5-Aminopyridine-2-carboxamide

Uses

5-Aminopyridine-2-carboxamide is a synthetic building block used as a reactant in the discovery of carboline analogs as potent MAPKAP-K2 inhibitors.

Synthesis

General procedure for the synthesis of 5-amino-2-pyridinecarboxamide from 3-amino-6-cyanopyridine: To an 18 mL reaction vial was added a mixed solution of 30% H2O2 (1 mL), 3 N NaOH (3 mL) and MeOH (2.5 mL). To the above mixed solution was added 3-amino-6-cyanopyridine (450 mg, 3.78 mmol) at room temperature. The reaction mixture was stirred at room temperature for 45 minutes and the progress of the reaction was monitored by thin layer chromatography (TLC) to confirm complete consumption of the ingredients. Upon completion of the reaction, the mixture was diluted with water and filtered to collect the solid product. The solid was washed with deionized water and dried to give 480 mg of 5-amino-2-pyridinecarboxamide in 92% yield.

References

[1] Patent: US9138427, 2015, B2. Location in patent: Page/Page column 287
[2] Journal of Medicinal Chemistry, 1994, vol. 37, # 1, p. 18 - 25
[3] Patent: WO2006/17443, 2006, A2. Location in patent: Page/Page column 151