Benzylamine → HCID 136138779, compound

Participants

Reaction Steps

A solution of 3-[4-(3-chlorophenyl)-2H-pyrazol-3-yl]-1H-pyrrolo[2,3-b]pyridine 7-oxide meta-chlorobenzoate salt (93 mg, 0.2 mmol), DIPEA (104 mg, 0.8 mmol) and benzylamine (45 mg, 0.4 mmol) in DMF was treated with PyBrOP (186 mg, 0.4 mmol) and the resulting solution stirred at room temperature overnight. After this time the reaction was diluted with EtOAc (150 ml) and washed with saturated sodium bicarbonate solution (2×50 mL) followed by saturated sodium chloride solution (50 mL). The organic layer was then dried over sodium sulfate and concentrated. The residue was purified by column chromatography (SiO2, 40-100% EtOAc in hexanes) followed by further purification by preparative TLC (SiO2, EtOAc). The resulting material was then combined with material obtained from a previous reaction, run under identical conditions, and the combined product treated with 1N HCl/MeOH (1:1, 5 mL). The resulting solution was then concentrated and the residue re-dissolved in water (5 mL). Subsequent isolation by lyophilization afforded the title compound as a white solid in 9% overall yield.

Provenance & Evidence