反应详情

A mixture of 5-fluoro-N-(isopropylcarbamoylmethyl)-2-nitrobenzamide (INTERMEDIATE IV.1) (400 mg, 1.4 mmol), 1-methylhomopiperazine (0.20 mL, 1.6 mmol) and potassium carbonate (1 g) in acetonitrile (20 mL) were heated at reflux temperature under an Argon atmosphere for 16 h. The mixture was cooled, filtered, the residue washed with DCM (2×1 mL) and the volatiles evaporated under reduced pressure. The red coloured residue was dissolved in DCM (15 mL), washed with 1 N NaOH (aq.) (2×5 mL) and brine (1×5 mL), dried (Na2SO4) and concentrated under reduced pressure to afford N-(isopropylcarbamoylmethyl)-5-(4-methylperhydro-1,4-diazepin-1-yl)-2-nitrobenzamide (510 mg, 1.4 mmol, 100%) as an orange-red solid. This was used in the next step without further purification.

1. temperaturewere heated
2. temperatureat reflux temperature under an Argon atmosphere for 16 h
3. temperatureThe mixture was cooled
4. filtrationfiltered
5. washthe residue washed with DCM (2×1 mL)
6. customthe volatiles evaporated under reduced pressure
7. dissolutionThe red coloured residue was dissolved in DCM (15 mL)
8. washwashed with 1 N NaOH (aq.) (2×5 mL) and brine (1×5 mL)
9. dry with materialdried (Na2SO4)
10. concentrationconcentrated under reduced pressure