Hydrogen Peroxide → 2-(4-(7-cyano-1-cyclopentyl-4-oxo-4,5-dihydro-1H-pyrrolo[3,2-c]pyridin-3-yl)-2-thienyl)acetamide
Reaction equation
[C:1]([CH2:3][C:4]1[S:8][CH:7]=[C:6]([C:9]2[C:13]3[C:14](=[O:20])[NH:15][CH:16]=[C:17]([C:18]#[N:19])[C:12]=3[N:11]([CH:21]3[CH2:25][CH2:24][CH2:23][CH2:22]3)[CH:10]=2)[CH:5]=1)#[N:2].C(=O)([O-])[O-:27].[K+].[K+].OO.O>CS(C)=O>[C:18]([C:17]1[C:12]2[N:11]([CH:21]3[CH2:25][CH2:24][CH2:23][CH2:22]3)[CH:10]=[C:9]([C:6]3[CH:5]=[C:4]([CH2:3][C:1]([NH2:2])=[O:27])[S:8][CH:7]=3)[C:13]=2[C:14](=[O:20])[NH:15][CH:16]=1)#[N:19]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 3-(5-(cyanomethyl)-3-thienyl)-1-cyclopentyl-4-oxo-4,5-dihydro-1H-pyrrolo[3,2-c]pyridine-7-carbonitrile (80 mg) obtained in Example 93 and 2M aqueous potassium carbonate solution (0.574 mL) in DMSO (3 mL) was added 30% hydrogen peroxide aqueous solution (0.235 mL) at 0° C., and the mixture was stirred at room temperature for 5 hr. To the reaction mixture was added water, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to give the title compound (13 mg).
Workup
- extractionthe mixture was extracted with ethyl acetate
- washThe organic layer was washed with water and saturated brine
- dry with materialdried over anhydrous magnesium sulfate
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-64e0aca9e1fe4d7192f2f43eb8e4f069
- Source dataset
- uspto-grants-2016_06
- Patent number
- US09371320B2
Reaction notes
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