Pyridine → N-(6-iodoimidazo[1,2-b]pyridazin-2-yl)acetamide

HRID 589902

Reaction equation

HRID 589902 reaction equation
[I: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.[C:12](OC(=O)C)(=[O:14])[CH3:13].N1C=CC=CC=1>CN(C)C1C=CN=CC=1.ClCCl>[I:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:8]=[C:9]([NH:11][C:12](=[O:14])[CH3:13])[N:10]=2)[N:7]=1

Participants

6

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 574410246-Iodoimidazo[1,2-B]pyridazin-2-amine

Product 1

HCID 57441059N-(6-iodoimidazo[1,2-b]pyridazin-2-yl)acetamide

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a 50-mL round bottom flask was added 6-iodo-imidazo[1,2-b]pyridazin-2-ylamine (130 mg, 0.5 mmol, 1 eq), anhydrous dichloromethane (10 mL), acetic anhydride (0.071 mL, 1.5 eq), pyridine (0.073 mL, 1.8 eq), and 4-(dimethylamino)pyridine (0.61 mg, 0.01 eq). After the mixture was stirred at room temperature for four hours, it was quenched with saturated aqueous sodium bicarbonate and extracted with i-PrOH—CHCl3 (1:4). The organic layer was isolated, washed with brine, and dried with anhydrous sodium sulfate. The upper clear solution was decanted, concentrated, and the residue was subject to a gradient column chromatography (from DCM to MeOH-DCM 1:30) to yield N-(6-iodoimidazo[1,2-b]pyridazin-2-yl)acetamide as a white solid in amount of 67 mg.

Workup

  1. customit was quenched with saturated aqueous sodium bicarbonate
  2. extractionextracted with i-PrOH—CHCl3 (1:4)
  3. customThe organic layer was isolated
  4. washwashed with brine
  5. dry with materialdried with anhydrous sodium sulfate
  6. customThe upper clear solution was decanted
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-ea3d1294d6934a98a922f30fb7b59a34
Source dataset
uspto-grants-2016_01
Patent number
US09233968B1

Linked notes

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