Piperidine → 3-[5-(6-Chloro-2-oxo-1,2-dihydroindol-3-ylidenemethyl)-4-methyl-1H-pyrrol-3-yl]-propionic acid

HRID 1937554

Reaction equation

HRID 1937554 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].[Cl:14][C:15]1[CH:23]=[C:22]2[C:18]([CH2:19][C:20](=[O:24])[NH:21]2)=[CH:17][CH:16]=1.N1CCCCC1>C(O)C>[Cl:14][C:15]1[CH:23]=[C:22]2[C:18]([C:19](=[CH:11][C:8]3[NH:9][CH:10]=[C:6]([CH2:5][CH2:4][C:1]([OH:3])=[O:2])[C:7]=3[CH3:13])[C:20](=[O:24])[NH:21]2)=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 8082PiperidineHCID 7363446-Chloro-1,3-dihydroindol-2-oneHCID 151607523-(5-formyl-4-methyl-1H-pyrrol-3-yl)propanoic acid

Product 1

HCID 545243353-[5-(6-Chloro-2-oxo-1,2-dihydroindol-3-ylidenemethyl)-4-methyl-1H-pyrrol-3-yl]-propionic acidYield 74.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4-(2-Carboxyethyl)-2-formyl-3-methylpyrrole (200 mg), 167.6 mg 6-chloro-2-oxindole, and 166 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 246 mg (74%) of the title compound as a brown 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-0ba2ce982a4544f79e7ee8e1b9f2f851
Source dataset
uspto-grants-2002_05
Patent number
US06395734B1

Linked notes

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