Hydrochloric Acid → 3-[6-(8-benzyl-2,8-diaza-spiro[5.5]undec-2-yl)-4-methyl-1H-benzoimidazol-2-yl]-4-chloro-1H-pyridin-2-one

Participants

Reaction Conditions

Reaction Steps

To a suspension of 2-benzyl-8-[2-(2-chloro-4-iodo-pyridin-3-yl)-7-methyl-3H-benzoimidazol-5-yl]-2,8-diaza-spiro[5.5]undecane (55 mg, 0.09 mmol) in H2O (0.75 mL) was added a solution of HCl in dioxane (4 M, 10 mL, 40 mmol). After it was heated at 85° C. for 18 h, the reaction mixture was evaporated to dryness under reduced pressure. The residue was purified by chromatography (170:10:1 CH2Cl2/MeOH/28% aqueous NH4OH) to afford the title compound (17 mg, 38%). 1H NMR (MeOH-d4) δ 1.23-1.35 (2H), 1.50-1.72 (6H), 2.09-2.31 (2H), 2.55 (s, 3H), 2.58-2.65 (2H), 2.88-3.72 (6H), 6.60 (d, J=6 Hz, 1H), 6.83 (s, 1H), 7.19-7.32 (6H), 7.52 (d, J=6 Hz, 1H). ESI-MS m/z 502 (MH+).

Provenance & Evidence