Triethylamine → N-{3-isobutyl-4-[2,2,2-trifluoro-1-(trifluoromethyl)ethyl]phenyl}-3-trifluoromethylpyrazine-2-carboxamide

HRID 2388635Notes

Reaction equation

HRID 2388635 reaction equation
[F:1][C:2]([F:13])([F:12])[C:3]1[C:4]([C:9]([OH:11])=O)=[N:5][CH:6]=[CH:7][N:8]=1.[CH2:14]([C:18]1[CH:19]=[C:20]([CH:22]=[CH:23][C:24]=1[CH:25]([C:30]([F:33])([F:32])[F:31])[C:26]([F:29])([F:28])[F:27])[NH2:21])[CH:15]([CH3:17])[CH3:16].[I-].ClC1C=CC=C[N+]=1C.C(N(CC)CC)C>C1COCC1.C(OCC)(=O)C>[CH2:14]([C:18]1[CH:19]=[C:20]([NH:21][C:9]([C:4]2[C:3]([C:2]([F:1])([F:13])[F:12])=[N:8][CH:7]=[CH:6][N:5]=2)=[O:11])[CH:22]=[CH:23][C:24]=1[CH:25]([C:30]([F:31])([F:32])[F:33])[C:26]([F:27])([F:28])[F:29])[CH:15]([CH3:17])[CH3:16]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 1670692-Chloro-1-methylpyridinium iodideHCID 536308603-(Trifluoromethyl)pyrazine-2-carboxylic acidHCID 866190043-Isobutyl-4-[2,2,2-trifluoro-1-(trifluoromethyl)ethyl]aniline

Product 1

HCID 86619011N-{3-isobutyl-4-[2,2,2-trifluoro-1-(trifluoromethyl)ethyl]phenyl}-3-trifluoromethylpyrazine-2-carboxamideYield 62%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

3-Trifluoromethyl-2-pyrazine carboxylic acid (192 mg, 1 mmol), 3-isobutyl-4-[2,2,2-trifluoro-1-(trifluoromethyl)ethyl]aniline (199 mg, 1 mmol), 2-chloro-1-methylpyridinium iodide (255 mg, 1 mmol) and triethylamine (303 mg, 3 mmol) were dissolved in THF (10 ml) and refluxed under heating for 2 hours. The reaction solution was diluted with ethyl acetate, followed by washing with water. The organic layer was dried over magnesium sulfate anhydride, and concentrated under reduced pressure, and then the solution was purified by using silica gel chromatography (hexane:ethyl acetate=2:1) to obtain 293 mg of the desired compound as paste state.

Workup

  1. temperaturerefluxed
  2. temperatureunder heating for 2 hours
  3. washby washing with water
  4. dry with materialThe organic layer was dried over magnesium sulfate anhydride
  5. concentrationconcentrated under reduced pressure
  6. customthe solution was purified

Sources & evidence

ORD record
ord-25b9b393f6b34b08ab3e150c6b3c814a
Source dataset
uspto-grants-2012_09
Patent number
US08269045B2

Reaction notes

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