Ethyl Acetate → HCID 68672510, compound

Participants

Reaction Conditions

Reaction Steps

To N-(4,4-dimethyl-2-oxohexyl)-3-(3-pyridin-2-yl-[1,2,4]oxadiazol-5-yl)propionamide (413 mg, 1.2 mmol) in acetic acid (3 mL) was added ammonium acetate (924 mg, 12 mmol), and the mixture was heated at 180° C. for 20 minutes in a microwave reactor (maximum 150 W). The reaction mixture was poured into ethyl acetate and water, and pH of the aqueous layer was adjusted to 9 with concentrated ammonium hydroxide. The organic layer was separated and concentrated to give a residue. The residue was purified by flash column chromatography (silica gel, eluting with 0-15% 9:1 methanol/ammonium hydroxide mixture in methylene chloride) to afford the title compound, which was converted to the HCl salt with 1M HCl in diethyl ether. 1H NMR (500 MHz, CD3OD) δ 8.83-8.85 (m, 1H), 8.32-8.35 (m, 2H), 7.84-7.89 (m, 1H), 7.22 (s, 1H), 3.59-3.61 (m, 4H), 2.21 (s, 2H), 1.26 (q, J=7.7 Hz, 2H), 0.85 (m, 9H); LC-MS: m/e 326 (M+H).

Provenance & Evidence