4-(Difluoromethoxy)-3-hydroxybenzaldehyde → HCID 136218058, compound

HRID 2202635Notes

Reaction equation

HRID 2202635 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)[CH:9]=2)[C:3]=1[C:15]([NH2:17])=O.FC(F)[O:20][C:21]1[CH:28]=[CH:27][C:24]([CH:25]=O)=[CH:23][C:22]=1O>CCO.N1CCCCC1>[C:3]([C:11]1[CH:12]=[CH:13][C:8]([NH:7][C:4]2[NH:5][N:6]=[C:2]([N:1]=[CH:25][C:24]3[CH:27]=[CH:28][C:21]([OH:20])=[CH:22][CH:23]=3)[C:3]=2[C:15]#[N:17])=[CH:9][CH:10]=1)([CH3:15])([CH3:4])[CH3:2]

Participants

5

Reactant 2

HCID 27582954-(Difluoromethoxy)-3-hydroxybenzaldehydeHCID 866989565-amino-3-((3-chlorophenyl)amino)-1H-pyrazole-4-carboxamide

Product 1

HCID 136218058HCID 136218058, 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 4-(difluoromethoxy)-3-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-f9186d9c420348f688bdff8c2a7ef999
Source dataset
uspto-grants-2016_06
Patent number
US09365556B2

Reaction notes

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