Hydrochloric Acid → 3-((8-(3-(3,3-Dimethyl-2-oxoindolin-1-yl)propyl)-1-(4-fluorophenyl)-4-oxo-1,3,8-triazaspiro[4.5]decan-3-yl)methyl)benzoic acid

Participants

Reaction Steps

To tert-butyl 3-((8-(3-(3,3-dimethyl-2-oxoindolin-1-yl)propyl)-1-(4-fluorophenyl)-4-oxo-1,3,8-triazaspiro[4.5]decan-3-yl)methyl)benzoate (0.16 g, 0.25 mmol) was added 4M solution of HCl in dioxane (2.5 mL) and triethylsilane (0.05 mL). After stirring at room temperature for 4 hours, the reaction mixture was concentrated in vacuo and lyophilized in acetonitrile/water (1:1) to obtain the title compound as a hydrochloride salt (0.14 g, 90%); 1H NMR (DMSO-d6): δ 1.28 (s, 6H), 1.91 (d, 2H, J=14 Hz), 2.07 (br, 2H), 2.71 (t, 2H, J=10 Hz), 3.17 (br, 2H), 3.45-3.71 (m, 4H), 3.76 (t, 2H, J=7.2 Hz), 4.62 (s, 4H), 7.04-7.07 (m, 5H), 7.15 (d, 1H, J=7.6 Hz), 7.27 (t, 1H, J=8 Hz), 7.36 (d, 1H, J=7.6 Hz), 7.50 (t, 1H, J=8 Hz), 7.55 (d, 1H, J=7.6 Hz), 7.87 (dd, 2H, J=6.8 and 1.6 Hz), 10.39 (br, 1H), 13.03 (br, 1H); MS for C34H37FN4O4 m/z 585.23 (M+H)+.

Provenance & Evidence