Potassium Carbonate → HCID 66999491, compound
Reaction equation
[N+:1]([C:4]1[CH:5]=[N:6][NH:7][CH:8]=1)([O-:3])=[O:2].[F:9][C:10]1[CH:15]=[C:14]([F:16])[CH:13]=[CH:12][C:11]=1[C@@:17]1([CH2:21][N:22]2[CH:26]=[N:25][CH:24]=[N:23]2)[C@H:19]([CH3:20])[O:18]1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[F:9][C:10]1[CH:15]=[C:14]([F:16])[CH:13]=[CH:12][C:11]=1[C@:17]([OH:18])([C@H:19]([N:6]1[CH:5]=[C:4]([N+:1]([O-:3])=[O:2])[CH:8]=[N:7]1)[CH3:20])[CH2:21][N:22]1[CH:26]=[N:25][CH:24]=[N:23]1Participants
Conditions
- Temperature
- 180 °C
Procedure
4-Nitropyrazole (0.5 g, 4.42 mmol) and 1-(((2R,3S)-2-(2,4-difluorophenyl)-3-methyloxiran-2-yl)methyl)-1H-1,2,4-triazol (0.93 g, 3.68 mmol) were suspended in N,N-dimethylformamide (20 mL), and anhydrous potassium carbonate (0.61 g, 4.44 mmol) was added thereto, followed by heating at 180° C. for 5 minutes by microwave irradiation while stirring. After completion of the reaction, the resulting mixture was extracted with ethyl acetate (200 mL), and the extract was washed successively with saturated ammonium chloride (200 mL) and brine (200 mL). The organic layer was dried over anhydrous magnesium sulfate and concentrated by evaporation under a reduced pressure. The resulting residue was purified by silica gel chromatography to obtain the title compound (1.0 g, yield 75%).
Workup
- customAfter completion of the reaction
- extractionthe resulting mixture was extracted with ethyl acetate (200 mL)
- washthe extract was washed successively with saturated ammonium chloride (200 mL) and brine (200 mL)
- dry with materialThe organic layer was dried over anhydrous magnesium sulfate
- concentrationconcentrated by evaporation under a reduced pressure
- customThe resulting residue was purified by silica gel chromatography
Sources & evidence
- ORD record
- ord-35772ab0d513412abe87e70faae25951
- Source dataset
- uspto-grants-2011_11
- Patent number
- US08063229B2
Reaction notes
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