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Acetic Acid → 3-[2-(5-isopropylaminosulfonyl-2-oxo-1,2-dihydroindol-3-ylidenemethyl)-4,5,6,7-tetrahydro-1H-indol-3-yl]-propionic acid

HRID 24523
Notes
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Reaction equation

HRID 24523 reaction equation
[CH:1]([C:3]1[NH:4][C:5]2[CH2:6][CH2:7][CH2:8][CH2:9][C:10]=2[C:11]=1[CH:12]([CH3:16])C(O)=O)=O.[CH:17]([NH:20][S:21]([C:24]1[CH:25]=[C:26]2[C:30](=[CH:31][CH:32]=1)[NH:29][C:28](=[O:33])[CH2:27]2)(=[O:23])=[O:22])([CH3:19])[CH3:18].N1CCCCC1.[C:40]([OH:43])(=[O:42])C>C(O)C>[CH:17]([NH:20][S:21]([C:24]1[CH:25]=[C:26]2[C:30](=[CH:31][CH:32]=1)[NH:29][C:28](=[O:33])[C:27]2=[CH:1][C:3]1[NH:4][C:5]2[CH2:6][CH2:7][CH2:8][CH2:9][C:10]=2[C:11]=1[CH2:12][CH2:16][C:40]([OH:43])=[O:42])(=[O:23])=[O:22])([CH3:19])[CH3:18]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 8082PiperidineHCID 219156105-Isopropylaminosulfonyl-2-oxindoleHCID 22571120(2-Formyl-4,5,6,7-tetrahydro-1H-indol-3-yl)-propionic acid

Product 1

HCID 697650683-[2-(5-isopropylaminosulfonyl-2-oxo-1,2-dihydroindol-3-ylidenemethyl)-4,5,6,7-tetrahydro-1H-indol-3-yl]-propionic acidYield 80%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of (2-Formyl-4,5,6,7-tetrahydro-1H-indol-3-yl)-propionic acid (5.4 g), 5.7 g of 5-isopropylaminosulfonyl-2-oxindole and 2.7 g of piperidine in 25 mL of ethanol was refluxed for 4 hours. Upon addition of acetic acid (8 mL), a precipitate formed. The mixture was refluxed for 5 minutes and cooled to ambient temperature. The precipitate was collected by vacuum filtration and washed with 20 mL of ethanol. The solids were slurry-washed in 30 mL of reflushing ethanol, cooled, collected by vacuum filtration, washed with 30 mL of ethanol and vacuum dried to give 8.1 g (80% yield) of 3-[2-(5-isopropylaminosulfonyl-2-oxo-1,2-dihydroindol-3-ylidenemethyl)-4,5,6,7-tetrahydro-1H-indol-3-yl]-propionic acid as an orange solid.

Workup

  1. temperaturewas refluxed for 4 hours
  2. customa precipitate formed
  3. temperatureThe mixture was refluxed for 5 minutes
  4. filtrationThe precipitate was collected by vacuum filtration
  5. washwashed with 20 mL of ethanol
  6. washThe solids were slurry-washed in 30 mL of reflushing ethanol
  7. temperaturecooled
  8. filtrationcollected by vacuum filtration
  9. washwashed with 30 mL of ethanol and vacuum
  10. customdried

Sources & evidence

ORD record
ord-138332c436e545ea902322b6f6ee39a1
Source dataset
uspto-grants-2005_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06855730B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes