Diethyl Ether → 6-Iodoimidazo[1,2-B]pyridazin-2-amine

HRID 2391115Notes

Reaction equation

HRID 2391115 reaction equation
[I:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:8]=[C:9]([NH:11]C(=O)OC(C)(C)C)[N:10]=2)[N:7]=1.Cl.C(OCC)(=O)C.C(OCC)C>C(OCC)(=O)C>[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

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 21866389Hydrogen chloride-ethyl acetateHCID 46941915Tert-butyl (6-iodoimidazo[1,2-b]pyridazin-2-yl)carbamate

Product 1

HCID 574410246-Iodoimidazo[1,2-B]pyridazin-2-amineYield 67%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of tert-butyl (6-iodoimidazo[1,2-b]pyridazin-2-yl)carbamate (10.2 g, 28.3 mmol) in ethyl acetate (50 mL) was added 4N hydrochloric acid/ethyl acetate (75 mL), and the mixture was stirred at room temperature for 4 hr. Diethyl ether (200 mL) was added to the reaction mixture, and the precipitate was filtrated. After washing with saturated aqueous sodium hydrogencarbonate solution, the filtrate was washed with water, acetonitrile and diethyl ether to give the title compound (4.9 g, 67%) as a green powder.

Workup

  1. filtrationthe precipitate was filtrated
  2. washAfter washing with saturated aqueous sodium hydrogencarbonate solution
  3. washthe filtrate was washed with water, acetonitrile and diethyl ether

Sources & evidence

ORD record
ord-41f02720e9e64582a77fdc7ee8f556f0
Source dataset
uspto-grants-2012_09
Patent number
US08273741B2

Reaction notes

Loading…