Dimethylformamide → HCID 69842605, compound

HRID 1169045Notes

Reaction equation

HRID 1169045 reaction equation
[H-].[Na+].[C:3]1([CH:9]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[O:10][CH:11]2[CH2:16][CH2:15][N:14]([CH2:17][CH2:18][CH2:19][OH:20])[CH2:13][CH2:12]2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.Cl[C:28]1[CH:29]=[CH:30][C:31]2[N:32]([CH:34]=[C:35]([C:37]([CH3:46])([CH3:45])[C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39])[N:36]=2)[N:33]=1.CN(C)[CH:49]=[O:50]>>[C:49]([OH:50])(=[O:10])/[CH:35]=[CH:37]/[C:38]([OH:40])=[O:39].[C:49]([OH:50])(=[O:10])/[CH:35]=[CH:37]/[C:38]([OH:40])=[O:39].[C:21]1([CH:9]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=2)[O:10][CH:11]2[CH2:16][CH2:15][N:14]([CH2:17][CH2:18][CH2:19][O:20][C:28]3[CH:29]=[CH:30][C:31]4[N:32]([CH:34]=[C:35]([C:37]([CH3:46])([CH3:45])[C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39])[N:36]=4)[N:33]=3)[CH2:13][CH2:12]2)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 10891764HCID 10891764, compoundHCID 229892644-(Diphenylmethoxy)piperidinepropanol

Product 1

HCID 69842605HCID 69842605, compound

Procedure

70 mg of 60% sodium hydride dispersion in mineral oil was dissolved in 5 ml of N,N-dimethylformamide; 570 mg of 4-(diphenylmethoxy)-1-piperidinepropanol was added, followed by stirring at room temperature under reduced pressure for 30 minutes. After 520 mg of t-butyl 2-(6-chloroimidazo[1,2-b]pyridazin-2-yl)-2-methylpropionate was added, followed by stirring at room temperature for 8 hours. Ice water was added, followed by extraction with ethyl acetate; 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 (195:5:1). The desired fraction was collected and dissolved in 5 ml of ethyl acetate; a solution of 233 mg of fumaric acid in 10 ml of methanol was added, followed by concentration. The crystal precipitated was collected by filtration, washed with acetone and dried to yield 631 mg of the title compound.

Workup

  1. stirringby stirring at room temperature for 8 hours
  2. extractionfollowed by extraction with ethyl acetate
  3. washthe extract was washed with saturated saline
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. washeluted with ethyl acetate:methanol:triethylamine (195:5:1)
  7. customThe desired fraction was collected
  8. dissolutiondissolved in 5 ml of ethyl acetate
  9. additiona solution of 233 mg of fumaric acid in 10 ml of methanol was added
  10. concentrationfollowed by concentration
  11. customThe crystal precipitated
  12. filtrationwas collected by filtration
  13. washwashed with acetone
  14. customdried

Sources & evidence

ORD record
ord-0a551d25360a45cda423b3d92c2a1e47
Source dataset
uspto-grants-2003_09
Patent number
US06627630B1

Reaction notes

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