Hydrogen Peroxide → 4-(1-(1-methoxybutan-2-yl)-4-oxo-4,5-dihydro-1H-pyrrolo[3,2-c]pyridin-3-yl)benzamide
Reaction equation
[CH3:1][O:2][CH2:3][CH:4]([N:7]1[C:15]2[CH:14]=[CH:13][NH:12][C:11](=[O:16])[C:10]=2[C:9]([C:17]2[CH:24]=[CH:23][C:20]([C:21]#[N:22])=[CH:19][CH:18]=2)=[CH:8]1)[CH2:5][CH3:6].C(=O)([O-])[O-:26].[K+].[K+].OO>CS(C)=O.O>[CH3:1][O:2][CH2:3][CH:4]([N:7]1[C:15]2[CH:14]=[CH:13][NH:12][C:11](=[O:16])[C:10]=2[C:9]([C:17]2[CH:18]=[CH:19][C:20]([C:21]([NH2:22])=[O:26])=[CH:23][CH:24]=2)=[CH:8]1)[CH2:5][CH3:6]Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Procedure
To a solution of 4-(1-(1-methoxybutan-2-yl)-4-oxo-4,5-dihydro-1H-pyrrolo[3,2-c]pyridin-3-yl)benzonitrile (20.0 mg) obtained in Example 24 in DMSO (0.5 mL) was added potassium carbonate (10.3 mg) at 0° C., 30% aqueous hydrogen peroxide (0.019 mL) was added thereto, and the mixture was stirred overnight at room temperature. The reaction mixture was diluted with water, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (basic silica gel, ethyl acetate to ethyl acetate/methanol) to give the title compound (18.1 mg).
Workup
- extractionthe mixture was extracted with ethyl acetate
- washThe organic layer was washed with saturated brine
- dry with materialdried over anhydrous sodium sulfate
- concentrationconcentrated under reduced pressure
- customThe residue was purified by silica gel column chromatography (basic silica gel, ethyl acetate to ethyl acetate/methanol)
Sources & evidence
- ORD record
- ord-b58feef3f75a4b18b827d1f81351c756
- Source dataset
- uspto-grants-2016_06
- Patent number
- US09371320B2
Reaction notes
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