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

HRID 907150Notes

Reaction equation

HRID 907150 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) was heated at reflux for 1.5 h. After cooling to room temperature, the reaction was concentrated and the residue was 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. temperaturewas heated
  2. temperatureat reflux for 1.5 h
  3. concentrationthe reaction was concentrated
  4. customthe residue was purified by flash chromatography (acetone/EtOAc, 2/98) over silica gel

Sources & evidence

ORD record
ord-453de111de0246aea6944d57aa9a8b28
Source dataset
uspto-grants-2011_09
Patent number
US08013006B2

Reaction notes

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