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Methyl acetoacetate → 1-tert-Butyl-3-cyclobutyl-4-methyl-1,7-dihydro-pyrazolo[3,4-b]pyridin-6-one

HRID 1594391
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1594391
[C:1]([N:5]1[C:9]([NH2:10])=[CH:8][C:7]([CH:11]2[CH2:14][CH2:13][CH2:12]2)=[N:6]1)([CH3:4])([CH3:3])[CH3:2].[C:15](OC)(=[O:20])[CH2:16][C:17]([CH3:19])=O>C(O)(=O)C>[C:1]([N:5]1[C:9]2[NH:10][C:15](=[O:20])[CH:16]=[C:17]([CH3:19])[C:8]=2[C:7]([CH:11]2[CH2:14][CH2:13][CH2:12]2)=[N:6]1)([CH3:4])([CH3:2])[CH3:3]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

4

Edukt 2

HCID 7757Methyl acetoacetateHCID 529880121-tert-butyl-3-Cyclobutyl-1H-pyrazol-5-amine

Produkt 1

HCID 1361404991-tert-Butyl-3-cyclobutyl-4-methyl-1,7-dihydro-pyrazolo[3,4-b]pyridin-6-oneAusbeute 52 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Reaktionsbedingungen

Temperatur
105 °C

Versuchsvorschrift

To 2-tert-butyl-5-cyclobutyl-2H-pyrazol-3-ylamine (5.0 g, 25.9 mmol) in acetic acid (25 mL) was added methyl acetoacetate (5.5 mL, 51.8 mmol), and the reaction was heated to 105° C. After 19 hr, the reaction mixture was cooled to room temperature, concentrated to a viscous oil, and then taken up in EtOAc. The reaction mixture was quenched by the slow addition of an aqueous solution of NaHCO3. The layers were separated and the organic layer was dried over MgSO4, filtered, and concentrated under reduced pressure. Purification of this material was accomplished by trituration with hexanes to give, after two crops, the title compound (0.7 g, 52% yield) as a colorless solid. 400 MHz 1H NMR (CD3OD) d 6.09 (s, 1H), 3.83 (dddd, J=8.3, 8.3, 8.3, 8.3 Hz, 1H), 2.50-2.27 (m, 7H), 2.08-2.01 (m, 1H), 1.99-1.85 (m, 1H), 1.71 (s, 9H). LRMS m/z (APCI+) 260 (M+1).

Aufarbeitung

  1. temperaturethe reaction mixture was cooled to room temperature
  2. concentrationconcentrated to a viscous oil
  3. customThe reaction mixture was quenched by the slow addition of an aqueous solution of NaHCO3
  4. customThe layers were separated
  5. dry with materialthe organic layer was dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customPurification of this material
  9. customto give

Quellen und Nachweise

ORD-Eintrag
ord-9b0e448e0fe2414aac46b379b30d7ded
Quelldatensatz
uspto-grants-2007_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07300944B2

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