1,8-Diazabicyclo(5.4.0)undec-7-ene → 4'-{[4-(1,4-Dioxaspiro[4.5]dec-8-yl)-5-oxo-7-propyl-2-(trifluoromethyl)-4,5-dihydro[1,2,4]triazolo[1,5-a]pyrimidin-6-yl]methyl}biphenyl-2-carbonitrile

HRID 1688744Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1688744
[O:1]1[C:5]2([CH2:10][CH2:9][CH:8]([NH:11][C:12]3[N:16]=[C:15]([C:17]([F:20])([F:19])[F:18])[NH:14][N:13]=3)[CH2:7][CH2:6]2)[O:4][CH2:3][CH2:2]1.[C:21]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[C:29]1[CH:34]=[CH:33][C:32]([CH2:35][CH:36]([C:42](=O)[CH2:43][CH2:44][CH3:45])[C:37](OCC)=[O:38])=[CH:31][CH:30]=1)#[N:22].N12CCCN=C1CCCCC2>C(N(CC)C1C=CC=CC=1)C.C(OCC)(=O)C>[O:1]1[C:5]2([CH2:10][CH2:9][CH:8]([N:11]3[C:37](=[O:38])[C:36]([CH2:35][C:32]4[CH:33]=[CH:34][C:29]([C:24]5[C:23]([C:21]#[N:22])=[CH:28][CH:27]=[CH:26][CH:25]=5)=[CH:30][CH:31]=4)=[C:42]([CH2:43][CH2:44][CH3:45])[N:13]4[N:14]=[C:15]([C:17]([F:20])([F:18])[F:19])[N:16]=[C:12]34)[CH2:7][CH2:6]2)[O:4][CH2:3][CH2:2]1

Komponenten

6

Edukt 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 10020734Ethyl 2-[(2'-cyanobiphenyl-4-yl)methyl]-3-oxohexanoateHCID 67008537N-(1,4-dioxaspiro[4.5]dec-8-yl)-5-(trifluoromethyl)-1H-1,2,4-triazol-3-amine

Produkt 1

HCID 670096644'-{[4-(1,4-Dioxaspiro[4.5]dec-8-yl)-5-oxo-7-propyl-2-(trifluoromethyl)-4,5-dihydro[1,2,4]triazolo[1,5-a]pyrimidin-6-yl]methyl}biphenyl-2-carbonitrileAusbeute 41 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 7061N,N-DiethylanilineLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A solution of N-(1,4-dioxaspiro[4.5]dec-8-yl)-5-(trifluoromethyl)-1H-1,2,4-triazol-3-amine (9.87 g), ethyl 2-[(2′-cyanobiphenyl-4-yl)methyl]-3-oxohexanoate (23.59 g) and 1,8-diazabicyclo[5.4.0]undec-7-ene (5.05 mL) in N,N-diethylaniline (50 mL) was stirred at 180° C. for 16 hr. The reaction mixture was diluted with ethyl acetate, and the mixture was washed with 1 N hydrochloric acid and then with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel chromatography [eluent: hexane/ethyl acetate=80/20→60/40 (volume ratio)], and crystallized from diisopropyl ether to give the title compound as a colorless solid (7.91 g, 41%).

Aufarbeitung

  1. washthe mixture was washed with 1 N hydrochloric acid
  2. dry with materialwith saturated brine, and dried over anhydrous magnesium sulfate
  3. customThe solvent was evaporated under reduced pressure
  4. customthe residue was purified by silica gel chromatography [eluent: hexane/ethyl acetate=80/20→60/40 (volume ratio)]
  5. customcrystallized from diisopropyl ether

Quellen und Nachweise

ORD-Eintrag
ord-1f2d39f4790f47d2b912c41a82afe8be
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08148383B2

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