1-Hydroxybenzotriazole → HCID 58237094, compound

Participants

Reaction Steps

To an ice-cooled and stirred mixture of methylamine hydrochloride (48 mg) and triethylamine (0.10 mL) in N,N-dimethylformamide (10 mL) were added (2-{7-methoxy-5-[4-(methylsulfonyl)phenoxy]-1H-indol-2-yl}-4,5-dihydro-1,3-thiazol-5-yl)acetic acid (0.16 g), 1-hydroxybenzotriazole (94 mg) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (134 mg). After stirring at 4° C. to room temperature for 7 h, the reaction mixture was partitioned between ethyl acetate and water. The organic layer was washed successively with aqueous sodium hydrogen carbonate solution and brine, dried (MgSO4), filtered, and concentrated to give a pale yellow oil, which was purified by silica gel chromatography (ethyl acetate:methanol=100:0 to 90:10, volume ratio) to give a colorless oil. The oil was crystallized from ethyl acetate-hexane to give the title compound (144 mg, 88%) as colorless needles. MS 474 (MH+). mp 125-126° C.

Provenance & Evidence