Sodium Sulfite → N-[5-(2-methoxyethoxy)-2-(8-oxido-1,8-dithia-3-azaspiro[4.5]dec-2-en-2-yl)-1H-indol-7-yl]-N-methylpyridine-2-sulfonamide

HRID 2239178Notes

Reaction equation

HRID 2239178 reaction equation
[S:1]1[C:5]2([CH2:10][CH2:9][S:8][CH2:7][CH2:6]2)[CH2:4][N:3]=[C:2]1[C:11]1[NH:12][C:13]2[C:18]([CH:19]=1)=[CH:17][C:16]([O:20][CH2:21][CH2:22][O:23][CH3:24])=[CH:15][C:14]=2[N:25]([CH3:35])[S:26]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][N:30]=1)(=[O:28])=[O:27].[OH:36]OS([O-])=O.[K+].S([O-])([O-])=O.[Na+].[Na+]>CO.O.ClCCl>[CH3:24][O:23][CH2:22][CH2:21][O:20][C:16]1[CH:17]=[C:18]2[C:13](=[C:14]([N:25]([CH3:35])[S:26]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][N:30]=3)(=[O:27])=[O:28])[CH:15]=1)[NH:12][C:11]([C:2]1[S:1][C:5]3([CH2:6][CH2:7][S:8](=[O:36])[CH2:9][CH2:10]3)[CH2:4][N:3]=1)=[CH:19]2

Participants

7

Reactant 3

HCID 24437Sodium SulfiteHCID 23707502Potassium hydroxy sulfiteHCID 59135931N-[2-(1,8-dithia-3-azaspiro[4.5]dec-2-en-2-yl)-5-(2-methoxyethoxy)-1H-indol-7-yl]-N-methylpyridine-2-sulfonamide

Product 1

HCID 59135707N-[5-(2-methoxyethoxy)-2-(8-oxido-1,8-dithia-3-azaspiro[4.5]dec-2-en-2-yl)-1H-indol-7-yl]-N-methylpyridine-2-sulfonamideYield 20%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of N-[2-(1,8-dithia-3-azaspiro[4.5]dec-2-en-2-yl)-5-(2-methoxyethoxy)-1H-indol-7-yl]-N-methylpyridine-2-sulfonamide (50.7 mg) in methanol (2 mL), water (1 mL) and dichloromethane (1 mL) was added OXONE (registered trade mark, 29 mg) at room temperature, and the mixture was stirred for 18 hr. Aqueous sodium sulfite solution was added to the reaction mixture, and the mixture was stirred for 30 min. The organic solvent was evaporated under reduced pressure. The residue was extracted with ethyl acetate, and the organic layer was washed with water and saturated brine, dried (MgSO4), and concentrated. The residue was subjected to basic silica gel column chromatography, and eluted with ethyl acetate to give two steric isomers (10.3 mg, yield 20% (retention time: shorter), and 1.7 mg, yield 3% (retention time: longer)) of the title compound as a colorless amorphous solid, respectively.

Workup

  1. stirringthe mixture was stirred for 30 min
  2. customThe organic solvent was evaporated under reduced pressure
  3. extractionThe residue was extracted with ethyl acetate
  4. washthe organic layer was washed with water and saturated brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated
  7. washeluted with ethyl acetate
  8. customto give two steric isomers (10.3 mg, yield 20% (retention time: shorter), and 1.7 mg, yield 3% (retention time

Sources & evidence

ORD record
ord-b5f97c4f6f4149c89214026cedbcea6e
Source dataset
uspto-grants-2010_05
Patent number
US07718798B2

Reaction notes

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