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

HRID 1874551Notes

Reaction equation

HRID 1874551 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[CH:25]=[CH:24][CH:23]=[C:22]([CH3:26])[N:21]=4)=[O:19])[CH:14]=[CH:15][CH:16]=3)=[CH:6][N:5]2[CH:27]=1.[CH3:28][O:29][CH2:30][C:31](Cl)=[O:32].CO.C(=O)([O-])[O-].[Na+].[Na+]>CN(C)C(=O)C.O1CCCC1>[CH3:28][O:29][CH2:30][C:31]([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[CH:25]=[CH:24][CH:23]=[C:22]([CH3:26])[N:21]=4)=[O:19])[CH:14]=[CH:15][CH:16]=3)=[CH:6][N:5]2[CH:27]=1)=[O:32]

Participants

7

Reactant 4

HCID 887MethanolHCID 10340Sodium CarbonateHCID 96623Methoxyacetyl chlorideHCID 57749229N-{3-[(2-aminoimidazo[1,2-a]pyridin-6-yl)oxy]phenyl}-6-methylpyridine-2-carboxamide

Product 1

HCID 57749179N-[3-({2-[(methoxyacetyl)amino]imidazo[1,2-a]pyridin-6-yl}oxy)phenyl]-6-methylpyridine-2-carboxamideYield 32%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 31374DimethylacetamideSolvent

Procedure

To a solution of N-{3-[(2-aminoimidazo[1,2-a]pyridin-6-yl)oxy]phenyl}-6-methylpyridine-2-carboxamide (300 mg, 0.835 mmol) in N,N-dimethylacetamide (5 mL) was added methoxyacetyl chloride (92.0 μL, 1.01 mmol), and the mixture was stirred at room temperature for 15 hr. Methanol, tetrahydrofuran and aqueous sodium carbonate solution were added to the reaction mixture, and the mixture was stirred at 60° C. for 17 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 (NH silica gel, 0%→85% ethyl acetate-hexane) to give the title compound (115 mg, 32%) as a white solid.

Workup

  1. stirringthe mixture was stirred at 60° C. for 17 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 (NH silica gel, 0%→85% ethyl acetate-hexane)

Sources & evidence

ORD record
ord-b23fa04e332b40e69c408c8c70c23f72
Source dataset
uspto-grants-2012_11
Patent number
US08304557B2

Reaction notes

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