O:2][C@H:3]1[CH2:4][N:5]([c:6]2[cH:7][cH:8][n:9][c:10]3[cH:11][cH:12][c:13]([Br:14])[cH:15][c:16]23)[CH2:17][C@@H:18]1[O:19][CH3:20] | CO[C@H]1CNC[C@@H]1OC.Clc1ccnc2ccc(Br)cc12 | CO[C@H]1CN(c2ccnc3ccc(Br)cc23)C[C@@H]1OC | null | null | null | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | 89f800d0b5c6eace023ec0f16ed65844f5dd409e156b3b4845e1db5de9a38872 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc2c(N3CCCC3)ccnc2c1 | Cl-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8].[C:9]1-[C:10]-[C:11]-[C:12]-[NH;D2;+0:13]-1>>[c:6]:[c:5]1:[#7;a:4]:[c:3]:[c:2]:[c;H0;D3;+0:1](-[N;H0;D3;+0:13]2-[C:9]-[C:10]-[C:11]-[C:12]-2):[c:7]:1:[c:8] | 35.7 | [{"value": 35.7, "product": "BrC=1C=C2C(=CC=NC2=CC1)N1C[C@@H]([C@H](C1)OC)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 697 mg 6-bromo-4-chloroquinoline and 482 mg (3S,4S)-3,4-dimethoxytetrahydro-1H pyrrole monohydrochloride were reacted by the same method as in Production Example 82, to give 346 mg of the title compound as pale brown crystals.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | C1CCNC1.c1ccc2ncccc2c1 | C1CC[NH]C1.c1ccc2ncccc2c1 | C1CC[NH]C1.c1ccc2ncccc2c1 | HCl | null | null | null | CO[C@H]1CNC[C@@H]1OC.Clc1ccnc2ccc(Br)cc12>>CO[C@H]1CN(c2ccnc3ccc(Br)cc23)C[C@@H]1OC |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-44a5b37683ee46fc947e367ce6e12229 | CO[C@@H]1CCNC1.Clc1ccnc2ccc(Br)cc12>>CO[C@@H]1CCN(c2ccnc3ccc(Br)cc23)C1 | BrC=1C=C2C(=CC=NC2=CC1)Cl.Cl.CO[C@H]1CNCC1>>BrC=1C=C2C(=CC=NC2=CC1)N1C[C@@H](CC1)OC | [CH3:1][O:2][C@@H:3]1[CH2:4][CH2:5][NH:6][CH2:18]1.Cl[c:7]1[cH:8][cH:9][n:10][c:11]2[cH:12][cH:13][c:14]([Br:15])[cH:16][c:17]12>>[CH3:1][O:2][C@@H:3]1[CH2:4][CH2:5][N:6]([c:7]2[cH:8][cH:9][n:10][c:11]3[cH:12][cH:13][c:14]([Br:15])[cH:16][c:17]23)[CH2:18]1 | CO[C@@H]1CCNC1.Clc1ccnc2ccc(Br)cc12 | CO[C@@H]1CCN(c2ccnc3ccc(Br)cc23)C1 | null | null | null | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | 89f800d0b5c6eace023ec0f16ed65844f5dd409e156b3b4845e1db5de9a38872 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc2c(N3CCCC3)ccnc2c1 | Cl-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8].[C:9]1-[C:10]-[C:11]-[C:12]-[NH;D2;+0:13]-1>>[c:6]:[c:5]1:[#7;a:4]:[c:3]:[c:2]:[c;H0;D3;+0:1](-[N;H0;D3;+0:13]2-[C:9]-[C:10]-[C:11]-[C:12]-2):[c:7]:1:[c:8] | 44.8 | [{"value": 44.8, "product": "BrC=1C=C2C(=CC=NC2=CC1)N1C[C@@H](CC1)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 500 mg 6-bromo-4-chloroquinoline and 300 mg (3R)-3-methoxy pyrrolidine monohydrochloride were reacted by the same method as in Production Example 82, to give 284 mg of the title compound as a yellow oil.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | C1CCNC1.c1ccc2ncccc2c1 | C1CC[NH]C1.c1ccc2ncccc2c1 | C1CC[NH]C1.c1ccc2ncccc2c1 | HCl | null | null | null | CO[C@@H]1CCNC1.Clc1ccnc2ccc(Br)cc12>>CO[C@@H]1CCN(c2ccnc3ccc(Br)cc23)C1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-2b980d3bc2484497869d7efaf50a8779 | Clc1ccnc2ccc(Br)cc12.c1ccc(OC2CCNCC2)nc1>>Brc1ccc2nccc(N3CCC(Oc4ccccn4)CC3)c2c1 | BrC=1C=C2C(=CC=NC2=CC1)Cl.Cl.Cl.N1CCC(CC1)OC1=NC=CC=C1>>BrC=1C=C2C(=CC=NC2=CC1)N1CCC(CC1)OC1=NC=CC=C1 | Cl[c:9]1[cH:8][cH:7][n:6][c:5]2[cH:4][cH:3][c:2]([Br:1])[cH:24][c:23]21.[NH:10]1[CH2:11][CH2:12][CH:13]([O:14][c:15]2[cH:16][cH:17][cH:18][cH:19][n:20]2)[CH2:21][CH2:22]1>>[Br:1][c:2]1[cH:3][cH:4][c:5]2[n:6][cH:7][cH:8][c:9]([N:10]3[CH2:11][CH2:12][CH:13]([O:14][c:15]4[cH:16][cH:17][cH:18][cH:19][n:20]4)[CH2:21][CH2:22... | Clc1ccnc2ccc(Br)cc12.c1ccc(OC2CCNCC2)nc1 | Brc1ccc2nccc(N3CCC(Oc4ccccn4)CC3)c2c1 | null | null | null | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | 6ca896bdf5cf17e98a9402041cc62e117ebb3e6ff582ec413fbc5219ab9874c5 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc(OC2CCN(c3ccnc4ccccc34)CC2)nc1 | Cl-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8].[C:9]-[C:10]-[NH;D2;+0:11]-[C:12]-[C:13]>>[C:9]-[C:10]-[N;H0;D3;+0:11](-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8])-[C:12]-[C:13] | 79.4 | [{"value": 79.4, "product": "BrC=1C=C2C(=CC=NC2=CC1)N1CCC(CC1)OC1=NC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 500 mg 6-bromo-4-chloroquinoline and 540 mg 2-(4-piperidyloxy) pyridine dihydrochloride were reacted by the same method as in Production Example 82, to give 629 mg of the title compound as an orange oil.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | c1ccc2ncccc2c1.C1CCNCC1 | c1ccc2ncccc2c1.C1CC[NH]CC1 | c1ccc2ncccc2c1.C1CC[NH]CC1.c1ccncc1 | HCl | null | null | null | Clc1ccnc2ccc(Br)cc12.c1ccc(OC2CCNCC2)nc1>>Brc1ccc2nccc(N3CCC(Oc4ccccn4)CC3)c2c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-f7a48dd0422e4d15afe9cbf385fb152a | CCOC(=O)C1CCNCC1.Clc1ccnc2ccc(Br)cc12>>CCOC(=O)C1CCN(c2ccnc3ccc(Br)cc23)CC1 | BrC=1C=C2C(=CC=NC2=CC1)Cl.N1CCC(CC1)C(=O)OCC>>BrC=1C=C2C(=CC=NC2=CC1)N1CCC(CC1)C(=O)OCC | [CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]1[CH2:7][CH2:8][NH:9][CH2:21][CH2:22]1.Cl[c:10]1[cH:11][cH:12][n:13][c:14]2[cH:15][cH:16][c:17]([Br:18])[cH:19][c:20]12>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]1[CH2:7][CH2:8][N:9]([c:10]2[cH:11][cH:12][n:13][c:14]3[cH:15][cH:16][c:17]([Br:18])[cH:19][c:20]23)[CH2:21][CH2:22]1 | CCOC(=O)C1CCNCC1.Clc1ccnc2ccc(Br)cc12 | CCOC(=O)C1CCN(c2ccnc3ccc(Br)cc23)CC1 | null | null | null | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | 6ca896bdf5cf17e98a9402041cc62e117ebb3e6ff582ec413fbc5219ab9874c5 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc2c(N3CCCCC3)ccnc2c1 | Cl-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8].[C:9]-[C:10]-[NH;D2;+0:11]-[C:12]-[C:13]>>[C:9]-[C:10]-[N;H0;D3;+0:11](-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8])-[C:12]-[C:13] | 64.1 | [{"value": 64.1, "product": "BrC=1C=C2C(=CC=NC2=CC1)N1CCC(CC1)C(=O)OCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 500 mg 6-bromo-4-chloroquinoline and 340 mg ethyl 4-piperidine carboxylate were reacted by the same method as in Production Example 74, to give 480 mg of the title compound as a yellow oil.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | C1CCNCC1.c1ccc2ncccc2c1 | C1CC[NH]CC1.c1ccc2ncccc2c1 | C1CC[NH]CC1.c1ccc2ncccc2c1 | HCl | null | null | null | CCOC(=O)C1CCNCC1.Clc1ccnc2ccc(Br)cc12>>CCOC(=O)C1CCN(c2ccnc3ccc(Br)cc23)CC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-4b79f5dff96f4fe7a29b5ace3d4445d4 | CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[c]1cccs1.Clc1ncnc2ccc(Br)cc12>>Brc1ccc2ncnc(-c3cccs3)c2c1 | BrC=1C=C2C(=NC=NC2=CC1)Cl.C(CCC)[Sn](C=1SC=CC1)(CCCC)CCCC>>BrC=1C=C2C(=NC=NC2=CC1)C=1SC=CC1 | CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[c:10]1[cH:11][cH:12][cH:13][s:14]1.Cl[c:9]1[n:8][cH:7][n:6][c:5]2[cH:4][cH:3][c:2]([Br:1])[cH:16][c:15]21>>[Br:1][c:2]1[cH:3][cH:4][c:5]2[n:6][cH:7][n:8][c:9](-[c:10]3[cH:11][cH:12][cH:13][s:14]3)[c:15]2[cH:16]1 | CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[c]1cccs1.Clc1ncnc2ccc(Br)cc12 | Brc1ccc2ncnc(-c3cccs3)c2c1 | null | null | C1(=CC=CC=C1)C | C-C Coupling | Stille reaction_aryl | 9d6933a964770fa23bac63577249a9b6209b9d6653ec0f7df7a6a7fbd8151548 | db27eeefac0475c6d74fa10b3167e95a61caaae74e8bbafd45892452c0c3d4d6 | c1csc(-c2ncnc3ccccc23)c1 | C-C-C-[CH2]-[Sn](-[CH2]-C-C-C)(-[CH2]-C-C-C)-[c;H0;D3;+0:1]1:[#16;a:2]:[c:3]:[c:4]:[c:5]:1.Cl-[c;H0;D3;+0:6]1:[#7;a:7]:[c:8]:[#7;a:9]:[c:10](:[c:11]):[c:12]:1:[c:13]>>[c:13]:[c:12]1:[c:10](:[c:11]):[#7;a:9]:[c:8]:[#7;a:7]:[c;H0;D3;+0:6]:1-[c;H0;D3;+0:1]1:[#16;a:2]:[c:3]:[c:4]:[c:5]:1 | null | [] | 80 | CELSIUS | 24 | HOUR | 0.6 g 6-bromo-4-chloroquinazoline was dissolved in 18 mL toluene, and 0.82 mL tri-n-butyl(2-thienyl)stannane and 0.14 g tetrakis (triphenylphosphine)palladium (0) were added thereto and stirred at 80° C. for 24 hours under nitrogen atmosphere. After the solvent was evaporated, the residue was purified by silica gel chr... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Tin | null | c1ccsc1.c1ccc2ncncc2c1 | c1ccc2ncncc2c1.c1ccsc1 | c1ccc2ncncc2c1.c1ccsc1 | HCl.Sn | C1(=CC=CC=C1)C | 80 | 24 | CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[c]1cccs1.Clc1ncnc2ccc(Br)cc12>C1(=CC=CC=C1)C>Brc1ccc2ncnc(-c3cccs3)c2c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-3c5a26d55dd54e2e9666e23a47ffb5d3 | Clc1ncnc2ccc(Br)cc12.FC(F)(F)c1cccc(N2CCNCC2)c1>>FC(F)(F)c1cccc(N2CCN(c3ncnc4ccc(Br)cc34)CC2)c1 | BrC=1C=C2C(=NC=NC2=CC1)Cl.FC(C=1C=C(C=CC1)N1CCNCC1)(F)F.C(C)N(CC)CC>>BrC=1C=C2C(=NC=NC2=CC1)N1CCN(CC1)C1=CC(=CC=C1)C(F)(F)F | Cl[c:14]1[n:15][cH:16][n:17][c:18]2[cH:19][cH:20][c:21]([Br:22])[cH:23][c:24]12.[F:1][C:2]([F:3])([F:4])[c:5]1[cH:6][cH:7][cH:8][c:9]([N:10]2[CH2:11][CH2:12][NH:13][CH2:25][CH2:26]2)[cH:27]1>>[F:1][C:2]([F:3])([F:4])[c:5]1[cH:6][cH:7][cH:8][c:9]([N:10]2[CH2:11][CH2:12][N:13]([c:14]3[n:15][cH:16][n:17][c:18]4[cH:19][cH:... | Clc1ncnc2ccc(Br)cc12.FC(F)(F)c1cccc(N2CCNCC2)c1 | FC(F)(F)c1cccc(N2CCN(c3ncnc4ccc(Br)cc34)CC2)c1 | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | bf3493eee827560da1b96eed7238401d257cea1a4f36eecd786eab0e1b0d6849 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc(N2CCN(c3ncnc4ccccc34)CC2)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8].[#7:9]1-[C:10]-[C:11]-[NH;D2;+0:12]-[C:13]-[C:14]-1>>[c:6]:[c:5]1:[#7;a:4]:[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[N;H0;D3;+0:12]2-[C:11]-[C:10]-[#7:9]-[C:14]-[C:13]-2):[c:7]:1:[c:8] | 66.8 | [{"value": 66.8, "product": "BrC=1C=C2C(=NC=NC2=CC1)N1CCN(CC1)C1=CC(=CC=C1)C(F)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 4 | HOUR | A mixture of 300 mg 6-bromo-4-chloroquinazoline, 350 mg 1-[3-(trifluoromethyl)phenyl]piperazine, 0.18 mL triethylamine and 5 mL N,N-dimethylformamide was stirred at room temperature for 4 hours. After the solvent was evaporated, the residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | c1ccc2ncncc2c1.C1C[NH]CCN1 | C1C[NH]CC[NH]1.c1ccc2ncncc2c1 | c1ccccc1.C1C[NH]CC[NH]1.c1ccc2ncncc2c1 | HCl | CN(C=O)C | null | 4 | Clc1ncnc2ccc(Br)cc12.FC(F)(F)c1cccc(N2CCNCC2)c1>CN(C=O)C>FC(F)(F)c1cccc(N2CCN(c3ncnc4ccc(Br)cc34)CC2)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-e03a8a5d6a4d424ba1fe1ef24c7a44ef | N#CCc1ccc(F)cc1.O=[N+]([O-])c1ccc(Br)cc1>>Fc1ccc(-c2onc3ccc(Br)cc23)cc1 | O.BrC1=CC=C(C=C1)[N+](=O)[O-].FC1=CC=C(C=C1)CC#N.[OH-].[Na+]>>BrC1=CC=2C(=NOC2C2=CC=C(C=C2)F)C=C1 | N#C[CH2:6][c:5]1[cH:4][cH:3][c:2]([F:1])[cH:17][cH:16]1.O=[N+:8]([O-:7])[c:9]1[cH:10][cH:11][c:12]([Br:13])[cH:14][cH:15]1>>[F:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[o:7][n:8][c:9]3[cH:10][cH:11][c:12]([Br:13])[cH:14][c:15]23)[cH:16][cH:17]1 | N#CCc1ccc(F)cc1.O=[N+]([O-])c1ccc(Br)cc1 | Fc1ccc(-c2onc3ccc(Br)cc23)cc1 | null | null | C(C)O | Aromatic Heterocycle Formation | OtherReaction | 0f22d84b2a4c2a0e4579a9b5d1adb0e1a3a85c6a163e0b5818a361e01201e52a | b0095d38e0fbba4b05f88363393446922ef1c66394cfc608f7c1cd4fc808583a | c1ccc(-c2onc3ccccc23)cc1 | N#C-[CH2;D2;+0:1]-[c;H0;D3;+0:2](:[c:3]:[c:4]):[c:5]:[c:6].O=[N+;H0;D3:7](-[O-;H0;D1:8])-[c:9](:[c:10]):[cH;D2;+0:11]:[c:12]:[c:13]>>[c:10]:[c:9]1:[n;H0;D2;+0:7]:[o;H0;D2;+0:8]:[c;H0;D3;+0:1](-[c;H0;D3;+0:2](:[c:3]:[c:4]):[c:5]:[c:6]):[c;H0;D3;+0:11]:1:[c:12]:[c:13] | null | [] | null | null | null | null | 13 g 1-bromo-4-nitrobenzene, 7.68 mL 2-(4-fluorophenyl)acetonitrile and 3.9 g sodium hydroxide were stirred in 130 mL ethanol at 40° C. for 24 hours. After the reaction solution was left and cooled, water was added thereto and the reaction solution was extracted with ethylacetate. The organic solvent was washed with br... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile.Nitro group | null | c1ccccc1 | c1ccc2nocc2c1 | c1ccccc1.c1ccc2nocc2c1 | HO- | C(C)O | null | null | N#CCc1ccc(F)cc1.O=[N+]([O-])c1ccc(Br)cc1>C(C)O>Fc1ccc(-c2onc3ccc(Br)cc23)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-4041fef8b4e54995b5089ae87eb6ab96 | COC(=O)c1ccc(-c2ccn(C(c3ccccc3)(c3ccccc3)c3ccccc3)n2)s1.O=C1CCC(=O)N1I>>COC(=O)c1ccc(-c2nn(C(c3ccccc3)(c3ccccc3)c3ccccc3)cc2I)s1 | C(C1=CC=CC=C1)(C1=CC=CC=C1)(C1=CC=CC=C1)N1N=C(C=C1)C1=CC=C(S1)C(=O)OC.IN1C(CCC1=O)=O.S(=S)(=O)([O-])[O-].[Na+].[Na+].C([O-])(O)=O.[Na+].IN1C(CCC1=O)=O>>IC=1C(=NN(C1)C(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)C1=CC=C(S1)C(=O)OC | [CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8](-[c:9]2[n:10][n:11]([C:12]([c:13]3[cH:14][cH:15][cH:16][cH:17][cH:18]3)([c:19]3[cH:20][cH:21][cH:22][cH:23][cH:24]3)[c:25]3[cH:26][cH:27][cH:28][cH:29][cH:30]3)[cH:31][cH:32]2)[s:34]1.O=C1CCC(=O)N1[I:33]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8](-[c:9]2[n:10][n:1... | COC(=O)c1ccc(-c2ccn(C(c3ccccc3)(c3ccccc3)c3ccccc3)n2)s1.O=C1CCC(=O)N1I | COC(=O)c1ccc(-c2nn(C(c3ccccc3)(c3ccccc3)c3ccccc3)cc2I)s1 | null | null | CN(C=O)C | Functional Group Interconversion | OtherReaction | 13d4025b7e4d89e18a4bdf4324e272b69308705ca7d8d86b51c72ac440b14757 | 0e444576b73669992a4073cc3f7b10ed52cb9df09f9f8e4042e39e6a602aa390 | c1ccc(C(c2ccccc2)(c2ccccc2)n2ccc(-c3cccs3)n2)cc1 | O=C1-C-C-C(=O)-N-1-[I;H0;D1;+0:1].