Hydrochloric Acid → 6-(4-(1-aminocyclopropyl)phenyl)-1-methyl-7-phenyl-1H-pyrido[2,3-b][1,4]oxazin-2(3H)-one

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Reaction Steps

To a solution of tert-butyl(1-(4-(1-methyl-2-oxo-7-phenyl-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazin-6-yl)phenyl)cyclopropyl)carbamate (60 mg, 0.127 mmol) in 1,4-dioxane (1 mL) was added dropwise 4M HCl in 1,4-dioxane (0.5 mL, 2.00 mmol) and the resulting solution stirred at room temperature for 1 hour. The reaction mixture was diluted by the dropwise addition of diethyl ether (6 mL) and stirred for 15 minutes to give a white precipitate. The layers were allowed to settle and the supernatant solution removed. The solid was washed twice more with diethyl ether (6 mL), allowing to settle and removing the supernatant solvent each time. The remaining solvent was removed by concentration to dryness under reduced pressure, then freeze-drying over the weekend to give the desired product as an off-white solid (27 mg, 52% yield). 1H-NMR (500 MHz, MeOD) δ 7.53 (1H, s), 7.34 (2H, d), 7.31 (2H, d), 7.25-7.29 (3H, m), 7.18-7.23 (2H, m), 4.94 (2H, s), 3.41 (3H, s), 1.29-1.35 (2H, m), 1.24-1.29 (2H, m). LCMS (Method D): RT=0.75 min, M+H+=372.10.

Provenance & Evidence