With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.14441-90-8,5-Phenylisoxazole-3-carboxylic acid,as a common compound, the synthetic route is as follows.
To a solution of 5-phenylisoxazole-3-carboxylic acid (117 mg, 0.620 mmol) in dichloromethane (2 mL) at 20 C. was added oxalyl chloride (1 mL). The reaction mixture was stirred at room temperature for 0.5 h. The volatiles were removed in vacuo. The crude residue was dissolved in dichloromethane (2 mL) and added to a mixture of 1-((4-(trifluoromethyl)pyridin-3-yl)methyl)-1H-pyrazol-4-amine (0.150 g, 0.620 mmol) and triethylamine (0.188 g, 1.86 mmol) in dichloromethane (5 mL) dropwise. The reaction mixture was stirred for 0.5 h and purified by prep-HPLC (the crude sample was dissolved in N,N-dimethylformamide and loaded onto Boston C18 21¡Á250 mm 10 mum column. The mobile phases were acetonitrile/0.01% aqueous trifluoroacetic acid) to offer 5-phenyl-N-(1-((4-(trifluoromethyl)pyridin-3-yl)methyl)-1H-pyrazol-4-yl)isoxazole-3-carboxamide (65.5 mg, 0.158 mmol, 25%) as a white solid. 1H NMR (500 MHz, Dimethylsulfoxide-d6) delta 11.09 (s, 1H), 8.81 (d, J=5.0 Hz, 1H), 8.34 (s, 1H), 8.29 (s, 1H), 7.98 (dd, J=7.6, 1.6 Hz, 2H), 7.80 (d, J=5.0 Hz, 1H), 7.75 (s, 1H), 7.59-7.56 (m, 3H), 7.47 (s, 1H), 5.61 (s, 2H); LCMS (ESI) m/z: 414.1 [M+H]+.
14441-90-8 5-Phenylisoxazole-3-carboxylic acid 151916, aIsoxazoles compound, is more and more widely used in various.
Reference£º
Patent; Yumanity Therapeutics, Inc.; WRONA, Iwona; TIVITMAHAISOON, Parcharee; TARDIFF, Daniel; PANDYA, Bhaumik; OZBOYA, Kerem; LUCAS, Matthew; BOURDONNEC, Bertrand Le; (259 pag.)US2019/330198; (2019); A1;,
Isoxazole – Wikipedia
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