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Cyclopentylamine → HCID 18446602, Verbindung

HRID 1269031
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1269031
Cl[C:2]1[N:7]2[N:8]=[C:9]([C:14]3[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=3)[C:10]([C:11](=[O:13])[CH3:12])=[C:6]2[CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[CH:26]1([NH2:31])[CH2:30][CH2:29][CH2:28][CH2:27]1.C(OCC)(=O)C>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(P(C2C=CC=CC=2)C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O>[CH:26]1([NH:31][C:2]2[N:7]3[N:8]=[C:9]([C:14]4[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=4)[C:10]([C:11](=[O:13])[CH3:12])=[C:6]3[CH:5]=[CH:4][CH:3]=2)[CH2:30][CH2:29][CH2:28][CH2:27]1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

9

Edukt 4

HCID 2906CyclopentylamineHCID 8857Ethyl AcetateHCID 10796Cesium carbonateHCID 18446599HCID 18446599, Verbindung

Produkt 1

HCID 18446602HCID 18446602, VerbindungAusbeute 80 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 167845
palladium(II) acetate
Katalysator
HCID 634876Binap, (A+-)-Katalysator
HCID 962WaterLösungsmittel
HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

To a solution of 1-[7-chloro-2-(4-pyridinyl)pyrazolo[1,5-a]pyridin-3-yl]ethanone (0.68 g, 2.5 mmol) in toluene (10 mL) was added successively rac-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (100 mg, 0.15 mmol), cesium carbonate (1.2 g, 3.8 mmol), cyclopentylamine (1.5 mL, 12.5 mmol), and palladium (II) acetate (25 mg, 0.1 mmol). The resulting mixture was stirred at 90° C. for 24 hours, at which time the reaction was judged complete by thin layer chromatography. The solution was cooled to room temperature and ethyl acetate and water were added to the reaction mixture. The phases were separated, and the aquous phase again extracted with ethyl acetate. The combined organic phases were dried (magnesium sulfate), filtered and concentrated. The resulting residue was purified by flash chromatography (1:1 hexanes-ethyl acetate) to give 1-[7-(cyclopentylamino)-2-(4-pyridinyl)pyrazolo[1,5-a]pyridin-3-yl]ethanone (0.64 g, 80%) as a yellow foam. 1H NMR (CDCl3): δ 8.80 (d, 2H), 7.65 (d, 1H), 7.60 (d, 2H), 7.50 (t, 1H), 6.20 (d, 1H), 6.06 (d, 1H), 4.0 (m, 1H), 2.26 (s, 3H), 1.6–2.2 (m, 8H); MS m/z 321 (M+1).

Aufarbeitung

  1. temperatureThe solution was cooled to room temperature
  2. customThe phases were separated
  3. extractionthe aquous phase again extracted with ethyl acetate
  4. dry with materialThe combined organic phases were dried (magnesium sulfate)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe resulting residue was purified by flash chromatography (1:1 hexanes-ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-8f9e6fb9f7154338b7e04243ea210dc9
Quelldatensatz
uspto-grants-2007_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07199120B2

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