Water → N-{2-[(piperidin-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 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 (1.37 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 7.99 g (2.50 mmol) of N-{2-[(piperidin-2-yl)methylamino]-2-oxoethyl}-5-formyl-2,4-dimethyl-1H-pyrrole-3-formamide. Yield 62.4%. 1HNMR (DMSO-d6) δ10.82 (s, br, 1H, NH), 7.71 (s, 1H), 7.67 (m, br, 1H, CONHCH2), 7.49 (t, br, 1H, NH), 4.40 (s, br, 1H, NH), 3.81-3.73 (d, 2H), 3.39-3.43 (m, 1H), 3.16-3.18 (m, 2H), 2.50 (s, 3H), 2.60 (s, 3H), 2.08-2.11 (m, 2H), 1.82-1.86 (m, 2H), 1.58-1.64 (m, 2H), 1.39-1.44 (m, 2H).

Provenance & Evidence