Sodium Chloride → HCID 22989305, compound

HRID 1169042Notes

Reaction equation

HRID 1169042 reaction equation
[C:1]1([CH:7]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[O:8][CH:9]2[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][CH2:17][OH:18])[CH2:11][CH2:10]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].Cl[C:28]1[CH:29]=[CH:30][C:31]2[N:32]([CH:34]=[C:35]([O:37][CH3:38])[N:36]=2)[N:33]=1.[Cl-].[Na+]>CN(C)C=O>[C:19]1([CH:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[O:8][CH:9]2[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][CH2:17][O:18][C:28]3[CH:29]=[CH:30][C:31]4[N:32]([CH:34]=[C:35]([O:37][CH3:38])[N:36]=4)[N:33]=3)[CH2:11][CH2:10]2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 24758Sodium hydrideHCID 229892644-(Diphenylmethoxy)piperidinepropanolHCID 229893386-Chloro-2-methoxyimidazo[1,2-b]pyridazine

Product 1

HCID 22989305HCID 22989305, compoundYield 45.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

758 mg of 4-(diphenylmethoxy)-1-piperidinepropanol was dissolved in 40 ml of N,N-dimethylformamide; 102 mg of a 60% sodium hydride dispersion in mineral oil was added, followed by stirring at 60° C. for 40 minutes. After cooling, 428 mg of 6-chloro-2-methoxyimidazo[1,2-b]pyridazine was added, followed by stirring at 100° C. for 2.5 hours. After cooling, ice water and sodium chloride were added, followed by extraction with ethyl acetate-tetrahydrofuran (1:2); the extract was washed with saturated saline, dried over magnesium sulfate and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography and eluted with ethyl acetate:methanol:triethylamine (50:5:1). The desired fraction was collected and concentrated; the crystal precipitated was recrystallized from ethanol to yield 499 mg of the title compound.

Workup

  1. temperatureAfter cooling
  2. stirringby stirring at 100° C. for 2.5 hours
  3. temperatureAfter cooling
  4. extractionfollowed by extraction with ethyl acetate-tetrahydrofuran (1:2)
  5. washthe extract was washed with saturated saline
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. washeluted with ethyl acetate:methanol:triethylamine (50:5:1)
  9. customThe desired fraction was collected
  10. concentrationconcentrated
  11. customthe crystal precipitated
  12. customwas recrystallized from ethanol

Sources & evidence

ORD record
ord-738a9676f5b14a80829c8b71d0cdaaa1
Source dataset
uspto-grants-2003_09
Patent number
US06627630B1

Reaction notes

Loading…