Ethyl Acetate → HCID 22989427, compound

HRID 1067502Notes

Reaction equation

HRID 1067502 reaction equation
Br[CH2:2][C:3]([NH:5][C:6]1[CH:7]=[CH:8][C:9]2[N:10]([N:12]=[CH:13][N:14]=2)[N:11]=1)=[O:4].[C:15]1([CH:21]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[N:22]2[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C>C(#N)C>[C:28]1([CH:21]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[N:22]2[CH2:23][CH2:24][N:25]([CH2:2][C:3]([NH:5][C:6]3[CH:7]=[CH:8][C:9]4[N:10]([N:12]=[CH:13][N:14]=4)[N:11]=3)=[O:4])[CH2:26][CH2:27]2)[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 70048BenzhydrylpiperazineHCID 22989435HCID 22989435, compound

Product 1

HCID 22989427HCID 22989427, compoundYield 49.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

6-(2-Bromoacetamido)[1,2,4]triazolo[1,5-b]pyridazine (636 mg) and 1-(diphenylmethyl)piperazine (627 mg) were dissolved in acetonitrile (20 ml), followed by addition of potassium carbonate (411 mg). The mixture was stirred at room temperature for 2 hours, followed by addition of ice-water and extraction with ethyl acetate. The extract was washed with aqueous sodium chloride saturated solution, dried over magnesium sulfate and concentrated under reduced pressure. The resulting crystals were collected by filtration and recrystalized from methanol to yield the captioned compound (525 mg).

Workup

  1. washThe extract was washed with aqueous sodium chloride saturated solution
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. filtrationThe resulting crystals were collected by filtration
  5. customrecrystalized from methanol

Sources & evidence

ORD record
ord-9665c71e822a4f92a9e0b49c2c9c0182
Source dataset
uspto-grants-2001_06
Patent number
US06248740B1

Reaction notes

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