Acetone → Hydrochloric Acid

Participants

Reaction Steps

Compound 4-(2-fluorobenzylamino)-6-(4-(piperidin-4-yl)phenylamino)nicotinamide (Example 106) HCl salt (110 mg, 0.24 mmol) was stirred in 5 mL 1,2-dichloroethane (DCE) and 5 mL dioxane. To the slurry were added DIEA (0.21 mL, 1.2 mmol) and acetone (0.18 mL, 2.4 mmol). The mixture was stirred at RT for 1 h. To the mixture were then added HOAc (0.25 mL) and NaBH(OAC)3 (260 mg, 1.2 mmol). The mixture was stirred at RT for overnight. Water (10 mL) was added. The mixture was concentrated in vacuo. The residue was subjected to reverse phase prep HPLC to isolate the title compound as HCl salt. UV=259 nm. M+H found for C27H32FN5O: 462.5. NMR (CD3OD): 8.18 (1H, s), 7.38 (1H, m), 7.30 (2H, d, J=8.8 Hz), 7.09 (3H, m), 7.04 (1H, m), 7.00 (1H, m), 5.82 (1H, s), 4.47 (2H, s), 3.58 (2H, m), 3.22 (3H, m), 2.95 (1H, m), 2.18 (2H, m), 2.01 (2H, m), 1.42 (6H, d, J=6.8 Hz) ppm.

Provenance & Evidence