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Diisopropylamine → 6-(7-hydroxy-6,7-dihydro-5H-pyrrolo[1,2-c]imidazol-7-yl)-N-methyl-2-naphthamide

HRID 724226
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 724226
[CH:1](NC(C)C)([CH3:3])[CH3:2].[CH2:8]([Li])[CH2:9]CC.C(OCC)(=O)C.[CH:19]([N:22](C(C)C)[C:23]([C:25]1C=C[C:32]2[C:27](=C[CH:29]=[C:30]([C:35]([C:37]3[N:38]=[CH:39][N:40](C(C4C=CC=CC=4)(C4C=CC=CC=4)C4C=CC=CC=4)[CH:41]=3)=[O:36])[CH:31]=2)[CH:26]=1)=[O:24])(C)C>C1COCC1.O>[OH:36][C:35]1([C:30]2[CH:31]=[C:32]3[C:1](=[CH:3][CH:29]=2)[CH:2]=[C:25]([C:23]([NH:22][CH3:19])=[O:24])[CH:26]=[CH:27]3)[C:37]2[N:38]([CH:39]=[N:40][CH:41]=2)[CH2:9][CH2:8]1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 7912DiisopropylamineHCID 8857Ethyl AcetateHCID 21879613N,N-diisopropyl-6-[(1-trityl-1H-imidazol-4-yl)carbonyl]-2-naphthamideHCID 178418339Butyllithium

Produkt 1

HCID 98830296-(7-hydroxy-6,7-dihydro-5H-pyrrolo[1,2-c]imidazol-7-yl)-N-methyl-2-naphthamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962
Water
Lösungsmittel
HCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
-70 °C

Versuchsvorschrift

Dry THF (600 ml) containing diisopropylamine (21.3 ml) was cooled to −70° C. and n-butyl lithium (1.6 M; 95.0 ml) was added dropwise. The mixture was stirred for 10 min and ethyl acetate (14.9 ml) was added dropwise. The mixture was stirred at the same temperature for 30 min. A solution of N,N-diisopropyl-6-[(1-trityl-1H-imidazol-4-yl)carbonyl]-2-naphthamide (60.0 g) in dry THF (150 ml) was added dropwise at −70° C. The mixture was stirred at the same temperature for 30 min and the reaction mixture was gradually warmed to −30° C. Water was added to stop the reaction. The organic layer was separated and the aqueous layer was extracted with a THF-toluene (1:1) mixture. The organic layers were combined, washed with saturated brine and dried over magnesium sulfate. The solvent was evaporated to give the title compound quantitatively as a pale yellow oil.

Aufarbeitung

  1. stirringThe mixture was stirred at the same temperature for 30 min
  2. stirringThe mixture was stirred at the same temperature for 30 min
  3. temperaturethe reaction mixture was gradually warmed to −30° C
  4. customthe reaction
  5. customThe organic layer was separated
  6. extractionthe aqueous layer was extracted with a THF-toluene (1:1) mixture
  7. washwashed with saturated brine
  8. dry with materialdried over magnesium sulfate
  9. customThe solvent was evaporated

Quellen und Nachweise

ORD-Eintrag
ord-9e33f6d1aeae4927a2acf4fea78309bc
Quelldatensatz
uspto-grants-2006_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07141598B2

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