Hydrochloric Acid → HCID 72199095, compound

Participants

Reaction Conditions

Reaction Steps

A solution of HCl in dioxane (4 M, 0.7 mL, 2.8 mmol) was added to a solution of (S)—N-((3S,5S,6R)-6-methyl-2-oxo-5-phenyl-1-(2,2,2-trifluoroethyl)piperidin-3-yl)-2′-oxo-1′-((2-(trimethylsilyl)ethoxy)methyl)-1′,2′,5,7-tetrahydrospiro[cyclopenta[b]pyridine-6,3′-pyrrolo[2,3-b]pyridine]-3-sulfonamide (0.027 g, 0.038 mmol) in dioxane (0.5 mL) pre-cooled to 0° C. The mixture was gradually warmed to ambient temperature, then heated at 60° C. for 22 h. The reaction mixture was concentrated in vacuo, and the residue was purified by reverse-phase HPLC (C18 column), eluting with 30% MeOH in water (0.1% TFA used as a modifier) initially, grading to 100% MeOH over 30 min with a flow rate of 15 mL/min to furnish the title compound. MS: m/z=586.2 (M+1). 1H NMR (400 MHz, CD3OD) δ 8.92 (s, 1H), 8.22 (s, 1H), 8.11 (d, 1H, J=4.3 Hz), 7.42-7.34 (m, 3H), 7.32-7.23 (m, 3H), 6.93 (dd, 1H, J=7.4, 5.4 Hz), 4.88 (obscured m, 1H), 4.62 (dq, 1H, J=15.2, 9.4 Hz), 4.30 (dd, 1H, J=11.7, 7.2 Hz), 3.84 (quintet, 1H, J=6.0 Hz), 3.68-3.57 (m, 3H), 3.36-3.29 (obscured m, 2H), 2.65-2.52 (m, 1H), 2.45-2.36 (m, 1H), 0.98 (d, 3H, J=6.5 Hz).

Provenance & Evidence