Methyl iodide → HCID 86683605, 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 iodomethane (7.5 μL, 0.118 mmol) in anhydrous N,N-dimethylformamide (1 mL) to give an orange suspension. The reaction mixture was stirred at room temperature for 2 hours, then 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 (50 mg, 97% yield). 1H-NMR (500 MHz, CDCl3) δ 7.24-7.47 (8H, m), 7.16-7.23 (2H, m), 5.23 (2H, s), 5.05 (1H, br s), 3.36 (3H, s), 2.20-2.65 (4H, m), 2.01-2.15 (1H, m), 1.77-1.90 (1H, m), 1.10-1.50 (9H, br m). LCMS (Method A) RT=7.16 min, M+H+=522.01.

Provenance & Evidence