Реакция #2146789

Уравнение реакции

{4-[6-methoxy-3-(3,4,5-trimethoxy-benzoyl)-benzofuran-2-yl]-pyrazol-1-yl}-acetic acid ethyl ester

ammonia

→

title compound

Выход 14.0%

2-{4-[6-Methoxy-3-(3,4,5-trimethoxy-benzoyl)-benzo[b]furan-2-yl]-pyrazol-1-yl}-acetamide

Выход 14.0%

Условия реакции

Обработка

1. 1
   Другоеthe resulting reaction mixture
2. 2
   ТемператураAfter cooling to room temperature the solution
3. 3
   Концентрированиеwas concentrated under vacuum
4. 4
   ДругоеThe resulting product was further purified by trituration with 1:1 hexane

Методика

{4-[6-methoxy-3-(3,4,5-trimethoxy-benzoyl)-benzofuran-2-yl]-pyrazol-1-yl}-acetic acid ethyl ester (30 mg, 0.061 mmol) was treated with 28% aqueous ammonia solution and the resulting reaction mixture was stirred at 80° C. for 3 h. After cooling to room temperature the solution was concentrated under vacuum and the residue subjected to flash column chromatography (silica gel, sequential elution—1:1 hexane:ethyl acetate, ethyl acetate). The resulting product was further purified by trituration with 1:1 hexane:diethyl ether to give the title compound as a yellow solid (4 mg, 14%). 1H-NMR (CDCl3) δ 8.29 (s, 1H), 8.14 (s, 1H), 7.13 (s, 2H), 7.12 (d, J=8.7 Hz, 1H), 7.05 (d, J=2.1 Hz, 1H), 6.81 (dd, J=8.7, 2.1 Hz, 1H), 6.14 (br s, N—H), 5.46 (br s, N—H), 4.83 (s, 2H), 3.93 (s, 3H), 3.86 (s, 3H), 3.78 (s, 6H).

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