Sodium hydride → HCID 22989387, compound

HRID 1169051Notes

Reaction equation

HRID 1169051 reaction equation
[H-].[Na+].[C:3]1([CH:9]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[O:10][CH:11]2[CH2:16][CH2:15][N:14]([CH2:17][CH2:18][O:19][CH2:20][CH2:21][OH:22])[CH2:13][CH2:12]2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.Cl[C:30]1[C:31]([CH3:39])=[CH:32][C:33]2[N:34]([N:36]=[CH:37][N:38]=2)[N:35]=1>O1CCCC1>[C:23]1([CH:9]([C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=2)[O:10][CH:11]2[CH2:16][CH2:15][N:14]([CH2:17][CH2:18][O:19][CH2:20][CH2:21][O:22][C:30]3[C:31]([CH3:39])=[CH:32][C:33]4[N:34]([N:36]=[CH:37][N:38]=4)[N:35]=3)[CH2:13][CH2:12]2)[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 118051586-Chloro-7-methyl-[1,2,4]triazolo[1,5-b]pyridazineHCID 22989379HCID 22989379, compound

Product 1

HCID 22989387HCID 22989387, compoundYield 64.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

190 mg of 60% sodium hydride in oil was suspended in 15 ml of tetrahydrofuran; 1.47 g of 2-[2-[4-(diphenylmethoxy)piperidino]ethoxy]ethanol was added, followed by heating and refluxing for 1 hour. After cooling, 660 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, dried over magnesium sulfate and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography and eluted with ethyl acetate-methanol a (10:1). The desired fraction was collected; the crystal precipitated was collected by filtration, washed with ethyl ether and dried to yield 1.23 g 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 over magnesium sulfate
  10. concentrationconcentrated under reduced pressure
  11. washeluted with ethyl acetate-methanol a (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-41cd4b3ae2f5470086438c4ce4e47d5a
Source dataset
uspto-grants-2003_09
Patent number
US06627630B1

Reaction notes

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