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【结 构 式】

【分子编号】64340

【品名】ethyl 3-{5-[(6-chloro-3-pyridinyl)carbonyl]-1-methyl-1H-pyrrol-2-yl}propanoate

【CA登记号】

【 分 子 式 】C16H17ClN2O3

【 分 子 量 】320.77536

【元素组成】C 59.91% H 5.34% Cl 11.05% N 8.73% O 14.96%

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:(V)

Wittig reaction of 1-methylpyrrole-2-carboxaldehyde (I) with (ethoxycarbonylmethylene)triphenylphosphorane furnishes the pyrrolylacrylate ester (II), which is subsequently hydrogenated over Pd/C to the pyrrolylpropionate (III). Friedel-Crafts acylation of pyrrole (III) with 6-chloronicotinoyl chloride (IV) gives rise to the pyrrolyl ketone (V). After alkaline hydrolysis of the ethyl ester group of (V), the resultant carboxylic acid (VI) is converted into the corresponding acid chloride (VII) employing oxalyl chloride and DMF. Finally, coupling of acid chloride (VII) with the known aniline derivative (VIII) leads to the desired amide.

1 Youngman, M.A.; Carson, J.R.; Lee, J.S.; Dax, S.L.; Zhang, S.-P.; Colburn, R.W.; Stone, D.J.; Codd, E.E.; Jetter, M.C.; Synthesis and structure-activity relationships of aroylpyrrole alkylamide bradykinin (B2) antagonists. Bioorg Med Chem Lett 2003, 13, 7, 1341.
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) 64337 1-methyl-1H-pyrrole-2-carbaldehyde C6H7NO 详情 详情
(II) 64338 ethyl 3-(1-methyl-1H-pyrrol-2-yl)-2-propenoate C10H13NO2 详情 详情
(III) 64339 ethyl 3-(1-methyl-1H-pyrrol-2-yl)propanoate C10H15NO2 详情 详情
(IV) 30256 6-chloronicotinoyl chloride 58757-38-3 C6H3Cl2NO 详情 详情
(V) 64340 ethyl 3-{5-[(6-chloro-3-pyridinyl)carbonyl]-1-methyl-1H-pyrrol-2-yl}propanoate C16H17ClN2O3 详情 详情
(VI) 64341 3-{5-[(6-chloro-3-pyridinyl)carbonyl]-1-methyl-1H-pyrrol-2-yl}propanoic acid C14H13ClN2O3 详情 详情
(VII) 64342 3-{5-[(6-chloro-3-pyridinyl)carbonyl]-1-methyl-1H-pyrrol-2-yl}propanoyl chloride C14H12Cl2N2O2 详情 详情
(VIII) 64343 2,4-dichloro-N-methyl-3-{[(2-methyl-8-quinolinyl)oxy]methyl}aniline; N-(2,4-dichloro-3-{[(2-methyl-8-quinolinyl)oxy]methyl}phenyl)-N-methylamine C18H16Cl2N2O 详情 详情
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