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

HRID 1169030Notes

Reaction equation

HRID 1169030 reaction equation
Cl[C:2]1[CH:3]=[CH:4][C:5]2[N:6]([N:8]=[C:9]([CH3:11])[N:10]=2)[N:7]=1.[C:12]1([CH:18]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[O:19][CH:20]2[CH2:25][CH2:24][N:23]([CH2:26][CH2:27][CH2:28][NH2:29])[CH2:22][CH2:21]2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(N(C(C)C)C(C)C)C.C(=O)([O-])O.[Na+]>C(O)CCC.C(OCC)(=O)C>[C:30]1([CH:18]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[O:19][CH:20]2[CH2:25][CH2:24][N:23]([CH2:26][CH2:27][CH2:28][NH:29][C:2]3[CH:3]=[CH:4][C:5]4[N:6]([N:8]=[C:9]([CH3:11])[N:10]=4)[N:7]=3)[CH2:22][CH2:21]2)[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 109693934-(Diphenylmethoxy)-1-piperidinepropaneamineHCID 122125266-Chloro-2-methyl-[1,2,4]triazolo[1,5-b]pyridazine

Product 1

HCID 110378166-[3-[4-(Diphenylmethoxy)piperidino]propylamino]-2-methyl[1,2,4]triazolo[1,5-b]pyridazineYield 30.9%

Reagents, catalysts & solvents 2

HCID 2631-ButanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

6-Chloro-2-methyl[1,2,4]triazolo[1,5-b]pyridazine (655 mg) and 4-(diphenylmethoxy)-1-piperidinepropanamine (1.26 g) was suspended in 1-butanol (20 ml), followed by addition of N-ethyldiisopropylamine (1.94 ml). The mixture was refluxed under heating for 22 hours, followed by addition of ice-water and sodium hydrogen carbonate 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 silica gel column chromatography and eluted with a mixture of ethyl acetate, methanol and triethylamine (50:5:1). Fractions containing the objective compound were collected and concentrated. The resulting crystals were washed with hexane and dried to yield the title compound (547 mg).

Workup

  1. temperatureThe mixture was refluxed
  2. temperatureunder heating for 22 hours
  3. washThe extract was washed with an aqueous sodium chloride saturated solution
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. washeluted with a mixture of ethyl acetate, methanol and triethylamine (50:5:1)
  7. additionFractions containing the objective compound
  8. customwere collected
  9. concentrationconcentrated
  10. washThe resulting crystals were washed with hexane
  11. customdried

Sources & evidence

ORD record
ord-69f7e9926b70468e866fc93246ca9d86
Source dataset
uspto-grants-2003_09
Patent number
US06627630B1

Reaction notes

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