Benzylamine → HCID 117874940, compound

HRID 715927Notes

Reaction equation

HRID 715927 reaction equation
[Br:1][C:2]1[N:6]2[N:7]=[C:8](Cl)[CH:9]=[CH:10][C:5]2=[N:4][CH:3]=1.[C:12]1([CH2:18][NH2:19])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[F-].[K+]>CS(C)=O>[CH2:18]([NH:19][C:8]1[CH:9]=[CH:10][C:5]2[N:6]([C:2]([Br:1])=[CH:3][N:4]=2)[N:7]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 7504BenzylamineHCID 522689Potassium FluorideHCID 128723233-Bromo-6-chloroimidazo(1,2-b)pyridazine

Product 1

HCID 117874940HCID 117874940, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
130 °C

Procedure

3-Bromo-6-chloroimidazo[1,2-b]pyridazine (20.0 g), phenylmethanamine (11.3 ml), and potassium fluoride (12.0 g) were dissolved in dimethyl sulfoxide (400 ml), and the solution was stirred at 130° C. for 24 hours. After standing to cool to room temperature, the reaction solution was poured into ice water (2.0 L). The resulting solid was collected by filtration and dried under reduced pressure. The obtained solid was dissolved in hot ethyl acetate, and the insoluble matter was filtered under heating. After distilling off the solvent, the solid was recrystallized from ethyl acetate to obtain the title compound (21.0 g).

Workup

  1. temperatureto cool to room temperature
  2. filtrationThe resulting solid was collected by filtration
  3. customdried under reduced pressure
  4. dissolutionThe obtained solid was dissolved in hot ethyl acetate
  5. filtrationthe insoluble matter was filtered
  6. temperatureunder heating
  7. distillationAfter distilling off the solvent
  8. customthe solid was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-404c43b391694267bf5ea593c0e4505f
Source dataset
uspto-grants-2015_11
Patent number
US09187489B2

Reaction notes

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