Phenylacetyl chloride → HCID 178514870, compound

Participants

Reaction Steps

To a suspension of 1-(3-fluorophenyl)-4-hydroxy-1,8-naphthyridin-2 (1H)-one (512 mg, 2.0 mmol, obtained in Synthetic Example 31 (3)) in DMF (8 ml) was added sodium hydride (about 60%, 192 mg, 4.8 mmol, 2.4 eq.), the mixture was stirred until the production of hydrogen was completed. Next, after phenylacetyl chloride (371 mg, 2.4 mmol, 1.2 eq.) was added, the mixture was stirred at room temperature, and treated with water. The resultant DMF layer was washed with hexane, acidified with hydrochloric acid, and filtered to give precipitates which were washed with water, and then suspended in DMF (8 mL). To the suspension was added hydrazine monohydrate (80%, 224 μl, 5.6 mmol, 2.8 eq.), and the mixture was stirred overnight at 100 to 110° C. The reaction mixture was admixed with water, and filtered to give precipitates which were washed with water, then dissolved in DMF, and treated with methanol and water. The mixture was filtered to give precipitates which were washed with water and dried to afford 3-benzyl-5-(3-fluorophenyl)-1H-pyrazolo[4,3-c][1,8]naphthyridin-4 (5H)-one (330 mg, 45%).

Provenance & Evidence