Hydrochloric Acid → HCID 178449884, compound

Participants

Reaction Steps

To a solution of 2-methyl-1-(1H-pyrrolo[2,3-c]pyridin-2-yl)-1-propanone (Example 80) (100 mg, 0.53 mmol) in ethanol (5 mL) were added aminoguanidine hydrochloride (58 mg, 0.53 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. Purification by column chromatography (silica gel, 5 to 20% methanol in methylene chloride) produced [[2-methyl-1-(1H-pyrrolo[2,3-c]pyridin-2-yl)propylidene]amino]guanidine dihydrochloride (28 mg, 26%) as a yellow solid: mp 242-245° C.; 1H NMR (500 MHz, CD3OD) δ 1.49 (6H, d, J=7.1 Hz), 3.50-3.54 (1H, m), 7.15 (1H, s), 7.72 (1H, d, J=5.5 Hz), 8.11 (1H, d, J=5.6 Hz), 8.77 (1H, s); ESI MS m/z 245 [C12H16N6+H]+; HPLC (Method A) >99% (AUC) tR=11.9 min.

Provenance & Evidence