Ammonium Chloride → N-[6-(4-amino-2-fluorophenoxy)[1,2,4]triazolo[1,5-a]pyridin-2-yl]cyclopropanecarboxamide

HRID 2095794Notes

Reaction equation

HRID 2095794 reaction equation
[F:1][C:2]1[CH:23]=[C:22]([N+:24]([O-])=O)[CH:21]=[CH:20][C:3]=1[O:4][C:5]1[CH:6]=[CH:7][C:8]2[N:9]([N:11]=[C:12]([NH:14][C:15]([CH:17]3[CH2:19][CH2:18]3)=[O:16])[N:13]=2)[CH:10]=1.[Cl-].[NH4+]>C(O)C.O>[NH2:24][C:22]1[CH:21]=[CH:20][C:3]([O:4][C:5]2[CH:6]=[CH:7][C:8]3[N:9]([N:11]=[C:12]([NH:14][C:15]([CH:17]4[CH2:19][CH2:18]4)=[O:16])[N:13]=3)[CH:10]=2)=[C:2]([F:1])[CH:23]=1

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 58158626N-[6-(2-fluoro-4-nitrophenoxy)[1,2,4]triazolo[1,5-a]pyridin-2-yl]cyclopropanecarboxamide

Product 1

HCID 58158482N-[6-(4-amino-2-fluorophenoxy)[1,2,4]triazolo[1,5-a]pyridin-2-yl]cyclopropanecarboxamideYield 34.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of N-[6-(2-fluoro-4-nitrophenoxy)[1,2,4]triazolo[1,5-a]pyridin-2-yl]cyclopropanecarboxamide (400 mg, 1.12 mmol), reduced iron (312 mg, 5.59 mmol) and ammonium chloride (600 mg, 11.2 mmol) in ethanol (8 mL) and water (2 mL) was heated under reflux for 1.5 hr. The reaction mixture was filtered through celite, and the filtrate was diluted with water and ethyl acetate and extracted 3 times with ethyl acetate. The combined organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and filtered, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane=1/2→ethyl acetate/methanol=9/1) to give the title compound (125 mg, 34%) as a white solid.

Workup

  1. temperatureunder reflux for 1.5 hr
  2. filtrationThe reaction mixture was filtered through celite
  3. additionthe filtrate was diluted with water and ethyl acetate
  4. extractionextracted 3 times with ethyl acetate
  5. washThe combined organic layer was washed with saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. customthe solvent was evaporated under reduced pressure
  9. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane=1/2→ethyl acetate/methanol=9/1)

Sources & evidence

ORD record
ord-a31faeeb75b1407786f86d9285caee28
Source dataset
uspto-grants-2013_05
Patent number
US08445509B2

Reaction notes

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