3-[4-(benzyloxy)phenyl]-1-ethyl-7-methyl-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one → HCID 58577432, Verbindung

HRID 82634Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 82634
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([N:15]2[C:19]3=[N:20][CH:21]=[CH:22][C:23]([CH3:24])=[C:18]3[N:17]([CH2:25][CH3:26])[C:16]2=[O:27])=[CH:11][CH:10]=1)C1C=CC=CC=1>CN(C=O)C.CCOC(C)=O.[Pd]>[CH2:25]([N:17]1[C:18]2[C:19](=[N:20][CH:21]=[CH:22][C:23]=2[CH3:24])[N:15]([C:12]2[CH:13]=[CH:14][C:9]([OH:8])=[CH:10][CH:11]=2)[C:16]1=[O:27])[CH3:26]

Komponenten

5

Edukt 1

HCID 585773813-[4-(benzyloxy)phenyl]-1-ethyl-7-methyl-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one

Produkt 1

HCID 58577432HCID 58577432, VerbindungAusbeute 84,6 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23938PalladiumKatalysatorHCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of 3-[4-(benzyloxy)phenyl]-1-ethyl-7-methyl-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one (88.3 g) in DMF (540 mL) and EtOAc (1080 mL) was added 10% Pd—C (9.0 g) at room temperature under Ar atmosphere. The mixture was hydrogenated under balloon pressure at room temperature for 5 h. The reaction mixture was filtered through celite, and then insoluble materials were washed with EtOAc (500 mL). The filtrate was concentrated in vacuo. The residue was suspended in EtOAc (350 mL), and the mixture was stirred at room temperature for 2 h. The precipitate was collected by filtration, washed with EtOAc (250 mL) and IPE (100 mL), and dried in vacuo to give 1-ethyl-3-(4-hydroxyphenyl)-7-methyl-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one (56.0 g) as light purple powder.

Aufarbeitung

  1. filtrationThe reaction mixture was filtered through celite
  2. washinsoluble materials were washed with EtOAc (500 mL)
  3. concentrationThe filtrate was concentrated in vacuo
  4. filtrationThe precipitate was collected by filtration
  5. washwashed with EtOAc (250 mL) and IPE (100 mL)
  6. customdried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-08225668b6804fc38c735ad3fc3b19e0
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846713B2

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