Tetrahydrofuran → 7-t-Butyl-6-[2-[2-[4-(Diphenylmethyl)-1-piperazinyl]ethoxy]ethoxy][1,2,4]triazolo[1,5-b]pyridazine Dihydrochloride

HRID 1169056ノート

反応式

HRID 1169056 の反応式
[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][CH:19](O)[CH3:20])[CH2:12][CH2:11]2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[C:28]([C:32]1[C:37]([Cl:38])=[N:36][N:35]2[N:39]=[CH:40][N:41]=[C:34]2[CH:33]=1)([CH3:31])([CH3:30])[CH3:29].[O:42]1CCCC1>>[ClH:38].[ClH:38].[C:28]([C:32]1[C:37]([O:42][CH2:20][CH2:19][O:18][CH2:17][CH2:16][N:13]2[CH2:12][CH2:11][N:10]([CH:9]([C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=3)[C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=3)[CH2:15][CH2:14]2)=[N:36][N:35]2[N:39]=[CH:40][N:41]=[C:34]2[CH:33]=1)([CH3:31])([CH3:30])[CH3:29]

参加物

5

反応物 4

HCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 229892436-Chloro-7-t-butyl[1,2,4]triazolo[1,5-b]pyridazineHCID 22989276[2-[4-(Diphenylmethyl)-1-piperazinyl]ethoxy]ethanol

生成物 1

HCID 229894027-t-Butyl-6-[2-[2-[4-(Diphenylmethyl)-1-piperazinyl]ethoxy]ethoxy][1,2,4]triazolo[1,5-b]pyridazine Dihydrochloride

実験手順

150 mg of 60% sodium hydride in oil was suspended in 20 ml of tetrahydrofuran; 1.05 g of [2-[4-(diphenylmethyl)-1-piperazinyl]ethoxy]ethanol was added, followed by heating and refluxing for 1 hour. After cooling, 650 mg of 7-t-butyl-6-chloro[1,2,4]triazolo[1,5-b]pyridazine was added, followed by heating and refluxing for 2 hours. After cooling, ice water was added, followed by extraction with ethyl acetate; the extract was washed with saturated saline, dried over magnesium sulfate and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography and eluted with ethyl acetate:methanol (10:1). The desired fraction was collected; the residue was dissolved in 5 ml of ethyl acetate; 2.1 ml of a 4N hydrogen chloride solution in ethyl acetate was added; the crystal precipitated was collected by filtration, washed with ethyl ether and dried to yield 1.55 g of the title compound.

後処理

  1. temperatureby heating
  2. temperaturerefluxing for 1 hour
  3. temperatureAfter cooling
  4. temperatureby heating
  5. temperaturerefluxing for 2 hours
  6. temperatureAfter cooling
  7. extractionfollowed by extraction with ethyl acetate
  8. washthe extract was washed with saturated saline
  9. dry with materialdried over magnesium sulfate
  10. concentrationconcentrated under reduced pressure
  11. washeluted with ethyl acetate:methanol (10:1)
  12. customThe desired fraction was collected
  13. dissolutionthe residue was dissolved in 5 ml of ethyl acetate
  14. addition2.1 ml of a 4N hydrogen chloride solution in ethyl acetate was added
  15. customthe crystal precipitated
  16. filtrationwas collected by filtration
  17. washwashed with ethyl ether
  18. customdried

出典と根拠

ORDレコード
ord-c4c5e1e19dd2459c9182ee7a1804d50b
出典データセット
uspto-grants-2003_09
特許番号
US06627630B1

反応ノート

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