Isopropylamine → (1Z)-1-[5-methyl-3-[4-(trifluoromethyl)phenyl]-1,3-thiazol-2-ylidene]-3-propan-2-ylurea

HRID 390722Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 390722
[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])C=1.[CH:27](N(C(C)C)CC)(C)C.CC(N)C>C(#N)C>[CH:6]([NH:5][C:8](/[N:10]=[C:11]1\[S:12][C:13]([CH3:26])=[CH:14][N:15]\1[C:16]1[CH:21]=[CH:20][C:19]([C:22]([F:24])([F:23])[F:25])=[CH:18][CH:17]=1)=[O:9])([CH3:27])[CH3:7]

Komponenten

5

Edukt 3

HCID 6363IsopropylamineHCID 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 87448515(1Z)-1-[5-methyl-3-[4-(trifluoromethyl)phenyl]-1,3-thiazol-2-ylidene]-3-propan-2-ylurea

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 (45 mg, 0.1 mmol, Example 18B) dissolved in acetonitrile (0.6 mL) was added followed by the addition of diisopropylethylamine (22 μL, 0.13 mmol) dissolved in acetonitrile (0.6 mL). Then to the solution was added propan-2-amine (6 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-32d152be99a0473bbf8395b9fd012430
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08383657B2

Notizen zur Reaktion

Wird geladen…