2-(3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)acetamide → 2-{3-[8-(2-Chloro-3,6-difluorobenzyl)-5,6,7,8-tetrahydropyrazino[2,3-b]pyrazin-2-yl]phenyl}acetamide

HRID 80549Notes

Reaction equation

HRID 80549 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.B1([C:31]2[CH:36]=[CH:35][CH:34]=[C:33]([CH2:37][C:38]([NH2:40])=[O:39])[CH:32]=2)OC(C)(C)C(C)(C)O1>>[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:31]3[CH:32]=[C:33]([CH2:37][C:38]([NH2:40])=[O:39])[CH:34]=[CH:35][CH:36]=3)=[N:7][C:6]1=2

Participants

3

Reactant 2

HCID 164142392-(3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)acetamideHCID 866594227-Bromo-1-(2-chloro-3,6-difluorobenzyl)-1,2,3,4-tetrahydropyrazino[2,3-b]pyrazine

Product 1

HCID 670082892-{3-[8-(2-Chloro-3,6-difluorobenzyl)-5,6,7,8-tetrahydropyrazino[2,3-b]pyrazin-2-yl]phenyl}acetamide

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 3-(2-Acetamidyl)phenylboronic acid pinacol ester using Suzuki coupling conditions as described in Example 1.

Sources & evidence

ORD record
ord-7392c6eab8ae442088ba806ced1c03cd
Source dataset
uspto-grants-2014_09
Patent number
US08846664B2

Reaction notes

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