1-Hydroxybenzotriazole → 1-(1-(4-chlorobenzyl)-1H-indole-2-carbonyl)-N-(1-(pyridin-4-yl)ethyl)piperidine-4-carboxamide

Participants

Reaction Steps

N1-((ethylimino)methylene)-N3,N3-dimethylpropane-1,3-diamine hydrochloride (259 mg, 1.350 mmol), 1-(1-(4-chlorobenzyl)-1H-indole-2-carbonyl)piperidine-4-carboxylic acid (428 mg, 1.080 mmol), and 1H-benzo[d][1,2,3]triazol-1-ol (182 mg, 1.350 mmol) were dissolved in 4.0 mL of DCM. The reaction was stirred at room temperature for ten minutes before Hunig's Base (0.236 ml, 1.350 mmol) and 1-(4-pyridinyl)ethanamine as a 1.0 mL DCM solution was added. The reaction was allowed to stir at room temperature overnight. The reaction was diluted with water and ethyl acetate. The organic phase was washed with water, saturated sodium bicarbonate (twice), and saturated sodium chloride. The organic phase was dried over magnesium sulfate, filtered and concentrated. The crude material was triturated with ether and ethyl acetate and filtered to obtain white solid as a product. (Yield: 37.9 mg, white solid) 1H-NMR (400 MHz, DMSO-d6) 8.52-8.45, 8.35, 7.62, 7.53, 7.36-7.30, 7.30-7.25, 7.24-7.18, 7.13-7.06, 6.72, 5.48, 4.87, 4.57-3.84, 2.93, 2.48-2.42, 1.71, 1.58-1.26

Provenance & Evidence