N-bromobutanimide → HCID 22139859, compound

HRID 2358175Notes

Reaction equation

HRID 2358175 reaction equation
[Br:1]N1C(=O)CCC1=O.FC(F)(F)C(O)=O.[F:16][C:17]1[C:32]([F:33])=[CH:31][C:20]2[NH:21][C:22]([NH:24][C:25]3[C:29]([CH3:30])=[CH:28][S:27][CH:26]=3)=[N:23][C:19]=2[CH:18]=1>C(O)(=O)C>[Br:1][C:26]1[S:27][CH:28]=[C:29]([CH3:30])[C:25]=1[NH:24][C:22]1[NH:21][C:20]2[CH:31]=[C:32]([F:33])[C:17]([F:16])=[CH:18][C:19]=2[N:23]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 68455350HCID 68455350, compound

Product 1

HCID 22139859HCID 22139859, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

At room temperature, a solution of N-bromosuccinimide (8 mg) in glacial acetic acid (0.5 ml) was added dropwise to a solution of (5,6-difluoro-1H-benzimidazol-2-yl)-(4-methylthiophen-3-yl)amine trifluoroacetic acid salt (15 mg, example 45) in glacial acetic acid (0.5 ml) in a ReactiVial, and the mixture was stirred at room temperature for 0.5 h. The acetic acid was then removed under reduced pressure and saturated potassium carbonate solution and ethyl acetate were added to the residue. The organic phase was removed and the aqueous phase was then extracted twice with ethyl acetate. The combined organic phases were dried using magnesium sulfate and the drying agent was then filtered off. The residue that remained after removal of the solvent under reduced pressure was purified by preparative chromatography. The product-containing fractions were combined and freed from acetonitrile, saturated sodium bicarbonate solution was added to the residue and the mixture was extracted three times with ethyl acetate. The organic phases were combined, dried (MgSO4) and filtered. After removal of the ethyl acetate under reduced pressure, the residue was coevaporated with toluene and then dried under high vacuum. This gave 8.1 mg of the desired compound.

Workup

  1. customThe acetic acid was then removed under reduced pressure and saturated potassium carbonate solution and ethyl acetate
  2. additionwere added to the residue
  3. customThe organic phase was removed
  4. extractionthe aqueous phase was then extracted twice with ethyl acetate
  5. customThe combined organic phases were dried
  6. filtrationthe drying agent was then filtered off
  7. customafter removal of the solvent under reduced pressure
  8. customwas purified by preparative chromatography
  9. additionwas added to the residue
  10. extractionthe mixture was extracted three times with ethyl acetate
  11. dry with materialdried (MgSO4)
  12. filtrationfiltered
  13. customAfter removal of the ethyl acetate under reduced pressure
  14. customdried under high vacuum

Sources & evidence

ORD record
ord-fb858758ac8149109801d61c7801ebc1
Source dataset
uspto-grants-2010_07
Patent number
US07763643B2

Reaction notes

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