Background and overview of preparation methods and application examples of 2-(2-aminoethyl)pyridine
2-(2-Aminoethyl)pyridine is a pharmaceutical intermediate that can be obtained from 2-(cyanomethyl)pyridine through the reduction of sodium borohydride. There are reports in the literature that it can be used to prepare arylcyclopropyl-amino-isoquinolinamide compounds.
Preparation methods and application examples of 2-(2-aminoethyl)pyridine
A solution of sodium borohydride (0.26 g, 7.00 mmol) in 30 mL of diethyl ether was added dropwise to 2-(cyanomethyl)pyridine (0.80 g, 6.82 mmol thienopyridine l) and AlCl3 (0.93 g, 7.00 mmol) in the mixture. The solution was stirred at room temperature for 6 hours. The solvent was removed and the resulting mixture was extracted with hot isopropyl ether (3 x 30 mL). The organic layers were combined and the solvent was removed under reduced pressure to obtain 2-(2-aminoethyl)pyridine. 1H NMR (CDCl3, MHz) δ = 1.54 (s, 2H), 2.91 (t, 2H, J = 6.7 Hz), 3.10 (t, 2H, J = 6.7 Hz), 7.09 (ddd, 1H, J = 7.5 Hz , J = 6.1 Hz, J = 1.1 Hz), 7.14 (ddd, 1H, J = 7.9 Hz, J = 0.9 Hz, J = 0.9 Hz), 7.57 (ddd, 1H, J = 7.6 Hz, J = 7.2 Hz, J = 1.9 Hz), 8.51 (ddd, 1H, J = 4.9 Hz, J = 1.9 Hz, J = 1.0 Hz); 13C NMR (CDCl3, 100 MHz) δ = 41.9, 121.2, 123.3, 136.3, 149.3, 160.0; MS (CI, NH3) m/z = 123.1 (100) [(sericite powder M + 1)+].
Preparation methods and application examples of 2-(2-aminoethyl)pyridine
2-(2-Aminoethyl)pyridine can be used to prepare arylcyclopropyl-amino-isoquinolinamide compounds with the following structure. This class of compounds can affect the function of kinases and other proteins in cells and can be used as or in conjunction with therapeutic agents. In particular, such compounds are useful in the treatment of ocular diseases such as glaucoma and retinal diseases, as anti-inflammatory agents, in the treatment of cardiovascular diseases, and in diseases characterized by abnormal growth (such as cancer).
References
[1]JC Lugo-González, P Gómez-Tagle, Flores-Alamo M, et al. Mechanistic study of carboxylic acid and phosphate ester cleavage by oximate metal complexes surpassing the limiting reactivity of highly basic free oximate anions[J] . Dalton Transactions, 2020, 49.
[2] From PCT Int. Appl., 2018183911, 04 Oct 2018
