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 1960575ノート

反応式

HRID 1960575 の反応式
[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

参加物

7

反応物 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

生成物 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-sulfonamide収率 20%

試薬・触媒・溶媒 3

HCID 887Methanol溶媒HCID 962Water溶媒HCID 6344Dichloromethane溶媒

実験手順

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. (retention time: shorter) 1H-NMR(CDCl3) δ: 2.08-2.17 (2H, m), 2.68-2.81 (4H, m), 3.05-3.21 (2H, m), 3.28 (3H, s), 3.46 (3H, s), 3.65-3.82 (2H, m), 4.06-4.18 (2H, m), 4.28 (2H, s), 6.79 (1H, d, J=1.9 Hz), 6.95 (1H, d, J=2.3 Hz), 7.07 (1H, d, J=1.9 Hz), 7.60-7.65 (1H, m), 7.98 (1H, td, J=7.8, 1.9 Hz), 8.06-8.11 (1H, m), 9.06 (1H, d, J=4.9 Hz), 11.98 (1H, d, J=1.5 Hz). (retention time: longer) 1H-NMR(CDCl3) δ: 1.98-2.25 (2H, m), 2.53-2.64 (2H, m), 2.96 (2H, t, J=10.6 Hz), 3.14-3.28 (2H, m), 3.31 (3H, s), 3.46 (3H, s), 3.74-3.78 (2H, m), 4.06-4.16 (2H, m), 4.26 (2H, s), 6.84 (1H, d, J=1.9 Hz), 6.90 (1H, d, J=2.3 Hz), 7.07 (1H, d, J=2.3 Hz), 7.60 (1H, dd, J=8.3, 5.3 Hz), 7.95 (1H, t, J=6.8 Hz), 8.00-8.17 (1H, m), 9.02 (1H, d, J=3.8 Hz), 11.66 (1H, brs).

後処理

  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

出典と根拠

ORDレコード
ord-507e5167d282452c83714e562976c28f
出典データセット
uspto-grants-2013_04
特許番号
US08410087B2

反応ノート

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