Triethylamine → 1-(propan-2-yl)-3-(tetrahydro-2H-pyran-4-yl)-1H-pyrazol-5-amine

HRID 518875

Reaktionsgleichung

Reaktionsgleichung von HRID 518875
C(N(CC)CC)C.O=[C:9]([CH:13]1[CH2:18][CH2:17][O:16][CH2:15][CH2:14]1)[CH2:10][C:11]#[N:12].Cl.[CH:20]([NH:23][NH2:24])([CH3:22])[CH3:21]>C(O)C>[CH3:21][CH:20]([N:23]1[C:11]([NH2:12])=[CH:10][C:9]([CH:13]2[CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)=[N:24]1)[CH3:22]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 855731-Isopropylhydrazine hydrochlorideHCID 629075903-(Oxan-4-yl)-3-oxopropanenitrile

Produkt 1

HCID 866980281-(propan-2-yl)-3-(tetrahydro-2H-pyran-4-yl)-1H-pyrazol-5-amineAusbeute 81,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

0.43 ml of triethylamine is added to a solution of 640 mg of 3-oxo-3-(tetrahydro-2H-pyran-4-yl)propanenitrile and 347 mg of isopropylhydrazine hydrochloride in 8 ml of ethanol under an argon atmosphere. The mixture is refluxed with magnetic stirring for 1 h and then concentrated to dryness under reduced pressure. The residue is taken up in 100 ml of ethyl acetate and the organic phase is washed twice with 40 ml of a saturated sodium hydrogen carbonate solution. The combined aqueous phases are extracted twice with 50 ml of ethyl acetate. The combined organic phases are dried over magnesium sulfate, filtered and concentrated under reduced pressure, so as to obtain 536 mg of 1-(propan-2-yl)-3-(tetrahydro-2H-pyran-4-yl)-1H-pyrazol-5-amine.

Aufarbeitung

  1. temperatureThe mixture is refluxed
  2. concentrationconcentrated to dryness under reduced pressure
  3. washthe organic phase is washed twice with 40 ml of a saturated sodium hydrogen carbonate solution
  4. extractionThe combined aqueous phases are extracted twice with 50 ml of ethyl acetate
  5. dry with materialThe combined organic phases are dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-2acc95365d0946c38ed57b369dd743ab
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09115140B2

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