2-Bromoethyl methyl ether → 1-[(5-Chloro-pyridin-2-ylcarbamoyl)-methyl]-4-(2-methoxy-ethoxymethyl)-1H-benzoimidazole-2-carboxylic acid (1-isopropyl-piperidin-4-yl)-amide

Participants

Reaction Steps

81.6 mg (0.065 mmol) 1-[(5-Chloro-pyridin-2-ylcarbamoyl)-methyl]-4-hydroxymethyl-1H-benzoimidazole-2-carboxylic acid (1-isopropyl-piperidin-4-yl)-amide were dissolved in 5 mL abs. DMF. At 0° C. 21.9 mg (0.195 mmol) potassium tert.butylate were added. After 5 min 12 μl (0.13 mmol) 1-bromo-2-methoxy-ethane were added and the reaction mixture was allowed to come to room temperature. After 3 h further 12 μl (0.13 mmol) 1-bromo-2-methoxy-ethane were added and the reaction mixture was stirred for 16 h. The solvent was distilled off and the resulting residue was purified by preparative RP-HPLC (CH3CN/H2O gradient+0.05% formic acid) to give 1-[(5-Chloro-pyridin-2-ylcarbamoyl)-methyl]-4-(2-methoxy-ethoxymethyl)-1H-benzoimidazole-2-carboxylic acid (1-isopropyl-piperidin-4-yl)-amide as a light brown amorphous solid. The title compound was obtained as its formiate. Yield: 12 mg MS (ES+): m/e=543, chloro pattern.

Provenance & Evidence