Ethylamine → N-Ethyl-6-(3-ethylureido)-4-(phenylamino)nicotinamide

Participants

Reaction Steps

To a solution of 6-(3-ethylureido)-4-(phenylamino)nicotinic acid (50 mg, 0.16 mmol, 1.0 eq) in THF (5.0 mL) was added EDCI.HCl (1-ethyl-3-(3-dimethylaminopropyl) carbodiimide hydrochloride, 46 mg, 0.24 mmol, 1.50 eq) followed by HOBt (N-hydroxybenzotriazole, 32 mg, 0.24 mmol, 1.50 eq), DMAP (4-dimethylaminopyridine, 29 mg, 0.24 mmol, 1.50 eq) and finally, ethyl amine (16 mg 70% solution, 0.24 mmol, 1.50 eq). The resulting reaction mixture was stirred overnight at room temperature. The reaction mass was then poured onto ice-cold water followed by extraction with EtOAc (3×20 mL). The organics were combined, washed with brine, dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The residue was purified over silica gel (60-120 M, 1-2.5% MeOH-DCM) to obtain Compound 8 (48 mg, 92%), 1H NMR (300 MHz, DMSO-d6): δ 10.43 (br s, 1H), 9.03 (br s, 1H), 8.52 (t, J=5.20 Hz, 1H), 8.41 (5, 1H), 7.94 (br s, 1H), 7.39 (m, 2H), 7.22 (m, 3H), 7.13 (m, 1H), 3.26 (m, 2H), 3.13 (m, 2H), 1.12 (t, J=7.20 HZ, 3H) and 1.05 (t, J=7.20 Hz, 3H). [M+H]+ m/z=328.18.

Provenance & Evidence