LY-508869

Chemical Name: 2,2,2-Trifluoro-N-[3-(2-methoxyphenoxy)phenyl]-N-(pyridin-3-ylmethyl)ethanesulfonamide
CAS No. 353229-45-5, 353235-52-6 (hydrochloride)
项目整合开发状态: Biological Testing
项目研究机构: Lilly (Originator)
合成路线:The reductive alkylation of 4-(2-methoxyphenoxy)aniline (I) with pyridine-3-carboxaldehyde (II) in the presence of NaBH4 leads to the N-pyridylmethyl aniline adduct (III) (1).Alternatively,4-bromoaniline (IV) is reductively alkylated with pyridine-3-carboxaldehyde (II) to produce (V).Subsequent copper-catalyzed bromide displacement of (V) with guaiacol (VI) affords intermediate (III) (2).Finally,acylation of amine (III) with 2,2,2-trifluoroethylsulfonyl chloride (VII) gives rise to the target sulfonamide (1,2).

合成路线:Coupling of 2-methoxyphenol (I) with 3-fluoronitrobenzene (II) produced the diaryl ether (III).The nitro group of (III) was then reduced by catalytic hydrogenation over Raney-Ni,yielding aniline (IV).Reductive alkylation of (IV) with pyridine-3-carboxaldehyde (V) using NaBH4 furnished the secondary amine (VI).This was finally acylated with 2,2,2-trifluoroethylsulfonyl chloride to produce the title sufonamide.