新产品编号:407083

Chemical Name: 5,6-Dichloro-1-(5-deoxy-beta-D-ribofuranosyl)-4-fluoro-N-isopropyl-1H-benzimidazol-2-amine
CAS No. 211693-84-4
项目整合开发状态: Biological Testing
项目研究机构: GlaxoSmithKline (Originator), University of Michigan (Originator)
合成路线:Fluorination of 4,5-dichloro-2-nitroaniline (I) with 1-fluoro-4-hydroxy-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoborate) (II) gave fluoroaniline (III).The nitro group of (III) was then reduced by hydrogenation over Raney-Ni to afford phenylenediamine (IV).This was cyclized with isopropyl isothiocyanate in the presence of 1-cyclohexyl-3-(2-morpholinoethyl)carbodiimide metho-p-toluenesulfonate as the desulfurizing agent to yield benzimidazole (V).Coupling with 1,2,3-tri-O-acetyl-5-deoxy-D-ribofuranose (VI) using trimethylsilyl triflate and N,O-bis(trimethylsilyl)acetamide produced a mixture of regioisomeric ribofuranosyl benzimidazoles (VII) and (VIII),which were separated by column chromatography.Finally,deprotection of the acetate esters from the major isomer (VII) with Na2CO3 provided the title compound.