Toluene → HCID 178478945, compound

HRID 2250510Notes

Reaction equation

HRID 2250510 reaction equation
[Cl:1][C:2]1[C:3]([NH:7][C:8]2[NH:12][C:11]3[CH:13]=[CH:14][C:15]([F:17])=[CH:16][C:10]=3[N:9]=2)=[CH:4][S:5][CH:6]=1.[Cl:18]N1C(=O)CCC1=O.C1(C)C=CC=CC=1>C(O)(=O)C>[ClH:1].[Cl:18][C:4]1[S:5][CH:6]=[C:2]([Cl:1])[C:3]=1[NH:7][C:8]1[NH:12][C:11]2[CH:13]=[CH:14][C:15]([F:17])=[CH:16][C:10]=2[N:9]=1

Participants

5

Reactant 3

HCID 1140TolueneHCID 31398Chlorosuccinimide2×HCID 178505472HCID 178505472, compound

Product 1

HCID 178478945HCID 178478945, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

(4-Chloro-thiophen-3-yl)-(5-fluoro-1H-benzoimidazol-2-yl)-amine (85 mg) was dissolved in acetic acid (4 ml) and under vigorous stirring at room temperature a solution of N-chlorosuccinimide (42 mg) in acetic acid (4 ml) was added. After stirring for 45 min. at room temperature, stirring was continued for 5 h at 50° C. After the addition of further N-chlorosuccinimide (4 mg) stirring was continued for one hour at 50° C. Then the reaction mixture was treated with toluene (20 ml) and solvent mixture distilled off. The residue was dissolved in ethyl acetate and washed with saturated potassium carbonate solution. The organic layer was dried (MgSO4), filtered and concentrated. The residue was purified by preparative HPLC, the product containing fractions were combined, the acetonitrile was removed, the aqueous residue made basic and extracted three times with ethyl acetate. The organic layers were combined, dried (MgSO4) and filtered. After removal of the solvent water and 2 N HCl were added to the residue. After freeze drying the desired product (17 mg) was obtained.

Workup

  1. additionwas added
  2. stirringstirring
  3. waitwas continued for 5 h at 50° C
  4. stirringstirring
  5. waitwas continued for one hour at 50° C
  6. distillationdistilled off
  7. dissolutionThe residue was dissolved in ethyl acetate
  8. washwashed with saturated potassium carbonate solution
  9. dry with materialThe organic layer was dried (MgSO4)
  10. filtrationfiltered
  11. concentrationconcentrated
  12. customThe residue was purified by preparative HPLC
  13. additionthe product containing fractions
  14. customthe acetonitrile was removed
  15. extractionextracted three times with ethyl acetate
  16. dry with materialdried (MgSO4)
  17. filtrationfiltered
  18. customAfter removal of the solvent water and 2 N HCl
  19. additionwere added to the residue
  20. dry with materialAfter freeze drying the desired product (17 mg)
  21. customwas obtained

Sources & evidence

ORD record
ord-0fe0065ae7944f84977d64426731bf29
Source dataset
uspto-grants-2008_01
Patent number
US07317033B2

Reaction notes

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