Hydrochloric Acid → HCID 70664903, compound

HRID 1854538Notes

Reaction equation

HRID 1854538 reaction equation
[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]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 70665037HCID 70665037, compoundHCID 178418689HCID 178418689, compound

Product 1

HCID 70664903HCID 70664903, compoundYield 52.2%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

200 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.

Workup

  1. customthe phases are separated
  2. dry with materialThe organic phase is dried over Na2SO4
  3. customthe solvent removed

Sources & evidence

ORD record
ord-846d3dd4285e4a85ab4c99197e261020
Source dataset
uspto-grants-2015_02
Patent number
US08962671B2

Reaction notes

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