2-Bromoethanol → HCID 58902377, compound

Participants

Reaction Steps

To a solution of 4-{[7-({[3-(aminomethyl)-5-(trifluoromethyl)phenyl]amino}-carbonyl)-5,6,7,8-tetrahydronaphthalen-2-yl]oxy}-N-methylpyridine-2-carboxamide (0.459 g, 0.921 mmol) in DMF (10 mL) was added 2-bromoethanol (0.100 mL, 1.41 mmol) and TEA (0.300 mL, 2.15 mmol). The reaction mixture was allowed to stir at rt overnight, and then diluted with water. The mixture was extracted with EtOAc and the combined organic solutions were washed with 10% aqueous LiCl, dried over MgSO4, filtered and concentrated. The residue was purified by column chromatography to give 4-{[7-({[3-{[(2-hydroxyethyl)amino]methyl}-5-(trifluoromethyl)phenyl]amino}carbonyl)-5,6,7,8-tetrahydronaphthalen-2-yl]oxy}-N-methylpyridine-2-carboxamide I-276 (0.352 g, 71%) as a white solid. 1H NMR (400 MHz, d6-DMSO, HCl salt) δ: 10.65 (s, 1H), 9.19-9.09 (br s, 1H), 8.85-8.77 (m, 1H), 8.50 (d, 1H), 8.17-8.02 (m, 2H), 7.66 (s, 1H), 7.41-7.36 (m, 1H), 7.28-7.21 (m, 1H), 7.19-7.14 (m, 1H), 7.04-6.94 (m, 2H), 4.22 (t, 2H), 3.83-3.76 (m, 2H), 3.67 (t, 2H), 3.03-2.81 (m, 5H), 2.77 (d, 3H), 2.17-2.08 (m, 1H), and 1.89-1.75 (m, 1H). LCMS: (FA) ES+543.2, ES−541.2.

Provenance & Evidence