Triethylamine → N-(4-Isopropylbenzenesulfonyl)-alpha-[2-n-propyl-4-[[(2-pyridylmethyl)amino]carbonyl]phenoxy]-3,4-methylenedioxyphenylacetamide

Participants

Reaction Conditions

Reaction Steps

To a solution of 200 mg (0.371 mmol) of N-(4-isopropylbenzenesulfonyl)-α-(4-carboxy-2-n-propylphenoxy)-3,4-methylenedioxyphenylacetamide (from Step D) in 2 mL of acetonitrile and 1 mL of dry THF was added 72.2 mg (0.445 mmol) of 1,1'-carbonyldiimidazole. The solution was stirred under N2 at 60° C. for 2 hours. Then 45.9 μL (48.1 mg; 0.445 mmol) of 2-(aminomethyl)pyridine was added, followed by 129 μL (93.7 mg; 0.928 mmol) of triethylamine. The solution was stirred overnight at 60° C. The cooled reaction mixture was quenched by addition of 5% citric acid solution (aqueous) and extracted twice with EtOAc. The combined organic extracts were washed twice with H2O, then with brine, dried over Na2SO4, and filtered. The filtrate was concentrated, and the residue was flash chromatographed (gradient elution with 1-6% MeOH in CH2Cl2) to give 191 mg (82%) of the title compound as a cream-colored solid, mp 168°-170° C.; homogeneous by TLC in 95:5 CH2Cl2 -MeOH. ESI mass spectrum m/e 630 (M+H)+.

Provenance & Evidence