HRID490532

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID14797

Potassium hydroxide

HKO

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

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

HCID67147982

未命名化合物

收率 49.3%

PROCEDURE

实验过程

{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 prepared as described in Example 179a starting With 0.15 g of {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 instead of the [2-(5,6-dimethoxy-1-methyl-1H-indol-3-yl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyrid-4-ylmethyl](4-trifluoromethylsulfanylbenzyl)amine used in Example 179a and 0.909 cm3 of 5N potassium hydroxide. After purification by flash-pack chromatography (SiO2, dichloromethane/methanol 95/5 by volume as eluent), 0.037 g of {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 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-cbf2abf5d5e642518188e0ce4b1db1c2
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

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