Reaction equation
[N+:1]([O-:4])(O)=[O:2].[C:5]([N:8]1[CH2:12][CH2:11][CH:10]([CH3:13])[CH:9]1[C:14]1[CH:19]=[CH:18][C:17]([NH:20][C:21]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=2)=[O:22])=[CH:16][C:15]=1[F:29])(=[O:7])[CH3:6]>>[C:5]([N:8]1[CH2:12][CH2:11][CH:10]([CH3:13])[CH:9]1[C:14]1[C:15]([F:29])=[CH:16][C:17]([NH:20][C:21]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=2)=[O:22])=[C:18]([N+:1]([O-:4])=[O:2])[CH:19]=1)(=[O:7])[CH3:6]Participants
3
Procedure
1 ml of fuming nitric acid was added to 70 mg of N-(4-(1-acetyl-3-methylpyrrolidin-2-yl)-3-fluorophenyl)pyridine-2-carboxamide, and the reaction liquid was stirred at room temperature for 2 hours. The reaction liquid was poured into a mixture of ice-aqueous saturated sodium bicarbonate, extracted with chloroform, and dried with anhydrous sodium carbonate. The solvent was evaporated away under reduced pressure, and the resulting residue was purified through partitioning thin-layer chromatography (Kieselgel™ 60F254, Art 5744 (by Merck), chloroform/methanol=20/1) to obtain the entitled compound as a yellow solid.
Workup
- customthe reaction liquid
- customThe reaction liquid
- additionwas poured into a mixture of ice-aqueous saturated sodium bicarbonate
- extractionextracted with chloroform
- dry with materialdried with anhydrous sodium carbonate
- customThe solvent was evaporated away under reduced pressure
- customthe resulting residue was purified
- customthrough partitioning thin-layer chromatography (Kieselgel™ 60F254, Art 5744 (by Merck), chloroform/methanol=20/1)
Sources & evidence
- ORD record
- ord-2541684330a54406917d1890e9fc82c6
- Source dataset
- uspto-grants-2010_06
- Patent number
- US07728025B2
Linked notes
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