Triethylamine → HCID 67050165, compound

Temperature

0 °C

To a suspension of 5-amino-2-cyanopyridine (1.00 g, 8.4 mmol) in dry dichloromethane (10 mL) was added triethylamine (1.27 g, 12.6 mmol) and the reaction mixture was stirred at 0° C. To the reaction mixture 3-chloropropionyl chloride (1.42 g, 12.6 mmol) was added drop wise over a period of 15 minutes, and the reaction mixture was stirred at 0° C. for 1 hour and then at room temperature for 4 hours. 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 over silica gel using methanol/chloroform as eluent. The pure fraction was concentrated to obtain 3-chloro-N-(6-cyanopyridin-3-yl)propionamide. To a solution of potassium hydroxide (0.1 g, 1.5 mmol) in dry methanol (20 mL) was added hydroxylamine hydrochloride (0.105 g, 1.5 mmol) and the mixture was stirred for 30 minutes. White precipitate of potassium chloride obtained was filtered and to the filtrate was added 3-chloro-N-(6-cyanopyridin-3-yl)propionamide (0.209 g, 1.0 mmol) as obtained herein above, and the reaction mixture was stirred at reflux temperature for 4 hours. The reaction mixture was then concentrated and the crude product obtained was triturated with diethyl ether to obtain a solid which was crystallized from ethyl acetate/petroleum ether to obtain the title compound.

1. stirringthe reaction mixture was stirred at 0° C. for 1 hour
2. washwashed with saturated sodium bicarbonate solution (50 mL) and water (50 mL)
3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
4. concentrationconcentrated
5. customto obtain the crude product, which
6. customwas purified over silica gel
7. concentrationThe pure fraction was concentrated

ORD record

ord-661482af5aae40ceab8348b22fac60cb

Source dataset

uspto-grants-2012_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08314103B2