Trifluoroacetic acid → (3R,3aR,6R,6aR)-6-((6-chloro-5-(4-phenylpiperidin-1-yl)-1H-imidazo[4,5-b]pyridin-2-yl)oxy)hexahydrofuro[3,2-b]furan-3-ol

Participants

Reaction Steps

To a r.t. solution of (3R,3aR,6R,6aR)-6-((6-chloro-5-(4-phenylpiperidin-1-yl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazo[4,5-b]pyridin-2-yl)oxy)hexahydrofuro[3,2-b]furan-3-ol (77 mg, 0.131 mmol) in dichloromethane (2 mL) was added trifluoroacetic acid (2 mL). The reaction was concentrated after 4 hours and diluted with ethyl acetate and saturated aqueous NaHCO3. This mixture was then extracted with ethyl acetate, and the combined the organic layers were washed with brine, dried over Na2SO4, and concentrated. This material was then purified via reverse phase HPLC on a 19×50 mm Waters Sunfire C18 column (5μ particle size) using a linear gradient with acetonitrile/water and buffering with 0.16% TFA at a flow rate 25 mL/min. The desired fractions were concentrated to obtain the title compound as a white sticky solid. LC-MS: calculated for C23H25ClN4O4 456.16 observed m/e: 457.33 (M+H)+ (Rt 1.08/2 min). 1H NMR δ (ppm) (DMSO): 7.76 (s, 1H), 7.30-7.28 (m, 4H), 7.19 (m, 1H), 5.38 (q, 1H), 4.80 (t, 1H), 4.33 (t, 1H), 4.14-4.09 (m, 2H), 3.85 (m, 1H), 3.74 (m, 1H), 3.59 (d, 2H), 3.40 (t, 1H), 2.85 (t, 2H), 2.68 (m, 1H), 1.85 (m, 4H).

Provenance & Evidence