Potassium Carbonate → HCID 86640099, compound

Participants

Reaction Conditions

Reaction Steps

(E)-4-(3-(1-Methylpiperidin-4-ylamino)-2-((naphthalen-1-yloxy)-methyl)-3-oxo-prop-1-enyl)benzoic acid (339 mg, 0.56 mM) obtained in Example (1-1-2) was dissolved in dimethylformamide (4 ml) and cooled to 0° C. To the resulting mixture, triethylamine (0.16 ml, 1.14 mM), N-hydroxy-6-trifluorobenzotriazole (FOBt; 171 mg, 0.84 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide.hydrochloride (EDC.HCl; 190 mg, 0.99 mmol) and tetrahydro-2H-pyran-2-yloxyamine (THPONH2; 107 mg, 0.91 mmol) were added at 0° C. and the resulting mixture was stirred at room temperature for 12 hrs. To the mixture, 10% potassium carbonate solution (20 ml) was added thereto. Then, the resultant was extracted with ethyl acetate (20 ml, 15 ml×2). The organic layer was separated, washed with brine (20 ml) and dried over anhydrous sodium sulfate, followed by removing the solvent under reduced pressure. The residue thus obtained was subjected to a silica gel column chromatography to obtain 333 mg of the title compound as a white solid (yield 80%).

Provenance & Evidence