methyl 3-[7-(benzyloxy)-3-quinolinyl]-2-chloropropanoate -Drug Synthesis Database

【结构式】

【分子编号】41514

【品名】methyl 3-[7-(benzyloxy)-3-quinolinyl]-2-chloropropanoate

【CA登记号】

【分子式】C₂₀H₁₈ClNO₃

【分子量】355.82056

【元素组成】C 67.51% H 5.1% Cl 9.96% N 3.94% O 13.49%

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)

Treatment of 3-nitro-7-hydroxyquinoline (I) with NaH and benzyl bromide (A) provides benzyloxyderivative (II), which is reduced with SnCl4 in HCl/EtOH to yield (III). Amine (III) is then converted into (IV) via the diazonium salt by treatment with NaNO2 in HCl followed by reaction with methyl acrylate (B) in presence of CuO. Cyclization of (IV) with thiourea in 2-methoxyethanol in presence of NaOAc affords imino-thiazolidinone (V), which is finally hydrolyzed with HCl and EtOH.

参考文献中间体

合成目标

【1】 Nomura, Y.; Sakuma, S.; Masui, S. (Nippon Chemiphar Co., Ltd.); Quinoline deriv.. EP 0787725; JP 1997100280; US 5693651; WO 9612719 .

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
	10180	Thiourea	62-56-6	CH₄N₂S	详情	详情
(A)	12912	1-(Bromomethyl)benzene; Alpha-bromotoluene	100-39-0	C₇H₇Br	详情	详情
(B)	14156	methyl acrylate	96-33-3	C₄H₆O₂	详情	详情
(I)	41511	3-nitro-7-quinolinol		C₉H₆N₂O₃	详情	详情
(II)	41512	7-(benzyloxy)-3-nitroquinoline; benzyl 3-nitro-7-quinolinyl ether		C₁₆H₁₂N₂O₃	详情	详情
(III)	41513	7-(benzyloxy)-3-quinolinamine; 7-(benzyloxy)-3-quinolinylamine		C₁₆H₁₄N₂O	详情	详情
(IV)	41514	methyl 3-[7-(benzyloxy)-3-quinolinyl]-2-chloropropanoate		C₂₀H₁₈ClNO₃	详情	详情
(V)	41515	5-[[7-(benzyloxy)-3-quinolinyl]methyl]-2-imino-1,3-thiazolidin-4-one		C₂₀H₁₇N₃O₂S	详情	详情

Extended Information