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

Participants

Reaction Steps

2-Chloro-6-fluoro-3-(propylsulfonamido)benzoic acid (75.7 mg, 0.256 mmol) in N,N-dimethylformamide (2.5 mL) was sequentially treated with 3-methoxy-1H-pyrazolo[3,4-b]pyridin-5-amine (46.2 mg, 0.282 mmol), EDCI (54.0 mg, 0.282 mmol), and HOBt (38.0 mg, 0.282 mmol). The reaction mixture was allowed to stir at ambient temperature for 24 hours. The mixture was then diluted with ethyl acetate and washed with water (4×), sodium bicarbonate (2×), and brine, dried over sodium sulfate and concentrated. The crude product was triturated with DCM to afford 2-chloro-6-fluoro-N-(3-methoxy-1H-pyrazolo[3,4-b]pyridin-5-yl)-3-(propylsulfonamido)benzamide (18.0 mg, 0.0407 mmol, 15.9% yield) as a solid. 1H NMR (400 MHz, d6-DMSO) δ 12.62-12.56 (s, 1H), 11.08-11.03 (s, 1H), 9.78-9.65 (s, 1H), 8.61-8.56 (s, 1H), 8.50-8.45 (s, 1H), 7.63-7.55 (m, 1H), 7.44-7.35 (m, 1H), 4.03-3.99 (s, 3H), 3.14-3.07 (m, 2H), 1.83-1.73 (m, 2H), 1.04-0.95 (t, 3H); MS (APCI-neg) m/z=440.1 (M−H).

Provenance & Evidence