Triethylamine → N-[3-(5-bromo-1H-benzimidazol-1-yl)phenyl]-N'-(2,2,2-trifluoro ethyl)urea

HRID 406970Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 406970
[Br:1][C:2]1[CH:17]=[CH:16][C:5]2[N:6]([C:9]3[CH:10]=[C:11]([CH:13]=[CH:14][CH:15]=3)[NH2:12])[CH:7]=[N:8][C:4]=2[CH:3]=1.Cl[C:19](OC1C=CC([N+]([O-])=O)=CC=1)=[O:20].C(N(CC)CC)C.[F:38][C:39]([F:43])([F:42])[CH2:40][NH2:41]>O1CCCC1.CN(C)C1C=CN=CC=1>[Br:1][C:2]1[CH:17]=[CH:16][C:5]2[N:6]([C:9]3[CH:10]=[C:11]([NH:12][C:19]([NH:41][CH2:40][C:39]([F:43])([F:42])[F:38])=[O:20])[CH:13]=[CH:14][CH:15]=3)[CH:7]=[N:8][C:4]=2[CH:3]=1

Komponenten

7

Edukt 4

HCID 8471TriethylamineHCID 9773Ethanamine, 2,2,2-trifluoro-HCID 821294-Nitrophenyl chloroformateHCID 679807243-(5-bromo-1H-benzimidazol-1-yl)aniline

Produkt 1

HCID 67980496N-[3-(5-bromo-1H-benzimidazol-1-yl)phenyl]-N'-(2,2,2-trifluoro ethyl)ureaAusbeute 56 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 3-(5-bromo-1H-benzimidazol-1-yl)aniline (1.0 g, 3.5 mmol) in tetrahydrofuran (20 mL) was added p-nitrophenyl chloroformate (980 mg, 4.8 mmol, Aldrich, Cat. 160210), triethylamine (1.4 mL, 10. mmol) and 4-dimethylaminopyridine (80 mg, 0.7 mmol, Aldrich, Cat. 107700). The solution was stirred at r.t. 1 h., then 2,2,2-trifluoroethanamine (520 mg, 5.2 mmol, Alfa Aesar, Cat. No. B20789) was added. The reaction mixture was stirred at r.t. overnight and quenched with NaHCO3 aqueous solution, extracted with ethyl acetate. The combined organic phases were washed with brine, and dried over MgSO4. After filtration, the filtrate was concentrated under reduced pressure. The residue was purified by flash chromatograph on a silica gel column using 85% ethyl acetate in methylene chloride as eluent to afford the desired compound (0.81 g, 56%). LCMS (M+H)+: m/z=413.0.

Aufarbeitung

  1. custom1 h.
  2. additionB20789) was added
  3. stirringThe reaction mixture was stirred at r.t. overnight
  4. customquenched with NaHCO3 aqueous solution
  5. extractionextracted with ethyl acetate
  6. washThe combined organic phases were washed with brine
  7. dry with materialdried over MgSO4
  8. filtrationAfter filtration
  9. concentrationthe filtrate was concentrated under reduced pressure
  10. customThe residue was purified by flash chromatograph on a silica gel column

Quellen und Nachweise

ORD-Eintrag
ord-49be7c4978094c82aeb6da96255dc2ed
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08754114B2

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