1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → N-(6-(4-(4-amino-5-chloro-2-methoxybenzoylaminomethyl)-piperidin-1-yl)hexyl)-1-methyl-1 H-indole-3-carboxamide

Participants

Reaction Conditions

Reaction Steps

4-Amino-N-(1-(6-aminohexyl)piperidin-4-ylmethyl)-5-chloro-2-methoxybenzamide (1.00 g) was dissolved in dimethylformamide (30 ml). 1-Methylindole-3-carboxylic acid (0.48 g) and 1-hydroxybenzotriazole (0.37 g) were added and the mixture was stirred at 0° C. for 15 min. Then, 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (0.53 g) was added, and the mixture was stirred at room temperature for 19 hr. The reaction mixture was concentrated under reduced pressure. Aqueous potassium carbonate solution was added to the residue and the mixture was extracted with ethyl acetate. The extract was dried over magnesium sulfate and concentrated under reduced pressure. The obtained residue was purified by silica gel chromatography to give 0.25 g of N-(6-(4-(4-amino-5-chloro-2-methoxybenzoylaminomethyl)-piperidin-1-yl)hexyl)-1-methyl-1 H-indole-3-carboxamide.

Provenance & Evidence