Hydrogen chloride-ethyl acetate → N-{5-[(2-aminoimidazo[1,2-b]pyridazin-6-yl)oxy]-2-fluorophenyl}-1,3-dimethyl-1H-pyrazole-5-carboxamide hydrochloride

HRID 1663861

Reaction equation

HRID 1663861 reaction equation
[Cl:1][C:2]1[C:7]([O:8][C:9]2[CH:10]=[CH:11][C:12]3[N:13]([CH:15]=[C:16]([NH:18]C(C4CC4)=O)[N:17]=3)[N:14]=2)=[CH:6][C:5]([NH:24][C:25]([C:27]2[N:31]([CH3:32])[N:30]=[C:29]([CH3:33])[CH:28]=2)=[O:26])=[C:4]([F:34])[CH:3]=1.Cl.C(OCC)(=O)C>CO>[ClH:1].[NH2:18][C:16]1[N:17]=[C:12]2[CH:11]=[CH:10][C:9]([O:8][C:7]3[CH:2]=[CH:3][C:4]([F:34])=[C:5]([NH:24][C:25]([C:27]4[N:31]([CH3:32])[N:30]=[C:29]([CH3:33])[CH:28]=4)=[O:26])[CH:6]=3)=[N:14][N:13]2[CH:15]=1

Participants

4

Reactant 2

HCID 21866389Hydrogen chloride-ethyl acetateHCID 57505597HCID 57505597, compound

Product 1

HCID 57505567N-{5-[(2-aminoimidazo[1,2-b]pyridazin-6-yl)oxy]-2-fluorophenyl}-1,3-dimethyl-1H-pyrazole-5-carboxamide hydrochlorideYield 101.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a suspension of N-[4-chloro-5-({2-[(cyclopropylcarbonyl)amino]imidazo[1,2-b]pyridazin-6-yl}oxy)-2-fluorophenyl]-1,3-dimethyl-1H-pyrazole-5-carboxamide (2.0 g, 4.72 mmol) in methanol (20 mL) was added 4N hydrochloric acid/ethyl acetate (16 mL) solution. After stirring at room temperature for 4 hr, the mixture was stirred at 50° C. for 12 hr. The solvent was evaporated under reduced pressure, and diisopropyl ether/ethanol (8 mL/2 mL) was added to the residue. The mixture was stirred at room temperature for 2 hr. The precipitate was collected by filtration and washed with diisopropyl ether to give the title compound (2.0 g, quant.) as a brown powder.

Workup

  1. stirringthe mixture was stirred at 50° C. for 12 hr
  2. customThe solvent was evaporated under reduced pressure, and diisopropyl ether/ethanol (8 mL/2 mL)
  3. additionwas added to the residue
  4. stirringThe mixture was stirred at room temperature for 2 hr
  5. filtrationThe precipitate was collected by filtration
  6. washwashed with diisopropyl ether

Sources & evidence

ORD record
ord-058a7a9329e94ce594a4289151fccf88
Source dataset
uspto-grants-2011_10
Patent number
US08034812B2

Linked notes

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