Water → HCID 86624091, compound

HRID 512474Notes

Reaction equation

HRID 512474 reaction equation
[F:1][C:2]([F:21])([C:17]([F:20])([F:19])[F:18])[C:3]([F:16])([F:15])[C:4]1[NH:9][C:8](=[O:10])[C:7]([C:11]([O:13][CH3:14])=[O:12])=[CH:6][CH:5]=1.[Cl:22]N1C(=O)CCC1=O.O>CN(C)C=O>[Cl:22][C:5]1[CH:6]=[C:7]([C:11]([O:13][CH3:14])=[O:12])[C:8](=[O:10])[NH:9][C:4]=1[C:3]([F:15])([F:16])[C:2]([F:1])([F:21])[C:17]([F:19])([F:18])[F:20]

Participants

5

Reactant 3

HCID 962WaterHCID 31398ChlorosuccinimideHCID 86624089HCID 86624089, compound

Product 1

HCID 86624091HCID 86624091, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

16.7 g (52 mmol) of methyl 6-(heptafluoropropyl)-2-oxo-1,2-dihydropyridine-3-carboxylate were dissolved in 160 ml of N,N-dimethylformamide, and 7.08 g (52 mmol) of N-chlorosuccinimide were added at room temperature. After 3 hours of stirring at 50° C., the reaction mixture was added to water and extracted repeatedly with ethyl acetate. The organic phase was then separated off, washed with water and dried. The resulting crude product was then purified by preparative RP-HPLC. This gave 10.1 g (54% of theory) of the product as a colorless powder.

Workup

  1. extractionextracted repeatedly with ethyl acetate
  2. customThe organic phase was then separated off
  3. washwashed with water
  4. customdried
  5. customThe resulting crude product was then purified by preparative RP-HPLC

Sources & evidence

ORD record
ord-57a74fb1f3c04336b0646c555a6a6a2a
Source dataset
uspto-grants-2015_08
Patent number
US09102623B2

Reaction notes

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