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N-methyl-2-oxoindoline-5-sulfonamide → 2-Methyl-6-[5-methylsulfamoyl-2-oxo-1,2-dihydro-indol-(3Z)-ylidene]-1,4,5,6-tetrahydro-cyclopenta[b]pyrrole-3-carboxylic acid

HRID 2213561
Notes
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Reaction equation

HRID 2213561 reaction equation
[CH3:1][NH:2][S:3]([C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[NH:11][C:10](=[O:15])[CH2:9]2)(=[O:5])=[O:4].[CH3:16][C:17]1[NH:21][C:20]2[C:22](=O)[CH2:23][CH2:24][C:19]=2[C:18]=1[C:26]([OH:28])=[O:27]>CN(C=O)C.N1CCCCC1>[CH3:16][C:17]1[NH:21][C:20]2/[C:22](=[C:9]3\[C:10](=[O:15])[NH:11][C:12]4[C:8]\3=[CH:7][C:6]([S:3](=[O:5])(=[O:4])[NH:2][CH3:1])=[CH:14][CH:13]=4)/[CH2:23][CH2:24][C:19]=2[C:18]=1[C:26]([OH:28])=[O:27]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 10176909N-methyl-2-oxoindoline-5-sulfonamideHCID 219575932-Methyl-6-oxo-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-3-carboxylic acid

Product 1

HCID 210515372-Methyl-6-[5-methylsulfamoyl-2-oxo-1,2-dihydro-indol-(3Z)-ylidene]-1,4,5,6-tetrahydro-cyclopenta[b]pyrrole-3-carboxylic acidYield 24.5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent
HCID 8082
Piperidine
Solvent

Conditions

Temperature
110 °C

Procedure

A mixture of 2-oxo-2,3-dihydro-1H-indole-5-sulfonic acid methylamide (905 mg, 4 mmol) and 2-methyl-6-oxo-1,4,5,6-tetrahydro-cyclopenta[b]pyrrole-3-carboxylic acid (Example B, 716 mg, 4 mmol) in DMF (50 mL) and piperidine (5 mL) was heated at 110° C. with stirring for 48 hours. The solvent was removed and the residue was suspended in methanol-ice-water and acidified with 2N HCl. The solid was collected by filtration and then suspended in DCM. The suspension was washed with 2N aq. NaOH for three times. The combined water layer was backwashed with DCM. The water layer was acidified with 2N HCl and filtered to give a brown solid, which was triturated with MeOH to afford 380 mg of the titled compound as a brown yellow solid. The combined organic layer was dried (Na2SO4) and evaporated to give 130 mg of 3-[2-methyl-4,5-dihydro-1H-cyclopenta[b]pyrrol-(6Z)-ylidene]-2-oxo-2,3-dihydro-1H-indole-5-sulfonic acid methylamide (Example 4) as a yellow solid.

Workup

  1. customThe solvent was removed
  2. filtrationThe solid was collected by filtration
  3. washThe suspension was washed with 2N aq. NaOH for three times
  4. filtrationfiltered
  5. customto give a brown solid, which
  6. customwas triturated with MeOH

Sources & evidence

ORD record
ord-184decfbdf104ec3b6610892664e8f86
Source dataset
uspto-grants-2006_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07105562B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes