Hydrogen chloride-ethyl acetate → N-{3-[(2-aminoimidazo[1,2-b]pyridazin-6-yl)oxy]phenyl}-3-(trifluoromethyl)benzamide

HRID 2391194Notes

Reaction equation

HRID 2391194 reaction equation
[F:1][C:2]([F:37])([F:36])[C:3]1[CH:4]=[C:5]([CH:33]=[CH:34][CH:35]=1)[C:6]([NH:8][C:9]1[CH:10]=[C:11]([CH:30]=[CH:31][CH:32]=1)[O:12][C:13]1[CH:14]=[CH:15][C:16]2[N:17]([CH:19]=[C:20]([NH:22]C(=O)OC(C)(C)C)[N:21]=2)[N:18]=1)=[O:7].Cl.C(OCC)(=O)C>CO>[NH2:22][C:20]1[N:21]=[C:16]2[CH:15]=[CH:14][C:13]([O:12][C:11]3[CH:10]=[C:9]([NH:8][C:6](=[O:7])[C:5]4[CH:33]=[CH:34][CH:35]=[C:3]([C:2]([F:37])([F:36])[F:1])[CH:4]=4)[CH:32]=[CH:31][CH:30]=3)=[N:18][N:17]2[CH:19]=1

Participants

4

Reactant 2

HCID 21866389Hydrogen chloride-ethyl acetateHCID 57387816Tert-butyl [6-(3-{[3-(trifluoromethyl)benzoyl]amino}phenoxy)imidazo[1,2-b]pyridazin-2-yl]carbamate

Product 1

HCID 57385788N-{3-[(2-aminoimidazo[1,2-b]pyridazin-6-yl)oxy]phenyl}-3-(trifluoromethyl)benzamideYield 82.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of tert-butyl [6-(3-{[3-(trifluoromethyl)benzoyl]amino}phenoxy)imidazo[1,2-b]pyridazin-2-yl]carbamate (2.37 g, 4.62 mmol), 4N hydrochloric acid-ethyl acetate solution (50 mL) and methanol (50 mL) was stirred at room temperature for 6 hr. The solvent was evaporated under reduced pressure, saturated aqueous sodium hydrogencarbonate solution was added to the residue, and the mixture was extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate and evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate alone→ethyl acetate/methanol=4:1) to give the title compound (1.57 g, 82%) as a green solid.

Workup

  1. customThe solvent was evaporated under reduced pressure, saturated aqueous sodium hydrogencarbonate solution
  2. additionwas added to the residue
  3. extractionthe mixture was extracted with ethyl acetate
  4. dry with materialThe extract was dried over anhydrous magnesium sulfate
  5. customevaporated under reduced pressure
  6. customthe residue was purified by silica gel column chromatography (ethyl acetate alone→ethyl acetate/methanol=4:1)

Sources & evidence

ORD record
ord-19f714471d3c4f579ce7940396be82d3
Source dataset
uspto-grants-2012_09
Patent number
US08273741B2

Reaction notes

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