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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 sequentially added to DMF (10 mL) with stirring at about 0° C. and stirred for 1.5 hrs, and the compound obtained in the above step (1.86 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 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 0.614 g (1.61 mmol) of N-{2-[(1-benzylpyrrolidin-3-yl)amino]-2-oxoethyl}-5-formyl-2,4-dimethyl-1H-pyrrole-3-formamide. Yield 40.2%. 1HNMR (DMSO-d6) δ10.81 (s, br, 1H, NH), 9.64 (s, 1H), 7.63 (m, br, 1H, CONHCH2), 6.92 (t, br, 1H, NH), 6.83-6.86 (m, 5H, benzene ring hydrogen), 3.81-3.75 (d, 2H), 3.67-3.68 (m, 1H), 3.50-3.669 (m, 2H), 3.16-3.17 (m, 2H), 2.32 (s, 3H), 2.33 (s, 3H), 1.71-1.82 (m, 2H), 1.10-1.11 (m, 2H).

1. stirringstirred for 1.5 hrs
2. customthe compound obtained in the above step (1.86 g, 8 mmol)
3. additionwas added
4. stirringThe reaction was stirred at room temperature until completion
5. extractionthe mixture was extracted with 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)