Azetidine → [2-(5-{1-[4-(azetidin-1-ylcarbonyl)phenyl]-2-(tetrahydro-2H-pyran-4-yl)ethyl}-1H-pyrrol-2-yl)-1,3-thiazol-5-yl]methanol

Participants

Reaction Steps

To a solution of 4-[1-{5-[5-(hydroxymethyl)-1,3-thiazol-2-yl]-1H-pyrrol-2-yl}-2-(tetrahydro-2H-pyran-4-yl)ethyl]benzoic acid (100 mg) in N,N-dimethylformamide (5 mL) were added 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (70.0 mg) and 1-hydroxybenzotriazole (50.0 mg), and the mixture was stirred for 30 min. To the reaction mixture was added azetidine (21.0 mg), and the mixture was stirred overnight at room temperature. The reaction mixture was diluted with ethyl acetate and washed with 1M hydrochloric acid. The ethyl acetate layer was washed with saturated aqueous sodium hydrogen carbonate and saturated brine, dried (MgSO4) and concentrated. The residue was subjected to silica gel column chromatography, and the title compound (30.0 mg, yield 28%) was obtained as a colorless amorphous solid from a fraction eluted with ethyl acetate-methanol (9:1, volume ratio). MS: 452 (MH+).

Provenance & Evidence