Potassium Hydroxide → HCID 25261574, compound

HRID 268809Notes

Reaction equation

HRID 268809 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-ba150b14bd0d4289b84a2041fe412d94
Source dataset
uspto-grants-2008_11
Patent number
US07446118B2

Reaction notes

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