2-Pyrazinecarboxylic acid → HCID 178513619, compound

HRID 2121355Notes

Reaction equation

HRID 2121355 reaction equation
[NH2:1][C:2]1[C:10]([NH2:11])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([NH2:6])=[O:5].C(N(CC)CC)C.[N:19]1[CH:24]=[CH:23][N:22]=[CH:21][C:20]=1[C:25](O)=O.ON1C2C=CC=CC=2N=N1.CN(C)CCCN=C=NCC>CN(C)C=O>[N:19]1[CH:24]=[CH:23][N:22]=[CH:21][C:20]=1[C:25]1[NH:1][C:2]2[C:3]([C:4]([NH2:6])=[O:5])=[CH:7][CH:8]=[CH:9][C:10]=2[N:11]=1

Participants

7

Reactant 5

HCID 10472-Pyrazinecarboxylic acidHCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 104870292,3-Diaminobenzamide

Product 1

HCID 178513619HCID 178513619, compoundYield 61.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 1.68 g (7.5 mmol) of 2,3-diaminobenzamide and 3.04 g (30 mmol) of triethylamine in 50 ml of dimethylformamide was stirred at room temperature for 1 hour. 0.93 g (7.5 mmol) of pyrazine-2-carboxylic acid and 1.01 g (7.5 mmol) of N-hydroxybenzotriazole (HOBt) were added. After stirring at room temp. for 15 minutes, the mixture was cooled to 0° C. 1.44 g (7.5 mmol) of N′-(3-dimethylaminopropyl)-N-ethylcarbodiimide (EDC) were added, and the mixture was stirred at room temp. for 16 hours. The reaction mixture was then concentrated in vacuo. The residue was partitioned between methylene chloride and saturated sodium bicarbonate solution. The aqueous phase was extracted with methylene chloride. The combined organic phases were dried over magnesium sulfate. The residue obtained after concentration in vacuo was taken up in 50 ml of glacial acetic acid and refluxed for 30 minutes. The reaction mixture was concentrated in vacuo, and the residue was stirred in diethyl ether. The precipitate was removed by filtration and dried at 40° C. in vacuo. 1.11 g of brown crystals were obtained.

Workup

  1. stirringthe mixture was stirred at room temp. for 16 hours
  2. concentrationThe reaction mixture was then concentrated in vacuo
  3. customThe residue was partitioned between methylene chloride and saturated sodium bicarbonate solution
  4. extractionThe aqueous phase was extracted with methylene chloride
  5. dry with materialThe combined organic phases were dried over magnesium sulfate
  6. customThe residue obtained
  7. concentrationafter concentration in vacuo
  8. temperaturerefluxed for 30 minutes
  9. concentrationThe reaction mixture was concentrated in vacuo
  10. stirringthe residue was stirred in diethyl ether
  11. customThe precipitate was removed by filtration
  12. customdried at 40° C. in vacuo

Sources & evidence

ORD record
ord-5c3308a3cbd3497a9b53c215226b178c
Source dataset
uspto-grants-2004_02
Patent number
US06696437B1

Reaction notes

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