Methanamine, N-methoxy-, hydrochloride (1:1) → HCID 58515992, compound

Participants

Reaction Steps

The N,N,N′,N′-tetramethyl-O-(7-azabenzotriazol-1-yl)uronium hexafluorophosphate (0.46 g, 1.2 mmol) was added to a solution of 4-chloro-7-(3-fluorophenyl)pyrazolo[1,5-a]pyridine-6-carboxylic acid (0.29 g, 1.0 mmol) in N,N-dimethylformamide (3.0 mL) containing N,N-diisopropylethylamine (0.35 mL, 2.0 mmol) and N,O-dimethylhydroxylamine hydrochloride (0.14 g, 1.5 mmol) at room temperature. The reaction was complete after stirring for 2 hours. This was taken up in ethyl acetate, washed with water, brine, dried over magnesium sulfate and concentrated to give the crude amide. The product was purified on silica gel eluting hexane:ethyl acetate gradient to give 4-chloro-7-(3-fluorophenyl)-N-methoxy-N-methylpyrazolo[1,5-a]pyridine-6-carboxamide (0.29 g, 88%) as a glass. LCMS calculated for C16H14ClFN3O2 (M+H)+: m/z=334.1. found: 333.9.

Provenance & Evidence