Chloroform → Tert-butyl 4-[2-(4-fluorophenyl)imidazo[1,2-b]pyridazin-6-yl]piperazine-1-carboxylate

HRID 80720Notes

Reaction equation

HRID 80720 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]3[CH:15]=[CH:14][C:13]([N:16]4[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]4)=[N:12][N:11]3[CH:22]=2)=[CH:4][CH:3]=1.CN([C:26]1[CH:31]=[CH:30]C=CN=1)C.[C:32](=[O:35])([O-])[OH:33].[Na+].[CH:37](Cl)(Cl)Cl>>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]3[CH:15]=[CH:14][C:13]([N:16]4[CH2:17][CH2:18][N:19]([C:32]([O:33][C:31]([CH3:30])([CH3:26])[CH3:37])=[O:35])[CH2:20][CH2:21]4)=[N:12][N:11]3[CH:22]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 4

HCID 6212Chloroform2×HCID 218852-DimethylaminopyridineHCID 516892Sodium BicarbonateHCID 59406970HCID 59406970, compound

Product 1

HCID 59406962Tert-butyl 4-[2-(4-fluorophenyl)imidazo[1,2-b]pyridazin-6-yl]piperazine-1-carboxylateYield 97%

Procedure

To a solution of 21.5 g (72.3 mmol) of 2-(4-fluorophenyl)-6-piperazin-1-ylimidazo[1,2-b]pyridazine and 0.44 g (3.6 mmol) of dimethylaminopyridine in 500 mL of chloroform is added dropwise a solution of tert-butyl anhydride dissolved in 100 mL of chloroform. After stirring for 30 minutes at room temperature, the medium is poured into saturated aqueous sodium hydrogen carbonate solution. The organic phase obtained is washed with water, dried over sodium sulfate and then concentrated under reduced pressure to give a brown solid. Finally, 28.0 g of a beige-colored powder are isolated after trituration in a mixture of 200 mL of diisopropyl ether and 10 mL of isopropanol at reflux, followed by cold filtration and drying.

Workup

  1. customThe organic phase obtained
  2. washis washed with water
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customto give a brown solid

Sources & evidence

ORD record
ord-b7906541942741acb92f950b19c21b7a
Source dataset
uspto-grants-2014_09
Patent number
US08846676B2

Reaction notes

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