Cesium carbonate → 1-({4-[4-chloro-1-(cyclopropylmethyl)-1H-benzotriazol-5-yl]cyclohex-3-en-1-yl}methyl)-3-methylimidazolidine-2,4-dione

Participants

Reaction Conditions

Reaction Steps

4-Chloro-1-(cyclopropylmethyl)-5-[4-(iodomethyl)cyclohex-1-en-1-yl]-1H-benzotriazole (0.12 g, 0.29 mmol), 3-methylimidazolidine-2,4-dione (67 mg, 0.58 mmol, 2 equiv) and potassium carbonate (0.20 g, 1.5 mmol, 5 equiv) were combined in acetonitrile (5 mL) and placed into a preheated oil bath at 85° C. for 3 hours. Additional 3-methylimidazolidine-2,4-dione (0.13 mg, 1.2 mmol, 4 equiv) and cesium carbonate (0.48 g, 1.5 mmol, 5 equiv) were added and the mixture was heated at 85° C. for an additional 45 minutes. The mixture was cooled to ambient temperature, poured into sodium bicarbonate (50 mL, aqueous saturated) and extracted with ethyl acetate (2×75 mL). The combined organic extracts were dried with sodium sulfate, filtered and concentrated in vacuo. The residue was purified by silica gel gradient chromatography (100:0 to 0:100; hexanes:ethyl acetate), providing the titled compound as a colorless foam: 1H-NMR (400 MHz, CDCl3) δ 7.41 (1H, d, J=8.5 Hz), 7.30 (1H, d, J=8.5 Hz), 5.77-5.72 (1H, m), 4.51 (2H, d, J=7.1 Hz), 3.94 (2H, s), 3.47 (1H, dd, J=14.0, 7.4 Hz), 3.40 (1H, dd, J=14.0, 7.2 Hz), 3.05 (3H, s), 2.53-2.38 (2H, m), 2.33 (1H, br d, J=17.7 Hz), 2.15-1.87 (3H, m), 1.61-1.51 (1H, m), 1.45-1.34 (1H, m), 0.69-0.64 (2H, m), 0.51-0.47 (2H, m) ppm; high resolution mass spectrometry (ES+) m/z 414.1702 [(M+H)+; calculated for C21H25ClN5O2: 414.1691].

Provenance & Evidence