PD-150714

Chemical Name: 1-Ethyl-4-phenyl-1,2,3,6-tetrahydropyridine-3-carboxylic acid hexyl ester oxalate
项目整合开发状态: Preclinical
项目研究机构: Pfizer (Originator)
合成路线:Treatment of oxazolylpyridine (I) with phenyllithium in THF at -78 C yielded the 4-phenyl dihydropyridine (II),which was aromatized to phenylpyridine (III) with sulfur in refluxing toluene.Hydrolysis of the oxazoline group of (III) with HCl afforded the phenylnicotinic acid (IV).This was converted to acid chloride (V) using SOCl2 and a catalytic amount of DMF,and subsequently condensed with n-hexyl alcohol (VI) in the presence of diisopropylethylamine to give ester (VII).Quaternization of the pyridine ring of (VII) with EtI in refluxing acetonitrile furnished pyridinium salt (VIII).Finally,reduction of this salt with NaBH4 in aqueous MeOH provided a mixture of the target tetrahydropyridine (X) and its isomer (IX) that were separated by flash chromatography.