Hydrogen Peroxide → 5-amino-3-(pyridin-3-ylamino)-1H-pyrazole-4-carboxamide

HRID 2202615Notes

Reaction equation

HRID 2202615 reaction equation
[NH2:1][C:2]1[NH:6][N:5]=[C:4]([NH:7][C:8]2[CH:9]=[N:10][CH:11]=[CH:12][CH:13]=2)[C:3]=1[C:14]#[N:15].C(=O)([O-])[O-:17].[K+].[K+].OO>CS(C)=O>[NH2:1][C:2]1[NH:6][N:5]=[C:4]([NH:7][C:8]2[CH:9]=[N:10][CH:11]=[CH:12][CH:13]=2)[C:3]=1[C:14]([NH2:15])=[O:17]

Participants

5

Reactant 3

HCID 784Hydrogen Peroxide2×HCID 11430Potassium CarbonateHCID 86698958HCID 86698958, compound

Product 1

HCID 866989595-amino-3-(pyridin-3-ylamino)-1H-pyrazole-4-carboxamide

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Dissolved 5-amino-3-(pyridin-3-ylamino)-1H-pyrazole-4-carbonitrile (100 mg) in DMSO (5 mL), added potassium carbonate (0.50 eq., 50 mg), then added hydrogen peroxide solution (40 uL of 50% solution in H2O) dropwise over ice bath over the course of 10 minutes. After the final addition, kept on ice bath for 2 hrs, then heated to room temperature and stirred until complete by TLC. After 24 hrs, reaction was incomplete so additional (120 uL) hydrogen peroxide was added and reaction was heated to 50 degrees C. Reaction was complete by TLC after 3 days of stirring at 50 degrees C. and was poured into 20 mL of ice water but no precipitate was observed. Extracted with EtOAc three times, washed with brine and dried with MgSO4. Volatiles were removed via vacuo. 5-amino-3-(pyridin-3-ylamino)-1H-pyrazole-4-carboxamide was obtained as a brown oil (100 mg, 92% yield).

Workup

  1. customover the course of 10 minutes
  2. additionAfter the final addition
  3. waitAfter 24 hrs
  4. customreaction
  5. additionwas added
  6. customreaction
  7. temperaturewas heated to 50 degrees C
  8. customReaction
  9. waitwas complete by TLC after 3 days
  10. stirringof stirring at 50 degrees C
  11. extractionExtracted with EtOAc three times
  12. washwashed with brine
  13. dry with materialdried with MgSO4
  14. customVolatiles were removed via vacuo

Sources & evidence

ORD record
ord-43e23a66c0634221ad6116233b3edfda
Source dataset
uspto-grants-2016_06
Patent number
US09365556B2

Reaction notes

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