VUF-5000

Chemical Name: cis-N-[4-(Fluoromethyl)cyclohexyl]-4-(4-imidazolyl)piperidine-1-carbothioamide
项目整合开发状态: Preclinical
项目研究机构: Vrije Universiteit (Originator)
合成路线:The reaction of cis-4-aminocyclohexylmethanol (I) with di-tert-butyl dicarbonate and triethylamine in methanol gives the corresponding carbamate (II),which is treated with tosyl chloride in pyridine yielding the tosylate (III).The reaction of (III) with tetrabutylammonium fluoride (TBAF) in acetonitrile affords the fluoromethyl derivative (IV),which is deprotected with chlorotrimethylsilane and KI to give 4-(fluoromethyl)cyclohexylamine (V).The reaction of (V) with 1,1'-thiocarbonyl-bis(pyridin-2(1H)-one (SCP) yields the isothiocyanate (VI),which is finally condensed with 4-(1H-imidazol-4-yl)piperidine (VII) by means of diisopropylethylamine (DIEA) in acetonitrile.