Ammonium Hydroxide → HCID 58237070, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of {2-[7-(1-methylethoxy)-5-{[5-(methylsulfonyl)pyridin-2-yl]oxy}-1H-indol-2-yl]-4,5-dihydro-1,3-thiazol-5-yl}acetic acid (230 mg), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (140 mg), 1-hydroxybenzotriazole (100 mg) and N,N-dimethylformamide (5 mL) was stirred at 50° C. for 30 min, and then cooled to 0° C. To the mixture was added aqueous ammonium hydroxide solution (10%, 1 mL). The whole was stirred at room temperature for 15 h. Water was added to the residue and the resultant was extracted with ethyl acetate. The organic layer was washed successively with saturated aqueous sodium hydrogen carbonate solution and brine, dried (MgSO4), filtered, and concentrated in vacuo. The residue was purified by silica gel chromatography (ethyl acetate:methanol=100:0 to 90:10, volume ratio) to give pale yellow crystals. The crystals were recrystallized from acetone-hexane to give the title compound (90 mg, 39%) as pale yellow prisms. MS 489 (MH+). mp 212-213° C.

Provenance & Evidence