Phenylboronic Acid → 3-Methyl-1-{3-methyl-1-[2-(4-methyl-piperazin-1-yl)-2-oxo-ethyl]-1H-pyrazol-4-yl}-8-phenyl-1,3-dihydro-imidazo[4,5-c]quinolin-2-one

HRID 445691Notes

Reaction equation

HRID 445691 reaction equation
Br[C:2]1[CH:11]=[CH:10][C:9]2[N:8]=[CH:7][C:6]3[N:12]([CH3:32])[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.[C:33]1(B(O)O)[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1>>[CH3:32][N:12]1[C:6]2[CH:7]=[N:8][C:9]3[CH:10]=[CH:11][C:2]([C:33]4[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=4)=[CH:3][C:4]=3[C:5]=2[N:14]([C:15]2[C:16]([CH3:30])=[N:17][N:18]([CH2:20][C:21]([N:23]3[CH2:28][CH2:27][N:26]([CH3:29])[CH2:25][CH2:24]3)=[O:22])[CH:19]=2)[C:13]1=[O:31]

Participants

3

Reactant 2

HCID 66827Phenylboronic AcidHCID 596197298-bromo-3-methyl-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

Product 1

HCID 596196743-Methyl-1-{3-methyl-1-[2-(4-methyl-piperazin-1-yl)-2-oxo-ethyl]-1H-pyrazol-4-yl}-8-phenyl-1,3-dihydro-imidazo[4,5-c]quinolin-2-one

Procedure

The title compound was synthesized in a similar manner as described for Example 1.1 using 8-bromo-3-methyl-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 134.1.1) and phenylboronic acid (Aldrich, Buchs, Switzerland) to give the title compound as a white solid. (HPLC: tR 2.32 min (Method A); M+H=496 MS-ES; 1H-NMR (d6-DMSO, 400 MHz) 8.96 (s, 1H), 8.11-8.07 (m, 2H), 7.96-7.92 (m, 1H), 7.81-7.79 (m, 1H), 7.69-7.65 (m, 2H), 7.45-7.39 (m, 2H), 7.37-7.32 (m, 1H), 5.28-5.16 (m, 21-1), 3.59-3.43 (m, 7H), 2.40-2.29 (m, 4H), 2.20 (s, 3H), 1.92 (s, 3H))

Workup

  1. customThe title compound was synthesized in a similar manner

Sources & evidence

ORD record
ord-8d5a604580544983b0a5fdc8569a7b05
Source dataset
uspto-grants-2013_07
Patent number
US08476294B2

Reaction notes

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