Application of 7170-01-6, New Advances in Chemical Research in 2021. As an important bridge between the micro and macro material world, chemistry is one of the main methods and means for humans to understand and transform the material world. 7170-01-6, name is 3-Methyl-1H-1,2,4-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 (S)-i sopropyl 2-(6-(bromomethyl)-4-(4,4- dimethylpiperidin- i-yl)-5 -(2-(4-fluoro-2-methylbenzyl)- 1,2,3 ,4-tetrahydroi soquinolin-6-yl)-2-methylpyridin-3 -yl)-2-(tert-butoxy)acetate (0.030 g, 0.042 mmol) and 3-methyl-i H1,2,4-triazole (0.02 g, 0.241 mmol) in THF (0.5 mL) was added t-BuOK (0.008 g, 0.071 mmol) and stirred at rt for 4 h. Sodium hydroxide (0.04 g, 1.000 mmol) was added and the reaction mixture was stirred at 80 C for 2 h. Then, cooled and purified by prep HPLC to afford three product.(S)-2-(tert-Butoxy)-2-(4-(4,4-dimethylpiperidin- 1 -yl)-5 -(2-(4-fluoro-2-methylbenzyl)- 1,2,3 ,4-tetrahydroisoquinolin-6-yl)-2-methyl-6-((3 -methyl- 1-i ,2,4-triazol- 1- yl)methyl)pyridin-3-yl)acetic acid (0.0037 g, 5.31 tmol, 12.79% yield). LCMS (M+H) =683.2.(S)-2-(tert-butoxy)-2-(4-(4,4-dimethylpiperidin- 1 -yl)-5 -(2-(4-fluoro-2-methylbenzyl)- 1,2,3 ,4-tetrahydroisoquinolin-6-yl)-2-methyl-6-((5-methyl- 1-i ,2,4-triazol- 1- yl)methyl)pyridin-3-yl)acetic acid (0.0086 g, 0.012 mmol, 29.1 % yield). (M+H) =683.2.(S)-2-(tert-butoxy)-2-(4-(4,4-dimethylpiperidin- 1 -yl)-5 -(2-(4-fluoro-2-methylbenzyl)-1,2,3 ,4-tetrahydroisoquinolin-6-yl)-2-methyl-6-((5-methyl- 1-i ,2,4-triazol- 1- yl)methyl)pyridin-3-yl)acetic acid (0.0112 g, 0.016 mmol, 38.3 % yield). (M+H) =683.2.
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Reference:
Patent; VIIV HEALTHCARE UK (NO.5) LIMITED; EASTMAN, Kyle J.; KADOW, John F.; NAIDU, B. Narasimhulu; PARCELLA, Kyle E.; PATEL, Manoj; SIVAPRAKASAM, Prasanna; TU, Yong; (275 pag.)WO2017/25915; (2017); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics