New discoveries in chemical research and development in 2021. The dynamic chemical diversity of the numerous elements, ions and molecules that constitute the basis of life provides wide challenges and opportunities for research. 16681-65-5, name is 1-Methyl-1H-1,2,3-triazole belongs to triazoles compound, it is a common compound, a new synthetic route is introduced below. Computed Properties of C3H5N3
To a flask containing 1-methyl-1H-1,2,3-triazole (160 mg, 1.93 mmol) was added THF (12 mL) and the colorless solution was cooled to -43 C. using a CH3CN-CO2 bath. Then, n-BuLi, (2.5 M in hexanes, 0.72 mL, 1.8 mmol) was added which afforded an opaque white suspension. The suspension was stirred at -40 C. for 20 minutes, then a homogeneous solution of (2-chloro-4-methoxy-3-(2,2,2-trifluoroethyl)quinolin-6-yl)(1,2-dimethyl-1H-imidazol-5-yl)methanone (350 mg, 0.88 mmol, Intermediate 59: step c) in 5 mL THF, was introduced at -40 C. The reaction mixture was allowed to warm gradually to 0 C. over 25 minutes, then quenched with aqueous NH4Cl solution. The aqueous portion was extracted with EtOAc (3*35 mL). The combined organics were washed with brine, dried over Na2SO4 and MgSO4, filtered and concentrated to give a brown solid. Chromatography on silica gel (3% MeOH-DCM increasing to 10% MeOH) provided the title compound as a tan amorphous solid. 1H NMR (500 MHz, CD3OD) delta ppm 8.22 (d, J=1.8 Hz, 1H), 8.05 (d, J=8.9 Hz, 1H), 7.70 (dd, J=8.9, 2.0 Hz, 1H), 7.48 (s, 1H), 6.91 (s, 1H), 4.09 (s, 3H), 4.03-3.89 (m, 5H), 3.69 (s, 3H), 2.66 (s, 3H). MS (ESI): mass calcd. for C21H20ClF3N6O2, 480.1. found, 481.1 (M+H)+.
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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