氢化钠 → 6-[2-[2-[4-(Diphenylmethyl)piperazino]ethoxy] ethoxy][1,2,4]triazolo[1,5-b]pyridazine dihydrochloride

HRID 1067512

反应方程式

HRID 1067512 反应方程式
[H-].[Na+].[C:3]1([CH:9]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[N:10]2[CH2:15][CH2:14][N:13]([CH2:16][CH2:17][O:18][CH2:19][CH2:20][OH:21])[CH2:12][CH2:11]2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[Cl:28][C:29]1[CH:30]=[CH:31][C:32]2[N:33]([N:35]=[CH:36][N:37]=2)[N:34]=1>O1CCCC1>[ClH:28].[ClH:28].[C:22]1([CH:9]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:10]2[CH2:11][CH2:12][N:13]([CH2:16][CH2:17][O:18][CH2:19][CH2:20][O:21][C:29]3[CH:30]=[CH:31][C:32]4[N:33]([N:35]=[CH:36][N:37]=4)[N:34]=3)[CH2:14][CH2:15]2)[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

参与物

5

反应物 3

HCID 24758氢化钠HCID 71135去氯羟嗪HCID 112406116-氯-[1,2,4]三唑并[1,5-B]哒嗪

产物 1

HCID 229894146-[2-[2-[4-(Diphenylmethyl)piperazino]ethoxy] ethoxy][1,2,4]triazolo[1,5-b]pyridazine dihydrochloride收率 157%

试剂、催化剂与溶剂 1

HCID 8028四氢呋喃溶剂

实验过程

100 mg of 60% sodium hydride in oil was suspended in 20 ml of tetrahydrofuran; 470 mg of 4-(diphenylmethyl)-1-[2-(2-hydroxyethoxy)ethyl]piperazine was added, followed by heating and refluxing for 1 hour. After cooling, 200 mg of 6-chloro[1,2,4]triazolo[1,5-b]pyridazine was added, followed by heating and refluxing for 4.5 hours. After cooling, ice water was added, followed by extraction with ethyl acetate; the extract was washed with saturated saline and dried with magnesium sulfate. After the dry product was concentrated under reduced pressure, the residue was subjected to silica gel column chromatography and eluted with dichloromethane-ethyl acetate-methanol (10:10:1). The desired fraction was collected and dissolved in 5 ml of ethyl acetate; 0.83 ml of a 4 N hydrogen chloride solution in ethyl acetate was added; the crystal precipitated was collected by filtration, washed with ethyl ether and dried to yield 0.54 g of the title compound.

后处理

  1. temperatureby heating
  2. temperaturerefluxing for 1 hour
  3. temperatureAfter cooling
  4. temperatureby heating
  5. temperaturerefluxing for 4.5 hours
  6. temperatureAfter cooling
  7. extractionfollowed by extraction with ethyl acetate
  8. washthe extract was washed with saturated saline
  9. dry with materialdried with magnesium sulfate
  10. concentrationAfter the dry product was concentrated under reduced pressure
  11. washeluted with dichloromethane-ethyl acetate-methanol (10:10:1)
  12. customThe desired fraction was collected
  13. dissolutiondissolved in 5 ml of ethyl acetate
  14. addition0.83 ml of a 4 N hydrogen chloride solution in ethyl acetate was added
  15. customthe crystal precipitated
  16. filtrationwas collected by filtration
  17. washwashed with ethyl ether
  18. customdried

来源与证据

ORD记录
ord-d09406e9a40245e086862f96d16a6045
来源数据集
uspto-grants-2001_06
专利号
US06248740B1

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