Hydrochloric Acid → HCID 67156256, compound

Participants

Reaction Steps

A solution of N-(2-(3-((2,2-dimethyl-1,3-dioxolan-4-yl)methoxy)phenyl)-1H-pyrrolo[2,3-b]pyridin-5-yl)-2,6-difluoro-3-(propylsulfonamido)benzamide (22 mg, 36 mmol) in 2:1 THF/MeOH (3 mL) was treated with 1N HCl (1 mL) and the mixture stirred at room temperature for 16 hours. The volatiles were removed via rotary evaporation, and the resulting residue was partitioned between EtOAc and aqueous NaHCO3. The layers were separated, and the organic layer was dried (MgSO4), filtered and concentrated to a solid. The solid was triturated with DCM and collected via vacuum filtration to afford N-(2-(3-(2,3-dihydroxypropoxy)phenyl)-1H-pyrrolo[2,3-b]pyridin-5-yl)-2,6-difluoro-3-(propylsulfonamido)benzamide (13 mg, 64%) as a solid. 1H NMR (400 MHz, d6-DMSO) δ 12.16 (s, 1H), 10.89 (s, 1H), 9.80 (s, 1H), 8.40-8.33 (m, 2H), 7.58-7.49 (m, 3H), 7.40-7.34 (m, 1H), 7.31-7.24 (m, 1H), 7.00-6.90 (m, 2H), 5.00-4.96 (m, 1H), 4.72-4.67 (m, 1H), 4.12-4.07 (m, 1H), 4.01-3.99 (m, 1H), 3.88-3.81 (m, 1H), 3.52-3.47 (m, 1H), 3.16-3.10 (m, 2H), 1.82-1.74 (m, 2H), 1.04-0.97 (m, 3H); m/z (APCI-pos) M+1=561.2.

Provenance & Evidence