Triethylamine → HCID 66684797, compound

Participants

Reaction Conditions

Reaction Steps

To the solution of compound 5-chloro-4-fluoro-N1-methylbenzene-1 2-diamine (0.3 g, 0.00172 mol) and 4-trifluoromethylnicotinic acid (0.36 g, 0.00189 mol) in DMF (5 ml) was added EDC-HCl (0.27 g, 0.00206 mol) followed by HOBt (0.39 g, 0.00206 mol) and Et3N (0.047 g, 0.00344 mol). Reaction mixture was heated at 80° C. for 12 h. Reaction mass was quenched with ice water and layers were separated. The aqueous layer was extracted with EtOAc (3×10 ml). The combined organic extracts were washed with sat NaHCO3 solution and brine dried over Na2SO4 and concentrated to get crude product which was purified by column chromatography to provide N-(4-chloro-5-fluoro-2-(methyl amino)phenyl)-4-(tri-fluoromethyl)nicotinamide as a brown colored solid. 1H NMR (400 MHz, DMSO-d6), δ: 10.08 (s, 1H), 9.20 (s, 1H), 8.99-8.98 (d, J=4.8 Hz, 1H), 8.75-8.74 (d, J=4.8 Hz, 1H), 7.91-7.89 (d, J=5.2 Hz, 1H), 7.39-7.37 (d, J=10.4 Hz, 1H), 6.72-6.71 (d, J=7.2 Hz, 1H), 5.36 (bs, 1H), 2.74-2.73 (d, J=4.0 Hz, 3H). MS (M+1): 348.12.

Provenance & Evidence