Water → HCID 86659148, compound

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 (1.59 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 0.768 g (2.21 mmol) of N-{1-[2-(1-methylpyrrolidin-2-yl)ethylamino]-1-oxoprop-2-yl}-5-formyl-2,4-dimethyl-1H-pyrrole-3-formamide. Yield 55.2%. 1HNMR (DMSO-d6) δ 10.83 (s, br, 1H, NH), 9.75 (s, 1H), 7.78 (m, br, 1H, CONHCH2), 7.77 (m, br, 1H, CONHCH2), 4.71 (m, 1H), 3.12-3.10 (m, 2H), 2.86 (m, 1H), 2.37-2.31 (m, 3H), 2.30-2.22 (m, 2H), 2.26-2.20 (s, 3H), 2.12-2.08 (m, 3H), 1.68-1.64 (m, 2H), 1.61-1.53 (m, 2H), 1.56-1.54 (m, 2H), 1.48-1.41 (d, 3H).

Provenance & Evidence