Potassium Carbonate → HCID 86683607, compound

Participants

Reaction Steps

In a 15 mL reaction tube was added tert-butyl(1-(4-(2,2-dioxido-7-phenyl-1H-pyrido[3,2-e][1,3,4]oxathiazin-6-yl)phenyl)cyclobutyl)carbamate (50 mg, 0.099 mmol), potassium carbonate (41 mg, 0.296 mmol) and 2-bromoacetonitrile (0.021 mL, 0.296 mmol) in anhydrous N,N-dimethylformamide (1 mL) to give a yellow suspension. The reaction mixture was stirred at room temperature 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 a colourless oil (32 mg, 59% yield). 1H-NMR (500 MHz, CDCl3) δ 8.04 (1H, s), 7.25-7.38 (7H, m), 7.17-7.25 (2H, m), 5.32 (2H, s), 5.05 (1H, br s), 4.73 (2H, s), 2.20-2.65 (4H, m), 2.00-2.18 (1H, m), 1.77-1.90 (1H, m), 1.05-1.55 (9H, br m). LCMS (Method D) RT=1.60 min, M+H+=547.10.

Provenance & Evidence