Fusaric Acid → 5-Butylpyridine-2-carbonyl chloride

Participants

Reaction Steps

A solution of 5-butylpicolinic acid (1 mL) in thionyl chloride (24 eq.) was heated at 60-70° C. for 1 hour to form 5-butylpicolinoyl chloride. Excess of thionyl chloride was removed. Methyl 2-(5-(4-aminophenyl)thiazole-2-carboxamido)-3-methylbutanoate (Intermediate 2, 200 mg) in DCM (5 mL) and pyridine (5 mL) was added to 5-butylpicolinoyl chloride and the reaction mixture was stirred for 1 hour at RT. Solvent was removed and ether was added to it. The solution was stirred, filtered, washed with water and dried obtain the title compound. 1H NMR (DMSO-d6; 300 MHz): δ 10.81 (s, 1H), 8.57 (d, 1H), 8.60 (s, 1H), 8.41 (s, 1H), 8.12 (m, 3H), 7.92 (d, 1H), 7.81 (d, 2H), 4.35 (t, 1H), 3.68 (s, 3H), 2.75 (t, 2H), 2.28 (m, 1H), 1.64 (m, 2H), 1.37 (m, 2H), 0.97 (m, 9H); MS (ESI) m/z 495.2 [M+H]+.

Provenance & Evidence