Water → Ethyl (6-iodoimidazo[1,2-B]pyridazin-2-YL)carbamate

HRID 1667803Notes

Reaction equation

HRID 1667803 reaction equation
[NH2:1][C:2]1[N:3]=[N:4][C:5]([I:8])=[CH:6][CH:7]=1.Cl[CH2:10][C:11]([NH:13][C:14](=[O:18])[O:15][CH2:16][CH3:17])=O.P([O-])([O-])(O)=O.[Na+].[Na+].O>CN(C)C(=O)C>[I:8][C:5]1[CH:6]=[CH:7][C:2]2[N:3]([CH:10]=[C:11]([NH:13][C:14](=[O:18])[O:15][CH2:16][CH3:17])[N:1]=2)[N:4]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24203Sodium Phosphate, DibasicHCID 233830Ethyl (2-chloroacetyl)carbamateHCID 108678346-Iodopyridazin-3-amine

Product 1

HCID 57386057Ethyl (6-iodoimidazo[1,2-B]pyridazin-2-YL)carbamateYield 81.4%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
110 °C

Procedure

To a solution of 3-amino-6-iodopyridazine (27.0 g, 122 mmol) in N,N-dimethylacetamide (270 mL) were added ethyl (chloroacetyl)carbamate (32.4 g, 195 mmol) and disodium hydrogenphosphate (43.4 g, 305 mmol), and the mixture was stirred at 110° C. for 3 hr. After cooling the mixture to room temperature, water (810 mL) was added, and the precipitated crystals were filtrated, and washed with acetonitrile and ether to give the title compound (33.0 g, 81%) as a dark brown powder.

Workup

  1. temperatureAfter cooling the mixture to room temperature
  2. filtrationthe precipitated crystals were filtrated
  3. washwashed with acetonitrile and ether

Sources & evidence

ORD record
ord-75c6ed287c34454f83014a4d1be27080
Source dataset
uspto-grants-2011_10
Patent number
US08044049B2

Reaction notes

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