HRID1184834

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID2795193

5-Pyrimidinylboronic acid

C4H5BN2O2

结构：Cc1ccc(NC(=O)c2cccc(C(C)(C)C#N)c2)cc1NC(=O)c1cc2nc(-c3cccnc3)cnc2s1

HCID86680167

未命名化合物

PRODUCTS

生成物

结构：Cc1ccc(NC(=O)c2cccc(C(C)(C)C#N)c2)cc1NC(=O)c1cc2nc(-c3cncnc3)cnc2s1

HCID86680168

未命名化合物

收率 7%

PROCEDURE

实验过程

Preparation analogous to the synthesis of 25h by using pyrimidine-5-boronic acid (1.5 eq). Purified by HPLC to give the title compound N-(5-(3-(2-cyanopropan-2-yl)benzamido)-2-methylphenyl)-2-(pyrimidin-5-yl)thieno[2,3-b]pyrazine-6-carboxamide 25j (2 mg, 7%). NMR (400 MHz, DMSO-d6) 1.76 (s, 6H), 2.28 (s, 3H), 7.33 (d, J=8.6 Hz, 1H), 7.58-7.67 (m, 2H), 7.76 (d, J=7.8 Hz, 1H), 7.9 (d, J=1.9 Hz, 1H), 7.95 (d, J=8.2 Hz, 1H), 8.06 (s, 1H), 8.63 (br s, 1H), 9.37 (s, 1H), 9.51 (s, 1H), 9.61 (s, 2H), 10.38 (br s, 1H). (m/z)=534 (M+H)+.

WORKUP

后处理

customPreparation
customPurified by HPLC

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-431599cdd324458199a5db141b526a85
来源数据集: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
专利: US08669256B2
来源说明: uspto-grants-2014_03

反应 SMILES

[C:1]([C:3]([C:6]1[CH:7]=[C:8]([CH:37]=[CH:38][CH:39]=1)[C:9]([NH:11][C:12]1[CH:13]=[CH:14][C:15]([CH3:36])=[C:16]([NH:18][C:19]([C:21]2[S:35][C:24]3=[N:25][CH:26]=[C:27]([C:29]4[CH:30]=[N:31][CH:32]=C[CH:34]=4)[N:28]=[C:23]3[CH:22]=2)=[O:20])[CH:17]=1)=[O:10])([CH3:5])[CH3:4])#[N:2].[N:40]1C=C(B(O)O)C=NC=1>>[C:1]([C:3]([C:6]1[CH:7]=[C:8]([CH:37]=[CH:38][CH:39]=1)[C:9]([NH:11][C:12]1[CH:13]=[CH:14][C:15]([CH3:36])=[C:16]([NH:18][C:19]([C:21]2[S:35][C:24]3=[N:25][CH:26]=[C:27]([C:29]4[CH:34]=[N:40][CH:32]=[N:31][CH:30]=4)[N:28]=[C:23]3[CH:22]=2)=[O:20])[CH:17]=1)=[O:10])([CH3:5])[CH3:4])#[N:2]