Chloroacetaldehyde → 6-(1-Methyl-1H-pyrazol-4-yl)-imidazo[1,2-b]pyridazine

HRID 69164Notes

Reaction equation

HRID 69164 reaction equation
[CH3:1][N:2]1[CH:6]=[C:5]([C:7]2[N:12]=[N:11][C:10]([NH2:13])=[CH:9][CH:8]=2)[CH:4]=[N:3]1.Cl[CH2:15][CH:16]=O.O.C([O-])(O)=O.[Na+]>CCO>[CH3:1][N:2]1[CH:6]=[C:5]([C:7]2[CH:8]=[CH:9][C:10]3[N:11]([CH:15]=[CH:16][N:13]=3)[N:12]=2)[CH:4]=[N:3]1

Participants

6

Reactant 4

HCID 33ChloroacetaldehydeHCID 962WaterHCID 516892Sodium BicarbonateHCID 622026836-(1-methyl-1H-pyrazol-4-yl)pyridazin-3-amine

Product 1

HCID 686316286-(1-Methyl-1H-pyrazol-4-yl)-imidazo[1,2-b]pyridazine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

6-(1-Methyl-1H-pyrazol-4-yl)-pyridazin-3-ylamine (Stage 8.3, 2.41 g, 13.8 mmol) was dissolved in EtOH (18 mL). Chloroacetaldehyde 55% in H2O (1.61 mL, 13.8 mmol) and NaHCO3 (2.3 g, 27.5 mmol) were added. The RM was stirred at 80° C. for 5 h. The solvent was removed and a solution of 5% NaHCO3 was added. The mixture was extracted twice with DCM/MeOH (9/1). The combined organic phases were washed with brine, dried over Na2SO4, and the solvent was removed to afford the title compound as a black solid (tR 1.0 min (conditions 2), MH+=200).

Workup

  1. customThe solvent was removed
  2. additiona solution of 5% NaHCO3 was added
  3. extractionThe mixture was extracted twice with DCM/MeOH (9/1)
  4. washThe combined organic phases were washed with brine
  5. dry with materialdried over Na2SO4
  6. customthe solvent was removed

Sources & evidence

ORD record
ord-1aaa71ba514744da87d2224d6ea85970
Source dataset
uspto-grants-2014_09
Patent number
US08822468B2

Reaction notes

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