Toluene → N,N-diisopropyl-6-[(1-trityl-1H-imidazol-4-yl)carbonyl]-2-naphthamide

HRID 724214

Reaktionsgleichung

Reaktionsgleichung von HRID 724214
C1(C)C=CC=CC=1.C([Li])CCC.Br[C:14]1[CH:15]=[C:16]2[C:21](=[CH:22][CH:23]=1)[CH:20]=[C:19]([C:24]([N:26]([CH:30]([CH3:32])[CH3:31])[CH:27]([CH3:29])[CH3:28])=[O:25])[CH:18]=[CH:17]2.CON(C)C(C[C:39]1[N:40]=[CH:41][N:42]([C:44]([C:57]2[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=2)([C:51]2[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=2)[C:45]2[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=2)[CH:43]=1)=O.C1C[O:67][CH2:66]C1>O>[CH:27]([N:26]([CH:30]([CH3:32])[CH3:31])[C:24]([C:19]1[CH:18]=[CH:17][C:16]2[C:21](=[CH:22][CH:23]=[C:14]([C:66]([C:39]3[N:40]=[CH:41][N:42]([C:44]([C:51]4[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=4)([C:45]4[CH:46]=[CH:47][CH:48]=[CH:49][CH:50]=4)[C:57]4[CH:58]=[CH:59][CH:60]=[CH:61][CH:62]=4)[CH:43]=3)=[O:67])[CH:15]=2)[CH:20]=1)=[O:25])([CH3:29])[CH3:28]

Komponenten

7

Edukt 5

HCID 1140TolueneHCID 8028Tetrahydrofuran2×HCID 21879639HCID 21879639, VerbindungHCID 54243787N-Methyl-N-methoxy-2-(1-triphenylmethyl-1H-imidazol-4-yl)acetamideHCID 178418339Butyllithium

Produkt 1

HCID 21879613N,N-diisopropyl-6-[(1-trityl-1H-imidazol-4-yl)carbonyl]-2-naphthamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
-70 °C

Versuchsvorschrift

Dry toluene (20 ml) was cooled to −70° C. and n-butyl lithium (1.6 M; 2.35 ml) was added dropwise. A solution of 6-bromo-N,N-diisopropyl-2-naphthamide (1.20 g) in dry THF (8 ml) was added dropwise to the reaction mixture. After stirring the mixture at −70° C. for 20 min, a solution of N-methoxy-N-methyl-1-trityl-1H-imidazole-4-carboxyamide (1.09 g) in dry THF (6 ml) was added dropwise to the reaction mixture. The mixture was stirred at −70° C. for 20 min and water was added at the same temperature to stop the reaction. The mixture was extracted with ethyl acetate, and the organic layer was washed with saturated brine and dried over magnesium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by column chromatography (hexane:ethyl acetate=2:1) to give the title compound (1.40 g) as a colorless powder. The physical and chemical data were identical with those obtained for the compound obtained of Reference Example 13.

Aufarbeitung

  1. stirringThe mixture was stirred at −70° C. for 20 min
  2. customthe reaction
  3. extractionThe mixture was extracted with ethyl acetate
  4. washthe organic layer was washed with saturated brine
  5. dry with materialdried over magnesium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. customthe residue was purified by column chromatography (hexane:ethyl acetate=2:1)

Quellen und Nachweise

ORD-Eintrag
ord-f83ff25fe42847548c13016112ee2d90
Quelldatensatz
uspto-grants-2006_11
Patentnummer
US07141598B2

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