HCID 131724952, compound → HCID 131724953, compound

HRID 2183529Notes

Reaction equation

HRID 2183529 reaction equation
[CH3:1][N:2]1[C:6]([CH2:7][O:8][C:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:12]3=[N:19][N:20]=[C:21]([C:22]4[CH:26]=[C:25]([CH3:27])[O:24][N:23]=4)[N:11]3[N:10]=2)=[N:5][C:4]([CH2:28][OH:29])=[N:3]1>C(Cl)(Cl)Cl.[O-2].[O-2].[Mn+4]>[CH3:1][N:2]1[C:6]([CH2:7][O:8][C:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:12]3=[N:19][N:20]=[C:21]([C:22]4[CH:26]=[C:25]([CH3:27])[O:24][N:23]=4)[N:11]3[N:10]=2)=[N:5][C:4]([CH:28]=[O:29])=[N:3]1

Participants

4

Reactant 1

HCID 131724952HCID 131724952, compound

Product 1

HCID 131724953HCID 131724953, compoundYield 32.1%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalyst2×HCID 6212ChloroformSolvent

Procedure

A mixture of [1-methyl-5-({[3-(5-methylisoxazol-3-yl)-[1,2,4]triazolo[3,4-α]phthalazin-6-yl]oxy}methyl]-1H-[1,2,4]triazol-3-yl}methanol (Example 20) (1 g, 2.55 mmol) in chloroform (120 ml) and manganese dioxide (4.4 g, 51 mmol) was heated at reflux for 60 h. More manganese dioxide (2.2 g, 25 mmol) was added and reflux continued for further 24 h. The cooled mixture was filtered through “Hyflo” eluting with chloroform. Solvent was evaporated in vacuo to give the crude carbaldehyde as a yellow solid (320 mg). MS (ES+) 391 (M+1).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 60 h
  3. temperaturereflux
  4. filtrationThe cooled mixture was filtered through “Hyflo”
  5. washeluting with chloroform
  6. customSolvent was evaporated in vacuo

Sources & evidence

ORD record
ord-103cc276c55a4ae2a9dd5039d8b2cdf2
Source dataset
uspto-grants-2005_05
Patent number
US06900209B2

Reaction notes

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