Sodium hydride → 6-[2-[2-[4-(Diphenylmethyl)piperazino]ethoxy]ethoxy]-7-methyl[1,2,4]triazolo[1,5-b]pyridazine

HRID 1067511Notes

Reaction equation

HRID 1067511 reaction equation
[H-].[Na+].[C:3]1([CH:9]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[N:10]2[CH2:15][CH2:14][N:13]([CH2:16][CH2:17][O:18][CH2:19][CH2:20][OH:21])[CH2:12][CH2:11]2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.Cl[C:29]1[C:30]([CH3:38])=[CH:31][C:32]2[N:33]([N:35]=[CH:36][N:37]=2)[N:34]=1>O1CCCC1>[C:22]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][O:18][CH2:19][CH2:20][O:21][C:29]3[C:30]([CH3:38])=[CH:31][C:32]4[N:33]([N:35]=[CH:36][N:37]=4)[N:34]=3)[CH2:14][CH2:15]2)[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 71135DecloxizineHCID 118051586-Chloro-7-methyl-[1,2,4]triazolo[1,5-b]pyridazine

Product 1

HCID 229893826-[2-[2-[4-(Diphenylmethyl)piperazino]ethoxy]ethoxy]-7-methyl[1,2,4]triazolo[1,5-b]pyridazineYield 48.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

260 mg of 60% sodium hydride dispersion in mineral oil was suspended in 20 ml of tetrahydrofuran; 1.15 g of 4-(diphenylmethyl)-1-[2-(2-hydroxyethoxy)ethyl]piperazine was added, followed by heating and refluxing for 1 hour. After cooling, 540 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 (10:10:1). The desired fraction was collected; the crystal precipitated was collected by filtration, washed with ethyl ether and dried to yield 730 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 (10:10:1)
  12. customThe desired fraction was collected
  13. customthe crystal precipitated
  14. filtrationwas collected by filtration
  15. washwashed with ethyl ether
  16. customdried

Sources & evidence

ORD record
ord-4d18ddf017224ddfa93ab79630c5e025
Source dataset
uspto-grants-2001_06
Patent number
US06248740B1

Reaction notes

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