Reaction equation
[F:1][C:2]([F:15])([F:14])[C:3]1[CH:4]=[C:5]([CH2:9][CH2:10][C:11]([OH:13])=O)[CH:6]=[CH:7][CH:8]=1.C(Cl)(=O)C(Cl)=O.[NH:22]1[C:30]2[C:25](=[CH:26][C:27]([C:31]([NH:33][NH2:34])=[O:32])=[CH:28][CH:29]=2)[CH:24]=[N:23]1.C(=O)([O-])O.[Na+]>CN(C)C=O.O1CCCC1.C(OCC)(=O)C>[F:14][C:2]([F:1])([F:15])[C:3]1[CH:4]=[C:5]([CH2:9][CH2:10][C:11]([NH:34][NH:33][C:31]([C:27]2[CH:26]=[C:25]3[C:30](=[CH:29][CH:28]=2)[NH:22][N:23]=[CH:24]3)=[O:32])=[O:13])[CH:6]=[CH:7][CH:8]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 3
Procedure
To a solution of 3-[3-(trifluoromethyl)phenyl]propionic acid (437 mg, 2.00 mmol) and N,N-dimethylformamide (1 drop) in tetrahydrofuran (4 mL) was added oxalyl chloride (0.183 mL, 2.10 mmol) at room temperature, and the resulting mixture was stirred for 30 min. The reaction mixture was added dropwise to a mixture of 1H-indazole-5-carbohydrazide (352 mg, 2.00 mmol), tetrahydrofuran (10 mL) and saturated aqueous sodium hydrogen carbonate solution (10 mL) at room temperature, and the resulting mixture was stirred for 2 hr. The reaction mixture was diluted with ethyl acetate, washed with water and saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was recrystallized from hexane/ethanol to give the title compound (383 mg, yield 51%) as colorless crystals.
Workup
- stirringthe resulting mixture was stirred for 2 hr
- washwashed with water and saturated brine
- dry with materialdried over anhydrous magnesium sulfate
- concentrationconcentrated under reduced pressure
- customThe residue was recrystallized from hexane/ethanol
Sources & evidence
- ORD record
- ord-69f4f92427c74619a90092a49b028bc5
- Source dataset
- uspto-grants-2013_07
- Patent number
- US08492378B2
Linked notes
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