Triethylamine → HCID 178522056, Verbindung

HRID 45814

Reaktionsgleichung

Reaktionsgleichung von HRID 45814
[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[C:8]([C:12]3[CH:13]=[C:14]([NH2:18])[CH:15]=[CH:16][CH:17]=3)=[N:9][NH:10][CH:11]=2)=[CH:3][CH:2]=1.[F:19][C:20]([F:31])([F:30])[C:21]1[CH:26]=[CH:25][C:24]([N:27]=[C:28]=[O:29])=[CH:23][CH:22]=1.C(N(CC)CC)C>N1C=CC=CC=1>[N:1]1[CH:2]=[CH:3][C:4]([C:7]2[C:8]([C:12]3[CH:13]=[C:14]([NH:18][C:28]([NH:27][C:24]4[CH:23]=[CH:22][C:21]([C:20]([F:19])([F:30])[F:31])=[CH:26][CH:25]=4)=[O:29])[CH:15]=[CH:16][CH:17]=3)=[N:9][NH:10][CH:11]=2)=[CH:5][CH:6]=1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 737684-(Trifluoromethyl)phenyl isocyanateHCID 178507541HCID 178507541, Verbindung

Produkt 1

HCID 178522056HCID 178522056, VerbindungAusbeute 75 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To 3-(4-Pyridin-4-yl-1H-pyrazol-3-yl)-phenylamine (700 mg, 3 mmol) in anhydrous pyridine (15 mL) at 0° C. 4-trifluoromethylphenylisocyanate (420 μL, 3 mmol) was added. The reaction was stirred for 2 hours at 0° C. under nitrogen atmosphere to give a mixture of monourea and bis-urea as regioisomeric mixture. Solvent was removed under reduced pressure. The residue was dissolved in methanol (15 mL) and triethylamine (1 mL, 7.8 mmol) was added and the reaction was stirred at room temperature overnight. After this time only the monourea could be detected by HPLC/MS. The solvent was removed under reduced pressure and the residue was dissolved in ethyl acetate (100 mL) and washed successively with water (3×50 mL). The crude was purified by silica gel column chromatography (DCM/methanol 9:1) to give the desired product as a white solid (75%).

Aufarbeitung

  1. customat 0° C
  2. customto give
  3. customSolvent was removed under reduced pressure
  4. dissolutionThe residue was dissolved in methanol (15 mL)
  5. stirringthe reaction was stirred at room temperature overnight
  6. customThe solvent was removed under reduced pressure
  7. dissolutionthe residue was dissolved in ethyl acetate (100 mL)
  8. washwashed successively with water (3×50 mL)
  9. customThe crude was purified by silica gel column chromatography (DCM/methanol 9:1)

Quellen und Nachweise

ORD-Eintrag
ord-568357e338334b369eb32b7a7405ce38
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08541575B2

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