3-Hydroxybenzaldehyde → HCID 178513734, compound

HRID 1049199Notes

Reaction equation

HRID 1049199 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].[OH:17][C:18]1[CH:19]=[C:20]([CH:23]=[CH:24][CH:25]=1)[CH:21]=O>CCO.N1CCCCC1>[OH:17][C:18]1[CH:19]=[C:20]([CH:23]=[CH:24][CH:25]=1)[CH:21]=[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]

Participants

5

Reactant 2

HCID 1013-HydroxybenzaldehydeHCID 866989595-amino-3-(pyridin-3-ylamino)-1H-pyrazole-4-carboxamide

Product 1

HCID 178513734HCID 178513734, compoundYield 55%

Reagents, catalysts & solvents 2

HCID 8082PiperidineCatalystHCID 702EthanolSolvent

Procedure

5-amino-3-(pyridin-3-ylamino)-1H-pyrazole-4-carboxamide (1.0 g) was suspended in EtOH (10 mL) and 3-hydroxybenzaldehyde (559 mg, 1 eq.) and piperidine (10 drops) were added. Stirred at reflux until intermediate was absent (HPLC). After reaction was complete (18 hrs) it was brought to room temperature and filtered to obtain 5-((3-hydroxybenzylidene)amino)-3-(pyridin-3-ylamino)-1H-pyrazole-4-carboxamide as a yellow powder. Powder was washed with EtOH. Product was allowed to dry under vacuum for 1 hr (800 mg, 55% yield).

Workup

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

Sources & evidence

ORD record
ord-6ce9e233951045d8bc0c83f6b8f1888b
Source dataset
uspto-grants-2016_07
Patent number
US09382237B2

Reaction notes

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