(trans)-Naphthalen-2-ylmethyl 3-hydroxy-4-(2-(7-(2-methoxyethoxy)imidazo[1,2-a]pyridin-3-yl)quinolin-8-yloxy)piperidine-1-carboxylate → (trans)-4-(2-(7-(2-Methoxyethoxy)imidazo[1.2-a]pyridin-3-yl)quinolin-8-yloxy)piperidin-3-ol

Participants

Reaction Steps

(trans)-Naphthalen-2-ylmethyl 3-hydroxy-4-(2-(7-(2-methoxyethoxy)imidazo[1,2-a]pyridin-3-yl)quinolin-8-yloxy)piperidine-1-carboxylate (0.045 g, 0.072 mmol) was dissolved in 95% EtOH/ethyl acetate (1:1, 2 mL) and treated with 10% Pd/C (Degeussa type, 20 mg). The reaction was purged with argon then subjected to hydrogen atmosphere at balloon pressure. After 19 hours, the reaction was purged with N2 and treated with fresh catalyst (ca. 5 mg) and re-subjected to hydrogen atmosphere for 5 hours. The reaction was filtered through a nylon membrane (0.45 uM) and concentrated in vacuo. The residue was purified by silica gel chromatography, eluting with a gradient from 1-20% (6% NH4OH in MeOH)/ethyl acetate. A solid was recovered after concentration in vacuo. The solid was dissolved in MeOH (2 mL) and treated with 4 M HCl in dioxane (0.5 mL). After stirring for 10 minutes the solution was concentrated in vacuo, then re-dissolved in MeOH and re-concentrated three times. The material was dissolved in MeOH (1 mL) then added dropwise to Et2O (40 mL). A precipitate formed, and after stirring for 20 minutes, this precipitate was collected by filtration, washed with Et2O and dried under a blanket of nitrogen (15 mg). 1H NMR (400 MHz, CD3OD) δ 10.72 (d, 1H), 8.75 (s, 1H), 8.45 (d, 1H), 8.11 (D, 1H), 7.65-7.59 (m, 2H), 7.49-7.43 (m, 1H), 7.43-7.38 (m, 2H), 4.94-4.87 (m, 1H), 4.48-4.43 (m, 2H), 4.37-4.32 (m, 1H), 3.89-3.84 (m, 2H), 3.64-3.57 (m, 1H), 3.49-3.40 (m, 1H), 3.46 (s, 3H), 3.37-3.31 (m, 1H), 2.58-2.48 (m, 1H), 2.27-2.18 (m, 1H). MS APCI (+) m/z 435.1 (M+1) detected.

Provenance & Evidence