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

HRID 1874552Notes

Reaction equation

HRID 1874552 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:30])[CH3:29].CO.C(=O)([O-])[O-].[Na+].[Na+]>CN(C)C(=O)C.C(=O)([O-])O.[Na+].O1CCCC1>[C:28]([NH: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)(=[O:30])[CH3:29]

Participants

8

Reactant 4

HCID 887MethanolHCID 6367Acetyl chlorideHCID 10340Sodium CarbonateHCID 57749390N-{3-[(2-aminoimidazo[1,2-a]pyridin-6-yl)oxy]phenyl}-3-methylpyridine-2-carboxamide

Product 1

HCID 57749193N-(3-{[2-(acetylamino)imidazo[1,2-a]pyridin-6-yl]oxy}phenyl)-3-methylpyridine-2-carboxamideYield 49.3%

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolventHCID 31374DimethylacetamideSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a solution of N-{3-[(2-aminoimidazo[1,2-a]pyridin-6-yl)oxy]phenyl}-3-methylpyridine-2-carboxamide (130 mg, 0.362 mmol) in N,N-dimethylacetamide (5 mL) was added acetyl chloride (26.0 μL, 0.366 mmol), and the mixture was stirred at room temperature for 3 hr. Methanol, tetrahydrofuran and aqueous sodium carbonate solution were added to the reaction mixture, and the mixture was stirred at 60° C. for 68 hr. The reaction mixture was 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 (71.7 mg, 49%) as a white solid.

Workup

  1. stirringthe mixture was stirred at 60° C. for 68 hr
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with aqueous sodium hydrogen carbonate solution and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltrated
  6. concentrationThe filtrate was concentrated under reduced pressure
  7. customthe residue was purified by silica gel column chromatography (0%→100% ethyl acetate-hexane)

Sources & evidence

ORD record
ord-101cbe45f43742ebb77df4d278282f2e
Source dataset
uspto-grants-2012_11
Patent number
US08304557B2

Reaction notes

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