Formic Acid → HCID 68468798, compound

HRID 506836Notes

Reaction equation

HRID 506836 reaction equation
[CH3:1][O:2][C:3]1[N:8]=[C:7]2[C:9]([C:13]3[N:24]([S:25]([C:28]4[CH:33]=[CH:32][C:31]([CH3:34])=[CH:30][CH:29]=4)(=[O:27])=[O:26])[C:16]4[N:17]=[CH:18][CH:19]=[C:20]([CH:21]=[N:22]O)[C:15]=4[CH:14]=3)=[CH:10][N:11]([CH3:12])[C:6]2=[CH:5][C:4]=1[O:35][CH3:36].C(O)=O.[OH-].[Na+]>C(O)C.O.CO.[Zn]>[CH3:1][O:2][C:3]1[N:8]=[C:7]2[C:9]([C:13]3[N:24]([S:25]([C:28]4[CH:33]=[CH:32][C:31]([CH3:34])=[CH:30][CH:29]=4)(=[O:27])=[O:26])[C:16]4=[N:17][CH:18]=[CH:19][C:20]([CH2:21][NH2:22])=[C:15]4[CH:14]=3)=[CH:10][N:11]([CH3:12])[C:6]2=[CH:5][C:4]=1[O:35][CH3:36]

Participants

8

Reactant 3

HCID 284Formic AcidHCID 14798Sodium HydroxideHCID 1363864872-(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

Product 1

HCID 68468798HCID 68468798, compound

Reagents, catalysts & solvents 4

HCID 23994ZincCatalystHCID 702EthanolSolventHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

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:

Workup

  1. concentrationThe reaction medium is concentrated under reduced pressure
  2. customThe residue obtained
  3. filtrationfiltered through Celite
  4. concentrationThe filtrate is concentrated under reduced pressure
  5. customthe residue obtained
  6. customis purified by flash-pack chromatography (SiO2, dichloromethane/methanol 95/05 by volume as eluents)

Sources & evidence

ORD record
ord-bce1dc6cb1564944986e9266f455d9bc
Source dataset
uspto-grants-2010_08
Patent number
US07786114B2

Reaction notes

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