Ammonia → HCID 67118739, compound

Participants

Reaction Steps

To an ice-cooled and stirred mixture of {2-[6-fluoro-7-(2-methoxyethoxy)-5-{[6-(methylsulfonyl)pyridin-3-yl]oxy}-1H-indol-2-yl]-4,5-dihydro-1,3-thiazol-5-yl}acetic acid (135 mg) in N,N-dimethylformamide (7 mL) were added 1-hydroxybenzotriazole (70 mg) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (100 mg). After stirring at 4° C. to room temperature for 15 h, the reaction mixture was cooled on an ice bath and 10% aqueous ammonia solution (1.0 mL) was added thereto. The mixture was stirred at room temperature for 5 h and partitioned between ethyl acetate and water. The organic layer was washed with aqueous sodium hydrogen carbonate solution and brine, dried (MgSO4), filtered, and concentrated to give light yellow crystals, which were recrystallized from tetrahydrofuran-ethyl acetate to give the title compound (84 mg) as pale yellow crystals. MS 523 (MH+). mp 143-144° C.

Provenance & Evidence