Hydrochloric Acid → HCID 178478832, compound

Participants

Reaction Steps

To a solution of phenyl(1H-pyrrolo[2,3-c]pyridin-2-yl)methanone (Example 35) (0.15 g, 0.67 mmol) in ethanol (6.7 mL) were added aminoguanidine hydrochloride (0.09 g, 0.81 mmol) and 6 N HCl (0.56 mL). The reaction mixture was heated to reflux under N2. After 3 h, heating was terminated and the reaction mixture was slowly cooled to room temperature overnight. The reaction mixture was concentrated to dryness. The residue was dissolved in water and washed with diethyl ether. The aqueous layer was made basic with 15% NaOH solution and extracted with ethyl acetate (2×). The organic extracts were combined and washed with water and saturated NaCl, and dried over Na2SO4. Filtration and concentration provided the crude residue, which was dissolved in methanol. To the methanol solution was added 2 N HCl in Et2O (0.67 mL, 1.34 mmol). The mixture was concentrated to dryness and the resulting solid was crystallized from EtOH/Et2O (9:1) to provide [[phenyl (1H-pyrrolo[2,3-c]pyridin-2-yl)methylene]amino]guanidine dihydrochloride (0.22 g, 93%) as an off-white solid: mp 306-310° C.; 1H NMR (300 MHz, CD3OD) δ6.71 (1H, s), 7.57-7.74 (5H, m), 8.07 (1H, d, J=6.5 Hz), 8.24 (1H, d, J=6.4 Hz), 9.10 (1H, s); ESI MS m/z 279 [C15H14N6+H]+; HPLC (Method A) >99% (AUC) tR=12.9 min.

Provenance & Evidence