Dimedone → HCID 12000661, compound

HRID 1696624Notes

Reaction equation

HRID 1696624 reaction equation
[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[S:10][C:11]1[O:15][C:14]([CH:16]=O)=[CH:13][CH:12]=1.[CH3:18][C:19]1([CH3:27])[CH2:26][C:24](=O)[CH2:23][C:21](=[O:22])[CH2:20]1.Cl.[NH2:29][C:30]1[CH:34]=[CH:33][NH:32][C:31]=1[C:35]([O:37][CH2:38][CH3:39])=[O:36].C(N(CC)C(C)C)(C)C>C(O)C.ClCCl>[CH2:38]([O:37][C:35]([C:31]1[NH:32][CH:33]=[C:34]2[CH:16]([C:14]3[O:15][C:11]([S:10][C:2]4[NH:1][C:5]5[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=5[N:3]=4)=[CH:12][CH:13]=3)[C:23]3[C:21](=[O:22])[CH2:20][C:19]([CH3:18])([CH3:27])[CH2:26][C:24]=3[NH:29][C:30]=12)=[O:36])[CH3:39]

Participants

7

Reactant 4

HCID 31358DimedoneHCID 81531DiisopropylethylamineHCID 6984275-[(1H-Benzimidazol-2-yl)sulfanyl]furan-2-carbaldehydeHCID 164270913-Amino-2-ethoxycarbonylpyrrole hydrochloride

Product 1

HCID 12000661HCID 12000661, compoundYield 47%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

430 mg (1.76 mmol) of 5-(1H-benzimidazol-2-ylsulfanyl)-furan-2-carbaldehyde are combined to 197 mg (1.405 mmol) of dimedone, 335 mg (1.76 mmol) of 3-amino-2-ethoxycarbonylpyrrole hydrochloride, 742 mg (5.741 mmol) of N,N-diisopropylethylamine in 10 ml ethanol. The stirred reaction mixture is refluxed overnight. Upon cooling to room temperature, reaction mixture was half concentrated under reduced pressure and then diluted with water and extracted with ethyl acetate. The organic layer is washed with water and with brine and then dried on magnesium sulfate, filtered and concentrated under reduced pressure giving crude product. The resulting oily residue is dissolved in 10 ml of dichloromethane and purified by chromatography on a prepacked 120 g 15-40 μm silica gel cartridge (eluting solvent: cyclohexane/ethyl acetate from 100/0 to 70/30 v/v; rate: 50 mL/min, in 50 min, from 70/30 to 50/50 v/v in 10 min, and then from 50/50 to 40/60 v/v in 30 min). The fractions containing the desired product are combined and concentrated to dryness under reduced pressure giving 330 mg of expected compound with 47% yield.

Workup

  1. customThe stirred reaction mixture
  2. temperatureis refluxed overnight
  3. customreaction mixture
  4. concentrationconcentrated under reduced pressure
  5. additiondiluted with water
  6. extractionextracted with ethyl acetate
  7. washThe organic layer is washed with water and with brine
  8. customdried on magnesium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated under reduced pressure
  11. customgiving crude product
  12. custompurified by chromatography on a prepacked 120 g 15-40 μm silica gel cartridge (
  13. washeluting solvent
  14. waitfrom 70/30 to 50/50 v/v in 10 min
  15. waitfrom 50/50 to 40/60 v/v in 30 min)
  16. additionThe fractions containing the desired product
  17. concentrationconcentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-bed45cd88806466e89cbfa949656fc21
Source dataset
uspto-grants-2012_04
Patent number
US08163768B2

Reaction notes

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