Mefenidil, McN-2378-46(fumarate), McN-2378, -Drug Synthesis Database

【结构式】

【药物名称】Mefenidil, McN-2378-46(fumarate), McN-2378

【化学名称】5-Methyl-2-phenyl-1H-imidazole-4-acetonitrile
　　　　　　4-Cyanomethyl-2-phenyl-5-methylimidazole

【CA登记号】58261-91-9, 83153-38-2 (fumarate)

【分子式】C₁₂H₁₁N₃

【分子量】197.24157

【开发单位】Ortho-McNeil (Originator)

【药理作用】CARDIOVASCULAR DRUGS, Hypertension, Treatment of, Vasodilators

合成路线1

The cyclization of benzamidine (I) with biacetyl (II) in water - isopropanol gives 4,5-dimethyl-2-phenylimidazoline-4,5-diol (III), which by treatment with refluxing aqueous 10% HCl is converted into 4-hydroxymethyl-2-phenyl-5-methylimidazole (IV). The reaction of (IV) with SOCl2 in refluxing benzene yields 4-chloromethyl-2-phenyl-5-methylimidazole (V), which is finally treated with NaCN in DMSO - water.

参考文献中间体

【1】 Rasmussen, C.R.; 2-Aryl-4-cyanomethyl-5-methylimidazoles. DE 2528640; FR 2296627; FR 2309540; FR 2309541; GB 1502142; JP 51034159; US 4093811 .
【2】 Blancafort, P.; Hillier, K.; Serradell, M.N.; Castaner, J.; McN-2378. Drugs Fut 1982, 7, 4, 262.

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)	37052	Benzamidine; benzenecarboximidamide		C₇H₈N₂	详情	详情
(II)	37053	biacetyl	431-03-8	C₄H₆O₂	详情	详情
(III)	37054	4,5-dimethyl-2-phenyl-4,5-dihydro-1H-imidazole-4,5-diol		C₁₁H₁₄N₂O₂	详情	详情
(IV)	37055	(5-methyl-2-phenyl-1H-imidazol-4-yl)methanol		C₁₁H₁₂N₂O	详情	详情
(V)	37056	4-(chloromethyl)-5-methyl-2-phenyl-1H-imidazole		C₁₁H₁₁ClN₂	详情	详情

Extended Information