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

HRID 1663619

Reaction equation

HRID 1663619 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-1094202de2f14325bc375ca47f4dffeb
Source dataset
uspto-grants-2011_10
Patent number
US08034812B2

Linked notes

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