3-Phenylpropyl isocyanate → N-(3-phenylpropyl)-N'-[(2,2-dimethoxy-2-(4-pyridyl)-1-(4-fluorophenyl)ethyl)] urea

HRID 719756Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 719756
[CH3:1][O:2][C:3]([O:19][CH3:20])([C:13]1[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=1)[CH:4]([C:6]1[CH:11]=[CH:10][C:9]([F:12])=[CH:8][CH:7]=1)[NH2:5].[N:21]([CH2:24][CH2:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[C:22]=[O:23]>C1COCC1>[C:27]1([CH2:26][CH2:25][CH2:24][NH:21][C:22]([NH:5][CH:4]([C:6]2[CH:7]=[CH:8][C:9]([F:12])=[CH:10][CH:11]=2)[C:3]([O:2][CH3:1])([O:19][CH3:20])[C:13]2[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=2)=[O:23])[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Komponenten

4

Edukt 2

HCID 34276663-Phenylpropyl isocyanateHCID 219018732,2-Dimethoxy-2-(4-pyridyl)-1-(4-fluorophenyl)ethanamine

Produkt 1

HCID 21901874N-(3-phenylpropyl)-N'-[(2,2-dimethoxy-2-(4-pyridyl)-1-(4-fluorophenyl)ethyl)] urea

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a solution of 2,2-dimethoxy-2-(4-pyridyl)-1-(4-fluorophenyl)ethanamine (1.22 g, 4.4 mmol) in THF (10 mL) was added a solution of (3-isocyanatopropyl)-benzene (1.61 g, 10 mmol) in THF (10 mL). The resulting mixture was stirred at room temperature for 30 minutes. The reaction was quenched by addition of water (50 mL) and extracted with ethyl acetate (2×50 mL). The combined ethyl acetate extract was washed with water (50 mL), brine (50 mL) and dried with Na2SO4. After removal of solvent, the crude product was purified by column chromatography to yield the product as a light brown solid.

Aufarbeitung

  1. customThe reaction was quenched by addition of water (50 mL)
  2. extractionextracted with ethyl acetate (2×50 mL)
  3. extractionThe combined ethyl acetate extract
  4. washwas washed with water (50 mL), brine (50 mL)
  5. dry with materialdried with Na2SO4
  6. customAfter removal of solvent
  7. customthe crude product was purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-7af0c282d60b4223892d0a22325ba8af
Quelldatensatz
uspto-grants-2006_11
Patentnummer
US07132544B2

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