Potassium Carbonate → HCID 86683585, compound

Participants

Reaction Conditions

Reaction Steps

In a 15 mL reaction tube was added tert-butyl 1-(4-(2-oxo-7-phenyl-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazin-6-yl)phenyl)cyclobutylcarbamate (50 mg, 0.106 mmol), potassium carbonate (44 mg, 0.318 mmol) and (bromomethyl)cyclopropane (0.031 mL, 0.318 mmol) in anhydrous N,N-dimethylformamide (1 mL) to give an orange suspension. The reaction mixture was stirred at 80° C. for one hour. The reaction mixture was allowed to cool to room temperature, diluted with saturated sodium bicarbonate solution (5 mL) and extracted into dichloromethane (3×3 mL). The combined organic phases were dried over Na2SO4, filtered and concentrated to dryness under reduced pressure to give a yellow oil. This was purified by Biotage chromatography (cyclohexane:ethyl acetate, gradient elution from 90:10 to 20:80) to give the desired product as an off-white solid (40 mg, 72% yield). 1H-NMR (500 MHz, CDCl3) δ 7.32 (1H, s), 7.10-7.28 (9H, m), 4.98 (1H, br s), 4.82 (2H, s), 3.79 (2H, d), 2.05-2.60 (4H, m), 1.90-2.05 (1H, m), 1.65-1.79 (1H, m), 1.00-1.45 (10H, br m), 0.45-0.57 (2H, m), 0.35-0.45 (2H, m). LCMS (Method A) RT=7.79 min, M+H+=526.18.

Provenance & Evidence