1,2-Dichloroethane → HCID 25224951, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 5-(3-chloro-5-methylphenyl)-2-(1-methyl-1H-pyrazol-4-yl)nicotinic acid (2-2, 0.050 g, 0.153 mmol) and 3,4-dimethoxybenzylamine (0.099 g, 0.595 mmol) in dimethylformamide (1 mL) was added EDC (0.132 g, 0.686 mmol), HOBt (0.105 g, 0.686 mmol) followed by N-methylmorpholine (0.250 mL, 2.28 mmol) and the system was stirred at 25° C. overnight. The reaction mixture was partitioned between ethyl acetate and water, washed with saturated sodium carbonate and dried over magnesium sulfate. The reaction mixture was filtered and purified via normal phase chromatography (0→5% MeOH in DCM) to afford the title compound (2-3) as a bone-colored powder. 1H NMR (500 MHz, CDCl3) δ 8.81 (d, J=2.5 Hz, 1H), 7.99 (s, 1H), 7.92 (d, J=2.5 Hz, 1H), 7.78 (s, 1H), 7.38 (s, 1H), 7.28 (m, 2H), 7.23 (s, 1H), 6.84 (s, 2H), 6.06 (m, 1H), 4.55 (d, J=6 Hz, 2H), 3.88(s, 3H), 3.87(s, 3H), 3.86(s, 3H), 2.42 (s, 3H). HRMS [M+H] C26H25ClN4O3 calc'd 477.1688, found 477.1682.

Provenance & Evidence