p-Toluenesulfonic acid → HCID 24771610, compound

HRID 645362Notes

Reaction equation

HRID 645362 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([C:11]2[N:12]=[C:13]3[CH:18]=[CH:17][C:16]([C:19](O)([CH3:21])[CH3:20])=[CH:15][N:14]3[CH:23]=2)=[O:10])=[CH:4][CH:3]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C(C)=CC=CC=1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9]([C:11]2[N:12]=[C:13]3[CH:18]=[CH:17][C:16]([C:19]([CH3:21])=[CH2:20])=[CH:15][N:14]3[CH:23]=2)=[O:10])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 68616693HCID 68616693, compound

Product 1

HCID 24771610HCID 24771610, compoundYield 65.6%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

A solution of 110 mg of N-(4-fluorophenyl)-6-(1-hydroxy-1-methylethyl)imidazo[1,2-a]pyridine-2-carboxamide and 3.3 mg of para-toluenesulfonic acid in 5 ml of xylene is heated at reflux for 6 hours and then evaporated to dryness under reduced pressure. The residue is taken up in 200 ml of dichloromethane and 20 ml of water. The organic phase is dried and concentrated, and the residue is purified by chromatography on silica, elution being carried out with a mixture of dichloromethane and ethyl acetate (95/5). The fractions comprising the expected product are combined and concentrated to dryness. The residue is triturated and washed with ethyl ether, filtered off and dried to give 68 mg of N-(4-fluorophenyl)-6-isopropenylimidazo[1,2-a]pyridine-2-carboxamide in the form of a beige solid.

Workup

  1. temperatureat reflux for 6 hours
  2. customevaporated to dryness under reduced pressure
  3. customThe organic phase is dried
  4. concentrationconcentrated
  5. customthe residue is purified by chromatography on silica, elution
  6. additionbeing carried out with a mixture of dichloromethane and ethyl acetate (95/5)
  7. concentrationconcentrated to dryness
  8. customThe residue is triturated
  9. washwashed with ethyl ether
  10. filtrationfiltered off
  11. customdried

Sources & evidence

ORD record
ord-70dfa5adbdef45c086482b50b1cdea3d
Source dataset
uspto-grants-2010_04
Patent number
US07704989B2

Reaction notes

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