Reaktion #1862260

Reaktionsgleichung

tert-butyl (1-(6-(5-(pyridin-3-yl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl)piperidin-4-yl)methylcarbamate

HCl

→

278

Ausbeute 50.2%

(1-(6-(5-(pyridin-3-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl)piperidin-4-yl)methanamine

Ausbeute 50.2%

Lösungsmittel

dioxane

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeUpon completion of the reaction
2. 2
   workup.DISTILLATIONthe solvent was distilled off
3. 3
   Sonstigethe crude material was purified via reverse phase
4. 4
   Waschenprep-HPLC eluting with 40% to 80% MeOH in aqueous 0.1% NH4OH solution

Vorschrift

To a solution of tert-butyl (1-(6-(5-(pyridin-3-yl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl)piperidin-4-yl)methylcarbamate (190 mg, 0.31 mmol) in dioxane (5 mL), was added 10% HCl (1 mL). The reaction mixture was heated at 70° C. for 2 h, and the reaction was monitored by LCMS. Upon completion of the reaction, the solvent was distilled off and the crude material was purified via reverse phase prep-HPLC eluting with 40% to 80% MeOH in aqueous 0.1% NH4OH solution to afford 278 as a yellow solid (60 mg, 50%). 1H NMR (400 MHz, DMSO) 9.23 (s, 2H), 8.95 (s, 1H), 8.61-8.60 (d, J=2.8, 1H), 8.40-8.38 (m, 1H), 7.68-7.65 (m, 1H), 7.58-7.55 (m, 1H), 7.48-7.46 (m, 1H), 4.96 (s, 1H), 4.53-4.50 (d, J=10.4, 1H), 3.38-3.36 (m, 3H), 2.69-2.68 (d, J=4, 2H), 188-1.86 (d, J=8.3H), 1.32-1.30 (m, 3H). ESI MS m/z=385.2 (M+1)

Quelle