Morpholine → HCID 44155427, compound

Participants

Reaction Steps

In a 100 mL round bottomed flask 3-[(3-{4-[(methylsulfonyl)amino]phenyl}-4-oxochromen-7-yloxy)methyl]benzoic acid (315.0 mg, 0.677 mmol) was treated with triethylamine (137.0 mg, 1.354 mmol, 2.0 equiv) and 2,4,6-trichlorobenzoyl chloride (198.2 mg, 0.812 mmol, 1.2 equiv) in THF (6 mL) under a nitrogen atmosphere. The mixture was stirred at room temperature for 1 hour. To the mixture were added a solution of 4-hydroxyethyl)morpholine (133.2 mg, 1.016 mmol, 1.5 equiv) in THF (3 mL) and dimethylaminopyridine (82.7 mg, 0.677 mmol, 1.0 equiv). Again, the mixture was stirred at room temperature for 1 hour. To the mixture were added H2O (50 mL) and the whole was extracted with EtOAc (50 mL×3). The combined organic layers were washed with brine (50 mL) and dried with Na2SO4. The solvent was removed under a reduced pressure to give a crude mixture. The crude mixture was purified by a column-chromatography (SiO2=80 g, 2.5% MeOH/CH2Cl2 to 5% MeOH/CH2Cl2) to give 2-morpholinoethyl 3-((3-(4-(methylsulfonamido)phenyl)-4-oxo-4H-chromen-7-yloxy)methyl)benzoate as a colorless solid.

Provenance & Evidence