Selenium Dioxide → HCID 11854408, compound

HRID 2102978Notes

Reaction equation

HRID 2102978 reaction equation
[CH3:1][C:2]1[CH:20]=[C:19]([C:21]#[C:22][C:23]([CH3:26])([CH3:25])[CH3:24])[CH:18]=[CH:17][C:3]=1[C:4]([NH:6][C:7]1[CH:8]=[CH:9][C:10]2[S:14][C:13]([CH3:15])=[N:12][C:11]=2[CH:16]=1)=[O:5].[Se](=O)=[O:28]>O1CCOCC1>[S:14]1[C:10]2[CH:9]=[CH:8][C:7]([NH:6][C:4](=[O:5])[C:3]3[CH:17]=[CH:18][C:19]([C:21]#[C:22][C:23]([CH3:24])([CH3:25])[CH3:26])=[CH:20][C:2]=3[CH3:1])=[CH:16][C:11]=2[N:12]=[CH:13]1.[OH:28][CH2:15][C:13]1[S:14][C:10]2[CH:9]=[CH:8][C:7]([NH:6][C:4](=[O:5])[C:3]3[CH:17]=[CH:18][C:19]([C:21]#[C:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[CH:20][C:2]=3[CH3:1])=[CH:16][C:11]=2[N:12]=1

Participants

5

Reactant 2

HCID 24007Selenium DioxideHCID 11853635HCID 11853635, compound

Product 2

HCID 11854408HCID 11854408, compoundHCID 11854409HCID 11854409, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 2-methyl-N-(2-methylbenzo[d]thiazol-5-yl)-4-(3,3-dimethylbut-1-ynyl)benzamide (50 mg, 0.14 mmol), selenium dioxide (46 mg, 0.41 mmol), and 1,4-dioxane (10 mL) was stirred under an atmosphere of nitrogen at 80° C. overnight. After cooling, the mixture was filtered through Celite® and the filtrate was treated with aq. NaHCO3 and extracted with EtOAc. The organic layer was washed with brine, dried (Na2SO4), and concentrated under vacuum. The residue was dissolved in THF-H2O (2:1) (10 mL) and NaBH4 (50 mg) was added slowly. The mixture was stirred at rt for 2 h and then acidified with 1N HCl. After treated with aq. NaHCO3, the mixture was extracted with EtOAc. The combined organic layers were washed with brine, dried (Na2SO4), and concentrated under vacuum. The residue was purified by preparative thin-layer chromatography to give N-(benzo[d]thiazol-5-yl)-2-methyl-4-(3,3-dimethylbut-1-ynyl)benzamide (compound 198-11 mg) as a light yellow solid and N-(2-(hydroxymethyl)benzo[d]thiazol-5-yl)-2-methyl-4-(3,3-dimethylbut-1-ynyl)benzamide (compound 197-27 mg) as a light yellow solid.

Workup

  1. temperatureAfter cooling
  2. filtrationthe mixture was filtered through Celite®
  3. additionthe filtrate was treated with aq. NaHCO3
  4. extractionextracted with EtOAc
  5. washThe organic layer was washed with brine
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated under vacuum
  8. dissolutionThe residue was dissolved in THF-H2O (2:1) (10 mL)
  9. additionNaBH4 (50 mg) was added slowly
  10. stirringThe mixture was stirred at rt for 2 h
  11. additionAfter treated with aq. NaHCO3
  12. extractionthe mixture was extracted with EtOAc
  13. washThe combined organic layers were washed with brine
  14. dry with materialdried (Na2SO4)
  15. concentrationconcentrated under vacuum
  16. customThe residue was purified by preparative thin-layer chromatography

Sources & evidence

ORD record
ord-11abf673a64043d2ba8d7a493b551f53
Source dataset
uspto-grants-2009_08
Patent number
US07576099B2

Reaction notes

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