Cyclohexylamine → N-cyclohexyl-5-nitro-1H-indazole-3-carboxamide

Participants

Reaction Steps

N-Cyclohexyl-5-nitro-1H-indazole-3-carboxamide can be obtained in the following way: a solution of 2.5 g of 5-nitro-1H-indazole-3-carboxylic acid, of 150 ml of dichloromethane, of 75 ml of dimethylformamide, 0.16 g of 1-hydroxybenzotriazole and of 2.75 g 1-ethyl-3-[3-(dimethylamino)propyl]carbodiimide hydrochloride is stirred for 15 minutes at a temperature of 25° C. 1.7 ml of cyclohexylamine and 1.7 ml of triethylamine are then added. The reaction medium is maintained with stirring for 70 hours and concentrated by evaporation under reduced pressure. The residue thus obtained is taken up with 50 ml of dichloromethane and 50 ml of diisopropyl ethyl. After filtration, the paste obtained is taken up with 80 ml of distilled water and the solid form is filtered through a sintered glass funnel, washed with two times 50 ml of water and then dried under reduced pressure. The resulting solid is taken up with 50 ml of ethyl acetate, filtered through a sintered glass filter, washed with two times 25 ml of ethyl acetate and dried at 50° C. under reduced pressure. 1.57 g of N-cyclohexyl-5-nitro-1H-indazole-3-carboxamide are thus obtained in the form of a beige solid (Rf=0.90, silica gel thin layer chromatography, eluent: chloroform/methanol/20% aqueous ammonia (12/3/0.5 by volume)).

Provenance & Evidence