Cesium carbonate → 1-(4-{3-[(2R)-2-methylpyrrolidin-1-yl]propoxy}phenyl)-1H-pyrazole-4-carboxylic acid ethyl ester

HRID 1364210Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1364210
I[C:2]1[CH:17]=[CH:16][C:5]([O:6][CH2:7][CH2:8][CH2:9][N:10]2[CH2:14][CH2:13][CH2:12][C@H:11]2[CH3:15])=[CH:4][CH:3]=1.[CH2:18]([O:20][C:21]([C:23]1[CH:24]=[N:25][NH:26][CH:27]=1)=[O:22])[CH3:19].CN[C@@H]1CCCC[C@H]1NC.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O.O.[Cu](I)I>[CH2:18]([O:20][C:21]([C:23]1[CH:24]=[N:25][N:26]([C:2]2[CH:17]=[CH:16][C:5]([O:6][CH2:7][CH2:8][CH2:9][N:10]3[CH2:14][CH2:13][CH2:12][C@H:11]3[CH3:15])=[CH:4][CH:3]=2)[CH:27]=1)=[O:22])[CH3:19]

Komponenten

8

Edukt 4

HCID 10796Cesium carbonateHCID 142179ethyl 1H-pyrazole-4-carboxylateHCID 2733821trans-N,N'-dimethyl-1,2-cyclohexanediamineHCID 57675747(2R)-1-[3-(4-iodophenoxy)propyl]-2-methylpyrrolidine

Produkt 1

HCID 595417211-(4-{3-[(2R)-2-methylpyrrolidin-1-yl]propoxy}phenyl)-1H-pyrazole-4-carboxylic acid ethyl ester

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 83717Copper iodideKatalysatorHCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A suspension of (2R)-1-[3-(4-iodophenoxy)propyl]-2-methylpyrrolidine obtained in Example 1-(2) (1.60 g), 1H-pyrazole-4-carboxylic acid ethyl ester (0.779 g), (rac-trans-N,N′-dimethylcyclohexane-1,2-diamine (0.263 g), copper iodide (0.088 g) and cesium carbonate (3.02 g) in N,N-dimethylformamide (2.5 mL) was stirred at 120° C. for 4 hours. The reaction mixture was cooled to room temperature, diluted with water and extracted with ethyl acetate. The organic layer was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (eluting solvent: n-hexane:ethyl acetate=3:1) to give the titled compound (1.11 g) as a yellow oil.

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. concentrationThe organic layer was concentrated under reduced pressure
  3. customthe resulting residue was purified by silica gel column chromatography (eluting solvent: n-hexane:ethyl acetate=3:1)

Quellen und Nachweise

ORD-Eintrag
ord-abe40779c6b943c4bd6ee96249ea942c
Quelldatensatz
uspto-grants-2011_02
Patentnummer
US07888354B2

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