Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 16681-65-5, name is 1-Methyl-1H-1,2,3-triazole, A new synthetic method of this compound is introduced below., SDS of cas: 16681-65-5
Example 89: (4-chloro-2-methoxy-3-(4-(trifluoromethyl)benzyl)quinolin-6-yl)(1-methyl-1H-1,2,3-triazol-5-yl)(1-methyl-1H-imidazol-5-yl)methanol To a flask containing 1 -methyl- lH-l,2,3-triazole (100 nig, 1 ,2 mmol) was added THF (10 mL) and the colorless solution was cooled to -43 C using a CH3CN-CO2bath. Then, w-BuLi (2.5 M in hexanes, 490 11L, 1.23 mmol) was added dropwise which afforded an opaque mixture. The mixture was stirred at -40 C for 30 minutes, then a homogeneous solution of (4-chloro-2- methoxy-3-(4-(trifluoromethyl)benzyl)quinolin-6-yl)(l -methyl- lH-imidazol-5-yl)methanone (255 mg, 0.54 mmol. Intermediate 80: step b) in 2 mL THF was introduced. After 5 minutes, the reaction mixture was then placed in an ice-water bath. The reaction was quenched after 20 minutes with aqueous NH4CI solution and the aqueous portion was extracted with EtOAc (3 x 30 mL) and EtOAciTHF (1 : 1, 30 mL). The combined organics were washed with brine, dried over MgS04, filtered and concentrated. The solid was triturated with MeOH and filtered to give a yellow filtrate which was concentrated and chromatographed on silica gel (3% MeOH-DCM increasing to 10% MeOH) to afford the title compound.JH NMR (500 MHz, CDCI3) delta 8.22 (d, J 2.1 Hz, 1H), 7.76 (d, ,/ 8.7 Hz, 2H), 7.49 (d, J = 8.1 Hz, 2H), 7.41 – 7.35 (m, 3H), 7.10 (s, 1H), 6.99 (s, 1H), 6.22 (s, I I I). 4.29 (s, 2H), 4.07 (s, 3H), 3.89 (s, 3H), 3.41 (s, 3H). MS (ESI): mass calcd. for Chemical Formula: C26H22CIF3N6O2; Exact Mass: 542.14, m/z found 542.9[Mu+EtaGamma.(4-Chloro-2-methoxy-3-(4-(trifiuoromethyi)benzyl)quinolin-6-yl)(l -methyl- lH-l ,2,3-triazo 1-5- yl)(l-methyl-lH-imidazol-5-yi)methanol was purified by chiral SFC (Stationary phase: CHIRALPAK AD-H 5 muetaiota, 250 x 20 mm, Mobile phase: 80% C02, 20% mixture of MeOH / “PrOH, 50/50 v/v (+ 0.3% /PrNEb)), to give Example 89b as the first compound eluted from the chiral column and Example 89e as the second compound eluted from the chiral column.
The synthetic route of 16681-65-5 has been constantly updated, and we look forward to future research findings.
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.; FOURIE, Anne; XUE, Xiaohua; CUMMINGS, Maxwell D.; JONES, William Moore; GOLDBERG, Steven; WO2015/57205; (2015); A1;,
1,2,3-Triazole – Wikipedia,
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