Potassium Carbonate → tert-butyl(1-(4-(1-((3-methyloxetan-3-yl)methyl)-2-oxo-7-phenyl-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazin-6-yl)phenyl)cyclobutyl)carbamate

Participants

Reaction Conditions

Reaction Steps

To a solution of tert-butyl(1-(4-(2-oxo-7-phenyl-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazin-6-yl)phenyl)cyclobutyl)carbamate (50 mg, 0.11 mmol) in dry DMF (1 mL) was added potassium carbonate (44 mg, 0.32 mmol) and 3-(chloromethyl)-3-methyloxetane (38 mg, 0.32 mmol) under nitrogen. The resulting mixture was stirred for 2.5 hours at 80° C. A saturated solution of NaHCO3 was added and the mixture was extracted with AcOEt (3×). The combined organic phases were dried over Na2SO4 and concentrated to dryness under reduced pressure. The resulting residue was purified by Biotage silica gel chromatography (gradient 0 to 40% EtOAc in cyclohexane) to give the title compound (21 mg, 36%). 1H NMR (500 MHz, CDCl3): 7.23-7.17 (8H, m), 7.09-7.07 (2H, m), 4.94 (2H, s), 4.83 (2H, s), 4.64 (2H, d), 4.23 (2H, d), 4.05 (2H, s), 2.52-2.20 (4H, m), 2.00-1.95 (1H, m), 1.79-1.65 (1H, m), 1.36 (3H, s), 1.40-1.10 (9H, br).

Provenance & Evidence