Methanol → HCID 68472339, compound

Participants

Reaction Conditions

Reaction Steps

(R)-tert-butyl 3-((3-(ethoxycarbonyl)-6-(6-(3-ethylureido)-4-(4-(trifluoromethyl)thiazol-2-yl)pyridin-3-yl)-4-oxoquinolin-1(4H)-yl)methyl)morpholine-4-carboxylate (Example 254, 0.150 g, 0.20 mmol) was suspended in MeOH (6 mL) in a microwave vessel (CEM). THF (3.00 mL) was added. A 2.0 M aq solution of LiOH (0.381 mL, 0.76 mmol) was added. The microwave vessel was heated in the microwave at 100° C. for 15 min After cooling to room temperature solvent was removed in vacuo and residue was taken up in dichloromethane (2 ml) and 4N HCl in dioxane (1 ml) was added. The mixture was stirred at room temperature for 1 h, then diluted with water (3 ml) and neutralized with saturate NaHCO3. The mixture was extracted with DCM three times, and the combined organic layers were dried over Na2SO4 and filtered. The filtrate was concentrated in vacuo, and the residue was purified by flash column chromatography on silica gel using (dichloromethane-methanol) to give (R)-tert-butyl 3-((3-(ethoxycarbonyl)-6-(6-(3-ethylureido)-4-(4-(trifluoromethyl)thiazol-2-yl)pyridin-3-yl)-4-oxoquinolin-1(4H)-yl)methyl)morpholine-4-carboxylic acid (0.042 g, 36%).

Provenance & Evidence