Synthetic Route of 16681-65-5, New Advances in Chemical Research in 2021.Reactions catalyzed within inorganic and organic materials and at electrochemical interfaces commonly occur at high coverage and in condensed media, 16681-65-5, name is 1-Methyl-1H-1,2,3-triazole, molecular formula is C3H5N3, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, below Introduce a new synthetic route.
A solution of n-BuLi (0.3 mL, 0.75 mmol, 2.5 M solution in hexane) was added slowly to a solution of 1-methyl-1H-1,2,3-triazole (65.6 mg, 0.789 mmol) in THF (4 mL) at -45 C. After addition, stirring was continued for an additional 30 minutes at 40 C. and (3-((4-(1H-pyrazol-1-yl)piperidin-1-yl)methyl)-4-chloro-2-methoxyquinolin-6-yl)(1,2-dimethyl-1H-imidazol-5-yl)methanone (189 mg, 0.395 mmol, Intermediate 42) dissolved in THF (2 mL) was slowly added. An additional 1 mL of THF was used to complete the quantitative addition. The mixture was stirred at -40 C. for 5 minutes then warmed to room temperature and stirred for 1 hour. The solution was quenched with saturated aqueous NH4Cl solution. H2O was added and layers were separated. The aqueous layer was extracted with EtOAc and the combined organic extracts washed with brine, dried over MgSO4, filtered, evaporated in vacuo. The crude product was purified using flash column chromatography (0 to 7% MeOH-DCM) to provide the title compound. MS m/e 562.6 (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,
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