Dimethylformamide → HCID 69842990, compound

HRID 1169060Notes

Reaction equation

HRID 1169060 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]([C:37]([CH3:45])([CH3:44])[C:38]([O:40][CH:41]([CH3:43])[CH3:42])=[O:39])[N:36]=2)[N:33]=1.CN(C)[CH:48]=[O:49]>>[C:48]([OH:49])(=[O:8])/[CH:35]=[CH:37]/[C:38]([OH:40])=[O:39].[C:48]([OH:49])(=[O:8])/[CH:35]=[CH:37]/[C:38]([OH:40])=[O:39].[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]([C:37]([CH3:44])([CH3:45])[C:38]([O:40][CH:41]([CH3:42])[CH3:43])=[O:39])[N:36]=4)[N:33]=3)[CH2:11][CH2:10]2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 22989226HCID 22989226, compoundHCID 229892644-(Diphenylmethoxy)piperidinepropanol

Product 1

HCID 69842990HCID 69842990, compound

Procedure

8.10 g of 4-(diphenylmethoxy)-1-piperidinepropanol was dissolved in 60 ml of N,N-dimethylformamide; 1.11 g of 60% sodium hydride in oil was added, followed by stirring at room temperature under reduced pressure for 1 hour. While the solution was ice cooled, 7.79 g of isopropyl 2-(6-chloroimidazo[1,2-b]pyridazin-2-yl]-2-methylpropionate was added, followed by stirring at constant temperature for 4 hours. Ice water was added, followed by extraction with ethyl acetate-tetrahydrofuran (1:1); 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 and concentrated under reduced pressure. The residue was dissolved in 10 ml of ethanol; 476 mg of fumaric acid was added, followed by concentration again. The residue was crystallized by the addition of ethyl acetate, collected by filtration, washed with ethyl acetate and dried to yield 1.05 g of the title compound.

Workup

  1. temperaturecooled
  2. stirringby stirring at constant temperature for 4 hours
  3. extractionfollowed by extraction with ethyl acetate-tetrahydrofuran (1:1)
  4. washthe extract was washed with saturated saline
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. washeluted with ethyl acetate
  8. customThe desired fraction was collected
  9. concentrationconcentrated under reduced pressure
  10. dissolutionThe residue was dissolved in 10 ml of ethanol
  11. addition476 mg of fumaric acid was added
  12. concentrationfollowed by concentration again
  13. customThe residue was crystallized by the addition of ethyl acetate
  14. filtrationcollected by filtration
  15. washwashed with ethyl acetate
  16. customdried

Sources & evidence

ORD record
ord-7055c2a9e9404a588f8762c660eb9326
Source dataset
uspto-grants-2003_09
Patent number
US06627630B1

Reaction notes

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