Some common heterocyclic compound, 641571-11-1, name is 3-(4-Methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)aniline, molecular formula is C11H10F3N3, 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. Application In Synthesis of 3-(4-Methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)aniline
To a solution of 2- (5-ethoxy-6- ( (4-methoxybenzyl) oxy) pyridin-3-yl) -4-ethylpyrimidine-5-carboxylic acid (150 mg 0.366 mmol) 3- (4-methyl-1H-imidazol-1-yl) -5- (trifluoromethyl) aniline (88 mg 0.366 mmol) and Et3N (55.6 mg 0.550 mmol) in 1 4-dioxane (10 mL) stirred under N2at 20 was added DPPA (121 mg 0.440 mmol) in one charge. The reaction mixture was stirred at 80 for 2 h. Then the solution was concentrated. The residue was purified by preparative TLC (DCM/MeOH 101 Rf 0.5) to yield a off white solid of 1- (2- (5-ethoxy-6- ( (4-methoxybenzyl) oxy) pyridin-3-yl) -4-ethylpyrimidin-5-yl) -3- (3- (4-methyl-1H-imidazol-1-yl) -5- (trifluoromethyl) phenyl) urea (50 mg 0.077 mmol 21.07yield) . TLC (DCM/MeOH 101 Rf 0.4) 1HNMR(400 MHz CD3OD) delta9.07 (s 1H) 8.74-8.72 (m 1H) 8.12 (d J 9.3 Hz 2H) 7.98 (br. s. 1H) 7.77-7.75 (m 1H) 7.50 (br. s. 1H) 7.41 (d J 8.6 Hz 2H) 7.35 (s 1H) 6.92 (d J 8.8 Hz 2H) 5.40 (s 2H) 4.17 (d J 7.1 Hz 2H) 3.79 (s 3H) 2.91 (d J 7.5 Hz 2H) 2.26 (s 3H) 1.42 (td J 7.3 14.6 Hz 6H) ES-LCMS m/z 648.3 (M+H)
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 641571-11-1, its application will become more common.
Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; GLAXOSMITHKLINE (CHINA) R & D COMPANY LIMITED; CHEUNG, Mui; DEMARTINO, Michael P.; EIDAM, Hilary Schenck; GUAN, Huiping Amy; QIN, Donghui; WU, Chengde; GONG, Zhen; YANG, Haiying; YU, Haiyu; ZHANG, Zhiliu; (391 pag.)WO2016/37578; (2016); A1;,
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