Cyclopropylamine → HCID 178489403, compound

Participants

Reaction Steps

20 mg (39 μmol) of 2-(2-bromo-acetylamino)-5-[3-(2-methoxy-phenyl)-1H-pyrazolo-[3,4-b]pyridin-5-yl]-N,N-dimethyl-benzamide was dissolved in 3 mL of dichloromethane. 14 μL (12 mg, 0.2 mmol) of cyclopropylamine was added at room temperature and the resulting mixture left at ambient temperature for 19 h. The resulting solution was evaporated and the residue purified by mass-triggered reverse-phase HPLC to afford 7.1 mg (15 μmol, 38%) of 2-(2-cyclopropylamino-acetylamino)-5-[3-(2-methoxy-phenyl)-1H-pyrazolo[3,4-b]pyridin-5-yl]-N,N-dimethyl-benzamide as a yellow solid. 1H NMR (500 MHz, DMSO-d6) δ 13.82 (s, 1H), 10.00 (s, 1H), 8.87 (d, 1H), 8.35 (d, 1H), 8.33 (d, 1H), 7.82 (dd, 1H), 7.72 (d, 1H), 7.65 (dd, 1H), 7.47 (dd(m), 1H), 7.23 (d(m), 1H), 7.11 (ddd, 1H), 3.84 (s, 3H), 3.30 (s, 2H), 3.04 (s, 3H), 2.94 (s, 3H), 2.17 (m, 1H), 0.40 (m, 2H), 0.32 (m, 2H), MS: m/z 485.2 (M+H+).

Provenance & Evidence