Diethyl cyanophosphonate → HCID 67067457, Verbindung

HRID 599570Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 599570
C(P(=O)(OCC)OCC)#N.[CH3:11][O:12][C:13]1[CH:14]=[C:15](/[CH:25]=[CH:26]/[C:27]([OH:29])=O)[CH:16]=[CH:17][C:18]=1[N:19]1[CH:23]=[C:22]([CH3:24])[N:21]=[CH:20]1.Cl.[NH2:31][CH2:32][C:33](=[O:42])[CH2:34][C:35]1[CH:40]=[CH:39][C:38]([F:41])=[CH:37][CH:36]=1.O.C(=O)(O)[O-].[Na+]>CN(C=O)C.C(OCC)(=O)C.C(N(CC)CC)C>[F:41][C:38]1[CH:37]=[CH:36][C:35]([CH2:34][C:33](=[O:42])[CH2:32][NH:31][C:27](=[O:29])/[CH:26]=[CH:25]/[C:15]2[CH:16]=[CH:17][C:18]([N:19]3[CH:23]=[C:22]([CH3:24])[N:21]=[CH:20]3)=[C:13]([O:12][CH3:11])[CH:14]=2)=[CH:40][CH:39]=1

Komponenten

8

Edukt 4

HCID 76257Diethyl cyanophosphonateHCID 132906742-Propanone, 1-amino-3-(4-fluorophenyl)-, hydrochloride (1:1)HCID 59528030(E)-3-[3-methoxy-4-(4-methylimidazol-1-yl)phenyl]acrylic acidHCID 86585896Sodium bicarbonate water

Produkt 1

HCID 67067457HCID 67067457, VerbindungAusbeute 13,6 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 6228DimethylformamideLösungsmittel2×HCID 8471TriethylamineLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Diethyl cyanophosphonate (0.12 mL) was added to a solution of (E)-3-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]acrylic acid (200 mg) and triethylamine (0.54 mL) in DMF (2 mL), and the reaction solution was stirred at 0° C. for 30 minutes. A solution of 1-amino-3-(4-fluorophenyl)propan-2-one hydrochloride (CAS #93102-98-8, 158 mg) in DMF (1 mL) was added dropwise to the reaction solution over 20 minutes, and the reaction solution was stirred at 0° C. for 1.5 hours. Ethyl acetate and saturated sodium bicarbonate water were added to the reaction solution, and the organic layer was separated. The resulting organic layer was dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (carrier: Chromatorex™ NH; elution solvent: ethyl acetate→ethyl acetate:methanol=5:1) to obtain 43 mg of the title compound. The property values of the compound are as follows.

Aufarbeitung

  1. stirringthe reaction solution was stirred at 0° C. for 1.5 hours
  2. customthe organic layer was separated
  3. dry with materialThe resulting organic layer was dried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (carrier: Chromatorex™ NH; elution solvent: ethyl acetate→ethyl acetate:methanol=5:1)

Quellen und Nachweise

ORD-Eintrag
ord-c90514c1d38044b2b9e0d225f94b4341
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07897632B2

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