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

Participants

Reaction Conditions

Reaction Steps

A solution 2-cyclohexylacetamide (0.104 g, 0.737 mmol) in DCE (4 mL) was treated with oxalyl chloride (0.129 mL, 1.474 mmol) and heated at 70° C. overnight. The mixture was concentrated to dryness, added to a solution of Example A2 (0.09 g, 0.368 mmol) and TEA (0.154 mL, 1.105 mmol) in THF (3 mL) and stirred at RT for 1 h. The mixture was treated with water, extracted with EtOAc (2×) and the combined organics were washed with brine, dried over Na2SO4 and concentrated to dryness. The resulting residue was suspended in 60% EtOAc/Hex, sonicated and the solid collected via filtration and dried to afford N-((5-((2-acetamidopyridin-4-yl)oxy)pyridin-2-yl)carbamoyl)-2-cyclohexylacetamide (77 mg, 51%) as a white solid. 1H NMR (400 MHz, DMSO-d6): δ 11.11 (s, 1H), 10.83 (s, 1H), 10.56 (s, 1H), 8.23 (d, J=2.9 Hz, 1H), 8.18 (d, J=5.7 Hz, 1H), 8.07 (d, J=9.0 Hz, 1H), 7.71 (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), 2.27 (d, J=7.0 Hz, 2H), 2.02 (s, 3H), 1.73-1.56 (br m, 5H), 1.18-1.13 (m, 4H), 0.97-0.94 (m, 2H); MS (ESI) m/z: 412.2 (M+H+).

Provenance & Evidence