Hydrochloric Acid → 7-(benzylamino)-N-(4-pyridinylmethyl)-1H-pyrrolo[2,3-c]pyridine-2-carboxamide

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Reaction Steps

Hydrogen (1 atm, balloon) was applied to a slurry of 7-(dibenzylamino)-N-(4-pyridinylmethyl)-1H-pyrrolo[2,3-c]pyridine-2-carboxamide (Example 41) (69 mg, 0.15 mmol), 10% palladium on carbon (wet, 100 mg) and HCl (saturated solution in 2-propanol, 5 M, 0.5 mL) in ethanol (4.5 mL) at room temperature for 3 h. The slurry was filtered to remove the catalyst, and the filtrate was concentrated in vacuo. The residue was partitioned between ethyl acetate and aqueous sodium hydrogen carbonate. The two layers were separated. The organic layer was dried over sodium sulfate and concentrated in vacuo. The residue was purified by column chromatography (silica gel, 2:1 to 1:2 hexanes/ethyl acetate). Recrystallization from hexanes/ethyl acetate gave 7-(benzylamino)-N-(4-pyridinylmethyl)-1H-pyrrolo[2,3-c]pyridine-2-carboxamide (13.2 mg, 24%) as colorless crystals: Rf 0.42 (silica gel, 20:80 methanol/ethyl acetate); mp 199-200° C. (recrystallized from hexanes/ethyl acetate); 1H NMR (300 MHz, CD3OD) δ4.63 (2H, s), 4.69 (2H, s), 6.91 (1H, d, J=6.0 Hz), 7.05 (1H, s), 7.22-7.43 (7H, m), 7.55 (1H, d, J=6.0 Hz), 8.48 (2H, d, J=6.0 Hz); ESI MS m/z 358 [C21H19N5O+H]+; HPLC (Method A) >99% (AUC), tR=13.2 min.

Provenance & Evidence