Water → N-((5-((2-acetamidopyridin-4-yl)oxy)pyridin-2-yl)carbamoyl)isobutyramide

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Reaction Steps

A solution of isobutyramide (0.071 g, 0.819 mmol) in DCE (3 mL) was treated with oxalyl chloride (0.104 g, 0.819 mmol), stirred at RT for 1 h, then heated at 75° C. for 1 h. The mixture was cooled to RT, treated with a solution of Example A2 (0.1 g, 0.409 mmol) and TEA (0.124 g, 1.228 mmol) in THF (3 mL) and stirred at RT for 1 h. The mixture was treated with water, extracted with 10% MeOH/DCM (1×), then DCM (1×) and the combined organics were washed with brine, dried over Na2SO4 and concentrated to dryness. The residue was treated with EtOAc, sonicated and the resulting solid collected via filtration. The solid was re-suspended in EtOAc, sonicated and again collected via filtration and dried to afford N-((5-((2-acetamidopyridin-4-yl)oxy)pyridin-2-yl)carbamoyl)isobutyramide (45 mg, 31%). 1H NMR (400 MHz, DMSO-d6): δ 11.11 (s, 1H), 10.85 (s, 1H), 10.56 (s, 1H), 8.24 (d, J=2.9 Hz, 1H), 8.18 (d, J=5.7 Hz, 1H), 8.08 (d, J=9.0 Hz, 1H), 7.72 (dd, J=9.0, 2.9 Hz, 1H), 7.64 (d, J=2.4 Hz, 1H), 6.68 (dd, J=5.7, 2.4 Hz, 1H), 2.68-2.66 (m, 1H), 2.03 (s, 3H), 1.09 (d, J=6.8 Hz, 6H); MS (ESI) m/z: 358.2 (M+H+).

Provenance & Evidence