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

HRID 534080노트

반응식

HRID 534080 반응식
[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]

참가 물질

7

반응물 3

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

생성물 1

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

시약·촉매·용매 3

HCID 887Methanol용매HCID 962Water용매2회HCID 25517Ammonium Chloride용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-6cd931cc70084eaa90fbbd2b077cb7ed
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08853409B2

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