Dichloromethane → 5-(2-Chloro-6-methylpyridin-4-yl)-3-methyl-1,3,4-oxadiazol-2(3H)-one

HRID 1056611Notes

Reaction equation

HRID 1056611 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([CH3:12])[N:11]=1)[C:5]([NH:7][NH2:8])=[O:6].FC(F)(F)[C:15](O)=[O:16].[CH2:20](Cl)Cl>>[Cl:1][C:2]1[CH:3]=[C:4]([C:5]2[O:6][C:15](=[O:16])[N:8]([CH3:20])[N:7]=2)[CH:9]=[C:10]([CH3:12])[N:11]=1

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 30290202-Chloro-6-methylpyridine-4-carbohydrazide

Product 1

HCID 900105625-(2-Chloro-6-methylpyridin-4-yl)-3-methyl-1,3,4-oxadiazol-2(3H)-oneYield 92%

Procedure

Step-2: 2-Chloro-6-methylisonicotinohydrazide: To a (0° C.) cooled solution of step-1 intermediate (3.0 g, 10.5 mmol) in DCM (15 mL) was added trifluoroacetic acid (15 mL). After stirring for 2 hat RT, solvent was evaporated under vacuum. Water (20 mL) was added to the resulting residue followed by ethyl acetate (30 mL). The layers were separated and the aqueous layer was extracted with ethyl acetate (2×50 mL). The combined organic layers were washed with brine (20 mL), dried (Na2SO4) and filtered. The filtrate was concentrated under vacuum and the crude product was purified by flash column chromatography to afford 1.80 g (92%) of the title compound as white solid.

Workup

  1. customwas evaporated under vacuum
  2. additionWater (20 mL) was added to the resulting residue
  3. customThe layers were separated
  4. extractionthe aqueous layer was extracted with ethyl acetate (2×50 mL)
  5. washThe combined organic layers were washed with brine (20 mL)
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationThe filtrate was concentrated under vacuum
  9. customthe crude product was purified by flash column chromatography

Sources & evidence

ORD record
ord-1b8407ad9fe143199067ef07f7c335d0
Source dataset
uspto-grants-2016_07
Patent number
US09399638B2

Reaction notes

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