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

HRID 2426937Notes

Reaction equation

HRID 2426937 reaction equation
COC1C=C(OC)C=CC=1C[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:9])=[O:8].C1(C)C=CC(S(O)(=O)=O)=CC=1>>[CH3:35][O:34][C:31]1[CH:32]=[C:33]2[C:28](=[CH:29][C:30]=1[O:36][CH3:37])[N:27]([CH3:38])[CH:26]=[C:25]2[C:23]1[NH:22][C:18]2=[N:19][CH:20]=[CH:21][C:16]([CH2:15][NH:6][S:7]([C:10]3[S:11][CH:12]=[CH:13][CH:14]=3)(=[O:9])=[O:8])=[C:17]2[CH:24]=1

Participants

3

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 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]amide

Product 1

HCID 67147671thiophene-2-sulfonic acid [2-(5,6-dimethoxy-1-methyl-1H-indol-3-yl)-1H-pyrrolo[2,3-b]pyrid-4-ylmethyl]amideYield 32.8%

Procedure

Thiophene-2-sulfonic acid [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 210 starting with 0.1 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 instead of the N-(2,4-dimethoxybenzyl)-N-[2-(5,6-dimethoxy-1-methyl-1H-indol-3-yl)-1H-pyrrolo[2,3-b]pyrid-4-ylmethyl]-4-trifluoromethoxybenzenesulfonamide used in Example 210 and 0.110 g of para-toluenesulfonic acid. 0.025 g of thiophene-2-sulfonic acid [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

  1. customThiophene-2-sulfonic acid [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-e8410138806a42e39d4b370766c5fbf6
Source dataset
uspto-grants-2011_06
Patent number
US07968566B2

Reaction notes

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