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 16681-65-5 as follows. Quality Control of 1-Methyl-1H-1,2,3-triazole
To a flask containing 1-methyl-1H-1,2,3-triazole (111 mg, 1.34 mmol) was added THF (10 mL) and the solution was cooled to -45 C. using a CH3CN-CO2 bath. n-BuLi (2.5 M in hexanes, 0.5 mL, 1.25 mmol) was added dropwise to provide a white suspension. The suspension was stirred at -45 C. for 25 minutes. A pre-warmed THF solution of (2,4-dichloro-3-(2,2,2-trifluoroethyl)quinolin-6-yl)(1,2-dimethyl-1H-imidazol-5-yl)methanone (470 mg, 1.17 mmol in 7 mL THF, Intermediate 70) was introduced at -45 C. The reaction temperature was allowed to warm gradually to room temperature over 70 minutes then quenched with aqueous NH4Cl solution. The aqueous portion was extracted with EtOAc (3*40 mL), and the combined organics were washed with brine, dried over MgSO4, filtered and concentrated. Chromatography on silica gel (2% MeOH-DCM increasing to 8% MeOH) afforded the title compound as a tan amorphous solid. MS (ESI): mass calcd. for C20H17Cl2F3N6O, 484.1. found, 485.0 (M+H)+. 1H NMR (500 MHz, CDCl3) delta ppm 8.60 (s, 1H), 8.44-8.40 (m, 2H), 7.95 (d, J=8.8 Hz, 1H), 7.62 (dd, J=8.8, 1.8 Hz, 2H), 6.95 (s, 1H), 5.89 (s, 1H), 4.05 (q, J=9.6 Hz, 2H), 3.89 (s, 3H), 3.32 (s, 3H).
According to the analysis of related databases, 16681-65-5, the application of this compound in the production field has become more and more popular.
Reference:
Patent; JOHNSON & JOHNSON; LEONARD, KRISTI A.; BARBAY, KENT; EDWARDS, JAMES P.; KREUTTER, KEVIN D.; KUMMER, DAVID A.; MAHAROOF, UMAR; NISHIMURA, RACHEL; URBANSKI, MAUD; VENKATESAN, HARIHARAN; WANG, AIHUA; WOLIN, RONALD L.; WOODS, CRAIG R.; FOURIE, ANNE; XUE, XIAOHUA; CUMMINGS, MAXWELL D.; MCCLURE, KELLY; TANIS, VIRGINIA; US2015/111870; (2015); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics