[CH3:1][C:2]([CH3:22])([CH3:21])[C:3](=[O:20])[CH2:4][NH:5][C:6]1[N:10]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[N:9]=[C:8]([C:17]([OH:19])=[O:18])[CH:7]=1.[CH3:23][Mg+].[Br-].O.Cl>C1COCC1.CCOC(C)=O>[OH:20][C:3]([CH3:23])([C:2]([CH3:22])([CH3:21])[CH3:1])[CH2:4][NH:5][C:6]1[N:10]([C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)[N:9]=[C:8]([C:17]([OH:19])=[O:18])[CH:7]=1200 mg (0.664 mmol) 5-(3,3-Dimethyl-2-oxo-butylamino)-1-phenyl-1H-pyrazole-3-carboxylic acid are dissolved in 10 ml dry THF under argon and cooled to 0° C. in an ice bath. 0.664 mmol (1 eq) of MeMgBr (3.0M solution in Et2O) are added within 5 minutes and the resulting mixture is allowed to reach RT overnight. 20 ml of water and EtOAc are added, then the pH is adjusted to 3-4 by addition of 10% HCl solution and the phases are separated. The organic phase is dried over Na2SO4 and the solvent removed to yield 110 mg (51%) of 5-(2-Hydroxy-2,3,3-trimethyl-butylamino)-1-phenyl-1H-pyrazole-3-carboxylic acid.
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