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1-Butanol → 3-tert-Butyl-6-[3-[4-(diphenylmethoxy)piperidino]propylamino][1,2,4]triazolo[4,3-b]pyridazine fumarate

HRID 397559
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HRID 397559 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][NH2:18])[CH2:11][CH2:10]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:25]([C:29]1[N:33]2[N:34]=[C:35](Cl)[CH:36]=[CH:37][C:32]2=[N:31][N:30]=1)([CH3:28])([CH3:27])[CH3:26].C(N(C(C)C)C(C)C)C.[C:48]([O:51]CC)(=[O:50])[CH3:49].C([OH:58])CCC>>[C:7]([OH:58])(=[O:8])/[CH:19]=[CH:49]/[C:48]([OH:51])=[O:50].[C:25]([C:29]1[N:33]2[N:34]=[C:35]([NH: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:36]=[CH:37][C:32]2=[N:31][N:30]=1)([CH3:28])([CH3:26])[CH3:27]
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참가 물질

6

반응물 5

HCID 2631-ButanolHCID 8857Ethyl AcetateHCID 81531DiisopropylethylamineHCID 109693934-(Diphenylmethoxy)-1-piperidinepropaneamineHCID 230003263-Tert-butyl-6-chloro-(1,2,4)triazolo(4,3-b)pyridazine

생성물 1

HCID 230003143-tert-Butyl-6-[3-[4-(diphenylmethoxy)piperidino]propylamino][1,2,4]triazolo[4,3-b]pyridazine fumarate

실험 절차

854 mg of 4-(diphenylmethoxy)-1-piperidinepropanamine and 554 mg of 3-tert-butyl-6-chloro[1,2,4]triazolo[4,3-b]pyridazine were dissolved in 10 ml of 1-butanol; 0.91 ml of N-ethyldiisopropylamine was added, followed by refluxing under heating for 21 hours. After cooling, ethyl acetate was added; the reaction mixture was washed with saturated aqueous sodium bicarbonate and saturated saline 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; 780 mg of the residue was dissolved in ethanol; a solution of 282 mg of fumaric acid in ethanol was added, followed by concentration under reduced pressure. The residue was crystallized from ethanol-ethyl acetate (1:5), washed with ethyl acetate, and dried, to yield 938 mg of the title compound.

후처리

  1. temperatureby refluxing
  2. temperatureunder heating for 21 hours
  3. temperatureAfter cooling
  4. washthe reaction mixture was washed with saturated aqueous sodium bicarbonate and saturated saline
  5. dry with materialdried over magnesium sulfate
  6. concentrationAfter concentration under reduced pressure
  7. washeluted with ethyl acetate-methanol-triethylamine (50:5:1)
  8. customThe desired fraction was collected
  9. concentrationconcentrated under reduced pressure
  10. dissolution780 mg of the residue was dissolved in ethanol
  11. additiona solution of 282 mg of fumaric acid in ethanol was added
  12. concentrationfollowed by concentration under reduced pressure
  13. customThe residue was crystallized from ethanol-ethyl acetate (1:5)
  14. washwashed with ethyl acetate
  15. customdried

출처 및 근거

ORD 기록
ord-3c9842364ab14ea19b65d75645c613a4
출처 데이터셋
uspto-grants-2003_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06610694B1

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