N,N-Dimethylethylenediamine → HCID 86723912, Verbindung

HRID 576808

Reaktionsgleichung

Reaktionsgleichung von HRID 576808
[CH3:1][N:2]1[C:7](=[O:8])[C:6]([C:9]2C(SC)=[CH:12][N:11]([C:16]3[CH:17]=[CH:18][CH:19]=[C:20]([CH:23]=3)[C:21]#[N:22])[N:10]=2)=[C:5]([CH3:24])[N:4]([C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([C:31]([F:34])([F:33])[F:32])[CH:26]=2)[C:3]1=[O:35].[Na].[CH3:37][S:38]([OH:40])=[O:39].[CH3:41]N(C)CCN>CS(C)=O.C(OCC)(=O)C.C1C=CC=CC=1.C(S([O-])(=O)=O)(F)(F)F.C(S([O-])(=O)=O)(F)(F)F.[Cu+].[Cu+]>[CH3:1][N:2]1[C:7](=[O:8])[C:6]([C:9]2[C:37]([S:38]([CH3:41])(=[O:40])=[O:39])=[CH:12][N:11]([C:16]3[CH:17]=[CH:18][CH:19]=[C:20]([CH:23]=3)[C:21]#[N:22])[N:10]=2)=[C:5]([CH3:24])[N:4]([C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([C:31]([F:34])([F:32])[F:33])[CH:26]=2)[C:3]1=[O:35]

Komponenten

7

Edukt 3

HCID 66053N,N-DimethylethylenediamineHCID 1621282420277-69-4HCID 867239105-(3,6-dimethyl-2,4-dioxo-1-(3-trifluoromethylphenyl)-1,2,3,4-tetrahydropyrimidin-5-yl-4-(methylthio)-1H-pyrazol-1-yl)benzonitrile

Produkt 1

HCID 86723912HCID 86723912, VerbindungAusbeute 41,4 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 2734754Benzene;bis(copper(1+));bis(trifluoromethanesulfonate)KatalysatorHCID 679Dimethyl SulfoxideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

To a solution of the compound prepared in Example 269 (2.84 g) in dimethyl sulfoxide (9.8 ml) were added methanesulfinic acid sodium (2.00 g), copper trifluoromethanesulfonate benzene complex (1.24 g), N,N-dimethylethylenediamine (529 mg) and the resulting mixture was stirred at 110° C. for seven hours. The reaction mixture was diluted with ethyl acetate (300 ml), and the organic layer was washed with 10% ammonia water (50 ml) and saturated saline (50 ml), dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate) to afford 4-(5-(3,6-dimethyl-2,4-dioxo-1-(3-trifluoromethylphenyl)-1,2,3,4-tetrahydropyrimidin-5-yl-4-(methylsulfonyl)-1H-pyrazol-1-yl)benzonitrile (1.25 g).

Aufarbeitung

  1. washthe organic layer was washed with 10% ammonia water (50 ml) and saturated saline (50 ml)
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-35e5bd401da64b9c8d637d157f70b4fa
Quelldatensatz
uspto-grants-2015_05
Patentnummer
US09040516B2

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