Reference of 5334-39-4, 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 5334-39-4 as follows.
To a solution of 245 mg (1.19 mmol) of a mixture of 1 -(4-fluorobenzyl)-5-methyl-1 H- pyrazol-4-amine and 1 -(4-fluorobenzyl)-3-methyl-1 H-pyrazol-4-amine (intermediate 1C) in 4.0 mL DMSO was added 453 mg (1.19 mmol) HATU, 0.26 mL N,N- diisopropylethylamine and 200 mg (0.99 mmol) commercially available 2,6- dimethylquinoline-4-carboxylic acid. The reaction mixture was stirred for 20 hours at 25 C. This mixture was directly purified via preparative HPLC (method A1 ) to obtain 92 mg (23%) of the desired title compound together with 208 mg (51%) of the regioisomer N-[1 -(4-fluorobenzyl)-3-methyl-1 H-pyrazol-4-yl]-2,6-dimethylquinoline-4- carboxamide. 1 H NMR (500 MHz, DMSO d6): delta (ppm) = 2.22 (s, 3H), 2.48 (s, 3H), 2.68 (s, 3H), 5.31 (s, 2H), 7.16 – 7.26 (m, 4H), 7.53 (s, 1 H), 7.60 (dd, 1 H), 7.79 (s, 1 H), 7.85 (s, 1 H), 7.89 (d, 1 H), 10.12 (s, 1 H).
According to the analysis of related databases, 5334-39-4, the application of this compound in the production field has become more and more popular.
Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; BUCHMANN, Bernd; HEISLER, Iring; MUeLLER, Thomas; CLEVE, Arwed; HEROULT, Melanie; NEUHAUS, Roland; PETRUL, Heike; QUANZ-SCHOeFFEL, Maria; (194 pag.)WO2016/12474; (2016); A1;,
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