新产品编号:1713815
Chemical Name: 4-[1-(4-Amino-6,7-dimethoxyquinazolin-2-yl)piperidin-4-ylamino]benzoic acid
项目整合开发状态: Preclinical
项目研究机构: Isis Pharmaceuticals (Originator)
合成路线:Palladium-catalyzed coupling of 4-amino-1-benzylpiperidine (I) with tert-butyl 4-bromobenzoate (II) afforded the anilinopiperidine derivative (III).Removal of the benzyl protecting group of (III) to give (IV) was achieved by transfer hydrogenolysis in the presence of ammonium formate and Pd/C.Piperidine (IV) was then coupled with 4-amino-2-chloro-6,7-dimethoxyquinazoline (V) in hot isoamyl alcohol yielding piperidino quinazoline (VI).The title carboxylic acid was finally obtained by acidic deprotection of tert-butyl ester of (VI).
📌 参考资料/链接：
参考文献标题:Antibacterial quinazoline cpds.
文献作者:Guinosso,C.J.; Cook,P.D.; Kung,P.-P.(Isis Pharmaceuticals,Inc.)
参考来源:US 6156758
📄 详细内容
合成路线:Palladium-catalyzed coupling of 4-amino-1-benzylpiperidine (I) with tert-butyl 4-bromobenzoate (II) afforded the anilinopiperidine derivative (III).Removal of the benzyl protecting group of (III) to give (IV) was achieved by transfer hydrogenolysis in the presence of ammonium formate and Pd/C.Piperidine (IV) was then coupled with 4-amino-2-chloro-6,7-dimethoxyquinazoline (V) in hot isoamyl alcohol yielding piperidino quinazoline (VI).The title carboxylic acid was finally obtained by acidic deprotection of tert-butyl ester of (VI).
参考文献标题:Structure-activity relationships of novel 2-substituted quinazoline antibacterial agents
文献作者:Kung,P.-P.; Casper,M.D.; Cook,K.L.; Wilson-Lingardo,L.; Risen,L.M.; Vickers,T.A.; Ranken,R.; Blyn,L.B.; Wyatt,J.R.; Cook,P.D.; Ecker,D.J.
参考来源:J Med Chem 1999,42(22),4705