16681-65-5, The chemical industry reduces the impact on the environment during synthesis 16681-65-5, name is 1-Methyl-1H-1,2,3-triazole, I believe this compound will play a more active role in future production and life.
Procedure A To a flask containing 1-methyl-1H-1,2,3-triazole (400 mg, 4.81 mmol, prepared according to PCT Int. Appl., 2008098104) was added THF (25 mL) and the colorless solution was cooled to -50 C. Then, n-BuLi (2.5 M in hexanes, 1.88 mL) was added drop wise which afforded a dark reddish-brown solution. The mixture was allowed to warm gradually to -10 C. over 30 minutes, then a solution of (4-chloro-2-methoxy-3-(4-(trifluoromethyl)benzyl)quinolin-6-yl)(1,2-dimethyl-1H-imidazol-5-yl)methanone (750 mg, 1.58 mmol, Intermediate 49: step b) in THF (5 mL) was introduced at -10 C. The reaction mixture became a dark brown color and was allowed to warm gradually to room temperature. The mixture was stirred for 60 minutes at room temperature, then quenched with aqueous NH4Cl solution. The aqueous portion was extracted with EtOAc-THF (?10:2, v/v) 5*50 mL. The combined organics were washed with brine, dried over MgSO4, filtered and concentrated to provide a brown foam. Chromatography on silica gel (5% MeOH-DCM increasing to 10% MeOH) provided the title compound as a yellow solid. MS m/e 557.2 [M+H]+. 1H NMR (500 MHz, CDCl3) delta 8.23 (d, J=1.8 Hz, 1H), 7.72 (d, J=8.7 Hz, 1H), 7.49 (d, J=11.5 Hz, 2H), 7.38 (d, J=8.0 Hz, 3H), 7.30 (s, 1H), 7.06 (d, J=5.9 Hz, 1H), 5.99 (s, 1H), 4.33-4.19 (m, 2H), 4.06 (s, 3H), 3.88 (s, 3H), 3.33 (s, 3H), 2.14 (s, 3H). The racemic material was separated into its individual enantiomers using the following conditions: Chiralpack OD column; 80% heptanes: 20% ethanol; wavelength=242 nM to provide the two enantiomers. The first eluting enantiomer was Example 80B and the second eluting enantiomer was Example 80C.
The chemical industry reduces the impact on the environment during synthesis 1-Methyl-1H-1,2,3-triazole. I believe this compound will play a more active role in future production and life.
Reference:
Patent; Janssen Pharmaceutica NV; 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.; Pierce, Joan; Goldberg, Steven; Fourie, Anne; Xue, Xiaohua; US2014/107094; (2014); A1;,
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