Reaktion #46807

Reaktionsgleichung

2-[4-(3-Oxo-morpholin-4-yl)-phenylcarbamoyl]-1H-benzoimidazole-4-carboxylic acid methyl ester

K2CO3

2-bromo-N-(5-Chloro-pyridin-2-yl-)-acetamide

→

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

Lösungsmittel

DMF

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   Waschenwashed with 50 mL of a saturated NaHCO3-solution
2. 2
   workup.ADDITIONto be added
3. 3
   WaschenThe organic layer was washed with brine
4. 4
   Trocknendried over anhydrous MgSO4
5. 5
   Einengenconcentrated under reduced pressure
6. 6
   SonstigeThe residue was purified by preparative HPLC (CH3CN/H2O gradient+0.05% formic acid)

Vorschrift

72.0 mg (0.183 mmol) 2-[4-(3-Oxo-morpholin-4-yl)-phenylcarbamoyl]-1H-benzoimidazole-4-carboxylic acid methyl ester were dissolved in 7 mL DMF. Sequentially 37.8 mg (0.274 mmol) K2CO3 and 54.6 mg (0.219 mmol) 2-bromo-N-(5-Chloro-pyridin-2-yl-)-acetamide were added and the resulting mixture was stirred for 4 h at 80°. The mixture was diluted with 200 mL toluene and washed with 50 mL of a saturated NaHCO3-solution. The product was not completely soluble in toluene, so ethyl acetate had to be added. The organic layer was washed with brine, dried over anhydrous MgSO4 and concentrated under reduced pressure. The residue was purified by preparative HPLC (CH3CN/H2O gradient+0.05% formic acid) to give 1-[(5-Chloro-pyridin-2-ylcarbamoyl)-methyl]-2-[4-(3-oxo-morpholin-4-yl)-phenylcarbamoyl]-1H-benzoimidazole-4-carboxylic acid methyl ester as a light brown amorphous solid.

Quelle