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

HRID 604816Notes

Reaction equation

HRID 604816 reaction equation
[CH3:1][C:2]1[C:3]([C:8]([OH:10])=O)=[N:4][CH:5]=[CH:6][N:7]=1.[CH2:11]([C:15]1[CH:16]=[C:17]([CH:19]=[CH:20][C:21]=1[CH:22]([C:27]([F:30])([F:29])[F:28])[C:23]([F:26])([F:25])[F:24])[NH2:18])[CH:12]([CH3:14])[CH3:13].[I-].ClC1C=CC=C[N+]=1C.C(N(CC)CC)C>O1CCCC1.C(OCC)(=O)C>[CH2:11]([C:15]1[CH:16]=[C:17]([NH:18][C:8]([C:3]2[C:2]([CH3:1])=[N:7][CH:6]=[CH:5][N:4]=2)=[O:10])[CH:19]=[CH:20][C:21]=1[CH:22]([C:27]([F:28])([F:29])[F:30])[C:23]([F:24])([F:25])[F:26])[CH:12]([CH3:14])[CH3:13]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 1670692-Chloro-1-methylpyridinium iodideHCID 131534683-Methylpyrazine-2-carboxylic acidHCID 866190043-Isobutyl-4-[2,2,2-trifluoro-1-(trifluoromethyl)ethyl]aniline

Product 1

HCID 11690266N-{3-isobutyl-4-[2,2,2-trifluoro-1-(trifluoromethyl)ethyl]phenyl}-3-methyl-pyrazine-2-carboxamideYield 69.2%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

3-Methylpyrazine-2-carboxylic acid (138 mg, 1 mmol), 3-isobutyl-4-[2,2,2-trifluoro-1-(trifluoromethyl)ethyl]aniline (299 mg, 1 mmol), 2-chloro-1-methylpyridinium iodide (255 mg, 1 mmol) and triethylamine (303 mg, 3 mmol) were dissolved in tetrahydrofuran (10 ml) and refluxed under heating for 3 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 residue was purified by using silica gel chromatography (hexane:ethyl acetate=2:1) to obtain 290 mg of the desired compound.

Workup

  1. temperaturerefluxed
  2. temperatureunder heating for 3 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 residue was purified

Sources & evidence

ORD record
ord-aba4b53984ad4b8c93a00d1e67bb4def
Source dataset
uspto-grants-2011_03
Patent number
US07910735B2

Reaction notes

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