N-{2-amino-4-[2-(1-piperidinyl)ethoxy]phenyl}-2-chloro-3-quinolinecarboxamide -Drug Synthesis Database

【结构式】

【分子编号】61949

【品名】N-{2-amino-4-[2-(1-piperidinyl)ethoxy]phenyl}-2-chloro-3-quinolinecarboxamide

【CA登记号】

【分子式】C₂₃H₂₅ClN₄O₂

【分子量】424.92996

【元素组成】C 65.01% H 5.93% Cl 8.34% N 13.18% O 7.53%

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：(VI)

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.

参考文献中间体

合成目标

【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