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. 16681-65-5
n-BuLi (1.23 M in hexanes, 447 muL, 0.55 mmol) was added dropwise to a stirred slurry of 1-methyl-1,2,3-triazole (46 mg, 0.55 mmol) in THF (1 mL) at -40 C. under nitrogen. After stirring for 30 minutes at -40 C., the mixture was treated dropwise with a solution of (2,4-dichloro-3-isopropoxyquinolin-6-yl)(1,2-dimethyl-1H-imidazol-5-yl)methanone (104 mg, 0.27 mmol, Intermediate 25) in THF (1 mL). The reaction was allowed to warm to room temperature over 1 hour. The reaction was then quenched with saturated aqueous NH4Cl. The mixture was poured into a separatory funnel and extracted with DCM (2*25 mL). The organics were combined, washed with brine, dried (Na2SO4), filtered and concentrated to dryness to afford an orange-brown foam. The crude material was purified by FCC (1-7.5% MeOH/DCM) followed by reverse-phase HPLC (acetonitrile/water+0.05% TFA) to provide the title compound as a clear colorless oil. 1H NMR (500 MHz, CDCl3) delta ppm 8.23-8.20 (m, 1H), 7.98 (d, J=8.8 Hz, 1H), 7.52-7.48 (m, 1H), 7.24 (s, 1H), 6.40 (s, 1H), 4.80-4.73 (m, 1H), 3.92 (s, 3H), 3.63 (s, 3H), 2.58 (s, 3H), 1.44-1.41 (m, 6H). MS (ESI): mass calcd. for C21H22Cl2N6O2, 460.1. m/z found, 461.1 [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