Benzenemethanamine, 3-chloro-N-methyl- → N-(3-chlorobenzyl)-2-(5-(4-methoxyphenyl)-2-oxopyridin-1(2H)-yl)-N-methylacetamide

Participants

Reaction Steps

According to Scheme 9 Step 3: To a solution of (3-chlorophenyl)-N-methylmethanamine (1 eq, 0.19 mmol, 0.03 g), 2-(5-(4-methoxyphenyl)-2-oxopyridin-1(2H)-yl)acetic acid (1 eq, 0.19 mmol, 0.05 g) and hydroxybenzotriazole (1.1 eq, 0.21 mmol, 0.03 g) in CH2Cl2 (2 mL) at room temperature was added EDCI.HCl (1.5 eq, 0.29 mmol, 55 mg). The reaction was stirred at room temperature for 12 hours then diluted with AcOEt. The reaction washed with brine and the organic phase extracted (×3). The combined organic fractions were dried (Na2SO4), filtered and concentrated under reduced pressure. The crude product was purified by flash chromatography over silica gel (AIT Flashsmart prepacked column 10 g SiO2) using CH2Cl2/AcOEt (50/50) as eluent to afford the N-(3-chlorobenzyl)-2-(5-(4-methoxyphenyl)-2-oxopyridin-1(2H)-yl)-N-methylacetamide (0.11 mmol, 44 mg, 57%) as a yellow oil.

Provenance & Evidence