D-4418
8-甲氧基-喹啉-5-甲酸Chemical Name: N-(3,5-Dichloro-4-pyridinyl)-8-methoxyquinoline-5-carboxamide
CAS No. 199871-63-1, 199871-80-2 (diHBr), 199871-79-9 (diHCl)
项目整合开发状态: Phase I
项目研究机构: Celltech (Originator), Schering-Plough (Codevelopment)
合成路线:8-Methoxyquinoline-5-carboxylic acid (III) was prepared by Skraup synthesis from 3-amino-4-methoxybenzoic acid (I) and glycerol (II) in sulfuric acid at 180 C.Subsequent treatment of (III) with oxalyl chloride using a catalytic amount of DMF gave the corresponding acid chloride (IV),which was finally coupled with 4-amino-3,5-dichloropyridine (V) in the presence of NaH in DMF to provide the target amide.
📌 参考资料/链接：
参考文献标题:Quinoline carboxamides as TNF inhibitors and as PDE-IV inhibitors
文献作者:Dyke,H.J.; Montana,J.G.; Lowe,C.; Kendall,H.J.; Sabin,V.M.(Celltech Group plc)
参考来源:EP 0952832; JP 2000510865; US 5804588; WO 9744036
📄 详细内容
合成路线:8-Methoxyquinoline-5-carboxylic acid (III) was prepared by Skraup synthesis from 3-amino-4-methoxybenzoic acid (I) and glycerol (II) in sulfuric acid at 180 C.Subsequent treatment of (III) with oxalyl chloride using a catalytic amount of DMF gave the corresponding acid chloride (IV),which was finally coupled with 4-amino-3,5-dichloropyridine (V) in the presence of NaH in DMF to provide the target amide.
参考文献标题:8-Methoxyquinoline-5-carboxamides as PDE4 inhibitors: A potential treatment for asthma
文献作者:Buckley,G.M.; Cooper,N.; Dyke,H.J.; Galleway,F.P.; Gowers,L.; Haughan,A.F.; Kendall,H.J.; Lowe,C.; Maxey,R.; Montana,J.G.; Naylor,R.; Oxford,J.; Peake,J.C.; Picken,C.L.; Runcie,K.A.; Sabin,V.; Sharpe,A.; Warneck,J.B.
参考来源:Bioorg Med Chem Lett 2002,12(12),1613
产品链接: CAS No. 199871-63-1››