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4-(Diphenylmethoxy)piperidinepropanol → 3-Tert-butyl-6-[3-[4-(diphenylmethoxy)piperidino]propoxy][1,2,4]triazolo[4,3-b]pyridazine

HRID 397560
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HRID 397560 반응식
[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+].[C:31]([C:35]1[N:39]2[N:40]=[C:41](Cl)[CH:42]=[CH:43][C:38]2=[N:37][N:36]=1)([CH3:34])([CH3:33])[CH3:32]>O1CCCC1>[C:31]([C:35]1[N:39]2[N:40]=[C:41]([O:18][CH2:17][CH2:16][CH2:15][N:12]3[CH2:13][CH2:14][CH:9]([O:8][CH:7]([C:1]4[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=4)[C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)[CH2:10][CH2:11]3)[CH:42]=[CH:43][C:38]2=[N:37][N:36]=1)([CH3:34])([CH3:32])[CH3:33]
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참가 물질

5

반응물 3

HCID 229892644-(Diphenylmethoxy)piperidinepropanolHCID 230003263-Tert-butyl-6-chloro-(1,2,4)triazolo(4,3-b)pyridazineHCID 23676156Sodium t-butoxide

생성물 1

HCID 230002943-Tert-butyl-6-[3-[4-(diphenylmethoxy)piperidino]propoxy][1,2,4]triazolo[4,3-b]pyridazine수율 32.9%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran
용매

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온도
60 °C

실험 절차

991 mg of 4-(diphenylmethoxy)-1-piperidinepropanol was dissolved in 20 ml of tetrahydrofuran; 322 mg of sodium tert-butoxide was added, followed by stirring at an external temperature of 60° C. for 2 hours. After cooling, 642 mg of 3-tert-butyl-6-chloro[1,2,4]triazolo[4,3-b]pyridazine was added, followed by refluxing under heating for 2 hours. After cooling, saline was added; the reaction mixture was extracted with ethyl acetate and dried over magnesium sulfate. After concentration under reduced pressure, the residue was subjected to silica gel column chromatography and eluted with ethyl acetate-methanol-triethylamine (50:5:1). The desired fraction was collected and concentrated under reduced pressure; 1.26 g of the residue was dissolved in 3 ml of pyridine; 1.5 ml of acetic anhydride was added, followed by stirring at room temperature for 6 hours. After the reaction mixture was concentrated under reduced pressure, the residue was subjected to silica gel column chromatography and eluted with ethyl acetate-methanol-triethylamine (50:5:1). The desired fraction was collected and concentrated under reduced pressure; the residue crystallized from ethyl acetate-diethyl ether (1:1), washed with diethyl ether, and dried, to yield 500 mg of the title compound.

후처리

  1. temperatureAfter cooling
  2. temperatureby refluxing
  3. temperatureunder heating for 2 hours
  4. temperatureAfter cooling
  5. additionsaline was added
  6. extractionthe reaction mixture was extracted with ethyl acetate
  7. dry with materialdried over magnesium sulfate
  8. concentrationAfter concentration under reduced pressure
  9. washeluted with ethyl acetate-methanol-triethylamine (50:5:1)
  10. customThe desired fraction was collected
  11. concentrationconcentrated under reduced pressure
  12. dissolution1.26 g of the residue was dissolved in 3 ml of pyridine
  13. addition1.5 ml of acetic anhydride was added
  14. stirringby stirring at room temperature for 6 hours
  15. concentrationAfter the reaction mixture was concentrated under reduced pressure
  16. washeluted with ethyl acetate-methanol-triethylamine (50:5:1)
  17. customThe desired fraction was collected
  18. concentrationconcentrated under reduced pressure
  19. customthe residue crystallized from ethyl acetate-diethyl ether (1:1)
  20. washwashed with diethyl ether
  21. customdried

출처 및 근거

ORD 기록
ord-8a0f8287676b4a76a47ecf441700a154
출처 데이터셋
uspto-grants-2003_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06610694B1

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