Piperidine → 2-Oxo-3-(4-oxo-4,5,6,7-tetrahydro-2H-pyrrolo[3,4-c]pyridin-1-ylmethylene)-2,3-dihydro-1H-indole-5-sulfonic acid methylamide

HRID 991846Notes

Reaction equation

HRID 991846 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].[O:16]=[C:17]1[C:22]2=[CH:23][NH:24][C:25]([CH:26]=O)=[C:21]2[CH2:20][CH2:19][NH:18]1.N1CCCCC1>C(O)C>[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])[C:9]2=[CH:26][C:25]1[NH:24][CH:23]=[C:22]2[C:21]=1[CH2:20][CH2:19][NH:18][C:17]2=[O:16])(=[O:5])=[O:4]

Participants

5

Reactant 3

HCID 8082PiperidineHCID 99641894-oxo-4,5,6,7-tetrahydro-2H-pyrrolo[3,4-c]pyridine-1-carbaldehydeHCID 10176909N-methyl-2-oxoindoline-5-sulfonamide

Product 1

HCID 697079232-Oxo-3-(4-oxo-4,5,6,7-tetrahydro-2H-pyrrolo[3,4-c]pyridin-1-ylmethylene)-2,3-dihydro-1H-indole-5-sulfonic acid methylamideYield 45%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 2-oxo-2,3-dihydro-1H-indole-5-sulfonic acid methylamide (66 mg, 0.3 mmol), 4-oxo-4,5,6,7-tetrahydro-2H-pyrrolo[3,4-c]pyridine-1-carbaldehyde (50 mg, 0.3 mmol) and 0.1 mL of piperidine in ethanol (1 mL) was heated in a sealed tube at 80° C. for 4 hours. The precipitate was collected by vacuum filtration, washed with cold ethanol and dried to give 50 mg (45%) of the title compound.

Workup

  1. filtrationThe precipitate was collected by vacuum filtration
  2. washwashed with cold ethanol
  3. customdried

Sources & evidence

ORD record
ord-a013bda7d99c4d78ad5bc214e92162a4
Source dataset
uspto-grants-2002_10
Patent number
US06465507B2

Reaction notes

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