Water → 6-(3-{[(1,3-dimethyl-1H-pyrazol-5-yl)carbonyl]amino}phenoxy)-N-methylimidazo[1,2-b]pyridazine-2-carboxamide

HRID 1667940Notes

Reaction equation

HRID 1667940 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:19]=[CH:20][CH:21]=1)[O:5][C:6]1[CH:7]=[CH:8][C:9]2[N:10]([CH:12]=[C:13]([C:15]([NH:17][CH3:18])=[O:16])[N:14]=2)[N:11]=1.[CH3:22][N:23]1[C:27]([C:28](Cl)=[O:29])=[CH:26][C:25]([CH3:31])=[N:24]1.O>CN(C)C(=O)C>[CH3:22][N:23]1[C:27]([C:28]([NH:1][C:2]2[CH:3]=[C:4]([CH:19]=[CH:20][CH:21]=2)[O:5][C:6]2[CH:7]=[CH:8][C:9]3[N:10]([CH:12]=[C:13]([C:15]([NH:17][CH3:18])=[O:16])[N:14]=3)[N:11]=2)=[O:29])=[CH:26][C:25]([CH3:31])=[N:24]1

Participants

5

Reactant 3

HCID 962WaterHCID 27362992,5-Dimethyl-2H-pyrazole-3-carbonyl chlorideHCID 575055106-(3-aminophenoxy)-N-methylimidazo[1,2-b]pyridazine-2-carboxamide

Product 1

HCID 575055116-(3-{[(1,3-dimethyl-1H-pyrazol-5-yl)carbonyl]amino}phenoxy)-N-methylimidazo[1,2-b]pyridazine-2-carboxamideYield 73.4%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

To a solution of 6-(3-aminophenoxy)-N-methylimidazo[1,2-b]pyridazine-2-carboxamide (250 mg, 0.88 mmol) in N,N-dimethylacetamide (2.5 mL) was added 1,3-dimethyl-1H-pyrazole-5-carbonyl chloride (253 mg, 1.59 mmol). After stirring at room temperature for 1 hr, water was added to the reaction mixture, and the precipitate was collected by filtration. The obtained residue was washed with water, acetonitrile and diethyl ether to give the title compound (262 mg, 73%) as a white powder.

Workup

  1. filtrationthe precipitate was collected by filtration
  2. washThe obtained residue was washed with water, acetonitrile and diethyl ether

Sources & evidence

ORD record
ord-1820b9804baf4277b2a523a92ec8a958
Source dataset
uspto-grants-2011_10
Patent number
US08044049B2

Reaction notes

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