tert-Butyl 4-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidin-2-yl)piperazine-1-carboxylate → 1-(2-Chloro-3,6-difluorobenzyl)-7-[2-(piperazin-1-yl)pyrimidin-5-yl]-1,2,3,4-tetrahydropyrazino[2,3-b]pyrazine

HRID 80540노트

반응식

HRID 80540 반응식
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.C([N:29]1[CH2:34][CH2:33][N:32]([C:35]2[N:40]=[CH:39][C:38](B3OC(C)(C)C(C)(C)O3)=[CH:37][N:36]=2)[CH2:31][CH2:30]1)(OC(C)(C)C)=O>>[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[C:6]2=[N:7][C:2]([C:38]3[CH:37]=[N:36][C:35]([N:32]4[CH2:33][CH2:34][NH:29][CH2:30][CH2:31]4)=[N:40][CH:39]=3)=[CH:3][N:4]=[C:5]2[NH:11][CH2:10][CH2:9]1

참가 물질

3

반응물 2

HCID 46739020tert-Butyl 4-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidin-2-yl)piperazine-1-carboxylateHCID 866594227-Bromo-1-(2-chloro-3,6-difluorobenzyl)-1,2,3,4-tetrahydropyrazino[2,3-b]pyrazine

생성물 1

HCID 670078461-(2-Chloro-3,6-difluorobenzyl)-7-[2-(piperazin-1-yl)pyrimidin-5-yl]-1,2,3,4-tetrahydropyrazino[2,3-b]pyrazine

실험 절차

The entitled compound was prepared from 7-bromo-1-(2-chloro-3,6-difluorobenzyl)-1,2,3,4-tetrahydropyrazino[2,3-b]pyrazine and 2-(4-Boc-piperazin-1-yl)pyrimidine-5-boronic acid pinacol ester using Suzuki coupling conditions as described in Example 1. The Suzuki coupling yielded the desired compound in its BOC protected form. The BOC protected intermediate was then treated with TFA in CH2Cl2 and purified by Silica gel column chromatography.

출처 및 근거

ORD 기록
ord-2282be6cc86d441fa3e1351186d8ea5c
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08846664B2

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