Methanol → 2-Amino-6-chloroimidazo[1,2-b]pyridazine

HRID 1162430Notes

Reaction equation

HRID 1162430 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:8]=[C:9]([NH:11]C(=O)C(F)(F)F)[N:10]=2)[N:7]=1.C1COCC1.CO.C(=O)([O-])[O-].[K+].[K+]>C(OCC)(=O)C.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:8]=[C:9]([NH2:11])[N:10]=2)[N:7]=1

Participants

7

Reactant 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 11430Potassium CarbonateHCID 57749420N-(6-Chloroimidazo[1,2-b]pyridazin-2-yl)-2,2,2-trifluoroacetamide

Product 1

HCID 497580212-Amino-6-chloroimidazo[1,2-b]pyridazineYield 90%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of N-(6-chloroimidazo[1,2-b]pyridazin-2-yl)-2,2,2-trifluoroacetamide (80 mg, 0.30 mmol) in a THF:methanol:water (1 mL each) mixture was added anhydrous potassium carbonate (400 mg, 3 mmol). The reaction mixture was refluxed for 8 hrs. After cooling to rt, the reaction mixture diluted with ethyl acetate and water. The phases were separated and the organic layer was washed with brine (2×5 mL), dried over sodium sulfate and concentrated to afford the title compound (45 mg, 90%). 1H NMR (DMSO-d6, 300 MHz): δ 5.65 (s, 2H), 7.02 (d, 1H), 7.7 (d, 1H).

Workup

  1. temperatureThe reaction mixture was refluxed for 8 hrs
  2. customThe phases were separated
  3. washthe organic layer was washed with brine (2×5 mL)
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-7b9917f65e5e4381b4a22e201fc71400
Source dataset
uspto-grants-2010_10
Patent number
US07820665B2

Reaction notes

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