Hydrochloric Acid → 8-((4-Fluoropiperidin-4-yl)methoxy)-2-(7-(2-methoxyethoxy)imidazo[1,2-a]pyridin-3-yl)quinoline

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Reaction Steps

tert-Butyl 4-fluoro-4-((2-(7-(2-methoxyethoxy)imidazo[1,2-a]pyridin-3-yl)quinolin-8-yloxy)methyl)piperidine-1-carboxylate (0.011 g, 0.020 mmol) was dissolved in dioxane (0.5 mL) and treated with 4 M hydrogen chloride in dioxane (0.126 ml, 0.504 mmol). The reaction was stirred at ambient temperature for 24 hours. The mixture was concentrated in vacuo, redissolved and re-concentrated from MeOH three times. The crude material was loaded onto a SiO2 column and eluted with a gradient from 1 to 20% (6% NH4OH in MeOH)/ethyl acetate to provide the desired product (3 mg). 1H NMR (400 MHz, CDCl3) δ 10.67 (d, 1H), 8.22 (s, 1H), 8.08 (d, 1H), 7.83 (s, 1H), 7.41-7.33 (m, 2H), 7/09-6.98 (m, 2H), 6.90-6.84 (m, 1H), 4.29-4.16 (m, 3H), 3.87-3.79 (m, 2H), 3.49 (s, 3H), 3.23-3.10 (m, 3H), 2.29-2.15 (m, 1H), 2.14-1.94 (m, 2H), 0.93-0.81 (m, 1H). MS APCI (+) m/z 451.2 (M+1) detected.

Provenance & Evidence