Morpholine → HCID 67247478, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of 2-[4-({[(1-isopropyl-5-methyl-2-oxo-1,2-dihydroquinolin-3-yl)carbonyl]amino}methyl)piperidin-1-yl]propanoic acid hydrochloride (243 mg, 0.54 mmol, step 2), morpholine (52 mg, 0.60 mmol), and diisopropylethylamine (0.19 mL, 1.08 mmol) in dichloromethane (15 mL) was added HBTU (226 mg, 0.60 mmol) at 0° C., and the mixture was stirred at 0° C. for 1 h and at room temperature for 3 h. Then, the resulting mixture was poured onto saturated aqueous sodium hydrogen carbonate (100 mL), and the aqueous layer was extracted with dichloromethane (100 mL×3). The combined organic layer was dried over magnesium sulfate, and concentrated in vacuo. The residue was chromatographed on a column of silica gel eluting with ammonia/methanol/dichloromethane (0.1:1:30) to give 265 mg of the title compound as salt free form. This was treated with 10% hydrogen chloride in methanol (5 mL), and the solvent removed in vacuo to give 194 mg (69%) of the title compound as a yellow amorphous.

Provenance & Evidence