4-Methylmorpholine → Tert-butyl 2-(3-{[3-(2-methyl-1,3-dioxolan-2-yl)propanoyl]amino}quinolin-4-yl)hydrazinecarboxylate

Participants

Reaction Conditions

Reaction Steps

A mixture of tert-butyl N′-(3-aminoquinolin-4-yl)hydrazinecarboxylate (4.50 g, 16.4 mmol), 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (3.93 g, 20.5 mmol), 4-methylmorpholine (2.29 mL, 20.5 mmol), and 4-dimethylaminopyridine (0.100 g, 0.82 mmol) in pyridine (120 mL) was chilled to 0° C. under an atmosphere of nitrogen. The mixture was treated drop-wise with a solution of 3-(2-methyl-[1,3]dioxolan-2-yl)-propionic acid (3.28 g, 20.5 mmol) in pyridine (30 mL). The reaction mixture was allowed to slowly come to ambient temperature. After 18 h, the reaction mixture was concentrated under reduced pressure to give a dark red oil. The oil was dissolved in chloroform (150 mL) and washed with 5% Na2CO3 aqueous solution (2×50 mL) and brine (50 mL), dried over Na2SO4, filtered, and concentrated under reduced pressure to yield 6.83 g of crude tert-butyl 2-(3-{[3-(2-methyl-1,3-dioxolan-2-yl)propanoyl]amino}quinolin-4-yl)hydrazinecarboxylate as a dark red oil.

Provenance & Evidence