HRID490533

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID15346872

tert-butyl N-(azetidin-3-ylmethyl)carbamate

C9H18N2O2

结构：COc1cc2c(-c3cc4c(CCl)ccnc4n3S(=O)(=O)c3ccc(C)cc3)cn(C)c2cc1OC

HCID67147535

未命名化合物

PRODUCTS

生成物

结构：COc1cc2c(-c3cc4c(CN5CC(CNC(=O)OC(C)(C)C)C5)ccnc4[nH]3)cn(C)c2cc1OC

HCID67147599

未命名化合物

收率 221.9%

结构：COc1cc2c(-c3cc4c(CN5CC(CNC(=O)OC(C)(C)C)C5)ccnc4n3S(=O)(=O)c3ccc(C)cc3)cn(C)c2cc1OC

HCID67147982

未命名化合物

PROCEDURE

实验过程

{1-[2-(5,6-Dimethoxy-1-methyl-1H-indol-3-yl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyrid-4-ylmethyl]azetidin-3-ylmethyl}carbamic acid tert-butyl ester is prepared as described in Example 200b starting with 0.14 g of 4-chloromethyl-2-(5,6-dimethoxy-1-methyl-1H-indol-3-yl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine and 0.123 g of azetidin-3-ylmethylcarbamic acid tert-butyl ester instead of the piperid-4-ol used in Example 200b. After purification by flash-pack chromatography (SiO2, dichloromethane/methanol 95/5 by volume as eluent), 0.154 g of {1-[2-(5,6-dimethoxy-1-methyl-1H-indol-3-yl)-1H-pyrrolo[2,3-b]pyrid-4-ylmethyl]azetidin-3-ylmethyl}carbamic acid tert-butyl ester is obtained, the characteristics of which are as follows:

WORKUP

后处理

customAfter purification by flash-pack chromatography (SiO2, dichloromethane/methanol 95/5 by volume as eluent)

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-9b93a00918ad4db9abd6d6cf7f798fd1
来源数据集: uspto-grants-2009_05
DOI: 10.6084/m9.figshare.5104873.v1
专利: US07528147B2
来源说明: uspto-grants-2009_05

反应 SMILES

Cl[CH2:2][C:3]1[CH:8]=[CH:7][N:6]=[C:5]2[N:9]([S:26]([C:29]3[CH:34]=[CH:33][C:32]([CH3:35])=[CH:31][CH:30]=3)(=[O:28])=[O:27])[C:10]([C:12]3[C:20]4[C:15](=[CH:16][C:17]([O:23][CH3:24])=[C:18]([O:21][CH3:22])[CH:19]=4)[N:14]([CH3:25])[CH:13]=3)=[CH:11][C:4]=12.[C:36]([O:40][C:41](=[O:48])[NH:42][CH2:43][CH:44]1[CH2:47][NH:46][CH2:45]1)([CH3:39])([CH3:38])[CH3:37]>>[C:36]([O:40][C:41](=[O:48])[NH:42][CH2:43][CH:44]1[CH2:45][N:46]([CH2:2][C:3]2[CH:8]=[CH:7][N:6]=[C:5]3[N:9]([S:26]([C:29]4[CH:34]=[CH:33][C:32]([CH3:35])=[CH:31][CH:30]=4)(=[O:28])=[O:27])[C:10]([C:12]4[C:20]5[C:15](=[CH:16][C:17]([O:23][CH3:24])=[C:18]([O:21][CH3:22])[CH:19]=5)[N:14]([CH3:25])[CH:13]=4)=[CH:11][C:4]=23)[CH2:47]1)([CH3:39])([CH3:37])[CH3:38].[C:36]([O:40][C:41](=[O:48])[NH:42][CH2:43][CH:44]1[CH2:45][N:46]([CH2:2][C:3]2[CH:8]=[CH:7][N:6]=[C:5]3[NH:9][C:10]([C:12]4[C:20]5[C:15](=[CH:16][C:17]([O:23][CH3:24])=[C:18]([O:21][CH3:22])[CH:19]=5)[N:14]([CH3:25])[CH:13]=4)=[CH:11][C:4]=23)[CH2:47]1)([CH3:39])([CH3:37])[CH3:38]