Diethylamine → HCID 57863428, compound

Participants

Reaction Steps

Dissolve 1-(5-tert-butyl-isoxazol-3-yl)-3-(2-fluoro-4-{7-[2-(3-oxo-propyl)-pyridin-4-yl]-imidazo[1,2-a]pyridin-3-yl}-phenyl)-urea hydrochloride (0.5 g, 0.89 mmol) in acetic acid (20 mL) under nitrogen. Add diethylamine (0.46 mL, 5 equiv.) and stir overnight at room temperature. In the morning, add sodium triacetoxyborohydride (0.38 g, 2 equiv.) and stir 20 minutes. At this point add excess diethylamine and stir overnight at room temperature. Concentrate to dryness and purify by silica gel (10% Methanol:DCM) to give impure product. Purify by reverse phase (25% MeCN:0.03% HCl in water→100% MeCN). Dilute product containing fractions with ethyl acetate then wash with 1 N NaOH followed by aqueous saturated sodium chloride. Dry the organics over MgSO4, filter and concentrate to give the freebase (0.083 g, 16%) as a yellow solid. LCMS (ES), m/z 584.2 (M+1).

Provenance & Evidence