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

HRID 1821842Notes

Reaction equation

HRID 1821842 reaction equation
[O:1]1[CH:5]=[CH:4][C:3]([C:6]([C:8]2[NH:16][C:11]3=[CH:12][N:13]=[CH:14][CH:15]=[C:10]3[CH:9]=2)=O)=[CH:2]1.[C:17]([O:21][C:22](=[O:28])[NH:23][CH2:24][CH2:25][O:26][NH2:27])([CH3:20])([CH3:19])[CH3:18].Cl>C(O)C>[O:1]1[CH:5]=[CH:4][C:3]([C:6](=[N:27][O:26][CH2:25][CH2:24][NH:23][C:22](=[O:28])[O:21][C:17]([CH3:19])([CH3:18])[CH3:20])[C:8]2[NH:16][C:11]3=[CH:12][N:13]=[CH:14][CH:15]=[C:10]3[CH:9]=2)=[CH:2]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 15610443tert-butyl N-(2-(aminooxy)ethyl)carbamateHCID 578934443-Furyl(1H-pyrrolo[2,3-c]pyridin-2-yl)methanone

Product 1

HCID 136365984tert-butyl 2-[[[(3-furyl)(1H-pyrrolo[2,3-c]pyridin-2-yl)methylene]amino]oxy]ethylcarbamateYield 45%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3-Furyl(1H-pyrrolo[2,3-c]pyridin-2-yl)methanone (Example 137) (63 mg, 0.30 mmol) and tert-butyl[2-(aminooxy)ethyl]carbamate (55 mg, 0.31 mmol) were combined in ethanol (5 mL). The pH of the mixture was adjusted to ca. 4 using 1 M ethereal hydrogen chloride and the reaction mixture was refluxed for 12 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 Biotage chromatography (silica gel, 2 to 18% methanol in dichloromethane) produced tert-butyl 2-[[[(3-furyl)(1H-pyrrolo[2,3-c]pyridin-2-yl)methylene]amino]oxy]ethylcarbamate (50 mg, 45%) as a yellow solid.

Workup

  1. temperaturethe reaction mixture was refluxed for 12 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 Biotage chromatography (silica gel, 2 to 18% methanol in dichloromethane)

Sources & evidence

ORD record
ord-9be96bf9de3a4879866258c2ebf5ff02
Source dataset
uspto-grants-2009_10
Patent number
US07608627B2

Reaction notes

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