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

HRID 406970Notes

Reaction equation

HRID 406970 reaction equation
[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

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-49be7c4978094c82aeb6da96255dc2ed
Source dataset
uspto-grants-2014_06
Patent number
US08754114B2

Reaction notes

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