Acetic Acid → 3-Tert-butyl-1-((tetrahydro-2h-pyran-2-yl)methyl)-1h-pyrazol-5-amine

HRID 452974

Reaktionsgleichung

Reaktionsgleichung von HRID 452974
[C:1]([C:5]1[CH:9]=[C:8](/[N:10]=C/N(C)C)[N:7]([CH2:15][CH:16]2[CH2:21][CH2:20][CH2:19][CH2:18][O:17]2)[N:6]=1)([CH3:4])([CH3:3])[CH3:2].NN.C(O)(=O)C>O1CCOCC1>[C:1]([C:5]1[CH:9]=[C:8]([NH2:10])[N:7]([CH2:15][CH:16]2[CH2:21][CH2:20][CH2:19][CH2:18][O:17]2)[N:6]=1)([CH3:4])([CH3:2])[CH3:3]

Komponenten

5

Edukt 3

HCID 176Acetic AcidHCID 9321HydrazineHCID 87440113N'-[3-tert-butyl-1-(oxan-2-ylmethyl)pyrazol-5-yl]-N,N-dimethylmethanimidamide

Produkt 1

HCID 675445333-Tert-butyl-1-((tetrahydro-2h-pyran-2-yl)methyl)-1h-pyrazol-5-amine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
85 °C

Versuchsvorschrift

To a solution of Example 63B (0.9 g, 3.1 mmol) in dioxane (10 mL) were added hydrazine (0.12 mL, 3.7 mmol, Aldrich) and acetic acid (0.35 mL, 6.2 mmol). After stirring at 85° C. for 16 hours, the reaction mixture was cooled and quenched with saturated NaHCO3 (10 mL). The aqueous layer was extracted with ethyl acetate (3×20 mL). The combined organic extracts were dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure to provide the title compound. MS (APCI+) m/z 238 (M+H)+.

Aufarbeitung

  1. temperaturethe reaction mixture was cooled
  2. customquenched with saturated NaHCO3 (10 mL)
  3. extractionThe aqueous layer was extracted with ethyl acetate (3×20 mL)
  4. dry with materialThe combined organic extracts were dried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-9f1e66612f644f2380608be7ebeefcdd
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08492371B2

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