1-butyl-4-(3-methoxyphenyl)-2-oxo-1,2-dihydro[1,8]naphthyridine-3-carboxylic acid -Drug Synthesis Database

【结构式】

【分子编号】63688

【品名】1-butyl-4-(3-methoxyphenyl)-2-oxo-1,2-dihydro[1,8]naphthyridine-3-carboxylic acid

【CA登记号】

【分子式】C₂₀H₂₀N₂O₄

【分子量】352.38988

【元素组成】C 68.17% H 5.72% N 7.95% O 18.16%

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：(IV)

Condensation of 2-amino-3-(3-methoxybenzoyl)pyridine (I) with diethyl malonate in refluxing pyridine provides the naphthyridine derivative (II), which is subsequently alkylated by butyl iodide in the presence of NaH to afford the N-butyl naphthyridinone (III). Alkaline hydrolysis of the ethyl ester group of (III) leads to the carboxylic acid (IV). This is then subjected to Curtius rearrangement in the presence of diphenylphosphoryl azide, and the obtained isocyanate (V) is further condensed with 2,6-diisopropylaniline (VI) producing urea (VII).

参考文献中间体

合成目标

【1】 Muraoka, M.; Ioriya, K.; Ohashi, N.; Yagi, H. (Sumitomo Pharmaceuticals Co., Ltd.); Novel naphthyridine derivs.. EP 0947515; JP 1998212288; WO 9823615 .

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)	63685	(2-amino-3-pyridinyl)(3-methoxyphenyl)methanone		C₁₃H₁₂N₂O₂	详情	详情
(II)	63686	ethyl 4-(3-methoxyphenyl)-2-oxo-1,2-dihydro[1,8]naphthyridine-3-carboxylate		C₁₈H₁₆N₂O₄	详情	详情
(III)	63687	ethyl 1-butyl-4-(3-methoxyphenyl)-2-oxo-1,2-dihydro[1,8]naphthyridine-3-carboxylate		C₂₂H₂₄N₂O₄	详情	详情
(IV)	63688	1-butyl-4-(3-methoxyphenyl)-2-oxo-1,2-dihydro[1,8]naphthyridine-3-carboxylic acid		C₂₀H₂₀N₂O₄	详情	详情
(V)	63689	1-butyl-3-isocyanato-4-(3-methoxyphenyl)[1,8]naphthyridin-2(1H)-one		C₂₀H₁₉N₃O₃	详情	详情
(VI)	21904	2,6-diisopropylaniline; 2,6-diisopropylphenylamine	24544-04-5	C₁₂H₁₉N	详情	详情
(VII)	63690	N-[1-butyl-4-(3-methoxyphenyl)-2-oxo-1,2-dihydro[1,8]naphthyridin-3-yl]-N'-(2,6-diisopropylphenyl)urea		C₃₂H₃₈N₄O₃	详情	详情

Extended Information