Hydrochloric Acid → N,N-diisopropyl-3-(3-chloro-5-trifluoromethylpyridin-2-yloxy)-5-methylpyrazole-1-carboxamide

HRID 644910Notes

Reaction equation

HRID 644910 reaction equation
[CH:1]([N:4]([CH:8]([CH3:10])[CH3:9])[C:5](Cl)=[O:6])([CH3:3])[CH3:2].[Cl:11][C:12]1[C:13]([O:22][C:23]2[CH:27]=[C:26]([CH3:28])[NH:25][N:24]=2)=[N:14][CH:15]=[C:16]([C:18]([F:21])([F:20])[F:19])[CH:17]=1.Cl>N1C=CC=CC=1>[CH:1]([N:4]([CH:8]([CH3:10])[CH3:9])[C:5]([N:25]1[C:26]([CH3:28])=[CH:27][C:23]([O:22][C:13]2[C:12]([Cl:11])=[CH:17][C:16]([C:18]([F:21])([F:20])[F:19])=[CH:15][N:14]=2)=[N:24]1)=[O:6])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 87890Diisopropylcarbamoyl chlorideHCID 178624573-(3-Chloro-5-trifluoromethylpyridin-2-yloxy)-5-methylpyrazole

Product 1

HCID 17862378N,N-diisopropyl-3-(3-chloro-5-trifluoromethylpyridin-2-yloxy)-5-methylpyrazole-1-carboxamideYield 86.7%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Conditions

Temperature
80 °C

Procedure

A solution of diisopropylcarbamoyl chloride (1.47 g, 9.0 mmol) in pyridine (5 ml) was added to a solution of 3-(3-chloro-5-trifluoromethylpyridin-2-yloxy)-5-methylpyrazole (1.67 g, 6.0 mmol) in pyridine (10 ml), and the mixture was stirred under heating at 80° C. for 20 hours. After completion of the reaction, the reaction mixture was poured into 2N hydrochloric acid, and the mixture was extracted with ethyl acetate (20 ml×3). An organic layer was washed with water, dried over anhydrous magnesium sulfate and filtered to remove a desiccant. 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,N-diisopropyl-3-(3-chloro-5-trifluoromethylpyridin-2-yloxy)-5-methylpyrazole-1-carboxamide (2.1 g, yield: 86.7%). mp: 58-60° C.; 1H-NMR (CDCl3, TMS, ppm): δ 1.28 (d, J=7.5 Hz, 12H), 2.29 (s, 3H), 3.50-4.10 (m, 2H), 6.00 (s, 1H), 7.98 (d, J=2.5 Hz, 1H), 8.31 (m, 1H).

Workup

  1. customAfter completion of the reaction
  2. extractionthe mixture was extracted with ethyl acetate (20 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
  7. distillationThe solvent was 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-8cfcb572e9d448e2988bffd0276fa8ae
Source dataset
uspto-grants-2010_04
Patent number
US07700786B2

Reaction notes

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