Sodium Methoxide → 3-(1-{[3-(methyloxy)propyl]sulfonyl}-4-piperidinyl)-5-phenyl-1H-indole-7-carboxamide

HRID 2267553Notes

Reaction equation

HRID 2267553 reaction equation
Cl[CH2:2][CH2:3][CH2:4][S:5]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[C:22]3[C:17](=[C:18]([C:29]([NH2:31])=[O:30])[CH:19]=[C:20]([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)[CH:21]=3)[NH:16][CH:15]=2)[CH2:10][CH2:9]1)(=[O:7])=[O:6].[CH3:32][O-:33].[Na+]>CO>[CH3:32][O:33][CH2:2][CH2:3][CH2:4][S:5]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[C:22]3[C:17](=[C:18]([C:29]([NH2:31])=[O:30])[CH:19]=[C:20]([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)[CH:21]=3)[NH:16][CH:15]=2)[CH2:10][CH2:9]1)(=[O:7])=[O:6]

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 590032803-{1-[(3-chloropropyl)sulfonyl]-4-piperidinyl}-5-phenyl-1H-indole-7-carboxamide

Product 1

HCID 590033563-(1-{[3-(methyloxy)propyl]sulfonyl}-4-piperidinyl)-5-phenyl-1H-indole-7-carboxamideYield 44%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The mixture of 3-{1-[(3-chloropropyl)sulfonyl]-4-piperidinyl}-5-phenyl-1H-indole-7-carboxamide (46.0 mg, 0.1 mmol), 0.1 M NaOMe (4 ml) in methanol (2 mL) was refluxed overnight. The reaction mixture was concentrated and purified by reverse phase HPLC (water/CH3CN, 0.1% TFA 10-90%) to give the title compound (20.0 mg, 44%).

Workup

  1. temperaturewas refluxed overnight
  2. concentrationThe reaction mixture was concentrated
  3. custompurified by reverse phase HPLC (water/CH3CN, 0.1% TFA 10-90%)

Sources & evidence

ORD record
ord-343cad488e9e4b629b010dfe9530e4ee
Source dataset
uspto-grants-2010_12
Patent number
US07858796B2

Reaction notes

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