Water → N-{5-[(5-aminopyridin-2-yl)oxy]-2-methylphenyl}-3-(1-cyanocyclopropyl)benzamide

HRID 1800451Notes

Reaction equation

HRID 1800451 reaction equation
[C:1]([C:3]1([C:6]2[CH:7]=[C:8]([CH:29]=[CH:30][CH:31]=2)[C:9]([NH:11][C:12]2[CH:17]=[C:16]([O:18][C:19]3[CH:24]=[CH:23][C:22]([N+:25]([O-])=O)=[CH:21][N:20]=3)[CH:15]=[CH:14][C:13]=2[CH3:28])=[O:10])[CH2:5][CH2:4]1)#[N:2].[Cl-].[Ca+2].[Cl-].O>C(O)C>[NH2:25][C:22]1[CH:23]=[CH:24][C:19]([O:18][C:16]2[CH:15]=[CH:14][C:13]([CH3:28])=[C:12]([NH:11][C:9](=[O:10])[C:8]3[CH:29]=[CH:30][CH:31]=[C:6]([C:3]4([C:1]#[N:2])[CH2:4][CH2:5]4)[CH:7]=3)[CH:17]=2)=[N:20][CH:21]=1

Participants

5

Reactant 3

HCID 962WaterHCID 5284359Calcium ChlorideHCID 684197213-(1-cyanocyclopropyl)-N-{2-methyl-5-[(5-nitropyridin-2-yl)oxy]phenyl}benzamide

Product 1

HCID 68417579N-{5-[(5-aminopyridin-2-yl)oxy]-2-methylphenyl}-3-(1-cyanocyclopropyl)benzamideYield 83.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

A suspension of 3-(1-cyanocyclopropyl)-N-{2-methyl-5-[(5-nitropyridin-2-yl)oxy]phenyl}benzamide (8.5 g, 20.5 mmol), calcium chloride (5.55 g, 50 mmol) and reduced iron (14.5 g, 260 mmol) in ethanol (500 mL)/water (50 mL) was stirred with heating at 80° C. for 4 hr. After the reaction mixture was cooled to room temperature, the insoluble material was filtered off through a pad filled with celite, and washed with ethanol. The filtrate and washing solution were combined, and concentrated under reduced pressure. The obtained residue was diluted with ethyl acetate (300 mL), washed with 5% aqueous sodium hydrogen carbonate solution (300 mL) and saturated brine (300 mL), and dried over anhydrous sodium sulfate. The insoluble material was filtered off, and the filtrate was concentrated under reduced pressure to give the title compound (6.57 g, 83%) as a green amorphous substance. The amorphous substance was used for the next reaction without further purification.

Workup

  1. temperatureAfter the reaction mixture was cooled to room temperature
  2. filtrationthe insoluble material was filtered off through a pad
  3. additionfilled with celite
  4. washwashed with ethanol
  5. washThe filtrate and washing solution
  6. concentrationconcentrated under reduced pressure
  7. additionThe obtained residue was diluted with ethyl acetate (300 mL)
  8. washwashed with 5% aqueous sodium hydrogen carbonate solution (300 mL) and saturated brine (300 mL)
  9. dry with materialdried over anhydrous sodium sulfate
  10. filtrationThe insoluble material was filtered off
  11. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-3826dc8bcaae4ffc99bfecb11db5345b
Source dataset
uspto-grants-2013_01
Patent number
US08344135B2

Reaction notes

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