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【结 构 式】

【分子编号】61954

【品名】tert-butyl 4-{[2-(2-oxo-1,2-dihydro-3-quinolinyl)-1H-benzimidazol-5-yl]carbonyl}-1-piperazinecarboxylate

【CA登记号】

【 分 子 式 】C26H27N5O4

【 分 子 量 】473.53168

【元素组成】C 65.95% H 5.75% N 14.79% O 13.51%

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:(VIII)

Treatment of 2-chloroquinoline-3-carboxylic acid (I) with oxalyl chloride affords acid chloride (II), which is subsequently coupled with methyl 3,4-diaminobenzoate (III) to yield amide (IV). Intramolecular cyclization of amino amide (IV) with Burgess reagent in refluxing THF produces the benzimidazole (V). Then, acidic hydrolysis of both methyl ester and chloroquinoline functions of (V) gives rise to the carboxylic acid (VI). Coupling of (VI) with N-Boc-piperazine (VII) furnishes amide (VIII). The N-Boc protecting group of (VIII) is finally removed by treatment with trifluoroacetic acid in CH2Cl2.

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) 61948 2-chloro-3-quinolinecarboxylic acid C10H6ClNO2 详情 详情
(II) 61950 2-chloro-3-quinolinecarbonyl chloride C10H5Cl2NO 详情 详情
(III) 34921 3-cyanobenzoyl chloride 1711-11-1 C8H4ClNO 详情 详情
(IV) 61951 methyl 3-amino-4-{[(2-chloro-3-quinolinyl)carbonyl]amino}benzoate C18H14ClN3O3 详情 详情
(V) 61952 methyl 2-(2-chloro-3-quinolinyl)-1H-benzimidazole-5-carboxylate C18H12ClN3O2 详情 详情
(VI) 61953 2-(2-oxo-1,2-dihydro-3-quinolinyl)-1H-benzimidazole-5-carboxylic acid C17H11N3O3 详情 详情
(VII) 13225 N-tert-Butoxycarbonyl piperazine; tert-butyl 1-piperazinecarboxylate;tert-butyl piperazine-1-carboxylate 143238-38-4 C9H18N2O2 详情 详情
(VIII) 61954 tert-butyl 4-{[2-(2-oxo-1,2-dihydro-3-quinolinyl)-1H-benzimidazol-5-yl]carbonyl}-1-piperazinecarboxylate C26H27N5O4 详情 详情
Extended Information