Sodium Methoxide → 3-(1-{[3-(methyloxy)propyl]sulfonyl}-4-piperidinyl)-5-(2-thienyl)-1H-indole-7-carboxamide

HRID 2267575Notes

Reaction equation

HRID 2267575 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:28]([NH2:30])=[O:29])[CH:19]=[C:20]([C:23]4[S:24][CH:25]=[CH:26][CH:27]=4)[CH:21]=3)[NH:16][CH:15]=2)[CH2:10][CH2:9]1)(=[O:7])=[O:6].[CH3:31][O-:32].[Na+]>CO.CS(C)=O>[CH3:31][O:32][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:28]([NH2:30])=[O:29])[CH:19]=[C:20]([C:23]4[S:24][CH:25]=[CH:26][CH:27]=4)[CH:21]=3)[NH:16][CH:15]=2)[CH2:10][CH2:9]1)(=[O:7])=[O:6]

Participants

5

Reactant 2

HCID 10942334Sodium MethoxideHCID 590033233-{1-[(3-chloropropyl)sulfonyl]-4-piperidinyl}-5-(2-thienyl)-1H-indole-7-carboxamide

Product 1

HCID 590032923-(1-{[3-(methyloxy)propyl]sulfonyl}-4-piperidinyl)-5-(2-thienyl)-1H-indole-7-carboxamide

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 887MethanolSolvent

Procedure

3-{1-[(3-chloropropyl)sulfonyl]-4-piperidinyl}-5-(2-thienyl)-1H-indole-7-carboxamide (35 mg, 0.075 mmol) was reacted with sodium methoxide (0.5 M in methanol, 1.0 mL, 0.488 mmol) in a mixture of methanol (4 ml) and DMSO (0.5 mL) at reflux for 16 h to form the desired product which was purified by reverse phase HPLC eluting with 10% B to 70% B, where A=H2O (0.1% trifluoroacetic acid) and B=CH3CN (0.1% trifluoroacetic acid) to give the title compound (15 mg, 43%).

Workup

  1. temperatureat reflux for 16 h

Sources & evidence

ORD record
ord-26b68c5993304e28a8b50540b2ffb8f0
Source dataset
uspto-grants-2010_12
Patent number
US07858796B2

Reaction notes

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