Potassium Carbonate → HCID 69084095, compound

HRID 1023418Notes

Reaction equation

HRID 1023418 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]([C:13]3[CH:18]=[CH:17][N:16]=[C:15]([NH2:19])[CH:14]=3)=[CH:11][C:10]([C:20]([F:23])([F:22])[F:21])=[N:9]2)=[CH:4][CH:3]=1.[C:24]([N:32]=C=O)(=[O:31])C1C=CC=CC=1.C(=O)([O-])[O-].[K+].[K+]>C(Cl)Cl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]([C:13]3[CH:18]=[CH:17][N:16]=[C:15]([NH:19][C:24]([NH2:32])=[O:31])[CH:14]=3)=[CH:11][C:10]([C:20]([F:21])([F:22])[F:23])=[N:9]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 78210Benzoyl isocyanateHCID 69083646HCID 69083646, compound

Product 1

HCID 69084095HCID 69084095, compoundYield 14%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
50 °C

Procedure

4-[2-(4-Fluoro-phenyl)-5-trifluoromethyl-2H-pyrazol-3-yl]-pyridin-2-ylamine (132 mg, 0.41 mmol) and benzoyl isocyanate (120 mg, 0.82 mmol) are mixed in DCM (4.0 mL) and the reaction mixture is heated at 50° C. for 16 hrs. After it is cooled down, the solvent is removed and the residue is dissolved in ethanol (2.5 mL). Potassium carbonate (70 mg, 0.49 mmol) is added and the reaction mixture is heated at 85° C. for 2 hrs before it is cooled down to room temperature. The solvent is removed and the residue is partitioned between water (30 mL) and EtOAc (50 mL). The organic layer is separated and concentrated to give the crude product. Purification by flash column chromatography using MeOH in DCM (gradient from 0% to 10%) affords 21 mg of the titled product.

Workup

  1. temperatureAfter it is cooled down
  2. customthe solvent is removed
  3. dissolutionthe residue is dissolved in ethanol (2.5 mL)
  4. temperaturethe reaction mixture is heated at 85° C. for 2 hrs before it
  5. temperatureis cooled down to room temperature
  6. customThe solvent is removed
  7. customthe residue is partitioned between water (30 mL) and EtOAc (50 mL)
  8. customThe organic layer is separated
  9. concentrationconcentrated
  10. customto give the crude product
  11. customPurification by flash column chromatography

Sources & evidence

ORD record
ord-4c6ab66b32ab4812980b0c166f700aa3
Source dataset
uspto-grants-2014_05
Patent number
US08722709B2

Reaction notes

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