2-Aminopyridine → HCID 10178227, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 3-cyclopentyl-2-(4-phenoxy-phenyl-propionic acid (prepared in Example 12A, 51 mg, 0.16 mmol) in methylene chloride (10 mL) and one drop of N,N-dimethylformamide was cooled to 0° C. and then treated with a 2.0M solution of oxalyl chloride in methylene chloride (0.10 mL, 0.18 mmol). The reaction mixture was stirred at 0° C. for 30 min and then treated with a solution of 2-aminopyridine (32 mg, 0.34 mmol) in tetrahydrofuran (2 mL) and N,N-diisopropylethylamine (0.07 mL, 0.39 mmol). The reaction mixture was stirred at 25° C. for 14 h. At this time, the reaction mixture was diluted with water (10 mL) and then extracted with methylene chloride (3×10 mL). The combined organic extracts were washed with water (1×10 mL), a 1N aqueous sodium hydroxide solution (1×10 mL), and a 1N aqueous hydrochloric acid solution (1×10 mL). The organic layer was dried over sodium sulfate, filtered, and concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 230-400 mesh, 90/10 hexanes/ethyl acetate) afforded 3-cyclopentyl-2-(4-phenoxy-phenyl)-N-pyridin-2-yl-propionamide (22 mg, 35%) as glassy solid: EI-HRMS m/e calcd for C25H26N2O2 (M+) 386.1994, found 386.2001.

Provenance & Evidence