1,3-Cyclohexanedione → HCID 59825691, compound

HRID 1696661Notes

Reaction equation

HRID 1696661 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].[Cl:12][C:13]1[C:29]([CH3:30])=[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:31]1(=O)[CH2:36][CH2:35][CH2:34][C:33](=[O:37])[CH2:32]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]=[C:29]([CH3:30])[C:13]([Cl:12])=[CH:14][C:15]=5[N:19]=4)=[CH:22][CH:23]=3)[C:32]3[C:33](=[O:37])[CH2:34][CH2:35][CH2:36][C:31]=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 86623883HCID 86623883, compound

Product 1

HCID 59825691HCID 59825691, compoundYield 11%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A mixture of 3-amino-2-ethoxycarbonyl-pyrrole (0.204 g, 1.32 mmol), 5-(5-chloro-6-methyl-1H-benzimidazol-2-ylsulfanyl)-furan-2-carbaldehyde (0.388 g, 1.32 mmol) and 1,3-cyclohexanedione (0.149 g, 1.32 mmol) in 10 ml of 1-butanol is heated at reflux temperature for 4 h. The reaction mixture is then concentrated under reduced pressure and purified on a silica gel column (34 g) eluted with a mixture of cyclohexane and ethylacetate (7/3, v/v). The fractions containing the expected product are concentrated under reduced pressure, and the residue is resuspended in 5 ml of acetonitrile and heated at reflux temperature for 15 minutes. After cooling to room temperature, the insoluble material is collected by filtration and dried under vacuum to yield 76 mg of 9-[5-(5-chloro-6-methyl-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. Yield=11%. Analytical LC/MS (method B): m/z=523 (positive ion mode, [M+H]+, 1 Cl present), m/z=521 (negative ion mode, [M−H]−, 1 Cl present).

Workup

  1. temperatureis heated
  2. temperatureat reflux temperature for 4 h
  3. concentrationThe reaction mixture is then concentrated under reduced pressure
  4. custompurified on a silica gel column (34 g)
  5. washeluted with a mixture of cyclohexane and ethylacetate (7/3
  6. additionThe fractions containing the expected product
  7. concentrationare concentrated under reduced pressure
  8. temperatureheated
  9. temperatureat reflux temperature for 15 minutes
  10. filtrationthe insoluble material is collected by filtration
  11. customdried under vacuum

Sources & evidence

ORD record
ord-2e237a6f9eb849a2a066fa30fca09ee6
Source dataset
uspto-grants-2012_04
Patent number
US08163768B2

Reaction notes

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