三乙胺 → 4-{N'-[2-(4-Nitro-phenyl)-4H-furo[3,2-b]pyrrole-5-carbonyl]-hydrazino}-butyric acid ethyl ester

HRID 1713052

反应方程式

HRID 1713052 反应方程式
C(O[C:4]([C:6]1[NH:10][C:9]2[CH:11]=[C:12]([C:14]3[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][CH:15]=3)[O:13][C:8]=2[CH:7]=1)=[O:5])C.[NH2:23][NH2:24].Br[CH2:26][CH2:27][CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30].C(N(CC)CC)C>CC(O)C>[CH2:32]([O:31][C:29](=[O:30])[CH2:28][CH2:27][CH2:26][NH:23][NH:24][C:4]([C:6]1[NH:10][C:9]2[CH:11]=[C:12]([C:14]3[CH:15]=[CH:16][C:17]([N+:20]([O-:22])=[O:21])=[CH:18][CH:19]=3)[O:13][C:8]=2[CH:7]=1)=[O:5])[CH3:33]

参与物

6

反应物 4

HCID 8471三乙胺HCID 9321肼(无水)HCID 763004-溴丁酸乙酯HCID 594634452-(4-nitro-phenyl)-4H-furo[3,2-b]pyrrole-5-carboxylic acid ethyl ester

产物 1

HCID 594634534-{N'-[2-(4-Nitro-phenyl)-4H-furo[3,2-b]pyrrole-5-carbonyl]-hydrazino}-butyric acid ethyl ester

试剂、催化剂与溶剂 1

HCID 3776异丙醇溶剂

反应条件

温度
80 °C

实验过程

As depicted in Scheme 31 below, 2-(4-nitro-phenyl)-4H-furo[3,2-b]pyrrole-5-carboxylic acid ethyl ester (0.1 mmol) is dissolved in 2-propanol (10 ml) and hydrazine (0.11 mmol) is added. The resulting mixture is heated at 80° C., while monitoring the reaction progress by TLC. Once the reaction is completed (the starting material is no longer detected), the solvents are evaporated under reduced pressure, dioxane (20 ml) is added to the crude mixture, followed by addition of ethyl 4-bromobutyrate (0.1 mmol) and triethylamine (0.1 mmol), and the resulting mixture is heated to reflux, while monitoring the reaction progress by TLC. Once the reaction is completed (the starting material is no longer detected), the solvent is evaporated, and a mixture of ethyl acetate and water is added. The phases are separated, and the aqueous phase is extracted with ethyl acetate. The combined organic phase is dried over Na2SO4, and the solvents are evaporated under reduced pressure to give crude 4-{N′-[2-(4-Nitro-phenyl)-4H-furo[3,2-b]pyrrole-5-carbonyl]-hydrazino}-butyric acid ethyl ester which is purified by column chromatography.

后处理

  1. customare evaporated under reduced pressure, dioxane (20 ml)
  2. additionis added to the crude mixture
  3. temperaturethe resulting mixture is heated
  4. temperatureto reflux
  5. customis evaporated
  6. additiona mixture of ethyl acetate and water
  7. additionis added
  8. customThe phases are separated
  9. extractionthe aqueous phase is extracted with ethyl acetate
  10. dry with materialThe combined organic phase is dried over Na2SO4
  11. customthe solvents are evaporated under reduced pressure

来源与证据

ORD记录
ord-970caa5248cd4993a821dc3b97c61455
来源数据集
uspto-grants-2010_09
专利号
US07795255B2

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