Triethylamine → 5-Bromo-N-[4-methoxy-3-(4-methyl-1-piperazinyl)phenyl]furan-2-carboxamide

HRID 355732Notes

Reaction equation

HRID 355732 reaction equation
[Br:1][C:2]1[O:6][C:5]([C:7]([OH:9])=O)=[CH:4][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][C:5]([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:4][CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 685115-Bromo-2-furanecarboxylic acidHCID 103311014-Methoxy-3-(4-methylpiperazin-1-yl)aniline

Product 1

HCID 189406735-Bromo-N-[4-methoxy-3-(4-methyl-1-piperazinyl)phenyl]furan-2-carboxamideYield 86.4%

Reagents, catalysts & solvents 1

HCID 24386Thionyl ChlorideSolvent

Procedure

5-Bromofuroic acid (0.432;2.26 mmol) was heated at reflux in thionyl chloride (10 ml) for 30 minutes, cooled, evaporated in vacuo and the residue azeotroped with toluene. The residue was redissolved in CH2 Cl2 (10 ml) and treated with dry triethylamine (0.32 ml;2.26 mmol) and 4-methoxy-3-(4-methyl-1-piperazinyl)benzenamine (0.5 g;2.26 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 2%MeOH/CHCl3 to yield the title compound as a pale yellow foam (0.77 g;86%), which was converted to the oxalate salt, mp=125°-127° C.

Workup

  1. temperaturecooled
  2. customevaporated in vacuo
  3. customthe residue azeotroped with toluene
  4. dissolutionThe residue was redissolved in CH2 Cl2 (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 2%MeOH/CHCl3

Sources & evidence

ORD record
ord-503aa297d5764add9fd996b7cd0c594e
Source dataset
uspto-grants-1998_11
Patent number
US05834471

Reaction notes

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