碳酸氢铯 → (S)-tert-butyl 3-((7-(4-morpholinophenyl)pyrido[4,3-b]pyrazin-5-ylamino)methyl)piperidine-1-carboxylate

HRID 57602

反应方程式

HRID 57602 反应方程式
Cl[C:2]1[N:11]=[C:10]([NH:12][CH2:13][C@@H:14]2[CH2:19][CH2:18][CH2:17][N:16]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:15]2)[C:9]2[C:4](=[N:5][CH:6]=[CH:7][N:8]=2)[CH:3]=1.[O:27]1[CH2:32][CH2:31][N:30]([C:33]2[CH:38]=[CH:37][C:36](B(O)O)=[CH:35][CH:34]=2)[CH2:29][CH2:28]1.C([O-])([O-])=O.[Cs+].[Cs+]>C(COC)OC.C(O)C.Cl[Pd]Cl>[O:27]1[CH2:32][CH2:31][N:30]([C:33]2[CH:38]=[CH:37][C:36]([C:2]3[N:11]=[C:10]([NH:12][CH2:13][C@@H:14]4[CH2:19][CH2:18][CH2:17][N:16]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:15]4)[C:9]4[C:4](=[N:5][CH:6]=[CH:7][N:8]=4)[CH:3]=3)=[CH:35][CH:34]=2)[CH2:29][CH2:28]1

参与物

6

反应物 3

HCID 10796碳酸氢铯HCID 27953594-吗啉苯硼酸HCID 86717378(S)-tert-butyl 3-((7-chloropyrido[4,3-b]pyrazin-5-ylamino)methyl)piperidine-1-carboxylate

产物 1

HCID 71113712(S)-tert-butyl 3-((7-(4-morpholinophenyl)pyrido[4,3-b]pyrazin-5-ylamino)methyl)piperidine-1-carboxylate收率 73%

试剂、催化剂与溶剂 2

HCID 24290氯化钯催化剂HCID 20074477Dimethoxyethane ethanol溶剂

反应条件

温度
160 °C

实验过程

A mixture of (S)-tert-butyl 3-((7-chloropyrido[4,3-b]pyrazin-5-ylamino)methyl)piperidine-1-carboxylate (0.15 mmol), 4-morpholinophenylboronic acid (0.23 mmol), PdCl2 (dppf) (0.015 mmol) and Cs2CO3 (0.30 mmol) in dimethoxyethane/ethanol was sealed in a microwave reaction and stirred at 160° C. for 45 minutes in a microwave reactor. The mixture was cooled to room temperature, concentrated, and purified by chromatography to afford the title compound (73% yield). MS (m/z): 505 (M+H)+.

后处理

  1. customwas sealed in a microwave reaction
  2. temperatureThe mixture was cooled to room temperature
  3. concentrationconcentrated
  4. custompurified by chromatography

来源与证据

ORD记录
ord-059884758c924940b47b252436c2fba7
来源数据集
uspto-grants-2016_09
专利号
US09434726B2

关联笔记

加载中…