(4-((2-(Diethylamino)ethyl)carbamoyl)phenyl)boronic acid hydrochloride → 4-[8-(2-chloro-3,6-difluorobenzyl)-5,6,7,8-tetrahydropyrazino[2,3-b]pyrazin-2-yl]-N-[2-(diethylamino)ethyl]benzamide

HRID 80551Notes

Reaction equation

HRID 80551 reaction equation
Br[C:2]1[N:7]=[C:6]2[N:8]([CH2:12][C:13]3[C:18]([F:19])=[CH:17][CH:16]=[C:15]([F:20])[C:14]=3[Cl:21])[CH2:9][CH2:10][NH:11][C:5]2=[N:4][CH:3]=1.Cl.[CH2:23]([N:25]([CH2:40][CH3:41])[CH2:26][CH2:27][NH:28][C:29]([C:31]1[CH:36]=[CH:35][C:34](B(O)O)=[CH:33][CH:32]=1)=[O:30])[CH3:24]>>[Cl:21][C:14]1[C:15]([F:20])=[CH:16][CH:17]=[C:18]([F:19])[C:13]=1[CH2:12][N:8]1[CH2:9][CH2:10][NH:11][C:5]2[N:4]=[CH:3][C:2]([C:34]3[CH:35]=[CH:36][C:31]([C:29]([NH:28][CH2:27][CH2:26][N:25]([CH2:40][CH3:41])[CH2:23][CH3:24])=[O:30])=[CH:32][CH:33]=3)=[N:7][C:6]1=2

Participants

3

Reactant 2

HCID 44119574(4-((2-(Diethylamino)ethyl)carbamoyl)phenyl)boronic acid hydrochlorideHCID 866594227-Bromo-1-(2-chloro-3,6-difluorobenzyl)-1,2,3,4-tetrahydropyrazino[2,3-b]pyrazine

Product 1

HCID 670081454-[8-(2-chloro-3,6-difluorobenzyl)-5,6,7,8-tetrahydropyrazino[2,3-b]pyrazin-2-yl]-N-[2-(diethylamino)ethyl]benzamide

Procedure

The entitled compound was prepared from 7-bromo-1-(2-chloro-3,6-difluorobenzyl)-1,2,3,4-tetrahydropyrazino[2,3-b]pyrazine and 4-{[2-(Diethylamino)ethyl]carbamoyl}benzeneboronic acid hydrochloride using Suzuki coupling conditions as described in Scheme 1.

Sources & evidence

ORD record
ord-1a5138b3c8d74f579440c419f67b8656
Source dataset
uspto-grants-2014_09
Patent number
US08846664B2

Reaction notes

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