4-Chloro-1-ethyl-1H-pyrazolo[3,4-b]pyridine-5-carboxylic acid → 4-{[4-(tert-butoxycarbonyl)cyclohexyl]amino}-1-ethyl-1H-pyrazolo[3,4-b]pyridine-5-carboxylic acid

HRID 1966804Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1966804
Cl[C:2]1[C:7]([C:8]([OH:10])=[O:9])=[CH:6][N:5]=[C:4]2[N:11]([CH2:14][CH3:15])[N:12]=[CH:13][C:3]=12.[NH2:16][CH:17]1[CH2:22][CH2:21][CH:20]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:19][CH2:18]1>C(#N)C>[C:26]([O:25][C:23]([CH:20]1[CH2:19][CH2:18][CH:17]([NH:16][C:2]2[C:7]([C:8]([OH:10])=[O:9])=[CH:6][N:5]=[C:4]3[N:11]([CH2:14][CH3:15])[N:12]=[CH:13][C:3]=23)[CH2:22][CH2:21]1)=[O:24])([CH3:29])([CH3:27])[CH3:28]

Komponenten

4

Edukt 2

HCID 183487784-Chloro-1-ethyl-1H-pyrazolo[3,4-b]pyridine-5-carboxylic acidHCID 18698345tert-Butyl 4-aminocyclohexane-1-carboxylate

Produkt 1

HCID 667332594-{[4-(tert-butoxycarbonyl)cyclohexyl]amino}-1-ethyl-1H-pyrazolo[3,4-b]pyridine-5-carboxylic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

A solution of 4-chloro-1-ethyl-1H-pyrazolo[3,4-b]pyridine-5-carboxylic acid (0.0088 mol) (example 4a) in acetonitrile is treated with tert-butyl 4-aminocyclohexanecarboxylate (0.026 mol). The reaction mixture is refluxed for about 3-4 hrs. Solvent is evaporated off and water is added and extraction is done with ethyl acetate. The organic layer is washed with brine, dried and concentrated under reduced pressure to give crude compound, which is purified by column chromatography.

Aufarbeitung

  1. temperatureThe reaction mixture is refluxed for about 3-4 hrs
  2. customSolvent is evaporated off
  3. additionwater is added
  4. extractionextraction
  5. washThe organic layer is washed with brine
  6. customdried
  7. concentrationconcentrated under reduced pressure
  8. customto give crude compound, which
  9. customis purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-07811eec4db54f89aa80530332fa589d
Quelldatensatz
uspto-grants-2013_04
Patentnummer
US08420666B2

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