Water → HCID 59136005, compound

HRID 1960567Notes

Reaction equation

HRID 1960567 reaction equation
[CH3:1][N:2]([S:29]([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][N:33]=1)(=[O:31])=[O:30])[C:3]1[CH:4]=[C:5]([O:24][CH2:25][C:26]([NH2:28])=[O:27])[CH:6]=[C:7]2[C:11]=1[NH:10][C:9]([C:12]1[S:13][CH:14]([CH2:17][N:18]3[CH2:23][CH2:22][S:21][CH2:20][CH2:19]3)[CH2:15][N:16]=1)=[CH:8]2.O.[OH:39]OS([O-])=O.[K+].S([O-])([O-])(=O)=S.[Na+].[Na+]>O1CCCC1.C(O)C.C(OCC)(=O)C>[CH3:1][N:2]([S:29]([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][N:33]=1)(=[O:31])=[O:30])[C:3]1[CH:4]=[C:5]([O:24][CH2:25][C:26]([NH2:28])=[O:27])[CH:6]=[C:7]2[C:11]=1[NH:10][C:9]([C:12]1[S:13][CH:14]([CH2:17][N:18]3[CH2:23][CH2:22][S:21](=[O:39])[CH2:20][CH2:19]3)[CH2:15][N:16]=1)=[CH:8]2

Participants

8

Reactant 4

HCID 962WaterHCID 24477Sodium ThiosulfateHCID 23707502Potassium hydroxy sulfiteHCID 57476416HCID 57476416, compound

Product 1

HCID 59136005HCID 59136005, compoundYield 48.2%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-({7-[methyl(pyridin-2-ylsulfonyl)amino]-2-[5-(thiomorpholinomethyl)-4,5-dihydro-1,3-thiazol-2-yl]-1H-indol-5-yl}oxy)acetamide (31.7 mg) in tetrahydrofuran (1 mL) and ethanol (1 mL) were added water (1 mL) and OXONE (registered trade mark, 20 mg), and the mixture was stirred at room temperature for 3 hr. Aqueous sodium thiosulfate solution was added, and the mixture diluted with ethyl acetate. The organic layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was crystallized from ethyl acetate-diisopropyl ether to give the title compound (15.7 mg, yield 48%) as colorless crystals. melting point 160-161° C.

Workup

  1. washThe organic layer was washed with water and saturated brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was crystallized from ethyl acetate-diisopropyl ether

Sources & evidence

ORD record
ord-906a45ec580a4e69935dc002c3e55d9a
Source dataset
uspto-grants-2013_04
Patent number
US08410087B2

Reaction notes

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