Sodium hydride → HCID 22989321, compound

HRID 1067549Notes

Reaction equation

HRID 1067549 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]3([C:40]([O:42]C(C)C)=[O:41])[CH2:39][CH2:38]3)[N:36]=2)[N:33]=1>CN(C)C(=O)C>[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]5([C:40]([OH:42])=[O:41])[CH2:39][CH2:38]5)[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 3

HCID 24758Sodium hydrideHCID 229892644-(Diphenylmethoxy)piperidinepropanolHCID 22989336HCID 22989336, compound

Product 1

HCID 22989321HCID 22989321, compoundYield 26.9%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

1.14 g of 4-(diphenylmethoxy)-1-piperidinepropanol was dissolved in 15 ml of N,N-dimethylacetamide; 140 mg of a 60% dispersion of sodium hydride in mineral oil was added, followed by stirring at room temperature under reduced pressure for 30 minutes. To the reaction mixture, 980 mg of isopropyl 1-(6-chloroimidazo[1,2-b]pyridazin-2-yl)cyclopropanecarboxylate was added under ice cooling conditions, followed by stirring at constant temperature for 4 hours. Ice water was added, followed by saturation with sodium chloride and subsequent extraction with ethyl acetate-tetrahydrofuran (1:1); the extract was dried with magnesium sulfate. The dry product was 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 to yield 496 mg of the title compound.

Workup

  1. stirringby stirring at constant temperature for 4 hours
  2. extractionfollowed by saturation with sodium chloride and subsequent extraction with ethyl acetate-tetrahydrofuran (1:1)
  3. dry with materialthe extract was dried with magnesium sulfate
  4. concentrationThe dry product was concentrated under reduced pressure
  5. washeluted with ethyl acetate
  6. customThe desired fraction was collected
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-855a6d68f0064ea49e180fc7ea28ef4c
Source dataset
uspto-grants-2001_06
Patent number
US06248740B1

Reaction notes

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