Potassium Hydroxide → HCID 66705591, compound

HRID 425335Notes

Reaction equation

HRID 425335 reaction equation
[OH-].[K+].[CH3:3][C:4]([CH3:38])([CH3:37])[CH2:5][C:6]1[N:7]=[C:8]([CH:17]([OH:36])[C:18]2([C:24]3[CH:29]=[CH:28][C:27]([C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][N:31]=4)=[CH:26][CH:25]=3)SCCCS2)[N:9]([S:11]([N:14]([CH3:16])[CH3:15])(=[O:13])=[O:12])[CH:10]=1>C(O)C.[Ni]>[CH3:3][C:4]([CH3:38])([CH3:37])[CH2:5][C:6]1[N:7]=[C:8]([CH:17]([OH:36])[CH2:18][C:24]2[CH:25]=[CH:26][C:27]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][N:31]=3)=[CH:28][CH:29]=2)[N:9]([S:11]([N:14]([CH3:16])[CH3:15])(=[O:13])=[O:12])[CH:10]=1

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 86637791HCID 86637791, compound

Product 1

HCID 66705591HCID 66705591, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

Rainey Nickel (600 mg) followed by 1 M aqueous potassium hydroxide (1 mL) were added to an ambient temperature solution of 4-(2,2-dimethylpropyl)-2-{hydroxy[2-(4-pyridin-2-ylphenyl)-1,3-dithian-2-yl]methyl}-N,N-dimethyl-1H-imidazole-1-sulfonamide (21 mg, 0.04 mmol) in ethanol (2 mL). After stirring at ambient temperature overnight, the reaction mixture was filtered through celite and concentrated in vacuo. Prep plate chromatography (70% ethyl acetate/hexane) afforded 4-(2,2-dimethyl-propyl)-2-[1-hydroxy-2-(4-pyridin-2-ylphenyl)ethyl]-N,N-dimethyl-1H-imidazole-1-sulfonamide.

Workup

  1. filtrationthe reaction mixture was filtered through celite and
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2738d5c2f8404b288ddd765f992cb842
Source dataset
uspto-grants-2012_01
Patent number
US08106070B2

Reaction notes

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