Water → 4,5-Difluoro-2-[[3-methyl-1-(2-pyridinyl)-1H-pyrazol-5-yl]amino]benzoic acid

HRID 497992Notes

Reaction equation

HRID 497992 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]=[C:22]([F:24])[C:21]([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>[F:24][C:22]1[C:21]([F:25])=[CH:20][C:16]([C:17]([OH:19])=[O:18])=[C:15]([NH:7][C:5]2[N:4]([C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=3)[N:3]=[C:2]([CH3:1])[CH:6]=2)[CH:23]=1

Participants

8

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 7351323-Methyl-1-(pyridin-2-yl)-1H-pyrazol-5-amineHCID 7371712-Chloro-4,5-difluorobenzoic acid

Product 1

HCID 223201954,5-Difluoro-2-[[3-methyl-1-(2-pyridinyl)-1H-pyrazol-5-yl]amino]benzoic acidYield 81%

Reagents, catalysts & solvents 3

HCID 8895Cupric acetateCatalystHCID 176Acetic AcidSolventHCID 6228DimethylformamideSolvent

Procedure

Under an argon atmosphere, a solution of 3-methyl-1-(2-pyridinyl)-1H-pyrazol-5-ylamine (6.01 g, 34.5 mmol), 2-chloro-4,5-difluorobenzoic acid (6.64 g, 34.5 mmol), copper acetate (II) (0.718 g, 3.95 mmol) and potassium carbonate (4.77 g, 34.5 mmol) in N,N-dimethylformamide (30 mL) was heated under reflux for 2 hours. The solution was cooled to room temperature, and poured into water. The solution was made weakly 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 (9.21 g, 81% yield).

Workup

  1. temperatureunder reflux for 2 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-93562eff33dc4f0482610bb09e6b1e61
Source dataset
uspto-grants-2005_09
Patent number
US06949648B2

Reaction notes

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