3-(5-formyl-2,4-dimethyl-1H-pyrrol-3-yl)propanoic Acid → HCID 69032833, compound

HRID 1937608Notes

Reaction equation

HRID 1937608 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].[CH3:15][O:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[C:23]1[CH:31]=[C:30]2[C:26]([CH2:27][C:28](=[O:32])[NH:29]2)=[CH:25][CH:24]=1>N1CCCCC1.C(O)C>[CH3:15][O:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[C:23]1[CH:31]=[C:30]2[C:26]([C:27](=[CH:12][C:9]3[NH:8][C:7]([CH3:14])=[C:6]([CH2:5][CH2:4][C:1]([OH:3])=[O:2])[C:10]=3[CH3:11])[C:28](=[O:32])[NH:29]2)=[CH:25][CH:24]=1

Participants

5

Reactant 2

HCID 15125203-(5-formyl-2,4-dimethyl-1H-pyrrol-3-yl)propanoic AcidHCID 105619756-(2-Methoxyphenyl)-1,3-dihydroindol-2-one

Product 1

HCID 69032833HCID 69032833, compoundYield 44%

Reagents, catalysts & solvents 2

HCID 8082PiperidineCatalystHCID 702EthanolSolvent

Procedure

3-(2-Carboxyethyl)-2,4-dimethyl-5-formylpyrrole (234 mg), 239 mg 6-(2-methoxyphenyl)-2-oxindole and 3 drops piperidine in 2 mL of ethanol were heated at 90° C. overnight. 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 crude solid was purified by chromatography on a silica gel column eluting with ethyl acetate:hexane 1:1 containing 0.1% acetic acid to give 182 mg (44%) 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 crude solid was purified by chromatography on a silica gel column
  7. washeluting with ethyl acetate:hexane 1:1 containing 0.1% acetic acid

Sources & evidence

ORD record
ord-857806d948494195b693ba12894e489f
Source dataset
uspto-grants-2002_05
Patent number
US06395734B1

Reaction notes

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