Triethylamine → 4-oxo-8-(2-phenylamino-thiazol-4-yl)-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline 1-ethyl carboxylate

HRID 1970074

반응식

HRID 1970074 반응식
[C:1]1([NH:7][C:8]([NH2:10])=[S:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[CH2:12][C:13]([C:15]1[CH:24]=[CH:23][C:22]2[NH:21][C:20](=[O:25])[C:19]3[NH:26][CH:27]=[CH:28][C:18]=3[C:17]=2[CH:16]=1)=O.[CH2:29]([C:31]([O-:33])=[O:32])[CH3:30].C(N(CC)CC)C>C(O)C>[O:25]=[C:20]1[C:19]2[NH:26][CH:27]=[CH:28][C:18]=2[C:17]2[CH:16]=[C:15]([C:13]3[N:10]=[C:8]([NH:7][C:1]4[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=4)[S:9][CH:12]=3)[CH:24]=[CH:23][C:22]=2[NH:21]1.[CH2:29]([C:31]([O-:33])=[O:32])[CH3:30]

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 676454PhenylthioureaHCID 866275838-(2-bromo-acetyl)-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline 1-ethyl carboxylate

생성물 1

HCID 866275854-oxo-8-(2-phenylamino-thiazol-4-yl)-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline 1-ethyl carboxylate수율 17%

시약·촉매·용매 1

HCID 702Ethanol용매

반응 조건

온도
90 °C

실험 절차

34 mg (1.5 mmol) of N-phenylthiourea is added to a suspension of 57 mg (0.15 mmol) of 8-(2-bromo-acetyl)-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline-1-ethyl carboxylate in 3 mL of ethanol. The mixture is stirred at 90° C. for 48 hours then the mixture is cooled to room temperature. Triethylamine (2 mmol) is added, then the solvent is evaporated and the product is purified by chromatography on silica (chloroform/methanol/triethylamine 8/2/1). After drying, 11 mg (17%) of 4-oxo-8-(2-phenylamino-thiazol-4-yl)-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline-1-ethyl carboxylate is obtained in the form of a beige solid.

후처리

  1. temperaturethe mixture is cooled to room temperature
  2. customthe solvent is evaporated
  3. customthe product is purified by chromatography on silica (chloroform/methanol/triethylamine 8/2/1)
  4. customAfter drying

출처 및 근거

ORD 기록
ord-57d4c5874a3e47b785455dd384764b16
출처 데이터셋
uspto-grants-2013_04
특허 번호
US08426437B2

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