4-Hydroxybenzaldehyde → HCID 178439213, compound

HRID 1049166Notes

Reaction equation

HRID 1049166 reaction equation
[NH2:1][C:2]1[NH:6][N:5]=[C:4]([NH:7][C:8]2[CH:13]=[CH:12][C:11]([CH:14]([CH3:16])[CH3:15])=[CH:10][CH:9]=2)[C:3]=1[C:17]([NH2:19])=[O:18].[OH:20][C:21]1[CH:28]=[CH:27][C:24]([CH:25]=O)=[CH:23][CH:22]=1.N1CCCCC1>C(O)C>[OH:20][C:21]1[CH:28]=[CH:27][C:24]([CH:25]=[N:1][C:2]2[NH:6][N:5]=[C:4]([NH:7][C:8]3[CH:9]=[CH:10][C:11]([CH:14]([CH3:16])[CH3:15])=[CH:12][CH:13]=3)[C:3]=2[C:17]([NH2:19])=[O:18])=[CH:23][CH:22]=1

Participants

5

Reactant 3

HCID 1264-HydroxybenzaldehydeHCID 8082PiperidineHCID 867018725-amino-3-((4-isopropylphenyl)amino)-1H-pyrazole-4-carboxamide

Product 1

HCID 178439213HCID 178439213, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

5-amino-3-((4-isopropylphenyl)amino)-1H-pyrazole-4-carboxamide (850 mg) was suspended in 15 mL of ethanol and 4-hydroxybenzaldehyde (601 mg, 1.5 eq.) and piperidine (0.50 eq, 168 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-((4-hydroxybenzylidene)amino)-3-((4-isopropylphenyl)amino)-1H-pyrazole-4-carboxamide as a yellow to orange powder. The product was washed with ethanol to remove any excess 4-hydroxybenzaldehyde. Product was allowed to dry under vacuum for 1 hr (1.15 g, 97% 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-f58dfb36e70a45e7b1fb9024adf777bb
Source dataset
uspto-grants-2016_07
Patent number
US09382237B2

Reaction notes

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