Dimethylformamide → HCID 86683573, compound

Participants

Reaction Steps

To a solution of tert-butyl(1-(4-(7-phenyl-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazin-6-yl)phenyl)cyclobutyl)carbamate (24 mg, 0.05 mmol) in dry DMF (1 ml) was added potassium carbonate (93 mg, 1.57 mmol) and bromoacetonitrile (110 μl, 1.57 mmol) under nitrogen. The resulting mixture was stirred for 4 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 60% EtOAc in cyclohexane) to give the title compound (5 mg, 19%). 1H NMR (500 MHz, CDCl3): 7.22-7.11 (9H, m), 6.93 (1H, s), 4.92 (1H, s), 4.51-4.49 (2H, m), 4.15 (2H, s), 3.39-3.37 (2H, m), 2.55-2.25 (4H, m), 1.99-1.94 (1H, m), 1.75-1.63 (1H, m), 1.44-1.15 (9H, br).

Provenance & Evidence