6-morpholin-4-ylpyrazine-2-carboxylic Acid → HCID 178522722, compound

HRID 414460Notes

Reaction equation

HRID 414460 reaction equation
[N:1]1([C:7]2[N:12]=[C:11]([C:13]([OH:15])=O)[CH:10]=[N:9][CH:8]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[NH2:16][C:17]1[NH:21][N:20]=[N:19][N:18]=1>O1CCCC1.C(N(CC)CC)C.C(Cl)(=O)C(C)(C)C>[N:1]1([C:7]2[N:12]=[C:11]([C:13]([NH:16][C:17]3[NH:21][N:20]=[N:19][N:18]=3)=[O:15])[CH:10]=[N:9][CH:8]=2)[CH2:2][CH2:3][O:4][CH2:5][CH2:6]1

Participants

6

Reactant 2

HCID 27625626-morpholin-4-ylpyrazine-2-carboxylic AcidHCID 178509299HCID 178509299, compound

Product 1

HCID 178522722HCID 178522722, compound

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolventHCID 62493Pivaloyl chlorideSolvent

Procedure

To a suspension of 2.50 g of 6-(4-morpholinyl) pyrazine-2-carboxylic acid in 50 ml of tetrahydrofuran, 3.60 ml of triethylamine and 1.60 ml of pivaloyl chloride were added dropwise successively at 0° C. under stirring. After stirring for 1 hour at 0° C., 1.12 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 12 hours. The reaction mixture was evaporated, and water was added to the residue. The precipitate was collected by filtration, and recrystalized from a mixture of dimethylsulfoxide and methanol affording 1.74 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 12 hours
  5. customThe reaction mixture was evaporated
  6. additionwater was added to the residue
  7. filtrationThe precipitate was collected by filtration
  8. customrecrystalized from a mixture of dimethylsulfoxide and methanol affording 1.74 g of the desired compound as yellow needles

Sources & evidence

ORD record
ord-f9395cf6d381407994d92ae65080620f
Source dataset
uspto-grants-1988_12
Patent number
US04792547

Reaction notes

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