Trifluoroacetic acid → 3-methoxy-5-phenyl-4-(piperazin-1-yl)-1H-pyrazolo[3,4-b]pyridine

HRID 387583Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 387583
C(O)(C(F)(F)F)=O.[CH3:8][O:9][C:10]1[C:18]2[C:13](=[N:14][CH:15]=[C:16]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[C:17]=2[N:19]2[CH2:24][CH2:23][N:22](C(OC(C)(C)C)=O)[CH2:21][CH2:20]2)[N:12](CC2C=CC(OC)=CC=2)[N:11]=1>C(Cl)Cl>[CH3:8][O:9][C:10]1[C:18]2[C:13](=[N:14][CH:15]=[C:16]([C:32]3[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=3)[C:17]=2[N:19]2[CH2:20][CH2:21][NH:22][CH2:23][CH2:24]2)[NH:12][N:11]=1

Komponenten

4

Edukt 2

HCID 6422Trifluoroacetic acid2×HCID 68759898tert-butyl 4-(3-methoxy-1-(4-methoxybenzyl)-5-phenyl-1H-pyrazolo[3,4-b]pyridin-4-yl)piperazine-1-carboxylate

Produkt 1

HCID 687585923-methoxy-5-phenyl-4-(piperazin-1-yl)-1H-pyrazolo[3,4-b]pyridineAusbeute 118,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

TFA (0.5 mL) was added to tert-butyl 4-(3-methoxy-1-(4-methoxybenzyl)-5-phenyl-1H-pyrazolo[3,4-b]pyridin-4-yl)piperazine-1-carboxylate (0.098 g, 0.185 mmol) in DCM (2 mL) and stirred at room temperature for 2 hours. The reaction mixture was then concentrated to dryness. The resulting residue was dissolved in TFA (2.85 mL, 37.01 mmol) and heated at 100° C. in a sealed tube for 5 hours. The reaction mixture was again concentrated to dryness. The resulting residue was dissolved in DCM (0.5 mL), followed by the addition of HCl in ether (2 mL, 2N). The resulting solid was collected by filtration to give 3-methoxy-5-phenyl-4-(piperazin-1-yl)-1H-pyrazolo[3,4-b]pyridine (0.068 g, 96%). MS APCI (+) m/z 310.1 detected.

Aufarbeitung

  1. concentrationThe reaction mixture was then concentrated to dryness
  2. temperatureheated at 100° C. in a sealed tube for 5 hours
  3. concentrationThe reaction mixture was again concentrated to dryness
  4. dissolutionThe resulting residue was dissolved in DCM (0.5 mL)
  5. additionfollowed by the addition of HCl in ether (2 mL, 2N)
  6. filtrationThe resulting solid was collected by filtration

Quellen und Nachweise

ORD-Eintrag
ord-cc4346c5c6b34f7db5a13e4f47795f6f
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08372842B2

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