Reaktion #2384864

ord-f6ab49fc28af4caaba07171e311138f7

Reaktionsgleichung

C#C[C@H]1O[C@@H](n2cnc3c(On4nnc5ccccc54)ncnc32)[C@H](OC(C)=O)[C@@H]1OC(C)=O
(2R,3R,4R,5R)-4-(acetyloxy)-2-[6-(1H-1,2,3-benzotriazol-1-yloxy)-9 H-purin-9-yl]-5-ethynyltetrahydrofuran-3-yl acetate
Nc1ccc(Cl)cc1F
2-fluoro-4-chloroaniline
→
C#C[C@H]1O[C@@H](n2cnc3c(Nc4ccc(Cl)cc4F)ncnc32)[C@H](OC(C)=O)[C@@H]1OC(C)=O
title compound
C#C[C@H]1O[C@@H](n2cnc3c(Nc4ccc(Cl)cc4F)ncnc32)[C@H](OC(C)=O)[C@@H]1OC(C)=O
(2R,3R,4R,5R)4-(acetyloxy)-2-[6-(4-chloro-2-fluoroanilino)-9H-purin-9-yl]-5-ethynyltetrahydrofuran-3-yl acetate

Edukte

C#C[C@H]1O[C@@H](n2cnc3c(On4nnc5ccccc54)ncnc32)[C@H](OC(C)=O)[C@@H]1OC(C)=O
(2R,3R,4R,5R)-4-(acetyloxy)-2-[6-(1H-1,2,3-benzotriazol-1-yloxy)-9 H-purin-9-yl]-5-ethynyltetrahydrofuran-3-yl acetate
Nc1ccc(Cl)cc1F
2-fluoro-4-chloroaniline

Reagenzien

Keine

Reaktionsbedingungen

Temperatur
60°CELSIUS
Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    SonstigeThe mixture was purified by chromatography on silica gel (Varian Bondelut cartridge)
  2. 2
    Wascheneluting with ethyl acetate:cyclohexane 10:90-60:40

Vorschrift

(2R,3R,4R,5R)-4-(acetyloxy)-2-[6-(1H-1,2,3-benzotriazol-1-yloxy)-9 H-purin-9-yl]-5-ethynyltetrahydrofuran-3-yl acetate was treated with 2-fluoro-4-chloroaniline (0.63 ml), and the mixture was heated at 60° C. for 22.5 h. The mixture was purified by chromatography on silica gel (Varian Bondelut cartridge), eluting with ethyl acetate:cyclohexane 10:90-60:40, to give the title compound (55 mg).

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US06492348B1uspto-grants-2002_12