N-Methylpropylamine → (3Z)-1-methyl-3-[5-methyl-3-[4-(trifluoromethyl)phenyl]-1,3-thiazol-2-ylidene]-1-propylurea

HRID 390720Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 390720
[I-].C[N+]1[CH:7]=[CH:6][N:5]([C:8](/[N:10]=[C:11]2\[S:12][C:13]([CH3:26])=[CH:14][N:15]\2[C:16]2[CH:21]=[CH:20][C:19]([C:22]([F:25])([F:24])[F:23])=[CH:18][CH:17]=2)=[O:9])[CH:4]=1.[CH:27](N(C(C)C)CC)(C)C.CNCCC>C(#N)C>[CH3:4][N:5]([CH2:6][CH2:7][CH3:27])[C:8](/[N:10]=[C:11]1\[S:12][C:13]([CH3:26])=[CH:14][N:15]\1[C:16]1[CH:17]=[CH:18][C:19]([C:22]([F:25])([F:23])[F:24])=[CH:20][CH:21]=1)=[O:9]

Komponenten

5

Edukt 3

HCID 12315N-MethylpropylamineHCID 81531DiisopropylethylamineHCID 87447393(NZ)-3-methyl-N-[5-methyl-3-[4-(trifluoromethyl)phenyl]-1,3-thiazol-2-ylidene]imidazol-3-ium-1-carboxamide;iodide

Produkt 1

HCID 87449087(3Z)-1-methyl-3-[5-methyl-3-[4-(trifluoromethyl)phenyl]-1,3-thiazol-2-ylidene]-1-propylurea

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel3×

Versuchsvorschrift

In a 20 mL vial a solution of 3-methyl-1-({[(2Z)-5-methyl-3-[4-(trifluoromethyl)phenyl]-1,3-thiazol-2(3H)-ylidene]amino}carbonyl)-1H-imidazol-3-ium iodide (50 mg, 0.10 mmol, Example 18B) dissolved in acetonitrile (0.6 mL) was added followed by the addition of diisopropylethylamine (28 μL, 0.13 mmol) dissolved in acetonitrile (0.6 mL). Then, to the solution was added N-methylpropan-1-amine (8 mg, 0.11 mmol) dissolved in acetonitrile (0.5 mL). The vial was capped and shaken overnight at room temperature. The reaction was concentrated to dryness. The residue was purified by reverse phase HPLC (C18, gradient 10-95% acetonitrile/water/0.1% trifluoroacetic acid) to provide the title compound.

Aufarbeitung

  1. additionwas added
  2. customThe vial was capped
  3. concentrationThe reaction was concentrated to dryness
  4. customThe residue was purified by reverse phase HPLC (C18, gradient 10-95% acetonitrile/water/0.1% trifluoroacetic acid)

Quellen und Nachweise

ORD-Eintrag
ord-5eb201ceb9f54bd8801ad13fc75c4b25
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08383657B2

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