Hydrochloric Acid → HCID 22320133, compound

HRID 498054Notes

Reaction equation

HRID 498054 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[N:7]1[C:11]([NH2:12])=[CH:10][CH:9]=[N:8]1.Cl[C:14]1[CH:22]=[C:21]([F:23])[C:20]([F:24])=[CH:19][C:15]=1[C:16]([OH:18])=[O:17].C(=O)([O-])[O-].[K+].[K+].Cl>CN(C)C=O.C([O-])(=O)C.[Cu+2].C([O-])(=O)C.O>[F:23][C:21]1[C:20]([F:24])=[CH:19][C:15]([C:16]([OH:18])=[O:17])=[C:14]([NH:12][C:11]2[N:7]([C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=3)[N:8]=[CH:9][CH:10]=2)[CH:22]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 7371712-Chloro-4,5-difluorobenzoic acidHCID 13007948HCID 13007948, compound

Product 1

HCID 22320133HCID 22320133, compoundYield 65.6%

Reagents, catalysts & solvents 3

HCID 8895Cupric acetateCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 1-(2-pyridinyl)-1H-pyrazol-5-ylamine (6.94 g, 43.3 mmol), 2-chloro-4,5-difluorobenzoic acid (10.0 g, 51.9 mmol), copper acetate (II) (0.787 g, 4.33 mmol) and potassium carbonate (5.98 g, 43.3 mmol) in N,N-dimethylformamide (40 mL) was heated under reflux under an argon atmosphere for 3 hours. The solution was allowed to cool to room temperature, and poured into water. The solution was made weakly acidic by the addition of 6N hydrochloric acid, and the resulting crude crystals were collected by filtration. The crystals were washed with water and air dried to give the title compound (8.99 g, 55% yield).

Workup

  1. temperatureunder reflux under an argon atmosphere for 3 hours
  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-48299844dc94414ea1a45cb3b76359c6
Source dataset
uspto-grants-2005_09
Patent number
US06949648B2

Reaction notes

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