tert-Butyl 4-(1-ethyl-2-oxo-7-phenyl-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazin-6-yl)benzylcarbamate → 6(4-(Aminomethyl)phenyl)-1-ethyl-7-phenyl-1H-pyrido[2,3-b][1,4]oxazin-2(3H)-one

HRID 1509329Notes

Reaction equation

HRID 1509329 reaction equation
[CH2:1]([N:3]1[C:8](=[O:9])[CH2:7][O:6][C:5]2[N:10]=[C:11]([C:20]3[CH:34]=[CH:33][C:23]([CH2:24][NH:25]C(=O)OC(C)(C)C)=[CH:22][CH:21]=3)[C:12]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[CH:13][C:4]1=2)[CH3:2]>C(O)(C(F)(F)F)=O>[NH2:25][CH2:24][C:23]1[CH:33]=[CH:34][C:20]([C:11]2[C:12]([C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=3)=[CH:13][C:4]3[N:3]([CH2:1][CH3:2])[C:8](=[O:9])[CH2:7][O:6][C:5]=3[N:10]=2)=[CH:21][CH:22]=1

Participants

3

Reactant 1

HCID 86683682tert-Butyl 4-(1-ethyl-2-oxo-7-phenyl-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazin-6-yl)benzylcarbamate

Product 1

HCID 532626706(4-(Aminomethyl)phenyl)-1-ethyl-7-phenyl-1H-pyrido[2,3-b][1,4]oxazin-2(3H)-oneYield 99.4%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

tert-Butyl 4-(1-ethyl-2-oxo-7-phenyl-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazin-6-yl)benzylcarbamate (45 mg, 0.098 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 (35 mg, 99%) as white solid. LCMS: RT=0.75 min, M+H+=360. 1H NMR (500 MHz, CDCl3): 8.34 (2H, br), 7.30-7.27 (5H, m), 7.18 (3H, m), 7.13-7.11 (2H, m), 4.80 (2H, s), 4.03-3.99 (2H, q), 3.96 (2H, s), 1.32-1.30 93H, t).

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-85b42f0efe79427983e95a90075b7861
Source dataset
uspto-grants-2015_12
Patent number
US09221838B2

Reaction notes

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