Citric Acid → HCID 57731537, compound

Participants

Reaction Steps

67 mg (0.11 mmol) of 5-[3-(2-methoxy-phenyl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-N,N-dimethyl-2-(pyrimidin-5-ylamino)-benzamide was dissolved in 3 mL of hot ethanol. 200 μL of 50% w/v aqueous potassium hydroxide was added and the mixture left at ambient temperature for 4.5 h. 10% w/v aqueous citric acid was added and the mixture partitioned between dichloromethane and water. The aqueous layer was extracted three times with dichloromethane. The combined organic phases were dried over sodium sulfate and evaporated. The residue was purified by mass-triggered reverse-phase HPLC to afford 21.9 mg (47 μmol, 43%) of 5-[3-(2-methoxy-phenyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-N,N-dimethyl-2-(pyrimidin-5-ylamino)-benzamide as a beige solid. 1H-NMR (500 MHz, d6-DMSO): δ 11.91 (s, br., 1H), 8.64 (s, 1H), 8.55 (d, 1H), 8.51 (s, 2H), 8.17 (d, 1H), 8.12 (s, 1H), 7.74 (d, 1H), 7.73 (dd, 1H), 7.63-7.61 (m, 2H), 7.39 (d, 1H), 7.30 (dd(d), 1H), 7.14 (d, 1H), 7.06 (t, 1H), 3.83 (s, 3H), 2.90 (s, 3H), 2.88 (s, 3H); MS: m/z 465.0 (M+H+).

Provenance & Evidence