Trifluoroacetic acid → N5-(3-(4-Amino-6-methyl-1,3,5-triazin-2-YL)pyridin-2-YL)-2-chloropyridine-3,5-diamine

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Reaction Steps

A solution of N-(5-(3-(4-(bis(4-methoxybenzyl)amino)-6-methyl-1,3,5-triazin-2-yl)pyridin-2-ylamino)-2-chloropyridin-3-yl)-4-fluorobenzenesulfonamide (0.087 g, 0.120 mmol) in trifluoroacetic acid (Aldrich) (0.622 mL, 8.37 mmol) and trifluoromethane sulfonic acid (TCI) (0.265 mL, 2.99 mmol) was heated at 80° C. in a sealed tube for 20 min. The reaction mixture was first neutralized with sat. NaHCO3 and then extracted with CHCl3 (3×15 mL). The combined organic layers were washed with water, brine, dried over MgSO4 and concentrated. The crude product was purified by column chromatography (40 g, 20% to 30% acetone in hexanes) to give the product as a white solid (0.025 g). m/z (ESI, +ve ion) 329.0 (M+H)+. 1H NMR (300 MHz, d6-DMSO) δ 12.01 (s, 1H); 8.79 (d, J=7.16 Hz, 1H); 8.37 (d, J=4.39 Hz, 1H); 7.96 (s, 2H); 7.61-7.88 (m, 2H); 6.96 (dd, J=7.89, 4.82 Hz, 1H); 5.48 (s, 2H); 2.45 (s, 3H).

Provenance & Evidence