Ethyl 6-Iodoimidazo[1,2-b]pyridazine-2-carboxylate → 6-iodo-N-methylimidazo[1,2-b]pyridazine-2-carboxamide

HRID 1667810Notes

Reaction equation

HRID 1667810 reaction equation
[I:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:8]=[C:9]([C:11]([O:13]CC)=O)[N:10]=2)[N:7]=1.[CH3:16][NH2:17].O1CCCC1>CO>[I:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:8]=[C:9]([C:11]([NH:17][CH3:16])=[O:13])[N:10]=2)[N:7]=1

Participants

4

Reactant 2

HCID 51063906Ethyl 6-Iodoimidazo[1,2-b]pyridazine-2-carboxylateHCID 66615946Methylamine tetrahydrofuran

Product 1

HCID 574410266-iodo-N-methylimidazo[1,2-b]pyridazine-2-carboxamideYield 71.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a suspension of ethyl 6-iodoimidazo[1,2-b]pyridazine-2-carboxylate (4.5 g, 14.8 mmol) in methanol (13.5 mL) was added dropwise a solution of methylamine/tetrahydrofuran (2 mol/L, 37.1 mL, 74.2 mmol), and the mixture was stirred at room temperature for 96 hr. The solvent was evaporated under reduced pressure, and the residue was washed with ethyl acetate, saturated brine and water to give the title compound (3.2 g, 71%) as a dark brown powder.

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. washthe residue was washed with ethyl acetate, saturated brine and water

Sources & evidence

ORD record
ord-0bb74e3288b3483bbbed4c890b621340
Source dataset
uspto-grants-2011_10
Patent number
US08044049B2

Reaction notes

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