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【结 构 式】

【分子编号】58241

【品名】7-{6-[acetyl(methyl)amino]-5-methyl-3-pyridinyl}-1-cyclopropyl-8-methyl-4-oxo-1,4-dihydro-3-quinolinecarboxylic acid

【CA登记号】

【 分 子 式 】C23H23N3O4

【 分 子 量 】405.45344

【元素组成】C 68.13% H 5.72% N 10.36% O 15.78%

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:(XII)

5-Bromo-2-chloro-3-methylpyridine (VII) is treated with aqueous methylamine to yield the aminopyridine derivative (VIII), which is further acetylated to (IX) using acetic anhydride in pyridine. Stannylation of the bromopyridine (IX) by means of hexabutylditin in the presence of palladium catalyst gives rise to the tributylstannyl pyridine (X). This compound is then subjected to Stille coupling with the bromoquinoline (VI) to furnish the corresponding pyridyl quinoline adduct (XI). Basic hydrolysis of the ethyl ester group of (XI) provides the quinolinecarboxylic acid (XII). The N-acetyl group of (XII) is finally hydrolyzed under acidic conditions to give the title compound.

1 Hayashi, K.; Yamakawa, T.; Kawafuchi, H.; Kito, T.; Mitsuyama, J.; Kuroda, H. (Toyama Chemical Co., Ltd.); Quinolonecarboxylic acid derivs. or salts thereof. EP 1070713; WO 9951588 .
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(VI) 58235 ethyl 7-bromo-1-cyclopropyl-8-methyl-4-oxo-1,4-dihydro-3-quinolinecarboxylate C16H16BrNO3 详情 详情
(VII) 58236 5-bromo-2-chloro-3-methylpyridine C6H5BrClN 详情 详情
(VIII) 58237 N-(5-bromo-3-methyl-2-pyridinyl)-N-methylamine; 5-bromo-N,3-dimethyl-2-pyridinamine C7H9BrN2 详情 详情
(IX) 58238 N-(5-bromo-3-methyl-2-pyridinyl)-N-methylacetamide C9H11BrN2O 详情 详情
(X) 58239 N-methyl-N-[3-methyl-5-(tributylstannyl)-2-pyridinyl]acetamide C21H38N2OSn 详情 详情
(XI) 58240 ethyl 7-{6-[acetyl(methyl)amino]-5-methyl-3-pyridinyl}-1-cyclopropyl-8-methyl-4-oxo-1,4-dihydro-3-quinolinecarboxylate C25H27N3O4 详情 详情
(XII) 58241 7-{6-[acetyl(methyl)amino]-5-methyl-3-pyridinyl}-1-cyclopropyl-8-methyl-4-oxo-1,4-dihydro-3-quinolinecarboxylic acid C23H23N3O4 详情 详情
Extended Information