Sodium hydride → 6-[2-[2-[4-(Diphenylmethyl)piperazino]ethoxy]ethoxy]-7-methyl[1,2,4]triazolo[1,5-b]pyridazine

HRID 1169046노트

반응식

HRID 1169046 반응식
[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[C:29]1[C:30]([CH3:38])=[CH:31][C:32]2[N:33]([N:35]=[CH:36][N:37]=2)[N:34]=1>O1CCCC1>[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[C:30]([CH3:38])=[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

참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 71135DecloxizineHCID 118051586-Chloro-7-methyl-[1,2,4]triazolo[1,5-b]pyridazine

생성물 1

HCID 229893826-[2-[2-[4-(Diphenylmethyl)piperazino]ethoxy]ethoxy]-7-methyl[1,2,4]triazolo[1,5-b]pyridazine수율 48.2%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

260 mg of 60% sodium hydride dispersion in mineral oil was suspended in 20 ml of tetrahydrofuran; 1.15 g of 2-[2-[4-(diphenylmethyl)-1-piperazinyl]ethoxy]ethanol was added, followed by heating and refluxing for 1 hour. After cooling, 540 mg of 6-chloro-7-methyl[1,2,4]triazolo[1,5-b]pyridazine was added, followed by heating and refluxing for 3 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 dichloromethane-ethyl acetate-methanol (10:10:1). The desired fraction was collected; the crystal precipitated was collected by filtration, washed with ethyl ether and dried to yield 730 mg of the title compound.

후처리

  1. temperatureby heating
  2. temperaturerefluxing for 1 hour
  3. temperatureAfter cooling
  4. temperatureby heating
  5. temperaturerefluxing for 3 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 dichloromethane-ethyl acetate-methanol (10:10:1)
  12. customThe desired fraction was collected
  13. customthe crystal precipitated
  14. filtrationwas collected by filtration
  15. washwashed with ethyl ether
  16. customdried

출처 및 근거

ORD 기록
ord-aafd52c8cd0e48d6bd97457348ac0adf
출처 데이터셋
uspto-grants-2003_09
특허 번호
US06627630B1

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