Ammonia → HCID 86721258, compound

HRID 1750414Notes

Reaction equation

HRID 1750414 reaction equation
[CH:1]1([N:7]2[C:11]([C:12]3[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=3)=[C:10]([C:19]([OH:21])=O)[CH:9]=[N:8]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.S(Cl)(Cl)=O.[NH3:26].C1COCC1>C1(C)C=CC=CC=1.O>[CH:1]1([N:7]2[C:11]([C:12]3[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=3)=[C:10]([C:19]([NH2:26])=[O:21])[CH:9]=[N:8]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

7

Reactant 4

HCID 222AmmoniaHCID 8028TetrahydrofuranHCID 24386Thionyl ChlorideHCID 86721259HCID 86721259, compound

Product 1

HCID 86721258HCID 86721258, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

A solution of 1-cyclohexyl-5-(4-fluorophenyl)-1H-pyrazole-4-carboxylic acid (300 mg, 1.04 mmol) and thionyl chloride (0.379 mL, 5.20 mmol) in toluene (3 mL) was stirred at 90° C. for 2 hr. The reaction mixture was concentrated under reduced pressure, and the residue was dissolved in THF (3 mL). 28% Aqueous ammonia (2 mL, 22.87 mmol) was added to the THF solution, and the mixture was stirred at room temperature for 14 hr. The reaction mixture was poured into water, and the precipitate was collected by filtration to give 1-cyclohexyl-5-(4-fluorophenyl)-1H-pyrazole-4-carboxamide (284 mg, 0.988 mmol, 95%) as a white powder.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. dissolutionthe residue was dissolved in THF (3 mL)
  3. filtrationthe precipitate was collected by filtration

Sources & evidence

ORD record
ord-fd8e2da2ecf244da9ad2fc4727a9e6cb
Source dataset
uspto-grants-2015_10
Patent number
US09156837B2

Reaction notes

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