D-4396, SCH-351591
Chemical Name: 3,5-Dichloro-4-[8-methoxy-2-(trifluoromethyl)quinolin-5-ylcarboxamido]pyridine-1-oxide; N-(3,5-Dichloro-1-oxidopyridin-4-yl)-8-methoxy-2-(trifluoromethyl)quinoline-5-carboxamide
CAS No. 266995-28-2
项目整合开发状态: Phase I
项目研究机构: Celltech (Originator), Schering-Plough (Licensee)
合成路线:8-Methoxy-2-trifluoromethylquinoline-5-carboxylic acid (I) was activated as the corresponding nitrophenyl ester (III) upon treatment with p-nitrophenol (II) and EDC.The p-nitrophenyl ester (III) was then coupled with 4-amino-3,5-dichloropyridine (IV) in the presence of NaH to produce amide (V).The pyridine ring of (V) was finally oxidized to the title N-oxide by treatment with peracetic acid.
📌 参考资料/链接：
参考文献标题:N-Oxides of heterocyclic cpds.with TNF and PDE-IV inhibiting activity
文献作者:Montana,J.G.; Dyke,H.J.(Celltech Group plc)
参考来源:EP 1045845; US 6262070; WO 0026208
📄 详细内容
合成路线:8-Methoxy-2-trifluoromethylquinoline-5-carboxylic acid (I) was activated as the corresponding nitrophenyl ester (III) upon treatment with p-nitrophenol (II) and EDC.The p-nitrophenyl ester (III) was then coupled with 4-amino-3,5-dichloropyridine (IV) in the presence of NaH to produce amide (V).The pyridine ring of (V) was finally oxidized to the title N-oxide by treatment with peracetic acid.
参考文献标题:Synthesis and profile of SCH351591,a novel PDE4 inhibitor
文献作者:Billah,M.; Cooper,N.; Cuss,F.; Davenport,R.J.; Dyke,H.J.; Egan,R.S.; Ganguly,A.K.; Gowers,L.; Hannah,D.R.; Haughan,A.F.; Kendall,H.J.; Lowe,C.; Minnicozzi,M.; Montana,J.G.; Naylor,R.; Oxford,J.; Peake,J.C.; Piwinski,J.J.; et al.
参考来源:Bioorg Med Chem Lett 2002,12(12),1621