Hydrochloric Acid → HCID 178478831, compound

Participants

Reaction Steps

To a solution of (5-chloro-1H-pyrrolo[2,3-c]pyridin-2-yl)(phenyl)methanone (Example 73) (65 mg, 0.25 mmol) in ethanol (5 mL) was added aminoguanidine hydrochloride (55 mg, 0.85 mmol) and 6 N HCl (0.2 mL). The reaction mixture was heated to reflux under N2. After 2 h, heating was terminated and the reaction mixture was cooled to room temperature forming a white precipitate. The precipitate was collected by filtration and dried under vacuum to provide [[(5-chloro-1H-pyrrolo[2,3-c]pyridin-2-yl)(phenyl)methylene]amino]guanidine dihydrochloride (78 mg, 100%) as a white solid: mp 274-278° C.; 1H NMR (300 MHz, CD3OD) δ 6.62 (1H, s), 7.49-7.58 (2H, m), 7.68-7.79 (4H, m), 8.04 (1H, s), 8.98 (1H, s); ESI MS m/z 313 [C15H13ClN6+H]+; HPLC (Method A) >99% (AUC) tR=16.5 min.

Provenance & Evidence