4-Hydroxybenzaldehyde → HCID 178441007, compound

HRID 1405133Notes

Reaction equation

HRID 1405133 reaction equation
[NH2:1][C:2]1[NH:6][N:5]=[C:4]([NH:7][C:8]2[CH:13]=[CH:12][C:11]([C:14]([CH3:17])([CH3:16])[CH3:15])=[CH:10][CH:9]=2)[C:3]=1[C:18]([NH2:20])=[O:19].[OH:21][C:22]1[CH:29]=[CH:28][C:25]([CH:26]=O)=[CH:24][CH:23]=1>CCO.N1CCCCC1>[C:14]([C:11]1[CH:10]=[CH:9][C:8]([NH:7][C:4]2[C:3]([C:18]([NH2:20])=[O:19])=[C:2]([N:1]=[CH:26][C:25]3[CH:28]=[CH:29][C:22]([OH:21])=[CH:23][CH:24]=3)[NH:6][N:5]=2)=[CH:13][CH:12]=1)([CH3:17])([CH3:15])[CH3:16]

Participants

5

Reactant 2

HCID 1264-HydroxybenzaldehydeHCID 86701893HCID 86701893, compound

Product 1

HCID 178441007HCID 178441007, compound

Reagents, catalysts & solvents 2

HCID 8082PiperidineCatalystHCID 702EthanolSolvent

Procedure

5-amino-3-((4-(tert-butyl)phenyl)amino)-1H-pyrazole-4-carboxamide was then suspended in 8 mL EtOH and 4-hydroxybenzaldehyde (325 mg, 1 eq.) and piperidine (4 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 3-((4-(tert-butyl)phenyl)amino)-5-((4-hydroxybenzylidene)amino)-1H-pyrazole-4-carboxamide as a yellow powder. Powder was washed with EtOH to remove any excess 4-hydroxybenzaldehyde. Product was allowed to dry under vacuum for 1 hr.

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-417509f23fcf4b7eb29f1f3149ab2f6d
Source dataset
uspto-grants-2014_12
Patent number
US08916555B2

Reaction notes

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