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Sodium Hydroxide → tert-butyl N-[[6-[(E)-hydroxyiminomethyl]-[1,2,4]triazolo[4,3-b]pyridazin-3-yl]methyl]carbamate

HRID 2176692
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HRID 2176692 반응식
[CH:1]([C:3]1[CH:4]=[CH:5][C:6]2[N:7]([C:9]([CH2:12][NH:13][C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[N:10][N:11]=2)[N:8]=1)=O.Cl.[NH2:22][OH:23].[OH-].[Na+]>C1COCC1>[OH:23]/[N:22]=[CH:1]/[C:3]1[CH:4]=[CH:5][C:6]2[N:7]([C:9]([CH2:12][NH:13][C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[N:10][N:11]=2)[N:8]=1
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참가 물질

5

반응물 3

HCID 14798Sodium HydroxideHCID 443297Hydroxyamine hydrochlorideHCID 57691111Tert-butyl (6-formyl-[1,2,4]triazolo[4,3-b]pyridazin-3-yl)methylcarbamate

생성물 1

HCID 135987477tert-butyl N-[[6-[(E)-hydroxyiminomethyl]-[1,2,4]triazolo[4,3-b]pyridazin-3-yl]methyl]carbamate수율 47.5%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

Tert-butyl (6-formyl-[1,2,4]triazolo[4,3-b]pyridazin-3-yl)methylcarbamate (400 mg, 1.44 mmol) and hydroxylamine hydrochloride (200 mg, 2.86 mmol) were combined in a flask with 25 mL of THF and 25 mL of 1 N NaOH solution. Stirred at rt for 1 h. Then added dichloromethane (50 mL) and extracted the aqueous layer 3 times with DCM (50 mL), dried over Na2SO4 and concentrated. Purified the oxime via MPLC (DCM/MeOH+1% NH4OH) to give title compound (200 mg, 47% yield) as a tan solid.

후처리

  1. extractionThen added dichloromethane (50 mL) and extracted the aqueous layer 3 times with DCM (50 mL)
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated
  4. customPurified the oxime via MPLC (DCM/MeOH+1% NH4OH)

출처 및 근거

ORD 기록
ord-cda78e7ecfaa43f18aab7f210c8258ed
출처 데이터셋
uspto-grants-2015_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09066954B2

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