Acetic Anhydride → n-(1-{5-[2-(4-Isopropoxyphenoxy)-1,3-thiazol-5-yl]thien-2-yl}ethyl)acetamide

Participants

Reaction Steps

To a solution of Example 3C (200 mg, 0.41 mmol) at room temperature in dichloromethane (5 mL) was added hydrazine hydrate (197 uL, 4.1 mmol). Ethanol was added until a clear, single phase was formed. After an hour at room temperature, the solvent was removed under vacuum and the reaction mixture was thoroughly dried. To the resulting mixture was added dichloromethane (5 mL), triethylamine (300 uL, 2.15 mmol) and acetic anhydride (150 uL, 1.59 mmol). After two hours at room temperature, methanol was added and the solution was stirred for additional hour. The mixture was concentrated and the product was isolated via silica column chromatography (using a gradient of 25 to 75% ethyl acetate in hexane) and yielded 40 mg of the title compound. 1H NMR (300 MHz, CDCl3) δ ppm 7.16-7.23 (m, 3H) 6.83-6.95 (m, 4H) 5.66 (d, J=8.09 Hz, 1H) 5.25-5.43 (m, 1H) 4.52 (heptet, J=6.25 Hz, 1H) 2.00 (s, 3H) 1.57 (d, J=6.99 3 H) 1.35 (d, J=6.25 Hz, 6H), MS (DCI): m/z 403 (M+H).

Provenance & Evidence