Aniline → 6-(dimethylamino)-N-phenylimidazo[1,2-a]pyridine-2-carboxamide

HRID 1952200Notes

Reaction equation

HRID 1952200 reaction equation
C[Al](C)C.[NH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[CH3:12][N:13]([CH3:28])[C:14]1[CH:15]=[CH:16][C:17]2[N:18]([CH:20]=[C:21]([C:23](OCC)=[O:24])[N:22]=2)[CH:19]=1.[Cl-].[NH4+]>C1(C)C=CC=CC=1>[CH3:12][N:13]([CH3:28])[C:14]1[CH:15]=[CH:16][C:17]2[N:18]([CH:20]=[C:21]([C:23]([NH:5][C:6]3[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=3)=[O:24])[N:22]=2)[CH:19]=1

Participants

6

Reactant 4

HCID 6115AnilineHCID 25517Ammonium ChlorideHCID 16682925TrimethylaluminumHCID 44124134Ethyl 6-dimethylaminoimidazo[1,2-a]pyridine-2-carboxylate

Product 1

HCID 247716096-(dimethylamino)-N-phenylimidazo[1,2-a]pyridine-2-carboxamide

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

0.46 ml of a 2M solution of trimethylaluminum in toluene is added dropwise to a solution, cooled to 0° C., of 60.8 μl of aniline in 3 ml of toluene, followed, at 20° C., by the addition of 76 mg of ethyl 6-dimethylaminoimidazo[1,2-a]pyridine-2-carboxylate. The reaction mixture is stirred at ambient temperature for 15 minutes. It is cooled to 0° C. and then 20 ml of a saturated ammonium chloride solution are added. The organic phase is dried over magnesium sulfate, filtered through Celite and evaporated to dryness under reduced pressure. The residue is chromatographed on a silica cartridge, elution being carried out with a mixture of dichloromethane and ethyl acetate. The fractions comprising the product are combined and concentrated to dryness under reduced pressure. The residue obtained is crystallized from methanol to give 36 mg of 6-(dimethylamino)-N-phenylimidazo[1,2-a]pyridine-2-carboxamide in the form of a gray powder.

Workup

  1. temperatureIt is cooled to 0° C.
  2. dry with materialThe organic phase is dried over magnesium sulfate
  3. filtrationfiltered through Celite
  4. customevaporated to dryness under reduced pressure
  5. customThe residue is chromatographed on a silica cartridge, elution
  6. additionbeing carried out with a mixture of dichloromethane and ethyl acetate
  7. concentrationconcentrated to dryness under reduced pressure
  8. customThe residue obtained
  9. customis crystallized from methanol

Sources & evidence

ORD record
ord-c62d9bb4571c456b832ee3039678223c
Source dataset
uspto-grants-2013_03
Patent number
US08404848B2

Reaction notes

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