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

HRID 1713052

반응식

HRID 1713052 반응식
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]

참가 물질

6

반응물 4

HCID 8471TriethylamineHCID 9321HydrazineHCID 76300Ethyl 4-bromobutyrateHCID 594634452-(4-nitro-phenyl)-4H-furo[3,2-b]pyrrole-5-carboxylic acid ethyl ester

생성물 1

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

시약·촉매·용매 1

HCID 3776Isopropanol용매

반응 조건

온도
80 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-970caa5248cd4993a821dc3b97c61455
출처 데이터셋
uspto-grants-2010_09
특허 번호
US07795255B2

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