Sch-59948

Chemical Name: 8-Chloro-11-[1-[2-(4-pyridyl)acetyl]piperidin-4-yl]-6,11-dihydro-5H-benzo[5,6]cyclohepta[1,2-b]pyridin-6-one oxime
项目整合开发状态: Biological Testing
项目研究机构: Schering-Plough (Originator)
合成路线:Carbamate (I) was hydrolyzed to amine (II) by treatment with an ethanolic solution of HCl,which was then isomerized to the endocyclic compound (III) on heating with trifluoromethanesulfonic acid.Compound III was protected as the carbamate (IV) by reaction with ethyl chloroformate,and further nitration was effected with tetra-n-butylammonium nitrate - trifluoroacetic anhydride (TFAA) reagent to afford nitro compound (V).Subsequent deprotection of carbamate was effected with ethanolic HCl,to give amine (VI),which was then condensed with 4-pyridylacetic acid (VII) to the amide (VIII).Reduction of the nitro group of (VIII) with tin (II) chloride yielded oxime (IX) (SCH 59948),and reaction of this compound with acetyl chloride gave the corresponding oxime acetate (SCH 60102).