Sodium Azide → 5-(4-Chlorophenyl)-4-[(2S)-3,3,3-trifluoro-2-hydroxypropyl]-2-({1-[2-(trifluoromethyl)phenyl]-1H-1,2,3-triazol-4-yl}methyl)-2,4-dihydro-3H-1,2,4-triazol-3-one

HRID 714710Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 714710
[N-:1]=[N+:2]=[N-:3].[Na+].[F:5][C:6]([F:17])([F:16])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1B(O)O.[Na].O=C1O[C@H]([C@H](CO)O)C(O)=C1O.[Cl:31][C:32]1[CH:37]=[CH:36][C:35]([C:38]2[N:39]([CH2:47][C@H:48]([OH:53])[C:49]([F:52])([F:51])[F:50])[C:40](=[O:46])[N:41]([CH2:43][C:44]#[CH:45])[N:42]=2)=[CH:34][CH:33]=1>CO.O.C(OCC)(=O)C.[OH-].[Na+].O.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[Cl:31][C:32]1[CH:37]=[CH:36][C:35]([C:38]2[N:39]([CH2:47][C@H:48]([OH:53])[C:49]([F:51])([F:52])[F:50])[C:40](=[O:46])[N:41]([CH2:43][C:44]3[N:1]=[N:2][N:3]([C:8]4[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=4[C:6]([F:17])([F:16])[F:5])[CH:45]=3)[N:42]=2)=[CH:34][CH:33]=1

Komponenten

10

Edukt 4

HCID 33557Sodium AzideHCID 27343872-(Trifluoromethyl)benzeneboronic acidHCID 66586226sodium L-ascorbic acidHCID 866909105-(4-Chlorophenyl)-2-(prop-2-yn-1-yl)-4-[(2S)-3,3,3-trifluoro-2-hydroxypropyl]-2,4-dihydro-3H-1,2,4-triazol-3-one

Produkt 1

HCID 866909335-(4-Chlorophenyl)-4-[(2S)-3,3,3-trifluoro-2-hydroxypropyl]-2-({1-[2-(trifluoromethyl)phenyl]-1H-1,2,3-triazol-4-yl}methyl)-2,4-dihydro-3H-1,2,4-triazol-3-one

Reagenzien, Katalysatoren, Lösungsmittel 5

HCID 165397Cupric acetate monohydrateKatalysatorHCID 887MethanolLösungsmittelHCID 962WaterLösungsmittel2×HCID 8857Ethyl AcetateLösungsmittelHCID 14798Sodium HydroxideLösungsmittel

Versuchsvorschrift

20 mg (0.31 mmol) of sodium azide were initially charged in 1 ml of methanol, and 58 mg (0.31 mmol) of 2-(trifluoromethyl)phenylboronic acid and 6 mg (0.03 mmol) of copper(II) acetate monohydrate were added. The mixture was stirred at RT for 18 h. 0.9 ml of water, 30 mg (0.15 mmol) of L-ascorbic acid sodium salt and 117 mg (0.34 mmol) of the compound from Example 14A were then added to the mixture. The mixture was stirred at RT for a further 18 h. For work-up, the mixture was diluted with 10 ml of water and 10 ml of ethyl acetate, and 5 ml 0.1 N aqueous sodium hydroxide solution were added with stirring. After phase separation, the aqueous phase was extracted three more times with in each case 10 ml of ethyl acetate. The combined organic phases were dried over sodium sulfate, filtered and concentrated under reduced pressure. The crude product was purified by chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 5:1, then 1:2). This gave 117 mg (71% of theory) of the target compound.

Aufarbeitung

  1. stirringThe mixture was stirred at RT for a further 18 h
  2. additionwere added
  3. stirringwith stirring
  4. customAfter phase separation
  5. extractionthe aqueous phase was extracted three more times with in each case 10 ml of ethyl acetate
  6. dry with materialThe combined organic phases were dried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe crude product was purified by chromatography on silica gel (mobile phase

Quellen und Nachweise

ORD-Eintrag
ord-b6eec341133f462bbff55dee25ccef0e
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09187466B2

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