Water → 6-Chloro-2-triphenylmethyl[1,2,4]triazolo[4,3-b]pyridazin-3(2H)-one

HRID 397573Notes

Reaction equation

HRID 397573 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8](=[O:11])[NH:9][N:10]=2)[N:7]=1.Cl[C:13]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(N(C(C)C)C(C)C)C.O>CN(C)C=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8](=[O:11])[N:9]([C:13]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)([C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=3)[C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)[N:10]=2)[N:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6456Trityl chlorideHCID 81531DiisopropylethylamineHCID 64071826-chloro-2H,3H-[1,2,4]triazolo[4,3-b]pyridazin-3-one

Product 1

HCID 230003076-Chloro-2-triphenylmethyl[1,2,4]triazolo[4,3-b]pyridazin-3(2H)-oneYield 71.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

0.341 g of 6-chloro[1,2,4]triazolo[4,3-b]pyridazin-3(2H)-one and 0.669 g of chlorotriphenylmethane were dissolved in 5 ml of N,N-dimethylformamide; 0.414 ml of N-ethyldiisopropylamine was added, followed by stirring at room temperature for 2 days. After water was added, the reaction mixture was extracted with ethyl acetate; the extract was washed with saline and dried over magnesium sulfate. After concentration under reduced pressure, the residue was subjected to silica gel column chromatography and eluted with hexane-ethyl acetate (2:1). The desired fraction was collected and concentrated; the crystal obtained was collected by filtration, washed with diethyl ether, and dried, to yield 0.591 g of the title compound.

Workup

  1. extractionthe reaction mixture was extracted with ethyl acetate
  2. washthe extract was washed with saline
  3. dry with materialdried over magnesium sulfate
  4. concentrationAfter concentration under reduced pressure
  5. washeluted with hexane-ethyl acetate (2:1)
  6. customThe desired fraction was collected
  7. concentrationconcentrated
  8. customthe crystal obtained
  9. filtrationwas collected by filtration
  10. washwashed with diethyl ether
  11. customdried

Sources & evidence

ORD record
ord-fbbef0e461ac4f1bafb5463b640ff18f
Source dataset
uspto-grants-2003_08
Patent number
US06610694B1

Reaction notes

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