Tert-Butylamine → N-[2-(t-butylamino)-5-chloro-3,6-difluoropyridin-4-yl]phthalimide

HRID 610232Notes

Reaction equation

HRID 610232 reaction equation
[Cl:1][C:2]1[C:3]([F:21])=[N:4][C:5](F)=[C:6]([F:19])[C:7]=1[N:8]1[C:12](=[O:13])[C:11]2=[CH:14][CH:15]=[CH:16][CH:17]=[C:10]2[C:9]1=[O:18].[C:22]([NH2:26])([CH3:25])([CH3:24])[CH3:23]>C(#N)C>[C:22]([NH:26][C:5]1[C:6]([F:19])=[C:7]([N:8]2[C:12](=[O:13])[C:11]3=[CH:14][CH:15]=[CH:16][CH:17]=[C:10]3[C:9]2=[O:18])[C:2]([Cl:1])=[C:3]([F:21])[N:4]=1)([CH3:25])([CH3:24])[CH3:23]

Participants

4

Reactant 2

HCID 6385Tert-ButylamineHCID 221212012-(3-Chloro-2,5,6-trifluoropyridin-4-yl)-1H-isoindole-1,3(2H)-dione

Product 1

HCID 22121242N-[2-(t-butylamino)-5-chloro-3,6-difluoropyridin-4-yl]phthalimide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To 150 ml of acetonitrile was added 30.0 g of N-(3-chloro-2,5,6-trifluoropyridin-4-yl)phthalimide together with 42.2 g of t-butylamine, and the mixture was heated under reflux with stirring for 30 minutes. The solution was concentrated under reduced pressure, then 200 ml of chloroform was added, and washed with 100 ml of distilled water. The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure to obtain about the title compound as colorless solid residue.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux
  3. concentrationThe solution was concentrated under reduced pressure
  4. addition200 ml of chloroform was added
  5. washwashed with 100 ml of distilled water
  6. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-1f8bd1df5c3b4bdfbcb3cab1bccd0210
Source dataset
uspto-grants-1999_12
Patent number
US05998436

Reaction notes

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