Potassium Carbonate → HCID 123139090, compound

Participants

Reaction Steps

In a 40 mL reaction tube was added tert-butyl 1-(4-(5-amino-6-oxo-3-phenyl-1,6-dihydropyridin-2-yl)phenyl)cyclobutylcarbamate (500 mg, 1.159 mmol) in anhydrous pyridine (5 mL) to give a yellow solution. After stirring at room temperature for 15 minutes, chloromethanesulfonyl chloride (126 μl, 1.390 mmol) was added and the resulting solution stirred at room temperature for 3 hours. The reaction mixture was concentrated to dryness under reduced pressure and redissolved in anhydrous methanol (5 mL), followed by the addition of potassium carbonate (641 mg, 4.63 mmol) and heating to 60° C. overnight. The reaction mixture was allowed to cool to room temperature and concentrated to dryness under reduced pressure. The residue was redissolved in ethyl acetate (5 mL) and washed with 50:50 water:brine (2×5 mL), dried over Na2SO4, filtered and concentrated to dryness under reduced pressure to give a brown oil. This was purified by Biotage chromatography (cyclohexane:ethyl acetate:dichloromethane:methanol, gradient elution from 80:10:10:0 to 0:90:10:0 then to 0:90:10) to give the desired product as an off-white solid (330 mg, 56% yield). 1H-NMR (500 MHz, d6-Acetone) δ 7.35 (1H, s), 7.23-7.32 (7H, m), 7.16-7.32 (2H, m), 5.39 (2H, s), 2.30-2.60 (4H, m), 2.00-2.12 (1H, m), 1.75-1.88 (1H, m), 1.05-1.40 (9H, br m). LCMS (Method A) RT=6.68 min, M+H+=508.01.

Provenance & Evidence