Synthesis of 2-Amino-5-methyl-2-(pyridin-3-yl)thiazole
In a microwave vial, tert-butyl {2-[5-methyl-2-(pyridin-3-yl)-1,3-thiazol-4-yl]-2-oxoethyl}carbamate (4.29 g, 12.87 mmol) was dissolved in 30 mL of methanol. Potassium cyanide (3.35 g, 51.47 mmol) and ammonium carbonate (4.95 g, 51.47 mmol) were added. The vial was sealed, and the mixture was stirred at 80 °C overnight. The salts were filtered off and rinsed with methanol. The filtrate was concentrated. The crude product was purified by preparative HPLC. Product containing samples were united, the solvents were evaporated with a rotary evaporator and the residue was lyophilized. 1.97 g (100% purity, 38% yield) of the title compound was obtained. LC–MS (Method 2): Rt = 1.21 min; MS (ESIpos): m/z = 404 [M + H]+.
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Meibom D., Wasnaire P., Beyer K., Broehl A., Cancho-Grande Y., Elowe N., Henninger K., Johannes S., Jungmann N., Krainz T., Lindner N., Maassen S., MacDonald B., Menshykau D., Mittendorf J., Sanchez G., Schaefer M., Stefan E., Torge A., Xing Y, & Zubov D. (2024). BAY-9835: Discovery of the First Orally Bioavailable ADAMTS7 Inhibitor. Journal of Medicinal Chemistry, 67(4), 2907-2940.
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