Diisopropylethylamine → HCID 58133386, compound

Participants

Reaction Steps

To a solution of 2-pyridyl-acetic acid hydrochloride (310 mg) and 2-amino-nicotinic acid methyl ester (270 mg) (Example 1.1) in dichloromethane (5 ml) was added diisopropylethylamine (0.32 ml). The reaction mixture was stirred at ambient temperature for 20 minutes. To this solution was added 4-dimethylaminopyridine (43 mg) and N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (“EDAC”) (410 mg). The reaction mixture was stirred at ambient temperature for 20 hours. The reaction mixture was partitioned between dichloromethane and water. The phases were separated and the organic layer concentrated. The residue was purified by column chromatography on silica gel (eluent: 15% acetone in dichloromethane) to give 2-(2-pyridin-2-yl-acetylamino)-nicotinic acid methyl ester as a yellow solid (86 mg). 1H-NMR (400 MHz, CDCl3): 11.14 (bs, 1H), 8.63-8.64 (m, 1H), 8.58-8.59 (dd, 1H), 8.25-8.27 (dd, 1H), 7.66-7.70 (m, 1H), 7.38 (d, 1H), 7.20-7.23 (m, 1H), 7.05-7.08 (dd, 1H), 4.11 (s, 2H), 3.92 (s, 3H) ppm.

Provenance & Evidence