Dimethylformamide → HCID 15512772, compound

Participants

Reaction Steps

To a 50 mL round-bottomed flask equipped with nitrogen inlet were added 200 mg (0.71 mmol) 6-((2-(piperazin-1-yl)ethyl)phenyl)-pyridin-2-ylamine, 10 mL dry dimethyformamide, 109 mg (0.71 mmol) 4-fluorophenylacetic acid, 204 mg (1.1 mmol) ethyl(3-dimethylaminoproryl)carbodiimide, and 0.36 mL (2.1 mmol) diisopropylethylamine. The reaction was stirred at room temperature for 18 hours, poured into water and extracted into ethyl acetate. The organic layer was extracted into 1 N hydrochloric acid, the aqueous layer washed with fresh ethyl acetate, and the aqueous layer basified with 1 N aqueous sodium hydroxide solution and extracted into ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate, and evaporated. The residue was chromatographed on silica gel using 3% methanol in methylene chloride to afford 100 mg (34%) of the product as a tan solid, mp 143-145° C.

Provenance & Evidence