Reaktion #532742

ord-a1c52982672547e1b4b85e1c151a5b97

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
OCc1ccc(B(O)O)cn1
6-(hydroxymethyl)pyridine-3-boronic acid
CCn1cc(-n2c(=O)n(C)c3cnc4ccc(-c5ccc(CO)nc5)cc4c32)c(C)n1
title compound
CCn1cc(-n2c(=O)n(C)c3cnc4ccc(-c5ccc(CO)nc5)cc4c32)c(C)n1
1-(1-Ethyl-3-methyl-1H-pyrazol-4-yl)-8-(6-hydroxymethyl-pyridin-3-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, 80 mg, 0.207 mmol) and 6-(hydroxymethyl)pyridine-3-boronic acid (Combi-Blocks, San Diego, USA, 39 mg, 0.254 mmol) to give the title compound as a white solid. (HPLC: tR 2.04 min (Method A); M+H=415 MS-ES; 1H-NMR (d6-DMSO, 400 MHz) 8.98 (s, 1H), 8.61-8.56 (m, 1H), 8.21-8.17 (m, 1H), 8.15-8.09 (m, 1H), 7.97-7.93 (m, 1H), 7.90-7.85 (m, 1H), 7.57-7.49 (m, 2H), 5.47 (t, 1H), 4.61-4.55 (m, 2H), 4.23-4.14 (m, 2H), 3.57 (s, 3H), 1.95 (s, 3H), 1.43 (t, 3H))

Quelle

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