Methanamine, hydrochloride (1:1) → HCID 66898570, compound

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A mixture of [2-(7-[2-methoxy-1-(methoxymethyl)ethoxy]-5-{[5-(methylsulfonyl)pyridin-2-yl]oxy}-1H-indol-2-yl)-4,5-dihydro-1,3-thiazol-5-yl]acetic acid (280 mg), N-ethyl-N′-(3-dimethylaminopropyl)carbodiimide hydrochloride (195 mg), 1-hydroxybenzotriazole (138 mg), methylammonium chloride (69 mg), triethylamine (0.14 mL) and N,N-dimethylformamide (15 mL) was stirred at room temperature for 2.5 h. The mixture was concentrated under reduced pressure. The residue was dissolved in water and the mixture was extracted with ethyl acetate-tetrahydrofuran. 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 5/95, volume ratio) to give a pale yellow amorphous solid. The amorphous solid was crystallized from acetonitrile-diethyl ether to give white crystals. The crystals were recrystallized from ethyl acetate-diethyl ether to give the title compound (174 mg, 61%) as colorless crystals. MS 563 (MH+). mp 123-125° C.

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