新产品编号:285269
Chemical Name: N-(2-Isopropoxyphenyl)-N'-(1,6-naphthyridin-2-yl)urea
CAS No. 197507-01-0
项目整合开发状态: Biological Testing
项目研究机构: Shire BioChem (Originator)
合成路线:Treatment of 2-isopropoxyphenylamine (I) with triphosgene (II) and DIEA in dichloromethane affords isocyanate (III),which is then converted into the desired urea derivative by treatment with amine (IV) in refluxing acetonitrile.
📌 参考资料/链接：
参考文献标题:Naphthyridine derivs.and their analogues inhibiting cytomegalovirus
文献作者:Jin,H.; Chan,L.C.-K.; Wang,W.; Stefanac,T.; Mansour,T.S.; Nguyen-Ba,P.; Lavallee,J.-F.; Falardeau,G.(Shire BioChem Inc.)
参考来源:EP 0984967; JP 2001515464; US 5945431; WO 9734894
📄 详细内容
合成路线:Oxidation of 5-hydroxy-5,6,7,8-tetrahydroisoquinoline (I) using CrO3 in pyridine produced the corresponding ketone (II).Subsequent condensation of (II) with methyl cyanoformate (A) in the presence of lithium hexamethyldisilazide gave ketoester (III),which was reduced to hydroxyester (IV) by means of catalytic hydrogenation.Dehydration of (IV) to the unsaturated ester (V) was achieved by treatment with methanesulfonyl chloride and triethylamine,followed by basic elimination with DBU.Saponification of the ester group of (V) produced carboxylic acid (VI).After activation of (VI) as the mixed anhydride (VII) with isopropyl chloroformate (B),coupling with tryptamine (VIII) furnished the title amide,which was finally isolated as the hydrochloride salt.
合成路线:Treatment of 2-isopropoxyphenylamine (I) with triphosgene (II) and DIEA in dichloromethane affords isocyanate (III),which is then converted into the desired urea derivative by treatment with amine (IV) in refluxing acetonitrile.
参考文献标题:Antiviral cpds.
文献作者:Bedard,J.; Rando,R.; Falardeau,G.; Lavallee,J.-F.(BioChem Pharma Inc.)
参考来源:WO 9929318