Cipropride, -Drug Synthesis Database

【结构式】

【药物名称】Cipropride

【化学名称】N-[1-(Cyclopropylmethyl)pyrrolidin-2-ylmethyl]-2-methoxy-5-sulfamoylbenzamide

【CA登记号】68475-40-1, 69046-23-7 (hydrochloride)

【分子式】C₁₇H₂₅N₃O₄S

【分子量】367.4705

【开发单位】

【药理作用】　

合成路线1

The esterification of proline (I) with SOCl2 and ethanol gives ethyl prolinate (II), which by treatment with NH3 in methanol is converted into prolinamide (III). The acylation of (III) with cyclopropylcarbonyl chloride (IV) by means of K2CO3 in acetone yields 1-cyclopropylcarbonyl-2-carbamoylpyrrolidine (V), which is reduced with LiAlH4 in ether to afford 1-cyclopropylmethyl-2-aminomethylpyrrolidine (VI) (1,2). Finally this compound is condensed with ethyl 5-sulfamoyl-2-methoxybenzoate (VII) by heating at 120 C

参考文献中间体

【1】 Kaplan, J.P.; et al. (Synthelabo, S.A.); BE 857544; DE 2735036; FR 2360572; FR 2372157; FR 2395261; GB 1555890; JP 7825563; NL 7708571; ZA 7704743 .
【2】 Kaplan, J.P.; et al. (Synthelabo, S.A.); BE 836752; CA 1039731; CH 612668; DE 2556457; FR 2294698; FR 2327771; FR 2331345; GB 1508880; JP 7748661; NL 7514620; US 4021567; US 4156060; US 4172143; US 4189495; ZA 7507828 .
【3】 (Synthelabo, S.A.); BE 861866; FR 2394529; GB 1560019; JP 7905969; NL 7713631; ZA 7706950 .
【4】 Blancafort, P.; Serradell, M.N.; Castaner, J.; Hillier, K.; Cipropride. Drugs Fut 1981, 6, 4, 220.
【5】 Obitz, D.C.L. (Synthelabo, S.A.); FR 2393794 .

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)	61051	ethyl 2-pyrrolidinecarboxylate		C₅H₉NO₂	详情	详情
(II)	61052	ethyl 2-pyrrolidinecarboxylate		C₇H₁₃NO₂	详情	详情
(III)	22654	2-pyrrolidinecarboxamide	2812-47-7	C₅H₁₀N₂O	详情	详情
(IV)	14601	N-(2-oxo-2-phenylethyl)acetamide		C₁₀H₁₁NO₂	详情	详情
(V)	61053	1-(cyclopropylcarbonyl)-2-pyrrolidinecarboxamide		C₉H₁₄N₂O₂	详情	详情
(VI)	61054	[1-(cyclopropylmethyl)-2-pyrrolidinyl]methanamine; [1-(cyclopropylmethyl)-2-pyrrolidinyl]methylamine		C₉H₁₈N₂	详情	详情
(VII)	61055	ethyl 5-(aminosulfonyl)-2-methoxybenzoate		C₁₀H₁₃NO₅S	详情	详情

Extended Information