HCID 67147423, compound → HCID 67147576, compound

HRID 2426814Notes

Reaction equation

HRID 2426814 reaction equation
[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[CH3:8][O:9][C:10]1[CH:11]=[C:12]2[C:16](=[CH:17][C:18]=1[O:19][CH3:20])[N:15]([CH2:21][CH2:22][N:23]([CH2:25][CH2:26][O:27][CH3:28])[CH3:24])[CH:14]=[C:13]2[C:29]1[N:37](S(C2C=CC(C)=CC=2)(=O)=O)[C:32]2=[N:33][CH:34]=[CH:35][CH:36]=[C:31]2[CH:30]=1>[OH-].[K+]>[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[CH3:8][O:9][C:10]1[CH:11]=[C:12]2[C:16](=[CH:17][C:18]=1[O:19][CH3:20])[N:15]([CH2:21][CH2:22][N:23]([CH2:25][CH2:26][O:27][CH3:28])[CH3:24])[CH:14]=[C:13]2[C:29]1[NH:37][C:32]2=[N:33][CH:34]=[CH:35][CH:36]=[C:31]2[CH:30]=1

Participants

3

Reactant 1

HCID 67147423HCID 67147423, compound

Product 1

HCID 67147576HCID 67147576, compoundYield 80.1%

Reagents, catalysts & solvents 1

HCID 14797Potassium HydroxideSolvent

Procedure

(2-{5,6-Dimethoxy-3-(1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]-pyridin-2-yl)indol-1-yl}ethyl)-(2-methoxyethyl)methylamine trifluoroacetate (0.0152 g; 22.46 μmol) is dissolved in a methanolic potassium hydroxide solution (0.5 ml; 0.1 g of potassium hydroxide/ml methanol) and then agitated at ambient temperature for 48 hours. After evaporation, the residue is taken up, with agitation, in 0.7 ml of a dimethyl sulfoxide and 12N aqueous hydrochloric acid (50/50 v/v). After returning to ambient temperature, dimethyl sulfoxide (0.35 ml) is added and then purification is carried out by reverse-phase liquid chromatography mass spectrometry (method B). The fractions containing the expected compound are combined and evaporated. {2-[5,6-Dimethoxy-3-(1H-pyrrolo[2,3-b]pyridin-2-yl)indol-1-yl]ethyl}-(2-methoxyethyl)methylamine trifluoroacetate (0.0094 g; 80%) is isolated, the characteristics of which are as follows:

Workup

  1. customAfter evaporation
  2. customAfter returning to ambient temperature
  3. additiondimethyl sulfoxide (0.35 ml) is added
  4. custompurification
  5. additionThe fractions containing the expected compound
  6. customevaporated

Sources & evidence

ORD record
ord-adafa211a6a14cb08734c7f9e7c69e17
Source dataset
uspto-grants-2011_06
Patent number
US07968566B2

Reaction notes

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