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0 °C

1-Ethyl-(3-dimethylaminopropyl) carbodiimide hydrochloride (1.074 g, 5.6 mmol), triethylamine (1.12 mL, 8 mmol), 5-formyl-2,4-dimethyl-1H-pyrrole-3-formic acid (0.668 g, 4 mmol) and 1-hydroxybenzotriazole (0.756 g, 5.6 mmol) were added to DMF (10 mL) with stirring at about 0° C. and stirred for 1.5 hrs, and the oily residue obtained in the above step (1.38 g, 8 mmol) was added. The reaction was stirred at room temperature until completion was indicated by thin layer chromatography (TLC). 1.2 mL of water and 1 mL of saturated salt water were added, and the mixture was extracted with organic solvents (10% methanol/dichloromethane) (25 mL×3), the combined organic phase was washed with saturated salt water (25 mL×3), dried over anhydrous Na2SO4, and the solvent was distilled off under reduced pressure. The residue was then chromatographed (silica gel column chromatography, eluent: methanol:ethyl acetate=1:2) to give 0.625 g (1.94 mmol) of N-{2-[2-(diethylamino)ethylamino]-2-oxoethyl}-5-formyl-2,4-dimethyl-1H-pyrrole-3-formamide. Yield 48.5%. 1HNMR (DMSO-d6) δ 10.83 (s, br, 1H, NH), 9.75 (s, 1H), 7.65 (m, br, 1H, CONHCH2), 7.64 (m, br, 1H, CONHCH2), 3.81-3.73 (d, 2H), 3.14-3.10 (m, 2H), 2.57-2.55 (m, 2H), 2.46-2.40 (m, 4H), 2.26-2.20 (s, 3H), 2.12-2.08 (m, 3H), 1.06-1.01 (m, 6H).

1. stirringstirred for 1.5 hrs
2. customthe oily residue obtained in the above step (1.38 g, 8 mmol)
3. additionwas added
4. stirringThe reaction was stirred at room temperature until completion
5. extractionthe mixture was extracted with organic solvents (10% methanol/dichloromethane) (25 mL×3)
6. washthe combined organic phase was washed with saturated salt water (25 mL×3)
7. dry with materialdried over anhydrous Na2SO4
8. distillationthe solvent was distilled off under reduced pressure
9. customThe residue was then chromatographed (silica gel column chromatography, eluent: methanol:ethyl acetate=1:2)