Cyclobutane-1,1-diyldimethanol → 4'-{[4-(6,13-Dioxadispiro[3.2.5.2]tetradec-10-yl)-5-oxo-7-propyl-4,5-dihydro[1,2,4]triazolo[1,5-a]pyrimidin-6-yl]methyl}-3'-fluorobiphenyl-2-carbonitrile

HRID 519633Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 519633
[F:1][C:2]1[CH:3]=[C:4]([C:29]2[C:30]([C:35]#[N:36])=[CH:31][CH:32]=[CH:33][CH:34]=2)[CH:5]=[CH:6][C:7]=1[CH2:8][C:9]1[C:10](=[O:28])[N:11]([CH:21]2[CH2:26][CH2:25][C:24](=[O:27])[CH2:23][CH2:22]2)[C:12]2[N:13]([N:18]=[CH:19][N:20]=2)[C:14]=1[CH2:15][CH2:16][CH3:17].[C:37]1([CH2:43]O)([CH2:41][OH:42])[CH2:40][CH2:39][CH2:38]1>O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C1(C)C=CC=CC=1>[CH2:38]1[C:37]2([CH2:41][O:42][C:24]3([CH2:23][CH2:22][CH:21]([N:11]4[C:10](=[O:28])[C:9]([CH2:8][C:7]5[CH:6]=[CH:5][C:4]([C:29]6[C:30]([C:35]#[N:36])=[CH:31][CH:32]=[CH:33][CH:34]=6)=[CH:3][C:2]=5[F:1])=[C:14]([CH2:15][CH2:16][CH3:17])[N:13]5[N:18]=[CH:19][N:20]=[C:12]45)[CH2:26][CH2:25]3)[O:27][CH2:43]2)[CH2:40][CH2:39]1

Komponenten

5

Edukt 2

HCID 4498243Cyclobutane-1,1-diyldimethanolHCID 670088843'-Fluoro-4'-{[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 670096164'-{[4-(6,13-Dioxadispiro[3.2.5.2]tetradec-10-yl)-5-oxo-7-propyl-4,5-dihydro[1,2,4]triazolo[1,5-a]pyrimidin-6-yl]methyl}-3'-fluorobiphenyl-2-carbonitrileAusbeute 86 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 521998p-Toluenesulfonic acid monohydrateKatalysatorHCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

A mixture of 3′-fluoro-4′-{[5-oxo-4-(4-oxocyclohexyl)-7-propyl-4,5-dihydro[1,2,4]triazolo[1,5-a]pyrimidin-6-yl]methyl}biphenyl-2-carbonitrile (3.5 g), cyclobutane-1,1-diyldimethanol (1 g), p-toluenesulfonic acid monohydrate (0.014 g) and toluene (60 mL) was subjected to an azeotropic dehydration reaction by stirring at 110° C. for 16 hr in a reaction vessel equipped with a Dean-stark trap. The reaction mixture was concentrated, and the obtained residue was purified by silica gel column chromatography to give the title compound as a colorless solid (3.6 g, 86%).

Aufarbeitung

  1. customwas subjected to an azeotropic dehydration reaction
  2. customequipped with a Dean-stark trap
  3. concentrationThe reaction mixture was concentrated
  4. customthe obtained residue was purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-486345a62e3545af8ebe8e0ad7038029
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09115136B2

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