Water → N-(4'-chlorobiphenyl-2-yl)-3-trifluoromethyl-pyrazine-2-carboxamide

HRID 1919479Notes

Reaction equation

HRID 1919479 reaction equation
C(N(CC)CC)C.[Cl:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[NH2:21])=[CH:11][CH:10]=1.[F:22][C:23]([F:34])([F:33])[C:24]1[C:25]([C:30](Cl)=[O:31])=[N:26][CH:27]=[CH:28][N:29]=1.O>C1COCC1>[Cl:8][C:9]1[CH:10]=[CH:11][C:12]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[NH:21][C:30]([C:25]2[C:24]([C:23]([F:33])([F:22])[F:34])=[N:29][CH:28]=[CH:27][N:26]=2)=[O:31])=[CH:13][CH:14]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 2622612-Amino-4'-chlorobiphenylHCID 871347812-Pyrazinecarbonyl chloride, 3-(trifluoromethyl)-

Product 1

HCID 66751032N-(4'-chlorobiphenyl-2-yl)-3-trifluoromethyl-pyrazine-2-carboxamideYield 85%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Triethylamine (0.32 g: 1.5 mmole) was added to a solution of 4′-chlorobiphenyl-2-ylamine (0.3 g: 1.5 mmole) and 3-trifluoromethylpyrazine-2-carboxylic acid chloride (0.32 g: 1.5 mmole) in THF (10 mL), followed by stirring at room temperature for 2 hours. Water was added to the reaction mixture to suspend the reaction, followed by extraction with ethyl acetate. The ethyl acetate layer was dried over anhydrous sodium sulfate and concentrated in vacuo, and the residue was purified by silica gel column chromatography to give the subject compound (0.47 g).

Workup

  1. customthe reaction
  2. extractionfollowed by extraction with ethyl acetate
  3. dry with materialThe ethyl acetate layer was dried over anhydrous sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-3fc1a1ebd7174e0e81979d453b229a3f
Source dataset
uspto-grants-2012_05
Patent number
US08168638B2

Reaction notes

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