Acetic Anhydride → HCID 59577666, compound

Participants

Reaction Steps

To a suspension of 1-[6-(benzothiazol-2-yloxy)-1H-indol-3-ylmethyl]-piperidin-4-ylamine 2HCl (200 mg, 0.44 mmol) in DCM (4 mL) was added Et3N (0.37 mL, 270 mg, 2.7 mmol) and acetic anhydride (0.067 mL, 68 mg, 0.66 mmol) and the resulting reaction mixture was stirred (rt, 24 h). The reaction mixture was partitioned with EtOAc (50 mL) and brine (50 mL) and the organic layer was dried, filtered and concentrated in vacuo. The resulting residue was purified silica gel flash column chromatography using MeOH (0.2 M NH3):DCM (0-15%) to provide the title compound as a white solid (111 mg, 60%). MS (ESI): mass calcd. for C23H24N4O2S, 420.5; m/z found, 421.2 [M+H]+. 1H NMR (500 MHz, CDCl3): 9.00 (s, 1H), 7.73 (d, J=6.0, 1H), 7.71 (d, J=5.2, 1H), 7.63 (d, J=7.5, 1H), 7.39-7.36 (m, 1H), 7.31 (br s, 1H), 7.26-7.24 (m, 1H), 7.10 (br s, 1H), 7.07 (dd, J=8.6, 2.1, 1H), 5.55 (br d, 1H), 3.80-3.70 (m, 1H), 3.68 (s, 2H), 2.89 (d, J=11.7, 2H), 2.17-2.13 (m, 2H), 1.96 (s, 3H), 1.89 (d, J=11.0, 2H), 1.48-1.40 (m, 2H).

Provenance & Evidence