Sodium Hydroxide → HCID 23080309, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of said mixture (157 mg of tert-butyl-2-[isopropyl(methyl)amino]-5-[(phenoxycarbonyl)amino]-1H-benzimidazole-1-carboxylate and tert-butyl 2-[isopropyl(methyl) amino]-6-[(phenoxycarbonyl)amino]-1H-benzimidazole-1-carboxylate in chloroform (3 ml), 4-(4-fluorophenyl)piperidine hydrochloride (76 mg) and triethylamine (0.16 ml) were added and heated at 60° C. for 1.5 hours. The reaction liquid was cooled and after addition of water, extracted with chloroform. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. The organic layer was condensed under reduced pressure and the resulting residue was purified on preparative TLC (hexane/ethyl acetate=1/9). Thus obtained compound was dissolved in trifluoroacetic acid (2 ml) and stirred for an hour. The reaction liquid was made alkaline by addition of 4N-aqueous NaOH solution and extracted with chloroform. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. The organic layer was condensed under reduced pressure and purified on preparative TLC (methanol/chloroform=1/9) to provide the title compound (11 mg).

Provenance & Evidence