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

HRID 1663618Notes

Reaction equation

HRID 1663618 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-32556e1f25014145a088040bee32c62b
Source dataset
uspto-grants-2011_10
Patent number
US08034812B2

Reaction notes

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