StartseiteMCPWorkbenchSkills
StartseiteWorkbenchBenachrichtigungenMein Bereich
llms.txt · MCP-AnleitungDatenschutz · Nutzungsbedingungen · Supportv1.8.0
  1. Startseite
  2. /Reaktion

Potassium Carbonate → N-[(1S)-1-(3-aminophenyl)ethyl]-4-(8-chloroimidazo[1,2-a]pyridin-3-yl)-5-fluoropyrimidine-2-amine

HRID 2238672
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2238672
[Cl:1][C:2]1[C:3]2[N:4]([C:8]([C:11]3[C:16]([F:17])=[CH:15][N:14]=[C:13](Cl)[N:12]=3)=[CH:9][N:10]=2)[CH:5]=[CH:6][CH:7]=1.[NH2:19][C@H:20]([C:22]1[CH:23]=[C:24]([CH:26]=[CH:27][CH:28]=1)[NH2:25])[CH3:21].C(=O)([O-])[O-].[K+].[K+]>CS(C)=O>[NH2:25][C:24]1[CH:23]=[C:22]([C@@H:20]([NH:19][C:13]2[N:12]=[C:11]([C:8]3[N:4]4[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[C:3]4=[N:10][CH:9]=3)[C:16]([F:17])=[CH:15][N:14]=2)[CH3:21])[CH:28]=[CH:27][CH:26]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 40637894(S)-3-(1-aminoethyl)anilineHCID 862274958-Chloro-3-(2-chloro-5-fluoropyrimidin-4-yl)imidazo[1,2-a]pyridine

Produkt 1

HCID 68690421N-[(1S)-1-(3-aminophenyl)ethyl]-4-(8-chloroimidazo[1,2-a]pyridin-3-yl)-5-fluoropyrimidine-2-amineAusbeute 20,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679
Dimethyl Sulfoxide
Lösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

90 mg of the 8-chloro-3-(2-chloro-5-fluoropyrimidin-4-yl)imidazo[1,2-a]pyridine [125-2] was dissolved in 3 mL of dimethylsulfoxide, then 46.6 mg of 3-[(1S)-1-aminoethyl]aniline and 100 mg of potassium carbonate were added thereto, and stirred at 60° C. for 5 hours. The reaction mixture was cooled back to room temperature, and purified by preparative reversed phase liquid chromatography. Thereto, a saturated aqueous solution of sodium hydrogen carbonate was added, and the mixture was extracted with chloroform. The organic layer was washed with saturated brine, and dried over anhydrous sodium sulfate. The insolubles were filtered, the filtrate was concentrated under reduced pressure, and 25 mg of N-[(1S)-1-(3-aminophenyl)ethyl]-4-(8-chloroimidazo[1,2-a]pyridin-3-yl)-5-fluoropyrimidine-2-amine [125-3] was obtained as a brown oily product.

Aufarbeitung

  1. temperatureThe reaction mixture was cooled back to room temperature
  2. custompurified by preparative reversed phase liquid chromatography
  3. additionThereto, a saturated aqueous solution of sodium hydrogen carbonate was added
  4. extractionthe mixture was extracted with chloroform
  5. washThe organic layer was washed with saturated brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationThe insolubles were filtered
  8. concentrationthe filtrate was concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-0d05363552c8450aa0ac5dab546a190a
Quelldatensatz
uspto-grants-2010_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07718801B2

Notizen zur Reaktion

Wird geladen…

Auf dieser SeiteKomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion