3-Methylsulfonylaminophenylboronic acid → HCID 49835470, compound

HRID 445594Notes

Reaction equation

HRID 445594 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.[CH3:24][S:25]([NH:28][C:29]1[CH:30]=[C:31](B(O)O)[CH:32]=[CH:33][CH:34]=1)(=[O:27])=[O:26]>>[CH3:20][N:18]1[CH:19]=[C:15]([N:14]2[C:5]3[C:4]4[CH:3]=[C:2]([C:33]5[CH:34]=[C:29]([NH:28][S:25]([CH3:24])(=[O:26])=[O:27])[CH:30]=[CH:31][CH:32]=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 27735353-Methylsulfonylaminophenylboronic 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 49835470HCID 49835470, 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-(Methanesulfonylamino)phenylboronic acid (ABCR, Karlsruhe, Germany, 28 mg, 0.126 mmol) to give the title compound as a white solid. (HPLC: tR 2.46 min (Method A); M+H=463 MS-ES; 1H-NMR (d6-DMSO, 400 MHz) 9.88 (s, 1H), 8.97 (s, 1H), 8.12-8.10 (m, 2H), 7.82-7.79 (m, 1H), 7.56-7.54 (m, 1H), 7.45-7.41 (m, 1H), 7.36-7.34 (m, 1H), 7.21-7.16 (m, 2H), 3.90 (s, 3H), 3.58 (s, 3H), 3.03 (s, 3H), 1.96 (s, 3H))

Workup

  1. customThe title compound was synthesized in a similar manner

Sources & evidence

ORD record
ord-5e2a252d64e64bed8470d72499a0bd2c
Source dataset
uspto-grants-2013_07
Patent number
US08476294B2

Reaction notes

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