6-Chloro-2-phenyl-[1,2,4]triazolo[1,5-b]pyridazine → 6-[3-[4-(Diphenylmethoxy)piperidino]propoxy]-2-phenyl[1,2,4]triazolo[1,5-b]pyridazine hydrochloride

HRID 1067506노트

반응식

HRID 1067506 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+].[Cl:31][C:32]1[CH:33]=[CH:34][C:35]2[N:36]([N:38]=[C:39]([C:41]3[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=3)[N:40]=2)[N:37]=1>O1CCCC1>[ClH:31].[C:19]1([CH:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[O:8][CH:9]2[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][CH2:17][O:18][C:32]3[CH:33]=[CH:34][C:35]4[N:36]([N:38]=[C:39]([C:41]5[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=5)[N:40]=4)[N:37]=3)[CH2:11][CH2:10]2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

참가 물질

5

반응물 3

HCID 14591196-Chloro-2-phenyl-[1,2,4]triazolo[1,5-b]pyridazineHCID 229892644-(Diphenylmethoxy)piperidinepropanolHCID 23676156Sodium t-butoxide

생성물 1

HCID 229892986-[3-[4-(Diphenylmethoxy)piperidino]propoxy]-2-phenyl[1,2,4]triazolo[1,5-b]pyridazine hydrochloride수율 44%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

4-(Diphenylmethoxy)-1-piperidinepropanol (487 mg) was dissolved in dried tetrahydrofuran (10 ml), followed by addition of sodium t-butoxide (144 mg). The mixture was refluxed under heating for 40 minutes. After the mixture was cooled, 6-chloro-2-phenyl[1,2,4]triazolo[1,5-b]pyridazine (315 mg) was added thereto. This mixture was refluxed under heating for 4 hours. After the mixture was cooled, ice-water was added thereto, followed by extraction with a mixture of ethyl acetate and tetrahydrofuran (2:1). The extract was washed with an aqueous sodium chloride saturated solution dried over magnesium sulfate and concentrated under reduced pressure. The residue was subjected to silica-gel column chromatography and eluted with a mixture of ethyl acetate and methanol (10:1). Fractions containing the objective compound were collected, concentrated and dissolved in ethyl acetate (10 ml), followed by addition of 4N HCl in ethyl acetate solution (0.25 ml) and concentrated under reduced pressure. The resulting crystals were recrystalized from ethanol to yield the title compound (0.334 g).

후처리

  1. temperatureThe mixture was refluxed
  2. temperatureunder heating for 40 minutes
  3. temperatureAfter the mixture was cooled
  4. temperatureThis mixture was refluxed
  5. temperatureunder heating for 4 hours
  6. temperatureAfter the mixture was cooled
  7. extractionfollowed by extraction with a mixture of ethyl acetate and tetrahydrofuran (2:1)
  8. washThe extract was washed with an aqueous sodium chloride saturated solution
  9. dry with materialdried over magnesium sulfate
  10. concentrationconcentrated under reduced pressure
  11. washeluted with a mixture of ethyl acetate and methanol (10:1)
  12. additionFractions containing the objective compound
  13. customwere collected
  14. concentrationconcentrated
  15. dissolutiondissolved in ethyl acetate (10 ml)
  16. additionfollowed by addition of 4N HCl in ethyl acetate solution (0.25 ml)
  17. concentrationconcentrated under reduced pressure
  18. customThe resulting crystals were recrystalized from ethanol

출처 및 근거

ORD 기록
ord-9d9018ede7d54e27afd51010f9ee28fb
출처 데이터셋
uspto-grants-2001_06
특허 번호
US06248740B1

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