Diisopropylethylamine → Methyl 4-({[(2-chloro-5-{[(3-chlorophenyl)methyl]oxy}phenyl)carbonyl]amino}methyl)benzoate

Participants

Reaction Conditions

Reaction Steps

A solution of 2-chloro-5-{[(3-chlorophenyl)methyl]oxy}benzoic acid (250 mg, 0.84 mmol) and N-[3-(dimethylamino)propyl]-N′-ethylcarbodiimide hydrochloride (250 mg, 1.3 mmol) in DCM (3 ml) was stirred at room temperature for 30 min. A solution of methyl 4-(aminomethyl)benzoate hydrochloride (262 mg, 1.3 mmol) in DCM (2 ml) was added followed by N-ethyl-N-(1-methylethyl)-2-propanamine (220 ul, 1.3 mmol). The mixture was heated at 40° C. overnight. The mixture was then diluted with methanol and purified by SCX cartridge eluting with methanol. The fractions were combined and evaporated to give the title compound as a white solid. MS (ES+) m/z 444 [M+H]− (C23H1935Cl2NO4). 1H-NMR (400 MHz, d6-DMSO) δ 3.85 (3H, s), 4.51 (2H, d, J 4), 5.17 (2H, s), 7.12 (2H, d, J 8), 7.42-7.49 (7H, m), 7.95 (2H, d, J 8), 9.06 (1H, s).

Provenance & Evidence