(Diethylamino)sulfur trifluoride → 4-(2,2-dimethylpropyl)-2-[1-fluoro-2-(4-pyridin-2-ylphenyl)ethyl]-N,N-dimethyl-1H-imidazole-1-sulfonamide

HRID 425337Notes

Reaction equation

HRID 425337 reaction equation
C(N(S(F)(F)[F:7])CC)C.[CH3:10][C:11]([CH3:40])([CH3:39])[CH2:12][C:13]1[N:14]=[C:15]([CH:24](O)[CH2:25][C:26]2[CH:31]=[CH:30][C:29]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][N:33]=3)=[CH:28][CH:27]=2)[N:16]([S:18]([N:21]([CH3:23])[CH3:22])(=[O:20])=[O:19])[CH:17]=1>C(Cl)Cl>[CH3:10][C:11]([CH3:40])([CH3:39])[CH2:12][C:13]1[N:14]=[C:15]([CH:24]([F:7])[CH2:25][C:26]2[CH:31]=[CH:30][C:29]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][N:33]=3)=[CH:28][CH:27]=2)[N:16]([S:18]([N:21]([CH3:23])[CH3:22])(=[O:20])=[O:19])[CH:17]=1

Participants

4

Reactant 2

HCID 123472(Diethylamino)sulfur trifluorideHCID 66705591HCID 66705591, compound

Product 1

HCID 667054274-(2,2-dimethylpropyl)-2-[1-fluoro-2-(4-pyridin-2-ylphenyl)ethyl]-N,N-dimethyl-1H-imidazole-1-sulfonamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Diethylaminosulfur trifluoride (0.1 mL, 0.8 mmol) was added to an ambient temperature solution of 4-(2,2-dimethylpropyl)-2-[1-hydroxy-2-(4-pyridin-2-ylphenyl)ethyl]-N,N-dimethyl-1H-imidazole-1-sulfonamide (for synthesis see Example 1) (71 mg, 0.16 mmol) in methylene chloride (5 mL). After stirring at ambient temperature overnight, the reaction mixture was quenched with saturated aqueous sodium bicarbonate and extracted with methylene chloride. The combined organic extracts were dried (magnesium sulfate) and concentrated in vacuo. Chromatography over silica eluting with 0-50% ethyl acetate/hexane afforded 4-(2,2-dimethylpropyl)-2-[1-fluoro-2-(4-pyridin-2-ylphenyl)ethyl]-N,N-dimethyl-1H-imidazole-1-sulfonamide.

Workup

  1. customthe reaction mixture was quenched with saturated aqueous sodium bicarbonate
  2. extractionextracted with methylene chloride
  3. dry with materialThe combined organic extracts were dried (magnesium sulfate)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0447c73a20eb493e8b08ea9cde968158
Source dataset
uspto-grants-2012_01
Patent number
US08106070B2

Reaction notes

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