Sodium Thiosulfate → HCID 178438710, compound

HRID 2048375Notes

Reaction equation

HRID 2048375 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:37]2[C:38]([C:43]#[N:44])=[CH:39][CH:40]=[CH:41][CH:42]=2)[CH:5]=[CH:6][C:7]=1[CH2:8][C:9]1[C:10](=[O:36])[N:11]([C@H:21]2[CH2:26][CH2:25][C@H:24]([O:27][CH2:28][C:29]3([CH:33]([OH:35])[CH3:34])[CH2:32][CH2:31][CH2:30]3)[CH2:23][CH2:22]2)[C:12]2[N:13]([N:18]=[CH:19][N:20]=2)[C:14]=1[CH2:15][CH2:16][CH3:17].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C1=CC=CC=2)=O.C(=O)([O-])O.[Na+].S([O-])([O-])(=O)=S.[Na+].[Na+]>C(#N)C>[C:33]([C:29]1([CH2:28][O:27][C@H:24]2[CH2:23][CH2:22][C@H:21]([N:11]3[C:10](=[O:36])[C:9]([CH2:8][C:7]4[CH:6]=[CH:5][C:4]([C:37]5[C:38]([C:43]#[N:44])=[CH:39][CH:40]=[CH:41][CH:42]=5)=[CH:3][C:2]=4[F:1])=[C:14]([CH2:15][CH2:16][CH3:17])[N:13]4[N:18]=[CH:19][N:20]=[C:12]34)[CH2:26][CH2:25]2)[CH2:32][CH2:31][CH2:30]1)(=[O:35])[CH3:34]

Participants

6

Reactant 4

HCID 24477Sodium ThiosulfateHCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 178438711HCID 178438711, compound

Product 1

HCID 178438710HCID 178438710, compoundYield 90.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

3′-Fluoro-4′-{[4-(trans-4-{[1-(1-hydroxyethyl)cyclobutyl]methoxy}cyclohexyl)-5-oxo-7-propyl-4,5-dihydro[1,2,4]triazolo[1,5-a]pyrimidin-6-yl]methyl}biphenyl-2-carbonitrile (0.72 g) was dissolved in acetonitrile (20 mL), 1,1,1-triacetoxy-1,1-dihydro-1,2-benziodoxol-3(1H)-one (0.77 g) was added, and the mixture was stirred at room temperature for 4 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 solid (0.65 g, 89%).

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-730da45786e1402e9c90f4f42ac7ccc9
Source dataset
uspto-grants-2013_11
Patent number
US08592431B2

Reaction notes

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