1,2-Diaminocyclohexane, trans- → 2-Fluoro-5-[3-(4-methyl-pyridin-3-yl)-2-oxo-imidazolidin-1-yl]-benzaldehyde

HRID 80144

Reaktionsgleichung

Reaktionsgleichung von HRID 80144
[CH3:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][C:3]=1[N:8]1[CH2:12][CH2:11][NH:10][C:9]1=[O:13].Br[C:15]1[CH:16]=[CH:17][C:18]([F:23])=[C:19]([CH:22]=1)[CH:20]=[O:21].N[C@@H]1CCCC[C@H]1N.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>[Cu](I)I.O1CCOCC1>[F:23][C:18]1[CH:17]=[CH:16][C:15]([N:10]2[CH2:11][CH2:12][N:8]([C:3]3[CH:4]=[N:5][CH:6]=[CH:7][C:2]=3[CH3:1])[C:9]2=[O:13])=[CH:22][C:19]=1[CH:20]=[O:21]

Komponenten

7

Edukt 4

HCID 438061,2-Diaminocyclohexane, trans-HCID 62657Potassium Phosphate, TribasicHCID 7363275-Bromo-2-fluorobenzaldehydeHCID 596361701-(4-Methylpyridin-3-yl)imidazolidin-2-one

Produkt 1

HCID 866493982-Fluoro-5-[3-(4-methyl-pyridin-3-yl)-2-oxo-imidazolidin-1-yl]-benzaldehydeAusbeute 70,35 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 83717Copper iodideKatalysatorHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

Using the same reaction conditions as in Example 14, 1-(4-methyl-pyridin-3-yl)-imidazolidin-2-one (I-14b: 200 mg, 1.12 mmol) was reacted with 5-bromo-2-fluoro-benzaldehyde (272 mg, 1.34 mmol), 1,4-dioxane (20 mL), copper iodide (18 mg, 0.098 mmol), trans-1,2-diamino cyclohexane (0.05 mL, 0.294 mmol) and potassium phosphate (520 mg, 2.54 mmol) to afford the crude product which was purified by column chromatography on silica gel (2-3% MeOH in CHCl3). The residue was washed with DCM and hexane in dry ice and dried to afford 235 mg of 2-Fluoro-5-[3-(4-methyl-pyridin-3-yl)-2-oxo-imidazolidin-1-yl]-benzaldehyde (70.35% yield).

Aufarbeitung

  1. customto afford the crude product which
  2. customwas purified by column chromatography on silica gel (2-3% MeOH in CHCl3)
  3. washThe residue was washed with DCM and hexane in dry ice
  4. customdried

Quellen und Nachweise

ORD-Eintrag
ord-bca9c6987cc44548b309c24ef7581a54
Quelldatensatz
uspto-grants-2014_09
Patentnummer
USRE045173E1

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