Acetic Anhydride → HCID 66700094, compound

Participants

Reaction Conditions

Reaction Steps

[Step 8] 70 mg of the N-(4-chlorophenyl)-2,2,2-trifluoro-N-[2-methyl-1,2,3,4-tetrahydro-1,8-naphthyridin-4-yl]acetoamide were dissolved in 0.3 mL of tetrahydrofuran followed by the addition of a 1.9 M sodium hexamethyldisilazane/tetrahydrofuran solution at −15° C. After stirring for 30 minutes at −15° C., 45 μL of acetic anhydride were added, and the solution was gradually returned to room temperature followed by stirring for 2 hours. Following completion of the reaction, the solution was neutralized with a saturated aqueous solution of ammonium chloride followed by extracting three times with ethyl acetate. After washing with saturated brine and dehydrating with anhydrous sodium sulfate, the solution was concentrated under reduced pressure and the resulting residue was purified using silica gel chromatography (ethyl acetate:hexane=2:1) to obtain 1.5 mg of the target compound in the form of a pale yellow oil (2.5%).

Provenance & Evidence