Ethylenediamine → 6-[(2-Aminoethyl)amino]pyridine-3-carbonitrile

Temperature

50 °C

6-Chloronicotinitrile (2.0 g) was treated with ethylenediamine (5 ml). The mixture was then heated at 50° C. for 22 hours. Excess ethylenediamine was removed by rotary evaporation. The residue was partitioned between 2.5 M aqueous sodium hydroxide and dichloromethane. The aqueous layer was extracted 4× more with dichloromethane. The combined organic layers were washed with a saturated sodium chloride solution, dried and then concentrated in vacuo to give 6-[(2-aminoethyl)amino]pyridine-3-carbonitrile as an amber liquid which solidified upon standing. The amine (0.97 g, 6 mmol) was shaken overnight with benzotriazole carboxamidinium 4-methylbenzenesulfonate (2.0 g, 6 mmol) and DIEA (1.05 ml, 6 mmol) in acetonitrile (10 ml). Addition of ether gave amino{2-[(5-cyano(2-pyridyl)amino]ethyl}carboxamidinium 4-methylbenzenesulfonate as a white solid.

1. customExcess ethylenediamine was removed by rotary evaporation
2. customThe residue was partitioned between 2.5 M aqueous sodium hydroxide and dichloromethane
3. extractionThe aqueous layer was extracted 4× more with dichloromethane
4. washThe combined organic layers were washed with a saturated sodium chloride solution
5. customdried
6. concentrationconcentrated in vacuo

ORD record

ord-6a9418f8b09349f89685e9ad9c963e8e

Source dataset

uspto-grants-2008_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07425557B2