hydrogen chloride gas was bubbled through until saturation was reached the mixture was then stirred at room temperature overnight it was concentrated in vacuo the residue was suspended in dry methanol 80 ml to the solution pyrrolidine 22 ml 264 mmol was added the mixture was then heated to reflux for 30 min during which time the mixture became clear it was then stirred at room temperature overnight it was concentrated in vacuo the residue was dissolved in methanol 90 ml to the solution et 2 o 170 ml was added after being cooled in fridge overnight the precipitated product was collected by filtration it was then dried on vacuum to give white solids 4 5 g ms 190 m h to a solution of 2 2 bromophenyl 2 4 chlorophenylaminocarbonylamino acetic acid from example 77 60 mg 0 16 mmol and 4 pyrrolidin 1 ylimino phenylamine 60 mg 0 31 mmol in dmf 4 ml and h 2 o 1 ml edc 120 mg 0 62 mmol was added after being stirred at room temperature for 2 h the mixture was concentrated in vacuo the residue was purified by hplc to give the titled compound as a powder 70 mg ms 554 2 and 556 2 m h cl br.