Synthetic Route of 884494-82-0, Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps,and cheap raw materials. 884494-82-0, name is 5-Fluoro-2-methoxynicotinic acid. A new synthetic method of this compound is introduced below.
[0361] To a solution of 5-fluoro-2-methoxynicotinic acid (372 mg, 2.172 mmol) in DCM (18.3 mL) was added oxalyl chloride (380 xL, 4.34 mmol) and DMF (8.41 mu, 0.109 mmol) at 0C. After stirring at 20C for 1 hour, the mixture was concentrated in vacuo. The residue was taken up in THF (1 mL) and added dropwise to a mixture of 5-amino-4-(4-(2,4- difluorophenoxy)piperidin-l-yl)-NJV-dimethylpicolinamide (545 mg, 1.448 mmol) and DIPEA (759 xL, 4.34 mmol) in THF (11 mL). The reaction mixture was stirred at 60C for 1 hour, then cooled to RT, and filtered. The filtrate was purified by HPLC, eluting with ACN in water. The solid product was recrystallized from 3: 1 MeOH/water solution and filtered. The solids were placed in a 70C vacuum oven overnight to give the title compound as an off-white solid (487 mg, 63.5%). NMR (500 MHz, DMSG-cfe) delta ppm 1.81 – 1.87 (m, 2 H), 2.06 – 2.10 (m, 2 H), 2.94 – 2.98 (m, 2 H), 2.99 (d, J=6,83 Hz, 6 H), 3.27 (dd,,1=1.96, 7.08 Hz, 2 H), 4.12 (s, 3 H), 4.55 (di,./ 7.93. 4.09 Hz, 1H), 6.99 – 7.05 (m, 1H), 7.27 – 7.34 (m, 3 H), 8.25 (dd,./ K.54. 3.17 Hz, 1H), 8.46 (d,./ 3.42 Hz, 1H), 9.15 is. 1H), 10.17 (s, 1H); ES1-MS m/z j M 1 .] 530.3.
At the same time, in my other blogs, there are other synthetic methods of this type of compound,884494-82-0, 5-Fluoro-2-methoxynicotinic acid, and friends who are interested can also refer to it.
Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; GREEN, Jason; HOPKINS, Maria; JONES, Benjamin; KIRYANOV, Andre A.; KUEHLER, Jon; MONENSCHEIN, Holger; MURPHY, Sean; NIXEY, Thomas; SUN, Huikai; (300 pag.)WO2018/183145; (2018); A1;,
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