3,3,3-Trifluoropropanehydrazide → Tert-butyl (1-(4-(8-phenyl-1-(2,2,2-trifluoroethyl)-4H-pyrido[2,3-b][1,2,4]triazolo[4,3-d][1,4]oxazin-7-yl)phenyl)cyclobutyl)carbamate

Participants

Reaction Conditions

Reaction Steps

A suspension of tert-butyl(1-(4-(7-phenyl-2-thioxo-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazin-6-yl)phenyl)cyclobutyl)carbamate (250 mg, 0.513 mmol) and 3,3,3-trifluoropropanehydrazide (145 mg, 1.205 mmol) in p-xylene (2 ml) was heated to 150° C. for 15 minutes under microwave irradiation. The resulting reaction mixture was concentrated to dryness under reduced pressure and purified by Biotage silica gel chromatography (gradient 0% to 20% ethyl acetate in n-hexanes) to give the title compound (38 mg, 13%). LCMS (Method D): RT=1.499 min, M+1=578. 1H NMR (500 MHz, CDCl3): 7.84 (1H, s), 7.36-7.32 (5H, m), 7.31-7.28 (2H, m), 7.23-7.18 (2H, m), 5.60 (2H, s), 4.12 (2H, q), 2.52-2.42 (4H, m), 2.12-2.01 (1H, m), 1.87-1.78 (1H, m), 1.44-1.26 (9H, bs).

Provenance & Evidence