新产品编号:851625
Chemical Name: N-Phenylcarbamic acid 2-[3-(1H-benzimidazol-2-ylsulfanylmethyl)-2-methylphenylsulfanyl]ethyl ester
CAS No. 339353-49-0
项目整合开发状态: Preclinical
项目研究机构: AstraZeneca (Originator)
合成路线:Diazotization of 3-amino-2-methylbenzoic acid (I),followed by coupling with methyl thioglycolate leads to thioether (II).Selective reduction of the carboxyl group of (II) with borane in THF yields the benzyl alcohol (III),which is chlorinated to (IV) employing SOCl2.Condensation of benzyl chloride (IV) with 2 mercaptobenzimidazole (V) under alkaline conditions furnishes adduct (VI).The ester group of (VI) is then reduced to alcohol (VII) with LiAlH4 in THF.Finally,coupling of alcohol (VII) with phenyl isocyanate provides the target carbamate compound.
📌 参考资料/链接：
参考文献标题:Compounds
文献作者:Shue,Y.-K.; K黨ler,T.; Abedi,J.; Carcanague,D.; Wuonola,M.(Pharmacia AB)
参考来源:WO 0134573
📄 详细内容
合成路线:Diazotization of 3-amino-2-methylbenzoic acid (I),followed by coupling with methyl thioglycolate leads to thioether (II).Selective reduction of the carboxyl group of (II) with borane in THF yields the benzyl alcohol (III),which is chlorinated to (IV) employing SOCl2.Condensation of benzyl chloride (IV) with 2 mercaptobenzimidazole (V) under alkaline conditions furnishes adduct (VI).The ester group of (VI) is then reduced to alcohol (VII) with LiAlH4 in THF.Finally,coupling of alcohol (VII) with phenyl isocyanate provides the target carbamate compound.
参考文献标题:Novel structures derived from 2-[[(2-pyridyl)methyl]thio]-1H-benzimidazole as anti-Helicobacter pylori agents,part 2
文献作者:Carcanague,D.; Shue,Y.-K.; Wuonola,M.A.; Uria-Nickelsen,M.; Joubran,C.; Abedi,J.K.; Jones,J.; K黨ler,T.C.
参考来源:J Med Chem 2002,45(19),4300