PNU-145185
Chemical Name: N-(4-Chlorobenzyl)-8-fluoro-4-hydroxyquinoline-3-carboxamide
CAS No. 228725-44-8
项目整合开发状态: Biological Testing
项目研究机构: Pfizer (Originator)
合成路线:The condensation of 2-fluoroaniline (I) with diethyl ethoxymethylene malonate (II) at 130 C afforded enamine (III),which was further cyclized to ethyl 8-fluoro-4-hydroxy-3-quinolinecarboxylate (IV) upon heating at 250 C.Condensation of (III) with neat 4-chlorobenzylamine (V) then provided the desired carboxamide.
合成路线:The condensation between 4-iodoaniline (I) and diethyl ethoxymethylenemalonate (II) at 130 C,followed by cyclization in diphenyl ether at 250 C,furnished ethyl 4-hydroxy-6-iodoquinoline-3-carboxylate (III).Subsequent reaction of ester (III) with 4-chlorobenzylamine (IV) at 180 C produced the corresponding amide (V).Finally,coupling of (V) with propargyl alcohol (VI) in the presence of CuI and palladium catalyst afforded the desired (hydroxypropynyl)quinoline.
📌 参考资料/链接：
参考文献标题:4-Hydroxyquinoline-3-carboxamides and hydrazides as antiviral agents
文献作者:Schnute,M.E.; Turner,S.R.; Cudahy,M.M.; Vaillancourt,V.A.; Thaisrivongs,S.; Strohbach,J.W.; Romines,K.R.; Tucker,J.A.(Pharmacia Corp.)
参考来源:EP 1042295; US 6093732; WO 9932450
📄 详细内容
合成路线:The condensation of 2-fluoroaniline (I) with diethyl ethoxymethylene malonate (II) at 130 C afforded enamine (III),which was further cyclized to ethyl 8-fluoro-4-hydroxy-3-quinolinecarboxylate (IV) upon heating at 250 C.Condensation of (III) with neat 4-chlorobenzylamine (V) then provided the desired carboxamide.
参考文献标题:4-Hydroxyquinoline-3-carboxamides as inhibitors of herpes virus DNA polymerases
文献作者:Cudahy,M.M.; Clayton,T.L.; Vailancourt,V.A.; et al.
参考来源:219th ACS Natl Meet (March 26 2000,San Francisco) 2000,Abst MEDI 135
产品链接: CAS No. 228725-44-8››