[#16;a:2]:[c:3]-[c:4]1:[#7;a:5]:[#7;a:6](-[C:7]):[c:8]:[cH;D2;+0:9]:1>>[#16;a:2]:[c:3]-[c:4]1:[#7;a:5]:[#7;a:6](-[C:7]):[c:8]:[c;H0;D3;+0:9]:1-[I;H0;D1;+0:1] | 95.7 | [{"value": 95.7, "product": "IC=1C(=NN(C1)C(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)C1=CC=C(S1)C(=O)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | 24 | HOUR | 20 g methyl 5-(1-trityl-1H-3-pyrazolyl)-2-thiophene carboxylate and 10.6 g N-iodosuccinimide were stirred in 200 mL N,N-dimethylformamide at 80° C. for 24 hours. Additional N-iodosuccinimide, 10.6 g, was added thereto and stirred at 80° C. for 24 hours, and then an aqueous solution of sodium thiosulfate and an aqueous ... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Tertiary amide | Aromatic halide | c1ccn[nH]1.C1CCNC1 | c1c[nH]nc1 | c1ccsc1.c1c[nH]nc1.c1ccccc1.c1ccccc1.c1ccccc1 | HO- | CN(C=O)C | 80 | 24 | COC(=O)c1ccc(-c2ccn(C(c3ccccc3)(c3ccccc3)c3ccccc3)n2)s1.O=C1CCC(=O)N1I>CN(C=O)C>COC(=O)c1ccc(-c2nn(C(c3ccccc3)(c3ccccc3)c3ccccc3)cc2I)s1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-d4c5a74becb748159582e59b4d9a4a5e | CC(=O)c1ccc(O)cc1.C[Si](C)(C)CCOCCl>>CC(=O)c1ccc(OCOCC[Si](C)(C)C)cc1 | C[Si](CCOCCl)(C)C.CC(=O)C=1C=CC(=CC1)O.C(C)(C)N(CC)C(C)C>>C[Si](CCOCOC1=CC=C(C=C1)C(C)=O)(C)C | [CH3:1][C:2](=[O:3])[c:4]1[cH:5][cH:6][c:7]([OH:8])[cH:17][cH:18]1.Cl[CH2:9][O:10][CH2:11][CH2:12][Si:13]([CH3:14])([CH3:15])[CH3:16]>>[CH3:1][C:2](=[O:3])[c:4]1[cH:5][cH:6][c:7]([O:8][CH2:9][O:10][CH2:11][CH2:12][Si:13]([CH3:14])([CH3:15])[CH3:16])[cH:17][cH:18]1 | CC(=O)c1ccc(O)cc1.C[Si](C)(C)CCOCCl | CC(=O)c1ccc(OCOCC[Si](C)(C)C)cc1 | null | null | ClCCl | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 6e90ffbf0683e1a3ee55c5e3ea453aefc5ddd369c0150ed0150f9546d7e47f4f | efd670663709b79afcad1306da9f69b33a0147cfa3639ca4c0b54b35ef4b1852 | c1ccccc1 | Cl-[CH2;D2;+0:1]-[#8:2]-[C:3].[OH;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[C:3]-[#8:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:4]-[c:5](:[c:6]):[c:7] | null | [] | null | null | 4 | HOUR | While 30 mL solution of 2.72 g 4-hydroxyacetophenone and 5.2 mL diisopropyl ethylamine in dichloromethane was stirred under ice-cooling in a stream of nitrogen, 4.2 mL 2-(trimethylsilyl)ethoxymethyl chloride was added thereto. Then, the reaction solution was stirred at room temperature for 4 hours. The reaction solutio... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ether.Aromatic alcohol | Ether.Ether | null | null | c1ccccc1 | HCl | ClCCl | null | 4 | CC(=O)c1ccc(O)cc1.C[Si](C)(C)CCOCCl>ClCCl>CC(=O)c1ccc(OCOCC[Si](C)(C)C)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-1b320b4caf48445d87272a3586e3dd76 | Nc1ccc(-c2nn(C(c3ccccc3)(c3ccccc3)c3ccccc3)cc2Br)cc1>>CN(C)c1ccc(-c2nn(C(c3ccccc3)(c3ccccc3)c3ccccc3)cc2Br)cc1 | C(C)(=O)O[BH-](OC(C)=O)OC(C)=O.[Na+].BrC=1C(=NN(C1)C(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)C1=CC=C(C=C1)N.C(=O)N.C([O-])(O)=O.[Na+]>>BrC=1C(=NN(C1)C(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)C1=CC=C(C=C1)N(C)C | [NH2:2][c:4]1[cH:5][cH:6][c:7](-[c:8]2[n:9][n:10]([C:11]([c:12]3[cH:13][cH:14][cH:15][cH:16][cH:17]3)([c:18]3[cH:19][cH:20][cH:21][cH:22][cH:23]3)[c:24]3[cH:25][cH:26][cH:27][cH:28][cH:29]3)[cH:30][c:31]2[Br:32])[cH:33][cH:34]1>>[CH3:1][N:2]([CH3:3])[c:4]1[cH:5][cH:6][c:7](-[c:8]2[n:9][n:10]([C:11]([c:12]3[cH:13][cH:14... | Nc1ccc(-c2nn(C(c3ccccc3)(c3ccccc3)c3ccccc3)cc2Br)cc1 | CN(C)c1ccc(-c2nn(C(c3ccccc3)(c3ccccc3)c3ccccc3)cc2Br)cc1 | null | null | O.ClCCCl.C(C)(=O)OCC | Miscellaneous | OtherReaction | 0295391ed0de2e86c7e882f3199152884d99da63bc1b927b39500202e1a00977 | 98c3809a8b4046b29490f9afb6277ec8718e0550ab1278bc09b7f0dc821fa6fe | c1ccc(-c2ccn(C(c3ccccc3)(c3ccccc3)c3ccccc3)n2)cc1 | [NH2;D1;+0:1]-[c:2](:[c:3]):[c:4]>>[C;D1;H3:5]-[N;H0;D3;+0:1](-[C;D1;H3:6])-[c:2](:[c:3]):[c:4] | null | [] | null | null | 3 | DAY | 2.54 g sodium triacetoxy borohydride was added little by little at room temperature to a mixture of 1.44 g 4-(4-bromo-1-trityl-1H-pyrazol-3-yl)phenylamine (compound in Production Example 152), 0.61 mL of 37% formamide and 40 mL 1,2-dichloroethane, and the mixture was stirred for 3 days. Ethyl acetate and an aqueous sat... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | Tertiary amine | null | null | c1ccccc1.c1c[nH]nc1.c1ccccc1.c1ccccc1.c1ccccc1 | Other | O.ClCCCl.C(C)(=O)OCC | null | 72 | Nc1ccc(-c2nn(C(c3ccccc3)(c3ccccc3)c3ccccc3)cc2Br)cc1>O.ClCCCl.C(C)(=O)OCC>CN(C)c1ccc(-c2nn(C(c3ccccc3)(c3ccccc3)c3ccccc3)cc2Br)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-9de829fad7074c198d36aaffabd3acbe | BrCCOCCBr.Nc1ccc(-c2nn(C(c3ccccc3)(c3ccccc3)c3ccccc3)cc2Br)cc1>>Brc1cn(C(c2ccccc2)(c2ccccc2)c2ccccc2)nc1-c1ccc(N2CCOCC2)cc1 | BrC=1C(=NN(C1)C(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)C1=CC=C(C=C1)N.BrCCOCCBr.[I-].[Na+].C([O-])([O-])=O.[K+].[K+]>>BrC=1C(=NN(C1)C(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)C1=CC=C(C=C1)N1CCOCC1 | Br[CH2:31][CH2:32][O:33][CH2:34][CH2:35]Br.[Br:1][c:2]1[cH:3][n:4]([C:5]([c:6]2[cH:7][cH:8][cH:9][cH:10][cH:11]2)([c:12]2[cH:13][cH:14][cH:15][cH:16][cH:17]2)[c:18]2[cH:19][cH:20][cH:21][cH:22][cH:23]2)[n:24][c:25]1-[c:26]1[cH:27][cH:28][c:29]([NH2:30])[cH:36][cH:37]1>>[Br:1][c:2]1[cH:3][n:4]([C:5]([c:6]2[cH:7][cH:8][c... | BrCCOCCBr.Nc1ccc(-c2nn(C(c3ccccc3)(c3ccccc3)c3ccccc3)cc2Br)cc1 | Brc1cn(C(c2ccccc2)(c2ccccc2)c2ccccc2)nc1-c1ccc(N2CCOCC2)cc1 | null | null | O.CN(C=O)C.C(C)(=O)OCC | Heteroatom Alkylation and Arylation | OtherReaction | 96e983e5a21a49df63baecef913e7d3b8dacd6365c270725738379ba775c02bb | 631870b1ab33be0edc94bc9ae10321f1c5ede4dd4db77035c9d3979e4a2118fb | c1ccc(C(c2ccccc2)(c2ccccc2)n2ccc(-c3ccc(N4CCOCC4)cc3)n2)cc1 | Br-[CH2;D2;+0:1]-[C:2]-[#8:3]-[C:4]-[CH2;D2;+0:5]-Br.[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[c:8]:[c:7](-[N;H0;D3;+0:6]1-[CH2;D2;+0:1]-[C:2]-[#8:3]-[C:4]-[CH2;D2;+0:5]-1):[c:9] | null | [] | 80 | CELSIUS | 3 | DAY | A mixture of 2.4 g 4-(4-bromo-1-trityl-1H-pyrazol-3-yl)phenylamine (compound in Production Example 152), 0.7 mL 2-bromoethyl ether, 80 mg sodium iodide, 1.52 g potassium carbonate and 50 mL N,N-dimethylformamide was stirred at 80° C. for 3 days. Ethyl acetate and water were added to the reaction solution, then water wa... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary halide.Primary amine | Tertiary amine | null | C1COCC[NH]1 | c1cn[nH]c1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1.C1COCC[NH]1 | HBr | O.CN(C=O)C.C(C)(=O)OCC | 80 | 72 | BrCCOCCBr.Nc1ccc(-c2nn(C(c3ccccc3)(c3ccccc3)c3ccccc3)cc2Br)cc1>O.CN(C=O)C.C(C)(=O)OCC>Brc1cn(C(c2ccccc2)(c2ccccc2)c2ccccc2)nc1-c1ccc(N2CCOCC2)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-7e06764fbfd84dcfb07798a6103e3bba | C=[C](OCC)[Sn]([CH2]CCC)([CH2]CCC)[CH2]CCC.Cc1ccc(Br)c(F)c1>>CC(=O)c1ccc(C)cc1F | BrC1=C(C=C(C=C1)C)F.C(CCC)[Sn](C(=C)OCC)(CCCC)CCCC>>FC1=C(C=CC(=C1)C)C(C)=O | CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[C:2](=[CH2:1])[O:3]CC.Br[c:4]1[cH:5][cH:6][c:7]([CH3:8])[cH:9][c:10]1[F:11]>>[CH3:1][C:2](=[O:3])[c:4]1[cH:5][cH:6][c:7]([CH3:8])[cH:9][c:10]1[F:11] | C=[C](OCC)[Sn]([CH2]CCC)([CH2]CCC)[CH2]CCC.Cc1ccc(Br)c(F)c1 | CC(=O)c1ccc(C)cc1F | null | [Pd].C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1 | [F-].[K+].C1(=CC=CC=C1)C.C(C)(=O)OCC | Acylation | OtherReaction | e81a9e4f1410d41358aeb55fc26a37a1b785aea938455868d964ef705a085ee2 | 63004495c3d76884d1ef7552ef244f48fc0c4b379316352f7c7b6b3ce0e8b2c8 | c1ccccc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[F;D1;H0:5]):[c:6].C-C-C-[CH2]-[Sn](-[CH2]-C-C-C)(-[CH2]-C-C-C)-[C;H0;D3;+0:7](=[CH2;D1;+0:8])-[O;H0;D2;+0:9]-C-C>>[CH3;D1;+0:8]-[C;H0;D3;+0:7](=[O;H0;D1;+0:9])-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[F;D1;H0:5]):[c:6] | 114.5 | [{"value": 114.5, "product": "FC1=C(C=CC(=C1)C)C(C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | 54 mL solution of 5.0 g 1-bromo-2-fluoro-4-methylbenzene, 10 g tributyl(1-ethoxyvinyl)tin and 1.53 g tetrakis (triphenylphosphine) palladium in toluene was heated at 120° C. for 2 hours. After cooling to room temperature, the reaction mixture was diluted with ethyl acetate, 10% aqueous potassium fluoride solution was a... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ether.Vinyl.Tin | Ketone | c1ccccc1 | c1ccccc1 | c1ccccc1 | HBr.Sn | [Pd].C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.[F-].[K+].C1(=CC=CC=C1)C.C(C)(=O)OCC | null | 0.5 | C=[C](OCC)[Sn]([CH2]CCC)([CH2]CCC)[CH2]CCC.Cc1ccc(Br)c(F)c1>[Pd].C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.[F-].[K+].C1(=CC=CC=C1)C.C(C)(=O)OCC>CC(=O)c1ccc(C)cc1F |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-f1c2816f2f184ef9a353812df19c64f4 | CC(=O)c1ccc(F)cc1F.COCCO>>COCCOc1cc(F)ccc1C(C)=O | O.COCCO.[H-].[Na+].FC1=C(C=CC(=C1)F)C(C)=O>>FC1=CC(=C(C=C1)C(C)=O)OCCOC | F[c:6]1[cH:7][c:8]([F:9])[cH:10][cH:11][c:12]1[C:13]([CH3:14])=[O:15].[CH3:1][O:2][CH2:3][CH2:4][OH:5]>>[CH3:1][O:2][CH2:3][CH2:4][O:5][c:6]1[cH:7][c:8]([F:9])[cH:10][cH:11][c:12]1[C:13]([CH3:14])=[O:15] | CC(=O)c1ccc(F)cc1F.COCCO | COCCOc1cc(F)ccc1C(C)=O | null | null | O1CCCC1 | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 4821d6d7238522ee9ef4538c00647e855becf4de3d9c939c0cec2b01c1e5e915 | a4cafa7bcd156e21cca6eaac1b32e28ec8540642a31181122e6957f3d7559631 | c1ccccc1 | F-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[C:5](-[C;D1;H3:6])=[O;D1;H0:7]):[c:8].[C:9]-[C:10]-[OH;D1;+0:11]>>[C:9]-[C:10]-[O;H0;D2;+0:11]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[C:5](-[C;D1;H3:6])=[O;D1;H0:7]):[c:8] | 69.6 | [{"value": 69.6, "product": "FC1=CC(=C(C=C1)C(C)=O)OCCOC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 24 | HOUR | A solution of 1.75 g 2-methoxy ethanol in tetrahydrofuran (23 mL) was added dropwise to a suspension of 0.84 g of 60% sodium hydride in tetrahydrofuran (21 mL), and subsequently a solution of 3.0 g 2′,4′-difluoroacetophenone in tetrahydrofuran (19 mL) was added dropwise thereto. The temperature of the mixture was incre... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary alcohol | Ether | c1ccccc1 | c1ccccc1 | c1ccccc1 | HF | O1CCCC1 | null | 24 | CC(=O)c1ccc(F)cc1F.COCCO>O1CCCC1>COCCOc1cc(F)ccc1C(C)=O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-2159859012fe4ea19678cdf3cfd8ed9c | C1CCCC1.CC(=O)c1ccc(O)cc1F>>CC(=O)c1ccc(OC2CCCC2)cc1F | [Br-].C1CCCC1.OC1=CC(=C(C=C1)C(C)=O)F.[Br-].C1CCCC1.C([O-])([O-])=O.[Cs+].[Cs+]>>C1(CCCC1)OC1=CC(=C(C=C1)C(C)=O)F | [CH2:9]1[CH2:10][CH2:11][CH2:12][CH2:13]1.[CH3:1][C:2](=[O:3])[c:4]1[cH:5][cH:6][c:7]([OH:8])[cH:14][c:15]1[F:16]>>[CH3:1][C:2](=[O:3])[c:4]1[cH:5][cH:6][c:7]([O:8][CH:9]2[CH2:10][CH2:11][CH2:12][CH2:13]2)[cH:14][c:15]1[F:16] | C1CCCC1.CC(=O)c1ccc(O)cc1F | CC(=O)c1ccc(OC2CCCC2)cc1F | null | null | C(C)#N.C(C)(=O)OCC | Heteroatom Alkylation and Arylation | OtherReaction | 1b0b141bf6b317fb3f4853d99c0e21f208620be70a498da9a42860eb95c70530 | 0f0966e3597a58033417ecee71659f4d0c082f95d46b1e52c95541e6e4a59086 | c1ccc(OC2CCCC2)cc1 | [C:1]1-[C:2]-[C:3]-[C:4]-[CH2;D2;+0:5]-1.[OH;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[c:8]:[c:7](-[O;H0;D2;+0:6]-[CH;D3;+0:5]1-[C:1]-[C:2]-[C:3]-[C:4]-1):[c:9] | null | [] | 70 | CELSIUS | null | null | A suspension of 2.5 g 4′-hydroxy-2′-fluoroacetophenone, 2.0 mL cyclopentane bromide and 7.9 g cesium carbonate in acetonitrile (35 mL) was heated for 1 hour under reflux and then heated at 70° C. for 15 hours. Further, 1.0 mL cyclopentane bromide was added thereto, and the mixture was heated for 3 hours under reflux. T... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic alcohol | Ether | C1CCCC1 | C1CCCC1 | c1ccccc1.C1CCCC1 | null | C(C)#N.C(C)(=O)OCC | 70 | null | C1CCCC1.CC(=O)c1ccc(O)cc1F>C(C)#N.C(C)(=O)OCC>CC(=O)c1ccc(OC2CCCC2)cc1F |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-4e23a5fb633e499fab4435e476f56b52 | CC(C)(C)OC(=O)N1CCC(C=O)CC1.CSc1ccc(Br)cc1>>CSc1ccc(C(O)C2CCN(C(=O)OC(C)(C)C)CC2)cc1 | C(CCC)[Li].[Cl-].