2-Thiophenecarbonyl chloride → Tert-butyl 4-(5-(2-thienyl)-1,2,4-oxadiazol-3-yl)piperazine-1-carboxylate

HRID 1677762Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1677762
[OH:1][NH:2][C:3](=[NH:17])[N:4]1[CH2:9][CH2:8][N:7]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:6][CH2:5]1.[S:18]1[CH:22]=[CH:21][CH:20]=[C:19]1[C:23](Cl)=O.CCN(C(C)C)C(C)C>C(Cl)Cl>[S:18]1[CH:22]=[CH:21][CH:20]=[C:19]1[C:23]1[O:1][N:2]=[C:3]([N:4]2[CH2:5][CH2:6][N:7]([C:10]([O:12][C:13]([CH3:14])([CH3:16])[CH3:15])=[O:11])[CH2:8][CH2:9]2)[N:17]=1

Komponenten

5

Edukt 3

HCID 789282-Thiophenecarbonyl chlorideHCID 81531DiisopropylethylamineHCID 178452346tert-butyl 4-(N-hydroxyamidino)-piperazine-1-carboxylate

Produkt 1

HCID 58487964Tert-butyl 4-(5-(2-thienyl)-1,2,4-oxadiazol-3-yl)piperazine-1-carboxylateAusbeute 20 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a cold (0° C.) solution of tert-butyl 4-[(hydroxyamino)(imino)methyl]piperazine-1-carboxylate (8 g, 32.7 mmol) in anhydrous DCM (150 mL) was added thiophene-2-carbonyl chloride (4.8 g, 32.7 mmol) followed by DIEA (7.2 mL, 39.2 mmol). The reaction mixture was stirred at RT for 12 hours and then filtered. The filtrate was evaporated and the residue was refluxed in pyridine (100 mL) for 3 hours. The solvent was removed under vacuum and the residue was dissolved in DCM. The organic layer was washed with a 10% aq. solution of sodium bicarbonate, water, brine and dried. The solvent was concentrated and the residue was purified by chromatography (Pet. Ether/EtOAc 7/3) to give 2.2 g (20%) of The title compound as a solid. TLC—Pet ether/EtOAc (9/1): Rf=0.75. HPLC purity>97%.

Aufarbeitung

  1. filtrationfiltered
  2. customThe filtrate was evaporated
  3. temperaturethe residue was refluxed in pyridine (100 mL) for 3 hours
  4. customThe solvent was removed under vacuum
  5. dissolutionthe residue was dissolved in DCM
  6. washThe organic layer was washed with a 10% aq. solution of sodium bicarbonate, water, brine
  7. customdried
  8. concentrationThe solvent was concentrated
  9. customthe residue was purified by chromatography (Pet. Ether/EtOAc 7/3)

Quellen und Nachweise

ORD-Eintrag
ord-ac61994c826d424797f17470b7c77301
Quelldatensatz
uspto-grants-2011_08
Patentnummer
US08008302B2

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