Amosulalol hydrochloride, YM-09538, Lowgan
氨磺洛尔 Chemical Name: (?-5-[1-Hydroxy-2-[[2-(o-methoxyphenoxy)ethyl]amino]ethyl]-o-toluenesulfonamide monohydrochloride; (?-5-[1-Hydroxy-2-[[2-(2-methoxyphenoxy)ethyl]amino]ethyl]-2-methylbenzenesulfonamide monohydrochloride
CAS No. 70958-86-0, 85320-68-9 (free base)
项目整合开发状态: Launched-1988
项目研究机构: Yamanouchi (Originator)
合成路线:The condensation of 2-methoxy-5-(2-bromopropionyl)benzenesulfonamide (I) with N-benzyl-2-(2 ethoxyphenoxy)ethylamine (II) in refluxing butanone gives the tertiary amine (III),which is reduced with sodium in ethanol to the alcohol (IV).Debenzylation of (IV) with H2 over Pd/C in methanol affords the hydroxyamine (V),which by reaction with SOCl2 in acetonitrile is converted to the corresponding chloro derivative (VI).Finally,this compound is dechlorinated by hydrogenolysis with H2 over Pd/C in methanol.
合成路线:The condensation of 2-methoxyphenol (I) with ethylene oxide (II) gives 2-(2-methoxyphenoxy)ethanol (III),which is treated with SOCl2 to yield 2-(2-methoxyphenoxy)ethyl chloride (IV).The reaction of (IV) with benzylamine (A) gives N-[2-(2-methoxyphenoxy)ethyl]benzylamine (V),which is condensed with 2-methyl-5-bromoacetylbenzenesulfonamide (VI) affording N-[2-(2-methoxyphenoxy)ethyl]-N-[(4-methyl-3-aminosulfonylbenzoyl)methyl]benzylamine (VII).The reduction of (VII) with NaBH4 affords the corresponding protected carbinol (VIII),which is finally debenzylated by hydrogenation with H2 over Pd/C.
📌 参考资料/链接：
参考文献标题:Phenylethanolamine derivatives
文献作者:Fujikura,T.; et al.(Yamanouchi Pharmaceutical Co.,Ltd.)
参考来源:DE 2843016; ES 474149; ES 481549; FR 2405931; GB 2006772
📄 详细内容
合成路线:The condensation of 2-methoxyphenol (I) with ethylene oxide (II) gives 2-(2-methoxyphenoxy)ethanol (III),which is treated with SOCl2 to yield 2-(2-methoxyphenoxy)ethyl chloride (IV).The reaction of (IV) with benzylamine (A) gives N-[2-(2-methoxyphenoxy)ethyl]benzylamine (V),which is condensed with 2-methyl-5-bromoacetylbenzenesulfonamide (VI) affording N-[2-(2-methoxyphenoxy)ethyl]-N-[(4-methyl-3-aminosulfonylbenzoyl)methyl]benzylamine (VII).The reduction of (VII) with NaBH4 affords the corresponding protected carbinol (VIII),which is finally debenzylated by hydrogenation with H2 over Pd/C.
参考文献标题:YM-09,538
文献作者:Serradell,M.N.; Blancafort,P.; Castar,J.; Leeson,P.A.; Mealy,N.E.
参考来源:Drugs Fut 1981,6(7),425
合成路线:The condensation of 2-methoxyphenol (I) with ethylene oxide (II) gives 2-(2-methoxyphenoxy)ethanol (III),which is treated with SOCl2 to yield 2-(2-methoxyphenoxy)ethyl chloride (IV).The reaction of (IV) with benzylamine (A) gives N-[2-(2-methoxyphenoxy)ethyl]benzylamine (V),which is condensed with 2-methyl-5-bromoacetylbenzenesulfonamide (VI) affording N-[2-(2-methoxyphenoxy)ethyl]-N-[(4-methyl-3-aminosulfonylbenzoyl)methyl]benzylamine (VII).The reduction of (VII) with NaBH4 affords the corresponding protected carbinol (VIII),which is finally debenzylated by hydrogenation with H2 over Pd/C.
参考文献标题:Synthesis of 14C-labeled 5-[1-hydroxy-2-[2-(o-methoxyphenoxy)ethylamino]ethyl]-2-methylbenzenesulfonamide hydochloride (YM-09538)
文献作者:Arima,H.; Tamazawa,K.
参考来源:J Label Compd Radiopharm 1983,20(7),803-811
产品链接: CAS No. 70958-86-0›› 产品链接: CAS No.85320-68-9››