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

HRID 1243493Notes

Reaction equation

HRID 1243493 reaction equation
[C:1]([CH2:4][CH2:5][C:6]1[C:10]([CH3:11])=[C:9]([CH:12]=O)[NH:8][C:7]=1[CH3:14])([OH:3])=[O:2].[N:15]1([C:21]2[CH:29]=[C:28]3[C:24]([CH2:25][C:26](=[O:30])[NH:27]3)=[CH:23][CH:22]=2)[CH2:20][CH2:19][O:18][CH2:17][CH2:16]1.N1CCCCC1>C(O)C>[CH3:14][C:7]1[NH:8][C:9]([CH:12]=[C:25]2[C:24]3[C:28](=[CH:29][C:21]([N:15]4[CH2:20][CH2:19][O:18][CH2:17][CH2:16]4)=[CH:22][CH:23]=3)[NH:27][C:26]2=[O:30])=[C:10]([CH3:11])[C:6]=1[CH2:5][CH2:4][C:1]([OH:3])=[O:2]

Participants

5

Reactant 3

HCID 8082PiperidineHCID 15125203-(5-formyl-2,4-dimethyl-1H-pyrrol-3-yl)propanoic AcidHCID 219256916-(Morpholin-4-yl)-2-oxindole

Product 1

HCID 539779193-[2,4-Dimethyl-5-(6-morpholin-4-yl-2-oxo-1,2-dihydroindol-3-ylidenemethyl)-1H-pyrrol-3-yl]-propionic acidYield 41.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3-(2-Carboxyethyl)-2,4-dimethyl-5-formylpyrrole (3.3 g), 4 g 6-(morpholin-4-yl)-2-oxindole and 1.8 mL piperidine in 60 mL of ethanol were heated at 90° C. for 7 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 overnight. The resulting solid was purified by chromatography on a silica gel column eluting with ethyl acetate-hexane-acetic acid to give 2.78 g (38% yield) 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 overnight
  6. customThe resulting solid was purified by chromatography on a silica gel column
  7. washeluting with ethyl acetate-hexane-acetic acid

Sources & evidence

ORD record
ord-56c6499c9ed34abdba1a4e57f43081bf
Source dataset
uspto-grants-2006_10
Patent number
US07119090B2

Reaction notes

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