Isopropylamine → HCID 86629520, compound

Participants

Reaction Conditions

Reaction Steps

2-Chloro-6-cyano-4-methyl-nicotinic acid (0.315 g, 1.61 mmol) in concentrated HCl (8 ml) was heated at 100° C. for 45 minutes and then all solvent was removed in vacuo to yield a pale yellow crystalline solid. The crude solid, EDCI (0.339 g, 1.77 mmol) and HOBt (0.239 g, 1.77 mmol) were combined in DMF (8 ml) to give a pale yellow solution. To this solution was added DIPEA (1.85 ml, 10.6 mmol) followed by isopropylamine (137 μL, 1.61 mmol) and the resulting mixture was stirred at 25° C. for 16 hours. The reaction mixture was quenched with water (3 ml) and then dry loaded onto silica gel and purified using column chromatography (MeCN/MeOH/NH4OH, 8:1:1, v/v/v) to give 2-chloro-6-isopropylcarbamoyl-4-methyl-nicotinic acid (0.195 g, 47%).

Provenance & Evidence