Sodium hydride → HCID 66875104, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 5-(methyl-phenyl-amino)-2H-pyridazin-3-one (74.3 mg, 0.36 mmol) in tetrahydrofuran (1.8 mL) cooled to 0° C. was treated with a 60% suspension of sodium hydride in mineral oil (19.7 mg, 0.49 mmol). Upon complete addition of the sodium hydride, the cooling bath was removed and additional tetrahydrofuran (1.8 mL) was added to facilitate stirring. The reaction was stirred at 25° C. for 2.25 h. After this time, the reaction was treated with 2-bromo-3-cyclopentyl-propionic acid methyl ester (Intermediate 10, 0.11 g, 0.46 mmol). The reaction was then warmed to 50° C., where it stirred overnight. After this time, the reaction was cooled to 25° C. and stirred overnight. At this point, the reaction was partitioned between water (25 mL) and methylene chloride (3×25 mL). The combined organic layers were washed with a saturated aqueous sodium chloride solution (1×25 mL), dried over magnesium sulfate, filtered and concentrated in vacuo. Silica gel column chromatography (AnaLogix 8 g, 15-35% ethyl acetate/hexanes) afforded 3-cyclopentyl-2-[4-(methyl-phenyl-amino)-6-oxo-6H-pyridazin-1-yl]-propionic acid methyl ester (67.4 mg, 51%) as a yellow oil.

Provenance & Evidence