Nitrogen → 3-Bromo-6-piperazin-1-yl-imidazo[1,2-b]pyridazine

HRID 870727Notes

Reaction equation

HRID 870727 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.[NH:12]1[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1.N#N>CO>[Br:1][C:2]1[N:6]2[N:7]=[C:8]([N:12]3[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]3)[CH:9]=[CH:10][C:5]2=[N:4][CH:3]=1

Participants

5

Reactant 3

HCID 947NitrogenHCID 4837PiperazineHCID 128723233-Bromo-6-chloroimidazo(1,2-b)pyridazine

Product 1

HCID 866964323-Bromo-6-piperazin-1-yl-imidazo[1,2-b]pyridazineYield 70.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
120 °C

Procedure

3-Bromo-6-chloro-imidazo[1,2-b]pyridazine [13526-66-4] (1.1 g, 4.5 mmol) and piperazine [110-85-0] (3.6 g, 41.8 mmol) were ground together in a mortar to an intimate mixture and transferred to a 15 mL round bottomed flask containing a magnetic stir bar. The flask was fitted to a reflux condenser, N2 blanketed, and the reaction pot immersed in an ambient temperature oil bath. While the neat solid mixture stirred, the bath was heated to 120° C. over 0.5 h and held at nominal temperature for a total of 17 h. The bath was removed and the molten reaction allowed to cool and to solidify. The solid mass was dissolved in methanol, transferred to a separatory funnel, and partitioned between brine (pH adjusted to 10 with 3N aqueous sodium hydroxide) and ethyl acetate. The phase separated extract was dried (MgSO4) and evaporated to afford 0.9 g of 3-bromo-6-piperazin-1-yl-imidazo[1,2-b]pyridazine as a light yellow solid which was used without further purification. LRMS (ESI) m/z 282.1/284.1 [(M+H)]+, calc'd for C10H12BrN5: 282.14.

Workup

  1. customtransferred to a 15 mL round bottomed flask
  2. additioncontaining a magnetic stir bar
  3. customThe flask was fitted to a reflux condenser
  4. customthe reaction
  5. custompot immersed in an ambient temperature
  6. customheld at nominal temperature for a total of 17 h
  7. customThe bath was removed
  8. customthe molten reaction
  9. temperatureto cool
  10. customtransferred to a separatory funnel
  11. custompartitioned between brine (
  12. customThe phase separated
  13. extractionextract
  14. dry with materialwas dried (MgSO4)
  15. customevaporated

Sources & evidence

ORD record
ord-fa0fdfd5cfd74f1abfb01392bd4bad15
Source dataset
uspto-grants-2015_03
Patent number
US08969565B2

Reaction notes

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