Trifluoroacetic acid → Pyridine-2-carboxylic acid-(4-(1-acetyl-pyrrolidin-2-yl)-5-fluoro-2-nitro-phenyl)-amide
Reaction equation
[N+:1]([O-:4])([O-])=[O:2].[K+].FC(F)(F)C(O)=O.[C:13]([N:16]1[CH2:20][CH2:19][CH2:18][CH:17]1[C:21]1[CH:26]=[CH:25][C:24]([NH:27][C:28]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][N:31]=2)=[O:29])=[CH:23][C:22]=1[F:36])(=[O:15])[CH3:14]>>[C:13]([N:16]1[CH2:20][CH2:19][CH2:18][CH:17]1[C:21]1[C:22]([F:36])=[CH:23][C:24]([NH:27][C:28]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][N:31]=2)=[O:29])=[C:25]([N+:1]([O-:4])=[O:2])[CH:26]=1)(=[O:15])[CH3:14]Participants
Procedure
94 mg of potassium nitrate was added to a trifluoroacetic acid (3 ml) solution of pyridine-2-carboxylic acid-(4-(1-acetyl-pyrrolidin-2-yl)-3-fluoro-phenyl)-amide, and the reaction liquid was stirred at room temperature for 2 days. The reaction liquid was distilled under reduced pressure, diluted with chloroform, and made basic with aqueous saturated sodium bicarbonate solution, and then extracted with chloroform. The organic layers were combined, washed with saturated saline, and dried with anhydrous magnesium sulfate. The solvent was evaporated away under reduced pressure, and the resulting residue was purified through silica gel column chromatography (developing solvent: chloroform/methanol=50/1) to obtain the entitled compound as a pale yellow solid.
Workup
- customthe reaction liquid
- customThe reaction liquid
- distillationwas distilled under reduced pressure
- additiondiluted with chloroform
- extractionextracted with chloroform
- washwashed with saturated saline
- dry with materialdried with anhydrous magnesium sulfate
- customThe solvent was evaporated away under reduced pressure
- customthe resulting residue was purified through silica gel column chromatography (developing solvent: chloroform/methanol=50/1)
Sources & evidence
- ORD record
- ord-6ca5e07cfbec406a8a5e0dc7c1a6c3de
- Source dataset
- uspto-grants-2010_06
- Patent number
- US07728025B2
Reaction notes
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