Methanol → 3-methyl-N-(3-{[2-(propanoylamino)imidazo[1,2-a]pyridin-6-yl]oxy}phenyl)pyridine-2-carboxamide

HRID 1874538Notes

Reaction equation

HRID 1874538 reaction equation
[NH2:1][C:2]1[N:3]=[C:4]2[CH:9]=[CH:8][C:7]([O:10][C:11]3[CH:12]=[C:13]([NH:17][C:18]([C:20]4[C:25]([CH3:26])=[CH:24][CH:23]=[CH:22][N:21]=4)=[O:19])[CH:14]=[CH:15][CH:16]=3)=[CH:6][N:5]2[CH:27]=1.[C:28](Cl)(=[O:31])[CH2:29][CH3:30].CO.C(=O)([O-])[O-].[Na+].[Na+]>CN(C)C(=O)C.O1CCCC1>[CH3:26][C:25]1[C:20]([C:18]([NH:17][C:13]2[CH:14]=[CH:15][CH:16]=[C:11]([O:10][C:7]3[CH:8]=[CH:9][C:4]4[N:5]([CH:27]=[C:2]([NH:1][C:28](=[O:31])[CH2:29][CH3:30])[N:3]=4)[CH:6]=3)[CH:12]=2)=[O:19])=[N:21][CH:22]=[CH:23][CH:24]=1

Participants

7

Reactant 4

HCID 887MethanolHCID 10340Sodium CarbonateHCID 62324Propionyl chlorideHCID 57749390N-{3-[(2-aminoimidazo[1,2-a]pyridin-6-yl)oxy]phenyl}-3-methylpyridine-2-carboxamide

Product 1

HCID 577491973-methyl-N-(3-{[2-(propanoylamino)imidazo[1,2-a]pyridin-6-yl]oxy}phenyl)pyridine-2-carboxamideYield 41.2%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 31374DimethylacetamideSolvent

Procedure

To a solution of N-{3-[(2-aminoimidazo[1,2-a]pyridin-6-yl)oxy]phenyl}-3-methylpyridine-2-carboxamide (129 mg, 0.359 mmol) in N,N-dimethylacetamide (6 mL) was added propionylchloride (34.3 μL, 0.395 mmol), and the mixture was stirred at room temperature for 22 hr. Methanol, tetrahydrofuran and aqueous sodium carbonate solution were added to the reaction mixture, and the mixture was stirred at 60° C. for 22 hr. The reaction mixture was concentrated under reduced pressure, diluted with aqueous sodium hydrogen carbonate solution and extracted with ethyl acetate. The organic layer was washed with aqueous sodium hydrogen carbonate solution and saturated brine, dried over anhydrous magnesium sulfate and filtrated. The filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (0%→100% ethyl acetate-hexane) to give the title compound (61.4 mg, 41%) as a white solid.

Workup

  1. stirringthe mixture was stirred at 60° C. for 22 hr
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. additiondiluted with aqueous sodium hydrogen carbonate solution
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with aqueous sodium hydrogen carbonate solution and saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltrated
  8. concentrationThe filtrate was concentrated under reduced pressure
  9. customthe residue was purified by silica gel column chromatography (0%→100% ethyl acetate-hexane)

Sources & evidence

ORD record
ord-7c52e50d50fd407e8041e6539316fd7a
Source dataset
uspto-grants-2012_11
Patent number
US08304557B2

Reaction notes

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