Acetic Anhydride → HCID 67273092, compound

HRID 600624Notes

Reaction equation

HRID 600624 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:8]=[C:9]([C:11]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)=[O:12])[N:10]=2)[CH:7]=1.[C:19](OC(=O)C)(=[O:21])[CH3:20]>C(O)(=O)C>[C:11]([C:9]1[N:10]=[C:5]2[CH:4]=[CH:3][C:2]([NH:1][C:19](=[O:21])[CH3:20])=[CH:7][N:6]2[CH:8]=1)(=[O:12])[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 67273847HCID 67273847, compound

Product 1

HCID 67273092HCID 67273092, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

The (6-aminoimidazo[1,2-a]pyridin-2-yl)(phenyl)methanone is dissolved in 7 mL of acetic acid and treated with 0.8 mL of acetic anhydride. The reaction medium is refluxed for 2 hours, cooled, filtered and concentrated to dryness. The residue is taken up in ethyl acetate and saturated sodium hydrogen carbonate solution. The organic phase is washed and concentrated, and the product obtained is chromatographed on a column of silica, eluting with a 95/5 mixture of dichloromethane and methanol. The fractions containing the expected product are combined and concentrated to give 150 mg of N-(2-benzoylimidazo[1,2-a]pyridin-6-yl)acetamide as a mixture with N-(3-benzoylimidazo[1,2-a]pyridin-6-yl)acetamide. The two isomers are separated by preparative LC/MS preparative to give 54 mg of purified N-(2-benzoylimidazo[1,2-a]pyridin-6-yl)acetamide in the form of a beige-colored solid.

Workup

  1. temperatureThe reaction medium is refluxed for 2 hours
  2. temperaturecooled
  3. filtrationfiltered
  4. concentrationconcentrated to dryness
  5. washThe organic phase is washed
  6. concentrationconcentrated
  7. customthe product obtained
  8. customis chromatographed on a column of silica
  9. washeluting with a 95/5 mixture of dichloromethane and methanol
  10. additionThe fractions containing the expected product
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-91cf372351614c37a4dd1370e32f9ff4
Source dataset
uspto-grants-2011_03
Patent number
US07902219B2

Reaction notes

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