[NH4+].C(=O)C1CCN(CC1)C(=O)OC(C)(C)C.BrC1=CC=C(C=C1)SC>>OC(C1CCN(CC1)C(=O)OC(C)(C)C)C1=CC=C(C=C1)SC | [CH:7](=[O:8])[CH:9]1[CH2:10][CH2:11][N:12]([C:13](=[O:14])[O:15][C:16]([CH3:17])([CH3:18])[CH3:19])[CH2:20][CH2:21]1.Br[c:6]1[cH:5][cH:4][c:3]([S:2][CH3:1])[cH:23][cH:22]1>>[CH3:1][S:2][c:3]1[cH:4][cH:5][c:6]([CH:7]([OH:8])[CH:9]2[CH2:10][CH2:11][N:12]([C:13](=[O:14])[O:15][C:16]([CH3:17])([CH3:18])[CH3:19])[CH2:20][C... | CC(C)(C)OC(=O)N1CCC(C=O)CC1.CSc1ccc(Br)cc1 | CSc1ccc(C(O)C2CCN(C(=O)OC(C)(C)C)CC2)cc1 | null | null | O1CCCC1.CCCCCC.O | C-C Coupling | Grignard_alcohol | 0c8bc0f755f4d9a2cfce93ae43a9a9a531fa8ad86ff120aed0a18ba03c84e4d7 | 1c0bd0afc1d5e370e3c8193faf738f03752295e40fa0eb99c756011e9a4be26b | c1ccc(CC2CCNCC2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[C:6]-[C:7](-[CH;D2;+0:8]=[O;H0;D1;+0:9])-[C:10]>>[C:6]-[C:7](-[CH;D3;+0:8](-[OH;D1;+0:9])-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5])-[C:10] | 23.8 | [{"value": 23.8, "product": "OC(C1CCN(CC1)C(=O)OC(C)(C)C)C1=CC=C(C=C1)SC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 1 | HOUR | 380 mg of 1-bromo-4-methylsulfanyl benzene was dissolved in 10 mL anhydrous tetrahydrofuran, and 1.24 mL solution of 1.59 M n-butyl lithium in hexane was added dropwise thereto at −70° C. After the mixture was stirred for 1 hour, 3 mL solution of 400 mg t-butyl 4-formyl-piperidine-1-carboxylate in anhydrous tetrahydrof... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aldehyde | Secondary alcohol | c1ccccc1 | c1ccccc1 | c1ccccc1.C1CC[NH]CC1 | Br- | O1CCCC1.CCCCCC.O | 0 | 1 | CC(C)(C)OC(=O)N1CCC(C=O)CC1.CSc1ccc(Br)cc1>O1CCCC1.CCCCCC.O>CSc1ccc(C(O)C2CCN(C(=O)OC(C)(C)C)CC2)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-d734a28c973d447fb5fa90364bc5b07d | Clc1cccnc1Cl.NCCO>>OCCNc1ncccc1Cl | ClC1=NC=CC=C1Cl.NCCO.C([O-])(O)=O.[Na+]>>ClC=1C(=NC=CC1)NCCO | Cl[c:5]1[n:6][cH:7][cH:8][cH:9][c:10]1[Cl:11].[OH:1][CH2:2][CH2:3][NH2:4]>>[OH:1][CH2:2][CH2:3][NH:4][c:5]1[n:6][cH:7][cH:8][cH:9][c:10]1[Cl:11] | Clc1cccnc1Cl.NCCO | OCCNc1ncccc1Cl | null | null | null | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | c026a7bf7aba66b20cf21a13c528689aaaa1c05901524d62b36ca0c3b0572cef | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccncc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4](-[Cl;D1;H0:5]):[c:6].[C:7]-[C:8]-[NH2;D1;+0:9]>>[C:7]-[C:8]-[NH;D2;+0:9]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4](-[Cl;D1;H0:5]):[c:6] | null | [] | null | null | null | null | After 11.46 g of 2,3-dichloropyridine and 9.8 mL 2-aminoethanol were heated at 100° C. for 24 hours, an aqueous saturated sodium bicarbonate solution was added thereto, and the reaction mixture was extracted with ethyl acetate. The extract was washed with brine, the organic layer was dried over anhydrous sodium sulfate... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccncc1 | c1ccncc1 | c1ccncc1 | HCl | null | null | null | Clc1cccnc1Cl.NCCO>>OCCNc1ncccc1Cl |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-015fb88594894c9e9b8be65f3fc280b6 | O=C1CCC(=O)N1Br.OCCNc1ncccc1Cl>>OCCNc1ncc(Br)cc1Cl | ClC=1C(=NC=CC1)NCCO.BrN1C(CCC1=O)=O>>BrC=1C=C(C(=NC1)NCCO)Cl | O=C1CCC(=O)N1[Br:9].[OH:1][CH2:2][CH2:3][NH:4][c:5]1[n:6][cH:7][cH:8][cH:10][c:11]1[Cl:12]>>[OH:1][CH2:2][CH2:3][NH:4][c:5]1[n:6][cH:7][c:8]([Br:9])[cH:10][c:11]1[Cl:12] | O=C1CCC(=O)N1Br.OCCNc1ncccc1Cl | OCCNc1ncc(Br)cc1Cl | null | null | ClCCl.C(C)(=O)OCC | Functional Group Interconversion | Bromination | 0c4eeb30070e87daf86c6fe6be8db4805f592c36398c82b1c29b987bb0b889d8 | 0e444576b73669992a4073cc3f7b10ed52cb9df09f9f8e4042e39e6a602aa390 | c1ccncc1 | O=C1-C-C-C(=O)-N-1-[Br;H0;D1;+0:1].[#7;a:2]1:[c:3]:[c:4]:[c:5]:[cH;D2;+0:6]:[c:7]:1>>[Br;H0;D1;+0:1]-[c;H0;D3;+0:6]1:[c:5]:[c:4]:[c:3]:[#7;a:2]:[c:7]:1 | 103.6 | [{"value": 103.6, "product": "BrC=1C=C(C(=NC1)NCCO)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1.5 | HOUR | 2.1 g of 2-(3-chloro-2-pyridinylamino)ethanol was dissolved in 25 mL dichloromethane, and 2.3 g N-bromosuccinimide was added little by little thereto at 0° C. and stirred for 1.5 hours. The reaction mixture was diluted with ethyl acetate and then washed with an aqueous saturated sodium bicarbonate and brine, the organi... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Tertiary amide | Aromatic halide | C1CCNC1.c1ccncc1 | c1ccncc1 | c1ccncc1 | HO- | ClCCl.C(C)(=O)OCC | null | 1.5 | O=C1CCC(=O)N1Br.OCCNc1ncccc1Cl>ClCCl.C(C)(=O)OCC>OCCNc1ncc(Br)cc1Cl |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-841344a4b5f34e848713fd145538d083 | ClC1=CC(Br)=CN2CCN=C12>>Clc1cc(Br)cn2ccnc12 | BrC=1C=C(C=2N(C1)CCN2)Cl>>BrC=1C=C(C=2N(C1)C=CN2)Cl | [Cl:1][C:2]1=[CH:3][C:4]([Br:5])=[CH:6][N:7]2[CH2:8][CH2:9][N:10]=[C:11]12>>[Cl:1][c:2]1[cH:3][c:4]([Br:5])[cH:6][n:7]2[cH:8][cH:9][n:10][c:11]12 | ClC1=CC(Br)=CN2CCN=C12 | Clc1cc(Br)cn2ccnc12 | null | [O-2].[O-2].[Mn+4] | CC(=O)C | Aromatic Heterocycle Formation | OtherReaction | f78e386d593b75391a5171d414f8e09c792e7ccc66325ae4c56fec3ba0d5884b | 2c84cf48ded06568363103656ecd004a95adf46ead3e1488fc2053dc37ca8452 | c1ccn2ccnc2c1 | [Br;D1;H0:1]-[C;H0;D3;+0:2]1=[CH;D2;+0:3]-[N;H0;D3;+0:4]2-[CH2;D2;+0:5]-[CH2;D2;+0:6]-[N;H0;D2;+0:7]=[C;H0;D3;+0:8]-2-[C;H0;D3;+0:9](-[Cl;D1;H0:10])=[CH;D2;+0:11]-1>>[Br;D1;H0:1]-[c;H0;D3;+0:2]1:[cH;D2;+0:11]:[c;H0;D3;+0:9](-[Cl;D1;H0:10]):[c;H0;D3;+0:8]2:[n;H0;D2;+0:7]:[cH;D2;+0:6]:[cH;D2;+0:5]:[n;H0;D3;+0:4]:2:[cH;D2... | 61.6 | [{"value": 61.6, "product": "BrC=1C=C(C=2N(C1)C=CN2)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 2.08 g of 6-bromo-8-chloro-2,3-dihydroimidazo[1,2-a]pyridine was dissolved in 36 mL acetone, and together with 9.1 g of manganese dioxide, the mixture was heated for 9 hours under reflux. The reaction solution was cooled to room temperature, filtered through Celite and washed with ethyl acetate. The solvent was removed... | 10.6084/m9.figshare.5104873.v1 | null | Enamine.Alkenyl halide.Alkenyl halide | Aromatic halide.Aromatic halide | C1=CC2=NCCN2C=C1 | c1ccn2ccnc2c1 | c1ccn2ccnc2c1 | null | [O-2].[O-2].[Mn+4].CC(=O)C | null | null | ClC1=CC(Br)=CN2CCN=C12>[O-2].[O-2].[Mn+4].CC(=O)C>Clc1cc(Br)cn2ccnc12 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-7826fd182752414c9f1a1263d827f13b | Brc1ccc(Br)nc1.COC(CN)OC>>COC(CNc1ccc(Br)cn1)OC | BrC1=NC=C(C=C1)Br.COC(CN)OC.C([O-])(O)=O.[Na+]>>BrC=1C=CC(=NC1)NCC(OC)OC | Br[c:6]1[cH:7][cH:8][c:9]([Br:10])[cH:11][n:12]1.[CH3:1][O:2][CH:3]([CH2:4][NH2:5])[O:13][CH3:14]>>[CH3:1][O:2][CH:3]([CH2:4][NH:5][c:6]1[cH:7][cH:8][c:9]([Br:10])[cH:11][n:12]1)[O:13][CH3:14] | Brc1ccc(Br)nc1.COC(CN)OC | COC(CNc1ccc(Br)cn1)OC | null | null | null | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | c026a7bf7aba66b20cf21a13c528689aaaa1c05901524d62b36ca0c3b0572cef | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccncc1 | Br-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5].[C:6]-[C:7]-[NH2;D1;+0:8]>>[C:6]-[C:7]-[NH;D2;+0:8]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5] | null | [] | null | null | null | null | After 50 g of 2,5-dibromopyridine and 50 mL aminoacetaldehyde dimethyl acetal were heated at 130° C. for 8 hours, an aqueous saturated sodium bicarbonate solution was added thereto, and the reaction mixture was extracted with ethyl acetate. The extract was washed with brine, the organic layer was dried over anhydrous s... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccncc1 | c1ccncc1 | c1ccncc1 | HBr | null | null | null | Brc1ccc(Br)nc1.COC(CN)OC>>COC(CNc1ccc(Br)cn1)OC |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-0dbdc9783d4d489ab198e2f789e8084b | Cc1ccc(S(=O)(=O)Cl)cc1.N#CC(O)CNc1ccc(Br)cn1>>Cc1ccc(S(=O)(=O)OC(C#N)CNc2ccc(Br)cn2)cc1 | C([O-])(O)=O.[Na+].C(C)(C)N(CC)C(C)C.C1(=CC=C(C=C1)S(=O)(=O)Cl)C.BrC=1C=CC(=NC1)NCC(C#N)O>>C1(=CC=C(C=C1)S(=O)(=O)OC(CNC1=NC=C(C=C1)Br)C#N)C | Cl[S:6]([c:5]1[cH:4][cH:3][c:2]([CH3:1])[cH:23][cH:22]1)(=[O:7])=[O:8].[OH:9][CH:10]([C:11]#[N:12])[CH2:13][NH:14][c:15]1[cH:16][cH:17][c:18]([Br:19])[cH:20][n:21]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([S:6](=[O:7])(=[O:8])[O:9][CH:10]([C:11]#[N:12])[CH2:13][NH:14][c:15]2[cH:16][cH:17][c:18]([Br:19])[cH:20][n:21]2)[cH:22][c... | Cc1ccc(S(=O)(=O)Cl)cc1.N#CC(O)CNc1ccc(Br)cn1 | Cc1ccc(S(=O)(=O)OC(C#N)CNc2ccc(Br)cn2)cc1 | null | null | ClCCl | Acylation | Formation of Sulfonic Esters | ad3deb6f5d4dc7823aa3ad2bfe24985be1f3e6860ff8cc0ba215d7624074ef69 | ec645297cfd3107bffb1a4753ac125e48856598e58005e939bb2f0e91bf5e57c | O=S(=O)(OCCNc1ccccn1)c1ccccc1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6].[C:7]-[C:8](-[OH;D1;+0:9])-[C:10]#[N;D1;H0:11]>>[C:7]-[C:8](-[C:10]#[N;D1;H0:11])-[O;H0;D2;+0:9]-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6] | 64.8 | [{"value": 64.8, "product": "C1(=CC=C(C=C1)S(=O)(=O)OC(CNC1=NC=C(C=C1)Br)C#N)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | 7.2 g of 3-(5-bromo-2-pyridinylamino)-2-hydroxypropionitrile was dissolved in 60 mL dichloromethane, and 7.8 mL diisopropyl ethylamine and 6.3 g of 4-toluenesulfonic acid chloride were added thereto, and while the temperature of the mixture was gradually increased to room temperature, the mixture was stirred for 2 hour... | 10.6084/m9.figshare.5104873.v1 | null | Tosylate.Secondary alcohol.Sulfonyl halide | Tosylate | null | null | c1ccccc1.c1ccncc1 | HCl | ClCCl | null | 2 | Cc1ccc(S(=O)(=O)Cl)cc1.N#CC(O)CNc1ccc(Br)cn1>ClCCl>Cc1ccc(S(=O)(=O)OC(C#N)CNc2ccc(Br)cn2)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-fa9d214665694c878069c3dfffe8226b | Cc1ccc(S(=O)(=O)OC(C#N)CNc2ccc(Br)cn2)cc1>>N#CC1CN=C2C=CC(Br)=CN21 | C1(=CC=C(C=C1)S(=O)(=O)OC(CNC1=NC=C(C=C1)Br)C#N)C>>BrC=1C=CC=2N(C1)C(CN2)C#N | Cc1ccc(S(=O)(=O)O[CH:3]([C:2]#[N:1])[CH2:4][NH:5][c:6]2[cH:7][cH:8][c:9]([Br:10])[cH:11][n:12]2)cc1>>[N:1]#[C:2][CH:3]1[CH2:4][N:5]=[C:6]2[CH:7]=[CH:8][C:9]([Br:10])=[CH:11][N:12]12 | Cc1ccc(S(=O)(=O)OC(C#N)CNc2ccc(Br)cn2)cc1 | N#CC1CN=C2C=CC(Br)=CN21 | null | null | C(C)#N | Functional Group Interconversion | OtherReaction | dfb00ee5de546e0f8b3b8ef7435d44beb16120a353397d2502be2cb89fa526ee | 390a9c1b7a8da6e20e8cfa51452dc793098cd16c7dd6f7fa10ccccabdec3ed20 | C1=CC2=NCCN2C=C1 | C-c1:c:c:c(-S(=O)(=O)-O-[CH;D3;+0:1](-[C:2]#[N;D1;H0:3])-[C:4]-[NH;D2;+0:5]-[c;H0;D3;+0:6]2:[cH;D2;+0:7]:[cH;D2;+0:8]:[c;H0;D3;+0:9](-[Br;D1;H0:10]):[cH;D2;+0:11]:[n;H0;D2;+0:12]:2):c:c:1>>[Br;D1;H0:10]-[C;H0;D3;+0:9]1=[CH;D2;+0:11]-[N;H0;D3;+0:12]2-[C;H0;D3;+0:6](=[N;H0;D2;+0:5]-[C:4]-[CH;D3;+0:1]-2-[C:2]#[N;D1;H0:3])... | 88.7 | [{"value": 88.7, "product": "BrC=1C=CC=2N(C1)C(CN2)C#N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 7.64 g of 2-(5-bromo-2-pyridinylamino)-1-cyanoethyl toluene-4-sulfonate was dissolved in 76 mL acetonitrile, and the mixture was heated for 15 hours under reflux. After the solvent was removed, an aqueous saturated sodium bicarbonate was poured into the reaction product which was then extracted with dichloromethane, an... | 10.6084/m9.figshare.5104873.v1 | null | Tosylate.Aromatic halide.Secondary amine | Enamine.Alkenyl halide | c1ccccc1.c1ccncc1 | C1=CC2=NCCN2C=C1 | C1=CC2=NCCN2C=C1 | TsOH.HO- | C(C)#N | null | null | Cc1ccc(S(=O)(=O)OC(C#N)CNc2ccc(Br)cn2)cc1>C(C)#N>N#CC1CN=C2C=CC(Br)=CN21 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-b62610f5636e4d9282ac7f4af0117a3c | N#CC1CN=C2C=CC(Br)=CN21>>N#Cc1cnc2ccc(Br)cn12 | BrC=1C=CC=2N(C1)C(CN2)C#N.ClC=1C(C(=C(C(C1Cl)=O)C#N)C#N)=O>>BrC=1C=CC=2N(C1)C(=CN2)C#N | [N:1]#[C:2][CH:3]1[CH2:4][N:5]=[C:6]2[CH:7]=[CH:8][C:9]([Br:10])=[CH:11][N:12]12>>[N:1]#[C:2][c:3]1[cH:4][n:5][c:6]2[cH:7][cH:8][c:9]([Br:10])[cH:11][n:12]12 | N#CC1CN=C2C=CC(Br)=CN21 | N#Cc1cnc2ccc(Br)cn12 | null | null | O1CCOCC1.C(C)(=O)OCC | Aromatic Heterocycle Formation | OtherReaction | c60c03c85889124314f6a87395250ea03917b381817a50165cf8f2ae91ef2584 | def58fdf0054f9e963777d727e2fcfe02b3d47acb5bb7e18c5e5cf5e7bf2ed6c | c1ccn2ccnc2c1 | [Br;D1;H0:1]-[C;H0;D3;+0:2]1=[CH;D2;+0:3]-[N;H0;D3;+0:4]2-[C;H0;D3;+0:5](=[N;H0;D2;+0:6]-[CH2;D2;+0:7]-[CH;D3;+0:8]-2-[C:9]#[N;D1;H0:10])-[CH;D2;+0:11]=[CH;D2;+0:12]-1>>[Br;D1;H0:1]-[c;H0;D3;+0:2]1:[cH;D2;+0:3]:[n;H0;D3;+0:4]2:[c;H0;D3;+0:8](-[C:9]#[N;D1;H0:10]):[cH;D2;+0:7]:[n;H0;D2;+0:6]:[c;H0;D3;+0:5]:2:[cH;D2;+0:11... | 85.4 | [{"value": 85.4, "product": "BrC=1C=CC=2N(C1)C(=CN2)C#N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Method 1) 3.83 g of 6-bromo-2,3-dihydroimidazo[1,2-a]pyridine-3-carbonitrile synthesized in Production Example 242 was dissolved in 34 mL 1,4-dioxane, and the solution together with 4.3 g of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone was heated at 90° C. for 2 hours. The reaction solution was diluted with ethyl acetate,... | 10.6084/m9.figshare.5104873.v1 | null | Enamine.Alkenyl halide | Aromatic halide | C1=CC2=NCCN2C=C1 | c1ccn2ccnc2c1 | c1ccn2ccnc2c1 | null | O1CCOCC1.C(C)(=O)OCC | null | null | N#CC1CN=C2C=CC(Br)=CN21>O1CCOCC1.C(C)(=O)OCC>N#Cc1cnc2ccc(Br)cn12 