Hydrogen Peroxide → HCID 178438743, compound

HRID 1412501Notes

Reaction equation

HRID 1412501 reaction equation
C([C@@H:4]1[CH2:7][C@H:6]([N:8]2[C:13](=[O:14])[C:12]([CH2:15][C:16]3[CH:21]=[CH:20][C:19]([C:22]4[C:23]([C:28]#[N:29])=[CH:24][CH:25]=[CH:26][CH:27]=4)=[CH:18][C:17]=3[F:30])=[C:11]([CH2:31][CH2:32][CH3:33])[N:10]3[N:34]=[C:35]([CH3:37])[N:36]=[C:9]23)[CH2:5]1)(=O)C.OO.FC(F)(F)C(OC(=O)C(F)(F)F)=[O:43].C(=O)([O-])O.[Na+].S([O-])([O-])(=O)=S.[Na+].[Na+]>C(Cl)(Cl)Cl>[F:30][C:17]1[CH:18]=[C:19]([C:22]2[C:23]([C:28]#[N:29])=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH:20]=[CH:21][C:16]=1[CH2:15][C:12]1[C:13](=[O:14])[N:8]([C@H:6]2[CH2:5][C@@H:4]([OH:43])[CH2:7]2)[C:9]2[N:10]([N:34]=[C:35]([CH3:37])[N:36]=2)[C:11]=1[CH2:31][CH2:32][CH3:33]

Participants

7

Reactant 5

HCID 784Hydrogen PeroxideHCID 9845Trifluoroacetic anhydrideHCID 24477Sodium ThiosulfateHCID 516892Sodium BicarbonateHCID 178438735HCID 178438735, compound

Product 1

HCID 178438743HCID 178438743, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
60 °C

Procedure

To a mixture of 4′-{[4-(cis-3-acetylcyclobutyl)-2-methyl-5-oxo-7-propyl-4,5-dihydro[1,2,4]triazolo[1,5-a]pyrimidin-6-yl]methyl}-3′-fluorobiphenyl-2-carbonitrile (2.83 g), 30% aqueous hydrogen peroxide solution (28.5 mL) and chloroform (30 mL) was added trifluoroacetic acid anhydride (15.75 mL), and the mixture was stirred at 60° C. for 15 hr. The reaction mixture was cooled to room temperature, saturated aqueous sodium hydrogen carbonate solution and sodium thiosulfate were added, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. To a solution of the obtained residue in tetrahydrofuran (5 mL)-methanol (5 mL) was added 2 N aqueous sodium hydroxide solution (4 mL), and the mixture was stirred at room temperature for 1 hr. The reaction mixture was acidified with 1 N hydrochloric acid, and extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by basic silica gel chromatography [eluent: hexane/ethyl acetate=60/40→35/65 (volume ratio)] to give the title compound as a colorless amorphous compound (1.70 g, 63%).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. additionTo a solution of the obtained residue in tetrahydrofuran (5 mL)-methanol (5 mL) was added 2 N aqueous sodium hydroxide solution (4 mL)
  7. stirringthe mixture was stirred at room temperature for 1 hr
  8. extractionextracted with ethyl acetate
  9. washThe extract was washed with saturated brine
  10. dry with materialdried over anhydrous magnesium sulfate
  11. customThe solvent was evaporated under reduced pressure
  12. customthe residue was purified by basic silica gel chromatography [eluent: hexane/ethyl acetate=60/40→35/65 (volume ratio)]

Sources & evidence

ORD record
ord-e51f0ba42e0041c983ee8ae16f3fa1b8
Source dataset
uspto-grants-2014_12
Patent number
US08921379B2

Reaction notes

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