Reaktion #532758

ord-abb77ebe45344631850132ae837964fe

Reaktionsgleichung

CCn1cc(-n2c(=O)n(C)c3cnc4ccc(Br)cc4c32)c(C)n1
8-bromo-1-(1-ethyl-3-methyl-1H-pyrazol-4-yl)-3-methyl-1,3-dihydro-imidazo[4,5-c]quinolin-2-one
CCn1cc(-n2c(=O)n(C)c3cnc4ccc(Br)cc4c32)c(C)n1
Intermediate F
CCn1cc(-n2c(=O)n(C)c3cnc4ccc(Br)cc4c32)c(C)n1
8-bromo-1-(1-ethyl-3-methyl-1H-pyrazol-4-yl)-3-methyl-1,3-dihydro-imidazo[4,5-c]quinolin-2-one
CCOc1cc(B(O)O)ccc1OC
3-ethoxy-4-methoxyphenylboronic acid
CCOc1cc(-c2ccc3ncc4c(c3c2)n(-c2cn(CC)nc2C)c(=O)n4C)ccc1OC
title compound
CCOc1cc(-c2ccc3ncc4c(c3c2)n(-c2cn(CC)nc2C)c(=O)n4C)ccc1OC
8-(3-Ethoxy-4-methoxy-phenyl)-1-(1-ethyl-3-methyl-1H-pyrazol-4-yl)-3-methyl-1,3-dihydro-imidazo[4,5-c]quinolin-2-one

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    SonstigeThe title compound was synthesized in a similar manner

Vorschrift

The title compound was synthesized in a similar manner as described for Example 1.1 using 8-bromo-1-(1-ethyl-3-methyl-1H-pyrazol-4-yl)-3-methyl-1,3-dihydro-imidazo[4,5-c]quinolin-2-one (Intermediate F, 39 mg, 0.100 mmol) and 3-ethoxy-4-methoxyphenylboronic acid (Combi-Blocks, San Diego, USA, 25.5 mg, 0.130 mmol) to give the title compound as an off-white foam. (HPLC: tR 2.86 min (Method A); M+H=458 MS-ES; 1H-NMR (d6-DMSO, 400 MHz) 8.92 (s, 1H), 8.16 (s, 1H), 8.08-8.01 (m, 1H), 7.93-7.87 (m, 1H), 7.52-7.46 (m, 1H), 7.06-6.96 (m, 3H), 4.20-4.03 (m, 4H), 3.77 (s, 3H), 3.57 (s, 3H), 1.97 (s, 3H), 1.45-1.33 (m, 6H))

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08476294B2uspto-grants-2013_07