Chloroacetyl chloride → HCID 57672251, compound

HRID 252065Notes

Reaction equation

HRID 252065 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:21]([NH:23][OH:24])=[NH:22])[CH:5]=[C:6]2[C:10]=1[C:9](=[O:11])[N:8]([CH2:12][CH:13]1[CH2:18][CH2:17][C:16]([F:20])([F:19])[CH2:15][CH2:14]1)[CH2:7]2.[Cl:25][CH2:26][C:27](Cl)=O.C([O-])([O-])=O.[K+].[K+]>C(#N)C.CN(C=O)C.O>[Cl:1][C:2]1[CH:3]=[C:4]([C:21]2[N:22]=[C:27]([CH2:26][Cl:25])[O:24][N:23]=2)[CH:5]=[C:6]2[C:10]=1[C:9](=[O:11])[N:8]([CH2:12][CH:13]1[CH2:14][CH2:15][C:16]([F:19])([F:20])[CH2:17][CH2:18]1)[CH2:7]2

Participants

7

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 11430Potassium CarbonateHCID 178513330HCID 178513330, compound

Product 1

HCID 57672251HCID 57672251, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolvent

Procedure

To a solution of 7-Chloro-N-hydroxy-1-oxo-2-[(4,4-difluorocyclohexyl)methyl]-2,3-dihydro-1H-isoindole-5-carboxamidine (450 mg, 1.26 mmol) in acetonitrile (10 ml), chloroacetyl chloride (170 mg, 1.51 mmol) was added, followed by K2CO3 (260 mg, 1.89 mmol). The mixture was stirred overnight. After diluter with EtOAc (20 ml), it was washed with water, brine, dried over anhydrous sodium sulphate, filtered and concentrated to provide a yellow foam. This foam was stirred in DMF (2 ml) at 140° C. for 3 hours. After cooled to room temperature, it was diluted with water (5 ml). The product was extracted with EtOAc. The organic layer was washed with water, brine, dried over anhydrous sodium sulphate, filtered and concentrated. The product was purified by column chromatography (40 to 60% EtOAc in hexanes) to yield the title compound as a white solid

Workup

  1. washAfter diluter with EtOAc (20 ml), it was washed with water, brine
  2. dry with materialdried over anhydrous sodium sulphate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto provide a yellow foam
  6. extractionThe product was extracted with EtOAc
  7. washThe organic layer was washed with water, brine
  8. dry with materialdried over anhydrous sodium sulphate
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customThe product was purified by column chromatography (40 to 60% EtOAc in hexanes)

Sources & evidence

ORD record
ord-9e7398a114d5453391323f1418f578d2
Source dataset
uspto-grants-2011_01
Patent number
US07868008B2

Reaction notes

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