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

HRID 456148Notes

Reaction equation

HRID 456148 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 solvents were removed under reduced pressure. The residue was diluted with water and its pH was adjusted to basic with aqueous NaHCO3, 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 silica gel column chromatography to give yellow solid 1-(3-(1-(6-fluoro-1-methyl-1H-indazol-5-yl)ethyl)imidazo[1,2-b]pyridazin-6-yl)ethanone (300 mg, 81%). LCMS (method B): [MH]+=338, tR=2.49 min.

Workup

  1. customthe solvents were 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 silica gel column chromatography

Sources & evidence

ORD record
ord-ab5b765f414c4fb7915170505b566a73
Source dataset
uspto-grants-2013_07
Patent number
US08497368B2

Reaction notes

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