Triethylamine → 5-Bromo-N-[4-methoxy-3-(4-methyl-1-piperazinyl)phenyl]furan-3-carboxamide

HRID 355733Notes

Reaction equation

HRID 355733 reaction equation
[Br:1][C:2]1[O:6][CH:5]=[C:4]([C:7]([OH:9])=O)[CH:3]=1.C(N(CC)CC)C.[CH3:17][O:18][C:19]1[CH:24]=[CH:23][C:22]([NH2:25])=[CH:21][C:20]=1[N:26]1[CH2:31][CH2:30][N:29]([CH3:32])[CH2:28][CH2:27]1>S(Cl)(Cl)=O>[Br:1][C:2]1[O:6][CH:5]=[C:4]([C:7]([NH:25][C:22]2[CH:23]=[CH:24][C:19]([O:18][CH3:17])=[C:20]([N:26]3[CH2:27][CH2:28][N:29]([CH3:32])[CH2:30][CH2:31]3)[CH:21]=2)=[O:9])[CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 103311014-Methoxy-3-(4-methylpiperazin-1-yl)anilineHCID 133335605-Bromofuran-3-carboxylic acid

Product 1

HCID 189406665-Bromo-N-[4-methoxy-3-(4-methyl-1-piperazinyl)phenyl]furan-3-carboxamide

Reagents, catalysts & solvents 1

HCID 24386Thionyl ChlorideSolvent

Procedure

5-Bromo-3-furancarboxylic acid (0.302;1.58 mmol) was heated at reflux in thionyl chloride (8 ml) for 30 minutes, cooled, evaporated in vacuo and the residue azeotroped with toluene. The residue was redissolved in CH2Cl2 (10 ml) and treated with dry triethylamine (0.22 ml; 1.58 mmol) and 4-methoxy-3-(4-methyl-1-piperazinyl)benzenamine (0.35 g;1.58 mmol). The solution was stirred under Ar (18 hours), evaporated in vacuo and partitioned satd. K2CO3 (aq)/EtOAc. The organic phases were combined, dried over Na2SO4, filtered and the filtrate evaporated in vacuo to a brown gum. The gum was purified by flash silica-gel chromatography and eluted with 3%MeOH/CHCl3 to yield the title compound as a tan solid after trituration with Et2O (0.3 g;48%), mp=185°-187° C.

Workup

  1. temperaturecooled
  2. customevaporated in vacuo
  3. customthe residue azeotroped with toluene
  4. dissolutionThe residue was redissolved in CH2Cl2 (10 ml)
  5. customevaporated in vacuo
  6. custompartitioned
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. customthe filtrate evaporated in vacuo to a brown gum
  10. customThe gum was purified by flash silica-gel chromatography
  11. washeluted with 3%MeOH/CHCl3

Sources & evidence

ORD record
ord-eb50bdd87df64043a04d22ee97836a89
Source dataset
uspto-grants-1998_11
Patent number
US05834471

Reaction notes

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