Sodium Hydroxide → HCID 23156199, compound

Participants

Reaction Conditions

Reaction Steps

Under argon atmosphere, a solution of aluminum trichloride (0.136 g, 1.02 mmol) in THF (2.5 mL) was dropped into a solution of lithium aluminum hydride (77.4 mg, 2.04 mmol) in THF (3.0 mL) at 0° C. Then, a solution of 1-methylpiperidine-4-carboxylic acid [4-(2,5,7-trimethyl-3H-imidazo[4,5-b]pyridin-3-ylmethyl)phenyl amide] (1.53 g, 3.31 mmol) obtained in Step 1 in THF (3.0 mL) was dropped into the mixture. The mixture was stirred at 0° C. for 15 minutes, then at room temperature for 1.5 hours. The reaction mixture was added with a 2 mol/L aqueous sodium hydroxide solution and extracted with ethyl acetate three times. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate, then concentrated under reduced pressure. The obtained crystals were recrystallized from ethanol-diisopropyl ether to obtain Compound 159 (44.3 mg, 0.12 mmol, 23%).

Provenance & Evidence