Hydrochloric Acid → HCID 17862388, compound

HRID 644878Notes

Reaction equation

HRID 644878 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH:7]([N:10]=[C:11]=[O:12])([CH3:9])[CH3:8].[Cl:13][C:14]1[C:15]([O:24][C:25]2[C:29]([CH3:30])=[C:28]([CH3:31])[NH:27][N:26]=2)=[N:16][CH:17]=[C:18]([C:20]([F:23])([F:22])[F:21])[CH:19]=1.Cl>CN(C=O)C>[CH:7]([NH:10][C:11]([N:27]1[C:28]([CH3:31])=[C:29]([CH3:30])[C:25]([O:24][C:15]2[C:14]([Cl:13])=[CH:19][C:18]([C:20]([F:23])([F:22])[F:21])=[CH:17][N:16]=2)=[N:26]1)=[O:12])([CH3:9])[CH3:8]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 61277Isopropyl isocyanateHCID 17862374HCID 17862374, compound

Product 1

HCID 17862388HCID 17862388, compoundYield 48.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Potassium carbonate (0.62 g, 4.5 mmol) and isopropyl isocyanate (0.26 g, 3.0 mmol) were added to a solution of 3-(3-chloro-5-trifluoromethylpyridin-2-yloxy)-4,5-dimethylpyrazole (0.88 g, 3.0 mmol) in DMF (10 ml), and the mixture was stirred at room temperature for 6 hours. After completion of the reaction, the reaction mixture was poured into 2N hydrochloric acid and extracted with ethyl acetate (10 ml×3). An organic layer was washed with water, dried over anhydrous magnesium sulfate and filtered to remove a desiccant, and the solvent was distilled off from the filtrate under reduced pressure. The resultant crude product was purified with a silica gel column (ethyl acetate/hexane=1/5), to give a white solid of N-isopropyl-3-(3-chloro-5-trifluoromethylpyridin-2-yloxy)-4,5-dimethylpyrazole-1-carboxamide (0.55 g, yield: 48.7%) mp: 78-80° C.; 1H-NMR (CDCl3, TMS, ppm): δ 1.24 (d, J=6.6 Hz, 6H), 1.78 (s, 3H), 2.58 (s, 3H), 3.95-4.15 (m, 1H), 6.70-6.95 (m, 1H), 8.02 (d, J=2.1 Hz, 1H), 8.32 (m, 1H).

Workup

  1. customAfter completion of the reaction
  2. extractionextracted with ethyl acetate (10 ml×3)
  3. washAn organic layer was washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customto remove a desiccant, and the solvent
  7. distillationwas distilled off from the filtrate under reduced pressure
  8. customThe resultant crude product was purified with a silica gel column (ethyl acetate/hexane=1/5)

Sources & evidence

ORD record
ord-5c7434ab122445a1a0454a74209d58e6
Source dataset
uspto-grants-2010_04
Patent number
US07700786B2

Reaction notes

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