Cyclohexanecarboxylic acid → N-{[5-(4-bromophenyl)-5H-imidazo[2,1-a]isoindol-5-yl]methyl}cyclohexanecarboxamide

Participants

Reaction Conditions

Reaction Steps

To a mixture of 5-(aminomethyl)-5-(4-bromophenyl)-5H-imidazo[2,1-a]isoindol-1-ium chloride (40 mg), EDC (28 mg) and HOAT (13 mg) in DMF (1 mL) was added Hunig's base (75 mg) followed by cyclohexanecarboxylic acid (19 mg). After stirring at 40° C. overnight the mixture was purified by reversed phase HPLC (21×100 mm Phenomenex Gemini, 15-75% MeCN/water containing 0.05% NH4OH over 20 min at 20 mL/min) to give title compound as a white solid. HRMS. Found, 450.1186; calcd for (M+H)+, 450.1176. 1H NMR (500 MHz, CDCl3): δ 7.85 (d, J=7.59 Hz, 1 H); 7.48 (d, J=8.42 Hz, 2 H); 7.46-7.40 (m, 1 H); 7.35-7.28 (m, 3 H); 7.07 (d, J=8.43 Hz, 2 H); 7.03 (d, J=1.34 Hz, 1 H); 4.84 (t, J=6.19 Hz, 1 H); 4.55 (dd, J=13.97, 6.66 Hz, 1 H); 4.24 (dd, J=13.99, 5.93 Hz, 1 H); 1.75-1.49 (m, 5 H); 1.39 (d, J=9.99 Hz, 1 H); 1.28 (d, J=12.70 Hz, 1 H); 1.05 (m, 4 H).

Provenance & Evidence