Benzylamine → HCID 59833796, compound

Participants

Reaction Steps

N-[3-(7-Chloro-1-methyl-2-oxo-1,2-dihydro-[1,6]naphthyridin-3-yl)-4-methyl-phenyl]-3-trifluoromethyl-benzamide (100 mg, 0.21 mmol) is mixed with benzylamine (35 mg, 0.32 mmol), Pd2(dba)2 (4.8 mg, 2.5%), 1,3-Bis(2,6-di-i-propylphenyl)imidazolium chloride (4.6 mg, 5%) and potassium tert-butanoxide (35.6 mg, 0.32 mmol) under an argon environment. 6 mL of anhydrous 1,4-dioxane is added and the reaction is continued at 100° C. for 14 hours. After cooling and removal of solvent under vacuum, the crude product is dissolved in DMSO and purified by reverse phase preparative HPLC to give the product N-[3-(7-Benzylamino-1-methyl-2-oxo-1,2-dihydro-[1,6]naphthyridin-3-yl)-4-methyl-phenyl]-3-trifluoromethyl-benzamide as pale solid. This product is dissolved into 10 mL of ethanol and 8 mg of 10% palladium carbon powder is added. The reaction is stirred at room temperature under a 50 psi hydrogen environment for 16 hours. After passing through a celite plug to remove the palladium carbon and removing the solvent, the crude product is dissolved in DMSO and purified by reverse phase preparative HPLC to give the final product as a white solid: 1H NMR 400 MHz (DMSO-d6) δ 10.42 (s, 1H), 8.35 (s, 1H), 8.31 (s, 1H), 8.26 (d, 1H, J=7.8 Hz), 7.96 (d, 1H, J=7.7 Hz), 7.78 (t, 1H, J=7.8 Hz), 7.69 (m, 2H), 7.61 (s, 1H), 7.24 (d, 1H, J=8.1 Hz), 6.53 (s, 2H), 6.29 (s, 1H), 3.49 (s, 3H), 2.12 (s, 3H); MS m/z 453.2 (M+1).

Provenance & Evidence