Potassium Carbonate → HCID 67256231, 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 (150 mg, 0.318 mmol), potassium carbonate (132 mg, 0.954 mmol) and chloromethyl methyl sulfide (0.079 mL, 0.954 mmol) in anhydrous N,N-dimethylformamide (2 mL) to give a yellow suspension. The reaction mixture was heated to 80° C. under a nitrogen atmosphere for 2 hours, then allowed to cool to room temperature, diluted with saturated sodium bicarbonate solution (10 mL) and extracted into dichloromethane (3×5 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 80:20) to give the desired product as a white solid (75 mg, 44% yield). 1H-NMR (500 MHz, CDCl3) δ 7.43 (1H, s), 7.23-7.35 (7H, m), 7.19-7.23 (2H, m), 5.09 (3H, br s), 4.94 (2H, s), 2.30-2.55 (4H, m), 2.26 (3H, s), 2.00-2.15 (1H, m), 1.75-1.90 (1H, m), 1.10-1.50 (9H, br s). LCMS (Method A) RT=7.42 min, M+H+=532.14.

Provenance & Evidence