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Hydrochloric Acid → HCID 178438769, Verbindung

HRID 2048598
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2048598
[O:1]1[C:5]2([CH2:10][CH2:9][CH:8]([N:11]3[C:16](=[O:17])[C:15]([CH2:18][C:19]4[CH:24]=[CH:23][C:22]([C:25]5[C:26]([C:31]#[N:32])=[CH:27][CH:28]=[CH:29][CH:30]=5)=[C:21]([O:33][CH3:34])[CH:20]=4)=[C:14]([CH2:35][CH2:36][CH3:37])[N:13]4[N:38]=[CH:39][CH:40]=[C:12]34)[CH2:7][CH2:6]2)[O:4][CH2:3][CH2:2]1.Cl.[OH-:42].[Na+].O1CC[CH2:46][CH2:45]1>C(OCC)(=O)C>[C:31]([C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=1[C:22]1[CH:23]=[CH:24][C:19]([CH2:18][C:15]2[C:16](=[O:17])[N:11]([C@H:8]3[CH2:7][CH2:6][C@H:5]([O:4][CH2:3][C:2]([O:1][CH2:45][CH3:46])=[O:42])[CH2:10][CH2:9]3)[C:12]3[N:13]([N:38]=[CH:39][CH:40]=3)[C:14]=2[CH2:35][CH2:36][CH3:37])=[CH:20][C:21]=1[O:33][CH3:34])#[N:32]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 670098494'-{[4-(1,4-Dioxaspiro[4.5]dec-8-yl)-5-oxo-7-propyl-4,5-dihydropyrazolo[1,5-a]pyrimidin-6-yl]methyl}-2'-methoxybiphenyl-2-carbonitrile

Produkt 1

HCID 178438769HCID 178438769, VerbindungAusbeute 53 %

Reagenzien, Katalysatoren, Lösungsmittel

1
HCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To a solution of 4′-{[4-(1,4-dioxaspiro[4.5]dec-8-yl)-5-oxo-7-propyl-4,5-dihydropyrazolo[1,5-a]pyrimidin-6-yl]methyl}-2′-methoxybiphenyl-2-carbonitrile (0.25 g) in tetrahydrofuran (3 mL) was added 3M hydrochloric acid (3 mL), and the mixture was stirred at 60° C. for 12 hr. The mixture was allowed to cool, and diluted with ethyl acetate, and the mixture was neutralized with 1 M aqueous sodium hydroxide solution. The mixture was extracted with ethyl acetate, and the organic layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated. The residue was dissolved in ethanol (3 mL)-tetrahydrofuran (3 mL). Thereto was added sodium borohydride (0.019 g) at 0° C. After stirring for 1 hr, ethyl acetate and saturated aqueous ammonium chloride solution were added. The mixture was extracted with ethyl acetate, and the organic layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated. The residue was dissolved in methylene chloride (2 mL), rhodium acetate (dimer, 0.020 g) and then ethyl diazoacetate (0.86 mL) were added dropwise, and the mixture was stirred for 3 hr. Ethyl acetate and water were added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and then with saturated brine, dried over anhydrous magnesium sulfate, and concentrated. The residue was purified by silica gel column chromatography to give the title compound as a pale-yellow amorphous solid (0.13 g, 53%).

Aufarbeitung

  1. temperatureto cool
  2. extractionThe mixture was extracted with ethyl acetate
  3. washthe organic layer was washed with water and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated
  6. dissolutionThe residue was dissolved in ethanol (3 mL)-tetrahydrofuran (3 mL)
  7. additionThereto was added sodium borohydride (0.019 g) at 0° C
  8. stirringAfter stirring for 1 hr
  9. additionethyl acetate and saturated aqueous ammonium chloride solution were added
  10. extractionThe mixture was extracted with ethyl acetate
  11. washthe organic layer was washed with water and saturated brine
  12. dry with materialdried over anhydrous magnesium sulfate
  13. concentrationconcentrated
  14. dissolutionThe residue was dissolved in methylene chloride (2 mL)
  15. additionrhodium acetate (dimer, 0.020 g) and then ethyl diazoacetate (0.86 mL) were added dropwise
  16. stirringthe mixture was stirred for 3 hr
  17. additionEthyl acetate and water were added to the reaction mixture
  18. extractionthe mixture was extracted with ethyl acetate
  19. washThe organic layer was washed with water
  20. dry with materialwith saturated brine, dried over anhydrous magnesium sulfate
  21. concentrationconcentrated
  22. customThe residue was purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-36a9fd0987f54a3a90f4075f2f7d859d
Quelldatensatz
uspto-grants-2013_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08592431B2

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