(3-Carbamoylphenyl)boronic acid → HCID 49835469, compound

HRID 445593Notes

Reaction equation

HRID 445593 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.B(O)(O)[C:25]1[CH:30]=[CH:29][CH:28]=[C:27]([C:31]([NH2:33])=[O:32])[CH:26]=1>>[CH3:20][N:18]1[CH:19]=[C:15]([N:14]2[C:5]3[C:4]4[CH:3]=[C:2]([C:25]5[CH:26]=[C:27]([CH:28]=[CH:29][CH:30]=5)[C:31]([NH2:33])=[O:32])[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 2737814(3-Carbamoylphenyl)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 49835469HCID 49835469, 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, 40 mg, 0.106 mmol) and benzamide-3-boronic acid (ABCR, Karlsruhe, Germany, 21 mg, 0.129 mmol) to give the title compound as a white solid. (HPLC: tR 2.34 min (Method A); M+H=413 MS-ES; 1H-NMR (d6-DMSO, 400 MHz) 8.98 (s, 1H), 8.19-8.16 (m, 1H), 8.14-8.10 (m, 1H), 8.09-8.04 (m, 1H), 8.02-7.95 (m, 2H), 7.89-7.83 (m, 1H), 7.65-7.59 (m, 2H), 7.58-7.47 (m, 2H), 3.94 (s, 3H), 3.58 (s, 3H), 1.93 (s, 3H))

Workup

  1. customThe title compound was synthesized in a similar manner

Sources & evidence

ORD record
ord-194bbb83b6b948e3ac5cb6fb4f02fc3a
Source dataset
uspto-grants-2013_07
Patent number
US08476294B2

Reaction notes

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