Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Formic Acid | HCID 284 | — |
| Reactant | Sodium Hydroxide | HCID 14798 | — |
| Reactant | 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-carbaldehyde oxime | HCID 136386487 | — |
| Catalyst | Zinc | HCID 23994 | — |
| Solvent | Ethanol | HCID 702 | — |
| Solvent | Methanol | HCID 887 | — |
| Solvent | Water | HCID 962 | — |
| Product | HCID 68468798 | HCID 68468798 | — |
Reaction Steps
To a solution of 0.5 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-carbaldehyde oxime in 30 cm3 of ethanol and 25 cm3 of water, at a temperature in the region of 20° C., are added 0.65 g of zinc and 17.5 cm3 of concentrated formic acid. The reaction medium is stirred at room temperature for 8 days. The reaction medium is concentrated under reduced pressure. The residue obtained is taken up in methanol, basified with sodium hydroxide (30%) to pH=9-10 and then filtered through Celite. The filtrate is concentrated under reduced pressure and the residue obtained is purified by flash-pack chromatography (SiO2, dichloromethane/methanol 95/05 by volume as eluents). 0.1 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-yl]methylamine is obtained with the following characteristics:
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07786114B2 |
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| Source dataset | uspto-grants-2010_08 |
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| ORD ID | ord-bce1dc6cb1564944986e9266f455d9bc |
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| Source note | uspto-grants-2010_08 |
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