Acetyl chloride → S-3-(methyl(5-(pyridin-3-yl)-1,3,4-thiadiazol-2-yl)amino)-3-oxopropyl ethanethioate

Participants

Reaction Conditions

Reaction Steps

Triethylamine (12 μL, 0.086 mmol, 1.2 equiv) and acetyl chloride (6 μL, 0.08 mmol, 1 equiv) were sequentially added to a stirred solution of 3-mercapto-N-methyl-N-(5-(pyridin-3-yl)-1,3,4-thiadiazol-2-yl)propanamide (20 mg, 0.071 mmol, 1.0 equiv) in 1,2-dichloroethane (1.4 mL) at 23° C. The resulting pale yellow solution was stirred at 23° C. for 16 h. The reaction mixture was directly subjected to silica gel column chromatography (ethyl acetate) to afford the title compound as a white powder (23 mg, 99%): mp 133-135° C.; 1H NMR (300 MHz, CDCl3) δ 9.14 (d, J=2 Hz, 1H), 8.69 (dd, J=5, 2 Hz, 1H), 8.27 (dt, J=8, 2 Hz, 1H), 7.42 (dd, J=8, 5 Hz, 1H), 3.82 (s, 3H), 3.26 (t, J=7 Hz, 2H), 3.03 (t, J=7 Hz, 2H), 2.36 (s, 3H); ESIMS m/z 323 ([M+H]+).

Provenance & Evidence