Hydrochloric Acid → HCID 178478833, compound

Participants

Reaction Steps

A mixture of [5-(dibenzylamino)-1H-pyrrolo[2,3-c]pyridin-2-yl](phenyl)methanone (Example 55) (129 mg, 0.31 mmol), aminoguanidine hydrochloride (36 mg, 0.32 mmol) and 6 N HCl (0.26 mL) in ethanol (10 mL) was heated to reflux under a nitrogen atmosphere for 2.5 h. TLC analysis showed the remaining ketone, therefore additional aminoguanidine hydrochloride (10 mg, 0.09 mmol) was added. The reaction mixture was refluxed until TLC analysis showed the reaction was completed (2 h). After concentration to dryness, the crude material was triturated with EtOAc. The solid was collected by filtration and dried to provide [[[5-(dibenzylamino)-1H-pyrrolo[2,3-c]pyridin-2-yl](phenyl)methylene]amino]guanidine dihydrochloride (60.6 mg, 36%) as a yellow solid: ESI MS m/z 474 [C29H27N7+H]+; HPLC (Method A) 89.3% (AUC), tR=17.5 min.

Provenance & Evidence