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-7c7fbe84916a4ebe8d9ff238d3978720 | Brc1ccc2ncc(I)n2c1.Cc1ccc(S(=O)(=O)C#N)cc1>>N#Cc1cnc2ccc(Br)cn12 | O.C1(=CC=C(C=C1)S(=O)(=O)C#N)C.BrC=1C=CC=2N(C1)C(=CN2)I.C(C)(C)[Mg]Br>>BrC=1C=CC=2N(C1)C(=CN2)C#N | I[c:3]1[cH:4][n:5][c:6]2[cH:7][cH:8][c:9]([Br:10])[cH:11][n:12]12.Cc1ccc(S(=O)(=O)[C:2]#[N:1])cc1>>[N:1]#[C:2][c:3]1[cH:4][n:5][c:6]2[cH:7][cH:8][c:9]([Br:10])[cH:11][n:12]12 | Brc1ccc2ncc(I)n2c1.Cc1ccc(S(=O)(=O)C#N)cc1 | N#Cc1cnc2ccc(Br)cn12 | null | null | O1CCCC1.C(C)(=O)OCC | C-C Coupling | OtherReaction | 1c185869e396ba40d6e6c73fdf1a72d984b9f87eb77d8ce186cddb8a9f25dc8c | 79fb0bb14338c3c783579b68b1bc350a3e7823991438eaa347be0f216d7b34eb | c1ccn2ccnc2c1 | C-c1:c:c:c(-S(=O)(=O)-[C;H0;D2;+0:1]#[N;D1;H0:2]):c:c:1.I-[c;H0;D3;+0:3]1:[c:4]:[#7;a:5]:[c:6](:[c:7]):[#7;a:8]:1:[c:9]>>[N;D1;H0:2]#[C;H0;D2;+0:1]-[c;H0;D3;+0:3]1:[c:4]:[#7;a:5]:[c:6](:[c:7]):[#7;a:8]:1:[c:9] | 71.6 | [{"value": 71.6, "product": "BrC=1C=CC=2N(C1)C(=CN2)C#N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 30 | MINUTE | Method 2) 80 g of 6-bromo-3-iodoimidazo[1,2-a]pyridine (compound in Production Example 49) was dissolved in 500 mL tetrahydrofuran, and 273 mL of 1.0 M isopropyl magnesium bromide in tetrahydrofuran was slowly added dropwise thereto at 0° C. and stirred for 30 minutes, and 380 mL of 68 g 4-toluenesulfonyl cyanide in te... | 10.6084/m9.figshare.5104873.v1 | null | Tosylate.Aromatic halide.Nitrile | Nitrile | c1ccn2ccnc2c1.c1ccccc1 | c1ccn2ccnc2c1 | c1ccn2ccnc2c1 | TsOH.HI | O1CCCC1.C(C)(=O)OCC | 0 | 0.5 | Brc1ccc2ncc(I)n2c1.Cc1ccc(S(=O)(=O)C#N)cc1>O1CCCC1.C(C)(=O)OCC>N#Cc1cnc2ccc(Br)cn12 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-b25c921be4ca48ae96c29e3739a4f638 | COC(=O)c1cnc2ccc(-c3cn(C(c4ccccc4)(c4ccccc4)c4ccccc4)nc3-c3ccc(F)cc3)cn12.NN>>NNC(=O)c1cnc2ccc(-c3cn(C(c4ccccc4)(c4ccccc4)c4ccccc4)nc3-c3ccc(F)cc3)cn12 | FC1=CC=C(C=C1)C1=NN(C=C1C=1C=CC=2N(C1)C(=CN2)C(=O)OC)C(C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2.O.NN>>FC1=CC=C(C=C1)C1=NN(C=C1C=1C=CC=2N(C1)C(=CN2)C(=O)NN)C(C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2 | CO[C:3](=[O:4])[c:5]1[cH:6][n:7][c:8]2[cH:9][cH:10][c:11](-[c:12]3[cH:13][n:14]([C:15]([c:16]4[cH:17][cH:18][cH:19][cH:20][cH:21]4)([c:22]4[cH:23][cH:24][cH:25][cH:26][cH:27]4)[c:28]4[cH:29][cH:30][cH:31][cH:32][cH:33]4)[n:34][c:35]3-[c:36]3[cH:37][cH:38][c:39]([F:40])[cH:41][cH:42]3)[cH:43][n:44]12.[NH2:1][NH2:2]>>[NH... | COC(=O)c1cnc2ccc(-c3cn(C(c4ccccc4)(c4ccccc4)c4ccccc4)nc3-c3ccc(F)cc3)cn12.NN | NNC(=O)c1cnc2ccc(-c3cn(C(c4ccccc4)(c4ccccc4)c4ccccc4)nc3-c3ccc(F)cc3)cn12 | null | null | C(C)O | Acylation | Aminolysis of esters | 2e40a14c7d71c6b9001f460fbb953805c923b2db988c8c04f234b9bb5f04424f | 3b636feb164ef0f3c8a4f1764f18a25b9eee32ed1463e3bb4b6f1becb871ca74 | c1ccc(-c2nn(C(c3ccccc3)(c3ccccc3)c3ccccc3)cc2-c2ccc3nccn3c2)cc1 | C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[c:4]:[#7;a:5]:[c:6]:[#7;a:7]:1:[c:8].[N;D1;H2:9]-[NH2;D1;+0:10]>>[N;D1;H2:9]-[NH;D2;+0:10]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[c:4]:[#7;a:5]:[c:6]:[#7;a:7]:1:[c:8] | null | [] | null | null | null | null | A mixture of 740 mg methyl 6-[3-(4-fluorophenyl)-1-trityl-1H-pyrazol-4-yl]imidazo[1,2-a]pyridine-3-carboxylate (compound in Production Example 273), 0.32 mL hydrazine monohydrate and 20 mL ethanol was heated for 6 hours under reflux. The reaction solution was evaporated, and the resulting residue was purified by NH sil... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Ester | Acylhydrazine | null | null | c1ccn2ccnc2c1.c1cn[nH]c1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | HO- | C(C)O | null | null | COC(=O)c1cnc2ccc(-c3cn(C(c4ccccc4)(c4ccccc4)c4ccccc4)nc3-c3ccc(F)cc3)cn12.NN>C(C)O>NNC(=O)c1cnc2ccc(-c3cn(C(c4ccccc4)(c4ccccc4)c4ccccc4)nc3-c3ccc(F)cc3)cn12 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-0bdc1355248043108d099b572644b3e7 | Brc1ccc2ncc(I)n2c1.CCOC(=O)Cl>>CCOC(=O)c1cnc2ccc(Br)cn12 | C(C)(C)[Mg]Br.C([O-])(O)=O.[Na+].C(OCC)(=O)Cl.BrC=1C=CC=2N(C1)C(=CN2)I>>BrC=1C=CC=2N(C1)C(=CN2)C(=O)OCC | I[c:6]1[cH:7][n:8][c:9]2[cH:10][cH:11][c:12]([Br:13])[cH:14][n:15]12.Cl[C:4]([O:3][CH2:2][CH3:1])=[O:5]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][n:8][c:9]2[cH:10][cH:11][c:12]([Br:13])[cH:14][n:15]12 | Brc1ccc2ncc(I)n2c1.CCOC(=O)Cl | CCOC(=O)c1cnc2ccc(Br)cn12 | null | null | O1CCCC1.O.C(C)(=O)OCC | C-C Coupling | OtherReaction | d25f86b249f115db5eee10f5e81a0de60ce8996fa162e499c0393c27c8ec46ac | e492b0c20aeea4be57b3b35f202d8ad0bd499fdae4bec30be882f32b4e25bf9b | c1ccn2ccnc2c1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C:4].I-[c;H0;D3;+0:5]1:[c:6]:[#7;a:7]:[c:8](:[c:9]):[#7;a:10]:1:[c:11]>>[C:4]-[#8:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c;H0;D3;+0:5]1:[c:6]:[#7;a:7]:[c:8](:[c:9]):[#7;a:10]:1:[c:11] | null | [] | 0 | CELSIUS | 1.5 | HOUR | A mixture of 9.69 g 6-bromo-3-iodoimidazo[1,2-a]pyridine (compound in Production Example 49) and 450 mL anhydrous tetrahydrofuran was added little by little to 4.5 mL isopropyl magnesium bromide (0.75 M tetrahydrofuran solution) under ice-cooling in a stream of nitrogen. Then, this reaction solution was returned to roo... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Aromatic halide | Ester | c1ccn2ccnc2c1 | c1ccn2ccnc2c1 | c1ccn2ccnc2c1 | I- | O1CCCC1.O.C(C)(=O)OCC | 0 | 1.5 | Brc1ccc2ncc(I)n2c1.CCOC(=O)Cl>O1CCCC1.O.C(C)(=O)OCC>CCOC(=O)c1cnc2ccc(Br)cn12 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-c14ea3baa17245c0a6469ad64bce125d | CCOC(=O)c1cnc2ccc(Br)cn12.NN>>NNC(=O)c1cnc2ccc(Br)cn12 | BrC=1C=CC=2N(C1)C(=CN2)C(=O)OCC.O.NN>>BrC=1C=CC=2N(C1)C(=CN2)C(=O)NN | CCO[C:3](=[O:4])[c:5]1[cH:6][n:7][c:8]2[cH:9][cH:10][c:11]([Br:12])[cH:13][n:14]12.[NH2:1][NH2:2]>>[NH2:1][NH:2][C:3](=[O:4])[c:5]1[cH:6][n:7][c:8]2[cH:9][cH:10][c:11]([Br:12])[cH:13][n:14]12 | CCOC(=O)c1cnc2ccc(Br)cn12.NN | NNC(=O)c1cnc2ccc(Br)cn12 | null | null | C(C)O | Acylation | Aminolysis of esters | 2e40a14c7d71c6b9001f460fbb953805c923b2db988c8c04f234b9bb5f04424f | 3b636feb164ef0f3c8a4f1764f18a25b9eee32ed1463e3bb4b6f1becb871ca74 | c1ccn2ccnc2c1 | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[c:4]:[#7;a:5]:[c:6]:[#7;a:7]:1:[c:8].[N;D1;H2:9]-[NH2;D1;+0:10]>>[N;D1;H2:9]-[NH;D2;+0:10]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[c:4]:[#7;a:5]:[c:6]:[#7;a:7]:1:[c:8] | null | [] | null | null | null | null | A mixture of 1.94 g ethyl 6-bromoimidazo[1,2-a]pyridine-3-carboxylate, 6 mL hydrazine monohydrate and 20 mL ethanol was heated for 1 hour under reflux. The precipitated crystals were collected by filtration, washed with ethanol and dried under reduced pressure by a vacuum pump to give 1.71 g of the title compound as pa... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Ester | Acylhydrazine | null | null | c1ccn2ccnc2c1 | HO- | C(C)O | null | null | CCOC(=O)c1cnc2ccc(Br)cn12.NN>C(C)O>NNC(=O)c1cnc2ccc(Br)cn12 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-6daa03a51b114bf9858fad4788a0195e | COc1ccc(P2(=S)SP(=S)(c3ccc(OC)cc3)S2)cc1.NNC(=O)c1cnc2ccc(Br)cn12.O=C(Cl)C1CC1>>Brc1ccc2ncc(-c3nnc(C4CC4)s3)n2c1 | C1(CC1)C(=O)Cl.BrC=1C=CC=2N(C1)C(=CN2)C(=O)NN.C([O-])(O)=O.[Na+].COC=1C=CC(=CC1)P2(=S)SP(=S)(S2)C=3C=CC(=CC3)OC.C1(=CC=CC=C1)C>>BrC=1C=CC=2N(C1)C(=CN2)C=2SC(=NN2)C2CC2 | COc1ccc(P2(=S)SP(c3ccc(OC)cc3)(=[S:16])S2)cc1.O=[C:9]([c:8]1[cH:7][n:6][c:5]2[cH:4][cH:3][c:2]([Br:1])[cH:18][n:17]21)[NH:10][NH2:11].O=[C:12](Cl)[CH:13]1[CH2:14][CH2:15]1>>[Br:1][c:2]1[cH:3][cH:4][c:5]2[n:6][cH:7][c:8](-[c:9]3[n:10][n:11][c:12]([CH:13]4[CH2:14][CH2:15]4)[s:16]3)[n:17]2[cH:18]1 | COc1ccc(P2(=S)SP(=S)(c3ccc(OC)cc3)S2)cc1.NNC(=O)c1cnc2ccc(Br)cn12.O=C(Cl)C1CC1 | Brc1ccc2ncc(-c3nnc(C4CC4)s3)n2c1 | null | null | O1CCCC1.O | Miscellaneous | OtherReaction | 6e7e92a80e6b5a414388b497b645e527fda43b733f7d88e9222f0050a0b49f09 | 9a3225718571e61518419c747e141a5e7b98877e2ba2174d3bb27bdb65f706d6 | c1ccn2c(-c3nnc(C4CC4)s3)cnc2c1 | C-O-c1:c:c:c(-P2(=S)-S-P(=[S;H0;D1;+0:1])(-c3:c:c:c(-O-C):c:c:3)-S-2):c:c:1.Cl-[C;H0;D3;+0:2](=O)-[C:3]1-[C:4]-[C:5]-1.O=[C;H0;D3;+0:6](-[NH;D2;+0:7]-[NH2;D1;+0:8])-[c;H0;D3;+0:9]1:[c:10]:[#7;a:11]:[c:12](:[c:13]):[#7;a:14]:1:[c:15]>>[c:15]:[#7;a:14]1:[c:12](:[c:13]):[#7;a:11]:[c:10]:[c;H0;D3;+0:9]:1-[c;H0;D3;+0:6]1:[n... | null | [] | null | null | 8 | HOUR | 0.22 mL cyclopropane carbonyl chloride was added at room temperature to a mixture of 510 mg 6-bromoimidazo[1,2-a]pyridine-3-carboxylic acid hydrazide (compound in Production Example 276), 202 mg sodium bicarbonate, 15 mL tetrahydrofuran and 15 mL water, and the mixture was stirred overnight. The organic layer was separ... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Acylhydrazine.Ether.Ether.Monosulfide.Monosulfide | null | c1ccccc1.P1SPS1.c1ccccc1 | c1nncs1 | c1ccn2ccnc2c1.c1nncs1.C1CC1 | HCl | O1CCCC1.O | null | 8 | COc1ccc(P2(=S)SP(=S)(c3ccc(OC)cc3)S2)cc1.NNC(=O)c1cnc2ccc(Br)cn12.O=C(Cl)C1CC1>O1CCCC1.O>Brc1ccc2ncc(-c3nnc(C4CC4)s3)n2c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-d82e24a2be0747a08b3ebbc045c400ba | CI.NNC(=O)c1cnc2ccc(Br)cn12.S=C=S>>CSc1nnc(-c2cnc3ccc(Br)cn23)o1 | BrC=1C=CC=2N(C1)C(=CN2)C(=O)NN.[OH-].[Na+].C(=S)=S.CI.C([O-])([O-])=O.[K+].[K+]>>BrC=1C=CC=2N(C1)C(=CN2)C=2OC(=NN2)SC | I[CH3:1].[NH2:4][NH:5][C:6]([c:7]1[cH:8][n:9][c:10]2[cH:11][cH:12][c:13]([Br:14])[cH:15][n:16]12)=[O:17].S=[C:3]=[S:2]>>[CH3:1][S:2][c:3]1[n:4][n:5][c:6](-[c:7]2[cH:8][n:9][c:10]3[cH:11][cH:12][c:13]([Br:14])[cH:15][n:16]23)[o:17]1 | CI.NNC(=O)c1cnc2ccc(Br)cn12.S=C=S | CSc1nnc(-c2cnc3ccc(Br)cn23)o1 | null | null | O.CN(C=O)C.C(C)(=O)OCC.C(C)O | Aromatic Heterocycle Formation | OtherReaction | a15f2bb205835a52a07e1d5735ecf8c10312f9f9f9bd5bc3c4fe361d9edeb208 | 2490f837e85471307bcfdf18fc468adc3367e4e60eef0d0c8d14c76d34701a72 | c1ccn2c(-c3nnco3)cnc2c1 | I-[CH3;D1;+0:1].S=[C;H0;D2;+0:2]=[S;H0;D1;+0:3].[NH2;D1;+0:4]-[NH;D2;+0:5]-[C;H0;D3;+0:6](=[O;H0;D1;+0:7])-[c;H0;D3;+0:8]1:[c:9]:[#7;a:10]:[c:11](:[c:12]):[#7;a:13]:1:[c:14]>>[CH3;D1;+0:1]-[S;H0;D2;+0:3]-[c;H0;D3;+0:2]1:[n;H0;D2;+0:4]:[n;H0;D2;+0:5]:[c;H0;D3;+0:6](-[c;H0;D3;+0:8]2:[c:9]:[#7;a:10]:[c:11](:[c:12]):[#7;a:... | null | [] | null | null | 10 | MINUTE | A mixture of 1 g 6-bromoimidazo[1,2-a]pyridine-3-carboxylic acid hydrazide (compound in Production Example 276), 0.24 mL carbon disulfide, 157 mg sodium hydroxide, 15 mL ethanol and 15 mL water was heated for 5 hours under reflux. The reaction solution was poured into a mixture of iced water and an aqueous saturated am... | 10.6084/m9.figshare.5104873.v1 | null | Acylhydrazine | Monosulfide | null | c1nnco1 | c1nnco1.c1ccn2ccnc2c1 | HI | O.CN(C=O)C.C(C)(=O)OCC.C(C)O | null | 0.166667 | CI.NNC(=O)c1cnc2ccc(Br)cn12.S=C=S>O.CN(C=O)C.C(C)(=O)OCC.C(C)O>CSc1nnc(-c2cnc3ccc(Br)cn23)o1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-0797dd6832b142a3b1f415dd8aed0253 | CSc1nnc(-c2cnc3ccc(Br)cn23)o1>>CS(=O)(=O)c1nnc(-c2cnc3ccc(Br)cn23)o1 | ClC1=CC(=CC=C1)C(=O)OO.BrC=1C=CC=2N(C1)C(=CN2)C=2OC(=NN2)SC.ClCCl.S(=S)(=O)([O-])[O-].[Na+].[Na+]>>BrC=1C=CC=2N(C1)C(=CN2)C=2OC(=NN2)S(=O)(=O)C | [CH3:1][S:2][c:5]1[n:6][n:7][c:8](-[c:9]2[cH:10][n:11][c:12]3[cH:13][cH:14][c:15]([Br:16])[cH:17][n:18]23)[o:19]1>>[CH3:1][S:2](=[O:3])(=[O:4])[c:5]1[n:6][n:7][c:8](-[c:9]2[cH:10][n:11][c:12]3[cH:13][cH:14][c:15]([Br:16])[cH:17][n:18]23)[o:19]1 | CSc1nnc(-c2cnc3ccc(Br)cn23)o1 | CS(=O)(=O)c1nnc(-c2cnc3ccc(Br)cn23)o1 | null | null | C(C)(=O)OCC | Oxidation | OtherReaction | 20dd6d48007b4fe7cd760226f21413eb5e71e6468db112596c2e7ea4858c8ac1 | 5cedc1bf0f43f21d78a249521ecfcec19fc5ac4895c41eed0e84f0c2618149fa | c1ccn2c(-c3nnco3)cnc2c1 | [C;D1;H3:1]-[S;H0;D2;+0:2]-[c:3]1:[#7;a:4]:[#7;a:5]:[c:6]:[#8;a:7]:1>>[C;D1;H3:1]-[S;H0;D4;+0:2](=[O;D1;H0:8])(=[O;D1;H0:9])-[c:3]1:[#7;a:4]:[#7;a:5]:[c:6]:[#8;a:7]:1 | null | [] | null | null | 8 | HOUR | 1.16 g of m-chloroperbenzoic acid was added to a mixture of 981 mg 6-bromo-3-(5-methylsulfanyl[1,3,4]oxadiazol-2-yl)imidazo[1,2-a]pyridine (compound in Production Example 279) and 30 mL dichloromethane under ice-coolingd water, then retuned to room temperature and stirred overnight. Ethyl acetate and an aqueous saturat... | 10.6084/m9.figshare.5104873.v1 | null | Monosulfide | Sulfone | null | null | c1nnco1.c1ccn2ccnc2c1 | null | C(C)(=O)OCC | null | 8 | CSc1nnc(-c2cnc3ccc(Br)cn23)o1>C(C)(=O)OCC>CS(=O)(=O)c1nnc(-c2cnc3ccc(Br)cn23)o1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-2c35e213c542401e8ac9e4c82950976c | CC(C)O.CS(=O)(=O)c1nnc(-c2cnc3ccc(Br)cn23)o1>>CC(C)Oc1nnc(-c2cnc3ccc(Br)cn23)o1 | BrC=1C=CC=2N(C1)C(=CN2)C=2OC(=NN2)S(=O)C.BrC=1C=CC=2N(C1)C(=CN2)C=2OC(=NN2)S(=O)(=O)C.[Cl-].