Benzoic Acid → HCID 68450074, Verbindung

HRID 1169656Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1169656
[CH:1]1[C:10]2[C:5](=[C:6]([NH:11][C:12]([CH3:16])([CH3:15])[C:13]#N)[CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][N:2]=1.C(O)(=[O:24])C1C=CC=CC=1.[F:26][C:27]([F:39])([F:38])[S:28][C:29]1[CH:34]=[CH:33][C:32]([N:35]=[C:36]=[O:37])=[CH:31][CH:30]=1>ClC1C=CC=CC=1>[CH:1]1[C:10]2[C:5](=[C:6]([N:11]3[C:12]([CH3:16])([CH3:15])[C:13](=[O:24])[N:35]([C:32]4[CH:31]=[CH:30][C:29]([S:28][C:27]([F:38])([F:26])[F:39])=[CH:34][CH:33]=4)[C:36]3=[O:37])[CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][N:2]=1

Komponenten

5

Edukt 3

HCID 243Benzoic AcidHCID 27333921-Isocyanato-4-[(trifluoromethyl)sulfanyl]benzeneHCID 684491322-(Isoquinolin-5-ylamino)-2-methylpropionitrile

Produkt 1

HCID 68450074HCID 68450074, VerbindungAusbeute 677,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 7964ChlorobenzeneLösungsmittel

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

500 mg (2.4 mmol) of 2-(isoquinolin-5-ylamino)-2-methylpropionitrile, 1.6 mg (0.013 mmol) of benzoic acid and 526 mg (2.4 mmol) of 4-(trifluoromethylthio)phenyl isocyanate in 4 ml of chlorobenzene were refluxed for 2 days. The resulting mixture was filtered and the filtrate was evaporated to dryness. The intermediate imine was separated out by preparative HPLC chromatography (RP 18, acetonitrile, water, 0.01% TFA). 60 mg of the resulting product were stirred for 1 hour at 40° C. with 1N hydrochloric acid. The solvent was evaporated off and the residue was taken up in sodium hydrogen carbonate solution and extracted with ethyl acetate. The combined organic phases were dried and the residue remaining after evaporation was purified by flash chromatography (SiO2, methylene chloride/methanol=98/2), to give 38 mg of the desired product.

Aufarbeitung

  1. filtrationThe resulting mixture was filtered
  2. customthe filtrate was evaporated to dryness
  3. customThe intermediate imine was separated out by preparative HPLC chromatography (RP 18, acetonitrile, water, 0.01% TFA)
  4. customThe solvent was evaporated off
  5. extractionextracted with ethyl acetate
  6. customThe combined organic phases were dried
  7. customafter evaporation
  8. customwas purified by flash chromatography (SiO2, methylene chloride/methanol=98/2)

Quellen und Nachweise

ORD-Eintrag
ord-e7ff54e28e4f4933b0f11e91ff432df8
Quelldatensatz
uspto-grants-2010_11
Patentnummer
US07825115B2

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