Triethylamine → HCID 66744081, compound

Participants

Reaction Steps

A mixture of 3-(benzylamino)-5-(pyridin-4-yl)thiophene-2-carboxylic acid (1.16 g, 3.73 mmol), ammonium chloride (2.00 g, 37.3 mmol), triethylamine (5.23 mL, 3.80 g, 37.3 mmol) and DMF (19 mL) was stirred for 10 min. Then, 1-hydroxybenzotri-azole (1.51 g, 11.2 mmol) and 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide hydrochloride (2.15 g, 11.2 mmol) were added and stirring was continued for 3 days. The mixture was then poured into sat. aqueous sodium hydrogen carbonate (100 mL) and water (100 mL). The mixture was extracted with ethyl acetate (2×100 mL), and the organic layer was washed with sat. aqueous sodium hydrogen carbonate and brine, dried over magnesium sulfate and filtrated. The filtrate was concentrated at reduced pressure to give a yellow solid. This solid was triturated with dichloromethane (20 mL), and the precipitate was collected by filtration to afford the title compound (0.689 g, 59%) as a yellow solid. The filtrate was purified by column chromatography (Combiflash, 12 g silica gel, dichloromethane to ethyl acetate) to afford the additional title compound (0.103 g, 8.9%) as an yellow solid:

Provenance & Evidence