Water → N-{2-[(1-ethylpyrrolidin-2-yl)methylamino]-2-oxoethyl}-5-formyl-2,4-dimethyl-1H-pyrrole-3-formamide

Participants

Reaction Conditions

Reaction Steps

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 oily residue obtained in the above step (1.48 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 0.786 g (2.35 mmol) of N-{2-[(1-ethylpyrrolidin-2-yl)methylamino]-2-oxoethyl}-5-formyl-2,4-dimethyl-1H-pyrrole-3-formamide. Yield 58.8%. 1HNMR (DMSO-d6) δ10.83 (s, br, H, NH), 9.75 (s, 1H), 7.74 (m, br, 1H, CONHCH2), 7.51 (m, br, 1H, CONHCH2), 3.85-3.83 (d, 2H), 3.07-3.03 (m, 2H), 2.85 (m, 1H), 2.49-2.46 (m, 2H), 2.32-2.30 (m, 2H), 2.37-2.33 (m, 3H), 2.14-2.10 (m, 3H), 1.68-1.64 (m, 2H), 1.56-1.54 (m, 2H), 1.06-1.01 (m, 3H).

Provenance & Evidence