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

HRID 1663625Notes

Reaction equation

HRID 1663625 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-60a707966e3f4d2a9b068881a61dc94f
Source dataset
uspto-grants-2011_10
Patent number
US08034812B2

Reaction notes

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