1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → N-(6-chloro-7-methoxy-9H-beta-carbolin-8-yl)-2-methylnicotinamide

Participants

Reaction Conditions

Reaction Steps

6-chloro-7-methoxy-9H-β-carbolin-8-ylamine (100 mg, 0.4 mmol), EDCI (125 mg, 0.64 mmol) and 2-methyl nicotinic acid (66 mg, 0.48 mmol) were taken in a round-bottom flask and suspended in pyridine (2 ml). The resulting mixture was heated at 80° C. overnight. The pyridine was then removed by rotary evaporation and 5% Na2CO3 solution was added. The resulting solid that precipitated out was collected by filtration. Chromatographic purification gave the desired product in 50-70% yield. 1H-NMR (300 MHz, DMSO-d6): δ 2.71 (s, 3H), 3.89 (s, 3H), 7.45 (dd, 1H), 8.15 (d, 1H), 8.21 (d, 1H), 8.38 (d, 1H), 8.45 (s, 1H), 8.61 (d, 1H), 8.92 (s, 1H), 10.33 (s, 1H), 11.57 (s, 1H). Retention Time (LC, method: ammonium acetate standard): 1.77 min. MS (M+H+): 367.1.

Provenance & Evidence