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

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.

1. stirringstirred for 15 minutes
2. customto give a white precipitate
3. customthe supernatant solution removed
4. washThe solid was washed twice more with diethyl ether (6 mL)
5. customremoving the supernatant solvent each time
6. customThe remaining solvent was removed by concentration to dryness under reduced pressure
7. customfreeze-drying over the weekend

ORD record

ord-73d2ffdfe9de427cb451be2e3a83b2d7

Source dataset

uspto-grants-2015_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09221838B2