Water → N-(6-chloro-7-ethylsulfanyl-9H-beta-carbolin-8-yl)-2-methyl-nicotinamide

Participants

Reaction Conditions

Reaction Steps

A 25 ml round-bottom flask with magnetic stirrer was charged with 6-chloro-7-ethylsulfanyl-9H-β-carbolin-8-ylamine (37.2 mg, 0.13 mmol) and 2-methylnicotinic acid (36.2 mg, 0.26 mmol) in 3 ml anhydrous pyridine. To the resulting light-orange mixture at RT was added solid 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (73.2 mg, 0.38 mmol) and the resulting reaction mixture was heated to 80° C. for 5 days. Next, the reaction mixture was cooled to RT and concentrated to afford a brown, viscous syrup. The syrup was dissolved in a minimal amount of MeOH (−2 ml), slowly added to a 5:1 mixture of H2O/saturated sodium bicarbonate (20 ml), and stirred at RT for 2.5 hr. The resulting precipitated solid was collected via suction filtration, washed with 1:1 hexanes/diethyl ether (2×20 ml), and air-dried to afford 21.0 mg of N-(6-chloro-7-ethylsulfanyl-9H-β-carbolin-8-yl)-2-methyl-nicotinamide as a tan solid (˜38%). LCMS (ammonium acetate standard method) retention time=2.33 min. (M+=397; M−=395). 1H-NMR (300 MHz, CD3OD, ppm) δ 8.89 (1H, s) 8.63-8.58 (1H, m) 8.44-8.38 (2H, m) 8.36 (1H, d) 8.15 (1H, d) 7.52-7.44 (1H, m) 2.98 (2H, q) 2.84 (3H, s) 1.20 (3H, t).

Provenance & Evidence