1,1'-Carbonyldiimidazole → 6-[2-[4-(Diphenylmethyl)piperazino-carbonyloxyl]ethoxy][1,2,4]triazolo[1,5-b]pyridazine

HRID 1067504ノート

反応式

HRID 1067504 の反応式
[OH:1][CH2:2][CH2:3][O:4][C:5]1[CH:6]=[CH:7][C:8]2[N:9]([N:11]=[CH:12][N:13]=2)[N:10]=1.[C:14](N1C=CN=C1)(N1C=CN=C1)=[O:15].[C:26]1([CH:32]([C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[N:33]2[CH2:38][CH2:37][NH:36][CH2:35][CH2:34]2)[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.C(N(C(C)C)C(C)C)C>O1CCCC1>[C:39]1([CH:32]([C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)[N:33]2[CH2:34][CH2:35][NH:36][CH:37]([C:14]([O:1][CH2:2][CH2:3][O:4][C:5]3[CH:6]=[CH:7][C:8]4[N:9]([N:11]=[CH:12][N:13]=4)[N:10]=3)=[O:15])[CH2:38]2)[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1

参加物

6

反応物 4

HCID 682631,1'-CarbonyldiimidazoleHCID 70048BenzhydrylpiperazineHCID 81531DiisopropylethylamineHCID 229892366-(2-Hydroxyethoxy)[1,2,4]triazolo[1,5-b]pyridazine

生成物 1

HCID 702352096-[2-[4-(Diphenylmethyl)piperazino-carbonyloxyl]ethoxy][1,2,4]triazolo[1,5-b]pyridazine収率 40.5%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

6-(2-Hydroxyethoxy)[1,2,4]triazolo[1,5-b]pyridazine (450 mg) was dissolved in tetrahydrofuran (20 ml), followed by addition of carbonyldiimidazole (649 mg). The mixture was stirred at room temperature for 3 hours, followed by addition of 1-(diphenylmethyl)piperazine (1.07 g) and N-ethyldiisopropylamine (0.73 ml). The mixture was stirred at 60° C. for 17 hours and concentrated under reduced pressure. Ice-water was added to the residue, followed by extraction with ethyl acetate. The extract was washed with an aqueous sodium chloride saturated solution, dried over magnesium sulfate and concentrated under reduced pressure. The residue was subjected to silica-gel column chromatography and eluted with a mixture of ethyl acetate and hexane (1:1). Fractions containing the objective compound were collected and concentrated. The resulting crystals were recrystalized from ethyl acetate to yield the title compound (464 mg).

後処理

  1. stirringThe mixture was stirred at 60° C. for 17 hours
  2. concentrationconcentrated under reduced pressure
  3. additionIce-water was added to the residue
  4. extractionfollowed by extraction with ethyl acetate
  5. washThe extract was washed with an aqueous sodium chloride saturated solution
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. washeluted with a mixture of ethyl acetate and hexane (1:1)
  9. additionFractions containing the objective compound
  10. customwere collected
  11. concentrationconcentrated
  12. customThe resulting crystals were recrystalized from ethyl acetate

出典と根拠

ORDレコード
ord-507fcf75b79f4f489f185d7b1fe55e7b
出典データセット
uspto-grants-2001_06
特許番号
US06248740B1

反応ノート

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