Indoline → (NZ)-N-[5-methyl-3-[4-(trifluoromethyl)phenyl]-1,3-thiazol-2-ylidene]-2,3-dihydroindole-1-carboxamide

HRID 390718Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 390718
[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.C(N(C(C)C)CC)(C)C.N1C2[C:39](=[CH:40][CH:41]=CC=2)[CH2:38][CH2:37]1>C(#N)C>[CH3:26][C:13]1[S:12]/[C:11](=[N:10]\[C:8]([N:5]2[C:4]3[C:37](=[CH:38][CH:39]=[CH:40][CH:41]=3)[CH2:7][CH2:6]2)=[O:9])/[N:15]([C:16]2[CH:21]=[CH:20][C:19]([C:22]([F:25])([F:24])[F:23])=[CH:18][CH:17]=2)[CH:14]=1

Komponenten

5

Edukt 3

HCID 10328IndolineHCID 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 87444127(NZ)-N-[5-methyl-3-[4-(trifluoromethyl)phenyl]-1,3-thiazol-2-ylidene]-2,3-dihydroindole-1-carboxamide

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 (62 mg, 0.13 mmol, Example 18B) dissolved in acetonitrile (0.6 mL) was added followed by the addition of diisopropylethylamine (28 μL, 0.16 mmol) dissolved in acetonitrile (0.6 mL). Then, to the solution was added indoline (17 mg, 0.14 mmol) dissolved in acetonitrile (0.7 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-a780f4a473714a76863fa73dbab83f21
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08383657B2

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