Sodium hydride → 6-[6-[4-(Diphenylmethoxy)piperidino]hexyloxy]-7-methyl[1,2,4]triazolo[1,5-b]pyridazine Hydrochloride

HRID 1169050노트

반응식

HRID 1169050 반응식
[H-].[Na+].[C:3]1([CH:9]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[O:10][CH:11]2[CH2:16][CH2:15][N:14]([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][OH:23])[CH2:13][CH2:12]2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[Cl:30][C:31]1[C:32]([CH3:40])=[CH:33][C:34]2[N:35]([N:37]=[CH:38][N:39]=2)[N:36]=1>O1CCCC1>[ClH:30].[C:3]1([CH:9]([C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)[O:10][CH:11]2[CH2:16][CH2:15][N:14]([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][O:23][C:31]3[C:32]([CH3:40])=[CH:33][C:34]4[N:35]([N:37]=[CH:38][N:39]=4)[N:36]=3)[CH2:13][CH2:12]2)[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 118051586-Chloro-7-methyl-[1,2,4]triazolo[1,5-b]pyridazineHCID 229893784-(Diphenylmethoxy)-1-piperidinehexanol

생성물 1

HCID 229894326-[6-[4-(Diphenylmethoxy)piperidino]hexyloxy]-7-methyl[1,2,4]triazolo[1,5-b]pyridazine Hydrochloride수율 38.7%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

160 mg of 60% sodium hydride in oil was suspended in 20 ml of tetrahydrofuran; 1.24 g of 4-(diphenylmethoxy)-1-piperidinehexanol was added, followed by heating and refluxing for 1 hour. After cooling, 570 mg of 6-chloro-7-methyl[1,2,4]triazolo[1,5-b]pyridazine was added, followed by heating and refluxing for 1 hour. 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 and dissolved in 5 ml of ethyl acetate; 0.54 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 0.70 g of the title compound.

후처리

  1. temperatureby heating
  2. temperaturerefluxing for 1 hour
  3. temperatureAfter cooling
  4. temperatureby heating
  5. temperaturerefluxing for 1 hour
  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. dissolutiondissolved in 5 ml of ethyl acetate
  14. addition0.54 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

출처 및 근거

ORD 기록
ord-424b1bc115ab40ab969141cc0b6eb39d
출처 데이터셋
uspto-grants-2003_09
특허 번호
US06627630B1

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