4-Hydroxybenzaldehyde → HCID 178513709, compound

HRID 527288Notes

Reaction equation

HRID 527288 reaction equation
[C:1]1([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:6]=[CH:5][C:4]([NH:7][C:8]2[C:12]([C:13]([NH2:15])=[O:14])=[C:11]([NH2:16])[NH:10][N:9]=2)=[CH:3][CH:2]=1.[OH:23][C:24]1[CH:31]=[CH:30][C:27]([CH:28]=O)=[CH:26][CH:25]=1>CCO.N1CCCCC1>[C:1]1([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:6]=[CH:5][C:4]([NH:7][C:8]2[C:12]([C:13]([NH2:15])=[O:14])=[C:11]([N:16]=[CH:28][C:27]3[CH:30]=[CH:31][C:24]([OH:23])=[CH:25][CH:26]=3)[NH:10][N:9]=2)=[CH:3][CH:2]=1

Participants

5

Reactant 2

HCID 1264-HydroxybenzaldehydeHCID 86701888HCID 86701888, compound

Product 1

HCID 178513709HCID 178513709, compound

Reagents, catalysts & solvents 2

HCID 8082PiperidineCatalystHCID 702EthanolSolvent

Procedure

3-([1,1′-biphenyl]-4-ylamino)-5-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-([1,1′-biphenyl]-4-ylamino)-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-8c6330e25cd74115a5436c0b5473ac6d
Source dataset
uspto-grants-2016_05
Patent number
US09346792B2

Reaction notes

Loading…