Phenylmethanesulfonyl chloride → HCID 10345947, compound

Participants

Reaction Steps

α-Toluenesulfonyl chloride (0.023 g, 0.12 mmol) and diisopropylethylamine (0.026 mL, 0.15 mmol) were added to a solution of 2-(5-benzo[1,3]dioxol-5-yl-2-piperidin-4-yl-3H-imidazol-4-yl)-pyridine (0.035 g, 0.10 mmol, in 3 mL of anhydrous THF), which was prepared with 4-(4-benzo[1,3]dioxol-5-yl-5-pyridin-2-yl-1H-imidazol-2-yl)-piperidine-1-carboxylic acid benzyl ester in a similar manner as described in Example 9. The reaction mixture was stirred at room temperature for 3 hours. Solvent was removed under reduced pressure, and the residue was dissolved in 1 mL DMSO. The DMSO solution was filtered and injected onto preparative HPLC. HPLC purification eluting with acetonitrile:water gave 0.005 g (10%) of the title compound as a yellow solid. MS (ESP+) m/z 503.1 (M+1). 1H NMR (400 MHz, Methanol-d4) δ 8.67 (m, 1H), 7.82 (m, 1H), 7.42 (m. 7H), 7.02 (m, 3H), 6.07 (s, 2H), 4.38 (s, 2H), 3.81 (m, 2H), 3.17 (m, 1H), 2.85 (m, 1H), 2.10 (m, 2H), 1.90 (m, 2H).

Provenance & Evidence