Hydrochloric Acid → HCID 178472391, Verbindung

HRID 518635Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 518635
C([O:8][CH2:9][CH2:10][O:11][C:12]1[N:17]=[CH:16][C:15]2[NH:18]/[C:19](=[N:32]\[C:33](=[O:41])[C:34]3[CH:39]=[CH:38][CH:37]=[C:36]([F:40])[CH:35]=3)/[N:20]([C@@H:21]3[CH2:26][CH2:25][C@H:24]([C:27]([O:29][CH2:30][CH3:31])=[O:28])[CH2:23][CH2:22]3)[C:14]=2[CH:13]=1)C1C=CC=CC=1.Cl>CCO.[Pd]>[F:40][C:36]1[CH:35]=[C:34]([CH:39]=[CH:38][CH:37]=1)[C:33](/[N:32]=[C:19]1/[N:20]([C@@H:21]2[CH2:22][CH2:23][C@H:24]([C:27]([O:29][CH2:30][CH3:31])=[O:28])[CH2:25][CH2:26]2)[C:14]2[CH:13]=[C:12]([O:11][CH2:10][CH2:9][OH:8])[N:17]=[CH:16][C:15]=2[NH:18]/1)=[O:41]

Komponenten

5

Edukt 2

HCID 313Hydrochloric AcidHCID 178472392HCID 178472392, Verbindung

Produkt 1

HCID 178472391HCID 178472391, VerbindungAusbeute 100,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 702EthanolLösungsmittel2×

Versuchsvorschrift

A round bottom flask under nitrogen was charged with cis-ethyl 4-((E)-6-(2-(benzyloxy)ethoxy)-2-(3-fluorobenzoylimino)-2,3-dihydro-1H-imidazo[4,5-c]pyridin-1-yl)cyclohexanecarboxylate (2.5 g, 4.46 mmol), 10% Pd/C (0.712 g, 0.669 mmol), EtOH (8.92 mL), and concentrated HCl (0.372 mL, 4.46 mmol). The reaction mixture was stirred under an atmosphere of hydrogen for 24 hours. The mixture was diluted with EtOH (50 mL) and filtered through Celite® brand filter aid. The cake was washed with DCM (50 mL), EtOH (50 mL), and MeOH (50 mL), and the filtrate was concentrated to dryness. The residue was dissolved in 2% MeOH/DCM (100 mL) and washed with aqueous NaHCO3 (50 mL). The organic layer was dried over sodium sulfate and concentrated under reduced pressure to afford cis-ethyl 4-((E)-2-(3-fluorobenzoylimino)-6-(2-hydroxyethoxy)-2,3-dihydro-1H-imidazo[4,5-c]pyridin-1-yl)cyclohexanecarboxylate as a tan solid (2.1 g, 100% yield). MS m/z=471.2 [M+H]. Calc'd for C24H27FN4O5: 470.2.

Aufarbeitung

  1. filtrationfiltered through Celite® brand
  2. filtrationfilter aid
  3. washThe cake was washed with DCM (50 mL), EtOH (50 mL), and MeOH (50 mL)
  4. concentrationthe filtrate was concentrated to dryness
  5. dissolutionThe residue was dissolved in 2% MeOH/DCM (100 mL)
  6. washwashed with aqueous NaHCO3 (50 mL)
  7. dry with materialThe organic layer was dried over sodium sulfate
  8. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-67ac1d74fe44468b8671d815a1564928
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09115127B2

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