8-bromo-1-(1-ethyl-3-methyl-1H-pyrazol-4-yl)-3-methyl-1,3-dihydro-imidazo[4,5-c]quinolin-2-one → 8-(3,4-Diethoxy-phenyl)-1-(1-ethyl-3-methyl-1H-pyrazol-4-yl)-3-methyl-1,3-dihydro-imidazo[4,5-c]quinolin-2-one

HRID 445574

Reaktionsgleichung

Reaktionsgleichung von HRID 445574
Br[C:2]1[CH:11]=[CH:10][C:9]2[N:8]=[CH:7][C:6]3[N:12]([CH3:24])[C:13](=[O:23])[N:14]([C:15]4[C:16]([CH3:22])=[N:17][N:18]([CH2:20][CH3:21])[CH:19]=4)[C:5]=3[C:4]=2[CH:3]=1.[CH2:25]([O:27][C:28]1[CH:29]=[C:30](B2OC(C)(C)C(C)(C)O2)[CH:31]=[CH:32][C:33]=1[O:34][CH2:35][CH3:36])[CH3:26]>>[CH2:35]([O:34][C:33]1[CH:32]=[C:31]([C:2]2[CH:11]=[CH:10][C:9]3[N:8]=[CH:7][C:6]4[N:12]([CH3:24])[C:13](=[O:23])[N:14]([C:15]5[C:16]([CH3:22])=[N:17][N:18]([CH2:20][CH3:21])[CH:19]=5)[C:5]=4[C:4]=3[CH:3]=2)[CH:30]=[CH:29][C:28]=1[O:27][CH2:25][CH3:26])[CH3:36]

Komponenten

3

Edukt 2

HCID 596196758-bromo-1-(1-ethyl-3-methyl-1H-pyrazol-4-yl)-3-methyl-1,3-dihydro-imidazo[4,5-c]quinolin-2-one2×HCID 596199022-(3,4-Diethoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Produkt 1

HCID 596198508-(3,4-Diethoxy-phenyl)-1-(1-ethyl-3-methyl-1H-pyrazol-4-yl)-3-methyl-1,3-dihydro-imidazo[4,5-c]quinolin-2-one

Versuchsvorschrift

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, 49 mg, 0.126 mmol) and 2-(3,4-diethoxy-phenyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane (stage 27.1.1, 47 mg, 0.161 mmol) to give the title compound as an off-white solid. (HPLC: tR 3.02 min (Method A); M+H=472 MS-ES; 1H-NMR (d6-DMSO, 400 MHz) 8.97 (s, 1H), 8.18 (s, 1H), 8.08-8.02 (m, 1H), 7.95-7.84 (m, 1H), 7.52-7.48 (m, 1H), 7.06-6.97 (m, 3H), 4.22-3.98 (m, 6H), 3.58 (s, 3H), 1.97 (s, 3H) 1.45-1.25 (m, 9H))

Aufarbeitung

  1. customThe title compound was synthesized in a similar manner

Quellen und Nachweise

ORD-Eintrag
ord-7c30e7791bf1498f9d598d27edb324d4
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08476294B2

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