6-Chloro-2-methyl-[1,2,4]triazolo[1,5-b]pyridazine → 6-[3-[4-(Diphenylmethoxy)piperidino]propoxy]-2-methyl[1,2,4]triazolo[1,5-b]pyridazine

HRID 1067501ノート

反応式

HRID 1067501 の反応式
[C:1]1([CH:7]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[O:8][CH:9]2[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][CH2:17][OH:18])[CH2:11][CH2:10]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CC(C)([O-])C.[Na+].Cl[C:32]1[CH:33]=[CH:34][C:35]2[N:36]([N:38]=[C:39]([CH3:41])[N:40]=2)[N:37]=1>O1CCCC1>[C:19]1([CH:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[O:8][CH:9]2[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][CH2:17][O:18][C:32]3[CH:33]=[CH:34][C:35]4[N:36]([N:38]=[C:39]([CH3:41])[N:40]=4)[N:37]=3)[CH2:11][CH2:10]2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

参加物

5

反応物 3

HCID 122125266-Chloro-2-methyl-[1,2,4]triazolo[1,5-b]pyridazineHCID 229892644-(Diphenylmethoxy)piperidinepropanolHCID 23676156Sodium t-butoxide

生成物 1

HCID 108634356-[3-[4-(Diphenylmethoxy)piperidino]propoxy]-2-methyl[1,2,4]triazolo[1,5-b]pyridazine収率 67.2%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
60 °C

実験手順

4-(Diphenylmethoxy)-1-piperidinepropanol (743 mg) was dissolved in dried terahydrofuran (17 ml), followed by addition of sodium t-butoxide (241 mg). The mixture was heated to 60° C. and stirred for 30 minutes. After the mixture was cooled, 6-chloro-2-methyl[1,2,4]triazolo[1,5-b]pyridazine (384 mg) was added thereto, followed by reflux under heating for 21 hours. After the mixture was cooled, ice-water was added thereto, 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, methanol and triethylamine (50:5:1). Fractions containing the objective compound were collected. The resulting crystals were washed with ethylether and dried to yield the title compound (700 mg).

後処理

  1. temperatureAfter the mixture was cooled
  2. temperatureby reflux
  3. temperatureunder heating for 21 hours
  4. temperatureAfter the mixture was cooled
  5. extractionfollowed by extraction with ethyl acetate
  6. washThe extract was washed with an aqueous sodium chloride saturated solution
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. washeluted with a mixture of ethyl acetate, methanol and triethylamine (50:5:1)
  10. additionFractions containing the objective compound
  11. customwere collected
  12. washThe resulting crystals were washed with ethylether
  13. customdried

出典と根拠

ORDレコード
ord-13c15766f94b4f188fedf50765277a27
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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