Ethyl Acetate → HCID 178418796, compound

HRID 2219127Notes

Reaction equation

HRID 2219127 reaction equation
I[CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([NH:12][CH:13]=[C:14]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[NH:16][C:15]2=[O:23])=[CH:8][CH:7]=1.[CH3:24][N:25]1[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]1.CCOC(C)=O>C1COCC1>[CH3:24][N:25]1[CH2:30][CH2:29][N:28]([CH2:2][CH2:3][CH2:4][O:5][C:6]2[CH:11]=[CH:10][C:9]([NH:12][CH:13]=[C:14]3[C:22]4[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=4)[NH:16][C:15]3=[O:23])=[CH:8][CH:7]=2)[CH2:27][CH2:26]1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 531671-MethylpiperazineHCID 178418721HCID 178418721, compound

Product 1

HCID 178418796HCID 178418796, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

A solution of 3-{[4-(3-Iodo-propoxy)-phenylamino]-methylene}-1,3-dihydro-indol-2-one (66 mg, 0.157 mmol) in 1 mL THF is treated with 1-methylpiperazine (37.2 μL, 2.2 equiv.) and the resulting reaction mixture is heated at 50° C. for 4 h. The reaction mixture is cooled to room temperature and concentrated under reduced pressure. The residue is partitioned between EtOAc and H2O. The organic layer is collected and washed with saturated aqueous NaHCO3, brine, and dried over anhydrous Na2SO4. The yellow solid residue obtained upon evaporation is broken up in 1:9 EtOAc:hexane and collected by filtration to give the named compound as a yellow solid.

Workup

  1. customthe resulting reaction mixture
  2. temperatureThe reaction mixture is cooled to room temperature
  3. concentrationconcentrated under reduced pressure
  4. customThe residue is partitioned between EtOAc and H2O
  5. customThe organic layer is collected
  6. washwashed with saturated aqueous NaHCO3, brine
  7. dry with materialdried over anhydrous Na2SO4
  8. customThe yellow solid residue obtained upon evaporation
  9. filtrationhexane and collected by filtration

Sources & evidence

ORD record
ord-8abec5405a5f46e4b918640fd7cc8eda
Source dataset
uspto-grants-2008_08
Patent number
US07414054B2

Reaction notes

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