网站主页>>>项目整合精选>>>项目整合精选>>>Leminoprazole, NC-1300-O-3, Leminon

Leminoprazole, NC-1300-O-3, Leminon

来明拉唑Chemical Name: (?-2-[2-(N-Isobutyl-N-methylamino)benzylsulfinyl]benzimidazole
CAS No. 104340-86-5 (undefined isomer)
项目整合开发状态: Phase III
项目研究机构: Nippon Chemiphar (Originator), Kyorin (Codevelopment)
合成路线:By condensation of pyrrolidine (I) with paraformaldehyde (II) and 4-ethylpropiophenone (III) by means of dry HCl in refluxing ethyl acetate.

合成路线:The condensation of 2-(dimethylamino)benzyl chloride (I) with 2-mercaptobenzimidazole (II) by means of NaHCO3 in ethanol gives 2-[2-(dimethylamino)benzylthio]benzimidazole (III),which is then oxidized with m-chloroperbenzoic acid (IV) in CHCl3-methanol.

合成路线:The acylation of methylanthranilate (I) with isobutyryl chloride (II) gives 2-isobutyramidobenzoic acid methyl ester (III),which is reduced with LiAlH4 to 2-(isobutylamino)benzyl alcohol (IV).The methylation of (IV) with dimethyl sulfate yields 2-(N-isobutyl-N-methylamino)benzyl alcohol (V),which is treated with SOCl2 to afford the corresponding benzyl chloride (VI).The condensation of (VI) with benzimidazole-2-thiol (VII) by means of NaOH yields 2-[2-(N-isobutyl-N-methylamino)benzylsulfanyl)benzimidazole (VIII),which is finally oxidized with m-chloroperbenzoic acid (MCPBA) as usual.
📌 参考资料/链接:
参考文献标题:Benzimidazole derivs.and antiulcer agents contain
文献作者:Susumu,O.; Masaru,S.; Tomio,Y.; Yutaka,N.; Masatoshi,H.(Nippon Chemiphar Co.,Ltd.)
参考来源:AU 8546409; BE 0903128; CH 665417; DE 3531487; ES 8703142; FR 2569691; GB 2163747; JP 1986060660; JP 1986221175; JP 1986221176; JP 1991223260; JP 1991223261; JP 1991223262; JP 1991227927

📄 详细内容


合成路线:The acylation of methylanthranilate (I) with isobutyryl chloride (II) gives 2-isobutyramidobenzoic acid methyl ester (III),which is reduced with LiAlH4 to 2-(isobutylamino)benzyl alcohol (IV).The methylation of (IV) with dimethyl sulfate yields 2-(N-isobutyl-N-methylamino)benzyl alcohol (V),which is treated with SOCl2 to afford the corresponding benzyl chloride (VI).The condensation of (VI) with benzimidazole-2-thiol (VII) by means of NaOH yields 2-[2-(N-isobutyl-N-methylamino)benzylsulfanyl)benzimidazole (VIII),which is finally oxidized with m-chloroperbenzoic acid (MCPBA) as usual.

参考文献标题:Cytoprotective agents for stomach and intestine
文献作者:Okabe,S.; Sato,M.; Yamakawa,T.; Nomura,T.; Hayashi,M.(Nippon Chemiphar Co.,Ltd.)
参考来源:JP 1988230633


合成路线:The acylation of methylanthranilate (I) with isobutyryl chloride (II) gives 2-isobutyramidobenzoic acid methyl ester (III),which is reduced with LiAlH4 to 2-(isobutylamino)benzyl alcohol (IV).The methylation of (IV) with dimethyl sulfate yields 2-(N-isobutyl-N-methylamino)benzyl alcohol (V),which is treated with SOCl2 to afford the corresponding benzyl chloride (VI).The condensation of (VI) with benzimidazole-2-thiol (VII) by means of NaOH yields 2-[2-(N-isobutyl-N-methylamino)benzylsulfanyl)benzimidazole (VIII),which is finally oxidized with m-chloroperbenzoic acid (MCPBA) as usual.

参考文献标题:Method for the preparation of benzimidazole cpds
文献作者:Mazaki,M.; Yamakawa,T.; Nomura,Y.(Nippon Chemiphar Co.,Ltd.)
参考来源:JP 1990078665


合成路线:The acylation of methylanthranilate (I) with isobutyryl chloride (II) gives 2-isobutyramidobenzoic acid methyl ester (III),which is reduced with LiAlH4 to 2-(isobutylamino)benzyl alcohol (IV).The methylation of (IV) with dimethyl sulfate yields 2-(N-isobutyl-N-methylamino)benzyl alcohol (V),which is treated with SOCl2 to afford the corresponding benzyl chloride (VI).The condensation of (VI) with benzimidazole-2-thiol (VII) by means of NaOH yields 2-[2-(N-isobutyl-N-methylamino)benzylsulfanyl)benzimidazole (VIII),which is finally oxidized with m-chloroperbenzoic acid (MCPBA) as usual.
参考文献标题:Leminoprazole
文献作者:Mealy,N.; Castar,J.
参考来源:Drugs Fut 1996,21(2),155


产品链接: CAS No. 104340-86-5››