Sulfamide → HCID 66681709, compound

HRID 530314Notes

Reaction equation

HRID 530314 reaction equation
[S:1]([NH2:5])([NH2:4])(=[O:3])=[O:2].N[C:7]1[CH:12]=[CH:11][C:10]([C:13]2[N:14]=[CH:15][N:16]([C:18]([N:20]([CH:22]3[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]3)[CH3:21])=[O:19])[CH:17]=2)=[CH:9][CH:8]=1>O1CCOCC1>[CH:22]1([N:20]([CH3:21])[C:18]([N:16]2[CH:17]=[C:13]([C:10]3[CH:11]=[CH:12][C:7]([NH:4][S:1](=[O:3])(=[O:2])[NH2:5])=[CH:8][CH:9]=3)[N:14]=[CH:15]2)=[O:19])[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27]1

Participants

4

Reactant 2

HCID 82267Sulfamide2×HCID 66682011HCID 66682011, compound

Product 1

HCID 66681709HCID 66681709, compoundYield 6%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Sulfamide (0.089 g, 0.922 mmol) was added to a stirred suspension of 4-(4-aminophenyl)-N-cyclohexyl-N-methyl-1H-imidazole-1-carboxamide (0.250 g, 0.838 mmol) in dioxane (2 mL) at room temperature. The suspension was heated at reflux for 4 h to give a clear solution, whereupon more sulfamide (0.089 g, 0.922 mmol) was added and the mixture was heated at reflux for a further 2.5 h. The solvent was removed and the brown residue was purified by chromatography (silica, dichloromethane/methanol, 1%, 2%, 5%). Homogenous fractions were pooled and evaporated. The residue was triturated with ethyl acetate and the colourless solid that formed was removed by filtration. The filtrate was evaporated and purified again by preparative TLC (silica, dichloromethane/10% methanol). The product was extracted from the silica with a mixture of ethyl acetate/10% methanol. Evaporation of the solvent gave a clear oil, that was triturated with a mixture of ethyl acetate and methanol to give the product as an off-white solid (19 mg, 6%).

Workup

  1. temperatureThe suspension was heated
  2. temperatureat reflux for 4 h
  3. customto give a clear solution
  4. temperaturethe mixture was heated
  5. temperatureat reflux for a further 2.5 h
  6. customThe solvent was removed
  7. customthe brown residue was purified by chromatography (silica, dichloromethane/methanol, 1%, 2%, 5%)
  8. customevaporated
  9. customThe residue was triturated with ethyl acetate
  10. customthe colourless solid that formed
  11. customwas removed by filtration
  12. customThe filtrate was evaporated
  13. custompurified again by preparative TLC (silica, dichloromethane/10% methanol)
  14. extractionThe product was extracted from the silica with a mixture of ethyl acetate/10% methanol
  15. customEvaporation of the solvent
  16. customgave a clear oil, that
  17. customwas triturated with a mixture of ethyl acetate and methanol

Sources & evidence

ORD record
ord-3395a83747bf4d49b7958248e8f0a525
Source dataset
uspto-grants-2016_05
Patent number
US09353082B2

Reaction notes

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