Sodium Chloride → HCID 22989305, compound

HRID 1067509Notes

Reaction equation

HRID 1067509 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 and dried with magnesium sulfate. After the dry product was 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 with magnesium sulfate
  7. concentrationAfter the dry product was concentrated 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-2178beb6d6c7426f80fcbe8679a00def
Source dataset
uspto-grants-2001_06
Patent number
US06248740B1

Reaction notes

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