Triacetoxyperiodinane → 7,8-bis(4-chlorophenyl)-2-(3-ethoxy-2-oxopropyl)-[1,2,4]triazolo[4,3-b]pyridazin-3(2H)-one

HRID 2224230Notes

Reaction equation

HRID 2224230 reaction equation
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[Cl:23][C:24]1[CH:29]=[CH:28][C:27]([C:30]2[CH:35]=[N:34][N:33]3[C:36](=[O:46])[N:37]([CH2:39][CH:40]([OH:45])[CH2:41][O:42][CH2:43][CH3:44])[N:38]=[C:32]3[C:31]=2[C:47]2[CH:52]=[CH:51][C:50]([Cl:53])=[CH:49][CH:48]=2)=[CH:26][CH:25]=1>C(Cl)Cl>[Cl:23][C:24]1[CH:25]=[CH:26][C:27]([C:30]2[CH:35]=[N:34][N:33]3[C:36](=[O:46])[N:37]([CH2:39][C:40](=[O:45])[CH2:41][O:42][CH2:43][CH3:44])[N:38]=[C:32]3[C:31]=2[C:47]2[CH:48]=[CH:49][C:50]([Cl:53])=[CH:51][CH:52]=2)=[CH:28][CH:29]=1

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 59716624HCID 59716624, compound

Product 1

HCID 597168797,8-bis(4-chlorophenyl)-2-(3-ethoxy-2-oxopropyl)-[1,2,4]triazolo[4,3-b]pyridazin-3(2H)-oneYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The Dess-Martin reagent (56 mg, 0.131 mmol) was added to a solution of 7,8-bis(4-chlorophenyl)-2-(3-ethoxy-2-hydroxypropyl)-[1,2,4]triazolo[4,3-b]pyridazin-3(2H)-one, prepared as described in Example 29, (50 mg, 0.109 mmol) in 1 mL of CH2Cl2. The reaction was stirred for 2 h., filtered, and concentrated under reduced pressure. The crude material was purified by reverse phase HPLC to give the title compound, 7,8-bis(4-chlorophenyl)-2-(3-ethoxy-2-oxopropyl)-[1,2,4]triazolo[4,3-b]pyridazin-3(2H)-one, (47 mg, 95% yield) as a yellow solid. MS [M+H]+: found 457.

Workup

  1. customprepared
  2. filtrationfiltered
  3. concentrationconcentrated under reduced pressure
  4. customThe crude material was purified by reverse phase HPLC

Sources & evidence

ORD record
ord-992ed50cedb54492a032b1b4ce723156
Source dataset
uspto-grants-2008_05
Patent number
US07378418B2

Reaction notes

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