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【结 构 式】 
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【药物名称】 【化学名称】3-[5-[2-(1-Piperidinyl)ethoxy]-1H-benzimidazol-2-yl]quinolin-2(1H)-one 【CA登记号】335672-08-7 【 分 子 式 】C23H24N4O2 【 分 子 量 】388.47333 |
【开发单位】Merck & Co. (Originator) 【药理作用】Oncolytic Drugs, Angiogenesis Inhibitors, VEGFR-2 (FLK-1/KDR) Inhibitors |
合成路线1
Alkylation of 4-amino-3-nitrophenol (I) with 1-(2-chloroethyl)piperidine (II) provides ether (III). Subsequent nitro group reduction in (III) to afford diamine (IV) is performed by means of zinc powder in AcOH. Coupling of diamine (IV) with 2-chloroquinoline-3-carboxylic acid (V) furnishes amide (VI). Then, intramolecular cyclization of amino amide (VI) with Burgess reagent, followed by hydrolysis in boiling 6 M HCl gives rise to the title benzimidazolyl quinolinone.
| 【1】 Hungate, R.W.; Fraley, M.E.; Hambaugh, S.R. (Merck & Co., Inc.); Tyrosine kinase inhibitors. JP 2003512353; US 6479512; WO 0128993 . |
| 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) | 61945 | 4-amino-3-nitrophenol | C6H6N2O3 | 详情 | 详情 | |
| (II) | 10117 | 1-(2-Chloroethyl)piperidine; N-(2-Chloroethyl)piperidine | 1932-03-2 | C7H14ClN | 详情 | 详情 |
| (III) | 61946 | 2-nitro-4-[2-(1-piperidinyl)ethoxy]aniline; 2-nitro-4-[2-(1-piperidinyl)ethoxy]phenylamine | C13H19N3O3 | 详情 | 详情 | |
| (IV) | 61947 | 2-amino-4-[2-(1-piperidinyl)ethoxy]phenylamine; 4-[2-(1-piperidinyl)ethoxy]-1,2-benzenediamine | C13H21N3O | 详情 | 详情 | |
| (V) | 61948 | 2-chloro-3-quinolinecarboxylic acid | C10H6ClNO2 | 详情 | 详情 | |
| (VI) | 61949 | N-{2-amino-4-[2-(1-piperidinyl)ethoxy]phenyl}-2-chloro-3-quinolinecarboxamide | C23H25ClN4O2 | 详情 | 详情 |
Extended Information