Pyridine → HCID 66611143, compound

Participants

Reaction Steps

A dark brown solution of hydroxyammonium chloride (0.700 g, 10.07 mmol), 5-(4-(bis(4-methoxybenzyl)amino)-6-methyl-1,3,5-triazin-2-yl)-6-(5-fluoro-6-methoxypyridin-3-ylamino)nicotinaldehyde (Example 143, 2.00 g, 3.36 mmol) and pyridine (0.815 mL, 10.07 mmol) in 15 mL DMF was allowed to stir 2 h. The reaction was partitioned between water and EtOAc. The organic layer was washed with water 2 times, saturated aqueous NaCl once, and the organics were dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo to give an orange solid, 2.0 g. This was treated with acetic anhydride (15.84 mL, 168 mmol), and the flask fitted with a water-cooled reflux condenser, and placed in an oil bath. The reaction was heated to reflux for 5 h, and then the reaction was cooled and stirred overnight. The slurry was treated with 80 mL MeOH, filtered and dried in vacuo to give 5-(4-(bis(4-methoxybenzyl)amino)-6-methyl-1,3,5-triazin-2-yl)-6-(5-fluoro-6-methoxypyridin-3-ylamino)nicotinonitrile (1.50 g, 2.53 mmol, 75% yield) as a green-brown solid. m/z (ESI, +ve ion) 593 (M+H)+. 1H NMR (400 MHz, CDCl3) δ 12.46 (s, 1H), 8.99 (d, J=2.3 Hz, 1H), 8.52 (d, J=2.3 Hz, 1H), 7.99 (d, J=2.3 Hz, 1H), 7.92 (dd, J=11.7, 2.2 Hz, 1H), 7.12-7.25 (m, 4H), 6.82-6.94 (m, 4H), 4.88 (s, 2H), 4.82 (s, 2H), 4.04 (s, 3H), 3.82 (s, 3H), 3.81 (s, 3H), 2.61 (s, 3H).

Provenance & Evidence