Trifluoroacetic acid → 1-isopropyl-1H-imidazo[4,5-c]pyridin-6-amine

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Reaction Conditions

Reaction Steps

Trifluoroacetic acid (2.42 ml, 31.4 mmol) was added to a solution of 1-isopropyl-N-(4-methoxybenzyl)-1H-imidazo[4,5-c]pyridin-6-amine (intermediate 25, 596 mg, 2.01 mmol) in DCM (12 ml) and then the mixture was stirred at 40° C. for 24 h. The reaction mixture was diluted with DCM and washed with sat. aq. NaHCO3 (strong gas evolution) and H2O. The aqueous phase was extracted with DCM (2×). The combined organic layers were dried over Na2SO4 and evaporated. The crude material was applied to a 24 g RediSep® silica column and purified by normal phase chromatography, eluting with 9:1 CH2Cl2/MeOH. Product-containing fractions were combined and evaporated to give the title compound as a beige solid. (UPLC-MS 6) tR 0.33; ESI-MS 177.1 [M+H]+.

Provenance & Evidence