Potassium Carbonate → 2-methylpropan-2-yl 4-[4-(6-cyanopyridin-3-yl)-9H-carbazol-9-yl]-2-[(8-methyl-8-azabicyclo[3.2.1]oct-3-yl)amino]benzoate

HRID 1877521Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1877521
C(=O)([O-])[O-].[K+].[K+].[CH3:7][N:8]1[CH:13]2[CH2:14][CH2:15][CH:9]1[CH2:10][CH:11]([NH2:16])[CH2:12]2.[C:17]([C:19]1[N:24]=[CH:23][C:22]([C:25]2[C:37]3[C:36]4[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=4)[N:30]([C:38]4[CH:50]=[CH:49][C:41]([C:42]([O:44][C:45]([CH3:48])([CH3:47])[CH3:46])=[O:43])=[C:40](F)[CH:39]=4)[C:29]=3[CH:28]=[CH:27][CH:26]=2)=[CH:21][CH:20]=1)#[N:18]>CS(C)=O.O>[C:17]([C:19]1[N:24]=[CH:23][C:22]([C:25]2[C:37]3[C:36]4[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=4)[N:30]([C:38]4[CH:39]=[CH:40][C:41]([C:42]([O:44][C:45]([CH3:46])([CH3:47])[CH3:48])=[O:43])=[C:49]([NH:16][CH:11]5[CH2:10][CH:9]6[N:8]([CH3:7])[CH:13]([CH2:14][CH2:15]6)[CH2:12]5)[CH:50]=4)[C:29]=3[CH:28]=[CH:27][CH:26]=2)=[CH:21][CH:20]=1)#[N:18]

Komponenten

6

Edukt 3

HCID 11430Potassium CarbonateHCID 4083948-Methyl-8-azabicyclo[3.2.1]octan-3-amineHCID 583382932-methylpropan-2-yl 4-[4-(6-cyanopyridin-3-yl)-9H-carbazol-9-yl]-2-fluorobenzoate

Produkt 1

HCID 673091362-methylpropan-2-yl 4-[4-(6-cyanopyridin-3-yl)-9H-carbazol-9-yl]-2-[(8-methyl-8-azabicyclo[3.2.1]oct-3-yl)amino]benzoateAusbeute 27 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 679Dimethyl SulfoxideLösungsmittelHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

0.89 g of potassium carbonate and 6 g of 8-methyl-8-azabicyclo[3.2.1]octan-3-amine are successively added to a solution of 1 g of 2-methylpropan-2-yl 4-[4-(6-cyanopyridin-3-yl)-9H-carbazol-9-yl]-2-fluorobenzoate, obtained in stage 1 of Example 49, in 8 ml of dimethyl sulphoxide. The reaction mixture is heated at 100° C. for 1 hour and 40 minutes 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 dichloromethane and methanol (92/8 as mixtures), so as to give 0.34 g of 2-methylpropan-2-yl 4-[4-(6-cyanopyridin-3-yl)-9H-carbazol-9-yl]-2-[(8-methyl-8-azabicyclo[3.2.1]oct-3-yl)amino]benzoate in the form of a white powder, 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 dichloromethane and methanol (92/8 as mixtures)

Quellen und Nachweise

ORD-Eintrag
ord-90a2c2bf65c04ece8132aeb3aa1b13f9
Quelldatensatz
uspto-grants-2012_11
Patentnummer
US08309721B2

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