Quinoline-3-boronic acid → HCID 59619693, compound

HRID 445587Notes

Reaction equation

HRID 445587 reaction equation
Br[C:2]1[CH:11]=[CH:10][C:9]2[N:8]=[CH:7][C:6]3[N:12]([CH3:23])[C:13](=[O:22])[N:14]([C:15]4[C:16]([CH3:21])=[N:17][N:18]([CH3:20])[CH:19]=4)[C:5]=3[C:4]=2[CH:3]=1.[N:24]1[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[CH:27]=[C:26](B(O)O)[CH:25]=1>>[CH3:20][N:18]1[CH:19]=[C:15]([N:14]2[C:5]3[C:4]4[CH:3]=[C:2]([C:26]5[CH:25]=[N:24][C:33]6[C:28]([CH:27]=5)=[CH:29][CH:30]=[CH:31][CH:32]=6)[CH:11]=[CH:10][C:9]=4[N:8]=[CH:7][C:6]=3[N:12]([CH3:23])[C:13]2=[O:22])[C:16]([CH3:21])=[N:17]1

Participants

3

Reactant 2

HCID 2734663Quinoline-3-boronic acidHCID 596197398-Bromo-1-(1,3-dimethyl-1H-pyrazol-4-yl)-3-methyl-1,3-dihydro-imidazo[4,5-c]quinolin-2-one2×

Product 1

HCID 59619693HCID 59619693, compound

Procedure

The title compound was synthesized in a similar manner as described for Example 1.1 using 8-bromo-1-(1,3-dimethyl-1H-pyrazol-4-yl)-3-methyl-1,3-dihydro-imidazo[4,5-c]quinolin-2-one (Intermediate A, 39 mg, 0.105 mmol) and 3-quinolineboronic acid (Aldrich, Buchs, Switzerland, 22 mg, 0.127 mmol) to give the title compound as an off-white solid. (HPLC: tR 2.40 min (Method A); M+H=421 MS-ES; 1H-NMR (d6-DMSO, 400 MHz) 9.03-8.96 (m, 2H), 8.52 (s, 1H), 8.21-7.99 (m, 5H), 7.83-7.76 (m, 1H), 7.75-7.71 (m, 1H), 7.71-7.65 (m, 1H), 3.95 (s, 3H), 3.59 (s, 3H), 1.98 (s, 3H))

Workup

  1. customThe title compound was synthesized in a similar manner

Sources & evidence

ORD record
ord-a288455135c5418b9b524eec41457d8e
Source dataset
uspto-grants-2013_07
Patent number
US08476294B2

Reaction notes

Loading…