Triethylamine → HCID 44574292, compound

Temperature

0 °C

To a suspension of 5-amino-2-cyanopyridine (2.00 g, 16.8 mmol) in dry dichloromethane (50 mL) was added triethylamine (2.54 g, 25.21 mmol) and the mixture was stirred at 0° C. To the reaction mixture 2-thiophene carbonyl chloride (3.70 g, 25.21 mmol) was added drop wise over a period of 15 minutes, and the reaction mixture was stirred at 0° C. for about 1 hour and then at room temperature overnight. The reaction mixture was diluted with dichloromethane (50 mL) and washed with saturated sodium bicarbonate solution (50 mL) and water (50 mL). The organic layer was dried over anhydrous sodium sulfate and concentrated to obtain the crude product, which was purified by column chromatography (silica gel, 20-50% ethyl acetate in petroleum ether as an eluent) to obtain N-(6-cyanopyridin-3-yl)thiophene-2-carboxamide (compound 25a) Yield: 0.430 g (7.74%) and N-(6-cyanopyridin-3-yl)-N-(thiophene-2-carbonyl)thiophene-2-carboxamide (compound 25b). Yield: 1.3 g (33.75%).

1. stirringthe reaction mixture was stirred at 0° C. for about 1 hour
2. customat room temperature
3. customovernight
4. washwashed with saturated sodium bicarbonate solution (50 mL) and water (50 mL)
5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
6. concentrationconcentrated
7. customto obtain the crude product, which
8. customwas purified by column chromatography (silica gel, 20-50% ethyl acetate in petroleum ether as an eluent)

ORD record

ord-993325876f574cf4965371205c869431

Source dataset

uspto-grants-2012_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08314103B2