Hydrochloric Acid → HCID 136138781, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 3-(4-phenyl-2H-pyrazol-3-yl)-1H-pyrrolo[2,3-b]pyridine 7-oxide meta-chlorobenzoate salt (247 mg, 0.57 mmol) in acetonitrile (3 mL) was added dimethylsulfate (124 mg, 0.98 mmol) and the mixture heated to 60° C. for 16 hours. After this time the reaction was cooled to room temperature and benzylamine (490 mg, 4.57 mmol) added. The reaction was then reheated to 55° C. and held at this temperature for 7 hours. Additional benzylamine (245 mg, 2.28 mmol) was then added and heating continued for an additional 17 hours. The mixture was then cooled to room temperature and diluted with EtOAc (50 mL). The organic was then washed with 10% sodium bicarbonate solution (50 mL) and dried over sodium sulfate. Filtration, concentration and purification of the residue by preparative thin layer chromatography afforded an oil. This material was treated with 1.25M Hydrogen Chloride in methanol (5 mL) and the solution concentrated. Trituration of the residue with diethyl ether and isolation of the resulting solids gave the title compound as a light yellow solid in 2% yield.

Provenance & Evidence