Hydrochloric Acid → 1-(piperidin-3-yl)-1H-imidazo[4,5-c]pyridin-6-amine hydrochloride

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Reaction Steps

To a solution of tert-butyl 3-(6-((diphenylmethylene)amino)-1H-imidazo[4,5-c]pyridin-1-yl)piperidine-1-carboxylate (400 mg, 0.83 mmol, 1.0 eq) in THF (4 mL) was added HCl (4 N solution in 1,4 dioxane, 4 mL). The mixture was stirred at rt for 3 h and concentrated in vacuo to afford a residue which was washed with EtOAc (10 mL×3) to give crude title compound (180 mg, 95%) as brown solid. 1H NMR (400 MHz, DMSO-d6) δ: 9.82 (s, 1H), 8.73-8.65 (m, 1H), 7.74-7.70 (m, 1H), 7.58-7.56 (m, 1H), 4.04-4.02 (m, 1H), 3.67-3.66 (m, 0.5H), 3.48-3.32 (m, 2H), 2.95-2.79 (m, 1.5H), 2.18 (s, 1H), 1.99-1.96 (m, 3H), 1.75-1.73 (m, 1H). ESI-MS (M+H+): 218.0.

Provenance & Evidence