Ethyl Acetate → HCID 89496150, compound

HRID 476215Notes

Reaction equation

HRID 476215 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])/[C:5]/2=[CH:12]\[C:13]1[NH:17][C:16]([CH3:18])=[C:15]([NH:19][C:20](=[O:24])[CH2:21][CH2:22]Br)[C:14]=1[CH3:25].[CH2:26]([N:28]1[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]1)[CH3:27].C(OCC)(=O)C>CN(C=O)C>[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])/[C:5]/2=[CH:12]\[C:13]1[NH:17][C:16]([CH3:18])=[C:15]([NH:19][C:20](=[O:24])[CH2:21][CH2:22][N:31]2[CH2:32][CH2:33][N:28]([CH2:26][CH3:27])[CH2:29][CH2:30]2)[C:14]=1[CH3:25]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 791961-EthylpiperazineHCID 89496102HCID 89496102, compound

Product 1

HCID 89496150HCID 89496150, compoundYield 32%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N-{5-[5-fluoro-2-oxo-1,2-dihydro-indol-(3Z)-ylidenemethyl]-2,4-dimethyl-1H-pyrrol-3-yl}-3-bromo-propionamide (548 mg, 1.0 eq) was dissolved in 4 ml of DMF, stirred at room temperature to obtain a solution. To the solution was added 4-ethylpiperazine (850 mg, 4.0 eq). The reaction mixture was heated to 50° C. and reacted for 4 h. Once the reaction was completed as indicated by TLC, the reaction solution was added to 200 ml of ethyl acetate. Solid product was formed, collected by filtration, washed with ethyl acetate, dried, and purified by column chromatograph to obtain the target compound of 312 mg (yield 32%).

Workup

  1. customto obtain a solution
  2. temperatureThe reaction mixture was heated to 50° C.
  3. customreacted for 4 h
  4. customSolid product was formed
  5. filtrationcollected by filtration
  6. washwashed with ethyl acetate
  7. customdried
  8. custompurified by column chromatograph
  9. customto obtain the target compound of 312 mg (yield 32%)

Sources & evidence

ORD record
ord-1d1038d22a0f4008b005b4e486c6cfd8
Source dataset
uspto-grants-2014_01
Patent number
US08637681B2

Reaction notes

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