Reaktion #41576

Reaktionsgleichung

1-methyl-1H-pyrazole-3-carboxylic acid

hydroxybenzotriazole

1-(3-dimethylaminopropyl)-3-ethylcarbodiimide monohydrochloride

4-(2-fluoro-phenoxy)-5-(6-methanesulfonyl-pyridin-3-yloxy)-benzene-1,2-diamine

→

compound

5-(2-Fluoro-phenoxy)-2-(1-methyl-1H-pyrazol-3-yl)-6-(6-methanesulfonyl-pyridin-3-yloxy)-1H-benzimidazole

Lösungsmittel

dimethylformamide

ethyl acetate

chloroform

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigethe reaction liquid
2. 2
   SonstigeThe reaction liquid
3. 3
   Waschenwashed with water
4. 4
   Trocknendried with anhydrous sodium sulfate
5. 5
   SonstigeThe solvent was evaporated away under reduced pressure, and 3 mg of p-toluenesulfonic acid
6. 6
   workup.ADDITIONwas added to the resulting residue
7. 7
   Sonstigethe reaction liquid
8. 8
   workup.STIRRINGwas stirred at 120° C. for 2 hours
9. 9
   SonstigeThe reaction liquid
10. 10
    Waschenwashed with water
11. 11
    Trocknendried with anhydrous sodium sulfate
12. 12
    SonstigeThe solvent was evaporated away under reduced pressure
13. 13
    Sonstigethe resulting residue was purified
14. 14
    Sonstigethrough partitioning thin-layer chromatography (Kieselgel™ 60F254, Art 5744 (by Merck), chloroform/methanol=15/1)

Vorschrift

4.3 mg of 1-methyl-1H-pyrazole-3-carboxylic acid, 6.0 mg of hydroxybenzotriazole and 8.5 mg of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide monohydrochloride were added to a dimethylformamide (0.5 ml) solution of 15 mg of 4-(2-fluoro-phenoxy)-5-(6-methanesulfonyl-pyridin-3-yloxy)-benzene-1,2-diamine obtained in Example 200, and the reaction liquid was stirred overnight at room temperature. The reaction liquid was diluted with chloroform, washed with water, and dried with anhydrous sodium sulfate. The solvent was evaporated away under reduced pressure, and 3 mg of p-toluenesulfonic acid was added to the resulting residue, and the reaction liquid was stirred at 120° C. for 2 hours. The reaction liquid was diluted with ethyl acetate, washed with water, and dried with anhydrous sodium sulfate. The solvent was evaporated away under reduced pressure, and the resulting residue was purified through partitioning thin-layer chromatography (Kieselgel™ 60F254, Art 5744 (by Merck), chloroform/methanol=15/1) to obtain the entitled compound as a white solid.

Quelle