Bis(trifluoroacetoxy)iodobenzene → 4-(2,2-dimethylbutyl)-2-[1-hydroxy-2-oxo-2-(4-pyridin-2-ylphenyl)ethyl]-N,N-dimethyl-1H-imidazole-1-sulfonamide

HRID 216409

Reaction equation

HRID 216409 reaction equation
FC(F)(F)C(OI(C1C=CC=CC=1)OC(=O)C(F)(F)F)=[O:4].[CH3:22][C:23]([CH3:58])([CH2:56][CH3:57])[CH2:24][C:25]1[N:26]=[C:27]([CH:36]([OH:55])[C:37]2([C:43]3[CH:48]=[CH:47][C:46]([C:49]4[CH:54]=[CH:53][CH:52]=[CH:51][N:50]=4)=[CH:45][CH:44]=3)SCCCS2)[N:28]([S:30]([N:33]([CH3:35])[CH3:34])(=[O:32])=[O:31])[CH:29]=1>C(#N)C.O>[CH3:22][C:23]([CH3:58])([CH2:56][CH3:57])[CH2:24][C:25]1[N:26]=[C:27]([CH:36]([OH:55])[C:37](=[O:4])[C:43]2[CH:48]=[CH:47][C:46]([C:49]3[CH:54]=[CH:53][CH:52]=[CH:51][N:50]=3)=[CH:45][CH:44]=2)[N:28]([S:30]([N:33]([CH3:35])[CH3:34])(=[O:32])=[O:31])[CH:29]=1

Participants

4

Reactant 2

HCID 102317Bis(trifluoroacetoxy)iodobenzeneHCID 866385154-(2,2-dimethylbutyl)-2-{hydroxy[2-(4-pyridin-2-ylphenyl)-1,3-dithian-2-yl]methyl}-N,N-dimethyl-1H-imidazole-1-sulfonamide

Product 1

HCID 686682854-(2,2-dimethylbutyl)-2-[1-hydroxy-2-oxo-2-(4-pyridin-2-ylphenyl)ethyl]-N,N-dimethyl-1H-imidazole-1-sulfonamide

Reagents, catalysts & solvents 1

HCID 18373917Acetonitrile--water (1/1)Solvent

Conditions

Temperature
0 °C

Procedure

[Bis(trifluoroacetoxy)iodo]benzene (184 mg, 0.48 mmol) was added to a 0° C. solution of 4-(2,2-dimethylbutyl)-2-{hydroxy[2-(4-pyridin-2-ylphenyl)-1,3-dithian-2-yl]methyl}-N,N-dimethyl-1H-imidazole-1-sulfonamide (110 mg, 0.20 mmol) in acetonitrile/water (3:1) (4 mL). After stirring at 0° C. until no further reaction (LCMS), the reaction mixture was quenched with saturated aqueous sodium thiosulfate/saturated aqueous sodium bicarbonate (1:1) and extracted with methylene chloride. The combined organic extracts were dried (magnesium sulfate) and concentrated in vacuo to afford 4-(2,2-dimethylbutyl)-2-[1-hydroxy-2-oxo-2-(4-pyridin-2-ylphenyl)ethyl]-N,N-dimethyl-1H-imidazole-1-sulfonamide which was used in the next step without further purification.

Workup

  1. customthe reaction mixture was quenched with saturated aqueous sodium thiosulfate/saturated aqueous sodium bicarbonate (1:1)
  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-bf6df44a5f974b3592aaa97e974ac2d0
Source dataset
uspto-grants-2012_06
Patent number
US08193228B2

Linked notes

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