新型吡非尼酮衍生物的合成

Synthesis of Novel Pirfenidone Derivatives

2-氨基-5-甲基吡啶经重氮化,水解后得到中间体2-羟基-5-甲基吡啶,与对溴苯甲醛,在加热、无水碳酸钾和碘化铜条件下进行亲核取代反应,生成中间体4-(5-甲基-2-氧代吡啶-1(2H)-基)苯甲醛,再与顺式-1,2-环己二胺,在碘的作用下生成目标产物1-(4-(3a,4,5,6,7,7a-六氢-1H-苯并[d]咪唑-2-基)苯基)-5-甲基吡啶-2(1H)-酮,共制备4个目标化合物,收率为73%~87%。产物结构均经1H NMR、13C NMR和HRMS确认。

With 2-amino-5-methylpyridine as the starting material,after diazotation reaction,hydrolysis to obtain the intermediate 2-hydroxy-5-methylpyridine,in the presence of anhydrous potassium carbonate and copper iodide nucleophilic substitution reaction with p-bromobenzaldehyde to generate intermediate 4-(5-methyl-2-oxopyridine-1(2H)-yl)benzaldehyde,and then cis-1,2-cyclohexanediamine,under the action of iodine to generate target product 1-(4-(3a,4,5,6,7,7a-hexahydro-1H-benzo[d]Imidazol-2-yl)phenyl)-5-methylpyridine-2(1H)-one was prepared with a total of 4 target compounds and a yield of 73%~87%.The product structure was confirmed by 1H NMR,13C NMR and HRMS.