Ammonium Hydroxide → 2-[2-(7-[2-Methoxy-1-(methoxymethyl)ethoxy]-5-{[6-(methylsulfonyl)pyridin-3-yl]oxy}-1H-indol-2-yl)-4,5-dihydro-1,3-thiazol-5-yl]acetamide

Participants

Reaction Conditions

Reaction Steps

A mixture of [2-(7-[2-methoxy-1-(methoxymethyl)ethoxy]-5-{[6-(methylsulfonyl)pyridin-3-yl]oxy}-1H-indol-2-yl)-4,5-dihydro-1,3-thiazol-5-yl]acetic acid (190 mg), N-ethyl-N′-(3-dimethylaminopropyl)carbodiimide hydrochloride (133 mg), 1-hydroxybenzotriazole (93 mg) and N,N-dimethylformamide (5 mL) was stirred at 50° C. for 20 min. After cooling to room temperature, 10% aqueous ammonium hydroxide solution (0.5 mL) was added to the mixture and the mixture was stirred at room temperature for 14 h. The mixture was concentrated under reduced pressure. The residue was dissolved in water and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over magnesium sulfate, filtered and concentrated. The residual oil was crystallized from ethyl acetate. The resulting crystals were washed with diethyl. ether. The crystals were recrystallized from acetonitrile to give the title compound (139 mg, 74%) as colorless crystals. MS 549 (MH+). mp 172-173° C.

Provenance & Evidence