Cesium carbonate → 5-(2-Fluoro-phenoxy)-2-pyrazin-2-yl-6-(6-cyano-pyridin-3-yloxy)-1H-benzimidazole

HRID 13329

Reaktionsgleichung

Reaktionsgleichung von HRID 13329
Br[C:2]1[CH:3]=[N:4][C:5]([C:8]#[N:9])=N[CH:7]=1.[C:10](=O)([O-])[O-].[Cs+].[Cs+].[F:16][C:17]1[CH:39]=[CH:38][CH:37]=[CH:36][C:18]=1[O:19][C:20]1[C:34]([OH:35])=[CH:33][C:23]2[NH:24][C:25]([C:27]3[CH:32]=[N:31][CH:30]=[CH:29][N:28]=3)=[N:26][C:22]=2[CH:21]=1>CN1CCCC1=O>[F:16][C:17]1[CH:39]=[CH:38][CH:37]=[CH:36][C:18]=1[O:19][C:20]1[C:34]([O:35][C:2]2[CH:7]=[CH:10][C:5]([C:8]#[N:9])=[N:4][CH:3]=2)=[CH:33][C:23]2[NH:24][C:25]([C:27]3[CH:32]=[N:31][CH:30]=[CH:29][N:28]=3)=[N:26][C:22]=2[CH:21]=1

Komponenten

5

Edukt 3

HCID 10796Cesium carbonateHCID 6865465-Bromopyrimidine-2-carbonitrileHCID 1356979845-(2-fluorophenoxy)-6-hydroxy-2-pyrazin-2-yl-1H-benzimidazole

Produkt 1

HCID 231451425-(2-Fluoro-phenoxy)-2-pyrazin-2-yl-6-(6-cyano-pyridin-3-yloxy)-1H-benzimidazole

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 13387N-methyl-2-pyrrolidoneLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

7.0 mg of 5-bromo-2-cyano-pyrimidine and 15 mg of cesium carbonate were added to an N-methylpyrrolidinone (0.5 ml) solution of 7.0 mg of 5-(2-fluorophenoxy)-6-hydroxy-2-pyrazin-2-yl-1H-benzimidazole obtained in the step 1, and the reaction liquid was stirred at 90° C. for 15 minutes. The reaction mixture was purified through reversed-phase middle-pressure liquid chromatography [ODS-AS-360-CC (by YMC), mobile phase: water-acetonitrile-0.1% trifluoroacetic acid]. The resulting fraction was diluted with ethyl acetate, washed with aqueous saturated sodium bicarbonate, and dried with anhydrous sodium sulfate. The solvent was evaporated away under reduced pressure to obtain the entitled compound a colorless solid.

Aufarbeitung

  1. customobtained in the step 1
  2. customthe reaction liquid
  3. customThe reaction mixture was purified through reversed-phase middle-pressure liquid chromatography [ODS-AS-360-CC (by YMC), mobile phase: water-acetonitrile-0.1% trifluoroacetic acid]
  4. additionThe resulting fraction was diluted with ethyl acetate
  5. washwashed with aqueous saturated sodium bicarbonate
  6. dry with materialdried with anhydrous sodium sulfate
  7. customThe solvent was evaporated away under reduced pressure
  8. customto obtain the entitled compound a colorless solid

Quellen und Nachweise

ORD-Eintrag
ord-16448ad5041148a9ab574d8ff2b42526
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07728025B2

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