Potassium Hydroxide → HCID 67147624, compound

HRID 490505Notes

Reaction equation

HRID 490505 reaction equation
[OH-].[K+].[CH3:3][O:4][C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][C:13]=1[O:14][CH3:15])[N:10]([CH3:16])[CH:9]=[C:8]2[C:17]1[N:39](S(C2C=CC(C)=CC=2)(=O)=O)[C:20]2=[N:21][CH:22]=[CH:23][C:24]([CH2:25][NH:26][CH2:27][C:28]3[CH:33]=[CH:32][C:31]([S:34][C:35]([F:38])([F:37])[F:36])=[CH:30][CH:29]=3)=[C:19]2[CH:18]=1>CO.O>[CH3:3][O:4][C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][C:13]=1[O:14][CH3:15])[N:10]([CH3:16])[CH:9]=[C:8]2[C:17]1[NH:39][C:20]2=[N:21][CH:22]=[CH:23][C:24]([CH2:25][NH:26][CH2:27][C:28]3[CH:33]=[CH:32][C:31]([S:34][C:35]([F:37])([F:38])[F:36])=[CH:30][CH:29]=3)=[C:19]2[CH:18]=1

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 67147694HCID 67147694, compound

Product 1

HCID 67147624HCID 67147624, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

0.265 cm3 of 5N potassium hydroxide is added to a solution of 0.04 g of [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 in 2 cm3 of methanol, at a temperature in the region of 20° C. The reaction medium is refluxed for 6 hours. After cooling, the reaction medium is concentrated under reduced pressure. The residue obtained is taken up in 4 cm3 of water. The solid formed is filtered off on a sinter funnel, washed twice with 3 cm3 of water and then dried under vacuum to give 0.030 g of [2-(5,6-dimethoxy-1-methyl-1H-indol-3-yl)-1H-pyrrolo[2,3-b]pyrid-4-ylmethyl](4-trifluoromethylsulfanylbenzyl)amine, the characteristics of which are as follows:

Workup

  1. temperatureThe reaction medium is refluxed for 6 hours
  2. temperatureAfter cooling
  3. concentrationthe reaction medium is concentrated under reduced pressure
  4. customThe residue obtained
  5. customThe solid formed
  6. filtrationis filtered off on a sinter funnel
  7. washwashed twice with 3 cm3 of water
  8. customdried under vacuum

Sources & evidence

ORD record
ord-a7fbfbb3e1b04222a36902be33302880
Source dataset
uspto-grants-2009_05
Patent number
US07528147B2

Reaction notes

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