Hydrochloric Acid → 6-(4-chloro-3-isopropyl-1-methyl-1H-pyrazol-5-yl)-4-(3,3-dimethylpiperidin-1-yl)-2-(3-methyl-1-tosyl-1H-indol-4-yl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine

Participants

Reaction Conditions

Reaction Steps

Isopropanol (2.2 mL) was added to 4-chloro-6-(4-chloro-3-isopropyl-1-methyl-1H-pyrazol-5-yl)-2-(3-methyl-1-tosyl-1H-indol-4-yl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine (85 mg, 0.139 mmol) in a microwave vial. Then diisopropylethylamine (0.1 mL, 0.573 mmol) was added followed by the HCl salt of 3,3-dimethylpiperidine (25 mg, 0.167 mmol). The vessel was sealed and heated via microwave irradiation at 120° C. for 2.5 h then cooled to room temperature and diluted with dichloromethane and brine. The layers were separated and the organic layer was dried over Na2SO4, filtered, and concentrated. The resulting residue was purified via silica gel flash chromatography (25-55% ethyl acetate/heptanes) to provide 6-(4-chloro-3-isopropyl-1-methyl-1H-pyrazol-5-yl)-4-(3,3-dimethylpiperidin-1-yl)-2-(3-methyl-1-tosyl-1H-indol-4-yl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine. MS (ESI+) m/z 686.4 (M+H)+.

Provenance & Evidence