Hydrochloric Acid → (6-(1,4-Diazepan-1-yl)pyridin-2-yl)(2-amino-5-bromopyridin-3-yl)methanone

Participants

Reaction Steps

To a suspension of tert-butyl 4-(6-(2-amino-5-bromonicotinoyl)pyridin-2-yl)-1,4-diazepane-1-carboxylate (50 mg, 0.1 mmol) in 1,4-dioxane (2 ml) at 0° C. was added 4 M HCl in 1,4-dioxane (1 ml). The resulting mixture was stirred at room temperature for 5 hours. The reaction mixture was concentrated to dryness to leave an orange solid which was further purified by reverse phase preparative HPLC [Waters Sunfire C18, 10M, 100 Å column, gradient 10%-95% B (solvent A: 0.05% TFA in water; solvent B: CH3CN) over 16 minutes at 25 mL/min]. The fractions were collected, passed through a sodium bicarbonate cartridge and freeze-dried to give the title compound as a yellow solid (13.5 mg, 36% yield).

Provenance & Evidence