Reaktion #1540948

ord-e2bfcd55775c4a4e9e2dc3278d3f486b

Reaktionsgleichung

Cc1c(C2=NN(CCOc3ccccc3)S(=O)(=O)c3ccccc32)c2cc(F)ccc2n1CC(=O)OC(C)(C)C
{3-[2-(2-Phenoxy-ethyl)-1,1-dioxo-1,2-dihydro-1λ6-benzo[e][1,2,3]thiadiazin-4-yl]-5-fluoro-2-methyl-indol-1-yl}-acetic acid tert-butyl ester
O=C(O)C(F)(F)F
TFA
→
Cc1c(C2=NN(CCOc3ccccc3)S(=O)(=O)c3ccccc32)c2cc(F)ccc2n1CC(=O)O
title compound
Cc1c(C2=NN(CCOc3ccccc3)S(=O)(=O)c3ccccc32)c2cc(F)ccc2n1CC(=O)O
{3-[2-(2-Phenoxy-ethyl)-1,1-dioxo-1,2-dihydro-1λ6-benzo[e][1,2,3]thiadiazin-4-yl]-5-fluoro-2-methyl-indol-1-yl}-acetic acid

Edukte

Cc1c(C2=NN(CCOc3ccccc3)S(=O)(=O)c3ccccc32)c2cc(F)ccc2n1CC(=O)OC(C)(C)C
{3-[2-(2-Phenoxy-ethyl)-1,1-dioxo-1,2-dihydro-1λ6-benzo[e][1,2,3]thiadiazin-4-yl]-5-fluoro-2-methyl-indol-1-yl}-acetic acid tert-butyl ester
O=C(O)C(F)(F)F
TFA

Reagenzien

Keine

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Einengenconcentrated
  2. 2
    Sonstigepurified by preparative LCMS

Vorschrift

{3-[2-(2-Phenoxy-ethyl)-1,1-dioxo-1,2-dihydro-1λ6-benzo[e][1,2,3]thiadiazin-4-yl]-5-fluoro-2-methyl-indol-1-yl}-acetic acid tert-butyl ester (61 μmol) was treated with TFA (2 mL) for 2 hours, concentrated, and purified by preparative LCMS to give the title compound. 1H NMR (d6-DMSO) δ 8.12 (d, 1H), 7.92 (t, 1H), 7.82 (t, 1H), 7.46 (m, 2H), 7.22 (m, 2H), 6.96 (m, 5H), 4.58 (s, 2H), 4.39 (t, 2H), 4.28 (t, 2H), 2.21 (s, 3H) ppm. MS calculated for C26H22FN3O5S—H: 506, observed: 506.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07476667B2uspto-grants-2009_01