Sodium hydride → HCID 123692355, compound

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 (48 mg, 0.10 mmol) in dry DMF (1 mL) was added sodium hydride (16 mg, 0.41 mmol) and 1-bromo-2-methoxyethane (28 mg, 0.20 mmol) under nitrogen. The resulting mixture was stirred for 2 hours at 80° C. A saturated solution of NaHCO3 was added and the mixture was extracted with dichloromethane (3×10 ml) using a phase separator (Isolute® SPE). The combined organic phases were 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 (10 mg, 18%). 1H NMR (500 MHz, CDCl3): 7.49 (1H, s), 7.23-7.17 (7H, m), 7.12-7.11 (2H, m), 4.95 (1H, s), 4.82 (2H, s), 4.05 (2H, t), 3.61 (2H, t), 3.29 (3H, s), 2.52-2.20 (4H, m), 2.00-1.95 (1H, m), 1.79-1.65 (1H, m), 1.40-1.10 (9H, br).

Provenance & Evidence