Cesium carbonate → Methyl 3-{[3-(4-chlorophenyl)-1-(2-methoxy-2-oxoethyl)-5-oxo-1,5-dihydro-4H-1,2,4-triazol-4-yl]methyl}benzenecarboxylate

HRID 714615Notes

Reaction equation

HRID 714615 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:12][C:11](=[O:13])[N:10]([CH2:14][C:15]([O:17][CH3:18])=[O:16])[N:9]=2)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:26][C:27]1[CH:28]=[C:29]([CH:34]=[CH:35][CH:36]=1)[C:30]([O:32][CH3:33])=[O:31]>CC(C)=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([CH2:26][C:27]3[CH:28]=[C:29]([C:30]([O:32][CH3:33])=[O:31])[CH:34]=[CH:35][CH:36]=3)[C:11](=[O:13])[N:10]([CH2:14][C:15]([O:17][CH3:18])=[O:16])[N:9]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 517981Methyl 3-(bromomethyl)benzoateHCID 136199105Methyl[3-(4-chlorophenyl)-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl]-acetate

Product 1

HCID 67407710Methyl 3-{[3-(4-chlorophenyl)-1-(2-methoxy-2-oxoethyl)-5-oxo-1,5-dihydro-4H-1,2,4-triazol-4-yl]methyl}benzenecarboxylate

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

200 mg (0.75 mmol) of methyl [3-(4-chlorophenyl)-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl]acetate [preparation according to WO 2007/134862 Example 222A] were suspended in 7.5 ml of acetone, 365 mg (1.12 mmol) of cesium carbonate and 223 mg (0.97 mmol) of methyl 3-bromomethylbenzoate were added and the mixture was heated at the boil for 1 h. After cooling, the mixture was filtered through Extrelut and the filter cake was rinsed with acetone. The filtrate was concentrated under reduced pressure and the residue was purified by chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 4:1→1:1). The target compound was obtained as a colorless foam (165 mg, 53% of theory).

Workup

  1. temperaturethe mixture was heated at the boil for 1 h
  2. temperatureAfter cooling
  3. filtrationthe mixture was filtered through Extrelut
  4. washthe filter cake was rinsed with acetone
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. customthe residue was purified by chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 4:1→1:1)
  7. customThe target compound was obtained as a colorless foam (165 mg, 53% of theory)

Sources & evidence

ORD record
ord-8f9a18ce0d794674bece491ab6bf7324
Source dataset
uspto-grants-2015_11
Patent number
US09187466B2

Reaction notes

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