Hydrochloric Acid → HCID 86683572, compound

Participants

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 (26 mg, 0.05 mmol) in dry DMF (1 ml) was added sodium hydride (5 mg, 0.13 mmol) at 0° C. under nitrogen. After 1 hour at 0° C., 2-(chloromethyl)-1H-imidazole.HCl (10 mg, 0.07 mmol) was added and the resulting mixture was stirred for an additional 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 preparative HPLC (method G, gradient 5 to 95% 0.1% FA/ACN in 0.1% FA/H2O) to give the title compound (5 mg, 17%). 1H NMR (500 MHz, CDCl3): 7.83 (1H, s), 7.22-7.15 (7H,m), 7.14-7.13 (2H,m), 6.94 (2H,s), 6.22 (1H, br s), 5.14 (2H, s), 4.98 (1H, br s), 4.83 (2H, s), 2.52-2.20 (4H, m), 2.00-1.95 (1H, m), 1.75-1.70 (1H, m), 1.44-1.15 (9H, br).

Provenance & Evidence