Cesium carbonate → HCID 117843200, Verbindung

HRID 2209064Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2209064
FC(F)(F)S(O[CH2:7][C:8]([F:11])([F:10])[F:9])(=O)=O.[CH3:14][O:15][C:16]1[CH:17]=[C:18]([C:24]2[N:29]=[C:28]([O:30][C@@H:31]([C@H:33]3[CH2:37][NH:36][C:35](=[O:38])[CH2:34]3)[CH3:32])[C:27]3[NH:39][CH:40]=[N:41][C:26]=3[CH:25]=2)[CH:19]=[CH:20][C:21]=1[O:22][CH3:23].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C.C(OCC)(=O)C>[CH3:14][O:15][C:16]1[CH:17]=[C:18]([C:24]2[N:29]=[C:28]([O:30][C@@H:31]([C@H:33]3[CH2:37][NH:36][C:35](=[O:38])[CH2:34]3)[CH3:32])[C:27]3[N:39]([CH2:7][C:8]([F:11])([F:10])[F:9])[CH:40]=[N:41][C:26]=3[CH:25]=2)[CH:19]=[CH:20][C:21]=1[O:22][CH3:23].[CH3:14][O:15][C:16]1[CH:17]=[C:18]([C:24]2[N:29]=[C:28]([O:30][C@@H:31]([C@H:33]3[CH2:37][NH:36][C:35](=[O:38])[CH2:34]3)[CH3:32])[C:27]3[N:39]=[CH:40][N:41]([CH2:7][C:8]([F:11])([F:10])[F:9])[C:26]=3[CH:25]=2)[CH:19]=[CH:20][C:21]=1[O:22][CH3:23]

Komponenten

7

Edukt 3

HCID 10796Cesium carbonateHCID 803662,2,2-Trifluoroethyl trifluoromethanesulfonateHCID 178488441HCID 178488441, Verbindung

Produkt 2

HCID 117843200HCID 117843200, VerbindungHCID 117843532HCID 117843532, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

2,2,2-trifluoroethyl trifluoromethanesulfonate (13 mg, 0.056 mmol) was added to a solution of (R)-4-((R)-1-(6-(3,4-dimethoxyphenyl)-3H-imidazo[4,5-c]pyridin-4-yloxy)ethyl)pyrrolidin-2-one 3.09 (20 mg, 0.052 mmol) and cesium carbonate (43 mg, 0.132 mmol) in 5 mL of DMF at room temperature. After 1 h, reaction mixture was taken up in ethyl acetate (100 mL) and washed with saturated NaHCO3 (aq) (2×100 mL) and brine. The separated organic layers were dried (MgSO4), filtered, and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography to yield (R)-4-((R)-1-(6-(3,4-dimethoxyphenyl)-3-(2,2,2-trifluoroethyl)-3H-imidazo[4,5-c]pyridin-4-yloxy)ethyl)pyrrolidin-2-one 3.10 and (R)-4-((R)-1-(6-(3,4-dimethoxyphenyl)-1-(2,2,2-trifluoroethyl)-1H-imidazo[4,5-c]pyridin-4-yloxy)ethyl)pyrrolidin-2-one 3.11.

Aufarbeitung

  1. customreaction mixture
  2. washwashed with saturated NaHCO3 (aq) (2×100 mL) and brine
  3. dry with materialThe separated organic layers were dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting residue was purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-0f145a2b3c5a4aa5a31c7afbd8d3a659
Quelldatensatz
uspto-grants-2016_06
Patentnummer
US09376441B2

Notizen zur Reaktion

Wird geladen…