Diisopropylethylamine → 6-[3-[4-(Diphenylmethoxy)piperidino]propylamino]-2-phenyl[1,2,4]triazolo[1,5-b]pyridazine

HRID 1169037노트

반응식

HRID 1169037 반응식
Cl[C:2]1[CH:3]=[CH:4][C:5]2[N:6]([N:8]=[C:9]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[N:10]=2)[N:7]=1.[C:17]1([CH:23]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[O:24][CH:25]2[CH2:30][CH2:29][N:28]([CH2:31][CH2:32][CH2:33][NH2:34])[CH2:27][CH2:26]2)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C(N(C(C)C)C(C)C)C.C(=O)([O-])O.[Na+]>C(O)CCC>[C:35]1([CH:23]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[O:24][CH:25]2[CH2:30][CH2:29][N:28]([CH2:31][CH2:32][CH2:33][NH:34][C:2]3[CH:3]=[CH:4][C:5]4[N:6]([N:8]=[C:9]([C:11]5[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=5)[N:10]=4)[N:7]=3)[CH2:27][CH2:26]2)[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=1

참가 물질

6

반응물 4

HCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 14591196-Chloro-2-phenyl-[1,2,4]triazolo[1,5-b]pyridazineHCID 109693934-(Diphenylmethoxy)-1-piperidinepropaneamine

생성물 1

HCID 229893166-[3-[4-(Diphenylmethoxy)piperidino]propylamino]-2-phenyl[1,2,4]triazolo[1,5-b]pyridazine수율 37.6%

시약·촉매·용매 1

HCID 2631-Butanol용매

실험 절차

365 mg of 6-chloro-2-phenyl[1,2,4]triazolo[1,5-b]pyridazine and 0.513 g of 4-(diphenylmethoxy)-1-piperidinepropanamine were suspended in 8 ml of 1-butanol; 0.54 ml of N-ethyldiisopropylamine was added, followed by heating and refluxing for 19 hours. Ice water and sodium hydrogen carbonate were 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:triethylamine (50:5:1). The desired fraction was collected and concentrated; the resulting crystal was recrystallized from ethyl acetate to yield 308 mg of the title compound.

후처리

  1. temperatureby heating
  2. temperaturerefluxing for 19 hours
  3. extractionfollowed by extraction with ethyl acetate
  4. washthe extract was washed with saturated saline
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. washeluted with ethyl acetate:methanol:triethylamine (50:5:1)
  8. customThe desired fraction was collected
  9. concentrationconcentrated
  10. customthe resulting crystal was recrystallized from ethyl acetate

출처 및 근거

ORD 기록
ord-fcdd091e088a4c8c962258da02ec77d4
출처 데이터셋
uspto-grants-2003_09
특허 번호
US06627630B1

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