Hydrochloric Acid → 1-(3-(1-(6-Fluoro-1-methyl-1H-indazol-5-yl)ethyl)imidazo[1,2-b]pyridazin-6-yl)ethanone

HRID 1892371Notes

Reaction equation

HRID 1892371 reaction equation
C([O:3][C:4]([C:6]1[CH:7]=[CH:8][C:9]2[N:10]([C:12]([CH:15]([C:17]3[CH:18]=[C:19]4[C:23](=[CH:24][C:25]=3[F:26])[N:22]([CH3:27])[N:21]=[CH:20]4)[CH3:16])=[CH:13][N:14]=2)[N:11]=1)=[CH2:5])C.Cl>C(O)(=O)C>[F:26][C:25]1[CH:24]=[C:23]2[C:19]([CH:20]=[N:21][N:22]2[CH3:27])=[CH:18][C:17]=1[CH:15]([C:12]1[N:10]2[N:11]=[C:6]([C:4](=[O:3])[CH3:5])[CH:7]=[CH:8][C:9]2=[N:14][CH:13]=1)[CH3:16]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 581905236-(1-Ethoxyvinyl)-3-(1-(6-fluoro-1-methyl-1H-indazol-5-yl)ethyl)imidazo[1,2-b]pyridazine

Product 1

HCID 581905981-(3-(1-(6-Fluoro-1-methyl-1H-indazol-5-yl)ethyl)imidazo[1,2-b]pyridazin-6-yl)ethanoneYield 90.3%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of the 6-(1-ethoxyvinyl)-3-(1-(6-fluoro-1-methyl-1H-indazol-5-yl)ethyl)-imidazo[1,2-b]pyridazine (450 mg, 0.985 mmol) in acetic acid (8 mL) was added 3N HCl (0.5 mL). The solution was stirred at rt for 2 h and the solvent was removed under reduced pressure. The residue was diluted with water and its pH was adjusted to basic with aqueous NaHCO3 solution and extracted with DCM. The organic layer was washed with NaHCO3 (aq) and brine, dried over Na2SO4, and concentrated in vacuo. The residue was purified by column chromatography to give 300 mg (81%) of the title compound as a yellow solid. LCMS (method B): [MH]+=338, tR=2.49 min.

Workup

  1. customthe solvent was removed under reduced pressure
  2. additionThe residue was diluted with water and its pH
  3. extractionextracted with DCM
  4. washThe organic layer was washed with NaHCO3 (aq) and brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-8ff4c70a8c884ca38ac4ec08e8d0cd7f
Source dataset
uspto-grants-2013_08
Patent number
US08507676B2

Reaction notes

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