新产品编号:324819

Chemical Name: 5-[3,5-Bis(trifluoromethyl)phenyl]-4-(5-chloro-2-hydroxyphenyl)-3,4-dihydro-2H-1,2,4-triazol-3-one
CAS No. 202821-61-2
项目整合开发状态: Biological Testing
项目研究机构: Bristol-Myers Squibb (Originator)
合成路线:4-Bromobenzotrifluoride (I) is converted to the corresponding Grignard reagent (II),which undergoes addition to diethyl oxalate,yielding keto ester (III).Subsequent saponification of ester (III) gives the phenylglyoxylic acid derivative (IV).Condensation of (IV) with 5-chloro-2-methoxyphenylhydrazine (V) affords the aryl hydrazone (VI).Curtius rearrangement of the carboxyl moiety of (VI) by means of diphenylphosphoryl azide generates the corresponding isocyanate,which spontaneously cyclizes to the triazolone (VII).Methyl ether cleavage in (VII) with boron tribromide gives rise to the title phenol derivative.

合成路线:Acylation of 5-chloroanisidine (I) with 3,5-bis(trifluoromethyl)benzoyl chloride (II) affords benzamide (III).Treatment of amide (III) with PCl5,followed by reaction of the intermediate iminoyl chloride with hydrazine in THF generates the amidrazone (IV).Cyclization of (IV) with carbonyl diimidazole leads to triazolone (V).Finally,methyl ether cleavage in (V) employing pyridine hydrochloride at 225 C provides the target phenol compound.