Hydrochloric Acid → 2-{[(4-Fluorophenyl)methyl]oxy}-N-(2-fluoro-3-pyridinyl)-5-(4-morpholinylcarbonyl)benzamide

Participants

Reaction Conditions

Reaction Steps

To a solution of methyl 2-{[(4-fluorophenyl)methyl]oxy}-5-(4-morpholinylcarbonyl)benzoate (may be prepared as described in Description 109, 93 mg, 0.25 mmol) in tetrahydrofuran (4 ml) was added lithium hydroxide (19 mg, 0.79 mmol) and water (1 ml). The mixture was stirred at 50° C. for one hour, cooled and 2M hydrochloric acid (0.40 ml, 0.80 mmol) was added and the solvent removed in vacuo The residue was redissolved in N,N-dimethylformamide (4 ml) and diisopropylethylamine (0.11 ml, 0.62 mmol), 2-fluoro-3-pyridinamine (36.3 mg, 0.32 mmol) and HATU (284 mg, 0.75 mmol) were added. The solvent was removed in vacuo and the residue purified by MDAP to yield the title compound as an off-white solid. 5 mg.

Provenance & Evidence