Ethyl Acetate → HCID 178465998, compound

Participants

Reaction Steps

To a mixture of 2-(4-(5-ethoxy-6-((4-methoxybenzyl)oxy)pyridin-3-yl)-2-fluorophenyl)acetic acid (100 mg, 0.243 mmol) and 3-(1,1,1-trifluoro-2-methylpropan-2-yl)-1H-pyrazol-5-amine (51.6 mg, 0.267 mmol) in pyridine (3 mL) was added T3P® (EA solvate) (0.3 mL, 0.243 mmol) at 25° C. Then the mixture was stirred for 2 h, the mixture was concentrated to give a residue which was distributed between DCM (20 mL) and H2O (10 mL) and extracted with DCM (20 mL×2). The combined organic extracts were washed with brine (20 mL), dried over Na2SO4, filtered and concentrated to yield a white solid of 2-(4-(5-ethoxy-6-((4-methoxybenzyl)oxy)pyridin-3-yl)-2-fluorophenyl)-N-(3-(1,1,1-trifluoro-2-methylpropan-2-yl)-1H-pyrazol-5-yl)acetamide (100 mg, 0.102 mmol, 42.1% yield): 1H NMR (400 MHz, CD3OD) δ 8.52 (d, J=4.2 Hz, 1H), 7.93 (d, J=2.0 Hz, 1H), 7.48-7.33 (m, 6H), 6.90 (d, J=8.6 Hz, 2H), 5.35 (s, 2H), 4.19-4.09 (m, 2H), 3.78 (s, 3H), 3.70-3.63 (m, 2H), 1.54-1.36 (m, 9H). ES-LCMS m/z 587 (M+H).

Provenance & Evidence