1,2-Dichloroethane → HCID 25226075, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 5-(3-chloro-5-methylphenyl)-2-morpholin-4-ylnicotinic acid (4-2, 2.8 g, 8.41 mmol) and 3,4-dimethoxybenzylamine (6.30 mL, 42.1 mmol) in DCM (42 mL) was added EDC (4.84 g, 25.2 mmol), HOBt (3.87 g, 25.2 mmol) followed by N-methylmorpholine (9.25 mL, 84 mmol) and the system was stirred at 25° C. overnight. The reaction mixture was partitioned between ethyl acetate and water, washed with saturated sodium bicarbonate and dried over magnesium sulfate. The reaction mixture was filtered, concentrated and triturated with diethylether to afford the title compound (4-3) as a bone powder. 1H NMR (400 MHz, CDCl3) δ 8.82 (m, 1H), 8.53 (d, J=2.4 Hz, 1H), 8.49 (d, J=2.4 Hz, 1H), 7.35 (s, 1H), 7.16 (s, 1H), 6.90 (m, 2H), 6.84 (m, 1H), 4.56 (d, J=5.6 Hz, 2H), 3.86 (s, 3H), 3.85 (s, 3H), 3.55 (m, 4H), 3.12 (m, 4H), 2.37(s, 3H). HRMS [M+H] C26H28ClN3O4 calc'd 482.1841, found 482.1847.

Provenance & Evidence