Triethylamine → N,N,5-Trimethyl-3-oxo-4-[3-(trifluoromethyl)phenyl]-3,4-dihydropyrazine-2-carboxamide

HRID 1958298Notes

Reaction equation

HRID 1958298 reaction equation
[CH3:1][C:2]1[N:3]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:21])([F:20])[F:19])[CH:13]=2)[C:4](=[O:11])[C:5]([C:8](O)=[O:9])=[N:6][CH:7]=1.[CH3:22][N:23](C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)[CH3:24].F[P-](F)(F)(F)(F)F.CCN(CC)CC.Cl.CNC>CN(C=O)C.O>[CH3:22][N:23]([CH3:24])[C:8]([C:5]1[C:4](=[O:11])[N:3]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:20])([F:21])[F:19])[CH:13]=2)[C:2]([CH3:1])=[CH:7][N:6]=1)=[O:9]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 10473Dimethylamine, hydrochlorideHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 667387495-Methyl-3-oxo-4-[3-(trifluoromethyl)phenyl]-3,4-dihydropyrazine-2-carboxylic acid

Product 1

HCID 66738834N,N,5-Trimethyl-3-oxo-4-[3-(trifluoromethyl)phenyl]-3,4-dihydropyrazine-2-carboxamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 5-methyl-3-oxo-4-[3-(trifluoromethyl)phenyl]-3,4-dihydropyrazine-2-carboxylic acid (0.21 g, 0.7 mmol), HATU (0.266 g, 0.7 mmol) and Et3N (0.293 g, 2.9 mmol) in DMF (2 ml) was reacted with dimethylamine HCl. After 2 h, the reaction mixture was diluted with water and extracted with ethyl acetate (3×5 ml). The organic phase was dried (MgSO4), filtered and evaporated. No further purification was performed.

Workup

  1. extractionextracted with ethyl acetate (3×5 ml)
  2. dry with materialThe organic phase was dried (MgSO4)
  3. filtrationfiltered
  4. customevaporated
  5. customNo further purification

Sources & evidence

ORD record
ord-990f40a5b501402b95c76665386f8b4f
Source dataset
uspto-grants-2013_04
Patent number
US08410114B2

Reaction notes

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