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 41965-95-1 as follows. 41965-95-1
Methyl 2-chloro-4-[(3-chloro-4-methoxybenzyl)amino]-6-cyanoquinoline-3-carboxylate, 14 To a heterogenous mixture of quinoline 13 (3.56 mmol) and 3-chloro-4-methoxy benzylamine.HCl (3.92 mmol) in NMP (15 mL) was added iPr2NEt (8.90 mmol). The reaction mixture was heated to 80 C. for 3 h. Subsequently, cooled the reaction mixture to ambient temperature and added 1M aqueous HCl and EtOAc. The resulting layers were separated and the organic layer washed with water (3*) followed by brine (1*). The combined organic layers were dried over Na2SO4, filtered, and concentrated in vacuo. The residue was dissolved in a minimum amount of hot EtOAc and allowed to cool to ambient temperature. Hexanes was then added to the solution and the intermediate 14 (80% yield) precipitated out and was collected by vacuum filtration. 1H NMR (300 MHz, CDCl3) delta8.20 (s, 1H), 7.95 (d, 1H, J=8.4 Hz), 7.82 (d, 1H, J=7.5 Hz), 7.38 (s, 1H), 7.27-7.22 (m, 1H), 6.98 (d, 1H, J=8.4 Hz), 6.26 (s, 1H), 4.54 (d, 2H, J=4.8 Hz), 3.95 (s, 3H), 3.93 (s, 3H).
According to the analysis of related databases, 41965-95-1, the application of this compound in the production field has become more and more popular.
Reference:
Patent; THE TRUSTEES OF COLUMBIA UNIVERSITY IN THE CITY OF NEW YORK; Landry, Donald W.; Deng, Shixian; Arancio, Ottavio; Fiorito, Jole; Wasmuth, Andrew; (41 pag.)US10626113; (2020); B2;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics