Acetonitrile → 7-Bromo-2-oxo-4-pyridin-2-yl-1,2,4,5-tetrahydroimidazo[1,5,4-de][1,4]benzoxazine-4-carboxamide
Reaction equation
[Br:1]N1C(=O)CCC1=O.[O:9]=[C:10]1[N:18]2[C:19]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][N:26]=3)([C:22]([NH2:24])=[O:23])[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]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][N:26]=3)([C:22]([NH2:24])=[O:23])[N:18]3[C:10](=[O:9])[NH:11][C:12]([C:17]=23)=[CH:13][CH:14]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
N-Bromosuccinimide (40 mg, 0.2 mmol) was added to a solution of 2-oxo-4-pyridin-2-yl-1,2,4,5-tetrahydroimidazo[1,5,4-de][1,4]benzoxazine-4-carboxamide, acetonitrile (5 mL) and acetic acid (3 mL) and cooled to 0° C. The reaction mixture was stirred for 1 h and then concentrated to remove residual acetic acid. The resulting residue was 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 7-bromo-2-oxo-4-pyridin-2-yl-1,2,4,5-tetrahydroimidazo[1,5,4-de][1,4]benzoxazine-4-carboxamide (0.040 g. 60%). LCMS calculated for C15H12BrN4O3 (M+H)+: m/z=375.1, 377.1. found: 375.0, 376.9.
Workup
- concentrationconcentrated
- customto remove residual acetic acid
- customThe resulting residue was partitioned between ethyl acetate and saturated aqueous sodium bicarbonate
- washThe organic layer was washed with brine
- dry with materialdried over magnesium sulfate
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-005698c1020847ce9123df10a421effa
- Source dataset
- uspto-grants-2016_01
- Patent number
- US09227985B2
Reaction notes
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