5-Amino-3-(3-chloro-phenylamino)-4-cyano-pyrazole → HCID 178510301, compound

HRID 527301Notes

Reaction equation

HRID 527301 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:35])([F:34])[C:19]1[CH:20]=[CH:21][C:22]([O:25][C:26]2[CH:33]=[CH:32][C:29]([CH:30]=O)=[CH:28][CH:27]=2)=[N:23][CH:24]=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:30][C:29]3[CH:28]=[CH:27][C:26]([O:25][C:22]4[CH:21]=[CH:20][C:19]([C:18]([F:35])([F:17])[F:34])=[CH:24][N:23]=4)=[CH:33][CH:32]=3)[NH:6][N:5]=2)[CH:13]=[CH:12][CH:11]=1

Participants

5

Reactant 2

HCID 106811675-Amino-3-(3-chloro-phenylamino)-4-cyano-pyrazoleHCID 269857004-{[5-(Trifluoromethyl)pyridin-2-yl]oxy}benzaldehyde

Product 1

HCID 178510301HCID 178510301, compoundYield 52%

Reagents, catalysts & solvents 2

HCID 8082PiperidineCatalystHCID 702EthanolSolvent

Procedure

5-amino-3-((3-chlorophenyl)amino)-1H-pyrazole-4-carbonitrile (100 mg) was then suspended in EtOH (4 mL) and 4-[{5-(Trifluoromethyl)pyridin-2-yl}oxy]benzaldehyde (230 mg, 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 3-((3-chlorophenyl)amino)-5-((4-((5-(trifluoromethyl)pyridin-2-yl)oxy)benzylidene)amino)-1H-pyrazole-4-carbonitrile as a yellow powder. Powder was washed with EtOH. Product was allowed to dry under vacuum for 1 hr (217 mg, 52% yield).

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-a23021d2f3a64eef9f83a99e056c4bdd
Source dataset
uspto-grants-2016_05
Patent number
US09346792B2

Reaction notes

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