反応 #46886

反応方程式

(4-Amino-3-fluoro-phenyl)-pyrrolidin-1-yl-methanone

NaHCO3

2-Trichloromethyl-1H-benzoimidazole-4-carboxylic acid methyl ester

→

2-[2-Fluoro-4-(pyrrolidine-1-carbonyl)-phenylcarbamoyl]-1H-benzoimidazole-4-carboxylic acid methyl ester

溶媒

CH2Cl2

THF

water

反応条件

後処理

1. 1
   洗浄washed with a saturated NaHCO3-solution and with brine
2. 2
   乾燥The organic layer was dried over anhydrous MgSO4
3. 3
   濃縮concentrated under reduced pressure
4. 4
   その他Final purification by preparative RP-HPLC (CH3CN/H2O gradient+0.05% formic acid)

実験手順

59.0 mg (0.28 mmol) (4-Amino-3-fluoro-phenyl)-pyrrolidin-1-yl-methanone were dissolved in 6 mL THF and 3 mL water. 238.0 mg (2.83 mmol) NaHCO3 were added. Finally 75.6 mg (0.26 mmol) 2-Trichloromethyl-1H-benzoimidazole-4-carboxylic acid methyl ester were added and the resulting mixture was stirred vigorously for 3 h at room temperature. The mixture was diluted with CH2Cl2 and washed with a saturated NaHCO3-solution and with brine. The organic layer was dried over anhydrous MgSO4 and concentrated under reduced pressure. Final purification by preparative RP-HPLC (CH3CN/H2O gradient+0.05% formic acid) gave pure 2-[2-Fluoro-4-(pyrrolidine-1-carbonyl)-phenylcarbamoyl]-1H-benzoimidazole-4-carboxylic acid methyl ester in form of a colorless amorphous solid. Yield: 69 mg MS (ES+): m/e=411.

出典