4-(Trifluoromethyl)benzaldehyde → HCID 178510299, compound

HRID 2202620Notes

Reaction equation

HRID 2202620 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]#[N:16].[F:17][C:18]([F:28])([F:27])[C:19]1[CH:24]=[CH:23][C:22]([CH:25]=O)=[CH:21][CH:20]=1>CCO.N1CCCCC1>[Cl:14][C:10]1[CH:9]=[C:8]([NH:7][C:4]2[C:3]([C:15]#[N:16])=[C:2]([N:1]=[CH:25][C:22]3[CH:21]=[CH:20][C:19]([C:18]([F:17])([F:27])[F:28])=[CH:24][CH:23]=3)[NH:6][N:5]=2)[CH:13]=[CH:12][CH:11]=1

Participants

5

Reactant 2

HCID 679964-(Trifluoromethyl)benzaldehydeHCID 106811675-Amino-3-(3-chloro-phenylamino)-4-cyano-pyrazole

Product 1

HCID 178510299HCID 178510299, compoundYield 42%

Reagents, catalysts & solvents 2

HCID 8082PiperidineCatalystHCID 702EthanolSolvent

Procedure

5-amino-3-((3-chlorophenyl)amino)-1H-pyrazole-4-carbonitrile (100 mg) was suspended in EtOH (4 mL) and alpha,alpha,alpha-Trifluoro-p-tolualdehyde (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 A15 as a yellow powder. Powder was washed with EtOH. Product was allowed to dry under vacuum for 1 hr (71 mg, 42% yield).

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 A15 as a yellow powder
  7. washPowder was washed with EtOH
  8. customto dry under vacuum for 1 hr (71 mg, 42% yield)

Sources & evidence

ORD record
ord-12251530e15048df915bd75aab3374c5
Source dataset
uspto-grants-2016_06
Patent number
US09365556B2

Reaction notes

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