Synthesis of Two Analogs of AKT Inhibitor-IV via Amine-exchange Reactions

The N-methylphenylamino group conjugated to the 2 position of the benzimidazolium core via a vinyl group in the structure of AKT inhibitor IV was efficiently substituted by treating AKT inhibitor IV with excess of N-methylcyclohexanamine and N-methylbenzylamine. The two new compounds were characterized by H-1 and C-13 NMR, IR, and mass spectroscopy. The control experiment with benzimidazole precursor of AKT inhibitor IV resulted in no amine-exchange reaction, indicating that the positive charge in the benzimidazolium salt is the major factor for the activation of the terminal conjugated N-methylphenylamino group.