2-Pyrazinecarboxylic acid → N-Methoxy-N-methylpyrazine-2-carboxamide

HRID 577834

Reaction equation

HRID 577834 reaction equation
[N:1]1[CH:6]=[CH:5][N:4]=[CH:3][C:2]=1[C:7]([OH:9])=O.C(Cl)(=O)C(Cl)=O.Cl.[CH3:17][NH:18][O:19][CH3:20].C(N(CC)CC)C>C(Cl)Cl.CN(C=O)C>[CH3:20][O:19][N:18]([CH3:17])[C:7]([C:2]1[CH:3]=[N:4][CH:5]=[CH:6][N:1]=1)=[O:9]

Participants

7

Reactant 4

HCID 10472-Pyrazinecarboxylic acidHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)

Product 1

HCID 22613131N-Methoxy-N-methylpyrazine-2-carboxamideYield 92.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a 500 ml round bottom flask, pyrazine-2-carboxylic acid (58 g, 467.37 mmol) was suspended in dry CH2Cl2 (250 ml): oxalyl chloride (50.1 ml, 560.85 mmol) was added along with a few drops of DMF, and the mixture was stirred at room temperature for 12 hours. N,O-Dimethylhydroxylamine hydrochloride (54.7 g, 560.85 mmol) was added, and the resultant mixture was cooled down to 5° C. Triethylamine (195 ml, 1402.12 mmol) was added via a dropping funnel, and the reaction mixture was stirred at room temperature for 30 minutes before being filtered. The filter cake was washed with EtOAc, and the combined filtrate was washed with saturated sodium bicarbonate and brine, concentrated to an oil and dried under high vacuum to give the desired product (72 g).

Workup

  1. stirringthe reaction mixture was stirred at room temperature for 30 minutes
  2. filtrationbefore being filtered
  3. washThe filter cake was washed with EtOAc
  4. washthe combined filtrate was washed with saturated sodium bicarbonate and brine
  5. concentrationconcentrated to an oil
  6. customdried under high vacuum

Sources & evidence

ORD record
ord-720c37ba76b24097a3fe2d41606ddc87
Source dataset
uspto-grants-2015_05
Patent number
US09040528B2

Linked notes

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