Ammonium Hydroxide → HCID 67118604, compound

Participants

Reaction Steps

A mixture of [2-(7-methoxy-5-{[6-(methoxymethyl)pyridin-3-yl]oxy}-1H-indol-2-yl)-4,5-dihydro-1,3-thiazol-5-yl]acetic acid (160 mg), N-ethyl-N′-(3-dimethylaminopropyl)carbodiimide hydrochloride (144 mg), 1-hydroxybenzotriazole monohydrate (115 mg), 25% aqueous ammonium hydroxide solution (1 mL) and N,N-dimethylformamide (8 mL) was stirred at room temperature for 3.5 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 residue was purified by basic silica gel column chromatography (methanol/ethyl acetate=0/100 to 8/92, volume ratio) to give a white amorphous solid. The amorphous solid was crystallized from ethyl acetate-diethyl ether to give white crystals. The crystals were recrystallized from ethyl acetate-hexane to give the title compound (68 mg, 43%) as colorless crystals. MS 427 (MH+). mp 135-136° C.

Provenance & Evidence