Reaktion #837883

ord-1479bfdc24844a54abfc7d5d79b1fd5d

Reaktionsgleichung

Cc1c(C2=NN(Cc3cccc(F)c3)S(=O)(=O)c3ccccc32)c2cc(F)ccc2n1CC(=O)OC(C)(C)C
{3-[2-(3-Fluoro-benzyl)-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(Cc3cccc(F)c3)S(=O)(=O)c3ccccc32)c2cc(F)ccc2n1CC(=O)O
title compound
Cc1c(C2=NN(Cc3cccc(F)c3)S(=O)(=O)c3ccccc32)c2cc(F)ccc2n1CC(=O)O
{3-[2-(3-Fluoro-benzyl)-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(Cc3cccc(F)c3)S(=O)(=O)c3ccccc32)c2cc(F)ccc2n1CC(=O)OC(C)(C)C
{3-[2-(3-Fluoro-benzyl)-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-(3-Fluoro-benzyl)-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 8.17 (d, 1H), 7.95 (t, 1H), 7.86 (t, 1H), 7.42 (m, 3H), 7.19 (m, 3H), 6.89 (dt, 1H), 6.61 (dd, 1H), 5.09 (bs, 2H), 4.53 (s, 2H), 2.09 (s, 3H) ppm. MS calculated for C25H19F2N3O4S—H: 494, observed: 494.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07405215B2uspto-grants-2008_07