Morpholine → 2-Morpholin-4-yl-ethanesulfonic acid[4-(3-cyano-1-ethyl-6-methoxy-1h-indol-2-yl)-phenyl]amide

HRID 506050Notes

Reaction equation

HRID 506050 reaction equation
[C:1]([C:3]1[C:11]2[C:6](=[CH:7][C:8]([O:12][CH3:13])=[CH:9][CH:10]=2)[N:5]([CH2:14][CH3:15])[C:4]=1[C:16]1[CH:21]=[CH:20][C:19]([NH:22][S:23]([CH:26]=[CH2:27])(=[O:25])=[O:24])=[CH:18][CH:17]=1)#[N:2].[NH:28]1[CH2:33][CH2:32][O:31][CH2:30][CH2:29]1>CC#N>[C:1]([C:3]1[C:11]2[C:6](=[CH:7][C:8]([O:12][CH3:13])=[CH:9][CH:10]=2)[N:5]([CH2:14][CH3:15])[C:4]=1[C:16]1[CH:21]=[CH:20][C:19]([NH:22][S:23]([CH2:26][CH2:27][N:28]2[CH2:33][CH2:32][O:31][CH2:30][CH2:29]2)(=[O:24])=[O:25])=[CH:18][CH:17]=1)#[N:2]

Participants

4

Reactant 2

HCID 8083MorpholineHCID 59426235ethenesulfonic acid [4-(3-cyano-1-ethyl-6-methoxy-1H-indol-2-yl)-phenyl]amide

Product 1

HCID 594254352-Morpholin-4-yl-ethanesulfonic acid[4-(3-cyano-1-ethyl-6-methoxy-1h-indol-2-yl)-phenyl]amideYield 100%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A suspension of ethenesulfonic acid [4-(3-cyano-1-ethyl-6-methoxy-1H-indol-2-yl)-phenyl]amide, prepared above, (70 mg, 0.18 mmol), morpholine (0.05 mL, 0.55 mmol) in CH3CN (1.5 mL) is heated at reflux for 1.5 h. After cooling to room temperature, the reaction is concentrated and the residue is purified by flash chromatography (acetone/EtOAc, 2/98) over silica gel to afford 89 mg (100%) of 2-morpholin-4-yl-ethanesulfonic acid[4-(3-cyano-1-ethyl-6-methoxy-1H-indol-2-yl)-phenyl]amide as a tan foam.

Workup

  1. temperatureis heated
  2. temperatureat reflux for 1.5 h
  3. concentrationthe reaction is concentrated
  4. customthe residue is purified by flash chromatography (acetone/EtOAc, 2/98) over silica gel

Sources & evidence

ORD record
ord-3d9bf36f9d62491ebebf3204c603fcaa
Source dataset
uspto-grants-2010_08
Patent number
US07781478B2

Reaction notes

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