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

HRID 355732ノート

反応式

HRID 355732 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 24386Thionyl Chloride溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-503aa297d5764add9fd996b7cd0c594e
出典データセット
uspto-grants-1998_11
特許番号
US05834471

反応ノート

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