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

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.

1. washwashed with brine (3×5 mL)
2. dry with materialThe organic layers were dried over sodium sulfate
3. customdecanted
4. concentrationconcentrated under reduced pressure
5. customThe residue was purified via silica gel chromatography
6. washeluting with 5% MeOH

ORD record

ord-b413721b93cb45c9bde543c886756968

Source dataset

uspto-grants-2013_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08394795B2