Benzaldehyde → HCID 178513732, compound

HRID 1405125Notes

Reaction equation

HRID 1405125 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]([NH2:16])=[O:15].[CH:17](=O)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.N1CCCCC1>C(O)C>[CH:17](=[N: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]([NH2:16])=[O:15])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 240BenzaldehydeHCID 8082PiperidineHCID 866989595-amino-3-(pyridin-3-ylamino)-1H-pyrazole-4-carboxamide

Product 1

HCID 178513732HCID 178513732, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

5-amino-3-(pyridin-3-ylamino)-1H-pyrazole-4-carboxamide (1.0 g) was suspended in 10 mL of ethanol and benzaldehyde (463 μL, 1.0 eq.) and piperidine (0.10 eq, 47 μL) was added. Stirred the reaction at reflux until starting material was absent and confirmed by HPLC. After reaction was complete (18 hrs) it was brought to room temperature and filtered to obtain 5-(benzylideneamino)-3-(pyridin-3-ylamino)-1H-pyrazole-4-carboxamide as a yellow to orange powder. The product was washed with ethanol to remove any excess benzaldehyde. Product was allowed to dry under vacuum for 1 hr (800 mg, 57% yield).

Workup

  1. customthe reaction
  2. temperatureat reflux
  3. customAfter reaction
  4. custom(18 hrs) it
  5. customwas brought to room temperature
  6. filtrationfiltered

Sources & evidence

ORD record
ord-829c5077c47f4b50a0591ed9bcc0c4b7
Source dataset
uspto-grants-2014_12
Patent number
US08916555B2

Reaction notes

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