HCID 86683572, compound → 1-((1H-imidazol-2-yl)methyl)-6-(4-(1-aminocyclobutyl)phenyl)-7-phenyl-1H-pyrido[2,3-b][1,4]oxazin-2(3H)-one

HRID 1509145Notes

Reaction equation

HRID 1509145 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[C:2]1[CH2:6][N:7]1[C:12](=[O:13])[CH2:11][O:10][C:9]2[N:14]=[C:15]([C:24]3[CH:29]=[CH:28][C:27]([C:30]4([NH:34]C(=O)OC(C)(C)C)[CH2:33][CH2:32][CH2:31]4)=[CH:26][CH:25]=3)[C:16]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[CH:17][C:8]1=2>C(O)(C(F)(F)F)=O>[NH:1]1[CH:5]=[CH:4][N:3]=[C:2]1[CH2:6][N:7]1[C:12](=[O:13])[CH2:11][O:10][C:9]2[N:14]=[C:15]([C:24]3[CH:25]=[CH:26][C:27]([C:30]4([NH2:34])[CH2:33][CH2:32][CH2:31]4)=[CH:28][CH:29]=3)[C:16]([C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)=[CH:17][C:8]1=2

Participants

3

Reactant 1

HCID 86683572HCID 86683572, compound

Product 1

HCID 532620541-((1H-imidazol-2-yl)methyl)-6-(4-(1-aminocyclobutyl)phenyl)-7-phenyl-1H-pyrido[2,3-b][1,4]oxazin-2(3H)-oneYield 1,107.4%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

Tert-butyl (1-(4-(1-((1H-imidazol-2-yl)methyl)-2-oxo-7-phenyl-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazin-6-yl)phenyl)cyclobutyl)carbamate (5 mg, 0.001 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 DCM. The remaining solvent was removed under reduced pressure and dried to afford the title compound (5 mg, quantitative). LCMS (Method A): RT=2.80 min, M-NH2=435. 1H NMR (500 MHz, MeOD): 7.44 (1H, s), 7.41 (2H, s), 7.31-7.26 (4H,m), 7.18-7.16 (3H,m), 7.06-7.05 (2H, m), 5.44 (2H, s), 4.97 (2H, s), 2.66-2.60 (2H, m), 2.49-2.43 (2H, m), 2.14-2.10 (1H, m), 1.89-1.82 (1H, m).

Workup

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

Sources & evidence

ORD record
ord-dab1de0df0344a76be99edbd0b8a5bf1
Source dataset
uspto-grants-2015_12
Patent number
US09221838B2

Reaction notes

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