N-methyl-2-oxoindoline-5-sulfonamide → HCID 67282724, compound

HRID 1246166Notes

Reaction equation

HRID 1246166 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].[CH2:16]([O:18][C:19](=[O:32])[CH2:20][NH:21][C:22]([C:24]1[C:28]([CH3:29])=[C:27]([CH:30]=O)[NH:26][CH:25]=1)=[O:23])[CH3:17]>N1CCCCC1.C(O)C>[CH2:16]([O:18][C:19](=[O:32])[CH2:20][NH:21][C:22]([C:24]1[C:28]([CH3:29])=[C:27]([CH:30]=[C:9]2[C:8]3[C:12](=[CH:13][CH:14]=[C:6]([S:3](=[O:5])(=[O:4])[NH:2][CH3:1])[CH:7]=3)[NH:11][C:10]2=[O:15])[NH:26][CH:25]=1)=[O:23])[CH3:17]

Participants

5

Reactant 2

HCID 10176909N-methyl-2-oxoindoline-5-sulfonamideHCID 85786887HCID 85786887, compound

Product 1

HCID 67282724HCID 67282724, compoundYield 36%

Reagents, catalysts & solvents 2

HCID 8082PiperidineCatalystHCID 702EthanolSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 5-methylaminosulfonyl-2-oxindole (0.06 g, 0.22 mmol), [(5-formyl-4-methyl-1H-pyrrole-3-carbonyl)-amino]-acetic acid ethyl ester (0.075 g, 0.27 mmol) and piperidine (2 drops) in ethanol (5 mL) was heated in a sealed tube at 90° C. for 12 hrs. After cooling, the precipitate was collected by vacuum filtration, washed with ethanol, triturated with dichloromethane/ether and dried to give 0.035 g (36%) of the title compound as a yellowish brown solid.

Workup

  1. temperatureAfter cooling
  2. filtrationthe precipitate was collected by vacuum filtration
  3. washwashed with ethanol
  4. customtriturated with dichloromethane/ether
  5. customdried

Sources & evidence

ORD record
ord-a20659bcda26467aa882599df66a92e1
Source dataset
uspto-grants-2006_10
Patent number
US07125905B2

Reaction notes

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