Sodium Hydroxide → 3-(2-Ethylpyridin-3-yloxy)-5-(pyridin-2-ylthio)pyridin-2-amine

HRID 534080Notes

Reaction equation

HRID 534080 reaction equation
[CH2:1]([C:3]1[C:8]([O:9][C:10]2[C:11](C(N)=O)=[N:12][CH:13]=[C:14]([S:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=3)[CH:15]=2)=[CH:7][CH:6]=[CH:5][N:4]=1)[CH3:2].Br[N:27]1C(=O)CCC1=O.[OH-].[Na+]>CO.O.[NH4+].[Cl-]>[CH2:1]([C:3]1[C:8]([O:9][C:10]2[C:11]([NH2:27])=[N:12][CH:13]=[C:14]([S:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=3)[CH:15]=2)=[CH:7][CH:6]=[CH:5][N:4]=1)[CH3:2]

Participants

7

Reactant 3

HCID 14798Sodium HydroxideHCID 67184N-bromobutanimideHCID 674861443-(2-Ethylpyridin-3-yloxy)-5-(pyridin-2-ylthio)picolinamide

Product 1

HCID 674859303-(2-Ethylpyridin-3-yloxy)-5-(pyridin-2-ylthio)pyridin-2-amineYield 80.6%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolvent2×HCID 25517Ammonium ChlorideSolvent

Procedure

3-(2-Ethylpyridin-3-yloxy)-5-(pyridin-2-ylthio)picolinamide (71 g, 201 mmol) was dissolved in MeOH (1 L). 1-Bromopyrrolidine-2,5-dione (46.6 g, 262 mmol) was added and the reaction was stirred at ambient temperature for 5 minutes and then cooled in an ice bath. Sodium hydroxide (41.9 g, 1048 mmol) dissolved in water (200 mL) was added slowly and the reaction was stirred at ambient temperature for 1 hour, refluxed for 8 hours and then cooled to ambient temperature overnight. The reaction was diluted with 2.5 L water and 0.5 L NH4Cl and stirred for 30 minutes. The precipitate was filtered and dried to afford 3-(2-ethylpyridin-3-yloxy)-5-(pyridin-2-ylthio)pyridin-2-amine (52.6 g, 162 mmol, 80.5% yield) as a tan solid.

Workup

  1. temperaturecooled in an ice bath
  2. additionwas added slowly
  3. stirringthe reaction was stirred at ambient temperature for 1 hour
  4. temperaturerefluxed for 8 hours
  5. temperaturecooled to ambient temperature overnight
  6. stirringstirred for 30 minutes
  7. filtrationThe precipitate was filtered
  8. customdried

Sources & evidence

ORD record
ord-6cd931cc70084eaa90fbbd2b077cb7ed
Source dataset
uspto-grants-2014_10
Patent number
US08853409B2

Reaction notes

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