Diisopropylethylamine → 4-chloro-N-({4-chloro-3-[(3-chloro-5-cyclopropylphenyl)oxy]-2-fluorophenyl}methyl)-1-({[2-(trimethylsilyl)ethyl]oxy}methyl)-1H-imidazole-5-carboxamide

Participants

Reaction Steps

To a solution of ({4-chloro-3-[(3-chloro-5-cyclopropylphenyl)oxy]-2-fluorophenyl}methyl)amine (86 mg, 0.264 mmol), 4-chloro-1-({[2(trimethylsilyl)ethyl]oxy}methyl)-1H-imidazole-5-carboxylic acid (73.0 mg, 0.264 mmol) and HATU (100 mg, 0.264 mmol) in DMF (5 ml) was added diisopropylethyl amine (0.092 ml, 0.527 mmol) and the reaction mixture was stirred at rt for 45 minutes. The reaction mixture was diluted with EtOAc and washed with water. The solvent was removed and the crude material was purified via silica gel chromatography to give the desired compound which was only ˜85% pure. This was purified via reverse phase HPLC to give 4-chloro-N-({4-chloro-3-[(3-chloro-5-cyclopropylphenyl)oxy]-2-fluorophenyl}methyl)-1-({[2-(trimethylsilyl)ethyl]oxy}methyl)-1H-imidazole-5-carboxamide (98 mg, 0.168 mmol, 64% yield).

Provenance & Evidence