Triethylamine → 2-Phenethyl-5-pyridin-2-yl-2H-pyrazol-3-ylamine

HRID 1260316Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1260316
O=[C:2]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][N:7]=1)[CH2:3][C:4]#[N:5].C(N(CC)CC)C.[CH:19]1[CH:24]=[CH:23][C:22]([CH2:25][CH2:26][NH:27][NH2:28])=[CH:21][CH:20]=1.OS(O)(=O)=O.C(Cl)Cl.CO>CCO.CCOC(C)=O>[CH2:26]([N:27]1[C:4]([NH2:5])=[CH:3][C:2]([C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][N:7]=2)=[N:28]1)[CH2:25][C:22]1[CH:23]=[CH:24][CH:19]=[CH:20][CH:21]=1

Komponenten

7

Edukt 4

HCID 8471TriethylamineHCID 61100Phenelzine SulfateHCID 115718233-Oxo-3-(pyridin-2-yl)propanenitrileHCID 21226129Dichloromethane methanol

Produkt 1

HCID 672999082-Phenethyl-5-pyridin-2-yl-2H-pyrazol-3-ylamine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a stirred solution of 3-oxo-3-pyridin-2-yl-propionitrile (0.46 g, 3.1 mmol; CAS 54123-21-6) at r.t. in EtOH (10 ml) under an argon atmosphere were added triethylamine (2.6 ml, 18.9 mmol) and phenelzine sulfate salt (2.2 g, 9.4 mmol). The mixture was heated to reflux and stirring was continued for 2 hrs. The orange solution was cooled to r.t. The solids were filtered off. The filtrate was concentrated to leave an orange viscous oil which was taken up in EtOAc and washed with water. The aqueous layer was extracted with EtOAc and with CH2Cl2/MeOH 9:1. The combined organics were dried over MgSO4, filtered and concentrated. The product was obtained after silica gel chromatography using CH2Cl2/MeOH as gradient as off-white solid (0.722 g, 87%). MS: M=265.1 (M+H)+

Aufarbeitung

  1. temperatureThe mixture was heated
  2. temperatureto reflux
  3. filtrationThe solids were filtered off
  4. concentrationThe filtrate was concentrated
  5. customto leave an orange viscous oil which
  6. washwashed with water
  7. extractionThe aqueous layer was extracted with EtOAc and with CH2Cl2/MeOH 9:1
  8. dry with materialThe combined organics were dried over MgSO4
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customThe product was obtained after silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-3345add7cd204414b6fe60d36c6e73b3
Quelldatensatz
uspto-grants-2013_06
Patentnummer
US08470820B2

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