Cyclohexylamine → 2-(4-Methoxyphenyl)-5-methyl-2H-pyrazole-3-carboxylic acid cyclohexylamide

HRID 598774Notes

Reaction equation

HRID 598774 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[C:13]([C:14]([OH:16])=O)=[CH:12][C:11]([CH3:17])=[N:10]2)=[CH:5][CH:4]=1.[CH:18]1([NH2:24])[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1>C(Cl)Cl.CS(C)=O>[CH:18]1([NH:24][C:14]([C:13]2[N:9]([C:6]3[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=3)[N:10]=[C:11]([CH3:17])[CH:12]=2)=[O:16])[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1

Participants

5

Reactant 2

HCID 7965CyclohexylamineHCID 27695991-(4-Methoxyphenyl)-3-methyl-1H-pyrazole-5-carboxylic acid

Product 1

HCID 582568022-(4-Methoxyphenyl)-5-methyl-2H-pyrazole-3-carboxylic acid cyclohexylamideYield 62%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideCatalystHCID 6344DichloromethaneSolvent3×

Procedure

2-(4-Methoxyphenyl)-5-methyl-2H-pyrazole-3-carboxylic acid (752 mg, 3.24 mmol) was suspended in methylene chloride (25 mL) and DMSO (3 drops) was added. After the reaction was stirred at room temperature for 1 hour, it was concentrated in vacuo. The residue was diluted twice with methylene chloride (60 mL) and concentrated to dryness. The residue was diluted again with methylene chloride (45 mL), cyclohexylamine (650 μL, 5.68 mmol) was added, and the reaction was stirred at room temperature for 1 hour. The reaction was diluted further with methylene chloride, washed with NaOH (10%) and 1 N HCl, then dried over Na2SO4. Concentration gave 630 mg of the title compound, which was used in the next reaction without further purification. LC-MS (C18H23N3O2 calculated 313) m/z 314 (M+H).

Workup

  1. concentrationit was concentrated in vacuo
  2. additionThe residue was diluted twice with methylene chloride (60 mL)
  3. concentrationconcentrated to dryness
  4. additionwas added
  5. stirringthe reaction was stirred at room temperature for 1 hour
  6. washwashed with NaOH (10%) and 1 N HCl
  7. dry with materialdried over Na2SO4
  8. concentrationConcentration

Sources & evidence

ORD record
ord-8b3054f1b876447e90f785aa9c91b76f
Source dataset
uspto-grants-2011_03
Patent number
US07897634B2

Reaction notes

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