2-Pyrazinecarboxylic acid → N-(3-fluoro-4-((N-methoxy-N-methylamino)carbonyl)phenyl)pyrazine-2-carboxamide

HRID 13420Notes

Reaction equation

HRID 13420 reaction equation
[N:1]1[CH:6]=[CH:5][N:4]=[CH:3][C:2]=1[C:7]([OH:9])=O.Cl.C(N=C=NCCCN(C)C)C.[NH2:22][C:23]1[CH:34]=[CH:33][C:26]([C:27]([N:29]([O:31][CH3:32])[CH3:30])=[O:28])=[C:25]([F:35])[CH:24]=1>N1C=CC=CC=1>[F:35][C:25]1[CH:24]=[C:23]([NH:22][C:7]([C:2]2[CH:3]=[N:4][CH:5]=[CH:6][N:1]=2)=[O:9])[CH:34]=[CH:33][C:26]=1[C:27]([N:29]([O:31][CH3:32])[CH3:30])=[O:28]

Participants

5

Reactant 3

HCID 10472-Pyrazinecarboxylic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 231456994-amino-2-fluoro-N-methoxy-N-methylbenzamide

Product 1

HCID 23145190N-(3-fluoro-4-((N-methoxy-N-methylamino)carbonyl)phenyl)pyrazine-2-carboxamide

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

2.56 g of pyrazine-2-carboxylic acid and 4.66 g of 1-ethyl-3-(3′-dimethylaminopropyl)-carbodiimide hydrochloride were added to a pyridine (20 ml) solution of 3.7 g of 4-amino-2-fluoro-N-methoxy-N-methylbenzamide, and the reaction liquid was stirred at room temperature for 1 hour. Pyridine was evaporated away under reduced pressure, and the residue was diluted with ethyl acetate, washed with water, and dried with anhydrous magnesium sulfate. The solvent was evaporated away under reduced pressure, and the resulting solid was washed with a mixed solvent of ethyl acetate and hexane to obtain the entitled compound as a pale yellow solid.

Workup

  1. customthe reaction liquid
  2. customPyridine was evaporated away under reduced pressure
  3. additionthe residue was diluted with ethyl acetate
  4. washwashed with water
  5. dry with materialdried with anhydrous magnesium sulfate
  6. customThe solvent was evaporated away under reduced pressure
  7. washthe resulting solid was washed with a mixed solvent of ethyl acetate and hexane

Sources & evidence

ORD record
ord-f2e8ac05eb444e859d33d2bdfc902757
Source dataset
uspto-grants-2010_06
Patent number
US07728025B2

Reaction notes

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