新产品编号:1090507

Chemical Name: 1-[4-(3,5-Dibromo-8-chloro-11H-benzo[5,6]cyclohepta[1,2-b]pyridin-11-yl)piperidin-1-yl]-2-(1-oxidopyridin-4-yl)ethanone
项目整合开发状态: Biological Testing
项目研究机构: Schering-Plough (Originator)
合成路线:Isomerization of (I) in refluxing trifluoromethanesulfonic acid provided the endocyclic olefin (II).Further reaction with ethyl chloroformate and triethylamine in toluene gave carbamate (III),which was then nitrated with a cooled mixture tetra-n-butylammonium nitrate and trifluoroacetic anhydride in dicloromethane,to afford a mixture of nitrocompounds (IV) and (V).After separation by column chromatography on silica gel,nitrocompound (V )was reduced with iron powder and calcium chloride in refluxing aqueous ethanol to amine (VII).Diazotization of amine (VII) with NaNO2 in 48% HBr in the presence of bromine at -5 C gave a mixture of monobromide (VIII) and dibromide (IX),which were separated on column chromatography.The dibromocarbamate (IX) was hydrolyzed in refluxing HCl to amine (X),which was finally coupled with 4-pyridylacetic acid N-oxide (XI) by treatment with EDC and HOBT.