合成路线:The earlier synthesis starts with the reaction of 4-chloro-7-(trifluoromethyl)quinoline (I) with 4-aminobenzoic acid (II) in ethanol-HCl giving 4-(4-carboxyphenylamino)-7-(trifluoromethyl)quinoline (III),which is converted to its acyl chloride (IV) by treatment with SOCl2.The reaction of (IV) with piperazine (V) yields 1-[4-[7-(trifluoromethyl)quinolin-4-ylamino]benzoyl]piperazine (VI),which is finally acylated with 4-fluorobenzenesulfonyl chloride (VII) to give U-54669 F.However,this method is not economically efficient,since the most expensive compound [quinoline (I)] is already used in the first step of the synthesis.
合成路线:The condensation of 4-nitrobenzoyl chloride (I) with piperazine (II) in water by means of KOH gives 4-nitrobenzoylpiperazine (III),which is reduced with H2 over Pd/C in methanol yielding 4-aminobenzoyl piperazine (IV).The condensation of (IV) with 4-chloro-7-trifluoromethylquinoline (V) by means of HCl in refluxing ethanol affords 4-[4-[[7-(trifluoromethyl)-4-quinolinyl]amino]benzoyl]piperazine (VI),which is finally acylated with 4-fluorobenzenesulfonyl chloride (VII) by means of triethylamine in THF.
参考文献标题:Aminoquinolines
文献作者:McCall,J.M.(Pharmacia Corp.)
参考来源:GB 2021567
合成路线:The condensation of 4-nitrobenzoyl chloride (I) with piperazine (II) in water by means of KOH gives 4-nitrobenzoylpiperazine (III),which is reduced with H2 over Pd/C in methanol yielding 4-aminobenzoyl piperazine (IV).The condensation of (IV) with 4-chloro-7-trifluoromethylquinoline (V) by means of HCl in refluxing ethanol affords 4-[4-[[7-(trifluoromethyl)-4-quinolinyl]amino]benzoyl]piperazine (VI),which is finally acylated with 4-fluorobenzenesulfonyl chloride (VII) by means of triethylamine in THF.
参考文献标题:U-54669-F
文献作者:Castar,J.; Serradell,M.N.
参考来源:Drugs Fut 1984,9(1),36
产品链接: CAS No. 81435-67-8›› 产品链接: CAS No.72141-57-2››