[NH4+].C(C)(C)O>>BrC=1C=CC=2N(C1)C(=CN2)C=2OC(=NN2)OC(C)C | [CH3:1][CH:2]([CH3:3])[OH:4].CS(=O)(=O)[c:5]1[n:6][n:7][c:8](-[c:9]2[cH:10][n:11][c:12]3[cH:13][cH:14][c:15]([Br:16])[cH:17][n:18]23)[o:19]1>>[CH3:1][CH:2]([CH3:3])[O:4][c:5]1[n:6][n:7][c:8](-[c:9]2[cH:10][n:11][c:12]3[cH:13][cH:14][c:15]([Br:16])[cH:17][n:18]23)[o:19]1 | CC(C)O.CS(=O)(=O)c1nnc(-c2cnc3ccc(Br)cn23)o1 | CC(C)Oc1nnc(-c2cnc3ccc(Br)cn23)o1 | null | null | O1CCCC1.O.C(C)N(CC)CC.C(C)(=O)OCC | Heteroatom Alkylation and Arylation | OtherReaction | 8fad2d56540e14e643f6dc70b026544c6d73489f115c0eecdf01048bcbd555ae | 470422bbafd7315f89003b23963391a1a49ca3fe240736a0f6aea864ae217419 | c1ccn2c(-c3nnco3)cnc2c1 | C-S(=O)(=O)-[c;H0;D3;+0:1]1:[#7;a:2]:[#7;a:3]:[c:4](-[c:5](:[#7;a:6]):[c:7]:[#7;a:8]):[#8;a:9]:1.[C;D1;H3:10]-[C:11](-[C;D1;H3:12])-[OH;D1;+0:13]>>[#7;a:8]:[c:7]:[c:5](-[c:4]1:[#7;a:3]:[#7;a:2]:[c;H0;D3;+0:1](-[O;H0;D2;+0:13]-[C:11](-[C;D1;H3:10])-[C;D1;H3:12]):[#8;a:9]:1):[#7;a:6] | null | [] | null | null | null | null | A mixture consisting of 60 mg crude product of a mixture of 6-bromo-3-(5-methanesulfinyl[1,3,4]oxadiazol-2-yl)imidazo[1,2-a]pyridine and 6-bromo-3-(5-methylsulfonyl[1,3,4]oxadiazol-2-yl)imidazo[1,2-a]pyridine obtained in the synthesis process in Production Example 280, 2 mL isopropyl alcohol, 0.3 mL triethylamine and 3... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol.Sulfone | Ether | c1nnco1 | c1nnco1 | c1nnco1.c1ccn2ccnc2c1 | HO- | O1CCCC1.O.C(C)N(CC)CC.C(C)(=O)OCC | null | null | CC(C)O.CS(=O)(=O)c1nnc(-c2cnc3ccc(Br)cn23)o1>O1CCCC1.O.C(C)N(CC)CC.C(C)(=O)OCC>CC(C)Oc1nnc(-c2cnc3ccc(Br)cn23)o1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-116314e1f49e4302b21416115f54041d | CI.NNC(=O)c1cnc2ccc(Br)cn12.S=C=S>>CSc1nnc(-c2cnc3ccc(Br)cn23)s1 | [OH-].[K+].BrC=1C=CC=2N(C1)C(=CN2)C(=O)NN.C(=S)=S.CI.C([O-])(O)=O.[Na+].O.C1(=CC=C(C=C1)S(=O)(=O)O)C>>BrC=1C=CC=2N(C1)C(=CN2)C=2SC(=NN2)SC | I[CH3:1].O=[C:6]([NH:5][NH2:4])[c:7]1[cH:8][n:9][c:10]2[cH:11][cH:12][c:13]([Br:14])[cH:15][n:16]12.[S:2]=[C:3]=[S:17]>>[CH3:1][S:2][c:3]1[n:4][n:5][c:6](-[c:7]2[cH:8][n:9][c:10]3[cH:11][cH:12][c:13]([Br:14])[cH:15][n:16]23)[s:17]1 | CI.NNC(=O)c1cnc2ccc(Br)cn12.S=C=S | CSc1nnc(-c2cnc3ccc(Br)cn23)s1 | null | null | O.C1(=CC=CC=C1)C.C(C)(=O)OCC.CO.O1CCCC1 | Aromatic Heterocycle Formation | OtherReaction | c5033f81c247361e8d995dd2badb8a8d4561d2b50e44ef1df1a354362b1cc63c | 2490f837e85471307bcfdf18fc468adc3367e4e60eef0d0c8d14c76d34701a72 | c1ccn2c(-c3nncs3)cnc2c1 | I-[CH3;D1;+0:1].O=[C;H0;D3;+0:2](-[NH;D2;+0:3]-[NH2;D1;+0:4])-[c;H0;D3;+0:5]1:[c:6]:[#7;a:7]:[c:8](:[c:9]):[#7;a:10]:1:[c:11].[S;H0;D1;+0:12]=[C;H0;D2;+0:13]=[S;H0;D1;+0:14]>>[CH3;D1;+0:1]-[S;H0;D2;+0:14]-[c;H0;D3;+0:13]1:[n;H0;D2;+0:4]:[n;H0;D2;+0:3]:[c;H0;D3;+0:2](-[c;H0;D3;+0:5]2:[c:6]:[#7;a:7]:[c:8](:[c:9]):[#7;a:1... | 5.1 | [{"value": 5.1, "product": "BrC=1C=CC=2N(C1)C(=CN2)C=2SC(=NN2)SC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2.5 | HOUR | 66 mg potassium hydroxide (powder) was added to a mixture of 306 mg of 6-bromoimidazo[1,2-a]pyridine-3-carboxylic acid hydrazide (compound in Production Example 276), 195 mg carbon disulfide and 12 mL methanol under cooling with ice-water, and the mixture was stirred for 2.5 hours. Then, the reaction mixture was return... | 10.6084/m9.figshare.5104873.v1 | null | Acylhydrazine | Monosulfide | null | c1nncs1 | c1nncs1.c1ccn2ccnc2c1 | HI | O.C1(=CC=CC=C1)C.C(C)(=O)OCC.CO.O1CCCC1 | null | 2.5 | CI.NNC(=O)c1cnc2ccc(Br)cn12.S=C=S>O.C1(=CC=CC=C1)C.C(C)(=O)OCC.CO.O1CCCC1>CSc1nnc(-c2cnc3ccc(Br)cn23)s1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-ea58fd028a1c48f494e56cfad00eee8d | N#CCCCBr.Sc1cccs1>>N#CCCCSc1cccs1 | S1C(=CC=C1)S.BrCCCC#N.C([O-])([O-])=O.[K+].[K+]>>S1C(=CC=C1)SCCCC#N | Br[CH2:5][CH2:4][CH2:3][C:2]#[N:1].[SH:6][c:7]1[cH:8][cH:9][cH:10][s:11]1>>[N:1]#[C:2][CH2:3][CH2:4][CH2:5][S:6][c:7]1[cH:8][cH:9][cH:10][s:11]1 | N#CCCCBr.Sc1cccs1 | N#CCCCSc1cccs1 | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | thioether_nucl_sub | 26df88c6a3f5f203c89584658be4e126cb42994c98a2e16bc812e1036cdae857 | 8b2f52296c3a93039174c980b6042ba15754e04d6892a1284c3a32985220b214 | c1ccsc1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[SH;D1;+0:4]-[c:5](:[c:6]):[#16;a:7]:[c:8]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[S;H0;D2;+0:4]-[c:5](:[c:6]):[#16;a:7]:[c:8] | 93.7 | [{"value": 93.7, "product": "S1C(=CC=C1)SCCCC#N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 2.3 g of thiophen-2-thiol, 3.0 g of 4-bromobutyronitrile and 5.5 g of potassium carbonate were stirred in N,N-dimethylformamide at room temperature to give 3.4 g of 4-(2-thienylsulfanyl)butane nitrile. 3.4 g of 4-(2-thienylsulfanyl)butane nitrile was reacted with 5.4 g of N-iodosuccinimide in N,N-dimethylformamide, whe... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic thiol | Monosulfide | null | null | c1ccsc1 | HBr | CN(C=O)C | null | null | N#CCCCBr.Sc1cccs1>CN(C=O)C>N#CCCCSc1cccs1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-65f4b916b44c4c289686bb041aa72e0e | N#CCCCSc1cccs1.O=C1CCC(=O)N1I>>N#CCCCSc1ccc(I)s1 | S1C(=CC=C1)SCCCC#N.IN1C(CCC1=O)=O>>IC1=CC=C(S1)SCCCC#N | [N:1]#[C:2][CH2:3][CH2:4][CH2:5][S:6][c:7]1[cH:8][cH:9][cH:10][s:12]1.O=C1CCC(=O)N1[I:11]>>[N:1]#[C:2][CH2:3][CH2:4][CH2:5][S:6][c:7]1[cH:8][cH:9][c:10]([I:11])[s:12]1 | N#CCCCSc1cccs1.O=C1CCC(=O)N1I | N#CCCCSc1ccc(I)s1 | null | null | CN(C=O)C | Functional Group Interconversion | OtherReaction | a42d5393618d10b862dd7bd471fa3f4459c31017c8714cafb4e591f8ed4a8052 | 0e444576b73669992a4073cc3f7b10ed52cb9df09f9f8e4042e39e6a602aa390 | c1ccsc1 | O=C1-C-C-C(=O)-N-1-[I;H0;D1;+0:1].[#16;a:2]1:[c:3]:[c:4]:[c:5]:[cH;D2;+0:6]:1>>[I;H0;D1;+0:1]-[c;H0;D3;+0:6]1:[#16;a:2]:[c:3]:[c:4]:[c:5]:1 | 95.9 | [{"value": 95.9, "product": "IC1=CC=C(S1)SCCCC#N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 2.3 g of thiophen-2-thiol, 3.0 g of 4-bromobutyronitrile and 5.5 g of potassium carbonate were stirred in N,N-dimethylformamide at room temperature to give 3.4 g of 4-(2-thienylsulfanyl)butane nitrile. 3.4 g of 4-(2-thienylsulfanyl)butane nitrile was reacted with 5.4 g of N-iodosuccinimide in N,N-dimethylformamide, whe... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Tertiary amide | Aromatic halide | c1ccsc1.C1CCNC1 | c1ccsc1 | c1ccsc1 | HO- | CN(C=O)C | null | null | N#CCCCSc1cccs1.O=C1CCC(=O)N1I>CN(C=O)C>N#CCCCSc1ccc(I)s1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-7f4bc2a336c049ec819b1747c7048809 | ICI.N#CCCCc1nc2ccc(N)cc2s1>>N#CCCCc1nc2ccc(I)cc2s1 | NC1=CC2=C(N=C(S2)CCCC#N)C=C1.N(=O)OCCC(C)C.ICI>>IC1=CC2=C(N=C(S2)CCCC#N)C=C1 | IC[I:12].N[c:11]1[cH:10][cH:9][c:8]2[n:7][c:6]([CH2:5][CH2:4][CH2:3][C:2]#[N:1])[s:15][c:14]2[cH:13]1>>[N:1]#[C:2][CH2:3][CH2:4][CH2:5][c:6]1[n:7][c:8]2[cH:9][cH:10][c:11]([I:12])[cH:13][c:14]2[s:15]1 | ICI.N#CCCCc1nc2ccc(N)cc2s1 | N#CCCCc1nc2ccc(I)cc2s1 | null | [Cu]I | O1CCCC1 | Functional Group Interconversion | OtherReaction | 19efdc3671eccba483079778163c471f0ac1c0cc2cc14e140c8bd1068411c52f | a511902c9d47eba7e9fb55f1fce242c65253f2ae6cd2fe001fbf65238d3d696d | c1ccc2scnc2c1 | I-C-[I;H0;D1;+0:1].N-[c;H0;D3;+0:2]1:[c:3]:[c:4]:[c:5]2:[#7;a:6]:[c:7]:[#16;a:8]:[c:9]:2:[c:10]:1>>[I;H0;D1;+0:1]-[c;H0;D3;+0:2]1:[c:3]:[c:4]:[c:5]2:[#7;a:6]:[c:7]:[#16;a:8]:[c:9]:2:[c:10]:1 | null | [] | null | null | null | null | 1.1 g of 4-(6-amino-1,3-benzothiazol-2-yl)butane nitrile synthesized according to a method described in JP-A 5–194440, 2 mL isoamyl nitrite, 0.96 g of copper (I) iodide and 2 mL diiodomethane were heated in tetrahydrofuran at 80° C. for 1 hour. After the solvent was removed, the residue was purified by NH silica gel co... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary halide.Primary amine | Aromatic halide | c1ccc2scnc2c1 | c1ccc2scnc2c1 | c1ccc2scnc2c1 | HI | [Cu]I.O1CCCC1 | null | null | ICI.N#CCCCc1nc2ccc(N)cc2s1>[Cu]I.O1CCCC1>N#CCCCc1nc2ccc(I)cc2s1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-d4ee081e2c314b2999239ecf24ab5827 | NC(=O)CC[C@H](O)c1nc2ccc(I)cc2s1>>N#CCC[C@H](O)c1nc2ccc(I)cc2s1 | O.N1=CC=CC=C1.FC(C(=O)OC(C(F)(F)F)=O)(F)F.O[C@@H](CCC(=O)N)C=1SC2=C(N1)C=CC(=C2)I>>O[C@@H](CCC#N)C=1SC2=C(N1)C=CC(=C2)I | O=[C:2]([NH2:1])[CH2:3][CH2:4][C@H:5]([OH:6])[c:7]1[n:8][c:9]2[cH:10][cH:11][c:12]([I:13])[cH:14][c:15]2[s:16]1>>[N:1]#[C:2][CH2:3][CH2:4][C@H:5]([OH:6])[c:7]1[n:8][c:9]2[cH:10][cH:11][c:12]([I:13])[cH:14][c:15]2[s:16]1 | NC(=O)CC[C@H](O)c1nc2ccc(I)cc2s1 | N#CCC[C@H](O)c1nc2ccc(I)cc2s1 | null | null | O1CCCC1 | Miscellaneous | OtherReaction | 5094e9d814705bbdc421edbf7e9198e499e70e93916e2cec6eefbc82d1ba5440 | 32b9893bcb5223559a9d02852f8392cf6473aacfb044a52ba4e9cb9c29edb170 | c1ccc2scnc2c1 | O=[C;H0;D3;+0:1](-[NH2;D1;+0:2])-[C:3]-[C:4]>>[C:4]-[C:3]-[C;H0;D2;+0:1]#[N;H0;D1;+0:2] | 73.8 | [{"value": 73.8, "product": "O[C@@H](CCC#N)C=1SC2=C(N1)C=CC(=C2)I", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | 0.33 mL trifluoroacetic anhydride was added to a solution of 556 mg of (4S)-4-hydroxy-4-(6-iodo-1,3-benzothiazol-2-yl)butane amide obtained in Production Example 299 and 0.25 mL pyridine in tetrahydrofuran under ice-cooling, and the mixture was stirred for 2 hours. Water was added thereto, the reaction solution was the... | 10.6084/m9.figshare.5104873.v1 | null | Primary amide | Nitrile | null | null | c1ccc2scnc2c1 | HO- | O1CCCC1 | null | 2 | NC(=O)CC[C@H](O)c1nc2ccc(I)cc2s1>O1CCCC1>N#CCC[C@H](O)c1nc2ccc(I)cc2s1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-52e3b9d8c58f45aca3d21a2fe05817b7 | C[Si](C)(C)C=[N+]=[N-].Cc1csc(N)n1.O=S(=O)(Cl)c1ccc(I)cc1>>Cc1csc(N(C)S(=O)(=O)c2ccc(I)cc2)n1 | IC1=CC=C(C=C1)S(=O)(=O)Cl.NC=1SC=C(N1)C.C[Si](C)(C)C=[N+]=[N-]>>CN(S(=O)(=O)C1=CC=C(C=C1)I)C=1SC=C(N1)C | C[Si](C)(C)[CH:7]=[N+]=[N-].[CH3:1][c:2]1[cH:3][s:4][c:5]([NH2:6])[n:18]1.Cl[S:8](=[O:9])(=[O:10])[c:11]1[cH:12][cH:13][c:14]([I:15])[cH:16][cH:17]1>>[CH3:1][c:2]1[cH:3][s:4][c:5]([N:6]([CH3:7])[S:8](=[O:9])(=[O:10])[c:11]2[cH:12][cH:13][c:14]([I:15])[cH:16][cH:17]2)[n:18]1 | C[Si](C)(C)C=[N+]=[N-].Cc1csc(N)n1.O=S(=O)(Cl)c1ccc(I)cc1 | Cc1csc(N(C)S(=O)(=O)c2ccc(I)cc2)n1 | null | null | N1=CC=CC=C1.O1CCCC1.CO | Heteroatom Alkylation and Arylation | OtherReaction | 816d3dc285e0587d41466c78207a62d612d2f7a200de0e754a8cfb5e6b1d9bdc | 1b91dcd2bb04ce245a0a4cf680c1f998a98b34b516c56e0362ff42c38535ac5c | O=S(=O)(Nc1nccs1)c1ccccc1 | C-[Si](-C)(-C)-[CH;D2;+0:1]=[N+]=[N-].Cl-[S;H0;D4;+0:2](=[O;D1;H0:3])(=[O;D1;H0:4])-[c:5](:[c:6]):[c:7].[NH2;D1;+0:8]-[c:9]1:[#16;a:10]:[c:11]:[c:12]:[#7;a:13]:1>>[CH3;D1;+0:1]-[N;H0;D3;+0:8](-[c:9]1:[#16;a:10]:[c:11]:[c:12]:[#7;a:13]:1)-[S;H0;D4;+0:2](=[O;D1;H0:3])(=[O;D1;H0:4])-[c:5](:[c:6]):[c:7] | null | [] | null | null | 1 | HOUR | 760 mg of N1-(4-methyl-1,3-thiazol-2-yl)-4-iodo-1-benzene sulfonamide obtained by reacting 4-iodobenzenesulfonyl chloride with 2-amino-4-methylthiazole in pyridine was dissolved in a solvent mixture of 5 mL methanol and 3 mL tetrahydrofuran, then 1.1 mL (trimethylsilyl)diazomethane (2 M hexane solution) was added there... | 10.6084/m9.figshare.5104873.v1 | null | Diazo.Primary amine.Sulfonyl halide.Silyl protective group | Tertiary amine | null | null | c1cscn1.c1ccccc1 | HCl | N1=CC=CC=C1.O1CCCC1.CO | null | 1 | C[Si](C)(C)C=[N+]=[N-].Cc1csc(N)n1.O=S(=O)(Cl)c1ccc(I)cc1>N1=CC=CC=C1.O1CCCC1.CO>Cc1csc(N(C)S(=O)(=O)c2ccc(I)cc2)n1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-378eecc8f6da43fc94723245ce7e7e3f | Cc1csc(N)n1.O=C(O)c1ccc(-c2cnc3ccc(Br)cn23)cc1>>Cc1csc(NC(=O)c2ccc(-c3cnc4ccc(Br)cn34)cc2)n1 | BrC=1C=CC=2N(C1)C(=CN2)C2=CC=C(C(=O)O)C=C2.NC=1SC=C(N1)C.F[P-](F)(F)(F)(F)F.N1(N=NC2=C1C=CC=C2)O[P+](N(C)C)(N(C)C)N(C)C.C(C)N(CC)CC>>CC=1N=C(SC1)NC(C1=CC=C(C=C1)C1=CN=C2N1C=C(C=C2)Br)=O | [CH3:1][c:2]1[cH:3][s:4][c:5]([NH2:6])[n:25]1.O[C:7](=[O:8])[c:9]1[cH:10][cH:11][c:12](-[c:13]2[cH:14][n:15][c:16]3[cH:17][cH:18][c:19]([Br:20])[cH:21][n:22]23)[cH:23][cH:24]1>>[CH3:1][c:2]1[cH:3][s:4][c:5]([NH:6][C:7](=[O:8])[c:9]2[cH:10][cH:11][c:12](-[c:13]3[cH:14][n:15][c:16]4[cH:17][cH:18][c:19]([Br:20])[cH:21][n:... | Cc1csc(N)n1.O=C(O)c1ccc(-c2cnc3ccc(Br)cn23)cc1 | Cc1csc(NC(=O)c2ccc(-c3cnc4ccc(Br)cn34)cc2)n1 | null | null | ClCCl | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(Nc1nccs1)c1ccc(-c2cnc3ccccn23)cc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[NH2;D1;+0:6]-[c:7]1:[#16;a:8]:[c:9]:[c:10]:[#7;a:11]:1>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7]1:[#16;a:8]:[c:9]:[c:10]:[#7;a:11]:1)-[c:3](:[c:4]):[c:5] | 48.3 | [{"value": 48.3, "product": "CC=1N=C(SC1)NC(C1=CC=C(C=C1)C1=CN=C2N1C=C(C=C2)Br)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 159 mg of 4-(6-bromoimidazo[1,2-a]pyridin-3-yl)benzoic acid (compound in Production Example 54), 58 mg of 2-amino-4-methyl-1,3-thiazole, 243 mg benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate and 83 μL triethylamine were reacted overnight in 4 mL dichloromethane. The reaction solution was purifi... