Trifluoroacetic anhydride → N-{3-[(2-aminoimidazo[1,2-a]pyridin-6-yl)oxy]phenyl}-3-methylpyridine-2-carboxamide

HRID 1874537

Reaction equation

HRID 1874537 reaction equation
[NH2:1][C:2](=O)[CH2:3][N:4]1[C:9](=[N:10]S(C2C=CC(C)=CC=2)(=O)=O)[CH:8]=[CH:7][C:6]([O:21][C:22]2[CH:23]=[C:24]([NH:28][C:29]([C:31]3[C:36]([CH3:37])=[CH:35][CH:34]=[CH:33][N:32]=3)=[O:30])[CH:25]=[CH:26][CH:27]=2)=[CH:5]1.FC(F)(F)C(OC(=O)C(F)(F)F)=O>O1CCCC1>[NH2:1][C:2]1[N:10]=[C:9]2[CH:8]=[CH:7][C:6]([O:21][C:22]3[CH:23]=[C:24]([NH:28][C:29]([C:31]4[C:36]([CH3:37])=[CH:35][CH:34]=[CH:33][N:32]=4)=[O:30])[CH:25]=[CH:26][CH:27]=3)=[CH:5][N:4]2[CH:3]=1

Participants

4

Reactant 2

HCID 9845Trifluoroacetic anhydrideHCID 68990660N-(3-{[1-(2-amino-2-oxoethyl)-6-{[(4-methylphenyl)sulfonyl]imino}-1,6-dihydropyridin-3-yl]oxy}phenyl)-3-methylpyridine-2-carboxamide

Product 1

HCID 57749390N-{3-[(2-aminoimidazo[1,2-a]pyridin-6-yl)oxy]phenyl}-3-methylpyridine-2-carboxamideYield 69.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of N-(3-{[1-(2-amino-2-oxoethyl)-6-{[(4-methylphenyl)sulfonyl]imino}-1,6-dihydropyridin-3-yl]oxy}phenyl)-3-methylpyridine-2-carboxamide (9.68 g, 18.2 mmol), trifluoroacetic anhydride (30 mL) and tetrahydrofuran (250 mL) was stirred at room temperature for 2 hr. The reaction solution was concentrated under reduced pressure, ethanol (200 mL) and 4M aqueous sodium hydroxide solution (60 mL) were added to the residue, and the mixture was stirred at room temperature for 19 hr. The reaction solution was concentrated under reduced pressure, and ethyl acetate was added to the residue. The mixture was washed with water 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%→100% ethyl acetate-hexane) to give the title compound (4.52 g, 69%) as a pale-yellow oil.

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure, ethanol (200 mL) and 4M aqueous sodium hydroxide solution (60 mL)
  2. additionwere added to the residue
  3. stirringthe mixture was stirred at room temperature for 19 hr
  4. concentrationThe reaction solution was concentrated under reduced pressure, and ethyl acetate
  5. additionwas added to the residue
  6. washThe mixture was washed with water and saturated brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationfiltrated
  9. concentrationThe filtrate was concentrated under reduced pressure
  10. customthe residue was purified by silica gel column chromatography (NH silica gel, 0%→100% ethyl acetate-hexane)

Sources & evidence

ORD record
ord-ed652ae6717a496f8784681ba75973ae
Source dataset
uspto-grants-2012_11
Patent number
US08304557B2

Linked notes

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