4-Hydroxybenzaldehyde → HCID 178482857, compound

HRID 1405098Notes

Reaction equation

HRID 1405098 reaction equation
[NH2:1][C:2]1[NH:6][N:5]=[C:4]([NH:7][C:8]2[CH:13]=[CH:12][C:11]([N: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>[CH3:16][N:14]([CH3:15])[C:11]1[CH:10]=[CH:9][C:8]([NH:7][C:4]2[C:3]([C:17]([NH2:19])=[O:18])=[C:2]([N:1]=[CH:25][C:24]3[CH:27]=[CH:28][C:21]([OH:20])=[CH:22][CH:23]=3)[NH:6][N:5]=2)=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 1264-HydroxybenzaldehydeHCID 8082PiperidineHCID 867018655-amino-3-((4-(dimethylamino)phenyl)amino)-1H-pyrazole-4-carboxamide

Product 1

HCID 178482857HCID 178482857, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

5-amino-3-((4-(dimethylamino)phenyl)amino)-1H-pyrazole-4-carboxamide (900 mg) was suspended in 10 mL of ethanol and 4-hydroxybenzaldehyde (634 mg, 1.5 eq.) and piperidine (0.25 eq., 89 μL) was added. The reaction was stirred at reflux until the starting material was absent and confirmed by HPLC. After the reaction was complete (18 hrs) it was brought to room temperature and filtered to obtain 3-((4-(dimethylamino)phenyl)amino)-5-((4-hydroxybenzylidene)amino)-1H-pyrazole-4-carboxamide t 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 (1.130 g, 90% yield).

Workup

  1. temperatureat reflux until the starting material
  2. custom(18 hrs) it
  3. customwas brought to room temperature
  4. filtrationfiltered

Sources & evidence

ORD record
ord-ddec3095e9d74777866036e3e69d99f7
Source dataset
uspto-grants-2014_12
Patent number
US08916555B2

Reaction notes

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