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1cscn1.c1ccccc1.c1ccn2ccnc2c1 | HO- | ClCCl | null | null | Cc1csc(N)n1.O=C(O)c1ccc(-c2cnc3ccc(Br)cn23)cc1>ClCCl>Cc1csc(NC(=O)c2ccc(-c3cnc4ccc(Br)cn34)cc2)n1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-7d51ffea0f444886a4623476d3e4569f | CON(C)C(=O)[C@H](C)NC(=O)OC(C)(C)C.Fc1ccc(Br)cc1>>C[C@H](NC(=O)OC(C)(C)C)C(=O)c1ccc(F)cc1 | CON(C([C@H](C)NC(OC(C)(C)C)=O)=O)C.BrC1=CC=C(C=C1)F.[Mg].[Cl-].[NH4+]>>FC1=CC=C(C=C1)C([C@H](C)NC(OC(C)(C)C)=O)=O | CON(C)[C:11]([C@H:2]([CH3:1])[NH:3][C:4](=[O:5])[O:6][C:7]([CH3:8])([CH3:9])[CH3:10])=[O:12].Br[c:13]1[cH:14][cH:15][c:16]([F:17])[cH:18][cH:19]1>>[CH3:1][C@H:2]([NH:3][C:4](=[O:5])[O:6][C:7]([CH3:8])([CH3:9])[CH3:10])[C:11](=[O:12])[c:13]1[cH:14][cH:15][c:16]([F:17])[cH:18][cH:19]1 | CON(C)C(=O)[C@H](C)NC(=O)OC(C)(C)C.Fc1ccc(Br)cc1 | C[C@H](NC(=O)OC(C)(C)C)C(=O)c1ccc(F)cc1 | null | null | O1CCCC1 | C-C Coupling | OtherReaction | 99face78a8bbaa38ff4dd2141c4a0df3e690005988b6fb5a9a2afc6a90da7e24 | 7d9aa59f8ecc532475d910f9ab122332ecbb7f9444a37371b7c1bac80798d342 | c1ccccc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].C-O-N(-C)-[C;H0;D3;+0:6](=[O;D1;H0:7])-[C:8](-[C;D1;H3:9])-[#7:10]-[C:11](=[O;D1;H0:12])-[#8:13]-[C:14](-[C;D1;H3:15])(-[C;D1;H3:16])-[C;D1;H3:17]>>[C;D1;H3:15]-[C:14](-[C;D1;H3:16])(-[C;D1;H3:17])-[#8:13]-[C:11](=[O;D1;H0:12])-[#7:10]-[C:8](-[C;D1;H3:9])-[C;H0;D3;+0:6](=[O;D... | 97.4 | [{"value": 97.4, "product": "FC1=CC=C(C=C1)C([C@H](C)NC(OC(C)(C)C)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 5 | CELSIUS | 2 | HOUR | A solution of 2.32 g t-butyl N-{(1S)-2-[methoxy(methyl)amino]-1-methyl-2-oxoethyl}carbamate in tetrahydrofuran was added dropwise under ice-cooling to a tetrahydrofuran solution of Grignard reagent prepared from 5.2 g of 1-bromo-4-fluorobenzene and 1 g magnesium. The mixture was stirred at 5° C. for 2 hours, then poure... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Tertiary amide | Ketone | c1ccccc1 | c1ccccc1 | c1ccccc1 | HBr | O1CCCC1 | 5 | 2 | CON(C)C(=O)[C@H](C)NC(=O)OC(C)(C)C.Fc1ccc(Br)cc1>O1CCCC1>C[C@H](NC(=O)OC(C)(C)C)C(=O)c1ccc(F)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-de9f6a334b8946788a458cefe95465ad | CSc1cccc(N)c1.O=C(O)c1ccc(Br)cc1F>>CSc1cccc(NC(=O)c2ccc(Br)cc2F)c1 | BrC1=CC(=C(C(=O)O)C=C1)F.CSC=1C=C(N)C=CC1>>CSC=1C=C(C=CC1)NC(C1=C(C=C(C=C1)Br)F)=O | [CH3:1][S:2][c:3]1[cH:4][cH:5][cH:6][c:7]([NH2:8])[cH:19]1.O[C:9](=[O:10])[c:11]1[cH:12][cH:13][c:14]([Br:15])[cH:16][c:17]1[F:18]>>[CH3:1][S:2][c:3]1[cH:4][cH:5][cH:6][c:7]([NH:8][C:9](=[O:10])[c:11]2[cH:12][cH:13][c:14]([Br:15])[cH:16][c:17]2[F:18])[cH:19]1 | CSc1cccc(N)c1.O=C(O)c1ccc(Br)cc1F | CSc1cccc(NC(=O)c2ccc(Br)cc2F)c1 | null | null | null | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(Nc1ccccc1)c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9])-[c:3](:[c:4]):[c:5] | null | [] | null | null | null | null | 460 mg of N1-[3-(methylsulfanyl)phenyl]-4-bromo-2-fluorobenzamide obtained in the same manner as in Production Example 32 from 4-bromo-2-fluorobenzoic acid and 3-(methylthio)aniline was stirred for 1.5 hours together with 1.23 g oxone in 15 mL tetrahydrofuran, 10 mL methanol and 10 mL water. The reaction solution was e... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccccc1 | HO- | null | null | null | CSc1cccc(N)c1.O=C(O)c1ccc(Br)cc1F>>CSc1cccc(NC(=O)c2ccc(Br)cc2F)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-95d13c917d1e465a99ea0479340b0bfb | C=[CH][Sn]([CH2]CCC)([CH2]CCC)[CH2]CCC.Nc1ccc(Br)cn1>>C=Cc1ccc(N)nc1 | BrC=1C=CC(=NC1)N.C(CCC)[Sn](C=C)(CCCC)CCCC>>C(=C)C=1C=CC(=NC1)N | CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[CH:2]=[CH2:1].Br[c:3]1[cH:4][cH:5][c:6]([NH2:7])[n:8][cH:9]1>>[CH2:1]=[CH:2][c:3]1[cH:4][cH:5][c:6]([NH2:7])[n:8][cH:9]1 | C=[CH][Sn]([CH2]CCC)([CH2]CCC)[CH2]CCC.Nc1ccc(Br)cn1 | C=Cc1ccc(N)nc1 | null | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1 | C=1(C(=CC=CC1)C)C | C-C Coupling | Stille reaction_vinyl | 3dd1babd20b217bb4acf07044a72bf65da3bd9404d25a4b198b8fddcb5d9092e | ec03c739f58696d2a3659a73884744e1a490a20a587da6f115be382b663cf23d | c1ccncc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[#7;a:5]:[c:6]:1.C-C-C-[CH2]-[Sn](-[CH2]-C-C-C)(-[CH2]-C-C-C)-[CH;D2;+0:7]=[C;D1;H2:8]>>[C;D1;H2:8]=[CH;D2;+0:7]-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[#7;a:5]:[c:6]:1 | 45.3 | [{"value": 45.3, "product": "C(=C)C=1C=CC(=NC1)N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 4.13 g 5-bromopyridin-2-yl amine, 7.95 g tributyl(vinyl)tin and 1.38 g tetrakis(triphenylphosphine)palladium were heated in 70 mL xylene at 120° C. for 3 hours under nitrogen atmosphere. The solvent was removed, and the residue was purified by silica gel column chromatography (hexane/ethyl acetate), to give 1.3 g of th... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Vinyl.Tin | Vinyl | c1ccncc1 | c1ccncc1 | c1ccncc1 | HBr.Sn | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.C=1(C(=CC=CC1)C)C | null | null | C=[CH][Sn]([CH2]CCC)([CH2]CCC)[CH2]CCC.Nc1ccc(Br)cn1>C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.C=1(C(=CC=CC1)C)C>C=Cc1ccc(N)nc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-09aab869bb414c14b748af51fb8fca97 | C=Cc1ccc(N)nc1>>CCc1ccc(N)nc1 | C(=C)C=1C=CC(=NC1)N>>C(C)C=1C=CC(=NC1)N | [CH2:1]=[CH:2][c:3]1[cH:4][cH:5][c:6]([NH2:7])[n:8][cH:9]1>>[CH3:1][CH2:2][c:3]1[cH:4][cH:5][c:6]([NH2:7])[n:8][cH:9]1 | C=Cc1ccc(N)nc1 | CCc1ccc(N)nc1 | null | [C].[Pd] | C(C)(=O)OCC | Reduction | Hydrogenation (double to single) | 8276b4fb5ddc7d15dec6d92474e91e2dbb2fb8b81e5b5720762e5d89cb27aa69 | 1ccae9f2e86499601fc3421041ff4588c8e6fd53048e86c3b6ed12ae873609c0 | c1ccncc1 | [CH2;D1;+0:1]=[CH;D2;+0:2]-[c:3](:[c:4]):[c:5]:[#7;a:6]:[c:7]>>[CH3;D1;+0:1]-[CH2;D2;+0:2]-[c:3](:[c:4]):[c:5]:[#7;a:6]:[c:7] | 94.4 | [{"value": 94.4, "product": "C(C)C=1C=CC(=NC1)N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 0.25 g 5-vinylpyridin-2-yl amine (compound in Production Example 326) and 0.1 g of 10% palladium-carbon were stirred in 5 mL ethyl acetate at room temperature for 2 hours under hydrogen atmosphere. The reaction solution was purified by NH silica gel column chromatography (ethyl acetate), to give 0.24 g of the title com... | 10.6084/m9.figshare.5104873.v1 | null | Vinyl | null | null | null | c1ccncc1 | null | [C].[Pd].C(C)(=O)OCC | null | null | C=Cc1ccc(N)nc1>[C].[Pd].C(C)(=O)OCC>CCc1ccc(N)nc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-ceab4b5f989746cf9e16193cc124bb05 | CCOC(=O)c1ccc(Br)cc1F.Nc1ccccc1[N+](=O)[O-]>>CCOC(=O)c1ccc(Nc2ccccc2[N+](=O)[O-])cc1F | BrC1=CC(=C(C(=O)OCC)C=C1)F.[N+](=O)([O-])C1=C(N)C=CC=C1.C([O-])([O-])=O.[Cs+].[Cs+].C1(=CC=CC=C1)C>>FC1=C(C(=O)OCC)C=CC(=C1)NC1=C(C=CC=C1)[N+](=O)[O-] | Br[c:9]1[cH:8][cH:7][c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[c:21]([F:22])[cH:20]1.[NH2:10][c:11]1[cH:12][cH:13][cH:14][cH:15][c:16]1[N+:17](=[O:18])[O-:19]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][c:9]([NH:10][c:11]2[cH:12][cH:13][cH:14][cH:15][c:16]2[N+:17](=[O:18])[O-:19])[cH:20][c:21]1[F:22] | CCOC(=O)c1ccc(Br)cc1F.Nc1ccccc1[N+](=O)[O-] | CCOC(=O)c1ccc(Nc2ccccc2[N+](=O)[O-])cc1F | 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].C1(=CC=CC=C1)P(C1=C(C2=CC=CC=C2C=C1)C1=C(C=CC2=CC=CC=C12)P(C1=CC=CC=C1)C1=CC=CC=C1)C1=CC=CC=C1 | O | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | da9dae6a655c4bd18887b692f91621e77027436294d6e1fc7be7295afb364796 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2ccccc2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[c:8]:[c:7](-[NH;D2;+0:6]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5]):[c:9] | 77.1 | [{"value": 77.1, "product": "FC1=C(C(=O)OCC)C=CC(=C1)NC1=C(C=CC=C1)[N+](=O)[O-]", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 1.0 g ethyl 4-bromo-2-fluorobenzoate, 0.56 g 2-nitroaniline, 1.85 g cesium carbonate, 37 mg tris(dibenzylideneacetone)-dipalladium (0), 38 mg 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (racemic mixture) and 15 mL toluene were stirred at 100° C. for 24 hours under nitrogen atmosphere. Water was added thereto, then the ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1 | HBr | 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].C1(=CC=CC=C1)P(C1=C(C2=CC=CC=C2C=C1)C1=C(C=CC2=CC=CC=C12)P(C1=CC=CC=C1)C1=CC=CC=C1)C1=CC=CC=C1.O | null | null | CCOC(=O)c1ccc(Br)cc1F.Nc1ccccc1[N+](=O)[O-]>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].C1(=CC=CC=C1)P(C1=C(C2=CC=CC=C2C=C1)C1=C(C=CC2=CC=CC=C12)P(C1=CC=CC=C1)C1=CC=CC=C1)C1=CC=CC=C1.O>CCOC(=O)c1ccc(Nc2ccccc2[N+](=O)[O-])cc1F |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-bbef1b1f3ba844cbbbb945a5c679fabc | CCOC(=O)c1ccc(Nc2ccccc2[N+](=O)[O-])cc1F>>CCOC(=O)c1ccc(Nc2ccccc2N)cc1F | FC1=C(C(=O)OCC)C=CC(=C1)NC1=C(C=CC=C1)[N+](=O)[O-].[Cl-].[NH4+].CO>>NC1=C(C=CC=C1)NC1=CC(=C(C(=O)OCC)C=C1)F | O=[N+:17]([O-])[c:16]1[c:11]([NH:10][c:9]2[cH:8][cH:7][c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[c:19]([F:20])[cH:18]2)[cH:12][cH:13][cH:14][cH:15]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][c:9]([NH:10][c:11]2[cH:12][cH:13][cH:14][cH:15][c:16]2[NH2:17])[cH:18][c:19]1[F:20] | CCOC(=O)c1ccc(Nc2ccccc2[N+](=O)[O-])cc1F | CCOC(=O)c1ccc(Nc2ccccc2N)cc1F | null | [Fe] | O | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccc(Nc2ccccc2)cc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | 99.3 | [{"value": 99.3, "product": "NC1=C(C=CC=C1)NC1=CC(=C(C(=O)OCC)C=C1)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | 1 | HOUR | 200 mg ethyl 2-fluoro-4-(2-nitrophenylamino)benzoate (compound in Production Example 331), 180 mg iron powder, 350 mg ammonium chloride and 8 mL solution mixture of methanol and water (5:3) were stirred at 100° C. for 1 hour. Insolubles were filtered off with Celite, and water was added to the filtrate which was then e... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1.c1ccccc1 | Other | [Fe].O | 100 | 1 | CCOC(=O)c1ccc(Nc2ccccc2[N+](=O)[O-])cc1F>[Fe].O>CCOC(=O)c1ccc(Nc2ccccc2N)cc1F |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-f76b2293b0184ea5b1efefeb0b0b4eb7 | CCOC(=O)c1ccc(Nc2ccccc2N)cc1F.O=C1CCC(=O)N1Br>>CCOC(=O)c1ccc(Nc2cc(Br)ccc2N)cc1F | BrN1C(CCC1=O)=O.NC1=C(C=CC=C1)NC1=CC(=C(C(=O)OCC)C=C1)F.S(=S)(=O)([O-])[O-].[Na+].[Na+].C([O-])(O)=O.[Na+]>>NC1=C(C=C(C=C1)Br)NC1=CC(=C(C(=O)OCC)C=C1)F | [CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][c:9]([NH:10][c:11]2[cH:12][cH:13][cH:15][cH:16][c:17]2[NH2:18])[cH:19][c:20]1[F:21].O=C1CCC(=O)N1[Br:14]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][c:9]([NH:10][c:11]2[cH:12][c:13]([Br:14])[cH:15][cH:16][c:17]2[NH2:18])[cH:19][c:20]1[F:21] | CCOC(=O)c1ccc(Nc2ccccc2N)cc1F.O=C1CCC(=O)N1Br | CCOC(=O)c1ccc(Nc2cc(Br)ccc2N)cc1F | null | null | CN(C=O)C | Functional Group Interconversion | Bromination | 48c1dcf50945076da40bbd7976060ec1ea74b3478ef8c25d67664232b218095c | 0e444576b73669992a4073cc3f7b10ed52cb9df09f9f8e4042e39e6a602aa390 | c1ccc(Nc2ccccc2)cc1 | 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] | 68.2 | [{"value": 68.2, "product": "NC1=C(C=C(C=C1)Br)NC1=CC(=C(C(=O)OCC)C=C1)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | 179 mg ethyl 4-(2-amino-phenylamino)-2-fluoro-benzoate (compound in Production Example 332) was dissolved in 4 mL N,N-dimethylformamide, and 116 mg N-bromosuccinimide was added thereto under ice-cooling and stirred for 2 hours. An aqueous sodium thiosulfate solution and an aqueous sodium bicarbonate solution were added... