Cesium fluoride → HCID 178483994, Verbindung

HRID 81181Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 81181
[F-].[Cs+].[F:3][C:4]([F:9])([F:8])[CH2:5][NH:6][CH3:7].Br[C:11]1[N:28]([CH2:29][C@H:30]2[CH2:35][CH2:34][C@H:33]([CH3:36])[CH2:32][CH2:31]2)[C:14]2[C:15]([C:21]3[CH:22]=[N:23][CH:24]=[C:25]([Cl:27])[CH:26]=3)=[N:16][C:17]([C:19]#[N:20])=[CH:18][C:13]=2[N:12]=1>CS(C)=O.O>[Cl:27][C:25]1[CH:26]=[C:21]([C:15]2[C:14]3[N:28]([CH2:29][C@H:30]4[CH2:35][CH2:34][C@H:33]([CH3:36])[CH2:32][CH2:31]4)[C:11]([N:6]([CH3:7])[CH2:5][C:4]([F:9])([F:8])[F:3])=[N:12][C:13]=3[CH:18]=[C:17]([C:19]#[N:20])[N:16]=2)[CH:22]=[N:23][CH:24]=1

Komponenten

6

Edukt 3

HCID 25953Cesium fluorideHCID 5203012,2,2-trifluoro-N-methylethanamineHCID 178461197HCID 178461197, Verbindung

Produkt 1

HCID 178483994HCID 178483994, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 679Dimethyl SulfoxideLösungsmittelHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
150 °C

Versuchsvorschrift

To a sealed reaction vessel was added cesium fluoride (0.085 g, 0.56 mmol). The reaction vessel was heated to 150° C. for 3 hours with stirring, under high vacuum. The vial was cooled to ambient temperature under high vacuum. The reaction vessel was backfilled with argon, and next was added a solution of 2,2,2-trifluoro-N-methylethanamine (purchased from Enamine) (0.019 g, 0.17 mmol) and 2-bromo-4-(5-chloropyridin-3-yl)-3-((trans-4-methylcyclohexyl)methyl)-3H-imidazo[4,5-c]pyridine-6-carbonitrile (Preparative Example 3.1, 0.025 g, 0.056 mmol) in DMSO (0.30 mL). The reaction was heated to 100° C. for 12 hours. The reaction was cooled, diluted with H2O (2.0 mL) and extracted with EtOAc (2×5.0 mL). The combined organics were dried over anhydrous MgSO4, filtered and concentrated in vacuo to afford 4-(5-chloropyridin-3-yl)-2-(methyl(2,2,2-trifluoroethyl)amino)-3-((trans-4-methylcyclohexyl)methyl)-3H-imidazo[4,5-c]pyridine-6-carbonitrile as a crude residue. MS ESI calc'd. for C23H24ClF3N6 [M+H]+ 477. found 477.

Aufarbeitung

  1. customTo a sealed reaction vessel
  2. temperatureThe vial was cooled to ambient temperature under high vacuum
  3. temperatureThe reaction was heated to 100° C. for 12 hours
  4. temperatureThe reaction was cooled
  5. extractionextracted with EtOAc (2×5.0 mL)
  6. dry with materialThe combined organics were dried over anhydrous MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-d0813ab0276745f881554f8324239601
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846657B2

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