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

HRID 490547Notes

Reaction equation

HRID 490547 reaction equation
[CH3:1][O:2][C:3]1[CH:58]=[C:57]([O:59][CH3:60])[CH:56]=[CH:55][C:4]=1[CH2:5][N:6]([CH2:21][C:22]1[CH:27]=[CH:26][N:25]=[C:24]2[N:28](S(C3C=CC(C)=CC=3)(=O)=O)[C:29]([C:31]3[C:39]4[C:34](=[CH:35][C:36]([O:42][CH3:43])=[C:37]([O:40][CH3:41])[CH:38]=4)[N:33]([CH3:44])[CH:32]=3)=[CH:30][C:23]=12)[C:7]([NH:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][C:17]([F:20])([F:19])[F:18])=[CH:12][CH:11]=1)=[O:8].[OH-].[K+]>>[CH3:1][O:2][C:3]1[CH:58]=[C:57]([O:59][CH3:60])[CH:56]=[CH:55][C:4]=1[CH2:5][N:6]([CH2:21][C:22]1[CH:27]=[CH:26][N:25]=[C:24]2[NH:28][C:29]([C:31]3[C:39]4[C:34](=[CH:35][C:36]([O:42][CH3:43])=[C:37]([O:40][CH3:41])[CH:38]=4)[N:33]([CH3:44])[CH:32]=3)=[CH:30][C:23]=12)[C:7]([NH:9][C:10]1[CH:11]=[CH:12][C:13]([O:16][C:17]([F:18])([F:19])[F:20])=[CH:14][CH:15]=1)=[O:8]

Participants

3

Reactant 2

HCID 14797Potassium HydroxideHCID 67147518HCID 67147518, compound

Product 1

HCID 671474921-(2,4-dimethoxybenzyl)-1-[2-(5,6-dimethoxy-1-methyl-1H-indol-3-yl)-1H-pyrrolo[2,3-b]pyrid-4-ylmethyl]-3-(4-trifluoromethoxyphenyl)ureaYield 32.6%

Procedure

1-(2,4-Dimethoxybenzyl)-1-[2-(5,6-dimethoxy-1-methyl-1H-indol-3-yl)-1H-pyrrolo[2,3-b]pyrid-4-ylmethyl]-3-(4-trifluoromethoxyphenyl)urea is prepared as described in Example 179a starting with 0.150 g of 1-(2,4-dimethoxybenzyl)-1-[2-(5,6-dimethoxy-1-methyl-1H-indol-3-yl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyrid-4-ylmethyl]-3-(4-trifluoromethoxyphenyl)urea 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. 0.040 g of 1-(2,4-dimethoxybenzyl)-1-[2-(5,6-dimethoxy-1-methyl-1H-indol-3-yl)-1H-pyrrolo[2,3-b]pyrid-4-ylmethyl]-3-(4-trifluoromethoxyphenyl)urea is obtained, the characteristics of which are as follows:

Workup

  1. custom1-(2,4-Dimethoxybenzyl)-1-[2-(5,6-dimethoxy-1-methyl-1H-indol-3-yl)-1H-pyrrolo[2,3-b]pyrid-4-ylmethyl]-3-(4-trifluoromethoxyphenyl)urea is prepared

Sources & evidence

ORD record
ord-c72bccd6a98f497e8821d62dc784c53f
Source dataset
uspto-grants-2009_05
Patent number
US07528147B2

Reaction notes

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