New discoveries in chemical research and development in 2021. The dynamic chemical diversity of the numerous elements, ions and molecules that constitute the basis of life provides wide challenges and opportunities for research. 6523-49-5, name is 4-(1,2,4-Triazol-1-yl)aniline belongs to triazoles compound, it is a common compound, a new synthetic route is introduced below. 6523-49-5
General procedure: An aqueous solution of cesium carbonate (130 mg, 0.4 mmol) in water (300 ul) was dispensed into each well containing a pre-mixed solution of 4-chloro-N-(4-methoxyphenyl)pyridin-2-amine (58.8 mg, 0.2mmol), respective aniline (0.26 mmol), xantphos (13.9 mg, 0.024mmol) and palladium (II) acetate (3.6 mg, 0.016 mmol) in DMA (1.25 ml). The resultant plate was placed on a pre-heated SOPHAS base plate set at 150 oC and shaken for 1 hour. The plate was cooled to room temperature and MP-TMT resin (90 mg) added to each well prior to shaking overnight at room temperature. The following day each well was transferred to a 48 well filter plate, washing through with an extra aliquot of DMA (200 ul) before a final centrifuge. The crude filtrates were then purified by preparative HPLC (Waters XBridge Prep C18 OBD column, 5mu silica, 19 mm diameter, 100 mm length), using decreasingly polar mixtures of water (containing 1% NH3) and MeCN as eluents. Fractions containing the desired compound were evaporated to dryness to afford required N2-(4-methoxyphenyl)-N4-[aryl]pyridine-2,4-diamine (23-42%) N2-(4-methoxyphenyl)-N4-[4-(1,2,4-triazol-1-yl)phenyl]pyridine-2,4-diamine (5a) 28%, LCMS (tR = 2.49 min., purity = 100%), ESI+ m/z, 359.08 (M+H)+; 1H NMR (DMSO-d6, 500 MHz): delta 9.20 (1H, s); 8.72 (1H, s), 8.50 (1H, s), 8.20 (1H, s), 7.85 (1H, m), 7.78 (2H, m), 7.49 (2H, m), 7.32 (2H, m), 6.85 (2H, m), 6.45 (1H, s), 6.35 (1H, m), 3.72 (3H, s); 13C NMR (176 MHz, DMSO-d6) delta 157.53, 153.44, 152.03, 150.31, 147.99, 141.77, 140.89, 135.27, 130.70, 120.65, 120.15, 120.01, 113.79, 103.08, 92.70, 55.11; HRMS m/z (ESI+) calculated for C20H18ON6, 359.16149; found: 359.16107.
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Reference:
Article; Burton, Rebecca J.; Crowther, Mandy L.; Fazakerley, Neal M.; Fillery, Shaun M.; Hayter, Barry M.; Kettle, Jason G.; McMillan, Caroline A.; Perkins, Paula; Robins, Peter; Smith, Peter M.; Williams, Emma J.; Wrigley, Gail L.; Tetrahedron Letters; vol. 54; 50; (2013); p. 6900 – 6904;,
1,2,3-Triazole – Wikipedia,
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