Hydrochloric Acid → 2-Phenyl-5-(1-(2-(pyrrolidine-1-yl)ethyl)-1H-indazol-5-yl)furo[3,2-c]pyridine-4(5H)-one Hydrochloride

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Reaction Steps

A solution of 2-phenyl-5-(1-(2-(pyrrolidine-1-yl)ethyl)-1H-indazol-5-yl)furo[3,2-c]pyridine-4(5H)-one (27.6 mg, 0.065 mmol) in CH2Cl2 (0.5 mL) was treated with anhydrous HCl in diethyl ether (65.0 μL, 0.065 mmol, 1.0 M). After stirring at ambient temperature for one hour, the reaction mixture was diluted with Et2O (50 mL). The resulting solids were collected by filtration and dried in a vacuum oven to yield the title compound (14.6 mg, 48%) as a brown solid. 1H NMR (500 MHz, DMSO-d6) δ 10.07 (br s, 0.5H), 8.28 (s, 1H), 7.92-7.89 (m, 4H), 7.66 (d, J=7.5 Hz, 1H), 7.56-7.48 (m, 4H), 7.40 (t, J=7.5 Hz, 1H), 6.91 (d, J=7.5 Hz, 1H), 4.87 (t, J=6.0 Hz, 2H), 3.77-3.73 (m, 2H), 3.56-3.55 (m, 2H), 3.09-3.06 (m, 2H), 2.01 (br m, 2H), 1.89-1.84 (br m, 2H); ESI MS m/z 425 [M+H]+; HPLC (Method A) 95.4% (AUC), tR=15.3 min.

Provenance & Evidence