Potassium Carbonate → tert-butyl 3-((4-oxo-8-(3-(2-oxo-2,3-dihydro-1H-benzo[d]imidazol-1-yl)propyl)-1-phenyl-1,3,8-triazaspiro[4.5]decan-3-yl)methyl)benzoate

Participants

Reaction Conditions

Reaction Steps

A mixture of tert-butyl 3-((4-oxo-1-phenyl-1,3,8-triazaspiro[4.5]decan-3-yl)methyl)benzoate (500 mg, 1.19 mmol, 1 equiv), 1-(3-iodopropyl)-1,3-dihydro-2H-benzimidazol-2-one-one (358.8 mg, 1.19 mmol, 1 equiv), and potassium carbonate (493.4 mg, 3.57 mmol, 3 equiv) in N,N-dimethylformamide was heated at 65° C. for 16 h. After cooling to ambient temperature, the crude mixture was partitioned between ethyl acetate and water. The organic layer was dried over MgSO4, filtered, concentrated, and the crude residue was purified using preparatory thin layer chromatography in 10% methanol in dichloromethane to afford the title compound (548 mg, 77.4%); 1H NMR (400 MHz, DMSO-d6): δ 1.52 (s, 9H); 1.61 (d, 2H, J=12.8 Hz), 1.83 (t, 2H, J=6.8 Hz); 2.36 (t, 2H, J=6.8 Hz); 2.54-2.73 (m, 6H); 3.86 (t, 2H, J=6.8 and 6.4 Hz); 4.58 (s, 2H); 4.61 (s, 2H); 6.77 (t, 1H, J=7.6 and 7.2 Hz); 6.85 (d, 2H, J=8 Hz); 6.97 (d, 1H, J=2.8 Hz); 7.18-7.25 (m, 3H); 7.48-7.55 (m, 2H); 7.79-7.84 (m, 2H); 10.81 (s, 1H); MS for C35H41N5O4 m/z 596.16 (M+H)+.

Provenance & Evidence