Sodium Cyanide → (5-(4-(Bis(4-methoxybenzyl)amino)-6-methyl-1,3,5-triazin-2-YL)-6-(5-fluoro-6-methoxypyridin-3-ylamino)pyridin-3-YL)(4-hydroxypiperidin-1-YL)methanone

Participants

Reaction Steps

A solution of 5-(4-(bis(4-methoxybenzyl)amino)-6-methyl-1,3,5-triazin-2-yl)-6-(5-fluoro-6-methoxypyridin-3-ylamino)nicotinaldehyde (0.054 g, 0.091 mmol) in THF (1.0 mL) at room temperature was treated with sodium cyanide (4.44 mg, 0.091 mmol) (Sigma-Aldrich), piperidin-4-ol (0.046 g, 0.453 mmol) (Aldrich) and manganese (IV) oxide (0.118 g, 1.360 mmol) (Sigma-Aldrich). The mixture was stirred at room temperature. After 1 h the reaction was incomplete, so a few granules of NaCN, and another 15 equiv. of manganese (IV) oxide (0.118 g, 1.360 mmol) were added. The mixture was stirred at room temperature for 18 h, then filtered through Celite® (diatomaceous earth). The organic layer was washed with water, then brine, dried over MgSO4, filtered and concentrated to give the title compound as a yellow film (85%). 1H NMR (400 MHz, d6-DMSO) δ 11.86 (s, 1H); 8.77 (d, J=2.3 Hz, 1H); 8.38 (d, J=2.3 Hz, 1H); 8.02-8.11 (m, 2H); 7.23-7.32 (m, 2H); 7.19 (m, J=8.6 Hz, 2H); 6.91 (m, 2H); 6.83 (d, J=8.8 Hz, 2H); 4.72-4.87 (m, 5H); 3.90-3.95 (m, 3H); 3.66-3.76 (m, 8H); 3.17-3.28 (m, 2H); 2.58 (s, 3H); 1.71 (br. s., 2H); 1.36 (br. s., 2H). m/z (ESI, +ve ion) 695.0 (M+H)+.

Provenance & Evidence