1-(2,3-Dihydrobenzofuran-5-yl)cyclopropanecarboxylic acid (24.0 mg, 0.118 mmol) was placed in an oven-dried flask which was allowed to cool under nitrogen. Thionyl chloride (0.3 mL) and N,N-dimethylformamide (0.03 mL) were added and the solution was allowed to stir for 30 minutes. The excess thionyl chloride was removed under vacuum and the resulting oil was re-dissolved in dichloromethane containing triethylamine (0.0495 mL, 0.353 mmol). tert-Butyl 3-(6-amino-3-methylpyridin-2-yl)benzoate (33.4 mg, 0.118 mmol) was added and the reaction mixture was allowed to stir for 3 hours. Trifluoroacetic acid (1 mL) was added and the solution was allowed to stir for an additional 3 hours. The mixture was evaporated to dryness, dissolved in a minimum of N,N-dimethylformamide and then purified by reverse-phase preparative liquid chromatography utilizing a gradient of 0-99% acetonitrile in water containing 0.05% trifluoroacetic acid to yield 3-(6-(1-(2,3-dihydrobenzofuran-5-yl)cyclo-propanecarboxamido)-3-methylpyridin-2-yl)benzoic acid. ESI-MS m/z calc. 414.2, found; 415.0 (M+1)+Retention time 1.64 minutes.
