Patent ID: 7332605

Claim:
A process for synthesizing a product having Formula I′, wherein each R, R 1 , R 2 and R 3 is independently selected from the group consisting of halo, nitro, cyano, carboxylic acid, hydroxyl, thiol, amino, acyl, carboxylate, carboxamide, sulfonamide, and a heterocyclic group; or alkyl (C 1-10 ), alkenyl (C 2-10 ), alkynyl (C 2-10 ), aryl (C 5-12 ), arylalkyl, arylalkenyl, and arylalkynyl, each of which may optionally contain one or more heteroatoms selected from O, S, and N; or each R and/or R 2 can independently be H; k is 0-3; m is 0-4 and n is 1-6, comprising: (a) reacting a 5,6,7,8-tetrahydroquinolinylamine optionally substituted with R 1 with an alkyl aldehyde bearing a phthalimide protecting group or a di-tert-butoxycarbonyl protecting group to produce an imine; (b) reducing the imine in an organic solvent with a metal hydride reducing reagent and either an organic acid or a metal salt to form a secondary amine; (c) reacting the secondary amine with a 2-halomethylbenzimidazole optionally substituted with R 3 and optionally bearing a benzimidazole amine protecting group or other amine substitution (R 2 ) to form a phthalimido-protected or a di-tert-butoxycarbonyl-protected tertiary amine; and (d) hydrolyzing the protected tertiary amine to obtain the product of Formula I′.