Hydrochloric Acid → tert-butyl methyl[2-[[[phenyl(1H-pyrrolo[2,3-c]pyridin-2-yl)methylene]amino]oxy]ethyl]carbamate

HRID 1821899Notes

Reaction equation

HRID 1821899 reaction equation
[C:1]1([C:7]([C:9]2[NH:17][C:12]3=[CH:13][N:14]=[CH:15][CH:16]=[C:11]3[CH:10]=2)=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:18]([O:22][C:23](=[O:30])[N:24]([CH2:26][CH2:27][O:28][NH2:29])[CH3:25])([CH3:21])([CH3:20])[CH3:19].Cl>CCO.C(OCC)C>[CH3:25][N:24]([CH2:26][CH2:27][O:28][N:29]=[C:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[C:9]1[NH:17][C:12]2=[CH:13][N:14]=[CH:15][CH:16]=[C:11]2[CH:10]=1)[C:23](=[O:30])[O:22][C:18]([CH3:21])([CH3:19])[CH3:20]

Participants

6

Reactant 3

HCID 313Hydrochloric Acid2×HCID 23398498tert-butyl N-[2-(aminooxy)ethyl]-N-methylcarbamateHCID 57893467phenyl(1H-pyrrolo[2,3-c]pyridin-2-yl)methanone

Product 1

HCID 136386514tert-butyl methyl[2-[[[phenyl(1H-pyrrolo[2,3-c]pyridin-2-yl)methylene]amino]oxy]ethyl]carbamate

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 3283Diethyl EtherSolvent

Procedure

A mixture of phenyl(1H-pyrrolo[2,3-c]pyridin-2-yl)methanone (Example 35) (200 mg, 90 mmol) and tert-butyl[2-(aminooxy)ethyl]methylcarbamate (Reference Example 14) (180 mg, 94 mmol) in EtOH (20 mL) was adjusted to pH 4-5 with HCl (1.2 mL of a 1 N HCl solution in diethyl ether, 1.2 mmol). The reaction mixture was heated to reflux. After 15.5 h, the reaction mixture was concentrated under reduced pressure. The residue was diluted with EtOAc (25 mL) and washed with saturated NaHCO3 (2×10 mL). The combined organic layers were washed with saturated NaCl (10 mL), dried (Na2SO4) and concentrated under reduced pressure. Purification by column chromatography (silica gel, 99:1 CH2Cl2/MeOH to 95:5 CH2Cl2/MeOH) gave tert-butyl methyl[2-[[[phenyl(1H-pyrrolo[2,3-c]pyridin-2-yl)methylene]amino]oxy]ethyl]carbamate (geometry of the oxime double bond undefined).

Workup

  1. temperatureThe reaction mixture was heated to reflux
  2. concentrationthe reaction mixture was concentrated under reduced pressure
  3. additionThe residue was diluted with EtOAc (25 mL)
  4. washwashed with saturated NaHCO3 (2×10 mL)
  5. washThe combined organic layers were washed with saturated NaCl (10 mL)
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated under reduced pressure
  8. customPurification by column chromatography (silica gel, 99:1 CH2Cl2/MeOH to 95:5 CH2Cl2/MeOH)

Sources & evidence

ORD record
ord-955dfe4a9d8e4f0ca25f114553c3a67e
Source dataset
uspto-grants-2009_10
Patent number
US07608627B2

Reaction notes

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