1,4-Dioxane → HCID 90960549, compound

HRID 993240Notes

Reaction equation

HRID 993240 reaction equation
[C:1]([O:5][C:6](=[O:35])[CH2:7][CH:8](NCCNCCCC1C=CC=C(NCC2CC2)N=1)[C:9]1[CH:10]=[N:11][C:12]([O:15][CH3:16])=[CH:13][CH:14]=1)([CH3:4])([CH3:3])[CH3:2].CCN(C(C)C)C(C)C.O1CCOCC1>C(Cl)Cl>[C:1]([O:5][C:6](=[O:35])[CH2:7][CH2:8][C:9]1[CH:10]=[N:11][C:12]([O:15][CH3:16])=[CH:13][CH:14]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 312751,4-DioxaneHCID 81531DiisopropylethylamineHCID 70005271HCID 70005271, compound

Product 1

HCID 90960549HCID 90960549, compoundYield 147%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of diamine 2-7 (12.5 g, 25.8 mmol) and DIPEA (13.5 mL, 77.5 mmol) in CH2Cl2 (750 mL) at 0° C. was added p-NO2PhOCOCl (5.47 g, 27.1 mmol) in 4 portions. The resulting mixture was warmed to room temperature and 1,4-dioxane (750 mL) was added and refluxed for 6 h. After cooling, the solution was washed with 10% K2CO3 (3×400 mL) then brine. The organic layer was dried (Na2SO4), filtered, concentrated in vacuo, and purified by flash chromatography (silica, 50% EtOAc/hexanes) affording 9.0 g of cyclic urea 2-8.

Workup

  1. temperaturerefluxed for 6 h
  2. temperatureAfter cooling
  3. washthe solution was washed with 10% K2CO3 (3×400 mL)
  4. dry with materialThe organic layer was dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. custompurified by flash chromatography (silica, 50% EtOAc/hexanes)

Sources & evidence

ORD record
ord-60902cfbc51f46c583cff034650ebaf4
Source dataset
uspto-grants-2002_10
Patent number
US06472403B2

Reaction notes

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