Sodium Hydroxide → 6-(6-(3-Ethylureido)-4-(4-(trifluoromethyl)thiazol-2-yl)pyridin-3-yl)-1-((1-(2-morpholinoethyl)pyrrolidin-3-yl)methyl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

Participants

Reaction Steps

Ethyl 6-(6-(3-ethylureido)-4-(4-(trifluoromethyl)thiazol-2-yl)pyridin-3-yl)-1-((1-(2-morpholinoethyl)pyrrolidin-3-yl)methyl)-4-oxo-1,4-dihydroquinoline-3-carboxylate (Example 240, 340 mg) was dissolved in methanol (3 mL) and tetrahydrofuran (3 mL). To this solution was added 24 wt % sodium hydroxide (1 mL) and the reaction mixture was stirred at room temperature for 3 h. The solution was concentrated under reduced pressure to remove the organics. Water (7 mL) was added and the aqueous layer was carefully acidified to pH˜3 with 1N hydrochloric acid. A solid precipitated, and the mixture was centrifuged to help collect the solid which was then washed with cold water once and dried to give a light yellow solid (270 mg, 81.2%).

Provenance & Evidence