Sodium Bicarbonate → 1-{[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl}-2-[(1-cyclopropylpiperidin-4-yl)carbamoyl]-1H-benzimidazole-5-carboxylic acid

Beteiligte Stoffe

Reaktionsschritte

21.0 mg (0.098 mmol) (1-Cyclopropyl-piperidin-4-ylamine-dihydrochloride were dissolved in 3 mL CH3CN and 3 mL water. 82.3 mg (0.98 mmol, 10 equivalents) NaHCO3 were added. Then, a solution of 48.1 mg (0.098 mmol) 1-[5-(5-chloro-thiophen-2-yl)-isoxazol-3-ylmethyl]-2-trichloromethyl-1H-benzoimidazole-5-carboxylic acid methyl ester in 2 mL CH3CN was added and the resulting mixture was stirred vigorously for 3 h under reflux. The mixture was concentrated under reduced pressure. The residue was purified by preparative RP-HPLC (CH3CN/H2O gradient and 0.05% formic acid) to give pure 1-[5-(5-chloro-thiophen-2-yl)-isoxazol-3-ylmethyl]-2-(1-cyclopropyl-piperidin-4-ylcarbamoyl)-1H-benzoimidazole-5-carboxylic acid in form of a colorless amorphous solid. (Under these conditions the methyl ester was hydrolyzed simultaneously!)

Herkunft & Nachweise