Potassium Carbonate → Ethyl 4-[2-(tert-butoxycarbonylamino)ethylamino]-1,3-dimethyl-pyrazolo[3,4-b]pyridine-5-carboxylate

HRID 333088

Reaktionsgleichung

Reaktionsgleichung von HRID 333088
Cl[C:2]1[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:6][N:5]=[C:4]2[N:13]([CH3:17])[N:14]=[C:15]([CH3:16])[C:3]=12.C(=O)([O-])[O-].[K+].[K+].[NH2:24][CH2:25][CH2:26][NH:27][C:28](=[O:34])[O:29][C:30]([CH3:33])([CH3:32])[CH3:31]>C(#N)C>[C:30]([O:29][C:28]([NH:27][CH2:26][CH2:25][NH:24][C:2]1[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:6][N:5]=[C:4]2[N:13]([CH3:17])[N:14]=[C:15]([CH3:16])[C:3]=12)=[O:34])([CH3:33])([CH3:32])[CH3:31]

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 187201N-BOC-ethylenediamineHCID 2736380ethyl 4-chloro-1,3-dimethyl-1H-pyrazolo[3,4-b]pyridine-5-carboxylate

Produkt 1

HCID 86691173Ethyl 4-[2-(tert-butoxycarbonylamino)ethylamino]-1,3-dimethyl-pyrazolo[3,4-b]pyridine-5-carboxylateAusbeute 88,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

To a mixture of ethyl 4-chloro-1,3-dimethyl-1H-pyrazolo[3,4-b]pyridine-5-carboxylate (500 mg, 1.971 mmol) and potassium carbonate (817 mg, 5.91 mmol) in acetonitrile (15 ml) was slowly added tert-butyl N-(2-aminoethyl)carbamate (1.248 ml, 7.88 mmol) via a syringe. The reaction mixture was stirred at room temperature for 3 hours. The solids were filtered off over a glass filter and washed with a 1:1 mixture of EtOH and DCM. The combined filtrates were concentrated under reduced pressure to give a white semisolid, which was purified by column chromatography (silica gel using a gradient of ethanol (0-5%) in DCM) to yield 658 mg of a white solid (1.743 mmol, 88%). MS (ESI) m/z=378.2 [M+1]+.

Aufarbeitung

  1. filtrationThe solids were filtered off over a glass
  2. filtrationfilter
  3. washwashed with a 1:1 mixture of EtOH and DCM
  4. concentrationThe combined filtrates were concentrated under reduced pressure
  5. customto give a white semisolid, which
  6. customwas purified by column chromatography (silica gel using a gradient of ethanol (0-5%) in DCM)

Quellen und Nachweise

ORD-Eintrag
ord-b309a9572f61447b908ca284509cd18b
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08877934B2

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