Dimethylformamide → (Z)-5-Oxo-4-[1H-pyrrol-2-ylmethylene]-5,6-dihydro-4H-thieno [2,3-b]pyrrole-2-carboxylic acid (tetrahydro-pyran-2-yloxy)-amide

Participants

Reaction Steps

A solution of (Z)-5,6-dihydro-5-oxo-4-[(1H-pyrrol-2-yl)methylene]-4H-thieno[2,3-b]pyrrole-2-carboxylic acid (250 mg, 0.95 mmol), 1-hydroxybenzotriazole (1.1 mmol, 150 mg), 1-(tetrahydro-pyran-2-yloxy) amine (1.25 mmol, 146 mg), 1-(3-dimethoxyaminopropyl)-3-ethylcarbodiimide hydrochloride (1.1 mmol, 208 mg) and diisopropylethylamine (1.1 mmol, 190 mg) in dimethylformamide (4 ml) was stirred at room temperature for 3 hours then diluted with ethyl acetate and washed with 2M hydrochloric acid, saturated sodium bicarbonate and water. The resulting solution was dried over magnesium sulfate and evaporated to dryness. The residue was triturated with water/isopropyl alcohol to give 90 mg of (Z)-5-Oxo-4-[1H-pyrrol-2-ylmethylene]-5,6-dihydro-4H-thieno[2,3-b]pyrrole-2-carboxylic acid (tetrahydro-pyran-2-yloxy)-amide as a brown solid. MS(ES): m/e 360 [M+H].

Provenance & Evidence