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

HRID 456156Notes

Reaction equation

HRID 456156 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 10 mL AcOH was heated at 50° C. for 3 hour. The solvent was removed under reduced pressure. The residue was diluted with water and adjusted the pH value of solution to around 8 with aqueous NaHCO3, 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% pure). 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
  3. extractionextracted 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% pure)

Sources & evidence

ORD record
ord-7488dba1efe74934b7996af0cb5329f8
Source dataset
uspto-grants-2013_07
Patent number
US08497368B2

Reaction notes

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