S-1389, 711389-S
Chemical Name: 1-[2,5-Dichloro-6-[1-(1H-imidazol-1-yl)ethenyl]phenoxy]-3-[(1-methylethyl)amino]-2-propanol hydrochloride; 1-[1-[2-(3-Isopropylamino-2-hydroxypropoxy)-3,6-dichlorophenyl]vinyl]-1H-imidazole hydrochloride
CAS No. 90821-25-3 ((R)-(+)-isomer), 90821-27-5 ((S)-(-)-isomer), 90742-91-9 (racemate), 90742-90-8 (racemic free base)
项目整合开发状态: Phase I
项目研究机构: Shionogi (Originator)
合成路线:This 1-vinylimidazole compound (II) is obtained by reaction of N,N'-thionyldiimidazole (A) with 2-hydroxy-3,6-dichloroacetophenone (I) in dichloro-methane.Treatment of (II) with epibromohydrin (B) in DMF in the presence of NaH gives the epoxy compound (III),which is then treated with isopropylamine (C) to obtain the propanolamine compound (IV).The hydrochloride can be prepared by treatment of the free base (IV) with one molar equivalent of HCl in AcOEt.
📌 参考资料/链接：
参考文献标题:711389-S
文献作者:Ueda,M.
参考来源:Drugs Fut 1985,10(6),472
📄 详细内容
合成路线:This 1-vinylimidazole compound (II) is obtained by reaction of N,N'-thionyldiimidazole (A) with 2-hydroxy-3,6-dichloroacetophenone (I) in dichloro-methane.Treatment of (II) with epibromohydrin (B) in DMF in the presence of NaH gives the epoxy compound (III),which is then treated with isopropylamine (C) to obtain the propanolamine compound (IV).The hydrochloride can be prepared by treatment of the free base (IV) with one molar equivalent of HCl in AcOEt.
参考文献标题:Synthesis and antiarrhythmic activity of new 1-[1-[2-[3-(alkylamino)-2-hydroxypropoxy]phenyl]vinyl]-1H-imidazoles and related compounds
文献作者:Ogata,M.; Matsumoto,H.; Takahashi,K.; Shimizu,S.; Kida,S.; Ueda,M.; Kimoto,S.; Haruna,M.
参考来源:J Med Chem 1984,27(9),1142