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Hydrochloric Acid → tert-butyl 2-[[[(4-methylphenyl)(1H-pyrrolo[2,3-c]pyridin-2-yl)methylene]amino]oxy]ethylcarbamate

HRID 1821895
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HRID 1821895 반응식
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:10]2[NH:18][C:13]3=[CH:14][N:15]=[CH:16][CH:17]=[C:12]3[CH:11]=2)=O)=[CH:4][CH:3]=1.[C:19]([O:23][C:24](=[O:30])[NH:25][CH2:26][CH2:27][O:28][NH2:29])([CH3:22])([CH3:21])[CH3:20].Cl>C(O)C>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[N:29][O:28][CH2:27][CH2:26][NH:25][C:24](=[O:30])[O:23][C:19]([CH3:21])([CH3:20])[CH3:22])[C:10]2[NH:18][C:13]3=[CH:14][N:15]=[CH:16][CH:17]=[C:12]3[CH:11]=2)=[CH:4][CH:3]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

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반응물 3

HCID 313Hydrochloric AcidHCID 15610443tert-butyl N-(2-(aminooxy)ethyl)carbamateHCID 57893512(4-methylphenyl)(1H-pyrrolo[2,3-c]pyridin-2-yl)methanone

생성물 1

HCID 136386511tert-butyl 2-[[[(4-methylphenyl)(1H-pyrrolo[2,3-c]pyridin-2-yl)methylene]amino]oxy]ethylcarbamate

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

(4-Methylphenyl)(1H-pyrrolo[2,3-c]pyridin-2-yl)methanone (Example 100) (130 mg, 0.55 mmol) and tert-butyl[2-(aminooxy)ethyl]carbamate (99 mg, 0.56 mmol) were combined in ethanol (8 mL). The pH of the mixture was adjusted to ca. 4 using 1 M ethereal hydrogen chloride and the reaction mixture was refluxed for 14 h. The solvent was removed under vacuum. The residue was dissolved in ethyl acetate, washed with saturated sodium bicarbonate solution and then brine, dried over sodium sulfate, and concentrated to a solid. Purification by column chromatography (silica gel, 75 to 100% ethyl acetate in hexanes) produced tert-butyl 2-[[[(4-methylphenyl)(1H-pyrrolo[2,3-c]pyridin-2-yl)methylene]amino]oxy]ethylcarbamate (geometry of the oxime double bond undefined).

후처리

  1. temperaturethe reaction mixture was refluxed for 14 h
  2. customThe solvent was removed under vacuum
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. washwashed with saturated sodium bicarbonate solution
  5. dry with materialbrine, dried over sodium sulfate
  6. concentrationconcentrated to a solid
  7. customPurification by column chromatography (silica gel, 75 to 100% ethyl acetate in hexanes)

출처 및 근거

ORD 기록
ord-b2021fda479b4adea67d1665a2a3e5d9
출처 데이터셋
uspto-grants-2009_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07608627B2

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