Hydrochloric Acid → HCID 70451362, compound

Participants

Reaction Steps

To a suspension of 2-{[(4-fluorophenyl)methyl]oxy}-5-[(Z)-(hydroxyimino)methyl]-N-3-pyridinylbenzamide (may be prepared by Example 83; 215 mg, 0.57 mmol) in tetrahydrofuran (5 ml) was added 2M aqueous hydrochloric acid (1.72 ml, 56.7 mmol) followed by zinc (371 mg, 5.67 mmol) at room temperature. After stirring at room temperature for 30 min the mixture was heated to 60° C. for 30 min. On cooling, the mixture was treated with saturated sodium hydrogen carbonate (excess). A small amount of the solution was put aside to generate the amine. Methyl chloroformate (0.53 ml, 6.80 mmol) was added to the remainder and the pH was adjusted with further NaHCO3 to pH 9-10. The mixture was then stirred at room temperature for 1 hour. The tetrahydrofuran was evaporated under reduced pressure, and the resulting aqueous layer was extracted with ethyl acetate (2×30 ml), dried (MgSO4) and evaporated under reduced pressure. The residue was purified twice using MDAP to yield the title compound. 12 mg.

Provenance & Evidence