3-Cyanopyridine → HCID 178504799, compound

To a suspension of 4-(methylsulfonyl)aniline hydrochloride (6 g, 28.8 mmol) in toluene (150 ml) at 0° C., trimethylaluminum (2M solution in toluene, 21.6 ml, 43.2 mmol) was added over 15 minutes. The reaction mixture was warmed to room temperature and stirred for 2.5 hours. A solution of 3-cyanopyridine (6 g, 57.6 mmol) in toluene (150 ml) was added over 10 minutes and the reaction mixture was heated to 90-95° C. After 24 hours, the reaction mixture was cooled to room temperature and poured over a slurry of silica gel in chloroform. After filtration, the residue was washed with a mixture of methylene chloride/methanol and later methanol. The combined filtrates were concentrated and the resulting yellowish solid was stirred with ethyl acetate (1000 ml) and filtered. The pale yellow amidine (4.5 g, 34%) was used in the next reaction without further purification: mp (DSC) 265° C. Anal Calc'd. for C13H14N3SO2Cl.0.5 H2O: C, 48.67, H, 4.71, N, 13.10. Found: C, 48.34, H, 4.26, N, 12.77.

1. temperaturethe reaction mixture was heated to 90-95° C
2. waitAfter 24 hours
3. temperaturethe reaction mixture was cooled to room temperature
4. filtrationAfter filtration
5. washthe residue was washed with a mixture of methylene chloride/methanol and later methanol
6. concentrationThe combined filtrates were concentrated
7. stirringthe resulting yellowish solid was stirred with ethyl acetate (1000 ml)
8. filtrationfiltered
9. customThe pale yellow amidine (4.5 g, 34%) was used in the next reaction without further purification

ORD record

ord-0c3cf4fbdd9d4a779fb3cd29116109fc

Source dataset

uspto-grants-2003_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06613789B2