2-(N,N-dimethylsulphamoyl)benzeneboronic acid → 4'-(5-Aminopyrazin-2-yl)-N,N,3'-trimethylbiphenyl-2-sulfonamide

HRID 1524057Notes

Reaction equation

HRID 1524057 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[CH:10][C:11]([NH2:14])=[N:12][CH:13]=2)=[C:4]([CH3:15])[CH:3]=1.[CH3:16][N:17]([CH3:30])[S:18]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1B(O)O)(=[O:20])=[O:19]>>[NH2:14][C:11]1[N:12]=[CH:13][C:8]([C:5]2[CH:6]=[CH:7][C:2]([C:22]3[C:21]([S:18]([N:17]([CH3:30])[CH3:16])(=[O:19])=[O:20])=[CH:26][CH:25]=[CH:24][CH:23]=3)=[CH:3][C:4]=2[CH3:15])=[N:9][CH:10]=1

Participants

3

Reactant 2

HCID 41973482-(N,N-dimethylsulphamoyl)benzeneboronic acidHCID 903131615-(4-Bromo-2-methylphenyl)pyrazin-2-amine

Product 1

HCID 903142624'-(5-Aminopyrazin-2-yl)-N,N,3'-trimethylbiphenyl-2-sulfonamide

Procedure

The title compound was prepared in a manner similar to that described in Example 589 using 5-(4-bromo-2-methylphenyl)pyrazin-2-amine and (2-(N,N-dimethylsulfamoyl)phenyl)boronic acid. MS (ESI): mass calcd. for C19H20N4O2S, 368.46; m/z found, 369.1 [M+H]+. 1H NMR (500 MHz, CDCl3) δ 8.16 (d, J=1.5, 1H), 8.12 (dd, J=8.0, 1.3, 1H), 8.10 (d, J=1.5, 1H), 7.60-7.55 (m, 1H), 7.52-7.47 (m, 1H), 7.43 (d, J=7.8, 1H), 7.35-7.29 (m, 3H), 4.77 (s, 2H), 2.44 (s, 3H), 2.42 (s, 6H).

Sources & evidence

ORD record
ord-d87bec5a46ee41f287d17e9e2f10e5ef
Source dataset
uspto-grants-2015_07
Patent number
US09079866B2

Reaction notes

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