Diethyl Ether → HCID 178424516, compound

Participants

Reaction Steps

To a solution of 4-cyano-1H-imidazole-2-carboxylic acid (2-(4,4-dimethyl-cyclohex-1-enyl)-4-{1-[4-(2-hydroxy-ethyl)-piperazin-1-yl]-1-methyl-ethyl}-phenyl)-amide (as prepared in Example 62, 162.0 mg, 0.330 mmol) in 2 mL of EtOH was added a 2 N HCl ether solution (165 μL, 0.330 mmol). The mixture was stirred at RT for 0.5 h, 1 mL of diethyl ether (Et2O) was added and the resulting mixture was heated at 60° C. for 1 min until the solution turned clear. The mixture was cooled down to RT and the solid was collected by filtration and washed with Et2O. Upon drying in vacuo, the title compound (92 mg, 53%) was obtained as an off-white solid. 1H-NMR (CD3OD; 400 MHz): δ 8.42 (d, 1H, J=8.6 Hz), 8.04 (s, 1H), 7.70 (dd, 1H, J=8.6, 2.0 Hz), 7.64 (br s, 1H), 5.83 (m, 1H), 3.91 (m, 2H), 3.40-3.93 (m, 4H), 3.37 (m, 2H), 2.33-2.40 (m, 2H), 2.05-2.12 (m, 2H), 1.72-2.00 (br s, 6H), 1.62 (t, 2H, J=6.5 Hz), 1.07 (s, 6H). Mass spectrum (ESI, m/z): Calcd. for C28H38N6O2, 491.3 (M+H). found 491.1.

Provenance & Evidence