2-Ethoxypyridine-5-boronic Acid → 8-(6-Ethoxy-pyridin-3-yl)-1-{3-methyl-1-[2-(4-methyl-piperazin-1-yl)-2-oxo-ethyl]-1H-pyrazol-4-yl}-1,3-dihydro-imidazo[4,5-c]quinolin-2-one
Reaction equation
Br[C:2]1[CH:11]=[CH:10][C:9]2[N:8]=[CH:7][C:6]3[NH:12][C:13](=[O:31])[N:14]([C:15]4[C:16]([CH3:30])=[N:17][N:18]([CH2:20][C:21]([N:23]5[CH2:28][CH2:27][N:26]([CH3:29])[CH2:25][CH2:24]5)=[O:22])[CH:19]=4)[C:5]=3[C:4]=2[CH:3]=1.[CH2:32]([O:34][C:35]1[N:40]=[CH:39][C:38](B(O)O)=[CH:37][CH:36]=1)[CH3:33]>>[CH2:32]([O:34][C:35]1[N:40]=[CH:39][C:38]([C:2]2[CH:11]=[CH:10][C:9]3[N:8]=[CH:7][C:6]4[NH:12][C:13](=[O:31])[N:14]([C:15]5[C:16]([CH3:30])=[N:17][N:18]([CH2:20][C:21]([N:23]6[CH2:28][CH2:27][N:26]([CH3:29])[CH2:25][CH2:24]6)=[O:22])[CH:19]=5)[C:5]=4[C:4]=3[CH:3]=2)=[CH:37][CH:36]=1)[CH3:33]Participants
3
Reactant 2
Product 1
Procedure
The title compound was synthesized in a similar manner as described for Example 1.1 using 8-bromo-1-{3-methyl-1-[2-(4-methyl-piperazin-1-yl)-2-oxo-ethyl]-1H-pyrazol-4-yl}-1,3-dihydro-imidazo[4,5-c]quinolin-2-one (Stage 133.1.1) and 6-ethoxypyridine-3-boronic acid (ABCR, Karlsruhe, Germany) to give the title compound as a white solid. (HPLC: tR 2.27 min (Method A); M+H=527 MS-ES; 1H-NMR (d6-DMSO, 400 MHz) 11.69 (s, br, 1H), 8.71 (s, 1H), 8.45-8.42 (m, 1H), 8.08-8.03 (m, 2H), 7.96-7.88 (m, 2H), 7.74-7.71 (m, 1H), 6.81-6.67 (m, 1H), 5.27-5.11 (m, 2H), 4.32 (q, 2H), 3.58-3.38 (m, 4H), 2.38-2.26 (m, 4H), 2.19 (s, 3H), 1.92 (s, 3H), 1.31 (t, 2H))
Workup
- customThe title compound was synthesized in a similar manner
Sources & evidence
- ORD record
- ord-09ffb41f2a56473ea00274b1ed3f362b
- Source dataset
- uspto-grants-2013_07
- Patent number
- US08476294B2
Reaction notes
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