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

HRID 1067496Notes

Reaction equation

HRID 1067496 reaction equation
[C:1]1([CH:7]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[O:8][CH:9]2[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][CH2:17][CH2:18][NH2:19])[CH2:11][CH2:10]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl[C:27]1[CH:28]=[CH:29][C:30]2[N:31]([N:33]=[CH:34][N:35]=2)[N:32]=1.C(N(C(C)C)C(C)C)C>C(O)CCC>[C:20]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][CH2:18][NH:19][C:27]3[CH:28]=[CH:29][C:30]4[N:31]([N:33]=[CH:34][N:35]=4)[N:32]=3)[CH2:11][CH2:10]2)[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 112406116-Chloro-(1,2,4)triazolo(1,5-b)pyridazineHCID 117392591-Piperidinebutanamine, 4-(diphenylmethoxy)-

Product 1

HCID 110049766-[4-[4-(Diphenylmethoxy)piperidino]butylamino][1,2,4]triazolo[1,5-b]pyridazineYield 9.1%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

4-(Diphenylmethoxy)-1-piperidinebutanamine (1.83 g) and 6-chloro[1,2,4]triazolo[1,5-b]pyridazine (557 mg) were dissolved in n-butanol (30 ml), followed by addition of N-ethyldiisopropylamine (931 mg). The mixture was refluxed under heating for 14 hours. After being cooled, the mixture was concentrated under reduced pressure, followed by addition of ice-water and extraction with ethyl acetate. The extract was washed with an aqueous sodium chloride saturated solution, dried over sodium sulfate and concentrated under reduced pressure. The residue was subjected to a silica-gel column chromatography and eluted with a mixture of ethyl acetate, methanol and triethylamine (45:5:1). Fractions containing the objective compound were collected and concentrated. The resulting crystals were collected, washed with ethylether and dried to yield the title compound (149 mg).

Workup

  1. temperatureThe mixture was refluxed
  2. temperatureunder heating for 14 hours
  3. temperatureAfter being cooled
  4. concentrationthe mixture was concentrated under reduced pressure
  5. additionfollowed by addition of ice-water and extraction with ethyl acetate
  6. washThe extract was washed with an aqueous sodium chloride saturated solution
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated under reduced pressure
  9. washeluted with a mixture of ethyl acetate, methanol and triethylamine (45:5:1)
  10. additionFractions containing the objective compound
  11. customwere collected
  12. concentrationconcentrated
  13. customThe resulting crystals were collected
  14. washwashed with ethylether
  15. customdried

Sources & evidence

ORD record
ord-b9865e2c56ce4edcb9f3ddac547eb90e
Source dataset
uspto-grants-2001_06
Patent number
US06248740B1

Reaction notes

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