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

HRID 1509331Notes

Reaction equation

HRID 1509331 reaction equation
[CH:1]1([CH2:4][N:5]2[C:10](=[O:11])[CH2:9][O:8][C:7]3[N:12]=[C:13]([C:22]4[CH:36]=[CH:35][C:25]([CH2:26][NH:27]C(=O)OC(C)(C)C)=[CH:24][CH:23]=4)[C:14]([C:16]4[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=4)=[CH:15][C:6]2=3)[CH2:3][CH2:2]1>C(O)(C(F)(F)F)=O>[NH2:27][CH2:26][C:25]1[CH:35]=[CH:36][C:22]([C:13]2[C:14]([C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)=[CH:15][C:6]3[N:5]([CH2:4][CH:1]4[CH2:2][CH2:3]4)[C:10](=[O:11])[CH2:9][O:8][C:7]=3[N:12]=2)=[CH:23][CH:24]=1

Participants

3

Reactant 1

HCID 86683684tert-Butyl 4-(1-(cyclopropylmethyl)-2-oxo-7-phenyl-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazin-6-yl)benzylcarbamate

Product 1

HCID 532626716-(4-(Aminomethyl)phenyl)-1-(cyclopropylmethyl)-7-phenyl-1H-pyrido[2,3-b][1,4]oxazin-2(3H)-oneYield 70.9%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

tert-Butyl 4-(1-(cyclopropylmethyl)-2-oxo-7-phenyl-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazin-6-yl)benzylcarbamate (80 mg, 0.165 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 (45 mg, 70.9%) as white solid. LCMS: RT=0.84 min, M+H+=386. 1H NMR (500 MHz, CDCl3): 8.33 (2H, br), 7.41 (1H, s), 7.27-7.26 (4H, m), 7.18 (3H, m), 7.13-7.12 (2H, m), 4.82 (2H, s), 3.94 (2H, s), 3.87-3.85 (2H, d), 1.16-1.14 (1H, m), 0.60-0.57 (2H, m), 0.48-0.45 (2H, m).

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-894ad1bac52448258fd61f78bbb0ddda
Source dataset
uspto-grants-2015_12
Patent number
US09221838B2

Reaction notes

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