Oxalyl chloride → HCID 10185003, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 3-cyclopentyl-2-{4-[(pyridine-3-carbonyl)-amino]-phenyl}-propionic acid (233 mg, 0.66 mmol) in methylene chloride (10 mL) was cooled to 0° C. and then treated with a 2.0M solution of oxalyl chloride in methylene chloride (0.36 mL, 0.72 mmol) and a few drops of N,N-dimethylformamide. The reaction mixture was stirred at 0° C. for 15 min and at 25° C. for 30 min. The reaction mixture was then treated with a solution of 2-amino-thiazole-4-carboxylic acid ethyl ester (367 mg, 1.45 mmol) in tetrahydrofuran (5 mL) and N,N-diisopropylethylamine (0.40 mL, 2.31 mmol). This solution was stirred at 25° C. for 48 h. At this time, the reaction was concentrated in vacuo. High pressure liquid chromatography (Chromegasphere SI-60, 10 μM, 60 Å, 25 cm×23 cm ID, 95/5 ethyl acetate/heptane) afforded 2-(3-cyclopentyl-2-{4-[(pyridine-3-carbonyl)-amino]-phenyl}propionylamino)-thiazole-4-carboxylic acid ethyl ester (40.5 mg, 12.5%) as an off-white: mp 222-223° C.; EI-HRMS m/e calcd for C26H28N4O4S (M+) 492.1831, found 492.1835.

Provenance & Evidence