Application of 4434-13-3, In the chemical reaction process,reaction time,type of solvent,can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product.An updated downstream synthesis route of 4434-13-3 as follows.
To a mixture of 5-methylpicolinic acid (13.7 g) and thionyl chloride (150 mL) was added sodium bromide (20.6 g) by small portions, and the mixture was heated under reflux under a nitrogen atmosphere for 1 hr. DMF (2 mL) was added and the mixture was further heated under reflux under a nitrogen atmosphere for 16 hr. An operation to add toluene (100 mL) to the reaction mixture and evaporate the solvent under reduced pressure was repeated twice, and toluene (100 mL) was added to the obtained residue. To a mixture thereof were added DIPEA (25.8 g) and methanol (20 mL) under a nitrogen atmosphere at 0C, and the mixture was further stirred at 20C for 2 hr. The solvent was evaporated under reduced pressure and the obtained residue was purified by silica gel column chromatography (ethyl acetate/petroleum ether) to give the title compound (9.40 g). 1H NMR (400 MHz, CDCl3) delta2.43 (3H, s), 3.99 (3H, s), 8.10 (1H, s), 8.54 (1H, s).
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,4434-13-3, its application will become more common.
Reference:
Patent; Takeda Pharmaceutical Company Limited; OGINO, Masaki; KIMURA, Eiji; SUZUKI, Shinkichi; ASHIZAWA, Tomoko; IMAEDA, Toshihiro; FUJIMORI, Ikuo; ARAI, Ryosuke; (82 pag.)EP3156397; (2017); A1;,
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