Methoxyacetyl chloride → 2,2-Dimethylpropyl 4-[4-(5-methoxy-1,2,4-oxadiazol-3-yl)pyridin-2-yl]-1-piperazinecarboxylate

HRID 421824Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 421824
[NH2:1][C:2](=[N:23][OH:24])[C:3]1[CH:8]=[CH:7][N:6]=[C:5]([N:9]2[CH2:14][CH2:13][N:12]([C:15]([O:17][CH2:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:16])[CH2:11][CH2:10]2)[CH:4]=1.[CH3:25][O:26][CH2:27]C(Cl)=O>N1C=CC=CC=1.C(OCC)(=O)C>[CH3:25][O:26][C:27]1[O:24][N:23]=[C:2]([C:3]2[CH:8]=[CH:7][N:6]=[C:5]([N:9]3[CH2:14][CH2:13][N:12]([C:15]([O:17][CH2:18][C:19]([CH3:20])([CH3:21])[CH3:22])=[O:16])[CH2:11][CH2:10]3)[CH:4]=2)[N:1]=1

Komponenten

5

Edukt 2

HCID 96623Methoxyacetyl chlorideHCID 1363817182,2-Dimethylpropyl 4-{4-[amino(hydroxyimino)methyl]pyridin-2-yl}-1-piperazinecarboxylate

Produkt 1

HCID 119928012,2-Dimethylpropyl 4-[4-(5-methoxy-1,2,4-oxadiazol-3-yl)pyridin-2-yl]-1-piperazinecarboxylate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1049PyridineLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

2,2-Dimethylpropyl 4-{4-[amino(hydroxyimino)methyl]pyridin-2-yl}piperazine-1-carboxylate (84 mg) obtained in Example 26-1) was dissolved in pyridine (2 mL), and methoxyacetyl chloride (0.035 mL) was added thereto and heated under reflux for 90 minutes. The reaction liquid was diluted with ethyl acetate, washed with 1 N hydrochloric acid, aqueous saturated sodium hydrogencarbonate solution and saturated saline water, and dried with anhydrous sodium sulfate. The solvent was evaporated away, and the resulting residue was isolated and purified through silica gel column chromatography (hexane/ethyl acetate=7/3) to obtain 54 mg of the entitled compound as a colorless oil.

Aufarbeitung

  1. temperatureheated
  2. temperatureunder reflux for 90 minutes
  3. customThe reaction liquid
  4. washwashed with 1 N hydrochloric acid, aqueous saturated sodium hydrogencarbonate solution and saturated saline water
  5. dry with materialdried with anhydrous sodium sulfate
  6. customThe solvent was evaporated away
  7. customthe resulting residue was isolated
  8. custompurified through silica gel column chromatography (hexane/ethyl acetate=7/3)

Quellen und Nachweise

ORD-Eintrag
ord-722705bd20904383a923353b668d5155
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08101618B2

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