1-Amino-2-propanol → 4-[4-(6-fluoro-1H-benzimidazol-2-yl)-9H-carbazol-9-yl]-2-(2(R,S)-hydroxypropylamino)benzamide

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Reaction Steps

The process is carried out as in stage 3 of Example 3, but using 300 mg of 2-fluoro-4-[4-(6-fluoro-1H-benzimidazol-2-yl)carbazol-9-yl]benzonitrile, obtained according to stage 2 of Example 3, 296 mg of potassium carbonate and 1.073 g of 1-amino-2(R,S)-propanol in 3 ml of dimethyl sulphoxide. 1.357 ml of a 1M aqueous solution of sodium hydroxide, 1.313 ml of a 30% aqueous solution of hydrogen peroxide and 7 ml of ethanol are then added to the reaction medium. After treatment as in stage 3 of Example 3, and then purification by flash chromatography on silica gel, elution being carried out with mixtures of dichloromethane and ethanol (95/5 to 90/10 by volume), followed by crystallization from 10 ml of diisopropyl ether, 180 mg of 4-[4-(6-fluoro-1H-benzimidazol-2-yl)-9H-carbazol-9-yl]-2-(2(R,S)-hydroxypropylamino)benzamide are thus obtained in the form of a beige solid, the characteristics of which are the following:

Provenance & Evidence