Hydrochloric Acid → 4'-{[4-(2,3-Dimethyl-1,4-dioxaspiro[4.5]dec-8-yl)-2-methyl-5-oxo-7-propyl-4,5-dihydro[1,2,4]triazolo[1,5-a]pyrimidin-6-yl]methyl}-4-fluorobiphenyl-2-carbonitrile

HRID 1412343Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1412343
O1C2(C[CH2:9][CH:8]([N:11]3[C:16](=[O:17])[C:15]([CH2:18][C:19]4[CH:24]=[CH:23][C:22]([C:25]5[C:26]([C:32]#[N:33])=[CH:27][C:28]([F:31])=[CH:29][CH:30]=5)=[CH:21][CH:20]=4)=[C:14]([CH2:34][CH2:35][CH3:36])[N:13]4[N:37]=[C:38]([CH3:40])[N:39]=[C:12]34)[CH2:7][CH2:6]2)OCC1.Cl.O1CC[CH2:44][CH2:43]1.[C:47]([O:50][CH2:51][CH3:52])(=[O:49])[CH3:48]>>[CH3:52][CH:51]1[CH:43]([CH3:44])[O:49][C:47]2([CH2:6][CH2:7][CH:8]([N:11]3[C:16](=[O:17])[C:15]([CH2:18][C:19]4[CH:20]=[CH:21][C:22]([C:25]5[C:26]([C:32]#[N:33])=[CH:27][C:28]([F:31])=[CH:29][CH:30]=5)=[CH:23][CH:24]=4)=[C:14]([CH2:34][CH2:35][CH3:36])[N:13]4[N:37]=[C:38]([CH3:40])[N:39]=[C:12]34)[CH2:9][CH2:48]2)[O:50]1

Komponenten

5

Edukt 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 8857Ethyl AcetateHCID 670100244'-{[4-(1,4-Dioxaspiro[4.5]dec-8-yl)-2-methyl-5-oxo-7-propyl-4,5-dihydro[1,2,4]triazolo[1,5-a]pyrimidin-6-yl]methyl}-4-fluorobiphenyl-2-carbonitrile

Produkt 1

HCID 670096714'-{[4-(2,3-Dimethyl-1,4-dioxaspiro[4.5]dec-8-yl)-2-methyl-5-oxo-7-propyl-4,5-dihydro[1,2,4]triazolo[1,5-a]pyrimidin-6-yl]methyl}-4-fluorobiphenyl-2-carbonitrileAusbeute 100 %

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

A mixture of 4′-{[4-(1,4-dioxaspiro[4.5]dec-8-yl)-2-methyl-5-oxo-7-propyl-4,5-dihydro[1,2,4]triazolo[1,5-a]pyrimidin-6-yl]methyl}-4-fluorobiphenyl-2-carbonitrile (1.1 g), 3N hydrochloric acid (30 mL) and tetrahydrofuran (30 mL) was stirred at 70° C. for 16 hr. The reaction mixture was diluted with ethyl acetate, washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The obtained residue was dissolved in toluene (30 mL), 2,3-dimethylpropane-1,3-diol (0.2 g) and p-toluenesulfonic acid monohydrate (0.004 g) were added, and the mixture was subjected to an azeotropic dehydration reaction by stirring at 110° C. for 3 hr in a reaction vessel equipped with a Dean-stark trap. The reaction mixture was concentrated under reduced pressure, and the obtained residue was purified by silica gel column chromatography to give the title compound as a colorless solid (1.3 g, 100%).

Aufarbeitung

  1. washwashed with saturated brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. customThe solvent was evaporated under reduced pressure
  4. dissolutionThe obtained residue was dissolved in toluene (30 mL)
  5. addition2,3-dimethylpropane-1,3-diol (0.2 g) and p-toluenesulfonic acid monohydrate (0.004 g) were added
  6. customthe mixture was subjected to an azeotropic dehydration reaction
  7. stirringby stirring at 110° C. for 3 hr in a reaction vessel
  8. customequipped with a Dean-stark trap
  9. concentrationThe reaction mixture was concentrated under reduced pressure
  10. customthe obtained residue was purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-58aaee12f5a64c6591af3f8d65bfca47
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08921379B2

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