Reference of 129768-28-1,Some common heterocyclic compound, 129768-28-1, name is 5-(Trifluoromethyl)-1H-pyrazole-3-carboxylic acid, molecular formula is C5H3F3N2O2, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.
EXAMPLE 73SYNTHESIS OF N-(2-CHLOROBENZYL)-N-(2-( 1,1 -DIOXIDOTETRAHYDROTHIOPHEN-3 -YL)ETHYL)-3-(TRIFLUOROMETHYL)- 1H-PYRAz0LE-5-cARB0xAMIDE. To a solution of 3-trifluoro-1H-pyrazole-5-carboxylic acid (0.248 g, 1.377 mmol) and N-(2-chlorobenzyl)-2-(tetrahydro-2H-thiopyran-4-yl)ethanamine (0.372 g, 1.377 mmol) in ACN (5 mL) was added T3P (Propylphosphonic anhydride solution, 50 wt% in ethyl acetate) (0.460 g, 1.466 mmol) and TEA (0.495 g). Then the reaction mixture was stirred at r.t. for 1 day. The resulting reaction mixture was diluted with 30 mL DCM and washed with water 10 mL. The DCM phase was dried with Na2SO4 and evaporated. Preparative HPLC purification provided pure product N-(2- chlorobenzyl)-N-(2-(tetrahydro-2H-thiopyran-4-yl)ethyl)-3 -(trifluoromethyl)- 1 Hpyrazole-5-carboxamide (0.060 g, 0.139 mmol, 10% yield).?H-NMR (Acetone-d6/400 MHz): 7.41 (m, 4H), 6.80 (m, 1H), 4.95 (d, 2H), 3.61 (d, 2H), 2.60 (m, 4H), 1.99 (m, 1H), 1.61 (m, 2H), 1.30 (m, 4H). MS (ES, mlz): 432.4 (M+1, 100.0).
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-(Trifluoromethyl)-1H-pyrazole-3-carboxylic acid, its application will become more common.
Reference:
Patent; TOLERO PHARMACEUTICALS, INC.; HO, Koc-Kan; XU, Yong; SAUNDERS, Micheal, David; LIU, Xiaohui; PEARCE, Scott, Albert; WRIGHT, Kevin, Bret; FOULKS, Jason, Marc; PARNELL, Kenneth, Mark; KANNER, Steven, Brian; VOLLMER, David, Lee; LIU, Jihua; WO2014/62838; (2014); A2;,
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