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Tertiary amide | Aromatic halide | c1ccccc1.C1CCNC1 | c1ccccc1 | c1ccccc1.c1ccccc1 | HO- | CN(C=O)C | null | 2 | CCOC(=O)c1ccc(Nc2ccccc2N)cc1F.O=C1CCC(=O)N1Br>CN(C=O)C>CCOC(=O)c1ccc(Nc2cc(Br)ccc2N)cc1F |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-a61b24039bde45f7abef76817ce1bb39 | CCOC(=O)c1ccc(Nc2cc(Br)ccc2N)cc1F>>CCOC(=O)c1ccc(-n2cnc3ccc(Br)cc32)cc1F | NC1=C(C=C(C=C1)Br)NC1=CC(=C(C(=O)OCC)C=C1)F.C(C)OC(OCC)OCC>>BrC=1C=CC2=C(N(C=N2)C2=CC(=C(C(=O)OCC)C=C2)F)C1 | [CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][c:9]([NH:10][c:19]2[c:13]([NH2:12])[cH:14][cH:15][c:16]([Br:17])[cH:18]2)[cH:20][c:21]1[F:22]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][c:9](-[n:10]2[cH:11][n:12][c:13]3[cH:14][cH:15][c:16]([Br:17])[cH:18][c:19]23)[cH:20][c:21]1[F:22] | CCOC(=O)c1ccc(Nc2cc(Br)ccc2N)cc1F | CCOC(=O)c1ccc(-n2cnc3ccc(Br)cc32)cc1F | null | null | null | Aromatic Heterocycle Formation | OtherReaction | d9700fa3e76550743d6e0392726c4e3536c554578499775d8c87d842c6d8bad6 | c12bf4e666f812d0e692aca3756678364265d1c8b3469e9563c84f9ed1df94d2 | c1ccc(-n2cnc3ccccc32)cc1 | [NH2;D1;+0:1]-[c:2](:[c:3]):[c:4](-[NH;D2;+0:5]-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]):[c:11]>>[c:3]:[c:2]1:[n;H0;D2;+0:1]:[c:12]:[n;H0;D3;+0:5](-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]):[c:4]:1:[c:11] | null | [] | null | null | null | null | 917 mg ethyl 4-(2-amino-5-bromo-phenylamino)-2-fluoro-benzoate (compound in Production Example 333) and 7 mL triethoxymethane were stirred at 140° C. for 3 hours. The solvent was evaporated, and the residue was purified by NH silica gel chromatography (ethyl acetate/hexane). By recrystallization from ethyl acetate/hexa... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Secondary amine | null | c1ccccc1 | c1ccc2nc[nH]c2c1 | c1ccccc1.c1ccc2nc[nH]c2c1 | Other | null | null | null | CCOC(=O)c1ccc(Nc2cc(Br)ccc2N)cc1F>>CCOC(=O)c1ccc(-n2cnc3ccc(Br)cc32)cc1F |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-969424eeab0d4d7bac8784b2fdc5b2ac | O=[N+]([O-])c1cc(Br)ccc1F>>Nc1cc(Br)ccc1F | BrC=1C=CC(=C(C1)[N+](=O)[O-])F.[Cl-].[NH4+].CO>>BrC=1C=CC(=C(C1)N)F | O=[N+:1]([O-])[c:2]1[cH:3][c:4]([Br:5])[cH:6][cH:7][c:8]1[F:9]>>[NH2:1][c:2]1[cH:3][c:4]([Br:5])[cH:6][cH:7][c:8]1[F:9] | O=[N+]([O-])c1cc(Br)ccc1F | Nc1cc(Br)ccc1F | null | [Fe] | O | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccccc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | 93.8 | [{"value": 93.8, "product": "BrC=1C=CC(=C(C1)N)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 3.0 g of 5-bromo-2-fluoronitrobenzene, 3.8 g iron powder and 7.3 g ammonium chloride were heated at 80° C. for 2 hours in a solution mixture of 30 mL methanol and 30 mL water. The reaction mixture was filtered through Celite, the methanol was evaporated, and the reaction mixture was diluted with water and extracted wit... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1 | Other | [Fe].O | null | null | O=[N+]([O-])c1cc(Br)ccc1F>[Fe].O>Nc1cc(Br)ccc1F |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-cbb7fc0bd2bb4f25abd04ac36e999884 | Nc1cc(Br)ccc1F.O=C(c1ccccc1)c1ccccc1>>Fc1ccc(Br)cc1N=C(c1ccccc1)c1ccccc1 | BrC=1C=CC(=C(C1)N)F.C(C1=CC=CC=C1)(=O)C1=CC=CC=C1.C1(=CC=C(C=C1)S(=O)(=O)O)C>>C(C1=CC=CC=C1)(C1=CC=CC=C1)=NC1=C(C=CC(=C1)Br)F | [F:1][c:2]1[cH:3][cH:4][c:5]([Br:6])[cH:7][c:8]1[NH2:9].O=[C:10]([c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1)[c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1>>[F:1][c:2]1[cH:3][cH:4][c:5]([Br:6])[cH:7][c:8]1[N:9]=[C:10]([c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1)[c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1 | Nc1cc(Br)ccc1F.O=C(c1ccccc1)c1ccccc1 | Fc1ccc(Br)cc1N=C(c1ccccc1)c1ccccc1 | null | null | C1(=CC=CC=C1)C.C(C)(=O)OCC | Heteroatom Alkylation and Arylation | Addition of primary amines to ketones/thiocarbonyls | cb968592dec1a2c40e9f51052b6ef3c2d7edca4da22c8c4bb0fad7e1c1c69433 | 009cc6a97ebe0dc96c669f0ef59b95bcc20de7cae20b1b648ce8f8fa82309e57 | c1ccc(N=C(c2ccccc2)c2ccccc2)cc1 | O=[C;H0;D3;+0:1](-[c:2](:[c:3]):[c:4])-[c:5](:[c:6]):[c:7].[NH2;D1;+0:8]-[c:9](:[c:10]):[c:11]>>[c:3]:[c:2](-[C;H0;D3;+0:1](=[N;H0;D2;+0:8]-[c:9](:[c:10]):[c:11])-[c:5](:[c:6]):[c:7]):[c:4] | 42.2 | [{"value": 42.2, "product": "C(C1=CC=CC=C1)(C1=CC=CC=C1)=NC1=C(C=CC(=C1)Br)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | While a solution of 2.43 g 5-bromo-2-fluorophenylamine (compound in Production Example 335), 2.6 g benzophenone and 122 mg 4-toluenesulfonic acid in 50 ml toluene was azeotropically dehydrated, the mixture was heated for 6 hours under reflux. The reaction mixture was diluted with ethyl acetate and washed with brine, th... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Primary amine | Substituted imine | null | null | c1ccccc1.c1ccccc1.c1ccccc1 | HO- | C1(=CC=CC=C1)C.C(C)(=O)OCC | null | null | Nc1cc(Br)ccc1F.O=C(c1ccccc1)c1ccccc1>C1(=CC=CC=C1)C.C(C)(=O)OCC>Fc1ccc(Br)cc1N=C(c1ccccc1)c1ccccc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-af4e17e2607c4f4c8090d6044bb03da1 | CSC.Fc1ccc(Br)cc1N=C(c1ccccc1)c1ccccc1>>CSc1ccc(F)c(N=C(c2ccccc2)c2ccccc2)c1 | [Cl-].[NH4+].C(CCC)[Li].C(C1=CC=CC=C1)(C1=CC=CC=C1)=NC1=C(C=CC(=C1)Br)F.CSC>>C(C1=CC=CC=C1)(C1=CC=CC=C1)=NC1=C(C=CC(=C1)SC)F | C[S:2][CH3:1].Br[c:3]1[cH:4][cH:5][c:6]([F:7])[c:8]([N:9]=[C:10]([c:11]2[cH:12][cH:13][cH:14][cH:15][cH:16]2)[c:17]2[cH:18][cH:19][cH:20][cH:21][cH:22]2)[cH:23]1>>[CH3:1][S:2][c:3]1[cH:4][cH:5][c:6]([F:7])[c:8]([N:9]=[C:10]([c:11]2[cH:12][cH:13][cH:14][cH:15][cH:16]2)[c:17]2[cH:18][cH:19][cH:20][cH:21][cH:22]2)[cH:23]1 | CSC.Fc1ccc(Br)cc1N=C(c1ccccc1)c1ccccc1 | CSc1ccc(F)c(N=C(c2ccccc2)c2ccccc2)c1 | null | null | O1CCCC1.O | Heteroatom Alkylation and Arylation | OtherReaction | 8c6dc51512ab28d4cb9441689ce7cb87249900712ea999d5c69c20b93d2b2353 | c58e6934d5c82ddec3b0774dc166fdbb9c9ad3acfbb76cde182cbe53c5c1e68c | c1ccc(N=C(c2ccccc2)c2ccccc2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].C-[S;H0;D2;+0:6]-[C;D1;H3:7]>>[C;D1;H3:7]-[S;H0;D2;+0:6]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5] | null | [] | null | null | 15 | MINUTE | 2.2 mL n-butyl lithium (2.66 M hexane solution) was added dropwise to a solution of 1.85 g benzhydrylidene-(5-bromo-2-fluorophenyl)-amine (compound in Production Example 336) in 10 mL tetrahydrofuran at −70° C., then the mixture was stirred for 15 minutes, a solution of 0.53 mL methyl sulfide in 5 mL tetrahydrofuran wa... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Monosulfide | Monosulfide | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1 | HBr | O1CCCC1.O | null | 0.25 | CSC.Fc1ccc(Br)cc1N=C(c1ccccc1)c1ccccc1>O1CCCC1.O>CSc1ccc(F)c(N=C(c2ccccc2)c2ccccc2)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-301e0a8a384a44118b2bb5ca131ee775 | CS(=O)(=O)c1ccc(F)c(N)c1.ClCCNCCCl>>CS(=O)(=O)c1ccc(F)c(N2CCNCC2)c1 | C([O-])(O)=O.[Na+].FC1=C(C=C(C=C1)S(=O)(=O)C)N.Cl.ClCCNCCCl>>FC1=C(C=C(C=C1)S(=O)(=O)C)N1CCNCC1 | [CH3:1][S:2](=[O:3])(=[O:4])[c:5]1[cH:6][cH:7][c:8]([F:9])[c:10]([NH2:11])[cH:17]1.Cl[CH2:12][CH2:13][NH:14][CH2:15][CH2:16]Cl>>[CH3:1][S:2](=[O:3])(=[O:4])[c:5]1[cH:6][cH:7][c:8]([F:9])[c:10]([N:11]2[CH2:12][CH2:13][NH:14][CH2:15][CH2:16]2)[cH:17]1 | CS(=O)(=O)c1ccc(F)c(N)c1.ClCCNCCCl | CS(=O)(=O)c1ccc(F)c(N2CCNCC2)c1 | null | null | ClC1=C(C=CC=C1)Cl | Heteroatom Alkylation and Arylation | OtherReaction | dec7615731d236f383a5e0021b2ac4287f587bb876f98147d27e03daac7cbefb | 631870b1ab33be0edc94bc9ae10321f1c5ede4dd4db77035c9d3979e4a2118fb | c1ccc(N2CCNCC2)cc1 | Cl-[CH2;D2;+0:1]-[C:2]-[#7:3]-[C:4]-[CH2;D2;+0:5]-Cl.[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[c:8]:[c:7](-[N;H0;D3;+0:6]1-[CH2;D2;+0:1]-[C:2]-[#7:3]-[C:4]-[CH2;D2;+0:5]-1):[c:9] | 39 | [{"value": 39.0, "product": "FC1=C(C=C(C=C1)S(=O)(=O)C)N1CCNCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 10 mL solution of 432 mg 2-fluoro-5-methylsulfonylphenylamine (compound in Production Example 338) and 490 mg bis(2-chloroethyl)amine hydrochloride in 1,2-dichlorobenzene was stirred at 200° C. for 9 hours. The reaction mixture was neutralized by adding an aqueous saturated sodium bicarbonate solution and then extracte... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary halide.Primary amine | Tertiary amine | null | C1C[NH]CCN1 | c1ccccc1.C1C[NH]CCN1 | HCl | ClC1=C(C=CC=C1)Cl | null | null | CS(=O)(=O)c1ccc(F)c(N)c1.ClCCNCCCl>ClC1=C(C=CC=C1)Cl>CS(=O)(=O)c1ccc(F)c(N2CCNCC2)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-a7dcc9b3fced469691d85657b923039b | CC(C)(C)OC(=O)N1CCNCC1.N#Cc1cc(Br)ccc1F>>CC(C)(C)OC(=O)N1CCN(c2ccc(F)c(C#N)c2)CC1 | C([O-])([O-])=O.[Cs+].[Cs+].BrC=1C=CC(=C(C#N)C1)F.N1(CCNCC1)C(=O)OC(C)(C)C.C1(=CC=CC=C1)P(C1=C(C2=CC=CC=C2C=C1)C1=C(C=CC2=CC=CC=C12)P(C1=CC=CC=C1)C1=CC=CC=C1)C1=CC=CC=C1>>C(#N)C=1C=C(C=CC1F)N1CCN(CC1)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][NH:11][CH2:21][CH2:22]1.Br[c:12]1[cH:13][cH:14][c:15]([F:16])[c:17]([C:18]#[N:19])[cH:20]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][N:11]([c:12]2[cH:13][cH:14][c:15]([F:16])[c:17]([C:18]#[N:19])[cH:20]2)[CH2:21][CH2:22]1 | CC(C)(C)OC(=O)N1CCNCC1.N#Cc1cc(Br)ccc1F | CC(C)(C)OC(=O)N1CCN(c2ccc(F)c(C#N)c2)CC1 | null | [Pd].[Pd].C(C1=CC=CC=C1)=CC(=O)C=CC1=CC=CC=C1.C(C1=CC=CC=C1)=CC(=O)C=CC1=CC=CC=C1.C(C1=CC=CC=C1)=CC(=O)C=CC1=CC=CC=C1 | C1(=CC=CC=C1)C | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | d687b31bdda9f407fdde6ca57e67eee0681e173646c617afef7770c56d05bab9 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc(N2CCNCC2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[#7:6]1-[C:7]-[C:8]-[NH;D2;+0:9]-[C:10]-[C:11]-1>>[c:3]:[c:2]:[c;H0;D3;+0:1](-[N;H0;D3;+0:9]1-[C:10]-[C:11]-[#7:6]-[C:7]-[C:8]-1):[c:4]:[c:5] | null | [] | 80 | CELSIUS | 10 | MINUTE | 1.24 g of 2,2′-bis (diphenylphosphino)-1,1′-binaphthyl and 229 mg of tris (dibenzylideneacetone) dipalladium were dissolved in toluene and stirred at 80° C. for 10 minutes. The reaction mixture was returned to room temperature, and 2.28 g cesium carbonate, 1.0 g 5-bromo-2-fluorobenzonitrile and 1.09 g t-butyl 1-piperaz... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | C1C[NH]CCN1.c1ccccc1 | C1C[NH]CC[NH]1.c1ccccc1 | C1C[NH]CC[NH]1.c1ccccc1 | HBr | [Pd].[Pd].C(C1=CC=CC=C1)=CC(=O)C=CC1=CC=CC=C1.C(C1=CC=CC=C1)=CC(=O)C=CC1=CC=CC=C1.C(C1=CC=CC=C1)=CC(=O)C=CC1=CC=CC=C1.C1(=CC=CC=C1)C | 80 | 0.166667 | CC(C)(C)OC(=O)N1CCNCC1.N#Cc1cc(Br)ccc1F>[Pd].[Pd].C(C1=CC=CC=C1)=CC(=O)C=CC1=CC=CC=C1.C(C1=CC=CC=C1)=CC(=O)C=CC1=CC=CC=C1.C(C1=CC=CC=C1)=CC(=O)C=CC1=CC=CC=C1.C1(=CC=CC=C1)C>CC(C)(C)OC(=O)N1CCN(c2ccc(F)c(C#N)c2)CC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-f14653ef79f24d6b9ac4bda8f513752b | CC(C)(C)OC(=O)N1CCN(c2ccc(F)c(C#N)c2)CC1>>N#Cc1cc(N2CCNCC2)ccc1F | FC(C(=O)O)(F)F.C(#N)C=1C=C(C=CC1F)N1CCN(CC1)C(=O)OC(C)(C)C.O.N>>FC1=C(C#N)C=C(C=C1)N1CCNCC1 | CC(C)(C)OC(=O)[N:9]1[CH2:8][CH2:7][N:6]([c:5]2[cH:4][c:3]([C:2]#[N:1])[c:14]([F:15])[cH:13][cH:12]2)[CH2:11][CH2:10]1>>[N:1]#[C:2][c:3]1[cH:4][c:5]([N:6]2[CH2:7][CH2:8][NH:9][CH2:10][CH2:11]2)[cH:12][cH:13][c:14]1[F:15] | CC(C)(C)OC(=O)N1CCN(c2ccc(F)c(C#N)c2)CC1 | N#Cc1cc(N2CCNCC2)ccc1F | null | null | null | Reduction | Boc amine deprotection | 2c25e19aee181a3c5131cfdfda27035fd54d4379a11d745dfb75d386bacfd500 | a94b29c7264c852156fc1cdd4a0951a4fc26c06d0edc9e50c743825dbf79e3fd | c1ccc(N2CCNCC2)cc1 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1]1-[C:2]-[C:3]-[#7:4]-[C:5]-[C:6]-1>>[#7:4]1-[C:3]-[C:2]-[NH;D2;+0:1]-[C:6]-[C:5]-1 | 101.2 | [{"value": 101.2, "product": "FC1=C(C#N)C=C(C=C1)N1CCNCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Trifluoroacetic acid was added to 500 mg of t-butyl 4-(3-cyano-4-fluorophenyl)-1-piperazinecarboxylate (compound in Production Example 354) and stirred at room temperature for several hours. After the reaction solution was cooled on ice, ammonia water was added thereto and stirred, the aqueous layer was extracted with ... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Secondary amine | C1C[NH]CC[NH]1 | C1C[NH]CCN1 | c1ccccc1.C1C[NH]CCN1 | HO- | null | null | null | CC(C)(C)OC(=O)N1CCN(c2ccc(F)c(C#N)c2)CC1>>N#Cc1cc(N2CCNCC2)ccc1F |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-dc435eadabab4c7aab992d48ebc7c27f | C1CNCCN1.CS(=O)(=O)c1ccc(Br)cc1>>CS(=O)(=O)c1ccc(N2CCNCC2)cc1 | BrC1=CC=C(C=C1)S(=O)(=O)C.N1CCNCC1>>CS(=O)(=O)C1=CC=C(C=C1)N1CCNCC1 | [NH:9]1[CH2:10][CH2:11][NH:12][CH2:13][CH2:14]1.Br[c:8]1[cH:7][cH:6][c:5]([S:2]([CH3:1])(=[O:3])=[O:4])[cH:16][cH:15]1>>[CH3:1][S:2](=[O:3])(=[O:4])[c:5]1[cH:6][cH:7][c:8]([N:9]2[CH2:10][CH2:11][NH:12][CH2:13][CH2:14]2)[cH:15][cH:16]1 | C1CNCCN1.CS(=O)(=O)c1ccc(Br)cc1 | CS(=O)(=O)c1ccc(N2CCNCC2)cc1 | null | [I-].C(CCC)[N+](CCCC)(CCCC)CCCC | O | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | 1d452876efa46787ecd5eab4acf018720843b51fbe40244616ffd72f6a602335 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc(N2CCNCC2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[#7:6]1-[C:7]-[C:8]-[NH;D2;+0:9]-[C:10]-[C:11]-1>>[c:3]:[c:2]:[c;H0;D3;+0:1](-[N;H0;D3;+0:9]1-[C:8]-[C:7]-[#7:6]-[C:11]-[C:10]-1):[c:4]:[c:5] | 91.3 | [{"value": 91.3, "product": "CS(=O)(=O)C1=CC=C(C=C1)N1CCNCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 5 | HOUR | A mixture of 3.0 g 1-bromo-4-methylsulfonyl benzene, 3.3 g piperazine and 470 mg tetrabutyl ammonium iodide was stirred at 120° C. to 140° C. for 5 hours. Water was added to the mixture, then insolubles were filtered off, the filtrate was extracted with dichloromethane. The organic layer was washed with brine and dried... