Pyrazole → 4-(2,2-dimethylpropyl)-N,N-dimethyl-2-{[4-(1H-pyrazol-1-yl)phenyl]acetyl}-1H-imidazole-1-sulfonamide

HRID 425367Notes

Reaction equation

HRID 425367 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([C:11]2[N:12]([S:21]([N:24]([CH3:26])[CH3:25])(=[O:23])=[O:22])[CH:13]=[C:14]([CH2:16][C:17]([CH3:20])([CH3:19])[CH3:18])[N:15]=2)=[O:10])=[CH:4][CH:3]=1.[NH:27]1[CH:31]=[CH:30][CH:29]=[N:28]1.C(=O)([O-])[O-].[K+].[K+].CN[C@@H]1CCCC[C@H]1NC>C1(C)C=CC=CC=1.[Cu]I>[CH3:18][C:17]([CH3:20])([CH3:19])[CH2:16][C:14]1[N:15]=[C:11]([C:9](=[O:10])[CH2:8][C:5]2[CH:6]=[CH:7][C:2]([N:27]3[CH:31]=[CH:30][CH:29]=[N:28]3)=[CH:3][CH:4]=2)[N:12]([S:21]([N:24]([CH3:26])[CH3:25])(=[O:23])=[O:22])[CH:13]=1

Participants

7

Reactant 4

HCID 1048PyrazoleHCID 11430Potassium CarbonateHCID 2733821trans-N,N'-dimethyl-1,2-cyclohexanediamineHCID 591403972-[(4-bromophenyl)acetyl]-4-(2,2-dimethylpropyl)-N,N-dimethyl-1H-imidazole-1-sulfonamide2×

Product 1

HCID 667056664-(2,2-dimethylpropyl)-N,N-dimethyl-2-{[4-(1H-pyrazol-1-yl)phenyl]acetyl}-1H-imidazole-1-sulfonamide

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 1140TolueneSolvent

Procedure

2-[(4-bromophenyl)acetyl]-4-(2,2-dimethylpropyl)-N,N-dimethyl-1H-imidazole-1-sulfonamide (Intermediate 7) (1 g, 2.261 mmol) was added to a stirred, ambient temperature mixture of pyrazole (0.146 g, 2.148 mmol), potassium carbonate (0.656 g, 4.75 mmol), rac-trans-N,N′-dimethylcyclohexane-1,2-diamine (0.064 g, 0.452 mmol) and copper (I) iodide (0.022 g, 0.113 mmol) in toluene (2.5 mL). After stirring at reflux overnight, the reaction mixture was partitioned between water and ethyl acetate. The organic phase was washed with saturated brine, dried (sodium sulfate), filtered and concentrated in vacuo. Chromatography over silica eluting with 0-60% EtOAc/hexane afforded 4-(2,2-dimethylpropyl)-N,N-dimethyl-2-{[4-(1H-pyrazol-1-yl)phenyl]acetyl}-1H-imidazole-1-sulfonamide.

Workup

  1. temperatureat reflux overnight
  2. customthe reaction mixture was partitioned between water and ethyl acetate
  3. washThe organic phase was washed with saturated brine
  4. dry with materialdried (sodium sulfate)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3ddc1f44182e482aa1ca8a9c07ec5a88
Source dataset
uspto-grants-2012_01
Patent number
US08106070B2

Reaction notes

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