tert-Butyl 4-(2-oxo-7-phenyl-1-(2,2,2-trifluoroethyl)-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazin-6-yl)benzylcarbamate → 6-(4-(Aminomethyl)phenyl)-7-phenyl-1-(2,2,2-trifluoroethyl)-1H-pyrido[2,3-b][1,4]oxazin-2(3H)-one
Reaction equation
[O:1]=[C:2]1[CH2:7][O:6][C:5]2[N:8]=[C:9]([C:18]3[CH:32]=[CH:31][C:21]([CH2:22][NH:23]C(=O)OC(C)(C)C)=[CH:20][CH:19]=3)[C:10]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[CH:11][C:4]=2[N:3]1[CH2:33][C:34]([F:37])([F:36])[F:35]>C(O)(C(F)(F)F)=O>[NH2:23][CH2:22][C:21]1[CH:31]=[CH:32][C:18]([C:9]2[C:10]([C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=3)=[CH:11][C:4]3[N:3]([CH2:33][C:34]([F:37])([F:35])[F:36])[C:2](=[O:1])[CH2:7][O:6][C:5]=3[N:8]=2)=[CH:19][CH:20]=1Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Procedure
tert-Butyl 4-(2-oxo-7-phenyl-1-(2,2,2-trifluoroethyl)-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazin-6-yl)benzylcarbamate (45 mg, 0.088 mmol) was dissolved in TFA (1 mL). The resulting mixture was stirred for 30 seconds at room temperature and evaporated under reduced pressure. The deprotected compound was taken back twice into diethyl ether and the solid formed was washed twice with diethylether. The remaining solvent was removed under reduced pressure and dried to afford the title compound (34 mg, 94%) as off-white solid. LCMS (Method D): RT=0.82 min, M+H+=414. 1H NMR (500 MHz, CDCl3): 8.25 (2H, br), 7.47 (1H, s), 7.28-7.26 (4H, m), 7.20-7.18 (3H,m), 7.10-7.08 (2H, m), 4.88 (2H, s), 4.64-4.59 (2H, q), 3.92 (2H, s).