Water → HCID 178456700, Verbindung

HRID 433011

Reaktionsgleichung

Reaktionsgleichung von HRID 433011
Br[CH:2]([C:17]1[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=1)[C:3]([C:5]1[CH:16]=[CH:15][C:8]2[N:9]=[N:10][N:11]([CH:12]([CH3:14])[CH3:13])[C:7]=2[CH:6]=1)=O.C(=O)([O-])[O-].[Cs+].[Cs+].Cl.[C:31]([C:34]1[CH:35]=[N:36][CH:37]=[CH:38][CH:39]=1)(=[NH:33])[NH2:32].O>CN(C)C=O>[F:23][C:20]1[CH:21]=[CH:22][C:17]([C:2]2[N:33]=[C:31]([C:34]3[CH:35]=[N:36][CH:37]=[CH:38][CH:39]=3)[NH:32][C:3]=2[C:5]2[CH:16]=[CH:15][C:8]3[N:9]=[N:10][N:11]([CH:12]([CH3:14])[CH3:13])[C:7]=3[CH:6]=2)=[CH:18][CH:19]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 10796Cesium carbonateHCID 202042Nicotinamidine hydrochlorideHCID 187607892-bromo-2-(4-fluoro-phenyl)-1-(3-isopropyl-3H-benzotriazol-5-yl)-ethanone

Produkt 1

HCID 178456700HCID 178456700, VerbindungAusbeute 39,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

To a stirred solution of 29 mg of 2-bromo-2-(4-fluoro-phenyl)-1-(3-isopropyl-3H-benzotriazol-5-yl)-ethanone in 0.38 mL of N,N-dimethylformamide was added 75 mg of cesium carbonate and 24 mg of 3-amidinopyridine hydrochloride. The mixture was heated at 50° C. for 30 min. The orange-brown mixture was cooled to 22° C., transferred to a separatory funnel with water, and extracted with ethyl acetate (3×). The combined organic layers were washed with brine, dried (sodium sulfate), filtered, and the filtrate was concentrated to an orange oil. This oil was purified by flash chromatography (eluting with ethyl acetate) to give 12 mg of 6-[5-(4-fluoro-phenyl)-2-pyridin-3-yl-3H-imidazol-4-yl]-1-isopropyl-1H-benzotriazole as a white solid. LCMS m/z 399 (M+1).

Aufarbeitung

  1. temperatureThe orange-brown mixture was cooled to 22° C.
  2. extractionextracted with ethyl acetate (3×)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried (sodium sulfate)
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated to an orange oil
  7. customThis oil was purified by flash chromatography (eluting with ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-cd4a29b579b448c4a6427bdd90aad16a
Quelldatensatz
uspto-grants-2003_12
Patentnummer
US06664395B2

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