2-{[4-(5-fluoropyridin-2-yl)phenyl]acetyl}-N,N-dimethyl-4-[2-methyl-2-(trifluoromethyl)but-3-en-1-yl]-1H-imidazole-1-sulfonamide → 2-{2-[4-(5-fluoropyridin-2-yl)phenyl]-1-hydroxy-1-methylethyl}-N,N-dimethyl-4-[2-methyl-2-(trifluoromethyl)but-3-en-1-yl]-1H-imidazole-1-sulfonamide

HRID 425371Notes

Reaction equation

HRID 425371 reaction equation
[CH3:1][Mg]Br.[F:4][C:5]1[CH:6]=[CH:7][C:8]([C:11]2[CH:16]=[CH:15][C:14]([CH2:17][C:18]([C:20]3[N:21]([S:34]([N:37]([CH3:39])[CH3:38])(=[O:36])=[O:35])[CH:22]=[C:23]([CH2:25][C:26]([CH3:33])([C:29]([F:32])([F:31])[F:30])[CH:27]=[CH2:28])[N:24]=3)=[O:19])=[CH:13][CH:12]=2)=[N:9][CH:10]=1>O1CCCC1>[F:4][C:5]1[CH:6]=[CH:7][C:8]([C:11]2[CH:16]=[CH:15][C:14]([CH2:17][C:18]([C:20]3[N:21]([S:34]([N:37]([CH3:38])[CH3:39])(=[O:35])=[O:36])[CH:22]=[C:23]([CH2:25][C:26]([CH3:33])([C:29]([F:30])([F:32])[F:31])[CH:27]=[CH2:28])[N:24]=3)([OH:19])[CH3:1])=[CH:13][CH:12]=2)=[N:9][CH:10]=1

Participants

4

Reactant 2

HCID 667055982-{[4-(5-fluoropyridin-2-yl)phenyl]acetyl}-N,N-dimethyl-4-[2-methyl-2-(trifluoromethyl)but-3-en-1-yl]-1H-imidazole-1-sulfonamideHCID 178418573HCID 178418573, compound

Product 1

HCID 667056262-{2-[4-(5-fluoropyridin-2-yl)phenyl]-1-hydroxy-1-methylethyl}-N,N-dimethyl-4-[2-methyl-2-(trifluoromethyl)but-3-en-1-yl]-1H-imidazole-1-sulfonamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Methylmagnesium bromide (3 M in diethyl ether) (0.50 mL, 1.49 mmol) was added to a 0° C. solution of 2-{[4-(5-fluoropyridin-2-yl)phenyl]acetyl}-N,N-dimethyl-4-[2-methyl-2-(trifluoromethyl)but-3-en-1-yl]-1H-imidazole-1-sulfonamide (780 mg, 1.49 mmol) in tetrahydrofuran (10 mL). After stirring at 0° C. for 30 min, the reaction mixture was quenched with water and extracted with methylene chloride and ethyl acetate. The combined organic extracts were dried (magnesium sulfate) and concentrated in vacuo. Chromatography over silica eluting with 0-80% ethyl acetate/hexane afforded 2-{2-[4-(5-fluoropyridin-2-yl)phenyl]-1-hydroxy-1-methylethyl}-N,N-dimethyl-4-[2-methyl-2-(trifluoromethyl)but-3-en-1-yl]-1H-imidazole-1-sulfonamide.

Workup

  1. customthe reaction mixture was quenched with water
  2. extractionextracted with methylene chloride and ethyl acetate
  3. dry with materialThe combined organic extracts were dried (magnesium sulfate)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d1d220d7dd9540c7ad884720ef4c6c77
Source dataset
uspto-grants-2012_01
Patent number
US08106070B2

Reaction notes

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