Ethyl Acetate → HCID 68504957, compound

HRID 217267Notes

Reaction equation

HRID 217267 reaction equation
[NH2:1][C:2]1[CH:6]=[C:5]([C:7]2[CH:12]=[CH:11][C:10]([Br:13])=[CH:9][CH:8]=2)[S:4][C:3]=1C(O)=O.CN1CCNCC1.CN1CCCC1=O.CCOC(C)=O>O>[Br:13][C:10]1[CH:9]=[CH:8][C:7]([C:5]2[S:4][CH:3]=[C:2]([NH2:1])[CH:6]=2)=[CH:12][CH:11]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 13387N-methyl-2-pyrrolidoneHCID 531671-MethylpiperazineHCID 534434553-Amino-5-(4-bromophenyl)thiophene-2-carboxylic acid

Product 1

HCID 68504957HCID 68504957, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
160 °C

Procedure

3-amino-5-(4-bromophenyl)thiophene-2-carboxylic acid (11.21 mmol), N-methyl piperazine (11.21 mmol) and N-methylpyrrolidinone (13.5 mL) were mixed together The reaction mixture was stirred at 160° C. for 5 hours and cooled down to room temperature. EtOAc and water were added, organics were separated, dried over Na2SO4, concentrated under reduced pressure and filtrated over silica (DCM/MeOH). Diisopropyl ether was added to the crude material and the residue obtained was filtered to give Intermediate IX.1 as a beige solid in 44% yield, which was characterized by the following spectroscopic data: MS (ESI, EI+) m/z=255 (MH+).

Workup

  1. temperaturecooled down to room temperature
  2. customorganics were separated
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. filtrationfiltrated over silica (DCM/MeOH)
  6. additionDiisopropyl ether was added to the crude material
  7. customthe residue obtained
  8. filtrationwas filtered
  9. customto give Intermediate IX.1 as a beige solid in 44% yield, which

Sources & evidence

ORD record
ord-f5faa2ebe2b840d1a9f5e818eefa61b3
Source dataset
uspto-grants-2012_06
Patent number
US08193372B2

Reaction notes

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