Ammonium Chloride → 4-[4-(6-cyanopyridin-3-yl)-9H-carbazol-9-yl]-2-[(3-hydroxypropyl)amino]benzamide

Participants

Reaction Steps

260 mg of (1H-benzotriazol-1-yloxy)[tris(dimethylamino)]phosphonium hexafluorophosphate (BOP), 79 mg of hydroxybenzotriazole (HOBT), 41 mg (0.8 mmol) of ammonium chloride and 0.26 ml of diisopropylethylamine are successively added to a solution of 180 mg of 4-[4-(6-cyanopyridin-3-yl)-9H-carbazol-9-yl]-2-[(3-hydroxypropyl)amino]benzoic acid in 10 ml of N,N-dimethylformamide. The reaction mixture is stirred at ambient temperature for 4 hours and then diluted with distilled water and extracted with ethyl acetate. The organic phase is subsequently washed with distilled water and a saturated solution of sodium chloride, dried over magnesium sulphate, filtered and concentrated under reduced pressure. The residue is purified by silica gel chromatography, elution being carried out with a mixture of dichloromethane and methanol (96/4 by volume), and triturated in diisopropyl ether, so as to give 60 mg of 4-[4-(6-cyanopyridin-3-yl)-9H-carbazol-9-yl]-2-[(3-hydroxypropyl)amino]benzamide in the form of a white solid, the characteristics of which are the following:

Provenance & Evidence