Chloroacetaldehyde → Methyl 3-imidazo[1,2-b]pyridazin-7-ylbenzoate

HRID 407076Notes

Reaction equation

HRID 407076 reaction equation
[NH2:1][C:2]1[N:7]=[N:6][CH:5]=[C:4]([C:8]2[CH:9]=[C:10]([CH:15]=[CH:16][CH:17]=2)[C:11]([O:13][CH3:14])=[O:12])[CH:3]=1.Cl[CH2:19][CH:20]=O>O.C(O)(C)C>[N:1]1[CH:19]=[CH:20][N:7]2[C:2]=1[CH:3]=[C:4]([C:8]1[CH:9]=[C:10]([CH:15]=[CH:16][CH:17]=1)[C:11]([O:13][CH3:14])=[O:12])[CH:5]=[N:6]2

Participants

5

Reactant 2

HCID 33ChloroacetaldehydeHCID 67980189Methyl 3-(6-aminopyridazin-4-yl)benzoate

Product 1

HCID 67980108Methyl 3-imidazo[1,2-b]pyridazin-7-ylbenzoate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3776IsopropanolSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of methyl 3-(6-aminopyridazin-4-yl)benzoate (0.20 g, 0.87 mmol) and chloroacetaldehyde in water (0.3 mL, 50%) in isopropyl alcohol (3.0 mL) was stirred at 100° C. for 4 h. The solvent was removed and the residue was dissolved in ethyl acetate, washed with saturated NaHCO3, water and brine, dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by flash chromatography on a silica gel column with ethyl acetate in methylene chloride (0-30%) to afford the desired product (0.18 g). LCMS (M+H)+: m/z=254.1

Workup

  1. customThe solvent was removed
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. washwashed with saturated NaHCO3, water and brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by flash chromatography on a silica gel column with ethyl acetate in methylene chloride (0-30%)

Sources & evidence

ORD record
ord-0232e37fabdc4918b0b3d55ffea65bb1
Source dataset
uspto-grants-2014_06
Patent number
US08754114B2

Reaction notes

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