【结 构 式】 |
【分子编号】52180 【品名】[2-chloro-4-(5-methyl-1H-pyrazol-1-yl)phenyl][5H-pyrrolo[2,1-c][1,4]benzodiazepin-10(11H)-yl]methanone 【CA登记号】 |
【 分 子 式 】C23H19ClN4O 【 分 子 量 】402.88292 【元素组成】C 68.57% H 4.75% Cl 8.8% N 13.91% O 3.97% |
与该中间体有关的原料药合成路线共 1 条
合成路线1
该中间体在本合成路线中的序号:(IX)Acylation of the pyrrolobenzodiazepine (I) with 2-chloro-4-fluorobenzoyl chloride (V) prepared from the acid (VI) and oxalyl chloride and catalytic DMF with Hünig's base in dichloromethane gives the acylated pyrrolobenzodiazepine (VII). Treatment of (VII) with a solution of the sodium salt of 3-methylpyrazole (VIII) in DMF yields a 85:15 mixture of WAY-VNA-932 and its 5-methyl isomer (IX) which can be separated by column chromatography using an ethyl acetate/hexane mixture over silica gel.
【1】 Caggiano, T.J.; WAY-VNA-932. Drugs Fut 2002, 27, 3, 248. |
【2】 Trybulski, E.J.; Ashwell, M.A.; Molinari, A.J.; Bagli, J.F.; Chan, P.S.; Failli, A.A.; Dusza, J.P.; Albright, J.D.; Caggiano, T.J. (American Home Products Corp.); Tricyclic vasopressin agonists. EP 1000062; WO 9906409 . |
中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
---|---|---|---|---|---|---|
(I) | 21084 | 10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine | 22162-53-4 | C12H12N2 | 详情 | 详情 |
(V) | 37996 | 2-chloro-4-fluorobenzoyl chloride | 21900-54-9 | C7H3Cl2FO | 详情 | 详情 |
(VI) | 10801 | 2-Chloro-4-fluorobenzoic acid; 4-Fluoro-2-chlorobenzoic acid | 2252-51-9 | C7H4ClFO2 | 详情 | 详情 |
(VII) | 37997 | (2-chloro-4-fluorophenyl)[5H-pyrrolo[2,1-c][1,4]benzodiazepin-10(11H)-yl]methanone | C19H14ClFN2O | 详情 | 详情 | |
(VIII) | 37998 | 3-methyl-1H-pyrazole | 1453-58-3 | C4H6N2 | 详情 | 详情 |
(IX) | 52180 | [2-chloro-4-(5-methyl-1H-pyrazol-1-yl)phenyl][5H-pyrrolo[2,1-c][1,4]benzodiazepin-10(11H)-yl]methanone | C23H19ClN4O | 详情 | 详情 |
Extended Information