Triethylamine → HCID 58319377, Verbindung

HRID 444699Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 444699
Cl[C:2]([C:11]1[S:12][CH:13]=[C:14]([CH3:17])[C:15]=1[Cl:16])=[C:3]([C:9]#[N:10])[C:4]([O:6][CH2:7][CH3:8])=[O:5].Cl.[CH3:19][NH:20][C:21](=[O:25])[C@H:22]([CH3:24])[NH2:23].C(N(CC)CC)C>C(#N)C>[Cl:16][C:15]1[C:14]([CH3:17])=[CH:13][S:12][C:11]=1/[C:2](/[NH:23][C@H:22]([CH3:24])[C:21]([NH:20][CH3:19])=[O:25])=[C:3](\[C:9]#[N:10])/[C:4]([O:6][CH2:7][CH3:8])=[O:5]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 18595779(2S)-2-amino-N-methylpropanamide hydrochlorideHCID 76759590HCID 76759590, Verbindung

Produkt 1

HCID 58319377HCID 58319377, VerbindungAusbeute 60,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

To a solution of ethyl 3-chloro-3-(3-chloro-4-methyl-2-thienyl)-2-cyanoacrylate (0.351 g, 1.21 mmol, 1 eq.) in 3 ml of acetonitrile was added N-methyl-L-alaninamide hydrochloride (0.201 g, 1.45 mmol, 1.2 eq.) followed by triethylamine (TEA) (0.490 g, 4.84 mmol, 4 eq.). The reaction was microwaved (130° C., 300 s, fixed hold, high absorption) and the solvent evaporated. The residual oil was triturated in ethyl acetate and the white solid removed by filtration. After concentration under vacuum, the residual oil was subjected to column chromatography to give ethyl (2Z)-3-(3-chloro-4-methyl-2-thienyl)-2-cyano-3-{[(2R)-1-(methylamino)-1-oxopropan-2-yl]amino}acrylate (0.26 g, 57% yield) as a mixture of atropoisomers.

Aufarbeitung

  1. customThe reaction was microwaved
  2. custom(130° C., 300 s, fixed hold, high absorption)
  3. customthe solvent evaporated
  4. customThe residual oil was triturated in ethyl acetate
  5. customthe white solid removed by filtration
  6. concentrationAfter concentration under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-c07b7fe3a21c4708944482a536cc5258
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08476197B2

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