Phenyl 2-(6-amino-2-oxo-3,4-dihydroquinolin-1(2H)-yl)ethyl(methyl)carbamate → Phenyl methyl(2-(2-oxo-6-(thiophene-2-carboximidamido)-3,4-dihydroquinolin-1(2H)-yl)ethyl)carbamate

HRID 1922413Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1922413
I.[S:2]1[CH:6]=[CH:5][CH:4]=[C:3]1[C:7](SC)=[NH:8].[NH2:11][C:12]1[CH:13]=[C:14]2[C:19](=[CH:20][CH:21]=1)[N:18]([CH2:22][CH2:23][N:24]([CH3:34])[C:25](=[O:33])[O:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[C:17](=[O:35])[CH2:16][CH2:15]2>C(O)C>[CH3:34][N:24]([CH2:23][CH2:22][N:18]1[C:19]2[C:14](=[CH:13][C:12]([NH:11][C:7]([C:3]3[S:2][CH:6]=[CH:5][CH:4]=3)=[NH:8])=[CH:21][CH:20]=2)[CH2:15][CH2:16][C:17]1=[O:35])[C:25](=[O:33])[O:26][C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1

Komponenten

4

Edukt 2

HCID 59807067Phenyl 2-(6-amino-2-oxo-3,4-dihydroquinolin-1(2H)-yl)ethyl(methyl)carbamateHCID 66704664Methyl thiophene-2-carbimidothioate hydroiodide

Produkt 1

HCID 178484234Phenyl methyl(2-(2-oxo-6-(thiophene-2-carboximidamido)-3,4-dihydroquinolin-1(2H)-yl)ethyl)carbamate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

Methyl thiophene-2-carbimidothioate hydroiodide (1.62 g, 5.71 mmol) was weighed into a round bottom flask with a stirbar. Phenyl 2-(6-amino-2-oxo-3,4-dihydroquinolin-1(2H)-yl)ethyl(methyl)carbamate (0.969 g, 2.85 mmol) was dissolved in ethanol (50 mL) and added to the flask. The resulting suspension was stirred overnight at room temperature. When the reaction was finished, argon was bubbled through the reaction mixture for 1 h, then the mixture was neutralized with sodium carbonate (sat. aq. solution). The product was extracted with dichloromethane (3×). The combined organics were dried over sodium sulfate, filtered and concentrated. The residue was chromatographed in (1:1) ethyl acetate:CH2Cl2 then 10% (2M NH3 in methanol) in dichloromethane. Yield: 700 mg, 55%. 1H NMR (DMSO-d6) δ 7.91 (m, 2H), 7.38 (m, 2H), 7.26 (m, 3H), 7.04 (m, 4H), 4.23 and 4.14 (2m, 2H), 3.63 and 3.51 (2m, 2H), 3.06 and 2.92 (2s, 3H), 2.84 (t, 2H, J=6.9 Hz), 2.56 (t, 2H, J=6.9 Hz); ESI-MS (m/z, %): 449 (MH+, 100).

Aufarbeitung

  1. additionadded to the flask
  2. customargon was bubbled through the reaction mixture for 1 h
  3. extractionThe product was extracted with dichloromethane (3×)
  4. dry with materialThe combined organics were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was chromatographed in (1:1) ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-7bad77fb50fa49fca69a91862769f2d6
Quelldatensatz
uspto-grants-2012_05
Patentnummer
US08173813B2

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