Hydrochloric Acid → HCID 68582637, compound

Participants

Reaction Steps

To a solution of ethyl N-[2-[(4-chloro-2-methoxy-6-methylphenyl)amino]-1-methyl-1H-benzimidazol-7-yl]-N-(4-methoxyphenyl)glycinate (20 mg, 0.039 mmol) in methanol (0.5 ml) was added 1N sodium hydroxide (0.5 ml). The mixture was stirred at room temperature for 1.5 h, then neutralized with 1N hydrochloric acid (0.5 ml) and concentrated to dryness. To a mixture of the residue, diethylamine (0.0081 ml, 0.079 mmol) and N,N-dimethylformamide (3 ml) were added triethylamine (0.011 ml, 0.079 mmol) and O-benzotriazol-1-yl-N,N,N′,N′-tetramethyluronium hexafluorophosphate (22.4 mg, 0.079 mmol). The mixture was stirred at room temperature for 1.5 h. The mixture was diluted with water (20 ml) and extracted with ethyl acetate (30 ml). The extract was washed with water, dried over magnesium sulfate and evaporated in vacuo. The residue was flash chromatographed eluting with a 20% acetone/hexanes) to give the crude product. The crude product was purified by reverse phase HPLC (acetonitrile containing 0.1 trifluoroacetic acid/water containing 0.1% trifluoroacetic acid). The eluent was concentrated in vacuo and the residue was dissolved in methanol (2 ml) before 2M hydrogen chloride in diethylether (2 ml) was added. The mixture was concentrated in vacuo to give 9.6 mg (46%) of the title as a powder.

Provenance & Evidence