[3-(Pyrrolidine-1-sulfonyl)phenyl]boronic acid → HCID 49835468, compound

HRID 445591Notes

Reaction equation

HRID 445591 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([S:29]([C:32]2[CH:33]=[C:34](B(O)O)[CH:35]=[CH:36][CH:37]=2)(=[O:31])=[O:30])[CH2:28][CH2:27][CH2:26][CH2:25]1>>[CH3:20][N:18]1[CH:19]=[C:15]([N:14]2[C:5]3[C:4]4[CH:3]=[C:2]([C:36]5[CH:35]=[CH:34][CH:33]=[C:32]([S:29]([N:24]6[CH2:28][CH2:27][CH2:26][CH2:25]6)(=[O:30])=[O:31])[CH:37]=5)[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 44119834[3-(Pyrrolidine-1-sulfonyl)phenyl]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 49835468HCID 49835468, 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 3-(pyrrolidinylsulfonyl)phenylboronic acid (Combi-Blocks, San Diego, USA, 33 mg, 0.129 mmol) to give the title compound as a white solid. (HPLC: tR 2.78 min (Method A); M+H=503 MS-ES; 1H-NMR (d6-DMSO, 400 MHz) 9.00 (s, 1H), 8.16-8.11 (m, 2H), 8.02-7.96 (m, 1H), 7.94-7.89 (m, 1H), 7.83-7.78 (m, 1H), 7.77-7.71 (m, 2H), 7.69-7.65 (m, 1H), 3.92 (s, 3H), 3.58 (s, 3H), 3.21-3.14 (m, 4H), 1.95 (s, 3H), 1.70-1.63 (m, 4H))

Workup

  1. customThe title compound was synthesized in a similar manner

Sources & evidence

ORD record
ord-5b08e5e666e749fd8e447a6e8d3e32d6
Source dataset
uspto-grants-2013_07
Patent number
US08476294B2

Reaction notes

Loading…