HCID 22121270, compound → HCID 22121260, compound

HRID 1274741Notes

Reaction equation

HRID 1274741 reaction equation
[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[CH:6][C:5]([F:10])=[C:4]([NH:11][C:12]([CH3:15])([CH3:14])[CH3:13])[N:3]=1.C([O:18][CH:19]=[C:20]([C:26](=[O:37])[C:27]1[CH:32]=[C:31]([F:33])[C:30]([F:34])=[C:29]([Cl:35])[C:28]=1F)[C:21]([O:23][CH2:24][CH3:25])=[O:22])C>C(O)C>[C:12]([NH:11][C:4]1[N:3]=[C:2]([N:1]2[C:28]3[C:27](=[CH:32][C:31]([F:33])=[C:30]([F:34])[C:29]=3[Cl:35])[C:26](=[O:37])[CH:20]([C:21]([O:23][CH2:24][CH3:25])=[O:22])[C:19]2=[O:18])[C:7]([C:8]#[N:9])=[CH:6][C:5]=1[F:10])([CH3:15])([CH3:14])[CH3:13]

Participants

4

Reactant 2

HCID 22121270HCID 22121270, compoundHCID 54402571Ethyl 3-ethoxy-2-(3-chloro-2,4,5-trifluorobenzoyl)acrylate

Product 1

HCID 22121260HCID 22121260, compoundYield 45.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A solution of 300 mg of unpurified 2-amino-6-t-butylamino-3-cyano-5-fluoropyridine in 2 ml ethanol was added dropwise to a solution of 420 mg of ethyl 3-ethoxy-2-(3-chloro-2,4,5-trifluorobenzoyl)acrylate in 2 ml ethanol at room temperature, and the mixture was stirred overnight. The solvent was distilled off the reaction solution, and to the residue were added 3 ml of N,N-dimethylformamide and 210 mg of potassium carbonate, and the mixture was stirred at room temperature for 90 minutes and 80° C. for 2 hours. The reaction solution was extracted by adding water and ethyl acetate, and the organic layer was collected and dried over magnesium sulfate. The solvent was distilled off, and the residue was collected by filtration using ethanol and washed with diethylether to obtain 280 mg of the title compound as a pale yellow powder.

Workup

  1. distillationThe solvent was distilled off the reaction solution
  2. additionto the residue were added 3 ml of N,N-dimethylformamide and 210 mg of potassium carbonate
  3. stirringthe mixture was stirred at room temperature for 90 minutes and 80° C. for 2 hours
  4. extractionThe reaction solution was extracted
  5. additionby adding water and ethyl acetate
  6. customthe organic layer was collected
  7. dry with materialdried over magnesium sulfate
  8. distillationThe solvent was distilled off
  9. filtrationthe residue was collected by filtration
  10. washwashed with diethylether

Sources & evidence

ORD record
ord-61438da5e70d431db8e8f29937844d51
Source dataset
uspto-grants-2000_12
Patent number
US06156903

Reaction notes

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