Sodium Thiosulfate → 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

HRID 519746Notes

Reaction equation

HRID 519746 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:38]2[C:39]([C:44]#[N:45])=[CH:40][CH:41]=[CH:42][CH:43]=2)[CH:5]=[CH:6][C:7]=1[CH2:8][C:9]1[C:10](=[O:37])[N:11]([CH:21]2[CH2:26][CH2:25][CH:24]([O:27][CH:28]([C:30]3([CH:34]([OH:36])[CH3:35])[CH2:33][CH2:32][CH2:31]3)[CH3:29])[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)C2C=CC=CC1=2)=O.C(=O)([O-])O.[Na+].S([O-])([O-])(=O)=S.[Na+].[Na+]>C(#N)C>[C:34]([C:30]1([CH:28]([O:27][CH:24]2[CH2:25][CH2:26][CH:21]([N:11]3[C:10](=[O:37])[C:9]([CH2:8][C:7]4[CH:6]=[CH:5][C:4]([C:38]5[C:39]([C:44]#[N:45])=[CH:40][CH:41]=[CH:42][CH:43]=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)[CH2:22][CH2:23]2)[CH3:29])[CH2:33][CH2:32][CH2:31]1)(=[O:36])[CH3:35]

Participants

6

Reactant 4

HCID 24477Sodium ThiosulfateHCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 670092183'-Fluoro-4'-{[4-(4-{1-[1-(1-hydroxyethyl)cyclobutyl]ethoxy}cyclohexyl)-5-oxo-7-propyl-4,5-dihydro[1,2,4]triazolo[1,5-a]pyrimidin-6-yl]methyl}biphenyl-2-carbonitrile

Product 1

HCID 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-carbonitrileYield 88%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 3′-fluoro-4′-{[4-(4-{1-[1-(1-hydroxyethyl)cyclobutyl]ethoxy}cyclohexyl)-5-oxo-7-propyl-4,5-dihydro[1,2,4]triazolo[1,5-a]pyrimidin-6-yl]methyl}biphenyl-2-carbonitrile (13 g), Dess-Martin periodinane (10 g) and acetonitrile (130 mL) was stirred at room temperature for 30 min. Saturated aqueous sodium hydrogen carbonate solution and 1 M aqueous sodium thiosulfate solution were 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, and the residue was purified by silica gel column chromatography to give the title compound as a colorless solid (11 g, 88%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-bee9338f1fee4c1a9599738c9307c51e
Source dataset
uspto-grants-2015_08
Patent number
US09115136B2

Reaction notes

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