2-[1-(Aminocarbonyl)-2-[[5-(4-nitrophenyl)-2-furanyl]methylene]hydrazinyl]-acetic Acid Ethyl Ester synthesis

Yield:55227-60-6 65.2%

Reaction Conditions:

with ammonia in N,N-dimethyl-formamide at 20; for 12 h;

Steps:

4.1.3. Ethyl 2-{1-carbamoyl-2-[(5-(4-nitrophenyl)furan-2-yl)methylene]hydrazinyl}ethanoate (3)

To a solution of anhydrous ammonia (about 5%) in DMF (10 mL) 2a (100 mg, 0.2 mmol) was added. The reaction mixture was stirred at room temperature for 12 h. After removal of DMF under reduced pressure, the crude product was purified by column chromatography on silica gel under CH₂Cl₂/CH₃OH (from 0% to 3%) to give 3 (47 mg, 65.2%) as a yellow powder. ¹H NMR (DMSO-d₆) d: 8.28 (2H, d, J = 8.8 Hz), 7.84 (2H, d, J = 8.8 Hz), 7.30 (1H, s), 6.95 (1H, d, J = 3.7 Hz), 6.79 (1H, d, J = 3.7 Hz), 4.78 (2H, s), 4.26 (2H, q, J = 7.2 Hz), 1.30 (3H, t, J = 7.1 Hz); HRMS (FAB) calcd for C₁₆H₁₇N₄O₆, 361.1148; found, 361.1100.

References:

Kumata, Katsushi;Ogawa, Masanao;Takei, Makoto;Fujinaga, Masayuki;Yoshida, Yuichiro;Nengaki, Nobuki;Fukumura, Toshimitsu;Suzuki, Kazutoshi;Zhang, Ming-Rong [Bioorganic and Medicinal Chemistry,2012,vol. 20,# 1,p. 305 - 310] Location in patent:experimental part