Water → Tert-butyl (6-iodoimidazo[1,2-b]pyridazin-2-yl)carbamate

HRID 2391113Notes

Reaction equation

HRID 2391113 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:20])[O:15][C:16]([CH3:19])([CH3:18])[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:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])[N:1]=2)[N:4]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24203Sodium Phosphate, DibasicHCID 108678346-Iodopyridazin-3-amineHCID 14221822tert-Butyl (2-chloroacetyl)carbamate

Product 1

HCID 46941915Tert-butyl (6-iodoimidazo[1,2-b]pyridazin-2-yl)carbamateYield 63%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of 3-amino-6-iodopyridazine (10.0 g, 45.2 mmol) in N,N-dimethylacetamide (100 mL) were added tert-butyl (chloroacetyl)carbamate (14.0 g, 72.4 mmol) and disodium hydrogenphosphate (16.1 g, 113 mmol), and the mixture was stirred at 120° C. for 3 hr. After cooling the mixture to room temperature, water (400 mL) was added to the mixture, and the precipitated crystals were filtrated, and washed with acetonitrile and petroleum ether to give the title compound (10.2 g, 63%) as a green powder.

Workup

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

Sources & evidence

ORD record
ord-f0cb8e9b8a704cd4a633db5a4371938d
Source dataset
uspto-grants-2012_09
Patent number
US08273741B2

Reaction notes

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