1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 3-(N-ethyl-N-methylsulfamoylamino)-2,6-difluoro-N-(3-methoxy-1H-pyrazolo[3,4-b]pyridin-5-yl)benzamide

Participants

Reaction Steps

HOBt (0.017 g, 0.13 mmol), EDCI (0.054 g, 0.28 mmol), and 3-methoxy-1H-pyrazolo[3,4-b]pyridin-5-amine (0.046 g, 0.28 mmol) was added to 3-(N-ethyl-N-methylsulfamoylamino)-2,6-difluorobenzoic acid (0.075 g, 0.25 mmol) in DMF (1 mL). The reaction mixture was stirred at room temperature for 16 hours. The mixture was diluted with EtOAc (6 mL) and washed with brine (3×5 mL). The organic layers were dried over sodium sulfate, decanted, and concentrated under reduced pressure. The residue was purified via silica gel chromatography eluting with 5% MeOH:DCM to afford 3-(N-ethyl-N-methylsulfamoylamino)-2,6-difluoro-N-(3-methoxy-1H-pyrazolo[3,4-b]pyridin-5-yl)benzamide (0.055 g, 0.12 mmol, 49% yield). 1H NMR (400 MHz, CD3OD) δ 8.60-8.63 (m, 1H), 8.50-8.52 (m, 1H), 7.63-7.70 (m, 1H), 7.09-7.15 (m, 1H), 4.09 (s, 3H), 3.18-3.25 (m, 2H), 2.83 (s, 3H), 1.09-1.14 (m, 3H); m/z (APCI-neg) M−1=439.0.

Provenance & Evidence