Methanamine, N-methoxy-, hydrochloride (1:1) → 6-(4-benzyloxy-2-fluoro-phenyl)-3-methyl-1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid methoxy-methyl-amide

Participants

Reaction Steps

6-(4-Benzyloxy-2-fluoro-phenyl)-3-methyl-1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid (3.00 g) was dissolved in dichloromethane (50 mL), DIPEA (3.34 mL), N,O-dimethylhydroxylamine hydrochloride (0.63 g) and finally BEP (3.92 g) were added. The mixture was stirred at r.t. overnight, then extracted with sat. sodium carbonate solution, washed with 1N HCl and finally again with sodium carbonate solution. The solvent was evaporated and the residue was crystallized from methanol and filtered off giving 6-(4-benzyloxy-2-fluoro-phenyl)-3-methyl-1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid methoxy-methyl-amide (2.28 g, 70%) as a solid.

Provenance & Evidence