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

HRID 1970073

反応式

HRID 1970073 の反応式
[NH2:1][C:2]([NH2:4])=[S:3].Br[CH2:6][C:7]([C:9]1[CH:18]=[CH:17][C:16]2[NH:15][C:14](=[O:19])[C:13]3[NH:20][CH:21]=[CH:22][C:12]=3[C:11]=2[CH:10]=1)=O.[CH2:23]([C:25]([O-:27])=[O:26])[CH3:24].C(N(CC)CC)C>C(O)C>[NH2:1][C:2]1[S:3][CH:6]=[C:7]([C:9]2[CH:18]=[CH:17][C:16]3[NH:15][C:14](=[O:19])[C:13]4[NH:20][CH:21]=[CH:22][C:12]=4[C:11]=3[CH:10]=2)[N:4]=1.[CH2:23]([C:25]([O-:27])=[O:26])[CH3:24]

参加物

5

反応物 3

HCID 8471TriethylamineHCID 2723790ThioureaHCID 866275838-(2-bromo-acetyl)-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline 1-ethyl carboxylate

生成物 1

HCID 866275818-(2-amino-thiazol-4-yl)-4-oxo-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

17 mg (1.5 mmol) of thiourea 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 3 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, 9 mg (17%) of 8-(2-amino-thiazol-4-yl)-4-oxo-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-2a36d409b4ac487685d9e5ecde9ddaa5
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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