1-isopropyl-N-[(1R,5S)-8-methyl-8-azabicyclo[3.2.1]oct-3-yl]-2-oxo-1,2-dihydro-3-quinolinecarboxamide -Drug Synthesis Database

【结构式】

【分子编号】36337

【品名】1-isopropyl-N-[(1R,5S)-8-methyl-8-azabicyclo[3.2.1]oct-3-yl]-2-oxo-1,2-dihydro-3-quinolinecarboxamide

【CA登记号】

【分子式】C₂₁H₂₇N₃O₂

【分子量】353.4644

【元素组成】C 71.36% H 7.7% N 11.89% O 9.05%

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：(X)

Condensation of acid chloride (VIII) 3-aminotropane (IX) provided amide (X). N-Demethylation of (X) was then achieved by treatment with 1-chloroethyl chloroformate, followed by hydrolysis and decarboxylation of the intermediate carbamate (XI) with MeOH. The resulting secondary amine (XII) was then alkylated with 3-bromopropanol (XIII) to afford the target hydroxypropyl derivative.

参考文献中间体

合成目标

【1】 Yokomori, S.; Muramatsu, M.; Suzuki, M.; Ito, C.; Asanuma, H.; Isobe, Y.; Ohuchi, Y.; Kaneko, T.; Synthesis and evaluation of novel 2-oxo-1,2-dihydro-3-quinolinecarboxamide derivatives as potent and selective serotonin 5-HT4 receptor agonists. Chem Pharm Bull 2001, 49, 1, 29.
【2】 Ohuchi, Y.; Suzuki, M.; Asanuma, H.; Yokomori, S.; Hatayama, K. (Taisho Pharmaceutical Co., Ltd.); Quinolinecarboxylic acid deriv.. EP 0710662; JP 1996034784; US 5753673; WO 9531455 .

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
	22014	1-chloro-1-[(chlorocarbonyl)oxy]ethane	50893-53-3	C₃H₄Cl₂O₂	详情	详情
(VIII)	36336	1-isopropyl-2-oxo-1,2-dihydro-3-quinolinecarbonyl chloride		C₁₃H₁₂ClNO₂	详情	详情
(IX)	12412	(1R,5S)-8-Methyl-8-azabicyclo[3.2.1]octan-3-amine; (1R,5S)-8-Methyl-8-azabicyclo[3.2.1]oct-3-ylamine		C₈H₁₆N₂	详情	详情
(X)	36337	1-isopropyl-N-[(1R,5S)-8-methyl-8-azabicyclo[3.2.1]oct-3-yl]-2-oxo-1,2-dihydro-3-quinolinecarboxamide		C₂₁H₂₇N₃O₂	详情	详情
(XI)	36338	1-chloroethyl (1R,5S)-3-[[(1-isopropyl-2-oxo-1,2-dihydro-3-quinolinyl)carbonyl]amino]-8-azabicyclo[3.2.1]octane-8-carboxylate		C₂₃H₂₈ClN₃O₄	详情	详情
(XII)	36339	N-[(1R,5S)-8-azabicyclo[3.2.1]oct-3-yl]-1-isopropyl-2-oxo-1,2-dihydro-3-quinolinecarboxamide		C₂₀H₂₅N₃O₂	详情	详情
(XIII)	12573	3-Bromo-1-propanol; 3-Bromopropanol	627-18-9	C₃H₇BrO	详情	详情

Extended Information