2-Pyrazinecarboxylic acid → HCID 874157, compound

HRID 605227Notes

Reaction equation

HRID 605227 reaction equation
[N:1]1[CH:6]=[CH:5][N:4]=[CH:3][C:2]=1[C:7]([OH:9])=O.CCN(CC)CC.ClC(OCC)=O.[F:23][C:24]1[CH:30]=[CH:29][C:27]([NH2:28])=[CH:26][C:25]=1[N+:31]([O-:33])=[O:32]>C1COCC1>[F:23][C:24]1[CH:30]=[CH:29][C:27]([NH:28][C:7]([C:2]2[CH:3]=[N:4][CH:5]=[CH:6][N:1]=2)=[O:9])=[CH:26][C:25]=1[N+:31]([O-:33])=[O:32]

Participants

6

Reactant 4

HCID 10472-Pyrazinecarboxylic acidHCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 677684-Fluoro-3-nitroaniline

Product 1

HCID 874157HCID 874157, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
5 °C

Procedure

To a solution of pyrazine-2-carboxylic acid (2.00 g, 16.1 mmol) and Et3N (2.50 ml, 17.7 mmol) in THF (40 mL) was added ethyl chloroformate (1.74 mL, 17.7 mmol) dropwise at 5° C. and the mixture was stirred at 5° C. for 1 hour. 4-Fluoro-3-nitroaniline (2.80 g, 17.7 mmol) was added to the mixture at 5° C. The mixture was warmed to room temperature, stirred at room temperature for 4 hours, and then evaporated. The residue was suspended in a mixture of H2O (100 ml) and i-Pr2O (100 ml) and stirred at room temperature for 30 minutes. The resulting crystal was collected by filtration and washed with H2O and i-Pr2O to give the desired product as pale brown crystals (2.91 g, 69%).

Workup

  1. temperatureThe mixture was warmed to room temperature
  2. stirringstirred at room temperature for 4 hours
  3. customevaporated
  4. additionThe residue was suspended in a mixture of H2O (100 ml) and i-Pr2O (100 ml)
  5. stirringstirred at room temperature for 30 minutes
  6. filtrationThe resulting crystal was collected by filtration
  7. washwashed with H2O and i-Pr2O

Sources & evidence

ORD record
ord-aab0ed9c1055445e926baec6bd103489
Source dataset
uspto-grants-2011_03
Patent number
US07910595B2

Reaction notes

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