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

HRID 1169026Notes

Reaction equation

HRID 1169026 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 1-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 magnesium 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 ethyl ether 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 magnesium 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 ethyl ether
  15. customdried

Sources & evidence

ORD record
ord-a821833f505a4bc7b26d508fd2daf261
Source dataset
uspto-grants-2003_09
Patent number
US06627630B1

Reaction notes

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