反应详情

250 mg (0.40 mmol) 4-[2-(tert-Butyl-dimethyl-silanyloxy)-ethoxy]-1-[(5-chloro-pyridin-2-ylcarbamoyl)-methyl]-1H-benzoimidazole-2-carboxylic acid (1-isopropyl-piperidin-4-yl)-amide were dissolved in 15 mL THF. 435 μl of a 1 M TBAF-solution in THF and 26 μl acetic acid were added. The resulting mixture was stirred for 48 h at room temperature. The reaction mixture was concentrated under reduced pressure. The residue was taken up in 50 mL CH2Cl2 and washed once with a saturated NaHCO3-solution and five times with water. The organic layer was dried over anhydrous MgSO4 and concentrated under vacuo. Final purification by preparative RP-HPLC (CH3CN/H2O gradient+0.05% formic acid) gave pure 1-[(5-Chloro-pyridin-2-ylcarbamoyl)-methyl]-4-(2-hydroxy-ethoxy)-1H-benzoimidazole-2-carboxylic acid (1-isopropyl-piperidin-4-yl)-amide as its formiate in form of a colorless amorphous material. The title compound was transformed into its acetate. Yield: 132 mg MS (ES+): m/e=515, chloro pattern.

1. concentrationThe reaction mixture was concentrated under reduced pressure
2. washwashed once with a saturated NaHCO3-solution and five times with water
3. dry with materialThe organic layer was dried over anhydrous MgSO4
4. concentrationconcentrated under vacuo
5. customFinal purification by preparative RP-HPLC (CH3CN/H2O gradient+0.05% formic acid)