Chloroacetone → HCID 53261991, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of tert-butyl(1-(4-(2-oxo-1-(2-oxopropyl)-7-phenyl-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazin-6-yl)phenyl)cyclobutyl)carbamate (60 mg, 0.13 mmol) in dry DMF (2.5 mL) was added sodium hydride (5 mg, 0.14 mmol) at 0° C. under nitrogen. After 1 h at 0° C., chloroacetone (11 □L, 0.14 mmol) was added and the resulting mixture was stirred for two hours at 0° C. A saturated solution of NH4Cl was added while stirring, keeping the temperature below 10° C. The resulting mixture was extracted with dichloromethane (3×) using a phase separator (Isolute® SPE). The combined organic phases were concentrated to dryness under reduced pressure. The resulting residue was purified by Biotage chromatography (silica, hexane:ethyl acetate, gradient elution from 100:0 to 55:45) to give the desired product as a white solid (41 mg, 60% yield). 1H NMR (500 MHz, CDCl3): 7.12-7.28 (9H, m), 6.82 (1H,S), 4.95 (2H, s), 4.54 (2H, s), 2.36-2.52 (4H, m), 2.23 (3H, s), 1.98-2.12 (1H, m), 1.69-1.75 (1H, m), 1.47 (9H, br s). 1H NMR (Method A): RT=6.87 min, M+H+=528.

Provenance & Evidence