N-bromobutanimide → N-[(7-bromo-2-oxo-4-pyridin-2-yl-1,2,4,5-tetrahydroimidazo[1,5,4-de][1,4]benzoxazin-4-yl)methyl]acetamide

HRID 589073Notes

Reaction equation

HRID 589073 reaction equation
[Br:1]N1C(=O)CCC1=O.[O:9]=[C:10]1[N:18]2[C:19]([CH2:28][NH:29][C:30](=[O:32])[CH3:31])([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=3)[CH2:20][O:21][C:16]3=[C:17]2[C:12](=[CH:13][CH:14]=[CH:15]3)[NH:11]1>C(#N)C.C(O)(=O)C>[Br:1][C:15]1[C:16]2[O:21][CH2:20][C:19]([CH2:28][NH:29][C:30](=[O:32])[CH3:31])([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=3)[N:18]3[C:10](=[O:9])[NH:11][C:12]([C:17]=23)=[CH:13][CH:14]=1

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 90409826N-[(2-oxo-4-pyridin-2-yl-1,2,4,5-tetrahydroimidazo[1,5,4-de][1,4]benzoxazin-4-yl)methyl]acetamide

Product 1

HCID 90408820N-[(7-bromo-2-oxo-4-pyridin-2-yl-1,2,4,5-tetrahydroimidazo[1,5,4-de][1,4]benzoxazin-4-yl)methyl]acetamideYield 60%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
0 °C

Procedure

N-Bromosuccinimide (40 mg, 0.2 mmol) was added to a mixture of N-[(2-oxo-4-pyridin-2-yl-1,2,4,5-tetrahydroimidazo[1,5,4-de][1,4]benzoxazin-4-yl)methyl]acetamide in acetonitrile (5 mL) and acetic acid (3 mL), and cooled to 0° C. The reaction was stirred for 1 h, concentrated to remove residual acetic acid, and partitioned between ethyl acetate and saturated aqueous sodium bicarbonate. The organic layer was washed with brine, dried over magnesium sulfate, filtered, and concentrated to give crude N-[(7-bromo-2-oxo-4-pyridin-2-yl-1,2,4,5-tetrahydroimidazo[1,5,4-de][1,4]benzoxazin-4-yl)methyl]acetamide (0.040 g. 60%). LCMS calculated for C17H16BrN4O3 (M+H)+: m/z=403.1, 405.1. found: 402.9, 405.0.

Workup

  1. concentrationconcentrated
  2. customto remove residual acetic acid
  3. custompartitioned between ethyl acetate and saturated aqueous sodium bicarbonate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-48638ae5045c4c2a8228d5dfa6641f2a
Source dataset
uspto-grants-2016_01
Patent number
US09227985B2

Reaction notes

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