Methanamine, hydrochloride (1:1) → HCID 67118574, compound

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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 (300 mg), N-ethyl-N′-(3-dimethylaminopropyl)carbodiimide hydrochloride (270 mg), 1-hydroxybenzotriazole monohydrate (216 mg), methylammonium chloride (95 mg), triethylamine (0.2 mL) and N,N-dimethylformamide (13 mL) was stirred at room temperature for 2 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 5/95, volume ratio), followed by silica gel column chromatography (methanol/ethyl acetate=0/100 to 8/92, volume ratio) to give a yellow oil. The oil was crystallized from acetonitrile-diethyl ether to give white crystals. The crystals were recrystallized from acetonitrile-diethyl ether to give the title compound (204 mg, 66%) as colorless crystals. MS 441 (MH+). mp 102-104° C.

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