2-Pyrazinecarboxylic acid → HCID 178522717, compound

HRID 414448Notes

Reaction equation

HRID 414448 reaction equation
[N:1]1[CH:6]=[CH:5][N:4]=[CH:3][C:2]=1[C:7]([OH:9])=O.[NH2:10][C:11]1[NH:15][N:14]=[N:13][N:12]=1>O1CCCC1.C(N(CC)CC)C.C(Cl)(=O)OCC>[NH:12]1[C:11]([NH:10][C:7]([C:2]2[CH:3]=[N:4][CH:5]=[CH:6][N:1]=2)=[O:9])=[N:15][N:14]=[N:13]1

Participants

6

Reactant 2

HCID 10472-Pyrazinecarboxylic acidHCID 178509299HCID 178509299, compound

Product 1

HCID 178522717HCID 178522717, compound

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolventHCID 10928Ethyl chloroformateSolvent

Procedure

To a suspension of 1.50 g of pyrazine-2-carboxylic acid in 50 ml of tetrahydrofuran, 1.85 ml of triethylamine and 1.27 ml of ethyl chlorocarbonate were added dropwise successively at 0° C. under stirring. After stirring for 30 minutes at 0° C., 1.35 g of 5-amino-1H-tetrazole was added to the mixture, and the reaction mixture was stirred for 28.5 hours at room temperature. The precipitate was collected by filtration, and washed with dilute hydrochloric acid affording 2.05 g as colorless crystals, which was recrystalized from dimethylsulfoxide giving colorless crystals, m.p. 291°-296 ° C. (decomp.).

Workup

  1. additionwere added dropwise successively at 0° C.
  2. stirringAfter stirring for 30 minutes at 0° C.
  3. stirringthe reaction mixture was stirred for 28.5 hours at room temperature
  4. filtrationThe precipitate was collected by filtration
  5. washwashed with dilute hydrochloric acid affording 2.05 g as colorless crystals, which
  6. customwas recrystalized from dimethylsulfoxide giving colorless crystals, m.p. 291°-296 ° C. (decomp.)

Sources & evidence

ORD record
ord-1debadb719dd4fa3ab1774888bbb236a
Source dataset
uspto-grants-1988_12
Patent number
US04792547

Reaction notes

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