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Potassium Carbonate → tert-butyl 3-{2-[4-(2-cyano-7-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-2-(trifluoromethyl)phenoxy]ethyl}-8-azabicyclo[3.2.1]octane-8-carboxylate

HRID 522265
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 522265
CC1C=CC(S([O:11][CH2:12][CH2:13][CH:14]2[CH2:20][CH:19]3[N:21]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH:16]([CH2:17][CH2:18]3)[CH2:15]2)(=O)=O)=CC=1.C(=O)([O-])[O-].[K+].[K+].O[C:36]1[CH:41]=[CH:40][C:39]([C:42]2[C:43]3[CH:52]=[CH:51][N:50]([CH3:53])[C:44]=3[N:45]=[C:46]([C:48]#[N:49])[N:47]=2)=[CH:38][C:37]=1[C:54]([F:57])([F:56])[F:55]>CC(N(C)C)=O>[C:48]([C:46]1[N:47]=[C:42]([C:39]2[CH:40]=[CH:41][C:36]([O:11][CH2:12][CH2:13][CH:14]3[CH2:15][CH:16]4[N:21]([C:22]([O:24][C:25]([CH3:26])([CH3:27])[CH3:28])=[O:23])[CH:19]([CH2:18][CH2:17]4)[CH2:20]3)=[C:37]([C:54]([F:57])([F:56])[F:55])[CH:38]=2)[C:43]2[CH:52]=[CH:51][N:50]([CH3:53])[C:44]=2[N:45]=1)#[N:49]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 117899538Tert-butyl 3-(2-{[(4-methylphenyl)sulfonyl]oxy}ethyl)-8-azabicyclo[3.2.1]octane-8-carboxylateHCID 1370152264-[4-hydroxy-3-(trifluoromethyl)phenyl]-7-methyl-7H-pyrrolo[2,3-d]pyrimidine-2-carbonitrile

Produkt 1

HCID 117899598tert-butyl 3-{2-[4-(2-cyano-7-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-2-(trifluoromethyl)phenoxy]ethyl}-8-azabicyclo[3.2.1]octane-8-carboxylate
Ausbeute 83,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 31374DimethylacetamideLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

tert-Butyl 3-(2-{[(4-methylphenyl)sulfonyl]oxy}ethyl)-8-azabicyclo[3.2.1]octane-8-carboxylate (150 mg) and potassium carbonate (100 mg) were added to a solution of 4-[4-hydroxy-3-(trifluoromethyl)phenyl]-7-methyl-7H-pyrrolo[2,3-d]pyrimidine-2-carbonitrile (100 mg) in DMAc (2 mL) at room temperature, and the mixture was stirred at 80° C. for 1 hour. After the reaction mixture was cooled to room temperature, extraction thereof was performed using EtOAc, and the extract was washed with water and saturated brine. The organic layer was dried over MgSO4 and filtered, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (Hex:EtOAc=80:20 to 50:50), whereby tert-butyl 3-{2-[4-(2-cyano-7-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-2-(trifluoromethyl)phenoxy]ethyl}-8-azabicyclo[3.2.1]octane-8-carboxylate (146 mg) was obtained as a white solid.

Aufarbeitung

  1. temperatureAfter the reaction mixture was cooled to room temperature
  2. extractionextraction
  3. washthe extract was washed with water and saturated brine
  4. dry with materialThe organic layer was dried over MgSO4
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (Hex:EtOAc=80:20 to 50:50)

Quellen und Nachweise

ORD-Eintrag
ord-1d5bc843a85347e0a3f0c7ba562b6f86
Quelldatensatz
uspto-grants-2016_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09328118B2

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