Pyrazole → HCID 66599064, compound

HRID 1889039Notes

Reaction equation

HRID 1889039 reaction equation
[NH:1]1[CH:5]=[CH:4][CH:3]=[N:2]1.[H-].[Na+].Br[C:9]1[N:13]2[CH2:14][CH2:15][N:16]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:17][C:12]2=[N:11][N:10]=1>CN(C)C=O>[N:1]1([C:9]2[N:13]3[CH2:14][CH2:15][N:16]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:17][C:12]3=[N:11][N:10]=2)[CH:5]=[CH:4][CH:3]=[N:2]1

Participants

5

Reactant 3

HCID 1048PyrazoleHCID 24758Sodium hydrideHCID 17998723tert-butyl 3-bromo-5H,6H,7H,8H-(1,2,4)triazolo(4,3-a)pyrazine-7-carboxylate

Product 1

HCID 66599064HCID 66599064, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of pyrazole (33.7 mg, 0.495 mmol) and sodium hydride (19.79 mg, 0.495 mmol) in N,N-dimethylformamide (DMF) (1 ml) was cooled to 0° C. and 1,1-dimethylethyl 3-bromo-5,6-dihydro[1,2,4]triazolo[4,3-a]pyrazine-7(8H)-carboxylate (50 mg, 0.165 mmol, commercially available from e.g. Allichem, Ark Pharm or Bepharm) was added. After completion of the addition, the mixture was stirred at room temp for 30 mins and then at 110° C. After 3 h, the DMF was evaporated and a few drops of NH4Cl solution were added followed by ethyl acetate (50 ml). The solution was dried (Na2SO4), filtered and concentrated. The product was purified by MDAP to give desired product in 24.1 mg.

Workup

  1. additionAfter completion of the addition
  2. customat 110° C
  3. waitAfter 3 h
  4. customthe DMF was evaporated
  5. additiona few drops of NH4Cl solution were added
  6. dry with materialThe solution was dried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe product was purified by MDAP

Sources & evidence

ORD record
ord-09feec7bc7c04c4bbe3effaa02127972
Source dataset
uspto-grants-2013_08
Patent number
US08501946B2

Reaction notes

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