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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
Notes
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Reaction equation

HRID 1821895 reaction equation
[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
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 702Ethanol
Solvent

Procedure

(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).

Workup

  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)

Sources & evidence

ORD record
ord-b2021fda479b4adea67d1665a2a3e5d9
Source dataset
uspto-grants-2009_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07608627B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes