1,3-Cyclohexanedione → HCID 59825673, compound

HRID 1696623Notes

Reaction equation

HRID 1696623 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].[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[O:26][C:25]([CH:27]=O)=[CH:24][CH:23]=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:25]3[O:26][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)=[CH:23][CH:24]=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]

Participants

5

Reactant 3

HCID 104341,3-CyclohexanedioneHCID 6984275-[(1H-Benzimidazol-2-yl)sulfanyl]furan-2-carbaldehydeHCID 2773439Ethyl 3-amino-1H-pyrrole-2-carboxylate

Product 1

HCID 59825673HCID 59825673, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

Alternatively example 105 can be prepared by reacting 3-amino-2-ethoxycarbonyl-pyrrole (31.5 g, 204 mmol), 5-(1H-benzimidazol-2-ylsulfanyl)-furan-2-carbaldehyde (50 g, 204 mmol) and 1,3-cyclohexanedione (22.95 g 204 mmol) in 2.5 l of 1-butanol at reflux temperature for 3 hours. The reaction mixture is then concentrated under reduced pressure. The residue is resuspended in 1 l of ethanol and heated to reflux temperature for 2 hours and let to cool to room temperature. The formed insoluble material is collected by filtration, washed with ethanol (0.4 l), diisopropyl ether (0.4 l), pentane (0.4 l) and dried under vacuum. The residue is resuspended in 2 l of acetonitrile, heated to reflux temperature for 2 hours and let to cool to room temperature. The insoluble material is collected by filtration, washed with acetonitrile (0.6 l), diisopropyl ether (0.6 l), pentane (0.6 l) and dried under vacuum to yield 41.5 g of 9-[5-(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 in the base form as a light gray powder. Yield=43%. Analytical LC/MS method B: retention time=3.32 min. m/z=475.06 (positive ion mode).

Workup

  1. customAlternatively example 105 can be prepared
  2. temperatureat reflux temperature for 3 hours
  3. concentrationThe reaction mixture is then concentrated under reduced pressure
  4. temperatureheated
  5. temperatureto reflux temperature for 2 hours
  6. filtrationThe formed insoluble material is collected by filtration
  7. washwashed with ethanol (0.4 l), diisopropyl ether (0.4 l), pentane (0.4 l)
  8. customdried under vacuum
  9. temperatureheated
  10. temperatureto reflux temperature for 2 hours
  11. temperatureto cool to room temperature
  12. filtrationThe insoluble material is collected by filtration
  13. washwashed with acetonitrile (0.6 l), diisopropyl ether (0.6 l), pentane (0.6 l)
  14. customdried under vacuum

Sources & evidence

ORD record
ord-47cd1f5c61e843988db369186a0390a7
Source dataset
uspto-grants-2012_04
Patent number
US08163768B2

Reaction notes

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