Pyridine → HCID 23369829, compound

HRID 1900794Notes

Reaction equation

HRID 1900794 reaction equation
[NH2:1][C:2]([CH:4]1[O:18][C:7]2=[C:8]3[C:13](=[C:14]([CH3:16])[CH:15]=[C:6]2[CH2:5]1)[NH:12][C:11](=[O:17])[CH2:10][CH2:9]3)=O.N1C=CC=CC=1.FC(F)(F)C(OC(=O)C(F)(F)F)=O>C(Cl)Cl>[C:2]([CH:4]1[O:18][C:7]2=[C:8]3[C:13](=[C:14]([CH3:16])[CH:15]=[C:6]2[CH2:5]1)[NH:12][C:11](=[O:17])[CH2:10][CH2:9]3)#[N:1]

Participants

5

Reactant 3

HCID 1049Pyridine2×HCID 9845Trifluoroacetic anhydride2×HCID 23369701HCID 23369701, compound

Product 1

HCID 23369829HCID 23369829, compoundYield 94.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

The compound obtained in Example 259 (0.47 g, 1.9 mmol) was dissolved in methylene chloride (40 ml) and pyridine (0.64 ml, 8 mmol). To the obtained solution, trifluoroacetic anhydride (0.56 ml, 4 mmol) was added dropwise while cooling in an ice--water bath, and the mixture was stirred at 0° C. for 1.5 hours. Pyridine (0.64 ml, 8 mmol) and trifluoroacetic anhydride (0.56 ml, 4 mmol) were further added, and stirring was continued at 0° C. for 1 hour. After completion of the reaction, the solvent was distilled off under reduced pressure. To the resultant residue, saturated ammonia--methanol (30 ml) was added, and the mixture was stirred at room temperature for 1.5 hours. The solvent was distilled off under reduced pressure. The residue was combined with chloroform, and extracted. The organic phase was washed with water, aqueous 5% potassium hydrogensulfate, saturated aqueous sodium bicarbonate solution, and saturated aqueous NaCl solution in this order, and dries over magnesium sulfate. The solvent was reduced under reduced pressure, and the residue was subjected to silica gel column chromatography for separation and purification. As a result, 0.41 g of the title compound was obtained as pale yellow powder (94%).

Workup

  1. stirringstirring
  2. waitwas continued at 0° C. for 1 hour
  3. customAfter completion of the reaction
  4. distillationthe solvent was distilled off under reduced pressure
  5. additionTo the resultant residue, saturated ammonia--methanol (30 ml) was added
  6. stirringthe mixture was stirred at room temperature for 1.5 hours
  7. distillationThe solvent was distilled off under reduced pressure
  8. extractionextracted
  9. washThe organic phase was washed with water, aqueous 5% potassium hydrogensulfate, saturated aqueous sodium bicarbonate solution, and saturated aqueous NaCl solution in this order, and dries over magnesium sulfate
  10. customthe residue was subjected to silica gel column chromatography for separation and purification

Sources & evidence

ORD record
ord-cda59a68c67d4f9392f7b8a8bae053e1
Source dataset
uspto-grants-1996_11
Patent number
US05576324

Reaction notes

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