Cesium carbonate → HCID 14986894, compound

HRID 1493587Notes

Reaction equation

HRID 1493587 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1([CH2:12][N:13]2[CH:17]=[N:16][CH:15]=[N:14]2)[CH2:11][O:10]1.[CH3:18][CH:19]([N:22]1[C:26](=[O:27])[N:25]([C:28]2[CH:29]=[CH:30][C:31]([N:34]3[CH2:39][CH2:38][N:37]([C:40]4[CH:45]=[CH:44][C:43]([OH:46])=[CH:42][CH:41]=4)[CH2:36][CH2:35]3)=[N:32][CH:33]=2)[CH:24]=[N:23]1)[CH2:20][CH3:21].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[CH3:18][CH:19]([N:22]1[C:26](=[O:27])[N:25]([C:28]2[CH:29]=[CH:30][C:31]([N:34]3[CH2:35][CH2:36][N:37]([C:40]4[CH:41]=[CH:42][C:43]([O:46][CH2:11][C:9]([C:3]5[CH:4]=[CH:5][C:6]([Cl:8])=[CH:7][C:2]=5[Cl:1])([OH:10])[CH2:12][N:13]5[CH:17]=[N:16][CH:15]=[N:14]5)=[CH:44][CH:45]=4)[CH2:38][CH2:39]3)=[N:32][CH:33]=2)[CH:24]=[N:23]1)[CH2:20][CH3:21]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 104232291H-1,2,4-Triazole, 1-[[2-(2,4-dichlorophenyl)oxiranyl]methyl]-HCID 14986893HCID 14986893, compound

Product 1

HCID 14986894HCID 14986894, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)oxirane (0.3 g, 1.1 mmole), 2-(2-butyl)-4-(2-[4-(4-hydroxyphenyl)piperazin-1-yl]pyridin-5-yl)-1,2,4-triazolin-3-one (see Preparation 5) (0.263 g, 0.67 mmole) and cesium carbonate (0.29 g, 0.89 mmole) in DMF (15 ml) was heated at 80° for 6 hours. The solvent was removed by concentration under reduced pressure and the residue was azeotroped with xylene (2×20 ml) under reduced pressure. The resulting material was partitioned between methylene chloride and water, the aqueous phase separated and re-extracted with methylene chloride. The combined organic extracts were washed with brine, dried over magnesium sulphate and concentrated under reduced pressure. The residual material was purified by flash chromatography on silica gel eluting with methylene chloride (97):methanol (3):0.88 ammonia solution (1). The product obtained, after collection and evaporation of appropriate fractions, was further purified by flash chromatography on silica gel eluting with methylene chloride (94.5):methanol (5.5):0.88 ammonia solution (4.5). The resulting material obtained, after collection and evaporation of appropriate fractions, was triturated with hexane to yield the desired product, m.p. 84°-87° (0.16 g, 36%).

Workup

  1. temperaturewas heated at 80° for 6 hours
  2. customThe solvent was removed by concentration under reduced pressure
  3. customthe residue was azeotroped with xylene (2×20 ml) under reduced pressure
  4. customThe resulting material was partitioned between methylene chloride and water
  5. customthe aqueous phase separated
  6. extractionre-extracted with methylene chloride
  7. washThe combined organic extracts were washed with brine
  8. dry with materialdried over magnesium sulphate
  9. concentrationconcentrated under reduced pressure
  10. customThe residual material was purified by flash chromatography on silica gel eluting with methylene chloride (97)
  11. customThe product obtained
  12. customafter collection and evaporation of appropriate fractions
  13. customwas further purified by flash chromatography on silica gel eluting with methylene chloride (94.5)
  14. customThe resulting material obtained
  15. customafter collection and evaporation of appropriate fractions
  16. customwas triturated with hexane

Sources & evidence

ORD record
ord-ab7a6410ad3548dfb4c9f033d8f4f1b6
Source dataset
uspto-grants-1991_06
Patent number
US05023258

Reaction notes

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