Trifluoroacetic acid → 3-mercapto-N-methyl-N-(5-(pyridin-3-yl)-1,3,4-thiadiazol-2-yl)propanamide

Participants

Reaction Conditions

Reaction Steps

Triethylsilane (76 μL, 0.48 mmol, 5.0 equiv) and trifluoroacetic acid (710 μL, 5.7 mmol, 100 equiv) were sequentially added to a stirred solution of N-methyl-N-(5-(pyridin-3-yl)-1,3,4-thiadiazol-2-yl)-3-(tritylthio)propanamide (50 mg, 0.096 mmol, 1.0 equiv) in dichloromethane (1.3 mL) at 23° C. The resulting solution was stirred at 23° C. for 30 m. The reaction mixture was diluted with a saturated solution of sodium bicarbonate (40 mL) and extracted with ethyl acetate (3×30 mL). The combined organic layers were dried (Na2SO4), gravity-filtered, and concentrated by rotary evaporation. The residue was purified by silica gel column chromatography (ethyl acetate) to afford the title compound as a white powder (23 mg, 85%): mp 149-151° C.; 1H NMR (300 MHz, CDCl3) δ 9.17 (br s, 1H), 8.71 (m, 1H), 8.29 (m, 1H), 7.44 (dd, J=8, 5 Hz, 1H), 3.87 (s, 3H), 2.91-310 (m, 4H), 1.87 (t, J=8 Hz, 1H); ESIMS m/z 281 ([M+H]+).

Provenance & Evidence