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | C1CNCCN1.c1ccccc1 | c1ccccc1.C1C[NH]CCN1 | c1ccccc1.C1C[NH]CCN1 | HBr | [I-].C(CCC)[N+](CCCC)(CCCC)CCCC.O | null | 5 | C1CNCCN1.CS(=O)(=O)c1ccc(Br)cc1>[I-].C(CCC)[N+](CCCC)(CCCC)CCCC.O>CS(=O)(=O)c1ccc(N2CCNCC2)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-2459a44217094dd5933f672c4625039f | Brc1ccc2ncnc(-c3cccs3)c2c1.O=S(=O)(O)Cl>>O=S(=O)(Cl)c1ccc(-c2ncnc3ccc(Br)cc23)s1 | ClS(=O)(=O)O.S(=O)(Cl)Cl.BrC=1C=C2C(=NC=NC2=CC1)C=1SC=CC1>>BrC=1C=C2C(=NC=NC2=CC1)C1=CC=C(S1)S(=O)(=O)Cl | [cH:5]1[cH:6][cH:7][c:8](-[c:9]2[n:10][cH:11][n:12][c:13]3[cH:14][cH:15][c:16]([Br:17])[cH:18][c:19]23)[s:20]1.O[S:2](=[O:1])(=[O:3])[Cl:4]>>[O:1]=[S:2](=[O:3])([Cl:4])[c:5]1[cH:6][cH:7][c:8](-[c:9]2[n:10][cH:11][n:12][c:13]3[cH:14][cH:15][c:16]([Br:17])[cH:18][c:19]23)[s:20]1 | Brc1ccc2ncnc(-c3cccs3)c2c1.O=S(=O)(O)Cl | O=S(=O)(Cl)c1ccc(-c2ncnc3ccc(Br)cc23)s1 | null | null | O | Heteroatom Alkylation and Arylation | Aromatic sulfonyl chlorination | 8262cd7e2fb49c292864204e18c959a9ad65e1b79f29da3707f938430466ad5f | d32b60b8f9bfd187c6c9f1eef6a22a00f53525a7532b83aba763d5389c9e4280 | c1csc(-c2ncnc3ccccc23)c1 | O-[S;H0;D4;+0:1](-[Cl;D1;H0:2])(=[O;D1;H0:3])=[O;D1;H0:4].[#16;a:5]1:[c:6]:[c:7]:[c:8]:[cH;D2;+0:9]:1>>[Cl;D1;H0:2]-[S;H0;D4;+0:1](=[O;D1;H0:3])(=[O;D1;H0:4])-[c;H0;D3;+0:9]1:[#16;a:5]:[c:6]:[c:7]:[c:8]:1 | null | [] | 60 | CELSIUS | null | null | 0.18 mL chlorosulfonic acid and 0.19 mL thionyl chloride were added to 0.1 g of 6-bromo-4-(2-thienyl)quinazoline (compound in Production Example 96) under ice-cooling in a stream of nitrogen, and the mixture was heated for 13 hours at 60° C., then neutralized by adding water and a sodium bicarbonate solution and extrac... | 10.6084/m9.figshare.5104873.v1 | null | null | Sulfonyl halide | c1ccsc1 | c1ccsc1 | c1ccsc1.c1ccc2ncncc2c1 | HO- | O | 60 | null | Brc1ccc2ncnc(-c3cccs3)c2c1.O=S(=O)(O)Cl>O>O=S(=O)(Cl)c1ccc(-c2ncnc3ccc(Br)cc23)s1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-2f60f7cf671249b0acf69f03ed62bc04 | Brc1ccc2ncnc(-c3cccs3)c2c1.O=S(=O)(O)Cl>>O=S(=O)(Cl)c1ccc(-c2ncnc3ccc(Br)cc23)s1 | C([O-])(O)=O.[Na+].ClS(=O)(=O)O.S(=O)(Cl)Cl.BrC=1C=C2C(=NC=NC2=CC1)C=1SC=CC1>>BrC=1C=C2C(=NC=NC2=CC1)C1=CC=C(S1)S(=O)(=O)Cl | [cH:5]1[cH:6][cH:7][c:8](-[c:9]2[n:10][cH:11][n:12][c:13]3[cH:14][cH:15][c:16]([Br:17])[cH:18][c:19]23)[s:20]1.O=[S:2]([OH:1])(=[O:3])[Cl:4]>>[O:1]=[S:2](=[O:3])([Cl:4])[c:5]1[cH:6][cH:7][c:8](-[c:9]2[n:10][cH:11][n:12][c:13]3[cH:14][cH:15][c:16]([Br:17])[cH:18][c:19]23)[s:20]1 | Brc1ccc2ncnc(-c3cccs3)c2c1.O=S(=O)(O)Cl | O=S(=O)(Cl)c1ccc(-c2ncnc3ccc(Br)cc23)s1 | null | null | O | Protection | Aromatic sulfonyl chlorination | 218ad6407b184db382d4e28de34d7ac34a86551588ce92c2c215481758bc8ff4 | c731d053565135be022f3edbe36cf28a9b4364ca579bdb183b2db9578bab4695 | c1csc(-c2ncnc3ccccc23)c1 | O=[S;H0;D4;+0:1](-[Cl;D1;H0:2])(=[O;D1;H0:3])-[OH;D1;+0:4].[#16;a:5]1:[c:6]:[c:7]:[c:8]:[cH;D2;+0:9]:1>>[Cl;D1;H0:2]-[S;H0;D4;+0:1](=[O;D1;H0:3])(=[O;H0;D1;+0:4])-[c;H0;D3;+0:9]1:[#16;a:5]:[c:6]:[c:7]:[c:8]:1 | null | [] | 60 | CELSIUS | null | null | 14.4 mL chlorosulfonic acid and 14.42 mL thionyl chloride were added to 7.78 g of 6-bromo-4-(2-thienyl)quinazoline (compound in Production Example 96) under ice-cooling in a stream of nitrogen, and the mixture was heated at 60° C. for 16 hours, then poured into iced water, neutralized by adding a sodium bicarbonate sol... | 10.6084/m9.figshare.5104873.v1 | null | null | Sulfonyl halide | c1ccsc1 | c1ccsc1 | c1ccsc1.c1ccc2ncncc2c1 | HO- | O | 60 | null | Brc1ccc2ncnc(-c3cccs3)c2c1.O=S(=O)(O)Cl>O>O=S(=O)(Cl)c1ccc(-c2ncnc3ccc(Br)cc23)s1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-a7ce280c114f486cab7c929a87e21d54 | CN.O=S(=O)(Cl)c1ccc(-c2ncnc3ccc(Br)cc23)s1>>CNS(=O)(=O)c1ccc(-c2ncnc3ccc(Br)cc23)s1 | BrC=1C=C2C(=NC=NC2=CC1)C1=CC=C(S1)S(=O)(=O)Cl.CN>>CNS(=O)(=O)C=1SC(=CC1)C1=NC=NC2=CC=C(C=C12)Br | [CH3:1][NH2:2].Cl[S:3](=[O:4])(=[O:5])[c:6]1[cH:7][cH:8][c:9](-[c:10]2[n:11][cH:12][n:13][c:14]3[cH:15][cH:16][c:17]([Br:18])[cH:19][c:20]23)[s:21]1>>[CH3:1][NH:2][S:3](=[O:4])(=[O:5])[c:6]1[cH:7][cH:8][c:9](-[c:10]2[n:11][cH:12][n:13][c:14]3[cH:15][cH:16][c:17]([Br:18])[cH:19][c:20]23)[s:21]1 | CN.O=S(=O)(Cl)c1ccc(-c2ncnc3ccc(Br)cc23)s1 | CNS(=O)(=O)c1ccc(-c2ncnc3ccc(Br)cc23)s1 | null | null | O1CCCC1 | Miscellaneous | Sulfonamide synthesis (Schotten-Baumann) primary amine | a86b0632821e188c0a5dc5a5a2aac298ab3eccaee8a52ba46078c3d5975a290d | 50f8fbf3d327483c3eeff8f6cbd4065e4c7600bb501fbe08958a5c79a0926428 | c1csc(-c2ncnc3ccccc23)c1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[#16;a:6]:[c:7].[C;D1;H3:8]-[NH2;D1;+0:9]>>[C;D1;H3:8]-[NH;D2;+0:9]-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[#16;a:6]:[c:7] | null | [] | null | null | 1 | HOUR | 800 mg of 5-(6-bromoquinazolin-4-yl)-thiophen-2-sulfonyl chloride (compound in Production Example 377) was dissolved in 15 mL tetrahydrofuran, and 1.78 mL methylamine was added thereto and stirred at room temperature for 1 hour. The solvent was removed, and the residue was purified by silica gel column chromatography (... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Sulfonyl halide | Sulfonamide | null | null | c1ccsc1.c1ccc2ncncc2c1 | HCl | O1CCCC1 | null | 1 | CN.O=S(=O)(Cl)c1ccc(-c2ncnc3ccc(Br)cc23)s1>O1CCCC1>CNS(=O)(=O)c1ccc(-c2ncnc3ccc(Br)cc23)s1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-6519ac15518343e7928c1bc845e13259 | CCOC(OCC)c1ccc(-c2ncnc3ccc(Br)cc23)s1>>O=Cc1ccc(-c2ncnc3ccc(Br)cc23)s1 | BrC=1C=C2C(=NC=NC2=CC1)C=1SC(=CC1)C(OCC)OCC.FC(C(=O)O)(F)F.O>>BrC=1C=C2C(=NC=NC2=CC1)C1=CC=C(S1)C=O | CCO[CH:2]([O:1]CC)[c:3]1[cH:4][cH:5][c:6](-[c:7]2[n:8][cH:9][n:10][c:11]3[cH:12][cH:13][c:14]([Br:15])[cH:16][c:17]23)[s:18]1>>[O:1]=[CH:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[n:8][cH:9][n:10][c:11]3[cH:12][cH:13][c:14]([Br:15])[cH:16][c:17]23)[s:18]1 | CCOC(OCC)c1ccc(-c2ncnc3ccc(Br)cc23)s1 | O=Cc1ccc(-c2ncnc3ccc(Br)cc23)s1 | null | null | ClCCl | Miscellaneous | Acetal hydrolysis to aldehyde | 2c5baf4818f438d514702dbb9f9a64f069b67040aebce8bef29fab8232955599 | 84d5a69453aa750f462aa94a6bf2116fc17c5d88a9619aaa9eefb74b0c09848d | c1csc(-c2ncnc3ccccc23)c1 | C-C-O-[CH;D3;+0:1](-[O;H0;D2;+0:2]-C-C)-[c:3](:[c:4]):[#16;a:5]:[c:6]>>[O;H0;D1;+0:2]=[CH;D2;+0:1]-[c:3](:[c:4]):[#16;a:5]:[c:6] | 98.1 | [{"value": 98.1, "product": "BrC=1C=C2C(=NC=NC2=CC1)C1=CC=C(S1)C=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | 2.6 g of 6-bromo-4-(5-diethoxymethylthiophen-2-yl)quinazoline (compound in Production Example 380) was dissolved in 10 mL dichloromethane, then 5 mL trifluoroacetic acid was added thereto, and the mixture was stirred at room temperature for 3 hours, neutralized by adding water and a sodium bicarbonate solution, and ext... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether | Aldehyde | null | null | c1ccsc1.c1ccc2ncncc2c1 | HO- | ClCCl | null | 3 | CCOC(OCC)c1ccc(-c2ncnc3ccc(Br)cc23)s1>ClCCl>O=Cc1ccc(-c2ncnc3ccc(Br)cc23)s1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-9130d476b2234cf9a01bb669ea3c511b | O=Cc1ccc(-c2ncnc3ccc(Br)cc23)s1.[OH-]>>O=C(O)c1ccc(-c2ncnc3ccc(Br)cc23)s1 | BrC=1C=C2C(=NC=NC2=CC1)C1=CC=C(S1)C=O.[OH-].[Na+]>>BrC=1C=C2C(=NC=NC2=CC1)C1=CC=C(S1)C(=O)O | [O:1]=[CH:2][c:4]1[cH:5][cH:6][c:7](-[c:8]2[n:9][cH:10][n:11][c:12]3[cH:13][cH:14][c:15]([Br:16])[cH:17][c:18]23)[s:19]1.[OH-:3]>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][cH:6][c:7](-[c:8]2[n:9][cH:10][n:11][c:12]3[cH:13][cH:14][c:15]([Br:16])[cH:17][c:18]23)[s:19]1 | O=Cc1ccc(-c2ncnc3ccc(Br)cc23)s1.[OH-] | O=C(O)c1ccc(-c2ncnc3ccc(Br)cc23)s1 | null | [N+](=O)([O-])[O-].[Ag+] | O.CS(=O)C | Acylation | OtherReaction | 212580cf94343ba681451fe636f6c4d850d6e10e1bdc7e1852b33ddb4cd6898f | 37c4d4a9954dede23d940a212db876610ae18deb2faf143c8b44e17692b9193f | c1csc(-c2ncnc3ccccc23)c1 | [O;D1;H0:1]=[CH;D2;+0:2]-[c:3](:[c:4]):[#16;a:5]:[c:6].[OH-;D0:7]>>[O;D1;H0:1]=[C;H0;D3;+0:2](-[OH;D1;+0:7])-[c:3](:[c:4]):[#16;a:5]:[c:6] | 82.6 | [{"value": 82.6, "product": "BrC=1C=C2C(=NC=NC2=CC1)C1=CC=C(S1)C(=O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 24 | HOUR | A solution of 2.19 g silver nitrate in 40 mL water and a solution of 1.96 g 5-(6-bromoquinazolin-4-yl)thiophen-2-carboaldehyde (compound in Production Example 381) in 20 mL dimethyl sulfoxide were added little by little successively to a solution of 1.0 g sodium hydroxide in 40 mL water under ice-cooling, and the mixtu... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | Carboxylic acid | null | null | c1ccsc1.c1ccc2ncncc2c1 | null | [N+](=O)([O-])[O-].[Ag+].O.CS(=O)C | null | 24 | O=Cc1ccc(-c2ncnc3ccc(Br)cc23)s1.[OH-]>[N+](=O)([O-])[O-].[Ag+].O.CS(=O)C>O=C(O)c1ccc(-c2ncnc3ccc(Br)cc23)s1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-a33f2b4bd31c4863a209666470456a1f | Nc1ccc(F)cc1F.O=C(O)c1ccc(-c2ncnc3ccc(Br)cc23)s1>>O=C(Nc1ccc(F)cc1F)c1ccc(-c2ncnc3ccc(Br)cc23)s1 | C(C)N(CC)CC.C(OCC(C)C)(=O)Cl.BrC=1C=C2C(=NC=NC2=CC1)C1=CC=C(S1)C(=O)O.FC1=C(C=CC(=C1)F)N>>FC1=C(C=CC(=C1)F)NC(=O)C=1SC(=CC1)C1=NC=NC2=CC=C(C=C12)Br | [NH2:3][c:4]1[cH:5][cH:6][c:7]([F:8])[cH:9][c:10]1[F:11].O[C:2](=[O:1])[c:12]1[cH:13][cH:14][c:15](-[c:16]2[n:17][cH:18][n:19][c:20]3[cH:21][cH:22][c:23]([Br:24])[cH:25][c:26]23)[s:27]1>>[O:1]=[C:2]([NH:3][c:4]1[cH:5][cH:6][c:7]([F:8])[cH:9][c:10]1[F:11])[c:12]1[cH:13][cH:14][c:15](-[c:16]2[n:17][cH:18][n:19][c:20]3[cH... | Nc1ccc(F)cc1F.O=C(O)c1ccc(-c2ncnc3ccc(Br)cc23)s1 | O=C(Nc1ccc(F)cc1F)c1ccc(-c2ncnc3ccc(Br)cc23)s1 | null | null | O1CCCC1.O | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(Nc1ccccc1)c1ccc(-c2ncnc3ccccc23)s1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[#16;a:5]:[c:6].[NH2;D1;+0:7]-[c:8](:[c:9]):[c:10]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[NH;D2;+0:7]-[c:8](:[c:9]):[c:10])-[c:3](:[c:4]):[#16;a:5]:[c:6] | 42.8 | [{"value": 42.8, "product": "FC1=C(C=CC(=C1)F)NC(=O)C=1SC(=CC1)C1=NC=NC2=CC=C(C=C12)Br", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | 300 mg of 5-(6-bromoquinazolin-4-yl)thiophen-2-carboxylic acid (compound in Production Example 382) was dissolved in 4 mL tetrahydrofuran, then 0.37 mL triethylamine and 0.14 mL isobutyl chlorocarbonate were added thereto under ice-cooling, and the mixture was stirred for 1 hour under nitrogen atmosphere. This mixture ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccsc1.c1ccc2ncncc2c1 | HO- | O1CCCC1.O | null | 1 | Nc1ccc(F)cc1F.O=C(O)c1ccc(-c2ncnc3ccc(Br)cc23)s1>O1CCCC1.O>O=C(Nc1ccc(F)cc1F)c1ccc(-c2ncnc3ccc(Br)cc23)s1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-6166f5ee7a5447d7a41b08353050cb49 | NC1CC1.O=C(O)c1ccc(-c2ncnc3ccc(Cl)cc23)cc1F>>O=C(NC1CC1)c1ccc(-c2ncnc3ccc(Cl)cc23)cc1F | F[P-](F)(F)(F)(F)F.N1(N=NC2=C1C=CC=C2)O[P+](N(C)C)(N(C)C)N(C)C.ClC=1C=C2C(=NC=NC2=CC1)C1=CC(=C(C(=O)O)C=C1)F.C1(CC1)N.C(C)N(CC)CC>>ClC=1C=C2C(=NC=NC2=CC1)C1=CC(=C(C(=O)NC2CC2)C=C1)F | [NH2:3][CH:4]1[CH2:5][CH2:6]1.O[C:2](=[O:1])[c:7]1[cH:8][cH:9][c:10](-[c:11]2[n:12][cH:13][n:14][c:15]3[cH:16][cH:17][c:18]([Cl:19])[cH:20][c:21]23)[cH:22][c:23]1[F:24]>>[O:1]=[C:2]([NH:3][CH:4]1[CH2:5][CH2:6]1)[c:7]1[cH:8][cH:9][c:10](-[c:11]2[n:12][cH:13][n:14][c:15]3[cH:16][cH:17][c:18]([Cl:19])[cH:20][c:21]23)[cH:2... | NC1CC1.O=C(O)c1ccc(-c2ncnc3ccc(Cl)cc23)cc1F | O=C(NC1CC1)c1ccc(-c2ncnc3ccc(Cl)cc23)cc1F | null | null | ClCCl | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(NC1CC1)c1ccc(-c2ncnc3ccccc23)cc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[NH2;D1;+0:6]-[C:7]1-[C:8]-[C:9]-1>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[NH;D2;+0:6]-[C:7]1-[C:8]-[C:9]-1)-[c:3](:[c:4]):[c:5] | 71.7 | [{"value": 71.7, "product": "ClC=1C=C2C(=NC=NC2=CC1)C1=CC(=C(C(=O)NC2CC2)C=C1)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | 0.2 g 4-(6-chloroquinazolin-4-yl)-2-fluorobenzoic acid (compound in Production Example 386), 41 mg cyclopropylamine and 0.12 mL triethylamine were dissolved in 6 mL dichloromethane, then 320 mg benzotriazol-1-yloxytris(dimethylamino)-phosphonium hexafluorophosphate was added thereto, and the mixture was stirred at room... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | C1CC1.c1ccccc1.c1ccc2ncncc2c1 | HO- | ClCCl | null | 3 | NC1CC1.O=C(O)c1ccc(-c2ncnc3ccc(Cl)cc23)cc1F>ClCCl>O=C(NC1CC1)c1ccc(-c2ncnc3ccc(Cl)cc23)cc1F |
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