Cesium carbonate → HCID 117843135, Verbindung

HRID 2209073Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2209073
Br[CH:2]1[CH2:5][CH2:4][CH2:3]1.[CH3:6][O:7][C:8]1[CH:9]=[C:10]([C:16]2[N:21]=[C:20]([O:22][C@@H:23]([C@H:25]3[CH2:29][NH:28][C:27](=[O:30])[CH2:26]3)[CH3:24])[C:19]3[NH:31][CH:32]=[N:33][C:18]=3[CH:17]=2)[CH:11]=[CH:12][C:13]=1[O:14][CH3:15].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C.C(OCC)(=O)C>[CH:2]1([N:31]2[C:19]3[C:20]([O:22][C@@H:23]([C@H:25]4[CH2:29][NH:28][C:27](=[O:30])[CH2:26]4)[CH3:24])=[N:21][C:16]([C:10]4[CH:11]=[CH:12][C:13]([O:14][CH3:15])=[C:8]([O:7][CH3:6])[CH:9]=4)=[CH:17][C:18]=3[N:33]=[CH:32]2)[CH2:5][CH2:4][CH2:3]1

Komponenten

6

Edukt 3

HCID 10796Cesium carbonateHCID 78110BromocyclobutaneHCID 178488441HCID 178488441, Verbindung

Produkt 1

HCID 117843135HCID 117843135, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

Bromocyclobutane (18 mg, 0.137 mmol) was added to a mixture of (R)-4-((R)-1-(6-(3,4-dimethoxyphenyl)-3H-imidazo[4,5-c]pyridin-4-yloxy)ethyl)pyrrolidin-2-one 3.09 (50 mg, 0.131 mmol) and cesium carbonate (127 mg, 0.392 mmol) in 5 mL of DMF at room temperature. Reaction mixture was heated at 80° C. in a microwave reactor for one hour. Reaction mixture was taken up in ethyl acetate and washed with saturated NaHCO3 (aq) and brine. The separated organic layers were dried (MgSO4), filtered, and concentrated under reduced pressure. Residues were purified via reverse phase chromatography to yield (R)-4-((R)-1-(3-cyclobutyl-6-(3,4-dimethoxyphenyl)-3H-imidazo[4,5-c]pyridin-4-yloxy)ethyl)pyrrolidin-2-one 3.27.

Aufarbeitung

  1. customReaction mixture
  2. customReaction mixture
  3. washwashed with saturated NaHCO3 (aq) and brine
  4. dry with materialThe separated organic layers were dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customResidues were purified via reverse phase chromatography

Quellen und Nachweise

ORD-Eintrag
ord-44580f456a7842dfaff71eac34a6b44e
Quelldatensatz
uspto-grants-2016_06
Patentnummer
US09376441B2

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