THE SYNTHESIS OF FAVIPIRAVIR (AVIGAN) FROM 3-HYDROXYPYRAZINE-2-CARBOXAMIDE

• Main Author: Faura, Iqlima
• Format: Final Project
• Language: Indonesia
• Subjects: Kimia
• Online Access: https://digilib.itb.ac.id/gdl/view/65244
• Institution: Institut Teknologi Bandung

The recent COVID-19 pandemic caused by the SARS-CoV-2 virus belongs to the Coronaviridae family. Until now, specific drugs that are effective against SARS-CoV-2 have not been found and there are no drugs specifically designed to treat COVID-19. The provision of COVID-19 drugs is needed in a fast time considering the ongoing mutation of the virus variants. One of the currently recommended SARS-CoV antiviral drugs is Favipiravir. Favipiravir, commonly known as Avigan, is an antiviral drug that has been shown to treat COVID-19 with better performance than other antiviral drugs such as Oseltamivir, Remdesivir, Ribavirin, Triazavirin, and Umifenovir. Based on the literature study, the shortest Favipiravir synthesis is through 3 reaction steps. In this study, Favipiravir was synthesized from the 3-hydroxypyrazine-2-carboxymid and SelectfluorTM through only a one-step reaction. This fluorination reaction was carried out at 100?C for 3 hours with acetonitrile as solvent. The resulting compound was then evaporated to separate the solvent, followed by the addition of ethyl acetate to increase the solubility of Favipiravir in ethyl acetate, followed by filtration to separate the unreacted SelectfluorTM. Then, proceed with liquid extraction of the ethyl acetate fraction with water to separate the compound from the precursor. The final step is recrystallization to obtain high purity Favipiravir. Favipiravir characterization was carried out using 1D NMR 1H NMR 500 MHz, 13C NMR 125 MHz, dan 19F NMR 470 MHz in DMSO-d6 solvent. The best route of synthesis and purification is produced by the reaction of 3-hydroxypyrazine-2-carboxamide and SelectfluorTM with an equivalent mole ratio of 1:3 in acetonitrile and recrystallized at 0?C for 1 hour. The yield obtained is 4.57%.