1,3-Cyclohexanedione → HCID 178470349, compound

HRID 1696677Notes

Reaction equation

HRID 1696677 reaction equation
[NH2:1][C:2]1[CH:6]=[CH:5][NH:4][C:3]=1[C:7]([O:9][CH2:10][CH3:11])=[O:8].[F:12][C:13]1[CH:29]=[CH:28][C:16]2[NH:17][C:18]([S:20][C:21]3[O:25][C:24]([CH:26]=O)=[CH:23][CH:22]=3)=[N:19][C:15]=2[CH:14]=1.[C:30]1(=O)[CH2:35][CH2:34][CH2:33][C:32](=[O:36])[CH2:31]1>C(O)CCC>[CH2:10]([O:9][C:7]([C:3]1[NH:4][CH:5]=[C:6]2[CH:26]([C:24]3[O:25][C:21]([S:20][C:18]4[NH:17][C:16]5[CH:28]=[CH:29][C:13]([F:12])=[CH:14][C:15]=5[N:19]=4)=[CH:22][CH:23]=3)[C:31]3[C:32](=[O:36])[CH2:33][CH2:34][CH2:35][C:30]=3[NH:1][C:2]=12)=[O:8])[CH3:11]

Participants

5

Reactant 3

HCID 104341,3-CyclohexanedioneHCID 2773439Ethyl 3-amino-1H-pyrrole-2-carboxylateHCID 178519731HCID 178519731, compound

Product 1

HCID 178470349HCID 178470349, compoundYield 50.4%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A mixture of 3-amino-2-ethoxycarbonyl-pyrrole (0.235 g, 1.52 mmol), 5-(5-fluoro-1H-benzoimidazol-2-ylsulfanyl)-furan-2-carbaldehyde (0.40 g, 1.52 mmol) and 1,3-cyclohexanedione (0.171 g, 1.52 mmol) in 5 ml of 1-butanol is heated at reflux temperature for 2 hours. The reaction mixture is then concentrated under reduced pressure. The residue is resuspended in 5 ml of acetonitrile and the mixture is heated at reflux temperature for 30 minutes. The mixture is allowed to cool to room temperature and the insoluble material is collected by filtration, washed with diisopropylether (20 ml), pentane (20 ml) and dried under vacuum to yield 377 mg of 9-[5-(5-fluoro-1H-benzimidazol-2-ylsulfanyl)-furan-2-yl]-8-oxo-4,5,6,7,8,9-hexahydro-2H-pyrrolo[3,4-b]quinoline-3-carboxylic acid ethyl ester as a white powder. Yield=50%. Analytical LC/MS (method B): m/z=491 (negative ion mode, [M−H]−), m/z=493 (positive ion mode [M+H]+).

Workup

  1. temperatureis heated
  2. temperatureat reflux temperature for 2 hours
  3. concentrationThe reaction mixture is then concentrated under reduced pressure
  4. temperaturethe mixture is heated
  5. temperatureat reflux temperature for 30 minutes
  6. filtrationthe insoluble material is collected by filtration
  7. washwashed with diisopropylether (20 ml), pentane (20 ml)
  8. customdried under vacuum

Sources & evidence

ORD record
ord-8965c1aea97d425ea402555817a3219d
Source dataset
uspto-grants-2012_04
Patent number
US08163768B2

Reaction notes

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