Potassium Hydroxide → HCID 25261574, compound

HRID 1716683Notes

Reaction equation

HRID 1716683 reaction equation
CS([N:5]1[C:13]2[C:8](=[CH:9][C:10]([CH:14]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH2:15][CH2:16][NH:17][CH3:18])=[CH:11][CH:12]=2)[C:7]([S:25]([CH3:28])(=[O:27])=[O:26])=[CH:6]1)(=O)=O.[OH-].[K+]>CO>[CH3:28][S:25]([C:7]1[C:8]2[C:13](=[CH:12][CH:11]=[C:10]([CH:14]([C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)[CH2:15][CH2:16][NH:17][CH3:18])[CH:9]=2)[NH:5][CH:6]=1)(=[O:27])=[O:26]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 59831837HCID 59831837, compound

Product 1

HCID 25261574HCID 25261574, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a solution of [3-(1,3-bis-methanesulfonyl-1H-indol-5-yl)-3-phenyl-propyl]-methyl-amine LXXIX (36 mg, 0.0865 mmol) in MeOH (3 ml) was added a solution of KOH (7.29 mg, 0.13 mmol) in MeOH. After stirring for 50 minutes at room temperature, the mixture was concentrated, and the residue was partitioned between EtOAc and H2O. The combined organic layers were dried over Na2SO4, filtered, concentrated, and purified via flash chromatography (DCM/MeOH/NH4OH) to provide [3-(3-methanesulfonyl-1H-indol-5-yl)-3-phenyl-propyl]-methyl-amine LXXX as a white powder (13 mg, 36% yield). MS (M+H)=343.

Workup

  1. concentrationthe mixture was concentrated
  2. customthe residue was partitioned between EtOAc and H2O
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. custompurified via flash chromatography (DCM/MeOH/NH4OH)

Sources & evidence

ORD record
ord-b5dcbdf00b10467886affbc8a1e47b07
Source dataset
uspto-grants-2010_09
Patent number
US07803830B2

Reaction notes

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