Reaction equation
[CH3:1][N:2]1[CH:6]=[C:5]([C:7](O)=[O:8])[C:4]([C:10]([F:13])([F:12])[F:11])=[N:3]1.CN(C)C=O.[C:19]([C:23]1[C:24]([CH:30]=[CH2:31])=[C:25]([NH2:29])[CH:26]=[CH:27][CH:28]=1)([CH3:22])([CH3:21])[CH3:20].C(N(CC)CC)C>C(Cl)Cl>[C:19]([C:23]1[C:24]([CH:30]=[CH2:31])=[C:25]([NH:29][C:7]([C:5]2[C:4]([C:10]([F:13])([F:12])[F:11])=[N:3][N:2]([CH3:1])[CH:6]=2)=[O:8])[CH:26]=[CH:27][CH:28]=1)([CH3:22])([CH3:21])[CH3:20]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
197 mg (1,01 mmol) 1-methyl-3-trifluoromethyl-1H-pyrazole-4-carboxylic acid and 135 mg (1,07 mmol) oxalylic acid chloride are dissolved in 8 ml methylenechloride. The solution is stirred for 3 hours at room temperature in the presence of a catalytic amount of dimethylformamide (DMF). After this the solution is slowly added to a solution consisting of 180 mg (1,01 mmol) 3-tert-butyl-2-vinyl-phenylamine, 155 mg (1,52 mmol) triethylamine and 7 ml methylenechloride. The resulting reaction mixture is then stirred at room temperature for 16 hours. After removal of the solvent in a water jet vacuum, the residue is purified by flash chromatography over silicagel (eluent: hexane/ethylacetate 2:1). This gives 0,27 g 1-methyl-3-trifluoromethyl-1H-pyrazole-4-carboxylic acid (3-tert-butyl-2-vinylphenyl)amide in the form of a colourless solid (m.p. 118-119° C.; 76% of theory).
Workup
- additionAfter this the solution is slowly added to a solution
- customThe resulting reaction mixture
- customAfter removal of the solvent in a water jet vacuum
- customthe residue is purified by flash chromatography over silicagel (eluent: hexane/ethylacetate 2:1)
Sources & evidence
- ORD record
- ord-2ef4725139d742d496e09cfb23d1adca
- Source dataset
- uspto-grants-2010_08
- Patent number
- US07767625B2
Linked notes
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