Lithium Hydroxide → 1-({5-[3-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-3-yl}methyl)-1H-pyrazole-4-carboxylic acid

HRID 1257418Notes

Reaction equation

HRID 1257418 reaction equation
[F:1][C:2]([F:26])([F:25])[C:3]1[CH:4]=[C:5]([C:9]2[O:13][N:12]=[C:11]([CH2:14][N:15]3[CH:19]=[C:18]([C:20]([O:22]CC)=[O:21])[CH:17]=[N:16]3)[N:10]=2)[CH:6]=[CH:7][CH:8]=1.[OH-].[Li+]>C(O)C.O>[F:26][C:2]([F:1])([F:25])[C:3]1[CH:4]=[C:5]([C:9]2[O:13][N:12]=[C:11]([CH2:14][N:15]3[CH:19]=[C:18]([C:20]([OH:22])=[O:21])[CH:17]=[N:16]3)[N:10]=2)[CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 66939395ethyl 1-({5-[3-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-3-yl}methyl)-1H-pyrazole-4-carboxylate

Product 1

HCID 669395711-({5-[3-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-3-yl}methyl)-1H-pyrazole-4-carboxylic acidYield 28%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

The compound (0.85 g) obtained in Example 114b was dissolved in ethanol (8 mL) and water (2 ml), and lithium hydroxide (0.42 g) was added. The reaction mixture was stirred at room temperature overnight and concentrated under reduced pressure. The residue was diluted with water and adjusted to pH 5-6 with 1N hydrochloric acid. The resulting precipitate was collected by filtration and the obtained solid was recrystallized from ethyl acetate-petroleum ether to give the title compound (0.22 g) as a colorless solid.

Workup

  1. concentrationconcentrated under reduced pressure
  2. additionThe residue was diluted with water
  3. filtrationThe resulting precipitate was collected by filtration
  4. customthe obtained solid was recrystallized from ethyl acetate-petroleum ether

Sources & evidence

ORD record
ord-fcd64fa794aa45dcaad9cfad75e534d0
Source dataset
uspto-grants-2013_06
Patent number
US08461348B2

Reaction notes

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