Sodium Thiosulfate → HCID 136063688, compound

HRID 2048653Notes

Reaction equation

HRID 2048653 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([OH:42])[CH2:9][N:10]2[C:15](=[O:16])[C:14]([CH2:17][C:18]3[CH:23]=[CH:22][C:21]([C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=4[C:30]4[NH:34][C:33](=[O:35])[O:32][N:31]=4)=[CH:20][CH:19]=3)=[C:13]([CH2:36][CH2:37][CH3:38])[N:12]3[N:39]=[CH:40][N:41]=[C:11]23)=[CH:4][CH:3]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.C(=O)([O-])O.[Na+].S([O-])([O-])(=O)=S.[Na+].[Na+]>C(#N)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8](=[O:42])[CH2:9][N:10]2[C:15](=[O:16])[C:14]([CH2:17][C:18]3[CH:19]=[CH:20][C:21]([C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=4[C:30]4[NH:34][C:33](=[O:35])[O:32][N:31]=4)=[CH:22][CH:23]=3)=[C:13]([CH2:36][CH2:37][CH3:38])[N:12]3[N:39]=[CH:40][N:41]=[C:11]23)=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 24477Sodium ThiosulfateHCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 136063789HCID 136063789, compound

Product 1

HCID 136063688HCID 136063688, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 4-[2-(4-fluorophenyl)-2-hydroxyethyl]-6-{[2′-(5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)biphenyl-4-yl]methyl}-7-propyl[1,2,4]triazolo[1,5-a]pyrimidin-5(4H)-one (0.31 g), Dess-Martin reagent (0.35 g) and acetonitrile (10 mL) was stirred at room temperature for 2 hr. Saturated aqueous sodium hydrogen carbonate solution and sodium thiosulfate were added to the reaction mixture, and the mixture was stirred at room temperature for 2 hr, and extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography to give the title compound as a colorless amorphous solid (0.2 g, 65%).

Workup

  1. stirringthe mixture was stirred at room temperature for 2 hr
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-a3b4cc15b3fc44978d6061dbf2dfb22d
Source dataset
uspto-grants-2013_11
Patent number
US08592431B2

Reaction notes

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