Water → HCID 178482986, compound

HRID 414452Notes

Reaction equation

HRID 414452 reaction equation
[CH3:1][N:2]([CH3:12])[C:3]1[N:8]=[C:7]([C:9]([OH:11])=O)[CH:6]=[N:5][CH:4]=1.[NH2:13][C:14]1[NH:18][N:17]=[N:16][N:15]=1.O>O1CCCC1.C(N(CC)CC)C.C(Cl)(=O)C(C)(C)C>[CH3:12][N:2]([CH3:1])[C:3]1[N:8]=[C:7]([C:9]([NH:13][C:14]2[NH:18][N:17]=[N:16][N:15]=2)=[O:11])[CH:6]=[N:5][CH:4]=1

Participants

7

Reactant 3

HCID 962WaterHCID 12825366-(dimethylamino)pyrazine-2-carboxylic acidHCID 178509299HCID 178509299, compound

Product 1

HCID 178482986HCID 178482986, compound

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolventHCID 62493Pivaloyl chlorideSolvent

Procedure

To a suspension of 0.58 g of 6-(dimethylamino)pyrazine-2-carboxylic acid in 10 ml of tetrahydrofuran, 0.53 ml of triethylamine and 0.47 ml of pivaloyl chloride were added dropwise successively at 0 ° C. under stirring. After stirring for 1 hour at 0 ° C., 0.33 g of 5-amino-1H-tetrazole was added to the mixture, and the reaction mixture was stirred for 1 hour at room temperature, and then refluxed for 6 hours. After cooling, 70 ml of water was added to the reaction mixture. The precipitate was collected by filtration, and recrystalized from a mixture of dimethylsulfoxide and methanol affording 0.36 g of the desired compound as yellow needles. The obtained crystal was consistent with that of (a).

Workup

  1. additionwere added dropwise successively at 0 ° C.
  2. stirringAfter stirring for 1 hour at 0 ° C.
  3. stirringthe reaction mixture was stirred for 1 hour at room temperature
  4. temperaturerefluxed for 6 hours
  5. temperatureAfter cooling
  6. filtrationThe precipitate was collected by filtration
  7. customrecrystalized from a mixture of dimethylsulfoxide and methanol affording 0.36 g of the desired compound as yellow needles

Sources & evidence

ORD record
ord-f7b776dccfd146849e7c1a836c1dfa92
Source dataset
uspto-grants-1988_12
Patent number
US04792547

Reaction notes

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