Dimethylformamide → HCID 19921775, compound

Participants

Reaction Steps

In a 100-ml round-bottomed flask, 1.35 g (8.15 mmol) of 4-(5-methyl-1H-imidazol-4-yl)piperidine are placed in 15 ml of dichloromethane and 4 ml of dimethylformamide. 1.32 g (8.15 mmol) of 1H-indazole-3-carboxylic acid and 2.2 ml of triethylamine are added. The mixture is left stirring for 5 minutes. 3.5 ml of diphenylphosphoryl azide are added and the mixture is left stirring for 72 hours. Ethyl acetate is added and the mixture is extracted 3 times with 2N hydrochloric acid. The aqueous phase is recovered and alkalinized with sodium carbonate solution. It is extracted 3 times with ethyl acetate and the organic phase is collected, dried and evaporated to dryness. The residue is purified by chromatography on a column of silica gel, eluting with a dichloromethane/methanol/ammonia solution (90:10:1) mixture.

Provenance & Evidence