Reaktion #532954

ord-4760a23fb9ea4d19b75833b818d4ec5b

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
COc1ncc(B2OC(C)(C)C(C)(C)O2)c(OC)n1
2,4-dimethoxypyrimidine-5-boronic acid pinacol ester
CCn1cc(-n2c(=O)n(C)c3cnc4ccc(-c5cnc(OC)nc5OC)cc4c32)c(C)n1
title compound
CCn1cc(-n2c(=O)n(C)c3cnc4ccc(-c5cnc(OC)nc5OC)cc4c32)c(C)n1
8-(2,4-Dimethoxy-pyrimidin-5-yl)-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, 0.101 mmol) and 2,4-dimethoxypyrimidine-5-boronic acid pinacol ester (Frontier Scientific, Logan, USA, 0.119 mmol) to give the title compound as a white foam. (HPLC: tR 2.51 min (Method A); M+H=446 MS-ES; 1H-NMR (d6-DMSO, 400 MHz) 8.97 (s, 1H), 8.32 (s, 1H), 8.11 (s, 1H), 8.07-8.04 (m, 1H), 7.78-7.74 (m, 1H), 7.56-7.54 (m, 1H), 4.14 (q, 2H), 3.92 (s, 1H), 3.92 (s, 3H), 3.57 (s, 3H), 1.95 (s, 3H), 1.33 (t, 3H))

Quelle

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