N-bromobutanimide → HCID 178431881, compound

HRID 1825907Notes

Reaction equation

HRID 1825907 reaction equation
[ClH:1].[F:2][C:3]1[CH:18]=[CH:17][C:6]2[N:7]=[C:8]([NH:10][C:11]3[C:15]([CH3:16])=[CH:14][S:13][CH:12]=3)[NH:9][C:5]=2[CH:4]=1.[Br:19]N1C(=O)CCC1=O>C(O)(=O)C>[ClH:1].[Br:19][C:12]1[S:13][CH:14]=[C:15]([CH3:16])[C:11]=1[NH:10][C:8]1[NH:7][C:6]2[CH:17]=[CH:18][C:3]([F:2])=[CH:4][C:5]=2[N:9]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 69099864HCID 69099864, compound

Product 1

HCID 178431881HCID 178431881, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

(5-Fluoro-1H-benzimidazol-2-yl)-(4-methylthiophene-3-yl)amine (300 mg) (example 1) was dissolved in glacial acetic acid (50 ml). At room temperature, N-bromosuccinimide (207 mg) dissolved in glacial acetic acid (10 ml), was slowly added dropwise, with vigorous stirring. After the addition had ended, stirring was continued for another 10 min and the glacial acetic acid was then distilled off under reduced pressure, and the residue was dissolved in ethyl acetate and washed with saturated potassium carbonate solution. The organic phase was dried over magnesium sulfate, filtered and concentrated. The residue was purified by preparative chromatography and the product-containing fractions were combined, freed from acetonitrile, made basic and extracted three times with ethyl acetate. The organic phases were combined, dried (MgSO4) and filtered. Following removal of the solvent under reduced pressure, water and 2N hydrochloric acid were added to the residue and the mixture was freeze-dried. This gave 245 mg of the desired product.

Workup

  1. additionwas slowly added dropwise, with vigorous stirring
  2. additionAfter the addition
  3. distillationthe glacial acetic acid was then distilled off under reduced pressure
  4. dissolutionthe residue was dissolved in ethyl acetate
  5. washwashed with saturated potassium carbonate solution
  6. dry with materialThe organic phase was dried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue was purified by preparative chromatography
  10. extractionextracted three times with ethyl acetate
  11. dry with materialdried (MgSO4)
  12. filtrationfiltered
  13. customremoval of the solvent under reduced pressure, water and 2N hydrochloric acid
  14. additionwere added to the residue
  15. customthe mixture was freeze-dried

Sources & evidence

ORD record
ord-e62b454bc23342c9af1e3c34c6eacad8
Source dataset
uspto-grants-2006_05
Patent number
US07049333B2

Reaction notes

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