Potassium Hydroxide → thiophene-2-sulfonic acid (2,4-dimethoxybenzyl) [2-(5,6-dimethoxy-1-methyl-1H-indol-3-yl)-1H-pyrrolo[2,3-b]pyrid-4-ylmethyl]amide

HRID 490543Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:52]=[C:51]([O:53][CH3:54])[CH:50]=[CH:49][C:4]=1[CH2:5][N:6]([CH2:15][C:16]1[CH:21]=[CH:20][N:19]=[C:18]2[N:22](S(C3C=CC(C)=CC=3)(=O)=O)[C:23]([C:25]3[C:33]4[C:28](=[CH:29][C:30]([O:36][CH3:37])=[C:31]([O:34][CH3:35])[CH:32]=4)[N:27]([CH3:38])[CH:26]=3)=[CH:24][C:17]=12)[S:7]([C:10]1[S:11][CH:12]=[CH:13][CH:14]=1)(=[O:9])=[O:8].[OH-].[K+]>>[CH3:1][O:2][C:3]1[CH:52]=[C:51]([O:53][CH3:54])[CH:50]=[CH:49][C:4]=1[CH2:5][N:6]([CH2:15][C:16]1[CH:21]=[CH:20][N:19]=[C:18]2[NH:22][C:23]([C:25]3[C:33]4[C:28](=[CH:29][C:30]([O:36][CH3:37])=[C:31]([O:34][CH3:35])[CH:32]=4)[N:27]([CH3:38])[CH:26]=3)=[CH:24][C:17]=12)[S:7]([C:10]1[S:11][CH:12]=[CH:13][CH:14]=1)(=[O:8])=[O:9]

Participants

Reactant 2

HCID 14797Potassium Hydroxide

HCID 86612143HCID 86612143, compound

Product 1

HCID 67147563thiophene-2-sulfonic acid (2,4-dimethoxybenzyl) [2-(5,6-dimethoxy-1-methyl-1H-indol-3-yl)-1H-pyrrolo[2,3-b]pyrid-4-ylmethyl]amideYield 82.9%

Procedure

Thiophene-2-sulfonic acid (2,4-dimethoxybenzyl)[2-(5,6-dimethoxy-1-methyl-1H-indol-3-yl)-1H-pyrrolo[2,3-b]pyrid-4-ylmethyl]amide is prepared as described in Example 179a starting with 0.150 g of thiophene-2-sulfonic acid (2,4-dimethoxybenzyl)[2-(5,6-dimethoxy-1-methyl-1H-indol-3-yl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyrid-4-ylmethyl]amide 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 1 cm3 of 5N potassium hydroxide. 0.100 g of thiophene-2-sulfonic acid (2,4-dimethoxybenzyl)[2-(5,6-dimethoxy-1-methyl-1H-indol-3-yl)-1H-pyrrolo[2,3-b]pyrid-4-ylmethyl]amide is obtained, the characteristics of which are as follows:

Workup

customThiophene-2-sulfonic acid (2,4-dimethoxybenzyl)[2-(5,6-dimethoxy-1-methyl-1H-indol-3-yl)-1H-pyrrolo[2,3-b]pyrid-4-ylmethyl]amide is prepared

Sources & evidence

ORD record: ord-08f682b44259421cb26f9eb312281d6f
Source dataset: uspto-grants-2009_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07528147B2

Reaction notes

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