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Sodium Hydroxide → [1,2,4]Triazolo[1,5-a]pyridin-2-ylmethanol

HRID 1771990
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HRID 1771990 반응식
[NH2:1][N:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]1=[NH2+:8].CC1C=C(C)C=C(C)C=1S([O-])(=O)=O.[OH-].[Na+].[OH:24][CH2:25][C:26](OC)=O>CCO>[N:8]1[C:26]([CH2:25][OH:24])=[N:1][N:2]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=12
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참가 물질

5

반응물 3

HCID 14798Sodium HydroxideHCID 66774Methyl GlycolateHCID 178425983HCID 178425983, 화합물

생성물 1

HCID 18406865[1,2,4]Triazolo[1,5-a]pyridin-2-ylmethanol수율 59%

시약·촉매·용매 1

HCID 702Ethanol용매

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온도
60 °C

실험 절차

To a solution of 1-aminopyridin-2(1H)-iminium-2,4,6-trimethylbenzenesulfonate (1.24 g, 4 mmol) in EtOH (15 mL) was added NaOH (320 mg, 8 mmol). The mixture was heated to 60° C. and stirred for 1 h. Then methyl 2-hydroxyacetate (720 mg, 8 mmol) was added and the mixture was heated to 80° C. and stirred for 3 h. The resulting mixture was cooled to room temperature and concentrated under reduced pressure. The residue was washed with water (10 mL) and extracted with DCM (15 mL×3). The combined organic layers were washed with brine (10 mL), dried over anhydrous sodium sulfate and concentrated under reduced pressure to afford the title compound as a pale yellow solid (350 mg, 59% yield). ESI MS: m/z 150 [M+H]+.

후처리

  1. temperaturethe mixture was heated to 80° C.
  2. stirringstirred for 3 h
  3. temperatureThe resulting mixture was cooled to room temperature
  4. concentrationconcentrated under reduced pressure
  5. washThe residue was washed with water (10 mL)
  6. extractionextracted with DCM (15 mL×3)
  7. washThe combined organic layers were washed with brine (10 mL)
  8. dry with materialdried over anhydrous sodium sulfate
  9. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-86cbdd96d5d74dc282c1334c1a472f30
출처 데이터셋
uspto-grants-2016_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09249162B2

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