Phenylmethanesulfonyl chloride → HCID 10481670, compound

Participants

Reaction Steps

α-Toluenesulfonyl chloride (0.032 g, 0.17 mmol) and diisopropylethylamine (0.036 mL, 0.21 mmol) were added to a solution of 2-(5-benzo[1,3]dioxol-5-yl-2-piperidin-4-yl-3H-imidazol-4-yl)-6-methyl-pyridine (0.050 g, 0.14 mmol; see Example 9) in anhydrous THF (3 mL). 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 (7%) of the title compound as a yellow solid. MS (ESP+) m/z 517.2 (M+1). 1H NMR (400 MHz, Methanol-d4) δ 7.73 (t, 1H, J=7.7 Hz), 7.42 (m, 5H), 7.33 (d, 1H, J=7.3 Hz), 7.27 (d, 1H, J=7.3 Hz), 6.07 (s, 2H), 4.40 (s, 2H), 3.82 (m, 2H), 3.19 (m, 1H), 2.85 (m, 2H), 2.66 (s, 3H), 2.10 (m, 2H), 1.92 (m, 2H).

Provenance & Evidence