Hydrogen Peroxide → HCID 178438715, compound

HRID 2048487Notes

Reaction equation

HRID 2048487 reaction equation
C([C:4]1([CH:8]([O:10][CH:11]2[CH2:16][CH2:15][CH:14]([N:17]3[C:22](=[O:23])[C:21]([CH2:24][C:25]4[CH:30]=[CH:29][C:28]([C:31]5[C:32]([C:37]#[N:38])=[CH:33][CH:34]=[CH:35][CH:36]=5)=[CH:27][C:26]=4[F:39])=[C:20]([CH2:40][CH2:41][CH3:42])[N:19]4[N:43]=[CH:44][N:45]=[C:18]34)[CH2:13][CH2:12]2)[CH3:9])[CH2:7][CH2:6][CH2:5]1)(=O)C.OO.FC(F)(F)C(OC(=O)C(F)(F)F)=[O:51].C(=O)([O-])O.[Na+].S([O-])([O-])(=O)=S.[Na+].[Na+]>C(Cl)(Cl)Cl>[F:39][C:26]1[CH:27]=[C:28]([C:31]2[C:32]([C:37]#[N:38])=[CH:33][CH:34]=[CH:35][CH:36]=2)[CH:29]=[CH:30][C:25]=1[CH2:24][C:21]1[C:22](=[O:23])[N:17]([C@H:14]2[CH2:13][CH2:12][C@H:11]([O:10][CH:8]([C:4]3([OH:51])[CH2:7][CH2:6][CH2:5]3)[CH3:9])[CH2:16][CH2:15]2)[C:18]2[N:19]([N:43]=[CH:44][N:45]=2)[C:20]=1[CH2:40][CH2:41][CH3:42]

Participants

7

Reactant 5

HCID 784Hydrogen PeroxideHCID 9845Trifluoroacetic anhydrideHCID 24477Sodium ThiosulfateHCID 516892Sodium BicarbonateHCID 670094684'-[(4-{4-[1-(1-Acetylcyclobutyl)ethoxy]cyclohexyl]-5-oxo-7-propyl-4,5-dihydro[1,2,4]triazolo[1,5-a]pyrimidin-6-yl)methyl}-3'-fluorobiphenyl-2-carbonitrile

Product 1

HCID 178438715HCID 178438715, compoundYield 12%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
60 °C

Procedure

To a mixture of 4′-[(4-{4-[1-(1-acetylcyclobutyl)ethoxy]cyclohexyl}-5-oxo-7-propyl-4,5-dihydro[1,2,4]triazolo[1,5-a]pyrimidin-6-yl)methyl]-3′-fluorobiphenyl-2-carbonitrile (11 g), 30% hydrogen peroxide (157 mL) and chloroform (150 mL) was gradually added dropwise trifluoroacetic acid anhydride (105 mL), and the mixture was stirred at 60° C. for 24 hr and then at room temperature for 40 hr. Saturated aqueous sodium hydrogen carbonate solution and aqueous sodium thiosulfate solution were gradually added to the reaction mixture, and the mixture was 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 residue was mixed with tetrahydrofuran (100 mL), methanol (100 mL) and 1 M aqueous sodium hydroxide solution (100 mL), and the mixture was stirred at room temperature for 1 hr. The reaction mixture was neutralized with 1 M hydrochloric acid. After evaporation of the solvent under reduced pressure, the residue was 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, and the residue was purified by silica gel column chromatography to give the title compound as a colorless solid (1.3 g, 12%).

Workup

  1. waitat room temperature for 40 hr
  2. extractionthe mixture was extracted 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. additionThe residue was mixed with tetrahydrofuran (100 mL), methanol (100 mL) and 1 M aqueous sodium hydroxide solution (100 mL)
  7. stirringthe mixture was stirred at room temperature for 1 hr
  8. customAfter evaporation of the solvent under reduced pressure
  9. extractionthe residue was extracted with ethyl acetate
  10. washThe organic layer was washed with saturated brine
  11. dry with materialdried over anhydrous magnesium sulfate
  12. customThe solvent was evaporated under reduced pressure
  13. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-ffa40b3459f2489a926e56675e665475
Source dataset
uspto-grants-2013_11
Patent number
US08592431B2

Reaction notes

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