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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 519746
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 519746
[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]
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Komponenten

6

Edukt 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

Produkt 1

HCID 67009468
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
Ausbeute 88 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

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%).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-bee9338f1fee4c1a9599738c9307c51e
Quelldatensatz
uspto-grants-2015_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09115136B2

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