Pyridine → HCID 58243896, compound

HRID 389152Notes

Reaction equation

HRID 389152 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:14][C:15]([CH3:33])([C:17]2[N:21]([CH3:22])[C:20]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=3[C:29]([F:32])([F:31])[F:30])=[N:19][N:18]=2)[CH3:16])=[C:6]([CH:13]=1)[C:7]([NH:9][NH:10][CH:11]=O)=[O:8].N1C=CC=CC=1.FC(F)(F)S(OS(C(F)(F)F)(=O)=O)(=O)=O>ClCCl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:14][C:15]([CH3:16])([C:17]2[N:21]([CH3:22])[C:20]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=3[C:29]([F:30])([F:32])[F:31])=[N:19][N:18]=2)[CH3:33])=[C:6]([C:7]2[O:8][CH:11]=[N:10][N:9]=2)[CH:13]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 67749Trifluoromethanesulfonic anhydrideHCID 58243915HCID 58243915, compound

Product 1

HCID 58243896HCID 58243896, compoundYield 13%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-10 °C

Procedure

5-chloro-N′-formyl-2-(1-methyl-1-{4-methyl-5-[2-(trifluoromethyl)phenyl}-4H-1,2,4-triazol-3-yl)ethoxy)benzohydrazide (200 mg) was dissolved in dichloromethane (3 ml), pyridine (80 μl) was added thereto, followed by cooling to −10° C. Trifluoromethanesulfonic anhydride (140 μl) was added to the reaction solution, followed by stirring at room temperature for 20 hours. The reaction solution was concentrated under reduced pressure and water was added thereto, followed by extraction with ethyl acetate. The organic layer was washed with saturated aqueous sodium bicarbonate and saturated brine in this order, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:methanol=98:2 to 90:10), the resulting light yellow solid was dissolved in ethyl acetate (3 ml), and 4M hydrogen chloride-ethyl acetate (100 μl) was added thereto. The precipitated solid was collected by filtration, followed by drying and then drying under reduced pressure. The resulting hydrochloride was suspended in chloroform and the suspension was neutralized with saturated aqueous sodium bicarbonate. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by thin layer chromatography (ethyl acetate) and the resulting oily product was powdered with diisopropylether to obtain, as a colorless solid, 2-[5-chloro-2-(1-methyl-1-{4-methyl-5-[2-(trifluoromethyl)phenyl]-4H-1,2,4-triazol-3-yl}ethoxy)phenyl]-1,3,4-oxadiazole (25 mg).

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure and water
  2. additionwas added
  3. extractionfollowed by extraction with ethyl acetate
  4. washThe organic layer was washed with saturated aqueous sodium bicarbonate and saturated brine in this order
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (ethyl acetate:methanol=98:2 to 90:10)
  8. dissolutionthe resulting light yellow solid was dissolved in ethyl acetate (3 ml)
  9. addition4M hydrogen chloride-ethyl acetate (100 μl) was added
  10. filtrationThe precipitated solid was collected by filtration
  11. customby drying
  12. customdrying under reduced pressure
  13. washThe organic layer was washed with saturated brine
  14. dry with materialdried over anhydrous magnesium sulfate
  15. customthe solvent was evaporated under reduced pressure
  16. customThe residue was purified by thin layer chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-19625f74fb4c440cb08617929c6d36fe
Source dataset
uspto-grants-2013_02
Patent number
US08377923B2

Reaction notes

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