Chlorosuccinimide → HCID 22139832, compound

HRID 2358174Notes

Reaction equation

HRID 2358174 reaction equation
[Cl:1]N1C(=O)CCC1=O.[F:9][C:10]1[C:25]([F:26])=[CH:24][C:13]2[NH:14][C:15]([NH:17][C:18]3[C:22]([CH3:23])=[CH:21][S:20][CH:19]=3)=[N:16][C:12]=2[CH:11]=1>C(O)(=O)C>[ClH:1].[Cl:1][C:19]1[S:20][CH:21]=[C:22]([CH3:23])[C:18]=1[NH:17][C:15]1[NH:14][C:13]2[CH:24]=[C:25]([F:26])[C:10]([F:9])=[CH:11][C:12]=2[N:16]=1

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 22139818HCID 22139818, compound

Product 1

HCID 22139832HCID 22139832, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

At room temperature, a solution of N-chlorosuccinimide (124.6 mg) in glacial acetic acid (5 ml) was added dropwise to a solution of (5,6-difluoro-1H-benzimidazol-2-yl)-(4-methylthiophen-3-yl)amine (225 mg) in glacial acetic acid (5 ml). The mixture was then stirred at room temperature for 3.5 hours. The glacial acetic acid was then removed and the residue was taken up in water and adjusted to pH 10 using 2 M aqueous sodium hydroxide solution. The aqueous phase was extracted three times with ethyl acetate, the combined organic phases were dried over magnesium sulfate and the solvent was removed. 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), filtered and concentrated. The residue was taken up in water, acidified with 10% strength hydrochloric acid and freeze-dried. This gave 81 mg of the desired product as a solid.

Workup

  1. customThe glacial acetic acid was then removed
  2. extractionThe aqueous phase was extracted three times with ethyl acetate
  3. dry with materialthe combined organic phases were dried over magnesium sulfate
  4. customthe solvent was removed
  5. customThe residue was purified by preparative chromatography
  6. extractionextracted three times with ethyl acetate
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customfreeze-dried

Sources & evidence

ORD record
ord-610d27e3f00e4db9a6b411b2fed03010
Source dataset
uspto-grants-2010_07
Patent number
US07763643B2

Reaction notes

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