Chemical Properties
Off white powder
Uses
Methyl 2-Aminonicotinate is used to prepare 2-{4-[(3S)-Piperidin-3-yl]phenyl}-2H-indazole-7-carboxamide (MK-4827)as a novel oral poly(ADP-ribose)polymerase (PARP) inhibitor efficacious in BRCA-1 and -2 mutant tumors. It is also used to synthesize quinazolinone/quinazoline thione derivatives as phosphodiesterase 7 inhibitors.
Materials Uses
With the help of specific reactions, methyl 2-aminonicotinate can be introduced into the structure of polymer materials, endowing materials with special properties, such as improving the stability, solubility, and even giving them some functional response characteristics, which opens up new avenues for the development of materials science.
Synthesis
Concentrated sulfuric acid (96%, 144 mL, 2.69 mol, 18.6 eq.) was slowly added dropwise to a stirred suspension of 2-aminonicotinic acid (20.0 g, 0.145 mol) in methanol (228 mL, 7.12 mol, 49.2 eq.), and the reaction system was kept at 0 °C. Subsequently, the reaction mixture was irradiated in a microwave reactor (power input 300 W) at 60 °C and atmospheric pressure for 1.5 hours. Upon completion of the reaction, the light brown mixture was carefully poured into ice water, maintained at 0 °C, and solid sodium carbonate was added by batchwise addition until complete neutralization (pH > 8). The aqueous layer was extracted three times with ethyl acetate. The organic layers were combined, washed sequentially with saturated brine and deionized water, and then dried with anhydrous magnesium sulfate. Finally, the organic solvent was evaporated to afford methyl 2-aminopyridine-3-carboxylate (21.15 g, 93% yield) as colorless needle-like crystals with purity meeting the analytical requirements.
References
[1] Tetrahedron, 2014, vol. 70, # 35, p. 5541 - 5549
[2] European Journal of Medicinal Chemistry, 2012, vol. 52, p. 284 - 294
[3] Synthetic Communications, 2006, vol. 36, # 2, p. 181 - 186
[4] Patent: WO2005/32481, 2005, A2. Location in patent: Page/Page column 38
