5-Chloro-3-(1H-imidazol-1-yl)-1,2,4-thiadiazole → HCID 58654443, compound

Participants

Reaction Steps

2-Amino-N-(2-benzo[1,3]dioxol-5-yl-ethyl)-3-methyl-butyramide (135 mg, 0.51 mmol) was dissolved in DMSO (2 mL) and triethylamine (150 μL). Next, the 5-chloro-3-imidazol-1-yl-[1,2,4]thiadiazole (95.1 mg, 0.51 mmol) was added to the reaction vessel and it was stirred at room temperature for 16 hours. After this period, a portion of brine (50 mL) was added and the mixture was transferred to a separatory funnel and extracted with ethyl acetate (75 mL). The organic layer was dried over Na2SO4 and concentrated under vacuum. The crude material was purified by Flash Chromatography (0-50% ACN/DCM gradient) to afford 20.4 mg of pure product, N-(2-benzo[1,3]dioxol-5-yl-ethyl)-2-(3-imidazol-1-yl-[1,2,4]thiadiazol-5-ylamino)-3-methyl-butyramide. [M+H]+ 414.84; 1H NMR (400 MHz, CDCl3) δ 8.52 (s, 1H), 7.71 (s, 1H), 6.99 (s, 1H), 6.62-6.52 (m, 3H), 5.82-5.80 (m, 2H), 4.0 (Br s, 1H), 3.64-3.47 (m, 3H), 2.76-2.72 (m, 2H), 2.30-2.29 (m, 1H), 1.03-1.01 (m, 6H).

Provenance & Evidence