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 714615ノート

反応式

HRID 714615 の反応式
[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

参加物

5

反応物 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

生成物 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

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-8f9a18ce0d794674bece491ab6bf7324
出典データセット
uspto-grants-2015_11
特許番号
US09187466B2

反応ノート

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