Potassium Carbonate → HCID 86683590, 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 (59 mg, 0.424 mmol) and 4-(chloromethyl)thiazole HCl salt (54 mg, 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 0:100) to give the desired product as an off-white solid (54 mg, 90% yield). 1H-NMR (500 MHz, CDCl3) δ 8.70 (1H, s), 7.61 (1H, s), 7.28 (1H, s), 7.12-7.27 (7H, m), 7.03-7.12 (2H, m), 5.23 (2H, s), 4.99 (1H, br s), 4.86 (2H, s), 2.10-2.60 (4H, m), 2.41-2.06 (1H, m), 1.65-1.79 (1H, m), 1.00-1.45 (9H, br m). LCMS (Method A) RT=7.11 min, M+H+=569.14.

Provenance & Evidence