Dichloromethane → N-(2-benzo[1,3]dioxol-5-yl-ethyl)-2-(3-imidazol-1-yl-[1,2,4]thiadiazol-5-yl)-succinamic acid ethyl ester

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Reaction Steps

BOP-Cl (784 mg, 3.08 mmol) was added all at once to a solution 2-(3-imidazol-1-yl-[1,2,4]thiadiazol-5-yl)-succinic acid 1-ethyl ester (389 mg, 1.54 mmol) and DCM (10 mL) and stirred at room temperature for 30 min prior to addition of 2-benzo[1,3]dioxol-5-yl-ethylamine (620 mg, 3.08 mmol) and TEA (859 μL, 6.16 mmol). The reaction mixture stirred at r.t. for an additional 20 h. The solvent was evaporated to afford a white slurry oil, diluted with EtOAc (50 mL), washed with sat. NaHCO3 (50 mL), brine (50 mL), dried over Na2SO4, filtered and concentrated to a white solid. Purification was achieved using column chromatography (CH2Cl2 to 4:1 CH2Cl2/MeOH) to afford 17 mg (3%) of N-(2-benzo[1,3]dioxol-5-yl-ethyl)-2-(3-imidazol-1-yl-[1,2,4]thiadiazol-5-yl)-succinamic acid ethyl ester as a white solid. [M+H]+ 443.90; 1H NMR (400 MHz, CDCl3) δ 8.50 (s, 1H), 7.74 (s, 1H), 7.15 (s, 1H), 6.66-6.52 (m, 3H), 6.04 (br s, 1H), 5.86 (s, 2H), 4.31 (q, 2H), 3.78 (t, 1H), 3.63 (t, 2H), 3.16 (t, 2H), 2.83 (d, 2H), 1.32 (t, 3H).

Provenance & Evidence