Tetrahydrofuran → HCID 178438761, Verbindung

HRID 519898

Reaktionsgleichung

Reaktionsgleichung von HRID 519898
[CH3:1][C:2]1[CH:7]=[C:6]([CH2:8][C:9]2[C:10](=[O:29])[N:11]([CH:22]3[CH2:27][CH2:26][C:25](=[O:28])[CH2:24][CH2:23]3)[C:12]3[N:13]([N:18]=[C:19]([CH3:21])[N:20]=3)[C:14]=2[CH2:15][CH2:16][CH3:17])[CH:5]=[CH:4][C:3]=1[C:30]1[C:31]([C:36]#[N:37])=[CH:32][CH:33]=[CH:34][CH:35]=1.O1CCCC1.[BH4-].[Na+]>CO>[OH:28][C@H:25]1[CH2:26][CH2:27][C@H:22]([N:11]2[C:10](=[O:29])[C:9]([CH2:8][C:6]3[CH:5]=[CH:4][C:3]([C:30]4[C:31]([C:36]#[N:37])=[CH:32][CH:33]=[CH:34][CH:35]=4)=[C:2]([CH3:1])[CH:7]=3)=[C:14]([CH2:15][CH2:16][CH3:17])[N:13]3[N:18]=[C:19]([CH3:21])[N:20]=[C:12]23)[CH2:23][CH2:24]1

Komponenten

5

Edukt 3

HCID 8028TetrahydrofuranHCID 4311764Sodium borohydrideHCID 670096082'-Methyl-4'-{[2-methyl-5-oxo-4-(4-oxocyclohexyl)-7-propyl-4,5-dihydro[1,2,4]triazolo[1,5-a]pyrimidin-6-yl]methyl}biphenyl-2-carbonitrile

Produkt 1

HCID 178438761HCID 178438761, VerbindungAusbeute 91,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

To a mixture of 2′-methyl-4′-{[2-methyl-5-oxo-4-(4-oxocyclohexyl)-7-propyl-4,5-dihydro[1,2,4]triazolo[1,5-a]pyrimidin-6-yl]methyl}biphenyl-2-carbonitrile (1.10 g), tetrahydrofuran (10 mL) and methanol (10 mL) was added sodium borohydride (0.05 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 (1.01 g, 91%).

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-ccb1dea190894212844d5d609616440b
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09115136B2

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