Sodium hydride → HCID 22989375, compound

HRID 1067513Notes

Reaction equation

HRID 1067513 reaction equation
[H-].[Na+].[C:3]1([CH:9]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[N:10]2[CH2:15][CH2:14][N:13]([CH2:16][CH2:17][CH2:18][CH2:19][OH:20])[CH2:12][CH2:11]2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[Cl:27][C:28]1[C:29]([CH3:37])=[CH:30][C:31]2[N:32]([N:34]=[CH:35][N:36]=2)[N:33]=1>O1CCCC1>[ClH:27].[ClH:27].[C:21]1([CH:9]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:10]2[CH2:11][CH2:12][N:13]([CH2:16][CH2:17][CH2:18][CH2:19][O:20][C:28]3[C:29]([CH3:37])=[CH:30][C:31]4[N:32]([N:34]=[CH:35][N:36]=4)[N:33]=3)[CH2:14][CH2:15]2)[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 118051586-Chloro-7-methyl-[1,2,4]triazolo[1,5-b]pyridazineHCID 22989250HCID 22989250, compound

Product 1

HCID 22989375HCID 22989375, compoundYield 58.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

240 mg of a 60% sodium hydride dispersion in mineral oil was suspended in 20 ml of tetrahydrofuran; 0.99 g of 4-(diphenylmethyl)-1-piperazinebutanol was added, followed by heating and refluxing for 1 hour. After cooling, 510 mg of 6-chloro-7-methyl[1,2,4]triazolo[1,5-b]pyridazine was added, followed by heating and refluxing for 3 hours. After cooling, ice water was added, followed by extraction with ethyl acetate; 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 dichloromethane-ethyl acetate-methanol (20:20:1). The desired fraction was collected and dissolved in 5 ml of ethyl acetate; 0.64 ml of a 4 N hydrogen chloride solution in ethyl acetate was added; the crystal precipitated was collected by filtration, washed with ethyl ether and dried to yield 470 mg of the title compound.

Workup

  1. temperatureby heating
  2. temperaturerefluxing for 1 hour
  3. temperatureAfter cooling
  4. temperatureby heating
  5. temperaturerefluxing for 3 hours
  6. temperatureAfter cooling
  7. extractionfollowed by extraction with ethyl acetate
  8. washthe extract was washed with saturated saline
  9. dry with materialdried with magnesium sulfate
  10. concentrationAfter the dry product was concentrated under reduced pressure
  11. washeluted with dichloromethane-ethyl acetate-methanol (20:20:1)
  12. customThe desired fraction was collected
  13. dissolutiondissolved in 5 ml of ethyl acetate
  14. addition0.64 ml of a 4 N hydrogen chloride solution in ethyl acetate was added
  15. customthe crystal precipitated
  16. filtrationwas collected by filtration
  17. washwashed with ethyl ether
  18. customdried

Sources & evidence

ORD record
ord-2c2fd4020f904bb2aa8679335e80cbcc
Source dataset
uspto-grants-2001_06
Patent number
US06248740B1

Reaction notes

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