Synthetic Route of 167837-43-6 ,Some common heterocyclic compound, 167837-43-6, molecular formula is C8H8N2O2, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route.
Example 62; Preparation of (El-S-f-aminopyridin-S-v?-N-fCS-fluoro-S-methylbenzofblthiorjhen-?- ylimethvD-N-methylacrylamide hydrochloride;To a solution of (5-fluoro-l-methyl-lH-indol-2-yl)-N-methyhnethanamine (168 mg, 0.8 mmol) in DMF (5 mL) were added in sequential order (E)-3-(6-aminopyridin-3- yi)acrylic acid (120 mg, 0.73 mmol), 1-hydroxybenzotriazole (111 mg, 0.8 mmol), diisopropylethylamine (391 uL, 2.19 mmol), and N-(3-dimethylaminopropyl)-N’- ethylcarbodiimide (160 mg, 0.8 mmol). The mixture was stirred at room temperature overnight, cooled in an ice bath and water added with rapid stirring. The product was extracted with ethyl acetate (3 x 1OmL), dried, filtered and concentrated. The crude free base was re-solvated in methylene chloride (1OmL) to which was added HCl (1 mL, 4M in dioxane), with the product precipitating out with the addition of ether. The title compound is triturated with ether (2 x 10 mL) to yield the product as a pale brown solid (76 mg, 25%): 1HNMR (300 MHz, DMSO-J6) delta 8.2-8.49 (m, 3H), 7.86-7.99 (m, IH), 7.46-7.64 (m, 2H), 7.16-7.29 (m, 2H), 6.99 (d, J= 12.0 Hz, IH), 4.83-5.13 (rotamers, 2s, 2H), 2.95-3.16 (rotamers, 2s, 3H), 2.41 (s, 3H); MS (ESI) m/e 356 (C19H18FN3OS + H)+.
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,167837-43-6, its application will become more common.
Reference:
Patent; AFFINIUM PHARMACEUTICALS, INC.; WO2007/53131; (2007); A2;,
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