Reaction Steps
1-(5-(4-(bis(4-methoxybenzyl)amino)-6-methyl-1,3,5-triazin-2-yl)-6-(6-methoxypyridin-3-ylamino)pyridin-3-yl)ethanol (732.1 mg, 1.233 mmol) was dissolved in dichloromethane (22 mL) and the reaction flask was cooled in an ice water bath. The reaction was stirred under nitrogen, and triethylamine (0.77 mL, 5.5 mmol) and methanesulfonylchloride (0.37 mL, 4.8 mmol) were added via syringe. The reaction was stirred at 0° C. under nitrogen for 15 min and then was diluted with dichloromethane (125 mL) and treated with water (20 mL). The layers were separated, and the aqueous phase was extracted with dichloromethane. The organic extracts were combined, dried over sodium sulfate, filtered, concentrated, and dissolved in dichloromethane (13 mL). To this solution were added triethylamine (0.77 ml, 5.5 mmol) and 1-methanesulfonylpiperazine (648 mg, 3.95 mmol). The reaction was stirred under nitrogen at room temperature overnight and then concentrated and purified on a silica gel filter (150 mL fritted filter with about 2 inches of silica gel; 100:1 DCM/MeOH to elute impurities to 50:1 DCM/MeOH to elute product). The fractions with product were collected, concentrated, and washed with hexanes. The material dried under high vacuum at room temperature to give N,N-bis(4-methoxybenzyl)-4-(2-(6-methoxypyridin-3-ylamino)-5-(1-(4-(methylsulfonyl)piperazin-1-yl)ethyl)pyridin-3-yl)-6-methyl-1,3,5-triazin-2-amine (501.6 mg,). 1H NMR (CDCl3, 400 MHz) δ 11.63 (s, 1H), 8.70 (d, J=2.54 Hz, 1H), 8.28 (d, J=2.54 Hz, 1H), 8.22 (d, J=2.54 Hz, 1H), 7.92 (dd, J=9.00 Hz, 2.74 Hz, 1H), 7.22 (t, J=9.29 Hz, 4H), 6.86 (dd, J=18.58 Hz, 8.61 Hz, 4H), 6.72 (d, J=8.80 Hz, 1H), 4.93-4.76 (m, 4H), 3.93 (s, 3H), 3.82 (s, 3H), 3.79 (s, 3H), 3.54 (quartet, J=6.78 Hz, 1H), 3.16 (t, J=4.40 Hz, 4H), 2.68 (s, 3H), 2.61-2.49 (m, 7H), 1.38 (d, J=6.65 Hz, 3H). m/z (ESI, +ve ion) 740 (M+H)+.
