Pyridine → 5-Benzyloxycarbonylamino-2-(4-{2-methoxyethyl}-3-oxopiperazin-1-yl)fluorobenzene

HRID 1108587Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1108587
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([N:9]2[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][O:17][CH3:18])[C:11](=[O:19])[CH2:10]2)=[C:6]([F:8])[CH:7]=1.N1C=CC=CC=1.Cl[C:27]([O:29][CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)=[O:28]>ClCCl>[CH2:30]([O:29][C:27]([NH:1][C:2]1[CH:3]=[CH:4][C:5]([N:9]2[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][O:17][CH3:18])[C:11](=[O:19])[CH2:10]2)=[C:6]([F:8])[CH:7]=1)=[O:28])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

Komponenten

5

Edukt 3

HCID 1049PyridineHCID 10387Benzyl chloroformateHCID 187839025-Amino-2-(4-{2-methoxyethyl}-3-oxopiperazin-1-yl)fluorobenzene

Produkt 1

HCID 187839065-Benzyloxycarbonylamino-2-(4-{2-methoxyethyl}-3-oxopiperazin-1-yl)fluorobenzene

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
-20 °C

Versuchsvorschrift

5-Amino-2-(4-{2-methoxyethyl}-3-oxopiperazin-1-yl)fluorobenzene (3.5 g) was dissolved in dry dichloromethane (50 ml) under argon. Pyridine (1.33 ml) was added, and the mixture cooled to -20° C. Benzyl chloroformate (2.06 ml) was added, and the mixture stirred for 10 minutes at -20° C., before allowing the temperature to rise to ambient over 1.5 hours. Solvents were evaporated, the residue dissolved in dichloromethane and washed with sodium bicarbonate solution. After drying (MgSO4) and evaporation of solvent, the residue was chromatographed on silica, using as eluant a gradient increasing in polarity from 0 to 4% methanol in dichloromethane. Relevant fractions were combined and evaporated to give 5-benzyloxycarbonylamino-2-(4-{2-methoxyethyl}-3-oxopiperazin-1-yl)fluorobenzene (3.28 g).

Aufarbeitung

  1. waitto ambient over 1.5 hours
  2. customSolvents were evaporated
  3. dissolutionthe residue dissolved in dichloromethane
  4. washwashed with sodium bicarbonate solution
  5. customAfter drying
  6. custom(MgSO4) and evaporation of solvent
  7. customthe residue was chromatographed on silica
  8. temperaturea gradient increasing in polarity from 0 to 4% methanol in dichloromethane
  9. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-63f7b243b9444ded82b59f57879b9c03
Quelldatensatz
uspto-grants-2000_05
Patentnummer
US06069145

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