1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 16222146, Verbindung

HRID 1717428Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1717428
[CH:1](/[C:4]1[N:8]([C:9]2[CH:14]=[CH:13][C:12]([C:15]([NH:17][CH2:18][C:19]([F:22])([F:21])[F:20])=[O:16])=[CH:11][CH:10]=2)[N:7]=[N:6][C:5]=1[C:23](O)=[O:24])=[CH:2]\[CH3:3].[CH:26]1([NH2:29])[CH2:28][CH2:27]1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C>CN(C=O)C.C(OCC)(=O)C.O.C(N(CC)CC)C>[CH:26]1([NH:29][C:23]([C:5]2[N:6]=[N:7][N:8]([C:9]3[CH:14]=[CH:13][C:12]([C:15]([NH:17][CH2:18][C:19]([F:20])([F:21])[F:22])=[O:16])=[CH:11][CH:10]=3)[C:4]=2/[CH:1]=[CH:2]/[CH3:3])=[O:24])[CH2:28][CH2:27]1

Komponenten

9

Edukt 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 69828CyclopropylamineHCID 757711-HydroxybenzotriazoleHCID 68515283HCID 68515283, Verbindung

Produkt 1

HCID 16222146HCID 16222146, VerbindungAusbeute 52 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 8471TriethylamineLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of 5-[(1E)-prop-1-en-1-yl]-1-(4-{[(2,2,2-trifluoroethyl)amino]carbonyl}phenyl)-1H-1,2,3-triazole-4-carboxylic acid (1.96 g) obtained in Example 1215a) in DMF (22 ml) were successively added cyclopropylamine (0.46 ml), triethylamine (0.92 ml), HOBt (1.01 g) and WSC (1.27 g), and the reaction mixture was stirred at room temperature for 2.5 hr. Water and ethyl acetate were added to the reaction mixture and the organic layer was separated. The organic layer was dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column (ethyl acetate/hexane=1/1 to ethyl acetate) and recrystallized from ethyl acetate-diisopropyl ether to give the title compound as a white powder (1.13 g, 52%).

Aufarbeitung

  1. customthe organic layer was separated
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. customthe solvent was evaporated under reduced pressure
  4. customThe residue was purified by silica gel column (ethyl acetate/hexane=1/1 to ethyl acetate)
  5. customrecrystallized from ethyl acetate-diisopropyl ether

Quellen und Nachweise

ORD-Eintrag
ord-d8153be25fdb4657a77f0ee94e6ac9a4
Quelldatensatz
uspto-grants-2010_09
Patentnummer
US07803822B2

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