Sodium Hydroxide → 1-Cyclohexyl-2-(4-oxo-2-phenyl-4H-chromen-6-yl)-1H-benzoimidazole-5-carboxylic Acid

HRID 1788568

Reaktionsgleichung

Reaktionsgleichung von HRID 1788568
[O:1]=[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:12](O)=O)[CH:10]=2)[O:5][C:4]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:3]1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(C(C)C)CC)(C)C.C([O:56][C:57](=[O:72])[C:58]1[CH:63]=[CH:62][C:61]([NH:64][CH:65]2[CH2:70][CH2:69][CH2:68][CH2:67][CH2:66]2)=[C:60]([NH2:71])[CH:59]=1)C.[OH-].[Na+]>CN(C=O)C>[CH:65]1([N:64]2[C:61]3[CH:62]=[CH:63][C:58]([C:57]([OH:56])=[O:72])=[CH:59][C:60]=3[N:71]=[C:12]2[C:9]2[CH:10]=[C:11]3[C:6](=[CH:7][CH:8]=2)[O:5][C:4]([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)=[CH:3][C:2]3=[O:1])[CH2:66][CH2:67][CH2:68][CH2:69][CH2:70]1

Komponenten

7

Edukt 5

HCID 14798Sodium HydroxideHCID 81531DiisopropylethylamineHCID 4933774-Oxo-2-phenyl-4H-chromene-6-carboxylic acidHCID 4068248Ferrostatin-1HCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Produkt 1

HCID 114767971-Cyclohexyl-2-(4-oxo-2-phenyl-4H-chromen-6-yl)-1H-benzoimidazole-5-carboxylic Acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

4-Oxo-2-phenyl-4H-chromene-6-carboxylic acid (280 mg, 1.05 mmol) was dissolved in DMF (5 mL), and HATU (418 mg, 1.1 eq.) and diisopropyl ethylamine (402 μL) were added. After stirring at room temperature for 15 minutes, 3-amino-4-cyclohexylamino-benzoic acid ethyl ester (303 mg, 1.1 eq.) dissolved in 2 mL DMF was added. After stirring overnight, the reaction was evaporated, dissolved in ethyl acetate and washed with water and brine, dried with sodium sulfate, evaporated and dried overnight. The product was then refluxed in acetic acid for 4h, evaporated to dryness, and coevaporated 2 more times with toluene. Saponification proceeds by dissolving the residue in ethanol (10 mL), adding 10 eq. of 1N NaOH solution and stirring at 40° C. for 4 hr. The ethanol was evaporated, water was added and acidified. The resulting precipitate was purified via reverse-phase HPLC. Yield: 58 mg

Aufarbeitung

  1. additionwas added
  2. stirringAfter stirring overnight
  3. customthe reaction was evaporated
  4. dissolutiondissolved in ethyl acetate
  5. washwashed with water and brine
  6. dry with materialdried with sodium sulfate
  7. customevaporated
  8. customdried overnight
  9. temperatureThe product was then refluxed in acetic acid for 4h
  10. customevaporated to dryness
  11. dissolutionSaponification proceeds by dissolving the residue in ethanol (10 mL)
  12. stirringstirring at 40° C. for 4 hr
  13. customThe ethanol was evaporated
  14. additionwater was added
  15. customThe resulting precipitate was purified via reverse-phase HPLC

Quellen und Nachweise

ORD-Eintrag
ord-879bf9131e944162837b5e78db54c54a
Quelldatensatz
uspto-grants-2009_03
Patentnummer
US07511145B2

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