6-(Piperidin-1-yl)pyrazine-2-carboxylic acid → HCID 178522719, compound

HRID 414455Notes

Reaction equation

HRID 414455 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][CH2:4][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][CH2:4][CH2:5][CH2:6]1

Participants

6

Reactant 2

HCID 12825406-(Piperidin-1-yl)pyrazine-2-carboxylic acidHCID 178509299HCID 178509299, compound

Product 1

HCID 178522719HCID 178522719, compound

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolventHCID 62493Pivaloyl chlorideSolvent

Procedure

To a suspension fo 1.28 g of 6-(1-piperidinyl) pyrazine-2-carboxylic acid in 18 ml of tetrahydrofuran, 0.95 ml of triethylamine and 0.84 ml of pivaloyl chloride were added dropwise successively at 0 ° C. under stirring. After stirring for 1 hour at 0 ° C., 0.58 g of 5-amino-1H-tetrazole was added to the mixture, and the reaction mixture was stirred for 30 minutes 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 0.55 g of the desired compound as yellow columns. 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 30 minutes 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 0.55 g of the desired compound as yellow columns

Sources & evidence

ORD record
ord-ae69f077e70c41669af0d3b2dac91c0e
Source dataset
uspto-grants-1988_12
Patent number
US04792547

Reaction notes

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