4-Hydroxybenzaldehyde → HCID 178513725, compound

HRID 527293Notes

Reaction equation

HRID 527293 reaction equation
[NH2:1][C:2]1[NH:6][N:5]=[C:4]([NH:7][C:8]2[CH:16]=[CH:15][C:11]([C:12]([OH:14])=[O:13])=[CH:10][CH:9]=2)[C:3]=1[C:17](=[O:19])[NH2:18].[OH:20][C:21]1[CH:28]=[CH:27][C:24]([CH:25]=O)=[CH:23][CH:22]=1>CCO.N1CCCCC1>[C:17]([C:3]1[C:4]([NH:7][C:8]2[CH:16]=[CH:15][C:11]([C:12]([OH:14])=[O:13])=[CH:10][CH:9]=2)=[N:5][NH:6][C:2]=1[N:1]=[CH:25][C:24]1[CH:27]=[CH:28][C:21]([OH:20])=[CH:22][CH:23]=1)(=[O:19])[NH2:18]

Participants

5

Reactant 2

HCID 1264-HydroxybenzaldehydeHCID 86701896HCID 86701896, compound

Product 1

HCID 178513725HCID 178513725, compound

Reagents, catalysts & solvents 2

HCID 8082PiperidineCatalystHCID 702EthanolSolvent

Procedure

4-((5-amino-4-carbamoyl-1H-pyrazol-3-yl)amino)benzoic acid 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 4-((4-carbamoyl-5-((4-hydroxybenzylidene)amino)-1H-pyrazol-3-yl)amino)benzoic acid 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-b689c35d7aff409f931ec3757364af92
Source dataset
uspto-grants-2016_05
Patent number
US09346792B2

Reaction notes

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