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目的为加强质子泵抑制剂兰索拉唑原料药的质量控制,合成兰索拉唑的相关物质。方法以2-氯甲基-3-甲基-4-(2,2,2-三氟乙氧基)吡啶盐酸盐和2-巯基苯并咪唑为起始原料,用化学法合成了兰索拉唑3个有关物质:2-[[3-甲基-4-(2,2,2-三氟乙氧基)-2-吡啶基]甲基硫代]-1H-苯并咪唑(1)、2-[[3-甲基-4-(2,2,2-三氟乙氧基)-2-吡啶基]甲磺酰基]-1H-苯并咪唑(2)、2-[[3-甲基-1-氧-4-(2,2,2-三氟乙氧基)-2-吡啶基]甲基亚磺酰基]-1H-苯并咪唑(3)。结果与结论目标化合物的结构经质谱、核磁和红外光谱确证,可作为兰索拉唑原料药质量控制的有关物质对照品。所用方法原料易得、反应条件温和、操作简单。
Objective To enhance the quality control of the proton pump inhibitor lansoprazole and synthesize the related substances of lansoprazole. Methods Starting from 2-chloromethyl-3-methyl-4- (2,2,2-trifluoroethoxy) pyridine hydrochloride and 2-mercaptobenzimidazole, Sorazole 3 related substances: 2 - [[3-methyl-4- (2,2,2-trifluoroethoxy) -2- pyridyl] methylthio] -1H-benzimidazole 1) 2 - [[3-methyl-4- (2,2,2- trifluoroethoxy) -2- pyridinyl] methanesulfonyl] [3-methyl-1-oxo-4- (2,2,2-trifluoroethoxy) -2-pyridyl] methylsulfinyl] -1H-benzimidazole (3). Results and Conclusions The structure of the target compound was confirmed by MS, NMR and FTIR spectroscopy. It can be used as reference material for quality control of Lansoprazole API. The raw materials used are easy to obtain, the reaction conditions are mild and the operation is simple.