Lithium hydroxide, monohydrate → 5-{[3-(4-fluoro-phenyl)-5-methyl-isoxazol-4-ylmethyl]-amino}-2H-pyrazole-3-carboxylic acid
Reaction equation
C[O:2][C:3]([C:5]1[NH:6][N:7]=[C:8]([NH:10][CH2:11][C:12]2[C:13]([C:18]3[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=3)=[N:14][O:15][C:16]=2[CH3:17])[CH:9]=1)=[O:4].O.[OH-].[Li+]>C1COCC1.O>[F:24][C:21]1[CH:22]=[CH:23][C:18]([C:13]2[C:12]([CH2:11][NH:10][C:8]3[CH:9]=[C:5]([C:3]([OH:4])=[O:2])[NH:6][N:7]=3)=[C:16]([CH3:17])[O:15][N:14]=2)=[CH:19][CH:20]=1Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Procedure
5-{[3-(4-Fluoro-phenyl)-5-methyl-isoxazol-4-ylmethyl]-amino}-2H-pyrazole-3-carboxylic acid methyl ester (900 mg, 2.72 mmol) was then dissolved in THF (20 mL) and lithium hydroxide monohydrate (686 mg, 16.34 mmol) in water (15 mL) added and the resulting mixture stirred for 12 h. After evaporation the mixture was diluted with water (10 mL) and citric acid (10%) and extracted with ethyl acetate (2×80 mL). The combined extracts were then dried with sodium sulfate, filtered and evaporated to afford 5-{[3-(4-fluoro-phenyl)-5-methyl-isoxazol-4-ylmethyl]-amino}-2H-pyrazole-3-carboxylic acid (703 mg, 91%) as an off white solid. MS: m/e=317.4 [M+H]+.
Workup
- customAfter evaporation the mixture
- additionwas diluted with water (10 mL) and citric acid (10%)
- extractionextracted with ethyl acetate (2×80 mL)
- dry with materialThe combined extracts were then dried with sodium sulfate
- filtrationfiltered
- customevaporated
Sources & evidence
- ORD record
- ord-93059e5f3bbe4b108d6c89459ad39381
- Source dataset
- uspto-grants-2012_04
- Patent number
- US08163728B2
Reaction notes
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