3,5-Difluoro-4-hydroxybenzaldehyde → HCID 178513723, compound

HRID 2202638Notes

Reaction equation

HRID 2202638 reaction equation
[NH2:1][C:2]1[NH:6][N:5]=[C:4]([NH:7][C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([Cl:14])[CH:9]=2)[C:3]=1[C:15]([NH2:17])=[O:16].[F:18][C:19]1[CH:20]=[C:21]([CH:24]=[C:25]([F:28])[C:26]=1[OH:27])[CH:22]=O>CCO.N1CCCCC1>[Cl:14][C:10]1[CH:9]=[C:8]([NH:7][C:4]2[C:3]([C:15]([NH2:17])=[O:16])=[C:2]([N:1]=[CH:22][C:21]3[CH:20]=[C:19]([F:18])[C:26]([OH:27])=[C:25]([F:28])[CH:24]=3)[NH:6][N:5]=2)[CH:13]=[CH:12][CH:11]=1

Participants

5

Reactant 2

HCID 101925843,5-Difluoro-4-hydroxybenzaldehydeHCID 866989565-amino-3-((3-chlorophenyl)amino)-1H-pyrazole-4-carboxamide

Product 1

HCID 178513723HCID 178513723, compound

Reagents, catalysts & solvents 2

HCID 8082PiperidineCatalystHCID 702EthanolSolvent

Procedure

5-amino-3-((3-chlorophenyl)amino)-1H-pyrazole-4-carboxamide was then suspended in EtOH and 3,5-difluoro-4-hydroxybenzaldehyde (1 eq.) and piperidine (1 drop) 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 product as a yellow powder. Powder was washed with EtOH. 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
  6. customto obtain product as a yellow powder
  7. washPowder was washed with EtOH
  8. customto dry under vacuum for 1 hr

Sources & evidence

ORD record
ord-56a24256e399445d93089c4a2bd21ac9
Source dataset
uspto-grants-2016_06
Patent number
US09365556B2

Reaction notes

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