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

HRID 1892327Notes

Reaction equation

HRID 1892327 reaction equation
C([O:3][C:4]([C:6]1[CH:7]=[CH:8][C:9]2[N:10]([C:12]([CH2:15][C:16]3[CH:17]=[C:18]4[C:22](=[CH:23][CH:24]=3)[N:21]([CH3:25])[N:20]=[CH:19]4)=[CH:13][N:14]=2)[N:11]=1)=[CH2:5])C.Cl>CC(O)=O>[CH3:25][N:21]1[C:22]2[C:18](=[CH:17][C:16]([CH2:15][C:12]3[N:10]4[N:11]=[C:6]([C:4](=[O:3])[CH3:5])[CH:7]=[CH:8][C:9]4=[N:14][CH:13]=3)=[CH:24][CH:23]=2)[CH:19]=[N:20]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 581904976-(1-Ethoxy-vinyl)-3-(1-methyl-1H-indazol-5-ylmethyl)-imidazo[1,2-b]pyridazine

Product 1

HCID 581905161-(3-((1-Methyl-1H-indazol-5-yl)methyl)imidazo[1,2-b]pyridazin-6-yl)ethanone

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 6-(1-ethoxy-vinyl)-3-(1-methyl-1H-indazol-5-ylmethyl)-imidazo[1,2-b]pyridazine (50 mg, 0.15 mmol) and HCl (0.15 mL, 0.15 mmol) in AcOH (10 mL) was heated at 50° C. for 3 h. The solvent was removed under reduced pressure. The residue was diluted with water and pH of solution was adjusted to around 8 with saturated NaHCO3 solution, then was extracted with DCM three times. Organic layers were combined, dried over Na2SO4 and concentrated. The crude product was used in the next step without purification (45 mg, 75%, 76% purity). LCMS (method A): [MH]+=306, tR=5.03 min.

Workup

  1. customThe solvent was removed under reduced pressure
  2. additionThe residue was diluted with water and pH of solution
  3. extractionwas extracted with DCM three times
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customThe crude product was used in the next step without purification (45 mg, 75%, 76% purity)

Sources & evidence

ORD record
ord-3e96691b2524444ca9be5ada44729b79
Source dataset
uspto-grants-2013_08
Patent number
US08507676B2

Reaction notes

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