Morpholine → HCID 10347887, compound

Participants

Reaction Conditions

Reaction Steps

4-[5-(6-Methanesulfonyloxymethyl-4-oxo-4H-pyran-3-yloxy)-pentyloxy]-7-trifluoromethyl-quinoline-3-carboxylic acid ethyl ester 18 (123 mg, 0.214 mmol) was dissolved in dichloromethane (3 mL). Morpholine (47.3 μL, 0.537 mmol) was added via syringe. The mixture was stirred at 45° C. for 3 h. CH2Cl2 (50 ml) was added and the solution was washed with NaHCO3 10% (3×50 mL) and brine (3×50 mL). The organic layer was dried over MgSO4, filtered and evaporated. The crude product was purified by column chromatography on silica using as eluent CH2Cl2:MeOH=95:05. 4-[5-(6-Morpholin-4-ylmethyl-4-oxo-4H-pyran-3-yloxy)-pentyloxy]-7-trifluoromethyl-quinoline-3-carboxylic acid ethyl ester EHT 8935 was obtained (66 mg, 55%) as a colourless oil.

Provenance & Evidence