Potassium Hydroxide → HCID 68470144, compound

HRID 506814Notes

Reaction equation

[CH3:1][O:2][C:3]1[N:8]=[C:7]2[C:9]([C:13]3[N:30](S(C4C=CC(C)=CC=4)(=O)=O)[C:16]4=[N:17][CH:18]=[CH:19][C:20]([CH2:21][NH:22][CH:23]5[CH2:28][CH2:27][N:26]([CH3:29])[CH2:25][CH2:24]5)=[C:15]4[CH:14]=3)=[CH:10][N:11]([CH3:12])[C:6]2=[CH:5][C:4]=1[O:41][CH3:42].[OH-].[K+]>>[CH3:1][O:2][C:3]1[N:8]=[C:7]2[C:9]([C:13]3[NH:30][C:16]4=[N:17][CH:18]=[CH:19][C:20]([CH2:21][NH:22][CH:23]5[CH2:24][CH2:25][N:26]([CH3:29])[CH2:27][CH2:28]5)=[C:15]4[CH:14]=3)=[CH:10][N:11]([CH3:12])[C:6]2=[CH:5][C:4]=1[O:41][CH3:42]

Participants

Reactant 2

HCID 14797Potassium Hydroxide

HCID 68470735HCID 68470735, compound

Product 1

HCID 68470144HCID 68470144, compoundYield 92.1%

Procedure

The product is prepared by following the procedure described in example 34 stage (k) starting with 0.250 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]-(1-methylpiperidin-4-yl)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 2 cm3 of 5N potassium hydroxide. After purification by flash-pack chromatography (SiO2, dichloromethane/methanol 90/10 by volume as eluents), 0.170 g of [2-(5,6-dimethoxy-1-methyl-1H-pyrrolo[3,2-b]pyridin-3-yl)-1H-pyrrolo[2,3-b]pyridin-4-ylmethyl]-(1-methylpiperidin-4-yl)amine is obtained with the following characteristics:

Workup

customThe product is prepared
customAfter purification by flash-pack chromatography (SiO2, dichloromethane/methanol 90/10 by volume as eluents)

Sources & evidence

ORD record: ord-dd034535bcf94bab82425a2740303489
Source dataset: uspto-grants-2010_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07786114B2

Reaction notes

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