Methyl chloroformate → HCID 178501950, compound

Participants

Reaction Steps

Methyl chloroformate (42 ul, 0.53 mmol) was added dropwise to a solution of 2-amino-5-[3-(2-methoxy-phenyl)-1H-pyrazolo[3,4,b]pyridin-5-yl]-N,N-dimethyl-benzamide (21 mg, 0.05 mmol) in dichloromethane/saturated aqueous sodium bicarbonate (1:1) at 0° C. The mixture was stirred for another 3 hours, allowing to slowly warm to room temperature. The reaction was washed three times with water (5 ml), dried over sodium sulfate and concentrated to dryness. The crude was purified by flash chromatography on silica gel using a gradient of ethyl acetate and hexane to afford {2-dimethylcarbamoyl-4[3-(2-methoxy-phenyl)-1H-pyrazolo[3,4-b]pyridin-5-yl]-phenyl}-carbamic acid methyl ester (4.9 mg, 21% yield). 1H NMR (500 MHz, DMSO-d6) δ 2.88 (d, 6H), 3.58 (s, 3H), 3.77 (s, 3H), 7.03 (m, 1H), 7.15 (d, 1H), 7.40 (m, 1H), 7.58 (s, 1H), 7.64 (d, 1H), 7.73 (d, 1H), 8.27 (s, 1H), 8.78 (s, 1H), 9.03 (s, 1H). 13.75 (s, 1H); MS: m/z 446.1 (M+H+).

Provenance & Evidence