Selenium Dioxide → HCID 56598243, compound

HRID 1505467Notes

Reaction equation

HRID 1505467 reaction equation
N[C:2]1[C:3]2[C:27]3(CCOC3)[C:26](=[O:32])[NH:25][C:4]=2[N:5]=[C:6]([C:8]2[C:16]3[C:11](=[N:12][CH:13]=[CH:14][CH:15]=3)[N:10]([CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[F:24])[N:9]=2)[N:7]=1.[Se](=O)=[O:34]>O1CCOCC1>[F:24][C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=1[CH2:17][N:10]1[C:11]2=[N:12][CH:13]=[CH:14][CH:15]=[C:16]2[C:8]([C:6]2[N:7]=[CH:2][C:3]3[C:27](=[O:34])[C:26](=[O:32])[NH:25][C:4]=3[N:5]=2)=[N:9]1

Participants

4

Reactant 2

HCID 24007Selenium DioxideHCID 56598426HCID 56598426, compound

Product 1

HCID 56598243HCID 56598243, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

2.00 g (5.550 mmol) of Example 4 were initially charged in dioxane (200 ml), 3.079 g (27.751 mmol) of selenium dioxide were added and the mixture was heated at reflux for 2 h. After cooling, the mixture was filtered and the filtrate was concentrated and purified by chromatography on silica gel (mobile phase:cyclohexane/ethyl acetate 1:1). This gave 890 mg of the title compound (42% of theory).

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 2 h
  3. temperatureAfter cooling
  4. filtrationthe mixture was filtered
  5. concentrationthe filtrate was concentrated
  6. custompurified by chromatography on silica gel (mobile phase:cyclohexane/ethyl acetate 1:1)

Sources & evidence

ORD record
ord-0391916ede6640368fdc5c07d56a0498
Source dataset
uspto-grants-2015_12
Patent number
US09216978B2

Reaction notes

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