Hydrochloric Acid → N-acetyl-N-{4-[1-methoxy-2,2,2-trifluoro-1-(trifluoromethyl)ethyl]-2-methyl-5-n-propylphenyl}-1,3,5-trimethylpyrazole-4-carboxamide

HRID 1952264

Reaction equation

HRID 1952264 reaction equation
[H-].[Na+].[CH3:3][O:4][C:5]([C:14]1[C:19]([CH2:20][CH2:21][CH3:22])=[CH:18][C:17]([NH:23][C:24]([C:26]2[C:27]([CH3:33])=[N:28][N:29]([CH3:32])[C:30]=2[CH3:31])=[O:25])=[C:16]([CH3:34])[CH:15]=1)([C:10]([F:13])([F:12])[F:11])[C:6]([F:9])([F:8])[F:7].[C:35](OC(=O)C)(=[O:37])[CH3:36].Cl>O1CCCC1>[C:35]([N:23]([C:17]1[CH:18]=[C:19]([CH2:20][CH2:21][CH3:22])[C:14]([C:5]([O:4][CH3:3])([C:6]([F:9])([F:8])[F:7])[C:10]([F:13])([F:11])[F:12])=[CH:15][C:16]=1[CH3:34])[C:24]([C:26]1[C:27]([CH3:33])=[N:28][N:29]([CH3:32])[C:30]=1[CH3:31])=[O:25])(=[O:37])[CH3:36]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7918Acetic AnhydrideHCID 24758Sodium hydrideHCID 23628207N-{4-[1-methoxy-2,2,2-trifluoro-1-(trifluoromethyl)ethyl]-2-methyl-5-n-propylphenyl}-1,3,5-trimethylpyrazole-4-carboxamide

Product 1

HCID 86629857N-acetyl-N-{4-[1-methoxy-2,2,2-trifluoro-1-(trifluoromethyl)ethyl]-2-methyl-5-n-propylphenyl}-1,3,5-trimethylpyrazole-4-carboxamideYield 52%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

Sodium hydride (32 mg, 60%, 0.8 mmol) was suspended in tetrahydrofuran (10 ml), and a solution of N-{4-[1-methoxy-2,2,2-trifluoro-1-(trifluoromethyl)ethyl]-2-methyl-5-n-propylphenyl}-1,3,5-trimethylpyrazole-4-carboxamide (250 mg, 0.53 mmol) in tetrahydrofuran (5 ml) was added dropwise. After stirring at room temperature for 30 min, a solution of acetic anhydride (80 mg, 0.78 mmol) in tetrahydrofuran (2 ml) was added, and the mixture was stirred for one day. The reaction mixture was poured into diluted hydrochloric acid, and the mixture was extracted with ethyl acetate. The organic layer was washed with water, dried over magnesium sulfate and concentrated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:3) to give the desired compound (139 mg).

Workup

  1. stirringthe mixture was stirred for one day
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with water
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customthe obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:3)

Sources & evidence

ORD record
ord-0b048ce72b2a45008068e2adbcd3194e
Source dataset
uspto-grants-2013_03
Patent number
US08404861B2

Linked notes

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