Imidazole → HCID 178423529, compound

Participants

Reaction Steps

A suspension of 3-(2-methylpyridin-4-yl)-1-trityl-1H-pyrazolo[4,3-c]pyridin-6-amine (intermediate 5a; 33.4 mg, 0.071 mmol) and imidazole (14.59 mg, 0.214 mmol) in DCM (0.5 mL) was added to a solution of CDI (69.5 mg, 0.429 mmol) in DCM (0.5 mL) and the mixture was stirred at RT. After 3 h, 4-(aminomethyl)pyridine (0.062 mL, 0.571 mmol) was added and the mixture was left at the same temperature for additional 30 min. Volatiles were removed in vacuo and the residue was purified by chromatography on silica gel over a gradient of 0-50% (20% MeOH in EtOAc) in DCM to yield a solid, which was directly dissolved in DCM (1 mL), treated with triethylsilane (0.011 mL, 0.071 mmol) and TFA (0.1 mL, 1.298 mmol). After overnight stirring at RT the volatiles were concentrated in vacuo. The residue was purified via reverse phase HPLC over a gradient of 5-20% MeCN in H2O with 0.1% TFA to yield 2-methyl-4-(6-{[(pyridin-4-ylmethyl)carbamoyl]amino}-1H-pyrazolo[4,3-c]pyridin-3-yl)pyridinium trifluoroacetate (9 mg, 0.026 mmol, 36%) as a solid. MS ESI calc'd. for C19H18N7O [M+1]+ 360, found 360.

Provenance & Evidence