Hydrochloric Acid → HCID 59416074, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of (S)-ethyl 6-(6-(3-ethylureido)-4-(4-(trifluoromethyl)thiazol-2-yl)pyridin-3-yl)-1-(1-hydroxy-3-methylbutan-2-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylate (Example 110, 213 mg, 0.35 mmol) in tetrahydrofuran (1 mL) and methanol (1 mL) was added 2 M lithium hydroxide (0.259 mL, 0.52 mmol). The reaction mixture was heated at 100° C. for 15 min in a microwave reactor. The reaction mixture was cooled to room temperature, diluted with water, and treated with 1 N HCl until pH 3-4. The precipitate that formed was collected by filtration, washed with water and hexanes. Purification via reverse phase HPLC (C18, acetonitrile/water 0-95% gradient) provided (S)-6-(6-(3-ethylureido)-4-(4-(trifluoromethyl)thiazol-2-yl)pyridin-3-yl)-1-(1-hydroxy-3-methylbutan-2-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid as a light yellow solid (146.4 mg, 72%).

Provenance & Evidence