Hydrochloric Acid → HCID 178489394, compound

3-Chloro-2-hydroxy-5-[3-(2-methoxy-phenyl)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrazolo[3,4-b]pyridin-5-yl]-benzoic acid (143 mg, 0.3 mmol), dimethylamine (2M in THF, 0.4 ml, 0.6 mmol), O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (208 mg, 0.6 mmol), and N,N-di-iso-propylethylamine (0.1 ml, 0.6 mmol) were dissolved in DMF (2 ml). The reaction mixture was stirred at room temperature overnight. The mixture was distributed between ethyl acetate and 1 N aqueous hydrochloric acid. The organic layer was washed with saturated aqueous sodium bicarbonate and brine, dried over sodium sulfate and concentrated to dryness. The crude was purified by flash chromatography on silica gel. The resulting material was dissolved in 1 ml of a 5% v/v solution of 70% perchloric acid in acetic acid and stirred overnight at room temperature. The crude was filtered and purified by mass-triggered reverse phase HPLC to afford 11 mg (63 μmol, 21%) of 3-chloro-2-hydroxy-5-[3-(2-methoxy-phenyl)-1H-pyrazolo[3,4-b]pyridin-5-yl]-N,N-dimethylbenzamide. 1H-NMR (DMSO-d6): δ 2.94 (s, 6H), 3.82 (s, 3H), 7.09 (m, 1H), 7.21 (d, 1H), 7.47 (m, 2H), 7.63 (d, 1H), 7.81 (s, 1H), 8.29 (s, 1H), 8.81 (s, 1H). MS: m/z 423.0 (M+H+).

1. washThe organic layer was washed with saturated aqueous sodium bicarbonate and brine
2. dry with materialdried over sodium sulfate
3. concentrationconcentrated to dryness
4. customThe crude was purified by flash chromatography on silica gel
5. dissolutionThe resulting material was dissolved in 1 ml of a 5% v/v solution of 70% perchloric acid in acetic acid
6. stirringstirred overnight at room temperature
7. filtrationThe crude was filtered
8. custompurified by mass-triggered reverse phase HPLC

ORD record

ord-fd81d8c86b1146389bf7d29c3f5852c3

Source dataset

uspto-grants-2009_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07626021B2