Triethylamine → HCID 86633733, compound

Participants

Reaction Steps

Triethylamine (83 mL, 0.60 mol) was added to a solution of 4-(2-chloro-3-nitroquinolin-4-ylamino)butan-1-ol (44.34 g, 149.9 mmol). A solution of tert-butyldimethylsilyl chloride (100 g of a 50% w/w solution in toluene, 0.33 mol) in DMF (60 mL) was slowly added, and the reaction was then stirred at room temperature of five hours. Additional tert-butyldimethylsilyl chloride (50 g of a 50% w/w solution in toluene) was added, and the reaction was stirred at room temperature for three days. Additional tert-butyldimethylsilyl chloride (100 g of a 50% w/w solution in toluene, 0.33 mol) was added, and the reaction was stirred at room temperature for three hours. Finally, additional triethylamine (83 mL, 0.60 mol) and tert-butyldimethylsilyl chloride (100 g of a 50% w/w solution in toluene, 0.33 mol) were added, and the reaction was stirred at room temperature for 1.5 hours. The reaction mixture was filtered to remove a solid, and the filtrate was concentrated under reduced pressure. The residue was dissolved in chloroform (250 mL), and the resulting solution was washed sequentially with 5% w/w aqueous ammonium chloride (3×150 mL), saturated aqueous sodium bicarbonate (2×150 mL), and brine (150 mL), dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The resulting solid was further dried under vacuum and passed through a layer of silica gel (eluting with dichloromethane) to provide 56.04 g of N-[4-(tert-butyldimethylsilanyloxy)butyl]-2-chloro-3-nitroquinolin-4-amine as a yellow solid.

Provenance & Evidence