XJ-304

Chemical Name: N-[2-(4-Cyanophenyl)-1-methyl-4,4-bis(trifluoromethyl)-4,5-dihydro-1H-imidazol-5-yl]-N-methyl-4-propylcyclohexanecarboxamide
CAS No. 195812-62-5 ((-)-trans-isomer), 195812-63-6 ((+)-trans-isomer), 195812-53-4 (trans-isomer)
项目整合开发状态: Biological Testing
项目研究机构: Bristol-Myers Squibb (Originator)
合成路线:The oxidative ring opening of diphenylimidazole (I) with m-chloroperbenzoic acid (MCPBA) in refluxing chloroform or dichloromethane gives the intermediate,not isolated,bisbenzamide (II),which by acid catalyzed dehydrocyclization yields the imidazoline (III).The hydrogenation of the exo double bond of (III) with LiAlH4 in methanol affords N-imidazolinylbenzamide (IV),which is methylated with methyl iodide and NaH in DMF to provide the N-disubstituted benzamide (V).The hydrolysis of benzamide (V) with potassium tert-butoxide gives the seconday amine (VI),which is acylated with 4-propylcyclohexylcarbonyl chloride (VII) by means of DMAP and triethylamine or pyridine in dichloromethane or dichloroethane to yield the amide (VIII).Finally,this compound is treated with LiCN,KI and K2CO3 in DMSO at 130-40 C.