1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 178461064, compound

Participants

Reaction Steps

3-(cis-2-Methylcyclopropyl)-1H-pyrazolo[3,4-b]pyridin-5-amine (0.0399 g, 0.212 mmol), 2,6-difluoro-3-(propylsulfonamido)benzoic acid (0.0651 g, 0.233 mmol), EDCI (0.0488 g, 0.254 mmol), and HOBt (0.0344 g, 0.254 mmol) were dissolved in DMF and stirred overnight at room temperature. The solution was partitioned between water and EtOAc. The organic layer was washed with water (3×), brine, dried over Na2SO4 and concentrated to an oil, which was purified by column chromatography (1:2 hexanes/EtOAc) to give 2,6-difluoro-N-(3-((1R,2S)-2-methylcyclopropyl)-1H-pyrazolo[3,4-b]pyridin-5-yl)-3-(propylsulfonamido)benzamide (66 mg, 69%) as a solid. 1H NMR (400 MHz, d6-DMSO) 13.16 (s, 1H), 11.07 (s, 1H), 9.81 (s, 1H), 8.63 (s, 1H), 8.55 (s, 1H), 7.53-7.59 (m, 1H), 7.26-7.31 (m, 1H), 3.11-3.15 (m, 2H), 1.99-2.03 (m, 1H), 1.75-1.80 (m, 2H), 1.32-1.34 (m, 1H), 1.14-1.22 (m, 3H) 0.99-1.02 (m, 3H), 0.78-0.83 (m, 3H); m/z (APCI-pos) M+1=450.1.

Provenance & Evidence