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

Participants

Reaction Conditions

Reaction Steps

To a solution of tert-butyl 3-((4-oxo-1-phenyl-1,3,8-triazaspiro[4.5]decan-3-yl)methyl)benzoate (0.2 g, 0.47 mmol), potassium carbonate (0.097 g, 0.7 mmol) and sodium iodide (0.021 g, 0.14 mmol) in 2-butanone (5 mL), was added 1-(3-chloropropyl)-3-cyclopropyl-1H-benzo[d]imidazol-2(3H)-one (0.119 g, 0.47 mmol). After stirring at 78° C. for 18 hours, the reaction mixture was filtered, concentrated and isolated by preparatory TLC (10% methanol/dichloromethane) to obtain the title compound (0.27 g, 90%); 1H NMR (DMSO-d6): δ 0.84-0.88 (m, 2H), 1.01 (d, 2H, J=5.6 Hz), 1.51 (s, 9H), 1.61 (d, 2H, J=14.4 Hz), 1.81 (br, 2H), 2.34 (t, 2H, J=6.8 Hz), 2.48-2.55 (m, 2H), 2.67-2.71 (m, 4H), 2.85-2.88 (m, 1H), 3.86 (t, 2H, J=6.4 Hz), 4.59 (d, 4H, J=10 Hz), 6.77 (t, 1H, J=7.2 Hz), 6.85 (d, 2H, J=8 Hz), 7.03-7.05 (m, 2H), 7.18-7.24 (m, 4H), 7.48-7.54 (m, 2H), 7.79 (s, 1H), 7.83 (d, 1H, J=7.2 Hz); MS for C38H45N5O4 m/z 636.26 (M+H)+.

Provenance & Evidence