Hydrochloric Acid → HCID 66652432, compound

Participants

Reaction Steps

To tert-butyl 3-(5-methoxy-5-oxopentyl)-4-oxo-1-phenyl-1,3,8-triazaspiro[4.5]decane-8-carboxylate (0.09 g, 0.2 mmol) was added 4M solution of HCl in dioxane (1 mL). After stirring at room temperature for 2 hours, the reaction mixture was concentrated in vacuo to obtain methyl 5-(4-oxo-1-phenyl-1,3,8-triazaspiro[4.5]decan-3-yl)pentanoate as a hydrochloride salt. To a solution of the hydrochloride salt and potassium carbonate (0.069 g, 0.5 mmol) in N,N-dimethylformamide (2 mL), was added 1-(3-iodopropyl)-1,3-dihydro-2H-benzimidazol-2-one (0.06 g, 0.2 mmol). After stirring at 55° C. for 18 hours, the reaction mixture was diluted with ethyl acetate (25 mL), washed with water and brine. The organic phase was dried over MgSO4, filtered, concentrated and isolated by pTLC (10% methanol/dichloromethane) to obtain the product (0.05 g, 48%); 1H NMR (DMSO-d6): δ 1.50-1.57 (m, 6H), 1.81 (br, 2H), 2.32-2.36 (m, 4H), 2.60-2.67 (m, 8H), 3.57 (s, 3H), 3.84 (t, 2H, J=6.8 Hz), 4.64 (s, 2H), 6.77 (t, 1H, J=7.2 Hz), 6.88 (d, 2H, J=8 Hz), 6.96 (d, 3H, J=3.2 Hz), 7.17-7.19 (m, 1H), 7.25 (t, 2H, J=8.4 Hz), 10.8 (s, 1H); MS for C29H37N5O4 m/z 520.11 (M+H)+.

Provenance & Evidence