Sodium Cyanide → (5-(4-(Bis(4-methoxybenzyl)amino)-6-methyl-1,3,5-triazin-2-yl)-6-(6-methoxypyridin-3-ylamino)pyridin-3-yl)(4-(methylsulfonyl)piperazin-1-yl)methanone

Participants

Reaction Steps

A mixture of 5-(4-(bis(4-methoxybenzyl)amino)-6-methyl-1,3,5-triazin-2-yl)-6-(6-methoxypyridin-3-ylamino)nicotinaldehyde (Example 144, 1.00 g, 1.731 mmol), activated manganese (IV) oxide (<5 micron; 4.52 g, 51.9 mmol), sodium cyanide (0.053 mL, 1.731 mmol) and 1-(methylsulfonyl)piperazine (0.711 g, 4.33 mmol) in THF (15 mL) was stirred rapidly under nitrogen for 72 h. The reaction was filtered through Celite® (diatomaceous earth) rinsing with 10% MeOH/DCM followed by EtOAc. The filtrate was concentrated and adsorbed onto 5 g silica gel and passed through an 80 g column using 20-100% EtOAc/hexanes to give (5-(4-(bis(4-methoxybenzyl)amino)-6-methyl-1,3,5-triazin-2-yl)-6-(6-methoxypyridin-3-ylamino)pyridin-3-yl)(4-(methylsulfonyl)piperazin-1-yl)methanone (0.352 g, 0.476 mmol, 27.5% yield) as a yellow foam. m/z (ESI, +ve ion) 740 (M+H)+. 1H NMR (400 MHz, CDCl3) δ 12.02 (s, 1H); 8.91 (d, J=2.3 Hz, 1H); 8.42 (d, J=2.5 Hz, 1H); 8.29 (d, J=2.5 Hz, 1H); 7.90 (dd, J=8.8, 2.7 Hz, 1H); 7.11-7.24 (m, 4H); 6.80-6.94 (m, 4H); 6.75 (d, J=9.0 Hz, 1H); 4.85 (s, 2H); 4.82 (s, 2H); 3.95 (s, 3H); 3.82 (s, 3H); 3.80 (s, 3H); 3.71-3.78 (m, 4H); 3.17-3.25 (m, 4H); 2.70 (s, 3H); 2.60 (s, 3H).

Provenance & Evidence