Triethylamine → HCID 71254937, compound

Participants

Reaction Steps

To a solution of 4-((2R,3R)-3-hydroxy-5,7-dimethoxychroman-2-yl)-2-methoxybenzoic acid (20 mg, 0.08 mmol) and triethylamine (22 μL, 0.16 mmol) in DMF (1 mL) was added HATU (38 mg, 0.1 mmol). The mixture was stirred for 0.5 hr and N-methylpiperazine (20 μL, 0.16 mmol) was added and the reaction was stirred for 12 hr. The mixture was diluted with ethyl acetate, washed with sat. sodium carbonate and brine, dried over sodium sulfate, and concentrated. The crude product was purified by preparative reverse phase HPLC using a gradient of 5% to 30% acetonitrile/(0.2% formic acid/water) over 10 min, analyzing at 280 nm. The appropriate fractions were frozen and lyophilized to give (4-((2R,3R)-3-hydroxy-5,7-dimethoxychroman-2-yl)-2 methoxyphenyl)(4-methylpiperazin-1-yl)methanone.

Provenance & Evidence