Piperidine → HCID 54514641, compound

HRID 1937560Notes

Reaction equation

HRID 1937560 reaction equation
[C:1]([CH2:4][CH2:5][C:6]1[C:7]([CH3:13])=[C:8]([CH:11]=O)[NH:9][CH:10]=1)([OH:3])=[O:2].[NH2:14][S:15]([C:18]1[CH:19]=[C:20]2[C:24](=[CH:25][CH:26]=1)[NH:23][C:22](=[O:27])[CH2:21]2)(=[O:17])=[O:16].N1CCCCC1>C(O)C>[CH3:13][C:7]1[C:6]([CH2:5][CH2:4][C:1]([OH:3])=[O:2])=[CH:10][NH:9][C:8]=1[CH:11]=[C:21]1[C:20]2[C:24](=[CH:25][CH:26]=[C:18]([S:15](=[O:17])(=[O:16])[NH2:14])[CH:19]=2)[NH:23][C:22]1=[O:27]

Participants

5

Reactant 3

HCID 8082PiperidineHCID 101982322-Oxoindoline-5-sulfonamideHCID 151607523-(5-formyl-4-methyl-1H-pyrrol-3-yl)propanoic acid

Product 1

HCID 54514641HCID 54514641, compoundYield 70.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4-(2-Carboxyethyl)-2-formyl-3-methylpyrrole (90.6 mg), 106 mg 5-aminosulfonyl-2-oxindole, and 75 μL piperidine in 2 mL of ethanol were heated at 95° C. for 5 hours. The reaction mixture was cooled and concentrated. The residue was suspended in 6 N aqueous hydrochloric acid. The precipitate was filtered, washed with water to pH 6 and dried in a vacuum oven to give 132 mg (70%)of the title compound as a yellow solid.

Workup

  1. temperatureThe reaction mixture was cooled
  2. concentrationconcentrated
  3. filtrationThe precipitate was filtered
  4. washwashed with water to pH 6
  5. customdried in a vacuum oven

Sources & evidence

ORD record
ord-32b9e1b85d054a9c9d30d0ca1bf00d5a
Source dataset
uspto-grants-2002_05
Patent number
US06395734B1

Reaction notes

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