Methanol → (R)-methyl 2-(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)-2-phenylacetate

Participants

Reaction Conditions

Reaction Steps

A mixture of (R)-methyl 2-(4-oxo-1-phenyl-1,3,8-triazaspiro[4.5]decan-3-yl)-2-phenylacetate (355 mg, 0.854 mmol, 1 equiv), 1-(3-iodopropyl)-1,3-dihydro-2H-benzimidazol-2-one (258.06 mg, 0.854 mmol, 1 equiv) and potassium carbonate (354.1 mg, 2.562 mmol, 3 equiv) in N,N-dimethylformamide was heated at 65° C. for 16 h. The reaction was cooled to ambient temperature and worked up using 5% methanol in dichloromethane and water. The organic layer was dried over MgSO4, and concentrated in vacuo. The crude mixture was purified by preparatory thin layer chromatography using 7% methanol in dichloromethane. The purified extract was lyophilized to afford the title compound as a white solid (140 mg, ˜30%); 1H NMR (400 MHz, DMSO-d6): δ 1.59 (t, 2H, J=15.2 and 14.8 Hz), 1.81 (bs, 2H), 2.33 (bs, 4H); 2.54-2.64 (m, 2H); 2.69-2.73 (m, 2H); 3.74 (s, 3H); 3.84 (t, 2H, J=6.8 Hz); 4.14 (d, 1H, J=4.4 Hz); 4.79 (d, 1H, J=4.8 Hz); 5.89 (s, 1H)); 6.78-6.84 (m, 3H); 6.97 (d, 3H, J=2.4 Hz); 7.16-7.18 (m, 1H); 7.23 (t, 2H, J=7.2 and 8.8 Hz); 7.39-7.46 (m, 5H); 10.82 (s, 1H); MS for C32H35N5O4 m/z 554.07 (M+H)+.

Provenance & Evidence