Ethyl 3-chloro-2,4,5-trifluoro-6-nitrobenzoylacetate → HCID 22121269, compound

HRID 1274775Notes

Reaction equation

HRID 1274775 reaction equation
C(O[CH:4]=[C:5]([C:11](=[O:25])[C:12]1[C:17]([N+:18]([O-:20])=[O:19])=[C:16]([F:21])[C:15]([F:22])=[C:14]([Cl:23])[C:13]=1F)[C:6]([O:8][CH2:9][CH3:10])=[O:7])C.ClC1C(F)=C(C([N+]([O-])=O)=C(F)C=1F)C(CC(OCC)=O)=O.[NH2:47][C:48]1[C:53]([F:54])=[CH:52][C:51]([F:55])=[C:50]([NH:56][C:57]([CH3:60])([CH3:59])[CH3:58])[N:49]=1>C(Cl)(Cl)Cl>[C:57]([NH:56][C:50]1[N:49]=[C:48]([N:47]2[C:13]3[C:12](=[C:17]([N+:18]([O-:20])=[O:19])[C:16]([F:21])=[C:15]([F:22])[C:14]=3[Cl:23])[C:11](=[O:25])[C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4]2)[C:53]([F:54])=[CH:52][C:51]=1[F:55])([CH3:60])([CH3:58])[CH3:59]

Participants

5

Reactant 3

HCID 14896544Ethyl 3-chloro-2,4,5-trifluoro-6-nitrobenzoylacetateHCID 15896287N2-(tert-butyl)-3,5-difluoropyridine-2,6-diamineHCID 54224689HCID 54224689, compound

Product 1

HCID 22121269HCID 22121269, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
90 °C

Procedure

To 10 ml of chloroform solution of ethyl 3-ethoxy-2-(3-chloro-2,4,5-trifluoro-6-nitrobenzoyl)acrylate prepared from 3.25 g of ethyl 3-chloro-2,4,5-trifluoro-6-nitrobenzoylacetate by normal process was added 2.14 g of 2-amino-3,5-difluoro-6-t-butylaminopyridine. The solution was concentrated under reduced pressure, and to the residue were added 2.7 g of anhydrous potassium carbonate and 10 ml of N,N-dimethylformamide, and the mixture was stirred at 90° C. for 5 minutes and allowed to cool. The solution was separated by adding 100 ml of chloroform and 500 ml of 2% aqueous solution of citric acid, and the chloroform layer was washed twice with 500 ml of 2% aqueous solution of citric acid, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The precipitate was dispersed in ethanol, collected by filtration, washed with ethanol and diisopropylether successively to obtain 3.13 g of the title compound as a pale yellow powder.

Workup

  1. concentrationThe solution was concentrated under reduced pressure
  2. additionto the residue were added 2.7 g of anhydrous potassium carbonate and 10 ml of N,N-dimethylformamide
  3. temperatureto cool
  4. customThe solution was separated
  5. additionby adding 100 ml of chloroform and 500 ml of 2% aqueous solution of citric acid
  6. washthe chloroform layer was washed twice with 500 ml of 2% aqueous solution of citric acid
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. additionThe precipitate was dispersed in ethanol
  10. filtrationcollected by filtration
  11. washwashed with ethanol and diisopropylether successively

Sources & evidence

ORD record
ord-c675b39a2fe84302a3c83d4317e05ad6
Source dataset
uspto-grants-2000_12
Patent number
US06156903

Reaction notes

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