Triethylamine → Tert-butyl {[2-isobutyl-6-(4-{[methoxy(methyl)amino]carbonyl}-1,3-thiazol-2-yl)-4-(4-methylphenyl)quinolin-3-yl]methyl}carbamate

Participants

Reaction Steps

A mixture of 2-[3-{[(tert-butoxycarbonyl)amino]methyl}-2-isobutyl-4-(4-methylphenyl)-6-quinolinyl]-1,3-thiazole-4-carboxylic acid (0.27 g, 0.5 mmol), N,O-dimethylhydroxylamine hydrochloride (0.06 g, 0.6 mmol), ethyl-3(3-dimethylaminopropyl)carbodiimide hydrochloride (0.12 g, 0.6 mmol), 1-hydroxy-1H-benzotriazole (0.09 g, 0.6 mmol), triethylamine (0.08 ml, 0.6 mmol) and N,N-dimethylformamide (10 ml) was stirred at room temperature for 2 hrs. The reaction mixture was poured into water and extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the residue was crystallized from diisopropyl ether to give tert-butyl {[2-isobutyl-6-(4-{[methoxy(methyl)amino]carbonyl}-1,3-thiazol-2-yl)-4-(4-methylphenyl)quinolin-3-yl]methyl}carbamate (0.24 g, yield 85%) as white crystals.

Provenance & Evidence