Piperidine → HCID 67282350, compound

HRID 1815349Notes

Reaction equation

HRID 1815349 reaction equation
C([O:3][C:4](=[O:17])[CH2:5][NH:6][C:7]([C:9]1[C:13]([CH3:14])=[C:12]([CH:15]=O)[NH:11][CH:10]=1)=[O:8])C.[OH-].[Na+].[CH3:20][NH:21][S:22]([C:25]1[CH:26]=[C:27]2[C:31](=[CH:32][CH:33]=1)[NH:30][C:29](=[O:34])[CH2:28]2)(=[O:24])=[O:23].N1CCCCC1>CO.C(O)C>[CH3:14][C:13]1[C:9]([C:7]([NH:6][CH2:5][C:4]([OH:3])=[O:17])=[O:8])=[CH:10][NH:11][C:12]=1[CH:15]=[C:28]1[C:27]2[C:31](=[CH:32][CH:33]=[C:25]([S:22](=[O:23])(=[O:24])[NH:21][CH3:20])[CH:26]=2)[NH:30][C:29]1=[O:34]

Participants

7

Reactant 4

HCID 8082PiperidineHCID 14798Sodium HydroxideHCID 10176909N-methyl-2-oxoindoline-5-sulfonamideHCID 85786887HCID 85786887, compound

Product 1

HCID 67282350HCID 67282350, compoundYield 54.8%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 887MethanolSolvent

Procedure

A mixture of [(5-formyl-4-methyl-1H-pyrrole-3-carbonyl)-amino]-acetic acid ethyl ester (0.142 g, 0.59 mmol) and 1N NaOH (1.2 mL) in methanol (10 mL) was stirred at room temperature for 1 hr. The reaction was concentrated and the residue was condensed with 5-methylaminosulfonyl-2-oxindole (0.13 g, 0.48 mmol) and piperidine (0.12 mL) in ethanol (12 mL) to give 0.11 g (52%) of the title compound.

Workup

  1. concentrationThe reaction was concentrated

Sources & evidence

ORD record
ord-d32e4a62980343fa9b3d391437d8f404
Source dataset
uspto-grants-2005_04
Patent number
US06878733B1

Reaction notes

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