HCID 11596355, Verbindung → HCID 59769615, Verbindung

HRID 1367662Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1367662
C([O:8][C:9]1[C:14](=[O:15])[CH:13]=[C:12]([CH3:16])[N:11]([CH:17]2[CH2:19][CH2:18]2)[C:10]=1[C:20]([NH:22][CH2:23][CH:24]1[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1)=[O:21])C1C=CC=CC=1.[H][H]>C(O)C.CO.[Pd]>[CH:24]1([CH2:23][NH:22][C:20]([C:10]2[N:11]([CH:17]3[CH2:19][CH2:18]3)[C:12]([CH3:16])=[CH:13][C:14](=[O:15])[C:9]=2[OH:8])=[O:21])[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29]1

Komponenten

6

Edukt 2

HCID 11596355HCID 11596355, VerbindungHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 59769615HCID 59769615, VerbindungAusbeute 63 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23938PalladiumKatalysatorHCID 702EthanolLösungsmittelHCID 887MethanolLösungsmittel

Versuchsvorschrift

A mixture of 3-(benzyloxy)-N-(cyclohexylmethyl)-1-cyclopropyl-6-methyl-4-oxo-1,4-dihydropyridine-2-carboxamide (2.0 g, 4.8 mmol), Pd/C (10% wet, 0.45 g) in ethanol (150 mL) was hydrogenated in a Parr apparatus at 50 psi of hydrogen pressure for 16 h. The reaction mixture was filtered over a pad of Celite® and the Celite® was thoroughly washed with EtOH (25 mL). Evaporation of the solvent afforded a pale pink solid. The solid was dissolved in hot methanol, then cooled to RT as solid product precipitated out. The solid was collected by suction filtration. The mother liquor was concentrated in vacuo and the residual solid was again dissolved in hot methanol and cooled to RT to precipitate out the product, which was then collected. This process was repeated one more time. The three combined white solid fractions weighed 0.95 g (63% yield).

Aufarbeitung

  1. filtrationThe reaction mixture was filtered over a pad of Celite®
  2. washthe Celite® was thoroughly washed with EtOH (25 mL)
  3. customEvaporation of the solvent
  4. customafforded a pale pink solid
  5. customprecipitated out
  6. filtrationThe solid was collected by suction filtration
  7. concentrationThe mother liquor was concentrated in vacuo
  8. dissolutionthe residual solid was again dissolved in hot methanol
  9. temperaturecooled to RT
  10. customto precipitate out the product, which
  11. customwas then collected

Quellen und Nachweise

ORD-Eintrag
ord-13d1692ebddb4f1ebce29c248f5600f7
Quelldatensatz
uspto-grants-2011_02
Patentnummer
US07893269B2

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