Sodium Chloride → HCID 22989248, compound

HRID 1169043Notes

Reaction equation

HRID 1169043 reaction equation
[C:1]1([CH:7]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[N:8]2[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][CH2:16][OH:17])[CH2:10][CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].Cl[C:27]1[CH:28]=[CH:29][C:30]2[N:31]([CH:33]=[C:34]([O:36][CH3:37])[N:35]=2)[N:32]=1.[Cl-].[Na+]>CN(C)C=O>[C:18]1([CH:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[N:8]2[CH2:9][CH2:10][N:11]([CH2:14][CH2:15][CH2:16][O:17][C:27]3[CH:28]=[CH:29][C:30]4[N:31]([CH:33]=[C:34]([O:36][CH3:37])[N:35]=4)[N:32]=3)[CH2:12][CH2:13]2)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 24758Sodium hydrideHCID 155241464-Benzhydryl-1-piperazinepropanolHCID 229893386-Chloro-2-methoxyimidazo[1,2-b]pyridazine

Product 1

HCID 22989248HCID 22989248, compoundYield 26.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

251 mg of 4-(diphenylmethyl)-1-piperazinepropanol was dissolved in 14 ml of N,N-dimethylformamide; 36 mg of a 60% sodium hydride dispersion in mineral oil was added, followed by stirring at 60° C. for 30 minutes. After cooling, 149 mg of 6-chloro-2-methoxyimidazo[1,2-b]pyridazine was added, followed by stirring at 90° C. for 4.5 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. The desired fraction was collected; the crystal precipitated was recrystallized from ethyl acetate to yield 99 mg of the title compound.

Workup

  1. temperatureAfter cooling
  2. stirringby stirring at 90° C. for 4.5 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
  9. customThe desired fraction was collected
  10. customthe crystal precipitated
  11. customwas recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-b272c3576dc4491bb3a6884ead0d789f
Source dataset
uspto-grants-2003_09
Patent number
US06627630B1

Reaction notes

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