新产品编号:2398821

Chemical Name: 4-Fluoro-N-[1-[3-[6-[1-methyl-1-(methylsulfonyl)ethyl]quinolin-8-yl]phenyl]ethyl]-N-[4-(methylsulfonyl)phenyl]benzamide
项目整合开发状态: Preclinical
项目研究机构: Merck Frosst (Originator)
合成路线:2-Bromo-4-methylaniline (I) is converted to quinoline (II) upon condensation with glycerol under Skraup synthesis conditions.Radical bromination of (II) with N-bromosuccinimide affords the benzylic bromide (III),which is subsequently displaced with sodium methanesulfinate to yield sulfone (IV).Alkylation of sulfone (IV) with iodomethane in the presence of potassium tert-butoxide affords the dimethylated sulfone (V).This is then subjected to Suzuki coupling with the boronic acid (VI) to produce the 8-aryl quinoline (VII).Condensation of aldehyde (VII) with 4-(methylthio)aniline (VIII) generates imine (IX),to which methyllithium is added to furnish the alpha methylated amine (X).Acylation of amine (X) by 4-fluorobenzoyl chloride (XI) gives amide (XII).The methylsulfanyl group of (XII) is finally oxidized with oxone to the target bis-sulfone derivative.