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

HRID 1800460Notes

Reaction equation

HRID 1800460 reaction equation
[C:1]([C:3]([C:6]1[CH:7]=[C:8]([CH:29]=[CH:30][CH:31]=1)[C:9]([NH:11][C:12]1[CH:17]=[C:16]([O:18][C:19]2[CH:24]=[CH:23][C:22]([N+:25]([O-])=O)=[CH:21][N:20]=2)[CH:15]=[CH:14][C:13]=1[CH3:28])=[O:10])([CH3:5])[CH3:4])#[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]([C:1]#[N:2])([CH3:4])[CH3:5])[CH:7]=3)[CH:17]=2)=[N:20][CH:21]=1

Participants

5

Reactant 3

HCID 962WaterHCID 5284359Calcium ChlorideHCID 684167563-(1-cyano-1-methylethyl)-N-{2-methyl-5-[(5-nitropyridin-2-yl)oxy]phenyl}benzamide

Product 1

HCID 68416717N-{5-[(5-aminopyridin-2-yl)oxy]-2-methylphenyl}-3-(1-cyano-1-methylethyl)benzamideYield 99.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

A suspension of 3-(1-cyano-1-methylethyl)-N-{2-methyl-5-[(5-nitropyridin-2-yl)oxy]phenyl}benzamide (2.5 g, 6.0 mmol), calcium chloride (1.75 g, 15 mmol) and reduced iron (4.03 g, 72 mmol) in ethanol (300 mL)/water (30 mL) was stirred with heating at 80° C. for 2 days. 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×2), water (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. The obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=50/50→0/100), and the obtained solution was concentrated under reduced pressure to give the title compound (2.31 g, 99%) as a pale-yellow amorphous substance.

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×2), water (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
  12. customThe obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=50/50→0/100)
  13. concentrationthe obtained solution was concentrated under reduced pressure

Sources & evidence

ORD record
ord-7832775ab7e34022be2d67fd13b234a0
Source dataset
uspto-grants-2013_01
Patent number
US08344135B2

Reaction notes

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