Tetrahydrofuran → HCID 178438855, Verbindung

HRID 1412604Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1412604
[O:1]=[C:2]1[C:7]([CH:8]([C:10]2[CH:15]=[CH:14][C:13]([C:16]3[C:17]([C:22]#[N:23])=[CH:18][CH:19]=[CH:20][CH:21]=3)=[CH:12][CH:11]=2)[CH3:9])=[C:6]([CH2:24][CH2:25][CH3:26])[N:5]2[N:27]=[CH:28][N:29]=[C:4]2[N:3]1[CH:30]1[CH2:35][CH2:34][C:33](=[O:36])[CH2:32][CH2:31]1.O1CCCC1.[BH4-].[Na+]>CO>[OH:36][C@H:33]1[CH2:34][CH2:35][C@H:30]([N:3]2[C:2](=[O:1])[C:7]([CH:8]([C:10]3[CH:15]=[CH:14][C:13]([C:16]4[C:17]([C:22]#[N:23])=[CH:18][CH:19]=[CH:20][CH:21]=4)=[CH:12][CH:11]=3)[CH3:9])=[C:6]([CH2:24][CH2:25][CH3:26])[N:5]3[N:27]=[CH:28][N:29]=[C:4]23)[CH2:31][CH2:32]1

Komponenten

5

Edukt 3

HCID 8028TetrahydrofuranHCID 4311764Sodium borohydrideHCID 670104904'-{1-[5-Oxo-4-(4-oxocyclohexyl)-7-propyl-4,5-dihydro[1,2,4]triazolo[1,5-a]pyrimidin-6-yl]ethyl}biphenyl-2-carbonitrile

Produkt 1

HCID 178438855HCID 178438855, VerbindungAusbeute 89,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

To a mixture of 4′-{1-[5-oxo-4-(4-oxocyclohexyl)-7-propyl-4,5-dihydro[1,2,4]triazolo[1,5-a]pyrimidin-6-yl]ethyl}biphenyl-2-carbonitrile (1.38 g), tetrahydrofuran (15 mL) and methanol (10 mL) was added sodium borohydride (0.50 g) at 0° C., and the mixture was stirred at room temperature for 30 min. After evaporation of the solvent under reduced pressure, the residue was extracted with water and ethyl acetate. The obtained ethyl acetate layer was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography to give the title compound as a colorless oil (1.24 g, 89%).

Aufarbeitung

  1. customAfter evaporation of the solvent under reduced pressure
  2. extractionthe residue was extracted with water and ethyl acetate
  3. washThe obtained ethyl acetate layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customthe residue was purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-ea8645dcac1e4c028928f41ff24d4d77
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08921379B2

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