Methanol → 3-(5-(4-Chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazol-3-yl)-5-cyclopentyl-1H-1,2,4-triazole

HRID 254829Notes

Reaction equation

HRID 254829 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([C:13]3[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][C:14]=3[Cl:20])[N:11]=[C:10]([C:21]#[N:22])[C:9]=2[CH3:23])=[CH:4][CH:3]=1.[CH:24]1([C:29]([NH:31][NH2:32])=O)[CH2:28][CH2:27][CH2:26][CH2:25]1.C(=O)([O-])[O-].[K+].[K+].CO>C(O)CCC>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:12]([C:13]3[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][C:14]=3[Cl:20])[N:11]=[C:10]([C:21]3[N:22]=[C:29]([CH:24]4[CH2:28][CH2:27][CH2:26][CH2:25]4)[NH:31][N:32]=3)[C:9]=2[CH3:23])=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 11430Potassium CarbonateHCID 240040CyclopentanecarbohydrazideHCID 668444145-(4-chloro phenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carbonitrile

Product 1

HCID 248103323-(5-(4-Chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazol-3-yl)-5-cyclopentyl-1H-1,2,4-triazole

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A solution of 5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carbonitrile (300 mg, 0.83 mmol), cyclopentanecarbohydrazide (116 mg, 0.90 mmol) and potassium carbonate (57 mg, 0.41 mmol) dissolved in 1-butanol (2 ml) was placed in a sealed tube, stirred at room temperature for 10 minutes and then refluxed at 150° C. for 1 day. The mixture was cooled down to room temperature and methanol (4 ml) was added thereto, followed by filtering. The filtrate was purified by reverse phase preparative HPLC, to obtain the title compound as white solid.

Workup

  1. customwas placed in a sealed tube
  2. temperaturerefluxed at 150° C. for 1 day
  3. temperatureThe mixture was cooled down to room temperature
  4. filtrationby filtering
  5. customThe filtrate was purified by reverse phase preparative HPLC

Sources & evidence

ORD record
ord-6a40cbd8791844e59d509ce09792e693
Source dataset
uspto-grants-2011_01
Patent number
US07875647B2

Reaction notes

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