Sodium hydride → HCID 66919002, Verbindung

HRID 2354218Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2354218
[CH:1]1([NH:4][C:5]([C:7]2[CH:8]=[CH:9][C:10]([CH3:26])=[C:11]([NH:13][C:14](=[O:25])[C:15]3[CH:20]=[C:19](F)[CH:18]=[CH:17][C:16]=3[N+:22]([O-:24])=[O:23])[CH:12]=2)=[O:6])[CH2:3][CH2:2]1.C(OC([N:34]1[CH2:38][CH2:37][CH2:36][C@H:35]1[CH2:39][OH:40])=O)(C)(C)C.[H-].[Na+].[Cl-:43].[NH4+]>CN(C=O)C>[ClH:43].[CH:1]1([NH:4][C:5]([C:7]2[CH:8]=[CH:9][C:10]([CH3:26])=[C:11]([NH:13][C:14](=[O:25])[C:15]3[CH:20]=[C:19]([O:40][CH2:39][C@@H:35]4[CH2:36][CH2:37][CH2:38][NH:34]4)[CH:18]=[CH:17][C:16]=3[N+:22]([O-:24])=[O:23])[CH:12]=2)=[O:6])[CH2:3][CH2:2]1

Komponenten

6

Edukt 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 643448(S)-(-)-N-Boc-prolinolHCID 669189745-fluoro-N-{5-[(cyclopropylamino)carbonyl]-2-methylphenyl}-2-nitrobenzamide

Produkt 1

HCID 66919002HCID 66919002, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of N-{5-[(cyclopropylamino)carbonyl]-2-methylphenyl}-5-fluoro-2-nitrobenzamide (3.0 g) and (S)-(−)-1-(tert-butoxycarbonyl)-2-pyrrolidinemethanol (2.54 g) in DMF (45 ml) was added sodium hydride (1.34 g of a 60% dispersion in oil) portion-wise (ice bath cooling). The reaction was stirred for 24 hours at room temperature under an atmosphere of argon. The reaction mixture was then poured into a saturated aqueous ammonium chloride solution (200 ml) and the resulting precipitate was collected by filtration, dissolved in methanol (10 ml) and 4N HCl in dioxane (5 ml) added. The reaction mixture was stirred at room temperature for 16 hours, concentrated and re-precipitated from methanol/ethyl acetate to yield N-{5-[(cyclopropylamino)carbonyl]-2-methylphenyl}-2-nitro-5-[(2S)-pyrrolidin-2-ylmethoxy]benzamide hydrochloride salt (2.25 g) as a yellow solid which was used without further purification; Mass Spectrum: M+H+ 439.

Aufarbeitung

  1. temperatureportion-wise (ice bath cooling)
  2. filtrationthe resulting precipitate was collected by filtration
  3. dissolutiondissolved in methanol (10 ml)
  4. addition4N HCl in dioxane (5 ml) added
  5. stirringThe reaction mixture was stirred at room temperature for 16 hours
  6. concentrationconcentrated
  7. customre-precipitated from methanol/ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-acedb559e6834aa4a102c8e097492030
Quelldatensatz
uspto-grants-2010_07
Patentnummer
US07750154B2

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