Reaktion #2366315

ord-a2168188b1d042a4943d155b8e0a6fd3

Reaktionsgleichung

Cc1n[nH]c2nc(-c3ccc(O)cc3F)cc(CN3CC(C)(C)N(C[C@H]4COC(C)(C)O4)CC3(C)C)c12
4-{4-[4-((S)-2,2-Dimethyl-[1,3]dioxolan-4-ylmethyl)-2,2,5,5-tetramethyl-piperazin-1-ylmethyl]-3-methyl-1H-pyrazolo[3,4-b]pyridin-6-yl}-3-fluoro-phenol
→
Cc1n[nH]c2nc(-c3ccc(O)cc3F)cc(CN3CC(C)(C)N(C[C@H](O)CO)CC3(C)C)c12
title compound
Ausbeute 31.3%
Cc1n[nH]c2nc(-c3ccc(O)cc3F)cc(CN3CC(C)(C)N(C[C@H](O)CO)CC3(C)C)c12
(S)-3-{4-[6-(2-Fluoro-4-hydroxy-phenyl)-3-methyl-1H-pyrazolo[3,4-b]pyridin-4-ylmethyl]-2,2,5,5-tetramethyl-piperazin-1-yl}-propane-1,2-diol
Ausbeute 31.3%

Edukte

Cc1n[nH]c2nc(-c3ccc(O)cc3F)cc(CN3CC(C)(C)N(C[C@H]4COC(C)(C)O4)CC3(C)C)c12
4-{4-[4-((S)-2,2-Dimethyl-[1,3]dioxolan-4-ylmethyl)-2,2,5,5-tetramethyl-piperazin-1-ylmethyl]-3-methyl-1H-pyrazolo[3,4-b]pyridin-6-yl}-3-fluoro-phenol
—
hydrorchloric acid

Reagenzien

Keine

Lösungsmittel

O
water
C1COCCO1
dioxane

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    SonstigeAfter 1.5 h at rt the volatiles were removed in vacuo
  2. 2
    Sonstigethe residue was purified by HPLC

Vorschrift

208 mg 4-{4-[4-((S)-2,2-Dimethyl-[1,3]dioxolan-4-ylmethyl)-2,2,5,5-tetramethyl-piperazin-1-ylmethyl]-3-methyl-1H-pyrazolo[3,4-b]pyridin-6-yl}-3-fluoro-phenol were dissolved in 2 ml of dioxane and 0.3 ml of water. 2 ml of hydrorchloric acid (4M in dioxane) were added. After 1.5 h at rt the volatiles were removed in vacuo and the residue was purified by HPLC. 60 mg of the title compound ewre obtained.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US09133181B2uspto-grants-2015_09