Triethylamine → N-(2-Cyclohexylphenyl)-1-methyl-3-(trifluoromethyl)-1H-pyrazole-4-carboxamide

HRID 1588786Notes

Reaction equation

HRID 1588786 reaction equation
[CH3:1][N:2]1[CH:6]=[C:5]([C:7](Cl)=[O:8])[C:4]([C:10]([F:13])([F:12])[F:11])=[N:3]1.[CH:14]1([C:20]2[CH:26]=[CH:25][CH:24]=[CH:23][C:21]=2[NH2:22])[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1.C(N(CC)CC)C>C(Cl)Cl>[CH:14]1([C:20]2[CH:26]=[CH:25][CH:24]=[CH:23][C:21]=2[NH:22][C:7]([C:5]2[C:4]([C:10]([F:13])([F:12])[F:11])=[N:3][N:2]([CH3:1])[CH:6]=2)=[O:8])[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 4078992-CyclohexylbenzenamineHCID 27945811-methyl-3-(trifluoromethyl)-1H-pyrazole-4-carbonyl chloride

Product 1

HCID 19754740N-(2-Cyclohexylphenyl)-1-methyl-3-(trifluoromethyl)-1H-pyrazole-4-carboxamideYield 111.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 1-methyl-3-(trifluoromethyl)-1H-pyrazole-4-carboxylic acid chloride (1.6 g) in CH2Cl12 (25 mL) at 0° C. was added dropwise a solution of 2-cyclohexylaniline (1.3 g) and triethylamine (1.0 mL) in CH2Cl2 (25 mL). The contents were stirred overnight, coming to RT. The contents were washed with water, 2N HCl (2×100 mL), dried (MgSO4) and concentrated in vacuo leaving an amber foam (2.9 g). Crystallization from EtOAc/hexane gave the desired amide as white crystals (1.2 g). Most of the compounds of the present invention were made via this coupling procedure.

Workup

  1. customcoming to RT
  2. washThe contents were washed with water, 2N HCl (2×100 mL)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-11d9c13f5ebf4b6a92dc2e9a0a23d981
Source dataset
uspto-grants-1993_06
Patent number
US05223526

Reaction notes

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