Water → Diisopropyl Ether

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Reaction Steps

In a 10 ml round-bottomed flask, dissolve 200 mg of [4-(5-carboxy-1H-benzimidazol-2-yl)-9H-fluoren-9(R,S)-yl]amide of 1H-pyrrolo[2,3-b]pyridine-4-carboxylic acid, obtained in Example 206, in 2.5 ml of dimethylformamide, then add successively 100 μl of N,N-dimethylethylenediamine, 79 mg of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDCI) and 28 mg of 1-hydroxybenzotriazole (HOBT), and then stir for 20 hours at room temperature. Bring the dimethylformamide to dryness, add water, and drain the precipitate that formed and then wash with water and then with a 10% saturated solution of sodium hydrogen carbonate and, finally, with water. The crude solid obtained is dried and then purified by flash chromatography on silica gel (40-63 μm), eluting with a mixture of dichloromethane and ammonia as a 7N solution in methanol (95/5 then 9/1 by volume). After formation of a paste with diisopropyl ether, in this way we obtain 103 mg of 4-[5-(2-dimethylaminoethyl)aminocarbonyl-1H-benzimidazol-2-yl)-9H-fluoren-9(R,S)-yl]amide of 1H-pyrrolo[2,3-b]pyridine-4-carboxylic acid, in the form of an off-white powder with the following characteristics:

Provenance & Evidence