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Triethylamine → (E)-N-[2-[(2-Methyl-4-quinolyl)amino]ethyl]but-2-enamide

HRID 333098
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 333098
C[CH:2](C)/[CH:3]=[CH:4]/[C:5](O)=[O:6].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH3:33][C:34]1[CH:43]=[C:42]([NH:44][CH2:45][CH2:46][NH2:47])[C:41]2[C:36](=[CH:37][CH:38]=[CH:39][CH:40]=2)[N:35]=1.C(N(CC)CC)C>C(#N)C>[CH3:33][C:34]1[CH:43]=[C:42]([NH:44][CH2:45][CH2:46][NH:47][C:5](=[O:6])/[CH:4]=[CH:3]/[CH3:2])[C:41]2[C:36](=[CH:37][CH:38]=[CH:39][CH:40]=2)[N:35]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 6420393-Isopropyl acrylic acidHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 6471895N1-(2-Methylquinolin-4-yl)ethane-1,2-diamine

Produkt 1

HCID 86691181(E)-N-[2-[(2-Methyl-4-quinolyl)amino]ethyl]but-2-enamideAusbeute 68,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

(E)-4-Methylpent-2-enoic acid (190 mg, 1.3 mmol) was mixed together with HBTU (470 mg, 1.3 mmol) and N-(2-methyl-4-quinolyl)ethane-1,2-diamine (250 mg, 1.2 mmol) in acetonitrile (5 ml). Triethylamine (1 mll) was added with stirring at 0° C. over 15 minutes and the resulting mixture was stirred at room temperature overnight. The volatiles were removed under reduced pressure, the residue was dissolved in DCM and washed with a saturated solution of sodium bicarbonate. The combined aqueous solutions were extracted three times with DCM. The organic layers were combined, dried over sodium sulfate, the solvent was removed under reduced pressure to give 245 mg of a yellow solid (0.82 mmol, 66%). MS (APCI) m/z=298.2 [M+1]+.

Aufarbeitung

  1. stirringthe resulting mixture was stirred at room temperature overnight
  2. customThe volatiles were removed under reduced pressure
  3. dissolutionthe residue was dissolved in DCM
  4. washwashed with a saturated solution of sodium bicarbonate
  5. extractionThe combined aqueous solutions were extracted three times with DCM
  6. dry with materialdried over sodium sulfate
  7. customthe solvent was removed under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-5f64f7331f114d09a892ddee5f9bd4b8
Quelldatensatz
uspto-grants-2014_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08877934B2

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