New discoveries in chemical research and development in 2021. Chemo-enzymatic cascade processes are invaluable due to their ability to rapidly construct high-value products from available feedstock chemicals in a one-pot relay manner. 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
To a flask containing 1-methyl-1H-1,2,3-triazole (250 mg, 3.01 mmol) was added THF (20 mL) and the solution was cooled to -45 C. using a CH3CN-CO2 bath. n-BuLi (2.5 M in hexanes, 1.2 mL, 3 mmol) was added dropwise which produced an opaque suspension. The suspension was stirred at -45 C. for 20 minutes, then a homogeneous solution of (4-chloro-3-isobutyl-2-methoxyquinolin-6-yl)(2,6-dimethylpyridin-3-yl)methanone (848 mg, 2.21 mmol, Intermediate 66: step d) in 3 mL THF was introduced at -45 C. After 10 minutes, the reaction vessel was placed in an ice-water bath. The reaction mixture was quenched after 40 minutes with aqueous NH4Cl solution. The aqueous portion was extracted with EtOAc (4*30 mL) and EtOAc:THF (1:1, 30 mL). The combined organics were washed with brine, dried over MgSO4, filtered and concentrated. Chromatography on silica gel (100% DCM increasing to 5% MeOH-DCM) provided the title compound as an off white amorphous solid. 1H NMR (500 MHz, CDCl3) delta ppm 8.07 (d, J=2.2 Hz, 1H), 7.78 (d, J=8.7 Hz, 1H), 7.32 (dd, J=8.7, 2.2 Hz, 1H), 6.99-6.88 (m, 3H), 4.24 (s, 1H), 4.09 (s, 3H), 3.92 (s, 3H), 2.80 (d, J=7.3 Hz, 2H), 2.53 (s, 3H), 2.36 (s, 3H), 2.08 (hept, J=6.8 Hz, 1H), 0.95 (dd, J=6.7, 1.5 Hz, 6H). MS (ESI): mass calcd. for C25H28ClN5O2, 465.2. m/z found 466.0 [M+H]+. The racemate was separated by chiral chromatography using: Chiralpack OD-H column, 80% heptane/20% ethanol, to give Example 133b as the first compound eluted from the chiral column and Example 133c as the second compound eluted from the chiral column.
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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