Ammonium Chloride → N-{6-[(6-aminopyridin-3-yl)oxy]imidazo[1,2-a]pyridin-2-yl}cyclopropanecarboxamide

HRID 2095846Notes

Reaction equation

HRID 2095846 reaction equation
[N+:1]([C:4]1[N:9]=[CH:8][C:7]([O:10][C:11]2[CH:12]=[CH:13][C:14]3[N:15]([CH:17]=[C:18]([NH:20][C:21]([CH:23]4[CH2:25][CH2:24]4)=[O:22])[N:19]=3)[CH:16]=2)=[CH:6][CH:5]=1)([O-])=O.[Cl-].[NH4+]>C(O)C.O.C(OCC)(=O)C>[NH2:1][C:4]1[N:9]=[CH:8][C:7]([O:10][C:11]2[CH:12]=[CH:13][C:14]3[N:15]([CH:17]=[C:18]([NH:20][C:21]([CH:23]4[CH2:24][CH2:25]4)=[O:22])[N:19]=3)[CH:16]=2)=[CH:6][CH:5]=1

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 58158610N-{6-[(6-nitropyridin-3-yl)oxy]imidazo[1,2-a]pyridin-2-yl}cyclopropanecarboxamide

Product 1

HCID 58158570N-{6-[(6-aminopyridin-3-yl)oxy]imidazo[1,2-a]pyridin-2-yl}cyclopropanecarboxamideYield 45%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixed solution of N-{6-[(6-nitropyridin-3-yl)oxy]imidazo[1,2-a]pyridin-2-yl}cyclopropanecarboxamide (184 mg, 0.542 mmol), reduced iron (173 mg, 2.95 mmol) and ammonium chloride (315 mg, 5.89 mmol) in ethanol (2 mL) and water (0.5 mL) was stirred at 80° C. for 1 hr. The reaction mixture was diluted with ethyl acetate, and filtered through celite. Water was added to the filtrate, and the mixture was extracted twice with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and filtered. The solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (ethyl acetate-÷ethyl acetate/methanol=95/5) to give the title compound (75 mg, 45%) as a yellow solid.

Workup

  1. filtrationfiltered through celite
  2. additionWater was added to the filtrate
  3. extractionthe mixture was extracted twice with ethyl acetate
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customThe solvent was evaporated under reduced pressure
  8. customThe obtained residue was purified by silica gel column chromatography (ethyl acetate-÷ethyl acetate/methanol=95/5)

Sources & evidence

ORD record
ord-491b4cb588224e62bf0e321f7e324b49
Source dataset
uspto-grants-2013_05
Patent number
US08445509B2

Reaction notes

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