Application of 112110-07-3, With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.112110-07-3, name is 5-(Trifluoromethyl)pyridin-3-amine, molecular formula is C6H5F3N2, molecular weight is 162.11, as common compound, the synthetic route is as follows.
General procedure: l-methyl-4-[(3-methyloxetan-3-yl)sulfamoyl]-lH-pyrrole-2-carboxylic acid (200 mg, (0182) 0.729 mmol) was dissolved in DMF (1.7 mL) and triethylamine (0.41 mL, 2.9 mmol) and HATU (360 mg, 0.95 mmol) were added. After 10 minutes 4-aminopyridine-2-carbonitrile (174 mg, 1.46 mmol) was added. The reaction mixture was stirred at room temperature for 1 hour and heated at 65C for 42 hours. The mixture was poured into water (50 mL) and the organics were extracted with ethyl acetate (3 x 40 mL). The combined organic layers were dried (Na2S04) and concentrated to dryness. The residue was purified using silica gel column chromatography (ethyl acetate in heptane from 0 to 100%) followed by prep. HPLC (Stationary phase: RP SunFire Prep C18 OBD-IotaOmicronmuiotaeta, 30 x 150mm), Mobile phase: 0.5% NH4OAc solution in water + 10% CH3CN, MeOH), resulting in compound 1 (4.6 mg). 1H NMR (400 MHz, DMSO-d6) delta ppm 1.54 (s, 3 H), 3.94 (s, 3 H), 4.14 (d, J=6.4 Hz, 2 H), 4.60 (d, J=5.9 Hz, 2 H), 7.43 (s, 1 H), 7.66 (d, J=1.3 Hz, 1 H), 7.86 – 8.12 (m, 2 H), 8.26 (d, J=2.0 Hz, 1 H), 8.60 (d, J=5.7 Hz, 1 H), 10.68 (br. s., 1 H). Method A; Rt: 1.22 min. m/z : 374.0 (M-H)- Exact mass: 375.1. Compound 2 was prepared similarly as described for compound 1, using 5-(trifluoromethyl)-3- aminopyridine instead of 4-aminopyridine-2-carbonitrile. The reaction mixture was stirred at room temperature for 1 hour and heated at 65C for 4 hours. The mixture was poured into water (50 mL), the formed precipitate was filtered and the solids were washed with water and recrystallised from methanol/ethyl acetate (10 mL, 1 : 1). The white solids were filtered, washed with methanol (2 x 3 mL) and dried overnight in vacuum oven resulting in compound 2 (74 mg) as a white solid. 1H NMR (400 MHz, DMSO-d6) delta ppm 1.55 (s, 3 H), 3.94 (s, 3 H), 4.14 (d, J=6.2 Hz, 2 H), 4.60 (d, J=5.9 Hz, 2 H), 7.41 (s, 1 H), 7.63 (s, 1 H), 8.01 (br. s., 1 H), 8.56 (s, 1 H), 8.66 (s, 1 H), 9.13 (s, 1 H), 10.55 (br. s., 1 H). Method B; Rt: 0.84 min. m/z : 417.1 (M-H)~ Exact mass: 418.1.
Statistics shows that 112110-07-3 is playing an increasingly important role. we look forward to future research findings about 5-(Trifluoromethyl)pyridin-3-amine.
Reference:
Patent; JANSSEN SCIENCES IRELAND UC; VANDYCK, Koen; HACHE, Geerwin Yvonne Paul; LAST, Stefaan Julien; ROMBOUTS, Geert; VERSCHUEREN, Wim Gaston; RABOISSON, Pierre Jean-Marie Bernard; WO2015/118057; (2015); A1;,
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