Reaktion #46821

Reaktionsgleichung

1-[(5-Chloro-pyridin-2-ylcarbamoyl)-methyl]-2-[4-(3-oxo-morpholin-4-yl)-phenylcarbamoyl]-1H-benzoimidazole-4-carboxylic acid methyl ester

BBr3

BBr3

→

1-[(5-Chloro-pyridin-2-ylcarbamoyl)-methyl]-2-[4-(3-oxo-morpholin-4-yl)-phenylcarbamoyl]-1H-benzoimidazole-4-carboxylic acid

Lösungsmittel

CH2Cl2

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeAt 0° C
2. 2
   workup.STIRRINGAfter stirring for 24 h at room temperature the reaction mixture
3. 3
   Einengenwas concentrated
4. 4
   Sonstigepurified by preparative HPLC (CH3CN/H2O gradient+0.05% formic acid)

Vorschrift

127 mg (0.20 mmol) 1-[(5-Chloro-pyridin-2-ylcarbamoyl)-methyl]-2-[4-(3-oxo-morpholin-4-yl)-phenylcarbamoyl]-1H-benzoimidazole-4-carboxylic acid methyl ester were dissolved in 15 mL CH2Cl2. At 0° C. 1.8 mL (1.8 mmol) of a 1 M BBr3-solution were added. The reaction mixture was stirred for 24 h at room temperature. Because of incomplete conversion further 0.9 mL (0.9 mmol) of a 1 M BBr3-solution were added. After stirring for 24 h at room temperature the reaction mixture was concentrated and purified by preparative HPLC (CH3CN/H2O gradient+0.05% formic acid). 1-[(5-Chloro-pyridin-2-ylcarbamoyl)-methyl]-2-[4-(3-oxo-morpholin-4-yl)-phenylcarbamoyl]-1H-benzoimidazole-4-carboxylic acid was obtained as a light brown, amorphous solid. Yield: 73 mg MS (ES+): m/e=549, chloro pattern.

Quelle