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Diisopropylethylamine → HCID 22989232, compound

HRID 1169025
Notes
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Reaction equation

HRID 1169025 reaction equation
[C:1]1([CH:7]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[O:8][CH:9]2[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl[C:22]1[CH:23]=[CH:24][C:25]2[N:26]([N:28]=[CH:29][N:30]=2)[N:27]=1.C(N(C(C)C)C(C)C)C>C(O)CCC>[C:15]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]([C:22]3[CH:23]=[CH:24][C:25]4[N:26]([N:28]=[CH:29][N:30]=4)[N:27]=3)[CH2:11][CH2:10]2)[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 30175844-BenzhydryloxypiperidineHCID 112406116-Chloro-(1,2,4)triazolo(1,5-b)pyridazine

Product 1

HCID 22989232HCID 22989232, compoundYield 54.4%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

4-(Diphenylmethoxy)piperidine (1.12 g) and 6-chloro[1,2,4]triazolo[1,5-b]pyridazine (558 mg) were dissolved in 1-butanol (25 ml), followed by addition of N-ethyldiisopropylamine (700 mg). The mixture was refluxed under heating for 17 hours. After being cooled, the mixture was concentrated under reduced pressure. Ice-water was added to the residue, followed by extraction with ethyl acetate. 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 hexane and ethyl acetate (1:3). Fractions containing the objective compound were collected and recrystallized from ethanol to yield the title compound (757 mg).

Workup

  1. temperatureThe mixture was refluxed
  2. temperatureunder heating for 17 hours
  3. temperatureAfter being cooled
  4. concentrationthe mixture was concentrated under reduced pressure
  5. additionIce-water was added to the residue
  6. extractionfollowed by extraction with ethyl acetate
  7. washThe extract was washed with an aqueous sodium chloride saturated solution
  8. dry with materialdried over magnesium sulfate
  9. concentrationconcentrated under reduced pressure
  10. washeluted with a mixture of hexane and ethyl acetate (1:3)
  11. additionFractions containing the objective compound
  12. customwere collected
  13. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-92087ce920ee4f36a882bbee89f9d7f6
Source dataset
uspto-grants-2003_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06627630B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes