Chlorosuccinimide → HCID 67114955, compound

HRID 1408516Notes

Reaction equation

HRID 1408516 reaction equation
[CH:1]1([C:4]2[N:8]([C:9]3[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][N:10]=3)[N:7]=[C:6]([C:18]([F:21])([F:20])[F:19])[CH:5]=2)[CH2:3][CH2:2]1.[Cl:22]N1C(=O)CCC1=O>CN(C=O)C>[Cl:22][C:5]1[C:6]([C:18]([F:19])([F:20])[F:21])=[N:7][N:8]([C:9]2[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][N:10]=2)[C:4]=1[CH:1]1[CH2:2][CH2:3]1

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 67115283HCID 67115283, compound

Product 1

HCID 67114955HCID 67114955, compoundYield 48.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Intermediate 16 (1.5 g, 5.0 mmol) was dissolved in DMF and to this N-Chlorosuccinimide (0.8 g, 6 mmol) was added at 0° C. Then reaction was allowed to stir at rt for 2 h. After completion of the reaction, work up (EtOAc) and purification afforded the title compound (0.802 g). 1H-NMR (δ ppm, DMSO-d6, 400 MHz): 9.34 (d, J 2.5, 1H), 8.65 (dd, J 2.5, 9, 1H), 8.09 (d, J 9, 1H), 2.48-2.38 (m, 1H), 1.13-1.03 (m, 2H), 0.90-0.82 (m, 2H).

Workup

  1. additionwas added at 0° C
  2. customThen reaction
  3. customAfter completion of the reaction, work
  4. customup (EtOAc) and purification

Sources & evidence

ORD record
ord-f8032fb42cbd4ca5b673572f1112168a
Source dataset
uspto-grants-2014_12
Patent number
US08921364B2

Reaction notes

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