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

HRID 1970074

反応式

HRID 1970074 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

反応条件

温度
90 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-57d4c5874a3e47b785455dd384764b16
出典データセット
uspto-grants-2013_04
特許番号
US08426437B2

関連ノート

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