Sulmepride, -Drug Synthesis Database

【结构式】

【药物名称】Sulmepride

【化学名称】5-(Aminosulfonyl)-2-methoxy-N-(1-methylpyrrolidin-2-ylmethyl)benzamide

【CA登记号】57479-88-6

【分子式】C₁₄H₂₁N₃O₄S

【分子量】327.40517

【开发单位】

【药理作用】　

合成路线1 合成路线2

合成路线1

A new procedure for the synthesis of sulmepride has been reported: 5-chlorosulfonyl-2-methoxybenzoic acid (I) reacts with 2-(aminomethyl)-1-methylpyrrolidine (II) and thionyl chloride to give 5-chlorosulfonyl-N-[(1-methyl-2-pyrrolidinyl)methyl]-2-methoxybenzamide (III) which is treated with ammonia

参考文献中间体

【1】 FR 2478093 .

中间体序号	中间体编号	品名	分子式	供应商	用于合成
(I)	21354	5-(chlorosulfonyl)-2-methoxybenzoic acid	C₈H₇ClO₅S	详情	详情
(II)	60759	(1-methyl-2-pyrrolidinyl)methylamine; (1-methyl-2-pyrrolidinyl)methanamine	C₆H₁₄N₂	详情	详情
(III)	60760	4-methoxy-3-({[(1-methyl-2-pyrrolidinyl)methyl]amino}carbonyl)benzenesulfonyl chloride	C₁₄H₁₉ClN₂O₄S	详情	详情

合成路线2

The reaction of imidazole (I) with phosgene (II) in hot benzene gives carbonyldiimidazole (III), which is condensed with 5-sulfamoyl-2-methoxybenzoic acid (IV) in THF yielding 1-(5-sulfamoyl-2-methoxybenzoyl)imidazole (V). Finally this compound is condensed with 1-methyl-2-aminomethylpyrrolidine (VI) in THF at room temperature

参考文献中间体

【1】 (Société d'Estude Scientifiques et Industrielles de I'lle-de-France.); BE 658250; CA 801043; CH 468377; DE 1595915; DE 1795723; FR 1472025; GB 1088531; JP 6706913; JP 6923496; NL 6500326; US 3342826; ZA 6406127
【2】 CH 468377 .

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)	10255	Imidazole; 1H-Imidazole	288-32-4	C₃H₄N₂	详情	详情
(III)	11353	1,1'-Carbonyldiimidazole; Di(1H-imidazol-1-yl)methanone; N,N-Carbonyldiimidazole; 1,1'-Carbonylbis(1H-imidazole)	530-62-1	C₇H₆N₄O	详情	详情
(IV)	21355	5-(aminosulfonyl)-2-methoxybenzoic acid; 2-methoxy-5-sulfamoylbenzoic acid	22117-85-7	C₈H₉NO₅S	详情	详情
(V)	60761	3-(1H-imidazol-1-ylcarbonyl)-4-methoxybenzenesulfonamide		C₁₁H₁₁N₃O₄S	详情	详情
(VI)	60759	(1-methyl-2-pyrrolidinyl)methylamine; (1-methyl-2-pyrrolidinyl)methanamine		C₆H₁₄N₂	详情	详情

Extended Information