Reaktion #837879

ord-19a03bf244a34b5cae138c23ed6b218b

Reaktionsgleichung

COc1ccc(CN2N=C(c3c(C)n(CC(=O)OC(C)(C)C)c4ccc(F)cc34)c3ccccc3S2(=O)=O)cc1
{3-[2-(4-Methoxy-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
→
COc1ccc(CN2N=C(c3c(C)n(CC(=O)O)c4ccc(F)cc34)c3ccccc3S2(=O)=O)cc1
title compound
COc1ccc(CN2N=C(c3c(C)n(CC(=O)O)c4ccc(F)cc34)c3ccccc3S2(=O)=O)cc1
{3-[2-(4-Methoxy-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

COc1ccc(CN2N=C(c3c(C)n(CC(=O)OC(C)(C)C)c4ccc(F)cc34)c3ccccc3S2(=O)=O)cc1
{3-[2-(4-Methoxy-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-(4-Methoxy-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 8.12 (d, 1H), 7.91 (t, 1H), 7.81 (t, 1H), 7.44 (d, 1H), 7.32 (m, 3H), 6.92 (m, 3H), 6.62 (dd, 1H), 4.99 (bs, 2H), 4.51 (s, 2H), 3.73 (s, 3H), 2.09 (s, 3H) ppm. MS calculated for C26H22FN3O5S—H: 506, observed: 506.

Quelle

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