Potassium Hydroxide → [2-(5,6-dimethoxy-1-methyl-1H-pyrrolo[3,2-b]pyridin-3-yl)-1H-pyrrolo[2,3-b]pyridin-4-ylmethyl]-[2-(3-methyl-3H-imidazol-4-yl)ethyl]amine

HRID 506816Notes

Reaction equation

HRID 506816 reaction equation
[CH3:1][O:2][C:3]1[N:8]=[C:7]2[C:9]([C:13]3[N:31](S(C4C=CC(C)=CC=4)(=O)=O)[C:16]4=[N:17][CH:18]=[CH:19][C:20]([CH2:21][NH:22][CH2:23][CH2:24][C:25]5[N:26]([CH3:30])[CH:27]=[N:28][CH:29]=5)=[C:15]4[CH:14]=3)=[CH:10][N:11]([CH3:12])[C:6]2=[CH:5][C:4]=1[O:42][CH3:43].[OH-].[K+]>>[CH3:1][O:2][C:3]1[N:8]=[C:7]2[C:9]([C:13]3[NH:31][C:16]4=[N:17][CH:18]=[CH:19][C:20]([CH2:21][NH:22][CH2:23][CH2:24][C:25]5[N:26]([CH3:30])[CH:27]=[N:28][CH:29]=5)=[C:15]4[CH:14]=3)=[CH:10][N:11]([CH3:12])[C:6]2=[CH:5][C:4]=1[O:42][CH3:43]

Participants

3

Reactant 2

HCID 14797Potassium HydroxideHCID 68469651[2-(5,6-dimethoxy-1-methyl-1H-pyrrolo[3,2-b]pyridin-3-yl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridin-4-ylmethyl]-[2-(3-methyl-3H-imidazol-4-yl)ethyl]amine

Product 1

HCID 68468899[2-(5,6-dimethoxy-1-methyl-1H-pyrrolo[3,2-b]pyridin-3-yl)-1H-pyrrolo[2,3-b]pyridin-4-ylmethyl]-[2-(3-methyl-3H-imidazol-4-yl)ethyl]amineYield 92.3%

Procedure

The product is prepared by following the procedure described in example 34 stage (k), starting with 0.070 g of [2-(5,6-dimethoxy-1-methyl-1H-pyrrolo[3,2-b]pyridin-3-yl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridin-4-ylmethyl]-[2-(3-methyl-3H-imidazol-4-yl)ethyl]amine instead of the cyclopropyl-[2-(5,6-dimethoxy-1-methyl-1H-pyrrolo[3,2-b]pyridin-3-yl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridin-4-ylmethyl]amine used in example 34 stage (k) and 0.5 cm3 of 5N potassium hydroxide. 0.048 g of [2-(5,6-dimethoxy-1-methyl-1H-pyrrolo[3,2-b]pyridin-3-yl)-1H-pyrrolo[2,3-b]pyridin-4-ylmethyl]-[2-(3-methyl-3H-imidazol-4-yl)ethyl]amine is obtained with the following characteristics:

Workup

  1. customThe product is prepared

Sources & evidence

ORD record
ord-2ccd6cbbb1494bdbbfeff5c0fac34158
Source dataset
uspto-grants-2010_08
Patent number
US07786114B2

Reaction notes

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