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

HRID 1509322Notes

Reaction equation

HRID 1509322 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]=1

Participants

3

Reactant 1

HCID 86683677tert-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

Product 1

HCID 532626686-(4-(Aminomethyl)phenyl)-7-phenyl-1-(2,2,2-trifluoroethyl)-1H-pyrido[2,3-b][1,4]oxazin-2(3H)-oneYield 94%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

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).

Workup

  1. customevaporated under reduced pressure
  2. customthe solid formed
  3. washwas washed twice with diethylether
  4. customThe remaining solvent was removed under reduced pressure
  5. customdried

Sources & evidence

ORD record
ord-3924181ac0724392bfd53a897eedd0b4
Source dataset
uspto-grants-2015_12
Patent number
US09221838B2

Reaction notes

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