新产品编号:1444875

Chemical Name: endo-1-Isopropyl-N-(8-methyl-8-azabicyclo[3.2.1]oct-3-yl)benzimidazole-2-carboxamide fumarate
项目整合开发状态: Preclinical
项目研究机构: FAES (Originator)
合成路线:The reaction of 8-methyl-8-azabicyclo[3.2.1]octan-3-one (I) with hydroxylamine and pyridine in refluxing ethanol gives the oxime (II),which is reduced with LiAlH4 in refluxing 10% H2SO4 yielding endo-methyl-8-azabicyclo[3.2.1]octan-3-amine (III).Finally,this compound is condensed with 1-isopropylbenzimidazole-2-carboxylic acid isopropyl ester (IV) by means of Al(CH3)3 in refluxing toluene.The intermediate 1-isopropylbenzimidazole-2-carboxylic acid isopropyl ester (IV) has been obtained as follows: The cyclization of o-phenylenediamine (V) with 2-hydroxyacetic acid (VI) in refluxing 4N HCl gives 1H-benzyldazole-2-ylmethanol (VII),which is oxidized with KMnO4 to the corresponding carboxylic acid (VIII).Finally,this compound is alkylated and esterified with isopropyl chloride and NaH in DMF.