Potassium Iodide → HCID 11711303, compound

Participants

Reaction Steps

A solution of benzo[1,3]dioxol-5-ylmethyl-(2-chloro-ethyl)-methyl-ammonium hydrochloride (130 mg, 492 μmol), 3-imidazol-1-yl-5-pyrrolidin-2-yl-[1,2,4]thiadiazole (110 mg, 497 μmol), potassium iodide (20 mg, 120 μmol), and TEA (200 μL, 1.44 mmol) in DMF (1.8 mL) was heated at 140 C for 7 min. The reaction mixture was cooled to r.t. and poured into 10 mL of 1N K2HPO4(aq)/EtOAc (1:1). The organic layer was isolated and concentrated to crude residue. Purification was achieved using reverse phase HPLC (5% to 100% Acetonitrile/H2O, 0.1% TFA) to afford 10 mg (4%) of benzo[1,3]dioxol-5-ylmethyl-{2-[2-(3-imidazol-1-yl-[1,2,4]thiadiazol-5-yl)-pyrrolidin-1-yl]-ethyl}-methyl-amine as the TFA salt. [M+H]+ 412.85; 1H NMR (400 MHz, CDCl3) δ 9.23 (s, 1H), 7.95 (s, 1H), 7.46 (s, 1H), 6.88 (s, 1H), 6.81 (m, 2H), 6.01 (s, 2H), 4.24 (m, 1H), 4.15 (m, 2H), 3.0-3.4 (m, 5H), 2.72 (s, 3H), 2.58 (m, 1H), 2.40 (m, 1H), 1.98 (m, 2H), 1.90 (m, 1H).

Provenance & Evidence