Acetyl chloride → HCID 86683571, 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 (22 mg, 0.05 mmol) in dry DCM (1 ml) was added triethyl amine (10 μl, 0.07 mmol) and acetyl chloride (5 μl, 0.07 mmol) under nitrogen. The resulting mixture was stirred for 1 h at room temperature. 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 80% EtOAc in cyclohexane) to give the title compound (20 mg, 83%). 1H NMR (500 MHz, CDCl3): 8.50 (1H, br s), 7.25 (2H, d), 7.19-7.17 (5H, m), 7.11-7.10 (2H,m), 4.95 (1H, s), 4.43 (2H, t), 3.94 (2H, br s), 2.55-2.25 (7H, m), 2.06-1.98 (1H, m), 1.82-1.73 (1H, m), 1.44-1.15 (9H, br).

Provenance & Evidence