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【结 构 式】

【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