Hydrochloric Acid → 4-(3-aminopyridin-4-ylamino)-N-isopropylcyclohexanecarboxamide

Participants

Reaction Steps

To a solution of cis-4-(2-chloro-5-nitropyridin-4-ylamino)-N-isopropylcyclohexanecarboxamide (100 mg, 0.293 mmol) and conc. HCl (0.072 mL, 0.880 mmol) in EtOH (3.0 mL) under nitrogen was added Pd/C (10% wt) (156 mg, 0.147 mmol) and ammonium formate (185 mg, 2.93 mmol), and the mixture was stirred at RT for 30 minutes. The mixture was filtered through a pad of Celite® brand filter aid and evaporated. The residue was diluted with 10% IPA in DCM, and washed with 1 N NaOH and then with saturated aqueous NaHCO3. The organic layer was dried over Na2SO4, filtered and the solvent was removed to afford 4-(3-aminopyridin-4-ylamino)-N-isopropylcyclohexanecarboxamide as an off-white solid.

Provenance & Evidence