Ethyl Acetate → HCID 22989427, compound

HRID 1169032Notes

Reaction equation

HRID 1169032 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

2-Bromo-N-([1,2,4]triazolo[1,5-b]pyridazin-6-yl)acetamide (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 recrystallized from methanol to yield the title 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. customrecrystallized from methanol

Sources & evidence

ORD record
ord-df1a914df793463c8fb3a3343d5ab49b
Source dataset
uspto-grants-2003_09
Patent number
US06627630B1

Reaction notes

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