Water → HCID 68458152, compound

Participants

Reaction Steps

A solution of Example 104B (37 mg, 0.1 mmol), N-(4-chloromethyl-phenyl)-acetamide (22 mg, 0.12 mmol), cesium carbonate (130 mg, 0.4 mmol) and tetrabutylammonium iodide (0.001 g) in DMF (1 ml) was stirred at room temperature for 16 hours. The mixture was poured into water and extracted by ethyl acetate. The organic layer was dried with magnesium sulfate, filtered and concentrated under vacuum giving the title compound. The residue was added dichloromethane (2 mL) and trifluoroacetic acid (2 mL) and stirred at room temperature for 2 hours. The solvent was evaporated and the crude residue was purified by chromatography on silica eluting with 2% methanol in dichloromethane to 5% methanol in dichloromethane to give the title compound as a trifluoroacetic acid salt (11 mg, 21%). 1H NMR (300 MHz, DMSO-d6) δ ppm 2.00 (s, 3 H) 2.31 (s, 3 H) 2.74 (s, 3 H) 5.05 (s, 2 H) 6.36 (d, J=6.99 Hz, 1 H) 7.12 (d, J=8.46 Hz, 2 H) 7.25 (m, 3 H) 7.40 (d, J=8.46 Hz, 2 H) 7.73 (d, J=8.46 Hz, 1 H) 8.43 (d, J=6.99 Hz, 1 H) 8.98 (d, J=8.46 Hz, 1 H) 9.89 (s, 1 H) 10.65 (s, 1 H) 14.25 (s, 1 H); MS (ESI+) m/z 413 (M+H)+.

Provenance & Evidence