Water → HCID 22320171, compound

HRID 497980Notes

Reaction equation

HRID 497980 reaction equation
[CH3:1][C:2]1[CH:6]=[C:5]([NH2:7])[N:4]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=2)[N:3]=1.Cl[C:15]1[CH:23]=[CH:22][C:21]([C:24]([F:27])([F:26])[F:25])=[CH:20][C:16]=1[C:17]([OH:19])=[O:18].C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O.C([O-])(=O)C.[Cu+2].C([O-])(=O)C.C(O)(=O)C>[CH3:1][C:2]1[CH:6]=[C:5]([NH:7][C:15]2[CH:23]=[CH:22][C:21]([C:24]([F:25])([F:27])[F:26])=[CH:20][C:16]=2[C:17]([OH:19])=[O:18])[N:4]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=2)[N:3]=1

Participants

8

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 6881822-Chloro-5-(trifluoromethyl)benzoic acidHCID 7351323-Methyl-1-(pyridin-2-yl)-1H-pyrazol-5-amine

Product 1

HCID 22320171HCID 22320171, compoundYield 97.7%

Reagents, catalysts & solvents 3

HCID 8895Cupric acetateCatalystHCID 176Acetic AcidSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 3-methyl-1-(2-pyridinyl)-1H-pyrazol-5-ylamine (8.71 g, 50.0 mmol), 2-chloro-5-(trifluoromethyl)benzoic acid (12.4 g, 55.0 mmol), copper acetate (II) (1.00 g, 5.50 mmol) and potassium carbonate (7.60 g, 55.0 mmol) in N,N-dimethylformamide (50 mL) was heated under reflux for 1.5 hours under an argon atmosphere. The solution was cooled to room temperature, and poured into water. The solution was made acidic by the addition of acetic acid, and the resulting crude crystals were collected by filtration. The crystals were washed with water and air dried to give the title compound (17.7 g, 89% yield).

Workup

  1. temperatureunder reflux for 1.5 hours under an argon atmosphere
  2. filtrationthe resulting crude crystals were collected by filtration
  3. washThe crystals were washed with water and air
  4. customdried

Sources & evidence

ORD record
ord-c4abe00ecc1947dc8989074214a672f8
Source dataset
uspto-grants-2005_09
Patent number
US06949648B2

Reaction notes

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