HRID1486713

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID521157

Ethylboronic acid

C2H7BO2

HCID7175833

未命名化合物

HCID11138942

2-Bromo-5-nitrobenzaldehyde

C7H4BrNO3

结构：CC(C)(C)NC(=O)C1CCN(Cc2cc([N+](=O)[O-])ccc2Br)CC1

HCID131736807

未命名化合物

PRODUCTS

生成物

结构：CCc1ccc(N)cc1CN1CCC(C(=O)NC(C)(C)C)CC1

HCID131736805

未命名化合物

结构：CCc1ccc([N+](=O)[O-])cc1CN1CCC(C(=O)NC(C)(C)C)CC1

HCID131736806

未命名化合物

PROCEDURE

实验过程

The title compound is prepared according to the reactions described above starting from 2-bromo-5-nitro-benzaldehyde and piperidine-4-carboxylic acid tert-butylamide yielding after reductive amination 1-(2-bromo-5-nitro-benzyl)-piperidine-4-carboxylic acid tert-butylamide; LC-MS A: tR=0.62 min; [M+H]+=397.99; followed by alkylation with ethylboronic acid yielding 1-(2-ethyl-5-nitro-benzyl)-piperidine-4-carboxylic acid tert-butylamide; LC-MS A: tR=0.66 min; [M+H]+=348.34, followed by reduction with stannous chloride the title compound; LC-MS A: tR=0.49 min; [M+H]+=318.21.

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-9ad1479c911d422a847323f8b24fae5e
来源数据集: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
专利: US09428456B2
来源说明: uspto-grants-2016_08

反应 SMILES

Br[C:2]1C=CC([N+]([O-])=O)=C[C:3]=1C=O.[C:13](NC(C1CCNCC1)=O)(C)(C)[CH3:14].[C:26]([NH:30][C:31]([CH:33]1[CH2:38][CH2:37][N:36]([CH2:39][C:40]2[CH:45]=[C:44]([N+:46]([O-:48])=[O:47])[CH:43]=[CH:42][C:41]=2Br)[CH2:35][CH2:34]1)=[O:32])([CH3:29])([CH3:28])[CH3:27].C(B(O)O)C>>[C:26]([NH:30][C:31]([CH:33]1[CH2:38][CH2:37][N:36]([CH2:39][C:40]2[CH:45]=[C:44]([NH2:46])[CH:43]=[CH:42][C:41]=2[CH2:2][CH3:3])[CH2:35][CH2:34]1)=[O:32])([CH3:29])([CH3:28])[CH3:27].[C:26]([NH:30][C:31]([CH:33]1[CH2:38][CH2:37][N:36]([CH2:39][C:40]2[CH:45]=[C:44]([N+:46]([O-:48])=[O:47])[CH:43]=[CH:42][C:41]=2[CH2:13][CH3:14])[CH2:35][CH2:34]1)=[O:32])([CH3:29])([CH3:28])[CH3:27]