HCID 18762004, Verbindung → HCID 69905062, Verbindung

HRID 430903Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 430903
[CH3:1][N:2]1[CH2:6][CH2:5][CH2:4][CH:3]1[C:7]1[CH:8]=[C:9]([C:13]#[C:14][C:15]2[CH:24]=[CH:23][C:18]([C:19]([O:21][CH3:22])=[O:20])=[CH:17][CH:16]=2)[CH:10]=[N:11][CH:12]=1>CO>[CH3:1][N:2]1[CH2:6][CH2:5][CH2:4][CH:3]1[C:7]1[CH:12]=[N:11][CH:10]=[C:9]([CH2:13][CH2:14][C:15]2[CH:16]=[CH:17][C:18]([C:19]([O:21][CH3:22])=[O:20])=[CH:23][CH:24]=2)[CH:8]=1

Komponenten

3

Edukt 1

HCID 18762004HCID 18762004, Verbindung

Produkt 1

HCID 69905062HCID 69905062, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

A mixture of YH19 (0.15 g, 0.468 mmol) and Pd(C) (10%, 20 mg) in MeOH (10 mL) was hydrogenated at atmospheric pressure and room temperature for one day. The catalyst was removed by filtration through Celite and the filtrate was concentrated. The residue was chromatographed [SiO2, CHCl3/MeOH (60:1)] to give 0.15 g (95%) of YH22; 1H NMR (400 MHz, CDCl3) δ 8.38 (br s, 2H), 7.91-7.80 (m, 2H), 7.40 (s, 1H), 7.16-7.14 (m, 2H), 3.85 (s, 3H), 3.23-3.16 (m, 1H), 3.05-2.87 (m, 5H), 2.30-2.22 (m, 1H), 2.18-2.08 (m, 1H), 2.09 (s, 3H), 1.92-1.84 (m, 1H), 1.81-1.72 (m, 1H), 1.67-1.57 (m, 1H); 13C NMR (400 MHz, CDCl3) δ 166.9, 148.6, 147.3, 146.2, 138.3, 136.5, 134.5, 129.7, 128.0, 68.6, 56.9, 51.9, 40.2, 37.4, 35.0, 34.4, 22.4;

Aufarbeitung

  1. customThe catalyst was removed by filtration through Celite
  2. concentrationthe filtrate was concentrated
  3. customThe residue was chromatographed [SiO2, CHCl3/MeOH (60:1)]
  4. customto give 0.15 g (95%) of YH22

Quellen und Nachweise

ORD-Eintrag
ord-30ee736460c943088a8e7d2681e63854
Quelldatensatz
uspto-grants-2003_12
Patentnummer
US06656469B1

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