3-Methylbutanehydrazide → Tert-butyl (1-(4-(1-isobutyl-8-phenyl-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 (200 mg, 0.410 mmol) and 3-methylbutanehydrazide (47 mg, 0.410 mmol) in p-xylene (1.5 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 (15 mg, 5%). LCMS (Method D): RT=1.5687 min, M+1=552. 1H NMR (500 MHz, CDCl3): 7.80 (1H, s), 7.36-7.31 (5H, m), 7.30-7.27 (2H, m), 7.23-7.19 (2H, m), 5.57 (2H, s), 2.98 (2H, d), 2.54-2.41 (4H, m), 2.33-2.24 (1H, m), 2.13-2.01 (1H, m), 1.88-1.76 (1H, m), 1.44-1.26 (9H, bs), 1.11 (6H, d).

Provenance & Evidence