1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 6-chloro-2-fluoro-3-(propylsulfonamido)-N-(1H-pyrazolo[3,4-b]pyridin-5-yl)benzamide

1H-Pyrazolo[3,4-b]pyridin-5-amine (1.55 g, 11.6 mmol), 6-chloro-2-fluoro-3-(propylsulfonamido)benzoic acid (3.59 g, 12.1 mmol), EDCI (2.44 g, 12.7 mmol), and HOBt (0.25 g, 0.16 mmol) were dissolved in DMF (30 mL) and stirred at room temperature for 16 hours. The reaction mixture was concentrated. The residue was diluted with ethyl acetate (500 mL), and the organic layers were washed with water (3×50 mL). The organic layers were dried, filtered and concentrated. The crude solids were washed with DCM (3×50 mL) to give 6-chloro-2-fluoro-3-(propylsulfonamido)-N-(1H-pyrazolo[3,4-b]pyridin-5-yl)benzamide (2.7 g, 58%) as a solid. 1H NMR (400 MHz, CD3OD) δ 8.7 (s, 1H), 8.6 (s, 1H), 8.1 (s, 1H), 7.7 (m, 1H), 7.4 (m, 1H), 3.1 (m, 2H), 1.9 (m, 2H), 1.1 (t, J=7.6 Hz, 3H); m/z (APCI-neg) M−1=410.2, 412.2.

1. concentrationThe reaction mixture was concentrated
2. additionThe residue was diluted with ethyl acetate (500 mL)
3. washthe organic layers were washed with water (3×50 mL)
4. customThe organic layers were dried
5. filtrationfiltered
6. concentrationconcentrated
7. washThe crude solids were washed with DCM (3×50 mL)

ORD record

ord-f6ef0cb3a9244b1b8276d58ac7ea1f86

Source dataset

uspto-grants-2013_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08394795B2