Water → 6-Chloro-N-phenylimidazo[1,2-a]pyridine-2-carboxamide

HRID 645358Notes

Reaction equation

HRID 645358 reaction equation
CN(C)C=O.[Cl:6][C:7]1[CH:8]=[CH:9][C:10]2[N:11]([CH:13]=[C:14]([C:16]([OH:18])=O)[N:15]=2)[CH:12]=1.[NH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.O>ClCCl.S(Cl)(Cl)=O>[Cl:6][C:7]1[CH:8]=[CH:9][C:10]2[N:11]([CH:13]=[C:14]([C:16]([NH:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[O:18])[N:15]=2)[CH:12]=1

Participants

7

Reactant 4

HCID 962WaterHCID 6115AnilineHCID 6228DimethylformamideHCID 27576146-chloroimidazo[1,2-a]pyridine-2-carboxylic acid

Product 1

HCID 247715586-Chloro-N-phenylimidazo[1,2-a]pyridine-2-carboxamide

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 24386Thionyl ChlorideSolvent

Procedure

1 ml of dimethylformamide is added to a solution of 0.196 g of 6-chloroimidazo[1,2-a]pyridine-2-carboxylic acid in 3 ml of dichloromethane and 0.146 ml of thionyl chloride. The reaction mixture is stirred at ambient temperature for 3 hours. 0.273 ml of aniline is added and the mixture is stirred at ambient temperature for 22 hours. 20 ml of dichloromethane and 10 ml of water are added. After separation by settling, the organic phase is dried over magnesium sulfate, filtered and evaporated to dryness under reduced pressure, and then the residue is purified on a silica column, elution being carried out with dichloromethane. The fractions comprising the product are combined and concentrated to dryness under reduced pressure to give 0.204 g of 6-chloro-N-phenylimidazo[1,2-a]pyridine-2-carboxamide in the form of a white solid.

Workup

  1. stirringthe mixture is stirred at ambient temperature for 22 hours
  2. customAfter separation
  3. dry with materialthe organic phase is dried over magnesium sulfate
  4. filtrationfiltered
  5. customevaporated to dryness under reduced pressure
  6. customthe residue is purified on a silica column, elution
  7. concentrationconcentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-8e1275b14bd1428eb97fe8deadbfd852
Source dataset
uspto-grants-2010_04
Patent number
US07704989B2

Reaction notes

Loading…