Potassium Carbonate → HCID 178450725, Verbindung

HRID 1877468Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1877468
[C:1](=[O:4])([O-])[O-].[K+].[K+].[C:7]([C:9]1[N:14]=[CH:13][C:12]([C:15]2[C:27]3[C:26]4[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=4)[N:20]([C:28]4[CH:40]=[CH:39][C:31]([C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])=[C:30](F)[CH:29]=4)[C:19]=3[CH:18]=[CH:17][CH:16]=2)=[CH:11][CH:10]=1)#[N:8]>CS(C)=O.O>[C:7]([C:9]1[N:14]=[CH:13][C:12]([C:15]2[C:27]3[C:26]4[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=4)[N:20]([C:28]4[CH:40]=[CH:39][C:31]([C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])=[C:30]([NH:20][C@H:19]5[CH2:27][CH2:26][C@H:1]([OH:4])[CH2:17][CH2:18]5)[CH:29]=4)[C:19]=3[CH:18]=[CH:17][CH:16]=2)=[CH:11][CH:10]=1)#[N:8]

Komponenten

5

Edukt 2

HCID 11430Potassium CarbonateHCID 583382932-methylpropan-2-yl 4-[4-(6-cyanopyridin-3-yl)-9H-carbazol-9-yl]-2-fluorobenzoate

Produkt 1

HCID 178450725HCID 178450725, VerbindungAusbeute 73,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 679Dimethyl SulfoxideLösungsmittelHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

0.3 g of potassium carbonate and 1.68 g of 4-trans-aminocyclohexanol are successively added to a solution of 0.34 g of 2-methylpropan-2-yl 4-[4-(6-cyanopyridin-3-yl)-9H-carbazol-9-yl]-2-fluorobenzoate in 6 ml of dimethyl sulphoxide. The reaction mixture is heated at 90° C. for 2 hours in a microwave, and then diluted with distilled water. The aqueous phase is extracted twice with ethyl acetate and the combined organic phases are washed with water and a saturated solution of sodium chloride, dried over magnesium sulphate and concentrated to dryness under reduced pressure. The residue is purified by silica gel chromatography, elution being carried out with a mixture of cyclohexane and ethyl acetate (75/25 by volume), so as to give 0.15 g of 2-methylpropan-2-yl 4-[4-(6-cyanopyridin-3-yl)-9H-carbazol-9-yl]-2-[(trans-4-hydroxycyclohexyl)amino]benzoate in the form of a white solid, the characteristics of which are the following:

Aufarbeitung

  1. extractionThe aqueous phase is extracted twice with ethyl acetate
  2. washthe combined organic phases are washed with water
  3. dry with materiala saturated solution of sodium chloride, dried over magnesium sulphate
  4. concentrationconcentrated to dryness under reduced pressure
  5. customThe residue is purified by silica gel chromatography, elution
  6. additionbeing carried out with a mixture of cyclohexane and ethyl acetate (75/25 by volume)

Quellen und Nachweise

ORD-Eintrag
ord-ee9de1a9b03c41169b756f4d9dd07ce2
Quelldatensatz
uspto-grants-2012_11
Patentnummer
US08309721B2

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