Triethylamine → HCID 18452691, compound

HRID 230116Notes

Reaction equation

HRID 230116 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10](=[O:15])[CH2:11][CH:12]2[CH2:14][O:13]2)=[CH:5][CH:4]=1.C(N(CC)CC)C.[CH3:23][C:24]1[CH:29]=[CH:28][CH:27]=[C:26]([CH3:30])[C:25]=1[NH:31][C:32](=[O:40])[CH2:33][N:34]1[CH2:39][CH2:38][NH:37][CH2:36][CH2:35]1>C(O)C>[CH3:23][C:24]1[CH:29]=[CH:28][CH:27]=[C:26]([CH3:30])[C:25]=1[NH:31][C:32]([CH2:33][N:34]1[CH2:35][CH2:36][N:37]([CH2:14][CH:12]([OH:13])[CH2:11][C:10]([NH:9][C:6]2[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)=[O:15])[CH2:38][CH2:39]1)=[O:40]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 2608606Cvt-2738HCID 58844915HCID 58844915, compound

Product 1

HCID 18452691HCID 18452691, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of crude N-(4-methoxyphenyl)-2-oxiran-2-ylacetamide (10) in ethanol (2.5 mL) was added triethylamine (0.5 mL), followed by N-(2,6-dimethylphenyl)-2-piperazinylacetamide, a compound of formula (4) (150 mg), and the mixture was heated to reflux for 18 hours. Solvent was removed from the reaction mixture under reduced pressure, and the residue purified by column chromatography on silica gel, eluting with 5% MeOH/dichloromethane, to give 4-(4-{[N-(2,6-dimethylphenyl)carbamoyl]methyl}-piperazinyl)-3-hydroxy-N-(4-methoxyphenyl)butanamide, a compound of Formula I as an off-white solid.

Workup

  1. temperatureto reflux for 18 hours
  2. customSolvent was removed from the reaction mixture under reduced pressure
  3. customthe residue purified by column chromatography on silica gel
  4. washeluting with 5% MeOH/dichloromethane

Sources & evidence

ORD record
ord-ca760d2cb8694ee58385eb72f841b3f4
Source dataset
uspto-grants-2009_07
Patent number
US07566717B2

Reaction notes

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