Sodium Carbonate → Ethyl 5-([2-(2-{[4-(5-chloro-1,3-benzoxazol-2-yl)benzyl]oxy}phenyl)ethyl]{2-[4-(methoxy-carbonyl)phenyl]ethyl}amino)-5,6,7,8-tetrahydroquinoline-2-carboxylate

HRID 875320Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 875320
I[CH2:2][CH2:3][C:4]1[CH:13]=[CH:12][C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:6][CH:5]=1.C(=O)([O-])[O-].[Na+].[Na+].[Cl:20][C:21]1[CH:22]=[CH:23][C:24]2[O:28][C:27]([C:29]3[CH:60]=[CH:59][C:32]([CH2:33][O:34][C:35]4[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=4[CH2:41][CH2:42][NH:43][CH:44]4[CH2:53][CH2:52][CH2:51][C:50]5[N:49]=[C:48]([C:54]([O:56][CH2:57][CH3:58])=[O:55])[CH:47]=[CH:46][C:45]4=5)=[CH:31][CH:30]=3)=[N:26][C:25]=2[CH:61]=1>C(#N)C>[Cl:20][C:21]1[CH:22]=[CH:23][C:24]2[O:28][C:27]([C:29]3[CH:60]=[CH:59][C:32]([CH2:33][O:34][C:35]4[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=4[CH2:41][CH2:42][N:43]([CH2:2][CH2:3][C:4]4[CH:13]=[CH:12][C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:6][CH:5]=4)[CH:44]4[CH2:53][CH2:52][CH2:51][C:50]5[N:49]=[C:48]([C:54]([O:56][CH2:57][CH3:58])=[O:55])[CH:47]=[CH:46][C:45]4=5)=[CH:31][CH:30]=3)=[N:26][C:25]=2[CH:61]=1

Komponenten

5

Edukt 3

HCID 10340Sodium CarbonateHCID 22639144Methyl 4-(2-iodoethyl)benzoate2×HCID 86709808Ethyl 5-{[2-(2-{[4-(5-chloro-1,3-benzoxazol-2-yl)benzyl]oxy}phenyl)ethyl]amino}-5,6,7,8-tetrahydroquinoline-2-carboxylate

Produkt 1

HCID 86709810Ethyl 5-([2-(2-{[4-(5-chloro-1,3-benzoxazol-2-yl)benzyl]oxy}phenyl)ethyl]{2-[4-(methoxy-carbonyl)phenyl]ethyl}amino)-5,6,7,8-tetrahydroquinoline-2-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

112 mg (0.39 mmol) of methyl 4-(2-iodoethyl)benzoate and 41 mg (0.39 mmol) of anhydrous sodium carbonate were added to a solution of 149 mg (0.26 mmol) of ethyl 5-{[2-(2-{[4-(5-chloro-1,3-benzoxazol-2-yl)benzyl]oxy}phenyl)ethyl]amino}-5,6,7,8-tetrahydroquinoline-2-carboxylate (Enantiomer 1, Example 61A) in 10 ml of dry acetonitrile, and the mixture was heated under reflux overnight. A further 112 mg of methyl 4-(2-iodoethyl)benzoate were then added, and the mixture was once more heated under reflux overnight. The reaction was then evaporated to dryness, the residue was taken up in water and ethyl acetate and the phases were separated. The organic phase was evaporated to dryness and the residue obtained was purified by preparative HPLC. This gave 72 mg (0.10 mmol, 38% of theory) of the title compound.

Aufarbeitung

  1. temperaturethe mixture was heated
  2. temperatureunder reflux overnight
  3. temperaturethe mixture was once more heated
  4. temperatureunder reflux overnight
  5. customThe reaction was then evaporated to dryness
  6. customethyl acetate and the phases were separated
  7. customThe organic phase was evaporated to dryness
  8. customthe residue obtained
  9. customwas purified by preparative HPLC

Quellen und Nachweise

ORD-Eintrag
ord-6321b601556a48a99dd4b3cafb8ee31a
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08981104B2

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