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1,3-Cyclohexanedione → 9-[2-(1H-benzimidazol-2-ylsulfanyl)-thiazol-5-yl]-8-oxo-4,5,6,7,8,9-hexahydro-2H-pyrrolo[3,4-b]quinoline-3-carboxylic acid ethyl ester

HRID 1696640
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HRID 1696640 반응식
[NH2:1][C:2]1[CH:6]=[CH:5][NH:4][C:3]=1[C:7]([O:9][CH2:10][CH3:11])=[O:8].[NH:12]1[C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=2[N:14]=[C:13]1[S:21][C:22]1[S:23][C:24]([CH:27]=O)=[CH:25][N:26]=1.[C:29]1(=O)[CH2:34][CH2:33][CH2:32][C:31](=[O:35])[CH2:30]1>C(O)CCC>[CH2:10]([O:9][C:7]([C:3]1[NH:4][CH:5]=[C:6]2[CH:27]([C:24]3[S:23][C:22]([S:21][C:13]4[NH:12][C:16]5[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=5[N:14]=4)=[N:26][CH:25]=3)[C:30]3[C:31](=[O:35])[CH2:32][CH2:33][CH2:34][C:29]=3[NH:1][C:2]=12)=[O:8])[CH3:11]
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참가 물질

5

반응물 3

HCID 104341,3-CyclohexanedioneHCID 2773439Ethyl 3-amino-1H-pyrrole-2-carboxylateHCID 598257462-(1H-benzimidazol-2-ylsulfanyl)-thiazole-5-carbaldehyde

생성물 1

HCID 598256709-[2-(1H-benzimidazol-2-ylsulfanyl)-thiazol-5-yl]-8-oxo-4,5,6,7,8,9-hexahydro-2H-pyrrolo[3,4-b]quinoline-3-carboxylic acid ethyl ester수율 31.8%

시약·촉매·용매 1

HCID 263
1-Butanol
용매

실험 절차

A suspension of 308.3 mg (2.0 mmol) of 3-amino-2-ethoxycarbonylpyrrole and 522.7 mg (2.0 mmol) of 2-(1H-benzimidazol-2-ylsulfanyl)-thiazole-5-carbaldehyde (obtained from step 1) in 10 mL of n-butanol under argon is stirred at room temperature for 0.5 hour. 1,3-Cyclohexanedione (224.3 mg, 2.0 mmol) is then added and the reaction mixture is heated at reflux temperature for 2 h. The mixture is then cooled to room temperature and concentrated under reduced pressure. The residue is purified by chromatography on a prepacked 70 g 15-40 μm silica gel cartridge (eluting solvent: ethyl acetate; rate: 40 mL/min). The fractions containing the desired product are combined and concentrated to dryness under reduced pressure. The residue is triturated in ethanol, filtered, washed with diethylether and dried under reduced pressure. 313 mg of 9-[2-(1H-benzimidazol-2-ylsulfanyl)-thiazol-5-yl]-8-oxo-4,5,6,7,8,9-hexahydro-2H-pyrrolo[3,4-b]quinoline-3-carboxylic acid ethyl ester are obtained as a yellow powder. mp: 194° C. LCMS: m/z 492: [M+H]+ (base peak); m/z 490: [M−H]− (base peak).

후처리

  1. temperaturethe reaction mixture is heated
  2. temperatureat reflux temperature for 2 h
  3. temperatureThe mixture is then cooled to room temperature
  4. concentrationconcentrated under reduced pressure
  5. customThe residue is purified by chromatography on a prepacked 70 g 15-40 μm silica gel cartridge (eluting solvent: ethyl acetate; rate: 40 mL/min)
  6. additionThe fractions containing the desired product
  7. concentrationconcentrated to dryness under reduced pressure
  8. customThe residue is triturated in ethanol
  9. filtrationfiltered
  10. washwashed with diethylether
  11. customdried under reduced pressure

출처 및 근거

ORD 기록
ord-4922f299ea50433890bda023df69416e
출처 데이터셋
uspto-grants-2012_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08163768B2

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