atmosphere at room temperature 1 3 dicyclohexylcarbodiimide 43 mg and 1 hydroxybenzotriazole 28 mg were added the mixture was stirred at room temperature for 2 days the mixture was diluted with ethyl acetate and transferred to a separatory funnel the solution was washed 2 u00d7 with saturated sodium bicarbonate solution 1 u00d7 water then 1 u00d7 brine the solution was dried over sodium sulfate filtered then concentrated the residue was separated by flash chromatography eluting with 1 1 hexanes ethyl acetate to give crude product as a yellow oil this was further purified by preparative tic eluting with 7 3 hexanes ethyl acetate to afford cis n 3 4 methyl 1 4 phenyl 1 piperazinyl cyclohexyl phenyl 4 cinnolinecarboxamide m p monohydrochloride 166 168 u00b0 c 5 chloroindazole 3 carboxylic acid 139 mg was suspended in 1 5 ml of dry thf at room temperature under a nitrogen atmosphere enough dry dmf was added to solubilize the acid the solution was cooled to 0 u00b0 c then triethylamine 216 ml followed by ethylchloroformate 148 ml was added the mixture was stirred at 0 u00b0 c for 25 minutes after which time 1 3 aminophenyl 1 4 phenylpiperazin 1 yl 4 methyl cyclohexane cis isomer 250 mg was added the mixture was stirred for 12 hours allowing to warm to room temperature the mixture was diluted with ethyl acetate and transferred to a separatory funnel it was washed 3 u00d7 with water then 1 u00d7 with brine the organic layer was dried over sodium.