2,4-Dimethoxypyrimidine-5-boronic acid pinacol ester → 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

HRID 445772

Reaktionsgleichung

Reaktionsgleichung von HRID 445772
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.[CH3:25][O:26][C:27]1[N:32]=[C:31]([O:33][CH3:34])[C:30](B2OC(C)(C)C(C)(C)O2)=[CH:29][N:28]=1>>[CH3:25][O:26][C:27]1[N:32]=[C:31]([O:33][CH3:34])[C:30]([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:29][N:28]=1

Komponenten

3

Edukt 2

HCID 162183882,4-Dimethoxypyrimidine-5-boronic acid pinacol esterHCID 596196758-bromo-1-(1-ethyl-3-methyl-1H-pyrazol-4-yl)-3-methyl-1,3-dihydro-imidazo[4,5-c]quinolin-2-one2×

Produkt 1

HCID 596198118-(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

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, 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))

Aufarbeitung

  1. customThe title compound was synthesized in a similar manner

Quellen und Nachweise

ORD-Eintrag
ord-4760a23fb9ea4d19b75833b818d4ec5b
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08476294B2

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