Hydrazine → HCID 178461049, compound

Participants

Reaction Steps

1-tert-butoxy-N,N,N′,N′-tetramethylmethanediamine (0.0132 mL, 0.0607 mmol) was added to N-(3-acetyl-1-(propylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-5-yl)-2,6-difluoro-3-(N-(propylsulfonyl)propylsulfonamido)benzamide (0.0197 g, 0.0304 mmol) in THF (0.3 mL). The solution was stirred at reflux for 4 hours, cooled to room temperature and concentrated under reduced pressure. The resulting residue was taken up in EtOH (0.3 mL), and hydrazine (0.00973 g, 0.304 mmol) was added. The solution was stirred at reflux for 8 hours. The solution was then cooled to room temperature and concentrated under reduced pressure. The resulting residue was purified by column chromatography (5% to 10% MeOH/DCM), then purified again with reversed phase (C-18) chromatography using gradient elution with 1% to 50% CH3CN/water to afford N-(3-(1H-pyrazol-3-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)-2,6-difluoro-3-(propylsulfonamido)benzamide (0.002 g, 0.0043 mmol, 14.3% yield). 1H NMR (400 MHz, CD3OD) δ 8.71-8.75 (m, 1H), 8.49-8.51 (m, 1H), 7.78 (s, 1H), 7.66-7.70 (m, 1H), 7.50-7.58 (m, 1H), 6.93-6.99 (m, 1H), 6.12-6.14 (m, 1H), 2.96-3.02 (m, 2H), 1.80-1.89 (m, 2H), 1.00-1.05 (m, 3H); m/z (APCI-pos) M+1=461.1.

Provenance & Evidence