新产品编号:2053945

Chemical Name: 4-[4-[2-[2(S)-Hydroxy-3-(4-hydroxyphenoxy)propylamino]ethyl]phenylamino]-N-octylpiperidine-1-carboxamide
项目整合开发状态: Preclinical
项目研究机构: Wyeth Pharmaceuticals (Originator)
合成路线:4-Benzyloxyphenol (I) was protected as the silyl ether (II) upon treatment with tert-butyldiphenylsilyl chloride and imidazole.Then,benzyl ether cleavage in (II) by means of transfer hydrogenolysis with cyclohexene and Pd/C furnished the silyloxy phenol (III).Coupling of phenol (III) with (R)-glycidol (IV) under Mitsunobu conditions yielded the intermediate glycidyl ether (V).

合成路线:The aliphatic amino group of 4-aminophenethylamine (VI) was regioselectively protected as the N-Boc derivative (VII) using Boc2O.Subsequent reductive alkylation of aniline (VII) with N-benzyl-4-piperidone (VIII) afforded the anilinopiperidine (IX).The N-benzyl group of (IX) was then removed by transfer hydrogenolysis,and the resulting piperidine (X) was condensed with octyl isocyanate (XI),yielding the corresponding urea (XII).After acidic cleavage of the N-Boc protecting group of (XII),the primary amine (XIII) was condensed with the intermediate epoxide (V) to produce the amino alcohol (XIV).Final desilylation of (XIV) gave rise to the title compound.