Pyridine → N-(5-{5-[(hydroxyimino)methyl]-2-thienyl}-4-methyl-1,3-thiazol-2-yl)acetamide

Participants

Reaction Conditions

Reaction Steps

N-[2-(5-Formyl-thiophen-2-yl)-4-methyl-thiazol-5-yl]-acetamide, Compound (1) (104 mg; 0.39 mmol; 1 eq.), is dissolved in a THF/Ethanol 1:1 mixture (10 ml) at room temperature. Hydroxylamine hydrochloride (275 mg; 3.9 mmol; 10 eq.) and pyridine (310 μl; 3.9 mmol; 10.0 eq.) are added and reaction mixture is heated at 70° C. for 30 minutes. Reaction mixture is cooled down to room temperature and solvents are evaporated. The crude material is dissolved in dichloromethane and filtrated through a small silica cartridge, affording Compound (14) as mixture of oxime isomers, a yellow solid (55 mg; 55%). 1H NMR (MeOH-d4, 300 MHz) δ 2.25 (s, 3H), 2.50 (s, 3H), 6.65 (s, 1H), 7.12 (d, J=6 Hz, 1H), 7.40 (d, J=6 Hz, 1H), 7.72 (s, 1H). M−(ESI): 280.36; M+(ESI): 282.40. HPLC, Rt: 2.64 min (purity: 87.8%).

Provenance & Evidence