Ethanol → HCID 68464556, compound

HRID 1994936Notes

Reaction equation

HRID 1994936 reaction equation
[CH3:1][N:2]([C:12]1[CH:13]=[C:14]([O:33][CH2:34][CH2:35][CH2:36][S:37]([CH3:40])(=[O:39])=[O:38])[CH:15]=[C:16]2[C:20]=1[NH:19][C:18]([C:21]1[S:22][CH:23]([CH2:26][N:27]3[CH2:32][CH2:31][S:30][CH2:29][CH2:28]3)[CH2:24][N:25]=1)=[CH:17]2)[S:3]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][N:7]=1)(=[O:5])=[O:4].C([OH:43])C.OOS([O-])=O.[K+].S([O-])([O-])=O.[Na+].[Na+]>O1CCCC1.O>[CH3:1][N:2]([C:12]1[CH:13]=[C:14]([O:33][CH2:34][CH2:35][CH2:36][S:37]([CH3:40])(=[O:38])=[O:39])[CH:15]=[C:16]2[C:20]=1[NH:19][C:18]([C:21]1[S:22][CH:23]([CH2:26][N:27]3[CH2:32][CH2:31][S:30](=[O:43])[CH2:29][CH2:28]3)[CH2:24][N:25]=1)=[CH:17]2)[S:3]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][N:7]=1)(=[O:5])=[O:4]

Participants

7

Reactant 4

HCID 702EthanolHCID 24437Sodium SulfiteHCID 23707502Potassium hydroxy sulfiteHCID 67487327HCID 67487327, compound

Product 1

HCID 68464556HCID 68464556, compoundYield 54%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of N-methyl-N-{5-[3-(methylsulfonyl)propoxy]-2-[5-(thiomorpholinomethyl)-4,5-dihydro-1,3-thiazol-2-yl]-1H-indol-7-yl}pyridine-2-sulfonamide (0.35 g), ethanol (60 mL), water (30 mL) and tetrahydrofuran (30 mL) was added OXONE (registered trade mark, 0.19 g), and the mixture was stirred at room temperature for 3 hr. Aqueous sodium sulfite solution was added to the reaction mixture, the mixture was stirred for 30 min, and the organic solvent was evaporated under reduced pressure. The residue was diluted with water, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained colorless crystals were recrystallized from ethyl acetate-hexane to give the title compound (193 mg, yield: 54%) as colorless crystals. MS: 641 (MH+). melting point 107-110° C.

Workup

  1. stirringthe mixture was stirred for 30 min
  2. customthe organic solvent was evaporated under reduced pressure
  3. additionThe residue was diluted with water
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe organic layer was washed with saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe obtained colorless crystals were recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-afca4c2b4bf944739d0734f80b6b2766
Source dataset
uspto-grants-2010_01
Patent number
US07652133B2

Reaction notes

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